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Last Updated: April 19, 2024

Claims for Patent: 9,643,972


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Summary for Patent: 9,643,972
Title:Immunoregulatory agents
Abstract: Compounds that modulate the oxidoreductase enzyme indoleamine 2,3-dioxygenase, and compositions containing the compounds, are described herein. The use of such compounds and compositions for the treatment and/or prevention of a diverse array of diseases, disorders and conditions, including cancer- and immune-related disorders, that are mediated by indoleamine 2,3-dioxygenase is also provided.
Inventor(s): Beck; Hilary Plake (Emerald Hills, CA), Jaen; Juan Carlos (Burlingame, CA), Osipov; Maksim (Belmont, CA), Powers; Jay Patrick (Pacifica, CA), Reilly; Maureen Kay (Belmont, CA), Shunatona; Hunter Paul (San Francisco, CA), Walker; James Ross (Menlo Park, CA), Zibinsky; Mikhail (Lodi, CA), Balog; James Aaron (Lambertville, NJ), Williams; David K. (Delran, NJ), Markwalder; Jay A. (Lahaska, PA), Cherney; Emily Charlotte (Newtown, PA), Shan; Weifang (Princeton, NJ), Huang; Audris (New Hope, PA)
Assignee: Flexus Biosciences, Inc. (Princeton, NJ)
Application Number:14/933,863
Patent Claims:1. A compound having the formula (I): ##STR00284## or a pharmaceutically acceptable salt, hydrate or solvate thereof, wherein, the subscript n is 1; the subscript p is 1; the ring designated as A is phenyl, 5- or 6-membered heteroaryl, or C.sub.5-7 cycloalkyl; Z is O; B is N, C(OR.sup.5a), or C(R.sup.3a); each X is independently CHR.sup.5, C(O), or CH(OR.sup.5a); Q is N, C(CN), or CR.sup.6; D is a bond, O, C(R.sup.5).sub.2, or NR.sup.5a; E is an optionally substituted 9- or 10-membered fused bicyclic heteroaryl; R.sup.1 and R.sup.2 are independently hydrogen, halogen, optionally substituted C.sub.1-C.sub.4 haloalkyl, optionally substituted C.sub.3-C.sub.6 cycloalkyl, optionally substituted 3- to 6-membered cycloheteroalkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C.sub.1-C.sub.4 alkyl, optionally substituted C.sub.1-C.sub.4 alkoxy, CN, SO.sub.2NH.sub.2, NHSO.sub.2CH.sub.3, NHSO.sub.2CF.sub.3, OCF.sub.3, SO.sub.2CH.sub.3, SO.sub.2CF.sub.3, or CONH.sub.2, and when R.sup.1 and R.sup.2 are on adjacent vertices of a phenyl ring they may be joined together to form a 5- or 6-membered cycloheteroalkyl ring having one or two ring vertices independently selected from O, N and S, wherein said cycloheteroalkyl ring is optionally substituted with from one to three members selected from fluoro and C.sub.1-C.sub.3 alkyl; R.sup.3, R.sup.3a and R.sup.4 are independently hydrogen, optionally substituted C.sub.1-C.sub.6 alkyl, optionally substituted C.sub.2-C.sub.6 alkenyl, optionally substituted C.sub.2-C.sub.6 alkynyl, optionally substituted C.sub.1-C.sub.6 haloalkyl, optionally substituted C.sub.3-C.sub.6 cycloalkyl-C.sub.1-C.sub.4 alkyl, optionally substituted aryl-C.sub.1-C.sub.6 alkyl, fluorine, OH, CN, CO.sub.2H, C(O)NH.sub.2, N(R.sup.5).sub.2, optionally substituted --O--C.sub.1-C.sub.6 alkyl, --(CR.sup.5R.sup.5).sub.m--OH, --(CR.sup.5R.sup.5).sub.m--CO.sub.2H, --(CR.sup.5R.sup.5).sub.m--C(O)NH.sub.2, --(CR.sup.5R.sup.5).sub.m--C(O)NHR.sup.5, --(CR.sup.5R.sup.5).sub.mN(R.sup.5).sub.2, --NH(CR.sup.5R.sup.5).sub.mCO.sub.2H or --NH(CR.sup.5R.sup.5).sub.m--C(O)NH.sub.2; each R.sup.5 is independently H, F, OH, or optionally substituted C.sub.1-C.sub.6 alkyl; each R.sup.5a is independently H, or optionally substituted C.sub.1-C.sub.6 alkyl; R.sup.6 is H, OH, F, optionally substituted C.sub.1-C.sub.6 alkyl, optionally substituted --O--C.sub.1-C.sub.6 alkyl, or --N(R.sup.5a).sub.2; and each m is independently 1, 2, or 3.

