CA2418479C - Prodrugs of betulinic acid derivatives for the treatment of cancer - Google Patents

Prodrugs of betulinic acid derivatives for the treatment of cancer Download PDF

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Publication number
CA2418479C
CA2418479C CA002418479A CA2418479A CA2418479C CA 2418479 C CA2418479 C CA 2418479C CA 002418479 A CA002418479 A CA 002418479A CA 2418479 A CA2418479 A CA 2418479A CA 2418479 C CA2418479 C CA 2418479C
Authority
CA
Canada
Prior art keywords
c6alkyl
compound
group
betulinic acid
acceptable salt
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 - Fee Related
Application number
CA002418479A
Other languages
English (en)
French (fr)
Other versions
CA2418479A1 (en
Inventor
John M. Pezzuto
Jerome W. Ii Kosmeder
Ze-Qi Xu
Nian En Zhou
Miriam Elaine Goldsmith
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.)
Advanced Life Sciences Inc
University of Illinois System
Original Assignee
Advanced Life Sciences Inc
University of Illinois 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 Advanced Life Sciences Inc, University of Illinois System filed Critical Advanced Life Sciences Inc
Publication of CA2418479A1 publication Critical patent/CA2418479A1/en
Application granted granted Critical
Publication of CA2418479C publication Critical patent/CA2418479C/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Virology (AREA)
  • Neurology (AREA)
  • Epidemiology (AREA)
  • AIDS & HIV (AREA)
  • Urology & Nephrology (AREA)
  • Molecular Biology (AREA)
  • Neurosurgery (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Biomedical Technology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pulmonology (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA002418479A 2000-08-18 2001-08-15 Prodrugs of betulinic acid derivatives for the treatment of cancer Expired - Fee Related CA2418479C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US22653600P 2000-08-18 2000-08-18
US60/226,536 2000-08-18
PCT/US2001/025581 WO2002016395A1 (en) 2000-08-18 2001-08-15 Prodrugs of betulinic acid derivatives for the treatment of cancer and hiv

Publications (2)

Publication Number Publication Date
CA2418479A1 CA2418479A1 (en) 2002-02-28
CA2418479C true CA2418479C (en) 2007-12-18

Family

ID=22849310

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002418479A Expired - Fee Related CA2418479C (en) 2000-08-18 2001-08-15 Prodrugs of betulinic acid derivatives for the treatment of cancer

Country Status (9)

Country Link
US (3) US6569842B2 (enExample)
EP (1) EP1309605A1 (enExample)
JP (1) JP2004517045A (enExample)
AU (2) AU8494601A (enExample)
CA (1) CA2418479C (enExample)
NO (1) NO20030748L (enExample)
NZ (1) NZ524087A (enExample)
WO (1) WO2002016395A1 (enExample)
ZA (1) ZA200301269B (enExample)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6943260B2 (en) * 2002-02-02 2005-09-13 Boehringer Ingelheim Pharma Gmbh & Co. Kg Process for obtaining betulinic acid
ATE350383T1 (de) * 2002-08-23 2007-01-15 Sloan Kettering Inst Cancer Synthese von epothilonen, zwischenprodukte dafür, analoga und deren verwendungen
US7365221B2 (en) 2002-09-26 2008-04-29 Panacos Pharmaceuticals, Inc. Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof
EP1594885B8 (de) * 2003-02-11 2009-03-25 Novelix Pharmaceuticals, Inc. Medikament zur wachstumsinhibierung von tumoren
DE602004024966D1 (de) 2003-03-24 2010-02-25 Sterix Ltd Oestrogenderivate als steroid sulphatase inhibitoren
JP2007510621A (ja) * 2003-07-29 2007-04-26 シグニチャー アールアンドディー ホールディングス，エルエルシー． アミノ酸プロドラッグ
WO2005112929A2 (en) * 2004-05-20 2005-12-01 Cornell Research Foundation, Inc. Anti-hiv-1 activity of betulinol derivatives
EP2165709B1 (en) * 2004-08-02 2016-03-16 Ambrilia Biopharma Inc. Pharmaceutical compositions comprising a lysine based compound and an HIV antiviral or antiretroviral agent
US8008280B2 (en) * 2004-09-10 2011-08-30 Biorings Llc Betulinol derivatives as anti-HIV agents
AR051475A1 (es) * 2004-11-05 2007-01-17 Merck & Co Inc Procedimiento para acido{3- [2 (r) -[(1r) - 1-[ 3,5- bis( trifluorometil)- fenil] etoxi] -3 (s) - (4- fluorfenil) morfolin -4- il]metil -5-oxo-4,5-dihidro- [1,2,4]-triazol-1-il} fosfonico
JP4810642B2 (ja) * 2004-11-30 2011-11-09 秋田県 癌転移抑制用トリテルペン誘導体及び該トリテルペン誘導体を用いた癌転移抑制用組成物
WO2006105356A2 (en) * 2005-03-29 2006-10-05 Regents Of The University Of Minnesota Methods of manufacturing bioactive 3-esters of betulinic aldehyde and betulinic acid
US20070111936A1 (en) 2005-11-15 2007-05-17 Vladimir Pak Complex of alpha-fetoprotein and inducers of apoptosis for the treatment of cancer
ZA200805703B (en) * 2005-12-16 2009-10-28 Panacos Pharmaceuticals Inc Preparation of pharmaceutical salts of 3-0-(3',3'-dimethyl-succinyl) betulinic acid
GB0604535D0 (en) 2006-03-07 2006-04-12 Sndv Sprl Betulonic acid derivatives
US20110152229A1 (en) * 2006-11-22 2011-06-23 Duke University Betulinic acid derivatives as anti-hiv agents
WO2009020732A1 (en) * 2007-08-03 2009-02-12 Advanced Life Sciences, Inc. Lupane-type triterpenoids modified at 30-position and analogues thereof
EP2303280A2 (en) * 2008-05-30 2011-04-06 Novelix Pharmaceuticals, Inc. Compositions and methods for treatment of inflammation and hyperkeratotic lesions
US8372808B2 (en) * 2008-10-31 2013-02-12 Wisconsin Alumni Research Foundation Suppression of glial fibrillary acidic protein
WO2010068668A1 (en) * 2008-12-10 2010-06-17 Advanced Life Sciences, Inc. 23-substituted derivatives of lupane-type pentacyclic triterpenoids
RU2551647C2 (ru) * 2012-11-12 2015-05-27 Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук Трифенилфосфониевые соли лупановых тритерпеноидов, способ получения и применение в качестве противоопухолевых веществ
KR101531821B1 (ko) * 2013-11-27 2015-06-24 주식회사 휴메딕스 페길레이션된 베튤린 유도체를 포함하는 경구 투여용 항암제 조성물
CN107011406A (zh) * 2016-01-28 2017-08-04 思路迪（北京）医药科技有限公司 一种具有抗肿瘤作用的化合物及其制备方法和应用
CA3075729A1 (en) 2017-09-14 2019-03-21 Phoenix Biotechnology, Inc. Use of oleandrin to treatn viral infection
CN111417384A (zh) 2017-09-14 2020-07-14 菲尼克斯生物技术公司 用于治疗神经系统病况的方法和改进的神经保护性组合物
WO2020006510A1 (en) 2018-06-29 2020-01-02 Dfh Therapeutics Triterpene amine derivatives
WO2020124043A1 (en) * 2018-12-13 2020-06-18 Gordon Erlinda M Methods of exploiting oncogenic drivers along the human cyclin g1 pathway for cancer gene therapy
EP4295854A3 (en) 2020-03-31 2024-04-03 Phoenix Biotechnology, Inc. Method and compositions for treating coronavirus infection
KR20220151038A (ko) 2020-03-31 2022-11-11 피닉스 바이오테크놀러지 인코포레이티드. 코로나바이러스 감염 예방를 위한 조성물

