CA2368205A1 - Amines n-protege et leur utilisation en tant que promedicaments - Google Patents

Amines n-protege et leur utilisation en tant que promedicaments Download PDF

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Publication number
CA2368205A1
CA2368205A1 CA002368205A CA2368205A CA2368205A1 CA 2368205 A1 CA2368205 A1 CA 2368205A1 CA 002368205 A CA002368205 A CA 002368205A CA 2368205 A CA2368205 A CA 2368205A CA 2368205 A1 CA2368205 A1 CA 2368205A1
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CA
Canada
Prior art keywords
solution
mmol
etoac
nmr
och3
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.)
Abandoned
Application number
CA002368205A
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English (en)
Inventor
William Alexander Denny
Michael Patrick Hay
William Robert Wilson
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Auckland Uniservices Ltd
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Individual
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Filing date
Publication date
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Publication of CA2368205A1 publication Critical patent/CA2368205A1/fr
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 with nitro or nitroso radicals directly attached to ring carbon atoms
    • C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/16—Halogen atoms or 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

L'invention concerne des composés de formule (I) et (II), où X représente H, C1-6 alkyle ou C1-6 alkoxy, ledit alkyle ou alkoxy étant facultativement substitué par au moins un groupe, a est 0, 1, 2, 3, ou 4, Y représente H ou C1-6 alkyle, 1, 2 ou 3 des éléments Z de l'anneau aromatique à 5 branches sont sélectionnés indépendamment parmi -O-, -S-, -N= ou -NR-, où R représente H ou C1-6 alkyle facultativement substitué par au moins un des groupes, et E représente une fraction de telle manière que EH est un amine, étant stipulé que dans la formule (I) si a=0, alors Y?H. Cette invention concerne également un procédé de sélection de groupes de protection désirées en mesurant les taux de fragmentation des composés de la formule (I) ou (II), quand le groupe nitro est réduit.
CA002368205A 1999-04-26 2000-04-26 Amines n-protege et leur utilisation en tant que promedicaments Abandoned CA2368205A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9909612.5 1999-04-26
GBGB9909612.5A GB9909612D0 (en) 1999-04-26 1999-04-26 N-protected amines and their use as prodrugs
PCT/GB2000/001612 WO2000064864A1 (fr) 1999-04-26 2000-04-26 Amines n-protege et leur utilisation en tant que promedicaments

Publications (1)

Publication Number Publication Date
CA2368205A1 true CA2368205A1 (fr) 2000-11-02

Family

ID=10852308

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002368205A Abandoned CA2368205A1 (fr) 1999-04-26 2000-04-26 Amines n-protege et leur utilisation en tant que promedicaments

Country Status (7)

Country Link
EP (1) EP1173414A1 (fr)
JP (1) JP2002543059A (fr)
AU (1) AU762914B2 (fr)
CA (1) CA2368205A1 (fr)
GB (1) GB9909612D0 (fr)
NZ (1) NZ515044A (fr)
WO (1) WO2000064864A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103450091A (zh) * 2012-05-29 2013-12-18 南京大学 一类咪唑类衍生物及其制备方法与用途
CN103910681A (zh) * 2013-01-09 2014-07-09 南京大学 一类甲硝唑查尔酮衍生物及其制备方法与抗菌活性

