EA199700139A1 - Усовершенствованный синтез циклопропилацетилена - Google Patents

Усовершенствованный синтез циклопропилацетилена

Info

Publication number
EA199700139A1
EA199700139A1 EA199700139A EA199700139A EA199700139A1 EA 199700139 A1 EA199700139 A1 EA 199700139A1 EA 199700139 A EA199700139 A EA 199700139A EA 199700139 A EA199700139 A EA 199700139A EA 199700139 A1 EA199700139 A1 EA 199700139A1
Authority
EA
Eurasian Patent Office
Prior art keywords
cyclopropilatetylene
improved synthesis
temperature
pentine
protons
Prior art date
Application number
EA199700139A
Other languages
English (en)
Other versions
EA000074B1 (ru
Inventor
Эндрю С. Томпсон
Эдвард Г. Корли
Марта Хантингтон
Original Assignee
Мерк Энд Ко., Инк.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Мерк Энд Ко., Инк. filed Critical Мерк Энд Ко., Инк.
Publication of EA199700139A1 publication Critical patent/EA199700139A1/ru
Publication of EA000074B1 publication Critical patent/EA000074B1/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/04—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
    • C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
    • 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
    • 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
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Virology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Циклопропилацетилен получают путем смешивания сильного основания и 5-галоген-1-пентина в апротонном растворителе; температура поднимается от 0 до 150°C, и данная температура поддерживается по крайней мере в течение 15 мин. Реакционную смесь затем гасят источником протонов.
EA199700139A 1995-01-23 1996-01-19 Способ получения циклопропилацетилена EA000074B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/376,611 US5663467A (en) 1995-01-23 1995-01-23 Synthesis of cyclopropylacetylene
PCT/US1996/000628 WO1996022955A1 (en) 1995-01-23 1996-01-19 Improved synthesis of cyclopropylacetylene

Publications (2)

Publication Number Publication Date
EA199700139A1 true EA199700139A1 (ru) 1997-12-30
EA000074B1 EA000074B1 (ru) 1998-06-25

Family

ID=23485719

Family Applications (1)

Application Number Title Priority Date Filing Date
EA199700139A EA000074B1 (ru) 1995-01-23 1996-01-19 Способ получения циклопропилацетилена

Country Status (23)

