Abstract: Described are novel compounds of the formula (I), their derivatives, analogs,tautomeric forms,regioisomers,stereoisomers,polymorphs, solvates,intermediates,pharmaceutically acceptable salts, pharmaceutical compositions, metabolites and prodrugs thereof. These compounds are effective in lowering blood glucose,serum insulin,free fatty acids, cholesterol, triglyceride levels; treatment of obesity, inflammation, autoimmune diseases such as multiple sclerosis, rheumatoid arthritis; treatment and/or prophylaxis of type II diabetes. These compounds are more particularly dipeptidyl peptidase (DPP IV) inhibitors.
We Claim:
1, Compound of formula (I),
their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, intermediates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites and prodrugs thereof; wherein Y represents -0-, -S(0)p-, -CH2-» -CHOH-, -CHF- or -CF2-; m, n and p are integers independently selected from 0, 1, or 2; X represents a bond, C1-C5 aIkyleneor-C(=0)-;
R1 represents hydrogen, optionally substituted groups selected from alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heterocyciyl, heterocycloalkyl, heterocyclylalkyi, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, -N3, -S(O)pRi0, -NR10S(O)pRn, -CN, -COOR10, -CONR10Rn, -OR10, -NR,0RU or~NRl0CORu or a group selected from:
wherein R12 represents hydrogen or substituted or unsubstituted groups selected from alkyl, alkoxy, acyl, hydroxylalkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, aryl, arylalkyl, heteroaryl, heterocyclic ring, heterocycloalkyl heterocyclylalkyi, heteroarylalkyl, carboxylic acid or carboxylic acid derivatives selected from esters, amides, acid halides, hydroxamic acid and hydroxamates;
R2, R3 and R4 independently represents hydrogen, hydroxy, halogen, alkyl, haloalkyl, cyano, hydroxyalkyl, alkoxy, alkylsulfonyl, alkylthio, phenyl-S(0)p-alkyl, amino, -NRloRn or phenylalkyl, wherein said phenyl is optionally substituted independently with one or more alkyl, cycloalkyl, alkoxy, cyano, halogen, alkylsulfonyl, alkylthio, -CC^alkyl, -COOH, -CONH2, -CHO, -CH2OH, hydroxy!, haloalkyl, amino, nitro or R2 and R4 can be combined together to form an optionally substituted 4-10 membered ring having 0-4 hetero atoms selected from N, O and S;
R5 represents hydrogen or optionally substituted alkyl group;
R6 represents hydrogen or optionally substituted groups selected from alkyl, alkoxyalkyl,
hydroxyalkyl, amino, R^alkyl and R^C(NH)NHalkyl;
R and R independently represents hydrogen, alkyl or hydroxyl;
R8 is hydrogen, cyano, COOH, or an isosterate of a carboxylic acid comprising SO3H, B(OH)2, PO3R10Rn, SO2NR10Rn, tetrazole, -COOR10, *CONR10RM, -NR10CORU and -COOCOR10;
R10 and Ru independently represents hydrogen, nitro, hydroxy, cyano, formyl, acetyl, halogen or optionally substituted groups selected from amino, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl cycloalkylalkyl, cycloalkenyl, aryl, arylalkyl, heteroaryl, heterocyclyl, heterocycloalkyl, heterocyclylalkyl, heteroarylalkyl or a carboxylic acid or carboxylic acid derivatives selected from esters, amides, acid halides, hydroxamic acid and hydroxamates;
when the groups R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are substituted or when the term "substituted" is used, the substituents are one or more and are selected from halogens, hydroxy, nitro, cyano, azido, nitroso, oxo (=0), thioxo (=S), thioalkyl, amino, hydrazino, formyl, alkyl, haloalkyl group, alkoxy, haloalkoxy, arylalkoxy, cycloalkyl, cycloalkyloxy, aryl, heterocycloalkyl, heteroaryl, alkylamino, tolyl, -COORa, -C(0)Ra, -C(S)Ra, -C(0)NRaRb, -C(S)NRaRb, -NR^^NR^0, -NRaC(S)NRbRc, -N(Ra)SORb, -N(RB)S02R\ -NR8C(0)ORb, -NRflRb, -NRaC(0)Rb, -NRflC(S)Rb, -SONRaRb, -S02NRaRb, -ORfl, -0R8C(0)0Rb, -OC(0)NRaRb, -OC(0)Ra, -R'NR1^, -RflORb, -SRa, -SORa and -S02Ra; the substituents are further optionally substituted by one or more substituents as defined above;
wherein Ra, Rb and Rc independently represents hydrogen or substituted or unsubstituted groups selected from alkyl, alkylene, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, cycloalkyl and cylcoalkenyl; or RB and Rb can be combined together to form a ring structures having 4-8 atoms.
