US20010025035A1 - Water soluble prodrugs of hindered alcohols - Google Patents

Water soluble prodrugs of hindered alcohols Download PDF

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Publication number
US20010025035A1
US20010025035A1 US09/733,817 US73381700A US2001025035A1 US 20010025035 A1 US20010025035 A1 US 20010025035A1 US 73381700 A US73381700 A US 73381700A US 2001025035 A1 US2001025035 A1 US 2001025035A1
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United States
Prior art keywords
compound
group
formula
compound according
camptothecin
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US09/733,817
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US6451776B2 (en
Inventor
Valentino Stella
Jan Zygmunt
Ingrid Georg
Muhammad Safadi
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University of Kansas
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University of Kansas
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Priority to US09/733,817 priority Critical patent/US6451776B2/en
Publication of US20010025035A1 publication Critical patent/US20010025035A1/en
Priority to US10/208,647 priority patent/US6872838B2/en
Application granted granted Critical
Publication of US6451776B2 publication Critical patent/US6451776B2/en
Priority to US10/991,348 priority patent/US7244718B2/en
Assigned to UNIVERSITY OF KANSAS reassignment UNIVERSITY OF KANSAS ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SAFADI, MUHAMMAD S., GEORG, INGRID GUNDA, STELLA, VALENTINO J., ZYGMUNT, JAN J.
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    • 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • A61K38/13—Cyclosporins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P23/00—Anaesthetics
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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 System
    • 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
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with 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 System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
    • C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • 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 System
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/64—Cyclic peptides containing only normal peptide links
    • C07K7/645—Cyclosporins; Related peptides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • 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)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Biophysics (AREA)
  • Biotechnology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Anesthesiology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Saccharide Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Steroid Compounds (AREA)
US09/733,817 1998-08-07 2000-12-08 Water soluble prodrugs of hindered alcohols Expired - Lifetime US6451776B2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US09/733,817 US6451776B2 (en) 1998-08-07 2000-12-08 Water soluble prodrugs of hindered alcohols
US10/208,647 US6872838B2 (en) 1998-08-07 2002-07-29 Water soluble prodrugs of hindered alcohols
US10/991,348 US7244718B2 (en) 1998-08-07 2004-11-17 Water soluble prodrugs of hindered alcohols

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/131,385 US6204257B1 (en) 1998-08-07 1998-08-07 Water soluble prodrugs of hindered alcohols
US09/733,817 US6451776B2 (en) 1998-08-07 2000-12-08 Water soluble prodrugs of hindered alcohols

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US09/131,385 Division US6204257B1 (en) 1998-08-07 1998-08-07 Water soluble prodrugs of hindered alcohols

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/208,647 Division US6872838B2 (en) 1998-08-07 2002-07-29 Water soluble prodrugs of hindered alcohols

Publications (2)

Publication Number Publication Date
US20010025035A1 true US20010025035A1 (en) 2001-09-27
US6451776B2 US6451776B2 (en) 2002-09-17

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Family Applications (4)

Application Number Title Priority Date Filing Date
US09/131,385 Expired - Lifetime US6204257B1 (en) 1998-08-07 1998-08-07 Water soluble prodrugs of hindered alcohols
US09/733,817 Expired - Lifetime US6451776B2 (en) 1998-08-07 2000-12-08 Water soluble prodrugs of hindered alcohols
US10/208,647 Expired - Fee Related US6872838B2 (en) 1998-08-07 2002-07-29 Water soluble prodrugs of hindered alcohols
US10/991,348 Expired - Fee Related US7244718B2 (en) 1998-08-07 2004-11-17 Water soluble prodrugs of hindered alcohols

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US09/131,385 Expired - Lifetime US6204257B1 (en) 1998-08-07 1998-08-07 Water soluble prodrugs of hindered alcohols

Family Applications After (2)

Application Number Title Priority Date Filing Date
US10/208,647 Expired - Fee Related US6872838B2 (en) 1998-08-07 2002-07-29 Water soluble prodrugs of hindered alcohols
US10/991,348 Expired - Fee Related US7244718B2 (en) 1998-08-07 2004-11-17 Water soluble prodrugs of hindered alcohols

Country Status (27)

