JPS59128359A - バルブロイツクアシツドの１′−エトキシカルボニルオキシエチルエステル、その製造方法、およびそのエステルを含有する抗てんかん用薬剤 - Google Patents
バルブロイツクアシツドの１′−エトキシカルボニルオキシエチルエステル、その製造方法、およびそのエステルを含有する抗てんかん用薬剤Info
- Publication number
- JPS59128359A JPS59128359A JP58238999A JP23899983A JPS59128359A JP S59128359 A JPS59128359 A JP S59128359A JP 58238999 A JP58238999 A JP 58238999A JP 23899983 A JP23899983 A JP 23899983A JP S59128359 A JPS59128359 A JP S59128359A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ester
- ethoxycarbonyloxyethyl ester
- vpa
- producing
- 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
- 150000002148 esters Chemical class 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000001961 anticonvulsive agent Substances 0.000 title claims description 8
- 229960003965 antiepileptics Drugs 0.000 title claims description 4
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 title abstract description 31
- 229960000604 valproic acid Drugs 0.000 title abstract 3
- 239000002253 acid Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000006083 1-bromoethyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- -1 ethoxycarbonyloxyethyl ester Chemical class 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
- 230000036470 plasma concentration Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RKRZYVQFKUXDEZ-UHFFFAOYSA-N 1-bromoethyl ethyl carbonate Chemical compound CCOC(=O)OC(C)Br RKRZYVQFKUXDEZ-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 230000003556 anti-epileptic effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- OMOMUFTZPTXCHP-UHFFFAOYSA-N valpromide Chemical compound CCCC(C(N)=O)CCC OMOMUFTZPTXCHP-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 206010015037 epilepsy Diseases 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- CYYNKJKYWYSECY-UHFFFAOYSA-N 2-bromoethyl ethyl carbonate Chemical compound CCOC(=O)OCCBr CYYNKJKYWYSECY-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940016681 dipropylacetamide Drugs 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000008384 membrane barrier Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000011125 single therapy Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 229960001930 valpromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL67623A IL67623A (en) | 1983-01-05 | 1983-01-05 | 1'-ethoxycarbonyloxyethyl ester of valproic acid,its preparation and pharmaceutical compositions containing it |
| IL67623 | 1983-01-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59128359A true JPS59128359A (ja) | 1984-07-24 |
| JPS6229423B2 JPS6229423B2 (enExample) | 1987-06-25 |
Family
ID=11053985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58238999A Granted JPS59128359A (ja) | 1983-01-05 | 1983-12-20 | バルブロイツクアシツドの１′−エトキシカルボニルオキシエチルエステル、その製造方法、およびそのエステルを含有する抗てんかん用薬剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4595695A (enExample) |
| EP (1) | EP0114720B1 (enExample) |
| JP (1) | JPS59128359A (enExample) |
| AT (1) | ATE18197T1 (enExample) |
| AU (1) | AU558445B2 (enExample) |
| CA (1) | CA1284152C (enExample) |
| DE (1) | DE3460035D1 (enExample) |
| IL (1) | IL67623A (enExample) |
| ZA (1) | ZA838666B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6366153A (ja) * | 1986-06-19 | 1988-03-24 | チエシ・ファルマセウチシ・エッセ・ピ・ア | バルプロ酸または（ｅ）―２―バルプロエン酸誘導体、それらの製造法ならびにそれらを含有する抗てんかん剤または抗けいれん剤 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL67623A (en) * | 1983-01-05 | 1984-09-30 | Teva Pharma | 1'-ethoxycarbonyloxyethyl ester of valproic acid,its preparation and pharmaceutical compositions containing it |
| EP1487460A2 (en) | 2002-02-28 | 2004-12-22 | A & D Bioscience, Inc. | Glycuronamides, glycosides and orthoester glycosides of fluoxetine, analogs and uses thereof |
| WO2003079980A2 (en) * | 2002-03-19 | 2003-10-02 | A & D Bioscience, Inc. | Caboxylic acid glycuronides, glycosamides and glycosides of quinolones, penicillins, analogs, and uses thereof |
| US20050255038A1 (en) * | 2002-04-12 | 2005-11-17 | A And D Bioscience, Inc. | Conjugates comprising cancer cell specific ligands, a sugar and diagnostic agents and uses thereof |
| WO2003094842A2 (en) * | 2002-05-07 | 2003-11-20 | A & D Bioscience, Inc. | Conjugates comprising central nervous system active drug |
