GB950614A - Improvements in or relating to the process for the preparation of conanine derivatives and iminopregnenes - Google Patents

Improvements in or relating to the process for the preparation of conanine derivatives and iminopregnenes

Info

Publication number
GB950614A
GB950614A GB3043360A GB3043360A GB950614A GB 950614 A GB950614 A GB 950614A GB 3043360 A GB3043360 A GB 3043360A GB 3043360 A GB3043360 A GB 3043360A GB 950614 A GB950614 A GB 950614A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
hydroxy
acyloxy
formula
steroid
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
GB3043360A
Inventor
Vlasios Georgian
James Francis Kerwim
Ernst Wolff
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories Ltd
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 Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Priority to GB2512262A priority Critical patent/GB950616A/en
Priority to GB3043360A priority patent/GB950614A/en
Priority to GB2512162A priority patent/GB950615A/en
Priority to GB2512362A priority patent/GB950617A/en
Publication of GB950614A publication Critical patent/GB950614A/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
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • 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 (1) steroids of the formula: <FORM:0950614/C2/1> (wherein A and B are hydroxy, acyloxy or keto; R and R10 are hydrogen, hydroxy or acyloxy; R1 is hydrogen, hydroxy, acyloxy or methyl; R2 is hydrogen, fluoro, hydroxy, acyloxy or methyl; R3 is hydrogen or methyl; R5 is hydrogen or fluoro; and Z is C1-6 alkyl); (2) steroids of the formulae: <FORM:0950614/C2/2> <FORM:0950614/C2/3> (wherein R, R10, R1, R2, R3, R5 and Z have the above-defined meanings, except that at least one of R, R1, R2, R10 and R5 must be other than hydrogen, and D is hydroxy or acyloxy); (3) steroids of the formula: <FORM:0950614/C2/4> (4) steroids of the formula: <FORM:0950614/C2/5> <FORM:0950614/C2/6> <FORM:0950614/C2/7> (wherein X and Y are hydrogen, hydroxy, acyloxy or keto; R and R4 are hydrogen, hydroxy or acyloxy; W is a halogen of atomic weight less than 80; and R1, R2, R3 and R5 have the meanings defined in (1) above); (5) steroids of the formula: <FORM:0950614/C2/8> (wherein V and T are hydrogen, hydroxy or keto; R6 and R9 are hydrogen or hydroxy; R7 is hydrogen, hydroxy or methyl; R8 is hydrogen, hydroxy, methyl or fluoro; and R3 and R5 are as defined in (1) above; (6) the process of preparing steroid of formula XVI by irradiating with ultra-violet light in the presence of trifluoroacetic acid a steroid of the formula: <FORM:0950614/C2/9> (wherein X and W have the meanings defined under (4) above; Y is hydrogen, acyloxy or keto; R, R1, R2, R3, R5 and Z have the meanings defined under (1) above; and R4 is hydrogen or acyloxy) to form a steroid of the formula: <FORM:0950614/C2/100> treating this with an alkali to form a steroid of the formula: <FORM:0950614/C2/111> (in which V, T, R3, R5, R6, R9, R7 and R8 are as defined under (5) above; and Z is C1-6 alkyl), treating this with cyanogen bromide to form the corresponding N-cyano steroid, hydrolysing this to form the corresponding N-unsubstituted steroid, treating this with a halogenating agent to form the corresponding N-halo steroid and dehydrohalogenating this; and (7) the process of preparing a steroid of formula III by the first three stages of the process outlined under (6). Acyl radicals are defined as those derived from organic carboxylic acids of at most 6 carbon atoms. In the third stage of the process, the precise nature of the product depends on the amount of alkali used, the use of more than one equivalent resulting in the hydrolysis of one or more acyloxy substituents. Resulting free hydroxy groups may subsequently be re-acylated. Similarly hydrolysis of acyloxy groups may occur in other stages of the above synthesis where alkaline conditions are employed. Products containing 3- or 11-hydroxy substituents may be oxidized to the corresponding ketones, or the ketones may be reduced to the ols. Detailed examples are provided, a by-product in one cyanation process being 3-acetoxyconanine methobromide. 20a methylamino -19- nor -3- allopregnanone is prepared by oxidation of the 3b -ol. Specifications 950,615, 950,616 and 950,617 are referred to.
GB3043360A 1960-09-02 1960-09-02 Improvements in or relating to the process for the preparation of conanine derivatives and iminopregnenes Expired GB950614A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB2512262A GB950616A (en) 1960-09-02 1960-09-02 Improvements in or relating to 18-halo steroids
GB3043360A GB950614A (en) 1960-09-02 1960-09-02 Improvements in or relating to the process for the preparation of conanine derivatives and iminopregnenes
GB2512162A GB950615A (en) 1960-09-02 1960-09-02 Improvements in or relating to 20-(n-alkyl-n-halo-amino) steroids
GB2512362A GB950617A (en) 1960-09-02 1962-09-02 Improvements in or relating to 18,20-oxygenated steroid derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3043360A GB950614A (en) 1960-09-02 1960-09-02 Improvements in or relating to the process for the preparation of conanine derivatives and iminopregnenes

Publications (1)

Publication Number Publication Date
GB950614A true GB950614A (en) 1964-02-26

Family

ID=10307606

Family Applications (4)

Application Number Title Priority Date Filing Date
GB3043360A Expired GB950614A (en) 1960-09-02 1960-09-02 Improvements in or relating to the process for the preparation of conanine derivatives and iminopregnenes
GB2512262A Expired GB950616A (en) 1960-09-02 1960-09-02 Improvements in or relating to 18-halo steroids
GB2512162A Expired GB950615A (en) 1960-09-02 1960-09-02 Improvements in or relating to 20-(n-alkyl-n-halo-amino) steroids
GB2512362A Expired GB950617A (en) 1960-09-02 1962-09-02 Improvements in or relating to 18,20-oxygenated steroid derivatives

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB2512262A Expired GB950616A (en) 1960-09-02 1960-09-02 Improvements in or relating to 18-halo steroids
GB2512162A Expired GB950615A (en) 1960-09-02 1960-09-02 Improvements in or relating to 20-(n-alkyl-n-halo-amino) steroids
GB2512362A Expired GB950617A (en) 1960-09-02 1962-09-02 Improvements in or relating to 18,20-oxygenated steroid derivatives

Country Status (1)

Country Link
GB (4) GB950614A (en)

Also Published As

Publication number Publication date
GB950616A (en) 1964-02-26
GB950615A (en) 1964-02-26
GB950617A (en) 1964-02-26

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