Thienopyrimidine compounds

Patent metadata

Field	Value
Publication number	US-9920066-B2
Application number	US-201715436988-A
Country	US
Kind code	B2
Filing date	Feb 20, 2017
Priority date	Sep 21, 2007
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

Compounds of formula (I) are A 2B receptor antagonists:

Wherein R 1 is optionally substituted aryl or an optionally substituted 5- or 6-membered heteroaryl ring; R 2 and R 3 are independently selected from hydrogen, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-(C 1 -C 6 )-alkyl, aryl-(C 1 -C 6 )-alkyl optionally substituted in the ring part thereof, a 5- or 6-membered monocyclic heterocyclic group optionally linked via a C 1 -C 6 alkylene chain and optionally substituted in the ring part thereof, benzimidazol-2-yl-methyl, pyrid-3-yl-carbonyl, or (1-methyl-piperidin-4-yl)-carbonyl-methyl; or R 2 and R 3 taken together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring; R 4 is C 1 -C 3 alkyl, C 2 -C 3 alkenyl, —N(—R 5 )—R 6 , or optionally substituted heteroarylmethylamino; and R 5 and R 6 are independently selected from hydrogen or C 1 -C 3 alkyl; or R 5 and R 6 taken together with the nitrogen atom to which they are attached form an optionally substituted 4- to 6-membered saturated ring.

First claim

The invention claimed is:

1. A compound having the formula:

wherein
R 1 is a furan, thiophene, pyrrole, oxazole, thiazole, imidazole, or pyridine; optionally substituted with fluoro, chloro, bromo, cyano, methyl, trifluoromethyl, ethyl, hydroxyl, hydroxymethyl, or hydroxyethyl;
R 2 is hydrogen;
R 3 is a 5- or 6-membered monocyclic heterocyclic group optionally linked via a C 1 -C 6 alkylene chain and optionally substituted in the ring part thereof by fluoro, chloro, bromo, cyano, methyl, trifluoromethyl, ethyl, hydroxyl, hydroxymethyl, or hydroxyethyl;
R 4 is C 1 -C 3 alkyl.

2. The compound of claim 1 wherein R 1 is an unsubstituted furan, thiophene, pyrrole, oxazole, thiazole, imidazole, or pyridine.

3. The compound of claim 1 wherein R 1 is a furan, thiophene, pyrrole, oxazole, thiazole, imidazole, or pyridine; substituted with fluoro, chloro, bromo, cyano, methyl, trifluoromethyl, ethyl, hydroxyl, hydroxymethyl, or hydroxyethyl.

4. The compound of claim 1 wherein R 3 is a pyran piperidine, morpholine, imidazole, pyridine, pyrimidine, pyrazine, or tetrazole linked via a C 1 -C 6 alkylene chain and optionally substituted in the ring part thereof by fluoro, chloro, bromo, cyano, methyl, trifluoromethyl, ethyl, hydroxyl, hydroxymethyl, or hydroxyethyl.

5. The compound of claim 1 wherein R 3 is a pyridine linked via a C 1 -C 6 alkylene chain and optionally substituted in the ring part thereof by fluoro, chloro, bromo, cyano, methyl, trifluoromethyl, ethyl, hydroxyl, hydroxymethyl, or hydroxyethyl.

6. The compound of claim 1 wherein R 3 is a pyridine linked via an ethylene and optionally substituted in the ring part thereof by fluoro, chloro, bromo, cyano, methyl, trifluoromethyl, ethyl, hydroxyl, hydroxymethyl, or hydroxyethyl.

7. The compound of claim 1 wherein R 3 is a pyridine linked via an ethylene and substituted in the ring part thereof by fluoro, chloro, bromo, cyano, methyl, trifluoromethyl, ethyl, hydroxyl, hydroxymethyl, or hydroxyethyl.

8. A method of treating cancer, said method comprising administering to a subject in need thereof an effective amount of a compound of claim 1 .

Assignees

• Vernalis R&D Ltd

Inventors

• Jordan Allan
• Bedford Simon
• Burkhard Klenke
• Yule Ian
• Poullennec Karine

Classifications

• A61P35/00

  Antineoplastic agents · CPC title

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• A61P27/02

  Ophthalmic agents · CPC title