EA031815B8 - Процесс очищения l-альфа-глицерофосфорилхолина - Google Patents
Процесс очищения l-альфа-глицерофосфорилхолинаInfo
- Publication number
- EA031815B8 EA031815B8 EA201790005A EA201790005A EA031815B8 EA 031815 B8 EA031815 B8 EA 031815B8 EA 201790005 A EA201790005 A EA 201790005A EA 201790005 A EA201790005 A EA 201790005A EA 031815 B8 EA031815 B8 EA 031815B8
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- glycerophosphorylcholine
- purification
- dmso
- purity
- alpha
- Prior art date
Links
- SUHOQUVVVLNYQR-MRVPVSSYSA-N choline alfoscerate Chemical compound C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-N 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 4
- 238000000746 purification Methods 0.000 title abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000005526 G1 to G0 transition Effects 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 238000001514 detection method Methods 0.000 abstract 1
- 238000010828 elution Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 238000000105 evaporative light scattering detection Methods 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/106—Adducts, complexes, salts of phosphatides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/47—Scattering, i.e. diffuse reflection
- G01N21/49—Scattering, i.e. diffuse reflection within a body or fluid
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N2030/022—Column chromatography characterised by the kind of separation mechanism
- G01N2030/027—Liquid chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Immunology (AREA)
- Pathology (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
Описан процесс очищения L-альфа-глицерофосфорилхолина, в котором L-альфа-глицерофосфорилхолин кристаллизуют из диметилсульфоксида (ДМСО) или из смеси ДМСО как минимум с одним другим растворителем, предпочтительно выбранным из воды, спирта, галогенированных растворителей, простых и сложных эфиров и/или амидов. Такой процесс позволяет получить L-альфа-глицерофосфорилхолин с чистотой выше 99,5%, предпочтительно выше 99,7%, более предпочтительно даже выше или равной 99,9%. Также описан способ определения чистоты L-альфа-глицерофосфорилхолина, который включает элюирование L-альфа-глицерофосфорилхолина через ВЭЖХ колонку с неподвижной аминофазой и последующее детектирование самого L-альфа-глицерофосфорилхолина и всех его примесей, при помощи испарительного нефелометрического детектора.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI20141053 | 2014-06-10 | ||
PCT/IB2015/054346 WO2015189766A1 (en) | 2014-06-10 | 2015-06-09 | Process for the purification of l-alpha-glycerophosphorylcholine |
Publications (3)
Publication Number | Publication Date |
---|---|
EA201790005A1 EA201790005A1 (ru) | 2017-06-30 |
EA031815B1 EA031815B1 (ru) | 2019-02-28 |
EA031815B8 true EA031815B8 (ru) | 2019-11-29 |
Family
ID=51230038
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EA201790005A EA031815B8 (ru) | 2014-06-10 | 2015-06-09 | Процесс очищения l-альфа-глицерофосфорилхолина |
Country Status (17)
Country | Link |
---|---|
US (2) | US20170101425A1 (ru) |
EP (1) | EP3154993B1 (ru) |
JP (2) | JP6659592B2 (ru) |
KR (2) | KR101977691B1 (ru) |
CN (2) | CN109776601B (ru) |
AU (1) | AU2015273073B2 (ru) |
BR (1) | BR112016028911B1 (ru) |
CA (1) | CA2951365C (ru) |
CL (1) | CL2016003157A1 (ru) |
EA (1) | EA031815B8 (ru) |
ES (1) | ES2695505T3 (ru) |
MX (1) | MX370921B (ru) |
PE (1) | PE20170386A1 (ru) |
PL (1) | PL3154993T3 (ru) |
SA (1) | SA516380459B1 (ru) |
WO (1) | WO2015189766A1 (ru) |
ZA (1) | ZA201608307B (ru) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114113405B (zh) * | 2021-12-08 | 2023-06-09 | 中山百灵生物技术股份有限公司 | 一种甘油磷酸胆碱及其异构体的高效液相色谱分析方法 |
IT202200010199A1 (it) | 2022-05-17 | 2023-11-17 | Plantarei Biotech S R L | Glicerofosfoinositolo nella prevenzione e nel trattamento di infezioni da covid-19 e metodo per il suo ottenimento |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0575717A1 (en) * | 1992-06-24 | 1993-12-29 | CHEMI S.p.A. | A process for the preparation of glycerophospholipids |
