DD284674A5 - Verfahren zur synthese von levodopa - Google Patents
Verfahren zur synthese von levodopa Download PDFInfo
- Publication number
- DD284674A5 DD284674A5 DD89330685A DD33068589A DD284674A5 DD 284674 A5 DD284674 A5 DD 284674A5 DD 89330685 A DD89330685 A DD 89330685A DD 33068589 A DD33068589 A DD 33068589A DD 284674 A5 DD284674 A5 DD 284674A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- amino
- formula
- dimethoxyphenyl
- acid
- propionitrile
- Prior art date
Links
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 title claims abstract description 33
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 229960004502 levodopa Drugs 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 13
- 230000007062 hydrolysis Effects 0.000 claims abstract description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 11
- 230000017858 demethylation Effects 0.000 claims abstract description 7
- 238000010520 demethylation reaction Methods 0.000 claims abstract description 7
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims abstract description 6
- 150000007513 acids Chemical class 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 18
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 14
- -1 alkali metal cyanide Chemical class 0.000 claims description 14
- 239000000908 ammonium hydroxide Substances 0.000 claims description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical group N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 238000011081 inoculation Methods 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 abstract description 5
- 238000004090 dissolution Methods 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 5
- RIVVYJWUHXMGSK-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetaldehyde Chemical compound COC1=CC=C(CC=O)C=C1OC RIVVYJWUHXMGSK-UHFFFAOYSA-N 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000005219 aminonitrile group Chemical group 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BETCBHDWQFVCJI-UHFFFAOYSA-N Cl.COC=1C=C(C=CC1OC)C(C#N)C Chemical compound Cl.COC=1C=C(C=CC1OC)C(C#N)C BETCBHDWQFVCJI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960004441 tyrosine Drugs 0.000 description 2
- UFEIDPFGICDUHT-AWEZNQCLSA-N (2s)-2-benzamido-3-(3,4-dimethoxyphenyl)propanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1 UFEIDPFGICDUHT-AWEZNQCLSA-N 0.000 description 1
- UYRNFBHAWUOWGM-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(O)C(O)=C1 UYRNFBHAWUOWGM-UHFFFAOYSA-N 0.000 description 1
- LQQFFJFGLSKYIR-UHFFFAOYSA-N 3,4-dihydroxyphenylpyruvic acid Chemical class OC(=O)C(=O)CC1=CC=C(O)C(O)=C1 LQQFFJFGLSKYIR-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
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- SYOIWFNFUFXXMV-UHFFFAOYSA-N [Br].Cl Chemical compound [Br].Cl SYOIWFNFUFXXMV-UHFFFAOYSA-N 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 150000001510 aspartic acids Chemical class 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 150000002307 glutamic acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C229/34—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 containing six-membered aromatic rings
- C07C229/36—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 containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- 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
- C07C227/34—Preparation of optical isomers by separation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
- C07C255/43—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8821322A IT1226902B (it) | 1988-07-12 | 1988-07-12 | Processo per la sintesi del levodopa |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD284674A5 true DD284674A5 (de) | 1990-11-21 |
Family
ID=11180092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD89330685A DD284674A5 (de) | 1988-07-12 | 1989-07-11 | Verfahren zur synthese von levodopa |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4962223A (fr) |
| EP (1) | EP0357565B1 (fr) |
| JP (1) | JP2507069B2 (fr) |
| KR (1) | KR960004185B1 (fr) |
| AR (1) | AR248267A1 (fr) |
| AT (1) | ATE111439T1 (fr) |
| AU (1) | AU615083B2 (fr) |
| CA (1) | CA1338672C (fr) |
| DD (1) | DD284674A5 (fr) |
| DE (1) | DE68918207T2 (fr) |
| DK (1) | DK172106B1 (fr) |
| ES (1) | ES2063837T3 (fr) |
| FI (1) | FI101534B1 (fr) |
| HU (1) | HU203318B (fr) |
| IE (1) | IE65956B1 (fr) |
| IL (1) | IL90844A0 (fr) |
| IT (1) | IT1226902B (fr) |
| NO (1) | NO174293C (fr) |
| NZ (1) | NZ229910A (fr) |
| PL (1) | PL160103B1 (fr) |
| PT (1) | PT91144B (fr) |
| YU (1) | YU47907B (fr) |
| ZA (1) | ZA895255B (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5459145A (en) * | 1988-01-19 | 1995-10-17 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| IT1226903B (it) * | 1988-07-12 | 1991-02-21 | Mini Ricerca Scient Tecnolog | Processo per la sintesi di aminoacidi otticamente attivi |
| US5395935A (en) * | 1992-05-08 | 1995-03-07 | Pfizer Inc. | Endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents |
| DE19502967A1 (de) * | 1995-01-31 | 1996-08-01 | Basf Ag | Verfahren zur Racemattrennung von 2-Aryl-2-omega-alkylaminoalkannitrilen |
| JP3634207B2 (ja) * | 1999-09-14 | 2005-03-30 | 独立行政法人科学技術振興機構 | 光学活性なα−アミノニトリル並びにα−アミノ酸類の製造方法 |
| US20040002615A1 (en) * | 2002-06-28 | 2004-01-01 | Allen David Robert | Preparation of chiral amino-nitriles |
| EP1560569A4 (fr) * | 2002-10-11 | 2006-03-22 | Depomed Dev Ltd | Forme gastro-retentive pour administrer du levodopa |
| DE10261807A1 (de) * | 2002-12-19 | 2004-07-01 | Turicum Drug Development Ag | Deuterierte Catecholaminderivate sowie diese Verbindungen enthaltende Arzneimittel |
| EP1596808A4 (fr) * | 2003-02-07 | 2007-04-04 | Yissum Res Dev Co | Derives d'amide l-dopa et utilisations de ceux-ci |
| EA017983B1 (ru) | 2006-02-17 | 2013-04-30 | Бедс Фарма Гмбх Беролина Инновейтив Ресёч Энд Девелопмент Сёвисиз | Дейтерированные производные катехоламина и лекарственные средства, содержащие указанные соединения |
| US10258585B2 (en) | 2014-03-13 | 2019-04-16 | Neuroderm, Ltd. | DOPA decarboxylase inhibitor compositions |
| EP4299128A3 (fr) | 2014-03-13 | 2024-04-17 | Neuroderm Ltd. | Compositions d'inhibiteurs de dopa-décarboxylase |
| SG11202103183PA (en) | 2018-09-28 | 2021-04-29 | Univ Griffith | Agents and methods for modulating pathogen activity |
| US11844754B2 (en) | 2020-11-17 | 2023-12-19 | Neuroderm, Ltd. | Methods for treatment of Parkinson's disease |
| US11331293B1 (en) | 2020-11-17 | 2022-05-17 | Neuroderm, Ltd. | Method for treatment of Parkinson's disease |
| US11213502B1 (en) | 2020-11-17 | 2022-01-04 | Neuroderm, Ltd. | Method for treatment of parkinson's disease |
| US12161612B2 (en) | 2023-04-14 | 2024-12-10 | Neuroderm, Ltd. | Methods and compositions for reducing symptoms of Parkinson's disease |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA504449A (fr) * | 1954-07-20 | C. Britton Edgar | Alpha-amino-beta-alkoxy-butyronitriles et methode de fabrication | |
| NL299155A (fr) * | 1962-10-11 | |||
| US3845076A (en) * | 1971-04-20 | 1974-10-29 | Sagami Chem Res | Method of preparing aldehydes |
| JPS4920305A (fr) * | 1972-06-21 | 1974-02-22 | ||
| HU165026B (fr) * | 1972-08-11 | 1974-06-28 | ||
| US4072698A (en) * | 1976-12-02 | 1978-02-07 | The Upjohn Company | Resolution of aminonitriles |
| YU93877A (en) * | 1977-04-08 | 1982-06-30 | Krka | Process for the resolution of racemic alpha-aminonitrils |
| IL59048A (en) * | 1979-12-27 | 1984-01-31 | Plantex Ltd | Process for the preparation of alpha-amino-3-phenyl-propionitriles and novel benzylidene amino acetonitriles as intermediates therefor |
| DE3002543A1 (de) * | 1980-01-25 | 1981-07-30 | Basf Ag, 6700 Ludwigshafen | 4-tert.-butoxyphenylglycinnitril sowie verfahren zur herstellung von d-(-)- und l-(+)-4-hydroxyphenylglycin |
| JPS56115749A (en) * | 1980-02-18 | 1981-09-11 | Sagami Chem Res Center | Dopa derivative |
| JPS61275253A (ja) * | 1985-05-30 | 1986-12-05 | Nippon Kayaku Co Ltd | ３−（３，４−ジヒドロキシフエニル）−２−メチルアラニンの製造法 |
| FR2614626B1 (fr) * | 1987-04-30 | 1989-07-21 | Ranoux Claude | Conteneur pour fecondation des ovocytes et replacement des embryons chez l'homme et l'animal |
-
1988
- 1988-07-12 IT IT8821322A patent/IT1226902B/it active
-
1989
- 1989-07-03 IL IL90844A patent/IL90844A0/xx not_active IP Right Cessation
- 1989-07-03 US US07/375,131 patent/US4962223A/en not_active Expired - Fee Related
- 1989-07-07 AT AT89830316T patent/ATE111439T1/de not_active IP Right Cessation
- 1989-07-07 DE DE68918207T patent/DE68918207T2/de not_active Expired - Fee Related
- 1989-07-07 EP EP89830316A patent/EP0357565B1/fr not_active Expired - Lifetime
- 1989-07-07 ES ES89830316T patent/ES2063837T3/es not_active Expired - Lifetime
- 1989-07-11 DK DK342489A patent/DK172106B1/da not_active IP Right Cessation
- 1989-07-11 NO NO892861A patent/NO174293C/no not_active IP Right Cessation
- 1989-07-11 NZ NZ229910A patent/NZ229910A/en unknown
- 1989-07-11 AR AR89314355A patent/AR248267A1/es active
- 1989-07-11 FI FI893368A patent/FI101534B1/fi not_active IP Right Cessation
- 1989-07-11 ZA ZA895255A patent/ZA895255B/xx unknown
- 1989-07-11 PL PL89280528A patent/PL160103B1/pl unknown
- 1989-07-11 DD DD89330685A patent/DD284674A5/de not_active IP Right Cessation
- 1989-07-11 HU HU893486A patent/HU203318B/hu not_active IP Right Cessation
- 1989-07-11 IE IE222789A patent/IE65956B1/en not_active IP Right Cessation
- 1989-07-12 KR KR1019890009905A patent/KR960004185B1/ko not_active Expired - Fee Related
- 1989-07-12 PT PT91144A patent/PT91144B/pt not_active IP Right Cessation
- 1989-07-12 AU AU38057/89A patent/AU615083B2/en not_active Ceased
- 1989-07-12 JP JP1180152A patent/JP2507069B2/ja not_active Expired - Lifetime
- 1989-07-12 CA CA000605420A patent/CA1338672C/fr not_active Expired - Fee Related
- 1989-07-12 YU YU139989A patent/YU47907B/sh unknown
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