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

Macrocyclic indole derivatives useful as hepatitis c virus inhibitors Download PDF

Info

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
Authority
CA
Canada
Prior art keywords
compound
compounds
formula
synthesis
hcv
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
CA2729307A
Other languages
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
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Janssen Sciences Ireland ULC
Original Assignee
Janssen Sciences Ireland ULC
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
Application filed by Janssen Sciences Ireland ULC filed Critical Janssen Sciences Ireland ULC
Publication of CA2729307A1 publication Critical patent/CA2729307A1/en
Application granted granted Critical
Publication of CA2729307C publication Critical patent/CA2729307C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Biotechnology (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
EP08159965.6 2008-07-08
EP08159965 2008-07-08
EP08160254 2008-07-11
EP08160254.2 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 (enExample)
EP (1) EP2310396B1 (enExample)
JP (2) JP5426671B2 (enExample)
KR (1) KR101640374B1 (enExample)
CN (1) CN102089314B (enExample)
AP (1) AP2743A (enExample)
AR (1) AR072726A1 (enExample)
AU (1) AU2009267389B8 (enExample)
BR (1) BRPI0915887B8 (enExample)
CA (1) CA2729307C (enExample)
CL (1) CL2011000032A1 (enExample)
CO (1) CO6351793A2 (enExample)
CR (1) CR20110076A (enExample)
DK (1) DK2310396T3 (enExample)
EA (1) EA019008B1 (enExample)
EC (1) ECSP11010750A (enExample)
ES (1) ES2651038T3 (enExample)
HN (1) HN2011000072A (enExample)
HR (1) HRP20171892T1 (enExample)
HU (1) HUE035244T2 (enExample)
IL (1) IL210086A (enExample)
LT (1) LT2310396T (enExample)
MX (1) MX2011000276A (enExample)
NI (1) NI201100010A (enExample)
NO (1) NO2310396T3 (enExample)
NZ (2) NZ603343A (enExample)
SI (1) SI2310396T1 (enExample)
SV (1) SV2011003796A (enExample)
TW (1) TWI454476B (enExample)
UY (1) UY31973A (enExample)
WO (1) WO2010003658A1 (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8524716B2 (en) 2007-12-24 2013-09-03 Janssen R&D Ireland Macrocyclic indoles as hepatitis C virus inhibitors
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
NZ602552A (en) * 2010-04-13 2014-09-26 Janssen Pharmaceuticals Inc Combination of a macrocyclic inhibitor of hcv, a non-nucleoside and a nucleoside
WO2011161232A1 (en) 2010-06-24 2011-12-29 Tibotec Pharmaceuticals PREPARATION OF 13-CYCLOHEXYL-3-METHOXY-6-[METHYL-(2-{2-[METHYL-(SULPHAMOYL)-AMINO]-ETHOXY}-ETHYL)-CARBAMOYL]-7H-INDOLO-[2,1-a]-[2]-BENZAZEPINE-10-CARBOXYLIC ACID
EP2760821B1 (en) 2011-09-02 2017-10-11 Novartis AG Choline salt of an anti-inflammatory substituted cyclobutenedione compound
US8716275B2 (en) * 2011-10-20 2014-05-06 Bristol-Myers Squibb Company Compound for the treatment of hepatitis C
KR20150046083A (ko) 2012-08-31 2015-04-29 얀센 파마슈티칼즈, 인코포레이티드 Ｈｃｖ의 거대환형 프로테아제 저해제, 비­뉴클레오시드계 ｈｃｖ 저해제 및 리토나비르의 조합물
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
US11066357B2 (en) 2017-12-26 2021-07-20 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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CZ298463B6 (cs) 1996-04-23 2007-10-10 Vertex Pharmaceuticals Incorporated Deriváty mocoviny pro použití jako inhibitory IMPDH enzymu a farmaceutické prostredky, které je obsahují
