WO2012083090A3 - Methods and compounds for preparing 3alpha-oxygen substituted steroids - Google Patents

Methods and compounds for preparing 3alpha-oxygen substituted steroids Download PDF

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Publication number
WO2012083090A3
WO2012083090A3 PCT/US2011/065298 US2011065298W WO2012083090A3 WO 2012083090 A3 WO2012083090 A3 WO 2012083090A3 US 2011065298 W US2011065298 W US 2011065298W WO 2012083090 A3 WO2012083090 A3 WO 2012083090A3
Authority
WO
WIPO (PCT)
Prior art keywords
androst
linked
preparing
steroids
3alpha
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.)
Ceased
Application number
PCT/US2011/065298
Other languages
French (fr)
Other versions
WO2012083090A2 (en
Inventor
Yu Ge
Steven K. White
Yujin Huang
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.)
Harbor Biosciences Inc
Original Assignee
Harbor Biosciences Inc
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 Harbor Biosciences Inc filed Critical Harbor Biosciences Inc
Priority to EP11849491.3A priority Critical patent/EP2667876A2/en
Priority to CN2011800669602A priority patent/CN103347525A/en
Priority to AU2011343615A priority patent/AU2011343615A1/en
Publication of WO2012083090A2 publication Critical patent/WO2012083090A2/en
Publication of WO2012083090A3 publication Critical patent/WO2012083090A3/en
Anticipated expiration legal-status Critical
Ceased 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
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C07J1/0025—Esters
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
    • C07J1/0048—Alkynyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/001—Lactones
    • C07J21/003—Lactones at position 17
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0038—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an androstane skeleton, including 18- or 19-substituted derivatives, 18-nor derivatives and also derivatives where position 17-beta is substituted by a carbon atom not directly bonded to a further carbon atom and not being part of an amide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention relates to processes for preparing 3α-O-linked steroids including 3α-O-linked-androst-5-ene steroids and 3α-O-linked-5α-androstane steroids. In one process a 3α,4α-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3α,4α epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3α-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3β-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3α-O-linked-androst-5-ene steroid with reduced amounts of 3α,5α-cycloandrostane side-product impurities.
PCT/US2011/065298 2010-12-15 2011-12-15 Methods and compounds for preparing 3alpha-oxygen substituted steroids Ceased WO2012083090A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP11849491.3A EP2667876A2 (en) 2010-12-15 2011-12-15 Methods and compounds for preparing 3alpha-oxygen substituted steroids
CN2011800669602A CN103347525A (en) 2010-12-15 2011-12-15 Methods and compounds for preparing 3alpha-oxygen substituted steroids
AU2011343615A AU2011343615A1 (en) 2010-12-15 2011-12-15 Methods and compounds for preparing 3alpha-oxygen substituted steroids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US42345710P 2010-12-15 2010-12-15
US61/423,457 2010-12-15

Publications (2)

Publication Number Publication Date
WO2012083090A2 WO2012083090A2 (en) 2012-06-21
WO2012083090A3 true WO2012083090A3 (en) 2012-12-06

Family

ID=46245376

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/065298 Ceased WO2012083090A2 (en) 2010-12-15 2011-12-15 Methods and compounds for preparing 3alpha-oxygen substituted steroids

Country Status (5)

Country Link
US (1) US20120214987A1 (en)
EP (1) EP2667876A2 (en)
CN (1) CN103347525A (en)
AU (1) AU2011343615A1 (en)
WO (1) WO2012083090A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12403115B2 (en) 2017-08-28 2025-09-02 Zhejiang Jiachi Development Pharmaceuticals Ltd Asymmetric synthesis and uses of compounds in disease treatments

