AU2001284946B2 - Prodrugs of betulinic acid derivatives for the treatment of cancer and HIV - Google Patents

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

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Publication number
AU2001284946B2
AU2001284946B2 AU2001284946A AU2001284946A AU2001284946B2 AU 2001284946 B2 AU2001284946 B2 AU 2001284946B2 AU 2001284946 A AU2001284946 A AU 2001284946A AU 2001284946 A AU2001284946 A AU 2001284946A AU 2001284946 B2 AU2001284946 B2 AU 2001284946B2
Authority
AU
Australia
Prior art keywords
alkyl
compound
betulinic acid
cancer
treatment
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
AU2001284946A
Other languages
English (en)
Other versions
AU2001284946A1 (en
Inventor
Miriam Elaine Goldsmith
Jerome W. Kosmeder II
John M. Pezzuto
Ze-Qi Xu
Nian En Zhou
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 at Urbana Champaign
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 at Urbana Champaign, University of Illinois System filed Critical Advanced Life Sciences Inc
Publication of AU2001284946A1 publication Critical patent/AU2001284946A1/en
Application granted granted Critical
Publication of AU2001284946B2 publication Critical patent/AU2001284946B2/en
Anticipated expiration legal-status Critical
Ceased 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)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Neurology (AREA)
  • Virology (AREA)
  • Oncology (AREA)
  • Dermatology (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Neurosurgery (AREA)
  • AIDS & HIV (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Communicable Diseases (AREA)
  • Pulmonology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
AU2001284946A 2000-08-18 2001-08-15 Prodrugs of betulinic acid derivatives for the treatment of cancer and HIV Ceased AU2001284946B2 (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
AU2001284946A1 AU2001284946A1 (en) 2002-05-30
AU2001284946B2 true AU2001284946B2 (en) 2007-02-01

Family

ID=22849310

Family Applications (2)

Application Number Title Priority Date Filing Date
AU2001284946A Ceased AU2001284946B2 (en) 2000-08-18 2001-08-15 Prodrugs of betulinic acid derivatives for the treatment of cancer and HIV
AU8494601A Pending AU8494601A (en) 2000-08-18 2001-08-15 Prodrugs of betulinic acid derivatives for the treatment of cancer and HIV

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU8494601A Pending AU8494601A (en) 2000-08-18 2001-08-15 Prodrugs of betulinic acid derivatives for the treatment of cancer and HIV

Country Status (9)

Country Link
US (3) US6569842B2 (https=)
EP (1) EP1309605A1 (https=)
JP (1) JP2004517045A (https=)
AU (2) AU2001284946B2 (https=)
CA (1) CA2418479C (https=)
NO (1) NO20030748L (https=)
NZ (1) NZ524087A (https=)
WO (1) WO2002016395A1 (https=)
ZA (1) ZA200301269B (https=)

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US6943260B2 (en) * 2002-02-02 2005-09-13 Boehringer Ingelheim Pharma Gmbh & Co. Kg Process for obtaining betulinic acid
DE60330407D1 (de) * 2002-08-23 2010-01-14 Sloan Kettering Inst Cancer Synthese von Epothilonen, Zwischenprodukte davon, Analoga und ihre Verwendung
US7365221B2 (en) 2002-09-26 2008-04-29 Panacos Pharmaceuticals, Inc. Monoacylated betulin and dihydrobetulin derivatives, preparation thereof and use thereof
JP4722031B2 (ja) * 2003-02-11 2011-07-13 ノベリックス・ファーマシューティカルズ・インコーポレイテッド 腫瘍増殖を阻害するための医薬
ES2339450T3 (es) 2003-03-24 2010-05-20 Sterix Limited Derivados de estrogenos como inhibidores de esteroide sulfatasa.
CN101123878A (zh) * 2003-07-29 2008-02-13 信号研发控股有限责任公司 氨基酸前药
WO2005112929A2 (en) * 2004-05-20 2005-12-01 Cornell Research Foundation, Inc. Anti-hiv-1 activity of betulinol derivatives
WO2006012725A1 (en) * 2004-08-02 2006-02-09 Ambrilia Biopharma Inc. Lysine based compounds
EA200700611A1 (ru) * 2004-09-10 2008-02-28 Бридж Б. Саксена Производные бетулинола в качестве противораковых агентов
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
EP1869063A2 (en) * 2005-03-29 2007-12-26 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
BRPI0619936A2 (pt) * 2005-12-16 2011-10-25 Panacos Pharmaceuticals Inc preparação de sais farmacêuticos de ácido 3-o-(3',3'- dimetilsuccinil) betulìnico
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
US20090062243A1 (en) * 2007-08-03 2009-03-05 Advanced Life Sciences, Inc. Lupane-Type Triterpenoids Modified at 30-Position and Analogues Thereof
US20110077297A1 (en) * 2008-05-30 2011-03-31 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
US20100144688A1 (en) * 2008-12-10 2010-06-10 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
RU2020113341A (ru) 2017-09-14 2021-10-15 Феникс Байотекнолоджи, Инк. Способ и композиция для лечения вирусной инфекции
KR20200083969A (ko) 2017-09-14 2020-07-09 피닉스 바이오테크놀러지 인코포레이티드. 신경학적 상태를 치료하기 위한 방법 및 개선된 신경보호 조성물
CA3101643C (en) 2018-06-29 2023-02-21 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
JP7153083B2 (ja) 2020-03-31 2022-10-13 フェニックス・バイオテクノロジー・インコーポレイテッド コロナウイルス感染を治療するための方法および組成物
EP4009981B1 (en) 2020-03-31 2023-08-16 Phoenix Biotechnology, Inc. Method and compositions for treating coronavirus infection

