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WO2008126898A1 - （アザ）インドール誘導体及びその医薬用途 - Google Patents

（アザ）インドール誘導体及びその医薬用途 Download PDF

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Publication number
WO2008126898A1
WO2008126898A1 PCT/JP2008/057089 JP2008057089W WO2008126898A1 WO 2008126898 A1 WO2008126898 A1 WO 2008126898A1 JP 2008057089 W JP2008057089 W JP 2008057089W WO 2008126898 A1 WO2008126898 A1 WO 2008126898A1
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WO
WIPO (PCT)
Prior art keywords
independently represent
aza
indole derivative
prophylactic
cyano
Prior art date
Application number
PCT/JP2008/057089
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English (en)
French (fr)
Inventor
Kazuo Shimizu
Yasushi Takigawa
Hideki Fujikura
Masato Iizuka
Masahiro Hiratochi
Norihiko Kikuchi
Original Assignee
Kissei Pharmaceutical Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to CA2682391A priority Critical patent/CA2682391C/en
Priority to BRPI0810524A priority patent/BRPI0810524B8/pt
Priority to AU2008239017A priority patent/AU2008239017B2/en
Priority to DK08740190.7T priority patent/DK2133332T3/da
Priority to CN2008800189139A priority patent/CN101679251B/zh
Priority to MX2009010966A priority patent/MX337527B/es
Priority to SI200831107T priority patent/SI2133332T1/sl
Priority to ES08740190T priority patent/ES2431815T3/es
Priority to PL08740190T priority patent/PL2133332T3/pl
Priority to EP08740190.7A priority patent/EP2133332B1/en
Priority to US12/595,476 priority patent/US8003647B2/en
Priority to JP2009509371A priority patent/JP5330989B2/ja
Application filed by Kissei Pharmaceutical Co., Ltd. filed Critical Kissei Pharmaceutical Co., Ltd.
Priority to RU2009141614/04A priority patent/RU2477274C2/ru
Priority to KR1020097021438A priority patent/KR101502957B1/ko
Publication of WO2008126898A1 publication Critical patent/WO2008126898A1/ja
Priority to HK10106337.7A priority patent/HK1140197A1/xx
Priority to US13/116,389 priority patent/US8466152B2/en
Priority to US13/895,634 priority patent/US8993616B2/en
Priority to HRP20130900AT priority patent/HRP20130900T1/hr
Priority to US14/193,911 priority patent/US8829040B2/en

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    • 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
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • 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
    • A61K31/41—Heterocyclic 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
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/437—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 five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/535—Heterocyclic 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
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/04—Drugs for disorders of the urinary system for urolithiasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D417/02—Heterocyclic 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
    • C07D417/04—Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Rheumatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Indole Compounds (AREA)

Abstract

本発明は、血漿尿酸値異常に起因する疾患等の予防又は治療薬として有用な化合物を提供する。すなわち、本発明は、キサンチンオキシダーゼ阻害活性を有し、血漿尿酸値異常に起因する疾患の予防又は治療薬として有用な、下記一般式（Ｉ）で表される（アザ）インドール誘導体、そのプロドラッグ、又はその塩等に関する。式（Ｉ）中、Ｔはニトロ、シアノ等；環Ｊはアリール又はヘテロアリール；Ｑはカルボキシ、５－テトラゾリル等；ＹはＨ、ＯＨ、ＮＨ２、ハロゲン、ニトロ、アルキル、アルコキシ等；Ｘ１、Ｘ２、Ｘ３は独立してＣＲ２又はＮ；Ｒ１及びＲ２は独立してハロゲン、シアノ、ハロアルキル、Ａ－Ｄ－Ｅ－Ｇ、－Ｎ（－Ｄ－Ｅ－Ｇ）２等（式中、Ａは単結合、Ｏ、Ｓ等；Ｄ及びＧは独立して置換可アルキレン、シクロアルキレン、ヘテロシクロアルキレン、アリーレン、ヘテロアリーレン等；Ｅは単結合、Ｏ、Ｓ、ＣＯＯ、ＳＯ２等；である）である。
PCT/JP2008/057089 2007-04-11 2008-04-10 （アザ）インドール誘導体及びその医薬用途 WO2008126898A1 (ja)

Priority Applications (19)

