US4089958A
Expired / Lapsed
US
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2,3,4,4A-Tetrahydro-1H-pyrazino[1,2]quinoxalin-5(6)-ones and derivatives thereof
Assignee: Wyeth LLC
•
Filing: 1976-12-20
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Granted: 1978-05-16
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Expires: 1996-12-20
Abstract
Abstract Compounds of the formula ##STR1## WHEREIN R is hydrogen (lower)alkyl, phen(lower)-alkyl, benzoyl(lower)alkyl, or p-halobenzoyl-(lower)alkyl; R 1 is hydrogen or (lower)alkyl; R 2 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino in the 7-, 8-, or 9-position; R 3 is hydrogen, or (lower)alkyl; and R 4 is hydrogen, (lower)-alkyl, (lower)alkoxy, chlorine, fluorine, or trifluoromethyl in the 7-, 8-, or 9-position; or the non-toxic acid addition salts thereof; exert a hyptotensive effect in hypertensive animals.
Inventors
- 👤 Meier E. Freed
- 👤 John R. Potoski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 06:37
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; C07C; C07C205/00; C07C205/07; C07C205/11; C07C205/12; C07D241/00; C07D241/02; C07D241/04; C07D487/00; C07D487/02; C07D487/04; C07F; C07F1/00; C07F1/005; C07F1/08
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
68 words
A compound of the formula: ##STR6## wherein R is hydrogen, (lower)alkyl, phen(lower)alkyl, benzoyl(lower)alkyl, or p-halobenzoyl(lower)alkyl; R 1 is hydrogen or (lower)alkyl; R 2 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino in the 7-, 8-, or 9-position; R 3 is hydrogen or (lower)alkyl; and R 4 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, or trifluoromethyl in the 7-, 8-, or 9-position; or the non-toxic acid addition salts thereof.
Claim 2
Dependent Claim
68 words
A compound of the formula: ##STR6## wherein R is hydrogen, (lower)alkyl, phen(lower)alkyl, benzoyl(lower)alkyl, or p-halobenzoyl(lower)alkyl; R 1 is hydrogen or (lower)alkyl; R 2 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino in the 7-, 8-, or 9-position; R 3 is hydrogen or (lower)alkyl; and R 4 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, or trifluoromethyl in the 7-, 8-, or 9-position; or the non-toxic acid addition salts thereof.
Claim 3
Dependent Claim
50 words
A compound as defined in claim 1 of the formula: ##STR7## wherein R is hydrogen, (lower)alkyl, phen(lower)alkyl, benzoyl(lower)alkyl, or p-halobenzoyl(lower)alkyl; R 1 is hydrogen or (lower)alkyl; R 2 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino in the 7-, 8-, or 9-position; or the non-toxic acid addition salts thereof.
Claim 4
Dependent Claim
27 words
A compound as defined in claim 2 wherein R and R 1 are each hydrogen and R 2 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino.
Claim 5
Dependent Claim
10 words
The compound as defined in claim 3 which is 2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 6
Dependent Claim
18 words
A compound as defined in claim 3 wherein R 2 is (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino.
Claim 7
Dependent Claim
10 words
The compound as defined in claim 5 which is 7-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 8
Dependent Claim
10 words
The compound as defined in claim 5 which is 8-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 9
Dependent Claim
10 words
The compound as defined in claim 5 which is 9-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 10
Dependent Claim
10 words
The compound as defined in claim 5 which is 7-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 11
Dependent Claim
10 words
The compound as defined in claim 5 which is 8-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2a]quinoxalin-5(6H)-one.
Claim 12
Dependent Claim
10 words
The compound as defined in claim 5 which is 9-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 13
Dependent Claim
10 words
A compound as defined in claim 5 which is 2,3,4,4a-tetrahydro-9-methoxy-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 14
Dependent Claim
10 words
A compound as defined in claim 5 which is 2,3,4,4a-tetrahydro-8-trifluoromethyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 15
Dependent Claim
10 words
A compound as defined in claim 5 which is 8-amino-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 16
Dependent Claim
10 words
The compound as defined in claim 5 which is 2,3,4,4a-tetrahydro-8-methyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 17
Dependent Claim
15 words
A compound as defined in claim 15 wherein R 2 is (lower)alkyl in the 9-position.
Claim 18
Dependent Claim
10 words
The compound as defined in claim 16 which is 2,3,4,4a-tetrahydro-9-methyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 19
Dependent Claim
27 words
A compound as defined in claim 2 wherein R is hydrogen; R 1 is (lower)alkyl; and R 2 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino.
Claim 20
Dependent Claim
20 words
A compound as defined in claim 18 wherein R and R 2 are each hydrogen and R 1 is (lower)alkyl.
Claim 21
Dependent Claim
10 words
The compound as defined in claim 19 which is 2,3,4,4a-tetrahydro-6-methyl-1H-pyrazino-[1,2-a]quinoxalin-5(6H)-one.
Claim 22
Dependent Claim
31 words
A compound as defined in claim 2 wherein R is (lower)alkyl, phen(lower)alkyl, benzoyl(lower)alkyl, or p-halobenzyl(lower)alkyl; R 1 is hydrogen; and R 2 is hydrogen, (lower)-alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino.
Claim 23
Dependent Claim
24 words
A compound as defined in claim 21 wherein R is (lower)alkyl, phen(lower)alkyl, benzoyl(lower)alkyl, or p-halobenzoyl(lower)alkyl, and R 1 and R 2 are each hydrogen.
Claim 24
Dependent Claim
10 words
A compound as defined in claim 22 which is 2,3,4,4a-tetrahydro-3-(lower)alkyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 25
Dependent Claim
10 words
The compound as defined in claim 23 which is 2,3,4,4a-tetrahydro-3-methyl-1H-pyrazino[1,2-a]quinoxalin-5-(6H)-one.
Claim 26
Dependent Claim
10 words
The compound as defined in claim 22 which is 3-[4-(4-fluorophenyl)-4-oxobutyl]2,3,4,4a-tetrahydro-1H-pyrazino-[1,2-a]quinoxalin-5(6H)-one.
Claim 27
Dependent Claim
10 words
The compound as defined in claim 22 which is 2,3,4,4a-tetrahydro-2(2-phenethyl)-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 28
Dependent Claim
46 words
A compound as defined in claim 1 of the formula: ##STR8## wherein: R 1 and R 3 , independently, are hydrogen or (lower)alkyl; R 4 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, or trifluoromethyl in the 7-, 8-, or 9-position; or the non-toxic acid addition salts thereof.
Claim 29
Dependent Claim
10 words
The compound as defined in claim 27 which is 2,3,4,4a-,5,6-hexahydro-3-methyl-1H-pyrazino[1,2-a]quinoxaline.
Claim 30
Dependent Claim
31 words
A compound of the formula: ##STR9## wherein: R 1 is hydrogen or (lower)alkyl R 2 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, amino, or trifluoroacetamido in the 7-, 8-, or 9-position.
Claim 31
Dependent Claim
31 words
A compound of the formula: ##STR9## wherein: R 1 is hydrogen or (lower)alkyl R 2 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, amino, or trifluoroacetamido in the 7-, 8-, or 9-position.
Claim 32
Dependent Claim
10 words
The compound as defined in claim 29 which is 3-carbobenzoxy-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 33
Dependent Claim
10 words
The compound as defined in claim 29 which is 3-carbobenzoxy-7-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]-quinoxalin-5-(6H)-one.
Claim 34
Dependent Claim
10 words
A compound as defined in claim 29 which is 3-carbobenzoxy-8-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 35
Dependent Claim
10 words
A compound as defined in claim 29 which is 3-carbobenzoxy-9-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]-quinoxaline-5(6H)-one.
Claim 36
Dependent Claim
10 words
A compound as defined in claim 29 which is 3-carbobenzoxy-8-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one.
Claim 37
Dependent Claim
10 words
A compound as defined in claim 29 which is 3-carbobenzoxy-2,3,4,4a-tetrahydro-8-methyl-1H-pyrazino[1,2a]-quinoxalin-5(6H)-one.
Claim 38
Dependent Claim
10 words
A compound as defined in claim 29 which is 3-carbobenzoxy-2,3,4,4a-tetrahydro-9-methyl-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one.
