US4440929A
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Imidazoquinoxaline compounds
Assignee: USV Pharmaceutical Corp
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Filing: 1982-03-29
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Granted: 1984-04-03
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Expires: 2002-03-29
Abstract
Abstract Provided are imidazoquinoxalines of the structures: ##STR1## wherein R 1 , R 5 , R 6 and R 7 are independently H, alkyl, aryl, alkenyl, alkynyl, hydroxy, hydroxyalkyl, alkoxy, mercapto, mercaptoalkyl, alkylthio, amino, alkylamino, aminoalkyl, carboxaldehyde, carboxylic acid and salts thereof, carbalkoxy, alkanoyl, cyano, nitro, halo, trifluoromethyl, alkylsulfonyl, sulfonamido, or R 1 , R 5 , R 6 and R 7 may be taken together with the adjacent group to form a methylenedioxy group. R 4 is H, alkyl, alkenyl, alkynyl, aryl, aralkyl, hydroxy or alkanoyl. R 3 is H, cyano, tetrazolo, carboxaldehyde, hydroxyalkyl, carboxylic acid and salts thereof or derivatives thereof such as esters or amides in which the substituent on the ester oxygen or amide nitrogen is alkyl, aryl, hydroxyalkyl, alkoxyalkyl or amino alkyl. R 2 and R 8 are independently H, alkyl, aryl, halo, amino, alkylamino, arylamino, hydroxyamino, hydroxy, alkoxy, mercapto or alkylthio, and X is oxygen, sulfur, imino, and hydroxyimino.
Inventors
- 👤 Thomas D. Lee
- 👤 Richard E. Brown
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:25
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D233/00; C07D233/54; C07D233/66; C07D233/90
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
212 words
Imidazoquinoxalines selected from the group consisting of structures I and II ##STR18## wherein R 1 , R 5 , R 6 and R 7 are independently H, alkyl, aryl, alkenyl, alknyl, hydroxy, hydroxyalkyl, alkoxy, mercapto, mercaptoalkyl, alkylthio, amino, alkylamino, aminoalkyl, carboxaldehyde, ##STR19## wherein R 9 is H or pharmaceutically acceptable salts, carbalkoxy, alkanoyl, cyano, nitro, halo, trifluoromethyl, alkylsulfonyl, sulfonamido, or R 1 , R 5 , R 6 or R 7 taken together with an adjacent group from a methylenedioxy group; R 4 is H, alkyl, alkenyl, alkynyl, aryl, aralkyl, hydroxy or alkanoyl; R 3 is H, cyano, tetrazolo, carboxaldehyde, hydroxyalkyl or ##STR20## wherein Y is O or NH and R 10 is H, alkyl, aryl, hydroxyalkyl, alkoxyalkyl, aminoalkyl or pharmaceutically acceptable salt thereof; R 2 is H, alkyl, halo, amino, alkylamino, arylamino, hydroxyamino, hydroxy, alkoxy, mercapto, or alkylthio; R 8 is alkyl, halo, amino, alkylamino, arylamino, hydroxyamino, hydroxy, alkoxy, mercapto, or alkylthio; X is oxygen, sulfur, imino, or hydroxyimino; with the proviso that when R 2 is hydroxy it can be in enol or keto form; and wherein the alkyl of the alkyl, hydroxyalkyl, alkoxy, aminoalkyl, alkylamino, alkylthio, mercaptoalkyl, alkanoyl, aralkyl and carbalkoxy contains from 1 to 8 carbon atoms and the alkenyl and alkynyl contain 2 to 8 carbon atoms.
Claim 2
Dependent Claim
212 words
Imidazoquinoxalines selected from the group consisting of structures I and II ##STR18## wherein R 1 , R 5 , R 6 and R 7 are independently H, alkyl, aryl, alkenyl, alknyl, hydroxy, hydroxyalkyl, alkoxy, mercapto, mercaptoalkyl, alkylthio, amino, alkylamino, aminoalkyl, carboxaldehyde, ##STR19## wherein R 9 is H or pharmaceutically acceptable salts, carbalkoxy, alkanoyl, cyano, nitro, halo, trifluoromethyl, alkylsulfonyl, sulfonamido, or R 1 , R 5 , R 6 or R 7 taken together with an adjacent group from a methylenedioxy group; R 4 is H, alkyl, alkenyl, alkynyl, aryl, aralkyl, hydroxy or alkanoyl; R 3 is H, cyano, tetrazolo, carboxaldehyde, hydroxyalkyl or ##STR20## wherein Y is O or NH and R 10 is H, alkyl, aryl, hydroxyalkyl, alkoxyalkyl, aminoalkyl or pharmaceutically acceptable salt thereof; R 2 is H, alkyl, halo, amino, alkylamino, arylamino, hydroxyamino, hydroxy, alkoxy, mercapto, or alkylthio; R 8 is alkyl, halo, amino, alkylamino, arylamino, hydroxyamino, hydroxy, alkoxy, mercapto, or alkylthio; X is oxygen, sulfur, imino, or hydroxyimino; with the proviso that when R 2 is hydroxy it can be in enol or keto form; and wherein the alkyl of the alkyl, hydroxyalkyl, alkoxy, aminoalkyl, alkylamino, alkylthio, mercaptoalkyl, alkanoyl, aralkyl and carbalkoxy contains from 1 to 8 carbon atoms and the alkenyl and alkynyl contain 2 to 8 carbon atoms.
