TWI265927B - Novel compounds as NS3-serine protease inhibitors of hepatitis C virus - Google Patents

Novel compounds as NS3-serine protease inhibitors of hepatitis C virus

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Publication number
TWI265927B
TWI265927B TW092101229A TW92101229A TWI265927B TW I265927 B TWI265927 B TW I265927B TW 092101229 A TW092101229 A TW 092101229A TW 92101229 A TW92101229 A TW 92101229A TW I265927 B TWI265927 B TW I265927B
Authority
TW
Taiwan
Prior art keywords
novel compounds
hepatitis
virus
protease inhibitors
serine protease
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Application number
TW092101229A
Other languages
English (en)
Chinese (zh)
Other versions
TW200306311A (en
Inventor
Ashok Arasappan
Frank Bennett
Stephane L Bogen
Kevin X Chen
Edwin Jao
Original Assignee
Schering Corp
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Publication of TW200306311A publication Critical patent/TW200306311A/zh
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Publication of TWI265927B publication Critical patent/TWI265927B/zh

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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    • 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
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by 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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    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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
    • C07D213/72—Nitrogen atoms
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    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI400042B (zh) * 2007-06-08 2013-07-01 Tci Co Ltd 食品錠劑

Families Citing this family (67)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MXPA05013751A (es) * 2003-06-17 2006-03-08 Schering Corp Procedimiento e intermediarios para la preparacion de 3-(amino)-3-ciclobutilmetil-2-hidroxi-propionamida o sus sales.
CN1867579A (zh) * 2003-08-26 2006-11-22 先灵公司 丙肝病毒的新的肽模拟物ns3－丝氨酸蛋白酶抑制剂
MXPA06003455A (es) * 2003-09-26 2006-05-31 Schering Corp Inhibidores macrociclicos de la serina proteasa ns3 del virus de la hepatitis c.
EP1742913A1 (en) 2003-12-11 2007-01-17 Schering Corporation Inhibitors of hepatitis c virus ns3/ns4a serine protease
DK1713823T3 (da) 2004-01-30 2010-03-08 Medivir Ab HCV NS-3 serinproteaseinhibitorer
RU2006134000A (ru) * 2004-02-27 2008-04-10 Шеринг Корпорейшн (US) Новые кетоамиды с циклическим p4s, действующие как ингибиторы сериновой протеазы ns3 ируса гепатита с
US7192957B2 (en) 2004-02-27 2007-03-20 Schering Corporation Compounds as inhibitors of hepatitis C virus NS3 serine protease
WO2006113942A2 (en) * 2005-04-20 2006-10-26 Schering Corporation Method of inhibiting cathepsin activity
US20060276407A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods of treating hepatitis C virus
WO2006130552A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods of treating hepatitis c virus
US20060276405A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods for treating hepatitis C
ES2572980T3 (es) * 2005-06-02 2016-06-03 Merck Sharp & Dohme Corp. Combinación de inhibidores de la proteasa del VHC con un tensioactivo
US20060281689A1 (en) * 2005-06-02 2006-12-14 Schering Corporation Method for modulating activity of HCV protease through use of a novel HCV protease inhibitor to reduce duration of treatment period
US20070237818A1 (en) * 2005-06-02 2007-10-11 Malcolm Bruce A Controlled-release formulation of HCV protease inhibitor and methods using the same
WO2006130687A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Liver/plasma concentration ratio for dosing hepatitis c virus protease inhibitor
US20060275366A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Controlled-release formulation
