CA2729307C - Macrocyclic indole derivatives useful as hepatitis c virus inhibitors - Google Patents

Macrocyclic indole derivatives useful as hepatitis c virus inhibitors Download PDF

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Publication number
CA2729307C
CA2729307C CA2729307A CA2729307A CA2729307C CA 2729307 C CA2729307 C CA 2729307C CA 2729307 A CA2729307 A CA 2729307A CA 2729307 A CA2729307 A CA 2729307A CA 2729307 C CA2729307 C CA 2729307C
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Canada
Prior art keywords
compound
compounds
formula
synthesis
hcv
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CA2729307A
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English (en)
French (fr)
Other versions
CA2729307A1 (en
Inventor
Sandrine Marie Helene Vendeville
Pierre Jean-Marie Bernard Raboisson
Tse-I Lin
Abdellah Tahri
Katie Ingrid Eduard Amssons
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Janssen Sciences Ireland ULC
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Janssen Sciences Ireland ULC
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Classifications

    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • 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
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D515/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D515/18—Bridged systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
CA2729307A 2008-07-08 2009-07-08 Macrocyclic indole derivatives useful as hepatitis c virus inhibitors Active CA2729307C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
EP08159965 2008-07-08
EP08159965.6 2008-07-08
EP08160254.2 2008-07-11
EP08160254 2008-07-11
EP08161743.3 2008-08-04
EP08161743 2008-08-04
PCT/EP2009/004942 WO2010003658A1 (en) 2008-07-08 2009-07-08 Macrocyclic indole derivatives useful as hepatitis c virus inhibitors

Publications (2)

Publication Number Publication Date
CA2729307A1 CA2729307A1 (en) 2010-01-14
CA2729307C true CA2729307C (en) 2017-08-29

Family

ID=40972916

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2729307A Active CA2729307C (en) 2008-07-08 2009-07-08 Macrocyclic indole derivatives useful as hepatitis c virus inhibitors

Country Status (31)

Country Link
US (2) US8921355B2 (https=)
EP (1) EP2310396B1 (https=)
JP (2) JP5426671B2 (https=)
KR (1) KR101640374B1 (https=)
CN (1) CN102089314B (https=)
AP (1) AP2743A (https=)
AR (1) AR072726A1 (https=)
AU (1) AU2009267389B8 (https=)
BR (1) BRPI0915887B8 (https=)
CA (1) CA2729307C (https=)
CL (1) CL2011000032A1 (https=)
CO (1) CO6351793A2 (https=)
CR (1) CR20110076A (https=)
DK (1) DK2310396T3 (https=)
EA (1) EA019008B1 (https=)
EC (1) ECSP11010750A (https=)
ES (1) ES2651038T3 (https=)
HN (1) HN2011000072A (https=)
HR (1) HRP20171892T1 (https=)
HU (1) HUE035244T2 (https=)
IL (1) IL210086A (https=)
LT (1) LT2310396T (https=)
MX (1) MX2011000276A (https=)
NI (1) NI201100010A (https=)
NO (1) NO2310396T3 (https=)
NZ (2) NZ590073A (https=)
SI (1) SI2310396T1 (https=)
SV (1) SV2011003796A (https=)
TW (1) TWI454476B (https=)
UY (1) UY31973A (https=)
WO (1) WO2010003658A1 (https=)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2389994T3 (es) 2007-12-24 2012-11-05 Janssen R&D Ireland Indoles macrocíclicos como inhibidores del virus de la hepatitis C
TWI454476B (zh) * 2008-07-08 2014-10-01 Tibotec Pharm Ltd 用作ｃ型肝炎病毒抑制劑之巨環吲哚衍生物
UA108211C2 (uk) * 2009-11-04 2015-04-10 Янссен Рід Айрленд Бензімідазолімідазольні похідні
US20130028865A1 (en) * 2010-04-13 2013-01-31 Medivir Ab Combination of a Macrocyclic Inhibitor of HCV, A Non-Nucleoside and a Nucleoside
CA2801517C (en) * 2010-06-24 2017-12-12 Janssen R&D Ireland Preparation of 13-cyclohexyl-3-methoxy-6-[methyl-(2-{2-[methyl-(sulphamoyl)-amino]-ethoxy}-ethyl)-carbamoyl]-7h-indolo-[2,1-.alpha.]-[2]-benzazepine-10-carboxylic acid
HUE035751T2 (hu) 2011-09-02 2018-08-28 Novartis Ag Gyulladásgátló szubsztituált ciklobuténdion vegyület kolinsó
US8716275B2 (en) * 2011-10-20 2014-05-06 Bristol-Myers Squibb Company Compound for the treatment of hepatitis C
US20150209366A1 (en) 2012-08-31 2015-07-30 Janssen Pharmaceuticals, Inc. Combination of a macrocyclic protease inhibitor of hcv, a non-nucleoside hcv inhibitor and ritonavir
WO2014152275A1 (en) * 2013-03-14 2014-09-25 Concert Pharmaceuticals, Inc. Deuterium modified derivatives of the ns5b polymerase inhibitor tmc647055
US10450263B2 (en) 2017-02-10 2019-10-22 Southern Research Institute Benzo annulenes as antiviral agents
KR101974388B1 (ko) 2017-06-23 2019-05-02 (주)에니켐텍 알킬 디에틸렌 트리아민 유도체 및 이의 제조방법
WO2019133574A2 (en) * 2017-12-26 2019-07-04 Southern Research Institute Benzoannulene derivatives as antiviral agents
US12274700B1 (en) 2020-10-30 2025-04-15 Accencio LLC Methods of treating symptoms of coronavirus infection with RNA polymerase inhibitors
US12060148B2 (en) 2022-08-16 2024-08-13 Honeywell International Inc. Ground resonance detection and warning system and method
CN116425782A (zh) * 2023-03-22 2023-07-14 烟台盛凯伦化学科技有限公司 一种5-乙酰基-2-氟苯硼酸频哪醇酯的制备方法