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1109812B1 (fr) 1998-08-27 2005-05-04 Spirogen Limited Pyrrolo-benzodiazepines
GB9818730D0 (en) 1998-08-27 1998-10-21 Univ Portsmouth Collections of compounds
PE20040892A1 (es) * 2002-08-06 2004-11-19 Glaxo Group Ltd Antagonistas del receptor muscarinico m3 de acetilcolina
AU2003282624A1 (en) 2002-11-14 2004-06-03 Syntarga B.V. Prodrugs built as multiple self-elimination-release spacers
GB0226593D0 (en) 2002-11-14 2002-12-24 Consultants Ltd Compounds
ZA200507752B (en) * 2003-03-28 2007-01-31 Threshold Pharmaceuticals Inc Compositions and methods for treating cancer
GB0321295D0 (en) 2003-09-11 2003-10-15 Spirogen Ltd Synthesis of protected pyrrolobenzodiazepines
EP2336141B1 (fr) 2005-06-29 2016-03-30 Threshold Pharmaceuticals, Inc. Prodrogues d'alkylateur de phosphoramidate
RU2489423C2 (ru) * 2006-02-02 2013-08-10 Синтарга Б.В. Водорастворимые аналоги сс-1065 и их конъюгаты
US8552048B2 (en) 2006-12-26 2013-10-08 Threshold Pharmaceuticals, Inc. Phosphoramidate alkylator prodrugs for the treatment of cancer
EP2350664B1 (fr) 2008-10-21 2021-05-19 ImmunoGenesis, Inc. Traitement du cancer à l'aide du promédicament activé par l'hypoxie th-302 en combinaison avec le docetaxel ou le pemetrexed
JP6066421B2 (ja) 2010-07-12 2017-01-25 スレッショルド ファーマシューティカルズ、インク．Ｔｈｒｅｓｈｏｌｄ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ． 癌の治療のための低酸素活性化プロドラッグおよび血管新生阻害剤の投与方法
EP2793882A4 (fr) 2011-12-22 2015-04-29 Threshold Pharmaceuticals Inc Administration de promédicaments activés par l'hypoxie en combinaison à des inhibiteurs de chk1 pour le traitement du cancer
WO2013122112A1 (fr) 2012-02-13 2013-08-22 国立大学法人筑波大学 Promédicament à base de nitroimidazole
US9278124B2 (en) 2012-10-16 2016-03-08 Halozyme, Inc. Hypoxia and hyaluronan and markers thereof for diagnosis and monitoring of diseases and conditions and related methods
WO2015013448A1 (fr) 2013-07-26 2015-01-29 Threshold Pharmaceuticals, Inc. Traitement d'un cancer du pancréas au moyen d'une combinaison d'un promédicament activé par l'hypoxie et d'un taxane
WO2016001485A1 (fr) 2014-06-30 2016-01-07 Glykos Finland Oy Dérivé de saccharide d'une charge utile toxique et conjugués d'anticorps de celui-ci
CN105801434A (zh) * 2016-04-18 2016-07-27 宜兴市新宇化工有限公司 一种N,N-二(β-羟乙基)对苯二胺硫酸盐的生产工艺
CN107266407B (zh) * 2017-06-08 2020-08-21 浙江工业大学 一种响应硝基还原酶杀灭肿瘤细胞的光敏感靶向抗肿瘤前药及其制备方法与应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3450710A (en) * 1967-01-06 1969-06-17 Merck & Co Inc Process for the preparation of nitroimidazole carbamates
NL6717045A (fr) * 1967-01-06 1968-07-08
US5633158A (en) * 1991-10-23 1997-05-27 Cancer Research Campaign Technology Limited Bacterial nitroreductase for the reduction of CB 1954 and analogues thereof to a cytotoxic form
JP4155598B2 (ja) * 1996-09-12 2008-09-24 オークランド ユニサーヴィシズ リミテッド 抗癌剤としての縮合ｎ−アシルインドール
GB9625913D0 (en) * 1996-12-13 1997-01-29 Cancer Soc Auckland Div Nz Inc Novel cyclopropylindoles and their seco precursors,and their use as prodrugs

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103450091A (zh) * 2012-05-29 2013-12-18 南京大学 一类咪唑类衍生物及其制备方法与用途
CN103910681A (zh) * 2013-01-09 2014-07-09 南京大学 一类甲硝唑查尔酮衍生物及其制备方法与抗菌活性

Also Published As

Publication number Publication date
AU762914B2 (en) 2003-07-10
WO2000064864A1 (fr) 2000-11-02
GB9909612D0 (en) 1999-06-23
JP2002543059A (ja) 2002-12-17
EP1173414A1 (fr) 2002-01-23
NZ515044A (en) 2003-05-30
AU4421100A (en) 2000-11-10
WO2000064864A9 (fr) 2001-12-27

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