IP Library Granted Patent US 10,196,350
Granted Patent B2
US 10,196,350 · App. 15/829,226 · Granted Feb 5, 2019

ROR gamma (RORγ) modulators

Inventors: Joseph Maria Gerardus Barbara Cals (Oss, NL); David Machnik (Paris, FR); Sander Bernardus Nabuurs (Oss, NL); Jean-Francois Sabuco (Paris, FR)
Assignees: LEAD PHARMA HOLDING B.V.; SANOFI
C07C317/32A61K31/10A61K31/167A61P1/00A61P17/00A61P19/02A61P25/00C07C315/04C07C317/44C07C317/46C07C2601/02
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Quick Facts
Patent No.
US 10,196,350
App. No.
15/829,226
Granted
Feb 5, 2019
Kind
B2
Abstract

The present application relates to compounds according to (Formula IA) or (Formula IB): or a pharmaceutically acceptable salt thereof. The compounds can be used as inhibitors of RORγ and are useful for the treatment of RORγ mediated diseases.

Claims (25)

1. A compound of formula (I):

or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein the absolute configuration corresponds to a compound of Formula (IA), 2-{4-[(cyclopropylmethyl)sulfonyl]phenyl}-N-{4-[(1R)-1-(difluoromethyl)-2,2,2-trifluoro-1-hydroxyethyl]phenyl}acetamide:

3. The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein the absolute configuration corresponds to a compound of Formula (IB), 2-{4-[(cyclopropylmethyl)sulfonyl]phenyl}-N-{4-[(1S)-1-(difluoromethyl)-2,2,2-trifluoro-1-hydroxyethyl]phenyl}acetamide:

4. A compound of formula (VI):

wherein the compound is selected from the group consisting of:

2-[4-(cyclopropylmethylsulfinyl)phenyl]-N-[4-[1-(difluoromethyl)-2,2,2-trifluoro-1-hydroxy-ethyl]phenyl]acetamide;

(−)-2-[4-[(S)-cyclopropylmethylsulfinyl]phenyl]-N-[4-[(1R)-1-(difluoromethyl)-2,2,2-trifluoro-1-hydroxy-ethyl]phenyl]acetamide;

(−)-2-[4-[(S)-cyclopropylmethylsulfinyl]phenyl]-N-[4-[(1S)-1-(difluoromethyl)-2,2,2-trifluoro-1-hydroxy-ethyl]phenyl]acetamide;

(+)-2-[4-[(R)-cyclopropylmethylsulfinyl]phenyl]-N-[4-[(1R)-1-(difluoromethyl)-2,2,2-trifluoro-1-hydroxy-ethyl]phenyl]acetamide; and

(+)-2-[4-[(R)-cyclopropylmethylsulfinyl]phenyl]-N-[4-[(1S)-1-(difluoromethyl)-2,2,2-trifluoro-1-hydroxy-ethyl]phenyl]acetamide,

or a pharmaceutically acceptable salt thereof.

5. A process of preparing the compound of Formula (I) according to claim 1 , comprising reacting an amine of formula (II)

with a compound of formula (III):

to generate the compound of Formula (I).

6. A method for treatment of rheumatoid arthritis, psoriasis, inflammatory bowel disease, Crohn's disease or multiple sclerosis comprising administering to a patient in need thereof an effective amount of the compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

7. A method for treatment of rheumatoid arthritis, psoriasis, inflammatory bowel disease, Crohn's disease or multiple sclerosis comprising administering to a patient in need thereof an effective amount of the compound according to claim 4 , or a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition comprising the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.

9. The pharmaceutical composition comprising the compound according to claim 4 , or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.

10. A method for treatment of osteoarthritis or asthma comprising administering to a patient in need thereof an effective amount of the compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

11. A method for treatment of osteoarthritis or asthma comprising administering to a patient in need thereof an effective amount of the compound according to claim 4 , or a pharmaceutically acceptable salt thereof.

12. A method for treatment of mucosal leishmaniasis comprising administering to a patient in need thereof an effective amount of the compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

13. A method for treatment of mucosal leishmaniasis comprising administering to a patient in need thereof an effective amount of the compound according to claim 4 , or a pharmaceutically acceptable salt thereof.

14. A method for treatment of Kawaski disease or Hashimoto's thyroiditis comprising administering to a patient in need thereof an effective amount of the compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

15. A method for treatment of Kawaski disease or Hashimoto's thyroiditis comprising administering to a patient in need thereof an effective amount of the compound according to claim 4 , or a pharmaceutically acceptable salt thereof.

Assignments (4)
CHANGE OF ADDRESS Recorded Jul 3, 2024
From: SANOFI
To: SANOFI
Reel/Frame 068105/0767 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 22, 2018
From: CALS, JOSEPH MARIA GERARDUS BARBARA; NABUURS, SANDER BERNARDUS
To: LEAD PHARMA HOLDING B.V.
Reel/Frame 044692/0358 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 22, 2018
From: MACHNIK, DAVID; SABUCO, JEAN-FRANÇOIS
To: SANOFI-AVENTIS RECHERCHE & DEVELOPPEMENT
Reel/Frame 044692/0361 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 22, 2018
From: SANOFI-AVENTIS RECHERCHE & DEVELOPPEMENT
To: SANOFI
Reel/Frame 044692/0382 →
Priority Claims (1)
EP 16202175 · Dec 5, 2016 · regional
Continuity (1)
Related Publication 20180162808A1 · Jun 14, 2018