TWI455937B - 具有抗菌活性之2-羥乙基-1h-喹啉-2-酮衍生物及其氮雜等排類似物 - Google Patents
具有抗菌活性之2-羥乙基-1h-喹啉-2-酮衍生物及其氮雜等排類似物 Download PDFInfo
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- TWI455937B TWI455937B TW099110909A TW99110909A TWI455937B TW I455937 B TWI455937 B TW I455937B TW 099110909 A TW099110909 A TW 099110909A TW 99110909 A TW99110909 A TW 99110909A TW I455937 B TWI455937 B TW I455937B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/436—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
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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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (14)
- 一種式I化合物或該化合物之醫藥上可接受的鹽, 其中:R1 表示(C1 -C4 )烷氧基;U及V各表示CH,且W表示CH或N,或U表示N,V表示CH,且W表示CH或N,或U及V各表示N,且W表示CH;當W表示CH時,R2 表示氫或氟,或當W表示N時,R2 表示氫;A表示O或CH2 ;Y表示CH或N;Q表示O或S;及n表示0或1。
- 如請求項1之式I化合物或該化合物之醫藥上可接受的鹽,其係式Ip化合物: 其中R1 表示(C1 -C4 )烷氧基;U及W各獨立地表示CH或N;A表示O或CH2 ;Y表示CH或N;及Q表示O或S。
- 如請求項1或2之式I化合物或該化合物之醫藥上可接受的鹽,其中Y表示CH。
- 如請求項1或2之式I化合物或該化合物之醫藥上可接受的鹽,其中Q表示O。
- 如請求項1或2之式I化合物或該化合物之醫藥上可接受的鹽,其中R1 表示甲氧基。
- 如請求項1或2之式I化合物或該化合物之醫藥上可接受的鹽,其中A表示O。
- 如請求項1或2之式I化合物或該化合物之醫藥上可接受的鹽,其中A表示CH2 。
- 如請求項1或2之式I化合物或該化合物之醫藥上可接受的鹽,其中n表示1。
- 如請求項1之式I化合物或該化合物之醫藥上可接受的鹽,其中:R1 表示甲氧基;U表示N,而V表示CH且W表示N,或V表示N且W表示CH;R2 表示氫;A表示O或CH2 ;Y表示CH;Q表示O或S;及n表示1。
- 如請求項1之式I化合物或該化合物之醫藥上可接受的鹽,其選自以下化合物:1-((S)-2-{(2S,5R)-5-[(2,3-二氫-4-氧雜-1-硫雜-6-氮雜-萘-7-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-7-甲氧基-1H-[1,8]萘啶-2-酮;1-((2S)-2-{(2S,5R)-5-[(2,3-二氫-[1,4]二氧雜環己烯并[2,3-c]吡啶-7-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-7-甲氧基-1H-[1,8]萘啶-2-酮;1-((2S)-2-{(2S,5R)-5-[(2,3-二氫-[1,4]二氧雜環己烯并[2,3-c]吡啶-7-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-7-甲氧基-1H-喹噁啉-2-酮;4-((2S)-2-{(2S,5R)-5-[(2,3-二氫-[1,4]二氧雜環己烯并[2,3-c]吡啶-7-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-6-甲氧基-4H-吡啶并[2,3-b]吡嗪-3-酮; 1-((2S)-2-{(2S,5R)-5-[(6,7-二氫-[1,4]二氧雜環己烯并[2,3-c]噠嗪-3-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-7-甲氧基-1H-[1,8]萘啶-2-酮;1-((2R)-2-{4-[(2,3-二氫-[1,4]二氧雜環己烯并[2,3-c]吡啶-7-基甲基)-胺基]-環己基}-2-羥基-乙基)-7-甲氧基-1H-[1,8]萘啶-2-酮;1-((2R)-2-{4-[(2,3-二氫-[1,4]二氧雜環己烯并[2,3-c]吡啶-7-基甲基)-胺基]-環己基}-2-羥基-乙基)-7-甲氧基-1H-喹噁啉-2-酮;1-((2S)-2-{(2S,5R)-5-[(6,7-二氫-8-氧雜-5-硫雜-1,2-二氮雜-萘-3-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-7-甲氧基-1H-[1,8]萘啶-2-酮;1-((2S)-2-羥基-2-{(2S,5R)-5-[(3-氧雜-1-硫雜-5-氮雜-二氫化茚-6-基甲基)-胺基]-四氫-哌喃-2-基}-乙基)-7-甲氧基-1H-[1,8]萘啶-2-酮;3-氟-1-((2S)-2-羥基-2-{(2S,5R)-5-[(3-氧雜-1-硫雜-5-氮雜-二氫化茚-6-基甲基)-胺基]-四氫-哌喃-2-基}-乙基)-7-甲氧基-1H-[1,8]萘啶-2-酮;4-((2S)-2-{(2S,5R)-5-[(2,3-二氫-4-氧雜-1-硫雜-6-氮雜-萘-7-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-6-甲氧基-4H-吡啶并[2,3-b]吡嗪-3-酮;4-((2S)-2-{(2S,5R)-5-[(6,7-二氫-8-氧雜-5-硫雜-1,2-二氮雜-萘-3-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-6-甲氧基-4H-吡啶并[2,3-b]吡嗪-3-酮; 