CN1995010B - 一种合成丙酰左旋肉碱盐酸盐的方法 - Google Patents
一种合成丙酰左旋肉碱盐酸盐的方法 Download PDFInfo
- Publication number
- CN1995010B CN1995010B CN 200610135197 CN200610135197A CN1995010B CN 1995010 B CN1995010 B CN 1995010B CN 200610135197 CN200610135197 CN 200610135197 CN 200610135197 A CN200610135197 A CN 200610135197A CN 1995010 B CN1995010 B CN 1995010B
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- CN
- China
- Prior art keywords
- carnitine
- propionyl
- levo
- acetone
- carnitine hydrochloride
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 7
- -1 propionyl levo-carnitine Chemical compound 0.000 title claims description 35
- 229960001518 levocarnitine Drugs 0.000 title description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 46
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims abstract description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000003756 stirring Methods 0.000 claims abstract description 19
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 16
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 16
- 238000001816 cooling Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 11
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 229960000243 levocarnitine hydrochloride Drugs 0.000 claims description 30
- 238000002425 crystallisation Methods 0.000 claims description 22
- 230000008025 crystallization Effects 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 8
- 238000009413 insulation Methods 0.000 claims description 7
- 238000000967 suction filtration Methods 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 5
- 238000010025 steaming Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 6
- 229960004203 carnitine Drugs 0.000 abstract description 3
- 238000001704 evaporation Methods 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 239000010887 waste solvent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- JXXCENBLGFBQJM-UHFFFAOYSA-N (3-carboxy-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CC(O)=O JXXCENBLGFBQJM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000002107 myocardial effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 210000000518 sarcolemma Anatomy 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- RDHQFKQIGNGIED-MRVPVSSYSA-N O-acetyl-L-carnitine Chemical compound CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C RDHQFKQIGNGIED-MRVPVSSYSA-N 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007654 ischemic lesion Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000010016 myocardial function Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 208000018360 neuromuscular disease Diseases 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Images
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN 200610135197 CN1995010B (zh) | 2006-12-29 | 2006-12-29 | 一种合成丙酰左旋肉碱盐酸盐的方法 |
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CN 200610135197 CN1995010B (zh) | 2006-12-29 | 2006-12-29 | 一种合成丙酰左旋肉碱盐酸盐的方法 |
Publications (2)
Publication Number | Publication Date |
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CN1995010A CN1995010A (zh) | 2007-07-11 |
CN1995010B true CN1995010B (zh) | 2012-12-12 |
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CN 200610135197 Active CN1995010B (zh) | 2006-12-29 | 2006-12-29 | 一种合成丙酰左旋肉碱盐酸盐的方法 |
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Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101774934B (zh) * | 2009-12-31 | 2012-12-12 | 湖北海力化工科技有限公司 | 一种合成月桂酰左旋肉碱盐酸盐的方法 |
CN102391141A (zh) * | 2011-09-23 | 2012-03-28 | 李氏大药厂(香港)有限公司 | 丙酰左卡尼汀盐酸盐的制备方法及其药物用途 |
CN102432483A (zh) * | 2011-09-23 | 2012-05-02 | 李氏大药厂(香港)有限公司 | 乙酰左卡尼汀盐酸盐的制备方法及其药物用途 |
CN104163769B (zh) * | 2014-06-23 | 2016-06-15 | 海南霞迪药业有限公司 | 一种氯化丙酰左卡尼汀的制备方法 |
CN104586826B (zh) * | 2014-12-26 | 2018-06-01 | 东北制药集团沈阳第一制药有限公司 | 左卡尼汀及其衍生物在制备治疗或预防特发性肺纤维化药物中的应用 |
CN110559265A (zh) * | 2018-06-05 | 2019-12-13 | 辽宁科硕营养科技股份有限公司 | 一种乙酰左旋肉碱精氨酸二盐酸盐防潮颗粒的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0443996A1 (en) * | 1990-02-23 | 1991-08-28 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Esters of (R)(-)-carnitine and acyl (R)(-)-carnitines with beta-hydroxybutyric acid and pharmaceutical compositions containing them for inhibiting neuronal degeneration, liver proteolysis and for the treatment of coma |
EP0514359A2 (en) * | 1991-05-16 | 1992-11-19 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Alkanoyl L-carnitine amides with aminoacids and pharmaceutical compositions containing same, for promoting regeneration of the nervous tissue, inhibiting neuronal degeneration, enhancing the processes of learning and memory, and for the treatment of coma |
CN1865231A (zh) * | 2004-10-15 | 2006-11-22 | 山东齐都药业有限公司 | 丙酰-l-卡尼丁内盐的合成方法 |
-
2006
- 2006-12-29 CN CN 200610135197 patent/CN1995010B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0443996A1 (en) * | 1990-02-23 | 1991-08-28 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Esters of (R)(-)-carnitine and acyl (R)(-)-carnitines with beta-hydroxybutyric acid and pharmaceutical compositions containing them for inhibiting neuronal degeneration, liver proteolysis and for the treatment of coma |
EP0514359A2 (en) * | 1991-05-16 | 1992-11-19 | Sigma-Tau Industrie Farmaceutiche Riunite S.p.A. | Alkanoyl L-carnitine amides with aminoacids and pharmaceutical compositions containing same, for promoting regeneration of the nervous tissue, inhibiting neuronal degeneration, enhancing the processes of learning and memory, and for the treatment of coma |
CN1865231A (zh) * | 2004-10-15 | 2006-11-22 | 山东齐都药业有限公司 | 丙酰-l-卡尼丁内盐的合成方法 |
Non-Patent Citations (2)
Title |
---|
程青芳等.盐酸 L-肉碱和盐酸乙酰 L-肉碱的合成.有机化学26 7.2006,26(7),946-949. |
程青芳等.盐酸 L-肉碱和盐酸乙酰 L-肉碱的合成.有机化学26 7.2006,26(7),946-949. * |
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Publication number | Publication date |
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CN1995010A (zh) | 2007-07-11 |
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Owner name: LIAONING KONCEPNUTRA CO., LTD. Free format text: FORMER OWNER: SHENYANG KONCEPNUTRA CO., LTD. Effective date: 20120920 |
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Free format text: CORRECT: ADDRESS; FROM: 110172 SHENYANG, LIAONING PROVINCE TO: 117004 BENXI, LIAONING PROVINCE |
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Effective date of registration: 20120920 Address after: 117004 Liaoning city of Benxi province Cladrastis Road Economic Development Zone No. 100 Applicant after: Liaoning Keshuo Nutrition Technology Co., Ltd. Address before: 110172, Liaoning province Shenyang Dongling District Wang Zhen town under the official village Applicant before: Shenyang Keshuo Nutrition Technology Co., Ltd. |
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EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20070711 Assignee: Liaoning Nirvana Pharmaceutical Co., Ltd. Assignor: Liaoning Keshuo Nutrition Technology Co., Ltd. Contract record no.: 2013210000130 Denomination of invention: Method for synthesizing propionyl levo-carnitine hydrochlorate Granted publication date: 20121212 License type: Exclusive License Record date: 20130930 |
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LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
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Address after: 117000 No. 100 Huai Huai Road, Benxi Economic Development Zone, Benxi, Liaoning Patentee after: Liaoning Ke Shuo nutrition Polytron Technologies Inc Address before: 117004 No. 100, Xiang Huai Road, Benxi Economic Development Zone, Liaoning Patentee before: Liaoning Keshuo Nutrition Technology Co., Ltd. |