Country Link
US (1) US5663467A (ru)
EP (1) EP0805790B1 (ru)
JP (1) JP3107829B2 (ru)
KR (1) KR19980701577A (ru)
CN (1) CN1056824C (ru)
AR (1) AR000771A1 (ru)
AT (1) ATE186903T1 (ru)
AU (1) AU692674B2 (ru)
BR (1) BR9606782A (ru)
CA (1) CA2210577A1 (ru)
CZ (1) CZ234997A3 (ru)
DE (1) DE69605282T2 (ru)
DK (1) DK0805790T3 (ru)
EA (1) EA000074B1 (ru)
ES (1) ES2140062T3 (ru)
FI (1) FI973086A (ru)
GR (1) GR3032200T3 (ru)
HR (1) HRP960029B1 (ru)
HU (1) HUP9800849A3 (ru)
NZ (1) NZ301206A (ru)
SK (1) SK99997A3 (ru)
WO (1) WO1996022955A1 (ru)
YU (1) YU3696A (ru)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2260922A1 (en) * 1996-07-26 1998-02-05 Du Pont Pharmaceuticals Company A practical synthesis of benzoxazinones useful as hiv reverse transcriptase inhibitors
US5932726A (en) * 1996-12-16 1999-08-03 Dupont Pharmaceuticals Company Asymmetric synthesis of benzoxazinones
US6028237A (en) * 1996-12-16 2000-02-22 Dupont Pharmaceuticals Company Synthesis of cyclopropylacetylene
ZA9711256B (en) 1996-12-16 1999-06-15 Du Pont Merck Pharma Asymmetric synthesis of benzoxazinones
US5955627A (en) * 1996-12-16 1999-09-21 Kuraray Co., Ltd. Process for the preparation of cyclopropylacetylene derivatives
CZ297535B6 (cs) * 1997-02-05 2007-01-03 Merck & Co., Inc. Způsob krystalizace inhibitoru na bázi benzoxazinonu
US5965729A (en) * 1997-02-05 1999-10-12 Merck & Co., Inc. Process for the crystallization of a reverse transcriptase inhibitor using an anti-solvent
JP2001514636A (ja) 1997-03-07 2001-09-11 ビーエーエスエフ アクチェンゲゼルシャフト シクロプロピルアセチレンを製造するための改善法
AU6876898A (en) * 1997-04-07 1998-10-30 Du Pont Pharmaceuticals Company Asymmetric synthesis of benzoxazinones via new intermediates
AR011731A1 (es) * 1997-05-16 2000-08-30 Merck & Co Inc Un proceso de reaccion de adicion enantioselectiva eficiente utilizando un reactivo de organozinc.
PL338455A1 (en) * 1997-07-31 2000-11-06 Du Pont Pharm Co Metho dof obtaining cyclopropyl acetylene
US6072094A (en) * 1997-08-06 2000-06-06 Merck & Co., Inc. Efficient synthesis of cyclopropylacetylene
CA2298835A1 (en) * 1997-08-06 1999-02-18 Merck & Co., Inc. Efficient synthesis of cyclopropylacetylene
EP0922686B1 (de) * 1997-12-10 2002-02-06 Lonza A.G. Verfahren zur Herstellung von Ethinylcyclopropan
KR100350752B1 (ko) * 1998-02-06 2002-08-28 가부시키가이샤 구라레 시클로프로필아세틸렌 유도체의 제조방법
US5952537A (en) * 1998-03-13 1999-09-14 Wiley Organics, Inc. Preparation of cycloalkylacetylene compounds using dialkylaminomagnesium halide or bis(dialkylamino)magnesium
UA72207C2 (ru) 1998-04-07 2005-02-15 Брістол- Майєрс Сквібб Фарма Компані Фармацевтическая композиция эфавиренца в сочетании с ингредиентами, обеспечивающими распад таблеток, и способ изготовления быстрорастворимых таблеток и капсул эфавиренца
US20010014352A1 (en) 1998-05-27 2001-08-16 Udit Batra Compressed tablet formulation
US6235957B1 (en) 1998-06-29 2001-05-22 Dupont Pharmaceuticals Company Process for the preparation of cyclopropylacetylene
WO2000018706A1 (en) 1998-10-01 2000-04-06 Du Pont Pharmaceuticals Company Process for the preparation of cyclopropylacetylene
US6288297B1 (en) 1998-10-01 2001-09-11 Dupont Pharmaceuticals Company Process for the preparation of cyclopropylacetylene
GB2355724A (en) * 1999-10-28 2001-05-02 Merck & Co Inc Synthesis of cyclopropylacetylene from propiolic acid (2-propynoic acid)
GB2355988A (en) 1999-10-28 2001-05-09 Merck & Co Inc Synthesis of cyclopropylacetylene in a one-pot process using a diazo-keto-phos phonate
US8080655B2 (en) * 2009-07-20 2011-12-20 Apotex Pharmachem Inc. Methods of making efavirenz and intermediates thereof
EP2471783A1 (en) 2010-12-23 2012-07-04 Esteve Química, S.A. Novel polymorphic form of 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

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU578293A1 (ru) * 1972-02-04 1977-10-30 Институт Органической Химии Имени Н.Д.Зелинского Ан Ссср Способ получени циклопропилацетилена
SU555079A1 (ru) * 1976-01-30 1977-04-25 Институт органической химии им.Н.Д.Зелинского АН СССР Способ получени циклопропилацетилена
SU572445A1 (ru) * 1976-04-05 1977-09-15 Институт Органической Химии Имени Н.Д. Зелинского Ан Ссср Способ получени циклопропилацетилена

Also Published As

Publication number Publication date
EA000074B1 (ru) 1998-06-25
US5663467A (en) 1997-09-02
ES2140062T3 (es) 2000-02-16
KR19980701577A (ko) 1998-05-15
AU692674B2 (en) 1998-06-11
CZ234997A3 (cs) 1998-02-18
SK99997A3 (en) 1998-05-06
ATE186903T1 (de) 1999-12-15
EP0805790B1 (en) 1999-11-24
EP0805790A1 (en) 1997-11-12
CA2210577A1 (en) 1996-08-01
HRP960029A2 (en) 1997-08-31
DE69605282D1 (en) 1999-12-30
CN1056824C (zh) 2000-09-27
BR9606782A (pt) 1997-12-30
DK0805790T3 (da) 2000-05-01
NZ301206A (en) 1998-11-25
JPH10512880A (ja) 1998-12-08
CN1169137A (zh) 1997-12-31
HUP9800849A2 (hu) 1999-01-28
MX9705562A (es) 1997-10-31
YU3696A (sh) 1998-11-05
AR000771A1 (es) 1997-08-06
JP3107829B2 (ja) 2000-11-13
WO1996022955A1 (en) 1996-08-01
HRP960029B1 (en) 2000-12-31
HUP9800849A3 (en) 2001-01-29
GR3032200T3 (en) 2000-04-27
FI973086A0 (fi) 1997-07-22
DE69605282T2 (de) 2000-07-13
AU4657496A (en) 1996-08-14
FI973086A (fi) 1997-07-22

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Legal Events

Date Code Title Description
MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): AZ BY KG TJ TM

MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): KZ RU