IT1237444B - 6-Alpha-halo-9,11-oxido-pregna-1,4-diene derivs. prepn. - by halogenation of 3-alkoxy or acyloxy-1,3,5-tri:ene prepd. by acylation of etherification of 3-keto 9,11-oxido-pregna-1,4-diene - Google Patents

6-Alpha-halo-9,11-oxido-pregna-1,4-diene derivs. prepn. - by halogenation of 3-alkoxy or acyloxy-1,3,5-tri:ene prepd. by acylation of etherification of 3-keto 9,11-oxido-pregna-1,4-diene

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Publication number
IT1237444B
IT1237444B IT2204979A IT2204979A IT1237444B IT 1237444 B IT1237444 B IT 1237444B IT 2204979 A IT2204979 A IT 2204979A IT 2204979 A IT2204979 A IT 2204979A IT 1237444 B IT1237444 B IT 1237444B
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Prior art keywords
halo
alpha
pregna
diene
derivs
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IT2204979A
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Italian (it)
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IT7922049A0 (en
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Blasinachim S P A Milano
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Priority to IT2204979A priority Critical patent/IT1237444B/en
Publication of IT7922049A0 publication Critical patent/IT7922049A0/en
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Publication of IT1237444B publication Critical patent/IT1237444B/en

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Abstract

Prepn. of 6 alpha-halo-3-keto-pregna-1,4-diene derivs of formula (III) comprises reaction of 3-keto-pregna-1,4-diene derivs. (I) with an acylating or etherifying agent (such as acyl anhydrides, isopropenyl acetate or trialkyl orthoformates) in the presence of acid catalysts (such as p-toluene sulphonic acid)to give novel corresp. 3-enol deriv. of formula (II), and reaction of this with an appropriate halogenating agent. (such as a N-halo-amide or perchloryl fluoride). (where R,Z=H, hydroxy or =9C carboxylic acyloxy or W and Z together may be -O-CMe2-O--W=H hydroxy or methyl, X= halo pref. Cl or F and R1=lower alkyl or lower acyl) The cpds are useful as intermediates. The epoxy ring may be opened by reaction with hydrohalic acids to give the 6alpha, 9alpha-dihalo-11-beta-hydroxy-pregna-1,4-diene-3-one derivs. The 9 halo cpd. (not 9-F) may be dehalogenated by known methods. Typical products prepared from (III) include fluocinonide which may be deacylated to give fluocinolone acetonide, 6 alpha, 9 alpha-difluoro prednisolone, flumethasone, flurisolide, diflucortolone, diflorasone etc. The process gives (II) as te 6-alpha-halo epimer or a mixture in which the 6 alpha-epimer predominates.
IT2204979A 1979-04-23 1979-04-23 6-Alpha-halo-9,11-oxido-pregna-1,4-diene derivs. prepn. - by halogenation of 3-alkoxy or acyloxy-1,3,5-tri:ene prepd. by acylation of etherification of 3-keto 9,11-oxido-pregna-1,4-diene IT1237444B (en)

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Application Number Priority Date Filing Date Title
IT2204979A IT1237444B (en) 1979-04-23 1979-04-23 6-Alpha-halo-9,11-oxido-pregna-1,4-diene derivs. prepn. - by halogenation of 3-alkoxy or acyloxy-1,3,5-tri:ene prepd. by acylation of etherification of 3-keto 9,11-oxido-pregna-1,4-diene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT2204979A IT1237444B (en) 1979-04-23 1979-04-23 6-Alpha-halo-9,11-oxido-pregna-1,4-diene derivs. prepn. - by halogenation of 3-alkoxy or acyloxy-1,3,5-tri:ene prepd. by acylation of etherification of 3-keto 9,11-oxido-pregna-1,4-diene

Publications (2)

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IT7922049A0 IT7922049A0 (en) 1979-04-23
IT1237444B true IT1237444B (en) 1993-06-05

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IT2204979A IT1237444B (en) 1979-04-23 1979-04-23 6-Alpha-halo-9,11-oxido-pregna-1,4-diene derivs. prepn. - by halogenation of 3-alkoxy or acyloxy-1,3,5-tri:ene prepd. by acylation of etherification of 3-keto 9,11-oxido-pregna-1,4-diene

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