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WO2013043009A3 - 1-팔미토일-3-아세틸글리세롤의 제조방법 및 이를 이용한 1-팔미토일-2-리놀레오일-3-아세틸글리세롤의 제조방법 - Google Patents

1-팔미토일-3-아세틸글리세롤의 제조방법 및 이를 이용한 1-팔미토일-2-리놀레오일-3-아세틸글리세롤의 제조방법 Download PDF

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Publication number
WO2013043009A3
WO2013043009A3 PCT/KR2012/007644 KR2012007644W WO2013043009A3 WO 2013043009 A3 WO2013043009 A3 WO 2013043009A3 KR 2012007644 W KR2012007644 W KR 2012007644W WO 2013043009 A3 WO2013043009 A3 WO 2013043009A3
Authority
WO
WIPO (PCT)
Prior art keywords
palmitoyl
acetylglycerol
preparation
preparing
optically active
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2012/007644
Other languages
English (en)
French (fr)
Other versions
WO2013043009A2 (ko
Inventor
이태석
육진수
유창현
이철민
김은경
이주철
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Enzychem Lifesciences Corp
Original Assignee
Enzychem Lifesciences Corp
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
Priority to IN2166DEN2014 priority Critical patent/IN2014DN02166A/en
Priority to US14/346,783 priority patent/US20140243548A1/en
Priority to ES12834214.4T priority patent/ES2620103T3/es
Priority to JP2014531727A priority patent/JP5799171B2/ja
Priority to RU2014116232/04A priority patent/RU2566826C1/ru
Priority to AU2012310342A priority patent/AU2012310342B2/en
Priority to CN201280046277.7A priority patent/CN103827075B/zh
Priority to EP12834214.4A priority patent/EP2759529B1/en
Application filed by Enzychem Lifesciences Corp filed Critical Enzychem Lifesciences Corp
Priority to CA2849289A priority patent/CA2849289C/en
Publication of WO2013043009A2 publication Critical patent/WO2013043009A2/ko
Publication of WO2013043009A3 publication Critical patent/WO2013043009A3/ko
Anticipated expiration legal-status Critical
Priority to US14/958,734 priority patent/US9701613B2/en
Priority to US15/448,728 priority patent/US20170183287A1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/30—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with trihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • 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)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

컬럼크로마토그래피에 의한 정제 과정 없이, 고순도 및 고수율로 1-팔미토일-3-아세틸글리세롤을 제조하는 방법 및 이를 핵심 중간체로 사용하여 고순도 및 고수율로 1-팔미토일-2-리놀레오일-3-아세틸글리세롤을 제조하는 방법이 개시된다. 상기 1-팔미토일-3-아세틸글리세롤 제조방법은 라세믹체 또는 광학활성체인 명세서의 화학식 2로 표시되는 1-팔미토일글리세롤을 아세틸화제와 반응시켜 라세믹체 또는 광학활성체인 명세서의 화학식 1로 표시되는 1-팔미토일-3-아세틸글리세롤을 포함하는 반응 혼합물을 형성하는 단계; 및 상기 반응 혼합물을 탄소수 5 내지 7의 포화탄화수소 용매 중에서 결정화시켜 상기 광학활성 1-팔미토일-3-아세틸글리세롤을 분리하는 단계를 포함한다.
PCT/KR2012/007644 2011-09-23 2012-09-24 1-팔미토일-3-아세틸글리세롤의 제조방법 및 이를 이용한 1-팔미토일-2-리놀레오일-3-아세틸글리세롤의 제조방법 Ceased WO2013043009A2 (ko)

Priority Applications (11)

Application Number Priority Date Filing Date Title
CN201280046277.7A CN103827075B (zh) 2011-09-23 2012-09-24 1-棕榈酰-3-乙酰基甘油的制备方法及使用其制备1-棕榈酰-2-亚油酰基-3-乙酰基甘油的方法
ES12834214.4T ES2620103T3 (es) 2011-09-23 2012-09-24 Método de preparación de 1-palmitoil-3-acetilglicerol y procedimiento de preparación de 1-palmitoil-2-linoleoil-3-acetilglicerol usando el mismo
JP2014531727A JP5799171B2 (ja) 2011-09-23 2012-09-24 １−パルミトイル−３−アセチルグリセロールの製造方法およびこれを利用した１−パルミトイル−２−リノレオイル−３−アセチルグリセロールの製造方法
RU2014116232/04A RU2566826C1 (ru) 2011-09-23 2012-09-24 Способ получения 1-пальмитоил-3-ацетилглицерина и способ получения 1-пальмитоил-2-линолеоил-3-ацетилглицерина с использованием этого соединения
AU2012310342A AU2012310342B2 (en) 2011-09-23 2012-09-24 Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same
EP12834214.4A EP2759529B1 (en) 2011-09-23 2012-09-24 Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same
CA2849289A CA2849289C (en) 2011-09-23 2012-09-24 Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same
IN2166DEN2014 IN2014DN02166A (ko) 2011-09-23 2012-09-24
US14/346,783 US20140243548A1 (en) 2011-09-23 2012-09-24 Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same
US14/958,734 US9701613B2 (en) 2011-09-23 2015-12-03 Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same
US15/448,728 US20170183287A1 (en) 2011-09-23 2017-03-03 Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020110096341A KR101278874B1 (ko) 2011-09-23 2011-09-23 1-팔미토일-3-아세틸글리세롤의 제조방법 및 이를 이용한 1-팔미토일-2-리놀레오일-3-아세틸글리세롤의 제조방법
KR10-2011-0096341 2011-09-23

