CH561183A5 - - Google Patents
Info
- Publication number
- CH561183A5 CH561183A5 CH30674A CH30674A CH561183A5 CH 561183 A5 CH561183 A5 CH 561183A5 CH 30674 A CH30674 A CH 30674A CH 30674 A CH30674 A CH 30674A CH 561183 A5 CH561183 A5 CH 561183A5
- Authority
- CH
- Switzerland
- Prior art keywords
- product
- alpha
- pyridoxal
- ketoglutarate
- ethanol
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 12
- 241000699670 Mus sp. Species 0.000 claims description 12
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims description 12
- MUXYIGOUJRUBPG-UHFFFAOYSA-N 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde;2-oxopentanedioic acid Chemical compound OC(=O)CCC(=O)C(O)=O.CC1=NC=C(CO)C(C=O)=C1O MUXYIGOUJRUBPG-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 claims description 6
- 229940009533 alpha-ketoglutaric acid Drugs 0.000 claims description 6
- 229960003581 pyridoxal Drugs 0.000 claims description 6
- 235000008164 pyridoxal Nutrition 0.000 claims description 6
- 239000011674 pyridoxal Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 206010010071 Coma Diseases 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 4
- 230000001773 anti-convulsant effect Effects 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 229960003965 antiepileptics Drugs 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 230000001934 delay Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 208000007848 Alcoholism Diseases 0.000 claims description 2
- 206010002091 Anaesthesia Diseases 0.000 claims description 2
- 206010052770 Coma states Diseases 0.000 claims description 2
- 206010012373 Depressed level of consciousness Diseases 0.000 claims description 2
- 241000282326 Felis catus Species 0.000 claims description 2
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 241000699666 Mus <mouse, genus> Species 0.000 claims description 2
- 206010029333 Neurosis Diseases 0.000 claims description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 claims description 2
- 208000029808 Psychomotor disease Diseases 0.000 claims description 2
- 241000700159 Rattus Species 0.000 claims description 2
- 208000010513 Stupor Diseases 0.000 claims description 2
- 206010047700 Vomiting Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 230000004075 alteration Effects 0.000 claims description 2
- 230000037005 anaesthesia Effects 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 230000036772 blood pressure Effects 0.000 claims description 2
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000007705 chemical test Methods 0.000 claims description 2
- 230000007665 chronic toxicity Effects 0.000 claims description 2
- 231100000160 chronic toxicity Toxicity 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000002920 convulsive effect Effects 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
- 208000002173 dizziness Diseases 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 230000035876 healing Effects 0.000 claims description 2
- 208000006454 hepatitis Diseases 0.000 claims description 2
- 231100000283 hepatitis Toxicity 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 229910001867 inorganic solvent Inorganic materials 0.000 claims description 2
- 239000003049 inorganic solvent Substances 0.000 claims description 2
- 231100000566 intoxication Toxicity 0.000 claims description 2
- 230000035987 intoxication Effects 0.000 claims description 2
- 238000010253 intravenous injection Methods 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 231100000636 lethal dose Toxicity 0.000 claims description 2
- 230000003137 locomotive effect Effects 0.000 claims description 2
- 231100000053 low toxicity Toxicity 0.000 claims description 2
- 230000002503 metabolic effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 208000015238 neurotic disease Diseases 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229960001412 pentobarbital Drugs 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 230000001107 psychogenic effect Effects 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000004904 shortening Methods 0.000 claims description 2
- 238000007619 statistical method Methods 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 231100000331 toxic Toxicity 0.000 claims description 2
- 230000002588 toxic effect Effects 0.000 claims description 2
- 231100000419 toxicity Toxicity 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 claims description 2
- 230000000472 traumatic effect Effects 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/347—Saturated compounds containing more than one carboxyl group containing keto groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE790118D BE790118A (fr) | 1972-10-09 | Derives de l'alpha-cetoglutarate de pyridoxal et de pyridoxamine, | |
| CH30674A CH561183A5 (enrdf_load_stackoverflow) | 1972-10-09 | 1972-10-09 | |
| GB4712172A GB1346014A (en) | 1972-10-09 | 1972-10-12 | Derivatives of alpha-ketoglutaric acid and their preparation |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH30674A CH561183A5 (enrdf_load_stackoverflow) | 1972-10-09 | 1972-10-09 | |
