5-(R3-O-)-5,6-DIHYDROPYRAN WHERE C(-) AND A ARE JOINED
WHEREIN R1, R2 AND R3 EACH ARE LOWER ALKYL; N IS THE INTEGER 1 OR 2; A--B IS CH--CH2 OR C=CH; X IS OH, ALKOXY OF 1--10 CARBON ATOMS, ALKANOYLOXY OF 1-10 CARBON ATOMS OR BENZYLOXY AND Y IS H.
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 R IS HYDROGEN, ALKYL, TETRADROPYRANYL OR AN ACID RESIDUE. TO FORM THE COMPOUNDS, THE 4-UNSUBSTITUTED 6-CHLOROESTRADIENE IS SUBJECTED TO THE ACTION OF AN AGENT FURNISHING POSITIVE AND NEGATIVE CHLORINE, THEREBY FORMING THE 6,6,7-TRICHLORO-SUBSTITUTED COMPOUND, FOLLOWED BY TREATMENT OF THE LATTER COMPOUND WITH A BASE. THE COMPOUNDS HAVE A VERY HIGH PROGESTERONE 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.
摘要:
17-Chloro anti-inflammatory steroids of the formula
WHEREIN X is H or Cl; Y is F or Cl; Z is OH, F or, when Y is Cl, Cl; and R is a free or esterified OH group, are produced by simultaneously reacting, in the presence of a sulfone, the corresponding 17-hydrogen compound or the corresponding Delta 9(11)-17-hydrogen compound with hydrogen fluoride and with an Nchloroacylamide or N-chloroacylimide.
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:
4,6-dichlor- Delta 4,6-steroids of the pregnane and androstane series are produced by reacting a 4-chlor- or a 6-chlor- Delta 4,6-steroid which includes a group of the formula:
WHEREIN X1 and X2 are different and respectively denote hydrogen or chlorine, and wherein each of R1'' and R2respectively, is hydrogen, or R1'' and R2'' jointly denote a methylene group, with compounds capable of forming, respectively, positive and negative chlorine ions; and treating the thus-obtained reaction product with a base. The thus-obtained novel compounds, in the form of pharmaceutical compositions for oral or intramuscular administration are useful in the treatment of gynecological disorders and as contraceptive.
摘要:
17 Beta -Hydroxy-17 Alpha -ethynyl steroids are converted to 17-ethers and 17-esters of 17 Alpha -hydroxy-20-keto-pregnane steroids by forming a 17-sulfite ester of the 17 Beta -hydroxy group with thionyl chloride in the presence of base and then reacting the sulfite ester with an alcohol or carboxylic acid in the presence of an Hg salt.
WHEREIN -A-B-IS ONE OF THE GROUPS-CH2-CH2-CH=CH-, OR-CC1=CH, AND X IS A HALOGEN ATOM, HAVE EXCELLENT ANTI-INFLAMMATORY ACTIVITY, ESPECIALLY TOPICAL ANTI-INFLAMMATORY ACTIVITY, WITH A LOW INCIDENCE OF SIDE EFFECTS, E.G., SODIUM RETENTION, AND POTASSIUM EXCRETION.