JP5662940B2 - 新規な抗微生物薬 - Google Patents

新規な抗微生物薬 Download PDF

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Publication number
JP5662940B2
JP5662940B2 JP2011537013A JP2011537013A JP5662940B2 JP 5662940 B2 JP5662940 B2 JP 5662940B2 JP 2011537013 A JP2011537013 A JP 2011537013A JP 2011537013 A JP2011537013 A JP 2011537013A JP 5662940 B2 JP5662940 B2 JP 5662940B2
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JP
Japan
Prior art keywords
heteroaryl
alkoxy
alkyl
aryl
heterocyclyl
Prior art date
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Expired - Fee Related
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JP2011537013A
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Japanese (ja)
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JP2012509313A (ja
JP2012509313A5 (https=
Inventor
ラジェッシュ ジェーン
ラジェッシュ ジェーン
サンジェイ トレハン
サンジェイ トレハン
ジャガッタラン ダス
ジャガッタラン ダス
サンディープ カンワー
サンディープ カンワー
シタラム クマール マガディ
シタラム クマール マガディ
スディール クマール シャルマ
スディール クマール シャルマ
Original Assignee
パナセア バイオテック リミテッド
パナセア バイオテック リミテッド
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Publication of JP2012509313A5 publication Critical patent/JP2012509313A5/ja
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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic 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
    • C07D487/04Ortho-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42Oxazoles
    • A61K31/422Oxazoles not condensed and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • A61P31/06Antibacterial agents for tuberculosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • A61P31/16Antivirals for RNA viruses for influenza or rhinoviruses
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/18Oxygen atoms
    • C07D263/20Oxygen atoms attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Pulmonology (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
JP2011537013A 2008-11-20 2009-11-18 新規な抗微生物薬 Expired - Fee Related JP5662940B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN2623/DEL/2008 2008-11-20
IN2623DE2008 2008-11-20
PCT/IN2009/000658 WO2010058423A2 (en) 2008-11-20 2009-11-18 Novel antimicrobials

Publications (3)

Publication Number Publication Date
JP2012509313A JP2012509313A (ja) 2012-04-19
JP2012509313A5 JP2012509313A5 (https=) 2012-12-27
JP5662940B2 true JP5662940B2 (ja) 2015-02-04

Family

ID=42198604

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2011537013A Expired - Fee Related JP5662940B2 (ja) 2008-11-20 2009-11-18 新規な抗微生物薬

Country Status (12)

Country Link
US (1) US8841306B2 (https=)
EP (1) EP2367820B1 (https=)
JP (1) JP5662940B2 (https=)
KR (1) KR20110092309A (https=)
CN (1) CN102224151A (https=)
AR (1) AR074387A1 (https=)
AU (1) AU2009318783A1 (https=)
CA (1) CA2743971A1 (https=)
MX (1) MX2011005365A (https=)
RU (1) RU2522582C2 (https=)
WO (1) WO2010058423A2 (https=)
ZA (1) ZA201103978B (https=)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2532703T3 (es) 2010-10-13 2015-03-31 Glaxo Group Limited Derivados de 3-amino-pirazol útiles contra la tuberculosis
PT106651A (pt) * 2012-11-20 2014-05-20 Tecnimede Sociedade Tecnico Medicinal S A Quinolil hidrazonas para o tratamento de tuberculose e doenças relacionadas
CN103450173B (zh) * 2013-09-07 2015-06-03 吉首大学 吡咯酮-苯基-噁唑烷酮型化合物及其制法和用途
WO2017156519A1 (en) 2016-03-11 2017-09-14 The Board Of Trustees Of The University Of Illinois Small-molecules active against gram-negative bacteria
US11274106B2 (en) 2017-06-23 2022-03-15 The Board Of Trustees Of The University Of Illinois Topoisomerase inhibitors with antibacterial and anticancer activity
AU2021217225A1 (en) * 2020-02-07 2022-10-06 University Of South Florida Inhibition of beta-arrestin oligomerization in tauopathy

Family Cites Families (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE146783T1 (de) 1991-11-01 1997-01-15 Upjohn Co Substituierte aryl- und heteroaryl- phenyloxazolidinone
SK283420B6 (sk) * 1992-05-08 2003-07-01 Pharmacia & Upjohn Company Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny
WO1995007272A1 (fr) 1993-09-06 1995-03-16 Fujisawa Pharmaceutical Co., Ltd. Compose de cyclodepsipeptide
NZ306310A (en) 1995-05-11 2001-05-25 Upjohn Co Spirocyclic and bicyclic diazinyl and carbazinyl oxazolidinones
RU2175324C2 (ru) 1995-09-01 2001-10-27 Фармация Энд Апджон Компани Фенилоксазолидиноны, имеющие с-с-связь с 4-8-членными гетероциклическими кольцами
GB9702213D0 (en) * 1996-02-24 1997-03-26 Zeneca Ltd Chemical compounds
TR200003595T2 (tr) * 1998-06-05 2001-07-23 Astrazeneca Ab Kimyasal bileşikler
JP2000204084A (ja) * 1998-11-11 2000-07-25 Hokuriku Seiyaku Co Ltd チオカルバミド酸誘導体
WO2000029396A1 (de) 1998-11-17 2000-05-25 Bayer Aktiengesellschaft Neue substituierte phenyloxazolidon-derivate
ES2203473T3 (es) 1999-05-27 2004-04-16 PHARMACIA & UPJOHN COMPANY Oxazolidinonas biciclicas como agentes antibacterianos.
US6608081B2 (en) 1999-08-12 2003-08-19 Ortho-Mcneil Pharmaceutical, Inc. Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods
BR0111280A (pt) 2000-06-05 2003-06-10 Dong A Pharm Co Ltd Novos derivados de oxazolidinona e um processo para a preparação dos mesmos
ES2245698T3 (es) 2000-06-30 2006-01-16 PHARMACIA & UPJOHN COMPANY LLC Composiciones para el tratamiento de infecciones bacterianas que contienen un compuesto de oxazolidinona, sulbactam y ampicilina.
DOP2002000333A (es) 2001-02-14 2002-09-30 Warner Lambert Co Derivados de acido isoftalico como inhibidores de metaloproteinasas de la matriz
ES2268011T3 (es) 2001-04-07 2007-03-16 Astrazeneca Ab Oxazolidinonas que contienen un grupo sulfonimida como antibioticos.
GB0108793D0 (en) 2001-04-07 2001-05-30 Astrazeneca Ab Chemical compounds
AU2002333233A1 (en) 2001-07-09 2003-01-29 Pharmacia Italia Spa Interaction inhibitors of tcf-4 with beta-catenin
EP1409464A4 (en) 2001-07-16 2005-11-02 Ranbaxy Lab Ltd OXAZOLIDINONE DERIVATIVES AS POTENTIAL ANTIMICROBIALS
AR038536A1 (es) 2002-02-25 2005-01-19 Upjohn Co N-aril-2-oxazolidinona-5- carboxamidas y sus derivados
US20050209248A1 (en) 2002-05-15 2005-09-22 Biswajit Das Plymorphic forms of phenyl oxazolidinone derivatives
WO2003097640A1 (en) 2002-05-22 2003-11-27 Orchid Chemicals & Pharmaceuticals Ltd. Oxazolidinone derivatives as antibacterial agents
WO2004009587A1 (en) 2002-07-22 2004-01-29 Orchid Chemicals & Pharmaceuticals Ltd Oxazolidinone derivatives as antibacterial agents
MXPA05001199A (es) 2002-07-29 2005-05-16 Ranbaxy Lab Ltd Derivados de oxazolidinona como antimicrobianos.
EP1578734A1 (en) 2002-08-22 2005-09-28 Orchid Chemicals and Pharmaceuticals Ltd Novel antibacterial agents
US6875784B2 (en) 2002-10-09 2005-04-05 Pharmacia & Upjohn Company Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives
JP2006509035A (ja) * 2002-11-21 2006-03-16 ファルマシア・アンド・アップジョン・カンパニー・エルエルシー 抗菌剤としてのn−(4−(ピペラジン−1−イル)−フェニル−2−オキサゾリジノン−5−カルボキサミド誘導体および関連化合物
GB0229526D0 (en) 2002-12-19 2003-01-22 Astrazeneca Ab Chemical compounds
GB0229518D0 (en) 2002-12-19 2003-01-22 Astrazeneca Ab Chemical compounds
CN1237056C (zh) * 2002-12-25 2006-01-18 中国科学院上海药物研究所 噁唑烷酮类化合物、其制备方法和用途
