GB912036A - 11-methylene-5ª--steroids - Google Patents

11-methylene-5ª--steroids

Info

Publication number
GB912036A
GB912036A GB2206760A GB2206760A GB912036A GB 912036 A GB912036 A GB 912036A GB 2206760 A GB2206760 A GB 2206760A GB 2206760 A GB2206760 A GB 2206760A GB 912036 A GB912036 A GB 912036A
Authority
GB
United Kingdom
Prior art keywords
methylene
steroids
hydroxy
spirostan
acetate
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
GB2206760A
Inventor
David Neville Kirk
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 GB2206760A priority Critical patent/GB912036A/en
Publication of GB912036A publication Critical patent/GB912036A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J11/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 3

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) a process for preparing steroids having, apart from substituents at the 16- and 17-positions, the formula <FORM:0912036/IV (b)/1> (wherein R is CHOH, CHO Acyl or CO) which comprises dehydrating and isomerizing with an acidic reagent the corresponding 11b -hydroxy-11a -methyl-5a -steroids; and (2) as new steroids, 17b - hydroxy-11-methylene-5a -androstan-3-one and the 17-acetate and -propionate thereof, 3b ,20b -dihydroxy - 11 - methylene-5a -pregnane and the diacetate thereof, 11-methylene - 5a ,25D - spirostan-3-one and 3b -hydroxy - 11 - methylene-5a ,25D-spirostan and the 3-acetate thereof. The process may be performed in one operation using formic, perchloric, sulphuric or toluene-p-sulphonic acid which may be dissolved in a lower fatty acid or anhydride or mixture thereof, or in two stages using thionyl chloride in pyridine at -20 to 40 DEG C. to effect dehydration to an 11-methyl-D 9(11)-5a -steroid which is then treated with formic acid in an inert solvent or one of the other acids referred to above in a lower fatty acid. If the starting material is a 3b ,11b -dihydroxy steroid it may be wholly or partially transformed by the acidic treatment into a 3-acyl derivative of the 11-methylene product, which may then be saponified to the free hydroxy compound or fully acylated. Examples are given. Specification 912,035 is referred to.
GB2206760A 1960-06-23 1960-06-23 11-methylene-5ª--steroids Expired GB912036A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2206760A GB912036A (en) 1960-06-23 1960-06-23 11-methylene-5ª--steroids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2206760A GB912036A (en) 1960-06-23 1960-06-23 11-methylene-5ª--steroids

Publications (1)

Publication Number Publication Date
GB912036A true GB912036A (en) 1962-12-05

Family

ID=10173366

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2206760A Expired GB912036A (en) 1960-06-23 1960-06-23 11-methylene-5ª--steroids

Country Status (1)

Country Link
GB (1) GB912036A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2361120A1 (en) * 1972-12-09 1974-06-12 Akzo Nv 11,11-ALKYLIDAL STEROIDS AND METHOD FOR MANUFACTURING THEREOF
EP1042352A1 (en) * 1997-11-26 2000-10-11 Research Triangle Institute Androgenic steroid compounds and a method of making and using the same
WO2015075693A1 (en) 2013-11-25 2015-05-28 Richter Gedeon Nyrt. Process for the synthesis of (11 beta.17alpha)-17-acetoxy-1 1 -methyl-19-norpregn-4-en-3.20-dione

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2361120A1 (en) * 1972-12-09 1974-06-12 Akzo Nv 11,11-ALKYLIDAL STEROIDS AND METHOD FOR MANUFACTURING THEREOF
EP1042352A1 (en) * 1997-11-26 2000-10-11 Research Triangle Institute Androgenic steroid compounds and a method of making and using the same
EP1042352A4 (en) * 1997-11-26 2004-12-22 Res Triangle Inst Androgenic steroid compounds and a method of making and using the same
WO2015075693A1 (en) 2013-11-25 2015-05-28 Richter Gedeon Nyrt. Process for the synthesis of (11 beta.17alpha)-17-acetoxy-1 1 -methyl-19-norpregn-4-en-3.20-dione

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