SK286155B6 - Spôsob prípravy vnútornej soli L-karnitínu, medziprodukty na jej prípravu a ich použitie - Google Patents
Spôsob prípravy vnútornej soli L-karnitínu, medziprodukty na jej prípravu a ich použitie Download PDFInfo
- Publication number
- SK286155B6 SK286155B6 SK1601-2001A SK16012001A SK286155B6 SK 286155 B6 SK286155 B6 SK 286155B6 SK 16012001 A SK16012001 A SK 16012001A SK 286155 B6 SK286155 B6 SK 286155B6
- Authority
- SK
- Slovakia
- Prior art keywords
- reduction
- carnitine
- compound
- inner salt
- acid
- Prior art date
Links
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000008569 process Effects 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 239000000543 intermediate Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 230000009467 reduction Effects 0.000 claims abstract description 35
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000004678 hydrides Chemical class 0.000 claims abstract description 11
- 239000012448 Lithium borohydride Substances 0.000 claims abstract description 7
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- ZKASOSSCYHQHDU-REOHCLBHSA-N (2s)-2-chlorobutanedioyl dichloride Chemical compound ClC(=O)[C@@H](Cl)CC(Cl)=O ZKASOSSCYHQHDU-REOHCLBHSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 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 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 5
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 230000009466 transformation Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005905 mesyloxy group Chemical group 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 102100027456 Cytochrome c oxidase subunit 2 Human genes 0.000 abstract 1
- 101000725401 Homo sapiens Cytochrome c oxidase subunit 2 Proteins 0.000 abstract 1
- 101000605127 Homo sapiens Prostaglandin G/H synthase 2 Proteins 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000047 product Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 239000003638 chemical reducing agent Substances 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 150000002367 halogens Chemical group 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229960004203 carnitine Drugs 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JXXCENBLGFBQJM-FYZOBXCZSA-N [(2r)-3-carboxy-2-hydroxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C[C@H](O)CC(O)=O JXXCENBLGFBQJM-FYZOBXCZSA-N 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
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- 230000008020 evaporation Effects 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- QEGKXSHUKXMDRW-REOHCLBHSA-N (2s)-2-chlorobutanedioic acid Chemical compound OC(=O)C[C@H](Cl)C(O)=O QEGKXSHUKXMDRW-REOHCLBHSA-N 0.000 description 3
- PHIQHXFUZVPYII-LURJTMIESA-N (S)-carnitine Chemical compound C[N+](C)(C)C[C@@H](O)CC([O-])=O PHIQHXFUZVPYII-LURJTMIESA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 229960005261 aspartic acid Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- YFAYPUHAMBJFRH-BYPYZUCNSA-N dimethyl (2s)-2-chlorobutanedioate Chemical compound COC(=O)C[C@H](Cl)C(=O)OC YFAYPUHAMBJFRH-BYPYZUCNSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 206010058892 Carnitine deficiency Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- 229910000085 borane Inorganic materials 0.000 description 2
- QQWGVQWAEANRTK-UHFFFAOYSA-N bromosuccinic acid Chemical compound OC(=O)CC(Br)C(O)=O QQWGVQWAEANRTK-UHFFFAOYSA-N 0.000 description 2
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 2
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- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
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- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 description 2
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000003319 supportive effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- 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)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (4)
| 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. |
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK16012001A3 SK16012001A3 (sk) | 2002-04-04 |
| SK286155B6 true SK286155B6 (sk) | 2008-04-07 |
Family
ID=27274166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1601-2001A SK286155B6 (sk) | 1999-05-18 | 2000-05-12 | Spôsob prípravy vnútornej soli L-karnitínu, medziprodukty na jej prípravu a ich použitie |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US6677476B1 (da) |
| EP (2) | EP1468979A1 (da) |
| JP (2) | JP4584464B2 (da) |
| KR (2) | KR100789468B1 (da) |
| CN (1) | CN1158244C (da) |
| AT (1) | ATE346838T1 (da) |
| AU (1) | AU4612100A (da) |
| CA (1) | CA2372424A1 (da) |
| CY (1) | CY1107566T1 (da) |
| CZ (1) | CZ20013816A3 (da) |
| DE (1) | DE60032139T2 (da) |
| DK (1) | DK1187805T3 (da) |
| ES (1) | ES2277838T3 (da) |
| HU (1) | HUP0201418A3 (da) |
| MX (1) | MXPA01011758A (da) |
| PL (1) | PL203993B1 (da) |
| PT (1) | PT1187805E (da) |
| SK (1) | SK286155B6 (da) |
| WO (1) | WO2000069808A1 (da) |
Families Citing this family (7)
| 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 |
| KR101097006B1 (ko) | 2006-11-09 | 2011-12-20 | 미츠비시 레이온 가부시키가이샤 | 베타인의 제조 방법 |
| 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 |
| EP2595973B1 (en) * | 2010-07-21 | 2017-07-12 | Lonza Ltd. | A process for the production of carnitine from beta-lactones |
| KR101110206B1 (ko) * | 2011-05-02 | 2012-02-15 | 송명호 | 개폐가 용이하도록 완충기가 구비된 진동선별장치 |
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 |
| DE3144697A1 (de) * | 1981-11-11 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hydantoinen |
| DE3144698A1 (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 EP EP04013530A patent/EP1468979A1/en not_active Withdrawn
- 2000-05-12 AT AT00927737T patent/ATE346838T1/de not_active IP Right Cessation
- 2000-05-12 SK SK1601-2001A patent/SK286155B6/sk not_active IP Right Cessation
- 2000-05-12 HU HU0201418A patent/HUP0201418A3/hu unknown
- 2000-05-12 DK DK00927737T patent/DK1187805T3/da active
- 2000-05-12 EP EP00927737A patent/EP1187805B1/en not_active Expired - Lifetime
- 2000-05-12 KR KR1020067021556A patent/KR100789468B1/ko not_active IP Right Cessation
- 2000-05-12 PL PL351646A patent/PL203993B1/pl not_active IP Right Cessation
- 2000-05-12 WO PCT/IT2000/000187 patent/WO2000069808A1/en active IP Right Grant
- 2000-05-12 CZ CZ20013816A patent/CZ20013816A3/cs unknown
- 2000-05-12 ES ES00927737T patent/ES2277838T3/es not_active Expired - Lifetime
- 2000-05-12 US US09/959,717 patent/US6677476B1/en not_active Expired - Fee Related
- 2000-05-12 AU AU46121/00A patent/AU4612100A/en not_active Abandoned
- 2000-05-12 DE DE60032139T patent/DE60032139T2/de not_active Expired - Lifetime
- 2000-05-12 JP JP2000618226A patent/JP4584464B2/ja not_active Expired - Fee Related
- 2000-05-12 PT PT00927737T patent/PT1187805E/pt unknown
- 2000-05-12 CA CA002372424A patent/CA2372424A1/en not_active Abandoned
- 2000-05-12 KR KR1020017014397A patent/KR100684379B1/ko not_active IP Right Cessation
- 2000-05-12 CN CNB008076502A patent/CN1158244C/zh not_active Expired - Fee Related
- 2000-05-12 MX MXPA01011758A patent/MXPA01011758A/es active IP Right Grant
-
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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20110512 |