In the list above, the numbers refer to the embodiments according to their numbering provided hereinabove whereas "+" indicates the dependency from another embodiment. The different individualized embodiments are separated by commas. In other words, "14+8+1" for example refers to embodiment 14) depending on embodiment 8), depending on embodiment 1), i.e. embodiment "14+8+1" corresponds to the compounds of embodiment 1) further limited by the features of the embodiments 8) and 14).
17) A further embodiment relates to compounds of Formula (I) according to embodiment 1) which are selected from the following compounds:
2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1,1-dioxo-1l6-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-piperidin-1-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-morpholin-4-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-diethylamino-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-methoxy-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-hydroxy-3-methyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-dimethylamino-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-morpholin-4-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-caitoxylicacid{2-[methyl-(3-methyl-oxetan-3-yl)-amino]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[3-(1,1-dioxo-1l6-thiomorpholin-4-yl)-azetidin-1-yl]-benzooxazol-5-yl}-amide;
2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-hydroxy-3-methyl-[1,3']biazetidinyl-1 '-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.4]oct-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-5-aza-spiro[3.5]non-5-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-8-aza-spiro[4.5]dec-8-yl)-benzooxazol-5-yl]-amide;

2,3-Dihydro-benzofuran-5-carboxylic acid [2-(7-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(5-oxa-2-aza-spiro[3.4]oct-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[3-(4-hydroxy-piperidin-1-yl)-azetidin-1-yl]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-methyl-2,6-diaza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(5-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide; 1-{5-[(2,3-Dihydro-benzofuran-5-carbonyl)-amino]-benzooxazol-2-yl}-azetidine-3-carboxylicacidtert-butyl ester; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxo-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid[2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide; 4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide;
(R)-N-(2-(3-hydroxypiperidin-1-yl)benzo[d]oxazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((S)-3-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-isopropoxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((R)-3-hydroxy-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((S)-3-hydroxy-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-phenyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-ethoxymethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[(3-fluoro-oxetan-3-ylmethyl)-methyl-amino]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-oxetan-3-yl-piperazin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[methyl-(1-oxetan-3-yl-piperidin-4-yl)-amino]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(methyl-oxetan-3-ylmethyl-amino)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(methyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-methoxymethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylaminomethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-phenyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-pyrrolidin-1-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[3-(1-hydroxy-1-methyl-ethyl)-azetidin-1-yl]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylaminomethyl-azetidin-1-yl)-benzooxazol-5-yl]-amide;

2,3-Dihydro-benzofuran-5-carboxylic acid [2-(7-methyl-1,7-diaza-spiro[3.5]non-1 -yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(7-methyl-2,7-diaza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylamino-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2,2-dioxo-2l6-thia-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1,1-dioxo-1l6-thia-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylamino-3-methyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-2-aza-spiro[3.4]oct-2-yl)-benzooxazol-5-yl]-amide; 2-(4-Methyl-piperazin-1-yl)-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide; 2-Piperidin-1-yl-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide; 2-Morpholin-4-yl-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide; 2-Diethylamino-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide; 2-Pyrrolidin-1-yl-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide; 2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-piperidin-1-yl-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-morpholin-4-yl-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-methyl-piperazin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-pyrrolidin-1-yl-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-diethylamino-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-dimethylamino-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-azetidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1,1 -dioxo-1 l6-thiomorpholin-4-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-methoxy-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-methoxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-hydroxy-3-methyl-azetidin-1-yl)-benzothiazol-5-yl]-amide; (S)-N-(2-(3-hydroxypyrrolidin-1-yl)benzo[d]thiazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[methyl-(1-oxetan-3-yl-piperidin-4-yl)-amino]-benzothiazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(methyl-oxetan-3-yl-amino)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-methoxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-hydroxy-azetidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide;

2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-phenyl-azetidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((R)-3-hydroxy-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-methoxymethyl-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((S)-3-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.4]oct-6-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((R)-3-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-dimethylaminomethyl-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-azetidin-1-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid(2-ethylamino-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-pyridin-2-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid(2-piperidin-1-yl-benzooxazol-5-yl)-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid (2-morpholin-4-yl-benzooxazol-5-yl)-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylicacid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid (2-diethylamino-benzooxazol-5-yl)-amide; Chroman-6-carboxylic acid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylicacid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide; Chroman-6-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylicacid(2-piperidin-1-yl-benzooxazol-5-yl)-amide; Chroman-6-carboxylic acid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide;

Chroman-6-carboxylic acid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide;
Chroman-6-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide;
Chroman-6-carboxylic acid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide;
Chroman-6-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide;
Chroman-6-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide;
Chroman-6-carboxylicacid(2-morpholin-4-yl-benzooxazol-5-yl)-amide;
Chroman-6-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide;
Chroman-6-carboxylicacid(2-diethylamino-benzooxazol-5-yl)-amide;
Chroman-6-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid[2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid(2-piperidin-1-yl-benzooxazol-5-yl)-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid[2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid[2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid[2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid (2-morpholin-4-yl-benzooxazol-5-yl)-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid[2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid (2-diethylamino-benzooxazol-5-yl)-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid(2-piperidin-1-yl-benzooxazol-5-yl)-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide;

4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid(2-morpholin-4-yl-benzooxazol-5-yl)-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid(2-diethylamino-benzooxazol-5-yl)-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-
amide;
2-Piperidin-1-yl-benzothiazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(4-Methoxy-piperidin-1-yl)-benzothiazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(4-Methyl-piperazin-1-yl)-benzothiazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(6-Oxa-1-aza-spiro[3.4]oct-1-yl)-benzothiazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylicacid(2,3-dihydro-benzo[1,4]dioxin-6-yl)-amide;
2-(6-Oxa-1-aza-spiro[3.4]oct-1-yl)-benzothiazole-5-carboxylicacid(2,3-dihydro-benzo[1,4]dioxin-6-yl)-amide; and
2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylicacidbenzo[1,3]dioxol-5-ylamide.
The compounds of compounds of formula (I) as defined in any one of embodiments 1) to 17) and their pharmaceutical^ acceptable salts can be used as medicaments, e.g. in the form of pharmaceutical compositions for enteral (such especially oral, e.g. in form of a tablet or capsule) or parenteral administration (including intravenous, intraperitoneal, subcutaneous, or topical application, or inhalation).
The production of the pharmaceutical compositions can be effected in a manner which will be familiar to any person skilled in the art (see for example Remington, The Science and Practice of Pharmacy, 21st Edition (2005), Part 5, "Pharmaceutical Manufacturing" [published by Lippincott Williams & Wilkins]) by bringing the described compounds of Formula (I) or their pharmaceutical^ acceptable salts, optionally in combination with other therapeutically valuable substances, into a galenical administration form together with suitable, non-toxic, inert, pharmaceutical^ acceptable solid or liquid carrier materials and, if desired, usual pharmaceutical adjuvants.

The compounds of compounds of formula (I) as defined in any one of embodiments 1) to 17) and their pharmaceutical^ acceptable salts are useful for modulating NOX4, especially for the prevention or treatment of fibrotic diseases; and/or diseases or disorders associated with an impaired reactive oxygen species (ROS) production.
Fibrotic diseases may defined as comprising pulmonary fibrosis, especially idiopathic pulmonary fibrosis (IPF); scleroderma, especially systemic sclerosis; pancreatic fibrosis; liver fibrosis; chronic kidney disease, especially diabetic nephropathy; and cardiomyopathy (associated with fibrosis) including heart failure resulting from chronic cardiomyopathy, diabetic cardiomyopathy, and hypertrophic cardiomyopathy.
Diseases or disorders associated with impaired reactive oxygen species (ROS) production may defined as comprising pulmonary hypertension; hypertension; asthma; acute respiratory distress syndrome (ARDS); myocardial infarction; acute heart failure; cardiac and skeletal myopathy including Barth syndrome; stroke; traumatic brain injury; neuropathic pain; ataxia telangiectasia (Louis-Bar syndrome); ocular diseases, such as diabetic Tenopathy; and cancer (especially ovarian cancer, renal cell carcinoma, glioblastoma multiforme, head and neck squamous cell carcinoma (HNSCC), pancreatic adenocarcinoma, colon cancer, urothelial cancer, prostate cancer, breast cancer, non-small cell lung cancer, and metastasis).
In particular, diseases or disorders associated with impaired reactive oxygen species (ROS) production may defined as comprising heart and vascular remodeling in response to pulmonary hypertension; hypertension; asthma; acute respiratory distress syndrome (ARDS); acute myocardial infarction; acute heart failure; heart failure associated with uncontrolled neurohormonal excitation; cardiac and skeletal myopathy including Barth syndrome; acute stroke; and acute traumatic brain injury.
For avoidance of any doubt, if compounds are described as being useful for the prevention or treatment of certain diseases, such compounds are likewise suitable for use in the preparation of a medicament for the prevention or treatment of said diseases.
The present invention also relates to a method for the prevention or treatment of a disease or disorder mentioned herein comprising administering to a subject in need thereof a pharmaceutical^ active amount of a compound of formula (I) as defined in any one of embodiments 1) to 17).
In a preferred embodiment of the invention, the administered amount of such a compound of formula (I) as defined in any one of embodiments 1) to 17) is comprised between 1 mg and 1000 mg per day, particularly between 5 mg and 500 mg per day, more particularly between 10 mg and 400 mg per day.

The present invention also relates to a method of inhibition of myofibroblast differentiation in a subject (by modulating NOX4), comprising administering to said subject an effective amount of a compound of formula (I) as defined in any one of embodiments 1) to 17); wherein especially said subject has been diagnosed to have a fibrotic disease, and/or a disease or disorder associated with impaired reactive oxygen species (ROS) production.
Said inhibition of myofibroblast differentiation may especially be monitored by
• reduced levels of ROS in organ biopsies (Gorin, Y., et al. Targeting NADPH oxidase with a novel dual NOX1/NOX4 inhibitor attenuates renal pathology in type 1 diabetes. Am J Physiol Renal Physiol, ajprenal 00396 02014 (2015)); and/or
• reduced levels of ROS in exhaled breath condensate (Psathakis, K., et al. Exhaled markers of oxidative stress in idiopathic pulmonary fibrosis. Eur J Clin Invest 36, 362-367 (2006)); and/or
• reduced levels of alpha smooth muscle actin; and/or
• reduced levels of deposited extracellular matrix protein in tissue biopsies (Hecker, L, et al. NADPH oxidase-4 mediates myofibroblast activation and fibrogenic responses to lung injury. Nat Med 15, 1077-1081 (2009));
of said subject (e.g. when compared to the respective levels before said subject has been administered the compound of formula (I)).
The present invention also relates to the use of a compound of Formula (I) for the preparation of a pharmaceutical composition, optionally for use in combination with one or several anti-fibrotic agents [such as, but not limited to kinase inhibitors (more specifically: receptor tyrosine kinase antagonists and/or p38 kinase inhibitors), and/or antagonists of the renin-angiotensin system (RAS), and/or endothelin receptor antagonists, and or stimulators of guanylate cyclase, and/or ligands of peroxisome proliferator activated nuclear receptor gamma (PPARc), and/or antagonists of serotonin signalling, and/or antagonists of integrin-mediated signalling, and/or antagonists of cytokine signalling, and/or antagonists of lysophosphatidic acid (LPA) receptors, and/or therapies targeting M2 type macrophage biology- for the prevention or treatment of the diseases and disorders mentioned herein.
Preparation of the compounds of Formula (I)
The compounds of Formula (I) can be manufactured by the methods given below, by the methods given in the Examples or by analogous methods. Optimum reaction conditions may vary with the particular reactants or solvents used, but such conditions can be determined by a person skilled in the art by routine optimisation procedures.
Compounds of the Formula (I) of the present invention can be prepared according to the general sequence of reactions outlined below, by known literature methods, by the methods

given in the experimental part or by analogous methods. Only a few of the synthetic possibilities leading to compounds of Formula (I) are described. Optimum reaction conditions may vary with the particular reactants or solvents used, but such conditions can be determined by a person skilled in the art by routine optimisation procedures. In some instances the generic groups L, Y, and ring (A) may be incompatible with the assembly illustrated in the schemes below and will require the use of protecting groups. The use of protecting groups is well known in the art (see for example "Protective Groups in Organic Synthesis", T.W. Greene, P.G.M. Wuts, Wiley-lnterscience, 1999). For the purposes of this discussion, it will be assumed that such protecting groups as necessary are in place. The compounds obtained may also be converted into pharmaceutically acceptable salts thereof in a manner known per se. In the general sequence of reactions outlined below, the generic groups L, X, Y, and ring (A) are as defined for formula (I).
Compounds of Formula (I) wherein L represents -CO-NH- are prepared by reacting a compound of Structure 1 with a compound of Structure 2 by using a coupling reagent such as HATU, TBTU, EDC, etc. in the presence or absence of HOBt, in the presence of a base such Et3N, DIPEA, etc. and in a solvent such as DMF, DCM, THF, etc. Alternatively, coupling of a compound of Structure 1 to a compound of Structure 2 may also be affected by reacting the corresponding acid chloride of a compound of Structure 1.

Compounds of Structure 1 are either commercially available or are prepared according to procedures know to the person skilled in the art.
Compounds of Structure 2 are prepared by reducing a compound of Struture 3 e.g. with a hydrogen gas in the presence of a catalyst such as Pd/C, Pt/C, Pt02 in a solvent such as MeOH, EtOH, EA, THF, etc. or mixtures thereof, or with Fe in a solvent such as acetic acid.

Compounds of Structure 3 are prepared by reacting a compound of Structure 4 with a compound of Structure 5 in the presence or absence of a base such as Et3N, DIPEA, NaHC03, K2C03, KOtBu, etc. in a solvent such as THF, DMF, DMSO, etc. or in analogy to literature

procedures (e.g. R. E. Martin et al. Bioorg. Med. Chem. Lett. 19 (2009) 6106-6113; F. Hayat et al. Bull. Korean Chem. Soc. 34 (2013) 495-499).

Compounds of Structure 4 are either commercially available or are prepared by reacting a compound of Structure 6 with a chlorinating agent such as SOCI2, S02CI2, POCI3, or PCI5 in the presence or absence of a solvent such as DCM, CHCI3, DMF, etc. preferrably at temperatures between 20 and 80°C.
Compounds of Structure 5 are either commercially available or are prepared according to procedures known to a person skilled in the art.

Compounds of structure 6 are either commercially available or are prepared according to known literature procedures e.g. L. Zhu et al. J. Heterocycl. Chem. 42 (2005) 727-730, J. C. Mannion et al. WO2011/112602; G. M. Wynne et al. WO2007/091106.
Alternatively, compounds of Formula (I) wherein L represents -CO-NH-* may also be prepared by reacting a compound of structure 7 wherein L represents -CO-NH-* with a compound of structure 5 in the presence or absence of a base such as Et3N, DIPEA, NaHC03, K2C03, KOtBu, etc. in a solvent such as THF, DMF, DMSO, etc.

Compounds of structure 7 are prepared by treating a compound of structure 8 wherein L represents -CO-NH-* with a chlorinating reagent such aus SOCI2, in presence or absence of a solvent such as DCM, DMF, or DMA.


Compounds of structure 8 can be prepared by reacting a compound of structure 10 with a compound of structure 9 with a base such as Et3N, DIPEA, etc., in a solvent such as DCM, or by reacting a compound of structure 10 with a compound of structure 1 in the presence of a base and in the presence of a coupling reagent such as TBTU, HATU, EDC, etc. in a solvent such as DMF. A compound of structure 10 can also be reacted with a compound of structure 1 by chlorinating a compound structure 1 in situ in the presence of a chlorinating agent such as SOCI2 in the presence or absence of a catalytic amount of DMF in a solvent such as DCM.

Compounds of structure 9 are either commercially available or may be prepared from a compound of structure 1 following known procedures.
Compounds of structure 10 are either commercially available or are prepared according to known procedures, e.g. L. Katz et al. J. Org. Chem. 19 (1954) 758-766, K. D. Rynearson, Bioorg. Med. Chem. Lett. 24 (2014) 3521-3525, D. S. B. Ongarora et al. Bioorg. Med. Chem. Lett. 22 (2012) 5046-5050, L. Zhu et al. J. Heterocycl. Chem. 42 (2005) 727-730, Y. Murti et al. J. Pharm. Res. 7(2008) 153-155.
Compounds of Formula (I) wherein L represents -NH-CO-* are prepared by reacting a compound of Structure 11 with a compound of Structure 12 by using a coupling reagent such as 1-chloro-N,N-2-trimethylpropenylamine (Ghosez' reagent), HATU, TBTU, EDC, or POCI3 etc. in the presence or absence of HOBt, in the presence of a base such Et3N, DIPEA, etc. and in a solvent such as DCM, DMF, THF, pyridine, or mixtures thereof. Alternatively, coupling of a compound of Structure 11 to a compound of Structure 12 may also be achieved by reacting the corresponding acid chloride of a compound of Structure 12 with a compound of Structure 11.

Compounds of Structure 11 are commercially available or well known in the art.
Compounds of Structure 12 are prepared by saponification of Structure 13, wherein R represents C^-alkyl, under conditions know to a person skilled in the art, e.g. by exposing a compound of structure 13 to a mixture of aq. NaOH, methanol and THF or to aq. HCI.

Compounds of Structure 13 are prepared by reacting a compound of Structure 14 with a compound of Structure 5 in the presence or absence of a base such as Et3N, DIPEA, NaHC03, K2C03, KOtBu, etc. in a solvent such as THF, DMF, DMSO, etc., preferrably at temperatures between 20 and 80°C.

Compounds of Stucture 14 are either commercially available or are prepared following literature procedures (e.g. A. Binggeli, WO2007025897), or by chlorinating a compound of Structure 15 with a chlorinating agent such as POCI3, PCI5, SOCI2, S02CI2 in a solvent such as DCM, CHCI3, DMF, etc.

Compounds of Structure 15 are either commercially available or are obtained following literature procedures (e.g. S. Hachiya, WO2008059854, J.-L. Chen WO2005086904).
Experimental Part
The following examples illustrate the invention but do not at all limit the scope thereof.
All temperatures are stated in °C. Compounds are characterized by 1H-NMR (Bruker Avance II, 400 MHz UltraShield™, 400 MHz (1H), 100 MHz (13C); or Bruker Avance III HD, Ascend 500 MHz (1H), 125 MHz (13C) magnet equiped with DCH cryoprobe); chemical shifts are given in ppm relative to the solvent used; multiplicities: s = singlet, d = doublet, t = triplet, p = pentuplet, hex = hexet, hept = heptet, m = multiplet, br = broad, coupling constants are given in Hz), in case non-deuterated DMSO was used as a solvent, the resonance of the solvent at 2.5 ppm was suppressed; by LC-MS: Finnigan MSQ™ plus or MSQ™ surveyor (Dionex, Switzerland), with HP 1100 Binary Pump and DAD (Agilent, Switzerland), column: ZorbaxSB-AQ, 5 urn, 120 A, 4.6x50 mm (Agilent), gradient: 5-95% acetonitrile in water containing 0.04% of trifluoroacetic acid, within 1 min, flow: 4.5 mL/min; tR is given in min, or by TLC (TLC-plates from Merck, Silica

gel 60 F254); or by melting point. Compounds are purified by preparative HPLC (column: X-terra RP18, 50x19 mm, 5 urn, gradient: 10-95% MeCN in water containing 0.5 % of formic acid).
Abbreviations (as used herein):
abs absolute
aq. aqueous
BSA bovine serum albumin
CC column chromatography on silica gel
DCM dichloromethane
DIPEA Huning's base, diethylisopropylamine
DMA N,N-dimethylacetamide
DMF dimethylformamide
DMSO dimethylsulfoxide
EA ethyl acetate
EDC N-(3-dimethylaminopropyl)-N'-ethyl-carbodiimide
Et ethyl
EtOH ethanol
h hour(s)
HATU 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b] pyridinium 3-
oxid hexafluorophosphate
HBTU 0-(benzotriazol-1 -yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
HOBt 1-hydroxy-benzotriazole
HPLC high performance liquid chromatography
HV high vacuum conditions
LC-MS liquid chromatography - mass spectrometry
KOtBu potassium tert.-butylate
Lit. literature
Me methyl
MeCN acetonitrile
MeOH methanol
min minute(s)
NEt3 triethylamine
org. organic
PPh3 triphenylphosphine
PyBOP benzotriazol-1 -yl-oxy-tris-pyrrolidino-phosphonium-
hexafluoro-phosphate
prep. preparative
rt room temperature

sat. saturated
TBTU 2-(1H-benzotriazole-1-yr)-1,2,3,3-tetramethyluronium tetrafluoroborate
tert. tertiary
TFA trifluoroacetic acid
THF tetrahydrofuran
TLC thin layer chromatography
tR retention time
Preparation of Building Blocks
5-Nitrobenzo[d]oxazole-2-thiol
To a solution of 2-amino-4-nitrophenol (10 g, 64.2 mmol) in abs. EtOH (150 ml_) potassium ethyl xanthogenate (12.6 g, 77.1 mmol) was added. The mixture was stirred under reflux for 5 h before it was cooled to rt and concetrated. The residue was dissolved in water (300 ml_) and treated with 1 M aq. HCI (75 ml_) with vigorous stirring. The precipitate that formed was collected, washed with water (50 ml_) and dried under HV for 2 days to give the title compound (ortautomer) (11.9 g) as a grey-beige solid; LC-MS: tR = 0.71 min; [M+H]+ = not detectable; 1H NMR (400 MHz, D6-DMSO) 5: 14.33 (s br, 1 H), 8.21 (dd, J, = 2.3 Hz, J2 = 8.9 Hz, 1 H), 7.96 (d, J = 2.3 Hz, 1 H), 7.75 (d, J = 8.9 Hz, 1 H). 2-Chloro-5-nitrobenzo[d]oxazole
To a suspension of 5-nitrobenzo[d]oxazole-2-thiol (5.9 g, 30 mmol) in thionyl chloride (54.7 ml_, 751 mmol) DMF (0.04 ml_, 0.456 mmol) was added. The mixture was heated to 65°C and stirred for 1 h. The mixture was cooled to rt and concentrated. The residue was suspended in toluene (30 ml_) and the solvent was again evaporated. The residue was then taken up in DCM (25 ml_) and purified by CC eluting with heptane:EA 4:1 to give the title compound (4.4 g) as a beige solid; LC-MS: tR = 0.78 min; [M+H]+ = not detectable; 1H NMR (400 MHz, CDCI3) 5: 8.61 (d, J = 2.3 Hz, 1 H), 8.38 (dd, J, = 2.3 Hz, J2 = 9.0 Hz, 1 H), 7.68 (d, J = 9.0 Hz, 1 H). 5-Nitrobenzo[d]oxazole-2-thiol
A mixture of 2-amino-4-nitrophenol (4.0 g, 26 mmol) and potassium xanthogenate (5.0 g, 31.2 mmol) in EtOH (100 ml_) was refluxed for 24 h before it was stirred at rt for two additional days. The precipitat that formed was collected, washed with EtOH and dried to give the title compound (or tautomer) (5.3 g) as an orange solid; LC-MS: tR = 0.71 min; [M+H]+ = not detectable; 1H NMR (400 MHz, D6-DMSO) 5: 7.85 (dd, J, = 2.4 Hz, J2 = 8.6 Hz, 1 H), 7.82 (d, J = 2.3 Hz, 1 H), 7.28 (d, J = 8.6 Hz, 1 H). 5-Aminobenzo[d]oxazole-2 -thiol
To a suspension of 5-nitrobenzo[d]oxazole-2-thiol (1.0 g, 5.1 mmol) in EtOH (38 mL,) and H20 (38 mL) at 80°C was added NH4CI (545 mg, 10.2 mmol), followed by Fe (1.40 g, 25 mmol). The resulting mixture was stirred at 80°C for 1.5 h. The mixture was cooled to rt, filtered and the

filtrate was concentrated. The precipitate that formed was collected, washed with water and
dried to give the title compound (or tautomer) (640 mg) as a beige powder; LC-MS: tR = 0.37
min; [M+H]+ = 208.06; 1H NMR (400 MHz, D6-DMSO) 5: 13.39 (s br, 1 H), 7.13 (d, J = 8.6 Hz, 1
H), 6.36-6.51 (m, 2 H), 5.26 (s br, 2 H).
Methyl 2-mercaptobenzo[d]oxazole-5-carboxylate
To a solution of methyl 3-amino-5-hydroxybenzoate (1.0 g, 5.98 mmol) in MeOH (13.5 ml_)
KOH (468 mg, 7.18 mmol) was added. The mixture was stirred at rt until all KOH had dissolved.
Then CS2 (9.02 ml_, 150 mmol) was added and the mixture was stirred at 60°C for 16 h before
it was cooled to 0°C and diluted with EA (50 ml_). 1M aq. HCI (8.6 mL) was added to acidify the
mixture to pH 1. The organic layer was separated, washed with water (25 mL), dried over
MgS04, filtered and concentrated to give the title compound (or tautomer) (1.18 g) as a solid;
LC-MS: tR = 0.72 min; [M+H]+ = 209.96; 1H NMR (400 MHz, D6-DMSO) 5: 14.14 (s, 1 H), 7.89
(dd, J, = 1.7 Hz, J2 = 8.5 Hz, 1 H), 7.69 (d, J = 1.5 Hz, 1 H), 7.63 (d, J = 8.5 Hz, 1 H), 3.88 (s, 3
H).
Methyl 2-chlorobenzo[d]oxazole-5-carboxylate
To a solution of methyl 2-mercaptobenzo[d]oxazole-5-carboxylate 1.08 g, 5.16 mmol) in DCM
(5.5 mL) POCI3 (4.25 mL, 46.5 mmol) followed by PCI5 (1.29 g, 6.19 mmol) was added. The
mixture was stirred at rt for 8 h before it was concentrated. The remaining oil was cooled with
an ice bath before sat. aq. NaHC03 solution (50 mL) was added. When the evolution of gas
had ceased the mixture was transferred to a separating funnel and extracted twice with DCM
(2x50 mL). The combined organic extracts were dried over MgS04, filtered and concentrated.
The crude product was suspended in diethyl ether (10 mL). The suspension was stirred for 10
min before it was filtered. The filtrate was concentrated and dried to give the title compound
(0.62 g) as a solid; LC-MS: tR = 0.80 min; [M+H+CH3CN]+ = 253.04; 1H NMR (400 MHz, CDCI3)
5: 8.40 (d, J = 1.2 Hz, 1 H), 8.15 (dd, J, = 1.6 Hz, J2 = 8.7 Hz, 1 H), 7.58 (d, J = 8.6 Hz, 1 H),
3.99 (s, 3 H).
5-Nitrobenzo[d]thiazole-2-thiol
To a solution of 2-fluoro-5-nitroaniline (3.12 g, 20 mmol) in DMF (15 mL) potassium ethyl
xanthogenate (3.93 g, 24 mmol) was added. The mixture was stirred at 100°C for 5 h before it
was cooled to rt, diluted with water (25 mL) and 1 M aq. HCI (35 mL). The precipitate that
formed was collected, washed with water (15 mL) and dried to give the title compound (or
tautomer) (3.99 g) as a beige solid; LC-MS: tR = 0.76 min; [M+H]+ = not detectable; 1H NMR
(400 MHz, D6-DMSO)<5: 14.17 (s, 1 H), 8.15 (dd, J, = 2.2 Hz, J2 = 8.8 Hz, 1 H), 7.99 (d, J = 9.0
Hz), 7.97 (d, J = 2.3 Hz).
2-Chloro-5-nitrobenzo[d]thiazole
Solid 5-nitrobenzo[d]thiazole-2-thiol (4.0 g, 18.8 mmol) was placed in a round bottom flask and
cooled to 0°C while S02CI2 (9.1 mL, 113 mmol) was slowly added at 0°C. Upon complete

additions, the yellow suspension was stirred at 0°C for 5 min, then at rt for 2 h. The mixture was poured onto ice/water (200 ml_) and stirred for 1h. The precipitate that formed was collected, washed with water and dried under high vacuum. The material was slurried in EA (25 ml_), vigorously stirred for 15 min and filtered. The filtrate was concentrated and dried. The obtained solid absorbed to silica gel and purified by CC eluting with heptane:EA 4:1 to give the title compound (2.02 g) as a solid; LC-MS: tR = 0.84 min; [M+H]+ = 214.51; 1H NMR (400 MHz, CDCI3) 5: 8.84 (d, J = 2.2 Hz, 1 H), 8.35 (dd, J, = 2.2 Hz, J2 = 8.9 Hz, 1 H), 7.98 (d, J = 8.9 Hz, 1 H).
2-Chlorobenzo[d]thiazol-5-amine
To a solution of 2-chloro-5-nitrobenzo[d]thiazole (2.18 g, 10.2 mmol) in EtOH:acetic acid 91:9 (102 ml_) iron powder (5.70 g, 102 mmol) was carefully added. The mixture was refluxed for 1.5 h before it was filtered. The filtrate was concentrated to about one third of the volume and the pH of the solution was adjusted to pH 8 by adding 10% aq. NaOH solution. The mixture was extracted with EA (150 ml_). The organic extract was washed with brine, dried over Na2S04, filtered and concentrated. The crude product was suspended in EtOH (4 ml_), filtered, washed with additional EtOH (0.5 ml_) and dried to give the title compound (1.55 g) as a solid; LC-MS: tR = 0.78 min; [M+H]+ = 185.03; 1H NMR (400 MHz, D6-DMSO) 5: 7.65 (d, J = 8.7 Hz, 1 H), 7.06 (d, J = 1.9 Hz, 1 H), 6.79 (dd, J, = 2.0 Hz, J2 = 8.7 Hz, 1 H), 5.43 (s, 2 H). 2-Chloro-benzothiazole-5-carbonyl chloride
To a mixture of 2-sulfanyl-1,3-benzothiazole-5-carboxylic acid (50.1 mg, 0.237 mmol), PCI5 (158 mg, 0.745 mmol) and POCI3 (0.446 ml_, 4.74 mmol), DMF (0.042 ml_, 0.524 mmol) was carefully added. The mixture became warm and the thick suspension was stirred at rt for 3 h to become a clear solution. The mixture was concentrated and diluted with DCM, solid material was filtered off and the filtrate was concentrated and dried to give the crude title compound (92 mg) as a pale yellow resin which was used without further purification; LC-MS: tR = 0.91 min; [M+H]+ = not detectable.
Preparation of Intermediates
Intermediate A1 4-(5-Aminobenzo[d]oxazol-2-yl)thiomorpholine 1,1 -dioxide
a) To a solution of 2-chloro-5-nitrobenzo[d]oxazole (1.0 g, 5.0 mmol) and Et3N (2.1 mL, 15.1 mmol) in THF (25 mL) thiomorpholine 1,1-dioxide (715 mg, 5.29 mmol) was added. The mixture was stirred at 70°C for 3 h before it was diluted with water (100 mL) and extracted with EA (200 mL) followed by DCM (100 mL). The combined org. extracts were dried over MgS04, filtered and concentrated. The remaining solid was suspended in DCM (10 mL), filtered off, washed with additonal DCM (5 mL) and dried to give a first batch of the title compound (698 mg). The filtrate was concentrated and once more suspended in DCM (2 mL). Solid material was

collected, washed with a small amount of DCM and dried to give a second batch of the title
compound (460 mg). The obtained solid materials were combined; LC-MS: tR = 0.69 min;
[M+H]+ = 297.98; 1H NMR (400 MHz, D6-DMSO) 5: 8.15 (d, J = 2.3 Hz, 1 H), 8.04 (dd, J, = 2.3
Hz, J2 = 8.8 Hz, 1 H), 7.71 (d, J = 8.8 Hz, 1 H), 4.08-4.16 (m, 4 H), 3.35-3.42 (m, 4 H).
b) To a solution of 4-(5-nitrobenzo[d]oxazol-2-yl)thiomorpholine 1,1-dioxide (1.10 g, 3.7 mmol)
in acetic acid (25 ml_) iron powder (2.07 g, 37 mmol) was added carefully. The mixture was
stirred at 40°C for 2 h before it was filtered. The filtrate is diluted with water (50 ml_) and the pH
was adjusted to 13-14 by adding 5 M aq. NaOH solution. The mixture was extracted twice with
DCM (2x100 ml_), the combined org. extracts were dried over MgS04, filtered and dried to give
the title compound (908 mg) as a grey solid; LC-MS: tR = 0.38 min; [M+H]+ = 268.07; 1H NMR
(400 MHz, D6-DMSO) 5: 7.07 (d, J = 8.5 Hz, 1 H), 6.53 (d, J = 2.1 Hz, 1 H), 6.28 (dd, J, = 2.2
Hz, J2 = 8.5 Hz, 1 H), 4.84 (s, 2 H), 3.98-4.05 (m, 4 H), 3.26-3.32 (m, 4 H).
or alternatively:
b) To a mixture of 4-(5-nitrobenzo[d]oxazol-2-yl)thiomorpholine 1,1-dioxide (10 mg, 0.05 mmol)
in degassed EA (0.5 ml_) wet Pd/C (10 mg) was added before it was stirred under 4 bar of H2 at
rt for 16 h. The catalyst was removed by filtration and the filtrate was concentrated and dried to
give the title compound (5 mg).
Intermediates A2 to A38
The following 5-amino-benzo[d]oxazol derivatives were obtained in analogy to Intermediate A1:

Intermediate Name LU-Mb

tR [min] [M+H]*
A2 2-(piperidin-1-yl)benzo[d]oxazol-5-amine 0.52 218.31
A3 2-(pyrrolidin-1-yl)benzo[d]oxazol-5-amine 0.46 204.29
A4 2-(4-methylpiperazin-1-yl)benzo[d]oxazol-5-amine 0.17 233.29
A5 2-morpholinobenzo[d]oxazol-5-amine 0.42 220.30
A6 N2,N2-diethylbenzo[d]oxazole-2,5-diamine 0.50 206.27
A7 2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)benzo[d]oxazol-5-amine 0.42 232.24
A8 2-(4,4-difluoropiperidin-1-yl)benzo[d]oxazol-5-amine 0.54 254.24
A9 2-(3,3-difluoroazetidin-1-yl)benzo[d]oxazol-5-amine 0.46 267.26*
A10 2-(3,3-difluoropyrrolidin-1-yl)benzo[d]oxazol-5-amine 0.50 240.24
A11 2-(3-methoxypyrrolidin-1-yl)benzo[d]oxazol-5-amine 0.45 234.12
A12 2-(4-methoxypiperidin-1-yl)benzo[d]oxazol-5-amine 0.49 248.29
A13 1-(5-aminobenzo[d]oxazol-2-yl)-3-methylazetidin-3-ol 0.40 220.24
A14 N2-(2-(dimethylamino)ethyl)-N2-methylbenzo[d]oxazole-2,5-diamine 0.18 234.93
A15 2-(4-(dimethylamino)piperidin-1-yl)benzo[d]oxazol-5-amine 0.29 261.33
A16 2-(6-oxa-1-azaspiro[3.3]heptan-1-yl)benzo[d]oxazol-5-amine 0.42 232.24

A17
2-(3,3-difluoropiperidin-1-yl)benzo[d]oxazol-5-amine 0.53 254.26
A18 2-(3-morpholinoazetidin-1-yl)benzo[d]oxazol-5-amine 0.24 275.16
A19 N2-methyl-N2-(3-methyloxetan-3-yl)benzo[d]oxazole-2,5-diamine 0.45 234.24
A20 4-(1-(5-aminobenzo[d]oxazol-2-yl)azetidin-3-yl)thiomorpholine 1,1-
dioxide 0.43 323.00
A21 1'-(5-aminobenzo[d]oxazol-2-yl)-3-methyl-[1,3'-biazetidin]-3-ol 0.24 275.05
A22 2-(1-oxa-6-azaspiro[3.3]heptan-6-yl)benzo[d]oxazol-5-amine 0.44 232.11
A23 2-(2-oxa-6-azaspiro[3.4]octan-6-yl)benzo[d]oxazol-5-amine 0.44 246.15
A24 2-(6-oxa-2-azaspiro[3.5]nonan-2-yl)benzo[d]oxazol-5-amine 0.50 260.15
A25 2-(2-oxa-5-azaspiro[3.4]octan-5-yl)benzo[d]oxazol-5-amine 0.45 246.14
A26 2-(1-oxa-6-azaspiro[3.5]nonan-6-yl)benzo[d]oxazol-5-amine 0.46 260.15
A27 2-(2-oxa-5-azaspiro[3.5]nonan-5-yl)benzo[d]oxazol-5-amine 0.49 260.15
A28 2-(1-oxa-7-azaspiro[3.5]nonan-7-yl)benzo[d]oxazol-5-amine 0.47 260.16
A29 2-(8-oxa-2-azaspiro[4.5]decan-2-yl)benzo[d]oxazol-5-amine 0.49 274.16
A30 2-(1-oxa-8-azaspiro[4.5]decan-8-yl)benzo[d]oxazol-5-amine 0.53 274.16
A31 2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)benzo[d]oxazol-5-amine 0.48 260.16
A32 2-(5-oxa-2-azaspiro[3.4]octan-2-yl)benzo[d]oxazol-5-amine 0.48 246.15
A33 1-(1-(5-aminobenzo[d]oxazol-2-yl)azetidin-3-yl)piperidin-4-ol 0.20 289.15
A34 2-(6-methyl-2,6-diazaspiro[3.5]nonan-2-yl)benzo[d]oxazol-5-amine 0.34 273.18
A35 2-(5-oxa-2-azaspiro[3.5]nonan-2-yl)benzo[d]oxazol-5-amine 0.52 260.15
A36 2-(1-azaspiro[3.3]heptan-1-yl)benzo[d]oxazol-5-amine 0.55 230.18
A37 2-(7-oxa-1-azaspiro[3.5]nonan-1-yl)benzo[d]oxazol-5-amine 0.48 260.16
A38 tert-butyl 1-(5-aminobenzo[d]oxazol-2-yl)azetidine-3-carboxylate 0.60 290.15
* represents [M+H+CH3CN] .
Intermediate A5: 1H NMR (500 MHz, D6-DMSO) 5: 7.04 (d, J = 8.4 Hz, 1 H), 6.50 (d, J = 2.1
Hz, 1 H), 6.25 (dd, J, = 2.2 Hz, J2 = 8.4 Hz, 1 H), 4.81 (s, 2 H), 3.67-3.73 (m, 4 H), 3.48-3.55
(m, 4 H).
Intermediate A39
1-(5-Aminobenzo[d]oxazol-2-yl)pyrrolidin-2-one
a) To a solution of 2-chloro-5-nitrobenzo[d]oxazole (800 mg, 4.03 mmol) in DCM (25 ml_) were added ethyl 4-aminobutyrate hydrochloride (810 mg, 4.83 mmol) followed by DIPEA (1.59 ml_, 9.27 mmol) at 0°C. The mixture was stirred at rt overnight before it was concentrated in vacuo, diluted with EA, washed with brine, dried over MgS04, filtered and concentrated. The crude product was purified by CC eluting with heptane:EA 1:1 to give ethyl 4-((5-nitrobenzo[d]oxazol-2-yl)amino)butanoate (1.01 g) as a yellow powder, LC-MS: tR = 0.77 min; [M+H]+ = 294.1.
b) A suspension of ethyl 4-((5-nitrobenzo[d]oxazol-2-yl)amino)butanoate (1.01 g, 3.44 mmol) in EtOH (20 ml_) and 1M aq. NaOH (5.2 ml_) was stirred at rt overnight before it was cooled with

an ice bath. 1 M aq. HCI was added (5.2 ml_) and the mixture was concentrated and dried to give crude 4-((5-nitrobenzo[d]oxazol-2-yl)amino)butanoic acid (1.22 g) as a yellow powder, LC-MS: tR = 0.60 min; [M+H]+ = 266.14. This material was dissolved in DCM (25 mL) and SOCI2 (0.89 mL, 12.1 mmol) was added. The mixture was stirred at rt for 2 h before it was concentrated in vacuo, dissolved in pyridine (10 mL) and stirred at rt for 1 h. The mixture was again concentrated, diluted with DCM and washed with brine. The organic extract was separated and the precipitate that formed was removed by filtration (unreacted SM). The filtrate was dried over MgS04, filtered and concentrated. The crude product was first purified by CC eluting with DCM:MeOH 10:1, then by prep. HPLC to give 1-(5-nitrobenzo[d]oxazol-2-yl)pyrrolidin-2-one (133 mg) as a white solid, LC-MS: tR = 0.64 min; [M+H]+ = 248.11; 1H NMR (400 MHz, CDCI3) 5: 8.50 (d, J = 2.3 Hz, 1 H), 8.25 (dd, J, = 2.3 Hz, J2 = 8.9 Hz, 1 H), 7.65 (d, J= 8.8 Hz, 1 H), 4.17-4.23 (m, 2 H), 2.76 (t, J= 7.9 Hz, 2 H), 2.30-2.39 (m, 2 H). c) To a solution of 1-(5-nitrobenzo[d]oxazol-2-yl)pyrrolidin-2-one (133 mg, 0.538 mmol) in EA (2 mL) Pd/C (7 mg, 10% Pd, 50% wet) was added. The mixture was stirred under 1 bar of H2 at rt for 18 h before the catalyst was removed by filtration. The filtrate was concentrated and dried to give 1-(5-aminobenzo[d]oxazol-2-yl)pyrrolidin-2-one (105 mg) as a white solid, LC-MS: tR = 0.32 min; [M+H]+ = 218.11.

Intermediate Name LC-MS

tR [min] [M+H]*
A40 2-Azetidin-1-yl-benzooxazol-5-ylamine 0.43 190.16
A41 1-(5-Amino-benzooxazol-2-yl)-piperidin-4-ol 0.54 234.15
A42 2-(2-Oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-ylamine 0.64 260.15
A43 1-(5-Amino-benzooxazol-2-yl)-azetidin-3-ol 0.50 206.15
A44 N2-Cyclopropyl-N2-oxetan-3-yl-benzooxazole-2,5-diamine 0.65 246.12
A45 2-(6-Oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-ylamine 0.62 246.14
A46 2-(2-Oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-ylamine 0.66 260.14
A47 N2-Ethyl-benzooxazole-2,5-diamine 0.36 178.18
A48 2-(3-Pyridin-2-yl-azetidin-1-yl)-benzooxazol-5-ylamine 0.38 267.08
Intermediate B1 N-(2-Mercaptobenzo[d]oxazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide
To a mixture of 5-aminobenzo[d]oxazole-2-thiol (540 mg, 3.25 mmol) in pyridine (27 ml_) was added 2,3-dihydrobenzofuran-5-carbonyl chloride (593 mg, 3.25 mmol) at rt. The reaction mixture was stirred at rt for 1.5 h before another portion of 2,3-dihydrobenzofuran-5-carbonyl

chloride (30 mg, 0.16 mmol) was added. Stirring was continued at rt for 1 h before the mixture was concentrated. The residue was treated with water, the resulting suspension was sonicated before the solid material was collected by filtration, washed and dried to give the title compound (890 mg) as a pink solid; LC-MS: tR = 0.77 min; [M+H]+ = 312.97; 1H NMR (400 MHz, D6-DMSO) 5: 13.84 (s br, 1 H), 10.21 (s, 1 H), 7.93 (d, J= 1.7 Hz, 1 H), 7.88 (s, 1 H), 7.80 (dd, J, = 1.3 Hz, J2 = 8.3 Hz, 1 H), 7.55 (dd, J, = 1.8 Hz, J2 = 8.8 Hz, 1 H), 7.48 (d, J = 8.8 Hz, 1 H), 6.90 (d, J = 8.4 Hz, 1 H), 4.64 (t, J = 8.8 Hz, 2 H), 3.27 (t, J = 8.8 Hz, 2 H). Intermediate C1 2-(4-methylpiperazin-1 -yl)benzo[d]oxazole-5-carboxylic acid
a) To a solution of methyl 2-chlorobenzo[d]oxazole-5-carboxylate (98.5 mg, 465 umol) in THF(1.5 ml_) Et3N (195 oL, 1.4 mmol) followed by 1-methylpiperazine (63 oL, 559 umol) was added. The mixture was stirred at 65°C for 16 h before it was cooled to rt and concentrated. The residue was dissolved in CH3CN (1 ml_) and DMF (1 ml_), filtered and the filtrate was separated by prep. HPLC to give methyl 2-(4-methylpiperazin-1-yl)benzo[d]oxazole-5-carboxylate (80 mg) as a solid; LC-MS: tR = 0.51 min; [M+H]+ = 276.16; 1H NMR (400 MHz, CDCI3) 5: 8.04 (d, J = 1.5 Hz, 1 H), 7.83 (dd, J, = 1.7 Hz, J2 = 8.4 Hz, 1 H), 7.29 (d, J = 8.3 Hz, 1 H), 3.94 (s, 3 H), 3.77-3.82 (m, 4 H), 2.57-2.62 (m, 4 H), 2.41 (s, 3 H).
b) To a solution of methyl 2-(4-methylpiperazin-1-yl)benzo[d]oxazole-5-carboxylate (76 mg, 0.28 mmol) in THF (1 mL) and MeOH (1 mL) a 1 M aq. solution of NaOH (0.55 mL) was added. The mixture was stirred at rt for 18 h before it was neutralized by adding 1 M aq. HCI. The precipitate that formed was collected and dried to give tht title compound (49 mg) as hydrochloride salt as a white solid; LC-MS: tR = 0.43 min; [M+H]+ = 262.11; 1H NMR (400 MHz, DMSO)<5: 12.93 (s, 1 H), 11.04 (s, 1 H), 7.85 (d, J = 1.5 Hz, 1 H), 7.75 (dd, J, = 1.7 Hz, J2 = 8.4 Hz, 1 H), 7.56 (d, J = 8.4 Hz, 1 H), 4.21-4.37 (m, 2 H), 3.43-3.71 (m, 4 H), 3.08-3.27 (m, 2 H), 2.80 (s, 3 H).
Intermediateds C2 to C6
The following 2-aminobenzo[d]oxazole-5-carboxylic acid derivatives were obtained in analogy
to Intermediate C1:

Intermediate Name LC-MS

tR [min] [M+H]*
C2 2-Piperidin-1-yl-benzooxazole-5-carboxylicacid 0.70 247.13
C3 2-Morpholin-4-yl-benzooxazole-5-carboxylicacid 0.61 249.11
C4 2-Diethylamino-benzooxazole-5-carboxylicacid 0.68 235.11
C5 2- Pyrrol idi n-1 -y l-benzooxazole-5-carboxy I ic acid 0.61 233.16
C6 2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazole-5-carboxylicacid 0.60 261.04

Intermediate C2: 1H NMR (400 MHz, D6-DMSO) 5: 12.82 (s, 1 H), 7.76 (d, J = 1.5 Hz, 1 H),
7.66 (dd, J, = 1.7 Hz, J2 = 8.3 Hz, 1 H), 7.47 (d, J = 8.3 Hz, 1 H), 3.59-3.65 (m, 4 H), 1.57-1.68
(m, 6 H).
Intermediate C3: 1H NMR (400 MHz, D6-DMSO) 5: 12.86 (s, 1 H), 7.81 (d, J = 1.6 Hz, 1 H),
7.70 (dd, J, = 1.6 Hz, J2 = 8.3 Hz, 1 H), 7.51 (d, J = 8.3 Hz, 1 H), 3.71-3.76 (m, 4 H), 3.60-3.65
(m, 4 H).
Intermediate C4: 1H NMR (400 MHz, D6-DMSO) 5: 12.80 (s, 1 H), 7.76 (d, J = 1.6 Hz, 1 H),
7.65 (dd, J, = 1.7 Hz, J2 = 8.3 Hz, 1 H), 7.48 (d, J = 8.3 Hz, 1 H), 3.56 (q, J = 7.1 Hz, 4 H), 1.22
(t, J = 7.1 Hz, 7H).
Intermediate C5: 1H NMR (400 MHz, D6-DMSO) 5: 12.80 (s, 1 H), 7.77 (d, J = 1.6 Hz, 1 H),
7.65 (dd, J, = 1.7 Hz, J2 = 8.3 Hz, 1 H), 7.48 (d, J = 8.3 Hz, 1 H), 3.54-3.60 (m, 4 H), 1.95-2.01
(m, 4 H).
Intermediate C6: 1H NMR (400 MHz, D6-DMSO) 5: 12.88 (s, 1 H), 7.87 (d, J = 1.5 Hz, 1 H),
7.72 (dd, J, = 1.7 Hz, J2 = 8.3 Hz, 1 H), 7.57 (d, J = 8.4 Hz, 1 H), 5.22 (d, J = 7.7 Hz, 2 H), 4.67
(d, J = 7.7 Hz, 2 H), 4.04 (t, J = 7.2 Hz, 2 H), 2.73 (t, J = 7.3 Hz, 2 H).
Intermediate D1
2-(Piperidin-1-yl)benzo[d]thiazol-5-amine
a) To a solution of 2-chloro-5-nitrobenzo[d]thiazole (200 mg, 931 umol) in THF (1.5 ml_) Et3N (0.195 ml_, 1.4 mmol) followed by piperidine (0.138 ml_, 1.4 mmol) was added. The mixture was stirred at 65°C for 1 h before it was diluted with EA (50 ml_) and washed with water (50 ml_). The organic extract was dried over MgS04, filtered and concentrated to give 5-nitro-2-(piperidin-1-yl)benzo[d]thiazole (250 mg) as a solid; LC-MS: tR = 0.92 min; [M+H]+ = 264.18.
b) To a solution of 5-nitro-2-(piperidin-1-yl)benzo[d]thiazole (245 mg, 0.93 mmol) in EtOH (15 ml_) Pd/C (125 mg, 10% Pd, 50% water wet) was added. The mixture was stirred under 1 atm of H2 for 4 days before the catalyst was removed by filtration and the filtrate was evaporated. The crude product was purified by prep. HPLC to give the title compound (73 mg) as a solid; LC-MS: tR = 0.54 min; [M+H]+ = 234.17; 1H NMR (400 MHz, CDCI3) 5: 7.33 (d, J = 8.3 Hz, 1 H), 6.93 (d, J = 2.2 Hz, 1 H), 6.49 (dd, J, = 2.2 Hz, J2 = 8.3 Hz, 1 H), 3.77 (s br, 2 H), 3.56-3.64 (m, 4H), 1.67-1.77 (m, 6 H).
Intermediates D2 to D17
The following 5-amino-benzo[d]thiazol derivatives were obtained in analogy to Intermediate D1:

Intermediate Name LC-MS

tR [min] [M+H]*
D2 2-Morpholin-4-yl-benzothiazol-5-ylamine 0.46 236.16
D3 2-(4-Methyl-piperazin-1-yl)-benzothiazol-5-ylamine 0.27 249.19
D4 2-Pyrrolidin-1-yl-benzothiazol-5-ylamine 0.48 220.11

D5 N2,N2-Diethyl-benzothiazole-2,5-diamine 0.52 222.13
D6 N2,N2-Dimethyl-benzothiazole-2,5-diamine 0.42 194.12
D7 2-(3,3-Difluoro-azetidin-1-yl)-benzothiazol-5-ylamine 0.52 241.95
D8 2-(3,3-Difluoro-pyrrolidin-1-yl)-benzothiazol-5-ylamine 0.54 256.10
D9 2-(3,3-Difluoro-piperidin-1-yl)-benzothiazol-5-ylamine 0.57 270.10
D10 2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazol-5-ylamine 0.47 248.12
D11 2-(2-Oxa-6-aza-spiro[3.3]hept-6-yl)-benzothiazol-5-ylamine 0.45 248.12
D12 2-(1,1-Dioxo-1l6-thiomorpholin-4-yl)-benzothiazol-5-ylamine 0.43 284.04
D13 N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,5-diamine 0.33 251.15
D14 2-(3-Methoxy-pyrrolidin-1-yl)-benzothiazol-5-ylamine 0.48 250.12
D15 2-(4-Methoxy-piperidin-1-yl)-benzothiazol-5-ylamine 0.52 264.15
D16 1-(5-Amino-benzothiazol-2-yl)-3-methyl-azetidin-3-ol 0.44 236.11
D17 2-(4-Dimethylamino-piperidin-1-yl)-benzothiazol-5-ylamine 0.35 277.14
Intermediate D2: 1H NMR (400 MHz, CDCI3) 5: 7.37 (d, J = 8.3 Hz, 1 H), 6.96 (d, J = 2.2 Hz, 1 H), 6.54 (dd, J, = 2.2 Hz, J2 = 8.3 Hz, 1 H), 3.83-3.87 (m, 4 H), 3.60-3.66 (m, 4 H). Intermediate D3: 1H NMR (400 MHz, CDCI3) 5: 7.36 (d, J = 8.3 Hz, 1 H), 6.93 (d, J = 2.2 Hz, 1 H), 6.52 (dd, J, = 2.2 Hz, J2 = 8.3 Hz, 1 H), 3.70 (s br, 2 H), 3.63-3.68 (m, 4 H), 2.51-2.61 (m, 4 H), 2.39 (s, 3 H).
Intermediated D9: 1H NMR (400 MHz, CDCI3) 5: 7.36 (d, J = 8.3 Hz, 1 H), 6.96 (d, J = 2.2 Hz, 1 H), 6.54 (dd, J, = 2.2 Hz, J2 = 8.4 Hz, 1 H), 3.88 (t, J = 11.4 Hz, 2 H), 3.62-3.68 (m, 2 H), 2.07-2.19 (m, 2 H), 1.92-2.00 (m, 2 H).
Intermediate D10: 1H NMR (400 MHz, CDCI3) 5: 7.38 (d, J = 8.4 Hz, 1 H), 7.09 (s, 1 H), 6.57 (dd, J, = 1.8 Hz, J2 = 8.5 Hz, 1 H), 5.48 (d, J = 7.7 Hz, 2 H), 4.75 (d, J = 7.7 Hz, 2 H), 4.15 (t, J = 7.2 Hz, 2 H), 2.74 (t, J = 7.4 Hz, 2 H). Intermediate E1
N-(2-Chlorobenzo[d]thiazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide To a solution of 2,3-dihydrobenzo[b]furan carboxylic acid (1.27 g, 7.5 mmol) in DMF (22.5 ml_) TBTU (2.48 g, 7.5 mmol) followed by DIPEA (3.93 ml_, 22.5 mmol) was added. The mixture was stirred at rt for 15 min before 2-chlorobenzo[d]thiazol-5-amine (1.52 g, 7.5 mmol) was added. Stirring is continued at 55°C for 18 h. The mixture was concentrated, diluted with DCM (250 ml_) and washed with sat. aq. NaHC03 solution (125 ml_). The organic extract was separated and concentrated. The crude product was purified by CC eluting with a gradient of heptane:EE 1:2 to pure EA to give the title compound (980 mg) as a solid; LC-MS*: tR = 1.01 min; [M+H]+ = 330.95 (* = 0.5 % NH4OH instead of TFA in eluting solvent.); 1H NMR (400 MHz, DMSO) 5: 10.32 (s, 1 H), 8.50 (d, J= 1.9 Hz, 1 H), 8.04 (d, J= 8.8 Hz, 1 H), 7.92 (s, 1 H), 7.87

(dd, J, = 2.0 Hz, J2 = 8.8 Hz, 1 H), 7.83 (dd, J, = 1.9 Hz, J2 = 8.4 Hz, 1 H), 6.91 (d, J = 8.4 Hz, 1
H), 4.65 (t, J = 8.8 Hz, 2 H), 3.28 (t, J = 8.7 Hz, 2 H).
Intermediate E2
2-Chloro-N-(2,3-dihydrobenzofuran-5-yl)benzo[d]thiazole-5-carboxamide
A solution of 2,3-dihydro-1-benzofuran-5-amine (33.7 mg, 0.237 mmol) and DIPEA (0.21 ml_,
1.18 mmol) in DCM (1 ml_) was cooled to 0°C before crude 2-chloro-benzothiazole-5-carbonyl
chloride (92 mg, 0.237 mmol) dissolved in DCM (1 ml_) was added. The mixture was stirred at
rt for 30 min. The mixture was diluted with DCM (5 ml_) and washed with water (5 ml_). the
organic extract was dried over Na2S04, filtered and concentrated to give the crude title
compound (69 mg) as a pale yellow resin; LC-MS: tR = 0.86 min; [M+H]+ = 330.97; 1H NMR
(400 MHz, D6-DMSO): 5 10.28 (s, 1 H), 8.56 (d, J = 1.1 Hz, 1 H), 8.26 (d, J = 8.5 Hz, 1 H), 8.07
(dd, J, = 1.5 Hz, J2 = 8.5 Hz, 1 H), 7.70 (s, 1 H), 7.45 (dd, J, = 1.7 Hz, J2 = 8.5 Hz, 1 H), 6.76
(d, J = 8.5 Hz, 1 H), 4.54 (t, J = 8.7 Hz, 2 H), 3.21 (t, J = 8.7 Hz, 2 H).
Intermediate E3
N-Benzo[d][1,3]dioxol-5-yl)-2-chlorobenzo[d]thiazole-5-carboxamide
The title compound was prepared in analogy to Intermediate E2; LC-MS: tR = 0.86 min; [M+H]+
= 332.98; 1H NMR (400 MHz, D6-DMSO): 5 10.34 (s, 1 H), 8.56 (d, J = 1.3 Hz, 1 H), 8.27 (d, J =
8.5 Hz, 1 H), 8.06 (dd, J-, = 1.6 Hz, J2 = 8.5 Hz, 1 H), 7.48 (d, J = 1.9 Hz, 1 H), 7.23 (dd, J, = 2.0
Hz, J2 = 8.4 Hz, 1 H), 6.93 (d, J = 8.4 Hz, 1 H), 6.03 (s, 2 H).
Intermediate E4
2-Chloro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzo[d]thiazole-5-carboxamide
The title compound was prepared in analogy to Intermediate E2; LC-MS: tR = 0.87 min; [M+H]+
= 346.90; 1H NMR (400 MHz, D6-DMSO): 5 10.28 (s, 1 H), 8.56 (d, J= 1.4 Hz, 1 H), 8.26 (d, J =
8.5 Hz, 1 H), 8.06 (dd, J1 = 1.6 Hz, J2 = 8.5 Hz, 1 H), 7.43 (d, J = 2.4 Hz, 1 H), 7.24 (dd, J1 = 2.4
Hz, J2 = 8.8Hz, 1 H), 6.85 (d, J = 8.7 Hz, 1 H), 4.19-4.32 (m, 4 H).
Example 1
2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1,1 -dioxo-1 l6-thiomorpholin-4-yl)-
benzooxazol-5-yl]-amide
To a solution of 2,3-dihydrobenzo[b]furan-5-carboxylic acid (18.5 mg, 113 umol) in DCM (2 mL) 1-chloro-N,N-2-trimethylpropenylamine (17 uL, 124 umol) was added. The mixture was stirred at rt for 15 min before DIPEA (96 oL, 563 umol) and 4-(5-aminobenzo[d]oxazol-2-yl)thiomorpholine 1,1-dioxide (30.1 mg, 113 mmol) was added. Stirring was continued at rt for 30 min. The mixture was diluted with DMF (2 mL) and separated using prep. HPLC (column: XBridge Prep C18, 30x75 mm, 10 urn, gradient of MeCN in water containing 0.5 % of 15 M aq. NH4OH) to give the title compound (30 mg) as a white solid; LC-MS: tR = 0.73 min; [M+H]+ = 414.05; 1H NMR (400 MHz, D6-DMSO) 5: 10.03 (s, 1 H), 7.88 (s, 1 H), 7.77-7.82 (m, 2 H), 7.38-

7.46 (m, 2 H), 6.88 (d, J = 8.4 Hz, 1 H), 4.64 (t, J = 8.8 Hz, 2 H), 4.04-4.11 (m, 4 H), 3.32-3.39 (m, 4 H), 3.26 (t, J =8.7 Hz, 2 H).
Examples 2 to 41
The following Example compounds were prepared in analogy to Example 1 starting from the appropriate Intermediates A2 to A39 and 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid, 2,3-dihydrobenzofuran-5-carboxylic acid, 4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carboxylic acid, benzo[d][1,3]dioxole-5-carboxylic acid, or chromane-6-carboxylic acid.

Example Name LO-IVIS

tR [min] [M+H]*
2 2,3-Dihydro-benzofuran-5-carboxylicacid(2-piperidin-1-yl-benzooxazol-5- 0.78 364.26

yl)-amide

3 2,3-Dihydro-benzofuran-5-carboxylicacid(2-pyrrolidin-1-yl-benzooxazol-5-
yl)-amide 0.71 350.29
4 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(4-methyl-piperazin-1-yl)- 0.59 379.23

benzooxazol-5-yl]-amide

5 2,3-Dihydro-benzofuran-5-carboxylicacid(2-morpholin-4-yl-benzooxazol-5- 0.76 366.25

yl)-amide

6 2,3-Dihydro-benzofuran-5-carboxylicacid(2-diethylamino-benzooxazol-5- 0.75 352.29

yl)-amide

7 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4,4-difluoro-piperidin-1-yl)- 0.86 400.20

benzooxazol-5-yl]-amide

8 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-azetidin-1 -yl)-
benzooxazol-5-yl]-amide 0.82 372.10
9 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide 0.93 386.04
10 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-methoxy-pyrrolidin-1-yl)- 0.84 380.04

benzooxazol-5-yl]-amide

11 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-methoxy-piperidin-1-yl)- 0.89 394.09

benzooxazol-5-yl]-amide

12 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-hydroxy-3-methyl-azetidin-1 -yl)-benzooxazol-5-yl]-amide 0.78 366.04
13 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[(2-dimethylamino-ethyl)- 0.60 381.08

methyl-amino]-benzooxazol-5-yl}-amide; compound with formic acid

14 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-dimethylamino-piperidin-1- 0.78 406.95

yl)-benzooxazol-5-yl]-amide; compound with formic acid

15 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide 0.75 378.23
16 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide 0.85 400.21
17 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-morpholin-4-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.59 421.02
18 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[methyl-(3-methyl-oxetan-3-yl)-amino]-benzooxazol-5-yl}-amide 0.78 380.20
19 2,3-Dihydro-benzofuran-5-carboxylic acid {2- [3-( 1,1 -dioxo-116-
thiomorpholin-4-yl)-azetidin-1-yl]-benzooxazol-5-yl}-amide 0.70 469.10
20 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-hydroxy-3-methyl-[1,3']biazetidinyl-1 '-yl)-benzooxazol-5-yl]-amide 0.61 421.20
21 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide 0.74 378.20
22 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(2-oxa-6-aza-spiro[3.4]oct-6-yl)-benzooxazol-5-yl]-amide 0.70 392.20
23 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide 0.77 406.11
24 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide 0.76 392.11
25 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide 0.75 406.11
26 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-5-aza-spiro[3.5]non-5-yl)-benzooxazol-5-yl]-amide 0.84 406.12
27 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide 0.76 406.09
28 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide 0.73 420.13
29 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-8-aza-spiro[4.5]dec-8-yl)-benzooxazol-5-yl]-amide 0.80 420.12
30 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(7-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide 0.76 406.11
31 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(5-oxa-2-aza-spiro[3.4]oct-2-yl)-benzooxazol-5-yl]-amide 0.78 392.11
32 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[3-(4-hydroxy-piperidin-1-yl)-azetidin-1-yl]-benzooxazol-5-yl}-amide 0.58 435.15

33 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(6-methyl-2,6-diaza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide 0.61 419.14
34 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(5-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide 0.82 406.12
35 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide 0.83 376.10
36 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide 0.75 406.11
37 1-{5-[(2,3-Dihydro-benzofuran-5-carbonyl)-amino]-benzooxazol-2-yl}-azetidine-3-carboxylic acid tert-butyl ester 0.88 436.11
38 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxo-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide 0.66 364.15
39 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide 0.73 429.90
40 Chroman-6-carboxylic acid [2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-
5-yl]-amide 0.77 427.97
41 4-Methyl-3]4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide 0.75 442.94
Example 3: 1H NMR (400 MHz, D6-DMSO) 5: 10.01 (s, 1 H), 7.83 (s, 1 H), 7.74 (d, J = 8.8 Hz,
1 H), 7.64 (s, 1 H), 7.27-7.33 (m, 2 H), 6.85 (d, J = 8.1 Hz, 1 H), 4.60 (t, J = 8.8 Hz, 2 H), 3.50-
3.55 (m, 4 H), 3.23 (t, J = 8.3 Hz, 2 H), 1.91-1.99 (m, 4 H).
Example 5: 1H NMR (400 MHz, D6-DMSO) 5: 10.04 (s, 1 H), 7.84 (s, 1 H), 7.75 (d, J = 8.2 Hz,
1 H), 7.71 (s, 1 H), 7.35 (s, 2 H), 6.85 (dd, J, = 2.2 Hz, J2 = 8.3 Hz, 1 H), 4.56-4.65 (m, 2 H),
3.51-3.69 (m, 8 H), 3.19-3.27 (m, 2 H).
Example 6: 1H NMR (400 MHz, D6-DMSO) 5: 10.01 (s, 1 H), 7.83 (s, 1 H), 7.75 (d, J = 8.6 Hz,
1 H), 7.63 (s, 1 H), 7.23-7.33 (m, 2 H), 6.85 (d, J = 8.3 Hz, 1 H), 4.60 (t, J = 8.7 Hz, 2 H), 3.50
(q, J = 6.7 Hz, 4 H), 3.23 (t, J = 8.6 Hz, 2 H), 1.18 (t, J = 6.9 Hz, 6 H).
Example 15: 1H NMR (400 MHz, DMSO) 5: 10.04 (s, 1 H), 7.89 (s, 1 H), 7.78-7.83 (m, 2 H),
7.43 (s, 2 H), 6.89 (d, J = 8.4 Hz, 1 H), 5.22 (d, J = 7.5 Hz, 2 H), 4.61-4.69 (m, 4 H), 4.02 (t, J =
7.3 Hz, 2 H), 3.27 (t, J = 8.7 Hz, 2 H), 2.73 (t, J = 7.2 Hz, 2 H).
Example 23: 1H NMR (400 MHz, DMSO) 5: 10.02 (s, 1 H), 7.89 (s, 1 H), 7.80 (d, J= 8.3 Hz, 1
H), 7.76 (d, J = 1.2 Hz, 1 H), 7.34-7.43 (m, 2 H), 6.89 (d, J = 8.4 Hz, 1 H), 4.65 (t, J = 8.7 Hz, 2
H), 3.87-3.95 (m, 4 H), 3.68 (s, 2 H), 3.51-3.56 (m, 2 H), 3.27 (t, J= 8.6 Hz, 2 H), 1.84-1.91 (m,
2H), 1.50-1.58 (m, 2 H).

Example 26: 1H NMR (400 MHz, DMSO) 5: 10.05 (s, 1 H), 7.88 (s, 1 H), 7.76-7.81 (m, 2 H),
7.40 (s, 2 H), 6.89 (d, J = 8.4 Hz, 1 H), 4.79-4.84 (m, 2 H), 4.64 (t, J = 8.7 Hz, 2 H), 4.43-4.48
(m, 2 H), 3.27 (t, J = 8.7 Hz, 2 H), 2.02-2.09 (m, 2 H), 1.69-1.77 (m, 2 H), 1.39-1.47 (m, 2 H).
Example 30: 1H NMR (400 MHz, DMSO) 5: 10.01 (s, 1 H), 7.89 (s, 1 H), 7.80 (d, J= 8.4 Hz, 1
H), 7.76 (d, J = 1.2 Hz), 7.34-7.43 (m, 2 H), 6.89 (d, J = 8.4 Hz, 1 H), 4.65 (t, J = 8.7 Hz, 2 H),
3.98 (s, 4 H), 3.53-3.60 (m, 2 H), 3.27 (t, J = 8.7 Hz, 2 H), 1.76-1.84 (m, 4 H).
Example 34: 1H NMR (400 MHz, CDCI3) 5: 7.82 (s, 1 H), 7.80 (s, 1 H), 7.68 (dd, J, = 1.4 Hz, J2
= 8.3 Hz, 1 H), 7.53 (d, J = 1.9 Hz, 1 H), 7.43 (dd, J, = 2.0 Hz, J2 = 8.6 Hz, 1 H), 7.25 (d, J = 8.6
Hz, 1 H), 6.85 (d, J = 8.3 Hz, 1 H), 4.68 (t, J = 8.8 Hz, 2 H), 4.21 (d, J = 8.7 Hz, 2 H), 4.11 (d, J
= 8.7 Hz, 2 H), 3.69-3.73 (m, 2 H), 3.29 (t, J = 8.7 Hz, 2 H), 1.86-1.92 (m, 2 H), 1.68-1.75 (m, 2
H), 1.57-1.64 (m, 2 H).
Example 39: 1H NMR (400 MHz, DMSO) 5: 10.06 (s, 1 H), 7.77 (s, 1 H), 7.47-7.53 (m, 2 H),
7.40 (s, 2 H), 6.98 (d, J = 8.3 Hz, 1 H), 4.26-4.35 (m, 4 H), 4.03-4.11 (m, 4 H), 3.30-3.37 (m, 4
H).
Example 41: 1H NMR (400 MHz, DMSO) 5: 9.99 (s, 1 H), 7.77 (s, 1 H), 7.39 (s, 2 H), 7.23-7.29
(m, 2 H), 6.77 (d, J = 8.8 Hz, 1 H), 4.26-4.33 (m, 2 H), 4.03-4.11 (m, 4 H), 3.30-3.37 (m, 4 H),
3.24-3.30 (m, 2 H), 2.90 (s, 3 H).
Example 37
1-{5-[(2,3-Dihydro-benzofuran-5-carbonyl)-amino]-benzooxazol-2-yl}-azetidine-3-carboxylic acid tert-butyl ester
To a solution of 2,3-dihydrobenzofuran-5-carboxylic acid (10 mg, 63 umol) and HBTU (24 mg, 63 umol) in DMF (1 ml_) DIPEA (33 uL, 190 umol) was added. The mixtures were stirred at rt for 30 min before by tert-butyl 1-(5-aminobenzo[d]oxazol-2-yl)azetidine-3-carboxylate (18 mg, 63 umol) was added. Stirring was continued at 55°C for 16 h. The mixture was separated by prep. HPLC to give 1-{5-[(2,3-dihydro-benzofuran-5-carbonyl)-amino]-benzooxazol-2-yl}-azetidine-3-carboxylic acid tert-butyl ester (4 mg) as a colourless resin; LC-MS: tR = 0.88 min; [M+H]+ = 436.11. Example 42
(R)-N-(2-(3-hydroxypiperidin-1-yl)benzo[d]oxazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide
To a mixture of N-(2-mercaptobenzo[d]oxazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide (Intermediate B1) (20 mg, 64 umol) in DCM (1 mL) and SOCI2 (0.1 mL) DMF (20 uL) was added. The suspension was stirred at rt for 1 h before the solvent was removed in vacuo to give crude N-(2-chlorobenzo[d]oxazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamid; LC-MS: tR = 0.85 min; [M+H]+ = 314.96. To this material a solution of (R)-piperidin-3-ol (7.8 mg, 77 umol) in DMF (0.8 mL) and K2C03 (27 mg, 192 umol) was added. The mixture was stirred at 70°C for 16

h before it was cooled to rt and separated by prep. HPLC to give the title compound (7 mg) as a colourless resin; LC-MS: tR = 0.68 min; [M+H]+ = 380.15; 1H NMR (400 MHz, DMSO) 5: 9.99 (s, 1 H), 7.86 (s, 1 H), 7.77 (d, J = 8.3 Hz, 1 H), 7.69 (s, 1 H), 7.30-7.36 (m, 2 H), 6.87 (d, J = 8.3 Hz, 1 H), 5.06 (d, J = 4.0 Hz, 1 H), 4.63 (t, J = 8.6 Hz, 2 H), 3.88 (dd, J, = 3.4 Hz, J2 = 13.0 Hz, 1 H), 3.73-3.79 (m, 1 H), 3.59-3.65 (m, 1 H), 3.29-.3.36 (m, 1 H), 3.25 (t, J = 8.8 Hz, 2 H), 3.14 (dd, J, = 8.1 Hz, J2 = 12.5 Hz, 1 H), 1.79-1.90 (m, 2 H), 1.37-1.54 (m, 2 H). Examples 43 to 74
The following Example compounds were prepared in analogy to Example 42 starting from Intermediate B1 and the appropriate amines.

Example Name

tR [min] [M+H]*
43 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((S)-3-hydroxy-piperidin-1-yl)- 0.74 380.08

benzooxazol-5-yl]-amide

44 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-isopropoxy-azetidin-1-yl)- 0.94 394.05

benzooxazol-5-yl]-amide

45 2,3-Dihydro-benzofuran-5-carboxylic acid [2-((R)-3-hydroxy-pyrrolidin-1 -yl)- 0.63 366.20

benzooxazol-5-yl]-amide

46 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((S)-3-hydroxy-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide 0.71 365.76
47 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(3-hydroxy-azetidin-1-yl)- 0.70 352.03

benzooxazol-5-yl]-amide

48 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-hydroxy-piperidin-1-yl)- 0.73 380.02

benzooxazol-5-yl]-amide

49 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(3-phenyl-azetidin-1-yl)-benzooxazol-5-yl]-amide 1.02 411.94
50 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)- 0.81 405.99

benzooxazol-5-yl]-amide

51 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-ethoxymethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide 1.02 408.02
52 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[(3-fluoro-oxetan-3-ylmethyl)- 0.82 397.73

methyl-amino]-benzooxazol-5-yl}-amide

53 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-oxetan-3-yl-piperazin-1-yl)-benzooxazol-5-yl]-amide 0.59 421.18
54 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[methyl-(1-oxetan-3-yl-piperidin-4-yl)-amino]-benzooxazol-5-yl}-amide 0.74 448.93

55
2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide 0.78 405.94
56 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(methyl-oxetan-3-ylmethyl-amino)-benzooxazol-5-yl]-amide 0.77 379.94
57 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(methyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide 0.77 365.71
58 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-methoxymethyl-pyrrolidin-1 -yl)-benzooxazol-5-yl]-amide 0.95 393.95
59 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide 0.87 393.98
60 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylaminomethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide 0.86 407.04
61 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-dimethylaminomethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide 0.66 407.24
62 rac-2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-phenyl-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.96 412.01
63 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide 0.82 391.99
64 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-pyrrolidin-1-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.78 405.02
65 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[3-(1-hydroxy-1-methyl-ethyl)-azetidin-1-yl]-benzooxazol-5-yl}-amide 0.76 393.80
66 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylaminomethyl-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.76 392.93
67 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(7-methyl-1,7-diaza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide 0.62 419.15
68 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(7-methyl-2,7-diaza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide 0.77 419.03
69 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylamino-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.78 379.01
70 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(2,2-dioxo-2l6-thia-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide 0.76 425.87
71 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide 0.80 391.99
72 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(1,1-dioxo-1l6-thia-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide 0.75 425.90

73
2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylamino-3-methyl- 0.81 393.02

azetidin-1-yl)-benzooxazol-5-yl]-amide

74 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-2-aza-spiro[3.4]oct-2-yl)-benzooxazol-5-yl]-amide 0.77 391.95
Example 44: 1H NMR (400 MHz, DMSO) 5: 10.02 (s, 1 H), 7.86 (s, 1 H), 7.77 (dd, J, = 1.2 Hz,
J2 = 8.3 Hz, 1 H), 7.74 (d, J = 1.2 Hz, 1 H), 7.38 (dd, J, = 1.7 Hz, J2 = 8.8 Hz, 1 H), 7.35 (d, J =
8.6 Hz, 1 H), 6.87 (d, J = 8.3 Hz, 1 H), 4.63 (t, J = 8.7 Hz, 2 H), 4.52-4.58 (m, 1 H), 4.38-4.44
(m, 2 H), 3.99 (dd, J, = 4.6 Hz, J2 = 9.0 Hz, 2 H), 3.65 (hept, J = 6.6 Hz, 1 H), 3.25 (t, J = 8.6
Hz, 2H), 1.11 (d, J = 6.1 Hz, 6 H).
Example 47: 1H NMR (400 MHz, DMSO) 5: 10.01 (s, 1 H), 7.86 (s, 1 H), 7.77 (d, J= 8.3 Hz, 1
H), 7.73 (d, J = 0.7 Hz, 1 H), 7.32-7.40 (m, 2 H), 6.87 (d, J = 8.3 Hz, 1 H), 5.93 (d, J = 6.8 Hz, 1
H), 4.59-4.66 (m, 3 H), 4.38 (t, J = 7.8 Hz, 2 H), 3.95 (dd, J, = 4.6 Hz, J2 = 8.6 Hz, 2 H), 3.25 (t,
J = 8.6 Hz, 2 H).
Example 50: 1H NMR (400 MHz, DMSO) 5: 10.00 (s, 1 H), 7.86 (s, 1 H), 7.77 (dd, J, = 0.7 Hz,
J2 = 8.3 Hz, 1 H), 7.70 (s, 1 H), 7.30-7.37 (m, 2 H), 6.87 (d, J = 8.3 Hz, 1 H), 4.62 (t, J = 8.8 Hz,
2 H), 4.36 (s, 4 H), 3.52-3.57 (m, 2 H), 3.25 (t, J = 8.8 Hz, 2 H), 1.85-1.91 (m, 4 H).
Example 57: 1H NMR (400 MHz, DMSO) 5: 10.02 (s,1 H), 7.86 (s,1 H), 7.77 (d, J = 8.6 Hz, 1
H), 7.73 (s, 1 H), 7.30-7.40 (m, 2 H), 6.87 (d, J = 8.3 Hz,1 H), 5.25 (quint, J = 6.8 Hz, 1 H),
4.76-4.83 (m, 4 H), 4.62 (t, J = 8.6 Hz, 2 H), 3.25 (t, J = 8.6 Hz, 2 H), 3.23 (s, 3 H).
Example 70: 1H NMR (400 MHz, DMSO) 5: 10.03 (s, 1 H), 7.87 (s, 1 H), 7.76-7.80 (m, 2 H),
7.36-7.44 (m, 2 H), 6.87 (d, J = 8.3 Hz, 1 H), 4.63 (t, J = 8.6 Hz,2 H), 4.54 (s, 4 H), 4.45 (s, 4
H), 3.25 (t, J = 8.8 Hz, 2 H).
Example 71: 1H NMR (400 MHz, DMSO) 5: 10.01 (s, 1 H), 7.87 (s, 1 H), 7.78 (dd, J, = 1.0 Hz,
J2 = 8.3 Hz, 1 H), 7.74 (s, 1 H), 7.33-7.41 (m, 2 H), 6.87 (d, J = 8.4 Hz, 1 H), 4.63 (t, J = 8.7 Hz,
2 H), 3.98-4.12 (m, 4 H), 3.77-3.88 (m, 2 H), 3.26 (t, J = 9.0 Hz, 2 H), 2.54-2.64 (m, 2 H), 2.09-
2.20 (m, 2 H).
Example 72: 1H NMR (400 MHz, DMSO) 5: 10.06 (s, 1 H), 7.87 (s, 1 H), 7.85 (s, 1 H), 7.78 (d,
J = 8.3 Hz), 7.38-7.46 (m, 2 H), 6.88 (d, J = 8.4 Hz, 1 H), 5.03-5.11 (m, 2 H), 4.63 (t, J = 8.6 Hz,
2 H), 4.44-4.52 (m, 2 H), 4.13-4.19 (m, 2 H), 3.26 (t, J = 8.6 Hz, 2 H), 2.89 (t, J = 6.8 Hz, 2 H).
Example 75
2-(4-Methyl-piperazin-1 -yl)-benzooxazole-5-carboxylic acid (2,3-dihydro-benzofuran-5-yl)-
amide
To a solution of 2-(4-methylpiperazin-1-yl)benzo[d]oxazole-5-carboxylic acid (45 mg, 172 umol)
and 5-amino-2,3-dihydrobenzofuran (47 mg, 344 umol) in DCM (2 ml_) and pyridine (0.14 ml_)
POCI3 (17 uL, 189 jamol) was added. The mixture was stirred at rt for 30 min gefore it was
concentrated. The residue was dissolved in acetonitrile (1 ml_) and separated by prep. HPLC to

give the title compound (35 mg) as a beige solid; LC-MS: tR = 0.57 min; [M+H]+ = 379.19; 1H NMR (400 MHz, CDCI3) 5: 7.81 (s, 1 H), 7.75 (s, 1 H), 7.67 (s, 1 H), 7.62 (d, J = 8.3 Hz, 1 H), 7.33 (d, J =8.3 Hz, 1 H), 7.16 (dd, J, = 0.7 Hz, J2 = 8.2 Hz, 1 H), 6.78 (d, J = 8.5 Hz, 1 H), 4.61 (t, J = 8.7 Hz, 2 H), 3.76-3.85 (m, 4 H), 3.25 (t, J = 8.7 Hz, 2 H), 2.56-2.66 (m, 4 H), 2.41 (s, 3 H).
Examples 76 to 80
The following Example compoundss were prepared in analogy to Example 75 starting from Intermediates C2 to C6 and 5-amino-2,3-dihydrobenzofuran.

Example Name

tR [min] [M+H]*
76 2-Piperidin-1-yl-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-
yl)-amide 0.84 364.01
77 2-Morpholin-4-yl-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-
5-yl)-amide 0.76 366.14
78 2-Diethylamino-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-5-
yl)-amide 0.81 352.05
79 2-Fyrrolidin-1-yl-benzooxazole-5-carboxylicacid(2,3-dihydro-benzofuran-
5-yl)-amide 0.76 350.02
80 2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazole-5-carboxylic acid (2,3-dihydro-benzofuran-5-yl)-amide 0.75 377.98
Example 76: 1H NMR (400 MHz, CDCI3) 5: 7.81 (s, 2 H), 7.67 (s, 1 H), 7.63 (d, J = 8.3 Hz, 1 H), 7.32 (d, J= 8.3 Hz, 1 H), 7.17 (dd, J, = 1.5 Hz, J2 = 8.3 Hz, 1 H), 6.78 (d, J = 8.5 Hz, 1 H), 4.61 (t, J = 8.7 Hz, 2 H), 3.69-3.77 (m, 4 H), 3.26 (t, J = 8.7 Hz, 2 H), 1.70-1.78 (m, 6 H). Example 77: 1H NMR (400 MHz, CDCI3) 5: 7.84 (s, 1 H), 7.75 (s, 1 H), 7.63-7.69 (m, 2 H), 7.36 (d, J = 8.3 Hz, 1 H), 7.16 (dd, J, = 1.1 Hz, J2 = 8.4 Hz, 1 H), 6.79 (d, J = 8.4 Hz, 1 H), 4.61 (t, J = 8.7 Hz, 2 H), 3.84-3.89 (m, 4 H), 3.73-3.79 (m, 4 H), 3.26 (t, J = 8.7 Hz, 2 H). Example 78: 1H NMR (400 MHz, CDCI3) 5: 7.80 (d, J = 0.8 Hz, 1 H), 7.75 (s, 1 H), 7.68 (s, 1 H), 7.60 (dd, 4 = 1.2 Hz, J2 = 8.3 Hz, 1 H), 7.33 (d, J = 8.3 Hz, 1 H), 7.16 (dd, J, = 1.5 Hz, J2 = 8.3 Hz), 6.78 (d, J = 8.5 Hz, 1 H), 4.61 (t, J = 8.7 Hz, 2 H), 3.64 (q, J = 7.1 Hz, 4 H), 3.26 (t, J = 8.6 Hz, 2 H), 1.33 (t, J = 7.1 Hz, 6 H).
Example 79: 1H NMR (400 MHz, CDCI3) 5: 7.82 (d, J = 0.7 Hz, 1 H), 7.80 (s, 1 H), 7.68 (s, 1 H), 7.61 (dd, J, = 1.4 Hz, J2 = 8.3 Hz, 1 H), 7.34 (d, J = 8.3 Hz, 1 H), 7.17 (dd, J, = 1.5 Hz, J2 =
8.5 Hz, 1 H), 6.78 (d, J = 8.5 Hz, 1 H), 4.61 (t, J = 8.7 Hz, 2 H), 3.67-3.74 (m, 4 H), 3.26 (t, J =
8.6 Hz, 2 H), 2.03-2.13 (m, 4 H).

Example 80: 1H NMR (400 MHz, CDCI3) 5: 7.90 (s, 1 H), 7.79 (s br, 1 H), 7.66-7.71 (m, 2 H), 7.43 (d, J = 8.3 Hz, 1 H), 7.17 (d, J = 8.3 Hz, 1 H), 6.79 (d, J = 8.5 Hz, 1 H), 5.43 (d, J = 7.5 Hz, 2 H), 4.79 (d, J = 7.5 Hz, 2 H), 4.61 (t, J = 8.7 Hz, 2 H), 4.15 (t, J = 7.3 Hz, 2 H), 3.26 (t, J = 8.6 Hz, 2 H), 2.80 (t, J =7.2 Hz, 2 H).
Example 81
2,3-Dihydro-benzofuran-5-carboxylic acid (2-piperidin-1-yl-benzothiazol-5-yl)-amide
To a solution of 2-(piperidin-1-yl)benzo[d]thiazol-5-amine (53 mg, 226 umol) and 2,3-dihydrobenzo[b]furan-5-carboxylic acid (37 mg, 226 umol) in MeCN (2 ml_) pyridine (0.18 ml_) followed by POCI3 (0.23 ml_, 248 umol) was added. The mixture was stirred at rt for 15 in before it was diluted with water (0.25 ml_) and then concentrated. The residue was dissolved in DMF (1.5 ml_) and formic acid (0.1 ml_) and separated by prep. HPLC to give the title compound (31 mg) as a solid; LC-MS: tR = 0.76 min; [M+H]+ = 380.25; 1H NMR (400 MHz, CDCI3) 5: 7.80 (s, 2 H), 7.66-7.71 (m, 2 H), 7.56 (s, 2 H), 6.86 (d, J = 8.3 Hz, 1 H), 4.68 (t, J = 8.8 Hz, 2 H), 3.60-3.67 (m, 4 H), 3.29 (t, J = 8.7 Hz, 2 H), 1.68-1.78 (m, 6 H).
Examples 82 to 97
The following Example compounds were prepared in analogy to Example 81 starting from Intermediates D2 to D17 and 2,3-dihydrobenzo[b]furan-5-carboxylic acid.

Example Name LC-MS

tR [min] [M+H]*
82 2,3-Dihydro-benzofuran-5-carboxylic acid(2-morpholin-4-yl-benzothiazol-5-
yl)-amide 0.76 382.23
83 2,3-Dihydro-benzofuran-5-carboxylic acid[2-(4-methyl-piperazin-1-yl)-benzothiazol-5-yl]-amide 0.62 395.22
84 2,3-Dihydro-benzofuran-5-carboxylic acid(2-pyrrolidin-1-yl-benzothiazol-5-
yl)-amide 0.69 366.17
85 2,3-Dihydro-benzofuran-5-carboxylic acid(2-diethylamino-benzothiazol-5-
yl)-amide 0.73 367.98
86 2,3-Dihydro-benzofuran-5-carboxylic acid(2-dimethylamino-benzothiazol-
5-yl)-amide 0.66 344.01
87 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3,3-difluoro-azetidin-1 -yl)-
benzothiazol-5-yl]-amide 0.85 388.11
88 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3,3-difluoro-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide 0.84 401.96

89
2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3,3-difluoro-piperidin-1-yl)-benzothiazol-5-yl]-amide 0.89 416.07
90 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazol-5-yl]-amide 0.75 394.12
91 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-benzothiazol-5-yl]-amide 0.69 394.12
92 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(1,1-dioxo-1l6-thiomorpholin-4-yl)-benzothiazol-5-yl]-amide 0.78 430.01
93 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-5-yl}-amide 0.64 397.16
94 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-methoxy-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide 0.70 396.14
95 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-methoxy-piperidin-1-yl)-benzothiazol-5-yl]-amide 0.77 410.12
96 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-hydroxy-3-methyl-azetidin-1 -yl)-benzothiazol-5-yl]-amide 0.67 382.14
97 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-dimethylamino-piperidin-1-yl)-benzothiazol-5-yl]-amide 0.62 423.13
Example 82: 1H NMR (400 MHz, CDCI3) 5: 7.80 (s, 2 H), 7.76 (d, J = 1.7 Hz, 1 H), 7.69 (dd, J,
= 1.8 Hz, J2 = 8.3 Hz, 1 H), 7.58 (m, 2 H), 6.86 (d, J = 8.3 Hz, 1 H), 4.69 (t, J = 8.8 Hz, 2 H),
3.86 (m, 4 H), 3.66 (m, 4 H), 3.30 (t, J = 8.8 Hz, 2 H).
Example 83:1H NMR (400 MHz, D6-DMSO) 5: 10.06 (s, 1 H), 7.98 (d, J= 1.9 Hz, 1 H), 7.89 (s,
1 H), 7.80 (dd, J, = 1.8 Hz, J2 = 8.4 Hz, 1 H), 7.69 (d, J = 8.5 Hz, 1 H), 7.48 (dd, J, = 2.0 Hz, J2
= 8.6 Hz, 1 H), 6.89 (d, J = 8.4 Hz, 1 H), 4.64 (t, J = 8.8 Hz, 2 H), 3.56-3.61 (m, 4 H), 3.27 (t, J
= 8.7 Hz, 2 H), 2.49-2.53 (m, 4 H), 2.30 (s, 3 H).
Example 87: 1H NMR (400 MHz, CDCI3) 5: 7.84 (s, 1 H), 7.81 (s, 2 H), 7.69 (dd, J, = 1.8 Hz, J2
= 8.8 Hz), 7.59-7.65 (m, 2 H), 6.87 (d, J = 8.3 Hz, 1 H), 4.70 (t, J = 8.8 Hz, 2 H), 4.59 (t, J =
11.7 Hz, 4 H), 3.30 (t, J = 8.7 Hz, 2 H).
Example 90: 1H NMR (400 MHz, D6-DMSO) 5: 10.09 (s, 1 H), 8.07 (s, 1 H), 7.90 (s, 1 H), 7.81
(d, J = 8.1 Hz, 1 H), 7.75 (d, J = 8.3 Hz, 1 H), 7.50 (d, J = 8.6 Hz, 1 H), 6.91 (d, J = 8.2 Hz, 1
H), 5.34 (d, J = 7.2 Hz, 2 H), 4.59-4.74 (m, 4 H), 3.90-4.02 (m, 2 H), 3.29 (t, J = 8.7 Hz, 2 H),
2.68-2.79 (m, 2 H).
Example 92: 1H NMR (400 MHz, D6-DMSO) 5: 10.08 (s, 1 H), 8.04 (d, J= 1.9 Hz, 1 H), 7.89 (s,
1 H), 7.80 (dd, J, = 1.6 Hz, J2 = 8.4 Hz, 1 H), 7.74 (d, J = 8.6 Hz, 1 H), 7.51 (dd, J, = 1.9 Hz, J2
= 8.6 Hz, 1 H), 6.89 (d, J = 8.4 Hz, 1 H), 4.64 (t, J = 8.8 Hz, 2 H), 4.04-4.09 (m, 4 H), 3.31-3.34
(m, 4 H), 3.27 (t, J =8.8 Hz, 2 H).

Example 96: 1H NMR (400 MHz, D6-DMSO) 5: 10.05 (s, 1 H), 7.96 (d, J= 1.9 Hz, 1 H), 7.88 (s, 1 H), 7.79 (dd, J^ = ^A Hz, J2 = 8.4 Hz, 1 H), 7.68 (d, J = 8.6 Hz, 1 H), 7.48 (dd, J, = 1.9 Hz, J2 = 8.6 Hz, 1 H), 6.89 (d, J = 8.4 Hz, 1 H), 5.85 (s br, 1 H), 4.64 (t, J = 8.8 Hz, 2 H), 3.95-4.04 (m, 4 H), 3.27 (t, J = 8.7 Hz, 2 H), 1.47 (s, 3 H).
Example 98
(S)-N-(2-(3-hydroxypyrrolidin-1-yl)benzo[d]thiazol-5-yl)-2,3-dihydrobenzofuran-5-
carboxamide
To a solution of (S)-pyrrolidin-3-ol (8 mg, 91 umol) and Et3N (51 oL, 362 umol) in THF (0.6 mL) N-(2-chlorobenzo[d]thiazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide (30 mg, 72.5 umol) was added and the mixture was stirred at 65°C for 16 h. The mixture was concentrated, dissolved in DMSO (0.6 mL) and separated by prep. HPLC to give the title compound (17 mg) as a white solid; LC-MS: tR = 0.80 min; [M+H]+ = 382.00; 1H NMR (400 MHz, DMSO) 5: 10.06 (s, 1 H), 7.89 (s, 1 H), 7.85 (s, H), 7.76 (d, J = 8.3 Hz, 1 H), 7.64 (d, J = 8.6 Hz, 1 H), 7.39 (d, J = 8.3 Hz, 1 H), 6.86 (d, J = 8.3 Hz, 1 H), 5.28 (d, J = 3.2 Hz, 1 H), 4.61 (t, J = 8.6 Hz, 2 H), 4.40-4.46 (m, 1 H), 3.66-3.82 (m, 4 H), 3.24 (t, J= 8.6 Hz, 2 H), 2.04-2.17 (m, 1 H), 1.89-2.00 (m, 1 H).
Examples 99 to 117
The following Example compounds were prepared in analogy to Example 98 starting from Intermediate E1 and the appropriate amines.

Example Name LC-MS

tR [min] [M+H]*
99 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzothiazol-5-yl]-amide 0.91 421.68
100 2,3-Dihydro-benzofuran-5-carboxylicacid{2-[methyl-(1-oxetan-3-yl-piperidin-4-yl)-amino]-benzothiazol-5-yl}-amide 0.87 465.05
101 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzothiazol-5-yl]-amide 0.93 421.70
102 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-oxetan-3-yl-piperazin-1-yl)-benzothiazol-5-yl]-amide 0.84 437.02
103 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(methyl-oxetan-3-yl-amino)-benzothiazol-5-yl]-amide 0.87 382.01
104 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(1-oxa-6-aza-spiro[3.3]hept-6-yl)-benzothiazol-5-yl]-amide 0.88 394.01
105 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-dimethylaminomethyl-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide 0.96 422.95

106
2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-isopropoxy-azetidin-1-yl)-benzothiazol-5-yl]-amide 1.01 410.05
107 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-ethoxymethyl-pyrrolidin-1 -yl)-benzothiazol-5-yl]-amide 1.07 424.05
108 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-methoxy-piperidin-1-yl)-benzothiazol-5-yl]-amide 0.98 410.02
109 2,3-Dihydro-benzofuran-5-carboxylicacid[2-(3-hydroxy-azetidin-1-yl)-benzothiazol-5-yl]-amide 0.79 367.97
110 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(4-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide 0.83 395.99
111 rac-2,3-Dihydro-benzofuran-5-carboxylicacid[2-(2-phenyl-azetidin-1-yl)-benzothiazol-5-yl]-amide 1.10 428.00
112 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((R)-3-hydroxy-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide 0.81 381.98
113 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-methoxymethyl-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide 1.00 410.01
114 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((S)-3-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide 0.85 396.00
115 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-oxa-6-aza-spiro[3.4]oct-6-yl)-benzothiazol-5-yl]-amide 0.87 408.02
116 2,3-Dihydro-benzofuran-5-carboxylicacid [2-((R)-3-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide 0.85 395.99
117 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(2-dimethylaminomethyl-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide 1.05 422.94
Example 101: 1H NMR (400 MHz, D6-DMSO) 5: 10.08 (s, 1 H), 7.90 (s, 1 H), 7.85 (s, 1 H), 7.76 (d, J = 8.5 Hz, 1 H), 7.65 (d, J = 8.5 Hz, 1 H), 7.42 (dd, J^ = ^.^ Hz, J2 = 8.5 Hz, 1 H), 6.86 (d, J = 8.3 Hz, 1 H), 4.61 (t, J = 8.7 Hz, 2 H), 4.31 (s br, 4 H), 3.79-3.82 (m, 2 H), 3.42-3.48 (m, 2 H), 3.24 (t, J = 8.7 Hz, 2 H), 1.84-1.90 (m, 2 H), 1.52-1.60 (m, 2 H).
Example 102: 1H NMR (400 MHz, D6-DMSO) 5: 10.09 (s, 1 H), 7.91 (s, 1 H), 7.84 (s, 1 H), 7.75 (d, J = 7.8 Hz, 1 H), 7.66 (d, J = 8.8 Hz, 1 H), 7.42 (d, J = 8.1 Hz, 1 H), 6.86 (d, J = 8.3 Hz, 1 H), 4.61 (t, J = 8.8 Hz, 2H), 4.53-4.58 (m, 2 H), 4.44-4.49 (m, 2 H), 3.62-3.70 (m, 2 H), 3.54-3.60 (m, 2 H), 3.43-3.49 (m, 1 H), 3.24 (t, J = 8.8 Hz, 2 H), 2.36-2.42 (m, 4 H). Example 103: 1H NMR (400 MHz, D6-DMSO) 5: 10.09 (s, 1 H), 7.93 (d, J= 1.4 Hz, 1 H), 7.84 (s, 1 H), 7.75 (d, J = 8.4 Hz, 1 H), 7.67 (d, J = 8.6 Hz, 1 H), 7.41 (dd, J, = 1.5 Hz, J2 = 8.3 Hz, 1 H), 6.86 (d, J = 8.3 Hz, 1 H), 5.25 (quint, J = 6.8 Hz, 1 H), 4.75-4.85 (m, 4 H), 4.61 (t, J = 8.6 Hz, 2 H), 3.22-3.27 (t, J = 8.6 Hz, 2 H), 3.21 (s, 3 H).

Example 109: 1H NMR (400 MHz, D6-DMSO) 5: 10.09 (s, 1 H), 7.90 (s, 1 H), 7.84 (s, 1 H), 7.76 (d, J = 8.4 Hz, 1 H), 7.66 (d, J = 8.5 Hz, 1 H), 7.43 (d, J = 8.5 Hz, 1 H), 6.86 (d, J = 8.4 Hz, 1 H), 6.09 (d, J = 6.5 Hz, 1 H), 4.64-4.70 (m, 1 H), 4.61 (t, J = 8.6 Hz, 2 H), 4.28-4.34 (m, 2 H), 3.87 (dd, J, = 4.4 Hz, J2 = 8.6 Hz, 2 H), 3.24 (t, J = 8.7 Hz, 2 H).
Example 116: 1H NMR (400 MHz, D6-DMSO) 5: 10.07 (s, 1 H), 7.85 (s, 1 H), 7.83 (s, 1 H), 7.75 (d, J = 8.3 Hz, 1 H), 7.62 (d, J = 8.6 Hz, 1 H), 7.38 (dd, J, = 1.0 Hz, J2 = 8.6 Hz, 1 H), 6.85 (d, J = 8.3 Hz, 1 H), 5.25 (d, J = 3.9 Hz, 1 H), 4.61 (t, J = 8.8 Hz, 2 H), 3.57-3.76 (m, 2 H), 3.19-3.30 (m, 3 H), 3.08 (dd, J, = 8.6 Hz, J2 = 12.7 Hz, 1 H), 1.75-1.91 (m, 2 H), 1.40-1.54 (m, 2 H).
Example 118
2,3-Dihydro-benzofuran-5-carboxylic acid (2-azetidin-1-yl-benzooxazol-5-yl)-amide
A solution of 2,3-dihydrobenzo[b]furan-5-carboxylic acid (30.3 mg, 0.185 mmol), HBTU (70.1 mg, 0.185 mmol) and DIPEA (95 uL, 0.554 mmol) in DMF (1 mL) was stirred at rt for 30 min before 2-azetidin-1-yl-benzooxazol-5-ylamine (35 mg, 0.185 mmol, Intermediate A40) was added. The mixture was stirred at 50°C for 16 h before it was separated by prep. HPLC to give the title compound (59 mg) as a colourless resin; LC-MS: tR = 0.72 min; [M+H]+ = 336.09; 1H NMR (400 MHz, CDCI3): 5 7.81 (s, 1 H), 7.77 (s, 1 H), 7.69 (d, J = 8.3 Hz, 1 H), 7.52 (s, 1 H), 7.42 (d, J = 8.7 Hz, 1 H), 7.24 (d, J = 8.6 Hz, 1 H), 6.86 (d, J = 8.3 Hz, 1 H), 4.69 (t, J = 8.8 Hz, 2 H), 4.33 (t, J = 7.6 Hz, 4 H), 3.30 (t, J = 8.7 Hz, 2 H), 2.54 (quint, J = 7.5 Hz).
Examples 119 to 195
The following Example compounds were prepared in analogy to Example 118 starting from Intermediates A2 to A6, A8, A12, A16, A17, A25, A36, A37, and A40 to A48 and the appropriate benzoic acid derivatives.

Example Name LC-MS

tR [min] [M+H]*
119 2,3-Dihydro-benzofuran-5-carboxylicacid(2-ethylamino-benzooxazol-5-yl)-
amide 0.67 324.09
120 2,3-Dihydro-benzofuran-5-carboxylicacid [2-(3-pyridin-2-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.66 413.26
121 Benzo[1,3]dioxole-5-carboxylicacid [2-(3,3-difluoro-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.89 374.02
122 Benzo[1,3]dioxole-5-carboxylicacid[2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.72 353.89
123 Benzo[1,3]dioxole-5-carboxylicacid [2-( 1 -aza-spiro[3.3]hept-1 -yI)-
benzooxazol-5-yl]-amide 1.01 378.07

124 Benzo[1,3]dioxole-5-carboxylic acid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)- 0.79 380.05

benzooxazol-5-yl]-amide

125 Benzo[1,3]dioxole-5-carboxylicacid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)- 0.83 394.06

benzooxazol-5-yl]-amide

126 Benzo[1,3]dioxole-5-carboxylic acid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide 0.85 408.10
127 Benzo[1,3]dioxole-5-carboxylic acid (2-pyrrolidin-1-yl-benzooxazol-5-yl)- 0.89 352.04

amide

128 Benzo[1,3]dioxole-5-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)- 0.76 394.26

benzooxazol-5-yl]-amide

129 Benzo[1,3]dioxole-5-carboxylic acid (2-piperidin-1 -yl-benzooxazol-5-yl)- 0.97 266.04

amide

130 Benzo[1,3]dioxole-5-carboxylicacid [2-(3,3-difluoro-piperidin-1-yl)- 0.94 401.83

benzooxazol-5-yl]-amide

131 Benzo[1,3]dioxole-5-carboxylicacid [2-(4-methoxy-piperidin-1-yl)- 0.88 396.08

benzooxazol-5-yl]-amide

132 Benzo[1,3]dioxole-5-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)- 0.83 408.10

benzooxazol-5-yl]-amide

133 Benzo[1,3]dioxole-5-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide 0.84 408.10
134 Benzo[1,3]dioxole-5-carboxylicacid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide 0.95 401.84
135 Benzo[1,3]dioxole-5-carboxylicacid[2-(4-hydroxy-piperidin-1-yl)- 0.75 382.08

benzooxazol-5-yl]-amide

136 Benzo[1,3]dioxole-5-carboxylic acid (2-morpholin-4-yl-benzooxazol-5-yl)- 0.81 368.03

amide

137 Benzo[1,3]dioxole-5-carboxylicacid[2-(4-methyl-piperazin-1-yl)- 0.79 381.10

benzooxazol-5-yl]-amide

138 Benzo[1,3]dioxole-5-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)- 0.84 394.07

benzooxazol-5-yl]-amide

139 Benzo[1,3]dioxole-5-carboxylic acid (2-diethylamino-benzooxazol-5-yl)-amide 0.95 353.90
140 Chroman-6-carboxylic acid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]- 0.78 366.05

amide

141 Chroman-6-carboxylicacid[2-(3,3-difluoro-azetidin-1-yl)-benzooxazol-5-yl]- 0.95 385.84

amide

142 Chroman-6-carboxylic acid [2-(1 -aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-
amide 1.06 390.10
143 Chroman-6-carboxylicacid[2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-
5-yl]-amide 0.85 392.09
144 Chroman-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-
5-yl]-amide 0.89 406.09
145 Chroman-6-carboxylic acid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-
5-yl]-amide 0.91 420.13
146 Chroman-6-carboxylicacid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide 0.94 364.06
147 Chroman-6-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-
5-yl]-amide 0.80 406.28
148 Chroman-6-carboxylicacid(2-piperidin-1-yl-benzooxazol-5-yl)-amide 1.03 378.09
149 Chroman-6-carboxylic acid [2-(4,4-difluoro-piperidin-1 -yl)-benzooxazol-5-yl]-
amide 1.01 414.11
150 Chroman-6-carboxylic acid [2-(3,3-difluoro-piperidin-1 -yl)-benzooxazol-5-yl]-
amide 1.00 141.09
151 Chroman-6-carboxylicacid[2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-
amide 0.81 394.10
152 Chroman-6-carboxylic acid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-
amide 0.94 408.13
153 Chroman-6-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-
5-yl]-amide 0.89 420.15
154 Chroman-6-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-
5-yl]-amide 0.90 420.14
155 Chroman-6-carboxylicacid(2-morpholin-4-yl-benzooxazol-5-yl)-amide 0.87 380.09
156 Chroman-6-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-
amide 0.85 393.11
157 Chroman-6-carboxylicacid(2-diethylamino-benzooxazol-5-yl)-amide 1.00 366.12
158 Chroman-6-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-
5-yl]-amide 0.90 406.12
159 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid[2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.72 368.04
160 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide 0.79 394.07

161 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide 1.01 392.08
162 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide 0.83 408.11
163 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide 0.86 422.12
164 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid (2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide 0.89 366.05
165 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide 0.76 408.27
166 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid(2-piperidin-1-yl-benzooxazol-5-yl)-amide 0.98 380.09
167 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide 0.75 396.09
168 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide 0.94 416.09
169 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide 0.88 410.11
170 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide 0.95 416.09
171 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide 0.85 422.12
172 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide 0.83 422.12
173 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid (2-morpholin-4-yl-benzooxazol-5-yl)-amide 0.81 382.09
174 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide 0.79 395.11
175 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid (2-diethylamino-benzooxazol-5-yl)-amide 0.95 368.07
176 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide 0.85 408.10
177 4-Methyl-3,4-dihydro-2/-/-benzo[1,4]oxazine-6-carboxylic acid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide 0.72 381.08

178
4-Methyl-3,4-dihydro-2/-/-benzo[ 1,4]oxazine-6-carboxylic acid [2-(3,3-difluoro- 0.92 401.03

azetidin-1-yl)-benzooxazol-5-yl]-amide

179 4-Methyl-3,4-dihydro-2H-benzo[ 1,4]oxazine-6-carboxylic acid [2-(1 -aza- 0.96 405.12

spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide

180 4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide 0.81 407.10
181 4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(6-oxa-1- 0.82 421.11

aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide

182 4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(7-oxa-1- 0.83 435.13

aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide

183 4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid(2-pyrrolidin-1- 0.79 379.13

yl-benzooxazol-5-yl)-amide

184 4-Methyl-3,4-dihydro-2H-enzo[1,4]oxazine-6-carboxylic acid [2-(2-oxa-5- 0.78 421.26

aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide

185 4-Methyl-3,4-dihydro-2H-enzo(1,4]oxazine 6-carboxylic acid[1- 0.90 393.12

yl-benzooxazol-5-yl)-amide

186 4-Methyl-3,4-dihydro-2H-nzo[14]oxazine-6-carboxylic acid [2-(4-hydroxy- 0.74 409.13

piperidin-1-yl)-benzooxazol-5-yl]-amide

187 4-Methyl-3,4-dihydro-2H-enzo[1,4oxazine-6-carboxylic acid-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide 0.97 429.12
188 4-Methyl-3,4-dihydro-2H-benzo[1,4azine-6-carboxylic acid [2-(3,3-difluoro-piperidin-1 -yl)-benzooxazol-5-yl]-amide 0.97 429.14
189 4-Methyl-3,4-dihydro-2H--benzo[1,4]oxazine-6-carboxylic acid [2-(2-oxa-6- 0.84 435.14

aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide

190 4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(2-oxa-7- 0.82 435.13

aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide

191 4-Methyl-3,4-dihydro-2H--benzo[1,4]oxazine-6-carboxylic acid [2-(4-methoxy- 0.86 423.15

piperidin-1 -yl)-benzooxazol-5-yl]-amide

192 4-Methyl-3,4-dihydro-2H--benzo[1,4]oxazine-6-carboxylic acid (2-morpholin-4- 0.82 395.09

yl-benzooxazol-5-yl)-amide

193 4-Methyl-3,4-dihydro-2H--benzo[1,4]oxazine-6-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide 0.67 408.15
194 4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid (2- 0.86 381.12

diethylamino-benzooxazol-5-yl)-amide

195
4-Methyl-3,4-dihydro-2/-/-benzo[ 1,4]oxazine-6-carboxylic acid [2-(cyclopropyl- 0.85 421.13