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US (4) US6204257B1 (US20010025035A1-20010927-C00016.png)
EP (2) EP1683803A1 (US20010025035A1-20010927-C00016.png)
JP (1) JP4554081B2 (US20010025035A1-20010927-C00016.png)
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CN (2) CN1198834C (US20010025035A1-20010927-C00016.png)
AT (1) ATE319723T1 (US20010025035A1-20010927-C00016.png)
AU (1) AU769755B2 (US20010025035A1-20010927-C00016.png)
BR (1) BR9912853A (US20010025035A1-20010927-C00016.png)
CA (1) CA2339834C (US20010025035A1-20010927-C00016.png)
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DE (1) DE69930269T2 (US20010025035A1-20010927-C00016.png)
DK (1) DK1102776T3 (US20010025035A1-20010927-C00016.png)
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HK (1) HK1047939B (US20010025035A1-20010927-C00016.png)
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NZ (1) NZ509795A (US20010025035A1-20010927-C00016.png)
PL (1) PL198141B1 (US20010025035A1-20010927-C00016.png)
PT (1) PT1102776E (US20010025035A1-20010927-C00016.png)
RU (1) RU2235727C2 (US20010025035A1-20010927-C00016.png)
TR (1) TR200100772T2 (US20010025035A1-20010927-C00016.png)
UA (1) UA73479C2 (US20010025035A1-20010927-C00016.png)
WO (1) WO2000008033A1 (US20010025035A1-20010927-C00016.png)
ZA (1) ZA200101039B (US20010025035A1-20010927-C00016.png)

Cited By (9)

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US20050107385A1 (en) * 2003-09-09 2005-05-19 Xenoport, Inc. Aromatic prodrugs of propofol, compositions and uses thereof
US20060041011A1 (en) * 2004-07-12 2006-02-23 Xenoport, Inc. Prodrugs of propofol, compositions and uses thereof
US20060100160A1 (en) * 2004-07-12 2006-05-11 Xenoport, Inc. Amino acid derived prodrugs of propofol, compositions and uses thereof
US20060205969A1 (en) * 2004-12-23 2006-09-14 Xenoport, Inc. Amino acid derived prodrugs of propofol, compositions, uses and crystalline forms thereof
US20080221069A1 (en) * 2005-09-02 2008-09-11 Auspex Pharmaceuticals, Inc. Novel Therapeutic Agents for the Treatment of Cancer, Metabolic Diseases and Skin Disorders
US20080234229A1 (en) * 2005-08-18 2008-09-25 Auspex Pharmaceuticals, Inc. Novel Therapeutic Agents for the Treatment of Cancer, Metabolic Diseases and Skin Disorders
US20080248093A1 (en) * 2003-10-24 2008-10-09 Auspex Pharmaceuticals, Inc. pH sensitive prodrugs of 2,6-diisopropylphenol
EP2292577A1 (en) 2007-05-09 2011-03-09 Pharmacofore, Inc. (+)-stereoisomer of 2,6-di-sec-butylphenol and analogs thereof
EP2392559A1 (en) 2007-05-09 2011-12-07 Pharmacofore, Inc. Therapeutic compounds

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US6204257B1 (en) * 1998-08-07 2001-03-20 Universtiy Of Kansas Water soluble prodrugs of hindered alcohols
WO2000010531A1 (en) * 1998-08-19 2000-03-02 Rtp Pharma Inc. Injectable aqueous dispersions of propofol
US6362172B2 (en) * 2000-01-20 2002-03-26 Bristol-Myers Squibb Company Water soluble prodrugs of azole compounds
US6362234B1 (en) * 2000-08-15 2002-03-26 Vyrex Corporation Water-soluble prodrugs of propofol for treatment of migrane
US6448401B1 (en) * 2000-11-20 2002-09-10 Bristol-Myers Squibb Company Process for water soluble azole compounds
AU2002245996B8 (en) * 2001-04-20 2005-07-14 Ophthalmopharma Ag Modified cyclosporine which can be used as a pro-drug and use thereof
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HU229293B1 (hu) * 2001-12-28 2013-10-28 Eisai Inc Propofol vízoldható elõgyógyszerét tartalmazó vizes alapú gyógyászati készítmények
KR20070087004A (ko) * 2002-04-08 2007-08-27 엠쥐아이 쥐피, 아이엔씨. 프로포폴의 수용성 프로드럭을 함유하는 약제학적 조성물및 그것을 투여하는 방법
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CN102174076A (zh) 2004-04-15 2011-09-07 普罗特奥里克斯公司 用于抑制蛋白酶体酶的化合物
US7232818B2 (en) * 2004-04-15 2007-06-19 Proteolix, Inc. Compounds for enzyme inhibition
US8198270B2 (en) * 2004-04-15 2012-06-12 Onyx Therapeutics, Inc. Compounds for proteasome enzyme inhibition
PL2030981T3 (pl) * 2004-05-10 2014-12-31 Onyx Therapeutics Inc Związki do enzymatycznej inhibicji proteasomu
WO2005111009A2 (en) * 2004-05-10 2005-11-24 Proteolix, Inc. Synthesis of amino acid keto-epoxides
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US20060014677A1 (en) * 2004-07-19 2006-01-19 Isotechnika International Inc. Method for maximizing efficacy and predicting and minimizing toxicity of calcineurin inhibitor compounds
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JP4981673B2 (ja) * 2005-09-13 2012-07-25 エーザイ・アール・アンド・ディー・マネジメント株式会社 安定性が改善されたクロロメチルフォスフェイト誘導体を含む組成物およびその製造方法
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