CN102093410A (zh) * | 2011-01-11 | 2011-06-15 | 江南大学 | 一种用硅胶柱层析法分离纯化甘油磷酸胆碱的方法 |
US20120244583A1 (en) * | 2011-03-24 | 2012-09-27 | Yuanfa Liu | Method for Preparing High Purity L-alpha Glycerylphosphorylcholine |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61158990A (ja) * | 1984-12-28 | 1986-07-18 | Nippon Oil & Fats Co Ltd | グリセロホスホリルコリンの製造方法 |
JPS63225387A (ja) * | 1987-03-13 | 1988-09-20 | Nippon Oil & Fats Co Ltd | ホスフアチジルコリンの製造方法 |
IT1229238B (it) | 1989-05-08 | 1991-07-26 | Istituto Chemioterapico | Procedimento per la preparazione di l-alfa-glicerilfosforilcolina e l alfa glicerilfosforiletanolammina. |
US6229605B1 (en) | 2000-03-10 | 2001-05-08 | Alltech Associates, Inc. | Evaporative light scattering device |
JP2002275187A (ja) * | 2001-03-21 | 2002-09-25 | Nof Corp | ホスファチジルコリンの製造方法 |
KR100966627B1 (ko) * | 2006-06-14 | 2010-06-29 | 주식회사 대웅제약 | L-α-글리세로포스포릴 콜린의 제조방법 |
CN102093140A (zh) * | 2010-12-29 | 2011-06-15 | 天津市金三农农业科技开发有限公司 | 一种能抗虫害的生物有机复合肥 |
JP5711272B2 (ja) | 2011-01-17 | 2015-04-30 | 築野食品工業株式会社 | ビタミンeの分析方法 |
CN102260286B (zh) * | 2011-05-27 | 2014-01-15 | 合肥工业大学 | 一种分离纯化粗产品L-α-甘油磷酸胆碱的方法 |
JP2013136025A (ja) | 2011-12-28 | 2013-07-11 | Tosoh Corp | アニオン交換体、その製造方法及びそれを用いた用途 |
CN102964377B (zh) * | 2012-11-30 | 2015-05-27 | 西北大学 | 一种天然L-α-甘油磷脂酰胆碱的制备方法 |
CN103193821A (zh) * | 2013-03-29 | 2013-07-10 | 山东罗欣药业股份有限公司 | L-α-甘油磷酰胆碱的合成方法 |
CN103172659A (zh) | 2013-03-29 | 2013-06-26 | 山东罗欣药业股份有限公司 | L-α-甘油磷酰胆碱晶型化合物 |
-
2015
- 2015-06-09 BR BR112016028911-0A patent/BR112016028911B1/pt active IP Right Grant
- 2015-06-09 PL PL15732957T patent/PL3154993T3/pl unknown
- 2015-06-09 MX MX2016016421A patent/MX370921B/es active IP Right Grant
- 2015-06-09 JP JP2016572684A patent/JP6659592B2/ja active Active
- 2015-06-09 AU AU2015273073A patent/AU2015273073B2/en active Active
- 2015-06-09 CN CN201910131704.5A patent/CN109776601B/zh active Active
- 2015-06-09 KR KR1020167012568A patent/KR101977691B1/ko active IP Right Grant
- 2015-06-09 ES ES15732957T patent/ES2695505T3/es active Active
- 2015-06-09 PE PE2016002696A patent/PE20170386A1/es unknown
- 2015-06-09 EP EP15732957.4A patent/EP3154993B1/en active Active
- 2015-06-09 KR KR1020157022718A patent/KR101622376B1/ko active IP Right Grant
- 2015-06-09 EA EA201790005A patent/EA031815B8/ru not_active IP Right Cessation
- 2015-06-09 US US15/317,441 patent/US20170101425A1/en not_active Abandoned
- 2015-06-09 CA CA2951365A patent/CA2951365C/en active Active
- 2015-06-09 WO PCT/IB2015/054346 patent/WO2015189766A1/en active Application Filing
- 2015-06-09 CN CN201580030638.2A patent/CN106459107B/zh active Active
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2016
- 2016-12-01 ZA ZA2016/08307A patent/ZA201608307B/en unknown
- 2016-12-07 CL CL2016003157A patent/CL2016003157A1/es unknown
- 2016-12-08 SA SA516380459A patent/SA516380459B1/ar unknown
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2019
- 2019-03-21 US US16/360,052 patent/US10787469B2/en active Active
- 2019-03-29 JP JP2019067180A patent/JP6792018B2/ja active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0575717A1 (en) * | 1992-06-24 | 1993-12-29 | CHEMI S.p.A. | A process for the preparation of glycerophospholipids |
CN102093410A (zh) * | 2011-01-11 | 2011-06-15 | 江南大学 | 一种用硅胶柱层析法分离纯化甘油磷酸胆碱的方法 |
US20120244583A1 (en) * | 2011-03-24 | 2012-09-27 | Yuanfa Liu | Method for Preparing High Purity L-alpha Glycerylphosphorylcholine |
Non-Patent Citations (1)
Title |
---|
KANGYI ZHANG; XINGGUO WANG; JIANHUA HUANG; YUANFA LIU;: "Purification of-alpha glycerylphosphorylcholine by column chromatography", JOURNAL OF CHROMATOGRAPHY A, ELSEVIER, AMSTERDAM, NL, vol. 1220, 1 December 2011 (2011-12-01), AMSTERDAM, NL, pages 108 - 114, XP028121751, ISSN: 0021-9673, DOI: 10.1016/j.chroma.2011.12.003 * |
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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): AM BY KG TJ TM |