Olefinic derivatives of amino acids

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

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26050111, 544358, 546348, 556175, 556183, C07C10128

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active

RE0319805

ABSTRACT:
Novel compounds of the following general formula are useful pharmacologic agents: ##STR1## R is [selected from] hydrogen[, alkylcarbonyl wherein the alkyl moiety contains from 1 to 4 carbon atoms, alkoxycarbonyl wherein the alkoxy moiety contains from 1 to 4 carbon atoms and may be straight or branched, and ##STR2## wherein R.sub.10 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl and p-hydroxybenzyl]; R.sub.2 is [selected from] hydroxy[, a straight or branched alkoxy group of from 1 to 8 carbon atoms, a lower alkylamino group wherein the alkyl moiety contains from 1 to 4 carbon atoms, and ##STR3## wherein R.sub.4 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl, and p-hydroxybenzyl]; R.sub.3 is [selected from] hydrogen[, chlorine, bromine, and iodine]; [A] is [selected from] ##STR4## [and --CH.dbd.CH--] wherein R.sub.1 is [selected from] hydrogen[, lower alkyl of from 1 to 4 carbon atoms, phenyl and substituted phenyl wherein the substituents on the substituted phenyl may be attached at the ortho, meta or para positions of the phenyl ring and are selected from halogen, lower alkoxy of from 1 to 4 carbon atoms, and lower alkyl of from 1 to 4 carbon atoms; n is an integer of from 1 to 5; and the lactams of said compounds wherein [A] represents ##STR5## R and R.sub.1 represent hydrogen] and n is the integer 2 [or 3] and pharmaceutically acceptable salts and individual optical isomers thereof.

REFERENCES:
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patent: 2531595 (1950-11-01), Albertson
patent: 2588969 (1952-03-01), Dickey et al.
patent: 3223729 (1965-12-01), Gobitz
Robert R. Rando, Chemistry and Enzymology of k.sub.cat Inhibitors, Science, vol. 185, pp. 320-324, (1974).
Robert R. Rando, Irreversible Inhibition of Aspartate Aminotransferase by 2-Amino-3-butenoic Acid, Biochemistry, vol. 13, No. 19, pp. 3859-3863, (1974).

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