AT403160B - Verfahren zur herstellung von pyridoxin 5-oxo-2-pyrrolidoncarboxylat - Google Patents
Verfahren zur herstellung von pyridoxin 5-oxo-2-pyrrolidoncarboxylat Download PDFInfo
- Publication number
- AT403160B AT403160B AT0900494A AT900494A AT403160B AT 403160 B AT403160 B AT 403160B AT 0900494 A AT0900494 A AT 0900494A AT 900494 A AT900494 A AT 900494A AT 403160 B AT403160 B AT 403160B
- Authority
- AT
- Austria
- Prior art keywords
- oxo
- pyridoxine
- preparation
- pyrrolidone carboxylate
- isopropanol
- Prior art date
Links
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 229940011671 vitamin b6 Drugs 0.000 claims description 7
- 235000008160 pyridoxine Nutrition 0.000 claims description 6
- 239000011677 pyridoxine Substances 0.000 claims description 6
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 4
- UNNBZWSRXVKJAA-UHFFFAOYSA-N O=C1CCC(N1)=O.N1=C(C)C(O)=C(CO)C(CO)=C1 Chemical compound O=C1CCC(N1)=O.N1=C(C)C(O)=C(CO)C(CO)=C1 UNNBZWSRXVKJAA-UHFFFAOYSA-N 0.000 claims description 4
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229940071139 pyrrolidone carboxylate Drugs 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010001605 Alcohol poisoning Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000019631 acid taste sensations Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AIXMJTYHQHQJLU-UHFFFAOYSA-N chembl210858 Chemical compound O1C(CC(=O)OC)CC(C=2C=CC(O)=CC=2)=N1 AIXMJTYHQHQJLU-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000642 iatrogenic effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 208000015706 neuroendocrine disease Diseases 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
- C07D213/67—2-Methyl-3-hydroxy-4,5-bis(hydroxy-methyl)pyridine, i.e. pyridoxine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI930340A IT1263956B (it) | 1993-02-23 | 1993-02-23 | Procedimento per la preparazione di 5-oxo-2-pirrolidoncarbossilato di piridossina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA900494A ATA900494A (de) | 1997-04-15 |
| AT403160B true AT403160B (de) | 1997-11-25 |
Family
ID=11365118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0900494A AT403160B (de) | 1993-02-23 | 1994-02-19 | Verfahren zur herstellung von pyridoxin 5-oxo-2-pyrrolidoncarboxylat |
Country Status (5)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105906559B (zh) * | 2016-06-14 | 2018-08-14 | 成都倍特药业有限公司 | 一种药用级美他多辛的一步合成法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313952A (en) * | 1980-06-30 | 1982-02-02 | Massimo Baldacci | Method of treating acute alcoholic intoxication with pyridoxine P.C.A. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR6990M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-03-13 | 1969-05-27 | ||
| FR2244466A1 (en) * | 1973-06-29 | 1975-04-18 | Dufour Claude | Salts of pyridoxine with aryloxy alkanoic acids - useful as antihyperlipemic agents for oral administration |
| FR2260330A1 (en) * | 1974-02-07 | 1975-09-05 | Innothera Lab Sa | Pyridoxine N-oxy nicotinate - hypolipaemiant and hypocholesterolemiant of good therapeutic index |
| FR2485372B1 (fr) * | 1980-06-30 | 1985-08-09 | Baldacci Lab Spa | Composition pharmaceutique pour le traitement des etats d'intoxication alcoolique aigue a base de 5-oxo-2-pyrrolidone carboxylate de pyridoxine et procede de preparation de ce dernier |
-
1993
- 1993-02-23 IT ITMI930340A patent/IT1263956B/it active IP Right Grant
- 1993-03-31 KR KR1019930005259A patent/KR100257967B1/ko not_active Expired - Fee Related
- 1993-05-21 TW TW082104025A patent/TW235962B/zh not_active IP Right Cessation
-
1994
- 1994-02-19 AT AT0900494A patent/AT403160B/de not_active IP Right Cessation
- 1994-02-19 WO PCT/EP1994/000517 patent/WO1994019324A1/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313952A (en) * | 1980-06-30 | 1982-02-02 | Massimo Baldacci | Method of treating acute alcoholic intoxication with pyridoxine P.C.A. |
Non-Patent Citations (1)
| Title |
|---|
| GARAU ET AL.: METADOXINE, ALCOHOL ALCOHOL, 1992, 27(5) SEITEN 501 - 504 (CHEM. ABSTR. 118: 139258P) * |
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI930340A0 (it) | 1993-02-23 |
| ITMI930340A1 (it) | 1994-08-23 |
| KR940019703A (ko) | 1994-09-14 |
| ATA900494A (de) | 1997-04-15 |
| KR100257967B1 (ko) | 2000-07-01 |
| WO1994019324A1 (en) | 1994-09-01 |
| IT1263956B (it) | 1996-09-05 |
| TW235962B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |