Substituted 1,5-cyclohexadiene carboxylic acid derivatives

• US 4,187,316 A
• Filed: 01/12/1978
• Issued: 02/05/1980
• Est. Priority Date: 01/12/1978
• Status: Expired due to Term

• Current Assignee: Merrell Toraude et Compagnie
• Original Assignee: Merrell Toraude et Compagnie
• Inventors: Metcalf, Brian W., Jung, Michel
• Primary Examiner(s): Thomas, Jr., James O.
• Assistant Examiner(s): Breitenstein, G. T.
• Application Number:
  US05/868,860
• Time in Patent Office: 754 Days
• Field of Search: 260/514 J, 260/501.11, 424/316, 424/305, 424/319, 560/125, 562/510
• US Class Current: 514/529
• CPC Class Codes: C07C 2601/16 the ring being unsaturated
• CPC Class Codes: C07C 333/32 Thiuramsulfides; Thiurampolysulfides

Abstract

Compounds of the following general formula and salts thereof are irreversible inhibitors of γ-aminobutyric acid transaminase: ##STR1## wherein R₁ is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, the radical ##STR2## wherein R₄ is hydrogen, a straight or branched alkyl group having from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R₂ is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, the group

-NR.sub.5 R.sub.6

wherein each of R₅ and R₆ is hydrogen or a straight or branched alkyl group having from 1 to 4 carbon atoms, or ##STR3## wherein R₇ is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and R₃ is hydrogen or bromine.

Claims

1. A compound of the formula ##STR14## wherein R₁ is hydrogen;

R₂ is hydroxy, or a straight or branched alkoxy group of from 1 to 8 carbon atoms;

R₃ is hydrogen or bromine; and

pharmaceutically acceptable salts and individual optical isomers thereof.

2. A compound of claim 1 wherein R₃ is hydrogen.

3. A compound of claim 1 wherein R₃ is bromine.

4. A compound of claim 1 wherein R₂ is hydroxy.

5. A compound of claim 4 which is 3-amino-1,5-cyclohexadiene carboxylic acid or a pharmaceutically acceptable salt thereof.

6. The compound of claim 4 which 3-amino-1,5-cyclohexadiene carboxylic acid trifluoroacetate.

7. A compound of claim 6 which is 3-amino-6-bromo-1,5-cyclohexadiene carboxylic acid or a phramceutically acceptable salt thereof.

8. A pharmaceutical composition in unit dosage form which comprises an effective amount of a compound of claim 1 and a significant quantity of a pharmaceutically acceptable carrier.

9. A composition of claim 8 wherein the effective quantity of compound is from 0.1 mg/kg to 150 mg/kg of body weight of the patient per unit dose.