SE303486B - - Google Patents

Info

Publication number
SE303486B
SE303486B SE728861A SE728861A SE303486B SE 303486 B SE303486 B SE 303486B SE 728861 A SE728861 A SE 728861A SE 728861 A SE728861 A SE 728861A SE 303486 B SE303486 B SE 303486B
Authority
SE
Sweden
Prior art keywords
hydroxy
steroids
steroid
oxo
groups
Prior art date
Application number
SE728861A
Inventor
A Wettstein
J Kalvoda
H Ueberwasser
G Anner
K Heusler
Original Assignee
Ciba Geigy
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 claimed from CH813360A external-priority patent/CH412874A/en
Priority claimed from CH1210760A external-priority patent/CH454840A/en
Priority claimed from CH1439360A external-priority patent/CH451925A/en
Application filed by Ciba Geigy filed Critical Ciba Geigy
Publication of SE303486B publication Critical patent/SE303486B/xx

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
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises D 5-3-hydroxy- or -acyloxy-steroids of the androstane, pregnane or spirostane series containing in the 10-position a hydroxymethyl, acyloxymethyl, formyl, carboxy or carbalkoxy group; and a process for the preparation of any steroid containing a D 5-double bond and the aforementioned 3- and 10-substituents wherein a 5a -halogeno-6b , 19-steroid, a 19,6b -lactone of a 5a - halogeno - 6b - hydroxy - steroid 19 - acid or a 19,6b -cyclohemiacetal of a 10-formyl-5a -halogeno - 6b - hydroxy - steroid is treated with a reducing agent and, if desired, any hydroxy or 10-carboxy compound obtained is esterified or any hydroxy or 10-formyl compound obtained is oxidized and/or any ester obtained is hydrolysed. The starting material may belong to any of the steroid series mentioned above or to the cholane, cholestane, stigmastane or cardanolide series, and may contain free, ketalized or enolized oxo groups, esterified or etherified hydroxyl groups, alkyl groups of at most 7 carbon atoms or halogen atoms in one or more positions of the steroid nucleus or 17-side chain. They may also contain double bonds and oxido groups. When alkali or alkaline earth metals in liquid ammonia are used as reducing agents D 5-19-hydroxy-steroids are formed, and this may be accompanied by the reduction of other oxido groups or of oxo groups unless they have previously been protected. 19,6b -hemiacetals of 5a -halogeno-6b -hydroxy - 19 - oxo - steroids and 19,6b - lactones of the corresponding 19-acids can be reduced under mild conditions e.g. the use of zinc and an alcohol or an acid, to yield, respectively, D 5-19-oxo-steroids and D 5-steroid-19-acids. These may also be prepared by oxidation of the 19-hydroxy-steroids. The steroids of the invention may further be converted to 19-oxygenated D 4 - 3 - oxo - steroids and these may then be heated with an alkali metal hydroxide in an anhydrous or aqueous solution to give 19-nor - D 4 - 3 - oxo - steroids. Examples are given and an extensive list of esterifying acids is provided. The 19,6b - lactone of 3b - acetoxy - 5a -chloro - 6b - hydroxy - 17 - oxo - androstane - 19-acid is prepared by chromic acid oxidation of the corresponding 6b ,19 - oxido compound. Specifications 994,764, 994,748 and 994,750 are referred to.
SE728861A 1960-07-15 1961-07-13 SE303486B (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH813360A CH412874A (en) 1960-07-15 1960-07-15 Process for the production of new 6B, 19-oxido-steroids
CH1210760A CH454840A (en) 1960-10-28 1960-10-28 Process for the production of steroid 19 acids
CH1439360A CH451925A (en) 1960-12-23 1960-12-23 Process for the preparation of 19-hydroxy steroids
CH399061 1961-04-05
CH648161 1961-06-02

Publications (1)

Publication Number Publication Date
SE303486B true SE303486B (en) 1968-09-02

Family

ID=27509171

Family Applications (1)

Application Number Title Priority Date Filing Date
SE728861A SE303486B (en) 1960-07-15 1961-07-13

Country Status (3)

Country Link
DK (1) DK105586C (en)
GB (1) GB994747A (en)
SE (1) SE303486B (en)

Also Published As

Publication number Publication date
GB994747A (en) 1965-06-10
DK105586C (en) 1966-10-17

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