GB890577A - Pregnadienes and pregnatrienes - Google Patents

Pregnadienes and pregnatrienes

Info

Publication number
GB890577A
GB890577A GB22565/59A GB2256559A GB890577A GB 890577 A GB890577 A GB 890577A GB 22565/59 A GB22565/59 A GB 22565/59A GB 2256559 A GB2256559 A GB 2256559A GB 890577 A GB890577 A GB 890577A
Authority
GB
United Kingdom
Prior art keywords
bromo
steroid
pregnadiene
lower alkanoyloxy
pregnatriene
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
GB22565/59A
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 GB890577A publication Critical patent/GB890577A/en
Expired legal-status Critical Current

Links

Classifications

    • 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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises compounds having the formula <FORM:0890577/IV (b)/1> in which R is a lower alkanoyl radical containing 1-6 carbon atoms, R1 is hydrogen or a lower alkanoyloxy radical containing 1-6 carbon atoms, X is a halogen atom and <FORM:0890577/IV (b)/2> is the trivalent radical of <FORM:0890577/IV (b)/3> where R2 is a lower alkyl or an aryl radical and a process for making said steroid compounds and the D 4,9(11)-3-one-16a -lower alkanoyloxy (or 16a -hydroxy)-17a -hydroxy derivatives thereof, which comprises (a) treating a D 4-3-one steroid of the formula <FORM:0890577/IV (b)/4> with a hydrohalic acid, and then converting the resulting D 4-3-one-16b -halo-17a -hydroxy compound to the corresponding D 3,5-3,17a -lower alkanoyloxy-16b -steroid of formula I (b) and, if the D 4,9(11)-3-one-16a -lower alkanoyloxy-17a -hydroxy steroid is desired, treating the compounds formed in step (a) with a salt of a lowercarboxylic acid (c) and, if the D 4,9(11)-3-one-16a ,17a -dihydroxy steroid is desired, hydrolysing the 16a -lower alkanoyloxy group of the compounds formed in step (b). Conversion to the D 3,5- 3, 17a - lower alkanoyloxy - 16b - halo - steroid may be effected by treating the d 4-3-one-16b -halo-17a -hydroxy compound with a lower aliphatic acid anhydride, preferably in the presence of an acid such as p-toluene sulphonic acid. Illustrative products of the invention are 3, 17a , 21 - triacetoxy - 16b - bromo - 11a - p - toluene - sulphonyloxy - 3, 5 - pregnadiene - 3, 20 - dione, 3, 17a , 21 - triacetoxy - 16b - bromo - 3, 5, 9 (11) - pregnatriene - 20 - one, 3, 17a , 21 - triacetoxy - 16b - iodo - 11a - p - toluene - sul - phonyloxy - 3, 5 - pregnadiene - 3, 20 - dione, 3, 17a , 21 - triacetoxy - 16b - bromo - 11a - methane - sulphonyloxy - 3, 5 - pregnadiene - 3, 20 - dione, 3, 17a - diacetoxy - 16b - bromo - 3, 5, 9 (11) - pregnatriene - 20 - one, 3, 17a - diacetoxy - 16 - iodo - 3, 5, 9 (11) - pregnatriene - 20 - one, 3, 17a - diacetoxy - 16b - bromo - 11a - methane - sulphonyloxy - 3, 5 - pregnadiene - 20 - one, 3, 17a - diacetoxy - 16b - chloro - 11a - methanesulphonyloxy - 3, 5 - pregnadiene - 20 - one and 3, 17a - di - n - butyryloxy - 16b - bromo - 3, 5, 9 (11) - pregnatriene - 20 - one. Specifications 824,351, 880,201 and 890,565 are referred to.
GB22565/59A 1958-07-09 1959-07-01 Pregnadienes and pregnatrienes Expired GB890577A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US890577XA 1958-07-09 1958-07-09

Publications (1)

Publication Number Publication Date
GB890577A true GB890577A (en) 1962-03-07

Family

ID=22215434

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22565/59A Expired GB890577A (en) 1958-07-09 1959-07-01 Pregnadienes and pregnatrienes

Country Status (1)

Country Link
GB (1) GB890577A (en)

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