IP Library Granted Patent US 10,196,354
Granted Patent B2
US 10,196,354 · App. 15/647,437 · Granted Feb 5, 2019

4-heteroaryl substituted benzoic acid compounds as RORgammaT inhibitors and uses thereof

Inventors: Kenneth J. Barr (Boston, MA); Corey E. Bienstock (Natick, MA); John K. Maclean (Brookline, MA); Hongjun Zhang (Newton, MA); Richard T. Beresis (Shanghai, CN); Dongshan Zhang (Shanghai, CN); Neville J. Anthony (Northborough, MA); Blair T. Lapointe (Brookline, MA); Yuan Tian (Boston, MA)
Assignee: Merck Sharp & Dohme Corp.
C07D209/26A61K31/404A61K31/416A61K31/437A61K31/4439A61K31/5377C07D231/56C07D401/04C07D401/06C07D403/04C07D403/06C07D405/06C07D405/12C07D409/04C07D413/04C07D413/06C07D417/04C07D471/04Y02A50/409
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,196,354
App. No.
15/647,437
Granted
Feb 5, 2019
Kind
B2
Abstract

The present invention relates to compounds according to Formula I (Formula I), and pharmaceutically acceptable salts or solvates thereof. Such compounds can be used in the treatment of RORgammaT-mediated diseases or conditions.

Claims (186)

1. A compound according to Formula I

or a pharmaceutically acceptable salt or solvate thereof, wherein:

Y is CH, CR a , or N;

n=0, 1, 2, 3 or 4;

R a is (C 1-4 )alkyl or (C 3-7 )cycloalkyl;

R 1 is

(i) (C 3-12 )carbocyclyl(C 0-4 )alkyl, or

(ii) a 4- to 12-membered heterocyclyl(C 0-4 )alkyl,

each being substituted with (i) one occurrence of R 8 that is (C 3-7 ) cycloalkyl and (ii) optionally one, two, three, or four other occurrences of R 8 ;

R 2 is hydroxycarbonyl, hydroxycarbonyl(C 1-10 )alkyl, (C 1-10 )alkylsulfoxyaminocarbonyl, or carbamoyl;

R 3 is hydrogen, halogen, cyano, hydroxy, (C 1-4 )alkylcarbonyloxy, (C 1-4 ) alkylsulfonylamino, (C 1-4 ) alkylcarbonylamino, (C 1-4 )alkyl, or (C 1-4 )alkoxy, wherein (C 1-4 )alkyl and (C 1-4 )alkoxy are optionally substituted with one or more halogen;

R 4 -R 7 independently are hydrogen, halogen, amino, cyano, hydroxy, (C 1-3 )alkoxy, (C 1-4 )-alkyl, (C 0-10 )alkylaminocarbonyl, (C 0-6 )alkyoxycarbonylamino, (di)(C 1-6 )alkylaminocarbonyl, (C 1-6 )alkylcarbonylamino, (C 1-4 )alkylamino, or amino(C 1-4 )alkyl, wherein (C 1-3 )alkoxy and (C 1-4 )alkyl are optionally substituted with one or more halogen; or a group having the formula

 optionally substituted with one or more of the following: (C 1-10 )alkyl, halogen, amino, cyano, hydroxy, (C 1-3 )alkoxy, and wherein m is 1, 2, 3, or 4; or

R 6 is additionally selected from:

(i) (C 3-7 )cycloalkyl or (C 3-5 )heterocycloalkyl, both optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, oxo (═O), (C 1-4 )alkyl or (C 1-3 )alkoxy;