2. The compound of claim 1, or a pharmaceutically acceptable salt, hydrate or solvate thereof, wherein, the subscript n is 1; the subscript p is 1; the ring designated as A is phenyl, 5- or 6-membered heteroaryl, or C.sub.5-7 cycloalkyl; Z is O; B is N, C(OR.sup.5a), or C(R.sup.3a); each X is independently CHR.sup.5, C(O), or CH(OR.sup.5a); Q is N, C(CN), or CR.sup.6; D is a bond, O, C(R.sup.5).sub.2, or NR.sup.5a; E is an optionally substituted 9- or 10-membered fused bicyclic heteroaryl; R.sup.1 and R.sup.2 are independently hydrogen, halogen, optionally substituted C.sub.1-C.sub.4 haloalkyl, optionally substituted C.sub.3-C.sub.6 cycloalkyl, optionally substituted 3- to 6-membered cycloheteroalkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C.sub.1-C.sub.4 alkyl, optionally substituted C.sub.1-C.sub.4 alkoxy, CN, SO.sub.2NH.sub.2, NHSO.sub.2CH.sub.3, NHSO.sub.2CF.sub.3, OCF.sub.3, SO.sub.2CH.sub.3, SO.sub.2CF.sub.3, or CONH.sub.2, and when R.sup.1 and R.sup.2 are on adjacent vertices of a phenyl ring they may be joined together to form a 5- or 6-membered cycloheteroalkyl ring having one or two ring vertices independently selected from O, N and S, wherein said cycloheteroalkyl ring is optionally substituted with from one to three members selected from fluoro and C.sub.1-C.sub.3 alkyl; R.sup.3, R.sup.3a and R.sup.4 are independently hydrogen, optionally substituted C.sub.1-C.sub.6 alkyl, optionally substituted C.sub.1-C.sub.6 haloalkyl, fluorine, OH, CN, CO.sub.2H, C(O)NH.sub.2, N(R.sup.5).sub.2, optionally substituted --O--C.sub.1-C.sub.6 alkyl, --(CR.sup.5R.sup.5).sub.m--OH, --(CR.sup.5R.sup.5).sub.m--CO.sub.2H, --(CR.sup.5R.sup.5).sub.m--C(O)NH.sub.2, --(CR.sup.5R.sup.5).sub.m--C(O)NHR.sup.5, --(CR.sup.5R.sup.5).sub.mN(R.sup.5).sub.2, --NH(CR.sup.5R.sup.5).sub.mCO.sub.2H or --NH(CR.sup.5R.sup.5).sub.m--C(O)NH.sub.2; each R.sup.5 is independently H, F, OH, or optionally substituted C.sub.1-C.sub.6 alkyl; each R.sup.5a is independently H, or optionally substituted C.sub.1-C.sub.6 alkyl; R.sup.6 is H, OH, F, optionally substituted C.sub.1-C.sub.6 alkyl, optionally substituted --O--C.sub.1-C.sub.6 alkyl, or --N(R.sup.5a).sub.2; and each m is independently 1, 2, or 3.

3. The compound of claim 1, having the formula: ##STR00285## wherein Q is C(CN) or CR.sup.6.

4. The compound of claim 3, having the formula: ##STR00286##

5. The compound of claim 4, having the formula: ##STR00287##

6. The compound of claim 5, having the formula: ##STR00288## wherein J.sup.1 is CH, N or optionally C(R.sup.2) when R.sup.2 is attached to the ring vertex identified as J.sup.1.

7. The compound of claim 6, having the formula: ##STR00289##

8. The compound of claim 7, having the formula: ##STR00290##

9. The compound of claim 8, having the formula: ##STR00291##

10. The compound of claim 8, having the formula: ##STR00292##

11. The compound of claim 10, having the formula: ##STR00293##

12. The compound of claim 11, having the formula: ##STR00294##

13. The compound of claim 11, having the formula: ##STR00295##

14. The compound of claim 11, having the formula: ##STR00296##

15. The compound of claim 11, having the formula: ##STR00297##

16. The compound of claim 11, having the formula: ##STR00298##

17. The compound of claim 11, having the formula: ##STR00299##

18. The compound of claim 11, having the formula: ##STR00300##

19. The compound of claim 11, having the formula: ##STR00301##

20. The compound of claim 11, having the formula: ##STR00302##

21. The compound of claim 11, having the formula: ##STR00303##

22. The compound of claim 17, having the formula: ##STR00304## which is substantially free of other isomers at the carbon atoms to which each of R.sup.3a and R.sup.6 are attached.

23. The compound of claim 17, having the formula: ##STR00305## which is substantially free of other isomers at the carbon atoms to which each of R.sup.3a and R.sup.6 are attached.

24. The compound of claim 17, having the formula: ##STR00306## wherein: R.sup.11 and R.sup.12 are independently hydrogen, halogen, optionally substituted C.sub.1-C.sub.4 haloalkyl, optionally substituted C.sub.3-C.sub.6 cycloalkyl, optionally substituted 3- to 6-membered cycloheteroalkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C.sub.1-C.sub.4 alkyl, optionally substituted C.sub.1-C.sub.4 alkoxy, CN, SO.sub.2NH.sub.2, NHSO.sub.2CH.sub.3, NHSO.sub.2CF.sub.3, OCF.sub.3, SO.sub.2CH.sub.3, SO.sub.2CF.sub.3, or CONH.sub.2, and when R.sup.1 and R.sup.2 are on adjacent vertices of a phenyl ring they may be joined together to form a 5- or 6-membered cycloheteroalkyl ring having one or two ring vertices independently selected from O, N and S, wherein said cycloheteroalkyl ring is optionally substituted with from one to three members selected from fluoro and C.sub.1-C.sub.3 alkyl.

25. The compound of claim 24, wherein R.sup.6 is H, and R.sup.11 and R.sup.12 are each independently selected from the group consisting of halogen, CN and optionally substituted C.sub.1-C.sub.4 alkyl.

26. The compound of claim 17, having the formula: ##STR00307## wherein: R.sup.11 and R.sup.12 are independently hydrogen, halogen, optionally substituted C.sub.1-C.sub.4 haloalkyl, optionally substituted C.sub.3-C.sub.6 cycloalkyl, optionally substituted 3- to 6-membered cycloheteroalkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C.sub.1-C.sub.4 alkyl, optionally substituted C.sub.1-C.sub.4 alkoxy, CN, SO.sub.2NH.sub.2, NHSO.sub.2CH.sub.3, NHSO.sub.2CF.sub.3, OCF.sub.3, SO.sub.2CH.sub.3, SO.sub.2CF.sub.3, or CONH.sub.2, and when R.sup.1 and R.sup.2 are on adjacent vertices of a phenyl ring they may be joined together to form a 5- or 6-membered cycloheteroalkyl ring having one or two ring vertices independently selected from O, N and S, wherein said cycloheteroalkyl ring is optionally substituted with from one to three members selected from fluoro and C.sub.1-C.sub.3 alkyl.