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9388210B2 (en) 2011-02-25 2016-07-12 Washington University Neuroactive 17(20)-Z-vinylcyano-substituted steroids, prodrugs thereof, and methods of treatment using same
EP3572417B1 (en) 2011-10-14 2025-12-17 Sage Therapeutics, LLC 3,3 disubstituted 19-nor pregnane compounds, compositions, and uses thereof
HUE039057T2 (en) 2012-12-18 2018-12-28 Univ Washington Neuroactive 19-alkoxy-17-substituted steroids, useful in methods of treatment
WO2014127201A1 (en) * 2013-02-15 2014-08-21 Washington University Neuroactive enantiomeric 15-, 16- and 17-substituted steroids as modulators for gaba type-a receptors
US9512170B2 (en) 2013-03-01 2016-12-06 Washington University Neuroactive 13, 17-substituted steroids as modulators for GABA type-A receptors
US9365502B2 (en) 2013-03-11 2016-06-14 Washington University Neuroactive substituted cyclopenta[b]phenanthrenes as modulators for GABA type-A receptors
US9562026B2 (en) 2013-03-14 2017-02-07 Washington University Neuroactive substituted cyclopent[a]anthracenes as modulators for GABA type-A receptors
US9725481B2 (en) 2013-04-17 2017-08-08 Sage Therapeutics, Inc. 19-nor C3, 3-disubstituted C21-C-bound heteroaryl steroids and methods of use thereof
KR102396328B1 (en) 2013-04-17 2022-05-10 세이지 테라퓨틱스, 인크. 19-nor c3,3-disubstituted c21-n-pyrazolyl steroids and methods of use thereof
EP2986624B1 (en) 2013-04-17 2020-03-25 Sage Therapeutics, Inc. 19-nor neuroactive steroids for methods of treatment
US20160068563A1 (en) 2013-04-17 2016-03-10 Boyd L. Harrison 19-nor neuroactive steroids and methods of use thereof
SI3021852T1 (en) 2013-07-19 2021-07-30 Sage Therapeutics, Inc. Neuroactive steroids, compositions, and uses thereof
AU2014308621C1 (en) 2013-08-23 2022-01-06 Sage Therapeutics, Inc. Neuroactive steroids, compositions, and uses thereof
US10246482B2 (en) 2014-06-18 2019-04-02 Sage Therapeutics, Inc. Neuroactive steroids, compositions, and uses thereof
CN117024501A (en) 2014-10-16 2023-11-10 萨奇治疗股份有限公司 Compositions and methods targeting CNS disorders
ME03809B (en) 2014-10-16 2021-04-20 Sage Therapeutics Inc COMPOSITIONS AND METHODS OF TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS
WO2016082789A1 (en) 2014-11-27 2016-06-02 Sage Therapeutics, Inc. Compositions and methods for treating cns disorders
RS61530B1 (en) 2015-01-26 2021-04-29 Sage Therapeutics Inc Compositions and methods for treating cns disorders
EP4155314A1 (en) 2015-02-20 2023-03-29 Sage Therapeutics, Inc. Neuroactive steroids, compositions, and uses thereof
WO2018013615A1 (en) 2016-07-11 2018-01-18 Sage Therapeutics, Inc. C7, c12, and c16 substituted neuroactive steroids and their methods of use
MA45599A (en) 2016-07-11 2019-05-15 Sage Therapeutics Inc NEUROACTIVE STEROIDS SUBSTITUTED FOR C17, C20 AND C21 AND THEIR USE PROCEDURES
CN107501374B (en) * 2017-10-19 2019-05-07 湖北竹溪人福药业有限责任公司 A method of recycling dehydroepiandros-sterone from dehydroepiandros-sterone mother liquor object
SG11202112391UA (en) 2019-05-31 2021-12-30 Sage Therapeutics Inc Neuroactive steroids and compositions thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002089814A1 (en) * 2001-05-03 2002-11-14 Pherin Pharmaceuticals, Inc. 17-METHYLENE-ANDROSTAN-3α-OL ANALOGS AS CRH INHIBITORS
US20080153792A1 (en) * 2006-11-17 2008-06-26 Frincke James M Drug Identification and Treatment Method
US20090326251A1 (en) * 2008-06-06 2009-12-31 Hollis-Eden Pharmaceuticals, Inc. Methods for preparing 17-alkynyl-7-hydroxy steroids and related compounds
US7842680B2 (en) * 2003-04-01 2010-11-30 Harbor Biosciences, Inc. Diene and triene compounds and formulations

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
EP1212345B1 (en) * 1999-04-06 2003-08-06 Akzo Nobel N.V. Orally active 7-alpha-alkyl androgens

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002089814A1 (en) * 2001-05-03 2002-11-14 Pherin Pharmaceuticals, Inc. 17-METHYLENE-ANDROSTAN-3α-OL ANALOGS AS CRH INHIBITORS
US7842680B2 (en) * 2003-04-01 2010-11-30 Harbor Biosciences, Inc. Diene and triene compounds and formulations
US20080153792A1 (en) * 2006-11-17 2008-06-26 Frincke James M Drug Identification and Treatment Method
US20090326251A1 (en) * 2008-06-06 2009-12-31 Hollis-Eden Pharmaceuticals, Inc. Methods for preparing 17-alkynyl-7-hydroxy steroids and related compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BONINI ET AL.: "Synthesis and elaboration of trans 2,3-diaryloxiranes.", ARKIVOC, 2008, pages 150 - 182, XP055118803 *
MA ET AL.: "Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien- 3beta,17beta-diol.", MOLECULES, vol. 10, 2005, pages 572 - 582, XP055118802 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12403115B2 (en) 2017-08-28 2025-09-02 Zhejiang Jiachi Development Pharmaceuticals Ltd Asymmetric synthesis and uses of compounds in disease treatments

Also Published As

Publication number Publication date
AU2011343615A1 (en) 2013-05-09
CN103347525A (en) 2013-10-09
EP2667876A2 (en) 2013-12-04
US20120214987A1 (en) 2012-08-23
WO2012083090A2 (en) 2012-06-21

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