CA2120811C - Improved process for manufacturing l-(-)-carnitine from waste products having opposite configuration - Google Patents
Improved process for manufacturing l-(-)-carnitine from waste products having opposite configuration Download PDFInfo
- Publication number
- CA2120811C CA2120811C CA002120811A CA2120811A CA2120811C CA 2120811 C CA2120811 C CA 2120811C CA 002120811 A CA002120811 A CA 002120811A CA 2120811 A CA2120811 A CA 2120811A CA 2120811 C CA2120811 C CA 2120811C
- Authority
- CA
- Canada
- Prior art keywords
- carnitine
- general formula
- acyl
- precursor
- carnitinamide
- 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.)
- Expired - Fee Related
Links
- PHIQHXFUZVPYII-UHFFFAOYSA-N carnitine Chemical compound C[N+](C)(C)CC(O)CC([O-])=O PHIQHXFUZVPYII-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 239000002699 waste material Substances 0.000 title description 2
- 125000002252 acyl group Chemical group 0.000 claims abstract description 20
- 150000002596 lactones Chemical class 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 238000005903 acid hydrolysis reaction Methods 0.000 claims abstract description 3
- -1 p-toluenesulfonyl Chemical group 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 11
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- 239000003637 basic solution Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-M periodate Chemical compound [O-]I(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-M 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- PHIQHXFUZVPYII-LURJTMIESA-N (S)-carnitine Chemical compound C[N+](C)(C)C[C@@H](O)CC([O-])=O PHIQHXFUZVPYII-LURJTMIESA-N 0.000 abstract description 7
- 239000007858 starting material Substances 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000002906 microbiologic effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GUYHPGUANSLONG-SNAWJCMRSA-N (E)-4-(trimethylammonio)but-2-enoate Chemical compound C[N+](C)(C)C\C=C\C([O-])=O GUYHPGUANSLONG-SNAWJCMRSA-N 0.000 description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- VRNSCWCXWNQSLG-MRVPVSSYSA-N CS(=O)(=O)[C@@](O)(C[N+](C)(C)C)CC([O-])=O Chemical compound CS(=O)(=O)[C@@](O)(C[N+](C)(C)C)CC([O-])=O VRNSCWCXWNQSLG-MRVPVSSYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960004203 carnitine Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OCQAXYHNMWVLRH-QZTJIDSGSA-N (2r,3r)-2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound O=C([C@@](O)(C(=O)O)[C@](O)(C(O)=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 OCQAXYHNMWVLRH-QZTJIDSGSA-N 0.000 description 1
- KWIXGIMKELMNGH-ZCFIWIBFSA-O (R)-carnitinamide Chemical compound C[N+](C)(C)C[C@H](O)CC(N)=O KWIXGIMKELMNGH-ZCFIWIBFSA-O 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- YNOWULSFLVIUDH-UHFFFAOYSA-N 3-dehydrocarnitine Chemical compound C[N+](C)(C)CC(=O)CC([O-])=O YNOWULSFLVIUDH-UHFFFAOYSA-N 0.000 description 1
- JHPNVNIEXXLNTR-UHFFFAOYSA-N 4-(trimethylammonio)butanoate Chemical compound C[N+](C)(C)CCCC([O-])=O JHPNVNIEXXLNTR-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- 102000013658 Carnitine Acyltransferases Human genes 0.000 description 1
- 108010051527 Carnitine Acyltransferases Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000007836 Chlorogalum pomeridianum Nutrition 0.000 description 1
- 240000006670 Chlorogalum pomeridianum Species 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 229910017974 NH40H Inorganic materials 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000009895 amole Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000001700 mitochondrial membrane Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 208000027232 peripheral nervous system disease Diseases 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
