Title:
DUAL ACTION CARBONIC ANHYDRASE INHIBITORS
Document Type and Number:
WIPO Patent Application WO/2015/025283
Kind Code:
A3
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.
Inventors:
LAMBIN PHILIPPE (BE)
WINUM JEAN-YVES (FR)
WINUM JEAN-YVES (FR)
Application Number:
PCT/IB2014/063989
Publication Date:
July 23, 2015
Filing Date:
August 20, 2014
Export Citation:
Assignee:
STICHTING MAASTRICHT RADIATION ONCOLOGY MAASTRO CLINIC (NL)
International Classes:
C07F9/6506; A61K31/496; A61K31/5377; A61K31/664; A61P35/00; C07D233/91; C07D233/95; C07D403/06; C07H19/052
Domestic Patent References:
| WO2012087115A1 | 2012-06-28 | |||
| WO2013116385A1 | 2013-08-08 | |||
| WO2011098610A1 | 2011-08-18 | |||
| WO2012021963A1 | 2012-02-23 |
Other References:
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]
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
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
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
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
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
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
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
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
Attorney, Agent or Firm:
JANSEN, C.M. (Johan de Wittlaan 7, JR Den Haag, NL)
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