Acylated 2-aminothiazole derivatives and a process for the...

C - Chemistry – Metallurgy – 07 – D

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260/278.2, 260/2

C07D 417/14 (2006.01) C07D 277/46 (2006.01) C07D 417/04 (2006.01)

Patent

CA 1038379

ABSTRACT OF THE DISCLOSURE New acylated 2-aminothiazole derivatives of the general formula (I), Image (I) wherein R1 stands for phenyl group or a pyridyl group, R2 stands for hydrogen or lower alkyl, R3 stands for hydrogen, a lower alkyl group or benzyl group, and R4 and R5 each represent hydrogen, a C1-8 alkyl group, allyl group, a hydroxyalkyl group, a C3-6 cycloalkyl group, .beta.-dimethylaminoethyl group, .beta.-diethylaminoethyl group, benzyl group, 2-furylmethyl group, or a phenyl group having optionally a halogen, methyl, methoxy or tri- fluoromethyl substituent, or R4 and R5 may form, together with the adjacent nitrogen atom, a 5 to 8 membered polymethyleneimino group, morpholino group, piperazino group, N-methylpiperazino group or N-phenylpiperazino group, are prepared as follows: a) a thiazole derivative of the general formula (II), - 2 - Image (II) wherein R1 and R2 each have the same meanings as defined above, and Q stands for a group of the general formual X-CH(R3)-CO-, wherein R3 has the same meanings as de- fined above and X stands for halogen, is reacted with an amine of the general formula (III), Image (III) wherein R4 and R5 each have the same meanings as defined above and Y stands for hydrogen, or b) a thiazole derivative of the general formula (II), wherein R1 and R2 each have the same meanings as defined above and Q stands for hydrogen, is reacted with an amine of the general formula (III), wherein R4 and R5 each have the same meanings as defined above, and Y stands for a group of the general formula Z-CO-CH(R3)-, wherein R3 has the same meanings as defined above and Z represents halogen, a C1-4 alkoxy group or an azido group, or c) a haloketone of the general formula (IV), Image (IV) wherein R1, R2 and X each have the same meanings as - 3 - defined above, is reacted with an aminoacyl-thiourea of the general formula (V), Image (V) wherein R3, R4 and R5 each have the same meanings as defined above. The new compounds of the general formula (I) and their pharmaceutically acceptable acid addition salts possess valuable pharmacological properties, and can be applied primarily for the inhibition of the gastric hypersecretion as well as for the prophylaxis or treat- ment of gastric ulcer.

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