EA199900552A1 - Асимметрический способ получения бензоксазинонов - Google Patents
Асимметрический способ получения бензоксазиноновInfo
- Publication number
- EA199900552A1 EA199900552A1 EA199900552A EA199900552A EA199900552A1 EA 199900552 A1 EA199900552 A1 EA 199900552A1 EA 199900552 A EA199900552 A EA 199900552A EA 199900552 A EA199900552 A EA 199900552A EA 199900552 A1 EA199900552 A1 EA 199900552A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- benzoxasinones
- obtaining
- asymmetric method
- asymmetric
- cyclopropylethynyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 241000725303 Human immunodeficiency virus Species 0.000 abstract 2
- XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 abstract 1
- 102100034343 Integrase Human genes 0.000 abstract 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 abstract 1
- 238000011914 asymmetric synthesis Methods 0.000 abstract 1
- XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Настоящее изобретение относится к новым способам асимметрического синтеза (S)-6-хлор-4-циклопропилэтинил-4-трифторметил-1,4-дигидро-2Н-3,1-бензоксазин-2-она формулы (VI-i), который может использоваться как ингибитор обратной транскриптазы вируса иммунодефицита человека (ВИЧ).Международная заявка была опубликована вместе с отчетом о международном поиске.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3298096P | 1996-12-16 | 1996-12-16 | |
US08/838,838 US5932726A (en) | 1996-12-16 | 1997-04-11 | Asymmetric synthesis of benzoxazinones |
PCT/US1997/022674 WO1998027073A1 (en) | 1996-12-16 | 1997-12-15 | Asymmetric synthesis of benzoxazinones |
Publications (2)
Publication Number | Publication Date |
---|---|
EA199900552A1 true EA199900552A1 (ru) | 2000-02-28 |
EA002987B1 EA002987B1 (ru) | 2002-12-26 |
Family
ID=26709131
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EA199900552A EA002987B1 (ru) | 1996-12-16 | 1997-12-15 | Асимметрический способ получения бензоксазинонов |
Country Status (27)
Country | Link |
---|---|
US (1) | US5932726A (ru) |
EP (1) | EP0944610B1 (ru) |
JP (1) | JP4232911B2 (ru) |
KR (1) | KR100498665B1 (ru) |
CN (1) | CN1075063C (ru) |
AT (1) | ATE289296T1 (ru) |
AU (1) | AU750047B2 (ru) |
BR (1) | BR9714031A (ru) |
CA (1) | CA2275323C (ru) |
CZ (1) | CZ297168B6 (ru) |
DE (1) | DE69732525T2 (ru) |
EA (1) | EA002987B1 (ru) |
EE (1) | EE03920B1 (ru) |
ES (1) | ES2235265T3 (ru) |
HR (1) | HRP970688A2 (ru) |
HU (1) | HU225655B1 (ru) |
IL (2) | IL130684A (ru) |
LV (1) | LV12432B (ru) |
NO (1) | NO313236B1 (ru) |
NZ (1) | NZ336163A (ru) |
PL (1) | PL192661B1 (ru) |
PT (1) | PT944610E (ru) |
RO (1) | RO120844B1 (ru) |
SI (1) | SI20071A (ru) |
SK (1) | SK285258B6 (ru) |
UA (1) | UA66773C2 (ru) |
WO (1) | WO1998027073A1 (ru) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5874430A (en) * | 1996-10-02 | 1999-02-23 | Dupont Pharmaceuticals Company | 4,4-disubstitued-1,4-dihydro-2H-3,1-benzoxazin-2-ones useful as HIV reverse transcriptase inhibitors and intermediates and processes for making the same |
US6673372B1 (en) | 1998-06-11 | 2004-01-06 | Bristol-Myers Squibb Pharma Company | Crystalline Efavirenz |
TWI326283B (en) * | 2002-07-31 | 2010-06-21 | Du Pont | Method for preparing fused oxazinones |
WO2004087628A1 (fr) * | 2003-04-04 | 2004-10-14 | Shanghai Institute Of Organic Chemistry, Chinese Academy Of Sciences | Ligand amino-alcool et son utilisation dans la preparation d'alcools tertiaires propargyliques et d'amines tertiaires par le biais d'une reaction d'addition eniantioselective |
WO2010032259A2 (en) | 2008-05-30 | 2010-03-25 | Emcure Pharmaceuticals Limited | Novel process |
US8080655B2 (en) * | 2009-07-20 | 2011-12-20 | Apotex Pharmachem Inc. | Methods of making efavirenz and intermediates thereof |
CN101844990B (zh) * | 2010-05-27 | 2013-03-20 | 浙江沙星医药化工有限公司 | 中间体4-氯-2-(三氟乙酰基)苯胺盐酸盐水合物的合成方法 |
EP2441759A1 (en) | 2010-10-14 | 2012-04-18 | Lonza Ltd. | Process for the synthesis of cyclic carbamates |
EP2447255A1 (en) | 2010-10-14 | 2012-05-02 | Lonza Ltd. | Process for the synthesis of cyclic carbamates |
CN102584801B (zh) * | 2011-01-06 | 2015-02-18 | 中国科学院上海有机化学研究所 | Hiv逆转录酶抑制剂依法韦伦类化合物的一锅法不对称合成工艺 |
WO2015118515A1 (en) * | 2014-02-10 | 2015-08-13 | Discovery Intermediates Private Limited | An improved process for the preparation of a non-nucleoside reverse transcriptase inhibitor |
