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GB857080A - Cyclopentanophenanthrene derivatives and process for the production thereof - Google Patents

Cyclopentanophenanthrene derivatives and process for the production thereof

Info

Publication number
GB857080A
GB857080A GB16962/57A GB1696257A GB857080A GB 857080 A GB857080 A GB 857080A GB 16962/57 A GB16962/57 A GB 16962/57A GB 1696257 A GB1696257 A GB 1696257A GB 857080 A GB857080 A GB 857080A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
compounds
androsten
estrone
estradiol
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
GB16962/57A
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 GB857080A publication Critical patent/GB857080A/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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 1, 2-dimethyl-estrone, 1, 2-dimethyl-estradiol, 1, 2-dimethyl-17a -ethinyl-estradiol, the corresponding 6-dehydro compounds, their esters with hydrocarbon, carboxylic acids containing less than twelve carbon atoms, and a process for their preparation involving the steps of treating 2a -methyl-D 4-androsten-17b -ol-3-one with an oxidising agent to form 2a -methyl-D 4-androsten-3, 17-dione, treating this with 2 mols of bromine to form the corresponding 2, 6-dibromo compound, dehydrohalogenating the latter and rearranging the resulting D 1,4,6 triene by treatment with a lower fatty acid anhydride and thereafter saponifying the resulting 1, 2-dimethyl-6-dehydro-estrone 3-acylate. Subsequent transformations, viz., reaction with potassium acetylide, reduction of the 17-keto group, esterification, and hydrogenation of the D 6-bond yield the other compounds of the invention. Detailed examples illustrate the preparation of the new compounds. Specification 853,291 is referred to.
GB16962/57A 1956-05-29 1957-05-28 Cyclopentanophenanthrene derivatives and process for the production thereof Expired GB857080A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MX857080X 1956-05-29

Publications (1)

Publication Number Publication Date
GB857080A true GB857080A (en) 1960-12-29

Family

ID=19743111

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16962/57A Expired GB857080A (en) 1956-05-29 1957-05-28 Cyclopentanophenanthrene derivatives and process for the production thereof

Country Status (1)

Country Link
GB (1) GB857080A (en)

Cited By (9)

* 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
US6995278B2 (en) 2000-08-18 2006-02-07 Entre Med, Inc. Antiangiogenic agents
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
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 (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7291610B2 (en) 1993-08-06 2007-11-06 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
US7081477B2 (en) 1993-08-06 2006-07-25 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
US7109187B2 (en) 1993-08-06 2006-09-19 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
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
US6995278B2 (en) 2000-08-18 2006-02-07 Entre Med, Inc. Antiangiogenic agents
WO2002042319A2 (en) * 2000-11-27 2002-05-30 Entremed, Inc. 2-substituted estrogens as antiangiogenic agents
WO2002042319A3 (en) * 2000-11-27 2003-03-13 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
US8399440B2 (en) 2006-03-20 2013-03-19 Entremed, Inc. Disease modifying anti-arthritic activity of 2-methoxyestradiol

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