(ii) (C 2-9 )heteroaryl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(iii) (C 6-14 )aryl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(iv) (C 3-5 )heterocycloalkylcarbonyl or (C 3-5 )heterocycloalkylcarbonyl(C 1-4 )alkyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(v) (C 3-5 )heterocycloalkylamino, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(vi) (C 3-5 )cycloalkylaminocarbonyl or di(C 3-5 )cycloalkylaminocarbonyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(vii) (C 3-5 )cycloalkylcarbonylamino, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(viii) (C 3-5 )cycloalkyl(C 1-4 )alkyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(ix) (C 3-5 )cycloalkylamino, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(x) (C 3-5 )cycloalkylcarbonyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(xi) (C 2-9 )heteroaryl(C 1-4 )alkyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(xii) (C 2-9 )heteroarylcarbonyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

and

R 8 is halogen, cyano, amino, hydroxy, di(C 1-3 )alkylamino, (C 1-4 )alkyl, (C 3-5 )heterocycloalkyl, (C 1-4 )alkenyl, (C 3-6 )cycloalkoxy or (C 1-3 )alkoxy, wherein (C 1-4 )alkyl and (C 1-3 )alkoxy are optionally substituted with one, two or three halogens.

2. The compound of claim 1 having Formula Ia

or a pharmaceutically acceptable salt or solvate thereof.

3. The compound of claim 1 having Formula Ib

or a pharmaceutically acceptable salt or solvate thereof.

4. The compound of claim 3 , wherein Y is N.

5. The compound of claim 3 having Formula Ic

or a pharmaceutically acceptable salt or solvate thereof.

6. The compound of claim 5 having Formula Id

or a pharmaceutically acceptable salt or solvate thereof.

7. The compound of claim 6 , wherein Y is N.

8. The compound of claim 2 having Formula Ie

wherein x is 1, 2, 3, 4 or 5; and at least one occurrence of R 8 is (C 3-7 )cycloalkyl;

or a pharmaceutically acceptable salt or solvate thereof.

9. The compound of claim 8 having Formula If

or a pharmaceutically acceptable salt or solvate thereof; wherein at least one occurrence of R 8 is (C 3-7 )cycloalkyl.

10. The compound of claim 9 having Formula Ig

or a pharmaceutically acceptable salt or solvate thereof; wherein at least one occurrence of R 8 is (C 3-7 )cycloalkyl.

11. The compound of claim 10 having Formula Ih

or a pharmaceutically acceptable salt or solvate thereof; wherein R 8 is (C 3-7 )cycloalkyl.

12. The compound of claim 1 , wherein Y is N.

13. The compound of claim 1 , wherein R 1 is

(i) (C 3-7 )cycloalkyl or (C 3-5 )heterocycloalkyl, both being substituted with (i) one occurrence of R 8 that is (C 3-7 )cycloalkyl and (ii) optionally one, two, three, or four other occurrences of or five R 8 ;

(ii) (C 2-9 )heteroaryl(C 0-4 )alkyl, being substituted with (i) one occurrence of R 8 that is (C 3-7 )cycloalkyl and (ii) optionally one, two, three, or four other occurrences of R 8 ; or

(iii) (C 6-14 )aryl(C 0-4 )alkyl, being substituted with (i) one occurrence of R 8 that is (C 3-7 )cycloalkyl and (ii) optionally one, two, three, or four other occurrences of R 8 .

14. The compound of claim 13 , wherein R 1 is (i) (C 2-9 )heteroaryl, or (ii) (C 6-14 )aryl, both substituted with (i) one occurrence of R 8 that is (C 3-7 )cycloalkyl and (ii) optionally one, two, three, or four other occurrences of R 8 .

15. The compound of claim 14 , wherein R 1 is (C 6-14 )aryl substituted with (i) one occurrence of R 8 that is (C 3-7 )cycloalkyl and (ii) optionally one other occurrence of R 8 .

16. The compound of claim 15 , wherein R 1 is phenyl substituted with (i) one occurrence of R 8 that is (C 3-7 )cycloalkyl and (ii) optionally one other occurrence of R 8 .

17. The compound of claim 16 , wherein R 2 is C(O)OH.

18. The compound of claim 1 , wherein R 6 is

19. A compound selected from:

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-4-formyl-1H-indazol-3-yl)benzoic acid;

3-fluoro-4-(1-(2-phenylpropanoyl)-1H-indazol-3-yl)benzoic acid;

3-fluoro-4-[1-(methoxyacetyl)-1H-indazol-3-yl]benzoic acid;

3-fluoro-4-[1-(pyridin-3-ylcarbonyl)-1H-indazol-3-yl]benzoic acid;

