DK142364B - Analogifremgangsmåde til fremstilling af vincamin-pyridoxal-5-phosphat. - Google Patents
Analogifremgangsmåde til fremstilling af vincamin-pyridoxal-5-phosphat. Download PDFInfo
- Publication number
- DK142364B DK142364B DK204877AA DK204877A DK142364B DK 142364 B DK142364 B DK 142364B DK 204877A A DK204877A A DK 204877AA DK 204877 A DK204877 A DK 204877A DK 142364 B DK142364 B DK 142364B
- Authority
- DK
- Denmark
- Prior art keywords
- vincamine
- pyridoxal
- phosphate
- analogous process
- preparing
- Prior art date
Links
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 title description 39
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 title description 19
- 229960002726 vincamine Drugs 0.000 title description 19
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 title description 6
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 title description 6
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 title description 6
- 229960001327 pyridoxal phosphate Drugs 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 206010048962 Brain oedema Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CEEQUQSGVRRXQI-UHFFFAOYSA-N Pyridoxal 5-phosphate monohydrate Chemical compound O.CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O CEEQUQSGVRRXQI-UHFFFAOYSA-N 0.000 description 1
- 102000002852 Vasopressins Human genes 0.000 description 1
- 108010004977 Vasopressins Proteins 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000006752 brain edema Diseases 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940072644 pitressin Drugs 0.000 description 1
- 229960003581 pyridoxal Drugs 0.000 description 1
- 235000008164 pyridoxal Nutrition 0.000 description 1
- 239000011674 pyridoxal Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19290/76A GB1525885A (en) | 1976-05-11 | 1976-05-11 | Vincamine salt of pyridoxal phosphate |
| GB1929076 | 1976-05-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK204877A DK204877A (pm) | 1977-11-12 |
| DK142364B true DK142364B (da) | 1980-10-20 |
| DK142364C DK142364C (pm) | 1981-03-02 |
Family
ID=10126939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK204877AA DK142364B (da) | 1976-05-11 | 1977-05-10 | Analogifremgangsmåde til fremstilling af vincamin-pyridoxal-5-phosphat. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4137316A (pm) |
| JP (1) | JPS5312413A (pm) |
| AR (1) | AR210802A1 (pm) |
| AT (1) | AT352913B (pm) |
| AU (1) | AU504254B2 (pm) |
| BE (1) | BE854437A (pm) |
| CA (1) | CA1064496A (pm) |
| CH (1) | CH602629A5 (pm) |
| DE (1) | DE2721171C3 (pm) |
| DK (1) | DK142364B (pm) |
| EG (1) | EG12663A (pm) |
| ES (1) | ES458643A1 (pm) |
| FR (2) | FR2351117A1 (pm) |
| GB (1) | GB1525885A (pm) |
| HK (1) | HK58979A (pm) |
| IN (1) | IN145671B (pm) |
| MY (1) | MY8000068A (pm) |
| NL (1) | NL170096C (pm) |
| NZ (1) | NZ183912A (pm) |
| OA (1) | OA06089A (pm) |
| PT (1) | PT66495B (pm) |
| ZA (1) | ZA772489B (pm) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56117080A (en) * | 1980-02-16 | 1981-09-14 | Kobe Steel Ltd | Method of measuring location of surface layer of charge in vertical eurnace |
| DE3113132A1 (de) * | 1981-04-01 | 1982-10-21 | Heinrich Mack Nachf., 7918 Illertissen | Vincamin-cyclamat, verfahren zu seiner herstellung und dieses enthaltende arzneimittel |
| US4931002A (en) * | 1987-05-29 | 1990-06-05 | The University Of Vermont | Pyridoxal-5'-phosphate as an in vitro anticoagulant for whole blood |
| JPH0624581U (ja) * | 1992-07-13 | 1994-04-05 | 山水工業有限会社 | 衣服掛け |
| US6043259A (en) * | 1998-07-09 | 2000-03-28 | Medicure Inc. | Treatment of cardiovascular and related pathologies |
| WO2000053606A1 (en) | 1999-03-08 | 2000-09-14 | Medicure Inc. | Pyridoxal analogues for vitamin b-6 disorders |
| US6489345B1 (en) | 1999-07-13 | 2002-12-03 | Medicure, Inc. | Treatment of diabetes and related pathologies |
| EP1210117A2 (en) * | 1999-08-24 | 2002-06-05 | Medicure International Inc. | Compositons for the treatment of cardiovascular diseases containing pyridoxal compounds and cardiovascular compounds |
| US7442689B2 (en) * | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| ES2305994T3 (es) | 2000-02-29 | 2008-11-01 | Medicure International Inc. | Fosfonatos cardioprotectores. |
| CA2404329A1 (en) | 2000-03-28 | 2001-10-04 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| EP1299358B1 (en) | 2000-07-07 | 2007-06-13 | Medicure International Inc. | Pyridoxine and pyridoxal analogues as cardiovascular therapeutics |