| US20050215487A1 (en) * | 2002-06-27 | 2005-09-29 | Holick Michael F | Conjugates comprising an nsaid and a sugar and uses thereof |
| NZ540288A (en) | 2002-11-22 | 2009-06-26 | Univ Johns Hopkins | Target for therapy of cognitive impairment |
| US20080234213A1 (en) * | 2005-09-02 | 2008-09-25 | Matthias Wabl | Oncogenic regulatory RNAs for diagnostics and therapeutics |
| US7459280B2 (en) * | 2006-02-27 | 2008-12-02 | Picobella, Llc | Methods for diagnosing and treating kidney cancer |
| US7763650B2 (en) * | 2006-03-15 | 2010-07-27 | Medipharma S.A. | Pharmaceutical compound and method |
| US20080267977A1 (en) * | 2007-04-26 | 2008-10-30 | Friedrich-Alexander University Of Erlangen-Nuremberg | Combined immunological agent and sensitizing agent for the treatment of cancer |
| EP3260118B1 (en) | 2008-10-16 | 2021-03-24 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| US20110212928A1 (en) * | 2010-02-09 | 2011-09-01 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| AU2013257710B2 (en) * | 2012-05-08 | 2016-10-20 | Cellixbio Private Limited | Compositions and methods for the treatment of neurological disorders |
| WO2014078568A1 (en) | 2012-11-14 | 2014-05-22 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| EP2968220B1 (en) | 2013-03-15 | 2021-05-05 | Agenebio, Inc. | Methods and compositions for improving cognitive function |
| WO2014144663A1 (en) | 2013-03-15 | 2014-09-18 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| NZ738682A (en) | 2015-05-22 | 2022-01-28 | Agenebio Inc | Extended release pharmaceutical compositions of levetiracetam |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2442M (fr) * | 1962-10-17 | 1964-04-06 | Henry Eugene | L'acide dipropylacétique et ses dérivés en tant que nouveuax médicaments dépresseurs du systeme nerveux central. |
| US3646201A (en) * | 1969-07-31 | 1972-02-29 | Liggett & Myers Inc | Salicylate carbonate compounds |
| GB1598568A (en) * | 1977-04-19 | 1981-09-23 | Glaxo Lab Ltd | Esters of(6r,7r)-3-carbamoyloxymethyl-7-((z)-2-(fur-2-yl)-2-methoxyiminoacetamido)-ceph-3-em-4-carboxylic acid |
| ATE12224T1 (de) * | 1981-11-17 | 1985-04-15 | Kabivitrum Ab | Verbindungen mit antifibrinolytischer wirksamkeit. |
| US4542158A (en) * | 1981-12-21 | 1985-09-17 | Merck & Co., Inc. | Prodrug esters of diflunisal and related compounds |
| CA1191153A (en) * | 1981-12-21 | 1985-07-30 | Conrad P. Dorn | Forms of diflunisal and related compounds |
| US4426391A (en) * | 1982-09-15 | 1984-01-17 | Merck & Co., Inc. | [(Alkoxycarbonyl)oxy]alkyl esters of methyldopa |
| IL67445A (en) * | 1982-12-09 | 1985-11-29 | Teva Pharma | Ethoxycarbonyloxy ethyl esters of non-steroidal anti-inflammatory carboxylic acids |
| IL67623A (en) * | 1983-01-05 | 1984-09-30 | Teva Pharma | 1'-ethoxycarbonyloxyethyl ester of valproic acid,its preparation and pharmaceutical compositions containing it |
-
1983
- 1983-01-05 IL IL67623A patent/IL67623A/xx unknown
- 1983-11-14 CA CA000441017A patent/CA1284152C/en not_active Expired - Lifetime
- 1983-11-16 AU AU21421/83A patent/AU558445B2/en not_active Ceased
- 1983-11-16 US US06/552,336 patent/US4595695A/en not_active Expired - Fee Related
- 1983-11-21 ZA ZA838666A patent/ZA838666B/xx unknown
- 1983-12-20 JP JP58238999A patent/JPS59128359A/ja active Granted
-
1984
- 1984-01-05 DE DE8484300049T patent/DE3460035D1/de not_active Expired
- 1984-01-05 AT AT84300049T patent/ATE18197T1/de not_active IP Right Cessation
- 1984-01-05 EP EP84300049A patent/EP0114720B1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6366153A (ja) * | 1986-06-19 | 1988-03-24 | チエシ・ファルマセウチシ・エッセ・ピ・ア | バルプロ酸または（ｅ）―２―バルプロエン酸誘導体、それらの製造法ならびにそれらを含有する抗てんかん剤または抗けいれん剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6229423B2 (enExample) | 1987-06-25 |
| ATE18197T1 (de) | 1986-03-15 |
| US4595695A (en) | 1986-06-17 |
| EP0114720A1 (en) | 1984-08-01 |
| DE3460035D1 (en) | 1986-04-03 |
| CA1284152C (en) | 1991-05-14 |
| IL67623A (en) | 1984-09-30 |
| AU558445B2 (en) | 1987-01-29 |
| ZA838666B (en) | 1984-07-25 |
| AU2142183A (en) | 1984-07-12 |
| IL67623A0 (en) | 1983-05-15 |
| EP0114720B1 (en) | 1986-02-26 |
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