Patent GB-1152679-A (GB)
Title: Pharmaceutical and Veterinary Preparations
IPC: A23K1/16
Filed: 1967-02-21
Abstract: 1,152,679. Pharmaceutical and veterinary preparations. COMMERCIAL SOLVENTS CORP. 21 Feb., 1967 [2 March, 1966; 10 Feb., 1967], No. 8183/67. Heading A5B. Pharmaceutical and veterinary compositions for fertility control, estrogen therapy and increasing anabolic activity comprise as active ingredients:-(A) a compound having the structure: wherein R is a hydrogen atom, lower alkyl (i.e. having from I to 6 carbon atoms), lower saturated acyclic acyl or benzyl; B is -CH=CH-; wherein R<SP>1</SP> is a hydrogen atom, fluoride, hydroxyl or -N(R<SP>2</SP>) 2  wherein R<SP>2</SP> is a hydrogen atom, alkyl having from 1 to 15 carbon atoms; monocyclic aryl or an aralkyl having from 1 to 15 carbon atoms; Z is >C=O, -CH 2 -C-, -C-CH 2 -, >CHNHOH, >C=NOH or >C=NNHR<SP>5</SP> wherein R<SP>3</SP> is a hydrogen atom, a hydroxyl, a halogen atom, -OR<SP>6</SP> or NHR<SP>7</SP>, R<SP>6</SP> is lower alkyl, benzyl or lower saturated acyclic acyl and R<SP>7</SP> is a hydrogen atom, lower alkyl or monocyclic aryl; R<SP>4</SP> is alkyl, aryl, aralkyl, nitromethyl, aminomethyl, ethynyl, cyano, or -R<SP>9</SP>COOR<SP>8</SP> wherein R<SP>8</SP> is lower alkyl and R<SP>9</SP> is lower alkylene; X is a halogen atom, nitromethyl or aminomethyl; R<SP>5</SP> is lower alkyl, a hydrogen atom, carbamyl or monocyclic aryl; and E is an alkylene having from 2 to 3 carbon atoms; with the proviso that when Z is >CH 2 , >CHNHR<SP>7</SP> or >CHNHOH, B is -CH 2 -CH 2 - and  is a cyclohexane ring or a benzene ring of the formula . wherein X and Y are a hydrogen atom, nitro, amino, diazonium radical, cyano, hydroxyl, aryl, alkenyl, alkyl, acyl; alkoxy, carboxy, -SQ 3 H, -SO 3 R<SP>10</SP>, -SO 2 Cl or -SO 2 NHR<SP>11</SP> wherein R<SP>10</SP> is lower alkyl and R<SP>11</SP> is a hydrogen atom, an alkyl having from 1 to 20 carbon atoms, monocyclic aryl or a halogen atom, with the proviso that when one of X and Y is carboxy the other of X and Y is a hydrogen atom, that R is lower alkyl or benzyl when X or Y is -SO 2 Cl, and that when the radical of formula XI is. a cyclohexane ring, B is -CH 2 -CH 2 - and Z is >CH 2  or >CHOR<SP>6</SP>, and (B) benzestrol; dinestrol; estrone; diethylstilbestrol or a derivative thereof as represented by the structure: wherein A is or. R is H or lower alkyl; Z is H, -PO 3 , -SO 3 R<SP>1</SP> or O where R<SP>1</SP> is an aliphatic hydrocarbon radical having from 1 to 20 carbon atoms; n is 0 or 1 and when 0, R is H; estradiol or a derivative thereof as. represented by. the structure: . wherein Z<SP>1</SP> is H, benzoyl, R or where R is lower alkyl; R<SP>1</SP> is H or lower alkyl; n and n<SP>1</SP> are 0 or 1 ,  and when 0, C#CR<SP>1</SP> is H; a progestogen having the structure: wherein R is H or lower alkyl; Q is -OH or and R is a lower alkyl; Q<SP>1</SP> is H, acetoxy, O # -C#CH, -C#C-R or -CR, wherein R is lower alkyl; Y is lower alkyl or a halogen atom and n and .n<SP>1</SP> are 0 to 1 when n is 0,. R is H and when n<SP>1</SP> is 0, Y is H; or a tris-phenyl ethylene having, the structure wherein X is OH, lower alkoxy or acyloxy and Y<SP>1</SP> is a halogen atom or a hydrogen atom. The ingredient (B) may comprise, as diethylstilbestrol derivatives, diethylstilbestrol dipropionate, monomethyl ; ether,. dimethyl ether, dipalmitate, diphosphate-and disulphate, hexestrol and promethestrol dipropionate; as estradiol derivatives, estradiol benzoate and cyclopentyl.. propionate, estradioldipropionate, estriol ,  ethinyl estradiol and ethinyl estradiol-3- methyl ether; as progestogens, progesterone, dimethisterone, 17α-ethinyl-17#-hydroxy-5 (10) estren-3-one (norethynodrel), norethindrone. ohlormadinone acetate and medroxyprogestrone acetate; and as tris-phenyl ethylene compounds, tris(p-methoxy phenyl)ethylene, tris (p-hydroxyphenyl)ethylene and tris-(p-methoxyphenyl)-ohloro-ethylene. The compositions may be administered orally in the form of pressed or coated tablets, capsules, pills, syrups, solutions or suspensions or parenterally as sterile aqueous solutions or suspensions in oily media. The composition may also be in the form of an animal feed composition also comprising ediblenutrient' carriers and' conventional excipients. '