2. The compound according to claim 1, wherein: when alkoxy group is present, the alkoxy group is selected from methoxy, ethoxy, n-propoxy, isopropoxy, n»butoxy, isobutoxy and t-butoxy; when aryloxy group is present, the aryloxy group is selected from phenoxy and naphthyloxy; when halogen is present, the halogen is fluorine, chlorine, bromine or iodine; when alkyl group is present, the alkyl group is methyl, ethyl, n-propyl, isopropyl, butyl,isobutyl, /-butyl, pentyl, hexyl, heptyl or octyl; when alkenyl group is present, the alkenyl group is ethenyl, 1-propenyl, 2-propenyl, iso-propenyl, 2-methyl-l-propenyl, 1-butenyl or 2-butenyl; when the alkynyl group is present, the alkynyl group is ethynyl, propynyl or butynyl; when cycloalkyl group is present, the cycloalkyl group is cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclooctyl, cycloheptyl, perhydronaphthyl, adamantyl, bridged cyclic groups or spirobicyclic groups; when cycloalkenyl group is present, the cycloalkenyl group is selected from cyclopentenyl and cyclohexenyl; when heterocycloalkyl or heteroaryl group is present, the heterocycloalkyl or heteroaryl group is a heterocyclyl group selected from azetidinyl, acridinyl, benzodioxolyl, benzodioxanyl, benzofuranyl, carbazolyl, cinnolinyl, dioxolanyl, indolizinyl, naphthyridinyl, perhydroazepinyl, phenazinyl,phenothiazinyl, phenoxazinyl, phthalazinyl, pyridyl, pteridinyl, purinyl, quinazolinyl,quinoxalinyl, quinolinyl, isoquinolinyl, tetrazolyl, imidazolyl, tetrahydroisoquinolinyl, 2-oxoazepinyl, azepinyl, pyrrolyl, piperonyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrazolyl,oxazolyl, oxazolinyl, triazolyl, indanyl, isoxazolyl, isoxazolidinyl, thiazolyl, thiazolinyl,
thiazolidinyl, thienyl, isothiazolyl, quinuclidinyl, isothiazolidinyl, indolyl, isoindolyl,indolinyl, isoindolinyl, octahydroindolyl, octahydroisoindolyl, decahydroisoquinolyl,benzimidazolyl, thiadiazolyl, benzopyranyl, benzothiazolyl, benzothiadiazolyl,benzoxadiazolyl, benzotriazolyl, benzothienyl, benzoxazolyl, oxadiazolyl, benzindazolyl,indazolyl, phenylpiperidinyl, furyl, tetrahydrofuryl, tetrahydropyranyl, piperazinyl,homopiperazinyl, piperidyl, piperidopiperidyl, morpholinyl, thiomorpholinyl, piperidonyl, 2-oxopiperazinyl, 2-oxopiperidinyI, pyrrolidinyl, 2-oxopyrrolidinyl, oxazolidinyl, chromanyl, isochromanyl,oxabicyclo[3.2.1]octane,3-oxabicyclo[3.2.1]octanone,3-azabicyclo[3.2.1]octane-2,4-dione and 3-azabicyclo[3.2.1]octaoe; when aryl group is present,the aryl group is phenyl, naphthyl, anthracenyl, indanyl or biphenyl; when alkylene group is present, the alkylene group is methylene, ethylene, propylene or butylene; when hydroxyalkyl group is present, the hydroxyalkyl group is hydroxymethyl or hydroxyethyl; when haloalkyl group is present, the haloalkyl group is trifluoromethyl, tribromomethyl or trichloromethyl;when haloalkoxy group is present, the haloalkoxy group is selected from chloromethoxy,chloroethoxy, trifluoromethoxy, trifluoroethoxy and trichloromethoxy; when
heterocyclylalkyl group is present, the heterocyclylalkyl group is selected from
oxadiazolylmethyl,triazolylmethyl,tetrazolylmethyl,morpholinylmethyl,pyrrolidinylmethyl, piperidinylmethy 1,1,2-thiazinane 1 ,1 -dioxide-ylmethyl and isothiazolidine 1,1 -dioxide-ylmethyl; when heteroarylalkenyl group is present, the heteroarylalkenyl group is selected from pyridinylethenyl,thienylethenyl and triazolylethenyl; and when heteroarylalkynyl group is present, the heteroarylalkynyl group is
selected from pyridinylethynyl, thienylethynyl and triazolylethynyl.