WO2006130666A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Medicaments and methods combining a hcv protease inhibitor and an akr competitor
US8119602B2 (en) 2005-06-02 2012-02-21 Schering Corporation Administration of HCV protease inhibitors in combination with food to improve bioavailability
EP1898941A2 (en) * 2005-06-02 2008-03-19 Schering Corporation Controlled-release formulation useful for treating disorders associated with hepatitis c virus
PE20070211A1 (es) 2005-07-29 2007-05-12 Medivir Ab Compuestos macrociclicos como inhibidores del virus de hepatitis c
AR055395A1 (es) 2005-08-26 2007-08-22 Vertex Pharma Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c
KR20140098867A (ko) 2005-11-11 2014-08-08 버텍스 파마슈티칼스 인코포레이티드 Ｃ형 간염 바이러스 변이체
US7705138B2 (en) 2005-11-11 2010-04-27 Vertex Pharmaceuticals Incorporated Hepatitis C virus variants
CN101336229B (zh) 2005-12-23 2012-06-13 西兰岛药物有限公司 改性的拟赖氨酸化合物
US7816348B2 (en) 2006-02-03 2010-10-19 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
US20080045530A1 (en) * 2006-04-11 2008-02-21 Trixi Brandl Organic Compounds and Their Uses
CN101421292A (zh) * 2006-04-11 2009-04-29 诺瓦提斯公司 Hcv抑制剂
KR101059593B1 (ko) * 2006-04-11 2011-08-25 노파르티스 아게 Ｈｃｖ/ｈｉｖ 억제제 및 이들의 용도
WO2007120595A2 (en) * 2006-04-11 2007-10-25 Novartis Ag Amines for the treatment of hcv
CN101506167A (zh) 2006-08-17 2009-08-12 贝林格尔.英格海姆国际有限公司 病毒聚合酶抑制剂
WO2008057995A2 (en) * 2006-11-02 2008-05-15 Taigen Biotechnology Co., Ltd. Hcv protease inhibitors
CA2673111A1 (en) * 2006-12-07 2008-06-19 Schering Corporation Ph sensitive matrix formulation
JP2010513492A (ja) 2006-12-19 2010-04-30 シェーリング コーポレイション ３−（アミノ）−３−（シクロブチルメチル）−２−（ヒドロキシ）−プロピオンアミド塩酸塩の調製
US20080188545A1 (en) 2006-12-21 2008-08-07 Alimardanov Asaf R Synthesis of pyrrolidine compounds
US8242140B2 (en) 2007-08-03 2012-08-14 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
JP5095824B2 (ja) * 2007-10-10 2012-12-12 ノバルティス アーゲー スピロピロリジン類およびｈｃｖおよびｈｉｖ感染に対するその使用
WO2009055335A2 (en) * 2007-10-25 2009-04-30 Taigen Biotechnology Co., Ltd. Hcv protease inhibitors
BRPI0821342A2 (pt) 2007-12-19 2019-09-24 Boehringer Ingelheim Int inibidores da polimerase viral
JP5755449B2 (ja) * 2007-12-21 2015-07-29 セルジーン アビロミクス リサーチ， インコーポレイテッド Ｈｃｖプロテアーゼ阻害剤およびその使用
CN101951769B (zh) * 2007-12-21 2014-12-31 阿维拉制药公司 Hcv蛋白酶抑制剂和其用途
US8309685B2 (en) * 2007-12-21 2012-11-13 Celgene Avilomics Research, Inc. HCV protease inhibitors and uses thereof
US8293705B2 (en) 2007-12-21 2012-10-23 Avila Therapeutics, Inc. HCV protease inhibitors and uses thereof
CN101580535B (zh) * 2008-05-16 2012-10-03 太景生物科技股份有限公司 丙型肝炎病毒蛋白酶抑制剂
EP2334680A2 (en) 2008-08-20 2011-06-22 Sequoia Pharmaceuticals, Inc. Hcv protease inhibitors
CN102271699A (zh) 2009-01-07 2011-12-07 西尼克斯公司 用于治疗hcv和hiv感染的环孢菌素衍生物
US20110182850A1 (en) * 2009-04-10 2011-07-28 Trixi Brandl Organic compounds and their uses
US8512690B2 (en) 2009-04-10 2013-08-20 Novartis Ag Derivatised proline containing peptide compounds as protease inhibitors
US8980920B2 (en) 2009-05-29 2015-03-17 Merck Sharp & Dohme Corp. Antiviral compounds of three linked aryl moieties to treat diseases such as hepatitis C
EP2477980B1 (en) * 2009-09-15 2016-06-08 Taigen Biotechnology Co., Ltd. Hcv protease inhibitors
EP2503881B1 (en) 2009-11-25 2015-05-13 Merck Sharp & Dohme Corp. Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases
US20130156731A1 (en) 2009-12-22 2013-06-20 Kevin X. Chen Fused tricyclic compounds and methods of use thereof for the treatment of viral diseas
US20110178107A1 (en) * 2010-01-20 2011-07-21 Taigen Biotechnology Co., Ltd. Hcv protease inhibitors
CA2788155C (en) 2010-01-27 2018-04-24 AB Pharma Ltd. Polyheterocyclic compounds highly potent as hcv inhibitors
US8609635B2 (en) 2010-03-09 2013-12-17 Merck Sharp & Dohme Corp. Fused tricyclic silyl compounds and methods of use thereof for the treatment of viral diseases
