JP2002544252A5 - - Google Patents
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- Publication number
- JP2002544252A5 JP2002544252A5 JP2000618226A JP2000618226A JP2002544252A5 JP 2002544252 A5 JP2002544252 A5 JP 2002544252A5 JP 2000618226 A JP2000618226 A JP 2000618226A JP 2000618226 A JP2000618226 A JP 2000618226A JP 2002544252 A5 JP2002544252 A5 JP 2002544252A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- chlorosuccinic
- reaction
- compound
- described method
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 3
- 239000004317 sodium nitrate Substances 0.000 description 3
- 235000010344 sodium nitrate Nutrition 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- -1 Hydride Chemical compound 0.000 description 2
- 239000012448 Lithium borohydride Chemical group 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 125000005905 mesyloxy group Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZKASOSSCYHQHDU-REOHCLBHSA-N (2s)-2-chlorobutanedioyl dichloride Chemical compound ClC(=O)[C@@H](Cl)CC(Cl)=O ZKASOSSCYHQHDU-REOHCLBHSA-N 0.000 description 1
- YWWMSXSIVPRWJY-VKHMYHEASA-N (2s)-2-methylsulfonyloxybutanedioic acid Chemical compound CS(=O)(=O)O[C@H](C(O)=O)CC(O)=O YWWMSXSIVPRWJY-VKHMYHEASA-N 0.000 description 1
- MCMLJMMLKJFXBH-VKHMYHEASA-N (3s)-3-chloro-4-methoxy-4-oxobutanoic acid Chemical compound COC(=O)[C@@H](Cl)CC(O)=O MCMLJMMLKJFXBH-VKHMYHEASA-N 0.000 description 1
- RIHWJROUZAYQGA-REOHCLBHSA-N (3s)-3-chlorooxolane-2,5-dione Chemical compound Cl[C@H]1CC(=O)OC1=O RIHWJROUZAYQGA-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QEGKXSHUKXMDRW-UHFFFAOYSA-N 2-chlorosuccinic acid Chemical compound OC(=O)CC(Cl)C(O)=O QEGKXSHUKXMDRW-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1999RM000310 IT1306142B1 (it) | 1999-05-18 | 1999-05-18 | Procedimento per la preparazione di r-(-)-carnitina a partiredall'acido s-(-)-clorosuccinico. |
| IT1999RM000670 IT1306737B1 (it) | 1999-10-29 | 1999-10-29 | Procedimento per la preparazione di acidi carbossilici chirali. |
| IT2000RM000061 IT1316989B1 (it) | 2000-02-10 | 2000-02-10 | Procedimento per la preparazione di r-(-)- carnitina a partire daacido s-(-)- clorosuccinico o da un suo derivato. |
| IT99A000310 | 2000-02-10 | ||
| IT99A000670 | 2000-02-10 | ||
| IT2000A000061 | 2000-02-10 | ||
| PCT/IT2000/000187 WO2000069808A1 (en) | 1999-05-18 | 2000-05-12 | Process for preparing r-(-)-carnitine from s-(-)-chlorosuccinic acid or from a derivative thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010153891A Division JP2010229157A (ja) | 1999-05-18 | 2010-07-06 | Ｓ−（−）−クロロコハク酸またはその誘導体からｒ−（−）−カルニチンを調製するための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002544252A JP2002544252A (ja) | 2002-12-24 |
| JP2002544252A5 true JP2002544252A5 (enExample) | 2007-06-28 |
| JP4584464B2 JP4584464B2 (ja) | 2010-11-24 |
Family
ID=27274166
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000618226A Expired - Fee Related JP4584464B2 (ja) | 1999-05-18 | 2000-05-12 | Ｓ−（−）−クロロコハク酸またはその誘導体からｒ−（−）−カルニチンを調製するための方法 |
| JP2010153891A Pending JP2010229157A (ja) | 1999-05-18 | 2010-07-06 | Ｓ−（−）−クロロコハク酸またはその誘導体からｒ−（−）−カルニチンを調製するための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010153891A Pending JP2010229157A (ja) | 1999-05-18 | 2010-07-06 | Ｓ−（−）−クロロコハク酸またはその誘導体からｒ−（−）−カルニチンを調製するための方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US6677476B1 (enExample) |
| EP (2) | EP1187805B1 (enExample) |
| JP (2) | JP4584464B2 (enExample) |
| KR (2) | KR100684379B1 (enExample) |
| CN (1) | CN1158244C (enExample) |
| AT (1) | ATE346838T1 (enExample) |
| AU (1) | AU4612100A (enExample) |
| CA (1) | CA2372424A1 (enExample) |
| CY (1) | CY1107566T1 (enExample) |
| CZ (1) | CZ20013816A3 (enExample) |
| DE (1) | DE60032139T2 (enExample) |
| DK (1) | DK1187805T3 (enExample) |
| ES (1) | ES2277838T3 (enExample) |
| HU (1) | HUP0201418A3 (enExample) |
| MX (1) | MXPA01011758A (enExample) |
