Patent ID: 6596863
Filing Date: 2003-07-22
Classification: A61K,C07C,C07D

Abstract:
A process for producing a nitroetheneamine derivative represented by the formula (Iâ€²-1) wherein R1â€² is a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, a cycloalkyl group which may be substituted, a cycloalkenyl group which may be substituted or a cyano group; each of R2â€² and R3â€² which are independent of each other, is a hydrogen atom, an alkyl group which may be substituted (provided that a heterocyclic methyl group which may be substituted is excluded), a cycloalkyl group which may be substituted, a cycloaklenyl group which may be substituted, a hetercyclic group which may be substituted or a Aâ€²â€”R7â€² group (wherein Aâ€² is S, SO, SO3, CO or CO2, and R7â€² is a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, a cycloalkyl group which may be substituted, a cycloaklenyl group which may be substituted, an aryl group which may be substituted or a heterocyclic group which may be substituted); or R2â€² or or R3â€² may form, together with the N atom, a Nâ€”CR8â€²R9â€² group (wherein each of R8â€² and R9â€² which are independent of each other, is a hydrogen atom, an alkyl group which may be substituted, an aryl group which may be substituted, a heterocyclic group which may be substituted or an alkoxy group which may be substituted); R4â€² is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkoxyphenyl group, a haloalkyloxyphenyl group, which may be substituted, a cycloalkenyl group which may be substituted, an alkoxy group which may be substituted, aâ€”Aâ€²R7â€² group (wherein Aâ€² and R7â€² are as defined above) or an amino group which may be substituted; R6â€² is a hydrogen atom, a nitro group, a cyano group or a Aâ€²â€”R7â€² group (wherein Aâ€² and R7â€² are as defined above) or an alkyl group which may be substituted; at least two selected from R1â€², R2â€², R3â€² and R4â€² may together form a ring containing or not containing a hetero atom in addition to the nitrogen atom; provided that (1) a case wherein R1â€² or R4â€² is an alkyl group substituted by a hetero-ring which may be substituted, (2) a case where R1â€², R3â€² and R6â€² are all hydrogen atoms, R2â€² is a hydrogen atom, an alkyl group which may be substituted or an aryl group which may be substituted, and R4â€² is â€ƒ(wherein j is an integer of from 1 to 6), and (3) a case wherein R1â€² is a hydrogen atom; each of R2â€² and R3â€² which are independent of each other, is a hydrogen atom, and alkyl group which may be substituted or a phenyl group which may be substituted, R4â€² is an alkyl which may be substituted, a phenyl group which may be substituted, an Aâ€²â€”R7â€² group (wherein Aâ€² and R7â€² are as defined above) or an amino group which may be substituted; and R6â€² is a hydrogen atom, are excluded; or its stereoisomers, its tautomer or a salt thereof which comprises: (a) a first step of reacting a compound represented by the formula (XXIV-1) â€ƒwherein R4â€² is as defined above, Z is an alkyl group or an arylalkyl group, with a compound by the formula (XVII-1) R6â€²â€”CH2NO2 (wherein R6â€² is as defined above) to obtain a compound represented by the formula (XXV-1): â€ƒwherein R4â€², R6â€² and Z are as defined above, and (2) a second step of reacting the compound of the above formula (XXV-1) obtained in the first step with a compound represented by the formula (V-1) â€ƒ(wherein Y is a hydrogen atom or an alkali metal element, and R1â€², R2â€² and R4â€² are as defined above) to obtain a nitroetheneamine derivative of the above formula (Iâ€²-1).