AR098959A1 - Síntesis de un compuesto antiviral e intermediarios de la misma - Google Patents
Síntesis de un compuesto antiviral e intermediarios de la mismaInfo
- Publication number
- AR098959A1 AR098959A1 ARP140104910A ARP140104910A AR098959A1 AR 098959 A1 AR098959 A1 AR 098959A1 AR P140104910 A ARP140104910 A AR P140104910A AR P140104910 A ARP140104910 A AR P140104910A AR 098959 A1 AR098959 A1 AR 098959A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- crystal
- salt
- give
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 56
- 230000000840 anti-viral effect Effects 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 239000013078 crystal Substances 0.000 abstract 51
- 150000003839 salts Chemical class 0.000 abstract 51
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000006239 protecting group Chemical group 0.000 abstract 6
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 4
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 238000006254 arylation reaction Methods 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000010511 deprotection reaction Methods 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 239000007822 coupling agent Substances 0.000 abstract 1
- 238000005686 cross metathesis reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000010930 lactamization Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
- 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
- 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
Landscapes
- 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)
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361920446P | 2013-12-23 | 2013-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR098959A1 true AR098959A1 (es) | 2016-06-22 |
Family
ID=52278856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140104910A AR098959A1 (es) | 2013-12-23 | 2014-12-23 | Síntesis de un compuesto antiviral e intermediarios de la misma |
Country Status (20)
| Country | Link |
|---|---|
| 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) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT3027171T (pt) | 2013-07-30 | 2020-06-18 | Gilead Connecticut Inc | Formulação de inibidores da syk |
| 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 |
| 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 |
| 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 |
| KR102519417B1 (ko) | 2018-11-28 | 2023-04-10 | 삼성디스플레이 주식회사 | 스트레처블 표시 장치 |
| 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 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2006125446A (ru) * | 2003-12-15 | 2008-01-27 | Джапан Тобакко Инк. (Jp) | Производные n-замещенного n-сульфониламиноциклопропана и их фармацевтическое применение |
| CL2008003384A1 (es) | 2007-11-14 | 2009-12-11 | Enanta Pharm Inc | Compuestos derivados de quinoxalina macrocíclica, inhibidores de serina proteasa; composicion farmaceutica que los comprende; y su uso en el tratamiento de la hepatitis c. |
| US8211891B2 (en) | 2008-04-30 | 2012-07-03 | Enanta Pharmaceuticals, Inc. | Difluoromethyl-containing macrocyclic compounds as hepatitis C virus inhibitors |
| EP2540349B1 (en) * | 2008-07-22 | 2014-02-12 | Merck Sharp & Dohme Corp. | Pharmaceutical compositions comprising a macrocyclic quinoxaline compound which is an hcv ns3 protease inhibitor |
| US8283310B2 (en) | 2008-12-15 | 2012-10-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| EP2289880A1 (en) * | 2009-07-08 | 2011-03-02 | Bayer CropScience AG | 2-Pyridinylcyclopropylbenzamide fungicides |
| SG188618A1 (en) * | 2010-09-21 | 2013-04-30 | Enanta Pharm Inc | Macrocyclic proline derived hcv serine protease inhibitors |
| WO2012040040A1 (en) * | 2010-09-21 | 2012-03-29 | Merck Sharp & Dohme Corp. | Hcv ns3 protease inhibitors |
| AR084217A1 (es) * | 2010-12-10 | 2013-05-02 | Gilead Sciences Inc | Inhibidores macrociclicos de virus flaviviridae |
| UA119315C2 (uk) * | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| WO2015095430A1 (en) * | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Methods and intermediates for the preparation of macrolactams |
| AU2014370125B2 (en) | 2013-12-23 | 2017-11-16 | Gilead Sciences, Inc. | Synthesis of a macrocyclic HCV NS3 inhibiting tripeptide |
| ES2708993T3 (es) * | 2013-12-23 | 2019-04-12 | Gilead Sciences Inc | Formas cristalinas de un tripéptido macrocíclico inhibidor de NS3 del VHC |
-
2014
- 2014-12-18 AU AU2014370125A patent/AU2014370125B2/en active Active
- 2014-12-18 CN CN201480070017.2A patent/CN105849118B/zh active Active
- 2014-12-18 CA CA2934537A patent/CA2934537C/en active Active
- 2014-12-18 EA EA201691031A patent/EA201691031A1/ru unknown
- 2014-12-18 MX MX2016008452A patent/MX2016008452A/es unknown
- 2014-12-18 SG SG11201604482QA patent/SG11201604482QA/en unknown
- 2014-12-18 ES ES14822040T patent/ES2724460T3/es active Active
- 2014-12-18 KR KR1020167016776A patent/KR102366697B1/ko active Active
- 2014-12-18 PL PL14822040T patent/PL3087085T3/pl unknown
- 2014-12-18 SI SI201431166T patent/SI3087085T1/sl unknown
- 2014-12-18 PT PT14822040T patent/PT3087085T/pt unknown
- 2014-12-18 NZ NZ720745A patent/NZ720745A/en not_active IP Right Cessation
- 2014-12-18 CN CN202310617293.7A patent/CN116813596A/zh active Pending
- 2014-12-18 EP EP14822040.3A patent/EP3087085B1/en active Active
- 2014-12-18 TR TR2019/06413T patent/TR201906413T4/tr unknown
- 2014-12-18 WO PCT/US2014/071319 patent/WO2015100145A1/en not_active Ceased
- 2014-12-18 JP JP2016541595A patent/JP6425727B2/ja active Active
- 2014-12-18 US US14/576,143 patent/US9440991B2/en active Active
- 2014-12-18 CN CN202010152008.5A patent/CN111320610B/zh active Active
- 2014-12-22 TW TW109137288A patent/TWI762003B/zh active
- 2014-12-22 TW TW103144804A patent/TWI671292B/zh active
- 2014-12-22 TW TW108125271A patent/TWI710547B/zh active
- 2014-12-23 AR ARP140104910A patent/AR098959A1/es unknown
-
2016
- 2016-06-06 IL IL246064A patent/IL246064A0/en unknown
- 2016-08-03 US US15/227,527 patent/US10030033B2/en active Active
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