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US14/346,783 A-371-Of-International US20140243548A1 (en) 2011-09-23 2012-09-24 Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same
US14/958,734 Continuation US9701613B2 (en) 2011-09-23 2015-12-03 Preparation method of 1-palmitoyl-3-acetylglycerol, and preparation method of 1-palmitoyl-2-linoleoyl-3-acetylglycerol using same

Publications (2)

Publication Number Publication Date
WO2013043009A2 WO2013043009A2 (ko) 2013-03-28
WO2013043009A3 true WO2013043009A3 (ko) 2013-05-30

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/007644 Ceased WO2013043009A2 (ko) 2011-09-23 2012-09-24 1-팔미토일-3-아세틸글리세롤의 제조방법 및 이를 이용한 1-팔미토일-2-리놀레오일-3-아세틸글리세롤의 제조방법

Country Status (11)

Country Link
US (3) US20140243548A1 (ko)
EP (1) EP2759529B1 (ko)
JP (1) JP5799171B2 (ko)
KR (1) KR101278874B1 (ko)
CN (1) CN103827075B (ko)
AU (1) AU2012310342B2 (ko)
CA (1) CA2849289C (ko)
ES (1) ES2620103T3 (ko)
IN (1) IN2014DN02166A (ko)
RU (1) RU2566826C1 (ko)
WO (1) WO2013043009A2 (ko)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101278874B1 (ko) 2011-09-23 2013-06-26 주식회사 엔지켐생명과학 1-팔미토일-3-아세틸글리세롤의 제조방법 및 이를 이용한 1-팔미토일-2-리놀레오일-3-아세틸글리세롤의 제조방법
RU2636615C2 (ru) 2013-08-19 2017-11-24 Энзикем Лайфсайенсиз Корпорейшн Композиция для предотвращения или лечения астмы, содержащая моноацетилдиацилглицериновое соединение в качестве активного ингредиента
US9808438B2 (en) 2015-11-09 2017-11-07 Enzychem Lifesciences Corporation Method for treating mucositis
US10653657B2 (en) 2015-11-14 2020-05-19 Enzychem Lifesciences Corporation Method for treating hemolytic uremic syndrome
WO2017082708A1 (ko) 2015-11-14 2017-05-18 주식회사 엔지켐생명과학 발작성 야간 혈색소뇨증의 치료 방법
IL274974B2 (en) 2017-11-30 2025-03-01 Enzychem Lifesciences Corp Compositions for prevention or treatment of acute radiation syndrome
KR102333606B1 (ko) * 2019-10-15 2021-12-01 주식회사 엔지켐생명과학 1-팔미토일-2-리놀레오일-3-아세틸 글리세롤의 제조 방법
RU2758793C1 (ru) * 2021-03-29 2021-11-01 Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Образования «Новосибирский Государственный Технический Университет» Адаптивная стартер-генераторная система

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Also Published As

Publication number Publication date
US20170183287A1 (en) 2017-06-29
CA2849289A1 (en) 2013-03-28
US20140243548A1 (en) 2014-08-28
CN103827075B (zh) 2015-09-16
ES2620103T3 (es) 2017-06-27
AU2012310342A1 (en) 2014-04-03
KR20130032628A (ko) 2013-04-02
WO2013043009A2 (ko) 2013-03-28
CA2849289C (en) 2016-05-10
IN2014DN02166A (ko) 2015-05-15
US20160083329A1 (en) 2016-03-24
JP5799171B2 (ja) 2015-10-21
AU2012310342B2 (en) 2015-11-26
EP2759529B1 (en) 2016-12-21
EP2759529A2 (en) 2014-07-30
RU2566826C1 (ru) 2015-10-27
EP2759529A4 (en) 2015-05-20
US9701613B2 (en) 2017-07-11
KR101278874B1 (ko) 2013-06-26
CN103827075A (zh) 2014-05-28
JP2014528945A (ja) 2014-10-30

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