Family Cites Families (28)

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US6037157A (en) 1995-06-29 2000-03-14 Abbott Laboratories Method for improving pharmacokinetics
US5807876A (en) 1996-04-23 1998-09-15 Vertex Pharmaceuticals Incorporated Inhibitors of IMPDH enzyme
US6054472A (en) 1996-04-23 2000-04-25 Vertex Pharmaceuticals, Incorporated Inhibitors of IMPDH enzyme
US20050267836A1 (en) 1996-03-25 2005-12-01 Cfph, Llc Method and system for transacting with a trading application
CA2252465C (en) 1996-04-23 2007-07-03 Vertex Pharmaceuticals Incorporated Urea derivatives as inhibitors of impdh enzyme
DK0966465T3 (da) 1997-03-14 2003-10-20 Vertex Pharma Inhibitorer af IMPDH-enzymer
CA2367017C (en) 1999-03-19 2009-05-26 Vertex Pharmaceuticals Incorporated Inhibitors of impdh enzyme
JP4778665B2 (ja) 2000-08-30 2011-09-21 パナソニック株式会社 プラズマディスプレイ表示装置の製造方法
PL1713822T3 (pl) 2004-01-30 2010-08-31 Medivir Ab Inhibitory proteazy serynowej HCV NS-3
US7153848B2 (en) 2004-08-09 2006-12-26 Bristol-Myers Squibb Company Inhibitors of HCV replication
PE20070211A1 (es) 2005-07-29 2007-05-12 Medivir Ab Compuestos macrociclicos como inhibidores del virus de hepatitis c
AU2006286441A1 (en) 2005-09-02 2007-03-08 Janssen R&D Ireland Benzodiazepines as HCV inhibitors
US7399758B2 (en) * 2005-09-12 2008-07-15 Meanwell Nicholas A Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors
GB0522881D0 (en) 2005-11-10 2005-12-21 Angeletti P Ist Richerche Bio Therapeutic compounds
WO2007092000A1 (en) 2006-02-06 2007-08-16 Bristol-Myers Squibb Company Inhibitors of hcv replication
US7456166B2 (en) * 2006-05-17 2008-11-25 Bristol-Myers Squibb Company Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors
US7521443B2 (en) 2006-05-17 2009-04-21 Bristol-Myers Squibb Company Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors
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TWI454476B (zh) * 2008-07-08 2014-10-01 Tibotec Pharm Ltd 用作ｃ型肝炎病毒抑制劑之巨環吲哚衍生物
AR073603A1 (es) 2008-09-18 2010-11-17 Ortho Mcneil Janssen Pharm Combinaciones sinergicas de un inhibidor macrociclico del vhc y un nucleosido
PL2401272T3 (pl) 2009-02-27 2017-06-30 Janssen Pharmaceuticals, Inc. Amorficzna sól makrocyklicznego inhibitora HCV
US20130028865A1 (en) 2010-04-13 2013-01-31 Medivir Ab Combination of a Macrocyclic Inhibitor of HCV, A Non-Nucleoside and a Nucleoside
CA2801517C (en) 2010-06-24 2017-12-12 Janssen R&D Ireland Preparation of 13-cyclohexyl-3-methoxy-6-[methyl-(2-{2-[methyl-(sulphamoyl)-amino]-ethoxy}-ethyl)-carbamoyl]-7h-indolo-[2,1-.alpha.]-[2]-benzazepine-10-carboxylic acid
US20150209366A1 (en) 2012-08-31 2015-07-30 Janssen Pharmaceuticals, Inc. Combination of a macrocyclic protease inhibitor of hcv, a non-nucleoside hcv inhibitor and ritonavir

