DK142545B - Analogifremgangsmåde til fremstilling af derivater af vincamin eller apovincamin med glucose-1-phosphat eller 2,4-dihydroxybenzoesyre. - Google Patents
Analogifremgangsmåde til fremstilling af derivater af vincamin eller apovincamin med glucose-1-phosphat eller 2,4-dihydroxybenzoesyre. Download PDFInfo
- Publication number
- DK142545B DK142545B DK244377AA DK244377A DK142545B DK 142545 B DK142545 B DK 142545B DK 244377A A DK244377A A DK 244377AA DK 244377 A DK244377 A DK 244377A DK 142545 B DK142545 B DK 142545B
- Authority
- DK
- Denmark
- Prior art keywords
- vincamine
- apovincamine
- glucose
- phosphate
- derivatives
- Prior art date
Links
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical class 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 75
- OZDNDGXASTWERN-CTNGQTDRSA-N Apovincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-CTNGQTDRSA-N 0.000 title description 35
- 229950006936 apovincamine Drugs 0.000 title description 34
- OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 title description 34
- 229950010772 glucose-1-phosphate Drugs 0.000 title description 20
- HXXFSFRBOHSIMQ-VFUOTHLCSA-N alpha-D-glucose 1-phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O HXXFSFRBOHSIMQ-VFUOTHLCSA-N 0.000 title description 19
- 238000000034 method Methods 0.000 title description 15
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 title description 10
- 229940114055 beta-resorcylic acid Drugs 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 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 description 35
- 229960002726 vincamine Drugs 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000002490 cerebral effect Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 230000002035 prolonged effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- UIAFKZKHHVMJGS-UHFFFAOYSA-M 2-carboxy-5-hydroxyphenolate Chemical compound OC1=CC=C(C([O-])=O)C(O)=C1 UIAFKZKHHVMJGS-UHFFFAOYSA-M 0.000 description 4
- 230000017531 blood circulation Effects 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 150000004685 tetrahydrates Chemical class 0.000 description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- INXMOHFFQYLBED-CXWKFSMRSA-L disodium;[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate;tetrahydrate Chemical compound O.O.O.O.[Na+].[Na+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@@H]1O INXMOHFFQYLBED-CXWKFSMRSA-L 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 230000010415 tropism Effects 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- YGKAKNJJNTVSKB-YAFGAGFVSA-N vincamine hydrochloride Chemical compound Cl.C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 YGKAKNJJNTVSKB-YAFGAGFVSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
- YAVWDJDEOLOYQO-UHFFFAOYSA-N OOOOOOOOOO Chemical compound OOOOOOOOOO YAVWDJDEOLOYQO-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- WKACQPMBGWZDMR-UHFFFAOYSA-N Vincamin Natural products CC=C1/CN2CCC34CC2C1C(=C3Nc5ccccc45)C=O WKACQPMBGWZDMR-UHFFFAOYSA-N 0.000 description 1
- HXXFSFRBOHSIMQ-UHFFFAOYSA-N [3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate Chemical compound OCC1OC(OP(O)(O)=O)C(O)C(O)C1O HXXFSFRBOHSIMQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000001627 cerebral artery Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002123 temporal 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
- 210000002385 vertebral artery Anatomy 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH703976 | 1976-06-03 | ||
| CH703976A CH625240A5 (en) | 1976-06-03 | 1976-06-03 | Process for preparing novel derivatives of vincamine and apovincamine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK244377A DK244377A (cs) | 1977-12-04 |
| DK142545B true DK142545B (da) | 1980-11-17 |
| DK142545C DK142545C (cs) | 1981-03-30 |
Family
ID=4318961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK244377AA DK142545B (da) | 1976-06-03 | 1977-06-02 | Analogifremgangsmåde til fremstilling af derivater af vincamin eller apovincamin med glucose-1-phosphat eller 2,4-dihydroxybenzoesyre. |
Country Status (11)
| Country | Link |
|---|---|
| AR (1) | AR212821A1 (cs) |
| AT (1) | AT357694B (cs) |
| BE (1) | BE855298A (cs) |
| CH (1) | CH625240A5 (cs) |
| DK (1) | DK142545B (cs) |
| EG (1) | EG12998A (cs) |
| FI (1) | FI771764A7 (cs) |
| IT (1) | IT1074512B (cs) |
| OA (1) | OA05676A (cs) |
| SE (1) | SE7706384L (cs) |
| ZA (1) | ZA773346B (cs) |
-
1976
- 1976-06-03 CH CH703976A patent/CH625240A5/it not_active IP Right Cessation
-
1977
- 1977-06-01 BE BE178117A patent/BE855298A/fr unknown
- 1977-06-01 EG EG339/77A patent/EG12998A/xx active
- 1977-06-01 SE SE7706384A patent/SE7706384L/xx not_active Application Discontinuation
- 1977-06-02 FI FI771764A patent/FI771764A7/fi not_active Application Discontinuation
- 1977-06-02 DK DK244377AA patent/DK142545B/da unknown
- 1977-06-03 ZA ZA00773346A patent/ZA773346B/xx unknown
- 1977-06-03 OA OA56185A patent/OA05676A/xx unknown
- 1977-06-03 AT AT394177A patent/AT357694B/de not_active IP Right Cessation
- 1977-06-03 IT IT24386/77A patent/IT1074512B/it active
- 1977-06-03 AR AR267932A patent/AR212821A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1074512B (it) | 1985-04-20 |
| ATA394177A (de) | 1979-12-15 |
| DK244377A (cs) | 1977-12-04 |
| EG12998A (en) | 1980-07-31 |
| DK142545C (cs) | 1981-03-30 |
| BE855298A (fr) | 1977-10-03 |
| CH625240A5 (en) | 1981-09-15 |
| SE7706384L (sv) | 1977-12-04 |
| ZA773346B (en) | 1978-04-26 |
| FI771764A7 (cs) | 1977-12-04 |
| AT357694B (de) | 1980-07-25 |
| OA05676A (fr) | 1981-05-31 |
| AR212821A1 (es) | 1978-10-13 |
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