27. The compound of claim 17, having the formula: ##STR00308## wherein: R.sup.11 and R.sup.12 are independently hydrogen, halogen, optionally substituted C.sub.1-C.sub.4 haloalkyl, optionally substituted C.sub.3-C.sub.6 cycloalkyl, optionally substituted 3- to 6-membered cycloheteroalkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C.sub.1-C.sub.4 alkyl, optionally substituted C.sub.1-C.sub.4 alkoxy, CN, SO.sub.2NH.sub.2, NHSO.sub.2CH.sub.3, NHSO.sub.2CF.sub.3, OCF.sub.3, SO.sub.2CH.sub.3, SO.sub.2CF.sub.3, or CONH.sub.2, and when R.sup.1 and R.sup.2 are on adjacent vertices of a phenyl ring they may be joined together to form a 5- or 6-membered cycloheteroalkyl ring having one or two ring vertices independently selected from O, N and S, wherein said cycloheteroalkyl ring is optionally substituted with from one to three members selected from fluoro and C.sub.1-C.sub.3 alkyl.

28. The compound of claim 17, having the formula: ##STR00309##

29. The compound of claim 27, having the formula: ##STR00310## which is substantially free of other isomers at the stereocenters of the cyclohexane ring.

30. The compound of claim 27, having the formula: ##STR00311##

31. The compound of claim 27, having the formula: ##STR00312##

32. The compound of claim 28, having the formula: ##STR00313## which is substantially free of other isomers at each of the three stereocenters shown.

33. The compound of claim 28, having the formula: ##STR00314## which is substantially free of other isomers at each of the three stereocenters shown.

34. The compound of claim 31, wherein R.sup.1 is Cl, F, optionally substituted phenyl, or CN.

35. The compound of claim 31, having the formula: ##STR00315## wherein R.sup.1 is Cl, F, optionally substituted phenyl, or CN; and R.sup.2 is H or F; and which is substantially free of other isomers at each of the three stereocenters shown.

36. The compound of claim 34, wherein R.sup.1 is Cl.

37. The compound of claim 34, wherein R.sup.1 is Cl; and R.sup.3 is CH.sub.3.

38. The compound of claim 34, having the formula: ##STR00316## which is substantially free of other isomers at each of the two stereocenters shown.

39. The compound of claim 34, having the formula: ##STR00317## which is substantially free of other isomers at each of the two stereocenters shown.

40. The compound of claim 34, having the formula: ##STR00318## which is substantially free of other isomers at each of the three stereocenters shown.

