EP0204534A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Quinazolinone compounds and processes for the preparation thereof
Assignee: Tanabe Pharma Corp
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Filing: 1986-06-02
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Granted: —
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Expires: 2006-06-02
Abstract
Abstract There are described novel quinazolinone compounds of the formula: wherein R is hydrogen atom or a lower alkyl, R 1 is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R 3, R 4 and R 5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, ortwo adjacent groups of R 2 , R 3 , R 4 and R 5 when taken together form methylenedioxy and the other two are hydrogen atom, and salts thereof. The compounds are useful for the prophylaxis and treatment of various diabetic complications. There are also disclosed processes for the preparation of compound of formula I, and pharmaceutical compositions containing such compound as an active ingredient.
Inventors
- 👤 Yoshihisa Yamada
- 👤 Yuzo Matsuoka
- 👤 Mamoru Matsumoto
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-02 23:43
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/10; C07D239/00; C07D239/70; C07D239/72; C07D239/95; C07D239/96
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
95 words
A quinazolinone compound characterised by the formula: wherein R is hydrogen atom or a lower alkyl, R 1 is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R3, R4 and R5 are the same or different and are each hydrogen atom, a halogen, atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R 2 , R3, R 4 and R 5 when taken together form methylenedioxy and the other two are hydrogen atom, or a salt thereof.
Claim 2
Dependent Claim
95 words
A quinazolinone compound characterised by the formula: wherein R is hydrogen atom or a lower alkyl, R 1 is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R3, R4 and R5 are the same or different and are each hydrogen atom, a halogen, atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R 2 , R3, R 4 and R 5 when taken together form methylenedioxy and the other two are hydrogen atom, or a salt thereof.
Claim 3
Dependent Claim
24 words
A compound as claimed in claim 1, characterised in that Rl is a lower alkyl, phenyl, a lower alkyl-phenyl, a halogenophenyl or an aralkyl.
Claim 4
Dependent Claim
97 words
A compound as claimed in claim 1 or 2, characterised in that R is hydrogen or C l-4 alkyl; R l is C l - 4 alkyl, phenyl, C l - 4 alkyl-phenyl, halogenophenyl, or aralkyl; and R 2 , R3, R4 and R 5 are the same or different and are each hydrogen, halogen, C l - 4 alkyl, C 2 - 5 alkoxycarbonyl, or C 2 - 5 alkoxycarbonyl-C 2-4 alkenyl, or two adjacent groups of R 2 1 R3, R4 and R 5 when taken together form methylenedioxy and the other two are hydrogen.
Claim 5
Dependent Claim
105 words
A compound as claimed in any one of the preceding claims, characterised in that R is hydrogen or C 1-4 alkyl; R 1 is C l-4 alkyl, phenyl, C 1-4 alkyl-phenyl, halogenophenyl, or phenyl - C l - 2 alkyl; R 2 is hydrogen, halogen or C 1-4 alkyl; R 3 and R 4 are the same or different and are each hydrogen, halogen, C l - 4 alkyl, C 1-4 alkoxy, C 2 - 5 alkoxycarbonyl, or C 2 - 5 alkoxycarbonyl-C 2 - 4 alkenyl, or R 3 and R 4 when taken together form methylene-dioxy; and R 5 is hydrogen or halogen.
Claim 6
Dependent Claim
76 words
A compound as claimed in any one of the preceding claims, characterised in that R is hydrogen, .methyl or isobutyl; R l is methyl, n-butyl, phenyl, methylphenyl, chlorophenyl, or benzyl; R 2 is hydrogen, chlorine or methyl; R 3 and R 4 are the same or different and are each hydrogen, fluorine, chlorine, bromine, methyl, methoxy, ethoxycarbonyl, or ethoxycarbonyl-vinyl, or R3 and R4 when taken together form methylenedioxy; and R 5 is hydrogen, fluorine or chlorine.
Claim 7
Dependent Claim
69 words
A compound as claimed in any one of the preceding claims, characterised in that R is hydrogen or isobutyl; Rl is methyl, n-butyl, phenyl, methylphenyl, chlorophenyl, or benzyl; R 2 is hydrogen or methyl; R 3 is hydrogen, fluorine, chlorine, bromine, methyl or ethoxycarbonyl; R4 is hydrogen, fluorine, chlorine, methyl or methoxy, or R 3 and R4 when taken together form methylenedioxy; and R is hydrogen, fluorine or chlorine.
Claim 8
Dependent Claim
48 words
The compound as claimed in claim 4, characterised in that R is hydrogen or C 1-4 alkyl; R l is C l - 4 alkyl; R 2 is hydrogen; R 3 is halogen; R4 is hydrogen, halogen or C 1-4 alkyl; and R 5 is hydrogen or halogen.
Claim 9
Dependent Claim
47 words
A compound as claimed in any one of claims 1 to 4 or 7, characterised in that R is hydrogen or isobutyl; Rl is methyl; R2 is hydrogen; R3 is fluorine, chlorine or bromine; R4 is hydrogen, chlorine or methyl; and R 5 is hydrogen or chlorine.
Claim 10
Dependent Claim
6 words
6-chloro-3-methyl-spiroLl,2,3,4-tetrahydro- quinazolzne-4,4'-imidazolidine]-2,2',5'-trione or a salt thereof.