oxetan-3-yl-amino)-benzooxazol-5-yl]-amide

Example 124: 1H NMR (400 MHz, D6-DMSO): 5 10.07 (s, 1 H), 7.80 (s, 1 H), 7.59 (d, J = 8.0
Hz, 1 H), 7.53 (d, J = 0.7 Hz, 1 H), 7.40-7.47 (m, 2 H), 7.07 (d, J = 8.2 Hz, 1 H), 6.15 (s, 2 H),
5.23 (d, J = 7.4 Hz, 2 H), 4.67 (d, J = 7.4 Hz, 2 H), 4.02 (t, J = 7.2 Hz, 2 H), 2.73 (t, J = 7.1 Hz,
2H).
Example 133: 1H NMR (400 MHz, D6-DMSO): 5 10.04 (s, 1 H), 7.73 (s, 1 H), 7.59 (d, J = 8.2
Hz, 1 H), 7.53 (s, 1 H), 7.37 (s, 2 H), 7.07 (d, J = 8.1 Hz, 1 H), 6.15 (s, 2 H), 4.32 (s, 4 H), 3.84
(s, 2 H), 3.54 (t, J = 5.1 Hz, 2 H), 1.86-1.92 (m, 2 H), 1.54-1.62 (m, 2 H).
Example 144: 1H NMR (400 MHz, D6-DMSO): 5 10.00 (s, 1 H), 7.70-7.78 (m, 3 H), 7.34-7.41
(m, 2 H), 6.85 (d, J = 8.3 Hz, 1 H), 4.22 (t, J = 4.8 Hz, 2 H), 4.00-4.13 (m, 4 H), 3.79-3.90 (m, 2
H), 2.83 (t, J = 6.1 Hz, 2 H), 2.54-2.65 (m, 3 H), 2.11-2.20 (m, 1 H), 1.93-2.01 (m, 2 H).
Example 159: 1H NMR (400 MHz, DMSO): 5 10.03 (s, 1 H), 7.76 (s, 1 H), 7.49-7.55 (m, 2 H),
7.34-7.43 (m, 2 H), 7.00 (d, J = 8.4 Hz, 1 H), 5.91 (d, J = 6.7 Hz, 1 H), 4.62-4.70 (m, 1 H), 4.36-
4.43 (m, 2 H), 4.29-4.36 (m, 4 H), 3.94-4.00 (m, 2 H).
Example 176: 1H NMR (400 MHz, D6-DMSO): 5 10.04 (s, 1 H), 7.77 (s, 1 H), 7.48-7.55 (m, 2
H), 7.38-7.44 (m, 2 H), 7.00 (d, J = 8.3 Hz, 1 H), 4.89-5.00 (m, 3 H), 4.75 (t, J = 6.2 Hz, 2 H),
4.29-4.37 (m, 4 H), 2.93-3.01 (m, 1 H), 0.88-0.96 (m, 2 H), 0.76-0.82 (m, 2 H).
Example 186: 1H NMR (400 MHz, D6-DMSO): 5 9.94 (s, 1 H), 7.72 (s, 1 H), 7.34 (s, 2 H), 7.27
(m, 2 H), 6.77-6.81 (m, 1 H), 4.87 (d, J = 4.0 Hz, 1 H), 4.29-4.33 (m, 2 H), 3.88-3.96 (m, 2 H),
3.73-3.80 (m, 2 H), 3.27-3.31 (m, 2 H), 3.19 (d, J= 5.2 Hz, 1 H), 2.93 (s, 3 H), 1.82-1.90 (m, 2
H), 1.42-1.52 (m, 2 H).
Example 196
2-Piperidin-1 -yl-benzothiazole-5-carboxylic acid (2,3-dihydro-benzofuran-5-yl)-amide
To a solution of 2-chloro-N-(2,3-dihydrobenzofuran-5-yl)benzo[d]thiazole-5-carboxamide (62
mg, 0.174 mmol, Intermediate E2) and piperidine (17.2 oL, 0.174 mmol) in THF (1 ml_), DIPEA
(35 uL, 0.198 mmol) was added. The brown suspension was stirred at 70°C for 6 h before
another portion of piperidine (28 oL, 0.282 mmol) was added. Stirring was continued at 70°C
for 16 h. The mixture was concentrated and the residue was dissolved in DMF (2 ml_) and
purified by prep. HPLC to give the title compound (33 mg) as a pale yellow resin; LC-MS: tR =
0.84 min; [M+H]+ = 380.22; 1H NMR (500 MHz, CDCI3): 5 7.96 (d, J = 1.5 Hz, 1 H), 7.80 (s, 1
H), 7.67-7.72 (m, 2 H), 7.64 (dd, J, = 1.7 Hz, J2 = 8.2 Hz, 1 H), 7.16 (dd, J, = 2.2 Hz, J2 = 8.5
Hz, 1 H), 6.78 (d, J = 8.5 Hz, 1 H), 4.61 (t, J = 8.7 Hz, 2 H), 3.63-3.70 (m, 4 H), 3.26 (t, J = 8.7
Hz, 2H), 1.72-1.81 (m, 6 H).

Examples 197 to 212
The following Example compounds were prepared in analogy to Example 196 starting from Intermediates E2 to E4 and the appropriate aniline derivatives.

Example Name LC-MS

tR [min] [M+H]*
197 2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylic acid (2,3- 0.78 394.08

dihydro-benzofuran-5-yl)-amide

198 2-(4,4-Difluoro-piperidin-1-yl)-benzothiazole-5-carboxylic acid (2,3-dihydro- 0.89 416.09

benzofuran-5-yl)-amide

199 2-(1,1-Dioxo-thiomorpholin-4-yl)-benzothiazole-5-carboxylic acid (2,3-dihydro-benzofuran-5-yl)-amide 0.76 430.06
200 2-(4-Methoxy-piperidin-1 -yl)-benzothiazole-5-carboxylic acid (2,3-dihydro-benzofuran-5-yl)-amide 0.82 410.11
201 2-(4-Methyl-piperazin-1-yl)-benzothiazole-5-carboxylic acid (2,3-dihydro- 0.60 395.10

benzofuran-5-yl)-amide

202 2-(6-Oxa-1-aza-spiro[3.4]oct-1-yl)-benzothiazole-5-carboxylic acid (2,3- 0.76 408.07

dihydro-benzofuran-5-yl)-amide

203 2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylic acid (2,3- 0.79 410.04

dihydro-benzo[1,4]dioxin-6-yl)-amide

204 2-(4,4-Difluoro-piperidin-1-yl)-benzothiazole-5-carboxylic acid (2,3-dihydro- 0.89 432.07

benzo[1,4]dioxin-6-yl)-amide

205 2-(4-Methoxy-piperidin-1 -yl)-benzothiazole-5-carboxylic acid (2,3-dihydro- 0.83 426.08

benzo[1,4]dioxin-6-yl)-amide

206 2-(4-Methyl-piperazin-1-yl)-benzothiazole-5-carboxylic acid (2,3-dihydro- 0.60 411.00

benzo[1,4]dioxin-6-yl)-amide

207 2-Piperidin-1-yl-benzothiazole-5-carboxylic acid (2,3-dihydro- 0.85 396.06

benzo[1,4]dioxin-6-yl)-amide

208 2-(6-Oxa-1-aza-spiro[3.4]oct-1-yl)-benzothiazole-5-carboxylic acid (2,3-dihydro-benzo[1,4]dioxin-6-yl)-amide 0.77 424.09
209 2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylic acid 0.79 396.00

benzo[1,3]dioxol-5-ylamide

210 2-(4-Methoxy-piperidin-1-yl)-benzothiazole-5-carboxylic acid 0.83 411.96

benzo[1,3]dioxol-5-ylamide

211 2-(4-Methyl-piperazin-1-yl)-benzothiazole-5-carboxylic adbenzo[1,3]dioxol-
5-ylamide 0.60 397.06

Example 197. 1H NMR (500 MHz, D6-DMSO): 5 10.08 (s, 1 H), 8.21 (d, J= 1.6 Hz, 1 H), 7.95 (d, J= 8.2 Hz, 1 H), 7.71-7.73 (m, 1 H), 7.70 (dd, J, = 1.7 Hz, J2 = 8.2 Hz, 1 H), 7.46 (dd, J, = 2.2 Hz, J2 = 8.5 Hz, 1 H), 6.74 (d, J = 8.5 Hz, 1 H), 5.35 (d, J = 7.8 Hz, 2 H), 4.68 (d, J = 7.9 Hz, 2 H), 4.53 (t, J = 8.7 Hz, 2 H), 3.97 (t, J = 7.1 Hz, 2 H), 3.20 (m, J = 8.7 Hz, 2 H), 2.74 (t, J = 7.2 Hz, 2H), 1.23-1.30 (m, 2 H).
Example 198. 1H NMR (500 MHz, DMSO): 5 10.07 (s, 1 H), 8.10 (d, J = 1.6 Hz, 1 H), 7.93 (d, J = 8.3 Hz, 1 H), 7.69-7.71 (m, 1 H), 7.69 (d, J-, = 1.7 Hz, J2 = 8.4 Hz, 1 H), 7.44 (dd, J, = 2.2 Hz, J2 = 8.5 Hz, 1 H), 6.74 (d, J = 8.5 Hz, 1 H), 4.53 (t, J = 8.7 Hz, 2 H), 3.74-3.79 (m, 4 H), 3.20 (t, J= 8.7 Hz, 2 H), 2.12-2.21 (m, 4 H).
Example 207. 1H NMR (400 MHz, D6-DMSO): 5 10.05 (s, 1 H), 8.04 (d, J = 1.5 Hz, 1 H), 7.88 (d, J = 8.2 Hz, 1 H), 7.62 (dd, J, = 1.6 Hz, J2 = 8.2 Hz, 1 H), 7.43 (d, J = 2.4 Hz, 1 H), 7.25 (dd, 4 = 2.4 Hz, J2 = 8.8 Hz, 1 H), 6.82 (d, J = 8.8 Hz, 1 H), 4.15-4.32 (m, 4 H), 3.56-3.65 (m, 4 H), 1.57-1.73 (m, 6 H).
Example 211. 1H NMR (500 MHz, D6-DMSO): 5 10.13 (s, 1 H), 8.06 (d, J= 1.6 Hz, 1 H), 7.91 (d, J = 8.2 Hz, 1 H), 7.65 (dd, J, = 1.7 Hz, J2 = 8.2 Hz, 1 H), 7.48 (d, J = 2.0 Hz, 1 H), 7.24 (dd, 4 = 2.1 Hz, J2 = 8.4 Hz, 1 H), 6.90 (d, J = 8.4 Hz, 1 H), 6.01 (s, 2 H), 3.60 (m, 4 H), 2.44-2.48 (m, 4 H), 2.25 (s, 3 H).
Biological Assays
The nucleotide sequence and the amino acid sequence for the human NOX4 (Entrez Gene ID 50507) is known in the art and are published. The potency and efficacy of the compounds of Formula (I) are assessed for their potential to inhibit the formation of ROS in a cellular assay.
Plasmid production
The full-length human NOX4 (NM_016931.3) transcript was cloned into the pDONR™221 vector (Life Technologies™) in order to generate, by site-specific integration according to the recommendation of the manufacturer (Life Technologies™), a recombinant pJTI™ R4 DEST CMV-TO vector containing the NOX4 coding information controlled by tetracycline (tet) responsive tet-on cytomegalovirus promoter (hNOX4 pDEST). Cell Culture and Transfection
Modified human embryonic kidney cells overexpressing a tet receptor (Jump-In™ T-REx™ HEK293; Life Technologies™) were transfected with the NOX4- containing tet-on vector (hNOX4 pDEST) to generate a stable recombinant cell pool (hNOX4 T-REx-293). hNOX4 T-REx-293 cells were cultured in DMEM containing 4.5 g/L glucose supplemented with 10% fetal calf serum, penicillin (100 U/mL), streptomycin (100 |j.g/mL), geneticin (1 mg/mL), and blasticidin (5 ug/mL) at 37 °C in air with 5% CQ2. Human Nox4 expression was induced with tet

(1 jag/mL) for 24 h and extracellular H202 was quantified using the Amplex Red reagent (Life Technologies™).
Amplex Red Activity Assay
Inhibitory activities on NOX4 have been measured for each example compound using the
following procedure:
Compounds were prepared as 10 mM stock solution in DMSO vehicle, then diluted in 384-well plates using DMSO followed by a transfer of the dilutions into the assay plate. As a control, diphenylene iodonium was included at a final concentration of 10 uJVI. Compounds were tested at 10 concentrations in the range from 50 uJVI highest to 100 nM lowest.
Cellular H202 formation was measured using the Amplex Red reagent. Cells were washed with 1 x PBS, trypsinized with 1xTrypsin-EDTA, collected by centrifugation and resuspended in 1 x PBS. Cells were seeded into 384-well clear bottom plates at a density of 20 000 cells per well in presence or absence of compounds. The assay was started by the addition of Amplex Red and horseradish peroxidase at final concentrations of 25 uJVI and 0.1 U/mL, respectively. All wells contained 1.25 % of DMSO. The plates were kept at 25°C for 60 min. The amount of produced resorufin was detected with the Synergy™ Mx microplate reader (BioTek) with excitation and emission wavelengths set to 550 nm and 600 nm, respectively. Fluorescence was measured for each well and the fluorescence at 600 nm wavelength was compared to the fluorescence of the vehicle in place of compound. Inhibitory activities of example compounds were determined by calculating the IC50 value (the concentration of compound needed to inhibit 50% of the enzyme activity). The calculated IC50 values may fluctuate depending on the daily cellular assay performance. Fluctuations of this kind are known to those skilled in the art. In the case where IC50 values have been determined several times for the same compound, the geometric mean is given. IC50 values of exemplified compounds are displayed in the Table below.
Amplex Red Counter Screen Assay
In order to identify compounds that interfere with the activity assay either by inhibiting the activity of horseradish peroxidase or by directly interacting with the formed H202 a counter screen assay was established. This control assay is almost identical to the described Amplex Red activity assay with the only difference that the H202- generating cells are replaced by 1562.5 nMH202 in 1 xPBS.

Table 1

Compound of Example ICso
Amplex
[nM] ICso Control Compound of Example ICso
Amplex
[nM] ICso Control
1 344 >50 107 9510 >50
2 639 >50 108 2540 >50
3 899 >50 109 1780 >50
4 967 >50 110 2030 >50
5 627 >50 111 1090 >50
6 559 >50 112 2270 >50
7 358 >50 113 3250 >50
8 1890 >50 114 2940 >50
9 573 >50 115 3410 >50
10 711 >50 116 2170 >50
11 358 >50 117 3760 >50
12 688 >50 118 504 >50
13 5360 >50 119 990 >50
14 1700 >50 120 2340 >50
15 405 >50 121 9530 >50
16 389 >50 122 2110 >50
17 2300 >50 123 434 >50
18 568 >50 124 414 >50
19 2890 >50 125 772 >50
20 1400 >50 126 757 >50
21 1610 >50 127 1250 >50
22 505 >50 128 1740 >50
23 1470 >50 129 857 >50
24 352 >50 130 991 >50
25 804 >50 131 1050 >50
26 1490 >50 132 1080 >50
27 729 >50 133 614 >50
28 695 >50 134 870 >50
29 541 >50 135 1090 >50

30
1230 >50 136 1280 >50
31 2170 >50 137 1640 >50
32 2410 >50 138 1480 >50
33 2140 >50 139 1090 >50
34 1220 >50 140 2520 >50
35 379 >50 141 10600 >50
36 404 >50 142 891 >50
37 841 >50 143 681 >50
38 1750 >50 144 1540 >50
39 444 >50 145 1400 >50
40 812 >50 146 3180 >50
41 2520 >50 147 379 >50
42 566 >50 148 1880 >50
43 541 >50 149 1430 >50
44 1140 >50 150 2200 >50
45 573 >50 151 1410 >50
46 570 >50 152 1350 >50
47 657 >50 153 1300 >50
48 448 >50 154 1130 >50
49 1230 >50 155 756 >50
50 451 >50 156 1790 >50
51 4570 >50 157 2030 >50
52 899 >50 158 2860 >50
53 913 >50 159 1480 >50
54 2910 >50 160 541 >50
55 400 >50 161 665 >50
56 906 >50 162 954 >50
57 681 >50 163 1140 >50
58 1330 >50 164 1280 >50
59 731 >50 165 764 >50
60 1670 >50 166 1500 >50
61 5240 >50 167 1220 >50
62 702 >50 168 1140 >50

63
359 >50 169 793 >50
64 2130 >50 170 899 >50
65 851 >50 171 792 >50
66 4170 >50 172 8850 >50
67 3080 >50 173 1420 >50
68 1790 >50 174 1390 >50
69 1930 >50 175 1350 >50
70 889 >50 176 2970 >50
71 336 >50 177 6870 >50
72 524 >50 178 21800 >50
73 4100 >50 179 1740 >50
74 1080 >50 180 1770 >50
75 421 >50 181 2440 >50
76 414 >50 182 3390 >50
77 548 >50 183 8700 >50
78 417 >50 184 1890 >50
79 585 >50 185 3860 >50
80 312 >50 186 3450 >50
81 2450 >50 187 3390 >50
82 2350 >50 188 3640 >50
83 3540 >50 189 2190 >50
84 1320 >50 190 3580 >50
85 1650 >50 191 4380 >50
86 2680 >50 192 4320 >50
87 4100 >50 193 4040 >50
88 3660 >50 194 3580 >50
89 1920 >50 195 4440 >50
90 361 >50 196 2560 >50
91 4331 >50 197 728 >50
92 2460 >50 198 45200 >50
93 10300 >50 199 23900 >50
94 3290 >50 200 2750 >50
95 2140 >50 201 2870 >50

96 2670 >50 202 729 >50
97 6303 >50 203 1840 >50
98 2530 >50 204 25500 >50
99 3080 >50 205 26800 >50
100 3390 >50 206 21200 >50
101 2370 >50 207 12800 >50
102 9170 >50 208 2710 >50
103 3210 >50 209 1500 >50
104 6870 >50 210 6900 >50
105 14800 >50 211 8900 >50
106 9390 >50

Claims
1. A compound of the Formula (I),

wherein
ring (A) represents a non-aromatic 5- to 7-membered heterocyclic ring which is fused to the phenyl group; wherein said 5- to 7-membered heterocyclic ring contains one oxygen ring atom and optionally one further ring heteroatom independently selected from oxygen or nitrogen; wherein said 5- to 7-membered heterocyclic ring independently is unsubstituted, or mono-, or di-substituted, wherein the substituents are independently selected from:
• one oxo substituent attached to a ring carbon atom in alpha position to a ring oxygen and/or a ring nitrogen atom; and / or
• one C^-alkyl attached to a ring nitrogen atom having a free valency; or
• two fluoro substituents attached to the same ring carbon atom;
L represents -NH-CO-* or -CO-NH-*, wherein the asterisks (*) indicate the bond that is linked to the benzoxazole / the benzothiazole moiety;
X represents O or S; and
Y represents
• -NR1R2 wherein
> R1 represents
■ C^-alkyl;
■ C2-4-alkyl which is mono-substituted with di-(Ci.3-alkyl)amino, hydroxy or C^-alkoxy;
■ C3_5-cycloalkyl-L1-, wherein L1 represents a direct bond or C^-alkylene; and wherein the C3.5-cycloalkyl optionally contains one oxygen ring atom, and wherein said C3.5-cycloalkyl is unsubstituted, or mono-substituted with methyl or fluoro; or
■ a piperidin-3-yl, piperidin-4-yl or pyrrolidin-3-yl group, which groups are substituted on the ring nitrogen atom with C3.5-cycloalkyl, wherein said C3_5-cycloalkyl optionally contains one oxygen ring atom; and
> R2 represents hydrogen, C^-alkyl, or C3.5-cycloalkyl;

• or Y represents a saturated 4- to 7-membered monocyclic heterocyclyl selected from:
> morpholin-4-yl; 2-oxo-pyrrolidin-1-yl; 1,1-dioxidothiomorpholin-4-yl; or piperazin-1-yl optionally mono-substituted in position 4 with oxetan-3-yl or C1.3-alkyl;
> or azetidin-1-yl, pyrrolidin-1-yl, or piperidin-1-yl; wherein said azetidin-1-yl, pyrrolidin-1-yl, or piperidin-1-yl independently is unsubstituted, or substituted with:

■ two fluoro substituents attached to the same ring carbon atom; or
■ one substituent selected from unsubstituted phenyl, or unsubstituted 5-or6-membered heteroaryl; or
■ one substituent selected from hydroxy; C1.3-alkoxy; -CO-C1.4-alkoxy; di-(C1-3-alkyhamino; and C1-3-alkyl which is mono-substituted with di-(C1-3 alkyl)amino, hydroxy, or C1-3-alkoxy; or
■ two substituents, wherein one of said substituents is C1-4-alkyl, and the other is independently selected from hydroxy, or di-(C1-3-alkyrl)amino; or
■ one substituent selected from morpholin-4-yl; 1,1-dioxidothiomorpholin-4-yl; or piperazin-1-yl which is optionally mono-substituted in position 4 with C1-3-alkyl;
■ one substituent selected from azetidin-1-yl, pyrrolidin-1-yl, or piperidin-1-yl; wherein said groups independently are unsubstituted, or mono-substituted with hydroxy, ordii-substituted with methyl and hydroxy;
• or Y represents saturated 7- to 11-membered fused, bridged, or spiro-bicyclic
heterocyclyl containing at least one nitrogen atom, wherein said nitrogen atom is bound
to the benzoxazole / the benzothiazole moiety, and wherein said heterocyclyl optionally
contains one further ring heteroatom independently selected from oxygen, nitrogen and
sulfur; wherein said heterocyclyl is unsubstituted, or substituted with:
> two oxo substituents at a ring sulfur ring atom; or
> one C^-alkyl substituent attached to a ring nitrogen atom having a free valency;
or a pharmaceutical^ acceptable salt therof.