Claim 3
Dependent Claim
83 words
The compounds of claim 1 wherein R 1 and R 5 are hydrogen; R 2 is hydrogen, hydroxy, halo, mercapto or alkylthio; R 3 is hydrogen, ##STR21## wherein R 10 is H, alkyl, alkoxyethyl aminoalkyl or pharmaceutically acceptable salt thereof; R 4 is hydrogen, alkyl, alkenyl, aryl, aralkyl, hydroxy or alkanoyl; R 6 and R 7 are independently hydrogen, alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, or alkyl sulfonyl; R 8 is halo, amino, alkoxy, alkoxyamino, or mercapto; and X is oxygen, sulfur or imino.
Claim 4
Dependent Claim
10 words
The compounds of claim 1 wherein the structure is ##STR22##
Claim 5
Dependent Claim
16 words
The compound of claim 3 which is 7-Chloro-1-hydroxy-4-oxo-5-propyl-4,5-dihydroimidazo-[1,5-a]quinoxaline 3-carboxylic acid β-N,N-dimethylaminoethyl ester and its hydrochloride salt.
Claim 6
Dependent Claim
97 words
The compounds of claim 3 wherein R 1 and R 5 are hydrogen; R 2 is hydrogen, hydroxy, halo, mercapto or alkylthio; R 3 is hydrogen, ##STR23## wherein R 10 is H, alkyl, alkoxyethyl, aminoalkyl or pharmaceutically acceptable salt thereof; R 4 is hydrogen, alkyl, alkenyl, aryl, aralkyl, hydroxy or alkanoyl; R 6 and R 7 are independently hydrogen, alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, or alkyl sulfonyl; R 8 is halo, amino, alkoxy, alkoxyamino, or mercapto; and X is oxygen, sulfur or imino, wherein when R 2 is OH it can be in keto or enol form.
Claim 7
Dependent Claim
24 words
The compound of claim 3 which is 7-Chloro-1-hydroxy-4-oxo-5-propyl-4,5-dihydroimidazo[1,5-a]quinoxaline 3-carboxylic acid ethyl ester and its pharmaceutically acceptable salts and in both enol and keto form.
Claim 8
Dependent Claim
118 words
The compounds of claim 3 wherein R 1 and R 5 are hydrogen; R 2 is hydrogen, halo or hydroxy; R 3 is hydrogen, ##STR24## wherein R 10 is H, alkyl group having one to three carbons, an aminoalkyl or pharmaceutically acceptable salt thereof; R 4 is hydrogen, hydroxy, alkyl having 1 to 3 carbon atoms, aralkyl having 1 to 3 carbons in the alkyl, alkanoyl or alkoxy having 1 to 3 carbons; R 6 is hydrogen, alkyl having 1 to 3 carbon atoms, trifluoromethyl or alkyl sulfonyl; R 7 is hydrogen or alkyl having 1 to 3 carbon atoms; and X is oxygen, wherein when R 2 is OH it can be in keto or enol form.
Claim 9
Dependent Claim
75 words
The compounds of claim 5 wherein R 2 is hydrogen or hydroxy; R 3 is hydrogen, ##STR25## wherein R 10 is H, alkyl group having one to three carbons, an aminoalkyl or pharmaceutically acceptable salt thereof; R 4 is an alkyl having one to three carbons; R 6 is hydrogen, halo, or trifluoromethyl; R 7 is hydrogen; and X is oxygen; wherein when R 2 is OH it can be in keto or enol form.
Claim 10
Dependent Claim
10 words
The compounds of claim 1 wherein the structure is ##STR26##
Claim 11
Dependent Claim
66 words
The compounds of claim 9 wherein R 1 and R 5 are hydrogen; R 2 is hydrogen, hydroxy, halogen, mercapto or alkylthio; R 3 is hydrogen, ##STR27## wherein R 10 is H, alkyl, alkoxyethyl, aminoalkyl or pharmaceutically acceptable salts thereof; R 6 and R 7 are independently hydrogen, alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, or alkyl sulfonyl; and R 8 is halo, amino, alkoxy, alkoxyamino, or mercapto.
Claim 12
Dependent Claim
22 words
The compound of claim 3 which is 7-Chloro-1-hydroxy-4-oxo-5-propyl-4,5-dihydroimidazo[1,5-a]quinoxaline 3-carboxylic acid and its pharmaceutically acceptable salts and in both enol and keto forms.
Claim 13
Dependent Claim
57 words
The compounds of claim 9 wherein R 2 is a hydrogen or halogen; R 3 is ##STR28## wherein R 10 is C 1 -C 3 alkyl; R 6 is hydrogen or trifluoromethyl; R 1 , R 5 and R 7 are hydrogen, and R 8 is halogen, amino, alkoxy having 1 to 3 carbon atoms or mercapto.
Claim 14
Dependent Claim
17 words
The compound of claim 3 which is 5-Methyl-4-oxo-7-trifluoromethyl-4,5-dihydroimidazo[1,5-a]quinoxaline 3-carrboxylic acid ethyl ester and its pharmaceutically acceptable salts.
Claim 15
Dependent Claim
17 words
The compound of claim 3 which is 4-Oxo-5-propyl-4,5-dihydroimidazo[1,5-a]quinoxaline 3-carboxylic acid ethyl ester and its pharmaceutically acceptable salts.
Claim 16
Dependent Claim
17 words
The compound of claim 3 which is 7-Chloro-4-oxo-5-propyl-4,5-dihydroimidazo[1,5-a]quinoxaline 3-carboxylic acid ethyl ester and its pharmaceutically acceptable salts.
Claim 17
Dependent Claim
20 words
The compound of claim 3 which is 7-Chlorol-lhydroxy-4-oxo-5-propyl-4,5-dihydroimidazo[1,5-a]quinoxaline and its pharmaceutically acceptable salts, and in both enol and keto forms.
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) | 1987-04-03 | 1987-10-03 | 1988-04-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-04-03 | 1991-10-03 | 1992-04-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-04-03 | 1995-10-03 | 1996-04-03 | $7700.00 | Window Closed / Lapsed |