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US 4,058,539 AGranted
4,6,8(14)-Triene steroids
AssigneeSteele Chemicals Co. Ltd.
InventorGunther Kruger
Life of this patent
Estimating the term…
Abstract
There are provided novel 4,6,8(14)-triene-steroids as well as processes for preparing such compounds. The above compounds are useful as intermediates in the preparation of other steroids, which in turn, may be converted into valuable pharmaceutical agents.
Claims33
A process for preparing a compound of the formula ##STR39## wherein R is selected from the group consisting of:
- O-acyl;
- ##STR40## and CN, wherein Z is selected from the group consisting of tetrahydropyranyl, lower alkyl and substituted methyl, wherein the substituent on said methyl is selected from the group consisting of phenyl, CH.sub.2 =CH and HC.tbd.C;
- and acyl is selected from the group consisting of acetate, tri-lower-alkyl acetate, monohalo acetate and trihalo acetate;
- and R' is selected from the group consisting of:
- CH.sub.3 ;
- CH.sub.2 OH;
- CH.sub.2 --O--CO--NH--C(CH.sub.3).sub.3 ;
- CH.sub.2 OCOCH.sub.3 ;
- CHO and H, which process is selected from the group consisting of
- a. treating, with a base, a compound chosen from ##STR41## wherein R and R' are as defined above and R"' is AcO;
- and treating the resulting basic mixture with a dehydrogenating agent and a weak acid;
- b. reacting, with a dehydrogenating agent, a compound chosen from ##STR42## wherein R and R' are as defined above, and R'" is AcO or OH;
- c. treating, with ferric chloride and methanol, a compound of the formula (VI), and treating the intermediate obtained, of the formula (VII), with a strong mineral acid wherein R is as defined above and said compounds (VI) and (VII) have the formula ##STR43## d. treating, with a peracid, a compound of the formula ##STR44## wherein R is as defined above, to form a mixture of compounds having the formula ##STR45## wherein R is as defined above and Y is hydrogen, and if desired separating from said mixture the 7-hydroxy compound and acetylating, if desired, said 7-hydroxy compound to form a corresponding 7-acetoxy compound, reacting said mixture, said 7-hydroxy compound or said 7-acetoxy compound with a strong mineral acid;
- e. treating, with a base, a compound of the formula ##STR46## wherein R is as defined above, to form a mixture of compounds of the formula ##STR47## wherein R is as defined above, and treating said mixture with a dehydrating agent;
- f. reacting, with a peracid, a compound of the formula ##STR48## wherein R is as defined above, and treating the intermediate obtained with a base, and subsequently dehydrating the resulting compound of formula (X);
- and
- g. reacting, with a peracid, a compound of the formula ##STR49## wherein R is as defined above and R.sup.4 is chosen from H;
- CH.sub.3 ;
- and CH.sub.2 --O--CO--NH--C(CH.sub.3).sub.3, reacting the intermediate obtained with a base to form a compound of the formula ##STR50## wherein R and R.sup.4 are as defined above, and treating the latter compound with a dehydrating agent.
16 more elements
A compound of the formula ##STR54## wherein R" is selected from the group consisting of O-Z;
- ##STR55## wherein Z is selected from the group consisting of:
- tetrahydropyranyl, lower alkyl, and substituted methyl, wherein the substituent is selected from the group consisting of phenyl, CH.sub.2 =CH and HC.tbd.C;
- acyl represents a member selected from the group consisting of acetate, tri-lower-alkyl acetates, monohalo acetates and trihalo acetates;
- R' is selected from the group consisting of:
- CH.sub.3 ;
- CH.sub.2 OH;
- CH.sub.2 --O--CO--NH--C(CH.sub.3).sub.3 ;
- CH.sub.2 OCOCH.sub.3 ;
- CHO and H;
- the broken line represents an optional double bond;
- and Y is selected from the group consisting of keto, OH, H, OZ and acyl with the proviso that when Y is keto there is no optional double bond present in the compound.
8 more elements
Dependencies are inferred from the claim text.