BENZENESULFONAMIDE DERIVATIVES AS INVERSE AGONISTS OF RETINOID-RELATED ORPHAN RECEPTOR GAMMA (ROR GAMMA (T))

• US 20180170869A1
• Filed: 12/18/2015
• Published: 06/21/2018
• Est. Priority Date: 12/19/2014
• Status: Active Grant

• Current Assignee: Galderma Research And Development Snc (Nestle SA)
• Original Assignee: Galderma Research And Development Snc (Nestle SA)
• Inventors: MUSICKI, Branislav, BOUIX-PETER, Claire, OUVRY, Gilles, THOREAU, Etienne
• Granted Patent: US 10,457,637 B2
• Time in Patent Office: Days
• CPC Class Codes: A61P 17/10 Anti-acne agents
• CPC Class Codes: C07C 311/29 having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 381/10 Compounds containing sulfur atoms doubly-bound to nitrogen atoms
• CPC Class Codes: C07D 207/26 2-Pyrrolidones
• CPC Class Codes: C07D 211/22 by oxygen atoms
• CPC Class Codes: C07D 211/46 having a hydrogen atom as the second substituent in position 4
• CPC Class Codes: C07D 211/76 attached in position 2 or 6
• CPC Class Codes: C07D 211/96 Sulfur atom
• CPC Class Codes: C07D 213/30 Oxygen atoms
• CPC Class Codes: C07D 261/08 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 263/20 attached in position 2
• CPC Class Codes: C07D 263/24 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
• CPC Class Codes: C07D 271/08 1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
• CPC Class Codes: C07D 279/16 condensed with one six-membered ring
• CPC Class Codes: C07D 295/096 with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• CPC Class Codes: C07D 305/06 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
• CPC Class Codes: C07D 305/08 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms
• CPC Class Codes: C07D 307/93 condensed with a ring other than six-membered
• CPC Class Codes: C07D 309/04 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 309/06 Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 309/08 : with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 309/12 : only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
• CPC Class Codes: C07D 333/48 : by oxygen atoms
• CPC Class Codes: C07D 335/02 : not condensed with other rings
• CPC Class Codes: C07D 417/06 : linked by a carbon chain containing only aliphatic carbon atoms

Abstract

Benzenesulfonamide derivatives of formula (I), the pharmaceutically acceptable addition salts thereof, the hydrates and/or solvates thereof, and the use of same as inverse agonist of retinoid-related orphan receptor gamma (RORγt) are described. A pharmaceutical composition including such compounds, as well as the use thereof for the topical and/or oral treatment of RORγt receptor-medicated inflammatory diseases, in particular acne, psoriasis and/or atopic dermatitis are also described.

Claims

1. Compound of formula (I), and also the pharmaceutically acceptable addition salts thereof, hydrates thereof and/or solvates thereof:

2. Compound of formula (I) as claimed in claim 1, chosen from the compounds of formula (Ia) and/or (Ib) below:

3. Compound as claimed in claim 1 or 2, characterized in that L represents a single bond.

4. Compound of formula (I) as claimed in any one of claims 1 to 3, characterized in that R⁶ represents a heterocyclic radical chosen from the following heterocycles:

5. Compound of formula (I) as claimed in any one of claims 1 to 3, characterized in that R⁶ represents an aromatic or heteroaromatic radical chosen from:

6. Compound of formula (I) as claimed in any one of claims 1 to 5, characterized in that it is chosen from the compounds of formula (II) below:

7. The compound of formula (I) as claimed in any one of claims 1 to 5, characterized in that it is chosen from the compounds of formula (III) below:

8. Compound as claimed in any one of the preceding claims, characterized in that it is chosen from the following compounds, and also the pharmaceutically acceptable addition salts thereof, hydrates thereof and/or solvates thereof:

9. Compound as claimed in any one of the preceding claims, characterized in that it is chosen from:

10. Compound as claimed in any one of the preceding claims, as a medicament.

11. Compound as claimed in any one of the preceding claims, for its use in the treatment of inflammatory disorders and/or autoimmune diseases mediated by the RORγ

t receptor.

12. Compound as claimed in claim 10, for its use in the treatment of acne.

13. Compound as claimed in claim 10, for its use in the treatment of psoriasis.

14. Pharmaceutical composition comprising one or more compounds as defined in any one of claims 1 to 10.

15. Pharmaceutical composition as claimed in claim 14, characterized for its use for treating inflammatory disorders and/or autoimmune diseases mediated by the RORγ

t receptor, especially acne, atopic dermatitis and/or psoriasis.