US4242344A
Expired / Lapsed
US
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Piperazinyl-imidazo[1,2-a]pyrazines
Assignee: Merck and Co Inc
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Filing: 1979-09-07
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Granted: 1980-12-30
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Expires: 1999-09-07
Abstract
Abstract Piperazinyl-imidazo[1,2-a]pyrazines, derived from reactions between halo-imidazo[1,2-a]pyrazines with piperazine derivatives, are found to be active anorexic, antidepressant, antihypertensive, analgesic, antiarrhythmic, and/or anti-smoking agents.
Inventors
- 👤 William C. Lumma
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 10:57
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D241/00; C07D241/02; C07D241/10; C07D241/14; C07D241/20; C07D241/24; C07D241/26
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
196 words
A compound of the structural formula: ##STR23## or a pharmaceutically acceptable salt thereof, wherein: the piperazinyl group ##STR24## and Y are at positions 5, 6 or 8; R 1 and R 2 independently ar (a) hydrogen; (b) lower alkyl; (c) lower cycloalkyl; (d) lower alkylthio; (e) halo; (f) --CF 3 ; (g) CF 3 S--; (h) C 6 H 5 --; (i) phenyl-substituted by halogen; (j) phenyl-substituted by C 1-3 alkyl; (k) phenyl-substituted by C 1-3 alkoxy; (l ) ##STR25## wherein R 4 is hydrogen or C 1-6 alkyl; R 5 is C 1-6 alkyl; or R 4 and R 5 taken together form with the nitrogen atom to which they are attached, a piperidino group; (m) ##STR26## wherein R 6 and R 7 are independently hydrogen, C 1-3 alkyl, or phenyl; or R 1 and R 2 joined together form --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 CH 2 CH 2 --; R 3 is (a) hydrogen; (b) lower alkyl; (c) lower(cycloalkyl-alkyl); (d) lower cycloalkyl; or (e) lower alkanoyl; Y is (a) hydrogen; (b) halo; (c) --C.tbd.N; (d) --CF 3 ; (e) lower alkyl (f) lower alkoxy; or (g) --COOH.
Claim 2
Dependent Claim
196 words
A compound of the structural formula: ##STR23## or a pharmaceutically acceptable salt thereof, wherein: the piperazinyl group ##STR24## and Y are at positions 5, 6 or 8; R 1 and R 2 independently ar (a) hydrogen; (b) lower alkyl; (c) lower cycloalkyl; (d) lower alkylthio; (e) halo; (f) --CF 3 ; (g) CF 3 S--; (h) C 6 H 5 --; (i) phenyl-substituted by halogen; (j) phenyl-substituted by C 1-3 alkyl; (k) phenyl-substituted by C 1-3 alkoxy; (l ) ##STR25## wherein R 4 is hydrogen or C 1-6 alkyl; R 5 is C 1-6 alkyl; or R 4 and R 5 taken together form with the nitrogen atom to which they are attached, a piperidino group; (m) ##STR26## wherein R 6 and R 7 are independently hydrogen, C 1-3 alkyl, or phenyl; or R 1 and R 2 joined together form --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 CH 2 CH 2 --; R 3 is (a) hydrogen; (b) lower alkyl; (c) lower(cycloalkyl-alkyl); (d) lower cycloalkyl; or (e) lower alkanoyl; Y is (a) hydrogen; (b) halo; (c) --C.tbd.N; (d) --CF 3 ; (e) lower alkyl (f) lower alkoxy; or (g) --COOH.
Claim 3
Dependent Claim
175 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the piperazinyl group and Y are at position 6 or 8; R 1 and R 2 are independently (a) hydrogen; (b) halo; (c) CF 3 ; (d) CF 3 S; (e) C 6 H 5 ; (f) phenyl-substituted by halogen; (g) ##STR27## wherein R 6 and R 7 are independently hydrogen, C 1-3 alkyl, or phenyl; (h) ##STR28## wherein R 4 is hydrogen or C 1-6 alkyl; R 5 is C 1-6 alkyl; or R 4 and R 5 taken together form with the nitrogen atom to which they are attached, a piperidino group; or R 1 and R 2 are joined together form --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 CH 2 CH 2 --; R 3 is (a) hydrogen; (b) C 1-3 alkyl; (c) C 1-3 alkanoyl; (d) cyclopropylmethyl; or (e) cyclopropyl or cyclohexyl; and Y is (a) hydrogen; (b) Cl, F, Br, or I; (c) --C.tbd.N (d) --CF 3 ; or (e) CH 3 O--.
