CN101855219B - 6,11-桥联的联芳大环内酯类 - Google Patents

6,11-桥联的联芳大环内酯类 Download PDF

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Publication number
CN101855219B
CN101855219B CN200880115910.7A CN200880115910A CN101855219B CN 101855219 B CN101855219 B CN 101855219B CN 200880115910 A CN200880115910 A CN 200880115910A CN 101855219 B CN101855219 B CN 101855219B
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compound
substituted
group
compounds
hydrogen
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Chinese (zh)
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CN101855219A (zh
Inventor
金寅锤
刘同柱
龙江
王国强
邱遥龄
金希珍
王燕春
潘心理
柯日新
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Enanta Pharmaceuticals Inc
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Enanta Pharmaceuticals Inc
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    • 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
    • C07D417/14Heterocyclic 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 three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08Hetero rings containing eight or more ring members, e.g. erythromycins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D213/69Two or more oxygen atoms
    • 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79Acids; Esters
    • C07D213/80Acids; Esters in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D309/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C07D309/40Oxygen atoms attached in positions 3 and 4, e.g. maltol
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
CN200880115910.7A 2007-09-17 2008-09-17 6,11-桥联的联芳大环内酯类 Expired - Fee Related CN101855219B (zh)

Applications Claiming Priority (19)

Application Number Priority Date Filing Date Title
US97301707P 2007-09-17 2007-09-17
US60/973,017 2007-09-17
US97320107P 2007-09-18 2007-09-18
US60/973,201 2007-09-18
US5187508P 2008-05-09 2008-05-09
US5185708P 2008-05-09 2008-05-09
US5186208P 2008-05-09 2008-05-09
US61/051,857 2008-05-09
US61/051,875 2008-05-09
US61/051,862 2008-05-09
US7621308P 2008-06-27 2008-06-27
US7620808P 2008-06-27 2008-06-27
US61/076,208 2008-06-27
US61/076,213 2008-06-27
US9511108P 2008-09-08 2008-09-08
US9510008P 2008-09-08 2008-09-08
US61/095,100 2008-09-08
US61/095,111 2008-09-08
PCT/US2008/076731 WO2009075923A2 (en) 2007-09-17 2008-09-17 6, 11-bridged biaryl macrolides

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CN201410219293.2A Division CN104004039A (zh) 2007-09-17 2008-09-17 6,11-桥联的联芳大环内酯类

Publications (2)

Publication Number Publication Date
CN101855219A CN101855219A (zh) 2010-10-06
CN101855219B true CN101855219B (zh) 2014-06-25

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CN200880115910.7A Expired - Fee Related CN101855219B (zh) 2007-09-17 2008-09-17 6,11-桥联的联芳大环内酯类
CN201410219293.2A Pending CN104004039A (zh) 2007-09-17 2008-09-17 6,11-桥联的联芳大环内酯类

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US (2) US20090118506A1 (enExample)
EP (1) EP2203435B1 (enExample)
JP (2) JP5642548B2 (enExample)
KR (2) KR101223158B1 (enExample)
CN (2) CN101855219B (enExample)
AU (1) AU2008335668C1 (enExample)
CA (1) CA2699733C (enExample)
ES (1) ES2691252T3 (enExample)
MX (1) MX2010002932A (enExample)
NZ (2) NZ600635A (enExample)
WO (2) WO2009039177A1 (enExample)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8273720B2 (en) * 2007-09-17 2012-09-25 Enanta Pharmaceuticals, Inc. 6,11-bicyclolides: bridged biaryl macrolide derivatives
EP2203435B1 (en) * 2007-09-17 2018-07-18 Enanta Pharmaceuticals, Inc. 6, 11-bridged biaryl macrolides
US8354383B2 (en) * 2007-09-17 2013-01-15 Enanta Pharmaceuticals, Inc. 6,11-bridged biaryl macrolides
WO2009137787A1 (en) 2008-05-09 2009-11-12 Enanta Pharmaceuticals, Inc. Processes for the preparation of 2-fluoro 6-11 bicyclic erythromycin derivatives
WO2009137739A1 (en) * 2008-05-09 2009-11-12 Enanta Pharmaceuticals, Inc. Processes for the preparation of o-[5-[4-amino-thiazol-2-yl]-pyridin-2-ylmethyl]-hydroxylamine
TW200946109A (en) * 2008-05-09 2009-11-16 Enanta Pharm Inc Anti-bacterial activity of 9-hydroxy derivatives 6, 11-bicyclolides
RU2601550C2 (ru) * 2010-12-09 2016-11-10 Вокхардт Лимитед Кетолидные соединения
ES2969792T3 (es) * 2015-11-19 2024-05-22 Biohaven Therapeutics Ltd Profármacos de amina de compuestos farmacéuticos