3. A compound of formula (I), as claimed in claim 1, which is selected from:
1. (2S,4S)-l-(2-((lR,3S)-3-((lH-l,2,4-TriazoM-yl)methyl)-l,2,2-
trimethylcyclopentylamino)acetyl)-4-fluoropyrrolidine-2-carbonitrile;
2. (2S,4R)-l-(2-((lR,3S)-3-((lH-l,2J4-Triazol-l-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)-4-fluoropyrrolidine-2-carbonitrile methanesulfonate;
3. (2S,4S)-l-(2-((lS,3R)-3-((lH-l,2,4-Triazol-l-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)-4-fluoropyrrolidine-2-carbonitrile;
4. (2S,4S)-l-(2-((lS,3R)-3-((lH-l,2,4-Triazol-l-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)-4-fluoropyrrolidine-2-carbonitrile methanesulfonate;
5. (2S,4R)-l-(2-((lS)3R)-3-((lH-l12]4-Triazol-l-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)-4-fluoropyrroIidine-2-carbonitrile methanesulfonate;
6. (S)-l-(2-((lS,3R)-3-((lH-l,2,4-Triazol-l-yl)methyl)-l)2,2-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
7. (S)-l-(2-((lS,3R)-3-((lH-l,2,4-Triazol-l-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile methanesulfonate;
8. (S)-l-(2-((lR,3S)-3-((lH-l,2,4-Triazol-l-yI)methyl)-lJ2,2-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
9. (S)-l-(2-((1R,3S-H-l^-Triazol-l-yl)methyl)-1,2,2-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile methanesulfonate;
10. (2S,4S)-l-(2-((lR,3S)-3-((2H-l,2,3-Triazol-2-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyI)-4-fluoropyrrolidine-2-carbonitrile;
11. (2S)4S)-l-(2-((lR,3S)-3-((lH-l,2,3-TriazoI-l-yl)methyl)-l)2)2-
trimethylcyclopentylamino)acetyl)-4-fluoropyrrolidine-2-carbonitrile;
12. (2S,4S)-l-(2-((lS,3R)-3-((2H-l,2,3-TriazoI-2-yl)methyl)-lJ2t2-trimethylcyclopentylamino)acetyl)-4-fluoropyrrolidine-2-carbonitrile;
13. (2SJ4S)-l-(2-((lS,3R)-3-((lH-l,2,3-Triazol-l-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)-4-fluoropyrrolidine-2-carbonitrile methanesulfonate;
14. (2S,4S)-4-Fluoro-l-(2-((lR)3S)-l,2,2-trimethyl-3-(piperidine-l-carbonyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
15. (2S,4S)-4-Fluoro-I-(2-((lR,3S)-3-((4-(hydroxymethyl)-lH-l,2,3«triazol-l-yl)methyl)-l,2,24rimethylcyclopentylamino)acetyl)pyrroHdine-2-carbonilrile;
16. (2S,4S)-4-Fluoro-l-(2-((lS33R)-3-((4-(hydroxymethyl)-lH-l,2,3-triazol-l-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyI)pyrroIidine-2-carbonitrile;
17. N-(((lS,3R)-3-(2-((2S,4S)-2-Cyano-4-fluoropyrrolidin-l-yl)-2-oxoethylamino)-2s2,3-trimethylcycIopentyl)methyl)methanesulfonamide;
18. N-(((lR,3S)-3-(2-((2S,4S)-2-Cyano-4-fluoropyrTolidin-l-yl)-2-oxoethylamino)-2,2,3-trimethylcyclopentyl)methyl)methanesulfonamide;
19. N-(((lS,3R)-3-(2-((2S,4S)-2-Cyano-4-fluoropyrrolidin-l-yl)-2-oxoethylamino)-2,2,3-trimethylcyclopentyl)methyl)-4-fluorobenzenesulfonamide;
20. N-(((lR,3S)-3-(2-((2S,4S)-2-Cyano-4-fluoropyrrolidin-l-yl)-2-oxoethylamino)-2,2,3-trimethylcyclopentyl)methyl)-4-fluorobenzenesulfonamide;
