CH625240A5 - Process for preparing novel derivatives of vincamine and apovincamine - Google Patents
Process for preparing novel derivatives of vincamine and apovincamine Download PDFInfo
- Publication number
- CH625240A5 CH625240A5 CH703976A CH703976A CH625240A5 CH 625240 A5 CH625240 A5 CH 625240A5 CH 703976 A CH703976 A CH 703976A CH 703976 A CH703976 A CH 703976A CH 625240 A5 CH625240 A5 CH 625240A5
- Authority
- CH
- Switzerland
- Prior art keywords
- apovincamine
- phosphate
- glucose
- vincamine
- process according
- 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 claims abstract description 102
- 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 claims abstract description 55
- 229950006936 apovincamine Drugs 0.000 title claims abstract description 45
- 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 claims abstract description 45
- 238000004519 manufacturing process Methods 0.000 title 1
- 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 claims abstract description 45
- 229960002726 vincamine Drugs 0.000 claims abstract description 45
- 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 claims abstract description 18
- 229950010772 glucose-1-phosphate Drugs 0.000 claims abstract description 18
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 claims abstract description 11
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 claims abstract description 7
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000725 suspension Substances 0.000 claims abstract description 7
- 229940114055 beta-resorcylic acid Drugs 0.000 claims abstract description 5
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- UIAFKZKHHVMJGS-UHFFFAOYSA-M 2-carboxy-5-hydroxyphenolate Chemical compound OC1=CC=C(C([O-])=O)C(O)=C1 UIAFKZKHHVMJGS-UHFFFAOYSA-M 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 5
- 239000001488 sodium phosphate Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229940124549 vasodilator Drugs 0.000 claims description 5
- 239000003071 vasodilator agent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 210000004556 brain Anatomy 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- -1 salt vincamine glucose-1-phosphate salt Chemical class 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims 4
- 235000019800 disodium phosphate Nutrition 0.000 claims 2
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 150000002303 glucose derivatives Chemical class 0.000 claims 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000004087 circulation Effects 0.000 abstract description 2
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 12
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000003111 delayed effect Effects 0.000 description 7
- 230000000968 intestinal effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000036765 blood level Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000017531 blood circulation Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 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 class 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
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000002485 urinary effect Effects 0.000 description 2
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-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
- 206010002091 Anaesthesia Diseases 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- VFRROHXSMXFLSN-SLPGGIOYSA-N aldehydo-D-glucose 6-phosphate Chemical class OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O VFRROHXSMXFLSN-SLPGGIOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 210000001168 carotid artery common Anatomy 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940071221 dihydroxybenzoate Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 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 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)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH703976A CH625240A5 (en) | 1976-06-03 | 1976-06-03 | Process for preparing novel derivatives of vincamine and apovincamine |
| GB22545/77A GB1549501A (en) | 1976-06-03 | 1977-05-27 | Adducts of vincamine and apovincamine |
| US05/801,209 US4122179A (en) | 1976-06-03 | 1977-05-27 | Acid addition salts of vincamine and apovincamine |
| EG339/77A EG12998A (en) | 1976-06-03 | 1977-06-01 | Process for preparing of novel derivatives of vincamine and apovincamine |
| BE178117A BE855298A (fr) | 1976-06-03 | 1977-06-01 | Nouveaux derives de la vincamine et de l'apovincamine et leur procede de preparation |
| SE7706384A SE7706384L (sv) | 1976-06-03 | 1977-06-01 | Derivat av vinkamin och apovinkamin |
| AU25797/77A AU514744B2 (en) | 1976-06-03 | 1977-06-02 | Derivatives of vincamine and arovincamine |
| NL7706046A NL7706046A (nl) | 1976-06-03 | 1977-06-02 | Werkwijze voor de bereiding van nieuwe vincamine en apovincaminederivaten. |
| CA279,705A CA1085827A (en) | 1976-06-03 | 1977-06-02 | Derivatives of vincamine and apovincamine and related preparation process |
| 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. |
| MX777421U MX4755E (es) | 1976-06-03 | 1977-06-02 | Procedimiento para preparar derivados de vincamina y apovincamina |
| FI771764A FI771764A7 (cs) | 1976-06-03 | 1977-06-02 | |
| ES459423A ES459423A1 (es) | 1976-06-03 | 1977-06-02 | Procedimiento para la obtencion de derivados de la vincaminay de la apovincamina. |
| JP6492477A JPS52151715A (en) | 1976-06-03 | 1977-06-03 | Preparation of vincamine and apovincamine derivative |
| AT394177A AT357694B (de) | 1976-06-03 | 1977-06-03 | Verfahren zur herstellung neuer derivate von vincamin und apovincamin |
| OA56185A OA05676A (fr) | 1976-06-03 | 1977-06-03 | Procédé de préparation de la vincamine et de l'apovincamine et produits industriels nouveaux. |
| FR7717086A FR2353551A1 (fr) | 1976-06-03 | 1977-06-03 | Nouveaux derives de la vincamine et de l'apovincamine, leur procede de preparation et leur utilisation dans le traitement des affections circulatoires, cerebrales et cardiovasculaires |
| ZA00773346A ZA773346B (en) | 1976-06-03 | 1977-06-03 | Novel derivatives of vincamine and apovincamine and related preparation process |
| DE19772725246 DE2725246A1 (de) | 1976-06-03 | 1977-06-03 | Derivate von vincamin und apovincamin und diese enthaltende pharmazeutische praeparate |
| IT24384/77A IT1074400B (it) | 1976-06-03 | 1977-06-03 | Derivati della vincamina e dell'apovincamina e relativo procedimento di preparazione |
| AR267932A AR212821A1 (es) | 1976-06-03 | 1977-06-03 | Procedimiento para la preparacion de aductos de vincamina y apovincamina |
| IT24386/77A IT1074512B (it) | 1976-06-03 | 1977-06-03 | Derivati della vincamina e dell'apovincamina e relativo procedimento di preparazione |
| IE790258A IE790258L (en) | 1976-06-03 | 1979-02-12 | Salts of vincamone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH703976A CH625240A5 (en) | 1976-06-03 | 1976-06-03 | Process for preparing novel derivatives of vincamine and apovincamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH625240A5 true CH625240A5 (en) | 1981-09-15 |
Family
ID=4318961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH703976A CH625240A5 (en) | 1976-06-03 | 1976-06-03 | Process for preparing novel derivatives of vincamine and apovincamine |
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 |
| DK142545B (da) | 1980-11-17 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |