CA2445478A1 - Retinol derivatives potentiation of active substances by micellar preparation - Google Patents

Retinol derivatives potentiation of active substances by micellar preparation Download PDF

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Publication number
CA2445478A1
CA2445478A1 CA002445478A CA2445478A CA2445478A1 CA 2445478 A1 CA2445478 A1 CA 2445478A1 CA 002445478 A CA002445478 A CA 002445478A CA 2445478 A CA2445478 A CA 2445478A CA 2445478 A1 CA2445478 A1 CA 2445478A1
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CA
Canada
Prior art keywords
potentiation
active substances
micellar preparation
retinol derivatives
compounds
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.)
Granted
Application number
CA002445478A
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French (fr)
Other versions
CA2445478C (en
Inventor
Oleg Strelchenok
Julian Aleksov
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Vivesto AB
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Individual
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Publication of CA2445478A1 publication Critical patent/CA2445478A1/en
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Publication of CA2445478C publication Critical patent/CA2445478C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/203—Retinoic acids ; Salts thereof
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/22—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biophysics (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Epoxy Compounds (AREA)
  • Cosmetics (AREA)

Abstract

This invention relates to novel compounds, capable of potentiating the efficacy of therapeutically active compounds, for example cytotoxic compounds used in the treatment of cancer. The novel compounds have been shown to increase the pharmacological activity of a conventional paclitaxel formulation and to make it possible to manufacture a new formulation of paclitaxel, exhibiting improved solubility, improved storage properties, and increased therapeutic efficacy as shown in the enclosed examples. (Formula I, II, III, IV, V, VI)
CA002445478A 2001-05-15 2002-03-05 Retinol derivatives potentiation of active substances by micellar preparation Expired - Lifetime CA2445478C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
SE0101702-9 2001-05-15
SE0101702A SE0101702D0 (en) 2001-05-15 2001-05-15 Novel potentiating compounds
US30279001P 2001-07-03 2001-07-03
US60/302,790 2001-07-03
PCT/SE2002/000380 WO2002092600A1 (en) 2001-05-15 2002-03-05 Retinol derivatives potentiation of active substances by micellar preparation

Publications (2)

Publication Number Publication Date
CA2445478A1 true CA2445478A1 (en) 2002-11-21
CA2445478C CA2445478C (en) 2009-05-26

Family

ID=20284111

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002445478A Expired - Lifetime CA2445478C (en) 2001-05-15 2002-03-05 Retinol derivatives potentiation of active substances by micellar preparation

Country Status (13)

Country Link
US (1) US6642271B2 (en)
EP (3) EP1387844B1 (en)
JP (1) JP4147114B2 (en)
AT (2) ATE364586T1 (en)
AU (1) AU2002235085B2 (en)
CA (1) CA2445478C (en)
DE (2) DE60220666T2 (en)
DK (2) DK1387844T3 (en)
ES (2) ES2331264T3 (en)
HK (1) HK1110574A1 (en)
PT (2) PT1387844E (en)
SE (1) SE0101702D0 (en)
WO (1) WO2002092600A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4275706A2 (en) 2016-05-13 2023-11-15 Phytoceutical Limited Micelles of d-alpha-tocopheryl polyethylene glycol 1000 succinate

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SE0101702D0 (en) 2001-05-15 2001-05-15 Ardenia Investments Ltd Novel potentiating compounds
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SE0202311D0 (en) * 2002-07-23 2002-07-23 Ardenia Investments Ltd Novel compounds, cytotoxic preparations comprising said compounds, methods of manufacture of said preparations, as well as methods of treatment
US9572886B2 (en) 2005-12-22 2017-02-21 Nitto Denko Corporation Agent for treating myelofibrosis
US8003621B2 (en) * 2007-09-14 2011-08-23 Nitto Denko Corporation Drug carriers
WO2009078754A1 (en) 2007-12-19 2009-06-25 Ardenia Investments, Ltd. Drug delivery system for administration of poorly water soluble pharmaceutically active substances
WO2009078756A1 (en) * 2007-12-19 2009-06-25 Ardenia Investments, Ltd. Drug delivery system for administration of a water soluble, cationic and amphiphilic pharmaceutically active substance
WO2009078755A1 (en) * 2007-12-19 2009-06-25 Ardenia Investments, Ltd. Drug delivery system for administration of a water soluble, cationic and amphiphilic pharmaceutically active substance
CN102159247A (en) * 2008-07-30 2011-08-17 日东电工株式会社 Drug carriers
AU2016365535B2 (en) * 2015-12-09 2020-07-23 Oasmia Pharmaceutical Ab Method for producing N-retinoylcysteic acid alkyl ester
CN107149684B (en) * 2017-05-08 2019-10-25 西南大学 The new application of cysteine dioxygenase, gene and its catalysate cysteine sulfinic acid
CN110218168B (en) * 2018-03-02 2022-09-20 上海现代药物制剂工程研究中心有限公司 Preparation method of sodium salt of N- (all-trans-retinoyl) -L-methyl cysteic acid
CN112321465B (en) * 2019-07-18 2023-06-06 上海现代药物制剂工程研究中心有限公司 Phenyl-containing compound, intermediate thereof, preparation method and application
CN112239418B (en) * 2019-07-18 2023-07-07 上海现代药物制剂工程研究中心有限公司 Preparation method of retinol compound and sodium salt thereof
WO2024068553A1 (en) 2022-09-26 2024-04-04 Vivesto Ab Solubilizing compounds

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SE0101702D0 (en) 2001-05-15 2001-05-15 Ardenia Investments Ltd Novel potentiating compounds

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EP4275706A2 (en) 2016-05-13 2023-11-15 Phytoceutical Limited Micelles of d-alpha-tocopheryl polyethylene glycol 1000 succinate

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ATE364586T1 (en) 2007-07-15
SE0101702D0 (en) 2001-05-15
ATE438616T1 (en) 2009-08-15
PT1826198E (en) 2009-09-28
EP1387844A1 (en) 2004-02-11
JP2005508287A (en) 2005-03-31
DE60220666D1 (en) 2007-07-26
PT1387844E (en) 2007-08-24
WO2002092600A1 (en) 2002-11-21
HK1110574A1 (en) 2008-07-18
DE60233276D1 (en) 2009-09-17
EP1826198A1 (en) 2007-08-29
DE60220666T2 (en) 2008-02-28
EP2116524B1 (en) 2012-10-03
US6642271B2 (en) 2003-11-04
DK1826198T3 (en) 2009-12-07
ES2288183T3 (en) 2008-01-01
US20030050343A1 (en) 2003-03-13
EP1387844B1 (en) 2007-06-13
CA2445478C (en) 2009-05-26
EP1826198B1 (en) 2009-08-05
JP4147114B2 (en) 2008-09-10
DK1387844T3 (en) 2007-10-15
EP2116524A1 (en) 2009-11-11
AU2002235085B2 (en) 2006-12-07

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