3,4-methano pyrrolidine derivatives, compositions thereof...

A - Human Necessities – 01 – N

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A01N 43/38 (2006.01) A01N 47/16 (2006.01) A01N 47/38 (2006.01) C07D 209/02 (2006.01) C07D 209/52 (2006.01) C07D 403/06 (2006.01)

Patent

CA 1124738

ABSTRACT 3,4-Methano pyrrolidine derivatives of the general formula:- Image (I) in which R1 represents a hydrogen atom, an alkyl, alkenyl or alkynyl group of up to 10 carbon atoms, an aryl or aralkyl group of up to 10 carbon atoms, optionally substituted by up to two halogen atoms or alkyl or alkoxy groups of up to 6 carbon atoms, a group Image , wherein X represents an oxygen or sulphur atom and R3 repre- sents i) a group -NR4R5, wherein R4 and R5 each independently represent a hydrogen atom, an alkyl, alkenyl or alkynyl group of up to 10 carbon atoms or an aryl or aralkyl group of up to 10 carbon atoms, optionally substituted by up to two halogen atoms or alkyl or alkoxy groups of up to 6 carbon atoms, or one of R4 or R5 repre- sents a group -NR4'R5', wherein R4' and R5' have the same meaning as R4 and R5, respectively, with omission of the group NR4'R5', or R4 and R5 together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocyclic ring, or ii) a group (X)nR6, wherein n is 0 or 1 and R6 has the same meaning as R4 or R5 with the omission of the group NR4'R5' or when n is 1, R6 represents an alkali metal, alkaline earth metal, ammonium or an alkyl-substituted ammonium ion, the alkyl group of which each con- tains up to 6 carbon atoms; a cyano group; the group NO; or an alkyl- or arylsulphonyl group, the alkyl or aryl group of which each contains up to 10 carbon atoms; and R2 represents a group Image , wherein X and R3 have the same meaning as defined hereinbefore, a group -CH2(X)R6 or a group -CH(XR6)(XR7)or a group -CH(XR6)(XR7), wherein X and R6 have the same meaning as defined hereinbefore and R7 has the same meaning as R4 or R5 with omission of hydrogen and the group NR4'R5'; or the corresponding amine hydrogen chloride acid salt with the proviso that when the nitrogen atom on the ring is substituted with one hydrogen atom only, R2 does not represent a group -?-OR9, wherein R9 represents a hydrogen atom, an alkali metal, an alkaline earth metal, an ammonium ion or an alkyl group of up to 10 carbon atoms.

316469

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