WO2014030142A3 - Nitroimidazole compounds and their use in cancer therapy - Google Patents

Nitroimidazole compounds and their use in cancer therapy Download PDF

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Publication number
WO2014030142A3
WO2014030142A3 PCT/IB2013/056824 IB2013056824W WO2014030142A3 WO 2014030142 A3 WO2014030142 A3 WO 2014030142A3 IB 2013056824 W IB2013056824 W IB 2013056824W WO 2014030142 A3 WO2014030142 A3 WO 2014030142A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
cancer therapy
nitroimidazole compounds
compound
compounds
Prior art date
Application number
PCT/IB2013/056824
Other languages
French (fr)
Other versions
WO2014030142A2 (en
Inventor
Michael Hay
Jingli Wang
Frederik Bastiaan Pruijn
Muriel Bonnet
Kevin Hicks
Original Assignee
Auckland Uniservices Limited
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 Auckland Uniservices Limited filed Critical Auckland Uniservices Limited
Publication of WO2014030142A2 publication Critical patent/WO2014030142A2/en
Publication of WO2014030142A3 publication Critical patent/WO2014030142A3/en

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Classifications

    • 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
    • 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
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof, formula (I) wherein m, n, X, Y and Z are as defined herein. Also provided are pharmaceutical compositions containing compounds of Formula (I), and methods of treating cancer and/or improving the response of tumors to radiotherapy by administering a compound of Formula (I) to a warm-blooded animal.
PCT/IB2013/056824 2012-08-24 2013-08-23 Nitroimidazole compounds and their use in cancer therapy WO2014030142A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NZ602023 2012-08-24
NZ60202312 2012-08-24

Publications (2)

Publication Number Publication Date
WO2014030142A2 WO2014030142A2 (en) 2014-02-27
WO2014030142A3 true WO2014030142A3 (en) 2014-04-17

Family

ID=50150445

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2013/056824 WO2014030142A2 (en) 2012-08-24 2013-08-23 Nitroimidazole compounds and their use in cancer therapy

Country Status (1)

Country Link
WO (1) WO2014030142A2 (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1215858A (en) * 1968-05-03 1970-12-16 Merck & Co Inc Nitroimidazole derivatives
US3629431A (en) * 1969-06-16 1971-12-21 Pfizer Use of 1-alkylsulfonylalkyl-2-alkyl-5 - nitroimidazoles in controlling coccidiosis
AU3432971A (en) * 1970-10-08 1973-04-12 CARLO ERBA Sp. A Substituted 2,2-biimidazoles and process for their preperation
GB1399291A (en) * 1971-09-02 1975-07-02 Merck & Co Inc 5-cyano-4-nitroimidazoles and their preparation
DE2515110A1 (en) * 1974-04-19 1975-10-23 Crc Ricerca Chim PROCESS FOR THE PREPARATION OF 5-NITROIMIDAZOLE DERIVATIVES
CN1634041A (en) * 2004-10-29 2005-07-06 文斌 Use of anti-infective drug in treating cancer

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1215858A (en) * 1968-05-03 1970-12-16 Merck & Co Inc Nitroimidazole derivatives
US3629431A (en) * 1969-06-16 1971-12-21 Pfizer Use of 1-alkylsulfonylalkyl-2-alkyl-5 - nitroimidazoles in controlling coccidiosis
AU3432971A (en) * 1970-10-08 1973-04-12 CARLO ERBA Sp. A Substituted 2,2-biimidazoles and process for their preperation
GB1399291A (en) * 1971-09-02 1975-07-02 Merck & Co Inc 5-cyano-4-nitroimidazoles and their preparation
DE2515110A1 (en) * 1974-04-19 1975-10-23 Crc Ricerca Chim PROCESS FOR THE PREPARATION OF 5-NITROIMIDAZOLE DERIVATIVES
CN1634041A (en) * 2004-10-29 2005-07-06 文斌 Use of anti-infective drug in treating cancer

Non-Patent Citations (14)

* Cited by examiner, † Cited by third party
Title
BHUJANGA RAO, A. K. S. ET AL.: "Novel Synthesis of 4(5)-Cyclic Amino-5(4)- Nitroimidazoles", SYNTHETIC COMMUNICATIONS, vol. 24, no. 3, 1994, pages 341 - 351 *
BHUJANGA RAO, A. K. S. ET AL.: "Regioselective Alkylation of 4(5)-Nitro-1H-Imidazoles in Acetic Media: Study of Temperature Effects", J. CHEM. SOC. PERKINS TRANS., vol. 1, no. 17, 1994, pages 2399 - 2402 *
CHEMICAL ABSTRACTS, 16 November 1984, Columbus, Ohio, US; abstract no. 28795-25-7 *
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 52455-84-2 *
DESAI, D. G. ET AL.: "Synthesis and Antibacterial Activity of Nickel Complex of some Novel Nitroimidazole", PHARMA SCIENCE MONITOR, vol. 3, no. 2, April 2012 (2012-04-01), pages 133 - 141 *
HAY, M. P. ET AL.: "Hypoxia-Selective Antitumor Agents. 10. Bis nitroimidazoles) and Related Bis(nitroheterocycles): Development of Derivatives with Higher Rates of Metabolic Activation under Hypoxia and Improved Aqueous Solubility", J. MED. CHEM., vol. 38, 1996, pages 1928 - 1941 *
LONG, W. ET AL.: "Quantitative Structure Activity Relationship Modeling for Predicting Radiosensitization Effectiveness of Nitroimidazole Compounds", J. RADIAT. RES., vol. 51, 2010, pages 563 - 572 *
MARTIN BROWN, J. ET AL.: "Partition Coefficient as a Guide to the Development of Radiosensitizers which are Less Toxic than Misonidazole", RADIATION RESEARCH, vol. 82, no. 1, 1980, pages 171 - 190 *
RAMALHO, T. C. ET AL.: "Theoretical evaluation of adiabatic and vertical electron affinity of some radiosensitizers in solution using FEP, ab initio and DFT methods", BIOPHYSICAL CHEMISTRY, vol. 110, 2004, pages 267 - 279 *
SALAHUDDIN, A. ET AL.: "Metronidazole thiosalicylate conjugates: Synthesis, crystal structure, docking studies and antiamoebic activity", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 22, July 2012 (2012-07-01), pages 5694 - 5699 *
SCOTT, P. W. ET AL.: "A Novel Metabolite of Tinidazole involving Nitro-group migration", BIOCHEMICAL PHARMACOLOGY, vol. 34, no. 3, 1985, pages 451 - 458 *
SHANKER, S. ET AL.: "Sensitivity of Gardnerella Vaginalis to Metabolites of Metronidazole and Tinidazole", THE LANCET, 1982, pages 167 *
STRATFORD, M. R. L. ET AL.: "Radiosensitizer-DNA Interactions in Relation to Intracellular Uptake", INT. J. RADIATION ONCOLOGY BID PHYS.., vol. 16, 1989, pages 1007 - 1010 *
WINKELMANN, E. ET AL.: "Chemotherapeutically Active Nitro Compounds", ARZNEIM.- FORSCH., vol. 27, no. 12, 1977, pages 2251 - 2263 *

Also Published As

Publication number Publication date
WO2014030142A2 (en) 2014-02-27

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