TWI671292B - 抗病毒化合物之合成 - Google Patents

抗病毒化合物之合成 Download PDF

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Publication number
TWI671292B
TWI671292B TW103144804A TW103144804A TWI671292B TW I671292 B TWI671292 B TW I671292B TW 103144804 A TW103144804 A TW 103144804A TW 103144804 A TW103144804 A TW 103144804A TW I671292 B TWI671292 B TW I671292B
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Taiwan
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compound
formula
salt
crystal
another
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TW103144804A
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Chinese (zh)
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TW201609711A (zh
Inventor
艾咪 卡古拉達
Amy Cagulada
祖漢 陳
Johann CHAN
麗娜 陳
Lina Chan
丹尼斯 考畢
Denise A. Colby
卡皮爾 卡其
Kapil Kumar KARKI
達若 加藤
Darryl Kato
凱帝 奇頓
Katie Keaton
蘇德哈 康德佩利
Sudha Kondapally
克里斯 雷文斯
Chris Levins
亞當 力克
Adam Littke
魯班 馬汀尼茲
Ruben Martinez
多尼明加 派尚
Dominika Pcion
特洛伊 雷諾斯
Troy Reynolds
布魯斯 洛斯
Bruce Ross
麥可 山基
Mike Sangi
亞當 史基瑞爾
Adam James SCHRIER
潘蜜拉 賽恩
Pamela Seng
達斯汀 賽吉兒
Dustin Siegel
納森 夏普洛
Nathan Shapiro
文威 鄧
Donald Tang
詹姆士 泰勒
James G. Taylor
強納森 崔普
Jonathan Tripp
樂謙 余
Lawrence YU
安卓 華特曼
Andrew W. Waltman
Original Assignee
美商基利法瑪席特有限責任公司
Gilead Pharmasset Llc
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/18Bridged systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/02Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/09Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/04Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/10Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C251/12Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton being acyclic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • C07C255/61Carboxylic acid nitriles containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/32Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/34Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D241/00Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40Benzopyrazines
    • C07D241/44Benzopyrazines 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 carbon atoms of the hetero ring
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D453/00Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/16Peri-condensed systems
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    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K5/00Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08Tripeptides
    • C07K5/0802Tripeptides with the first amino acid being neutral
    • C07K5/0804Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/02Systems containing only non-condensed rings with a three-membered ring
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Virology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
TW103144804A 2013-12-23 2014-12-22 抗病毒化合物之合成 TWI671292B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361920446P 2013-12-23 2013-12-23
US61/920,446 2013-12-23

Publications (2)

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TW201609711A TW201609711A (zh) 2016-03-16
TWI671292B true TWI671292B (zh) 2019-09-11

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TW103144804A TWI671292B (zh) 2013-12-23 2014-12-22 抗病毒化合物之合成
TW109137288A TWI762003B (zh) 2013-12-23 2014-12-22 抗病毒化合物之合成
TW108125271A TWI710547B (zh) 2013-12-23 2014-12-22 抗病毒化合物之合成

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TW109137288A TWI762003B (zh) 2013-12-23 2014-12-22 抗病毒化合物之合成
TW108125271A TWI710547B (zh) 2013-12-23 2014-12-22 抗病毒化合物之合成

Country Status (20)

Country Link
US (2) US9440991B2 (https=)
EP (1) EP3087085B1 (https=)
JP (1) JP6425727B2 (https=)
KR (1) KR102366697B1 (https=)
CN (3) CN105849118B (https=)
AR (1) AR098959A1 (https=)
AU (1) AU2014370125B2 (https=)
CA (1) CA2934537C (https=)
EA (1) EA201691031A1 (https=)
ES (1) ES2724460T3 (https=)
IL (1) IL246064A0 (https=)
MX (1) MX2016008452A (https=)
NZ (1) NZ720745A (https=)
PL (1) PL3087085T3 (https=)
PT (1) PT3087085T (https=)
SG (1) SG11201604482QA (https=)
SI (1) SI3087085T1 (https=)
TR (1) TR201906413T4 (https=)
TW (3) TWI671292B (https=)
WO (1) WO2015100145A1 (https=)

Families Citing this family (15)

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Publication number Priority date Publication date Assignee Title
EA029281B1 (ru) 2013-07-30 2018-03-30 Джилид Коннектикут, Инк. Полиморф ингибиторов syk
CA2919522C (en) * 2013-07-30 2019-02-26 Gilead Connecticut, Inc. Formulation of syk inhibitors
TWI662037B (zh) 2013-12-23 2019-06-11 美商基利科學股份有限公司 脾酪胺酸激酶抑制劑
PT3087085T (pt) 2013-12-23 2019-06-04 Gilead Sciences Inc Síntese de um tripéptido macrocíclico inibidor de ns3 de hcv
US9809576B1 (en) 2014-07-18 2017-11-07 Abbvie Inc. Synthetic route to anti-viral agents
US9809534B1 (en) * 2014-07-21 2017-11-07 Abbvie Inc. Difluoroalkylcyclopropyl amino acids and esters, and syntheses thereof
US10059969B1 (en) 2014-10-03 2018-08-28 Abbvie Inc. Process for the preparation of (S)-2-amino-non-8-enoic acid
US10316338B1 (en) 2015-01-30 2019-06-11 Abb Vie Inc. Enzymatic process for the preparation of (1S,2R)-2-(difluoromethyl)-1-(propoxycarbonyl)cyclopropanecarboxylic acid
US10450291B2 (en) 2015-06-29 2019-10-22 Central Glass Company, Limited Method for producing fluorine-containing cyclopropane carboxylic acid compound
EP3577100A4 (en) 2017-02-01 2021-03-10 Abbvie Inc. ENZYMATIC PROCESS FOR THE PRODUCTION OF (±) -2- (DIFLUOROMETHYL) -1- (ALCOXYCARBONYL) -CYCLOPROPANECARBONIC ACID AND (±) -2- (VINYL) -1- (ALCOXYCARBONYLURE) -CYCLOPROPANEC
CN107739319A (zh) * 2017-10-31 2018-02-27 上海同昌生物医药科技有限公司 一种Glecaprevir合成中间体及其胺盐的制备方法
WO2019084740A1 (zh) * 2017-10-31 2019-05-09 上海同昌生物医药科技有限公司 一种Glecaprevir合成中间体及其胺盐的制备方法
CN107827748A (zh) * 2017-11-14 2018-03-23 安徽华胜医药科技有限公司 一种乙酸2‑烯丙基环丙酯消旋体的合成方法
KR102519417B1 (ko) 2018-11-28 2023-04-10 삼성디스플레이 주식회사 스트레처블 표시 장치
CN113950479A (zh) 2019-02-22 2022-01-18 克洛诺斯生物股份有限公司 作为syk抑制剂的缩合吡嗪的固体形式

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TW200938550A (en) * 2007-11-14 2009-09-16 Enanta Pharm Inc Quinoxaline-containing compounds as hepatitis C virus inhibitors
TW201023860A (en) * 2008-07-22 2010-07-01 Merck Sharp & Dohme Macrocyclic quinoxaline compounds as HCV NS3 protease inhibitors
TW201216979A (en) * 2010-09-21 2012-05-01 Enanta Pharm Inc Macrocyclic proline derived HCV serine protease inhibitors
TW201307355A (zh) * 2010-12-10 2013-02-16 吉李德科學股份有限公司 黃病毒科(Flaviviridae)病毒之巨環狀抑制劑

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KR20060109937A (ko) * 2003-12-15 2006-10-23 니뽄 다바코 산교 가부시키가이샤 N-치환-n-술포닐아미노시클로프로판 화합물 및 그의약제학적 용도
US8211891B2 (en) 2008-04-30 2012-07-03 Enanta Pharmaceuticals, Inc. Difluoromethyl-containing macrocyclic compounds as hepatitis C virus inhibitors
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UA119315C2 (uk) 2012-07-03 2019-06-10 Гіліад Фармассет Елелсі Інгібітори вірусу гепатиту с
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WO2015100144A1 (en) * 2013-12-23 2015-07-02 Gilead Sciences, Inc. Crystalline forms of a macrocyclic hcv ns3 inhibiting tripeptide
PT3087085T (pt) 2013-12-23 2019-06-04 Gilead Sciences Inc Síntese de um tripéptido macrocíclico inibidor de ns3 de hcv

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TW200938550A (en) * 2007-11-14 2009-09-16 Enanta Pharm Inc Quinoxaline-containing compounds as hepatitis C virus inhibitors
TW201023860A (en) * 2008-07-22 2010-07-01 Merck Sharp & Dohme Macrocyclic quinoxaline compounds as HCV NS3 protease inhibitors
TW201216979A (en) * 2010-09-21 2012-05-01 Enanta Pharm Inc Macrocyclic proline derived HCV serine protease inhibitors
TW201307355A (zh) * 2010-12-10 2013-02-16 吉李德科學股份有限公司 黃病毒科(Flaviviridae)病毒之巨環狀抑制劑

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JP2017509585A (ja) 2017-04-06
CN111320610B (zh) 2023-06-06
TW202106661A (zh) 2021-02-16
AU2014370125B2 (en) 2017-11-16
KR102366697B1 (ko) 2022-02-25
US9440991B2 (en) 2016-09-13
KR20160101934A (ko) 2016-08-26
CA2934537C (en) 2022-08-16
CA2934537A1 (en) 2015-07-02
AU2014370125A1 (en) 2016-06-23
TW201609711A (zh) 2016-03-16
AR098959A1 (es) 2016-06-22
ES2724460T3 (es) 2019-09-11
US10030033B2 (en) 2018-07-24
JP6425727B2 (ja) 2018-11-21
US20170210756A1 (en) 2017-07-27
EA201691031A1 (ru) 2017-01-30
US20150175626A1 (en) 2015-06-25
EP3087085B1 (en) 2019-02-20
TR201906413T4 (tr) 2019-05-21
PT3087085T (pt) 2019-06-04
CN105849118B (zh) 2020-03-31
TWI710547B (zh) 2020-11-21
WO2015100145A1 (en) 2015-07-02
TWI762003B (zh) 2022-04-21
MX2016008452A (es) 2016-10-14
CN111320610A (zh) 2020-06-23
HK1222401A1 (zh) 2017-06-30
SG11201604482QA (en) 2016-07-28
EP3087085A1 (en) 2016-11-02
NZ720745A (en) 2018-02-23
CN116813596A (zh) 2023-09-29
IL246064A0 (en) 2016-07-31
TW201938527A (zh) 2019-10-01
CN105849118A (zh) 2016-08-10
CN116813596B (zh) 2026-03-13
SI3087085T1 (sl) 2019-05-31
PL3087085T3 (pl) 2019-07-31

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