Patent GB-1013907-A (GB)
Title: Alkene derivatives
Inventor: HARPER MICHAEL JOHN KENNEDY
IPC: C07C49/796
Filed: 1962-09-13
Abstract: The invention comprises compounds of the formula <FORM:1013907/C2/1> and their acid addition salts, wherein the R1R2N(CH2)2O- group is borne in the m- or p-position relative to the CR3=CR4R5 group, R1 and R2 which may be the same or different, stand for C1-6 alkyl groups or the NR1R2 group stands for a nitrogen-containing heterocyclic radical, wherein n is an integer from 2 to 6, R3 and R4, which may be the same or different stand for aryl radicals, optionally substituted by one or more alkyl, alkoxy, and/or dialkylaminoalkoxy radicals and/or one or more halogen atoms and R5 stands for an alkyl, alkenyl or aralkyl radical and the preparation thereof (a) by dehydrating a compound of the formula <FORM:1013907/C2/2> where R stands for the group CR3(OH).CHR4R5 or CR3.C(OH)R4R5\h or (b) by reacting an aminoalkyl halide R1R2N(CH2)nX, wherein X is a halogen atom with a compound of the formula <FORM:1013907/C2/3> where M stands for hydrogen or an alkali metal atom.  Compounds of formula II, wherein R is CR3(OH)CHR4R5 are prepared from a Grignard reagent <FORM:1013907/C2/4> and a compound R3COCHR4R5 or from a compound <FORM:1013907/C2/5> and a Grignard reagent R3MgX and Compounds II, wherein R is -CHR3C(OH)R4R5 are prepared from a Grignard R4.MgX or R5MgX with a compound of the formula <FORM:1013907/C2/6> wherein R6 stands for R5 or R4 respectively. Compounds of Formula IV and V are prepared by reaction of an aminoalkyl halide on the corresponding substituted phenol. Compounds of the Formula III where M is hydrogen are prepared through the methyl ether which in turn is prepared by reacting anisyl magnesium halide with an appropriate carbonyl compound and dehydrating the alkanol so formed.  4-Chloro-a -methyldesoxybenzoi is prepared by reaction of 4-chlorodesoxybenzoin with methyl iodide. Similarly is prepared a ,4-dimethyldesoxybenzoin, 41 - chloro - 4 - methoxy - a  - methyldesoxybenzoin, a  - isopropyl - a  - propyl- and a  - allyl - 4 - methoxydesoxybenzoins. 4-Hydroxy-a -methyldesoxybenzoin is prepared by demethylation of the methyl ether.  Similarly are prepared 4-hydroxy - a  - propyl-, -isopropyl- and -allyldesoxybenzoins.ALSO:Pharmaceutical and veterinary compositions, useful for the modification of endocrine status in man and animals and for the control of hormone-dependent tumours or for the management of the sexual cycle and abenations thereof, comprise compounds of the formula <FORM:1013907/A5-A6/1> or acid addition salts thereof wherein the R1R2N(CH2)n O-group is borne in the m or p position relative to the -CR3=CR4R5 group, R1 and R2, which may be the same or different, stand for C1-6 alkyl radicals or the NR1R2 group stands for a N-containing heterocyclic radical, n stands for an integer from 2 to 6, R3 and R4, which may be the same or different stand for aryl radicals optionally substituted by one or more alkyl, alkoxy, and/or dialhylamino-alkyl radicals and/or one or more halogen atoms, and R5 stands for an alkyl, alkenyl or aralkyl radical, in admixture with a pharmaceutically-acceptable carrier a diluent and optionally together with at least one compound which is known to effect the endocrine status in man and animals, e.g. a known orally active progestational agent.  The compositions may be formulated as tablets, capsules solutions, suspensions, dispersible powders suitable for the preparation of liquid suspensions, mixtures with animal foodstuffs or premixes suitable for addition to animal foodstuffs, sterile solutions for injection or sterile dispersible powders suitable for the preparation of sterile liquid suspensions.