C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/267.2, 260/2
C07D 295/10 (2006.01) C07D 211/00 (2006.01) C07D 211/32 (2006.01) C07D 211/44 (2006.01) C07D 211/52 (2006.01) C07D 295/108 (2006.01)
Patent
CA 1077039
Abstract of the Disclosure A process for producing butyrophenone compounds having excellent psychotropic activities and represented by the formula: Image wherein Z is a group having one of the following formulae: Image [wherein R1 is a benzyl group, a 2,4-dichlorobenzyl group, a 4-chlorobenzyl group, a 3,4-dichlorobenzyl group, a 3- trifluoromethylphenyl group, a 3-trifluoromethyl-4-chloro- phenyl group or a 3,4-dichlorophenyl group]; Image [wherein R2 and R3 can be the same or different and each is selected from a hydrogen atom, a halogen atom, a trifluoromethyl group, a lower alkyl group or a lower alkoxy group]; Image [wherein the dotted line indicates the optional presence of an additional single bond linkage and R4 is a hydrogen atom - 1 - or a lower alkyl group]; Image [wherein R5 is a hydrogen atom or a lower alkyl group and R6 is a hydrogen atom or a halogen atom]; Image [wherein R7 is a hydrogen atom or a lower alkoxy group]; Image [wherein R8 and R9 can be the same or different and each is selected from a hydrogen atom, a lower alkyl group or a phenyl group optionally substituted with one substituent selected from the group consisting of halogen, lower alkyl and lower alkoxy]; Image [wherein R10 is a hydrogen atom, a lower alkyl group, a lower alkoxy group or a trifluoromethyl group and n is an integer of 1 to 4]; Image [wherein R11 is a hydrogen atom, a lower alkyl group or a - 2 - phenyl group optionally substituted with one or two sub- stituents selected from the group consisting of halogen, lower alkyl, lower alkoxy and trifluoromethyl, Y is an oxygen atom, a sulfur atom, a carbonyl group or a group of either one of the formulae: Image and Image (wherein R12 is a hydrogen atom, a lower alkyl group or a phenyl group optionally substituted with one or two substituents selected from the group consisting of halogen, lower alkyl, lower alkoxy and trifluoromethyl) and m is an integer of from I to 4); Image ; and Image ; which process comprises reacting a compound of the formula: Image (II) wherein A is a halogen atom and Image is a carbonyl group or a protected carbonyl group,with a compound of the formula: H-Z (III) wherein Z is as defined in claim 1 to give a compound of the formula: Image (IV) wherein W and Z are each as defined above, hydrolyzing those compounds of formula (IV) wherein -?=W is a protected carbonyl group, and when pharmaceutically acceptable salts are required, reacting those compounds of formula II] in the free base form with a corresponding acid addition or quaternary ammonium salt forming reagent. - 4 -
246882
Ono Keiichi
Sasajima Kikuo
Yamamoto Hisao
Na
Sumitomo Chemical Company
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