41. The compound of claim 1 that is N-(4-chlorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-cyanophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-cyanophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-fluorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-fluorophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-fluorophenyl)-2-(cis-4-(quinolin-3-yl)cyclohexyl)acetamide; N-(4-fluorophenyl)-2-(trans-4-(quinolin-3-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(cis-4-(quinolin-3-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(trans-4-(quinolin-3-yl)cyclohexyl)acetamide; N-(4-cyanophenyl)-2-(cis-4-(quinolin-3-yl)cyclohexyl)acetamide; N-(4-cyanophenyl)-2-(trans-4-(quinolin-3-yl)cyclohexyl)acetamide; 2-(4-(cis-1H-indazol-4-yl)cyclohexyl)-N-(4-cyanophenyl)acetamide; 2-(4-(trans-1H-indazol-4-yl)cyclohexyl)-N-(4-cyanophenyl)acetamide; 2-(4-(1H-indazol-4-yl)cyclohexyl)-N-(4-chlorophenyl)acetamide; N-(4-fluorophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)propanamide; N-(4-chlorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)propanamide; N-(4-chlorophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)propanamide; (R)--N-(4-chlorophenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)cyclohexyl)propan- amide; (S)--N-(4-chlorophenyl)-2-(trans-4-(quinolin-3-yl)cyclohexyl)propan- amide; (R)--N-(4-cyanophenyl)-2-(cis-4-(7-fluoroquinolin-4-yl)cyclohexyl)b- utanamide; (R)--N-(4-chlorophenyl)-2-(cis-4-(7-fluoroquinolin-4-yl)cyclohe- xyl)butanamide; (R)--N-(4-chlorophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)propamide; (R)--N-(4-cyanophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)propamide; (R)--N-(4-chlorophenyl)-2-(cis-4-(quinolin-4-yl)cyclohexyl)butanamide; (S)--N-(4-chlorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)butanamide; N-(4-chlorophenyl)-2-(cis-4-(quinolin-4-yloxy)cyclohexyl)propanamide; N-(4-chlorophenyl)-2-(cis-1-hydroxy-4-(quinolin-4-yl)cyclohexyl)acetamide- ; N-(4-fluorophenyl)-2-(cis-4-(isoquinolin-4-yloxy)cyclohexyl)acetamide; N-(4-fluorophenyl)-2-(trans-4-(isoquinolin-4-yloxy)cyclohexyl)acetamide; N-(4-cyanophenyl)-2-(cis-4-(quinolin-4-yloxy)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(trans-1-hydroxy-4-(quinolin-4-yl)cyclohexyl)acetami- de; N-(4-fluorophenyl)-2-(trans-1-hydroxy-4-(quinolin-4-yl)cyclohexyl)acet- amide; (R)--N-(4-cyanophenyl)-2-(cis-4-(quinolin-4-yloxy)cyclohexyl)propan- amide; (S)--N-(4-fluorophenyl)-2-(cis-4-(quinolin-4-yloxy)cyclohexyl)propa- namide; N-(4-chlorophenyl)-2-(trans-4-(quinolin-4-yl)cyclohexyl)pent-4-ena- mide; 2-(4-(1H-pyrazolo[3,4-b]pyridin-4-yl)cyclohexyl)-N-(4-chlorophenyl) acetamide; N-(4-fluorophenyl)-2-(cis-4-(quinazolin-4-yl)cyclohexyl)acetamide; N-(4-fluorophenyl)-2-(4-(quinazolin-4-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(cis-4-(quinazolin-4-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(trans-4-(quinazolin-4-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(4-(1,5-naphthyridin-4-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(cis-4-(quinolin-3-yl)cyclohexyl)propanamide; N-(4-fluorophenyl)-2-(trans-4-(quinolin-3-yl)cyclohexyl)propanamide; N-(4-chlorophenyl)-2-((trans)-4-(isoquinolin-1-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-((cis)-4-(isoquinolin-1-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-((cis)-4-(isoquinolin-8-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-((trans)-4-isoquinolin-8-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-((trans)-4-(isoquinolin-5-yl)cyclohexyl)acetamide; N-(4-fluorophenyl)-2-(cis-4-(quinolin-3-yl)cyclohexyl)propanamide; N-(4-cyanophenyl)-2-((cis)-4-(quinolin-4-yl)cyclohexyl)pent-4-enamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-phenylpropanamide; (R)--N-(4-fluoro-2-methylphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cycloh- exyl)propanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(4-(trifluoromethyl)p- henyl)propanamide; (R)--N-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-((cis)-4-(6-fluoroquinoli- n-4-yl)cyclohexyl)propanmide; (R)--N-(2-ethoxyphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(3-(difluoromethyl)phenyl)-2-((cis)-4-(6-fluoroquinolin-4-- yl)cyclohexyl)propanamide; (R)--N-(4-chloro-2-methylphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cycloh- exyl)propanamide; (R)--N-(3-chlorophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(3,4-dichlorophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyc- lohexyl)propanamide; methyl 3-((R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamido)benzoate; methyl 