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6878691B2 (en) * 2002-05-13 2005-04-12 Enanta Pharmaceuticals, Inc. 6-11 bicyclic ketolide derivatives

Family Cites Families (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN85103264A (zh) * 1984-04-13 1987-01-14 美国辉瑞有限公司 9a-氮杂-9a-高红霉素衍生物
KR960000434B1 (ko) * 1986-12-17 1996-01-06 다이쇼 세이야꾸 가부시끼가이샤 에리스로마이신 a유도체 및 그의 제조 방법
US4921836A (en) * 1989-05-17 1990-05-01 Burroughs Wellcome Co. Substituted glutamic acids
IL99995A (en) * 1990-11-21 1997-11-20 Roussel Uclaf Erythromycin derivatives, their preparation and pharmaceutical compositions containing them
US5403923A (en) * 1990-11-28 1995-04-04 Taisho Pharmaceutical Co., Ltd. 6-0-methylerythromycin A derivatives
US5202434A (en) * 1991-04-05 1993-04-13 Merck & Co., Inc. 8a-aza-8a-homoerythromycin lactams
US5556839A (en) * 1991-04-29 1996-09-17 Eli Lilly And Company Form II Dirithromycin
WO1993021199A1 (fr) * 1992-04-22 1993-10-28 Taisho Pharmaceutical Co., Ltd. Derive de 5-o-desosaminylerythronolide
US5527780A (en) * 1992-11-05 1996-06-18 Roussel Uclaf Erythromycin derivatives
US5441939A (en) * 1994-03-04 1995-08-15 Pfizer Inc. 3"-desmethoxy derivatives of erythromycin and azithromycin
FR2738571B1 (fr) * 1995-09-11 1997-10-17 Roussel Uclaf Nouveaux derives de la 5-0-desosaminyl 6-0-methyl- erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs
US6274715B1 (en) * 1995-11-08 2001-08-14 Abbott Laboratories Tricyclic erythromycin derivatives
BR9711661A (pt) * 1996-09-04 1999-08-24 Abbott Lab Composto composi-Æo farmac-utica e processos para controlar uma infec-Æo bacteriana em um mam¡fero e para preparar um composto
UA51730C2 (uk) * 1996-09-04 2002-12-16 Ебботт Лабораторіз 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців
US5922683A (en) * 1997-05-29 1999-07-13 Abbott Laboratories Multicyclic erythromycin derivatives
US5780605A (en) * 1997-09-08 1998-07-14 Abbott Laboratories 6,9-bridged erythromycin derivatives
US6046171A (en) * 1997-10-29 2000-04-04 Abbott Laboratories 6,11-bridged erythromycin derivatives
US6124269A (en) * 1997-10-29 2000-09-26 Abbott Laboratories 2-Halo-6-O-substituted ketolide derivatives
EP0941998B1 (en) * 1998-03-03 2004-09-01 Pfizer Products Inc. 3,6-ketal macrolide antibiotics
US6054435A (en) * 1999-03-19 2000-04-25 Abbott Laboratories 6-O-substituted macrolides having antibacterial activity
JP2002542197A (ja) * 1999-04-16 2002-12-10 オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド ケトライド抗菌剤
US6590083B1 (en) * 1999-04-16 2003-07-08 Ortho-Mcneil Pharmaceutical, Inc. Ketolide antibacterials
HRP990130B1 (en) * 1999-05-03 2004-06-30 Pliva D D HALOGEN DERIVATIVES 9a-N-(N'-ARYLCARBAMOYL)- AND 9a-N-(N'-ARYLTHIOCARBAMOYL)-9-DEOXO-9a-AZA-9a OF HOMOERYTHROMYCIN A
US6355620B1 (en) * 1999-05-14 2002-03-12 Abbott Laboratories C-2 modified erythromycin derivatives
US7273853B2 (en) * 2002-05-13 2007-09-25 Enanta Pharmaceuticals, Inc. 6-11 bicyclic ketolide derivatives
US6841664B2 (en) * 2002-07-25 2005-01-11 Enanra Pharmaceuticals, Inc. 6,11-4-carbon bridged ketolides
US7064110B2 (en) * 2002-05-13 2006-06-20 Enanta Pharmaceuticals, Inc. 6-11 bicycle ketolide derivatives
US7022679B2 (en) * 2002-05-13 2006-04-04 Enanta Pharmaceuticals, Inc. Processes for the preparation of 6-11 bicyclic erythromycin derivatives
US7910558B2 (en) * 2002-05-13 2011-03-22 Enanta Pharmaceuticals, Inc. Bridged macrocyclic compounds and processes for the preparation thereof
US6764998B1 (en) * 2003-06-18 2004-07-20 Enanta Pharmaceuticals, Inc. 6,11-4C-bicyclic 9a-azalide derivatives
US6753318B1 (en) * 2002-07-25 2004-06-22 Enanta Pharmaceuticals, Inc. 6,11-4-carbon bridged erythromycin derivatives
US7129221B2 (en) * 2002-05-13 2006-10-31 Enanta Pharmaceuticals, Inc. 6,11-bicyclic erythromycin derivatives
US7135573B2 (en) * 2002-05-13 2006-11-14 Enanta Pharmaceuticals, Inc. Processes for the preparation of O-(6-Pyrazol-1-yl-pyridin-3-ylmethyl)-hydroxylamine
EP1506214B1 (en) * 2002-05-13 2010-01-20 Enanta Pharmaceuticals, Inc. 6-11 bicyclic ketolide derivatives
US6645941B1 (en) * 2003-03-26 2003-11-11 Enanta Pharmaceuticals, Inc. 6,11-3C-bicyclic 9a-azalide derivatives
AU2003295869A1 (en) * 2003-11-20 2005-07-14 Enanta Pharmaceuticals, Inc. 6-11 bicyclic ketolide drivatives
WO2005067564A2 (en) * 2004-01-07 2005-07-28 Enanta Pharmaceuticals, Inc. 6-11 bicyclic erythromycin derivatives
WO2005070113A2 (en) * 2004-01-09 2005-08-04 Enanta Pharmaceuticals, Inc. 9n-substituted 6-11 bicyclic erythromycin derivatives
US7384921B2 (en) * 2004-02-20 2008-06-10 Enanta Pharmaceuticals, Inc. Polymorphic forms of 6-11 bicyclic ketolide derivatives
EP1794171A2 (en) * 2004-07-28 2007-06-13 Ranbaxy Laboratories, Ltd. Ketolide derivatives as antibacterial agents
US7229972B2 (en) * 2004-12-07 2007-06-12 Enanta Pharmaceuticals, Inc. 3,6-Bicyclolides
US20060252710A1 (en) * 2005-05-04 2006-11-09 Guoqiang Wang 6-11 Bridged oxime erythromycin derivatives
US7384922B2 (en) * 2005-05-04 2008-06-10 Enanta Pharmaceuticals, Inc. 6-11 bridged oxime erythromycin derivatives
US7589067B2 (en) * 2005-10-12 2009-09-15 Enanta Pharmaceuticals, Inc. 6, 11-bridged tricyclic macrolides
EP2203435B1 (en) * 2007-09-17 2018-07-18 Enanta Pharmaceuticals, Inc. 6, 11-bridged biaryl macrolides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6878691B2 (en) * 2002-05-13 2005-04-12 Enanta Pharmaceuticals, Inc. 6-11 bicyclic ketolide derivatives

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NZ600635A (en) 2013-06-28
US20090075915A1 (en) 2009-03-19
CA2699733C (en) 2013-01-22
AU2008335668B2 (en) 2012-07-26
WO2009075923A2 (en) 2009-06-18
CN101855219A (zh) 2010-10-06
EP2203435A2 (en) 2010-07-07
NZ584159A (en) 2012-08-31
CA2699733A1 (en) 2009-06-18
JP5642548B2 (ja) 2014-12-17
AU2008335668C1 (en) 2013-05-30
WO2009075923A3 (en) 2009-09-24
EP2203435B1 (en) 2018-07-18
US20090118506A1 (en) 2009-05-07
CN104004039A (zh) 2014-08-27
MX2010002932A (es) 2010-05-27
JP2015017139A (ja) 2015-01-29
WO2009039177A1 (en) 2009-03-26
KR20120132577A (ko) 2012-12-05
KR20100059990A (ko) 2010-06-04
EP2203435A4 (en) 2011-03-02
ES2691252T3 (es) 2018-11-26
JP2010539191A (ja) 2010-12-16
KR101223158B1 (ko) 2013-01-17
AU2008335668A1 (en) 2009-06-18

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Granted publication date: 20140625