GB857081A - Cyclopentanophenanthrene derivatives and process for the production thereof - Google Patents

Cyclopentanophenanthrene derivatives and process for the production thereof

Info

Publication number
GB857081A
GB857081A GB16963/57A GB1696357A GB857081A GB 857081 A GB857081 A GB 857081A GB 16963/57 A GB16963/57 A GB 16963/57A GB 1696357 A GB1696357 A GB 1696357A GB 857081 A GB857081 A GB 857081A
Authority
GB
United Kingdom
Prior art keywords
methyl
estrone
dehydro
estradiol
ethinyl
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
GB16963/57A
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.)
Syntex SA
Original Assignee
Syntex SA
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 Syntex SA filed Critical Syntex SA
Publication of GB857081A publication Critical patent/GB857081A/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

Abstract

The invention comprises 2-methyl-estrone, 2-methyl-estradiol, 2-methyl-17a -ethinyl-estra-diol, the corresponding 6-dehydro compounds; their esters with hydrocarbon carboxylic acids containing less than twelve carbon atoms, and a process for the preparation of 2-methyl-6-dehydro-estrone by heating 2-methyl-D 1,4,6-androstatriene-3,17-dione at approximately 600 DEG C, preferably in a hydrogen donor solvent, e.g., mineral oil, dihydro-or tetrahydro-naphthalene, dihydrophenanthrene and cyclohexene. The product may then be reduced, e.g. with sodium borohydride or lithium aluminium hydride to the diol, or reacted with potassium acetylide giving the 17a -ethinyl-17b -ol derivative, or hydrogenated, preferably over palladium or platinum, to 2-methyl-estrone and then treated as above. In Examples :-(1) 2-methyl-D 1,4,6-androstatriene-3, 17-dione in mineral oil is passed through a column of glass helices at 600 DEG C., the product diluted with hexane and chromatographed on alumina, washed well with hexane and 2-methyl-6-dehydro-estrone eluted with ether, and characterised as its 3-propionate, benzoate, cyclopentylpropionate and phenylpropionate; (2) reduction of 2-methyl-6-de-hydro-estrone with aqueous methanolic sodium borohydride gives 2-methyl-6-dehydro-estradiol, characterised as its 3, 17-dipropionate, dibenzoate, di-cyclopentylpropionate and diphenylpropionate; (3) 2-methyl-6-dehydro-estrone in benzene is treated under nitrogen with potassium in t-butanol and acetylene passed into the mixture giving 2-methyl-17a -ethinyl-6-dehydro-estradiol, which is esterified as above; (4) hydrogenation of 2-methyl-6-dehydro-estrone in ethyl acetate over 10 per cent. palladium-charcoal yields 2-methyl-estrone, which is reduced with sodium borohydride to 2-methyl-estradiol, and (5) treated with potassium acetylide as in (3) giving 2-methyl-17a -ethinyl-estradiol, the corresponding esters being also prepared. Specification 857,080 is referred to.
GB16963/57A 1956-05-29 1957-05-28 Cyclopentanophenanthrene derivatives and process for the production thereof Expired GB857081A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MX857081X 1956-05-29

Publications (1)

Publication Number Publication Date
GB857081A true GB857081A (en) 1960-12-29

Family

ID=19743112

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16963/57A Expired GB857081A (en) 1956-05-29 1957-05-28 Cyclopentanophenanthrene derivatives and process for the production thereof

Country Status (1)

Country Link
GB (1) GB857081A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002042319A2 (en) * 2000-11-27 2002-05-30 Entremed, Inc. 2-substituted estrogens as antiangiogenic agents
US6723858B2 (en) 1993-08-06 2004-04-20 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
WO2006003013A2 (en) * 2004-07-02 2006-01-12 Bayer Schering Pharma Aktiengesellschaft NOVEL 2-SUBSTITUTED ESTRA-1,3,5(10)-TRIEN-17-ONES USED IN THE FORM OF INHIBITORS OF 17β-HYDROXYSTEROIDDEHYDROGENASE OF TYPE 1
US7012070B2 (en) 1993-08-06 2006-03-14 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US7087592B1 (en) 1999-08-23 2006-08-08 Entre Med, Inc. Compositions comprising purified 2-methoxyestradiol and methods of producing same
US7135581B2 (en) 2000-08-18 2006-11-14 Entremed, Inc. Antiangiogenic agents
US7419972B2 (en) 2004-07-02 2008-09-02 Schering Ag 2-substituted estra-1,3,5(10)-trien-17-ones as inhibitors of 17β-hydroxy steroid dehydrogenase type 1
US7867975B2 (en) 1995-10-23 2011-01-11 The Children's Medical Center Corporation Therapeutic antiangiogenic endostatin compositions
US8158612B2 (en) 2004-03-12 2012-04-17 Entremed, Inc. Methods of treating disease states using antiangiogenic agents
US8399440B2 (en) 2006-03-20 2013-03-19 Entremed, Inc. Disease modifying anti-arthritic activity of 2-methoxyestradiol

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7081477B2 (en) 1993-08-06 2006-07-25 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US7109187B2 (en) 1993-08-06 2006-09-19 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US7381848B2 (en) 1993-08-06 2008-06-03 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US6908910B2 (en) 1993-08-06 2005-06-21 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US6930128B2 (en) 1993-08-06 2005-08-16 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US7291610B2 (en) 1993-08-06 2007-11-06 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US7012070B2 (en) 1993-08-06 2006-03-14 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US6723858B2 (en) 1993-08-06 2004-04-20 The Children's Medical Center Corporation Estrogenic compounds as anti-mitotic agents
US7867975B2 (en) 1995-10-23 2011-01-11 The Children's Medical Center Corporation Therapeutic antiangiogenic endostatin compositions
US7087592B1 (en) 1999-08-23 2006-08-08 Entre Med, Inc. Compositions comprising purified 2-methoxyestradiol and methods of producing same
US7235540B2 (en) 1999-08-23 2007-06-26 Entremed, Inc. Methods of using 2-methoxyestradiol of high purity
US7135581B2 (en) 2000-08-18 2006-11-14 Entremed, Inc. Antiangiogenic agents
WO2002042319A3 (en) * 2000-11-27 2003-03-13 Entremed Inc 2-substituted estrogens as antiangiogenic agents
WO2002042319A2 (en) * 2000-11-27 2002-05-30 Entremed, Inc. 2-substituted estrogens as antiangiogenic agents
US8158612B2 (en) 2004-03-12 2012-04-17 Entremed, Inc. Methods of treating disease states using antiangiogenic agents
WO2006003013A2 (en) * 2004-07-02 2006-01-12 Bayer Schering Pharma Aktiengesellschaft NOVEL 2-SUBSTITUTED ESTRA-1,3,5(10)-TRIEN-17-ONES USED IN THE FORM OF INHIBITORS OF 17β-HYDROXYSTEROIDDEHYDROGENASE OF TYPE 1
US7419972B2 (en) 2004-07-02 2008-09-02 Schering Ag 2-substituted estra-1,3,5(10)-trien-17-ones as inhibitors of 17β-hydroxy steroid dehydrogenase type 1
WO2006003013A3 (en) * 2004-07-02 2006-06-22 Schering Ag NOVEL 2-SUBSTITUTED ESTRA-1,3,5(10)-TRIEN-17-ONES USED IN THE FORM OF INHIBITORS OF 17β-HYDROXYSTEROIDDEHYDROGENASE OF TYPE 1
US8399440B2 (en) 2006-03-20 2013-03-19 Entremed, Inc. Disease modifying anti-arthritic activity of 2-methoxyestradiol

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