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United States Patent Office Patented Mar 3,504,003 United States Patent Office Patented Mar. 31, 1970 1 2 The present process is illustrated, for example, by the 3,504,003 following scheme of partial formulae: A-NOR-B-HOMOSTERODS Oskar Jeger, Zollikerberg, Zurich, and Kurt Schaffner, Zurich, Switzerland, assignors to Ciba Coporation, New York, N.Y., a corporation of Delaware No Drawing. Continuation-in-part of application Ser. No. 266,524, Mar. 20, 1963. This application July 14, 1964, Ser. No. 382,643 Claims priority, application Switzerland Mar. 23, 1962, 3,533/62; Aug. 17, 1962, 9,844/62; Dec. 7, 1962, 0. 14,422/62; Mar. 7, 1963, 2,880/63; July 19, 1963, 9,018/63; Feb. 7, 1964, 1,503/64; June 5, 1964, 7,334/64; June 12, 1964, 7,669/64 Int, C. CO7 c 171/02 U.S. C. 260-410 22 Claims ABSTRACT OF THE DISCLOSURE A-nor-B-homosteroids obtained in a novel and simpler R=H or CH; R = H or acyl manner by irradiating 3-oxo-4:5-oxidosteroids with ultra 20 The 3-oxo-4oz:5a- and 46:56-oxidosteroids, saturated violet light and, if desired, converting the resulting 3:6- in positions 1 and 2, used as starting materials can be pre dioxo-A-nor-B-homosteroids into their functional deriva pared in the manner known perse from the corresponding tives and/or metal salts, or by hydrogenating resulting A-3-oxo compounds, for example by treatment with alka A-3-oxo-6-acyloxy-A-nor-B-homosteroids. The products line hydrogen peroxide or per-acids, or by hydrogenation obtained are useful as anabolic agents, progestative of Al-3-oxo-4:5-oxidosteroids. The last-mentioned starting agents, anti-inflammatory agents and/or as intermediates. materials are new; surprisingly, they can be obtained di rectly from Ali'-3-oxosteroid-dienes by treatment with per-acids, for example with organic per-acids, such as This is a continuation in part of our application Ser. 30 lower aliphatic or aromatic per-acids, for example with No. 266,524 filed Mar. 20, 1963, now abandoned. peracetic, perbenzoic and monoperphthalic acid, or by The present invention relates to the manufacture of dehydrogenation of the above-mentioned 1:2-saturated A-nor-B-homosteroids, more particularly 3-oxo- and 3:6- 3-oxo-4:5-oxidosteroids, for example with selenium di dioxo-A-nor-B-homosteroids, starting from 3-oxo-4:5- oxide or dicyano-dichloroquinone. oxidosteroids, and to new compounds of this class which 35 The irradiation according to the invention of 3-oxo-4:5- are biologically active or represent intermediates for the oxidosteroids is advantageously performed in an organic manufacture of biologically active compounds. Such are solvent, for example in an aliphatic or cycloaliphatic e.g. the 3:6-dioxo-A-nor-B-homo-androstanes and -A- hydrocarbon such as pentane, hexane or methylcyclo androstenes, which have in position 176 a free or esterified hexane. Particularly suitable are aliphatic and cyclic 40 ethers such, for instance, as diethyl ether or dioxane. hydroxyl group, and also the corresponding 3-mono-oxo Suitable light is artificial or strong natural light; it is compounds; they display a high anabolic activity coupled advantageous to use ultra-violet light such as is emitted with a very low androgenic activity. The 3:6-dioxo-A-nor by mercury low-pressure or high-pressure burners, or B-homopregnane compounds, more especially those which strong sunlight. The irradiation is advantageously per contain in position 20, and possibly in position 11, an oxo 45 formed at a temperature ranging from 0 to --80' C. group, in positions 17 and/or 21 and 116 hydroxyl groups, In the 3:6-dioxo-A-nor-B-homosteroids obtained as are of very special importance as novel compounds hav reaction products, which, being 6-diketo compounds are ing a progestative or anti-inflammatory action respec predominantly present in the enol form, any present ester tively. Other compounds, such as the A-nor-B-homo or protective groups such, for example, as ketals or bis steroids of the androstane and pregnane series, which 50 methylenedioxy groups, may be split hydrolytically and have substituents which might be converted into those free hydroxyl groups may be oxidized to oxo groups. On named above typical for the biologically active com the other hand, the products of the present process may be pounds, are important as intermediates for said active converted in the known manner into their functional compounds. This also applies to the other steroid series ketone derivatives derived from the enol form, or into such as the A-nor-B-homo-steroids of the cholane, 55 metal salts. Thus, for example, acylation (for example cholestane, spirostane, cardanolide, and bufanolide series. treatment with a carboxylic anhydride, such as acetic or They may be transformed in a manner known per se into propionic anhydride) yields the corresponding enol esters; the active compounds of the androstane and pregnane with etherifying agents such, for example, as alcohols or series, for example, by an acylolytic, oxidative or micro thio-alcohols in the presence of an acid catalyst, the enol biological method. 60 ethers and respectively, thioenolethers are obtained. The hitherto known steroids having the A-nor-B-homo When the products of the present process are reacted, skeleton-namely 6-oxo-A-nor-B-homocholestane and 6 for example with hydrazines, cyclic hydrazones are ob oxo-176-hydroxy-5oz- and -5B-A-nor-B-homo-androstane tained which may also be looked upon as pyrazole deriva and their 17-benzoates-were obtained by basic treatment tives. Reaction with cupric salts furnishes the correspond of the corresponding 4oz-tosyloxy-5oz-hydroxy compounds. 65 ing copper complexes. It has been found that A-nor-B-homosteroids can be The A5-3-oxo-6-acyloxy-A-nor-B-homosteroids pre obtained in a novel and simpler manner by irradiating pared by the present process can be converted into the 3-oxo-4:5-oxidosteroids with ultra-violet light and, if corresponding saturated 6-unsubstituted 3-oxo-A-nor-B- desired, converting the resulting 3:6-dioxo-A-nor-B-homo homosteroids by catalytic hydrogenation in a manner steroids into their functional derivatives and/or metal 70 known per se, such as hydrogenation, for example, in salts, or by hydrogenating resulting A-3-oxo-6-acyloxy benzene or alcohol, with palladium carbon or palladium A-nor-B-homosteroids. barium carbonate catalyst. 3,504,003 3 4. The 3-oxo-4o:5oz- and 46:56-oxidosteroids used as of -H, -lower alkyl . lower alkyl, --OR . OR, starting materials in the present process belong prefer R4 for a member selected from the group consisting of ably to the androstane, pregnane, cholane, cholestane, spirostane or cardanolide series or to the corresponding 19-nor series and may contain, in addition to the afore OR OR OR OR mentioned groupings, in one or more than one of the =o, ( ( / 1 positions 1, 6, 7, 8, 9, 11, 12, 14, 15-21 further sub H , lower alkyl, lower alkenyl, lower alkinyl, stituents such as alkyl (for example methyl) groups and/ or halogen atoms, free or functionally converted oxo O groups, or free, esterified or etherified hydroxyl groups. O and 1 Yo O Furthermore, the starting materials may contain double w / bonds, more especially as mentioned above, between 'C.H. carbon atoms 1 and 2. It is also possible to use a mix ture of the two 4:5-isomeric epoxides. R5 for a member selected from the group consisting of Particularly important starting materials are, for ex 5 ample, the following compounds: O-acyl and 3-oxo-4o.:5oz-oxido- and 4,3:56-oxido-17-hydroxyandro H. , H , stane and its esters, w 3:17-dioxo-4o.:5o-oxido- and -46:56-oxidoandrostane and 20 its 17-ethyleneketal, Rs and R for a member selected from the group consist 3-oxo-4oz:5a-oxido- and -4.3:56-oxido-17 oz-alkyl-, -17a ing of . H. lower alkyl and . OR, Rs to alkenyl- and -17 oz-alkinyl-17(3-hydroxyandrostanes and gether with R1 a member selected from the group con their esters, such as, for example 3-oxo-40.:5a-oxido sisting of and -46:5p3-oxido-17 (3-hydroxy - 17o. - methyl-, -17a 25 ethyl-, -17ox-vinyl-, -17a-ethinyl- and -17 oz-allyl-andro Stane, 3:20-dioxo-4-cy:5o-oxido- and 43:56-oxidopregnane, 3:20-dioxo-4c.:5o-oxido- and 46:56-oxido-17a-hydroxy pregnane and their esters, 30 3:20-dioxo-4oz:5oz-oxido- and -46:53-oxido-21-hydroxy R8 for a member selected from the group consisting of pregnane and their esters, 3:20-dioxo-4c:5a-oxido- and -43:56-oxido-17o:21-dihy droxy-pregnane, their esters and 17:20; 20:21-bis -lower alkylene, and methylenedioxy compounds, 35 3:20-dioxo-4-ox:5o-oxido- and -46:56-oxido-116:17 c.:21 trihydroxypregnane, their esters and 17:20:20:21-bis methylenedioxy compounds, inter alia, for example, R9 for a member selected from the group consisting of the lactone of Al-3-oxo-4:5-oxido-17f8-hydroxy-17 oz -H and -O-R and R is a member selected from the ((3-carboxyethyl)-androstene and the 1-dehydro-4:5- 40 group consisting of -H, an acyl group, a hydrocarbon radical, X and Y each is a member selected from the oxidotestololactone; group consisting of hydrogen and methyl, and the 1-de furthermore the derivatives, unsaturated in positions 1 hydro derivatives, tautomeric forms and the enol esters and 2, of the above compounds.
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