IP Library Granted Patent US 11,919,854
Granted Patent B2
US 11,919,854 · App. 17/042,806 · Granted Mar 5, 2024

P2RX7 modulators in therapy

Inventors: Valérie Vouret (Nice, FR); Laetitia Douguet (Bailly, FR); Alina Ghinet (Lomme, FR); Germain Homerin (Lille, FR); Benoît Guy Marie Rigo (Lille, FR); Davy Jérémy Baudelet (Paris, FR); Xavier Dezitter (Marchiennes, FR); Régis Millet (Harnes, FR); Christophe Furman (Marcq en Baroeul, FR)
Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; CHRU DE LILLE; UNIVERSITE COTE D'AZUR; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); UNIVERSITE DE LILLE; JUNIA
C07D207/16A61K31/4015A61K31/4025A61K31/4439A61K39/395A61P1/00A61P35/00C07D401/12C07D409/12
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Quick Facts
Patent No.
US 11,919,854
App. No.
17/042,806
Granted
Mar 5, 2024
Kind
B2
Abstract

The present invention relates to compounds of formula (I), their enantiomers and their pharmaceutically acceptable salts, and their use in therapy, particularly for the treatment of cancer or inflammatory diseases.

Claims (26)

1. A compound chosen from compounds of formula (I), their enantiomers and their pharmaceutically acceptable salts:

in which:

R1 represents a C1 -C14 alkyl, a cycloalkyl group, a phenyl or biphenyl group, a benzyl group or a heteroaryl group selected from the group consisting of pyridine and thiophene, wherein said phenyl, biphenyl, benzyl or heteroaryl group is optionally substituted with at least one group selected from the group consisting of:

halogen atoms;

C1-C6 alkoxy radicals;

C1-C6 alkyl radicals; and

C1-C6 halogenoalkyl radicals, and

R2 represents an aryl group that is a phenyl, an aralkyl group that is a benzyl or phenethyl, or a cycloalkyl group, wherein said aryl group or said aralkyl group is optionally substituted with at least one group chosen from halogen atoms,

wherein R1 and R2 do not each simultaneously represent a phenyl group.

2. The compound according to claim 1 , wherein the γ-lactam moiety contains an (S) stereocenter .

3. The compound according to claim 1 , wherein the cycloalkyl group is a cyclic saturated hydrocarbon comprising 1 to 12 carbon atoms.

4. The compound according to claim 3 , wherein the cycloalkyl group is selected from the group consisting of cyclohexylmethyl, adamantyl and cyclohexyl.

5. The compound according to claim 1 , wherein the compound has the following formula (I′):

in which R1 is as defined in claim 1 .

6. The compound according to claim 1 , wherein the compound is selected from the group consisting of the following compounds and their pharmaceutically acceptable salts:

7. A pharmaceutical composition comprising the compound according to claim 1 and a pharmaceutically acceptable carrier.

8. A method for treating an inflammatory disease and/or a cancer in a subject in need thereof, comprising administering to said subject at least one compound according to claim 1 .

9. The method according to claim 8 , wherein the inflammatory disease is a chronic inflammatory disease selected from the group consisting of rheumatoid arthritis, Crohn's disease, inflammatory bowel disease, osteoarthrosis and osteoporosis; and/or the cancer is selected from the group consisting of a colon cancer, a colorectal cancer, a melanoma, a breast cancer, a thyroid cancer, a prostate cancer, an ovarian cancer, a lung cancer, a pancreatic cancer, a glioma, a cervical cancer, an endometrial cancer, a head and neck cancer, a liver cancer, a renal cancer, a skin cancer, a stomach cancer, a testis cancer, an urothelial cancer and an adrenocortical carcinoma and a non solid cancer.

10. A combination therapy in the treatment of a cancer comprising administering :

a) the compound according to claim 1 , and

b) at least one additional therapeutic agent simultaneously or sequentially.

11. The combination therapy according to claim 10 , wherein the additional therapeutic agent b) is an anti-checkpoint antibody.

12. The compound according to claim 1 , wherein said compound is a P2RX7 modulator.

13. The compound according to claim 1 , wherein the aryl is selected from the group consisting of chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 2-iodophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,4-dim ethoxyphenyl, 3-trifluoromethylphenyl, 3,5-bis(trifluoromethyl)phenyl and 2,4,6-trimethylphenyl.

14. The compound according to claim 1 , wherein the aralkyl group is selected from the group consisting of benzyl, 2-chlorobenzyl, 2,4-dichlorobenzyl, 3,4-dichlorobenzyl and 2,4-dichlorophenethyl.

15. The compound according to claim 1 , wherein the heteroaryl group is substituted with at least one halogen atom, one C1 -C6 alkoxy radical, and/or one C1-C6 halogenoalkyl radical.

Assignments (2)
CHANGE OF NAME Recorded Nov 16, 2021
From: YNCREA HAUTS DE FRANCE
To: JUNIA
Reel/Frame 058146/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 14, 2020
From: VOURET, VALÉRIE; DOUGUET, LAETITIA; GHINET, ALINA; HOMERIN, GERMAIN; RIGO, BENOÎT GUY MARIE; BAUDELET, DAVY JÉRÉMY; DEZITTER, XAVIER; MILLET, RÉGIS; FURMAN, CHRISTOPHE
To: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; CHRU DE LILLE; UNIVERSITE COTE D'AZUR; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); UNIVERSITÉ DE LILLE; YNCREA HAUTS DE FRANCE
Reel/Frame 054642/0175 →
Priority Claims (1)
EP 18305361 · Mar 29, 2018 · regional
Continuity (1)
Related Publication 20210017131A1 · Jan 21, 2021