AU2011286276A1 (en) 2010-07-26 2013-01-24 Merck Sharp & Dohme Corp. Substituted biphenylene compounds and methods of use thereof for the treatment of viral diseases
CA2812779A1 (en) 2010-09-29 2012-04-19 Merck Sharp & Dohme Corp. Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases
EA201391519A1 (ru) 2011-04-13 2014-03-31 Мерк Шарп И Доум Корп. 2'-замещенные нуклеозидные производные и способы их применения для лечения вирусных заболеваний
WO2012142075A1 (en) 2011-04-13 2012-10-18 Merck Sharp & Dohme Corp. 2'-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases
WO2012171332A1 (zh) 2011-06-16 2012-12-20 爱博新药研发(上海)有限公司 抑制丙型肝炎病毒的大环状杂环化合物及其制备和应用
WO2013033899A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Substituted benzofuran compounds and methods of use thereof for the treatment of viral diseases
WO2013033900A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Tetracyclic heterocycle compounds and methods of use thereof for the treatment of viral diseases
WO2013033901A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases
WO2013039876A1 (en) 2011-09-14 2013-03-21 Merck Sharp & Dohme Corp. Silyl-containing heterocyclic compounds and methods of use thereof for the treatment of viral diseases
CN103387510B (zh) * 2013-08-08 2015-09-09 苏州永健生物医药有限公司 一种β-氨基-alpha-羟基环丁基丁酰胺盐酸盐的合成方法
EP3063140A4 (en) 2013-10-30 2017-11-08 Merck Sharp & Dohme Corp. Pseudopolymorphs of an hcv ns5a inhibitor and uses thereof
US11324799B2 (en) 2017-05-05 2022-05-10 Zealand Pharma A/S Gap junction intercellular communication modulators and their use for the treatment of diabetic eye disease
US11351149B2 (en) 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU216017B (hu) 1987-11-18 1999-04-28 Chiron Corp. Eljárás HCV-1 polipeptidek, HCV-1 polinukleotidok, rekombináns vektorok és gazdasejtek, valamint immunesszé kit, hepatitis C vírusfertőzés elleni vakcinák, a fertőzés kimutatására szolgáló diagnosztikumok előállítására, és immunvizsgálati és vírustenyészt
ATE132182T1 (de) 1989-02-01 1996-01-15 Asahi Glass Co Ltd Azeotrope oder azeotropähnliche zusammensetzung auf der basis von chlorfluorkohlenwasserstoffen
DK0527788T3 (da) * 1990-04-04 2004-09-06 Chiron Corp Hepatitis C virus protease
US5922757A (en) 1996-09-30 1999-07-13 The Regents Of The University Of California Treatment and prevention of hepatic disorders
CN1133649C (zh) 1996-10-18 2004-01-07 沃泰克斯药物股份有限公司 丝氨酸蛋白酶、特别是丙型肝炎病毒ns3蛋白酶的抑制剂
GB9623908D0 (en) 1996-11-18 1997-01-08 Hoffmann La Roche Amino acid derivatives
US6143715A (en) 1997-08-11 2000-11-07 Boehringer Ingelheim (Canada) Ltd. Hepatitis C inhibitor peptide analogues
AR022061A1 (es) 1998-08-10 2002-09-04 Boehringer Ingelheim Ca Ltd Peptidos inhibidores de la hepatitis c, una composicion farmaceutica que los contiene, el uso de los mismos para preparar una composicion farmaceutica, el uso de un producto intermedio para la preparacion de estos peptidos y un procedimiento para la preparacion de un peptido analogo de los mismos.
US6323180B1 (en) 1998-08-10 2001-11-27 Boehringer Ingelheim (Canada) Ltd Hepatitis C inhibitor tri-peptides
ATE297946T1 (de) 2000-04-03 2005-07-15 Vertex Pharma Inhibitoren von serin proteasen, speziell der hepatitis-c-virus ns3-protease
AR029851A1 (es) * 2000-07-21 2003-07-16 Dendreon Corp Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c
AR034127A1 (es) * 2000-07-21 2004-02-04 Schering Corp Imidazolidinonas como inhibidores de ns3-serina proteasa del virus de hepatitis c, composicion farmaceutica, un metodo para su preparacion, y el uso de las mismas para la manufactura de un medicamento
SI1385870T1 (sl) * 2000-07-21 2010-08-31 Schering Corp Peptidi kot NS3-serin proteazni inhibitorji virusa hepatitisa C

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI400042B (zh) * 2007-06-08 2013-07-01 Tci Co Ltd 食品錠劑

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