Abstract: The invention relates to antibacterial compounds formula (I) wherein R1 is the group M, whereby M is one of the groups MA and MB represented below wherein A is a bond or C≡C; R1A is H or halogen; R2A is H or halogen; R3A is H, alkoxy, hydroxyalkoxy, hydroxyalkyl, dihydroxyalkyl, 2-hydroxyacetamido, substituted cycloprop-1-yl or substituted oxetan-3-yl; and R1B is hydroxyalkyl, dihydroxyalkyl, aminoalkyl, dialkylaminoalkyl, substituted cycloprop-1-yl, substituted cyclobutan-1-yl, substituted oxetan-3-yl, 3-hydroxythietan-3-yl, substituted azetidin-3-yl, trans-(cis-3,4-dihydroxy)-cyclopent-1-yl, 3-hydroxymethylbicyclo[1,1,1]pentan-1-yl, 4-hydroxytetrahydro-2H-pyran-4-yl, (3R,6S)-3-aminotetrahydro-2H-pyran-6-yl, piperidin-4-yl or 1-(2-hydroxyacetyl)piperidin-4-yl; and salts thereof.
Claims
1. A compound of formula I
wherein
R1 is the group M, whereby M is one of the groups MA and MB represented below
wherein A represents a bond or C=C;
R1A is H or halogen;
R 2 A is H or halogen; and
R3A is H, (C C3)alkoxy, hydroxy(C2-C4)alkoxy, hydroxy(d-C4)alkyl, dihy droxy(C2-C4)alkyl, 2-hydroxyacetamido, 1 -hydroxymethyl-cycloprop- 1 -yl, /ra«s-2-hydroxymethyl-cycloprop-l-yl, 3-hydroxyoxetan-3-yl, 3-(hydroxy(Ci-C3)alkyl)oxetan-3-yl, 3-aminooxetan-3-yl or 1-aminocycloprop-l-yl;
and wherein R1B is hydroxy(Ci-C4)alkyl, dihydroxy(C2-C4)alkyl, amino(Ci-C4)alkyl, di(Ci-C4)alkylamino(Ci-C3)alkyl, 1-amino-cycloprop-l-yl, 1-hydroxymethyl-cycloprop-1 -yl, /ra«s-2-hydroxymethyl-cycloprop- 1 -yl, tra«5-2-aminomethyl-cycloprop- 1 -yl, /ra«5-2-hydroxymethyl-l-methyl-cycloprop-l-yl, /ra«s-2-hydroxymethyl-2-methyl-cycloprop-l-yl, c/5-l-fluoro-2-(hydroxymethyl)cycloprop-l-yl, cz's-2-fluoro- 2- (hydroxymethyl)cycloprop- 1 -yl, 2-( 1 ,2-dihydroxyethyl)-cycloprop- 1 -yl, 1 -(hydroxymethyl)-cyclobutan- 1 -yl, cis-3 -(hydroxymethyl)- 1 -hydroxy-cyclobutan- 1 -yl, 3-hydroxyoxetan-3-yl, 3-hydroxyoxetan-3-yl-(C1-C3)alkyl, 3-aminooxetan-3-yl,
3- hydroxymethyl-oxetan-3-yl, tra«5-(c/5-3,4-dihydroxy)-cyclopent-l-yl, 3 -hydroxymethylbicyclo[ 1,1, 1 ]pentan- 1 -yl, 4-hydroxytetrahydro-2H-pyran-4-yl, (3R,<5S)-3-aminotetrahydro-2H-pyran-6-yl, piperidin-4-yl, l-(2-hydroxyacetyl)piperidin- 4- yl, 3-hydroxythietan-3-yl, l-(2-hydroxyacetyl)azetidin-3-yl or l-glycylazetidin-3-yl; or a salt thereof.
2. A compound of formula I according to claim 1, wherein R1 is the group MA;
or a salt thereof.
3. A compound of formula I according to claim 2, wherein
A represents a bond or C≡C;
R1A is H or halogen;
R2A is H; and
R3A is (Ci-C3)alkoxy, hydroxy(C1-C4)alkyl, 1-hydroxymethyl-cycloprop-l-yl, 3-hydroxyoxetan-3-yl, or 3-aminooxetan-3-yl;
or a salt thereof.