21. N-(((lS,3R)-3-(2-((2S)4S)-2-Cyano-4.fluoropyrrolidin-l-yl)-2-oxoethylamino)-2,2,3-trimethylcyclopentyl)methyl)-2-fluorobenzamide;
22. N-(((lSJ3R)-3-(2-((2S,4S)-2-Cyano-4-fluoropyrrolidin-l-yl).2-oxoethylamino)-2J2)3-trimethylcyclopentyl)methyl)-4,4-difluorocyclohexanecarboxamide;
23. N-(((lR(3S)-3-(2-((2S,4S)-2-Cyano-4-fluoropyrrolidin-l-yl)-2-oxoethylamino)-2,2,3-trimethylcyclopentyl)methyl)-4,4-difluorocycIohexanecarboxamide;
24. 6<((lS(3R)-3-(2-((2SJ4S)-2-Cyano-4-fluoropyrroltdin-l-yl)-2-oxoethylammo)-2,2,3-trimethylcyclopentyl)methylamino)nicotinonitrile;
25. 6-(((lR,3S)-3-(2-((2S,4S)-2-Cyano-4-fluoropyrrolidin-l-yl)-2-oxoethylamino)-2)2J3-trimethylcyclopentyl)methylamino)nicotinonitrile;
26. 2-(((lS,3R)-3-(2-((2S,4S)-2-Cyano-4-fluoropynx)Hdiii-l-yl)-2-oxoethyIamino)-2,2J3-trimethylcyclopentyl)methylamino)nicotinonitrile;
27. (2S,4S)-4-FIuoro-l-(2-((lR,3S)-l,2,2-trimethyl-3-((5-(trifluoromethyI)pyridin-2-ylamino)methyl)cyclopentylamino)acetyl)pyrroliditte-2-carbonitrile;
28. (2St4S)-l-(2-((lR,3S)-3-t(l)l-Dioxidoisothiazolidin-2-yl)methyl]-l,2,2-trimethylcyclopentylamino)acetyl)-4-fluoropyrroIidine-2-carbonitrile;
29. (2S,4S)-l-(2-((lS,3R)-3-[(l,l-Dioxidoisothiazolidin-2-yl)methyl]-lt2,2-trimethylcyclopentylamino)acetyl)-4-fluoropyrroIidine-2-carbonitrile;
30. (2SJ4S)-l-(2-((lS,3R)-3-[(l!l-Dioxido-l,2-thiazinan-2-yl)methyl]-l,2(2-trimethylcyclopentylamino)acetyl)-4-fluoropyrrolidine-2-carbonitrile;
31. (2S,4S)-1,2-((lR,3S)-3-((lH-Tetrazol-l-yI)methyl)-l,2>2-trimethylcyclopentyI
amino)acetyl)-4-fluoropyrrolidine-2-carbonitrilemethanesulfonate;
32. (2S,4S)-l-(2.((lS53R)-3-((lH-TetrazoI-l-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)-4-fluoropyn,olidine-2-carbonitrile;.
33. (2S,4S)-4-Fluoro-l-(2-((lR,3S)-l,2,24rimethyl-3-(morpholinomethyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitriIe;
34. (2S,4S)-4-Fluoro-l-(2-((lS,3R)-l)2J2-trimethyl-3-(morpholinomethyI)cyclopentylamino)acetyl)pyrroIidine-2-carbonitrile;
35. (2SJ4S)-4-Fluoro4-(2-((lS)3R)-l,2,2-trimethyl-3-(morpholinomethyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitriledimethanesulfonate;
36. (2S,4S)-4-Fluoro-l-(2-((lR)3S)-l,2,2-trimethyl-3-(pyrrolidin-l-ylmethyl)cyclo pentylamino)acetyl)pyrrolidine-2-carbonitrile;
37. (2SJ4S)-4-Fluoro-l-(2-((lSJ3R)-lJ2)2-trimethyl-3-(pyrroIidin-l-ylmethyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
38. (2S,4SH-Fluoro-l-(2-((lRJ3S)-3-(((R)-3-hydroxypym)lidin-l-yl)methyl)-l- trimethylcyclopentylamino)acetyl)pyiTolidine-2-carbonitrile;
39. (2S,4S)-4-Fluoro-l-(2-((lR(3S)-l,2,2-trimethyI-3-(piperidin-l-ylmethyl)cycIopentylamino)acetyl)pyrrolidine-2-carbonitrile;
40. (2S,4S)-4-Fluoro-l-(2-((lS,3R)-lJ212-trimethyl-3-(piperidin-l-ylmethyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