4-((R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamido)be- nzoate; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-methyl-N-pheny- lpropanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(3-(trifluoromethyl)p- henyl)propanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(4-phenoxyphenyl)prop- anamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(m-tolyl)prop- anamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(3-phenoxyphe- nyl)propanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(2-phenoxyphenyl)prop- anamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(pyridin-4-yl- )propanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(thiazol-2-yl)propana- mide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(pyridin-3-yl)pr- opanamide; (R)--N-(2-fluorophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclo- hexyl)propanamide; (R)--N-(4-ethoxyphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(3-cyanophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohex- yl)propanamide; (R)--N-(3-chloro-4-methylphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cycloh- exyl)propanamide; (R)--N-(3-fluorophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(3-cyano-4-(trifluoromethyl)phenyl)-2-((cis)-4-(6-fluoroqu- inolin-4-yl)cyclohexyl)propanamide; N-(4-chlorophenyl)-2-((trans)-4-((7-(trifluoromethyl)quinolin-4-yl)oxy)cy- clohexyl)butanamide; N-(4-chlorophenyl)-2-((trans)-4-((2-(trifluoromethyl)quinolin-4-yl)oxy)cy- clohexyl)butanamide; N-(4-chlorophenyl)-2-((trans)-4-(quinolin-4-yloxy)cyclohexyl)butanamide; N-(4-chlorophenyl)-2-((trans)-4-((8-(trifluoromethyl)quinolin-4-yl)oxy)cy- clohexyl)butanamide; 2-(4-((R)-3-((4-Chlorophenyl)amino)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyc- lohexyl)-3-oxopropyl)phenyl)-2-propanoic acid; N-(4-chlorophenyl)-2-((cis)-4-((2-(trifluoromethyl)quinolin-4-yl)oxy)cycl- ohexyl)butanamide; N-(4-chlorophenyl)-2-((cis)-4-((6-(trifluoromethyl)quinolin-4-yl)oxy)cycl- ohexyl)butanamide; N-(4-chlorophenyl)-2-(4-((4-chloroquinolin-6-yl)oxy)piperidin-1-yl)acetam- ide; N-(4-chlorophenyl)-2-(4-((4-chloroquinolin-6-yl)oxy)piperidin-1-yl)pr- opanamide; 2-(4-((4-chloroquinolin-6-yl)oxy)piperidin-1-yl)-N-(p-tolyl)pro- panamide; N-(4-chlorophenyl)-2-(4-((6-fluoroquinolin-4-yl)oxy)piperidin-1-- yl)acetamide; N-(4-chlorophenyl)-2-(4-((6-fluoroquinolin-4-yl)oxy)piperidin-1-yl)propan- amide; 2-(4-((6-fluoroquinolin-4-yl)oxy)piperidin-1-yl)-N-(p-tolyl)butanam- ide; N-(4-chlorophenyl)-2-(4-((6-fluoroquinolin-4-yl)oxy)piperidin-1-yl)bu- tanamide; N-(4-fluorophenyl)-2-(4-((6-fluoroquinolin-4-yl)oxy)piperidin-1-- yl)propanamide; N-(4-ethoxyphenyl)-2-(4-((6-fluoroquinolin-4-yl)oxy)piperidin-1-yl)propan- amide; 2-(4-((6-fluoroquinolin-4-yl)oxy)piperidin-1-yl)-N-(p-tolyl)propana- mide; N-(4-chlorophenyl)-2-(4-((6-fluoroquinolin-4-yl)oxy)piperidin-1-yl)-- 3-methylbutanamide; N-(4-chlorophenyl)-2-(1-(quinolin-4-ylmethyl)piperidin-4-yl)acetamide; N-(4-fluorophenyl)-(1-(quinolin-4-ylmethyl)piperidin-4-yl)acetamide; N-(4-fluorophenyl)-2-(1-(6-fluoroquinolin-4-yl)piperidin-4-yl)acetamide; N-(4-chlorophenyl)-2-(1-(6-fluoroquinolin-4-yl)piperidin-4-yl)acetamide; N-(4-bromophenyl)-2-(1(6-fluoroquinolin-4-yl)piperidin-4-yl)acetamide; N-(2-fluoro-4-methylphenyl)-2-(1-(6-fluoroquinolin-4-yl)piperidin-4-yl)ac- etamide; N-(4-chloro-2-methylphenyl)-2-(1-(6-fluoroquinolin-4-yl)piperidin- -4-yl)acetamide; N-(4-fluorophenyl)-2-(1-(6-fluoroquinolin-4-yl)-4-methylpiperidin-4-yl)ac- etamide; N-(4-chlorophenyl)-2-(1-(6-fluoroquinolin-4-yl)-4-methylpiperidin- -4-yl)acetamide; 2-(1-(6-fluoroquinolin-4-yl)-4-methylpiperidin-4-yl)-N-(2-methoxypyrimidi- n-5-yl)acetamide; N-(4-ethoxyphenyl)-2-(1-(6-fluoroquinolin-4-yl)-4-methylpiperidin-4-yl)ac- etamide; N-(4-chlorophenyl)-2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)pro- panamide; N-(4-fromophenyl)-2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)pro- panamide; 2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)-N-phenylpropanamide; N-(4-chlorophenyl)-2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)butanamide; 2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)-N-phenylbutanamide; N-(4-chlorophenyl)-2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)-3-methoxyp- ropanamide; N-(4-fluorophenyl)-2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)-3-methoxyp- ropanamide; 2-(4-((R)-3-((4-cyanophenyl)amino)-2-((cis)-4-(6-fluoroquinolin-4-yl)cycl- ohexyl)-3-oxopropyl)phenyl)propanoic acid; (R)--N-cyclohexyl-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamid- e; N-cyclohexyl-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(cis-trans-4-(pyrazolo[1,5-a]pyrimidin-7-yl)cyclohex- yl)propanamide; N-(4-chlorophenyl)-2-(trans-4-(pyrazolo[1,5-a]pyrimidin-7-yl)cyclohexyl)p- ropanamide; (S)--N-(4-chlorophenyl)-2-((cis)-4-(pyrazolo[1,5-a]pyrimidin-7-yl)cyclohe- xyl)propanamide; (R)--N-(4-chlorophenyl)-2-((cis)-4-(pyrazolo[1,5-a]pyrimidin-7-yl)cyclohe- xyl)propanamide; (R)--N-(4-chlorophenyl)-2-((trans)-4-(pyrazolo[1,5-a]pyrimidin-7-yl)cyclo- hexyl)propanamide; 2-(cis-4-(1,8-naphthyridin-4-yl)cyclohexyl)-N-(4-chlorophenyl)propanamide- ; 2-trans-4-(1,8-naphthyridin-4-yl)cyclohexyl)-N-(4-chlorophenyl)propanami- de; (S)-2-((cis)-4-(1,8-naphthyridin-4-yl)cyclohexyl)-N-(4-chlorophenyl)pr- opanamide; (R)-2-((cis)-4-(1,8-naphthyridin-4-yl)cyclohexyl)-N-(4-chloroph- enyl)propanamide; 