Claim 11
Dependent Claim
6 words
6-chloro-3-methyl-spiroLl,2,3,4-tetrahydro- quinazolzne-4,4'-imidazolidine]-2,2',5'-trione or a salt thereof.
Claim 12
Dependent Claim
5 words
d-6-chlor6-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione or a salt thereof.
Claim 13
Dependent Claim
5 words
d-6-chlor6-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione or a salt thereof.
Claim 14
Dependent Claim
16 words
An optically active isomer of a compound as claimed in any one of the preceding claims.
Claim 15
Dependent Claim
15 words
A compound as claimed in claim 11, characterised in that it is a dextro-rotatory isomer.
Claim 16
Dependent Claim
85 words
A compound characterised by the formula: wherein R l is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R2, R3, R 4 and R 5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R2, R3, R4 and R5 when taken together form methylenedioxy and the other two are hydrogen atom, and R 6 is a lower alkyl.
Claim 17
Dependent Claim
85 words
A compound characterised by the formula: wherein R l is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R2, R3, R 4 and R 5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R2, R3, R4 and R5 when taken together form methylenedioxy and the other two are hydrogen atom, and R 6 is a lower alkyl.
Claim 18
Dependent Claim
88 words
A compound characterised by the formula: wherein Rl is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R 3, R 4 and R 5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R2, R3, R 4 and R 5 when taken together form methylenedioxy and the other two are hydrogen atom, and R6 is a lower alkyl.
Claim 19
Dependent Claim
88 words
A compound characterised by the formula: wherein Rl is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R 3, R 4 and R 5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R2, R3, R 4 and R 5 when taken together form methylenedioxy and the other two are hydrogen atom, and R6 is a lower alkyl.
Claim 20
Dependent Claim
41 words
A pharmaceutical composition which comprises an effective amount of an active ingredient in admixture with a conventional pharmaceutically acceptable carrier or diluent, characterised in that the active ingredient comprises a compound as claimed in any one of claims 1 to 12.
Claim 21
Dependent Claim
131 words
A process for preparing a quinazolinone compound of the formula: wherein Rl is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R3, R4 and R5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R2, R3, R4 and R5 when taken together form methylenedioxy and the other two are hydrogen atom, or a salt thereof, characterised by subjecting a compound of the formula: wherein R 6 is a lower alkyl, and R l , R 2 , R 3, R 4 and R 5 are as defined above, to cyclization reaction, and optionally further converting the product into a salt thereof.
Claim 22
Dependent Claim
131 words
A process for preparing a quinazolinone compound of the formula: wherein Rl is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R3, R4 and R5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R2, R3, R4 and R5 when taken together form methylenedioxy and the other two are hydrogen atom, or a salt thereof, characterised by subjecting a compound of the formula: wherein R 6 is a lower alkyl, and R l , R 2 , R 3, R 4 and R 5 are as defined above, to cyclization reaction, and optionally further converting the product into a salt thereof.
Claim 23
Dependent Claim
156 words
A process for preparing a quinazolinone compound of the formula: wherein R' is a lower alkyl, Rl is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R 3 , R 4 and R 5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R 2 , R 3 , R4 and R5 when taken together form methylenedioxy and the other two are hydrogen atom, or a salt thereof, characterised by the steps of alkylating a compound of the formula: wherein X l and X 2 are a protecting group, and Rl, R2, R 3 , R 4 and R 5 are as defined above, or a salt thereof, removing the protecting group from the resulting product, and optionally converting the resulting product into a salt thereof.
Claim 24
Dependent Claim
156 words
A process for preparing a quinazolinone compound of the formula: wherein R' is a lower alkyl, Rl is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, and R 2 , R 3 , R 4 and R 5 are the same or different and are each hydrogen atom, a halogen atom, a lower alkyl, a lower alkoxy, a lower alkoxycarbonyl or a lower alkoxycarbonyl-lower alkenyl, or two adjacent groups of R 2 , R 3 , R4 and R5 when taken together form methylenedioxy and the other two are hydrogen atom, or a salt thereof, characterised by the steps of alkylating a compound of the formula: wherein X l and X 2 are a protecting group, and Rl, R2, R 3 , R 4 and R 5 are as defined above, or a salt thereof, removing the protecting group from the resulting product, and optionally converting the resulting product into a salt thereof.
Claim 25
Dependent Claim
92 words
A process for preparing a quinazolinone compound of the formula: wherein R is hydrogen atom or a lower alkyl, R 1 is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, R31 is a halogen atom, R 41 is hydrogen atom or a lower alkoxy, R 51 is hydrogen atom or a halogen atom, or a salt thereof, characterised by halogenating a compound of the formula: wherein R, Rl and R 41 are the same as above, or a salt thereof, and optionally converting the product to a salt thereof.
Claim 26
Dependent Claim
92 words
A process for preparing a quinazolinone compound of the formula: wherein R is hydrogen atom or a lower alkyl, R 1 is a lower alkyl, a substituted or unsubstituted phenyl or an aralkyl, R31 is a halogen atom, R 41 is hydrogen atom or a lower alkoxy, R 51 is hydrogen atom or a halogen atom, or a salt thereof, characterised by halogenating a compound of the formula: wherein R, Rl and R 41 are the same as above, or a salt thereof, and optionally converting the product to a salt thereof.
References Cited (Backward Citations)
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