Process for the production of new imino compounds

C - Chemistry – Metallurgy – 07 – D

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C07D 207/08 (2006.01) C07D 207/20 (2006.01) C07D 207/24 (2006.01) C07D 211/70 (2006.01) C07D 223/04 (2006.01) C07D 223/06 (2006.01) C07D 233/22 (2006.01) C07D 233/24 (2006.01)

Patent

CA 1085413

ABSTRACT OF THE DISCLOSURE The present invention provides processes for the pro- duction of new imino compounds of the general formula 1 Image (I) wherein R1 represents an aliphatic or cycloaliphatic hydrocarbon radi- cal, phenyl optionally substituted by halogen up to atomic number 35, lower alkyl and/or lower alkoxy, or mono- or di- phenyl-lower-alkyl, R2 represents phenyl or thienyl optionally substituted by halo- gen up to atomic number 35, lower alkyl and/or lower alkoxy, or represents lower alkyl, R3 represents hydrogen lower alkyl, a carbonyl group linked with R2 to form a five-membered ring, or the group R6-CO wherein R6 represents lower alkyl of phenyl, R4 if present represents hydrogen or lower alkyl which can be linked with R1 to form a five- to seven-membered ring which can contain as ring members two aromatic ring carbon atoms of a phenyl radical R1 optionally substituted as defined or of a phenyl-lower-alkyl radical R1, and as a six- or seven-membered ring also epoxy or lower alkylimino which is separated by two or more carbon atoms from the nitro- gen atom given in the formula I, if present represents hydrogen or lower alkyl, represents an optionally branched-chain lower alkylene having 2 to 4 chain members, represents imino or lower alkylimino, and m1 and m2 represent 0 or 1 and together always represent 1, n1 and n2 represent 0 or 1 and together always represent 1, and wherein two additional bonds, either corresponding to the dashed lines or corresponding to the dotted lines, are present, with m1 representing 0 in the former case and m2 representing 0 in the latter case, and of acid addition salts thereof. These new substances possess valuable pharmacological properties, particularly hypoglycaemic activity, and can be used for the treatment of hyperglycaemia in mammals, particularly for the oral treatment of Diabetes mellitus. - 1a -

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