CA2304557A1 - Polyamine transport inhibitors - Google Patents

Polyamine transport inhibitors Download PDF

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Publication number
CA2304557A1
CA2304557A1 CA002304557A CA2304557A CA2304557A1 CA 2304557 A1 CA2304557 A1 CA 2304557A1 CA 002304557 A CA002304557 A CA 002304557A CA 2304557 A CA2304557 A CA 2304557A CA 2304557 A1 CA2304557 A1 CA 2304557A1
Authority
CA
Canada
Prior art keywords
polyamine
inhibitors
uptake
cells
polyamines
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
CA002304557A
Other languages
French (fr)
Other versions
CA2304557C (en
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
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 CA2304557A1 publication Critical patent/CA2304557A1/en
Application granted granted Critical
Publication of CA2304557C publication Critical patent/CA2304557C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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

The present invention describes the design, synthesis and therapeutic use of a variety of novel inhibitors of polyamine transport. The main feature of this class of transport inhibitors is to incorporate a linker or side chain that prevents the uptake of polyamines and helps to conjugate polyamine analogs to form dimers with high inhibitory potency against polyamine uptake. These new compounds incorporate features that are designed to maximize their chemical and metabolic stability and their ability to bind to the polyamine transporter, and to minimize their toxicity by preventing their absorption by the cells. The purpose of such inhibitors is to prevent the uptake or salvaging of circulating polyamines by rapidly proliferating cells such as tumor cells, in order to potentiate the effect of therapeutic inhibitors of polyamine biosynthesis such as alpha-difluoromethylomithene.
CA002304557A 1998-04-21 1998-04-21 Polyamine transport inhibitors Expired - Fee Related CA2304557C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1998/007806 WO1999054283A1 (en) 1998-04-21 1998-04-21 Polyamine transport inhibitors

Publications (2)

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

Family

ID=22266863

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002304557A Expired - Fee Related CA2304557C (en) 1998-04-21 1998-04-21 Polyamine transport inhibitors

Country Status (4)

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

Families Citing this family (8)

* 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
EP1698629A3 (en) 1999-04-30 2006-11-29 Cellgate, Inc. Polyamines and their use in therapy
USRE43327E1 (en) 2001-01-08 2012-04-24 Aminex Therapeutics, Inc. Hydrophobic polyamine analogs and methods for their use
US6982351B2 (en) 2001-12-07 2006-01-03 Cellgate, Inc. Cycloalkyl substituted polyamines for cancer therapy and methods of synthesis therefor
CN102659605B (en) * 2012-05-08 2013-11-13 天津市普莱克医药科技有限公司 Synthesizing method of spermidine
EP3785706B1 (en) 2016-03-25 2023-06-07 Aminex Therapeutics, Inc. Bioavailable polyamines
CN114096240A (en) 2019-05-17 2022-02-25 癌症预防制药股份有限公司 Method for treating familial adenomatous polyposis
CA3193185A1 (en) 2020-09-30 2022-04-07 Mark R. Burns 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 (en) 2000-05-31
WO1999054283A1 (en) 1999-10-28
AU7131698A (en) 1999-11-08
CA2304557C (en) 2008-12-30

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EEER Examination request
MKLA Lapsed

Effective date: 20170421