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US4643999A
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2-substituted imidazo[1,2-c]pyrimidines having anxiolytic properties
Assignee: Sanofi Aventis France
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Filing: 1984-12-14
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Granted: 1987-02-17
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Expires: 2004-12-14
Abstract
Abstract Novel imidazo[1,2-c]pyrimidines of the formula ##STR1## wherein R is an aryl of 6 to 12 carbon atoms, R 1 is selected from the group consisting of hydrogen and alkyl, alkoxy and alkylthio of 1 to 5 carbon atoms when R 2 and R 3 together form a carbon-nitrogen bond or R 1 and R 2 together are ═0 when R 3 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and alkenyl of 2 to 5 carbon atoms, R 4 is selected from the group consisting of alkoxy and alkylthio of 1 to 5 carbon atoms, R 5 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having anxiolytic properties.
Inventors
- 👤 Wilfred R. Tully
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 20:16
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A61; A61P; A61P25/00; A61P25/20; C07C; C07C45/00; C07C45/51; C07C45/511; C07C45/515; C07C45/61; C07C45/63; C07C49/00; C07C49/76
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
131 words
A compound selected from the group consisting of imidazo[1,2-c]pyrimidines of the formula ##STR8## wherein R is phenyl or naphthyl, R 1 is selected from the group consisting of hydrogen and alkyl, alkoxy and alkylthio of 1 to 5 carbon atoms when R 2 and R 3 together form a carbon nitrogen bond or R 1 and R 2 together are ═O when R 3 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and alkenyl of 2 to 5 carbon atoms, R 4 is selected from the group consisting of alkoxy and alkylthio of 1 to 5 carbon atoms, R 5 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
131 words
A compound selected from the group consisting of imidazo[1,2-c]pyrimidines of the formula ##STR8## wherein R is phenyl or naphthyl, R 1 is selected from the group consisting of hydrogen and alkyl, alkoxy and alkylthio of 1 to 5 carbon atoms when R 2 and R 3 together form a carbon nitrogen bond or R 1 and R 2 together are ═O when R 3 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and alkenyl of 2 to 5 carbon atoms, R 4 is selected from the group consisting of alkoxy and alkylthio of 1 to 5 carbon atoms, R 5 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein R is phenyl.
Claim 4
Dependent Claim
16 words
A compound of claim 2 wherein R 4 is CH 3 O-- or CH 3 S--.
Claim 5
Dependent Claim
15 words
A compound of claim 3 wherein R 2 and R 3 form a carbon-nitrogen bond.
Claim 6
Dependent Claim
16 words
A compound of claim 3 wherein R 3 is alkyl of 1 to 5 carbon atoms.
Claim 7
Dependent Claim
16 words
A compound of claim 3 wherein R 3 is alkenyl of 2 to 5 carbon atoms.
Claim 8
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of 2-benzoyl-6-ethyl-7-methoxy-imidazo[1,2-c]pyrimidin-5-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 9
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of 2-benzoyl-7-methoxy-6-propyl-imidazo[1,2-c]pyrimidin-5-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 10
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of (5-ethyl-7-methoxy-imidazo[1,2-c]pyrimidin-2-yl) phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 11
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of (7-methoxy-5-methyl-imidazo[1,2-c]pyrimidin-2-yl) phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 12
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of 6-allyl-2-benzoyl-7-methoxy-imidazo[1,2-c]pyrimidin-5-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 13
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of (7-methoxy-5-methylthio-imidazo[1,2-c]pyrimidin-2-yl)phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 14
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of 2-benzoyl-6-ethyl-7-methylthio-imidazo[1,2-c]pyrimidin-5-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 15
Dependent Claim
20 words
An anxiolytic composition comprising an anxiolytically effective amount of at least one compound of claim 1 and a pharmaceutical carrier.
Claim 16
Dependent Claim
9 words
A composition of claim 14 wherein R is phenyl.
Claim 17
Dependent Claim
16 words
A composition of claim 15 wherein R 4 is CH 3 O-- or CH 3 S--.
Claim 18
Dependent Claim
15 words
A composition of claim 16 wherein R 2 and R 3 form a carbon-nitrogen bond.
Claim 19
Dependent Claim
16 words
A composition of claim 16 wherein R 3 is alkyl of 1 to 5 carbon atoms.
Claim 20
Dependent Claim
16 words
A composition of claim 16 wherein R 3 is alkenyl of 2 to 5 carbon atoms.
Claim 21
Dependent Claim
26 words
A method of inducing anxiolytic activity in warm-blooded animals comprising administering to warm-blooded animals an anxiolytically effective amount of at least one compound of claim 1.
Claim 22
Dependent Claim
9 words
A method of claim 20 wherein R is phenyl.
Claim 23
Dependent Claim
16 words
A method of claim 21 wherein R 4 is CH 3 O-- or CH 3 S--.
Claim 24
Dependent Claim
15 words
A method of claim 22 wherein R 2 and R 3 form a carbon-nitrogen bond.
Claim 25
Dependent Claim
16 words
A method of claim 22 wherein R 3 is alkyl of 1 to 5 carbon atoms.
Claim 26
Dependent Claim
16 words
A method of claim 22 wherein R 3 is alkenyl of 2 to 5 carbon atoms.
Claim 27
Dependent Claim
24 words
A method of claim 20 wherein the compound is selected from the group consisting of 2-benzoyl-6-ethyl-7-methoxy-imidazo[1,2-c]pyrimidin-5-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 28
Dependent Claim
24 words
A method of claim 20 wherein the compound is selected from the group consisting of 2-benzoyl-7-methoxy-6-propyl-imidazo[1,2-c]pyrimidin-5-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 29
Dependent Claim
24 words
A method of claim 20 wherein the compound is selected from the group consisting of (5-ethyl-7-methoxy-imidazo[1,2-c]pyrimidin-2-yl)phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 30
Dependent Claim
24 words
A method of claim 20 wherein the compound is selected from the group consisting of (7-methoxy-5-methyl-imidazo[1,2-c]pyrimidin-2-yl)phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 31
Dependent Claim
24 words
A method of claim 20 wherein the compound is selected from the group consisting of 6-allyl-2-benzoyl-7-methoxy-imidazo[1,2-c]pyrimidin-5-one and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 32
Dependent Claim
24 words
A method of claim 20 wherein the compound is selected from the group consisting of {7-methoxy-5-methylthio-imidazo[1,2-c]pyrimidin-2-yl}phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 33
Dependent Claim
24 words
A method of claim 20 wherein the compound is selected from the group consisting of 2-benzoyl-6-ethyl-7-methylthio-imidazo[1,2-c]pyrimidin-5-one and its non-toxic pharmaceutically acceptable acid addition salts.
References Cited (Backward Citations)
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| 7.5 Years (Year 8) | 1994-02-16 | 1994-08-18 | 1995-02-17 | $3760.00 | Window Closed / Lapsed |
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