| GB4712172 | 1972-10-12 | ||
| BE790118 | 1972-10-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH561183A5 true CH561183A5 (enrdf_load_stackoverflow) | 1975-04-30 |
Family
ID=27159418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH30674A CH561183A5 (enrdf_load_stackoverflow) | 1972-10-09 | 1972-10-09 |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE790118A (enrdf_load_stackoverflow) |
| CH (1) | CH561183A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1346014A (enrdf_load_stackoverflow) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6043259A (en) * | 1998-07-09 | 2000-03-28 | Medicure Inc. | Treatment of cardiovascular and related pathologies |
| US6339085B1 (en) | 1999-03-08 | 2002-01-15 | The University Of Manitoba | Therapeutics for cardiovascular and related diseases |
| US6417204B1 (en) | 2000-07-07 | 2002-07-09 | Medicure International Inc. | Pyridoxine AMD pyridoxal analogues: cardiovascular therapeutics |
| US6489345B1 (en) | 1999-07-13 | 2002-12-03 | Medicure, Inc. | Treatment of diabetes and related pathologies |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| US6586414B2 (en) | 2000-03-28 | 2003-07-01 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US6605612B2 (en) | 2000-02-29 | 2003-08-12 | Medicure International Inc. | Cardioprotective phosohonates and malonates |
| US6677356B1 (en) | 1999-08-24 | 2004-01-13 | Medicure International Inc. | Treatment of cardiovascular and related pathologies |
| US6897228B2 (en) | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US7442689B2 (en) | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| US7459468B2 (en) | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| US7812037B2 (en) | 2004-10-28 | 2010-10-12 | Medicure International, Inc. | Dual antiplatelet/anticoagulant pyridoxine analogs |
-
0
- BE BE790118D patent/BE790118A/xx unknown
-
1972
- 1972-10-09 CH CH30674A patent/CH561183A5/fr not_active IP Right Cessation
- 1972-10-12 GB GB4712172A patent/GB1346014A/en not_active Expired
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6043259A (en) * | 1998-07-09 | 2000-03-28 | Medicure Inc. | Treatment of cardiovascular and related pathologies |
| US6890943B2 (en) | 1999-03-08 | 2005-05-10 | Medicure Inc. | Pyridoxal analogues and methods of treatment |
| US6339085B1 (en) | 1999-03-08 | 2002-01-15 | The University Of Manitoba | Therapeutics for cardiovascular and related diseases |
| US7230009B2 (en) | 1999-03-08 | 2007-06-12 | Medicure, Inc. | Pyridoxal analogues and methods of treatment |
| US6489345B1 (en) | 1999-07-13 | 2002-12-03 | Medicure, Inc. | Treatment of diabetes and related pathologies |
| US7132430B2 (en) | 1999-08-24 | 2006-11-07 | Medicure International Inc. | Treatment of cardiovascular and related pathologies |
| US7115626B2 (en) | 1999-08-24 | 2006-10-03 | Medicure International Inc. | Treatment of cardiovascular and related pathologies |
| US7148233B2 (en) | 1999-08-24 | 2006-12-12 | Merrill Lynch Capital Canada Inc. | Treatment of cardiovascular and related pathologies |
| US6677356B1 (en) | 1999-08-24 | 2004-01-13 | Medicure International Inc. | Treatment of cardiovascular and related pathologies |
| US7144892B2 (en) | 1999-08-24 | 2006-12-05 | Merrill Lynch Capital Canada Inc. | Treatment of cardiovascular and related pathologies |
| US7125889B2 (en) | 1999-08-24 | 2006-10-24 | Medicure International Inc. | Treating of cardiovascular and related pathologies |
| US7115625B2 (en) | 1999-08-24 | 2006-10-03 | Medicure International Inc. | Treatment of cardiovascular and related pathologies |
| US6867215B2 (en) | 2000-02-29 | 2005-03-15 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| US6780997B2 (en) | 2000-02-29 | 2004-08-24 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| US7105673B2 (en) | 2000-02-29 | 2006-09-12 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| US7442689B2 (en) | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| US6605612B2 (en) | 2000-02-29 | 2003-08-12 | Medicure International Inc. | Cardioprotective phosohonates and malonates |
| US6667315B2 (en) | 2000-02-29 | 2003-12-23 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| US6861439B2 (en) | 2000-03-28 | 2005-03-01 | Medicure International, Inc. | Treatment of cerebrovascular disease |
| US6586414B2 (en) | 2000-03-28 | 2003-07-01 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US6897228B2 (en) | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US6417204B1 (en) | 2000-07-07 | 2002-07-09 | Medicure International Inc. | Pyridoxine AMD pyridoxal analogues: cardiovascular therapeutics |
| US7425570B2 (en) | 2000-07-07 | 2008-09-16 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| US7459468B2 (en) | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| US7812037B2 (en) | 2004-10-28 | 2010-10-12 | Medicure International, Inc. | Dual antiplatelet/anticoagulant pyridoxine analogs |
Also Published As
| Publication number | Publication date |
|---|---|
| BE790118A (fr) | 1973-02-01 |
| GB1346014A (en) | 1974-02-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |