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US4317825A
Expired / Lapsed
US
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Antitumor and immunosuppressive 4-carbamoyl imidazolium-5-olate derivatives
Assignee: Sumitomo Chemical Co Ltd
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Filing: 1980-08-05
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Granted: 1982-03-02
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Expires: 2000-08-05
Abstract
Abstract There are provided compounds of the formula: <IMAGE> wherein R is a heteroaroyl group containing a nitrogen, sulfur or oxygen atom which may be substituted with a lower alkyl group, an aralkyl group, an acyl group or a halogen atom; or a cycloalkanoyl group which may be substituted with a lower alkyl group, a lower alkenyl group, a halogen atom, a halogeno-lower alkenyl group, a phenyl group, a halogenophenyl group, a lower alkoxyphenyl group, a lower alkylphenyl group, a formyl group, a hydroxy group, an amino group, a carboxyl group, an aminomethyl group or an oxo group, its non toxic salt and a process for producing them. These compounds are useful as antitumor agents and immunosuppressants.
Inventors
- 👤 Toshio Atsumi
- 👤 Tetsutaro Sanjiki
- 👤 Takao Kiyohara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 09:41
CPC Classifications
A; A01; A01N; A01N53/00; C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/90; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
125 words
A compound of the formula ##STR6## wherein R is a substituted or unsubstituted five to six membered heteroaroyl group selected from the group consisting of furancarbonyl, thiophenecarbonyl, pyrrolecarbonyl, pyridinecarbonyl, pyridinecarbonyl N-oxide, pyrazinecarbonyl, imidazolecarbonyl, pyrazolecarbonyl or thiazolecarbonyl, said substituent being selected from a lower alkyl group, a C 7-8 aralkyl group, a lower alkanoyl group, a benzoyl group or a halogen atom; or a C 3-8 cycloalkanoyl group which may be substituted with a lower alkyl group, a lower alkenyl group, a halogen atom, a halogeno-lower alkenyl group, a phenyl group, a halogeno-phenyl group, a lower alkoxyphenyl group, a lower alkylphenyl group, a formyl group, a hydroxy group, an amino group, a carboxyl group, an aminomethyl group or an oxo group, or a non-toxic salt thereof.
Claim 2
Dependent Claim
125 words
A compound of the formula ##STR6## wherein R is a substituted or unsubstituted five to six membered heteroaroyl group selected from the group consisting of furancarbonyl, thiophenecarbonyl, pyrrolecarbonyl, pyridinecarbonyl, pyridinecarbonyl N-oxide, pyrazinecarbonyl, imidazolecarbonyl, pyrazolecarbonyl or thiazolecarbonyl, said substituent being selected from a lower alkyl group, a C 7-8 aralkyl group, a lower alkanoyl group, a benzoyl group or a halogen atom; or a C 3-8 cycloalkanoyl group which may be substituted with a lower alkyl group, a lower alkenyl group, a halogen atom, a halogeno-lower alkenyl group, a phenyl group, a halogeno-phenyl group, a lower alkoxyphenyl group, a lower alkylphenyl group, a formyl group, a hydroxy group, an amino group, a carboxyl group, an aminomethyl group or an oxo group, or a non-toxic salt thereof.
Claim 3
Dependent Claim
49 words
A compound according to claim 1, wherein R is a substituted or unsubstituted furancarbonyl, thiophenecarbonyl, pyrrolecarbonyl, pyridinecarbonyl, pyridinecarbonyl N-oxide, pyrazinecarbonyl, imidazolecarbonyl, pyrazolecarbonyl or thiazolecarbonyl, said substituent being selected from a lower alkyl group, a C 7-8 aralkyl group, a lower alkanoyl group, a benzoyl group or a halogen atom.
Claim 4
Dependent Claim
67 words
A compound according to claim 1, wherein R is a C 3-8 cycloalkanoyl group which may be substituted with a lower alkyl group, a lower alkenyl group, a halogen atom, a halogeno-lower alkenyl group, a phenyl group, a halogeno-phenyl group, a lower alkoxyphenyl group, a lower alkylphenyl group, a formyl group, a hydroxy group, an amino group, a carboxyl group, an aminomethyl group or an oxo group.
Claim 5
Dependent Claim
10 words
A compound according to claim 2, wherein R is 2-furancarbonyl.
Claim 6
Dependent Claim
10 words
A compound according to claim 2, wherein R is 2-thiophenecarbonyl.
Claim 7
Dependent Claim
10 words
A compound according to claim 2, wherein R is nicotinoyl.
Claim 8
Dependent Claim
10 words
A compound according to claim 2, wherein R is isonicotinoyl.
Claim 9
Dependent Claim
11 words
A compound according to claim 2, wherein R is isonicotinoyl hydrochloride.
Claim 10
Dependent Claim
10 words
A compound according to claim 2, wherein R is 3-furancarbonyl.
Claim 11
Dependent Claim
10 words
A compound according to claim 3, wherein R is 1-cyclohexanecarbonyl.
Claim 12
Dependent Claim
10 words
A compound according to claim 3, wherein R is 1-cyclopropanecarbonyl.
Claim 13
Dependent Claim
10 words
A compound according to claim 3, wherein R is 1-cyclobutanecarbonyl.
Claim 14
Dependent Claim
10 words
A compound according to claim 2, wherein R is N-methylpyrrole-2-carbonyl.
Claim 15
Dependent Claim
10 words
A compound according to claim 2, wherein R is 5-methyl-2-thiophenecarbonyl.
Claim 16
Dependent Claim
10 words
A compound according to claim 3, wherein R is 2,2-dimethyl-3-(2-methyl-1-propenyl)-1-cyclopropanecarbonyl.
Claim 17
Dependent Claim
10 words
A compound according to claim 3, wherein R is 2,2-dimethyl-3-(2,2-dichlorovinyl)-1-cyclopropanecarbonyl.
Claim 18
Dependent Claim
10 words
A compound according to claim 3, wherein R is 2,2,3,3-tetramethyl-1-cyclopropanecarbonyl.
Claim 19
Dependent Claim
10 words
A compound according to claim 3, wherein R is 1-(p-chlorophenyl)-1-cyclopropanecarbonyl.
Claim 20
Dependent Claim
10 words
A compound according to claim 3, wherein R is 1-methyl-1-cyclohexanecarbonyl.
Claim 21
Dependent Claim
10 words
A compound according to claim 3, wherein R is 1-methyl-1-cyclopropanecarbonyl.
Claim 22
Dependent Claim
10 words
A compound according to claim 3, wherein R is 2,2-dichloro-1-methyl-1-cyclopropanecarbonyl.
Claim 23
Dependent Claim
32 words
An antitumor composition which comprises an effective amount, for treating Lewis Lung Carcinoma in mice, of a compound of claim 1 as an active ingredient, and a pharmaceutically acceptable carrier or diluent.
Claim 24
Dependent Claim
25 words
An immunosuppressant composition which comprises an immunosuppressive amount of a compound of claim 1 as an active ingredient and a pharmaceutically acceptable carrier or diluent.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-03-01 | 1985-08-31 | 1986-03-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-03-01 | 1989-08-31 | 1990-03-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-03-01 | 1993-08-31 | 1994-03-02 | $7700.00 | Window Closed / Lapsed |