US 8,946,443 B2Granted

Cyclopropanecarboxylic acid derivative

AssigneeDaiichi Sankyo Company, Limited

InventorsTsutomu Nagata, Jun Kobayashi, Yoshiyuki Onishi, Masamichi Kishida, Kengo Noguchi

Life of this patent

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Abstract

A compound represented by the following general formula (I) or a pharmacologically acceptable salt thereof, wherein R1 represents a C1 to C6 alkyl group which may be substituted by one to three groups selected from substituent group A, or the like (substituent group A: a hydroxy group, a halogeno group, a cyano group, a nitro group, an amino group, a carboxy group, a C1 to C3 alkyl group, etc.); R2, R3, and R8 each independently represent a hydrogen atom or a C1 to C3 alkyl group; R4, R5, R6, R7, R9, and R10 each independently represent a hydrogen atom or the like; and R11 represents a hydrogen atom or the like, has TAFIa enzyme inhibitory activity and is useful as a therapeutic drug for myocardial infarction, angina pectoris, acute coronary syndrome, cerebral infarction, deep vein thrombosis, pulmonary embolism, or the like.

Claims31

Dependent claims

A compound of general formula (I):

or a pharmacologically acceptable salt thereof, wherein
R1 is selected from a C1 to C6 alkyl group which may be substituted by one to three identical or different groups selected from:
substituent group A,
a C2 to C6 alkenyl group which may be substituted by one to three identical or different groups selected from substituent group A,
a C3 to C8 cycloalkyl group which may be substituted by one to three identical or different groups selected from substituent group A,
an aryl group which may be substituted by one to three identical or different groups selected from substituent group A, provided that when the aryl group is a phenyl group having a substituent, the substituent is substituted at a meta or para position on the benzene ring,
a saturated heterocyclyl group which may be substituted by one to three identical or different groups selected from substituent group A, and
an unsaturated heterocyclyl group which may be substituted by one to three identical or different groups selected from substituent group A;
R2, R3, and R8 are each independently selected from a hydrogen atom and a C1 to C3 alkyl group;
R4, R5, R6, R7, R9, and R10 are each independently selected from a hydrogen atom, a fluoro group, and a C1 to C3 alkyl group;
R11 is selected from a hydrogen atom, a methyl group, and an ethyl group;
and
substituent group A consists of a hydroxy group, a halogeno group, a cyano group, a nitro group, an amino group, a carboxy group, a C1 to C3 alkyl group, a halogeno-C1 to C3 alkyl group, a C3 to C8 cycloalkyl group, a C1 to C3 alkoxy group, a halogeno-C1 to C3 alkoxy group, a C1 to C3 alkylsulfonyl group, an aryl group, a saturated heterocyclyl group, an unsaturated heterocyclyl group, and an aryloxy group.

10 more elements

A compound of general formula (I-1):

or a pharmacologically acceptable salt thereof, wherein
Ra is selected from:
a C3 to C6 branched alkyl group;
a C3 to C6 cycloalkyl group which may be substituted by one or two identical or different C1 to C3 alkyl groups;
a phenyl group which may be substituted by one or two identical or different groups selected from the group consisting of a C1 to C3 alkyl group, a C1 to C3 alkoxy group, a phenoxy group, a halogeno group, and a cyano group, wherein the substituent is substituted at the 3- or 4-position, or both, of the phenyl group;
a naphthyl group;
a 5- or 6-membered heteroaryl group which may be substituted by one or two identical or different groups selected from the group consisting of a C1 to C3 alkyl group, a C1 to C3 alkoxy group, a phenoxy group, a halogeno group, and a cyano group, wherein the heteroaryl group has one or more nitrogen atoms in the ring and may be condensed with a benzene ring;
and
a benzofuranyl group;
and
Rb and Re are each independently selected from a hydrogen atom or a C1 to C3 alkyl group.

8 more elements

A compound of general formula (I-2):

or a pharmacologically acceptable salt thereof, wherein
Ra is selected from:
a C3 to C6 branched alkyl group;
a C3 to C6 cycloalkyl group which may be substituted by one or two identical or different C1 to C3 alkyl groups;
a phenyl group which may be substituted by one or two identical or different groups selected from the group consisting of a C1 to C3 alkyl group, a C1 to C3 alkoxy group, a phenoxy group, a halogeno group, and a cyano group, wherein the substituent is substituted at the 3- or 4-position, or both, of the phenyl group;
a naphthyl group;
a 5- or 6-membered heteroaryl group which may be substituted by one or two identical or different groups selected from the group consisting of a C1 to C3 alkyl group, a C1 to C3 alkoxy group, a phenoxy group, a halogeno group, and a cyano group, wherein the heteroaryl group has one or more nitrogen atoms in the ring and may be condensed with a benzene ring;
and
a benzofuranyl group;
and
Rb and Rc are each independently selected from a hydrogen atom and a C1 to C3 alkyl group.

8 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/634,678Filed 14 Mar 2011
Priority: JP 2010-06215618 Mar 2010
Published: US 2013/0012532 A110 Jan 2013
Granted: 3 Feb 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification28 codes

A61K 31/4164
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,3-Diazoles
A61K 31/4178
1,3-Diazoles: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
A61K 31/427
Thiazoles: not condensed and containing further heterocyclic rings
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole