Claims for Patent: 3,669,965

Summary for Patent: 3,669,965

Title:	1-LOWER ALKYL OR ALKYLENE SUBSTITUTED-6,7-METHYLENEDIOXY-4(1H)-OXOCINNOLINE-3-CARBOXYLIC ACIDS AND METHODS FOR MAKING AND USING SAME
Abstract:	1-Lower alkyl or alkenyl substituted-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acids, active against Gram-negative bacteria and Mycoplasma organisms and methods for the preparation and use thereof.
Inventor(s):	White; William A. (Fountaintown, IN)
Assignee:	Eli Lilly and Company (Indianapolis, IN)
Application Number:	04/888,880
Patent Claims:	1. A compound of the class consisting of compounds of the following formula: ##SPC3## Wherein R is a member of the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, vinyl and allyl, and the cationic salts thereof formed with an alkali metal, or alkaline earth metal, ammonia, triethylamine, or pyrrolidine. 2. A compound according to claim 1 wherein the compound is 1-ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid. 3. A compound according to claim 1 wherein the compound is 1-methyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid. 4. A compound according to claim 1 wherein the compound is 1-vinyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid. 5. A compound according to claim 1 wherein the compound is 1-(n-propyl)-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid. 6. A compound according to claim 1 wherein the compound is 1-allyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid. 7. A compound according to claim 1 wherein the compound is 1-isopropyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid. 8. A compound according to claim 1 wherein the compound is 1-(n-butyl)-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carboxylic acid. 9. A method for the preparation of a compound of the class of compounds of the following formula: ##SPC4## Wherein R is a member of the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl and allyl which comprises: a. catalytically reducing 2'-nitro-4',5'-methylenedioxyacetophenone to 2'-amino-4',5' -methylenedioxyacetone. b. diazotizing 2' -amino-4',5' -methylenedioxyacetophenone with nitrous acid and cyclizing to yield 6,7-methylenedioxycinnoline-4-ol c. treating 6,7-methylenedioxycinnoline-4-ol with bromine to produce 3-bromo-6,7-methylene-dioxycinnoline-4-ol d. treating 3-bromo-6,7-methylenedioxycinnoline-4-ol with cuprous cyanide to form 6,7-methylenedioxy-cinnoline-4-ol-3-carbonitrile e. alkylating 6,7-methylenedioxycinnoline-4-ol-3-carbonitrile with an alkyl or alkylene bromide, chloride, iodide or sulfate to form a 1-lower alkyl or alkylene substituted-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitrile of the following formula: ##SPC5## Wherein R is a member of the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl and allyl and: f. hydrolyzing the 1-lower alkyl or alkylene substituted-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitrile 10. 3-Bromo-6,7-methylenedioxycinnoline-4-ol 11. 6,7-methylenedioxycinnoline-4-ol-3-carbonitrile 12. A compound of the class consisting of compounds of the following formula: ##SPC6## Wherein R is a member of the group consisting of methyl, ethyl, n-propyl, isoproply, n-butyl, .beta.-hydroxyethyl and allyl. 13. A compound according to claim 12 wherein the compound is 1-methyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitrile. 14. A compound according to claim 12 wherein the compound is 1-ethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitrile. 15. A compound according to claim 12 wherein the compound is 1-(n-propyl)-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitrile. 16. A compound according to claim 12 wherein the compound is 1-isopropyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitrile. 17. A compound according to claim 12 wherein the compound is 1-isopropyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitrile. 18. A compound according to claim 12 wherein the compound is 1-.beta.-hydroxylethyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitril e. 19. A compound according to claim 12 wherein the compound is 1-allyl-6,7-methylenedioxy-4(1H)-oxocinnoline-3-carbonitrile.