CZ297968B6 - Zpusob výroby klícového meziproduktu - Google Patents
Zpusob výroby klícového meziproduktuInfo
- Publication number
- CZ297968B6 CZ297968B6 CZ0404699A CZ404699A CZ297968B6 CZ 297968 B6 CZ297968 B6 CZ 297968B6 CZ 0404699 A CZ0404699 A CZ 0404699A CZ 404699 A CZ404699 A CZ 404699A CZ 297968 B6 CZ297968 B6 CZ 297968B6
- Authority
- CZ
- Czechia
- Prior art keywords
- key intermediate
- trifluoromethyl
- chloro
- producing key
- chiral addition
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/68—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Zpusob výroby klícového meziproduktu pri syntéze inhibitoru reverzní transkriptázy (-)-6-chlor-4-cyklopropylethinyl-4-trifluormethyl-1,4-dihydro-2H-3,1-benzoxazin-2-onu, známého také jako DMP-266, pri kterém se vyuzívá chirální adicní reakce na 4-chlor-2-trifluormethylketoanilin organozinecnatým komplexem za poskytnutí pozadovaného alkoholu. Popisovaný zpusob je siroce vyuzitelný pri chirální adici na jakýkoliv prochirální keton.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4671397P | 1997-05-16 | 1997-05-16 | |
GB9711599A GB9711599D0 (en) | 1997-06-05 | 1997-06-05 | Efficient enatioselective addition reation using an organozinc reagent |
US5788497P | 1997-09-03 | 1997-09-03 | |
GB9727129A GB9727129D0 (en) | 1997-12-22 | 1997-12-22 | Efficient enantioselective addition reaction using an organozinc reagent |
US8352598P | 1998-04-29 | 1998-04-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
CZ404699A3 CZ404699A3 (cs) | 2000-07-12 |
CZ297968B6 true CZ297968B6 (cs) | 2007-05-09 |
Family
ID=27547294
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CZ0404699A CZ297968B6 (cs) | 1997-05-16 | 1998-05-12 | Zpusob výroby klícového meziproduktu |
Country Status (26)
Country | Link |
---|---|
US (1) | US6015926A (cs) |
EP (1) | EP0981520B1 (cs) |
JP (1) | JP3273615B2 (cs) |
KR (1) | KR100566683B1 (cs) |
CN (1) | CN1106389C (cs) |
AR (1) | AR011731A1 (cs) |
AT (1) | ATE270666T1 (cs) |
AU (1) | AU739250B2 (cs) |
BR (1) | BR9809628A (cs) |
CA (1) | CA2289206C (cs) |
CZ (1) | CZ297968B6 (cs) |
DE (1) | DE69824958T2 (cs) |
DK (1) | DK0981520T3 (cs) |
EA (1) | EA002192B1 (cs) |
ES (1) | ES2224396T3 (cs) |
HR (1) | HRP980266B1 (cs) |
HU (1) | HU226881B1 (cs) |
NZ (1) | NZ500526A (cs) |
PL (1) | PL193448B1 (cs) |
PT (1) | PT981520E (cs) |
RS (1) | RS49860B (cs) |
SI (1) | SI0981520T1 (cs) |
SK (1) | SK285446B6 (cs) |
TW (1) | TWI221833B (cs) |
UA (1) | UA59396C2 (cs) |
WO (1) | WO1998051676A1 (cs) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6201158B1 (en) * | 1998-06-22 | 2001-03-13 | Merck & Co., Inc. | Process for making intermediate aldehydes |
CN1953967B (zh) | 2004-04-27 | 2013-03-13 | 惠氏公司 | 孕酮受体调节剂的纯化 |
US20090163601A1 (en) * | 2007-12-21 | 2009-06-25 | The Regents Of The University Of California | (r)-2-methyl-(2,5-dimethylphenyl)propanol and (s)-(2-methyl-2,5-dimethylphenyl)propanol |
US9073817B2 (en) | 2008-01-31 | 2015-07-07 | Laurus Labs Private Limited | Efficient process to induce enantioselectivity in procarbonyl compounds |
ZA200806473B (en) * | 2008-01-31 | 2009-04-29 | Aptuit Laurus Pvt Ltd | An efficient process to induce enantioselectivity in procarbonyl compounds |
US20110071287A1 (en) * | 2008-05-01 | 2011-03-24 | Ranbaxy Laboratories Limited | Process for the preparation of efavirenz |
US8604189B2 (en) * | 2008-05-30 | 2013-12-10 | Emcure Pharmaceuticals Limited | Process for the preparation of Efavirenz |
KR100878436B1 (ko) * | 2008-08-18 | 2009-01-13 | 주식회사 지씨에이치앤피 | 금은화 추출물을 포함하는 소화성 궤양 치료 또는 예방용 약학조성물 |
WO2010115638A2 (en) * | 2009-04-09 | 2010-10-14 | Lonza Ltd. | Autocatalytic process for the synthesis of chiral propargylic alcohols |
EP2417114A1 (en) * | 2009-04-09 | 2012-02-15 | Lonza Ltd. | Process for the synthesis of chiral cyclic carbamates |
WO2010115639A1 (en) * | 2009-04-09 | 2010-10-14 | Lonza Ltd | Process for the synthesis of a propargylic alcohol |
US20110172419A1 (en) * | 2009-04-09 | 2011-07-14 | Aleksander Warm | Process for the synthesis of cyclic carbamates |
WO2011000532A2 (de) | 2009-07-03 | 2011-01-06 | Archimica Gmbh | Verfahren zur enantioselektiven addition von organometallischen kohlenstoffnukleophilen an trifluormethylketone und verwendung des verfahrens in der synthese von hiv reverse transcriptase inhibitoren |