2. A compound according to claim 1, wherein the fragment
represents a group selected from:
wherein Ra represents hydrogen, or C-1-3-alkyl;
or a pharmaceutically acceptable salt therof.
3. A compound according to claim 1, wherein the fragment

or a pharmaceutically acceptable salt therof.
4. A compound according to any one of claims 1 to 3; wherein L represents -CO-NH-*,
wherein the asterisk (*) indicates the bond that is linked to the benzoxazole / the benzothiazole
moiety;
or a pharmaceutically acceptable salt therof.
5. A compound according to any one of claims 1 to 4; wherein X represents O; or a pharmaceutically acceptable salt therof.
6. A compound according to any one of claims 1 to 5; wherein Y represents a group -NR1R2, wherein
• R1 represents
> C1-4-alkyl;
> C2-4-alkyl which is mono-substituted with di-(C1-3-alkylamino;
> C3-5-cycloalkyl-L1-, wherein L1 represents a direct bond or C1.3-alkylene; and wherein the C3.5-cycloalkyl optionally contains one oxygen ring atom, and wherein said C3.5--cycloalkyl is unsubstituted, or mono-substituted with methyl or fluoro; or
> 1-(oxetan-3-yl)-piperidin-4-yl; and
• R2 represents hydrogen, C1-3-alkyl, or C3.5--cycloalkyl;


or Y represents a group
wherein
• r and q both represent the integer 2; and
Z represents O, SO2, or NRY1, wherein RY1 represents oxetan-3-yl or C1.3-alkyl; or
• r represents the integer 0,1,2, or 3; q represents the integer 1,2,3, or 4; and the sum of r
and q is 2, 3, or 4;
Z represents CH2, CHRY2, or CRY3RY4; wherein
> RY2 represents
■ unsubstituted phenyl, or unsubstituted 5- or 6-membered heteroaryl;
■ hydroxy; C1-3-alkoxy; -CO-C1--alkoxy; di(C1-3-alkyl)amino; or C1-3-alkyl which is mono-substituted with di-(C1-3-alkyl)amino, hydroxy, or C1.3-alkoxy;
■ morpholin-4-yl; 1,1-dioxidothiomorpholin-4-yl; or piperazin-1-yl which is optionally mono-substituted in position 4 with C1-3-alkyl; or
■ azetidin-1-yl, pyrrolidin-1-yl, or piperidin-1-yl; wherein said groups independently are unsubstituted, or mono-substituted with hydroxy, or di-substituted with methyl and hydroxy;
and
> RY3 represents C1.4-alkyl; and RY4 independently represents hydroxy, or di-(C1-3 alkyl)amino;
> or RY3 and RY4 both represent fluoro;
> or RY3 and RY4 together with the carbon atom to which they are attached to form

■ a 4- to 6-membered saturated carbocyclic ring; or
■ a 4- to 6-membered saturated heterocyclic ring, wherein said heterocyclic ring contains one ring heteroatom independently selected from oxygen, nitrogen and sulfur; and wherein said heterocyclic ring is unsubstituted, or substituted with:

■ two oxo substituents at a ring sulfur ring atom; or
■ one C1.3-alkyl substituent (especially methyl) attached to a ring nitrogen atom having a free valency;
or a pharmaceutically acceptable salt therof.

7. A compound according to any one of claims 1 to 5; wherein Y represents
• /V-C1-3--alkyl)amino, ./V./V-di-(C-1-3-alkyl)-amino, /V-[2-(di-C1.3-alkyl)amino)-ethyl]-/V-(C1.3-alkyl)-amino, /V-(C-1-4-alkyr)-/V-(oxetan-3-yr)-amino, /V-(C3.5-cycloalkyl)-A/-(oxetan-3-yl)-amino, /V-(C-1-4-alkyl)-/V-(oxetan-3-yl-methyr)-amino, /V--(3-methyl-oxetan-3-yr)-/V-methylamino, /V-(3-fluoro-oxetan-3-yl-methyl)-/V--methylamino, or /V--methyl-((/V-(oxetan-3-yl)-piperidin)-4-yl)-amino;
• or Y represents a saturated 4- to 7-membered monocyclic heterocyclyl selected from:

> morpholin-4-yl; 2-oxo-pyrrolidin-1-yl; 1,1-dioxidothiomorpholin-4-yl; or piperazin-1-yl optionally mono-substituted in position 4 with oxetan-3-yl or C13-alkyl;
> or azetidin-1-yl which is unsubstituted, or substituted with:

■ two fluoro substituents attached to the same ring carbon atom; or
■ one phenyl or pyridinyl substituent, wherein said phenyl or pyridinyl is unsubstituted; or
■ one substituent selected from hydroxy; C1.3-alkoxy; -CO-C1.4alkoxy; di-(C1.3-alkyl)amino; and C1.3-alkyl which is mono-substituted with di-(d-3-alkyl)amino, hydroxy, or C1.3-alkoxy; or
■ two substituents, wherein one of said substituents is C1.4-alkyl, and the other is independently selected from hydroxy, or di-(d-3-alkyl)amino; or
■ one substituent selected from morpholin-4-yl; 11-dioxidothiomorpholin-4-
yl;
■ one substituent selected from azetidin-1-yl, pyrrolidin-1-yl, or piperidin-1-
yl; wherein said groups independently are unsubstituted, or mono-
substituted with hydroxy, or di-substituted with methyl and hydroxy;
> or pyrrolidin-1-yl, or piperidin-1-yl; wherein said pyrrolidin-1-yl, or piperidin-1-yl
independently is unsubstituted, or substituted with:
■ two fluoro substituents attached to the same ring carbon atom; or
■ one substituent selected from hydroxy; C1.3-alkoxy; or di-(d-3-alkyl)amino;
• or Y represents saturated 7- to 11-membered spiro-bicyclic heterocyclyl containing at
least one nitrogen atom, wherein said nitrogen atom is bound to the benzoxazole / the
benzothiazole moiety, and wherein said heterocyclyl optionally contains one further ring
heteroatom independently selected from oxygen, nitrogen and sulfur; wherein said
heterocyclyl is unsubstituted, or substituted with:
> two oxo substituents at a ring sulfur ring atom; or
> one C1.3-alkyl substituent attached to a ring nitrogen atom having a free valency;
or a pharmaceutically acceptable salt therof.

8. A compound according to any one of claims 1 to 5; wherein Y represents a group independently selected from the following groups A), B), C), or D):

or a pharmaceutical^ acceptable salt therof.

9. A compound according to any one of claims 1 to 5; wherein Y represents a group independently selected from the following groups A), B), C), or D):

or a pharmaceutically acceptable salt therof.
10. A compound according to claim 1, which is selected from the group consisting of:
2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1,1-dioxo-1l6-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-piperidin-1-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acicid(2-morpholin-4-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic aciid(2-diethylamino-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3,3-difluoro-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3,3-difluoro-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-methoxy-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-hydroxy-3-methyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4-dimethylamino-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide;

2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-morpholin-4-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-cartoxylic acid{2-[methyl-(3-methyl-oxetan-3-yl)-amino]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid{2-[3-(1,1-dioxo-1l6-thiomorpholin-4-yl)-azetidin-1-yl]-benzooxazol-5-yl}-amide;
2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-hydroxy-3-methyl-[1,3']biazetidinyl-1 '-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1-oxa-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-6-aza-spiro[3.4]oct-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(6-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-5-aza-spiro[3.5]non-5-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1-oxa-8-aza-spiro[4.5]dec-8-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(7-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(5-oxa-2-aza-spiro[3.4]oct-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid{2-[3-(4-hydroxy-piperidin-1-yl)-azetidin-1-yl]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(6-methyl-2,6-diaza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(5-oxa-2-aza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide; 1-{5-[(2,3-Dihydro-benzofuran-5-carbonyl)-amino]-benzooxazol-2-yl}-azetidine-3-carboxylic acidtert-butyl ester; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxo-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid[2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide; 4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(1,1-dioxo-thiomorpholin-4-yl)-benzooxazol-5-yl]-amide;
(R)-N-(2-(3-hydroxypiperidin-1-yl)benzo[d]oxazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-((S)-3-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-isopropoxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-((R)-3-hydroxy-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-((S)-3-hydroxy-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-phenyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-ethoxymethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide;

2,3-Dihydro-benzofuran-5-carboxylic acid{2-[(3-fluoro-oxetan-3-ylmethyl)-methyl-amino]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4-oxetan-3-yl-piperazin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid{2-[methyl-(1-oxetan-3-yl-piperidin-4-yl)-amino]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(methyl-oxetan-3-ylmethyl-amino)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(methyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-methoxymethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-dimethylaminomethyl-pyrrolidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-phenyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-pyrrolidin-1-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid{2-[3-(1-hydroxy-1-methyl-ethyl)-azetidin-1-yl]-benzooxazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylic aciid [2-(3-dimethylaminomethyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(7-methyl-1,7-diaza-spiro[3.5]non-1 -yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(7-methyl-2,7-diaza-spiro[3.5]non-2-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-dimethylamino-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2,2-dioxo-2l6-thia-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1,1-dioxo-1l6-thia-6-aza-spiro[3.3]hept-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-dimethylamino-3-methyl-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(6-oxa-2-aza-spiro[3.4]oct-2-yl)-benzooxazol-5-yl]-amide; 2-(4-Methyl-piperazin-1-yl)-benzooxazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide; 2-Piperidin-1-yl-benzooxazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide; 2-Morpholin-4-yl-benzooxazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide; 2-Diethylamino-benzooxazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide; 2-Pyrrolidin-1-yl-benzooxazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide; 2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-piperidin-1-yl-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-morpholin-4-yl-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-pyrrolidin-1-yl-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-diethylamino-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-dimethylamino-benzothiazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3,3-difluoro-azetidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3,3-difluoro-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3,3-difluoro-piperidin-1-yl)-benzothiazol-5-yl]-amide;

2,3-Dihydro-benzofuran-5-carboxylic acid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(1,1 -dioxo-1 l6-thiomorpholin-4-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-methoxy-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4-methoxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-hydroxy-3-methyl-azetidin-1-yl)-benzothiazol-5-yl]-amide; (S)-N-(2-(3-hydroxypyrrolidin-1-yl)benzo[d]thiazol-5-yl)-2,3-dihydrobenzofuran-5-carboxamide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid{2-[methyl-(1-oxetan-3-yl-piperidin-4-yl)-amino]-benzothiazol-5-yl}-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(methyl-oxetan-3-yl-amino)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-methoxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-hydroxy-azetidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-phenyl-azetidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-((R)-3-hydroxy-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-methoxymethyl-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-((S)-3-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-oxa-6-aza-spiro[3.4]oct-6-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-((R)-3-hydroxy-piperidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(2-dimethylaminomethyl-pyrrolidin-1-yl)-benzothiazol-5-yl]-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-azetidin-1-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid(2-ethylamino-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzofuran-5-carboxylic acid [2-(3-pyridin-2-yl-azetidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid(2-piperidin-1-yl-benzooxazol-5-yl)-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide;

Benzo[1,3]dioxole-5-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid (2-morpholin-4-yl-benzooxazol-5-yl)-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide; Benzo[1,3]dioxole-5-carboxylic acid (2-diethylamino-benzooxazol-5-yl)-amide; Chroman-6-carboxylic acid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide; Chroman-6-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid(2-piperidin-1-yl-benzooxazol-5-yl)-amide; Chroman-6-carboxylic acid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid(2-morpholin-4-yl-benzooxazol-5-yl)-amide; Chroman-6-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide; Chroman-6-carboxylic acid(2-diethylamino-benzooxazol-5-yl)-amide; Chroman-6-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(3-hydroxy-azetidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid(2-pyrrolidin-1-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid(2-piperidin-1-yl-benzooxazol-5-yl)-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid[2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid[2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid[2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-amide; 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid (2-morpholin-4-yl-benzooxazol-5-yl)-amide;

2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid (2-diethylamino-benzooxazol-5-yl)-amide;
2,3-Dihydro-benzo[1,4]dioxine-6-carboxylicacid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(6-oxa-1-aza-spiro[3.4]oct-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylicacid [2-(7-oxa-1-aza-spiro[3.5]non-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(2-oxa-5-aza-spiro[3.4]oct-5-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid(2-piperidin-1-yl-benzooxazol-5-yl)-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(4-hydroxy-piperidin-1-yl)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(4,4-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(3,3-difluoro-piperidin-1-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(2-oxa-6-aza-spiro[3.5]non-6-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(2-oxa-7-aza-spiro[3.5]non-7-yl)-benzooxazol-5-yl]-
amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(4-methoxy-piperidin-1-yl)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid(2-morpholin-4-yl-benzooxazol-5-yl)-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(4-methyl-piperazin-1-yl)-benzooxazol-5-yl]-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid(2-diethylamino-benzooxazol-5-yl)-amide;
4-Methyl-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid [2-(cyclopropyl-oxetan-3-yl-amino)-benzooxazol-5-yl]-
amide;
2-Piperidin-1-yl-benzothiazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(6-oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(4-Methoxy-piperidin-1-yl)-benzothiazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(4-Methyl-piperazin-1-yl)-benzothiazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(6-Oxa-1-aza-spiro[3.4]oct-1-yl)-benzothiazole-5-carboxylic acid(2,3-dihydro-benzofuran-5-yl)-amide;
2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylic acid(2,3-dihydro-benzo[1,4]dioxin-6-yl)-amide;
2-(6-Oxa-1-aza-spiro[3.4]oct-1-yl)-benzothiazole-5-carboxylic acid(2,3-dihydro-benzo[1,4]dioxin-6-yl)-amide; and
2-(6-Oxa-1-aza-spiro[3.3]hept-1-yl)-benzothiazole-5-carboxylic acidbenzo[1,3]dioxol-5-ylamide;
or a pharmaceutically acceptable salt therof.

11. A pharmaceutical composition comprising, as active principle, one or more compounds according to any one of claims 1 to 10, or a pharmaceutically acceptable salt thereof, and at least one therapeutically inert excipient.
12. A compound according to any one of claims 1 to 10, or a pharmaceutically acceptable salt thereof, for use as a medicament.
13. A compound according to any one of claims 1 to 10, or a pharmaceutically acceptable salt thereof, for use in the prevention or treatment of a disease or disorder selected from a fibrotic disease; pulmonary hypertension; hypertension; asthma; acute respiratory distress syndrome; myocardial infarction; acute heart failure; cardiac and skeletal myopathy including Barth syndrome; stroke; traumatic brain injury; neuropathic pain; ataxia telangiectasia; ocular diseases; and cancer.
14. A compound according to any one of claims 1 to 10, or a pharmaceuticallly acceptable salt thereof, for use according to claim 13, wherein said fibrotic disease is pulmonary fibrosis; scleroderma; pancreatic fibrosis; liver fibrosis; chronic kidney disease; or cardiomyopathy.

15. Use of a compound according to any one of claims 1 to 10, or a pharmaceuticallly acceptable salt thereof, in the manufacture of a medicament for the prevention or treatment of a disease or disorder selected from a fibrotic disease; pulmonary hypertension; hypertension; asthma; acute respiratory distress syndrome; myocardial infarction; acute heart failure; cardiac and skeletal myopathy including Barth syndrome; stroke; traumatic brain injury; neuropathic pain; ataxia telangiectasia; ocular diseases; and cancer.
16.A method to prevent or treat a disease or disorder selected from a fibrotic disease; pulmonary hypertension; hypertension; asthma; acute respiratory distress syndrome; myocardial infarction; acute heart failure; cardiac and skeletal myopathy including Barth syndrome; stroke; traumatic brain injury; neuropathic pain; ataxia telangiectasia; ocular diseases; and cancer; comprising administering to a patient in need thereof, the compound of claim 1 or 10, in free or pharmaceuticallly acceptable salt form.
17.A method of inhibition of myofibroblast differentiation in a subject, comprising administering to said subject an effective amount of the compound of claim 1 or 10, in free or pharmaceuticallly acceptable salt form.