5-((2S)-2-{(2S,5R)-5-[(2,3-二氫-[1,4]二氧雜環己烯并[2,3-c]吡啶-7-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-3-甲氧基-5H-吡啶并[2,3-b]吡嗪-6-酮;5-((2S)-2-{(2S,5R)-5-[(2,3-二氫-4-氧雜-1-硫雜-6-氮雜-萘-7-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-3-甲氧基-5H-吡啶并[2,3-b]吡嗪-6-酮;5-((S)-2-{(2S,5R)-5-[(6,7-二氫-8-氧雜-5-硫雜-1,2-二氮雜-萘-3-基甲基)-胺基]-四氫-哌喃-2-基}-2-羥基-乙基)-3-甲氧基-5H-吡啶并[2,3-b]吡嗪-6-酮;或該化合物之醫藥上可接受的鹽。
- 一種醫藥組合物,其包含作為活性成分之如請求項1至10中任一項所定義之式I化合物或其醫藥上可接受的鹽,及至少一種治療上惰性賦形劑。
- 一種如請求項1至10中任一項所定義之式I化合物或其醫藥上可接受的鹽之用途,其係用於製備用於治療細菌感染之藥劑。
- 如請求項12之用途,其中該藥劑係用於治療選自由下列組成之群之細菌感染:呼吸道感染、中耳炎、腦膜炎、皮膚及軟組織感染、肺炎、菌血症、心內膜炎、腹腔內感染、胃腸感染、艱難梭狀桿菌(Clostridium difficile )感染、尿道感染、性傳播感染、外來物感染、骨髓炎、萊姆病、局部感染、眼部感染、結核病及熱帶病。
- 如請求項12之用途,其中該藥劑係用於治療選自由呼吸道感染、中耳炎、腦膜炎、皮膚及軟組織感染、肺炎及菌血症組成之群之細菌感染。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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IB2009051510 | 2009-04-09 |
Publications (2)
Publication Number | Publication Date |
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TW201040182A TW201040182A (en) | 2010-11-16 |
TWI455937B true TWI455937B (zh) | 2014-10-11 |
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TW099110909A TWI455937B (zh) | 2009-04-09 | 2010-04-08 | 具有抗菌活性之2-羥乙基-1h-喹啉-2-酮衍生物及其氮雜等排類似物 |
Country Status (15)
Country | Link |
---|---|
US (1) | US8415375B2 (zh) |
EP (1) | EP2417141B1 (zh) |
JP (1) | JP5639639B2 (zh) |
KR (1) | KR101729345B1 (zh) |
CN (1) | CN102361875B (zh) |
AR (1) | AR076222A1 (zh) |
AU (1) | AU2010233387B2 (zh) |
BR (1) | BRPI1015310A8 (zh) |
CA (1) | CA2756727C (zh) |
ES (1) | ES2438742T3 (zh) |
MX (1) | MX2011010358A (zh) |
PL (1) | PL2417141T3 (zh) |
RU (1) | RU2540862C2 (zh) |
TW (1) | TWI455937B (zh) |
WO (1) | WO2010116337A1 (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR076222A1 (es) | 2009-04-09 | 2011-05-26 | Actelion Pharmaceuticals Ltd | Derivados 2-hidroxietil-1h-quinolin-ona y sus analogos azaisotericos con actividad antibacteriana y composiciones farmaceuticas que los contienen |
AU2012275499A1 (en) * | 2011-06-27 | 2013-12-19 | Kyorin Pharmaceutical Co., Ltd. | Bridged bicyclic compounds for the treatment of bacterial infections |
TW201313726A (zh) | 2011-09-16 | 2013-04-01 | Actelion Pharmaceuticals Ltd | 製造合成之中間體之方法 |
TW201833120A (zh) | 2017-02-17 | 2018-09-16 | 瑞士商愛杜西亞製藥有限公司 | 芳基噁唑啶酮抗生素化合物 |
Citations (1)
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WO2006137485A1 (ja) * | 2005-06-24 | 2006-12-28 | Toyama Chemical Co., Ltd. | 新規な含窒素複素環化合物およびその塩 |
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SU1095611A1 (ru) * | 1982-09-10 | 2007-06-27 | Краснодарский ордена Трудового Красного Знамени политехнический институт | Хлорид 5-хлорметил-2-этил-8-метил-4Н-м-диоксино-(4,5-с)-пиридиния, обладающий антимикробной активностью |