4. A compound of formula I according to claim 2, wherein A represents a bond;
or a salt thereof.
5. A compound of formula I according to claim 4, wherein
R1A is H or halogen;
R2A is H; and
R3A is (Ci-C3)alkoxy;
or a salt thereof.
6. A compound of formula I according to claim 2, wherein A represents C≡C;
or a salt thereof.
7. A compound of formula I according to claim 6, wherein
R1A and R2A are both H; and
R3A is hydroxy(Ci-C4)alkyl, 1 -hydroxymethyl-cycloprop- 1-yl, 3-hydroxyoxetan-3-yl, or 3 -aminooxetan-3 -yl;
or a salt thereof.
8. A compound of formula I according to claim 1, wherein R1 is the group MB;
or a salt thereof.
9. A compound of formula I according to claim 8, wherein R1B is hydroxy(Ci-C4)alkyl, dihydroxy(C2-C4)alkyl, amino(Ci-C4)alkyl, di(Ci-C4)alkylamino(Ci-C3)alkyl, 1-amino-cycloprop-l-yl, 1 -hydroxymethyl-cycloprop- 1-yl, tra«s-2-hydroxymethyl-cycloprop-l-yl, /ra«5-2-hydroxymethyl- 1 -methyl-cycloprop- 1 -yl, cis- 1 -fluoro- 2- (hydroxymethyl)cycloprop-l-yl, c/5-2-fluoro-2-(hydroxymethyl)cycloprop-l-yl, 1 -(hydroxymethyl)-cyclobutan- 1 -yl, cis-3 -(hydroxymethyl)- 1 -hydroxy-cyclobutan- 1 -yl,
3- hydroxyoxetan-3-yl, 3-hydroxyoxetan-3-yl-(Ci-C3)alkyl, 3 -aminooxetan-3 -yl, 3-hydroxymethyl-oxetan-3-yl, tra«5-(c/5-3,4-dihydroxy)-cyclopent-l-yl,
4- hydroxytetrahydro-2H-pyran-4-yl, (3R,6S)-3-aminotetrahydro-2H-pyran-6-yl, piperidin-4-yl, or l-(2-hydroxyacetyl)piperidin-4-yl;
or a salt thereof.
10. A compound of formula I according to claim 9, wherein R1B is hydroxy(Ci-C4)alkyl, dihydroxy(C2-C4)alkyl, amino(Ci-C4)alkyl, 1-amino-cycloprop-l-yl, 1 -hydroxymethyl-cycloprop- 1 -yl, tra«s-2-hydroxymethyl-cycloprop- 1 -yl, tra«5-2-hydroxymethyl- 1 -methyl-cycloprop- 1-yl, c/5-l-fluoro-2-(hydroxymethyl)cycloprop-l-yl, cz's-2-fluoro-2-(hydroxymethyl)cycloprop- 1-yl, 3 -hydroxy oxetan-3 -yl, 3 -hydroxy oxetan-3 -yl-(Ci-C3)alkyl, 3-hydroxymethyl-oxetan-3-yl, or tra«s-(cz's-3,4-dihydroxy)-cyclopent-l-yl;
or a salt thereof.
11. A compound of formula I according to claim 1, wherein
R1 is the group MA, A represents a bond,
R1A is halogen,
R2A is H, and
R is (Ci-C3)alkoxy;
or R1 is the group MA, A represents C≡C,
R1A and R2A are both H, and
R3A is 1-hydroxymethyl-cycloprop-l-yl;
or R1 is the group MB and R1B is di(Ci-C4)alkylamino(Ci-C3)alkyl, l-(hydroxymethyl)-cyclobutan- 1 -yl, cis-3 -(hydroxymethyl)- 1 -hydroxy-cyclobutan- 1 -yl, 3 -aminooxetan-3 -yl, 4-hydroxytetrahydro-2H-pyran-4-yl, (3R,6S)-3-aminotetrahydro-2H-pyran-6-yl, piperidin-4-yl, or l-(2-hydroxyacetyl)piperidin-4-yl;
or a salt thereof.
