Piperidin-1-yl and azepin-1-yl carboxylates as muscarinic M4 receptor agonists

Patent metadata

Field	Value
Publication number	US-10030012-B2
Application number	US-201715455946-A
Country	US
Kind code	B2
Filing date	Mar 10, 2017
Priority date	Feb 7, 2013
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

The present invention provides muscarinic M4 receptor agonists of formula (I) and pharmaceutically acceptable salts thereof, wherein m, n, p, q, R, R 2 and R 3 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases such as schizophrenia, Alzheimer's disease and various cognitive disorders as well as in the treatment or alleviation of pain.

First claim

The invention claimed is:

1. A compound selected from the group consisting of:
Ethyl 4-[4-(1-methyl-1H-imidazol-2-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-{[3-(1H-pyrazol-1-yl)azetidin-1-yl]methyl}piperidine-1-carboxylate,
Ethyl 4-[4-(pyridin-4-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-[4-(6-methoxypyridin-2-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-[4-(2-methoxypyridin-3-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-[4-(2-methylpyrimidin-4-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-[4-(4,6-dimethoxypyrimidin-2-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-[4-(2-methylpyridin-3-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-[4-(2-ethoxy-5-methylpyridin-3-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-[4-(1,3-thiazol-2-yl)piperidin-1-yl]piperidine-1-carboxylate,
Ethyl 4-[4-(6-ethoxypyridin-2-yl)piperidin-1-yl]piperidine-1-carboxylate,
Methyl 4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)pyrrolidin-1-yl]methyl}piperidine-1-carboxylate,
Ethyl 4-{[3-(3,5-dimethyl-1H-pyrazol-1-yl)pyrrolidin-1-yl]methyl}piperidine-1-carboxylate,
and pharmaceutically acceptable salts thereof.

2. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof, in association with a pharmaceutically acceptable adjuvant, diluent or carrier.

Assignees

• Heptares Therapeutics Ltd

Inventors

• Livermore David
• White Kathryn
• Congreve Miles
• Brown Giles
• O'Brien Michael

Classifications

• A61P43/00

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

• A61P25/30

  for treating abuse or dependence · CPC title

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61P25/18

  Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia · CPC title

• A61P25/04

  Centrally acting analgesics, e.g. opioids · CPC title