3-fluoro-4-{1-[(2-oxopyrrolidin-1-yl)acetyl]-1H-indazol-3-yl}benzoic acid;

3-fluoro-4-[1-(naphthalen-1-ylcarbonyl)-1H-indazol-3-yl]benzoic acid;

3-fluoro-4-{1-[(1-methyl-1H-indol-2-yl)carbonyl]-1H-indazol-3-yl}benzoic acid;

4-{1-[(2-bromo-3-methylphenyl)carbonyl]-1H-indazol-3-yl}-3-fluorobenzoic acid;

4-[1-(2,3-dihydro-1H-inden-4-ylcarbonyl)-1H-indazol-3-yl]-3-fluorobenzoic acid;

4-(1-{[3-(tertbutoxycarbonyl)-3-azabicyclo[3.1.0]hex-6-yl]carbonyl}-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-[1-(2,3-dihydro-1-benzofuran-7-ylcarbonyl)-1H-indazol-3-yl]-3-fluorobenzoic acid;

4-[1-(1-benzofuran-7-ylcarbonyl)-1H-indazol-3-yl]-3-fluorobenzoic acid;

4-{1-[(2-bromo-3-chlorophenyl)carbonyl]-1H-indazol-3-yl}-3-fluorobenzoic acid;

3-fluoro-4-(1-(tetrahydrofuran-2-carbonyl)-1H-indazol-3-yl)benzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(morpholine-4-carbonyl)-1H-indazol-3-yl)benzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-((2S,6R)-2,6-dimethylmorpholine-4-carbonyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(4-oxopiperidine-1-carbonyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

2-acetamido-4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol -3-yl)benzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl) benzoyl)-6-(3-hydroxyazetidin-1-yl)-1H-indazol-3-yl)benzoic acid;

4-(6-(azetidin-1-yl)-1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(cyclopropylamino)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(oxetan-3-ylamino)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(3-hydroxypyrrolidin-1-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-morpholino-1H-indazol-3-yl)benzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(methoxycarbonylamino)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(N-methylacetamido)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(cyclopropanecarboxamido)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(methylsulfonamido)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(3-methylureido)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(6-acetamido-1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(N-methylmethylsulfonamido)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(1,3-dimethylureido)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(2-oxo-imidazolidin-1-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(2-oxoazetidin-1-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(6-(2-carboxyethylamino)-1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(3-methyl-2-oxoimidazolidin-1-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(2-oxopyrrolidin-1-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(morpholine-4-carbonyl)-1H-indazol-3-yl)benzoic acid;

3-(4-carboxyphenyl)-1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazole-6-carboxylic acid;

sodium 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(5-methyloxazol-2-yl)-1H-indazol-3-yl)benzoate;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(5-methyloxazol-2-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(3-hydroxyprop-1-ynyl)-1H-indazol-3-yl)benzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(3-hydroxybut-1-ynyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(6-(3-aminoprop-1-ynyl)-1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-ethynyl-1H-indazol-3-yl)benzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(5-(hydroxymethyl)oxazol-2-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(1-methyl-1H-imidazol-4-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(oxazol-2-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(6-(5-bromooxazol-2-yl)-1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

(E)-4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(N′-cyano-N,N-dimethylcarbamimidoyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(4H-1,2,4-triazol-3-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(1-methyl-1H-imidazol-2-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(1-methyl-1H-imidazol-5-yl)-1H-indazol-3-yl]benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(5-methylthiophen-3-yl)-1H-indazol-3-yl]benzoic acid;

4-(1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-pyrimidin-2-yl-1H-indazol-3-yl)benzoic acid;

4-(1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-pyrimidin-4-yl-1H-indazol-3-yl)benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(1-methyl-1H-imidazol-4-yl)-1H-indazol-3-yl]benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(1,3-thiazol-4-yl)-1H-indazol-3-yl]benzoic acid;

4-(6-[4-(aminomethyl)pyridin-2-yl]-1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-1H-indazol-3-yl)benzoic acid;

4-(1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-pyridin-2-yl-1H-indazol-3-yl)benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(1,3-thiazol-5-yl)-1H-indazol-3-yl]benzoic acid;

