abstract |
PROCEDURE FOR PREPARING NEW DERIVATIVES OF 3-CETO DELTA-4,9-19-NOR- STEROIDS OF GENERAL FORMULA I, WHERE R1 IS AMONG OTHER NAFTHYL, PHENYLPHENYL, ALKYL, FENOXY, FENYLUT, FENYLENE, EVETUALLY ETHYL, R3 IS AMONG OTHER SUBSTITUTED ALKYL, -OH, ACETYL, HYDROXY-OIL, CARBOXIALCOXI, R4 IS HYDROGEN, -OH, ALKYL, EVENTUALLY SUBSTITUTED ALKYNYL, R5 IS HYDROGEN OR METHYL IN POSITION; X IS OXYGEN OR HYDROXIMINE OR ALCOXIMINE, IN A SIN-ANTI POSITION; A AND B REPRESENT ALPHA-EPOXY OR A SECOND LINK BETWEEN CARBONS 9 AND 10; EXCEPT SOME COMBINATIONS IN PARTICULAR. A PRODUCT OF GENERAL FORMULA IS SUBMITTED (II), IN WHICH K IS A BLOCKED KETONIC GROUP IN THE FORM OF CETAL, THIOCETAL, OXIMA OR METHYLLOXIME, R3 HAS THE VALUES OF R3 BEFORE INDICATED AND FURTHER ACETILO BLOCKED, R'1 IS R1 INDICATED AND ALSO PHENYL SUBSTITUTED WITH PROTECTED HYDROXY, HAVING R2, R4 AND R5 THE VALUES ABOVE INDICATED, IN REACTION WITH AN ACID DEHYDRATION ION TO RELEASE THE PROTECTED FUNCTIONS, TO OBTAIN A PRODUCT OF FORMULA (IA), IF SUBMIT IN ANY ORDER TO ONE OR MORE OF THE FOLLOWING REACTIONS: A) OXIDATION, A&B FORM EPOXIDE AND SULFOXIDES OR SULPHONES IN R1, B) REACTION WITH HYDROXYLAMINE (X REPRESENTS A HYDROXYMIN OR ALCOXYXYMINE); C) HYDROLYSIS AND SALIFICATION. |