US4355040A
Expired / Lapsed
US
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Hypotensive imidazole-5-acetic acid derivatives
Assignee: Takeda Pharmaceutical Co Ltd
•
Filing: 1980-11-05
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Granted: 1982-10-19
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Expires: 2000-11-05
Abstract
Abstract Novel imidazole-5-acetic acid derivatives of the formula: <IMAGE> wherein R1 is lower alkyl, cycloalkyl or, phenyl which may be substituted with one to three of halogen, nitro, amino, mono(lower alkyl)amino, di(lower alkyl)amino, lower alkyl, lower alkoxyl, benzyloxyl or/and hydroxyl; X1, X2 and X3 are each hydrogen, halogen, nitro, amino, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl; Y is halogen and R2 is hydrogen or lower alkyl; provided that X1 is halogen, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl when R1 is unsubstituted or substituted phenyl only with one halogen, di(lower alkyl)amino, lower alkyl or lower alkoxyl, and its salts have hypotensive activity.
Inventors
- 👤 Yoshiyasu Furukawa
- 👤 Shoji Kishimoto
- 👤 Kohei Nishikawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 00:57
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/68; A; A61; A61P; A61P9/00; A61P9/12
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
54 words
A compound of the formula: ##STR138## wherein alk is lower alkyl or lower cycloalkyl; each of X 1 , X 2 and X 3 is independently hydrogen, halogen, nitro, amino, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl; Y is halogen and R 2 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
54 words
A compound of the formula: ##STR138## wherein alk is lower alkyl or lower cycloalkyl; each of X 1 , X 2 and X 3 is independently hydrogen, halogen, nitro, amino, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl; Y is halogen and R 2 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1, wherein Y is chlorine.
Claim 4
Dependent Claim
11 words
A compound according to claim 1, wherein R 2 is hydrogen.
Claim 5
Dependent Claim
10 words
A compound according to claim 1, which is 1-(2-chlorobenzyl)-2-n-butyl-4-chloroimidazole-5-acetic acid.
Claim 6
Dependent Claim
83 words
A compound of the formula: ##STR139## wherein R 1 is phenyl which is substituted with only one nitro, amino, monobutylamino or hydroxyl, or with two or three of halogen, nitro, amino, mono(lower alkyl)amino, di(lower alkyl)amino, lower alkyl, lower alkoxyl, benzyloxyl or/and hydroxyl groups; each of X 1 , X 2 and X 3 is independently hydrogen, halogen, nitro, amino, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl; Y is halogen and R 2 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
83 words
A compound of the formula: ##STR139## wherein R 1 is phenyl which is substituted with only one nitro, amino, monobutylamino or hydroxyl, or with two or three of halogen, nitro, amino, mono(lower alkyl)amino, di(lower alkyl)amino, lower alkyl, lower alkoxyl, benzyloxyl or/and hydroxyl groups; each of X 1 , X 2 and X 3 is independently hydrogen, halogen, nitro, amino, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl; Y is halogen and R 2 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
41 words
A compound according to claim 5, wherein R 1 is phenyl substituted with two to three of halogen, mono(lower alkyl)amino, di(lower alkyl)amino, lower alkyl, lower alkoxyl, benzyloxyl or/and hydroxyl, and X 1 , X 2 and X 3 are each hydrogen.
Claim 9
Dependent Claim
10 words
A compound according to claim 5, wherein Y is chlorine.
Claim 10
Dependent Claim
11 words
A compound according to claim 5, wherein R 2 is hydrogen.
Claim 11
Dependent Claim
10 words
A compound according to claim 5, which is 1-benzyl-4-chloro-2-(4-chloro-3,5-dinitrophenyl)imidazole-5-acetic acid.
Claim 12
Dependent Claim
75 words
A compound of the formula: ##STR140## wherein R 1 is unsubstituted phenyl or phenyl substituted only with one halogen, di(lower alkyl)amino, lower alkyl or lower alkoxyl; X 1 is halogen, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl, and each of X 2 and X 3 is independently hydrogen, halogen, nitro, amino, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl; Y is halogen and R 2 is hydrogen or lower alkyl or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
75 words
A compound of the formula: ##STR140## wherein R 1 is unsubstituted phenyl or phenyl substituted only with one halogen, di(lower alkyl)amino, lower alkyl or lower alkoxyl; X 1 is halogen, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl, and each of X 2 and X 3 is independently hydrogen, halogen, nitro, amino, lower alkyl, lower alkoxyl, benzyloxyl or hydroxyl; Y is halogen and R 2 is hydrogen or lower alkyl or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
30 words
A compound according to claim 10, wherein R 1 is unsubstituted phenyl, and X 1 is C 1-4 alkyl, X 2 is C 1-4 alkoxyl and X 3 is hydrogen.
Claim 15
Dependent Claim
10 words
A compound according to claim 10, wherein Y is chlorine.
Claim 16
Dependent Claim
11 words
A compound according to claim 10, wherein R 2 is hydrogen.
Claim 17
Dependent Claim
10 words
A compound according to claim 10, which is 4-chloro-1-(4-methoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid.
Claim 18
Dependent Claim
10 words
A compound according to claim 10, which is 4-chloro-1-(4-ethoxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid.
Claim 19
Dependent Claim
35 words
A pharmaceutical composition which contains an amount effective for producing hypotensive activity in a mammal of a compound of claim 2, 6, 11, 1-15 or 3, and a pharmaceutically acceptable carrier, vehicle or diluent therefor.
Claim 20
Dependent Claim
30 words
A method for producing hypotensive activity in a mammal, which comprises administering to said mammal a hypotensively effective amount of a compound of claim 2, 6, 11, 1-15 or 3.
References Cited (Backward Citations)
GB1535566A
Cited
US4207324A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-10-18 | 1986-04-19 | 1986-10-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-10-18 | 1990-04-19 | 1990-10-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-10-18 | 1994-04-19 | 1994-10-19 | $7700.00 | Window Closed / Lapsed |