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010142A1 (fr) * 1991-11-13 1993-05-27 Rhone-Poulenc Rorer S.A. Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent
WO1994026725A1 (fr) * 1993-05-11 1994-11-24 Rhone-Poulenc Rorer S.A. Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent
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
AU4331700A (en) * 1999-04-07 2000-10-23 Virginia Commonwealth University Anti-tumor activity of vitamin e, cholesterol, taxol and betulinic acid derivatives
US6225353B1 (en) * 1995-03-21 2001-05-01 The Board Of Trustees Of The University Of Illinois Method and composition for selectively inhibiting melanoma

Family Cites Families (8)

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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
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
AU766599B2 (en) 1998-11-18 2003-10-16 Dabur Pharma Ltd. Novel betulinic acid derivatives, processes for preparing such derivatives and its use as cancer growth inhibitors
WO2002009719A1 (en) 2000-07-31 2002-02-07 The Nisshin Oillio, Ltd. Antitumor agents

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010142A1 (fr) * 1991-11-13 1993-05-27 Rhone-Poulenc Rorer S.A. Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent
WO1994026725A1 (fr) * 1993-05-11 1994-11-24 Rhone-Poulenc Rorer S.A. Nouveaux derives du lupane, leur preparation et les compositions pharmaceutiques qui les contiennent
US6225353B1 (en) * 1995-03-21 2001-05-01 The Board Of Trustees Of The University Of Illinois Method and composition for selectively inhibiting melanoma
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
AU4331700A (en) * 1999-04-07 2000-10-23 Virginia Commonwealth University Anti-tumor activity of vitamin e, cholesterol, taxol and betulinic acid derivatives

Non-Patent Citations (13)

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Kashiwada et al Journal of Medicinal Chemistry vol 39, no 5, 1996, 1016-1017 *
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Ma et al Chem Pharm Bull (1999), 47(2), 141-145 *
Macias et al Phytochemistry vol 49, no 3, 1998, 709-717 *
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Yasukawa et al Phytomedicine vol 4, 1995, 309-313 *

Also Published As

Publication number Publication date
AU8494601A (en) 2002-03-04
EP1309605A1 (en) 2003-05-14
US6569842B2 (en) 2003-05-27
US20030186945A1 (en) 2003-10-02
CA2418479A1 (en) 2002-02-28
NO20030748L (no) 2003-04-15
US20070072835A1 (en) 2007-03-29
WO2002016395A1 (en) 2002-02-28
CA2418479C (en) 2007-12-18
JP2004517045A (ja) 2004-06-10
NO20030748D0 (no) 2003-02-17
US20020052352A1 (en) 2002-05-02
NZ524087A (en) 2004-08-27
US7091195B2 (en) 2006-08-15
ZA200301269B (en) 2003-11-03

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Legal Events

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DA3 Amendments made section 104

Free format text: THE NATURE OF THE AMENDMENT IS: ADD A CO-INVENTOR: GOLDSMITH, MIRIAM ELAINE.

FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired