EP0191735A2
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EP
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Novel oxaluric acid derivatives and pharmaceutical compositions containing them
Assignee: Nippon Zoki Pharmaceutical Co Ltd
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Filing: 1986-02-10
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Granted: —
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Expires: 2006-02-10
Abstract
Abstract Oxaluric acid derivatives of the formula (I): <CHEM> wherein each of R1 and R2, which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R1 and R2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R3 represents a hydrogen atom or an alkyl group as well as pharmaceutically acceptable salts and metal complexes thereof are disclosed. Pharmaceutical compositions containing the compounds as active ingredients are disclosed. The compounds possess hypoglycemic activity and are useful in the treatment of diabetes.
Inventors
- 👤 Kazuharu Nippon Zoki Pharmaceutical Co.Ltd Ienaga
- 👤 Ko Nippon Zoki Pharmaceutical Co.Ltd Nakamura
- 👤 Akira Nippon Zoki Pharmaceutical Co.Ltd Ishii
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 06:53
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/20; C07D295/215; A; A61; A61P; A61P3/00; A61P3/08; A61P3/10; C07C; C07C275/00; C07C275/46; C07C275/48; C07C275/50; C07C2601/00; C07C2601/06; C07C2601/08; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
67 words
An oxaluric acid derivative of the general formula I wherein each of R 1 and R 2 , which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
67 words
An oxaluric acid derivative of the general formula I wherein each of R 1 and R 2 , which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
15 words
An oxaluric acid derivative according to claim 1, wherein R 2 represents a hydrogen atom.
Claim 4
Dependent Claim
18 words
An oxaluric acid derivative according to claim 1 or claim 2, wherein R 3 represents a hydrogen atom.
Claim 5
Dependent Claim
50 words
An oxaluric acid derivative according to claim 1, wherein one or both of R 1 and R 25 which may the same or different, represents a straight or branched chain alkyl group having from 1 to 20 carbon atoms or a cycloalkyl group having from 3 to 8 carbon atoms.
Claim 6
Dependent Claim
59 words
An oxaluric acid derivative according to claim 4 wherein one or both of R 1 and R 2 , which may be the same of different, represents methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, sec-butyl, tert.-butyl, pentyl, iso-pentyl, neo-pentyl, tert.-pentyl, hexyl, iso-hexyl, dimethylbutyl, heptyl, octyl, nonyl, decyl, stearyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, aziridino,pyrrolodono, piperidino, piperazi- no or morpholino.
Claim 7
Dependent Claim
31 words
An oxaluric acid derivative as claimed in any one of the preceding claims wherein R 3 represents a straight or branched chain alkyl group having from 1 to 20 carbon atoms.
Claim 8
Dependent Claim
34 words
An oxaluric acid derivative according to claim 6, wherein R 3 represents a methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, sec-butyl, tert-butyl, pentyl, iso-pentyl, neo-pentyl, tert-pentyl, hexyl, iso-hexyl, diemthylbutyl, heptyl, octyl, nonyl,decyl or stearyl group.
Claim 9
Dependent Claim
85 words
5-Methyloxaluric acid ammonium salt, 5-ethyloxaluric acid ammonium salt, 5-butyloxaluric acid, 5-iso-butyloxaluric acid, 5-tert-butyloxaluric acid, 5-hexyloxaluric acid, 5-(1,3-dimethyl)oxaluric, 5-decyloxaluric acid, 5-cyclopentyloxaluric acid, 5-cyclohexyloxaluric acid, 5-methyloxaluric acid methyl ester, 5-methyloxaluric acid ethyl ester, 5-butyloxaluric acid methyl ester, 5-iso-butyloxaluric acid ethyl ester, 5,5 dimethyloxaluric acid methyl ester, 5,5-dimethyloxaluric acid ethyl ester, 5-cyclohexyloxaluric acid ethyl ester, N-(piperidylcarbonyl)oxamic acid methyl ester, N-(1-piperidylcarbonyl)oxamic acid ethyl ester, 5-methyloxaluric acid butyl ester, 5-methyloxaluric acid iso-butyl ester, 5-methyloxaluric acid octyl ester, 5-butyloxaluric acid butyl ester, 5-cyclohexyloxaluric acid iso-propyl ester or 5-cyclohexyloxaluric acid butyl ester.
Claim 10
Dependent Claim
85 words
5-Methyloxaluric acid ammonium salt, 5-ethyloxaluric acid ammonium salt, 5-butyloxaluric acid, 5-iso-butyloxaluric acid, 5-tert-butyloxaluric acid, 5-hexyloxaluric acid, 5-(1,3-dimethyl)oxaluric, 5-decyloxaluric acid, 5-cyclopentyloxaluric acid, 5-cyclohexyloxaluric acid, 5-methyloxaluric acid methyl ester, 5-methyloxaluric acid ethyl ester, 5-butyloxaluric acid methyl ester, 5-iso-butyloxaluric acid ethyl ester, 5,5 dimethyloxaluric acid methyl ester, 5,5-dimethyloxaluric acid ethyl ester, 5-cyclohexyloxaluric acid ethyl ester, N-(piperidylcarbonyl)oxamic acid methyl ester, N-(1-piperidylcarbonyl)oxamic acid ethyl ester, 5-methyloxaluric acid butyl ester, 5-methyloxaluric acid iso-butyl ester, 5-methyloxaluric acid octyl ester, 5-butyloxaluric acid butyl ester, 5-cyclohexyloxaluric acid iso-propyl ester or 5-cyclohexyloxaluric acid butyl ester.
Claim 11
Dependent Claim
17 words
A metal complex of an oxaluric acid derivative as claimed in any one of the preceding claims.
Claim 12
Dependent Claim
14 words
Oxaluric acid derivtives substantially as hereinbefore described with reference to the foregoing working Examples.
Claim 13
Dependent Claim
14 words
Oxaluric acid derivtives substantially as hereinbefore described with reference to the foregoing working Examples.
Claim 14
Dependent Claim
76 words
A pharmaceutical composition containing a compound of the general formula I wherein each of R 1 and R 25 which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof together with a pharmaceutically acceptable carrier or diluent.
Claim 15
Dependent Claim
76 words
A pharmaceutical composition containing a compound of the general formula I wherein each of R 1 and R 25 which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof together with a pharmaceutically acceptable carrier or diluent.
Claim 16
Dependent Claim
23 words
A pharmaceutical composition as claimed in claim 11 containing an oxaluric acid derivative as claimed in any one of claims 2 to 10.
Claim 17
Dependent Claim
76 words
The use of an oxaluric acid derivative of the general formula I wherein each of R 1 and R 2 , which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof, for the manufacture of hypoglycemic agents.
Claim 18
Dependent Claim
76 words
The use of an oxaluric acid derivative of the general formula I wherein each of R 1 and R 2 , which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof, for the manufacture of hypoglycemic agents.
Claim 19
Dependent Claim
25 words
The use as claimed in claim 13 wherein the oxaluric acid derivative is a compound as claimed in any one of claims 1 to 10.
Claim 20
Independent Claim
83 words
A method for the treatment of mammals suffering from diabetes, which comprises treating said mammal with an oxaluric acid derivative of the general formula I wherein each of R 1 and R 2 , which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof.
Claim 21
Independent Claim
83 words
A method for the treatment of mammals suffering from diabetes, which comprises treating said mammal with an oxaluric acid derivative of the general formula I wherein each of R 1 and R 2 , which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim
123 words
A process for the preparation of an oxaluric acid derivatives of the general formula I, wherein each of R 1 and R 2 , which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof which comprises, a) reacting an oxalyl halide with an N-monoalkylurea, b) effecting an N-alkylation reaction on an unsubstituted imidazolidiene, c) reacting an N-monoalkylurea, N-monocycloalkylurea or N,N I- dialkylurea with an alkyloxalyl halide, d) reacting water or alcohol with an oxalyl halide and then adding an N-monoalkylurea, N-monocycloalkylurea or N,N'dialkyl- urea.
Claim 23
Dependent Claim
123 words
A process for the preparation of an oxaluric acid derivatives of the general formula I, wherein each of R 1 and R 2 , which may be the same or different, represents a hydrogen atom, an alkyl or cycloalkyl group, or R 1 and R 2 taken together with the adjacent nitrogen atom form a heterocyclic ring and R 3 represents a hydrogen atom or an alkyl group, and pharmaceutically acceptable salts thereof which comprises, a) reacting an oxalyl halide with an N-monoalkylurea, b) effecting an N-alkylation reaction on an unsubstituted imidazolidiene, c) reacting an N-monoalkylurea, N-monocycloalkylurea or N,N I- dialkylurea with an alkyloxalyl halide, d) reacting water or alcohol with an oxalyl halide and then adding an N-monoalkylurea, N-monocycloalkylurea or N,N'dialkyl- urea.
Claim 24
Dependent Claim
15 words
A process as claimed in claim 16 wherein the oxalyl halide is an oxalyl chloride.
Claim 25
Dependent Claim
25 words
Processes for the preparation of an oxaluric acid derivati ves of the general formula I as hereinbefore defined especially with reference to the foregoing Examples.
Claim 26
Dependent Claim
25 words
Processes for the preparation of an oxaluric acid derivati ves of the general formula I as hereinbefore defined especially with reference to the foregoing Examples.
Claim 27
Dependent Claim
14 words
Each and every novel feature of the invention hereinbefore disclosed in the foregoing specification.
Claim 28
Dependent Claim
14 words
Each and every novel feature of the invention hereinbefore disclosed in the foregoing specification.
References Cited (Backward Citations)
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