| US6897228B2 (en) * | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US20040121988A1 (en) * | 2001-03-28 | 2004-06-24 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US20040186077A1 (en) * | 2003-03-17 | 2004-09-23 | Medicure International Inc. | Novel heteroaryl phosphonates as cardioprotective agents |
| US20060019929A1 (en) * | 2004-07-07 | 2006-01-26 | Albert Friesen | Combination therapies employing platelet aggregation drugs |
| US20070060549A1 (en) * | 2004-08-10 | 2007-03-15 | Friesen Albert D | Combination therapies employing ace inhibitors and uses thereof for the treatment of diabetic disorders |
| US7459468B2 (en) * | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| US20060094749A1 (en) * | 2004-10-28 | 2006-05-04 | Medicure International Inc. | Substituted pyridoxines as anti-platelet agents |
| AU2005304220A1 (en) * | 2004-10-28 | 2006-05-18 | Medicure International Inc. | Dual antiplatelet/anticoagulant pyridoxine analogs |
| AU2006317440A1 (en) * | 2005-11-28 | 2007-05-31 | Medicure International Inc. | Selected dosage for the treatment of cardiovascular and related pathologies |
| CA2590605A1 (en) * | 2007-05-28 | 2008-11-28 | Medicure International Inc. | Improvement of mood, memory and cognitive function with pyridoxal 5'-phosphate |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2828315A (en) * | 1957-01-16 | 1958-03-25 | Merck & Co Inc | Procaine salt of pyridoxal phosphate and process |
| FR2176516B1 (pm) * | 1972-03-22 | 1975-03-14 | Synthelabo | |
| FR2191891B1 (pm) * | 1972-07-13 | 1975-08-08 | Roussel Uclaf | |
| CH585226A5 (en) * | 1974-03-08 | 1977-02-28 | Vifor Sa | Slightly soluble vincamine pamoates - with long duration of action as cerebral vasodilators |
| FR2275211A2 (fr) * | 1974-06-19 | 1976-01-16 | Synthelabo | Nouveaux amides de l'acide dihydroapovincaminique, leurs sels, leur preparation et les medicaments qui en contiennent |
| FR2283669A1 (fr) * | 1974-09-06 | 1976-04-02 | Elmu Sa | 2-cetoglutarate de vincamine et son procede de preparation |
-
1976
- 1976-05-11 GB GB19290/76A patent/GB1525885A/en not_active Expired
-
1977
- 1977-04-25 ZA ZA00772489A patent/ZA772489B/xx unknown
- 1977-04-27 IN IN628/CAL/77A patent/IN145671B/en unknown
- 1977-04-29 PT PT66495A patent/PT66495B/pt unknown
- 1977-05-03 CH CH549177A patent/CH602629A5/xx not_active IP Right Cessation
- 1977-05-05 AT AT320277A patent/AT352913B/de not_active IP Right Cessation
- 1977-05-05 NZ NZ183912A patent/NZ183912A/xx unknown
- 1977-05-05 AU AU24894/77A patent/AU504254B2/en not_active Expired
- 1977-05-06 CA CA277,920A patent/CA1064496A/en not_active Expired
- 1977-05-09 OA OA56163A patent/OA06089A/xx unknown
- 1977-05-09 BE BE177422A patent/BE854437A/xx unknown
- 1977-05-09 US US05/794,938 patent/US4137316A/en not_active Expired - Lifetime
- 1977-05-09 EG EG277/77A patent/EG12663A/xx active
- 1977-05-10 NL NLAANVRAGE7705129,A patent/NL170096C/xx not_active IP Right Cessation
- 1977-05-10 DK DK204877AA patent/DK142364B/da not_active IP Right Cessation
- 1977-05-10 ES ES458643A patent/ES458643A1/es not_active Expired
- 1977-05-10 JP JP5270177A patent/JPS5312413A/ja active Granted
- 1977-05-11 FR FR7714334A patent/FR2351117A1/fr active Granted
- 1977-05-11 AR AR267580A patent/AR210802A1/es active
- 1977-05-11 FR FR7714333A patent/FR2350842A1/fr active Granted
- 1977-05-11 DE DE2721171A patent/DE2721171C3/de not_active Expired
-
1979
- 1979-08-23 HK HK589/79A patent/HK58979A/xx unknown
-
1980
- 1980-12-31 MY MY198068A patent/MY8000068A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES458643A1 (es) | 1978-03-16 |
| JPS5312413A (en) | 1978-02-03 |
| GB1525885A (en) | 1978-09-20 |
| PT66495A (en) | 1977-05-01 |
| AT352913B (de) | 1979-10-10 |
| PT66495B (en) | 1978-09-29 |
| DK204877A (pm) | 1977-11-12 |
| NL7705129A (nl) | 1977-11-15 |
| US4137316A (en) | 1979-01-30 |
| JPS5618598B2 (pm) | 1981-04-30 |
| FR2351117A1 (fr) | 1977-12-09 |
| OA06089A (fr) | 1981-06-30 |
| NL170096C (nl) | 1982-10-01 |
| NL170096B (nl) | 1982-05-03 |
| FR2350842A1 (fr) | 1977-12-09 |
| CH602629A5 (pm) | 1978-07-31 |
| AR210802A1 (es) | 1977-09-15 |
| HK58979A (en) | 1979-08-31 |
| NZ183912A (en) | 1978-09-25 |
| IN145671B (pm) | 1985-01-05 |
| BE854437A (fr) | 1977-09-01 |
| DE2721171B2 (de) | 1979-10-31 |
| CA1064496A (en) | 1979-10-16 |
| DE2721171C3 (de) | 1980-07-10 |
| DE2721171A1 (de) | 1977-11-24 |
| FR2351117B1 (pm) | 1980-06-27 |
| FR2350842B1 (pm) | 1980-05-09 |
| AU2489477A (en) | 1978-11-09 |
| MY8000068A (en) | 1980-12-31 |
| EG12663A (en) | 1979-12-31 |
| ATA320277A (de) | 1979-03-15 |
| ZA772489B (en) | 1978-05-30 |
| DK142364C (pm) | 1981-03-02 |
| AU504254B2 (en) | 1979-10-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |