PI3K (delta) selective inhibitors

Inventor: Congxin Liang (Palm Beach Gardens, FL)

Assignee: Xcovery Holding Company, LLC

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Quick Facts

Patent No.: US 8,569,296
App. No.: 13/498,770
Granted: Oct 29, 2013
Kind: B2

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Abstract

Novel PI3K, especially PI3K delta isoform, selective inhibitors are disclosed. The compounds are useful in treating disorders related to abnormal PI3K or PI3Kδ activities such as cancer, immune disorders, cardiovascular disease, viral infection, inflammation, metabolism/endocrine disorders and neurological disorders.

Claims (55)

1. A compound that is

4-{4-[2-(difluoromethyl)benzimidazolyl]-6-morpholin-4-ylpyrazolo[5,4-d]pyrimidinyl}piperidyl 4-methylpiperazinyl ketone.

2. A compound that is

1-(2-{4-[2-(difluoromethyl)benzimidazolyl]-6-morpholin-4-ylpyrazolo[5,4-d]pyrimidinyl}ethyl)-4-(methylsulfonyl)piperazine;

4-{6-[2-(difluoromethyl)benzimidazolyl]-2-morpholin-4-ylpurin-9-yl}piperidyl 4-methylpiperazinyl ketone;

[4-[6-[2-(difluoromethyl)benzimidazol-1-yl]-2-morpholino-purin-9-yl]-1-piperidyl]-(4-fluorophenyl)methanone;

[4-[6-[2-(difluoromethyl)benzimidazol-1-yl]-2-morpholino-purin-9-yl]-1-piperidyl]-(4-pyridyl)methanone;

[4-[6-[2-(difluoromethyl)benzimidazol-1-yl]-2-morpholino-purin-9-yl]-1-piperidyl]-(3-pyridyl)methanone;

(4-{6-[2-(difluoromethyl)benzimidazolyl]-2-morpholin-4-ylpurin-9-yl}piperidyl)-N,N-dimethylcarboxamide;

methyl 4-{6-[2-(difluoromethyl)benzimidazolyl]-2-morpholin-4-ylpurin-9-yl}piperidinecarboxylate;

4-{6-[2-(difluoromethyl)benzimidazolyl]-2-morpholin-4-ylpurin-9-yl}-1-(methylsulfonyl)piperidine;

(2R)-1-(4-{6-[2-(difluoromethyl)benzimidazolyl]-2-morpholin-4-ylpurin-9-yl}piperidyl)-2-hydroxypropan-1-one;

4-{6-[2-(difluoromethyl)benzimidazolyl]-2-morpholin-4-ylpurin-9-yl}piperidyl pyrrolidinyl ketone;

4-{6-[2-(difluoromethyl)-4-methoxybenzimidazolyl]-2-morpholin-4-ylpurin-9-yl}piperidyl 4-methylpiperazinyl ketone;

4-{6-[2-(difluoromethyl)-4-methoxybenzimidazolyl]-2-morpholin-4-ylpurin-9-yl}-1-(methylsulfonyl)piperidine;

1-(9-(2H-3,4,5,6-tetrahydropyran-4-yl)-2-morpholin-4-ylpurin-6-yl)-2-(difluoromethyl)-4-methoxybenzimidazole;

(3-{6-[2-(difluoromethyl)benzimidazolyl]-2-morpholin-4-ylpurin-9-yl}pyrrolidinyl)-N,N-dimethylcarboxamide; or

4-{3-(2H-3,4,5,6-tetrahydropyran-4-yl)-7-[2-(difluoromethyl)benzimidazolyl]-1,2,3-triazolo[5,4-d]pyrimidin-5-yl}morpholine.

3. A method of treating a PI-3 kinase mediated disease in a subject having said disease comprising administering to the subject a compound selected from:

4-{4-[2-(difluoromethyl)benzimidazolyl]-6-morpholin-4-ylpyrazolo[5,4-d]pyrimidinyl}piperidyl 4-methylpiperazinyl ketone;

1-(2-{4-[2-(difluoromethyl)benzimidazolyl]-6-morpholin-4-ylpyrazolo[5,4-d]pyrimidinyl}ethyl)-4-(methylsulfonyl)piperazine;

4-{6-[2-(difluoromethyl)benzimidazolyl]-2-morpholin-4-ylpurin-9-yl}piperidyl 4-methylpiperazinyl ketone;

[4-[6-[2-(difluoromethyl)benzimidazolyl-1-yl]-2-morpholin-purin-9-yl]-1-piperidyl]-(4-fluorophenyl)methanone;

[4-[6-[2-(difluoromethyl)benzimidazolyl-1-yl]-2-morpholino-purin-9-yl]-1-piperidyl]-(4-pyridyl)methanone;

[4-[6-[2-(difluoromethyl)benzimidazolyl-1-yl]-2-morpholino-purin-9-yl]-1-piperidyl]-(3-pyridyl)methanone;