IP Library › Granted Patent US 10,005,756
Granted Patent B2
US 10,005,756 · App. 15/501,494 · Granted Jun 26, 2018

Pyrrolidinone derivatives as MetAP-2 inhibitors

Inventors: Timo Heinrich (Gross-Umstadt, DE); Frank Zenke (Darmstadt, DE); Felix Rohdich (Worfelden, DE); Manja Friese-Hamim (Moerfelden-Walldorf, DE); Diane Hahn (Seeheim-Jugenheim, DE)
Assignee: Merck Patent GmbH
C07D401/04A61K31/00A61K31/4015A61K31/4025C07D207/277C07D401/06C07D401/12C07D403/04C07D403/12C07D405/04C07D405/12C07D405/14C07D409/12C07D413/10C07D413/12C07D471/04
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Quick Facts
Patent No.
US 10,005,756
App. No.
15/501,494
Granted
Jun 26, 2018
Kind
B2
Abstract

Compounds according to Claim 1 , are inhibitors of methionine aminopeptidase and can be employed for the treatment of tumors.

Claims (19)

1. A compound of the formula

“A78”

  (S)-3-Hydroxy-2-oxo-1-(1H-pyrrolo[2,3-b]pyridin-5-yl)- pyrrolidine-3-carboxylic acid 3,5-difluoro-benzylamide

“A79”

  (S)-1-(3-Chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-hydroxy-2- oxo-pyrrolidine-3-carboxylic acid 3,5-difluoro-benzylamide

or pharmaceutically usable salts, tautomers or stereoisomers thereof, including mixtures thereof in all ratios.

2. The compound according to claim 1 of the formula

“A78”

  (S)-3-Hydroxy-2-oxo-1-(1H-pyrrolo[2,3-b]pyridin-5-yl)- pyrrolidine-3-carboxylic acid 3,5-difluoro-benzylamide

or pharmaceutically usable salts, tautomers or stereoisomers thereof, including mixtures thereof in all ratios.

3. The compound according to claim 1 of the formula

“A79”

  (S)-1-(3-Chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-hydroxy- 2-oxo-pyrrolidine-3-carboxylic acid 3,5-difluoro- benzylamide

or pharmaceutically usable salts, tautomers or stereoisomers thereof, including mixtures thereof in all ratios.

4. A pharmaceutical composition comprising at least one compound according to claim 1 and/or pharmaceutically usable salts, tautomers or stereo-isomers thereof, including mixtures thereof in all ratios, and a pharmaceutically acceptable carrier.

5. A method for the treatment of tumours, tumour metastases, proliferative diseases of the mesangial cells, haemangioma, proliferative retinopathy, rheumatoid arthritis, atherosclerotic neovascularisation, psoriasis, ocular neovascularisation, osteoporosis, diabetes and obesity, lymphoid leukaemia, lymphoma, malaria is prostate hypertrophy, comprising administering to a host in need thereof an effective amount of a compound according to claim 1 , or pharmaceutically usable salt, tautomer, stereoisomer or mixture thereof.

6. The method according to claim 5 , where the tumour disease is of the squamous epithelium, the bladder, the stomach, the kidneys, of head and neck, the esophagus, the cervix, the thyroid, the intestine, the liver, the brain, the prostate, the urogenital tract, the lymphatic system, the stomach, the larynx, the lung, or of the skin, or is monocytic leukaemia, lung adenocarcinoma, small-cell lung carcinoma, pancreatic cancer, glio-blastoma, breast carcinoma, acute myeloid leukaemia, chronic myeloid leukaemia, acute lymphatic leukaemia, chronic lymphatic leukaemia, Hodgkin's lymphoma, or non-Hodgkin's lymphoma.

7. The method according to claim 5 , comprising administering a therapeutically effective amount of a compound according to claim 1 in combination with a compound that is 1) an oestrogen receptor modulator, 2) an androgen receptor modulator, 3) a retinoid receptor modulator, 4) a cytotoxic agent, 5) a antiproliferative agent, 6) a prenyl-protein transferase inhibitor, 7) a HMG-CoA reductase inhibitor, 8) a HIV protease inhibitor, 9) a reverse transcriptase inhibitor or 10) an angiogenesis inhibitor.

8. The method according to claim 5 , comprising administering a therapeutically effective amount of a compound according to claim 1 in combination with radiotherapy and 1) an oestrogen receptor modulator, 2) an androgen receptor modulator, 3) a retinoid receptor modulator, 4) a cytotoxic agent, 5) an antiproliferative agent, 6) a prenyl-protein transferase inhibitor, 7) an HMG-CoA reductase inhibitor, 8) an HIV protease inhibitor, 9) a reverse transcriptase inhibitor or 10) an angiogenesis inhibitor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2017
From: HEINRICH, TIMO; ZENKE, FRANK; ROHDICH, FELIX; FRIESE-HAMIM, MANJA; HAHN, DIANE
To: MERCK PATENT GMBH
Reel/Frame 041165/0460 →
Priority Claims (1)
EP 14002720 · Aug 4, 2014 · regional
Continuity (1)
Related Publication 20170226080A1 · Aug 10, 2017
Cited By (1)
US 12,378,225