GB989503A - 6,16-disubstituted androstenes and process for the preparation thereof - Google Patents

6,16-disubstituted androstenes and process for the preparation thereof

Info

Publication number
GB989503A
GB989503A GB3315562A GB3315562A GB989503A GB 989503 A GB989503 A GB 989503A GB 3315562 A GB3315562 A GB 3315562A GB 3315562 A GB3315562 A GB 3315562A GB 989503 A GB989503 A GB 989503A
Authority
GB
United Kingdom
Prior art keywords
acyloxy
ones
treating
give
preparation
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
GB3315562A
Inventor
Derek Burn
Vladimir Petrow
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.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals 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 BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB3315562A priority Critical patent/GB989503A/en
Publication of GB989503A publication Critical patent/GB989503A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 3b -acyloxy-6-methyl-16 - methylene - androst - 5 - en - 17 - ones; 3b - acyloxy - 6,16b - dimethyl - androst - 5 - en - 17 - ones and the corresponding free 3b -ol; and 6a ,16b - dimethylandrost - 4 - ene - 3,17 - dione; and their preparation by treating a 3b -acyloxy-16b - dimethylaminomethyl - 6 - methylandrost-5-en-17-one with an acetic acid/acetic anhydride mixture to give the corresponding 16-methylene compound, hydrogenating this and treating the resultant mixture of isomers with hydrochloric acid in acetic acid to give the corresponding 16b -methyl compound (from which the free 3b -ol is prepared by saponification) and treating this with aluminium t.-butoxide in cyclohexanone and toluene to give the D 4-3-one. The acyl groups are derived from aliphatic carboxylic acids of at most 8 carbon atoms. Examples are given. 3b - acyloxy - 16b - dimethylaminomethyl - 6 - methylandrost-5-e -17-ones are prepared from the corresponding 16-unsubstituted compounds, dimethylamine hydrochloride and formaldehyde.
GB3315562A 1962-08-29 1962-08-29 6,16-disubstituted androstenes and process for the preparation thereof Expired GB989503A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3315562A GB989503A (en) 1962-08-29 1962-08-29 6,16-disubstituted androstenes and process for the preparation thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3315562A GB989503A (en) 1962-08-29 1962-08-29 6,16-disubstituted androstenes and process for the preparation thereof

Publications (1)

Publication Number Publication Date
GB989503A true GB989503A (en) 1965-04-22

Family

ID=10349254

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3315562A Expired GB989503A (en) 1962-08-29 1962-08-29 6,16-disubstituted androstenes and process for the preparation thereof

Country Status (1)

Country Link
GB (1) GB989503A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0133995A2 (en) * 1983-08-02 1985-03-13 Research Corporation Technologies, Inc. Steroids and therapeutic compositions containing same
US4898694A (en) * 1987-11-25 1990-02-06 Schwartz Arthur G 17-Hydroxy-steroids
US5001119A (en) * 1987-11-25 1991-03-19 Schwartz Arthur G 16-substituted androstanes and 16-substituted androstenes
US5028631A (en) * 1987-11-25 1991-07-02 Schwartz Arthur G Homoandrostan-17-one and homoandrosten-17-ones
US5175154A (en) * 1987-11-25 1992-12-29 Research Corporation Technologies, Inc. 5 α-pregnan-20-ones and 5-pregnen-20-ones and related compounds
US5696106A (en) * 1983-08-02 1997-12-09 Research Corporation Technologies, Inc. Steroids useful as anti-cancer and anti-obesity agents
US5714481A (en) * 1983-08-02 1998-02-03 Research Corporation Technologies, Inc. Derivatives of 5-androsten-17 ones and 5-androstan-17-ones
US5804576A (en) * 1983-08-02 1998-09-08 Research Corporation Technologies, Inc. Derivatives of 5-androsten-17-ones and 5-androstan-17-ones

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0133995A2 (en) * 1983-08-02 1985-03-13 Research Corporation Technologies, Inc. Steroids and therapeutic compositions containing same
EP0133995A3 (en) * 1983-08-02 1985-11-27 Research Corporation Steroids and therapeutic compositions containing same
US5696106A (en) * 1983-08-02 1997-12-09 Research Corporation Technologies, Inc. Steroids useful as anti-cancer and anti-obesity agents
US5700793A (en) * 1983-08-02 1997-12-23 Research Corporation Technologies, Inc. Steroids useful as anti-cancer and anti-obesity agents
US5714481A (en) * 1983-08-02 1998-02-03 Research Corporation Technologies, Inc. Derivatives of 5-androsten-17 ones and 5-androstan-17-ones
US5744462A (en) * 1983-08-02 1998-04-28 Research Corporation Technologies, Inc. Steroids useful as anti-cancer and anti-obesity agents
US5804576A (en) * 1983-08-02 1998-09-08 Research Corporation Technologies, Inc. Derivatives of 5-androsten-17-ones and 5-androstan-17-ones
US4898694A (en) * 1987-11-25 1990-02-06 Schwartz Arthur G 17-Hydroxy-steroids
US5001119A (en) * 1987-11-25 1991-03-19 Schwartz Arthur G 16-substituted androstanes and 16-substituted androstenes
US5028631A (en) * 1987-11-25 1991-07-02 Schwartz Arthur G Homoandrostan-17-one and homoandrosten-17-ones
US5175154A (en) * 1987-11-25 1992-12-29 Research Corporation Technologies, Inc. 5 α-pregnan-20-ones and 5-pregnen-20-ones and related compounds

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