41. (2S,4S)-Fluoro-l-(2-((lR,3S)-3K(4-hydroxypiperidin-l-yI)methyl)-lJ2-2-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
42. (2S,4S)-4-Fluoro-l-(2-((lR,3S)-l,2,2-trimethyl-3-((4-(methylsulfonyl)phenylsulfonyl)methyl)cyclopentylamino)acetyl)pyrroiidine-2-carbonitrile;
43. (2S,4R)-4-Fluoro-l-(2-((lR,3S)*lJ2)2-trimethyl-3-((4-(methylsulfonyl)phenylsulfonyl)methyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
44. (S)-l-(2-((lR,3S)-l52,2-TrimethyI-3-((4-(methylsulfonyI)phenylsulfonyl)methyI)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
45. (2S,4S)-4-Fluoro-l-(2«lS,3R)-l,2,2-trimethyl-3-((4-(methylsulfonyl)phenylsulfonyl)methyl)cyclopentylamino)acetyl)pyrroHdine-2-carbonitrile;
46. (S)-1 -(2-((l S,3R)» 1 ,2,2-Trimethyl-3-((4-(methylsulfonyl) phenylsulfonyl)methyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
47. (2St4R)-4-F]uoro-l-(2-((lS,3R)-l12,2-trimethyl-3-((4-(methylsulfonyl)phenylsulfonyl)methyl)cyclopentyIamino)acetyl)pyrrolidine-2-carbonitrile;
48. (2S,4S)-4-Fluoro-l-(2-((lR(3S)-3-(3-(4-fluorophenyl)-l,2,4-oxadiazol-5-yl)-i,2,2-trimethylcyclopentyIamino)acetyl)pyrrolidine-2-carbonitrile;
49. (2S,4S)-4-Fluoro-l-(2-((lSJ3R)-3-(3-(4-fluorophenyl)-l)2J4-Oxadiazol-5-yl)-l,2,2-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
50. (2S,4S)-4-Fluoro-l-(2-((lR,3S)-l,2)2-trimethyl-3-(3-methyl-l,2,4-oxadiazoI-5-yl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
51. (2S,4S)-4-FIuoro-l-(2-((lSJ3R)-l)2,2-trimethyl-3-(3-methyl-l)2J4-oxadiazol-5-yl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
52. (2S,4S)-4-Fluoro-l-(2-((lR,3S)-3-(3-isopropyI-lJ2J4-oxadiazol-5.yl)-l,2,2-trimethylcyclopentylamino)acetyl)pyrroIidine-2-carbonitrile;
53. (2S)4S)-l-(2-((lR»3R)-3-(Cyanomethyl)-l)2t2-trimethylcyclopentyl amino)acetyl)-4-fluoropyrrolidine-2-carbonitrile;
54. (2S,4S)*4-Fluoro-l-(2-((lRJ3R)-l,2,2-trimethyl-3-((5-metiiyI-l)2)4-oxadiazol-3-yl)methyl)cyclopentylamino)8cetyl)pyrrolidine-2-carbonitriIe;
55. (2S,4S)-4-Fluoro-l-(2-((lS,3S)-l,2,2-trimethyl-3-((5-methyl-l,2)4-oxadiazoi-3-yl)methyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
56. (2S,4S)^4-Fluoro-l-(2-((lS)3S)-l)2)2-trimethyl-3-((5-(trifluoromethyl)-lJ2)4-oxadiazol-3-yl)methyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
57. (2S,4S)-4-Fluoro-l-(2-((lSJ3S)-lJ2)2-trimethyl-3-((5Ktrifluoromethyl)-lJ2)4-oxadiazol-3-yl)methyI)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile methanesulfonate;
58. (2SJ4S)-l-(2-((lS,3S)^3-((5-/e«-Butyl-l,2>4-oxadiazol-3-yI)methyl)-l,2,2-trimethylcyclopentyIamJno)acetyl)-4-fluoropyrrolidine-2-carbonitrile;
59. (2S,4S)-l-(2-((lS,3S)-3-((5.Cyclohexyl-l(2s4-oxadiazoN3-yl)methyl)-l,2,2-trimethylcycIopentylamino)acetyl)-4-fluoropyrroIidine-2-carbonitrile;
60. (2S,4S)^-F]uoro-K2-aiS,3S)-3™((5-(hydroxymethyl)-lJ2)4-oxadiazol-3-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
61. (2SJ4S)-4-Fluoro-l-(2-((lS,3S)-3-((5-isopropyl-l,2J4-oxadiazol-3-yl)methyl)-l,2J2-
trimethylcyclopentylamino)acetyl)pyrroIidine-2-carbonitrile methanesulfonate;
62. (2S,4S)-4-Fluoro-l-(2-((lSJ3S)-3-((5-(4-fluorophenyl)-l»2,4-oxadia2ol-3-yl)methyl)-l,2,2-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
63. (2S,4S)-4-Fluoro-l-(2-((lS,3S)-l)2)2-trimethyI-3-((5-(pyridin-4*yl)-l,2,4-oxadiazoI-3-yl)methyl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
64. (2S,4S)-4-Fluoro-l-(2-((lR,3S)-3-(3-(4-fluorophenyl)-l,2,4-oxadiazol-5-yl)-2t2,3-trimethylcyclopentylamino)acetyl)pyrroIidine-2-carbonttrile
65. (2SJ4S)-4-Fluoro-l-(2*((lS,3R)-3-(3-(4-fluorophenyl)4,2,4-oxadiazol-5-yl)-2,2,3-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
66. (S)-l-(2-((lS,3R)-3-(3-(4-Fluorophenyl)-l,2,4-oxadiazol-5-yl)-2J2,3-
trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrilemethane$ulfonate;
67. (2S,4S)-4-Fluoro-l-(2-((lS,3R)-3-(3-isopropy]-l,2,4-oxadiazol-5-yl)-2,2,3-trimethylcyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
68. (2S,4S)-4-Fluoro-l-(2-((lSJ3R)-2,2,3-trimethyl-3-(3-(pyridin-3-yl)-l,2,4-oxadiazol-5-yl)cyclopentylamino)acety|)pyrrolidine-2-carbonitrile;
69. (2SJ4S)-4-FIuoro-l-(2-((lR>3S)-2,2,3-lT!methyl-3-(3-(pyridin-3-yl)-l>2(4-oxadiazol-5-yI)cyclopentylamino)acetyl)pyrrolidine-2-oarbonitrile;
70. (2S,4S)-4-Fluoro-l-(2-((lS,3R)-2t2)3-trimethyl-3-(3-(pyridin-4-yl)-l>2J4-oxadiazol-5-yl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitriIe;
71. (2SJ4S)-4-FIuoro-l-(2-((lR,3S)-2,2,3-trimethyl-3-(3-(pyridin-4-yl)-l,2,4-oxadiazol-S-yOcyclopentylaminoJacetyOpyiTolidine^-carbonitrile;
72. (2SJ4S)-4-Fluoro-l-(2-((lS,3R)-2,2J3-trimetbyl-3-(3-(pyrazin-2-yl)-l,2,4-oxadiazol-5-yl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
73. (2S,4S)-4-Fluoro-l-(2-((lR)3S)-2J2,3-trimethyl-3-(3-methyl-l,2,4-oxadiazol-5-yl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
74. (2S,4S)-4-Fluoro-l-(2-((lS,3R)-2,2(3-trimethyl-3-(3-methyl-l>2,4-oxadiazol-5-yl)cyclopentylamino)acetyl)pyrrolidine-2-carbonitrile;
75. (S)-l-(2-((lR,5R)-3,5J8,8-Tetramethyl-2J4-dioxo-3-azabicyclo[3.2.1]octan-l-
ylamino)acetyl)pyrrolidine-2-carbonitrile;
76. (2S,4S)-4-Fluoro-l-(2-((lR,5R)-3,5,8,8-tetramethyl-3-azabicyclo[3.2.1]octan-l-ylamino)acetyl)pyrroUdine-2-carbonitrile;
77. (2S,4R)-4-Fluoro-l-(2-((lR,5R)-3,5,8,8-tetramethyl-3-azabicyclo[3.2.1]octan-l-ylamino)acetyl)pyrroIidine-2-carbonitrile;
78. (S)-1-(2-((1R,5R)-3,5,8,8-Tetramethyl-S-azabicyclotS^.lloctan-l-
ylamino)acetyl)pyrrolidine-2-carbonitrile;
79. (S)-l-(2-((lR,5R)-5,8)8-Trimethyl-2-oxo-3-oxabicyclo[3.2.1]octan-l-ylamino)acetyl)pyrrolidine-2-carbonitrile;
80. (S)-l-(2-((lR,5R)-5J8t8-Trimethyl-3-oxabicyclo[3.2.1]octan-l-yIamino)acetyl)pyrrolidine-2-carbonitrile;
81. (2S,4S)-4-Fluoro-l-(2-((lR,5R)-5,8,8-trimethyl-3-oxabicyclo[3,2fl]octan-l-ylamino)acetyl)pyrrolidine-2-carbonitrile;
