AU2003278628B2 - Nitroaniline-based alkylating agents and their use as prodrugs - Google Patents

Nitroaniline-based alkylating agents and their use as prodrugs Download PDF

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Publication number
AU2003278628B2
AU2003278628B2 AU2003278628A AU2003278628A AU2003278628B2 AU 2003278628 B2 AU2003278628 B2 AU 2003278628B2 AU 2003278628 A AU2003278628 A AU 2003278628A AU 2003278628 A AU2003278628 A AU 2003278628A AU 2003278628 B2 AU2003278628 B2 AU 2003278628B2
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AU
Australia
Prior art keywords
amino
conh
etoac
nmr
formula
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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.)
Ceased
Application number
AU2003278628A
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English (en)
Other versions
AU2003278628A1 (en
Inventor
Graham J. Atwell
William Alexander Denny
Adam V. Patterson
William Robert Wilson
Shangjin Yang
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Auckland Uniservices Ltd
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Auckland Uniservices Ltd
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
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Publication of AU2003278628A1 publication Critical patent/AU2003278628A1/en
Application granted granted Critical
Publication of AU2003278628B2 publication Critical patent/AU2003278628B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
AU2003278628A 2002-10-08 2003-10-08 Nitroaniline-based alkylating agents and their use as prodrugs Ceased AU2003278628B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
NZNZ521851 2002-10-08
NZ521851A NZ521851A (en) 2002-10-08 2002-10-08 Nitroaniline-based unsymmetrical mustard alkylating agents for gene dependent enzyme prodrug therapy
PCT/NZ2003/000225 WO2004033415A1 (en) 2002-10-08 2003-10-08 Nitroaniline-based alkylating agents and their use as prodrugs

Publications (2)

Publication Number Publication Date
AU2003278628A1 AU2003278628A1 (en) 2004-05-04
AU2003278628B2 true AU2003278628B2 (en) 2010-09-23

Family

ID=32089872

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2003278628A Ceased AU2003278628B2 (en) 2002-10-08 2003-10-08 Nitroaniline-based alkylating agents and their use as prodrugs

Country Status (8)

Country Link
US (1) US7776924B2 (enExample)
EP (1) EP1558568A4 (enExample)
JP (2) JP4582519B2 (enExample)
CN (1) CN100546976C (enExample)
AU (1) AU2003278628B2 (enExample)
CA (1) CA2501388C (enExample)
NZ (1) NZ521851A (enExample)
WO (1) WO2004033415A1 (enExample)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2004285831B2 (en) * 2003-10-31 2011-09-15 Auckland Uniservices Limited Novel nitrophenyl mustard and nitrophenylaziridine alcohols and their corresponding phosphates and their use as targeted cytotoxic agents
JP4761899B2 (ja) * 2005-09-12 2011-08-31 Ｈｏｙａ株式会社 電子内視鏡システム
NZ549659A (en) * 2006-09-04 2008-12-24 Auckland Uniservices Ltd Processes of preparing asymmetric dinitrobenzamide mustard compounds, intermediate compounds useful therein and products obtained therefrom
WO2010048330A1 (en) 2008-10-21 2010-04-29 Threshold Pharmaceuticals, Inc. Treatment of cancer using hypoxia activated prodrugs
CN101723932B (zh) * 2008-10-31 2013-11-20 北京以岭生物工程技术有限公司 硝基吡啶乙烯亚胺化合物、其药物组合物及其制备方法和用途
RU2597844C2 (ru) 2010-07-12 2016-09-20 Тресхолд Фармасьютикалз, Инк. Введение гипоксически активируемых пролекарств и средств, препятствующих ангиогенезу, для лечения рака
EP2793882A4 (en) 2011-12-22 2015-04-29 Threshold Pharmaceuticals Inc ADMINISTRATION OF HYPOXIA-ACTIVATED PRODRUGS IN COMBINATION WITH CHK1 INHIBITORS FOR THE TREATMENT OF CANCER
EP2888227B1 (en) * 2012-08-23 2020-07-29 Convert Pharmaceuticals SA Novel prodrugs and methods of use thereof
US10202408B2 (en) 2012-08-23 2019-02-12 Health Innovation Ventures B.V. Prodrugs and methods of use thereof
WO2014062856A1 (en) 2012-10-16 2014-04-24 Halozyme, Inc. Hypoxia and hyaluronan and markers thereof for diagnosis and monitoring of diseases and conditions and related methods
US20160158253A1 (en) 2013-07-26 2016-06-09 Threshold Pharmaceuticals, Inc. Treatment of pancreatic cancer with a combination of a hypoxia-activated prodrug and a taxane
AU2015332533B2 (en) 2014-10-14 2018-08-30 Halozyme, Inc. Compositions of adenosine deaminase-2 (ADA2), variants thereof and methods of using same
US20180169064A1 (en) 2015-06-24 2018-06-21 Threshold Pharmaceuticals, Inc. Aziridine containing dna alkylating agents
CN106995815B (zh) * 2016-01-22 2020-09-01 南京农业大学 硝基还原酶基因pnr及其编码的蛋白和应用
CN106905184B (zh) * 2017-03-05 2019-03-29 北京化工大学 含有苯甲酰胺基团的氮芥类化合物及其制备方法和用途
WO2019190331A1 (en) * 2018-03-29 2019-10-03 Achilles Medical Limited Prodrug compounds activated by akr1c3 and their use for treating hyperproliferative disorders
CN112961082B (zh) * 2021-02-22 2022-09-06 沈阳药科大学 一种血管阻断剂与双载药仿生脂质体联用的给药系统

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8705477D0 (en) 1987-03-09 1987-04-15 Carlton Med Prod Drug delivery systems
NZ240785A (en) * 1991-11-28 1995-08-28 Cancer Res Campaign Tech Substituted nitro aniline derivatives and medicaments

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Friedlos, F. et al., J. Med. Chem., 1997, 40, 1270-1275 *

Also Published As

Publication number Publication date
JP2010265272A (ja) 2010-11-25
CN100546976C (zh) 2009-10-07
AU2003278628A1 (en) 2004-05-04
CA2501388C (en) 2011-01-04
JP4582519B2 (ja) 2010-11-17
US20050256191A1 (en) 2005-11-17
US7776924B2 (en) 2010-08-17
JP2006502214A (ja) 2006-01-19
CN1711236A (zh) 2005-12-21
NZ521851A (en) 2005-02-25
EP1558568A4 (en) 2006-10-18
EP1558568A1 (en) 2005-08-03
CA2501388A1 (en) 2004-04-22
WO2004033415A1 (en) 2004-04-22

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Free format text: THE NATURE OF THE AMENDMENT IS:ADD CO-INVENTOR PATTERSON, ADAM V.

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MK14 Patent ceased section 143(a) (annual fees not paid) or expired