US8080655B2 (en) * | 2009-07-20 | 2011-12-20 | Apotex Pharmachem Inc. | Methods of making efavirenz and intermediates thereof |
EP2447247A1 (en) * | 2010-10-14 | 2012-05-02 | Lonza Ltd. | Process for the synthesis of chiral propargylic alcohols |
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 |
WO2012079235A1 (en) * | 2010-12-16 | 2012-06-21 | Lonza Ltd | Process for preparing efavirenz |
CN103254087B (zh) * | 2013-06-07 | 2015-03-18 | 郑州大学 | 依非韦伦中间体的制备方法 |
CN105330554B (zh) * | 2015-02-15 | 2017-07-11 | 上海迪赛诺药业股份有限公司 | 手性环丙基乙炔基叔醇类化合物的合成方法 |
DE202015104551U1 (de) | 2015-08-27 | 2015-12-03 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Reaktoren für die Herstellung von Efavirenz sowie Zwischenprodukte |
NL2018412B1 (en) | 2017-02-23 | 2018-09-17 | Univ Nelson Mandela Metropolitan | Method for the manufacture of efavirenz |
CN106946718A (zh) * | 2017-04-27 | 2017-07-14 | 武汉工程大学 | 一种合成依非韦伦中间体的方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995020389A1 (en) * | 1994-01-28 | 1995-08-03 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
WO1996037457A1 (en) * | 1995-05-25 | 1996-11-28 | Merck & Co., Inc. | Asymmetric synthesis of (-) 6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2h-3,1-benzoxazin-2-one |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5663169A (en) * | 1992-08-07 | 1997-09-02 | Merck & Co., Inc. | Benzoxazinones as inhibitors of HIV reverse transcriptase |
US5663467A (en) * | 1995-01-23 | 1997-09-02 | Merck & Co., Inc. | Synthesis of cyclopropylacetylene |
EP0973737A4 (en) * | 1997-01-10 | 2000-04-26 | Merck & Co Inc | EFFECTIVE SYNTHESIS OF A CHIRAL MEDIATOR |
SK284935B6 (sk) * | 1997-02-05 | 2006-02-02 | Merck & Co., Inc. | Forma I (-)-6-chlór-4-cyklopropyletynyl-4-tri-fluórmetyl-1,4- dihydro-2H-3,1-benzoxazín-2-ónu a spôsob jej kryštalizácie |
HRP980056A2 (en) * | 1997-02-12 | 1998-12-31 | Edward J.J: Grabowski | Efficient synthesis of a 1,4-dihidro-2h-3,1-benzoxazin-2-one |
-
1998
- 1998-05-11 US US09/075,476 patent/US6015926A/en not_active Expired - Lifetime
- 1998-05-11 AR ARP980102177A patent/AR011731A1/es active IP Right Grant
- 1998-05-12 RS YUP-582/99A patent/RS49860B/sr unknown
- 1998-05-12 CN CN98805059A patent/CN1106389C/zh not_active Expired - Lifetime
- 1998-05-12 NZ NZ500526A patent/NZ500526A/en not_active IP Right Cessation
- 1998-05-12 SK SK1562-99A patent/SK285446B6/sk not_active IP Right Cessation
- 1998-05-12 PT PT98922084T patent/PT981520E/pt unknown
- 1998-05-12 EP EP98922084A patent/EP0981520B1/en not_active Expired - Lifetime
- 1998-05-12 WO PCT/US1998/008888 patent/WO1998051676A1/en active IP Right Grant
- 1998-05-12 SI SI9830670T patent/SI0981520T1/xx unknown
- 1998-05-12 PL PL98336717A patent/PL193448B1/pl unknown
- 1998-05-12 AU AU74707/98A patent/AU739250B2/en not_active Expired
- 1998-05-12 CZ CZ0404699A patent/CZ297968B6/cs not_active IP Right Cessation
- 1998-05-12 CA CA002289206A patent/CA2289206C/en not_active Expired - Lifetime
- 1998-05-12 JP JP54926798A patent/JP3273615B2/ja not_active Expired - Lifetime
- 1998-05-12 DK DK98922084T patent/DK0981520T3/da active
- 1998-05-12 AT AT98922084T patent/ATE270666T1/de active
- 1998-05-12 BR BR9809628-1A patent/BR9809628A/pt not_active Application Discontinuation
- 1998-05-12 KR KR1019997010611A patent/KR100566683B1/ko not_active IP Right Cessation
- 1998-05-12 DE DE69824958T patent/DE69824958T2/de not_active Expired - Lifetime
- 1998-05-12 ES ES98922084T patent/ES2224396T3/es not_active Expired - Lifetime
- 1998-05-12 HU HU0003404A patent/HU226881B1/hu unknown
- 1998-05-12 EA EA199901040A patent/EA002192B1/ru not_active IP Right Cessation
- 1998-05-14 TW TW087107486A patent/TWI221833B/zh not_active IP Right Cessation
- 1998-05-15 HR HR980266A patent/HRP980266B1/xx not_active IP Right Cessation
- 1998-12-05 UA UA99126738A patent/UA59396C2/uk unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995020389A1 (en) * | 1994-01-28 | 1995-08-03 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
WO1996037457A1 (en) * | 1995-05-25 | 1996-11-28 | Merck & Co., Inc. | Asymmetric synthesis of (-) 6-chloro-4-cyclopropyl-ethynyl-4-trifluoromethyl-1,4-dihydro-2h-3,1-benzoxazin-2-one |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PD00 | Pending as of 2000-06-30 in czech republic | ||
MK4A | Patent expired |
Effective date: 20180512 |