82. (2S,4S)-4-FIuoro-l-(2-((lS,5S)-5)8,8-trimethyl-3-oxabicyclo[3.2.1]octan-l-ylamino)acetyl)pyrroIidine-2-carbonitrile;and
83. (2SJ4S)-l-(2"((lS,3R)-3-(3-(lH-l)2,4-TriazoM-yl)propyl)-2)2t3-trimethylcyclopen
| Section | Controller | Decision Date |
|---|---|---|
| # | Name | Date |
|---|---|---|
| 1 | 65-che-2009 form-5 07-01-2010.pdf | 2010-01-07 |
| 1 | 65-CHE-2009-Correspondence_06-03-2020.pdf | 2020-03-06 |
| 2 | 65-CHE-2009-Form27_License_06-03-2020.pdf | 2020-03-06 |
| 2 | 65-CHE-2009 FORM-2 07-01-2010.pdf | 2010-01-07 |
| 3 | Correspondence by Applicant_Form27_22-02-2019.pdf | 2019-02-22 |
| 3 | 65-che-2009 description(complete) 07-01-2010.pdf | 2010-01-07 |
| 4 | Form27_Working of the Patented Invention_22-02-2019.pdf | 2019-02-22 |
| 4 | 65-che-2009 correspondence others 07-01-2010.pdf | 2010-01-07 |
| 5 | Correspondence by Applicant_Renewal Fees_31-12-2018.pdf | 2018-12-31 |
| 5 | 65-che-2009 claims 07-01-2010.pdf | 2010-01-07 |
| 6 | Correspondence by Applicant_Form27_16-02-2018.pdf | 2018-02-16 |
| 6 | 65-che-2009 abstract 07-01-2010.pdf | 2010-01-07 |
| 7 | Form27_License_16-02-2018.pdf | 2018-02-16 |
| 7 | 65-CHE-2009 FORM-3 18-01-2010.pdf | 2010-01-18 |
| 8 | Correspondence by Applicant_Renewal fee_04-01-2018.pdf | 2018-01-04 |
| 8 | 65-CHE-2009 FORM-18 08-07-2010.pdf | 2010-07-08 |
| 9 | Correspondence by Applicant_Form27_22-03-2017.pdf | 2017-03-22 |
| 9 | 65-che-2009 form-3 06-09-2010.pdf | 2010-09-06 |
| 10 | 0065-che-2009 form-1.pdf | 2011-09-02 |
| 10 | Form27_License_22-03-2017.pdf | 2017-03-22 |
| 11 | 0065-che-2009 description(provisional).pdf | 2011-09-02 |
| 11 | Correspondence by Applicant_Renewal fee_29-12-2016.pdf | 2016-12-29 |
| 12 | 0065-che-2009 correspondence-others.pdf | 2011-09-02 |
| 12 | 65-CHE-2009_EXAMREPORT.pdf | 2016-07-02 |
| 13 | 0065-che-2009 abstract.pdf | 2011-09-02 |
| 13 | 65-CHE-2009-Abstract-300915.pdf | 2015-10-05 |
| 14 | 65-CHE-2009 FORM-3 12-10-2011.pdf | 2011-10-12 |
| 14 | 65-CHE-2009-Claims-300915.pdf | 2015-10-05 |
| 15 | 65-CHE-2009 CORRESPONDENCE OTHERS 12-10-2011.pdf | 2011-10-12 |
| 15 | 65-CHE-2009-Correspondence-300915.pdf | 2015-10-05 |
| 16 | 65-CHE-2009 FORM-3 27-03-2012.pdf | 2012-03-27 |
| 16 | 65-CHE-2009-Correspondence-090915.pdf | 2015-09-11 |
| 17 | 65-CHE-2009 FORM-6 05-10-2012.pdf | 2012-10-05 |
| 17 | 65-CHE-2009-Form 3-090915.pdf | 2015-09-11 |
| 18 | 65-CHE-2009 AMENDED PAGES OF SPECIFICATION 30-04-2015.pdf | 2015-04-30 |
| 18 | 65-CHE-2009 FORM-3 28-01-2013.pdf | 2013-01-28 |
| 19 | 65-CHE-2009 FORM-3 23-08-2013.pdf | 2013-08-23 |
| 19 | 65-CHE-2009 AMENDED CLAIMS 30-04-2015.pdf | 2015-04-30 |
| 20 | 65-CHE-2009 FORM-1 30-04-2015.pdf | 2015-04-30 |
| 20 | 65-CHE-2009 CORRESPONDENCE OTHERS 23-08-2013.pdf | 2013-08-23 |
| 21 | 65-CHE-2009 FORM-3 30-04-2015.pdf | 2015-04-30 |
| 21 | 65-CHE-2009 EXAMINATION REPORT REPLY RECEIVED 30-04-2015.pdf | 2015-04-30 |