Also Published As

Publication number Publication date
NO2310396T3 (https=) 2018-02-03
SI2310396T1 (en) 2018-01-31
HUE035244T2 (hu) 2018-05-02
AU2009267389A8 (en) 2013-07-04
BRPI0915887B8 (pt) 2021-05-25
HN2011000072A (es) 2013-09-01
IL210086A0 (en) 2011-02-28
WO2010003658A1 (en) 2010-01-14
UY31973A (es) 2010-01-29
JP2011527299A (ja) 2011-10-27
MX2011000276A (es) 2011-03-02
JP5426671B2 (ja) 2014-02-26
JP5808370B2 (ja) 2015-11-10
CN102089314B (zh) 2014-07-23
IL210086A (en) 2014-05-28
US20110105473A1 (en) 2011-05-05
KR101640374B1 (ko) 2016-07-18
CR20110076A (es) 2011-11-10
TWI454476B (zh) 2014-10-01
BRPI0915887B1 (pt) 2020-02-18
AR072726A1 (es) 2010-09-15
JP2014028818A (ja) 2014-02-13
NZ590073A (en) 2012-11-30
EP2310396A1 (en) 2011-04-20
LT2310396T (lt) 2017-12-27
AU2009267389B2 (en) 2013-05-30
HK1155734A1 (en) 2012-05-25
EA019008B1 (ru) 2013-12-30
AP2743A (en) 2013-09-30
ECSP11010750A (es) 2011-08-31
CL2011000032A1 (es) 2011-07-15
US9427440B2 (en) 2016-08-30
HRP20171892T1 (hr) 2018-01-12
EP2310396B1 (en) 2017-09-06
US8921355B2 (en) 2014-12-30
AP2010005521A0 (en) 2010-12-31
EA201170153A1 (ru) 2011-08-30
TW201014865A (en) 2010-04-16
NI201100010A (es) 2011-09-07
DK2310396T3 (en) 2017-12-11
KR20110040889A (ko) 2011-04-20
NZ603343A (en) 2013-08-30
AU2009267389A1 (en) 2010-01-14
AU2009267389B8 (en) 2013-07-04
CO6351793A2 (es) 2011-12-20
CN102089314A (zh) 2011-06-08
US20140107101A1 (en) 2014-04-17
CA2729307A1 (en) 2010-01-14
SV2011003796A (es) 2011-04-08
ES2651038T3 (es) 2018-01-23
BRPI0915887A2 (pt) 2015-11-03

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