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2683531B1 (fr) * 1991-11-13 1993-12-31 Rhone Poulenc Rorer Sa Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent.
FR2705097B1 (fr) * 1993-05-11 1995-08-04 Rhone Poulenc Rorer Sa Nouveaux dérivés du lupane, leur préparation et les compositions pharmaceutiques qui les contiennent.
US5869535A (en) 1995-03-21 1999-02-09 The Board Of Trustees Of The University Of Illinois Method and composition for selectively inhibiting melanoma
US5658947A (en) 1995-03-21 1997-08-19 Board Of Trustees Of The University Of Illinois Method and composition for selectively inhibiting melanoma using betalinic acid
US5962527A (en) 1995-03-21 1999-10-05 The Board Of Trustees Of The University Of Illinois Method and composition for treating cancers
JPH0987156A (ja) * 1995-09-19 1997-03-31 Pola Chem Ind Inc 光老化防止剤及び皮膚化粧料
US5804575A (en) 1997-03-27 1998-09-08 The Board Of Trustees Of The University Of Illinois Methods of manufacturing betulinic acid
US6048847A (en) * 1997-09-30 2000-04-11 Dabur Research Foundation Use of betulinic acid and its derivatives for inhibiting cancer growth and a method of monitoring this
US6670345B1 (en) * 1997-09-30 2003-12-30 Dabur Research Foundation Betulinic acid derivatives for inhabiting cancer growth and process for the manufacture of betulinic acid
DE69832363D1 (de) * 1998-03-18 2005-12-22 Dabur Pharma Ltd Betulinsauer Derivate zur Hemmung von Krebswachstum
EP1131337B1 (en) 1998-11-18 2009-01-14 Dabur Pharma Ltd. Novel betulinic acid derivatives, processes for preparing such derivatives and its use as cancer growth inhibitors
EP1189607A2 (en) 1999-04-07 2002-03-27 Washington State University Research Foundation Anti-tumor activity of vitamin e, cholesterol, taxol and betulinic acid derivatives
EP1321145A4 (en) * 2000-07-31 2006-03-22 Nisshin Oillio Ltd ANTITUMOR SUBSTANCES

Also Published As

Publication number Publication date
US20070072835A1 (en) 2007-03-29
US20020052352A1 (en) 2002-05-02
AU2001284946B2 (en) 2007-02-01
CA2418479A1 (en) 2002-02-28
NZ524087A (en) 2004-08-27
NO20030748D0 (no) 2003-02-17
US7091195B2 (en) 2006-08-15
ZA200301269B (en) 2003-11-03
AU8494601A (en) 2002-03-04
NO20030748L (no) 2003-04-15
EP1309605A1 (en) 2003-05-14
US6569842B2 (en) 2003-05-27
US20030186945A1 (en) 2003-10-02
JP2004517045A (ja) 2004-06-10
WO2002016395A1 (en) 2002-02-28

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