IL41138A - Antiandrogenic compositions containing (n-phenyl substituted)alkanimidic acid esters - Google Patents

Claims (8)

1. 41 33/2 2017 - ISRAEL ED/vl 1. A pharmaceutical composition comprising as active ingredient an anti-androgenically active N-substituted phenyl alkanimidic acid ester of the general formula I or a pharmaceutically acceptable acid addition salt thereof, in which formula Rj^ represents lower alkyl, X represents nitro, trifluoromethyl or halogen, Y represents hydrogen, halogen, nitro, lower alkyl, lower alkoxy or trifluoromethyl, A represents — , wherein 0 and R, inde- pendently represent Z-substituted-alkyl in which the alkyl moiety is straight or branched- chain and has up to 5 carbon atoms, Z represents hydrogen or hydroxy, and a suitable pharmaceutically acceptable carrier.

2. A composition as claimed in claim 1, wherein in formula I each Z is hydrogen. J. A composition as claimed in claim 2, wherein in formula I the group -A-Z ■ . 41138/2 2017 - ISRAEL ED/vl 4. A composition as claimed in claim 1 wherein in formula I one of the groups Z represents an hydroxy group and the others represent hydrogen. 5. A composition as claimed in claim 4, wherein in formula. I the group Z representing an hydroxy group, is attached to a tertiary carbon atom. 6. A composition as claimed in claim 5* wherein in formula I the group -A-Z represents —0H 7. A composition as claimed in any one of the preceding claims, wherein in formula I is ethyl. 8. A composition as claimed in any one of the preceding claims, wherein in formula I, X is nitro, iodo, bromo or chloro and Y is trifluoromethyl. 9. A composition as claimed in any one of claims 1 to 7, wherein in formula I, X is nitro and Y is bromo or chloro. 10. A composition as claimed in claim 1, wherein the active ingredient is ethyl N-(4-nitro-j5-trifluoro-methylphenyl ) -isobutyrimidate . 41138/2 2017 - ISRAEL ED/vl 11. A process for the preparation of a pharmaceutical composition as claimed in any one of claims 1 to 10 which comprises bringing the active ingredient into a form suitable for administration. 12. A process as claimed in claim 11 which comprises admixing the active ingredient with the pharmaceutically acceptable carrier. 15. A pharmaceutical composition as claimed in claim 1 and whenever obtained by a process as claimed in claim 11 or claim 12. 14. A composition as claimed in any one of claims 1 to 10 and lj5 in the form of a dosage unit. 15. A composition as claimed in claim 14, wherein the dosage unit is a shaped dosage unit. 16. A composition as claimed in claim 15* wherein the dosage unit is a tablet or capsule. 17. A composition as claimed in any one of claims 1 to 10 and 13 in the form of an elixir or syrup. 41118/2 2017 - ISRAEL ED/vl 18. A composition as claimed in any one of claims 1 to 10 and 13 in the form of a sterile pyrogen-free injectable solution or suspension. 19. A composition as claimed in any one of claims 1 to 10 and 13 in the form of a veterinary feed-stock or feed-additive. 20. A pharmaceutical composition as claimed in claim 1 and substantially as hereinbefore described. 21. A method of inducing an anti-adrogenic effect in a non-human animal which comprises administering an effective quantity of an N-substituted phenyl alkani-midic acid ester of the general formula I or a pharmaceutically acceptable acid addition salt thereof, in which formula R^ represents lower alkyl, X represents nitro, trifluoromethyl or halogen, Y represents hydrogen, halogen, nitro, lower alkyl, lower alkoxy or trifluoromethyl, 41138/2 2017 - ISRAEL ED/vl pen ently represent Z-substituted-alkyl in which the alkyl moiety is straight or branched- chain and has up to 5 carbon atoms, and represents hydrogen or hydroxy. 22. A method as claimed in claim 21 wherein in formula I each Z is hydrogen. 2

3. * A method as claimed in claim 22, wherein in formula I the group -A-Z . 2

4. A method as claimed in claim 21, wherein in formula I one of the groups Z represents an hydroxy group and the others represent hydrogen. 2

5. A method as claimed in claim 24, wherein in formula I the group Z representing an hydroxy group is attached to a tertiary carbon atom. 2

6. A method as claimed in claim 25, wherein in formula I the group -A-Z . 2

7. A method as claimed in any one of claims 21 to 26, wherein in formula I R-j^ is ethyl. 411 8/2 2017 - ISRAEL ED/vl 2

8. A method as claimed in any one of claims 21 to 27, wherein in formula I X is nitro, iodo, bromo or chloro and Y is trifluoromethyl. 29· A method as claimed in any one of claims 21 to 7* wherein in formula I X is nitro and Y is bromo or chloro. 30. A method as claimed in claim 21, wherein the N-arylimidate is ethyl N- ( -nitro-3-trifluoromethyl-phenyl )-isobutyrimidate. 31. A method as claimed in any one of claims 21 to 30, wherein the anti-androgenic effect is induced in the treatment of prostatic hyperplasia. 32. A method as claimed in any one of claims 21 to 30, wherein the anti-androgenic effect is induced in a meat-producing animal. 33· A method as claimed in claim 32, wherein the compound of the formula I is administered to a pregnant female animal just before and/or during the period of development of the fetal genitalia in an amount effective to result in the birth of hermaphrodites instead of males. 41118/3 2017 - ISRAEL ED/vl 3. . A method as claimed in claim 32, wherein the anti-androgenic effect is induced in a male animal shortly before and/or during the development of its secondary sex characteristics. 35· Meat-producing animals whenever p¾»©dxnre9 by a method as claimed in claim 33 or claim . 36. The meat of the animals claimed in claim 35·