Claim 39
Dependent Claim
10 words
A compound as defined in claim 29 which is 3-carbobenzoxy-2,3,4,4a-tetrahydro-8-trifluoromethyl-1H-pyrazino-[1,2-a]quinoxalin-5(6H)-one.
Claim 40
Dependent Claim
10 words
A compound as defined in claim 29 which is 3-carbobenzoxy-2,3,4,4a-tetrahydro-8-(2,2,2-trifluoroacetamido)-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 41
Dependent Claim
10 words
A compound as defined in claim 29 which is 3-carbobenzoxy-2,3,4,4a-tetrahydro-9-methoxy-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one.
Claim 42
Dependent Claim
10 words
A compound as defined in claim 29 which is 8amino-3-carbobenzoxy-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one.
Claim 43
Dependent Claim
10 words
The compound as defined in claim 29 which is 3-carbobenzoxy-2,3,4,4a-tetrahydro-6-methyl-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one.
Claim 44
Dependent Claim
83 words
An antihypertensive composition comprising (a) a hypotensive effective amount of a compound of the formula: ##STR10## wherein R is hydrogen, (lower)alkyl, phen(lower)alkyl, benzoyl(lower)alkyl, or p-halobenzoyl(lower)alkyl; R 1 is hydrogen or (lower)alkyl; R 2 is hydrogen (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino in the 7-, 8-, or 9-position; R 3 is hydrogen or (lower)alkyl; and R 4 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, or trifluoromethyl in the 7-,8-, or 9-position; or the non-toxic acid addition salts thereof; and (b) a pharmaceutically acceptable carrier;
Claim 45
Dependent Claim
83 words
An antihypertensive composition comprising (a) a hypotensive effective amount of a compound of the formula: ##STR10## wherein R is hydrogen, (lower)alkyl, phen(lower)alkyl, benzoyl(lower)alkyl, or p-halobenzoyl(lower)alkyl; R 1 is hydrogen or (lower)alkyl; R 2 is hydrogen (lower)alkyl, (lower)alkoxy, chlorine, fluorine, trifluoromethyl, or amino in the 7-, 8-, or 9-position; R 3 is hydrogen or (lower)alkyl; and R 4 is hydrogen, (lower)alkyl, (lower)alkoxy, chlorine, fluorine, or trifluoromethyl in the 7-,8-, or 9-position; or the non-toxic acid addition salts thereof; and (b) a pharmaceutically acceptable carrier;
Claim 46
Dependent Claim
29 words
A composition as defined in claim 42 wherein the compound is selected from the group consisting of: 2,3,4,4a-tetrahydro-1H-pyrazino-[1,2-a]quinoxalin-5(6H)-one; 2,3,4,4a-tetrahydro-6-methyl1H-pyrazino[1,2-a]quinoxaline-5(6H)-one; 2,3,4,4a-tetrahydro-9-methoxy-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one; 7-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one; 8-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one; 9-chloro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one; 2,3,4,4a-tetrahydro-8-trifluoromethyl-1-pyrazino[1,2-a[quinoxalin-5(6H)-one 2,3,4,4a-tetrahydro-9-methyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one; 7-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one; 8-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one; and 9-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxaline-5(6H)-one.
Claim 47
Dependent Claim
12 words
A composition as defined in claim 43 wherein the compound is 2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one.
Claim 48
Dependent Claim
12 words
A composition as defined in claim 43 wherein the compound is 2,3,4,4a-tetrahydro-6-methyl-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one.
Claim 49
Dependent Claim
12 words
A composition as defined in claim 43 wherein the compound is 7-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2a]-quinoxalin-5(6H)-one.
Claim 50
Dependent Claim
12 words
A composition as defined in claim 43 wherein the compound is 8-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one.
Claim 51
Dependent Claim
12 words
A composition as defined in claim 43 wherein the compound is 9-fluoro-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]-quinoxalin-5(6H)-one.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-15 | 1981-11-14 | 1982-05-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-15 | 1985-11-14 | 1986-05-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-15 | 1989-11-14 | 1990-05-16 | $7700.00 | Window Closed / Lapsed |