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Claims for Patent: 3,669,965

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Claims 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.
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