EP2944631A1 (en) * | 2014-05-12 | 2015-11-18 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of Efavirenz |
CN104016936B (zh) * | 2014-06-18 | 2016-08-17 | 中国科学院上海有机化学研究所 | 手性氨基酚配体在依法韦仑不对称合成中的应用 |
CN105801442A (zh) * | 2015-10-16 | 2016-07-27 | 浙江沙星医药化工有限公司 | 4-氯-2-(三氟乙酰基)苯胺盐酸盐水合物的制备方法 |
US11117873B2 (en) * | 2015-12-08 | 2021-09-14 | Dic Corporation | Oxazine compound, composition, and cured product |
CN108368218B (zh) * | 2015-12-08 | 2020-11-06 | Dic株式会社 | 恶嗪化合物、组合物及固化物 |
KR102644662B1 (ko) * | 2015-12-08 | 2024-03-07 | 디아이씨 가부시끼가이샤 | 옥사진 화합물, 조성물 및 경화물 |
NL2018412B1 (en) * | 2017-02-23 | 2018-09-17 | Univ Nelson Mandela Metropolitan | Method for the manufacture of efavirenz |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE343057C (de) * | 1914-06-21 | 1921-10-25 | Kalle & Co Aktien Ges | Verfahren zur Darstellung von 1-Arylamino-4-oxynaphthalinen |
US3280120A (en) * | 1964-03-09 | 1966-10-18 | Rexall Drug Chemical | Substituted benzoxazines, process therefor and intermediates |
US3526621A (en) * | 1966-08-03 | 1970-09-01 | Farmaceutical Italia Soc | Substituted 3,1-benzoxazin-2-one |
US3513166A (en) * | 1967-05-22 | 1970-05-19 | Robins Co Inc A H | 3-(omega-aminoalkyl)-4-substituted-1,3-benzoxazine-2-ones |
AU5960380A (en) * | 1979-08-30 | 1981-03-05 | A. Ehrenreich G.m.b.H. & Co. KG | Bellows seal and retaining ring |
DE3622262A1 (de) * | 1986-07-02 | 1988-01-07 | Bayer Ag | Chromogene 3,1-benzoxazine |
JPH0436252A (ja) * | 1990-05-30 | 1992-02-06 | Nippon Alkyl Alum Kk | 光学活性アルキニルアルコールの製造方法 |
US5519021A (en) * | 1992-08-07 | 1996-05-21 | Merck & Co., Inc. | Benzoxazinones as inhibitors of HIV reverse transcriptase |
IL106507A (en) * | 1992-08-07 | 1997-11-20 | Merck & Co Inc | Pharmaceutical compositions containing benzoxazinones and some novel compounds of this type |
AU1694295A (en) * | 1994-01-28 | 1995-08-15 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
US5663467A (en) * | 1995-01-23 | 1997-09-02 | Merck & Co., Inc. | Synthesis of cyclopropylacetylene |
US5633405A (en) * | 1995-05-25 | 1997-05-27 | Merck & Co., Inc. | Asymmetric synthesis of (-)-6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxanzin-2-one |
-
1997
- 1997-04-11 US US08/838,838 patent/US5932726A/en not_active Expired - Lifetime
- 1997-12-15 KR KR10-1999-7005331A patent/KR100498665B1/ko active IP Right Grant
- 1997-12-15 ES ES97953140T patent/ES2235265T3/es not_active Expired - Lifetime
- 1997-12-15 AT AT97953140T patent/ATE289296T1/de active
- 1997-12-15 NZ NZ336163A patent/NZ336163A/en not_active IP Right Cessation
- 1997-12-15 RO RO99-00672A patent/RO120844B1/ro unknown
- 1997-12-15 EE EEP199900243A patent/EE03920B1/xx unknown
- 1997-12-15 DE DE69732525T patent/DE69732525T2/de not_active Expired - Lifetime
- 1997-12-15 PT PT97953140T patent/PT944610E/pt unknown
- 1997-12-15 AU AU56944/98A patent/AU750047B2/en not_active Expired
- 1997-12-15 HU HU0000168A patent/HU225655B1/hu unknown
- 1997-12-15 IL IL13068497A patent/IL130684A/xx active IP Right Grant
- 1997-12-15 CN CN97181746A patent/CN1075063C/zh not_active Expired - Lifetime
- 1997-12-15 SK SK803-99A patent/SK285258B6/sk not_active IP Right Cessation
- 1997-12-15 PL PL334281A patent/PL192661B1/pl unknown
- 1997-12-15 CZ CZ0212899A patent/CZ297168B6/cs not_active IP Right Cessation
- 1997-12-15 SI SI9720079A patent/SI20071A/sl unknown
- 1997-12-15 EA EA199900552A patent/EA002987B1/ru not_active IP Right Cessation
- 1997-12-15 EP EP97953140A patent/EP0944610B1/en not_active Expired - Lifetime
- 1997-12-15 BR BR9714031-7A patent/BR9714031A/pt not_active Application Discontinuation
- 1997-12-15 WO PCT/US1997/022674 patent/WO1998027073A1/en active IP Right Grant
- 1997-12-15 UA UA99063227A patent/UA66773C2/ru unknown
- 1997-12-15 CA CA002275323A patent/CA2275323C/en not_active Expired - Lifetime
- 1997-12-15 JP JP52781198A patent/JP4232911B2/ja not_active Expired - Lifetime
- 1997-12-16 HR HR08/838,838A patent/HRP970688A2/hr not_active Application Discontinuation
-
1999
- 1999-06-15 NO NO19992914A patent/NO313236B1/no not_active IP Right Cessation
- 1999-07-30 LV LVP-99-96A patent/LV12432B/en unknown
- 1999-12-15 IL IL13068499A patent/IL130684A0/xx unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MK4A | Patent expired |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |