Benzenesulfonamide derivatives as inverse agonists of retinoid-related orphan receptor gamma (RORγ(T))

• US 10,457,637 B2
• Filed: 12/18/2015
• Issued: 10/29/2019
• 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
• Primary Examiner(s): Kifle, Bruck
• Application Number:
  US15/537,667
• Publication Number:
  US 20180170869A1
• Time in Patent Office: 1,411 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. A compound of formula (II), or a pharmaceutically acceptable addition salt thereof:

2. The compound of formula (II) as defined by claim 1, or the pharmaceutically acceptable addition salt thereof, wherein R⁶ represents a heterocyclic radical selected from the group consisting of:

3. The compound of formula (II) as defined by claim 1, or the pharmaceutically acceptable addition salt thereof, wherein R⁶ represents an aromatic or heteroaromatic radical selected from the group consisting of

4. The compound as defined by claim 1, wherein the compound is selected from the group consisting of the following compounds:

5. The compound as defined by claim 1, wherein the compound is selected from the group consisting of:

6. The compound as defined by claim 1, wherein the compound is selected from the group consisting of:

7. A method of treating an inflammatory disorder and/or autoimmune disease, the method comprising administering an effective amount of the compound as defined by claim 1, or the pharmaceutically acceptable addition salt thereof, to an individual subject in need thereof, wherein the inflammatory disorder and/or autoimmune disease is acne, atopic dermatitis and/or psoriasis.

8. A method of treating acne, the method comprising administering an effective amount of the compound as defined by claim 1, or the pharmaceutically acceptable addition salt thereof, to an individual subject in need thereof.

9. A method of treating psoriasis, the method comprising administering an effective amount of the compound as defined by claim 1, or a pharmaceutically acceptable addition salt thereof, to an individual subject in need thereof.

10. A pharmaceutical composition comprising one or more compounds as defined by claim 1 or a pharmaceutically acceptable addition salt thereof, and a pharmaceutically acceptable carrier.

11. The pharmaceutical composition as defined by claim 10, wherein the composition is formulated for treating is acne, atopic dermatitis and/or psoriasis.

12. The pharmaceutical composition as defined by claim 11, wherein the composition is formulated for treating acne.

13. The pharmaceutical composition as defined by claim 11, wherein the composition is formulated for treating atopic dermatitis.

14. The pharmaceutical composition as defined by claim 11, wherein the composition is formulated for treating psoriasis.

15. A method of treating atopic dermatitis, the method comprising administering an effective amount of the compound as defined by claim 1, or the pharmaceutically acceptable addition salt thereof, to an individual subject in need thereof.