IP Library › Granted Patent US 9,738,600

Granted Patent B2

US 9,738,600 · App. 15/102,098 · Granted Aug 22, 2017

ROR gamma (RORγ) modulators

Inventors: Joseph Maria Gerardus Barbara Cals (Oss, NL); Sander Bernardus Nabuurs (Oss, NL)

Assignee: LEAD PHARMA CEL MODELS IP B.V.

C07C317/44 A61K31/167 A61K31/18 A61K31/44 A61K45/06 C07C311/16 C07C311/20 C07C317/46 C07D213/75 C07C2101/02 C07C2101/04 C07C2101/08 C07C2101/14

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Quick Facts

Patent No.: US 9,738,600
App. No.: 15/102,098
Granted: Aug 22, 2017
Kind: B2

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Abstract

A 11-14 are N or CR 11-14 , respectively, maximum two of the four positions A simultaneously N; R 1 is C(1-6)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1-3)alkyl, (di)C(1-6)alkylamino, (di)C(3-6)cycloalkylamino or (di)(C(3-6)cycloalkylC(1-3)alkyl)amino, all alkyl and cycloalkyl group carbon atoms optionally substituted with F and F or methyl, respectively; R 2 and R 3 independently H, F, methyl, ethyl, hydroxy, methoxy or R 2 and R 3 together is carbonyl, all present alkyl groups optionally substituted with F; R 4 is H or C(1-6)alkyl; R 5 is H, hydroxyethyl, methoxyethyl, C(1-6)alkyl, C(6-10)aryl, C(6-10)arylC(1-3)alkyl, C(1-9)heteroaryl, C(1-9)heteroarylC(1-3)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1-3)alkyl, C(2-5)heterocycloalkyl or C(2-5)heterocycloalkylC(1-3)alkyl, all groups optionally substituted with F, Cl, C(1-2)alkyl, C(1-2)alkoxy or cyano; the sulfonyl group with R 1 represented by one of R 7-9 ; the remaining R 6-14 are independently H, halogen, C(1-3)alkoxy, (di)C(1-3)alkylamino or C(1-6)alkyl, all alkyl groups optionally substituted with F; and R 15-16 are independently H, C(1-6)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1-3)alkyl, C(6-10)aryl, C(6-10)arylC(1-3)alkyl, C(1-9)heteroaryl, C(1-9)heteroarylC(1-3)alkyl, C(2-5)heterocycloalkyl or C(2-5)heterocycloalkylC(1-3)alkyl, all groups optionally substituted with F, Cl, C(1-2)alkyl, C(1-2)alkoxy or cyano.

Claims (149)

1. A compound according to Formula I

or a pharmaceutically acceptable salt thereof wherein

A 11 -A 14 are N or CR 11 , CR 12 , CR 13 , CR 14 , respectively, with the proviso that no more than two of the four positions A can be simultaneously N;

R 1 is C(1-6)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1-3)alkyl, (di)C(1-6)alkylamino, (di)C(3-6)cycloalkylamino or (di)(C(3-6)cycloalkylC(1-3)alkyl)amino, with all carbon atoms of alkyl groups optionally substituted with one or more F and all carbon atoms of cycloalkyl groups optionally substituted with one or more F or methyl;

R 2 and R 3 are independently H, F, methyl, ethyl, hydroxy, methoxy or R 2 and R 3 together is carbonyl, all alkyl groups, if present, optionally being substituted with one or more F;

R 4 is H or C(1-6)alkyl;

R 5 is H, hydroxyethyl, methoxyethyl, C(1-6)alkyl, C(6-10)aryl, C(6-10)arylC(1-3)alkyl, C(1-9)heteroaryl, C(1-9)heteroarylC(1-3)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1-3)alkyl, C(2-5)heterocycloalkyl or C(2-5)heterocycloalkylC(1-3)alkyl, all groups optionally substituted with one or more F, Cl, C(1-2)alkyl, C(1-2)alkoxy or cyano;

the sulfonyl group with R 1 is represented by one of R 7 , R 8 or R 9 ;

the remaining R 6 -R 14 are independently H, halogen, C(1-3)alkoxy, (di)C(1-3)alkylamino or C(1-6)alkyl, all of the alkyl groups optionally being substituted with one or more F; and

R 15 and R 16 are independently H, C(1-6)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1-3)alkyl, C(6-10)aryl, C(6-10)arylC(1-3)alkyl, C(1-9)heteroaryl, C(1-9)heteroarylC(1-3)alkyl, C(2-5)heterocycloalkyl or C(2-5)heterocycloalkylC(1-3)alkyl, all groups optionally substituted with one or more F, Cl, C(1-2)alkyl, C(1-2)alkoxy or cyano.

2. The compound according to claim 1 wherein R 1 is C(1-2)alkyl, cyclopropyl, C(3-4)cycloalkylC(1-3)alkyl, methylamino or C(3-4)cycloalkylamino.

3. The compound according to claim 2 wherein R 1 is ethyl, cyclopropylamino or cyclopropylmethyl.

4. The compound according to claim 3 wherein R 1 is cyclopropylamino or cyclopropylmethyl.

5. The compound according to claim 4 wherein R 1 is cyclopropylmethyl.

6. The compound according to claim 1 wherein R 2 and R 3 are independently H, methyl or hydroxy.

7. The compound according to claim 6 wherein R 2 and R 3 are independently H or methyl.

8. The compound according to claim 1 wherein R 4 is H or C(1-2)alkyl.

9. The compound according to claim 1 where R 5 is H, hydroxyethyl, methoxyethyl or C(1-6)alkyl, all alkyl groups optionally being substituted with one or more F.

10. The compound according to claim 9 wherein R 5 is H or C(1-3)alkyl.

11. The compound according to claim 1 wherein R 5 is C(6)arylC(1-3)alkyl or C(3-6)cycloalkylC(1-3)alkyl.

12. The compound according to claim 11 wherein R 5 is benzyl.

13. The compound according to claim 1 wherein R 6 -R 10 are H with the proviso that one of the groups R 7 , R 8 or R 9 is the sulfonyl group with R 1 .

14. The compound according to claim 13 wherein R 8 is the sulfonyl group with R 1 .

15. The compound according to claim 1 wherein R 8 is the sulfonyl group with R 1 , and wherein R 10 is methyl, and the remaining R 6 , R 7 and R 9 are H.

16. The compound according to claim 1 wherein all of A 11 -A 14 are carbon.

17. The compound according to claim 1 wherein either A 11 or A 12 is nitrogen and the remaining A 11 -A 14 are carbon.

18. The compound according to claim 1 wherein R 11 -R 14 are independently H, halogen, methyl or methoxy.

19. The compound according to claim 18 wherein R 11 -R 14 is H.

20. The compound according to claim 1 wherein R 15 is CF 3 and R 16 is H, C(1-6)alkyl, C(3-6)cycloalkyl or C(3-6)cycloalkylC(1-3)alkyl.

21. The compound according to claim 20 wherein R 15 is CF 3 and R 16 is CF 3 , propyl, isopropyl, 2-methylpropyl, 2,2-dimethylpropyl, cyclopropyl, cyclopentyl or cyclohexylmethyl.

22. The compound according to claim 21 wherein both R 15 and R 16 are CF 3 .

23. The compound selected from claim 1 which is selected from the group of:

N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(methylsulfonyl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(isopropylsulfonyl)phenyl)acetamide;

N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(propylsulfonyl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)propanamide;

N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(N-methylsulfamoyl)phenyl)acetamide;

N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(N-isopropylsulfamoyl)phenyl)acetamide;

2-(4-(N-(cyclopropylmethyl)sulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(N-ethylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(N,N-dimethylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(3-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(3-(N-ethylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(3-(N,N-dimethylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(3-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylphenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-N-methylacetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-ethyl-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(3-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-N-methylacetamide;

N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(3-(N-methylsulfamoyl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(5-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methoxyphenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-2-yl)acetamide;

N-(5-chloro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methoxyphenyl)-2-(4-(ethylsulfonyl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2,6-dimethylphenyl)acetamide;

2-(3-(N-cyclobutylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(N-cyclobutylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(3-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylphenyl)acetamide;

N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(isobutylsulfonyl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(2-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-methylphenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(3-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylphenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-methylphenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(3-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylphenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(2-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(3-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-methylphenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(3-(N-cyclopropylsulfamoyl)phenyl)-N-(3-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(3-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylphenyl)acetamide;

2-(3-(N-cyclopropylsulfamoyl)phenyl)-N-(2-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(3-(N-(cyclopropylmethyl)sulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)-3-fluorophenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methylphenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-methylphenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(3-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(2-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)phenyl)acetamide;

N-(4-(2-ethoxy-1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl)-2-(4-(ethylsulfonyl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-propoxypropan-2-yl)phenyl)acetamide;

N-(4-(2-(benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl)-2-(4-(ethylsulfonyl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-isopropoxypropan-2-yl)phenyl)acetamide;

N-(4-(2-butoxy-1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(2-ethoxy-1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methoxyphenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-methoxyphenyl)acetamide;

