.alpha.-halomethyl derivatives of .alpha.-amino acids

C - Chemistry – Metallurgy – 07 – D

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260/523.1, 260/5

C07D 211/76 (2006.01) A61K 31/16 (2006.01) A61K 31/195 (2006.01) C07D 211/74 (2006.01) C07D 223/08 (2006.01) C07H 19/02 (2006.01) C07H 19/16 (2006.01) C07K 5/06 (2006.01) A61K 38/00 (2006.01)

Patent

CA 1091661

ABSTRACT OF THE DISCLOSURE Novel halomethyl derivatives of .alpha.-amino acids of the following general structure: Image wherein Y is FCH2-, F2CH-, FsC-, ClCH2-, Cl2CH2-; Z is .beta.- methylthioethyl, .beta.-thioethyl, .beta.-benzylthioethyl; S-(5'- desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, RaHN(CH2)N- wherein n is the integer 3 or 4 or Image wherein ?2 is FCH2-, F2CH-, or FsC-; each of Ra and Rb can be the same or different and is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxy- carbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or Image wherein R2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, -NR4R5 wherein each of R4 and R5 is hydrogen or a lower alkyl group of from 1 to 4 carbon atoms, or Image wherein R3 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and the lactams thereof when Z is RaHN(CH2)n- and each of Ra and Rb is hydrogen with the provisos that when Z is y-guanidinopropyl or .beta.-methylthio- ethyl, Y is FCH2-, F2CH- or F3C-; when Z is y-guanidino- propyl, R1 is hydroxy, and when Z is .beta.-thioethyl, .beta.-benzyl- thioethyl, S-(5'-desoxyadenos in-5'-yl)-S-methylthioethyl or Image , Y and Ya are FCH2-, F2CH-, or F3C- and are the same, each of Ra and Rb is hydrogen and R1 is hydroxy; and pharmaceutically acceptable salts and individual optical isomors thereof.

304918

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