JP6458270B2 - 置換されたヒドロキサム酸化合物 - Google Patents

置換されたヒドロキサム酸化合物 Download PDF

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Publication number
JP6458270B2
JP6458270B2 JP2016534884A JP2016534884A JP6458270B2 JP 6458270 B2 JP6458270 B2 JP 6458270B2 JP 2016534884 A JP2016534884 A JP 2016534884A JP 2016534884 A JP2016534884 A JP 2016534884A JP 6458270 B2 JP6458270 B2 JP 6458270B2
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alkyl
alkoxy
compound
heteroaryl
aryl
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Expired - Fee Related
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JP2016534884A
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Japanese (ja)
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JP2016535758A (ja
JP2016535758A5 (enExample
Inventor
ジョウ ペイ
ジョウ ペイ
ジェイ.トゥーン エリック
ジェイ.トゥーン エリック
エー.ニコラス ロバート
エー.ニコラス ロバート
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University of North Carolina at Chapel Hill
Duke University
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University of North Carolina at Chapel Hill
Duke University
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/63One oxygen atom
    • C07D213/64One oxygen atom attached in position 2 or 6
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic 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
    • C07D231/12Heterocyclic 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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/04Heterocyclic 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
    • C07D295/12Heterocyclic 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
    • C07D295/135Heterocyclic 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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic 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
    • C07D295/04Heterocyclic 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
    • C07D295/14Heterocyclic 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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155Heterocyclic 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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Communicable Diseases (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)
  • Enzymes And Modification Thereof (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Pyridine Compounds (AREA)
JP2016534884A 2013-08-16 2014-08-18 置換されたヒドロキサム酸化合物 Expired - Fee Related JP6458270B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201361866823P 2013-08-16 2013-08-16
US61/866,823 2013-08-16
US201361867933P 2013-08-20 2013-08-20
US61/867,933 2013-08-20
PCT/US2014/051459 WO2015024010A2 (en) 2013-08-16 2014-08-18 Substituted hydroxamic acid compounds

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2018224004A Division JP2019077688A (ja) 2013-08-16 2018-11-29 置換されたヒドロキサム酸化合物

Publications (3)

Publication Number Publication Date
JP2016535758A JP2016535758A (ja) 2016-11-17
JP2016535758A5 JP2016535758A5 (enExample) 2017-09-28
JP6458270B2 true JP6458270B2 (ja) 2019-01-30

Family

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JP2016534884A Expired - Fee Related JP6458270B2 (ja) 2013-08-16 2014-08-18 置換されたヒドロキサム酸化合物
JP2018224004A Pending JP2019077688A (ja) 2013-08-16 2018-11-29 置換されたヒドロキサム酸化合物

Family Applications After (1)

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JP2018224004A Pending JP2019077688A (ja) 2013-08-16 2018-11-29 置換されたヒドロキサム酸化合物

Country Status (6)

Country Link
US (1) US10647664B2 (enExample)
EP (1) EP3041354A4 (enExample)
JP (2) JP6458270B2 (enExample)
AU (1) AU2014306451B2 (enExample)
CA (1) CA2921427A1 (enExample)
WO (1) WO2015024010A2 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019077688A (ja) * 2013-08-16 2019-05-23 デューク ユニバーシティ 置換されたヒドロキサム酸化合物

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9796686B2 (en) 2014-05-16 2017-10-24 Idorsia Pharmaceuticals Ltd Antibacterial quinazoline-4(3H)-one derivatives
ES2909122T3 (es) 2015-11-09 2022-05-05 Forge Therapeutics Inc Compuestos a base de hidroxipiridinona e hidroxipirimidinona para el tratamiento de infecciones bacterianas
EP3374355A4 (en) 2015-11-09 2019-04-17 Forge Therapeutics, Inc. COMPOUNDS BASED ON PYRONE AND METHOD FOR THE TREATMENT OF BACTERIAL INFECTIONS
US11034649B2 (en) 2016-04-25 2021-06-15 Duke University Benzoylglycine derivatives and methods of making and using same
CN110072844B (zh) 2016-12-23 2023-06-02 英特维特国际股份有限公司 用于治疗溶血曼海姆菌或睡眠嗜组织菌感染的化合物
US11021471B2 (en) 2017-05-10 2021-06-01 Forge Therapeutics, Inc. Antibacterial compounds
SG11202007665RA (en) * 2018-02-10 2020-09-29 Kbp Biosciences Co Ltd Compound acting as antibiotics
CA3113226A1 (en) * 2018-09-20 2020-03-26 Forge Therapeutics, Inc. Antibacterial compounds
WO2021195260A1 (en) 2020-03-25 2021-09-30 Forge Therapeutics, Inc. Lpxc inhibitor and methods of making
DK4210700T3 (da) 2020-09-09 2025-09-08 Crinetics Pharmaceuticals Inc Formuleringer af en somatostatinmodulator
WO2023055686A1 (en) 2021-09-28 2023-04-06 Blacksmith Medicines, Inc. Lpxc inhibitors and uses thereof
WO2024077160A2 (en) * 2022-10-05 2024-04-11 Duke University Compositions comprising prodrugs of hydroxyamate-based compounds and methods of making and using same

