Claims
- 1. Imidazoquinoxalines selected from the group consisting of structures I and II ##STR18## wherein R.sub.1, R.sub.5, R.sub.6 and R.sub.7 are independently H, alkyl, aryl, alkenyl, alknyl, hydroxy, hydroxyalkyl, alkoxy, mercapto, mercaptoalkyl, alkylthio, amino, alkylamino, aminoalkyl, carboxaldehyde, ##STR19## wherein R.sub.9 is H or pharmaceutically acceptable salts, carbalkoxy, alkanoyl, cyano, nitro, halo, trifluoromethyl, alkylsulfonyl, sulfonamido, or
- R.sub.1, R.sub.5, R.sub.6 or R.sub.7 taken together with an adjacent group from a methylenedioxy group;
- R.sub.4 is H, alkyl, alkenyl, alkynyl, aryl, aralkyl, hydroxy or alkanoyl;
- R.sub.3 is H, cyano, tetrazolo, carboxaldehyde, hydroxyalkyl or ##STR20## wherein Y is O or NH and R.sub.10 is H, alkyl, aryl, hydroxyalkyl, alkoxyalkyl, aminoalkyl or pharmaceutically acceptable salt thereof;
- R.sub.2 is H, alkyl, halo, amino, alkylamino, arylamino, hydroxyamino, hydroxy, alkoxy, mercapto, or alkylthio;
- R.sub.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.sub.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.
- 2. The compounds of claim 1 wherein
- R.sub.1 and R.sub.5 are hydrogen;
- R.sub.2 is hydrogen, hydroxy, halo, mercapto or alkylthio;
- R.sub.3 is hydrogen, ##STR21## wherein R.sub.10 is H, alkyl, alkoxyethyl aminoalkyl or pharmaceutically acceptable salt thereof;
- R.sub.4 is hydrogen, alkyl, alkenyl, aryl, aralkyl, hydroxy or alkanoyl;
- R.sub.6 and R.sub.7 are independently hydrogen, alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, or alkyl sulfonyl;
- R.sub.8 is halo, amino, alkoxy, alkoxyamino, or mercapto; and
- X is oxygen, sulfur or imino.
- 3. The compounds of claim 1 wherein the structure is ##STR22##
- 4. 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 .beta.-N,N-dimethylaminoethyl ester and its hydrochloride salt.
- 5. The compounds of claim 3 wherein
- R.sub.1 and R.sub.5 are hydrogen;
- R.sub.2 is hydrogen, hydroxy, halo, mercapto or alkylthio;
- R.sub.3 is hydrogen, ##STR23## wherein R.sub.10 is H, alkyl, alkoxyethyl, aminoalkyl or pharmaceutically acceptable salt thereof;
- R.sub.4 is hydrogen, alkyl, alkenyl, aryl, aralkyl, hydroxy or alkanoyl;
- R.sub.6 and R.sub.7 are independently hydrogen, alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, or alkyl sulfonyl;
- R.sub.8 is halo, amino, alkoxy, alkoxyamino, or mercapto; and
- X is oxygen, sulfur or imino, wherein when R.sub.2 is OH it can be in keto or enol form.
- 6. 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.
- 7. The compounds of claim 3 wherein
- R.sub.1 and R.sub.5 are hydrogen;
- R.sub.2 is hydrogen, halo or hydroxy;
- R.sub.3 is hydrogen, ##STR24## wherein R.sub.10 is H, alkyl group having one to three carbons, an aminoalkyl or pharmaceutically acceptable salt thereof;
- R.sub.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.sub.6 is hydrogen, alkyl having 1 to 3 carbon atoms, trifluoromethyl or alkyl sulfonyl;
- R.sub.7 is hydrogen or alkyl having 1 to 3 carbon atoms;
- and
- X is oxygen, wherein when R.sub.2 is OH it can be in keto or enol form.
- 8. The compounds of claim 5 wherein
- R.sub.2 is hydrogen or hydroxy;
- R.sub.3 is hydrogen, ##STR25## wherein R.sub.10 is H, alkyl group having one to three carbons, an aminoalkyl or pharmaceutically acceptable salt thereof;
- R.sub.4 is an alkyl having one to three carbons;
- R.sub.6 is hydrogen, halo, or trifluoromethyl;
- R.sub.7 is hydrogen; and
- X is oxygen; wherein when R.sub.2 is OH it can be in keto or enol form.
- 9. The compounds of claim 1 wherein the structure is ##STR26##
- 10. The compounds of claim 9 wherein
- R.sub.1 and R.sub.5 are hydrogen;
- R.sub.2 is hydrogen, hydroxy, halogen, mercapto or alkylthio;
- R.sub.3 is hydrogen, ##STR27## wherein R.sub.10 is H, alkyl, alkoxyethyl, aminoalkyl or pharmaceutically acceptable salts thereof;
- R.sub.6 and R.sub.7 are independently hydrogen, alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, or alkyl sulfonyl;
- and
- R.sub.8 is halo, amino, alkoxy, alkoxyamino, or mercapto.
- 11. 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.
- 12. The compounds of claim 9 wherein
- R.sub.2 is a hydrogen or halogen;
- R.sub.3 is ##STR28## wherein R.sub.10 is C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen or trifluoromethyl;
- R.sub.1, R.sub.5 and R.sub.7 are hydrogen, and
- R.sub.8 is halogen, amino, alkoxy having 1 to 3 carbon atoms or mercapto.
- 13. 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.
- 14. 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.
- 15. 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.
- 16. 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.
Parent Case Info
This application is a continuation-in-part of application Ser. No. 283,717, filed July 16, 1981, now abandoned.
Non-Patent Literature Citations (2)
Entry |
Kollenz, Chem. Abs. 78, 16132r (1972). |
Van Nispen, Tet. Letters 3723-26 (1980). |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
283717 |
Jul 1981 |
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