AU6701598A (en) 1997-03-14 1998-09-29 Vertex Pharmaceuticals Incorporated Inhibitors of impdh enzyme
SK13332001A3 (sk) 1999-03-19 2002-02-05 Vertex Pharmaceuticals Incorporated Inhibítory IMPDH enzýmu a ich použitie
US6891331B2 (en) 2000-08-30 2005-05-10 Matsushita Electric Industrial Co., Ltd. Plasma display unit and production method thereof
KR20120090077A (ko) 2004-01-30 2012-08-16 얀센 알 앤드 디 아일랜드 Ｈｃｖ ｎｓ?３ 세린 프로테아제 저해제
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
RU2008112661A (ru) 2005-09-02 2009-10-10 Тиботек Фармасьютикалз Лтд. (Ie) Бензодиазепины в качестве ингибиторов hcv
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
US7521443B2 (en) * 2006-05-17 2009-04-21 Bristol-Myers Squibb Company Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors
US7456166B2 (en) 2006-05-17 2008-11-25 Bristol-Myers Squibb Company Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors
US7521441B2 (en) 2006-05-22 2009-04-21 Bristol-Myers Squibb Company Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors
WO2007140200A2 (en) * 2006-05-25 2007-12-06 Bristol-Myers Squibb Company Cyclopropyl fused indolobenzazepine hcv ns5b inhibitors
MX2009003452A (es) 2006-10-10 2009-04-14 Medivir Ab Inhibidores nucleosidicos del vhc.
CA2672250C (en) * 2006-12-20 2013-04-30 Ian Stansfield Antiviral indoles
JP2010533699A (ja) * 2007-07-17 2010-10-28 イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー Ｃ型肝炎感染症の治療のための大環状インドール誘導体
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
TW201023858A (en) 2008-09-18 2010-07-01 Ortho Mcneil Janssen Pharm Synergistic combinations of a macrocyclic inhibitor of HCV and a nucleoside
MX340792B (es) 2009-02-27 2016-07-25 Ortho-Mcneil-Janssen Pharmaceuticals Inc * Sal amorfa de un inhibidor macrociclico de virus de hepatitis c.
NZ602552A (en) 2010-04-13 2014-09-26 Janssen Pharmaceuticals Inc Combination of a macrocyclic inhibitor of hcv, a non-nucleoside and a nucleoside
WO2011161232A1 (en) 2010-06-24 2011-12-29 Tibotec Pharmaceuticals PREPARATION OF 13-CYCLOHEXYL-3-METHOXY-6-[METHYL-(2-{2-[METHYL-(SULPHAMOYL)-AMINO]-ETHOXY}-ETHYL)-CARBAMOYL]-7H-INDOLO-[2,1-a]-[2]-BENZAZEPINE-10-CARBOXYLIC ACID
KR20150046083A (ko) 2012-08-31 2015-04-29 얀센 파마슈티칼즈, 인코포레이티드 Ｈｃｖ의 거대환형 프로테아제 저해제, 비­뉴클레오시드계 ｈｃｖ 저해제 및 리토나비르의 조합물

Also Published As

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

Similar Documents

Publication Publication Date Title
DK2310396T3 (en) MACROCYCLIC INSIDE DERIVATIVES USED AS INHIBITORS OF HEPATITIS C VIRUS
CA2710644C (en) Macrocyclic indoles as hepatitis c virus inhibitors
CA2733762C (en) Macrocyclic indole derivatives useful as hepatitis c virus inhibitors
AU2013204963B2 (en) Macrocyclic indole derivatives useful as hepatitis C virus inhibitors
WO2008099022A1 (en) 10-sulfonyl-dibenzodiazepinones useful as hepatitis c virus inhibitors
HK1155734B (en) Macrocyclic indole derivatives useful as hepatitis c virus inhibitors
WO2008099021A1 (en) Dibenzodiazepinones useful as hepatitis c virus inhibitors

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20140702

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-4-4-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20251023

H13 Ip right lapsed

Free format text: ST27 STATUS EVENT CODE: N-4-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE

Effective date: 20260219

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT

Effective date: 20260219