CA2760953C - Triptolide prodrugs - Google Patents

Triptolide prodrugs Download PDF

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Publication number
CA2760953C
CA2760953C CA2760953A CA2760953A CA2760953C CA 2760953 C CA2760953 C CA 2760953C CA 2760953 A CA2760953 A CA 2760953A CA 2760953 A CA2760953 A CA 2760953A CA 2760953 C CA2760953 C CA 2760953C
Authority
CA
Canada
Prior art keywords
cancer
compound
formula
pharmaceutically acceptable
triptolide
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.)
Active
Application number
CA2760953A
Other languages
English (en)
French (fr)
Other versions
CA2760953A1 (en
Inventor
Ingrid Gunda Georg
Satish Prakash Patil
Ashok K. Saluja
Rohit Chugh
Selwyn M. Vickers
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 System
Original Assignee
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 System filed Critical University of Minnesota System
Priority to CA2964631A priority Critical patent/CA2964631A1/en
Publication of CA2760953A1 publication Critical patent/CA2760953A1/en
Application granted granted Critical
Publication of CA2760953C publication Critical patent/CA2760953C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • 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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings

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)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Epidemiology (AREA)
  • Urology & Nephrology (AREA)
  • Oncology (AREA)
  • Neurosurgery (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pulmonology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
CA2760953A 2009-05-07 2010-05-07 Triptolide prodrugs Active CA2760953C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2964631A CA2964631A1 (en) 2009-05-07 2010-05-07 Triptolide prodrugs

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US17624909P 2009-05-07 2009-05-07
US61/176,249 2009-05-07
PCT/US2010/034117 WO2010129918A1 (en) 2009-05-07 2010-05-07 Triptolide prodrugs

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2964631A Division CA2964631A1 (en) 2009-05-07 2010-05-07 Triptolide prodrugs

Publications (2)

Publication Number Publication Date
CA2760953A1 CA2760953A1 (en) 2010-11-11
CA2760953C true CA2760953C (en) 2017-05-30

Family

ID=42244313

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2760953A Active CA2760953C (en) 2009-05-07 2010-05-07 Triptolide prodrugs
CA2964631A Abandoned CA2964631A1 (en) 2009-05-07 2010-05-07 Triptolide prodrugs

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2964631A Abandoned CA2964631A1 (en) 2009-05-07 2010-05-07 Triptolide prodrugs

Country Status (17)

Country Link
US (1) US8507552B2 (enExample)
EP (1) EP2427467B1 (enExample)
JP (3) JP6000122B2 (enExample)
KR (1) KR101821823B1 (enExample)
CN (1) CN102596977B (enExample)
AU (1) AU2010245669B2 (enExample)
BR (1) BRPI1014802B8 (enExample)
CA (2) CA2760953C (enExample)
DK (1) DK2427467T3 (enExample)
EA (1) EA021135B1 (enExample)
ES (1) ES2552163T3 (enExample)
MX (1) MX2011011776A (enExample)
MY (1) MY160392A (enExample)
PL (1) PL2427467T3 (enExample)
PT (1) PT2427467E (enExample)
SG (1) SG175885A1 (enExample)
WO (1) WO2010129918A1 (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9150600B2 (en) 2009-05-07 2015-10-06 Regents Of The University Of Minnesota Triptolide prodrugs
ES2902651T3 (es) * 2012-08-23 2022-03-29 Senestech Inc Reducción de la capacidad reproductiva de mamíferos
WO2014047783A1 (zh) * 2012-09-25 2014-04-03 鼎泓国际投资（香港）有限公司 含有雷公藤甲素及雷公藤甲素类衍生物和Bcl-2抑制剂的药物组合物及其应用
WO2014167581A2 (en) * 2013-04-01 2014-10-16 Laurus Labs Private Limited An improved process for the preparation of triptolide prodrugs
SG11201802915WA (en) * 2015-09-11 2018-05-30 Ys Ac Co Ltd Cancer treatment composition combining anti-cd26 antibody and other anticancer agent
CN109942665B (zh) * 2018-04-02 2021-04-06 欣凯医药化工中间体（上海）有限公司 雷公藤内酯醇衍生物及其制备方法和应用
CN110551171B (zh) * 2018-05-31 2021-07-27 欣凯医药化工中间体（上海）有限公司 一种雷公藤内酯醇衍生物的制备方法
CA3112171A1 (en) * 2018-09-13 2020-03-19 Minneamrita Therapeutics, LLC Triptolide and prodrugs thereof for use in methods to treat fibrosis, nash, and nafld
WO2021221179A1 (ja) * 2020-04-28 2021-11-04 国立大学法人高知大学 ヒト膵癌オルガノイドを用いたマウスモデルの樹立
EP4200022A1 (en) 2020-08-21 2023-06-28 Reyoung Corporation Triptolide conjugates and uses thereof
CN115227829B (zh) * 2022-02-22 2023-10-13 成都中医药大学 酸敏感性适配体雷公藤甲素偶联物及应用
AU2023435819A1 (en) 2023-03-09 2025-10-02 Minneamrita Therapeutics Llc Drug combination for treatment of pancreatic cancer
WO2024186319A1 (en) 2023-03-09 2024-09-12 Minneamrita Therapeutics Llc Drug combination for treatment of gastric cancer
AU2025207356A1 (en) 2024-01-11 2026-08-06 Minneamrita Therapeutics Llc Triptolide formulations

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5843452A (en) 1992-11-09 1998-12-01 Pharmagenesis, Inc. Immunotherapy composition and method
US5759550A (en) 1993-05-06 1998-06-02 Pharmagenesis, Inc. Method for suppressing xenograft rejection
US5609991A (en) 1995-02-10 1997-03-11 Morton International, Inc. Photoimageable composition having improved alkaline process resistance and tack-free surface for contact imaging
US5663335A (en) 1996-03-01 1997-09-02 Pharmagenesis, Inc. Immunosuppressive compounds and methods
US5962516A (en) 1997-02-28 1999-10-05 Pharmagenesis, Inc. Immunosuppressive compounds and methods
US6204257B1 (en) * 1998-08-07 2001-03-20 Universtiy Of Kansas Water soluble prodrugs of hindered alcohols
US6548537B1 (en) * 1998-09-02 2003-04-15 Pharmagenesis, Inc. Triptolide prodrugs having high aqueous solubility
JP2002523495A (ja) * 1998-09-02 2002-07-30 ファーマジェネシス， インコーポレイテッド 高い水溶性を有するトリプトリドプロドラッグ
WO2000048619A1 (en) 1999-02-16 2000-08-24 The Board Of Trustees Of The Leland Stanford Junior University Combined therapy of diterpenoid triepoxides and trail for synergistic killing of tumor cells
AU5368699A (en) 1999-04-16 2000-11-02 Chengdu Diao Pharmaceutical Group Company Limited Derivatives of triptolide, and preparation and uses thereof
US6294546B1 (en) 1999-08-30 2001-09-25 The Broad Of Trustees Of The Leland Stanford Junior University Uses of diterpenoid triepoxides as an anti-proliferative agent
US6620843B2 (en) 2001-01-19 2003-09-16 Pharmagenesis Anticancer treatment using triptolide prodrugs
EP1390358A4 (en) 2001-03-15 2004-06-16 Pharmagenesis Inc AMINO ACID DERIVATIVES OF TRIPTOLIDE COMPOUNDS AS IMMUNOMODULATORS AND ANTICROPHES
KR101016969B1 (ko) * 2001-12-21 2011-02-25 에이자이 아이엔씨. 알콜 및 페놀의 수용성 포스포노옥시메틸 유도체를제조하는 방법
AU2003243351B2 (en) 2002-05-31 2009-04-30 Pharmagenesis, Inc. Triptolide derivatives for modulation of apoptosis and immunosuppression
CN100398544C (zh) * 2002-09-18 2008-07-02 成都达远药物有限公司 高免疫抑制活性的水溶性雷公藤内酯醇衍生物及其应用
WO2004058246A1 (en) 2002-12-17 2004-07-15 Pharmagenesis, Inc. Triptolide derivatives as immunomodulator and anticancer agents
CN1223595C (zh) 2002-12-27 2005-10-19 中国科学院上海药物研究所 雷公藤内酯醇衍生物及其应用
US6943259B2 (en) 2003-02-25 2005-09-13 Pharmagenesis, Inc. Halogenated triptolide derivatives as immunomodulators and anticancer agents
WO2005020887A2 (en) 2003-06-27 2005-03-10 Pharmagenesis, Inc. Method for treatment of severe acute respiratory syndrome
US7820834B2 (en) 2003-12-24 2010-10-26 Pharmagenesis, Inc. Triptolide 5,6-derivatives as immunomodulators and anticancer agents
JP5252765B2 (ja) 2003-12-26 2013-07-31 学校法人東京薬科大学 皮脂産生抑制剤及び皮脂腺発達抑制剤、並びに、皮膚外用剤
ES2385716T3 (es) 2004-03-02 2012-07-30 Pharmagenesis, Inc. Derivados en el anillo de lactona de triptolida como inmunomoduladores y agentes anticáncer
US20070244080A1 (en) 2004-06-25 2007-10-18 Pharmagenesis, Inc. Method for Treatment of Inflammatory Disorders Using Triptolide Compounds
WO2007025031A2 (en) * 2005-08-24 2007-03-01 Cephalon, Inc. Prodrugs of indanone and tetralone compounds
CN101049300A (zh) 2006-04-04 2007-10-10 中国科学院上海药物研究所 包含雷公藤内酯醇衍生物的药物组合物、其剂型和应用
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CN101622263B (zh) * 2007-03-06 2013-05-29 卫材R&D管理有限公司 稳定性被改善的含有磷酸氯甲酯衍生物的组合物及其制备方法
FI20070574A0 (fi) * 2007-07-30 2007-07-30 Kuopion Yliopisto Vesiliukoinen propofolin etylideenifosfaatti-aihiolääke
WO2009023201A1 (en) 2007-08-16 2009-02-19 Myelorx Llc Rigid derivatives of triptolide as anticancer, immune suppressant, anti-fibrosis, and cns protectant agents