Application Number Priority Date Filing Date Title
US12/595,476 US8003647B2 (en) 2007-04-11 2008-04-10 (Aza)indole derivative and use thereof for medical purposes
AU2008239017A AU2008239017B2 (en) 2007-04-11 2008-04-10 (Aza)indole derivative and use thereof for medical purposes
DK08740190.7T DK2133332T3 (da) 2007-04-11 2008-04-10 (aza)indolderivat og anvendelse deraf til medicinske formål
CN2008800189139A CN101679251B (zh) 2007-04-11 2008-04-10 (氮杂)吲哚衍生物及其医药用途
MX2009010966A MX337527B (es) 2007-04-11 2008-04-10 Derivado de (aza)indol y su uso para propositos medicos.
SI200831107T SI2133332T1 (sl) 2007-04-11 2008-04-10 (aza)indolinski derivat in njegova uporaba v medicinske namene
ES08740190T ES2431815T3 (es) 2007-04-11 2008-04-10 Derivado de (aza)indol y uso del mismo para fines médicos
PL08740190T PL2133332T3 (pl) 2007-04-11 2008-04-10 Pochodna aza(indolu) i jej zastosowanie do celów medycznych
EP08740190.7A EP2133332B1 (en) 2007-04-11 2008-04-10 (aza)indole derivative and use thereof for medical purposes
CA2682391A CA2682391C (en) 2007-04-11 2008-04-10 (aza)indole derivative and use thereof for medical purposes
BRPI0810524A BRPI0810524B8 (pt) 2007-04-11 2008-04-10 derivado de (aza)indol, inibidor de xantina oxidase e composição farmacêutica compreendendo o dito derivado
JP2009509371A JP5330989B2 (ja) 2007-04-11 2008-04-10 （アザ）インドール誘導体及びその医薬用途
RU2009141614/04A RU2477274C2 (ru) 2007-04-11 2008-04-10 Производное (аза)индола и его применение в лечебных целях
KR1020097021438A KR101502957B1 (ko) 2007-04-11 2008-04-10 (아자)인돌 유도체 및 그 의약 용도
HK10106337.7A HK1140197A1 (en) 2007-04-11 2010-06-29 (aza)indole derivative and use thereof for medical purposes ()
US13/116,389 US8466152B2 (en) 2007-04-11 2011-05-26 (aza)indole derivative and use thereof for medical purposes
US13/895,634 US8993616B2 (en) 2007-04-11 2013-05-16 (aza)indole derivative and use thereof for medical purposes
HRP20130900AT HRP20130900T1 (hr) 2007-04-11 2013-09-23 Derivat (aza)indola i njegova uporaba u medicinske svrhe
US14/193,911 US8829040B2 (en) 2007-04-11 2014-02-28 (aza)indole derivative and use thereof for medical purposes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007104096 2007-04-11
JP2007-104096 2007-04-11

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/595,476 A-371-Of-International US8003647B2 (en) 2007-04-11 2008-04-10 (Aza)indole derivative and use thereof for medical purposes
US13/116,389 Division US8466152B2 (en) 2007-04-11 2011-05-26 (aza)indole derivative and use thereof for medical purposes

Publications (1)

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WO2008126898A1 true WO2008126898A1 (ja) 2008-10-23

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PCT/JP2008/057089 WO2008126898A1 (ja) 2007-04-11 2008-04-10 （アザ）インドール誘導体及びその医薬用途

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Country Link
US (4) US8003647B2 (ja)
EP (2) EP2133332B1 (ja)
JP (1) JP5330989B2 (ja)
KR (1) KR101502957B1 (ja)
CN (1) CN101679251B (ja)
AU (1) AU2008239017B2 (ja)
BR (1) BRPI0810524B8 (ja)
CA (1) CA2682391C (ja)
CY (1) CY1114647T1 (ja)
DK (1) DK2133332T3 (ja)
ES (1) ES2431815T3 (ja)
HK (1) HK1140197A1 (ja)
HR (1) HRP20130900T1 (ja)
MX (1) MX337527B (ja)
PL (1) PL2133332T3 (ja)
PT (1) PT2133332E (ja)
RU (1) RU2477274C2 (ja)
SI (1) SI2133332T1 (ja)
WO (1) WO2008126898A1 (ja)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010093191A2 (en) * 2009-02-13 2010-08-19 Lg Life Sciences Ltd. Novel compounds effective as xanthine oxidase inhibitors, method for preparing the same, and pharmaceutical composition containing the same
WO2010113942A1 (ja) * 2009-03-31 2010-10-07 キッセイ薬品工業株式会社 インドリジン誘導体及びその医薬用途
WO2011043568A2 (en) 2009-10-07 2011-04-14 Lg Life Sciences Ltd. Novel compounds effective as xanthine oxidase inhibitors, method for preparing the same, and pharmaceutical composition containing the same
US7947707B2 (en) 2005-10-07 2011-05-24 Kissei Pharmaceutical Co., Ltd. Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same
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WO2022231261A1 (ko) * 2021-04-27 2022-11-03 주식회사 엘지화학 잔틴 옥시다아제 저해제 합성을 위한 중간체의 제조 방법
WO2023277660A1 (ko) * 2021-07-02 2023-01-05 주식회사 엘지화학 잔틴 옥시다아제 저해제의 제조 방법
US12084453B2 (en) 2021-12-10 2024-09-10 Incyte Corporation Bicyclic amines as CDK12 inhibitors

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US8829040B2 (en) 2014-09-09
BRPI0810524A2 (pt) 2014-10-21
DK2133332T3 (da) 2013-09-30
AU2008239017B2 (en) 2012-09-27
EP2402314B1 (en) 2013-07-31
KR101502957B1 (ko) 2015-03-16
CN101679251A (zh) 2010-03-24
MX337527B (es) 2016-03-09
BRPI0810524B1 (pt) 2019-09-10
JP5330989B2 (ja) 2013-10-30
BRPI0810524B8 (pt) 2021-05-25
US8003647B2 (en) 2011-08-23
RU2477274C2 (ru) 2013-03-10
HK1140197A1 (en) 2010-10-08
US20130252955A1 (en) 2013-09-26
EP2133332A1 (en) 2009-12-16
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US8993616B2 (en) 2015-03-31
PT2133332E (pt) 2013-10-03
SI2133332T1 (sl) 2014-02-28
US20140179932A1 (en) 2014-06-26
RU2009141614A (ru) 2011-05-20
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PL2133332T3 (pl) 2014-02-28
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