Showing papers by "Roussel Uclaf published in 1964"

3-keto-4, 9-dienic-11beta-hydroxy-19-nor steroids useful in the treatment of hypercholesterolemia

Abstract: A novel 3-enamino-13b -alkyl-gona-3,5(10),-9(11)-trien-17-one is obtained in a process which comprises reacting a corresponding 4,5-secogon-9-ene-3,5,17-trion or a corresponding gona-4,9-diene-3,17-dione with a secondary amine NHXY wherein the groups X and Y are either the same or different, each being an alkyl group containing from 1-6 carbon atoms, or form together an alkylene chain, e.g. pyrrolidine. Subsequent reaction of the 3-enamino compound with an aliphatic carboxylic acid gives the corresponding 3-keto compound.

Novel 13belta-alkyl-4, 9, 11-gonatriene-3-ones

Abstract: Novel 3-oximido-gona-4,9,11-triene derivatives having the general formula (in which R2 represents a hydrocarbon radical having from 1-18 carbon atoms, R3 is a hydrogen atom or an alkyl group, and R4 represents the oxygen atom of a keto group = C = O or the grouping H-b -OH are obtained in a process in which a 17b -hydroxy-gona-4,9,11triene-3-one derivative having the general formula is reacted with hydroxylamine or an alkyl ether thereof to form the corresponding 3-oximido - 17b - hydroxy - gona - 4,9,11 - triene which may be subjected to oxidation brought about by reaction with a ketone whereby a double exchange of functions occurs with the formation of the corresponding 3-oximido-gona - 4,9,11 - triene - 17 - one. The hydroxylamine may be in the form of the hydrochloride and the oxidation may be effected with aluminium isopropylate in cyclohexanone.

19-nor steroids oxygenated in the 11-position, process of preparation and utilization

Abstract: A novel 3-enamino-13b -alkyl-gona-3,5(10),-9(11)-trien-17-one is obtained in a process which comprises reacting a corresponding 4,5-secogon-9-ene-3,5,17-trion or a corresponding gona-4,9-diene-3,17-dione with a secondary amine NHXY wherein the groups X and Y are either the same or different, each being an alkyl group containing from 1-6 carbon atoms, or form together an alkylene chain, e.g. pyrrolidine. Subsequent reaction of the 3-enamino compound with an aliphatic carboxylic acid gives the corresponding 3-keto compound.

The lactone of 3'-[4-fluoro-4-androstene-17-ol-3-one-17-yl]-propionic acid and process utilized in the preparation thereof

Abstract: The invention comprises the lactones of b -(4-fluoro -17b - hydroxy-androst -5- en -3- on -17a - yl)-propionic acid, of b -(4-fluoro -17b - hydroxy-androst -4- en -3- on -17a - yl)-propionic acid and of b -(4-fluoro -17b - hydroxy-androsta-1, 4-dien -3- on -17a - yl)-propionic acid and a process for the production of 4-fluoro steroid compounds in which a 3-enamino -D 5- steroid is reacted with perchloryl fluoride in a basic solvent medium and at a temperature below 25 DEG C. so as to yield the corresponding 3-keto-4-fluoro -D 5- steroid. Reaction may be effected for example in aqueous methanol made alkaline with pyrrolidine. Subsequently the D 5-double bond may be isomerised to a D 4-double bond by treatment with strong alkali and if desired dehydrogenation may then be effected to obtain a D 1,4-compound. The dehydrogenation may be effected with Corynebacterium simplex. Specification 969,512 is referred to.