Classifications
-
- 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
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/10—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having one or more double bonds between ring members or between ring members and non-ring members
- C07D305/12—Beta-lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Processing Of Solid Wastes (AREA)
- Fertilizers (AREA)
- Switches Operated By Changes In Physical Conditions (AREA)
- Lighting Device Outwards From Vehicle And Optical Signal (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITRM930226A IT1261230B (it) | 1993-04-08 | 1993-04-08 | Procedimento migliorato per la preparazione di l-(-)-carnitina a partire da suoi precursori aventi opposta configurazione. |
| ITRM93A000226 | 1993-04-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2120811A1 CA2120811A1 (en) | 1994-10-09 |
| CA2120811C true CA2120811C (en) | 2004-10-26 |
Family
ID=11401703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002120811A Expired - Fee Related CA2120811C (en) | 1993-04-08 | 1994-04-07 | Improved process for manufacturing l-(-)-carnitine from waste products having opposite configuration |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5491260A (enExample) |
| EP (1) | EP0623588B1 (enExample) |
| JP (1) | JP3502657B2 (enExample) |
| KR (1) | KR100301951B1 (enExample) |
| AT (1) | ATE150003T1 (enExample) |
| CA (1) | CA2120811C (enExample) |
| DE (1) | DE69401979T2 (enExample) |
| DK (1) | DK0623588T3 (enExample) |
| ES (1) | ES2099563T3 (enExample) |
| GR (1) | GR3023594T3 (enExample) |
| IT (1) | IT1261230B (enExample) |
| TW (1) | TW275613B (enExample) |
| ZA (1) | ZA942428B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1261828B (it) | 1993-07-14 | 1996-06-03 | Sigma Tau Ind Farmaceuti | Esteri di acil l-carnitine e composizioni farmaceutiche che li contengono per il trattamento dello shock endotossico. |
| IT1276207B1 (it) * | 1995-09-29 | 1997-10-27 | Sigma Tau Ind Farmaceuti | Procedimento per la preparazione del (s)-b-idrossi-gamma- butirrolattone |
| KR100255039B1 (ko) * | 1997-07-28 | 2000-05-01 | 박영구 | L-카르니틴의제조방법 |
| IT1297120B1 (it) * | 1997-12-16 | 1999-08-03 | Sigma Tau Ind Farmaceuti | Procedimento per la produzione di (r)-3-idrossi-4-butirrolattone utile nella preparazione della (r)-carnitina |
| DE10027391B4 (de) * | 2000-06-02 | 2006-05-04 | Wella Ag | Oligomere und Polymere aus Crotonbetain oder Crotonbetainderivaten |
| KR20130093078A (ko) * | 2010-07-21 | 2013-08-21 | 론차리미티드 | 베타-락톤으로부터 카르니틴의 제조방법 |
| EP2468739A1 (en) * | 2010-12-22 | 2012-06-27 | Lonza Ltd. | A process for the production of carnitine from B-lactones |
| EP2409965A1 (en) * | 2010-07-21 | 2012-01-25 | Lonza Ltd. | A process for the production of carnitine by cycloaddition |
| EP2409972A1 (en) * | 2010-07-21 | 2012-01-25 | Lonza Ltd. | A process for the production of carnitine from B-lactones |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE664500A (enExample) * | ||||
| ES332080A1 (es) * | 1965-10-15 | 1967-10-01 | Otsuka Pharma Co Ltd | Procedimiento para obtencion de complejos de sales opticamente activas de hidroxido de nitrilo,carnitina y acidos glutamicos n-acilos. |
