Derivate von Thebain und Oripavin

摘要

1,164,671. Thebaine and oripavine derivatives. RECKITT & SONS Ltd. 26 March, 1968 [31 March, 1967], No. 14755/67. Heading C2C. Novel thebaine and oripavine derivatives of the general formula wherein Y represents the ethero (-CH = CH-) or the ethano (-CH 2 -CH 2 -) group, Q represents one of the radicals R represents a methyl group or a hydrogen atom, R1 represents a hydrogen atom, an alkyl or alkenyl group of up to 3 carbon atoms, a phenyl or a tolyl group, R2 represents a cycloalkyl group of 5 to 7 carbon atoms, an alkyl or alkenyl group of up to 8 carbon atoms, a benzyl or a phenethyl group, R3 represents an alkyl group of up to 5 carbon atoms, a cycloalkylmethyl of 4 to 6 carbon atoms, an allyl, methylallyl, dimethylallyl or crotyl group; R4 represents an alkyl group of up to 5 carbon atoms, and their acid addition salts; are prepared by dehydrogenating compounds of general formula wherein R, R3, Q and Y are as defined above. The above compounds where Q is the group may also be prepared by treating a compound of general formula (A) wherein Y, R, R1, R2 and R3 are as defined above and Q is the group with respectively a Grignard reagent R2MgX or an alkyl lithium, LiR2; or with a Grignard reagent R1MgX or an alkyl lithium LiR1, where X is a halogen atom. The above compounds where Q is the group may also be prepared by treating a compound of general Formula (A), wherein Y, R, R1, R2 and R3 are as defined above and Q is the group with lithium aluminium hydride or aluminium isopropoxide. The above compounds where Q is the group (where R1=R 2 ) may also be prepared by treating a compound of general Formula (A) wherein Y, R, R4, R1 and R3 are as defined above and Q is the group with two moles of a Grignard reagent R1MgX or an alkyl lithium LiR1, wherein X is a halogen atom. Pharmaceutical compositions containing the above compounds where Q = having analgesic and antitussive activity may be administered orally or parenterally.