DK3144295T3 - METHOD FOR LACOSAMIDE PREPARATION - Google Patents
METHOD FOR LACOSAMIDE PREPARATION Download PDFInfo
- Publication number
- DK3144295T3 DK3144295T3 DK15003058.3T DK15003058T DK3144295T3 DK 3144295 T3 DK3144295 T3 DK 3144295T3 DK 15003058 T DK15003058 T DK 15003058T DK 3144295 T3 DK3144295 T3 DK 3144295T3
- Authority
- DK
- Denmark
- Prior art keywords
- serine
- formula
- benzylamine
- benzyl
- acetamido
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- VPPJLAIAVCUEMN-GFCCVEGCSA-N lacosamide Chemical compound COC[C@@H](NC(C)=O)C(=O)NCC1=CC=CC=C1 VPPJLAIAVCUEMN-GFCCVEGCSA-N 0.000 title claims description 22
- 229960002623 lacosamide Drugs 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title description 18
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 36
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 21
- ONUNDAQVOOLWTH-RXMQYKEDSA-N methyl (2r)-2-acetamido-3-hydroxypropanoate Chemical compound COC(=O)[C@@H](CO)NC(C)=O ONUNDAQVOOLWTH-RXMQYKEDSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000007069 methylation reaction Methods 0.000 claims description 12
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 10
- 230000000269 nucleophilic effect Effects 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 5
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims 1
- XRKSCJLQKGLSKU-LLVKDONJSA-N O-Desmethyl-lacosamide Chemical compound CC(=O)N[C@H](CO)C(=O)NCC1=CC=CC=C1 XRKSCJLQKGLSKU-LLVKDONJSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 230000011987 methylation Effects 0.000 description 11
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 10
- 229930195711 D-Serine Natural products 0.000 description 10
- 238000004296 chiral HPLC Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 230000006340 racemization Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 238000006640 acetylation reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- NDBQJIBNNUJNHA-AENDTGMFSA-N methyl (2r)-2-amino-3-hydroxypropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](N)CO NDBQJIBNNUJNHA-AENDTGMFSA-N 0.000 description 3
- -1 methyl ester hydrochloride Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 102220079670 rs759826252 Human genes 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FHOAKXBXYSJBGX-RXMQYKEDSA-N (2r)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](CO)C(O)=O FHOAKXBXYSJBGX-RXMQYKEDSA-N 0.000 description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KNTFCRCCPLEUQZ-UHFFFAOYSA-N O-Methyl-DL-serine Chemical compound COCC(N)C(O)=O KNTFCRCCPLEUQZ-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- JJIHLJJYMXLCOY-SCSAIBSYSA-N (2r)-2-acetamido-3-hydroxypropanoic acid Chemical compound CC(=O)N[C@H](CO)C(O)=O JJIHLJJYMXLCOY-SCSAIBSYSA-N 0.000 description 1
- WYCNJBXJCACFCM-SECBINFHSA-N (2r)-2-amino-n-benzyl-3-hydroxypropanamide Chemical compound OC[C@@H](N)C(=O)NCC1=CC=CC=C1 WYCNJBXJCACFCM-SECBINFHSA-N 0.000 description 1
- HZEFRMKXCIOSOX-MUUNZHRXSA-N (2r)-n-benzyl-3-methoxy-2-(tritylamino)propanamide Chemical compound N([C@H](COC)C(=O)NCC=1C=CC=CC=1)C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HZEFRMKXCIOSOX-MUUNZHRXSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- XRKSCJLQKGLSKU-UHFFFAOYSA-N 2-acetamido-n-benzyl-3-hydroxypropanamide Chemical compound CC(=O)NC(CO)C(=O)NCC1=CC=CC=C1 XRKSCJLQKGLSKU-UHFFFAOYSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-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
- LQVXSNNAFNGRAH-QHCPKHFHSA-N BMS-754807 Chemical compound C([C@@]1(C)C(=O)NC=2C=NC(F)=CC=2)CCN1C(=NN1C=CC=C11)N=C1NC(=NN1)C=C1C1CC1 LQVXSNNAFNGRAH-QHCPKHFHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- MWHHJYUHCZWSLS-UHFFFAOYSA-N FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F Chemical compound FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F MWHHJYUHCZWSLS-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- ONUNDAQVOOLWTH-UHFFFAOYSA-N methyl 2-acetamido-3-hydroxypropanoate Chemical compound COC(=O)C(CO)NC(C)=O ONUNDAQVOOLWTH-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 238000012803 optimization experiment Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940089285 vimpat Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN5001CH2015 IN2015CH05001A (enExample) | 2015-09-18 | 2015-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK3144295T3 true DK3144295T3 (en) | 2019-03-25 |
