CN116813596B - 大环hcv ns3抑制三肽的合成 - Google Patents

大环hcv ns3抑制三肽的合成

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Publication number
CN116813596B
CN116813596B CN202310617293.7A CN202310617293A CN116813596B CN 116813596 B CN116813596 B CN 116813596B CN 202310617293 A CN202310617293 A CN 202310617293A CN 116813596 B CN116813596 B CN 116813596B
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compound
formula
salt
crystal
alkyl
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Chinese (zh)
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CN116813596A (zh
Inventor
A·卡库拉达
J·常
L·常
D·A·科尔比
K·K·卡尔基
D·卡托
K·A·凯顿
S·康达帕利
C·勒文斯
A·利特克
R·马丁内斯
D·皮乔恩
T·雷诺尔斯
B·罗斯
M·桑吉
A·J·施里尔
P·森
D·西格尔
N·夏皮罗
D·唐
J·G·泰勒
J·特里普
L·于
A·W·瓦特曼
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Gilead Sciences Inc
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Gilead Sciences Inc
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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)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • 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)
  • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
CN202310617293.7A 2013-12-23 2014-12-18 大环hcv ns3抑制三肽的合成 Active CN116813596B (zh)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201361920446P 2013-12-23 2013-12-23
US61/920,446 2013-12-23
CN201480070017.2A CN105849118B (zh) 2013-12-23 2014-12-18 大环hcv ns3抑制三肽的合成
PCT/US2014/071319 WO2015100145A1 (en) 2013-12-23 2014-12-18 Synthesis of a macrocyclic hcv ns3 inhibiting tripeptide

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CN201480070017.2A Division CN105849118B (zh) 2013-12-23 2014-12-18 大环hcv ns3抑制三肽的合成

Publications (2)

Publication Number Publication Date
CN116813596A CN116813596A (zh) 2023-09-29
CN116813596B true CN116813596B (zh) 2026-03-13

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CN202310617293.7A Active CN116813596B (zh) 2013-12-23 2014-12-18 大环hcv ns3抑制三肽的合成
CN201480070017.2A Active CN105849118B (zh) 2013-12-23 2014-12-18 大环hcv ns3抑制三肽的合成
CN202010152008.5A Active CN111320610B (zh) 2013-12-23 2014-12-18 大环hcv ns3抑制三肽的合成

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CN201480070017.2A Active CN105849118B (zh) 2013-12-23 2014-12-18 大环hcv ns3抑制三肽的合成
CN202010152008.5A Active CN111320610B (zh) 2013-12-23 2014-12-18 大环hcv ns3抑制三肽的合成

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US (2) US9440991B2 (enExample)
EP (1) EP3087085B1 (enExample)
JP (1) JP6425727B2 (enExample)
KR (1) KR102366697B1 (enExample)
CN (3) CN116813596B (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) TWI710547B (enExample)
WO (1) WO2015100145A1 (enExample)

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EA029281B1 (ru) 2013-07-30 2018-03-30 Джилид Коннектикут, Инк. Полиморф ингибиторов syk
PL3027171T3 (pl) 2013-07-30 2020-08-24 Gilead Connecticut, Inc. Formulacja inhibitorów syk
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
CA2934537C (en) 2013-12-23 2022-08-16 Gilead Sciences, Inc. Synthesis of an antiviral compound
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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
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
AU2020225455A1 (en) 2019-02-22 2021-09-09 Kronos Bio, Inc. Solid forms of condensed pyrazines as Syk inhibitors
CN116041181B (zh) * 2023-01-04 2026-05-01 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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TW201609711A (zh) 2016-03-16
EP3087085A1 (en) 2016-11-02
MX2016008452A (es) 2016-10-14
US20150175626A1 (en) 2015-06-25
CN116813596A (zh) 2023-09-29
SG11201604482QA (en) 2016-07-28
US9440991B2 (en) 2016-09-13
US20170210756A1 (en) 2017-07-27
NZ720745A (en) 2018-02-23
EA201691031A1 (ru) 2017-01-30
CN111320610B (zh) 2023-06-06
IL246064A0 (en) 2016-07-31
ES2724460T3 (es) 2019-09-11
SI3087085T1 (sl) 2019-05-31
KR20160101934A (ko) 2016-08-26
TW201938527A (zh) 2019-10-01
EP3087085B1 (en) 2019-02-20
TWI762003B (zh) 2022-04-21
TWI671292B (zh) 2019-09-11
CN105849118A (zh) 2016-08-10
CN111320610A (zh) 2020-06-23
PL3087085T3 (pl) 2019-07-31
HK1222401A1 (zh) 2017-06-30
AU2014370125A1 (en) 2016-06-23
JP2017509585A (ja) 2017-04-06
JP6425727B2 (ja) 2018-11-21
CN105849118B (zh) 2020-03-31
TR201906413T4 (tr) 2019-05-21
KR102366697B1 (ko) 2022-02-25
CA2934537A1 (en) 2015-07-02
AR098959A1 (es) 2016-06-22
WO2015100145A1 (en) 2015-07-02
CA2934537C (en) 2022-08-16
PT3087085T (pt) 2019-06-04
TWI710547B (zh) 2020-11-21
TW202106661A (zh) 2021-02-16
US10030033B2 (en) 2018-07-24
AU2014370125B2 (en) 2017-11-16

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