| 22 | 65-CHE-2009 FORM-5 30-04-2015.pdf | 2015-04-30 |
| 22 | 65-CHE-2009 OTHERS 30-04-2015.pdf | 2015-04-30 |
| 23 | 65-CHE-2009 FORM-5 30-04-2015.pdf | 2015-04-30 |
| 23 | 65-CHE-2009 OTHERS 30-04-2015.pdf | 2015-04-30 |
| 24 | 65-CHE-2009 FORM-3 30-04-2015.pdf | 2015-04-30 |
| 24 | 65-CHE-2009 EXAMINATION REPORT REPLY RECEIVED 30-04-2015.pdf | 2015-04-30 |
| 25 | 65-CHE-2009 CORRESPONDENCE OTHERS 23-08-2013.pdf | 2013-08-23 |
| 25 | 65-CHE-2009 FORM-1 30-04-2015.pdf | 2015-04-30 |
| 26 | 65-CHE-2009 AMENDED CLAIMS 30-04-2015.pdf | 2015-04-30 |
| 26 | 65-CHE-2009 FORM-3 23-08-2013.pdf | 2013-08-23 |
| 27 | 65-CHE-2009 AMENDED PAGES OF SPECIFICATION 30-04-2015.pdf | 2015-04-30 |
| 27 | 65-CHE-2009 FORM-3 28-01-2013.pdf | 2013-01-28 |
| 28 | 65-CHE-2009 FORM-6 05-10-2012.pdf | 2012-10-05 |
| 28 | 65-CHE-2009-Form 3-090915.pdf | 2015-09-11 |
| 29 | 65-CHE-2009 FORM-3 27-03-2012.pdf | 2012-03-27 |
| 29 | 65-CHE-2009-Correspondence-090915.pdf | 2015-09-11 |
| 30 | 65-CHE-2009 CORRESPONDENCE OTHERS 12-10-2011.pdf | 2011-10-12 |
| 30 | 65-CHE-2009-Correspondence-300915.pdf | 2015-10-05 |
| 31 | 65-CHE-2009 FORM-3 12-10-2011.pdf | 2011-10-12 |
| 31 | 65-CHE-2009-Claims-300915.pdf | 2015-10-05 |
| 32 | 0065-che-2009 abstract.pdf | 2011-09-02 |
| 32 | 65-CHE-2009-Abstract-300915.pdf | 2015-10-05 |
| 33 | 0065-che-2009 correspondence-others.pdf | 2011-09-02 |
| 33 | 65-CHE-2009_EXAMREPORT.pdf | 2016-07-02 |
| 34 | 0065-che-2009 description(provisional).pdf | 2011-09-02 |
| 34 | Correspondence by Applicant_Renewal fee_29-12-2016.pdf | 2016-12-29 |
| 35 | 0065-che-2009 form-1.pdf | 2011-09-02 |
| 35 | Form27_License_22-03-2017.pdf | 2017-03-22 |
| 36 | 65-che-2009 form-3 06-09-2010.pdf | 2010-09-06 |
| 36 | Correspondence by Applicant_Form27_22-03-2017.pdf | 2017-03-22 |
| 37 | Correspondence by Applicant_Renewal fee_04-01-2018.pdf | 2018-01-04 |
| 37 | 65-CHE-2009 FORM-18 08-07-2010.pdf | 2010-07-08 |
| 38 | Form27_License_16-02-2018.pdf | 2018-02-16 |
| 38 | 65-CHE-2009 FORM-3 18-01-2010.pdf | 2010-01-18 |
| 39 | Correspondence by Applicant_Form27_16-02-2018.pdf | 2018-02-16 |
| 39 | 65-che-2009 abstract 07-01-2010.pdf | 2010-01-07 |
| 40 | Correspondence by Applicant_Renewal Fees_31-12-2018.pdf | 2018-12-31 |
| 40 | 65-che-2009 claims 07-01-2010.pdf | 2010-01-07 |
| 41 | Form27_Working of the Patented Invention_22-02-2019.pdf | 2019-02-22 |
| 41 | 65-che-2009 correspondence others 07-01-2010.pdf | 2010-01-07 |
| 42 | Correspondence by Applicant_Form27_22-02-2019.pdf | 2019-02-22 |
| 42 | 65-che-2009 description(complete) 07-01-2010.pdf | 2010-01-07 |
| 43 | 65-CHE-2009 FORM-2 07-01-2010.pdf | 2010-01-07 |
| 43 | 65-CHE-2009-Form27_License_06-03-2020.pdf | 2020-03-06 |
| 44 | 65-che-2009 form-5 07-01-2010.pdf | 2010-01-07 |
| 44 | 65-CHE-2009-Correspondence_06-03-2020.pdf | 2020-03-06 |