12. A compound of formula I according to claim 1, wherein
A represents a bond or C≡C;
R1A is H or halogen;
R2A is H; and
R3A is (Ci-C3)alkoxy, hydroxy(Ci-C4)alkyl, 1-hydroxymethyl-cycloprop-l-yl, 3-hydroxyoxetan-3-yl, or 3 -aminooxetan-3 -yl;
and wherein R1B is hydroxy(Ci-C4)alkyl, dihydroxy(C2-C4)alkyl, amino(Ci-C4)alkyl, di(Ci-C4)alkylamino(Ci-C3)alkyl, 1-amino-cycloprop-l-yl, 1-hydroxymethyl-cycloprop-1 -yl, tra«5-2-hydroxymethyl-cycloprop- 1 -yl, tra«5-2-hydroxymethyl- 1 -methyl-cycloprop-1 -yl, cis- 1 -fluoro-2-(hydroxymethyl)cycloprop- 1 -yl, c/s-2-fluoro-2-(hydroxymethyl)cycloprop- 1 -yl, 1 -(hydroxymethyl)-cyclobutan- 1 -yl, cis-3 -(hydroxymethyl)- 1 -hydroxy-cyclobutan- 1 -yl, 3 -hydroxy oxetan-3 -yl,
3-hydroxyoxetan-3-yl-(Ci-C3)alkyl, 3 -aminooxetan-3 -yl, 3-hydroxymethyl-oxetan-3-yl, trans-{cis-3 ,4-dihydroxy)-cyclopent- 1 -yl, 4-hydroxytetrahydro-2H-pyran-4-yl, (3R,6S)-3-aminotetrahydro-2H-pyran-6-yl, piperidin-4-yl, or l-(2-hydroxyacetyl)piperidin-4-yl;
or a salt thereof.
13. A compound of formula I according to claim 1, which is selected from the group consisting of:
(R)-N-hydroxy-4-(6-((3-hydroxyoxetan-3-yl)buta-l,3-diyn-l-yl)benzo[
| # | Name | Date |
|---|---|---|
| 1 | Translated Copy of Priority Document [14-06-2017(online)].pdf | 2017-06-14 |
| 2 | PROOF OF RIGHT [14-06-2017(online)].pdf | 2017-06-14 |
| 3 | Priority Document [14-06-2017(online)].pdf | 2017-06-14 |
| 4 | Power of Attorney [14-06-2017(online)].pdf | 2017-06-14 |
| 5 | Form 5 [14-06-2017(online)].pdf | 2017-06-14 |
| 6 | Form 3 [14-06-2017(online)].pdf | 2017-06-14 |
| 7 | Form 1 [14-06-2017(online)].pdf | 2017-06-14 |
| 8 | Description(Complete) [14-06-2017(online)].pdf_27.pdf | 2017-06-14 |
| 9 | Description(Complete) [14-06-2017(online)].pdf | 2017-06-14 |
| 10 | CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [14-06-2017(online)].pdf | 2017-06-14 |
| 11 | Correspondence by Agent_Form1_19-06-2017.pdf | 2017-06-19 |
| 12 | 201747020711-FORM 3 [11-09-2017(online)].pdf | 2017-09-11 |
| 13 | 201747020711-PA [15-11-2017(online)].pdf | 2017-11-15 |
| 14 | 201747020711-ASSIGNMENT DOCUMENTS [15-11-2017(online)].pdf | 2017-11-15 |
| 15 | 201747020711-8(i)-Substitution-Change Of Applicant - Form 6 [15-11-2017(online)].pdf | 2017-11-15 |
| 16 | 201747020711-FORM 3 [30-11-2017(online)].pdf | 2017-11-30 |
| 17 | 201747020711-FORM 3 [17-03-2018(online)].pdf | 2018-03-17 |
| 18 | 201747020711-FORM 3 [31-08-2018(online)].pdf | 2018-08-31 |
| 19 | 201747020711-FORM 18 [16-11-2018(online)].pdf | 2018-11-16 |
| 20 | 201747020711-FORM 3 [19-02-2019(online)].pdf | 2019-02-19 |
| 21 | 201747020711-FER.pdf | 2020-01-29 |
| 1 | 2020-01-1311-25-33_13-01-2020.pdf |