Also Published As

Publication number Publication date
EP2427467B1 (en) 2015-08-05
MX2011011776A (es) 2012-08-03
BRPI1014802A2 (pt) 2016-04-05
ES2552163T3 (es) 2015-11-26
KR101821823B1 (ko) 2018-01-24
EA201190293A1 (ru) 2012-11-30
EA021135B1 (ru) 2015-04-30
JP2016065099A (ja) 2016-04-28
CN102596977B (zh) 2016-06-29
EP2427467A1 (en) 2012-03-14
AU2010245669A1 (en) 2011-12-01
WO2010129918A8 (en) 2011-01-20
JP2014185181A (ja) 2014-10-02
WO2010129918A1 (en) 2010-11-11
PT2427467E (pt) 2015-11-19
AU2010245669B2 (en) 2015-11-26
PL2427467T3 (pl) 2016-04-29
HK1168107A1 (en) 2012-12-21
KR20120015339A (ko) 2012-02-21
JP2012526148A (ja) 2012-10-25
JP6000122B2 (ja) 2016-09-28
CN102596977A (zh) 2012-07-18
SG175885A1 (en) 2011-12-29
US20120238529A1 (en) 2012-09-20
BRPI1014802B1 (pt) 2020-09-24
US8507552B2 (en) 2013-08-13
CA2964631A1 (en) 2010-11-11
BRPI1014802B8 (pt) 2021-05-25
DK2427467T3 (en) 2015-11-09
CA2760953A1 (en) 2010-11-11
MY160392A (en) 2017-03-15

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