US4140788A
Expired / Lapsed
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N-Substituted imidazolecarboxamide derivatives
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1977-11-07
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Granted: 1979-02-20
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Expires: 1997-11-07
Abstract
Abstract N-Substituted imidazolecarboxamide compounds represented by the formula; <IMAGE> (I) wherein R1 is hydrogen atom, lower alkyl, lower alkenyl, aralkyl, R2 is hydrogen atom, lower alkyl, lower alkenyl, aralkyl, 1-adamantyl, R3 is hydrogen atom, lower alkyl, aralkyl; with the proviso that one of R1, R2 or R3 is not hydrogen when the other two are hydrogen, are produced by reacting aminomalonamide derivative with orthoformate derivative in high yields. The compounds (I) exhibit anti-tumor activity against experimental tumors such as Sarcoma 180 in mice.
Inventors
- 👤 Toshio Atsumi
- 👤 Yuzo Tarumi
- 👤 Norboru Yoshida
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 05:34
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/90
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
78 words
A compound of the formula, ##STR25## wherein R 1 is hydrogen, lower alkyl, lower alkenyl benzyl or C 1 -C 3 alkoxy-substituted benzyl, R 2 is hydrogen, lower alkyl, lower alkenyl, benzyl, C 1 -C 3 alkoxy substituted benzyl or 1-adamantyl, R 3 is hydrogen, lower alkyl, benzyl or C 1 -C 3 alkoxy-substituted benzyl, with the proviso that one of R 1 , R 2 or R 3 is not hydrogen when the other two are hydrogen.
Claim 2
Dependent Claim
78 words
A compound of the formula, ##STR25## wherein R 1 is hydrogen, lower alkyl, lower alkenyl benzyl or C 1 -C 3 alkoxy-substituted benzyl, R 2 is hydrogen, lower alkyl, lower alkenyl, benzyl, C 1 -C 3 alkoxy substituted benzyl or 1-adamantyl, R 3 is hydrogen, lower alkyl, benzyl or C 1 -C 3 alkoxy-substituted benzyl, with the proviso that one of R 1 , R 2 or R 3 is not hydrogen when the other two are hydrogen.
Claim 3
Dependent Claim
40 words
A compound according to claim 1, wherein R 1 is lower alkyl, benzyl or C 1 -C 3 alkoxy substituted benzyl, R 2 is hydrogen, R 3 is hydrogen, lower alkyl, benzyl or C 1 -C 3 alkoxy substituted benzyl.
Claim 4
Dependent Claim
30 words
A compound according to claim 1, wherein R 1 is hydrogen, R 2 is lower alkyl, benzyl, C 1 -C 3 alkoxy substituted benzyl or 1-adamantyl, R 3 is hydrogen.
Claim 5
Dependent Claim
41 words
A compound according to claim 1, wherein R 1 and R 2 are lower alkyl, lower alkenyl benzyl or C 1 -C 3 alkoxy substituted benzyl, R 3 is hydrogen, lower alkyl, benzyl or C 1 -C 3 alkoxy substituted benzyl.
Claim 6
Dependent Claim
1 words
1-Benzyl-5-hydroxy-1H-imidazole-4-carboxamide.
Claim 7
Dependent Claim
1 words
1-Benzyl-5-hydroxy-1H-imidazole-4-carboxamide.
Claim 8
Dependent Claim
1 words
1-Methyl-5-hydroxy-1H-imidazole-4-carboxamide.
Claim 9
Dependent Claim
1 words
1-Methyl-5-hydroxy-1H-imidazole-4-carboxamide.
Claim 10
Dependent Claim
1 words
1-(p-Methoxybenzyl)-5-hydroxy-1H-imidazole-4-carboxamide.
Claim 11
Dependent Claim
1 words
1-(p-Methoxybenzyl)-5-hydroxy-1H-imidazole-4-carboxamide.
Claim 12
Dependent Claim
1 words
1-methyl-5-hydroxy-1H-imidazole-4-(N-methyl)-carboxamide.
Claim 13
Dependent Claim
1 words
1-methyl-5-hydroxy-1H-imidazole-4-(N-methyl)-carboxamide.
Claim 14
Dependent Claim
1 words
1-benzyl-5-hydroxy-1H-imidazol-4-(N-benzyl)-carboxamide.
Claim 15
Dependent Claim
1 words
1-benzyl-5-hydroxy-1H-imidazol-4-(N-benzyl)-carboxamide.
Claim 16
Dependent Claim
1 words
1-methyl-5-methoxy-1H-imidazole-4-(N-methyl)-carboxamide.
Claim 17
Dependent Claim
1 words
1-methyl-5-methoxy-1H-imidazole-4-(N-methyl)-carboxamide.
Claim 18
Dependent Claim
1 words
5-hydroxy-1H-imidazole-4-[N-(1-adamantyl)]-carboxamide.
Claim 19
Dependent Claim
1 words
5-hydroxy-1H-imidazole-4-[N-(1-adamantyl)]-carboxamide.
Claim 20
Dependent Claim
33 words
A pharmaceutical composition, which comprises an effective amount for treating the Sarcoma 180 tumor in mice of a compound of claim 1 as an active ingredient and a pharmaceutically acceptable carrier or diluent.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-02-19 | 1982-08-21 | 1983-02-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-19 | 1986-08-21 | 1987-02-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-19 | 1990-08-21 | 1991-02-20 | $7700.00 | Window Closed / Lapsed |