WO2015025283A3 - Dual action carbonic anhydrase inhibitors - Google Patents

Dual action carbonic anhydrase inhibitors Download PDF

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Publication number
WO2015025283A3
WO2015025283A3 PCT/IB2014/063989 IB2014063989W WO2015025283A3 WO 2015025283 A3 WO2015025283 A3 WO 2015025283A3 IB 2014063989 W IB2014063989 W IB 2014063989W WO 2015025283 A3 WO2015025283 A3 WO 2015025283A3
Authority
WO
WIPO (PCT)
Prior art keywords
carbonic anhydrase
dual action
anhydrase inhibitors
inhibitors
present
Prior art date
Application number
PCT/IB2014/063989
Other languages
French (fr)
Other versions
WO2015025283A2 (en
Inventor
Philippe Lambin
Jean-Yves Winum
Original Assignee
Stichting Maastricht Radiation Oncology "Maastro-Clinic"
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 Stichting Maastricht Radiation Oncology "Maastro-Clinic" filed Critical Stichting Maastricht Radiation Oncology "Maastro-Clinic"
Publication of WO2015025283A2 publication Critical patent/WO2015025283A2/en
Publication of WO2015025283A3 publication Critical patent/WO2015025283A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/91—Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed 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
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
    • 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
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
    • 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
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
    • C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
    • C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
    • C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system

Abstract

The present invention is directed to novel carbonic anhydrase IX inhibitors comprising a nitroimidazole moiety substituted with a heterocycle or phosphinate and having sulfonamide, sulfamate or sulfamide groups. The present invention is also related to the use of these novel carbonic anhydrase IX inhibitors in cancer treatment, especially radiotherapy and chemotherapy and the use in treatment of infections.
PCT/IB2014/063989 2013-08-20 2014-08-20 Dual action carbonic anhydrase inhibitors WO2015025283A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL2011320 2013-08-20
NL2011320 2013-08-20

Publications (2)

Publication Number Publication Date
WO2015025283A2 WO2015025283A2 (en) 2015-02-26
WO2015025283A3 true WO2015025283A3 (en) 2015-07-23

Family

ID=49486635

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2014/063989 WO2015025283A2 (en) 2013-08-20 2014-08-20 Dual action carbonic anhydrase inhibitors

Country Status (1)

Country Link
WO (1) WO2015025283A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016089208A2 (en) 2014-12-04 2016-06-09 Stichting Maastricht Radiation Oncology "Maastro-Clinic" Sulfonamide, sulfamate and sulfamide derivatives of anti-cancer agents
LT6401B (en) 2015-07-28 2017-06-12 Vilniaus Universitetas Selective inhibitors of carbonic anhydrase
US20200276338A1 (en) * 2017-09-19 2020-09-03 The Governors Of The University Of Alberta Bioreductively-activated compounds, their prodrugs, radiopharmaceuticals, the compositions, and their applications in multimodal theranostic management of hypoxia diseases including cancer

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011098610A1 (en) * 2010-02-12 2011-08-18 Universita Degli Studi Di Firenze Carbonic anhydrase inhibitors
WO2012021963A1 (en) * 2010-07-09 2012-02-23 Metasignal Therapeutics Inc. Novel sulfonamide compounds for inhibition of metastatic tumor growth
WO2012087115A1 (en) * 2010-12-24 2012-06-28 Stichting Maastricht Radiation Oncology "Maastro-Clinic" Cancer targeting using carbonic anhydrase isoform ix inhibitors
WO2013116385A1 (en) * 2012-01-31 2013-08-08 Threshold Pharmaceuticals, Inc. Predictive biomarker for hypoxia-activated prodrug therapy

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4713341B2 (en) 2002-11-26 2011-06-29 インスティトゥート オブ ヴァイロロジー CA-IX specific inhibitors
WO2006102759A1 (en) 2005-03-29 2006-10-05 The Governors Of The University Of Alberta Novel substituted 2-nitroimidazoles useful for hypoxic cell therapy and imaging
WO2006137092A1 (en) 2005-06-23 2006-12-28 Supuran Claudiu T Fluorescent sulfonamide derivatives having carbonic anhydrase inhibiting activity and their use as theapeutic and diagnostic agents
TWI384989B (en) 2005-06-29 2013-02-11 Threshold Pharmaceuticals Inc Phosphoramidate alkylator prodrugs
WO2008071421A1 (en) 2006-12-15 2008-06-19 Nicox S.A. Nitrate esters of carbonic anhydrase inhibitors
CA2711678A1 (en) 2008-01-09 2009-07-16 Molecular Insight Pharmaceuticals, Inc. Inhibitors of carbonic anhydrase ix

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011098610A1 (en) * 2010-02-12 2011-08-18 Universita Degli Studi Di Firenze Carbonic anhydrase inhibitors
WO2012021963A1 (en) * 2010-07-09 2012-02-23 Metasignal Therapeutics Inc. Novel sulfonamide compounds for inhibition of metastatic tumor growth
WO2012087115A1 (en) * 2010-12-24 2012-06-28 Stichting Maastricht Radiation Oncology "Maastro-Clinic" Cancer targeting using carbonic anhydrase isoform ix inhibitors
WO2013116385A1 (en) * 2012-01-31 2013-08-08 Threshold Pharmaceuticals, Inc. Predictive biomarker for hypoxia-activated prodrug therapy

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
ASTOR M ET AL: "Newly synthesized hypoxia-mediated drugs as radiosensitizers and cytotoxic agents", INTERNATIONAL JOURNAL OF RADIATION: ONCOLOGY BIOLOGY PHYSICS, PERGAMON PRESS, USA, vol. 8, no. 1, 1 January 1982 (1982-01-01), pages 75 - 83, XP026842441, ISSN: 0360-3016, [retrieved on 19820101] *
DATABASE REGISTRY [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 29 May 2011 (2011-05-29), XP002734043, retrieved from stn Database accession no. 1302509-63-2 *
DATABASE REGISTRY [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 8 February 2012 (2012-02-08), XP002734042, retrieved from stn Database accession no. 1355774-86-5 *
FRAME A S ET AL: "Synthesis of 5-Amino-4-sulfonamidoimidazole Nucleosides as Potential Inhibitors of Purine Nucleotide Biosynthesis, and of an Imidazothiadiazine Dioxide Analogue of Adenosine", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 52, no. 27, 1 July 1996 (1996-07-01), pages 9219 - 9236, XP004104008, ISSN: 0040-4020, DOI: 10.1016/0040-4020(96)00472-3 *
LUDWIG DUBOIS ET AL: "Targeting carbonic anhydrase IX by nitroimidazole based sulfamides enhances the therapeutic effect of tumor irradiation: A new concept of dual targeting drugs", RADIOTHERAPY AND ONCOLOGY, vol. 108, no. 3, 9 July 2013 (2013-07-09), pages 523 - 528, XP055159806, ISSN: 0167-8140, DOI: 10.1016/j.radonc.2013.06.018 *
NAGARAJAN K ET AL: "NITROIMIDAZOLES: PART XIX-STRUCTURE-ACTIVITY RELATIONSHIPS", INDIAN JOURNAL OF CHEMISTRY : IJC, COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH, IN, vol. 23B, no. 4, 1 April 1984 (1984-04-01), pages 342 - 362, XP009065746, ISSN: 0019-5103 *

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