4-(1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-pyridin-4-yl-1H-indazol-3-yl)benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(4-cyanophenyl)-1H-indazol-3-yl]benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(3-cyanophenyl)-1H-indazol-3-yl]benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(2-cyanophenyl)-1H-indazol-3-yl]benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(2-fluorophenyl)-1H-indazol-3-yl]benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(3-fluorophenyl)-1H-indazol-3-yl]benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(4-fluorophenyl)-1H-indazol-3-yl]benzoic acid;

4-[1-{[2-chloro-6-(trifluoromethyl)phenyl]carbonyl}-6-(1-methyl-1H-pyrazol-5-yl)-1H-indazol-3-yl]benzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(methylsulfonamidomethyl)-1H-indazol-3-yl)benzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(2,5-dioxoimidazolidin-4-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(4-chloro-1-(2-chloro-6-cyclopropylbenzoyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-cyclopropylbenzoyl)-4-fluoro-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-cyclopropylbenzoyl)-1H-indazol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-2-methyl-1H-indol-3-yl)-3-fluorobenzoic acid;

4-(2-methyl-1-(2-(trifluoromethyl)benzoyl)-1H-indol-3-yl)benzoic acid;

4-(1-(2-chloro-6-cyclopropylbenzoyl)-1H-indazol-3-yl)-3,5-difluorobenzoic acid;

4-(1-(2-chloro-6-cyclopropylbenzoyl)-4-fluoro-1H-indazol-3-yl)-3,5-difluorobenzoic acid;

4-(6-(azetidine-1-carbonyl)-1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indol-3-yl)-3-fluorobenzoic acid;

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(3-methoxy-azetidine-1-carbonyl)-1H-indol-3-yl)-3-fluorobenzoic acid; and

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-6-(oxetan-3-yl)-1H-indazol-3-yl)-3-fluorobenzoic acid.

20. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt or solvate thereof, and one or more pharmaceutically acceptable excipients.

21. A method for treating a disease or condition mediated by RORgammaT in a subject, comprising administering to the subject an amount of a compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, that is effective for treating the disease or condition mediated by RORgammaT in the subject, wherein the disease or condition is an autoimmune disease or inflammatory disease.

22. A method for treating a disease or condition mediated by RORgammaT in a subject, comprising administering to the subject an amount of a compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, that is effective for treating the disease or condition mediated by RORgammaT in the subject, wherein the disease or condition is multiple sclerosis, inflammatory bowel disease, Crohn's disease, ankylosing spondylitis, psoriasis, rheumatoid arthritis, asthma, osteoarthritis, Kawasaki disease, Hashimoto's thyroiditis, or mucosal leishmaniasis.

23. The compound of claim 7 , wherein:

R 2 is C(O)OH;

R 3 is hydrogen or halogen; and

R 4 , R 5 , and R 7 are hydrogen or halogen.

24. The compound of claim 23 , wherein R 6 is (C 3-5 )heterocycloalkylcarbonyl or (C 3-5 )heterocycloalkylcarbonyl(C 1-4 )alkyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy.

25. A pharmaceutical composition comprising a compound of claim 24 or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.

26. A compound according to the Formula:

or a pharmaceutically acceptable salt or solvate thereof, wherein:

Y is CH, CR a , or N;

n=0, 1, 2, 3 or 4;

R a is (C 1-4 )alkyl or (C 3-7 )cycloalkyl;

R 1 is

(i) (C 3-12 )carbocyclyl(C 0-4 )alkyl, or

(ii) a 4- to 12-membered heterocyclyl(C 0-4 )alkyl,

each optionally substituted with one, two, three, four or five R 8 ;

R 2 is hydroxycarbonyl, hydroxycarbonyl(C 1-10 )alkyl, (C 1-10 )alkylsulfoxyaminocarbonyl, or carbamoyl;

R 3 is hydrogen, halogen, cyano, nitro, hydroxy, (C 1-4 )alkylcarbonyloxy, (C 1-4 ) alkylcarbonylamino, (C 1-4 )alkyl, or (C 1-4 )alkoxy, wherein (C 1-4 )alkyl and (C 1-4 )alkoxy are optionally substituted with one or more halogen;

