WO2006105356A3 - Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid - Google Patents

Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid Download PDF

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Publication number
WO2006105356A3
WO2006105356A3 PCT/US2006/011793 US2006011793W WO2006105356A3 WO 2006105356 A3 WO2006105356 A3 WO 2006105356A3 US 2006011793 W US2006011793 W US 2006011793W WO 2006105356 A3 WO2006105356 A3 WO 2006105356A3
Authority
WO
WIPO (PCT)
Prior art keywords
betulinic
esters
compound
methods
formula
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/US2006/011793
Other languages
French (fr)
Other versions
WO2006105356A2 (en
Inventor
Pavel A Krasutsky
Oksana Kolomitsyna
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.)
University of Minnesota Twin Cities
University of Minnesota System
Original Assignee
University of Minnesota Twin Cities
University of Minnesota System
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 University of Minnesota Twin Cities, University of Minnesota System filed Critical University of Minnesota Twin Cities
Priority to EP06740132A priority Critical patent/EP1869063A2/en
Priority to US11/910,149 priority patent/US20090023698A1/en
Publication of WO2006105356A2 publication Critical patent/WO2006105356A2/en
Publication of WO2006105356A3 publication Critical patent/WO2006105356A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids

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  • 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 present invention provides a method for preparing a compound of formula (I), the method comprising contacting a compound of formula (II) with an effective amount of a compound of formula (III) or (IV). The present invention also provides a method for preparing a compound of formula (VI), the method comprising contacting a compound of formula (II) with an effective amount of one or more of 2,2-dimethylsuccinic acid, 2,2 dimethylbutanedioyl dichloride, 2,2-dimethylbutanedioyl dibromide, and 2,2 dimethylsuccinic anhydride. The present invention also provides a compound obtained from the method of the present invention.
PCT/US2006/011793 2005-03-29 2006-03-29 Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid Ceased WO2006105356A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP06740132A EP1869063A2 (en) 2005-03-29 2006-03-29 Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid
US11/910,149 US20090023698A1 (en) 2005-03-29 2006-03-29 Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US66602405P 2005-03-29 2005-03-29
US60/666,024 2005-03-29

Publications (2)

Publication Number Publication Date
WO2006105356A2 WO2006105356A2 (en) 2006-10-05
WO2006105356A3 true WO2006105356A3 (en) 2006-11-23

Family

ID=36794436

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/011793 Ceased WO2006105356A2 (en) 2005-03-29 2006-03-29 Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid

Country Status (3)

Country Link
US (1) US20090023698A1 (en)
EP (1) EP1869063A2 (en)
WO (1) WO2006105356A2 (en)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200628161A (en) * 2004-11-12 2006-08-16 Panacos Pharmaceuticals Inc Novel betulin derivatives, preparation thereof and use thereof
US9067966B2 (en) 2009-07-14 2015-06-30 Hetero Research Foundation, Hetero Drugs Ltd. Lupeol-type triterpene derivatives as antivirals
US8802727B2 (en) 2009-07-14 2014-08-12 Hetero Research Foundation, Hetero Drugs Limited Pharmaceutically acceptable salts of betulinic acid derivatives
CN102883608A (en) * 2010-02-11 2013-01-16 葛兰素史密丝克莱恩有限责任公司 Betulin Derivatives
WO2013020246A1 (en) * 2011-08-08 2013-02-14 Glaxosmithkline Llc Methylene derivatives of betulin
JO3387B1 (en) 2011-12-16 2019-03-13 Glaxosmithkline Llc Derivatives of betulin
KR20150093819A (en) 2012-12-14 2015-08-18 글락소스미스클라인 엘엘씨 Pharmaceutical compositions
US9637516B2 (en) 2012-12-31 2017-05-02 Hetero Research Foundation Betulinic acid proline derivatives as HIV inhibitors
US20170129916A1 (en) 2014-06-26 2017-05-11 Hetero Research Foundation Novel betulinic proline imidazole derivatives as hiv inhibitors
US10092523B2 (en) 2014-09-26 2018-10-09 Glaxosmithkline Intellectual Property (No. 2) Limited Long acting pharmaceutical compositions
MA40886B1 (en) 2015-02-09 2020-03-31 Hetero Research Foundation Novel c-3 triterpenone with c-28 reverse amide derivatives as hiv inhibitors
US10370405B2 (en) 2015-03-16 2019-08-06 Hetero Labs Limited C-3 novel triterpenone with C-28 amide derivatives as HIV inhibitors
PL227790B1 (en) 2015-08-13 2018-01-31 Slaski Univ Medyczny W Katowicach Phosphonates of acetylene derivatives of betulin with antitumour effects, method for producing them and applications
CN105884853B (en) * 2016-04-11 2017-10-20 哈尔滨理工大学 Phospholipid analogues, Preparation method and use containing betulinic acid
CN105837652B (en) * 2016-04-12 2017-10-13 哈尔滨理工大学 Betulinic acid phosphatide complexes, Preparation method and use

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1415601A (en) * 1973-03-14 1975-11-26 Biorex Laboratories Ltd Dihydrobetulinic acid derivatives
WO2000046235A1 (en) * 1998-11-18 2000-08-10 Dabur Research Foundation Novel betulinic acid derivatives, processes for preparing such derivatives and its use as cancer growth inhibitors
WO2001018029A1 (en) * 1999-09-09 2001-03-15 Dabur Research Foundation Novel betulinic acid derivatives having antiangiogenic activity, processes for producing such derivatives and their use for treating tumor associated angiogenesis
WO2001051451A2 (en) * 2000-01-11 2001-07-19 Regents Of The University Of Minnesota Methods for manufacturing betulinic acid
WO2002026761A1 (en) * 2000-09-29 2002-04-04 Regents Of The University Of Minnesota Triterpenes having fungicidal activity against yeast
JP2003113081A (en) * 2001-10-01 2003-04-18 Pola Chem Ind Inc Triterpene derivative and compound containing it
DE102004012951A1 (en) * 2004-03-17 2005-10-06 Boehringer Ingelheim Pharma Gmbh & Co. Kg Preparation of 3-hydroxy-protected betulinic acid comprises oxidation of 3-hydroxy-protected betulin and further oxidation of the obtained intermediate 3-hydroxy-protected-betulinaldehyde
WO2006053255A2 (en) * 2004-11-12 2006-05-18 Panacos Pharmaceuticals, Inc. Novel betulin derivatives, preparation thereof and use thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL136839A (en) * 2000-06-16 2006-12-10 Yissum Res Dev Co Pharmaceutical compositions comprising cannabidiol derivatives, and processes for the preparation of same
WO2002016395A1 (en) * 2000-08-18 2002-02-28 The Board Of Trustees Of The University Of Illinois Prodrugs of betulinic acid derivatives for the treatment of cancer and hiv

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1415601A (en) * 1973-03-14 1975-11-26 Biorex Laboratories Ltd Dihydrobetulinic acid derivatives
WO2000046235A1 (en) * 1998-11-18 2000-08-10 Dabur Research Foundation Novel betulinic acid derivatives, processes for preparing such derivatives and its use as cancer growth inhibitors
WO2001018029A1 (en) * 1999-09-09 2001-03-15 Dabur Research Foundation Novel betulinic acid derivatives having antiangiogenic activity, processes for producing such derivatives and their use for treating tumor associated angiogenesis
WO2001051451A2 (en) * 2000-01-11 2001-07-19 Regents Of The University Of Minnesota Methods for manufacturing betulinic acid
WO2002026761A1 (en) * 2000-09-29 2002-04-04 Regents Of The University Of Minnesota Triterpenes having fungicidal activity against yeast
JP2003113081A (en) * 2001-10-01 2003-04-18 Pola Chem Ind Inc Triterpene derivative and compound containing it
DE102004012951A1 (en) * 2004-03-17 2005-10-06 Boehringer Ingelheim Pharma Gmbh & Co. Kg Preparation of 3-hydroxy-protected betulinic acid comprises oxidation of 3-hydroxy-protected betulin and further oxidation of the obtained intermediate 3-hydroxy-protected-betulinaldehyde
WO2006053255A2 (en) * 2004-11-12 2006-05-18 Panacos Pharmaceuticals, Inc. Novel betulin derivatives, preparation thereof and use thereof

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
HASHIMOTO F ET AL: "Anti-AIDS Agents. XXVII. Synthesis and Anti-HIV Activity of Betulinic Acid and Dihydrobetulinic Acid Derivatives", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER SCIENCE LTD, GB, vol. 5, no. 12, 1997, pages 2133 - 2143, XP002102686, ISSN: 0968-0896 *
KVASNICA, M. ET AL.: "Synthesis of phthalates of betulinic acid and betulin with cytotoxic activity", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER SCIENCE LTD, GB, vol. 13, no. 10, 30 March 2005 (2005-03-30), pages 3447 - 3454, XP004859482, ISSN: 0968-0896 *
MA, C. ET AL.: "Inhibitory effects of constituents from Cynomorium songaricum and related triterpene derivatives on HIV-1 protease", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, TOKYO, JP, vol. 47, no. 2, 1999, pages 141 - 145, XP002184896, ISSN: 0009-2363 *
MUKHERJEE, R. ET AL.: "Synthesis and cytotoxic activity of 3-O-acyl/3-hydrazine/2-bromo/20,29-dibromo betulinic acid derivatives", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 15, 2004, pages 4087 - 4091, XP002395891 *
PATENT ABSTRACTS OF JAPAN vol. 2003, no. 08 6 August 2003 (2003-08-06) *

Also Published As

Publication number Publication date
WO2006105356A2 (en) 2006-10-05
EP1869063A2 (en) 2007-12-26
US20090023698A1 (en) 2009-01-22

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