US 7,622,487 B2Granted

Piperidine derivative, process for producing the same, and use

AssigneeTakeda Pharmaceutical Company Limited

InventorsYoshinori Ikeura, Tadatoshi Hashimoto, Naoki Tarui, Junya Shirai

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Abstract

The present invention provides a compound represented by the formula: wherein Ar is an aryl group, an aralkyl group or an aromatic heterocyclic group, each of which may be substituted, R1 is a hydrogen atom, an optionally substituted hydrocarbon group, an acyl group or an optionally substituted heterocyclic group, X is an oxygen atom or an optionally substituted imino group, Z is an optionally substituted methylene group, Ring A is an optionally further substituted piperidine ring, and Ring B is an optionally substituted aromatic ring, provided that when Z is a methylene group substituted with an oxo group, R1 is not a methyl group, and when Z is a methylene group substituted with a methyl group, Ring B is a substituted aromatic ring, or a salt thereof, which is a novel piperidine derivative having excellent antagonistic action for a tachykinin receptor and useful as a medicament, particularly an agent for preventing and/or treating urinary frequency and/or urinary incontinence.

A compound represented by the formula:

wherein
Ar is a phenyl group optionally having 1 to 4 substituents selected from
(A) a halogen atom,
(B) a C1-6 alkyl group, and
(C) a 5- or 6-membered aromatic heterocyclic group having 1 to 4 hetero atoms of one or two kinds selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to carbon atoms,
R1 is an acyl group represented by the formula:
—(C═O)—Ra,
wherein Ra is
(A) a hydrogen atom, or
(B)
(a) a C1-6 alkyl group, or
(b) a 5- or 6-membered aromatic or 4- to 6-membered non-aromatic heterocyclic group having 1 to 4 hetero atoms of one or two kinds selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to carbon atoms,
each of which optionally has 1 or 2 substituents selected from
(i) a halogen atom,
(ii) a C1-6 alkyl group optionally substituted with a 5- or 6-membered aromatic or non-aromatic heterocyclic group having 1 to 4 hetero atoms of one or two kinds selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to carbon atoms, a C1-6 alkanoyl group, or a C6-14 aryl-carbonyl group,
(iii) a C1-6 alkoxy group,
(iv) an amino group,
(v) a mono- or di-C1-6 alkylamino group,
(vi) a C1-6 alkanoylamino group,
(vii) a N—C1-6 alkyl-N′—C1-6 alkanoylamino group,
(viii) a C1-6 alkoxy-carbonyl group,
(ix) a C1-6 alkanoyl group optionally substituted with C1-6 alkoxy, mono- or
di-C1-6 alkylamino, halogeno C1-6 alkyl or a halogen atom,
(x) a C6-14 aryl-carbonyl group,
(xi) a C7-19 aralkyl-carbonyl group,
(xii) a C3-6 cycloalkyl-carbonyl group,
(xiii) a 5- or 6-membered aromatic or non-aromatic heterocyclic-carbonyl group having 1 to 4 hetero atoms of one or two kinds selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to carbon atoms,
(xiv) a hydroxy group,
(xv) a C7-19 aralkyloxy group,
(xvi) a C3-6 cycloalkyloxy group,
(xvii) a C1-6 alkoxy-C1-6 alkoxy group,
(xviii) a carbamoyl group,
(xix) a mono- or di-C1-6 alkylcarbamoyl group,
(xx) a C1-6 alkylsulfonyl group,
(xxi) a mono- or di-C1-6 alkylaminosulfonyl group,
(xxii) a formyl group,
(xxiii) a formylamino group,
(xxiv) an oxo group, and
(xxv) a 5- or 6-membered aromatic or non-aromatic heterocyclic group having 1 to 4 hetero atoms of one or two kinds selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to carbon atoms, which optionally has 1 or 2 substituents selected from C1-6 alkanoyl and C1-6 alkoxy-C1-6 alkanoyl,
X is an imino group,
Z is a methylene group,
Ring A is a piperidine ring, and
Ring B is a phenyl group substituted with a C1-6 alkoxy group and a tetrazolyl group substituted with a halogenated C1-6 alkyl group,
or a salt thereof.

41 more elements

Facts

Application

10/516,252Filed 29 May 2003

Priority

JP 2002-15933831 May 2002

Published

US 2006/0167052 A127 Jul 2006

Granted

24 Nov 2009

Term ends

Not estimatedThe source records don’t support an estimate.

Classification39 codes

C07D 405/14
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having…:…
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/08
Drugs for disorders of the alimentary tract or the digestive system: for nausea, cinetosis or vertigo; Antiemetics
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…

Abstract

Claims7