2-(trans-4-(1H-pyrazolo[4,3-b]pyridin-7-yl)cyclohexyl)-N-(4-chlorophenyl)- propanamide; (S)-2-((cis)-4-(1H-pyrazolo[4,3-b]pyridin-7-yl)cyclohexyl)-N-(4-chlorophe- nyl)propanamide; (R)-2-((cis)-4-(1H-pyrazolo[4,3-b]pyridin-7-yl)cyclohexyl)-N-(4-chlorophe- nyl)propanamide; (S)-2-((trans)-4-(1H-pyrazolo[4,3-b]pyridin-7-yl)cyclohexyl)-N-(4-chlorop- henyl)propanamide; (R)-2-((trans)-4-(1H-pyrazolo[4,3-b]pyridin-7-yl)cyclohexyl)-N-(4-chlorop- henyl)propanamide; N-(cis-4-chlorophenyl)-2-(4-(6-iodoquinolin-4-yl)cyclohexyl)propanamide; N-(trans-4-chlorophenyl)-2-(4-(6-iodoquinolin-4-yl)cyclohexyl)propanamide- ; (S)--N-(4-chlorophenyl)-2-((cis)-4-(6-iodoquinolin-4-yl)cyclohexyl)propa- namide; (R)--N-(4-chlorophenyl)-2-((cis)-4-(6-iodoquinolin-4-yl)cyclohexyl- )propanamide; (S)--N-(4-chlorophenyl)-2-((trans)-4-(6-iodoquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(4-chlorophenyl)-2-((trans)-4-(6-iodoquinolin-4-yl)cyclohe- xyl)propanamide; 2-((trans)-4-((1,8-naphthyridin-4-yl)oxy)cyclohexyl)-N-(4-chlorophenyl)pr- opanamide; N-(4-chlorophenyl)-2-(4-(6-fluoroquinolin-4-yl)cyclohexyl)butan- amide; (R)--N-(4-chlorophenyl)-4-hydroxy-2-((cis)-4-(quinolin-4-yl)cyclohe- xyl)butanamide; N-(4-chlorophenyl)-2-((cis)-4-cyano-4-(quinolin-4-yl)cyclohexyl)acetamide- ; N-(4-chlorophenyl)-2-((trans)-4-cyano-4-(quinolin-4-yl)cyclohexyl)acetam- ide; (R)--N-(4-chlorophenyl)-5-hydroxy-2-((cis)-4-(quinolin-4-yl)cyclohexy- l)pentanamide; N-(4-chlorophenyl)-2-(1-methoxy-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-fluorophenyl)-2-(4-hydroxy-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(4-hydroxy-4-(quinolin-4-yl)cyclohexyl)acetamide; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(7-fluoroquinolin-4-yl)cyclohexyl)pr- opanamide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(7-fluoroquinolin-4-yl)cyc- lohexyl)propanamide; (R)--N-(4-cyanophenyl)-2-((1S,4S)-4-(7-fluoroquinolin-4-yl)cyclohexyl)pro- panamide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(7-fluoroquinolin-4-yl)cycl- ohexyl)butanamide; (R)--N-(4-chlorophenyl)-2-((1R,4R)-4-(quinolin-4-yl)cyclohexyl)butanamide- ; (R)--N-(4-fluorophenyl)-2-((1R,4R)-4-(quinolin-4-yl)cyclohexyl)butanamid- e; (S)--N-(4-cyanophenyl)-2-((1R,4S)-4-(quinolin-4-yl)cyclohexyl)butanamid- e; (R)--N-(4-chlorophenyl)-2-((1S,4R)-4-(quinolin-4-yl)cyclohexyl)pent-4-y- namide; N-(4-chlorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)pentanam- ide; 5-((4-chlorophenyl)amino)-5-oxo-4-((1S,4S)-4-(quinolin-4-yl)cyclohexy- l)pentanoic acid; N-(4-chlorophenyl)-2-((1S,4S)-4-(8-fluoroquinolin-4-yl)cyclohexyl)acetami- de; N-(4-fluorophenyl)-2-((1R,4R)-4-(8-fluoroquinolin-4-yl)cyclohexyl)acet- amide; (R)--N-(2-fluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)prop- anamide; (R)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)-N-(4-(trifluoromethox- y)phenyl)propanamide; (R)--N-(3-fluoro-4-(trifluoromethyl)phenyl)-2-((1S,4S)-4-(quinolin-4-yl)c- yclohexyl)propanamide; (R)--N-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-((1S,4S)-4-(quinolin-4-yl- )cyclohexyl)propanamide; (R)--N-(3-chloro-4-fluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)p- ropanamide; (R)--N-(4-chlorophenyl)-5-methyl-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)h- ex-4-enamide; (S)--N-(4-chlorophenyl)-2-((1S,4R)-4-(quinolin-4-yl)cyclohexyl)propanamid- e; (R)--N-(4-chloro-2-fluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl- )propanamide; N-(4-cyanophenyl)-2-((1R,4R)-4-(quinolin-4-yl)cyclohexyl)pent-4-enamide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)propanamid- e; (R)--N-(5-chloropyridin-2-yl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)pr- opanamide; (R)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)-N-(4-(trifluorometh- yl)phenyl)propanamide; (R)--N-(4-chloro-3-fluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)p- ropanamide; (R)--N-(4-cyano-3-fluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)pr- opanamide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)- pent-4-enamide; (R)--N-(3,4-difluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)propan- amide; N-(4-chlorophenyl)-2-((1S,4S)-4-(6,8-difluoroquinolin-4-yl)cyclohex- yl)acetamide; 2-((1S,4S)-4-(6,8-difluoroquinolin-4-yl)cyclohexyl)-N-(4-fluorophenyl)ace- tamide; 2-((1R,4R)-4-(6,8-difluoroquinolin-4-yl)cyclohexyl)-N-(4-fluorophe- nyl)acetamide; N-(4-chlorophenyl)-2-((1R,4R)-4-(quinolin-4-yloxy)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-((1S,4S)-4-(quinolin-4-yloxy)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-(1-hydroxy-4-(quinolin-4-yl)cyclohexyl)acetamide; N-(4-cyanophenyl)-2-((1R,4R)-4-(quinolin-4-yloxy)cyclohexyl)acetamide; N-(4-chlorophenyl)-2-((1R,4R)-1-hydroxy-4-(quinolin-4-yl)cyclohexyl)aceta- mide; N-(4-fluorophenyl)-2-((1R,4R)-1-hydroxy-4-(quinolin-4-yl)cyclohexyl)- acetamide; N-(4-chlorophenyl)-2-((1S,4S)-1-hydroxy-4-(quinolin-4-yl)cycloh- exyl)acetamide; (S)--N-(4-fluorophenyl)-2-((1R,4S)-1-hydroxy-4-(quinolin-4-yl)cyclohexyl)- propanamide; (S)--N-(4-cyanophenyl)-2-((1R,4S)-1-hydroxy-4-(quinolin-4-yl)cyclohexyl)p- ropanamide; N-(4-chlorophenyl)-2-((1S,4S)-4-(2-(trifluoromethyl)quinolin-4-yl)cyclohe- xyl)acetamide;