Family
ID=54398495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK15003058.3T DK3144295T3 (en) | 2015-09-18 | 2015-10-23 | METHOD FOR LACOSAMIDE PREPARATION |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9447024B1 (enExample) |
| EP (1) | EP3144295B1 (enExample) |
| KR (1) | KR101886643B1 (enExample) |
| CN (1) | CN106543018A (enExample) |
| DK (1) | DK3144295T3 (enExample) |
| ES (1) | ES2708176T3 (enExample) |
| HR (1) | HRP20190403T1 (enExample) |
| HU (1) | HUE043136T2 (enExample) |
| IN (1) | IN2015CH05001A (enExample) |
| SI (1) | SI3144295T1 (enExample) |
| TR (1) | TR201901398T4 (enExample) |
| TW (1) | TWI634100B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107641087A (zh) * | 2017-06-01 | 2018-01-30 | 合肥远志医药科技开发有限公司 | 一种工业化拉科酰胺的制备方法 |
| CN108558690B (zh) * | 2018-03-28 | 2021-04-20 | 浙江海正药业股份有限公司 | 环丝氨酸酯化物盐酸盐的晶型及其制备方法 |
| CN110320291A (zh) * | 2019-06-21 | 2019-10-11 | 山东省药学科学院 | 一种hplc法定量检测拉考沙胺注射液含量的方法 |
| CN115825300B (zh) * | 2022-11-30 | 2024-12-06 | 山东百诺医药股份有限公司 | 一种检测拉考沙胺对映异构体的反相液相色谱方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5773475A (en) | 1997-03-17 | 1998-06-30 | Research Corporation Technologies, Inc. | Anticonvulsant enantiomeric amino acid derivatives |
| EP1642889A1 (en) | 2004-10-02 | 2006-04-05 | Schwarz Pharma Ag | Improved synthesis scheme for lacosamide |
| US8093426B2 (en) | 2007-12-04 | 2012-01-10 | Ranbaxy Laboratories Limited | Intermediate compounds and their use in preparation of lacosamide |
| JP5564570B2 (ja) | 2009-09-25 | 2014-07-30 | カディラ・ヘルスケア・リミテッド | ラコサミドおよびその中間体の調製方法 |
| IT1398044B1 (it) * | 2010-01-29 | 2013-02-07 | Archimica Srl | Processo per la preparazione della lacosamide |
| EP2534128A1 (en) * | 2010-02-08 | 2012-12-19 | Natco Pharma Limited | A process for the preparation of lacosamide |
| WO2011099033A1 (en) * | 2010-02-09 | 2011-08-18 | Msn Laboratories Limited | Process for preparing (r)-2-acetamido-n-benzyl-3-methoxy-propionamide |
| WO2011144983A2 (en) * | 2010-05-17 | 2011-11-24 | Aurobindo Pharma Limited | An improved process for the preparation of lacosamide |
| EP2399901A1 (en) * | 2010-06-23 | 2011-12-28 | Archimica GmbH | Intermediate for producing lacosamide and a process for its preparation and conversion to lacosamide |
| PL2444390T3 (pl) * | 2010-10-19 | 2017-06-30 | Euticals Gmbh | Sposób wytwarzania Lakozamidu |
| EP2487152A1 (en) | 2010-11-17 | 2012-08-15 | UCB Pharma GmbH | Process for the preparation of Lacosamide including resolution of O-methyl-DL-serine |
| CN103113256A (zh) * | 2011-11-17 | 2013-05-22 | 苏州洪瑞医药科技有限公司 | 一种拉科酰胺的合成方法 |
| CN104892450A (zh) * | 2015-06-01 | 2015-09-09 | 江苏海岸药业有限公司 | 一种拉科酰胺的制备方法 |
-
2015
- 2015-09-18 IN IN5001CH2015 patent/IN2015CH05001A/en unknown
- 2015-10-16 US US14/885,321 patent/US9447024B1/en active Active
- 2015-10-23 DK DK15003058.3T patent/DK3144295T3/en active
- 2015-10-23 EP EP15003058.3A patent/EP3144295B1/en active Active
- 2015-10-23 SI SI201530610T patent/SI3144295T1/sl unknown
- 2015-10-23 HU HUE15003058A patent/HUE043136T2/hu unknown
- 2015-10-23 ES ES15003058T patent/ES2708176T3/es active Active
- 2015-10-23 TR TR2019/01398T patent/TR201901398T4/tr unknown
- 2015-11-10 KR KR1020150157145A patent/KR101886643B1/ko active Active
- 2015-12-25 TW TW104143667A patent/TWI634100B/zh active
- 2015-12-29 CN CN201511017774.6A patent/CN106543018A/zh active Pending
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2019
- 2019-03-01 HR HRP20190403TT patent/HRP20190403T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP3144295A1 (en) | 2017-03-22 |
| HUE043136T2 (hu) | 2019-07-29 |
| TR201901398T4 (tr) | 2019-02-21 |
| TWI634100B (zh) | 2018-09-01 |
| EP3144295B1 (en) | 2018-12-05 |
| ES2708176T3 (es) | 2019-04-09 |
| US9447024B1 (en) | 2016-09-20 |
| TW201711992A (zh) | 2017-04-01 |
| IN2015CH05001A (enExample) | 2015-10-16 |
| SI3144295T1 (sl) | 2019-03-29 |
| CN106543018A (zh) | 2017-03-29 |
| KR20170034281A (ko) | 2017-03-28 |
| HRP20190403T1 (hr) | 2019-05-03 |
| KR101886643B1 (ko) | 2018-08-08 |
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