Pyridylaminoacetic acid compound
The present invention provides a novel pyridylaminoacetic acid compound represented by the following formula (1): (wherein R 1 , R 2 , R 3 , Y and Z are as defined in the description and claims), or a pharmacologically acceptable salt thereof. The pyridylaminoacetic acid compound has EP2 agonistic action and is therefore useful as a therapeutic and/or prophylactic agent for respiratory diseases such as asthma or chronic obstructive pulmonary disease.
1. A pyridylaminoacetic acid compound represented by the formula (1):
wherein,
R 1 , R 2 and R 3 respectively and independently represent a hydrogen atom or a C 1 -C 6 alkyl group,
Y represents a -Q 1 -Q 2 group, wherein Q 1 represents an arylene group and Q 2 represents a pyrazolyl group which may be substituted with a group(s) selected from the group consisting of a halogen atom, a hydroxy group, a C 1 -C 6 alkyl group, a halogeno-C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group and a halogeno-C 1 -C 6 alkoxy group, and
Z represents a pyridyl group which may be substituted with a group(s) selected from the group consisting of a halogen atom, a C 1 -C 6 alkyl group, a halogeno-C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group and a halogeno-C 1 -C 6 alkoxy group,
or a pharmacologically acceptable salt thereof.
2. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein R 2 and R 3 respectively and independently represent a hydrogen atom or a C 1 -C 4 alkyl group.
3. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein Q 2 may be substituted with a group(s) selected from the group consisting of a halogen atom, a hydroxy group, a C 1 -C 4 alkyl group, a halogeno-C 1 -C 4 alkyl group, a C 1 -C 4 alkoxy group and a halogeno-C 1 -C 4 alkoxy group.
4. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein Z may be substituted with a group(s) selected from the group consisting of a halogen atom, a C 1 -C 4 alkyl group, a halogeno-C 1 -C 4 alkyl group, a C 1 -C 4 alkoxy group and a halogeno-C 1 -C 4 alkoxy group.
5. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein Y a -Q 1 -Q 2 group, wherein Q 1 represents a phenylene group and Q 2 represents a pyrazolyl group which may be substituted with a group(s) selected from the group consisting of a halogen atom, a hydroxy group, a C 1 -C 4 alkyl group, a halogeno-C 1 -C 4 alkyl group, a C 1 -C 4 alkoxy group and a halogeno-C 1 -C 4 alkoxy group.
6. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 5 , wherein Y represents a -Q 1 -Q 2 group, wherein Q 1 represents a phenylene group and Q 2 represents a pyrazolyl group, which may be substituted with a group(s) selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a hydroxy group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a difluoromethyl group, a trichloromethyl group, a dichloromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a tert-butoxy group, a trifluoromethoxy group, a difluoromethoxy group, a trichloromethoxy group and a dichloromethoxy group.
7. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein Z represents a pyridyl group which may be substituted with a group(s) selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a difluoromethyl group, a trichloromethyl group, a dichloromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a tert-butoxy group, a trifluoromethoxy group, a difluoromethoxy group, a trichloromethoxy group and a dichloromethoxy group.
8. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein R 2 and R 3 respectively and independently represent a hydrogen atom or a methyl group.
9. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein Z represents a pyridyl group which may be substituted with a group(s) selected from the group consisting of a halogen atom and a C 1 -C 4 alkoxy group.
10. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein R 1 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group or a hexyl group,
R 2 and R 3 respectively and independently represent a hydrogen atom or a methyl group,
Y represents a 4-(pyrazol-1-yl)phenyl
Z represents a a pyridin-2-yl group, a 5-fluoropyridin-2-yl group, a 5-chloropyridin-2-yl group, a 5-methylpyridin-2-yl group, a 5-ethylpyridin-2-yl group, a 5-trifluoromethylpyridin-2-yl group, a 5-methoxypyridin-2-yl group, a 5-difluoromethoxypyridin-2-yl group, a pyridin-3-yl group, a 6-fluoropyridin-3-yl group, a 6-chloropyridin-3-yl group, a 6-methylpyridin-3-yl group, a 6-ethylpyridin-3-yl group, a 6-trifluoromethylpyridin-3-yl group, a 6-methoxypyridin-3-yl group, a 6-difluoromethoxypyridin-3-yl group, or a pyridin-4-yl group.
11. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein R 1 represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group or a hexyl group,
R 2 and R 3 respectively and independently represent a hydrogen atom or a methyl group,
Y represents a 4-(pyrazol-1-yl)phenyl group and
Z represents a pyridin-2-yl group, a 5-fluoropyridin-2-yl group, a 5-chloropyridin-2-yl group, a 5-methoxypyridin-2-yl group, a pyridin-3-yl group, a 6-fluoropyridin-3-yl group, a 6-chloropyridin-3-yl group, a 6-methoxypyridin-3-yl group or a pyridin-4-yl group.
12. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein R 1 represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group or a hexyl group,
R 2 and R 3 both represent hydrogen atoms,
Y represents a 4 (pyrazol-1-yl)phenyl group, and
Z represents a pyridin-2-yl group or a pyridin-3-yl group.
13. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein R 1 represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group or a hexyl group,
R 2 and R 3 both represent hydrogen atoms,
Y represents a 4 (pyrazol-1-yl)phenyl group, and
Z represents a pyridin-2-yl group or a pyridin-3-yl group.
14. The pyridylaminoacetic acid compound or pharmacologically acceptable salt thereof according to claim 1 , wherein the pyridylaminoacetic acid compound is:
(6-{[4-(pyrazol-1-yl)benzyl](pyridin-2-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetic acid,
(6-{[4-(pyrazol-1-yl)benzyl](pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetic acid,
ethyl (6-{[4-(pyrazol-1-yl)benzyl](pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetate, or
isopropyl (6-{[4-(pyrazol-1-yl)benzyl](pyridin-3-ylsulfonyl)aminomethyl}pyridin-2-ylamino)acetate.
15. A pharmaceutical composition comprising the pyridylaminoacetic acid compound according to claim 1 , or a pharmacologically acceptable salt thereof as an active ingredient; and
one or more additive selected from the group consisting of vehicles, lubricants, binders, disintegrators, emulsifiers, stabilizers, corrigents and diluents.