Claim 4
Dependent Claim
107 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the piperazinyl group is at position 8; and Y is at position 6; R 1 and R 2 are independently (a) hydrogen; (b) Cl, Br or F; (c) CF 3 ; (d) CF 3 S; (e) o-Cl--C 6 H 4 --; (f) --SO 2 N(CH 3 ) 2 ; (g) ##STR29## or where R 1 and R 2 are joined together they form --CH 2 CH 2 CH 2 CH 2 --; R 3 is (a) hydrogen; (b) --CH 3 ; or (c) cyclopropylmethyl; and Y is (a) hydrogen; or (b) Cl, F, or Br.
Claim 5
Dependent Claim
55 words
The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the piperazinyl group is at position 8; and Y is at position 6; R 1 and R 2 are independently (a) hydrogen; or (b) Cl; R 3 is (a) hydrogen; or (b) --CH 3 ; and Y is (a) hydrogen; or (b) Cl.
Claim 6
Dependent Claim
14 words
The compound of claim 1 which is 3-chloro-6-(1-piperazinyl)imidazol[1,2-a]pyrazine or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
14 words
The compound of claim 1 which is 8-(1-piperazinyl)imidazo[1,2-a]pyrazine or a pharmaceutically acceptable salt thereof.
Claim 8
Independent Claim
215 words
A method of decreasing appetite, which comprises the administration to a mammalian species in need of such treatment an effective amount of a compound of formula: ##STR30## or a pharmaceutically acceptable salt thereof, wherein: the piperazinyl group ##STR31## and Y are at positins 5, 6 or 8; R 1 and R 2 independently are (a) hydrogen; (b) lower alkyl; (c) lower cycloalkyl; (d) lower alkylthio; (e) halo; (f) --CF 3 ; (g) CF 3 S--; (h) C 6 H 5 --; (i) phenyl-substituted by halogen; (j) phenyl-substituted by C 1-3 alkyl; (k) phenyl-substituted by C 1-3 alkoxy; (l) ##STR32## wherein R 4 is hydrogen or C 1-6 alkyl; R 5 is C 1-6 alkyl; or R 4 and R 5 taken together form with the nitrogen atom to which they are attached, a piperidino group; (m) ##STR33## wherein R 6 and R 7 are independently hydrogen, C 1-3 alkyl, or phenyl; or R 1 and R 2 joined together form --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 CH 2 CH 2 --; R 3 is (a) hydrogen; (b) lower alkyl; (c) lower(cycloalkyl-alkyl); (d) lower cycloalkyl; or (e) lower alkanoyl; Y is (a) hydrogen; (b) halo; (c) --C.tbd.N; (d) --CF 3 ; (e) lower alkyl; (f) lower alkoxy; or (g) --COOH.
Claim 9
Independent Claim
215 words
A method of decreasing appetite, which comprises the administration to a mammalian species in need of such treatment an effective amount of a compound of formula: ##STR30## or a pharmaceutically acceptable salt thereof, wherein: the piperazinyl group ##STR31## and Y are at positins 5, 6 or 8; R 1 and R 2 independently are (a) hydrogen; (b) lower alkyl; (c) lower cycloalkyl; (d) lower alkylthio; (e) halo; (f) --CF 3 ; (g) CF 3 S--; (h) C 6 H 5 --; (i) phenyl-substituted by halogen; (j) phenyl-substituted by C 1-3 alkyl; (k) phenyl-substituted by C 1-3 alkoxy; (l) ##STR32## wherein R 4 is hydrogen or C 1-6 alkyl; R 5 is C 1-6 alkyl; or R 4 and R 5 taken together form with the nitrogen atom to which they are attached, a piperidino group; (m) ##STR33## wherein R 6 and R 7 are independently hydrogen, C 1-3 alkyl, or phenyl; or R 1 and R 2 joined together form --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 CH 2 CH 2 --; R 3 is (a) hydrogen; (b) lower alkyl; (c) lower(cycloalkyl-alkyl); (d) lower cycloalkyl; or (e) lower alkanoyl; Y is (a) hydrogen; (b) halo; (c) --C.tbd.N; (d) --CF 3 ; (e) lower alkyl; (f) lower alkoxy; or (g) --COOH.
Claim 10
Dependent Claim
215 words
A pharmaceutical composition for decreasing appetite, in a mammalian species comprising a pharmaceutical carrier and an effective amount of a compound of formula: ##STR34## or a pharmaceutically acceptable salt thereof, wherein: the piperazinyl group ##STR35## and Y are at positions 5, 6 or 8; R 1 and R 2 independently are (a) hydrogen; (b) lower alkyl; (c) lower cycloalkyl; (d) lower alkylthio; (e) halo; (f) --CF 3 ; (g) CF 3 S--; (h) C 6 H 5 --; (i) phenyl-substituted by halogen; (j) phenyl-substituted by C 1-3 alkyl; (k) phenyl-substituted by C 1-3 alkoxy; (l) ##STR36## wherein R 4 is hydrogen or C 1-6 alkyl; R 5 is C 1-6 alkyl; or R 4 and R 5 taken together form with the nitrogen atom to which they are attached, a 5 or 6 membered heterocycle; (m) ##STR37## wherein R 6 and R 7 are independently hydrogen, C 1-3 alkyl, or phenyl; or R 1 and R 2 joined together form --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 CH 2 CH 2 --; R 3 is (a) hydrogen; (b) lower alkyl; (c) lower(cycloalkyl-alkyl); (d) lower cycloalkyl; or (e) lower alkanoyl; Y is (a) hydrogen; (b) halo; (c) --C.tbd.N (d) --CF 3 ; (e) lower alkyl; (f) lower alkoxy; or (g) --COOH.
Claim 11
Dependent Claim
215 words
A pharmaceutical composition for decreasing appetite, in a mammalian species comprising a pharmaceutical carrier and an effective amount of a compound of formula: ##STR34## or a pharmaceutically acceptable salt thereof, wherein: the piperazinyl group ##STR35## and Y are at positions 5, 6 or 8; R 1 and R 2 independently are (a) hydrogen; (b) lower alkyl; (c) lower cycloalkyl; (d) lower alkylthio; (e) halo; (f) --CF 3 ; (g) CF 3 S--; (h) C 6 H 5 --; (i) phenyl-substituted by halogen; (j) phenyl-substituted by C 1-3 alkyl; (k) phenyl-substituted by C 1-3 alkoxy; (l) ##STR36## wherein R 4 is hydrogen or C 1-6 alkyl; R 5 is C 1-6 alkyl; or R 4 and R 5 taken together form with the nitrogen atom to which they are attached, a 5 or 6 membered heterocycle; (m) ##STR37## wherein R 6 and R 7 are independently hydrogen, C 1-3 alkyl, or phenyl; or R 1 and R 2 joined together form --CH 2 CH 2 CH 2 -- or --CH 2 CH 2 CH 2 CH 2 --; R 3 is (a) hydrogen; (b) lower alkyl; (c) lower(cycloalkyl-alkyl); (d) lower cycloalkyl; or (e) lower alkanoyl; Y is (a) hydrogen; (b) halo; (c) --C.tbd.N (d) --CF 3 ; (e) lower alkyl; (f) lower alkoxy; or (g) --COOH.
Claim 12
Dependent Claim
19 words
The pharmaceutical composition of claim 8 wherein the compound is that of claim 2, 3, 4, 5 or 6.
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) | 1983-12-30 | 1984-06-30 | 1984-12-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-30 | 1988-06-30 | 1988-12-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-30 | 1992-06-30 | 1992-12-30 | $7700.00 | Window Closed / Lapsed |