GB933868A - Process for fluorinating steroids - Google Patents

Process for fluorinating steroids

Info

Publication number
GB933868A
GB933868A GB2319361A GB2319361A GB933868A GB 933868 A GB933868 A GB 933868A GB 2319361 A GB2319361 A GB 2319361A GB 2319361 A GB2319361 A GB 2319361A GB 933868 A GB933868 A GB 933868A
Authority
GB
United Kingdom
Prior art keywords
steroid
reacting
following general
group
general configuration
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
GB2319361A
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
American Cyanamid Co
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
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB933868A publication Critical patent/GB933868A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 2-fluoro-progesterone, 2,21-difluoroprogesterone, 21,21-di-fluoroprogesterone, 2,9a -difluoro-11b ,21-di-hydroxy- 16a , 17a -isopropylidenedioxyprogesterone, and a process for preparing a steroid having the following general configuration in its structure:- <FORM:0933868/IV(a)/1> wherein F is a fluorine atom attached to a carbon atom of the steroid molecule 'a ' to a carbonyl function at position 3, 17 or 20 characterised by reacting the salt formed from a steroid having the following general configuration in its structure: <FORM:0933868/IV(a)/2> wherein R is a hydrogen, carbalkoxy, carboxy, or an OH radical, and wherein the <FORM:0933868/IV(a)/3> group is attached to a carbon of the steroid molecule 'a ' to a carbonyl function at position 3, 17, or 20, with perchloryl fluoride and then hydrolysing the product formed in the presence of an alkaline reagent, and wherein any group on the reacting steroid which is sensitive to the reagents used under the reaction conditions is suitably protected. By this process at least one fluorine is introduced into the 2, 4, 16 and/or 21-positions of the steroid.
GB2319361A 1958-12-08 1959-12-08 Process for fluorinating steroids Expired GB933868A (en)

Applications Claiming Priority (3)

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

Publications (1)

Publication Number Publication Date
GB933868A true GB933868A (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 Before (1)

Application Number Title Priority Date Filing Date
GB4166359A Expired GB933867A (en) 1958-12-08 1959-12-08 Fluorinated steroids

Country Status (3)

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

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX3864E (en) * 1975-05-27 1981-08-26 Syntex Corp A PROCESS TO PREPARE THE CRYSTALLINE COMPOUND 6-FLUIRO-11B 21-DIHIROXI-16 17-ISOPROPILIDENDIOXIPREGNA-1 4-DIEN-3 20-DIONA
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
AU2006259604A1 (en) * 2005-06-14 2006-12-28 Gilead Sciences, Inc. Substituted phenylphosphates as mutual prodrugs of steroids and beta -agonists for the treatment of pulmonary inflammation and bronchoconstriction
MX2010003698A (en) 2007-10-04 2010-04-21 Astrazeneca Ab Steroidal [3, 2-c] pyrazole compounds, with glucocorticoid activity.
MX2010009022A (en) * 2008-02-27 2010-09-07 Astrazeneca Ab 16 alpha, 17 alpa-acetal glucocorticosteroidal derivatives and their use.
UY32520A (en) 2009-04-03 2010-10-29 Astrazeneca Ab COMPOUNDS THAT HAVE AGONIST ACTIVITY OF THE GLUCOCORTICOESTEROID RECEPTOR
KR20220119529A (en) 2016-06-02 2022-08-29 애브비 인코포레이티드 Glucocorticoid receptor agonist and immunoconjugates thereof
WO2019106609A1 (en) 2017-12-01 2019-06-06 Abbvie Inc. Glucocorticoid receptor agonist and immunoconjugates thereof

Also Published As

Publication number Publication date
GB933867A (en) 1963-08-14
BE585432A (en) 1960-06-08
ES254059A1 (en) 1960-05-01

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