N-(4-chlorophenyl)-2-((1R,4R)-4-(2-(trifluoromethyl)quinolin-4-yl)cyclohe- xyl)acetamide; N-(4-fluorophenyl)-2-((1R,4R)-4-(2-(trifluoromethyl)quinolin-4-yl)cyclohe- xyl)acetamide; N-(4-fluorophenyl)-2-((1S,4S)-4-(2-(trifluoromethyl)quinolin-4-yl)cyclohe- xyl)acetamide; N-(4-fluorophenyl)-2-((1S,4S)-4-(8-(trifluoromethyl)quinolin-4-yl)cyclohe- xyl)acetamide; N-(4-chlorophenyl)-2-((1R,4R)-4-(8-(trifluoromethyl)quinolin-4-yl)cyclohe- xyl)acetamide; N-(4-chlorophenyl)-2-((1S,4S)-4-(8-trifluoromethyl)quinolin-4-yl)cyclohex- yl)acetamide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)pr- opanamide; (R)--N-(4-cyanophenyl)-2-((1S,4S)-4-(8-fluoroquinolin-4-yl)cycl- ohexyl)propanamide; 2-(4-((R)-3-((4-chlorophenyl)amino)-3-oxo-2-((1S,4S)-4-(quinolin-4-yl)cyc- lohexyl)propyl)phenyl)acetic acid; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(8-fluoroquinolin-4-yl)cyclohexyl)pr- opanamide; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(quinolin-3-yl)cyclohexyl)- propanamide; (R)--N-(4-chlorophenyl)-2-((1R,4R)-4-(quinolin-3-yl)cyclohexyl)propanamid- e; (S)--N-(4-chlorophenyl)-2-((1S,4R)-4-(quinolin-3-yl)cyclohexyl)propanam- ide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)butana- mide; (S)--N-(4-fluorophenyl)-2-((1R,4S)-4-(quinolin-4-yl)cyclohexyl)butan- amide; N-(4-chlorophenyl)-2-((1R,4R)-4-(8-fluoroquinolin-4-yl)cyclohexyl)a- cetamide; N-(4-fluorophenyl)-2-((1S,4S)-4-(8-fluoroquinolin-4-yl)cyclohexy- l)acetamide; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(quinolin-4-yl)cyclohexyl)pent-4-ena- mide; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(8-(trifluoromethyl)quinolin-4-- yl)cyclohexyl)propanamide; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(2-(trifluoromethyl)quinolin-4-yl)cy- clohexyl)propanamide; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(quinolin-4-yloxy)cyclohexyl)propana- mide; (S)--N-(4-chlorophenyl)-2-((1S,4R)-4-(quinolin-4-yloxy)cyclohexyl)pr- opanamide; N-(4-chlorophenyl)-2-(trans-4-(6-fluoroquinolin-4-yl)-1-hydroxy- cyclohexyl)propanamide; N-(4-chlorophenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)-1-hydroxycyclohexyl)p- ropanamide; N-(4-chlorophenyl)-2-(trans-1-fluoro-4-(6-fluoroquinolin-4-yl)cyclohexyl)- propanamide; N-(4-chlorophenyl)-2-(trans-4-(6-fluoroquinolin-4-yl)-4-hydroxycyclohexyl- )propanamide; N-(4-chlorophenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)-4-hydroxycyclohexyl)p- ropanamide; (R)--N-(4-chloro-2-hydroxyphenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)cyclohe- xyl)propanamide; (R)--N-(4-chloro-3-hydroxyphenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)cyclohe- xyl)propanamide; (R)--N-((2S)-bicyclo[2.2.1]heptan-2-yl)-2-(cis-4-(6-fluoroquinolin-4-yl)c- yclohexyl)propanamide; (R)--N-(2-amino-4-chlorophenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)cyclohexy- l)pent-4-enamide; 2-(1-(6-fluoroquinolin-4-yl)-4-methylpiperidin-4-yl)-N-(1-methylcyclohexy- l)acetamide; N-(4-chlorophenyl)-2-(1-(6-fluoroquinolin-4-yl)piperidin-4-yl)butanamide; N-(4-chlorophenyl)-2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)pentanamide- ; 2-(4-(6-fluoroquinolin-4-yl)piperazin-1-yl)-N-(1-methylcyclohexyl)pentan- amide; cis-N-(4-chlorophenyl)-2-(4-(3-methyl-3H-imidazo[4, 5-b]pyridin-7-yl)cyclohexyl)propanamide; trans-N-(4-chlorophenyl)-2-(4-(3-methyl-3H-imidazo[4,5-b]pyridin-7-yl)cyc- lohexyl)propanamide; or N-(4-chlorophenyl)-2-(4-(3-methyl-3H-imidazo[4,5-b]pyridin-7-yl)cyclohexy- l)propanamide; or a stereoisomer thereof or a pharmaceutically acceptable salt thereof.

