C - Chemistry – Metallurgy – 07 – J
Patent
C - Chemistry, Metallurgy
07
J
195/30, 260/83
C07J 7/00 (2006.01) C07J 13/00 (2006.01) C07J 71/00 (2006.01) C12P 33/08 (2006.01)
Patent
CA 1159822
Abstract Novel halogenated steroids of the formula Image (A), in which X represents a halogen atom having a maximum atomic number of 17, Y represents a hydrogen atom or hydroxyl, and R represents an alkyl radical having a maximum of 6 carbon atoms, and their 1,2-dehydro derivatives are manufactured by a novel process by, in succession, ABSTRACT a) introducing the halogen atom X into the 21-position of 3.beta.-hydroxy-16-methyl-pregna-5,16-dien-20-one or a 3- carboxylic acid ester thereof, b) esterifying the resulting 21-X-3.beta.-hydroxy-16-methyl- pregna-5,6-dien-20-one to form a 3-lower alkanoyl ester and treating with a peracid, c) in a resulting 5,6;16,17-diepoxide, rearranging the 16.alpha.,17.alpha.-epoxide ring with a strong acid to form the 16- methylene-17.alpha.-hydroxy grouping, converting the 5.alpha.,6.alpha.- epoxide ring using hydrogen fluoride into the 6.beta.-fluoro- 5.alpha.-hydroxy grouping and esterifying the free 5- and 17- hydroxyl groups formed d) catalytically hydrogenating the resulting 21-X-6.beta.- fluoro-3.beta.,5.alpha.,17.alpha.-trihydroxy-16-methylene-pregnan-20-one 3-lower alkanoyl-5,17-di-lower alkanecarbonyl ester, e) in the resulting corresponding 16.beta.-methyl compound, freeing the esterified 3-hydroxyl group by selective hydrolysis and converting it into the 3-oxo group by treatment with an oxidising agent, f) in a resulting 21-X-6.beta.-fluoro-5.alpha.,17.alpha.-di-lower alkane- carbonyloxy-16.beta.-methyl-pregnane-3,20-dione, removing the 5-positioned lower alkanecarbonyloxy group by means of acid and isomerising the 6.beta.-fluoro by catalysis with a strong acid into the 6.alpha.-configuration, and if desired, hydroxylating in the 11.beta.-position the resulting 21-X-6.alpha.-fluoro-17.alpha.-lower alkanecarbonyloxy-16.beta.- methyl-pregn-4-ene-3,20-dione or a 1,2-dehydro derivative thereof by means of the enzymatic system of a 11.beta.- hydroxylating micro-organism, and/or dehydrogenating a 1,2-saturated and product in the 1,2-position. Compounds of the formula A have a strong anti-inflammatory action and may be used as anti-inflammatory agents. In addition, they also serve as valuable intermediates for the manufacture of highly anti-inflammatorily active poly- halogenated corticosteroids.
376307
Fetherstonhaugh & Co.
Novartis Ag
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