US20080214565A1 (en) * 2003-04-07 2008-09-04 Anita Mehta Oxazolidinone Derivatives as Antimicrobials
BRPI0409217A (pt) 2003-04-09 2006-03-28 Pharmacia & Upjohn Co Llc derivados e análogos antimicrobianos da [3.1.0]bicicloexilfeniloxazolidinona
WO2004113329A1 (en) 2003-06-20 2004-12-29 Orchid Chemicals And Pharmaceuticals Ltd. Oxazole derivatives as antibacterial agents
WO2005003087A2 (en) 2003-07-01 2005-01-13 Orchid Chemicals And Pharmaceuticals Ltd. Oxazole derivatives as antibacterial agents
CA2529294A1 (en) 2003-07-02 2005-01-20 Merck & Co., Inc. Oxazolidinone antibiotics and derivatives thereof
WO2005005399A1 (en) 2003-07-02 2005-01-20 Merck & Co., Inc. Oxazolidinone antibiotics and derivatives thereof
WO2005036169A2 (en) * 2003-10-03 2005-04-21 Cumbre Inc. Fluorescent probes for ribosomes and method of use
KR100854211B1 (ko) 2003-12-18 2008-08-26 동아제약주식회사 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물
WO2005082897A1 (en) 2004-01-28 2005-09-09 Pharmacia & Upjohn Company Llc Oxazolidinone antibacterial agents
WO2005082900A2 (en) 2004-01-28 2005-09-09 Pharmacia & Upjohn Company Llc Oxazolidinone amidoximes as antibacterial agents
WO2005116024A1 (en) 2004-05-25 2005-12-08 Astrazeneca Ab 3- (4- (2-dihydroisoxazol-3-ylpyridin-5-yl) phenyl) -5-triazol-1-ylmethyloxazolidin-2-one derivaives as mao inhibitors for the treatment of bacterial infections
US20080064689A1 (en) 2004-05-25 2008-03-13 Astrazeneca Ab 3-[4-(6-Pyridin-3-Yl)-3-Phenyl] -5-(1H-1,2,3-Triazol-1-Ylmethyl)-1,3-Oxazolidin-2-Ones as Antibacterial Agents
WO2006035283A1 (en) 2004-09-27 2006-04-06 Ranbaxy Laboratories Limited Oxazolidinone derivatives as antimicrobials
WO2006043121A1 (en) 2004-10-20 2006-04-27 Ranbaxy Laboratories Limited Oxazolidinone derivatives as antimicrobials
JP5289043B2 (ja) 2005-04-12 2013-09-11 ヴィコール・ファルマ・アーベー 新規な三環系アンジオテンシンiiアゴニスト
EP1745784A1 (en) 2005-06-27 2007-01-24 Ferrer Internacional, S.A. Oxazolidinone derivatives and use thereof as antibiotics
WO2007004037A1 (en) 2005-07-06 2007-01-11 Pharmacia & Upjohn Company Llc Oxazolidinone carboxamides containing azetidine and cyclobutane as antibacterial agents
KR20070038236A (ko) 2005-10-05 2007-04-10 일동제약주식회사 신규 옥사졸리디논 포름 아미드 유도체 및 그 제조방법
JP2009523764A (ja) * 2006-01-19 2009-06-25 ラボラトリオス・サルバト・ソシエダッド・アノニマ 抗菌活性を有するジカルボニル化合物
US20090318431A1 (en) 2006-02-14 2009-12-24 Pfizer Inc. Benzoxazinone and benzoxazepinone oxazolidinones as antibacterial agents
CN100406455C (zh) 2006-02-20 2008-07-30 中国科学院上海药物研究所 含三氮唑基的噁唑烷酮类化合物及其制备方法和用途
KR20080110877A (ko) 2006-03-31 2008-12-19 재단법인 이쯔우 연구소 헤테로환을 갖는 신규 화합물
WO2009001192A2 (en) * 2007-06-22 2008-12-31 Orchid Research Laboratories Limited Novel compounds and their use
CN101434584A (zh) * 2007-11-15 2009-05-20 中山大学 具有抗菌活性的手性噁唑烷酮类化合物

Also Published As

Publication number Publication date
EP2367820A4 (en) 2012-06-20
WO2010058423A2 (en) 2010-05-27
EP2367820A2 (en) 2011-09-28
CA2743971A1 (en) 2010-05-27
WO2010058423A9 (en) 2011-04-28
RU2011124795A (ru) 2012-12-27
US8841306B2 (en) 2014-09-23
US20110245258A1 (en) 2011-10-06
AR074387A1 (es) 2011-01-12
ZA201103978B (en) 2012-09-26
MX2011005365A (es) 2011-06-24
RU2522582C2 (ru) 2014-07-20
KR20110092309A (ko) 2011-08-17
AU2009318783A1 (en) 2011-06-23
EP2367820B1 (en) 2016-09-21
JP2012509313A (ja) 2012-04-19
WO2010058423A3 (en) 2010-12-09
CN102224151A (zh) 2011-10-19

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