42. A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable excipient.

43. A combination comprising a compound of claim 1 and at least one additional therapeutic agent.

44. The combination of claim 43, wherein the at least one additional therapeutic agent is a chemotherapeutic agent, an immune- and/or inflammation-modulating agent, an anti-hypercholesterolemia agent, or an anti-infective agent.

45. The combination of claim 43, wherein the at least one additional therapeutic agent is an immune checkpoint inhibitor.

46. The combination of claim 45, wherein said immune checkpoint inhibitor is selected from the group consisting of ipilimumab, nivolumab and pembroluzimab.

47. The compound of claim 1 that is (R)--N-(4-chlorophenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)cyclohexyl)propan- amide; (R)--N-(4-cyanophenyl)-2-(cis-4-(7-fluoroquinolin-4-yl)cyclohexyl)b- utanamide; (R)--N-(4-chlorophenyl)-2-(cis-4-(7-fluoroquinolin-4-yl)cyclohe- xyl)butanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-phenylpropanamide; (R)--N-(4-fluoro-2-methylphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cycloh- exyl)propanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(4-(trifluoromethyl)p- henyl)propanamide; (R)--N-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-2-((cis)-4-(6-fluoroquinoli- n-4-yl)cyclohexyl)propanmide; (R)--N-(2-ethoxyphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(3-(difluoromethyl)phenyl)-2-((cis)-4-(6-fluoroquinolin-4-- yl)cyclohexyl)propanamide; (R)--N-(4-chloro-2-methylphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cycloh- exyl)propanamide; (R)--N-(3-chlorophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(3,4-dichlorophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyc- lohexyl)propanamide; methyl 3-((R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamido)benzoate; methyl 4-((R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamido)be- nzoate; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-methyl-N-pheny- lpropanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(3-(trifluoromethyl)p- henyl)propanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(4-phenoxyphenyl)prop- anamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(m-tolyl)prop- anamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(3-phenoxyphe- nyl)propanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(2-phenoxyphenyl)prop- anamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(pyridin-4-yl- )propanamide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(thiazol-2-yl)propana- mide; (R)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-N-(pyridin-3-yl)pr- opanamide; (R)--N-(2-fluorophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclo- hexyl)propanamide; (R)--N-(4-ethoxyphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(3-cyanophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohex- yl)propanamide; (R)--N-(3-chloro-4-methylphenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cycloh- exyl)propanamide; (R)--N-(3-fluorophenyl)-2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(3-cyano-4-(trifluoromethyl)phenyl)-2-((cis)-4-(6-fluoroqu- inolin-4-yl)cyclohexyl)propanamide; N-(cis-4-chlorophenyl)-2-(4-(6-iodoquinolin-4-yl)cyclohexyl)propanamide; N-(trans-4-chlorophenyl)-2-(4-(6-iodoquinolin-4-yl)cyclohexyl)propanamide- ; (S)--N-(4-chlorophenyl)-2-((cis)-4-(6-iodoquinolin-4-yl)cyclohexyl)propa- namide; (R)--N-(4-chlorophenyl)-2-((cis)-4-(6-iodoquinolin-4-yl)cyclohexyl- )propanamide; (S)--N-(4-chlorophenyl)-2-((trans)-4-(6-iodoquinolin-4-yl)cyclohexyl)prop- anamide; (R)--N-(4-chlorophenyl)-2-((trans)-4-(6-iodoquinolin-4-yl)cyclohe- xyl)propanamide; N-(4-chlorophenyl)-2-(4-(6-fluoroquinolin-4-yl)cyclohexyl)butanamide; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(7-fluoroquinolin-4-yl)cyclohexyl)pr- opanamide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(7-fluoroquinolin-4-yl)cyc- lohexyl)propanamide; (R)--N-(4-cyanophenyl)-2-((1S,4S)-4-(7-fluoroquinolin-4-yl)cyclohexyl)pro- panamide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(7-fluoroquinolin-4-yl)cycl- ohexyl)butanamide; N-(4-chlorophenyl)-2-((1S,4S)-4-(8-fluoroquinolin-4-yl)cyclohexyl)acetami- de; N-(4-fluorophenyl)-2-((1R,4R)-4-(8-fluoroquinolin-4-yl)cyclohexyl)acet- amide; N-(4-chlorophenyl)-2-((1S,4S)-4-(6,8-difluoroquinolin-4-yl)cyclohex- yl)acetamide; 2-((1S,4S)-4-(6,8-difluoroquinolin-4-yl)cyclohexyl)-N-(4-fluorophenyl)ace- tamide; 2-((1R,4R)-4-(6,8-difluoroquinolin-4-yl)cyclohexyl)-N-(4-fluorophe- nyl)acetamide; (R)--N-(4-fluorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)pr- opanamide; (R)--N-(4-cyanophenyl)-2-((1S,4S)-4-(8-fluoroquinolin-4-yl)cycl- ohexyl)propanamide; (R)--N-(4-chlorophenyl)-2-((1S,4S)-4-(8-fluoroquinolin-4-yl)cyclohexyl)pr- opanamide; N-(4-chlorophenyl)-2-((1R,4R)-4-(8-fluoroquinolin-4-yl)cyclohex- yl)acetamide; N-(4-fluorophenyl)-2-((1S,4S)-4-(8-fluoroquinolin-4-yl)cyclohexyl)acetami- de; N-(4-chlorophenyl)-2-(trans-4-(6-fluoroquinolin-4-yl)-1-hydroxycyclohe- xyl)propanamide; N-(4-chlorophenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)-1-hydroxycyclohexyl)p- ropanamide; N-(4-chlorophenyl)-2-(trans-1-fluoro-4-(6-fluoroquinolin-4-yl)cyclohexyl)- propanamide; N-(4-chlorophenyl)-2-(trans-4-(6-fluoroquinolin-4-yl)-4-hydroxycyclohexyl- )propanamide; N-(4-chlorophenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)-4-hydroxycyclohexyl)p- ropanamide; (R)--N-(4-chloro-2-hydroxyphenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)cyclohe- xyl)propanamide; or (R)--N-(4-chloro-3-hydroxyphenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)cyclohe- xyl)propanamide; or a stereoisomer thereof or a pharmaceutically acceptable salt thereof.

Details for Patent 9,643,972

Applicant Tradename Biologic Ingredient Dosage Form BLA Approval Date Patent No. Expiredate
Bristol-myers Squibb Company YERVOY ipilimumab Injection 125377 03/25/2011 ⤷  Try a Trial 2034-11-05
Bristol-myers Squibb Company OPDIVO nivolumab Injection 125554 12/22/2014 ⤷  Try a Trial 2034-11-05
Bristol-myers Squibb Company OPDIVO nivolumab Injection 125554 10/04/2017 ⤷  Try a Trial 2034-11-05
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Approval Date >Patent No. >Expiredate

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