EG20543A (en) * | 1992-10-30 | 1999-07-31 | Procter & Gamble | Process for preparing of novel antimicrobial -5- (n-heterosubstituted amino) quinolones |
WO1998007703A1 (fr) * | 1996-08-22 | 1998-02-26 | Meiji Seika Kaisha, Ltd. | Derives quinoleine et agent psychotrope |
GB0112834D0 (en) * | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
TW200406413A (en) * | 2002-06-26 | 2004-05-01 | Glaxo Group Ltd | Compounds |
US7691850B2 (en) | 2004-06-15 | 2010-04-06 | Glaxo Group Limited | Antibacterial agents |
CA2580621A1 (en) * | 2004-09-24 | 2006-03-30 | Actelion Pharmaceuticals Ltd | New bicyclic antibiotics |
US7981886B2 (en) * | 2005-05-25 | 2011-07-19 | Actelion Pharmaceutical Ltd. | Antibiotics derivatives |
MY150958A (en) * | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
CN101341126A (zh) * | 2005-10-13 | 2009-01-07 | 莫弗凯姆联合化学股份公司 | 具有抗菌活性的5-喹啉衍生物 |
EP2022793B1 (en) * | 2006-05-26 | 2014-06-04 | Toyama Chemical Co., Ltd. | Novel heterocyclic compound or salt thereof and intermediate thereof |
EP1992628A1 (en) | 2007-05-18 | 2008-11-19 | Glaxo Group Limited | Derivatives and analogs of N-ethylquinolones and N-ethylazaquinolones |
WO2008071981A1 (en) | 2006-12-15 | 2008-06-19 | Astrazeneca Ab | Piperidines for the treatment of bacterial infections |
TW200831517A (en) | 2006-12-15 | 2008-08-01 | Astrazeneca Ab | Chemical compounds |
WO2008071962A1 (en) | 2006-12-15 | 2008-06-19 | Astrazeneca Ab | Pteridines and pyrimidinopyridines as antibacterial agents |
WO2008071964A1 (en) | 2006-12-15 | 2008-06-19 | Astrazeneca Ab | Naphthyridine bactericides |
AU2008240764C1 (en) | 2007-04-20 | 2011-10-20 | Glaxo Group Limited | Tricyclic nitrogen containing compounds as antibacterial agents |
EP2005995A1 (en) | 2007-06-22 | 2008-12-24 | Glaxo Group Limited | Heterocyclic compounds for the treatment of tuberculosis |
WO2009001126A1 (en) | 2007-06-27 | 2008-12-31 | Astrazeneca Ab | Substituted piperidine derivatives and their use as antibaterial agents |
GB0800367D0 (en) | 2008-01-09 | 2008-02-20 | Glaxo Group Ltd | Compounds |
WO2009104159A1 (en) | 2008-02-22 | 2009-08-27 | Actelion Pharmaceuticals Ltd | Oxazolidinone derivatives |
BRPI0913093A2 (pt) * | 2008-06-03 | 2018-02-06 | Actelion Pharmaceuticals Ltd | Compostos derivados de [4-(1-amino-etil)-cicloexil]- metil-amina e [6-(1-amino-etil)-tetraidro-piran-3-il]- metil-amina, medicamento, composição farmacêutica que contêm esse composto e uso dos mesmos |
EP2344485B1 (en) | 2008-10-10 | 2017-03-22 | Actelion Pharmaceuticals Ltd | Oxazolidinyl antibiotics |
JP4955835B2 (ja) | 2008-12-12 | 2012-06-20 | アクテリオン ファーマシューティカルズ リミテッド | 5−アミノ−2−(1−ヒドロキシ−エチル)−テトラヒドロピラン誘導体 |
AR076222A1 (es) | 2009-04-09 | 2011-05-26 | Actelion Pharmaceuticals Ltd | Derivados 2-hidroxietil-1h-quinolin-ona y sus analogos azaisotericos con actividad antibacteriana y composiciones farmaceuticas que los contienen |
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2010
- 2010-04-07 AR ARP100101165A patent/AR076222A1/es unknown
- 2010-04-08 CN CN201080013196.8A patent/CN102361875B/zh not_active Expired - Fee Related
- 2010-04-08 CA CA2756727A patent/CA2756727C/en not_active Expired - Fee Related
- 2010-04-08 JP JP2012504122A patent/JP5639639B2/ja not_active Expired - Fee Related
- 2010-04-08 KR KR1020117023354A patent/KR101729345B1/ko active IP Right Grant
- 2010-04-08 WO PCT/IB2010/051517 patent/WO2010116337A1/en active Application Filing
- 2010-04-08 BR BRPI1015310A patent/BRPI1015310A8/pt not_active Application Discontinuation
- 2010-04-08 AU AU2010233387A patent/AU2010233387B2/en not_active Ceased
- 2010-04-08 EP EP10714481.8A patent/EP2417141B1/en not_active Not-in-force
- 2010-04-08 ES ES10714481.8T patent/ES2438742T3/es active Active
- 2010-04-08 MX MX2011010358A patent/MX2011010358A/es active IP Right Grant
- 2010-04-08 US US13/263,922 patent/US8415375B2/en not_active Expired - Fee Related
- 2010-04-08 PL PL10714481T patent/PL2417141T3/pl unknown
- 2010-04-08 RU RU2011145052/04A patent/RU2540862C2/ru not_active IP Right Cessation
- 2010-04-08 TW TW099110909A patent/TWI455937B/zh not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2006137485A1 (ja) * | 2005-06-24 | 2006-12-28 | Toyama Chemical Co., Ltd. | 新規な含窒素複素環化合物およびその塩 |
Also Published As
Publication number | Publication date |
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CA2756727C (en) | 2017-05-02 |
EP2417141B1 (en) | 2013-10-16 |
JP2012523407A (ja) | 2012-10-04 |
EP2417141A1 (en) | 2012-02-15 |
AU2010233387B2 (en) | 2015-01-15 |
CN102361875B (zh) | 2014-08-20 |
ES2438742T3 (es) | 2014-01-20 |
US8415375B2 (en) | 2013-04-09 |
TW201040182A (en) | 2010-11-16 |
AU2010233387A1 (en) | 2011-11-24 |
CN102361875A (zh) | 2012-02-22 |
BRPI1015310A8 (pt) | 2017-12-26 |
KR20120014240A (ko) | 2012-02-16 |
US20120040989A1 (en) | 2012-02-16 |
PL2417141T3 (pl) | 2014-03-31 |
CA2756727A1 (en) | 2010-10-14 |
JP5639639B2 (ja) | 2014-12-10 |
MX2011010358A (es) | 2011-11-01 |
KR101729345B1 (ko) | 2017-04-21 |
RU2011145052A (ru) | 2013-05-20 |
AR076222A1 (es) | 2011-05-26 |
BRPI1015310A2 (pt) | 2016-05-24 |
WO2010116337A1 (en) | 2010-10-14 |
RU2540862C2 (ru) | 2015-02-10 |
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