2-R1,3-(R3O-CO-CH(-OR2)-),3A,6-DI(H3C-),5-Z,6,7-(-B-A-CO- WHEREIN THE GROUP OR2 IS IN THE AF- OR BF-POSITION; X IS HYDROGEN, HALOGEN OR METHYL; Y IS HYDROGEN OR HALOGEN; Z IS HYDROXY OR HALOGEN HAVING AN ATOMIC WEIGHT NO GREATER THAN Y; R1 IS HYDROGEN OR METHYL; R2 IS HYDROGEN OR ACYL AND R3 IS HYDROGEN, ALKALI METAL OR SATURATED OR UNSATURATED UNSUBSTITUTED OR SUBSTITUTED HYDROCARBON OF 1-18 CARBON ATOMS, OR COLLECTIVELY R2 AND R3 ARE DIALKYLMETHYLENE OR CYCLOALKYLIDENE; AND AT LEAST ONE OF X, Y AND R1 ARE OTHER THAN HYDROGEN; AND -A-B- IS
-CH2-CH2-, -CH=CH- OR -CCL=CH;
POSSESS PRONOUNCED TOPICAL ANTI-INFLAMMATORY ACTIVITY AS WELL AS BEING INTERMEDIATES FOR THE PRODUCTION OF THE CORRESPONDING 20-KETO STEROIDS.
摘要:
R1,R3 AND Y HAVE THE SAME ABOVE-INDICATED MEANINGS AND R2. STANDS FOR HYDROGEN OR LOWER ALKYL IN A POLAR ORGANIC SOLVENT, IN THE PRESENCE OF AN ALKALI OR ALKALINE EARTH SALT OF A LOWER ALKANOIC ACID OF 1-5 CARBON ATOMS, OF A CARBONIC ACID, OF OF AN AROMATIC CARBOXYLIC ACID TO FORM SAID 21-ACYLOXY-STEROID.
C1--C2, C5---C7,
IS A DOUBLE BOND, R2 IS H OR LOWER ALKYL, R3 IS LOWER ALKANOYL IS OF 1-5 CARBON ATOMS AND Y IS HYDROGEN OR FLUORINE, WHICH COMPRISES HEATING AT A TEMPERATURE FROM ABOUT 80*C. TO THE BOILING POINT OF THE REACTION SOLVENT A NON-ESTERIFIED 11B, 17, 21 - TRIHYDROXY-2-KETO-PREGNANE OF THE FORMULA 3,21-DI(O=),6-R1,9-Y,11-(HO-),16-R2,20-(R3-O-)PREGNA-1,4,6,16-TETRAENE PREGNA-1,4,6,17(20)-TETRAENE WHEREIN
C6-----7
IS A SINGLE BOND, OR FLUORINE, CHLORINE, BROMINE OR METHYL WHEN
C6-----7
EACH REPRESENT A SATURATED OR UNSATURATED CARBON-TO-CARBON BOND, R1 IS H OR METHYL IN THE A- OR B-POSITION WHEN
C1-------C2 AND C6 -------C7
1. A PROCESS FOR THE PRODUCTION OF $4.16-11B-HYDROXY3,20-DIKETO-21-ACYLOXY STEROIDS OF THE FORMULA 3,20-DI(O=),6-R1,9-Y,11-(HO-),16-R2,21-(R3-O-)-18-NORWHEREIN
摘要:
1. A PROCESS FOR THE PRODUCTION OF $9(11),16-20-KETO STEROIDS WHICH COMPRISES HEATING A NITRATE 11,17:DIESTER OF AN 11B, 17A-DIHYDROXY-20-KETO STEROID HAVING A HYDROGEN ATOMS AT THE 9-POSITION AT A TEMPRATURE OF ABOVE 80* C, IN THE PRESENCE OF AN ALKALI SALT OR ALKALINE EARTH SALT OF A LOWER CARBOXYLIC ACID.
WHEREIN R1 IS ALKYL OF 1-3 CARBON ATOMS; R2 IS =O,
(R3-O-),(R4-)
IN WHICH R3 IS HYDROGEN OR ACYL OF UP TO 6 CARBON ATOMS AND R4 IS HYDROGEN OR SATURATED OR UNSATURATED ALKYL OF UP TO 4 CARBON ATOMS, OR
(R5-CH2-CO-),(R6-)
IN WHICH R5 AND R6 ARE HYDROGEN, HYDROXY OR ACYLOXY, AND R7 IS HYDROGEN, ALKYL OF UP TO 4 CARBON ATOMS OR ACYL, ARE PREPARED BY REACTING A 3-KETONE-$4-STEROID OF THE GENERAL FORMULA
13-R1,17-(R2=)GON-4-EN-3-ONE
WHEREIN R1 AND R2 HAVE THE VALUES GIVEN ABOVE, WITH A BASIC REAGENT IN A HIGH-BOILING POLAR SOLVENT IN THE PRESENCE OF OXYGEN AT TEMPERATURES OF 70-150* C.; AND OPTIONALLY THEREAFTER ESTERIFYING OR ETHERIFYING ANY FREE HYDROXY GROUPS PRESENT IN THE PRODUCT IN A CONVENTIONAL MANNER.
摘要:
7A-METHYL-1A,2A-METHYLENE-ANDROSTENOLONES OF THE FORMULA 1,2-(-CH2-),3-(O=),7-(CH3-),17-(R-O-)ANDROST-4-ENE POSSESS ANABOLIC ACTIVITY WITH MINIMAL ASSOCIATED ANDROGENIC ACTIVITY.
WHEREIN X IS HYDROGEN,HALOGEN,ORMETHYL; Y IS HYDROGEN ORHALOGEN; Z IS HYDROXY OR HALOGEN HAVING AN ATOMIC WEIGHT NO GREATER THAN Y; R1 IS HYDROGEN OR METHYL; R2 IS HYDROGEN, ALKALI METAL OR SUBSTITUTED OR UNSUBSTITUTED HYDROCARBON OF 1-8 CARBON ATOMS WHICH IS UNSUBSTITUTED OR SUBSTITUTED BY HYDROXY, HALO, ALKOXY, CARBOXY, CARBALKOXY, AMINO, ALKYLAMINO, DIALKYLAMINO, NITRO OR SULFATO, WHEREIN ALKYL IN EACH INSTANCE CONTAINS 1-4 CARBON ATOMS; AND --A--B--IS--CH=CH--,--CCI=CH-- OR, WHEN AT LEAST ONE OF X, Y AND R1 IS OTHER THAN HYDROGEN, --CH2--CH2; PROCESS PRONOUNCED TOPICAL ANTI-INFLAMMATORY ACTIVITY.
WHEREIN R1 AND R2 ARE E.G., H, ALKYL, CYCLOALKYL, ARYL OR HETEROARYL, POSSESS LONG ACTING PROGESTIONAL ACTIVITY AND ARE PRODUCED BY THE ACID CATALYZED CONDENSATION OF THE CORRESPONDING 16B-HYDROXY-17A-MERCAPTO STEROIDS WITH A KETONE OR ALDEHYDE UNDER EPIMERIZATION OF THE SUBSTITUENT ON CARBON ATOM C-16.