JPS602295B2 - ２−プロピル吉草酸ピバロイルオキシメチル、その製法および抗てんかん剤または鎮痙剤 - Google Patents
２−プロピル吉草酸ピバロイルオキシメチル、その製法および抗てんかん剤または鎮痙剤Info
- Publication number
- JPS602295B2 JPS602295B2 JP55075747A JP7574780A JPS602295B2 JP S602295 B2 JPS602295 B2 JP S602295B2 JP 55075747 A JP55075747 A JP 55075747A JP 7574780 A JP7574780 A JP 7574780A JP S602295 B2 JPS602295 B2 JP S602295B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- propylvalerate
- pev
- pivaloyloxymethyl
- acid
- 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
Links
- 239000001961 anticonvulsive agent Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- DJEFRLDEQKSNLM-UHFFFAOYSA-N valproate pivoxil Chemical compound CCCC(CCC)C(=O)OCOC(=O)C(C)(C)C DJEFRLDEQKSNLM-UHFFFAOYSA-N 0.000 title claims 4
- 230000003556 anti-epileptic effect Effects 0.000 title claims 2
- 229940124575 antispasmodic agent Drugs 0.000 title 1
- 239000000812 cholinergic antagonist Substances 0.000 title 1
- NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical group 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 23
- 229960000604 valproic acid Drugs 0.000 description 23
- 238000012360 testing method Methods 0.000 description 16
- 239000008280 blood Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 8
- 229940084026 sodium valproate Drugs 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010034759 Petit mal epilepsy Diseases 0.000 description 1
- 208000037012 Psychomotor seizures Diseases 0.000 description 1
- 241000700157 Rattus norvegicus Species 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
- 208000007536 Thrombosis Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009534 blood test Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 230000001037 epileptic effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000008288 physiological mechanism Effects 0.000 description 1
- -1 pivaloyloxymethyl Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23392A/79 | 1979-06-08 | ||
| IT23392/79A IT1121282B (it) | 1979-06-08 | 1979-06-08 | Composto ad attivita'antiepilettica e anticonvulsivante,processo per la sua preparazione e composizioni farmaceutiche relative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5655344A JPS5655344A (en) | 1981-05-15 |
| JPS602295B2 true JPS602295B2 (ja) | 1985-01-21 |
Family
ID=11206673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55075747A Expired JPS602295B2 (ja) | 1979-06-08 | 1980-06-04 | ２−プロピル吉草酸ピバロイルオキシメチル、その製法および抗てんかん剤または鎮痙剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4442124A (index.php) |
| JP (1) | JPS602295B2 (index.php) |
| BE (1) | BE883631A (index.php) |
| CA (1) | CA1140580A (index.php) |
| DE (1) | DE3021169C2 (index.php) |
| FR (1) | FR2458534A1 (index.php) |
| GB (1) | GB2052500B (index.php) |
| IT (1) | IT1121282B (index.php) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL72381A (en) * | 1983-07-20 | 1988-03-31 | Sanofi Sa | Pharmaceutical composition based on valproic acid |
| US5185159A (en) * | 1983-07-20 | 1993-02-09 | Sanofi | Pharmaceutical composition based on valproic acid and a process for preparing it |
| IT1190133B (it) * | 1986-06-19 | 1988-02-10 | Chiesi Farma Spa | Derivati di acido valproico e di acido (e)-2-valproenoico,procedimento per la loro preparazione e relative composizioni farmaceutiche |
| US6110955A (en) * | 1997-03-11 | 2000-08-29 | Beacon Laboratories, Inc. | Metabolically stabilized oxyalkylene esters and uses thereof |
| US5939455A (en) * | 1997-03-11 | 1999-08-17 | Beacon Laboratories, Inc. | Therapeutic augmentation of oxyalkylene diesters and butyric acid derivatives |
| EP1928807A4 (en) * | 2005-09-02 | 2011-05-04 | Picobella Llc | ONCOGENIC REGULATORS RNA FOR DIAGNOSIS AND THERAPY |
| US7459280B2 (en) * | 2006-02-27 | 2008-12-02 | Picobella, Llc | Methods for diagnosing and treating kidney cancer |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3148207A (en) * | 1957-12-09 | 1964-09-08 | Monsanto Co | Process for preparing alkyl esters |
| US3076839A (en) * | 1958-09-15 | 1963-02-05 | Glidden Co | Process for producing allylic esters |
| 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. |
| US3993684A (en) * | 1971-08-20 | 1976-11-23 | Western Litho Plate & Supply Co. | Monomeric compounds |
-
1979
- 1979-06-08 IT IT23392/79A patent/IT1121282B/it active
-
1980
- 1980-06-02 US US06/155,588 patent/US4442124A/en not_active Expired - Lifetime
- 1980-06-04 BE BE0/200882A patent/BE883631A/fr not_active IP Right Cessation
- 1980-06-04 CA CA000353336A patent/CA1140580A/en not_active Expired
- 1980-06-04 GB GB8018350A patent/GB2052500B/en not_active Expired
- 1980-06-04 DE DE3021169A patent/DE3021169C2/de not_active Expired
- 1980-06-04 FR FR8012425A patent/FR2458534A1/fr active Granted
- 1980-06-04 JP JP55075747A patent/JPS602295B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2458534A1 (fr) | 1981-01-02 |
| IT7923392A0 (it) | 1979-06-08 |
| IT1121282B (it) | 1986-04-02 |
| DE3021169A1 (de) | 1980-12-11 |
| FR2458534B1 (index.php) | 1983-02-11 |
| US4442124A (en) | 1984-04-10 |
| GB2052500A (en) | 1981-01-28 |
| JPS5655344A (en) | 1981-05-15 |
| GB2052500B (en) | 1983-04-27 |
| BE883631A (fr) | 1980-10-01 |
| CA1140580A (en) | 1983-02-01 |
| DE3021169C2 (de) | 1983-07-07 |
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