CA2304557C - Inhibiteurs du transport des polyamines - Google Patents

Inhibiteurs du transport des polyamines Download PDF

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Publication number
CA2304557C
CA2304557C CA002304557A CA2304557A CA2304557C CA 2304557 C CA2304557 C CA 2304557C CA 002304557 A CA002304557 A CA 002304557A CA 2304557 A CA2304557 A CA 2304557A CA 2304557 C CA2304557 C CA 2304557C
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CA
Canada
Prior art keywords
compound
polyamine
less
cancer
spermine
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 - Fee Related
Application number
CA002304557A
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English (en)
Other versions
CA2304557A1 (fr
Inventor
Richard Poulin
Marie Audette
Rene Charest-Gaudrealt
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.)
Universite Laval
Original Assignee
Universite Laval
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 Universite Laval filed Critical Universite Laval
Publication of CA2304557A1 publication Critical patent/CA2304557A1/fr
Application granted granted Critical
Publication of CA2304557C publication Critical patent/CA2304557C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Cette invention se rapporte à la conception, à la synthèse et à l'utilisation thérapeutique d'une variété de nouveaux inhibiteurs de transport des polyamines. La caractéristique principale de cette classe d'inhibiteurs de transport consiste à incorporer un segment de liaison ou une chaîne latérale qui empêche l'assimilation des polyamines et contribue à conjuguer des analogues de polyamines pour former des dimères ayant un pouvoir inhibiteur élevé contre l'assimilation des polyamines. Ces nouveaux composés incorporent des caractéristiques qui sont conçues pour maximiser leur stabilité chimique et métabolique et leur capacité à se fixer au transporteur de polyamines, ainsi qu'à minimiser leur toxicité en empêchant leur absorption par les cellules. L'objectif de ces inhibiteurs est d'empêcher l'assimilation ou la récupération des polyamines en circulation par des cellules proliférant rapidement, telles que les cellules tumorales, afin de renforcer l'effet des inhibiteurs thérapeutiques de la biosynthèse des polyamines, telle que l'alpha-difluorométhylornithène.
CA002304557A 1998-04-21 1998-04-21 Inhibiteurs du transport des polyamines Expired - Fee Related CA2304557C (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1998/007806 WO1999054283A1 (fr) 1998-04-21 1998-04-21 Inhibiteurs du transport des polyamines

Publications (2)

Publication Number Publication Date
CA2304557A1 CA2304557A1 (fr) 1999-10-28
CA2304557C true CA2304557C (fr) 2008-12-30

Family

ID=22266863

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002304557A Expired - Fee Related CA2304557C (fr) 1998-04-21 1998-04-21 Inhibiteurs du transport des polyamines

Country Status (4)

Country Link
EP (1) EP1003715A1 (fr)
AU (1) AU7131698A (fr)
CA (1) CA2304557C (fr)
WO (1) WO1999054283A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6646149B1 (en) * 1997-07-15 2003-11-11 Nicolaas M. J. Vermeulin Polyamine analogues as therapeutic and diagnostic agents
ES2269138T3 (es) 1999-04-30 2007-04-01 Cellgate, Inc. Poliaminas y su uso en terapia.
MXPA01011008A (es) 1999-04-30 2003-06-30 Slil Biomedical Corp Conjugados analogos de poliamina y conjugados de quinona novedosos como terapia para canceres y enfermedades de la prostata.
AU2002235126A1 (en) 2000-11-08 2002-05-21 Slil Biomedical Corporation Novel polyamine analog-amino acid conjugates useful as anticancer agents
USRE43327E1 (en) 2001-01-08 2012-04-24 Aminex Therapeutics, Inc. Hydrophobic polyamine analogs and methods for their use
IL161428A0 (en) 2001-10-16 2004-09-27 Slil Biomedical Corp Oligoamine derivatives, methods for the production thereof and pharmaceutical compositions containing the same
CA2469354A1 (fr) 2001-12-07 2003-06-19 Slil Biomedical Corporation Polyamines substituees par un cycloalkyle pour le traitement du cancer, et procedes de synthese de celles-ci
CN102659605B (zh) * 2012-05-08 2013-11-13 天津市普莱克医药科技有限公司 一种亚精胺的合成方法
CA3015849A1 (fr) 2016-03-25 2017-09-28 Mark R. Burns Polyamides biodisponibles
US10945981B2 (en) 2019-05-17 2021-03-16 Cancer Prevention Pharmaceuticals, Inc. Methods for treating familial adenomatous polyposis
US11865095B2 (en) 2020-09-30 2024-01-09 Aminex Therapeutics, Inc. Combination drug substance of polyamine transport inhibitor and DFMO

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5242947A (en) * 1988-02-10 1993-09-07 New York University Use of polyamines as ionic-channel regulating agents
US5456908A (en) * 1994-03-01 1995-10-10 The University Of Kentucky Research Foundation Polyamine-polyamine and polyamine-protein transport inhibitor conjugates and their use as pharmaceuticals and in research relating to polyamine transport
US6083496A (en) * 1996-10-22 2000-07-04 Universite Laval Polyamine transport inhibitors

Also Published As

Publication number Publication date
EP1003715A1 (fr) 2000-05-31
WO1999054283A1 (fr) 1999-10-28
CA2304557A1 (fr) 1999-10-28
AU7131698A (en) 1999-11-08

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Effective date: 20170421