CA2223989C - Prodrugs of pharmaceuticals with improved bioavailability - Google Patents

Prodrugs of pharmaceuticals with improved bioavailability Download PDF

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Publication number
CA2223989C
CA2223989C CA2223989A CA2223989A CA2223989C CA 2223989 C CA2223989 C CA 2223989C CA 2223989 A CA2223989 A CA 2223989A CA 2223989 A CA2223989 A CA 2223989A CA 2223989 C CA2223989 C CA 2223989C
Authority
CA
Canada
Prior art keywords
alkyl
group
acyl
compound according
octadecyl
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 - Lifetime
Application number
CA2223989A
Other languages
English (en)
French (fr)
Other versions
CA2223989A1 (en
Inventor
Karl Y. Hostetler
Ganesh D. Kini
James R. Beadle
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2223989A1 publication Critical patent/CA2223989A1/en
Application granted granted Critical
Publication of CA2223989C publication Critical patent/CA2223989C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • 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
    • A61P31/04—Antibacterial agents
    • 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
    • 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
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/098—Esters of polyphosphoric acids or anhydrides
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/10—Phosphatides, e.g. lecithin
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
    • C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Biophysics (AREA)
  • Dispersion Chemistry (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2223989A 1995-06-07 1996-06-07 Prodrugs of pharmaceuticals with improved bioavailability Expired - Lifetime CA2223989C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/487,081 US7517858B1 (en) 1995-06-07 1995-06-07 Prodrugs of pharmaceuticals with improved bioavailability
US08/487,081 1995-06-07
PCT/US1996/010054 WO1996039831A1 (en) 1995-06-07 1996-06-07 Prodrugs of pharmaceuticals with improved bioavailability

Publications (2)

Publication Number Publication Date
CA2223989A1 CA2223989A1 (en) 1996-12-19
CA2223989C true CA2223989C (en) 2010-11-23

Family

ID=23934330

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2223989A Expired - Lifetime CA2223989C (en) 1995-06-07 1996-06-07 Prodrugs of pharmaceuticals with improved bioavailability

Country Status (9)

Country Link
US (1) US7517858B1 (enExample)
EP (1) EP0837630B1 (enExample)
JP (1) JP4301571B2 (enExample)
AT (1) ATE382051T1 (enExample)
AU (1) AU711774B2 (enExample)
CA (1) CA2223989C (enExample)
DE (1) DE69637381T2 (enExample)
ES (1) ES2299178T3 (enExample)
WO (1) WO1996039831A1 (enExample)

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US6410328B1 (en) 1998-02-03 2002-06-25 Protiva Biotherapeutics Inc. Sensitizing cells to compounds using lipid-mediated gene and compound delivery
IL131887A0 (en) * 1999-09-14 2001-03-19 Dpharm Ltd Phospholipid prodrugs of anti-proliferative drugs
KR20020073494A (ko) * 1999-12-29 2002-09-26 더 리전트 오브 더 유니버시티 오브 캘리포니아 약물내성 인체 면역결핍 바이러스 감염의 치료
EP1460082A1 (en) * 2003-03-19 2004-09-22 Heidelberg Pharma Holding GmbH Phospholipid esters of clofarabine derivatives
JP2008518886A (ja) * 2004-11-03 2008-06-05 リプラサム ファーマ アー／エス 非天然ホスホリパーゼａ２分解性脂質誘導体を含有する脂質ベースの薬剤送達系およびその治療的使用
NZ554783A (en) 2004-11-15 2010-12-24 Ceptyr Inc Protein tyrosine phosphatase inhibitors and methods of use thereof
US8101745B2 (en) 2004-12-16 2012-01-24 The Regents Of The University Of California Lung-targeted drugs
WO2007107161A2 (en) * 2006-03-23 2007-09-27 Liplasome Pharma A/S Lipid based drug delivery systems comprising phospholipase a2 degradable lipids that perform an intramolecular cyclization reaction upon hydrolysis
ES2600792T3 (es) * 2006-05-03 2017-02-10 Chimerix, Inc. Alcoxialquilésteres metabólicamente estables de fosfonatos, fosfonatos nucleosídicos y fosfatos nucleosídicos antivirales o antiproliferativos
WO2009061208A1 (en) * 2007-11-09 2009-05-14 Pronova Biopharma Norge As Lipid compounds for use in cosmetic products, as food supplement or as a medicament
EP2070938A1 (en) * 2007-12-13 2009-06-17 Heidelberg Pharma AG Clofarabine dietherphospholipid derivatives
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US8586625B2 (en) * 2008-01-16 2013-11-19 Anwar Rayan Derivatives of taxol and closely related compounds
EP2147910A1 (en) * 2008-07-15 2010-01-27 Pronova BioPharma Norge AS Novel lipid compounds
KR101783817B1 (ko) 2009-05-08 2017-10-23 프로노바 바이오파마 너지 에이에스 심혈관 질병, 대사 질병, 및 염증성 질환 분야관련 질병의 치료를 위한 다중 불포화 지방산
US8884027B2 (en) 2010-10-22 2014-11-11 University Of Rochester Melampomagnolide B derivatives as antileukemic and cytotoxic agents
SG10201509127YA (en) 2010-11-05 2015-12-30 Pronova Biopharma Norge As Methods of treatment using lipid compounds
US11351139B2 (en) 2013-02-28 2022-06-07 Basf As Composition comprising a lipid compound, a triglyceride, and a surfactant, and methods of using the same
KR20150130355A (ko) 2013-03-15 2015-11-23 더 리전트 오브 더 유니버시티 오브 캘리포니아 비환식 뉴클레오사이드 포스포네이트 디에스테르
MX2016011897A (es) 2014-03-14 2017-04-27 Alltech Inc Composiciones de compuestos selenoorganicos y metodos de uso de los mismos.
MX377983B (es) 2014-09-15 2025-03-04 Univ California Análogos de nucleótidos.
CN106999506A (zh) 2014-11-26 2017-08-01 脉管生物生长有限公司 氧化脂质以及纤维化的治疗或预防
US9771385B2 (en) * 2014-11-26 2017-09-26 Vascular Biogenics Ltd. Oxidized lipids
FI3265102T3 (fi) 2015-03-06 2025-10-31 Atea Pharmaceuticals Inc Beta-d-2'-deoksi-2'-alfa-fluori-2'-beta-c-substituoituja-2-modifioituja-n6-substituoituja puriininukleotideja hcv-hoitoa varten
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US20220226480A1 (en) * 2019-03-22 2022-07-21 Integrated Nanotherapeutics Inc. Lipid conjugate prepared from scaffold moiety
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Also Published As

Publication number Publication date
AU711774B2 (en) 1999-10-21
EP0837630B1 (en) 2007-12-26
DE69637381D1 (de) 2008-02-07
EP0837630A4 (en) 1998-11-25
ATE382051T1 (de) 2008-01-15
EP0837630A1 (en) 1998-04-29
WO1996039831A1 (en) 1996-12-19
US7517858B1 (en) 2009-04-14
CA2223989A1 (en) 1996-12-19
DE69637381T2 (de) 2008-12-11
ES2299178T3 (es) 2008-05-16
JPH11512078A (ja) 1999-10-19
AU6171796A (en) 1996-12-30
JP4301571B2 (ja) 2009-07-22

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Effective date: 20160607