Process for the preparation of compounds with antiulcer action

Details Process for the preparation of compounds with antiulcer action Process for the preparation of compounds with antiulcer action

C - Chemistry, Metallurgy

07

D

260/314, 260/353

C07D 233/64 (2006.01) C07D 307/52 (2006.01) C07D 317/58 (2006.01) C07D 407/12 (2006.01)

Patent

CA 1329615

ABSTRACT OF THE DISCLOSURE The invention relates to a process for the preparation of compounds of the formula Ar-CH2-S-(CH2)n-NH-?-NH-R1 (V) wherein R1 is selected from the group consisting of hydrogen, alkyl and Image Ar is selected from the group consisting of Image and Image n=1,2,3,4,5 or 6 and X represents CH-NO2 or N-C?N. The process of the invention comprises the steps of: (a)reacting a carbamate of the formula: Image (VIII) wherein Z is H, halogen or NO2 with a bisdi- thioalkylamine of the formula: H2N-(CH2)n-S-S-(CH2)n-NH2 (IX) to obtain a urea of the formula: R1-NH-?-NH-(CH2)n-S-S-(CH2)n-NH-?-NH-R1 (I) wherein R1 and n have the meaning recited above; (b)reacting the urea of formula (I) with a compound capable of converting the compound of formula (I) into the corresponding biscarbodiimide of the formula: R1-N=C=N-(CH2)n-S-S-(CH2)n-N=C=N-R (II) (c)reacting the carbodiimide of formula (II) with a compound selected from the group consisting of nitromethane and a saline derivative of cyanamide to form a product of the formula: R1-NH-?-NH-(CH2)n-S-S-(CH2)n-NH-?-NH-R1 (III) wherein X is CH-NO2 or N-C?N, the nitromethane being used in the presence of a strong base; (d)reacting the compound of formula (III) with a compound which reduces the -S-S- group to obtain a compound of formula: R1-NH-?-NH-(CH2)n-SH (IV) and (e)reacting the compound of formula (IV) with a reactant of the formula Ar-CH2-C1 to obtain the desired product of formula (V). The compounds of formula (V) exhibit antiulcer activity.

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