N-(2-amino-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

N-(4-(2-(2-cyclopropylethoxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

N-(4-(2-(benzyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-propoxypropan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-propoxypropan-2-yl)phenyl)acetamide;

N-(3-chloro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxypentan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxyhexan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-3-methylbutan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-4-methylpentan-2-yl)phenyl)acetamide;

N-(4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxyethyl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

N-(4-(3-cyclopentyl-1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

N-(4-(3-cyclohexyl-1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxyhexan-2-yl)phenyl)acetamide;

N-(4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxyethyl)phenyl)-2-(4-(ethylsulfonyl)phenyl)acetamide;

N-(4-(3-cyclohexyl-1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(ethylsulfonyl)phenyl)acetamide;

N-(4-(1-cyclopentyl-2,2,2-trifluoro-1-hydroxyethyl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-4-methylpentan-2-yl)phenyl)acetamide;

2-(3-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-4-methylpentan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxybutan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxypentan-2-yl)phenyl)acetamide;

2-(3-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxypentan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-4,4-dimethylpentan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxybutan-2-yl)phenyl)acetamide;

N-(3-chloro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(ethylsulfonyl)phenyl)acetamide;

N-(4-(1-cyclopentyl-2,2,2-trifluoro-1-hydroxyethyl)phenyl)-2-(4-(ethylsulfonyl)phenyl)acetamide;

N-(4-(3-cyclopentyl-1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(ethylsulfonyl)phenyl)acetamide;

2-(4-cyclopropylmethanesulfonylphenyl)-N-[4-(1,1,1-trifluoro-2-hydroxy-3-phenylpropan-2-yl)phenyl]acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl)acetamide;

N-(3-chloro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(N-cyclopropylsulfamoyl)phenyl)acetamide;

N-(4-(1-cyclopentyl-2,2,2-trifluoro-1-hydroxyethyl)phenyl)-2-(4-(N-cyclopropylsulfamoyl)phenyl)acetamide;

N-(3-chloro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(3-(N-cyclopropylsulfamoyl)phenyl)acetamide;

N-(4-(1-cyclopentyl-2,2,2-trifluoro-1-hydroxyethyl)phenyl)-2-(3-(N-cyclopropylsulfamoyl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)-2-methylphenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-4,4-dimethylpentan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-3-methylbutan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-4,4-dimethylpentan-2-yl)phenyl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl)acetamide;

N-(2-chloro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-((cyclopropylmethyl)sulfonyl)phenyl)acetamide;

N-(4-(3-cyclopentyl-1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(N-cyclopropylsulfamoyl)phenyl)acetamide;

N-(4-(3-cyclohexyl-1,1,1-trifluoro-2-hydroxypropan-2-yl)phenyl)-2-(4-(N-cyclopropylsulfamoyl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-oxoacetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(2-hydroxypropan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-5-methylhexan-2-yl)phenyl)acetamide;

2-(4-(N-cyclopropylsulfamoyl)phenyl)-N-(5-fluoro-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methoxyphenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(dicyclopropyl(hydroxy)methyl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-2-yl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1-trifluoro-2-hydroxy-6-methylheptan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)propanamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-3-yl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl) pyridin-3-yl)acetamide;

2-(4-(ethylsulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-(2,2,2-trifluoroethoxy)propan-2-yl)phenyl)acetamide;

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-(2,2,2-trifluoroethoxy)propan-2-yl)phenyl)acetamide and

2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl)-2-hydroxyacetamide.

24. The compound according to claim 23 which is 2-(4-((cyclopropylmethyl)sulfonyl)phenyl)-N-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxy propan-2-yl)phenyl)acetamide.

25. A pharmaceutical composition which comprises a compound of Formula I according to claim 1 or a pharmaceutically acceptable salt thereof and one or more pharmaceutically acceptable excipients.

26. A pharmaceutical composition according to claim 25 , which further comprises at least one additional therapeutically active agent.

Assignments (2)

MERGER AND CHANGE OF NAME Recorded Mar 15, 2018

From: LEAD PHARMA CEL MODELS IP B.V.; LEAD PHARMA HOLDING B.V.

To: LEAD PHARMA HOLDING B.V.

Reel/Frame 046560/0436 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2016

From: CALS, JOSEPH MARIA GERARDUS BARBARA; NABUURS, SANDER BERNARDUS

To: LEAD PHARMA CEL MODELS IP B.V.

Reel/Frame 039136/0605 →

Priority Claims (2)

EP 13195813 · Dec 5, 2013 · regional

EP 14183274 · Sep 2, 2014 · regional

Continuity (1)

Related Publication 20160304448A1 · Oct 20, 2016