Preparation of amino-acid derivatives useful as pharmaceuticals

Details Preparation of amino-acid derivatives useful as pharmaceuticals Preparation of amino-acid derivatives useful as pharmaceuticals

C - Chemistry, Metallurgy

07

D

260/515.4, 260/5

C07D 317/68 (2006.01) A61K 31/165 (2006.01) A61K 31/19 (2006.01) A61K 31/195 (2006.01) A61K 31/215 (2006.01) A61K 31/275 (2006.01)

Patent

CA 1165328

ABSTRACT Process for preparing compounds useful as munoregulatory and antineoplastic agents wh1ch are amino-acid derivatives of formula: Image (I) wherein:- n is an integer from 1 to 5; R1 is a hydrogen atom, an alkyl group, a haloalkyl group, a halogen atom, a mercapto group, an alkylmercapto group, a hydroxy group, an alkoxy group, an acyloxy group, a carboxyl group, an alkoxycarbonyl group, an amino group, an alkyl-substituted amino group, an aryl-substituted amino group, an acylamino group, a haloalkoxycarbonylamino group, an alkanesulphonyl group, a nitro group or a cyano group (and, when n is an integer from 2 to 5 the rad1cals R1 may be the same or different); R2 and R3 may be the same or different and each is a hydrogen atom or an alkyl group; R4 is a hydrogen atom, an alkyl group, a cyano group, cyanoalkyl group, a hydroxyalkyl group, an alkoxycarbonyl group, a carboxyl group, an aryl group, an aralkyl group, a mercaptoalkyl group, an alkylthioalkyl group, or a thioalkyl group (the free bond of the sulphur in sa1d thioalkyl group being joined to the sulphur ABSTRACT of another moiety of the same formula); and A is a hydroxy group, an alkoxy group, an amino group, an alkyl-substituted amino group (optionally halogen- or carbomyl- substituted in the alkyl moiety), a hydrazino group, an alkyl- or aryl- substituted hydrazino group, a hydroxylamino group, an alkoxyamino group or an aralkyloxyamino group; or a pharmaceutically acceptable salt thereof, which process comprises:- (a) Reacting a compound of formula: Image with a compound of formula: Image (in which either: Z is a halogen atom, G is the group: Image ABSTRACT and C?C is CH--CH; or: Z is the group: Image G is a hydrogen atom, and C?C is C-C) in the presence of a base, to give a compound formula: Image IV (wherein R1,R2,R3,R4 and n are defined above: and M1 is and alkyl group); (b) Optionally hydrolysing the product of step (a) to give a compound of formula: Image VI 4 ABSTRACT wherein R1, R2, R3, R4 and n are as defined above); (c) Optionally heating the product of step (b) where R4 represents a carboxy group, to give a compound of formula: Image XIII wherein R1, R2, R3 and n are as defined above); (d) Optional1y condensing the product of step (b) to give an oxazoione of formula: Image JX and reacting the oxazolone thus obtained with a compound of formula: HM2 (where M2 has the same meaning as A defined above, other than hydroxy or alkoxy) to give a compound of formula: Image XI (wherein R1,R2,R3,R4, n and M2 are as defined above); and (e) When the product of any of steps (a)-(d) is an acid, optionally salifying the said product so as to obtained a pharmaceutically acceptable salt thereof. twherein M2 has the same meaning as A def1ned at,ove, other than hydroxy or alkoxy) to give a ccmpound of formula. Image Xl l~here~n 8~, R2, R3, R4, n and M2 are as defined above); and te) hhen the product of any of steps ta) - (d) is an acid, optionally salifying the said product so as to obtain a pharmaceutically aoceDtable szlt thereof.

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