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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compound
formula
salt
crystal
another
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TW103144804A
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TW201609711A (zh
Inventor
艾咪 卡古拉達
祖漢 陳
麗娜 陳
丹尼斯 考畢
卡皮爾 卡其
達若 加藤
凱帝 奇頓
蘇德哈 康德佩利
克里斯 雷文斯
亞當 力克
魯班 馬汀尼茲
多尼明加 派尚
特洛伊 雷諾斯
布魯斯 洛斯
麥可 山基
亞當 史基瑞爾
潘蜜拉 賽恩
達斯汀 賽吉兒
納森 夏普洛
文威 鄧
詹姆士 泰勒
強納森 崔普
樂謙 余
安卓 華特曼
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美商基利法瑪席特有限責任公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic 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
    • C07D498/18—Bridged systems
    • A—HUMAN NECESSITIES
    • 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
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic 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
    • C07C233/09—Carboxylic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/04—Compounds 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
    • C07C251/10—Compounds 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
    • C07C251/12—Compounds 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/61—Carboxylic acid nitriles containing cyano groups and nitrogen atoms being part of imino groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/34—Esters 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic 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
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/12—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic 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
    • C07D498/16—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design 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)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Communicable Diseases (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)
  • Epidemiology (AREA)
  • Immunology (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)

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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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TW109137288A TWI762003B (zh) 2013-12-23 2014-12-22 抗病毒化合物之合成
TW103144804A TWI671292B (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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US (2) US9440991B2 (cg-RX-API-DMAC7.html)
EP (1) EP3087085B1 (cg-RX-API-DMAC7.html)
JP (1) JP6425727B2 (cg-RX-API-DMAC7.html)
KR (1) KR102366697B1 (cg-RX-API-DMAC7.html)
CN (3) CN116813596A (cg-RX-API-DMAC7.html)
AR (1) AR098959A1 (cg-RX-API-DMAC7.html)
AU (1) AU2014370125B2 (cg-RX-API-DMAC7.html)
CA (1) CA2934537C (cg-RX-API-DMAC7.html)
EA (1) EA201691031A1 (cg-RX-API-DMAC7.html)
ES (1) ES2724460T3 (cg-RX-API-DMAC7.html)
IL (1) IL246064A0 (cg-RX-API-DMAC7.html)
MX (1) MX2016008452A (cg-RX-API-DMAC7.html)
NZ (1) NZ720745A (cg-RX-API-DMAC7.html)
PL (1) PL3087085T3 (cg-RX-API-DMAC7.html)
PT (1) PT3087085T (cg-RX-API-DMAC7.html)
SG (1) SG11201604482QA (cg-RX-API-DMAC7.html)
SI (1) SI3087085T1 (cg-RX-API-DMAC7.html)
TR (1) TR201906413T4 (cg-RX-API-DMAC7.html)
TW (3) TWI762003B (cg-RX-API-DMAC7.html)
WO (1) WO2015100145A1 (cg-RX-API-DMAC7.html)

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KR20170116203A (ko) 2013-07-30 2017-10-18 질레드 코네티컷 인코포레이티드 Ｓｙｋ 억제제의 제제
NZ715776A (en) 2013-07-30 2017-04-28 Gilead Connecticut Inc Polymorph of syk inhibitors
TWI735853B (zh) 2013-12-23 2021-08-11 美商克洛諾斯生技有限公司 脾酪胺酸激酶抑制劑
AU2014370125B2 (en) 2013-12-23 2017-11-16 Gilead Sciences, Inc. Synthesis of a macrocyclic HCV NS3 inhibiting tripeptide
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
US10689675B2 (en) 2017-02-01 2020-06-23 Abbvie Inc. Enzymatic processes for the preparation of (±)-2-(difluoromethyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acid and (±)-2-(vinyl)-1-(alkoxycarbonyl)-cyclopropanecarboxylic acid
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
US11339168B2 (en) 2019-02-22 2022-05-24 Kronos Bio, Inc. Crystalline forms of 6-(6-aminopyrazin-2-yl)-N-(4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)imidazo[1,2-a]pyrazin-8-amine as Syk inhibitors
CN116041181A (zh) * 2023-01-04 2023-05-02 广州巨元生化有限公司 一种制备4-卤代-2-甲基-2-丁烯酸烃基酯的方法

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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 Gilead Sciences Inc 黃病毒科（Ｆｌａｖｉｖｉｒｉｄａｅ）病毒之巨環狀抑制劑

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

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