R 4 , R 5 , and R 7 independently are hydrogen, halogen, amino, cyano, hydroxy, (C 1-3 )alkoxy, (C 1-4 )alkyl, (C 0-10 )alkylaminocarbonyl, (C 0-6 )alkyoxycarbonylamino, (di)(C 1-6 )alkylaminocarbonyl, (C 1-6 )alkylcarbonylamino, (C 1-4 )alkylamino, or amino(C 1-4 )alkyl, wherein (C 1-3 )alkoxy and (C 1-4 )alkyl are optionally substituted with one or more halogen; or a group having the formula

 optionally substituted with one or more of the following: (C 1-10 )alkyl, halogen, amino, cyano, hydroxy, (C 1-3 )alkoxy, and wherein m is 1, 2, 3, or 4;

R 6 is:

(i) (C 3-7 )cycloalkyl or (C 3-5 )heterocycloalkyl, both optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, oxo (═O), (C 1-4 )alkyl or (C 1-3 )alkoxy;

(ii) (C 2-9 )heteroaryl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(iii) (C 6-14 )aryl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(iv) (C 3-5 )heterocycloalkylamino, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(v) (C 3-5 )cycloalkyl(C 1-4 )alkyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(vi) (C 3-5 )cycloalkylamino, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(vii) (C 3-5 )cycloalkylcarbonyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(viii) (C 2-9 )heteroaryl(C 1-4 )alkyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(ix) (C 2-9 )heteroarylcarbonyl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

and

R 8 is halogen, cyano, amino, hydroxy, di(C 1-3 )alkylamino, (C 1-4 )alkyl, (C 3-5 )heterocycloalkyl, (C 1-4 )alkenyl, (C 3-6 )cycloalkoxy or (C 1-3 )alkoxy, wherein (C 1-4 )alkyl and (C 1-3 )alkoxy are optionally substituted with one, two or three halogens.

27. The compound of claim 26 , wherein:

Y is N;

R 2 is C(O)OH;

R 3 is hydrogen or halogen; and

R 4 , R 5 , and R 7 are hydrogen or halogen.

28. The compound of claim 27 , wherein R 6 is:

(i) (C 3-7 )cycloalkyl or (C 3-5 )heterocycloalkyl, both optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy;

(ii) (C 2-9 )heteroaryl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 )alkyl or (C 1-3 )alkoxy; or

(iii) (C 6-14 )aryl, optionally substituted with one or more groups selected from halogen, amino, amino(C 1-4 )alkyl, cyano, hydroxyl, (C 1-4 alkyl or (C 1-3 )alkoxy.

29. A pharmaceutical composition comprising a compound of claim 26 or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.

Assignments (8)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
SECURITY INTEREST Recorded Jan 3, 2019
From: LYCERA CORP.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 048002/0201 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2018
From: BARR, KENNETH JAY; BIENSTOCK, COREY; MACLEAN, JOHN; ZHANG, HONGJUN
To: MERCK SHARP & DOHME CORP.
Reel/Frame 046341/0727 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2018
From: BERESIS, RICHARD THOMAS; ZHANG, DONGSHAN
To: SHANGHAI CHEMPARTNER CO. LTD.
Reel/Frame 046341/0752 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2018
From: BERESIS, RICHARD THOMAS; ZHANG, DONGSHAN
To: SHANGHAI CHEMPARTNER CO. LTD.
Reel/Frame 046341/0778 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2018
From: SHANGHAI CHEMPARTNER CO. LTD.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 046341/0786 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2018
From: SHANGHAI CHEMPARTNER CO. LTD.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 046341/0791 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2018
From: BARR, KENNETH JAY; BIENSTOCK, COREY; MACLEAN, JOHN; ZHANG, HONGJUN; ANTHONY, NEVILLE; LAPOINTE, BLAIR; TIAN, YUAN
To: MERCK SHARP & DOHME CORP.
Reel/Frame 046341/0695 →
Priority Claims (1)
WO PCT/CN2012/080131 · Aug 15, 2012 · international
Continuity (2)
Continuation 14421048
Related Publication 20180022701A1 · Jan 25, 2018