| IT1156852B (it) * | 1978-07-10 | 1987-02-04 | Sigma Tau Ind Farmaceuti | Procedimento industriale per la preparazione del d'canforato della l carnitinammide e del d canforato della d carnitinammide e sue applicazioni |
| IT1136945B (it) * | 1981-03-18 | 1986-09-03 | Anic Spa | Processo per la preparazione di l-carnitina |
| JPS59183694A (ja) * | 1983-04-05 | 1984-10-18 | Hamari Yakuhin Kogyo Kk | 光学活性なカルニチンの生化学的製造法 |
| JPS59192095A (ja) * | 1983-04-13 | 1984-10-31 | Ajinomoto Co Inc | Ｌ−カルニチンの製造法 |
| DD221905B1 (de) * | 1983-11-03 | 1987-03-18 | Univ Leipzig | Verfahren zur herstellung von l(-)-carnitin und seinen derivaten |
| CH664374A5 (de) * | 1985-02-27 | 1988-02-29 | Lonza Ag | Verfahren zur herstellung von l-carnitin auf mikrobiologischem weg. |
| US5200526A (en) * | 1987-04-27 | 1993-04-06 | The Governors Of The University Of Alberta | Syntheses of optically pure α-amino acids from 3-amino-2-oxetanone salts |
| JPH0291049A (ja) * | 1988-09-21 | 1990-03-30 | Lonza Ag | ｒ―ブチロベタインの製造方法 |
| IT1231751B (it) * | 1989-04-12 | 1991-12-21 | Sigma Tau Ind Farmaceuti | Procedimento per la produzione di r(+) amminocarnitina e s(-) amminocarnitina |
| CA2021869C (en) * | 1989-07-28 | 2000-09-05 | Frans Hoeks | Process for microbiological batch production of l-carnitine |
| IT1240833B (it) * | 1990-05-14 | 1993-12-17 | Sigma Tau Ind Farmaceuti | Procedimento biocatalitico per la produzione di l-(-)- carnitina da crotonilbetaina e ceppi di proteeae per l'uso in tale procedimento |
| IT1245699B (it) * | 1991-05-29 | 1994-10-14 | Sigma Tau Ind Farmaceuti | Derivati della l-carnitina quali agenti terapeutici per il trattamento delle miopatie, della degenarazione neuronale e per inibire la proteolisi |
| IT1256705B (it) * | 1992-12-21 | 1995-12-12 | Sigma Tau Ind Farmaceuti | Procedimento per la preparazione di l-(-)-carnitina a partire da un prodotto di scarto avente opposta configurazione. |
-
1993
- 1993-04-08 IT ITRM930226A patent/IT1261230B/it active IP Right Grant
-
1994
- 1994-03-31 DK DK94830152.8T patent/DK0623588T3/da active
- 1994-03-31 ES ES94830152T patent/ES2099563T3/es not_active Expired - Lifetime
- 1994-03-31 AT AT94830152T patent/ATE150003T1/de active
- 1994-03-31 DE DE69401979T patent/DE69401979T2/de not_active Expired - Lifetime
- 1994-03-31 EP EP94830152A patent/EP0623588B1/en not_active Expired - Lifetime
- 1994-04-07 JP JP06928994A patent/JP3502657B2/ja not_active Expired - Fee Related
- 1994-04-07 US US08/224,522 patent/US5491260A/en not_active Expired - Lifetime
- 1994-04-07 CA CA002120811A patent/CA2120811C/en not_active Expired - Fee Related
- 1994-04-08 ZA ZA942428A patent/ZA942428B/xx unknown
- 1994-04-08 KR KR1019940007343A patent/KR100301951B1/ko not_active Expired - Fee Related
- 1994-04-19 TW TW083103475A patent/TW275613B/zh not_active IP Right Cessation
-
1997
- 1997-05-30 GR GR970401237T patent/GR3023594T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69401979T2 (de) | 1997-06-26 |
| ES2099563T3 (es) | 1997-05-16 |
| EP0623588A1 (en) | 1994-11-09 |
| IT1261230B (it) | 1996-05-09 |
| DE69401979D1 (de) | 1997-04-17 |
| JPH06311888A (ja) | 1994-11-08 |
| US5491260A (en) | 1996-02-13 |
| GR3023594T3 (en) | 1997-08-29 |
| HK1005867A1 (en) | 1999-01-29 |
| ZA942428B (en) | 1994-11-29 |
| JP3502657B2 (ja) | 2004-03-02 |
| TW275613B (enExample) | 1996-05-11 |
| ATE150003T1 (de) | 1997-03-15 |
| EP0623588B1 (en) | 1997-03-12 |
| CA2120811A1 (en) | 1994-10-09 |
| KR100301951B1 (ko) | 2001-10-22 |
| DK0623588T3 (da) | 1997-07-21 |
| ITRM930226A0 (it) | 1993-04-08 |
| ITRM930226A1 (it) | 1994-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140408 |