KR102366697B1 - 마크로시클릭 hcv ns3 억제 트리펩티드의 합성 - Google Patents

마크로시클릭 hcv ns3 억제 트리펩티드의 합성 Download PDF

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KR102366697B1
KR102366697B1 KR1020167016776A KR20167016776A KR102366697B1 KR 102366697 B1 KR102366697 B1 KR 102366697B1 KR 1020167016776 A KR1020167016776 A KR 1020167016776A KR 20167016776 A KR20167016776 A KR 20167016776A KR 102366697 B1 KR102366697 B1 KR 102366697B1
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formula
compound
salt
alkyl
benzene
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KR20160101934A (ko
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에이미 카구라다
조한 찬
리나 찬
데니스 에이. 콜비
카필 쿠마르 카르키
다릴 카토
케이티 안 키톤
수다 콘다팔리
크리스 레빈스
아담 리트케
루벤 마티네즈
도미니카 사이언
트로이 레이놀즈
브루스 로스
마이클 산기
아담 제이. 슈리어
파멜라 셍
더스틴 시겔
나단 사피로
도날드 탕
제임스 지. 테일러
조나단 트립
로렌스 유
앤드류 더블유. 월트만
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길리애드 사이언시즈, 인코포레이티드
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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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/06—Tripeptides
    • 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
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    • 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
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    • 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
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    • 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
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    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
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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
    • C07D498/16—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
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    • 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)
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  • General Health & Medical Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
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  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Virology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
KR1020167016776A 2013-12-23 2014-12-18 마크로시클릭 hcv ns3 억제 트리펩티드의 합성 Active KR102366697B1 (ko)

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US201361920446P 2013-12-23 2013-12-23
US61/920,446 2013-12-23
PCT/US2014/071319 WO2015100145A1 (en) 2013-12-23 2014-12-18 Synthesis of a macrocyclic hcv ns3 inhibiting tripeptide

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KR20160101934A KR20160101934A (ko) 2016-08-26
KR102366697B1 true KR102366697B1 (ko) 2022-02-25

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US (2) US9440991B2 (enExample)
EP (1) EP3087085B1 (enExample)
JP (1) JP6425727B2 (enExample)
KR (1) KR102366697B1 (enExample)
CN (3) CN105849118B (enExample)
AR (1) AR098959A1 (enExample)
AU (1) AU2014370125B2 (enExample)
CA (1) CA2934537C (enExample)
EA (1) EA201691031A1 (enExample)
ES (1) ES2724460T3 (enExample)
IL (1) IL246064A0 (enExample)
MX (1) MX2016008452A (enExample)
NZ (1) NZ720745A (enExample)
PL (1) PL3087085T3 (enExample)
PT (1) PT3087085T (enExample)
SG (1) SG11201604482QA (enExample)
SI (1) SI3087085T1 (enExample)
TR (1) TR201906413T4 (enExample)
TW (3) TWI762003B (enExample)
WO (1) WO2015100145A1 (enExample)

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MX2016001304A (es) 2013-07-30 2016-04-07 Gilead Connecticut Inc Polimorfo de inhibidores de syk.
AU2014370125B2 (en) 2013-12-23 2017-11-16 Gilead Sciences, Inc. Synthesis of a macrocyclic HCV NS3 inhibiting tripeptide
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
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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
JP2020505952A (ja) 2017-02-01 2020-02-27 アッヴィ・インコーポレイテッド （±）−２−（ジフルオロメチル）−１−（アルコキシカルボニル）シクロプロパンカルボン酸及び（±）−２−（ビニル）−１−（アルコキシカルボニル）シクロプロパンカルボン酸の酵素的製造方法
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
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
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
KR20210131372A (ko) 2019-02-22 2021-11-02 크로노스 바이오, 인코포레이티드 Syk 억제제로서의 축합된 피라진의 고체 형태
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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US20100150866A1 (en) 2008-12-15 2010-06-17 Bristol-Myers Squibb Company Hepatitis C Virus Inhibitors
US20140017198A1 (en) 2012-07-03 2014-01-16 Gilead Sciences, Inc. Inhibitors of hepatitis c virus

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CN105849118B (zh) 2020-03-31
HK1222401A1 (zh) 2017-06-30
CA2934537A1 (en) 2015-07-02
TW201609711A (zh) 2016-03-16
TWI762003B (zh) 2022-04-21
CN116813596A (zh) 2023-09-29
AU2014370125A1 (en) 2016-06-23
JP6425727B2 (ja) 2018-11-21
US20170210756A1 (en) 2017-07-27
AU2014370125B2 (en) 2017-11-16
SI3087085T1 (sl) 2019-05-31
TWI671292B (zh) 2019-09-11
TWI710547B (zh) 2020-11-21
CA2934537C (en) 2022-08-16
US9440991B2 (en) 2016-09-13
EP3087085A1 (en) 2016-11-02
IL246064A0 (en) 2016-07-31
MX2016008452A (es) 2016-10-14
KR20160101934A (ko) 2016-08-26
CN111320610A (zh) 2020-06-23
US10030033B2 (en) 2018-07-24
JP2017509585A (ja) 2017-04-06
SG11201604482QA (en) 2016-07-28
NZ720745A (en) 2018-02-23
CN111320610B (zh) 2023-06-06
US20150175626A1 (en) 2015-06-25
EP3087085B1 (en) 2019-02-20
TR201906413T4 (tr) 2019-05-21
WO2015100145A1 (en) 2015-07-02
PL3087085T3 (pl) 2019-07-31
ES2724460T3 (es) 2019-09-11
TW202106661A (zh) 2021-02-16
TW201938527A (zh) 2019-10-01
EA201691031A1 (ru) 2017-01-30
AR098959A1 (es) 2016-06-22
CN105849118A (zh) 2016-08-10
PT3087085T (pt) 2019-06-04

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