Patent US3629367A successfully refreshed from Google Patents.
Patent US4532243A successfully refreshed from Google Patents.
US4532243A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Imidazo(1,2-a)pyrimidines and their salts useful for treating anxiety
Assignee: Sanofi Aventis France
•
Filing: 1983-08-24
•
Granted: 1985-07-30
•
Expires: 2003-08-24
Abstract
Abstract Novel imidazo[1,2-a]pyrimidines of the formula <IMAGE> I wherein R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, thienyl and pyridyl, each of said group being optionally substituted with at least one member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 alkyl carbon atoms and dialkylamino with alkyl of 1 to 5 carbons atoms, R1 and R2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, benzyl and phenethyl, or taken together form alkylene of 3 to 5 carbon atoms, each of said groups being optionally substituted with at least one member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 alkyl carbon atoms and dialkylamino with alkyls of 1 to 5 carbon atoms, X is selected from the group consisting of oxygen and sulfur and R3 is alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts, having anxiolytic activity and novel intermediates.
Inventors
- 👤 Wilfred R. Tully
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 20:03
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/47; A; A61; A61P; A61P25/00; A61P25/18; A61P25/24; C07D239/70; C07D239/72; C07D239/95; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
232 words
A compound selected from the group consisting of imidazo[1,2-a]pyrimidines of the formula ##STR33## wherein R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, phenyl, naphthyl, thienyl and pyridyl, each of said group optionally substituted with a member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 alkyl carbon atoms and dialkylamino with alkyl of 1 to 5 carbon atoms, R 1 and R 2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, benzyl and phenethyl, each of said groups being optionally substituted with a member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 carbon atoms and dialkylamino with alkyls of 1 to 5 carbon atoms, X is selected from the group consisting of oxygen and sulfur and R 3 is alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
232 words
A compound selected from the group consisting of imidazo[1,2-a]pyrimidines of the formula ##STR33## wherein R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, phenyl, naphthyl, thienyl and pyridyl, each of said group optionally substituted with a member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 alkyl carbon atoms and dialkylamino with alkyl of 1 to 5 carbon atoms, R 1 and R 2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, benzyl and phenethyl, each of said groups being optionally substituted with a member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms, alkoxy and alkylthio of 1 to 5 carbon atoms, trifluoromethyl, amino, alkylamino of 1 to 5 carbon atoms and dialkylamino with alkyls of 1 to 5 carbon atoms, X is selected from the group consisting of oxygen and sulfur and R 3 is 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
35 words
A compound of claim 1 wherein R 1 and R 2 are individually selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, hexyl, allyl and benzyl and R 3 is methyl or ethyl.
Claim 5
Dependent Claim
9 words
A compound of claim 3 wherein R is phenyl.
Claim 6
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of [6-ethyl-5-methyl-7-(methylthio)imidazo[1,2-a]pyrimidin-2-yl]phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 7
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of [5-(methylthio)cyclopenta[e]imidazo[1,2-a]pyrimidin-2-yl]phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 8
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of [7-methoxy-5-methyl-6-(1-methylethyl)-imidazo[1,2-a]pyrimidin-2-yl]phenylmethanone 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 [6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl]phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 10
Dependent Claim
125 words
A compound of claim 1 wherein R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, pyridyl and thienyl, R 1 and R 2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, benzyl and phenethyl, each of R, R 1 and R 2 being optionally substituted with a member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms and alkoxy of 1 to 5 carbon atoms.
Claim 11
Dependent Claim
21 words
An anxiolytic composition comprising an anxiolytically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 12
Dependent Claim
9 words
A composition of claim 10 wherein R is phenyl.
Claim 13
Dependent Claim
35 words
A composition of claim 10 wherein R 1 and R 2 are individually selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, hexyl, allyl and benzyl and R 3 is methyl or ethyl.
Claim 14
Dependent Claim
9 words
A composition of claim 12 wherein R is phenyl.
Claim 15
Dependent Claim
25 words
A composition of claim 10 wherein the active compound is selected from the group consisting of [6-ethyl-5-methyl-7-(methylthio)imidazo[1,2-a]pyrimidin-2-yl]phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 16
Dependent Claim
25 words
A composition of claim 10 wherein the active compound is selected from the group consisting of [5-(methylthio)cyclopenta[e]imidazo[1,2-a]pyrimidin-2-yl]phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 17
Dependent Claim
25 words
A composition of claim 10 wherein the active compound is selected from the group consisting of [7-methoxy-5-methyl-6-(1-methylethyl)-imidazo[1,2-a]pyrimidin-2-yl]phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 18
Dependent Claim
25 words
A composition of claim 10 wherein the active compound is selected from the group consisting of [6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl]phenylmethanone and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 19
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.
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) | 1988-07-29 | 1989-01-28 | 1989-07-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-29 | 1993-01-28 | 1993-07-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-29 | 1997-01-28 | 1997-07-30 | $7700.00 | Window Closed / Lapsed |