| PL (1) | PL203993B1 (enExample) |
| PT (1) | PT1187805E (enExample) |
| SK (1) | SK286155B6 (enExample) |
| WO (1) | WO2000069808A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI367882B (en) | 2003-03-26 | 2012-07-11 | Du Pont | Preparation and use of 2-substituted-5-oxo-3-pyrazolidinecarboxylates |
| WO2007139238A1 (en) * | 2006-05-26 | 2007-12-06 | Enzytech, Ltd. | Process for l-carnitine and acetyl l-carnitine hydrochloride |
| CN101573326B (zh) | 2006-11-09 | 2013-05-01 | 三菱丽阳株式会社 | 甜菜碱的制造方法 |
| EP2325164A1 (en) * | 2009-11-18 | 2011-05-25 | Lonza Ltd. | Methods for the production of l-carnitine |
| US8310256B2 (en) | 2009-12-22 | 2012-11-13 | Teradyne, Inc. | Capacitive opens testing in low signal environments |
| JP6034287B2 (ja) * | 2010-07-21 | 2016-11-30 | ロンザ リミテッドＬｏｎｚａ Ｌｉｍｉｔｅｄ | β−ラクトンからのカルニチンの製造のためのプロセス |
| KR101110206B1 (ko) * | 2011-05-02 | 2012-02-15 | 송명호 | 개폐가 용이하도록 완충기가 구비된 진동선별장치 |
| CN118638020B (zh) * | 2024-08-08 | 2024-11-19 | 杭州海尔希畜牧科技有限公司 | L-天门冬氨酸l(-)肉碱(1:1)的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL45594A (en) * | 1973-11-12 | 1977-12-30 | Stauffer Chemical Co | Bis-substituted succinamides and their use as herbicides |
| GB1513257A (en) * | 1975-02-03 | 1978-06-07 | Stauffer Chemical Co | Bis-substituted succinamides and the use thereof as herbicides |
| US4265247A (en) * | 1979-11-07 | 1981-05-05 | Research Corporation | Malic acid polymers |
| ZA826022B (en) * | 1981-08-21 | 1983-08-31 | Univ Miami | Novel complex amido and imido derivatives of carboxyalkyl peptides and thioethers and ethers of peptides |
| DE3144698A1 (de) | 1981-11-11 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hydantoinen |
| DE3144697A1 (de) * | 1981-11-11 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hydantoinen |
| US5473104A (en) * | 1994-09-13 | 1995-12-05 | Neurocrine Biosciences, Inc. | Process for the preparation of L-carnitine |
| KR100255039B1 (ko) | 1997-07-28 | 2000-05-01 | 박영구 | L-카르니틴의제조방법 |
-
2000
- 2000-05-12 ES ES00927737T patent/ES2277838T3/es not_active Expired - Lifetime
- 2000-05-12 HU HU0201418A patent/HUP0201418A3/hu unknown
- 2000-05-12 WO PCT/IT2000/000187 patent/WO2000069808A1/en not_active Ceased
- 2000-05-12 PT PT00927737T patent/PT1187805E/pt unknown
- 2000-05-12 DK DK00927737T patent/DK1187805T3/da active
- 2000-05-12 DE DE60032139T patent/DE60032139T2/de not_active Expired - Lifetime
- 2000-05-12 CA CA002372424A patent/CA2372424A1/en not_active Abandoned
- 2000-05-12 AU AU46121/00A patent/AU4612100A/en not_active Abandoned
- 2000-05-12 KR KR1020017014397A patent/KR100684379B1/ko not_active Expired - Fee Related
- 2000-05-12 AT AT00927737T patent/ATE346838T1/de not_active IP Right Cessation
- 2000-05-12 EP EP00927737A patent/EP1187805B1/en not_active Expired - Lifetime
- 2000-05-12 MX MXPA01011758A patent/MXPA01011758A/es active IP Right Grant
- 2000-05-12 CZ CZ20013816A patent/CZ20013816A3/cs unknown
- 2000-05-12 US US09/959,717 patent/US6677476B1/en not_active Expired - Fee Related
- 2000-05-12 KR KR1020067021556A patent/KR100789468B1/ko not_active Expired - Fee Related
- 2000-05-12 SK SK1601-2001A patent/SK286155B6/sk not_active IP Right Cessation
- 2000-05-12 PL PL351646A patent/PL203993B1/pl not_active IP Right Cessation
- 2000-05-12 JP JP2000618226A patent/JP4584464B2/ja not_active Expired - Fee Related
- 2000-05-12 EP EP04013530A patent/EP1468979A1/en not_active Withdrawn
- 2000-05-12 CN CNB008076502A patent/CN1158244C/zh not_active Expired - Fee Related
-
2003
- 2003-11-20 US US10/716,453 patent/US6984739B2/en not_active Expired - Fee Related
-
2005
- 2005-07-07 US US11/175,356 patent/US7247747B2/en not_active Expired - Fee Related
-
2007
- 2007-02-26 CY CY20071100268T patent/CY1107566T1/el unknown
-
2010
- 2010-07-06 JP JP2010153891A patent/JP2010229157A/ja active Pending
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