Family Cites Families (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993014077A1 (en) 1992-01-21 1993-07-22 Glaxo Group Limited Piperidineacetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation
TW448172B (en) 1996-03-08 2001-08-01 Pharmacia & Upjohn Co Llc Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation
US5925659A (en) 1996-05-07 1999-07-20 Merck & Co., Inc. Antibacterial agents
GB9725782D0 (en) 1997-12-05 1998-02-04 Pfizer Ltd Therapeutic agents
JP2000344752A (ja) * 1999-04-01 2000-12-12 Sumitomo Pharmaceut Co Ltd 点眼剤
US6511993B1 (en) 1999-06-03 2003-01-28 Kevin Neil Dack Metalloprotease inhibitors
PL207295B1 (pl) * 2002-01-29 2010-11-30 Serono Lab Podstawione pochodne metylenoamidowe , ich zastosowanie i sposób ich wytwarzania oraz kompozycja farmaceutyczna
BR0309671A (pt) 2002-04-25 2005-05-03 Pharmacia Corp ácidos de piperidinil- e piperazinil-sulfonilmetil hidroxâmicos e seu uso como inibidores de protease
KR101011373B1 (ko) 2002-07-11 2011-01-28 비큐론 파마슈티컬스 인코포레이티드 항균작용을 갖는 n-히드록시아미드 유도체
ES2552247T3 (es) * 2003-01-08 2015-11-26 The University Of Washington Agentes antibacterianos
US20050154022A1 (en) 2004-01-14 2005-07-14 H. Lundbeck A/S 4-aryl piperidines
US7638513B2 (en) 2004-06-02 2009-12-29 Schering Corporation Compounds for the treatment of inflammatory disorders
AT502219B1 (de) 2005-08-04 2007-04-15 Sanochemia Pharmazeutika Ag Verfahren zur reindarstellung von 5-substituierten tetrazolen
EP1957449A1 (en) 2005-12-01 2008-08-20 Schering Corporation Compounds for the treatment of inflammatory disorders and microbial diseases
CN101528711A (zh) 2006-08-31 2009-09-09 先灵公司 可用作抗细菌剂的乙内酰脲衍生物
WO2008105515A1 (ja) 2007-02-28 2008-09-04 Taisho Pharmaceutical Co., Ltd. 新規なヒドロキサム酸誘導体
CN101765585B (zh) 2007-06-12 2017-03-15 尔察祯有限公司 抗菌剂
JP2011525927A (ja) 2008-06-25 2011-09-29 シェーリング コーポレイション 複素環式抗菌剤の合成および使用
CA2732045A1 (en) 2008-08-04 2010-02-11 Schering Corporation Urea derivatives as antibacterial agents
JP5455913B2 (ja) 2008-08-27 2014-03-26 大正製薬株式会社 ナフチリジン−n−オキシドを有する新規ヒドロキサム酸誘導体
US8372885B2 (en) * 2008-09-17 2013-02-12 Novartis Ag Organic compounds and their uses
WO2010100475A1 (en) 2009-03-02 2010-09-10 Astrazeneca Ab Hydroxamic acid derivatives as gram-negative antibacterial agents
WO2011005355A1 (en) 2009-05-07 2011-01-13 Achaogen, Inc. Combinations comprising a lpxc inhibitor and an antibiotic for use in the treatment of infections caused by gram-negative bacteria
CA2774250C (en) 2009-10-13 2013-12-17 Pfizer Inc. C-linked hydroxamic acid derivatives useful as antibacterial agents
US8389536B2 (en) 2009-10-27 2013-03-05 Hoffmann-La Roche Inc. Positive allosteric modulators (PAM)
SI2512474T1 (sl) 2009-12-16 2014-12-31 Pfizer Inc. N-vezani derivati hidroksamske kisline, uporabni kot protibakterijska sredstva
SMT201900482T1 (it) * 2010-04-20 2019-09-09 Fujifilm Toyama Chemical Co Ltd Derivato dell'acido idrossammico
US9738604B2 (en) * 2010-09-03 2017-08-22 Duke University Ethynylbenzene derivatives
US8772300B2 (en) * 2011-04-19 2014-07-08 Hoffmann-La Roche Inc. Phenyl or pyridinyl-ethynyl derivatives
WO2013049255A1 (en) * 2011-09-26 2013-04-04 Vanderbilt University Substitued 5-(prop-1-yn-1-yl)picolinamide analogs as allosteric modulators of mglur5 receptors
JP6006609B2 (ja) * 2011-10-19 2016-10-12 大正製薬株式会社 新規なヒドロキサム酸誘導体を含有する医薬
WO2013170165A1 (en) * 2012-05-10 2013-11-14 Achaogen, Inc. Antibacterial agents
SI2975022T1 (sl) * 2013-03-15 2019-08-30 Fujifilm Toyama Chemical Co., Ltd. Novi derivati hidroksamske kisline ali soli le-teh
WO2015024010A2 (en) * 2013-08-16 2015-02-19 Duke University Substituted hydroxamic acid compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019077688A (ja) * 2013-08-16 2019-05-23 デューク ユニバーシティ 置換されたヒドロキサム酸化合物

Also Published As

Publication number Publication date
EP3041354A2 (en) 2016-07-13
EP3041354A4 (en) 2017-06-14
WO2015024010A2 (en) 2015-02-19
AU2014306451A1 (en) 2016-03-03
JP2016535758A (ja) 2016-11-17
WO2015024010A3 (en) 2015-04-16
AU2014306451B2 (en) 2019-01-17
JP2019077688A (ja) 2019-05-23
US20160221934A1 (en) 2016-08-04
CA2921427A1 (en) 2015-02-19
US10647664B2 (en) 2020-05-12

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