GB933867A - Fluorinated steroids - Google Patents

Fluorinated steroids

Info

Publication number
GB933867A
GB933867A GB4166359A GB4166359A GB933867A GB 933867 A GB933867 A GB 933867A GB 4166359 A GB4166359 A GB 4166359A GB 4166359 A GB4166359 A GB 4166359A GB 933867 A GB933867 A GB 933867A
Authority
GB
United Kingdom
Prior art keywords
steroid
radicals
treating
streptomyces
form
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB4166359A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
Wyeth Holdings LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US77859558A priority Critical
Priority to US82563959A priority
Priority to US83585659A priority
Application filed by Wyeth Holdings LLC filed Critical Wyeth Holdings LLC
Publication of GB933867A publication Critical patent/GB933867A/en
Application status is Expired legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J71/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J1/00Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J5/00Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J75/00Processes for the preparation of steroids in general

Abstract

The invention comprises a compound having the formula: <FORM:0933867/IV(a)/1> wherein -C1-C2 and -C4-C5- are -CH2-CH2- or -CH=CH-; -C9-C11- is <FORM:0933867/IV(a)/2> different and are hydrogen atoms, alkyl radicals, alkaryl radicals, aryl radicals, cycloalkyl radicals or heterocyclic radicals or taken together are cycloalkyl or heterocyclic radicals; and Y is hydrogen, fluoro, OH or OR, in which R is a lower alkanoyl radical, a tetrahydropyran-2-yl-oxy radical or a tetrahydrofuran-2-yl-oxy radical, and the preparation thereof by treating a steroid of formula I lacking one or more of the above specified substituents or structures in accordance with one or more of the following reactions performed in any desired order; (1) forming the D 1 and/or D 4 unsaturation by use of a dehydrogenating agent such as SeO2 or by use of a microorganism such as the Nocardia type; (2) treating the 9,11-oxide with HF preferably in a suitable inert solvent to form the 9a -fluoro-11b -hydroxy steroid, and, if desired, oxidising the 11-hydroxy to 11-keto at any time in the reaction sequence; (3) reacting the 16a -17a -dihydroxy steroid in the presence of an acidic agent with a carbonyl compound <FORM:0933867/IV(a)/3> wherein R1 and R11 are as defined above; (4) introducing the 6a -fluoro atom by treating the corresponding 5a ,6a -epoxy steroid with HF and then dehydrating; (5) where the 6a -mono-fluoro compounds are prepared forming the 11b -hydroxy group microbiologically, employing for example Botrytus cinerea. The 16a ,17a -dihydroxy steroid may be obtained by treating the corresponding 17a -hydroxy steroid with an organism such as Streptomyces roseochromogenus, Streptomyces viridus, Streptomyces olivaceous, and Streptomyces argenteolus.
GB4166359A 1958-12-08 1959-12-08 Fluorinated steroids Expired GB933867A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US77859558A true 1958-12-08 1958-12-08
US82563959A true 1959-07-08 1959-07-08
US83585659A true 1959-08-25 1959-08-25

Publications (1)

Publication Number Publication Date
GB933867A true GB933867A (en) 1963-08-14

Family

ID=27419743

Family Applications (2)

Application Number Title Priority Date Filing Date
GB4166359A Expired GB933867A (en) 1958-12-08 1959-12-08 Fluorinated steroids
GB2319361A Expired GB933868A (en) 1958-12-08 1959-12-08 Process for fluorinating steroids

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2319361A Expired GB933868A (en) 1958-12-08 1959-12-08 Process for fluorinating steroids

Country Status (3)

Country Link
BE (1) BE585432A (en)
ES (1) ES254059A1 (en)
GB (2) GB933867A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51144719A (en) * 1975-05-27 1976-12-13 Syntex Inc Preparation of crystalline frunisolide and ittcontaining composition
WO1994025478A1 (en) * 1993-04-29 1994-11-10 Instytut Farmaceutyczny 16α,17α-ACETAL GLUCOCORTICOSTEROIDAL DERIVATIVES
WO2005028495A1 (en) * 2003-09-24 2005-03-31 Glaxo Group Limited Anti-inflammatory glucocorticoids
EP1893220A1 (en) * 2005-06-14 2008-03-05 Gilead Sciences, Inc. Substituted phenylphosphates as mutual prodrugs of steroids and beta -agonists for the treatment of pulmonary inflammation and bronchoconstriction
WO2009108118A1 (en) * 2008-02-27 2009-09-03 Astrazeneca Ab 16 alpha, 17 alpa-acetal glucocorticosteroidal derivatives and their use
US8163724B2 (en) 2007-10-04 2012-04-24 Astrazeneca Ab Glucocorticosteroids, processes for their preparation, pharmaceutical compositions containing them and their use in therapy
US8338587B2 (en) 2009-04-03 2012-12-25 Astrazeneca Ab Compounds

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51144719A (en) * 1975-05-27 1976-12-13 Syntex Inc Preparation of crystalline frunisolide and ittcontaining composition
DE2624924A1 (en) * 1975-05-27 1977-12-15 Syntex Inc Flunisolide and their pharmaceutical use
JPS6247880B2 (en) * 1975-05-27 1987-10-09 Syntex Inc
WO1994025478A1 (en) * 1993-04-29 1994-11-10 Instytut Farmaceutyczny 16α,17α-ACETAL GLUCOCORTICOSTEROIDAL DERIVATIVES
WO2005028495A1 (en) * 2003-09-24 2005-03-31 Glaxo Group Limited Anti-inflammatory glucocorticoids
EP1893220A1 (en) * 2005-06-14 2008-03-05 Gilead Sciences, Inc. Substituted phenylphosphates as mutual prodrugs of steroids and beta -agonists for the treatment of pulmonary inflammation and bronchoconstriction
EP1893220A4 (en) * 2005-06-14 2011-06-15 Gilead Sciences Inc Substituted phenylphosphates as mutual prodrugs of steroids and beta -agonists for the treatment of pulmonary inflammation and bronchoconstriction
US8163724B2 (en) 2007-10-04 2012-04-24 Astrazeneca Ab Glucocorticosteroids, processes for their preparation, pharmaceutical compositions containing them and their use in therapy
WO2009108118A1 (en) * 2008-02-27 2009-09-03 Astrazeneca Ab 16 alpha, 17 alpa-acetal glucocorticosteroidal derivatives and their use
US8338587B2 (en) 2009-04-03 2012-12-25 Astrazeneca Ab Compounds

Also Published As

Publication number Publication date
GB933868A (en) 1963-08-14
ES254059A1 (en) 1960-05-01
BE585432A (en) 1960-06-08
BE585432A1 (en)

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