NO136198B - - Google Patents
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- Publication number
- NO136198B NO136198B NO3716/72A NO371672A NO136198B NO 136198 B NO136198 B NO 136198B NO 3716/72 A NO3716/72 A NO 3716/72A NO 371672 A NO371672 A NO 371672A NO 136198 B NO136198 B NO 136198B
- Authority
- NO
- Norway
- Prior art keywords
- methoxy
- solution
- eburnane
- carboxy
- apovincamine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 7
- 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 claims description 6
- 229950006936 apovincamine Drugs 0.000 claims description 6
- OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 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 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000002490 cerebral effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229960002726 vincamine Drugs 0.000 description 4
- 229930013930 alkaloid Natural products 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- VLFDXKBCNKXRBE-YTQUADARSA-N (+)-Isoeburnamine Natural products O[C@@H]1n2c3c(c4c2[C@H]2[C@@](CC)(C1)CCC[N+]2CC4)cccc3 VLFDXKBCNKXRBE-YTQUADARSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- HONLKDDLTAZVQV-NZSAHSFTSA-N Eburnamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@H]3[C@@]4(CC)C[C@@H](O)N5C2=C1 HONLKDDLTAZVQV-NZSAHSFTSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- -1 alkali metal methoxide Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- HONLKDDLTAZVQV-UHFFFAOYSA-N eburnamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)N5C2=C1 HONLKDDLTAZVQV-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000000304 vasodilatating 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO761366A NO761366L (enrdf_load_stackoverflow) | 1971-11-03 | 1976-04-22 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI455A HU166474B (enrdf_load_stackoverflow) | 1971-11-03 | 1971-11-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136198B true NO136198B (enrdf_load_stackoverflow) | 1977-04-25 |
| NO136198C NO136198C (no) | 1977-08-03 |
Family
ID=11000881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3716/72A NO136198C (no) | 1971-11-03 | 1972-10-17 | Analogifremgangsm}te ved fremstilling av terapeutisk aktivt 16-carboxy-17-methoxy-eburnan. |
Country Status (23)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU532001B2 (en) * | 1978-11-20 | 1983-09-15 | Sumitomo Chemical Company, Limited | Polycyclic indole derivatives |
| US4316028A (en) * | 1978-11-20 | 1982-02-16 | Sumitomo Chemical Company, Limited | Process for producing eburnane derivatives |
| HU187139B (en) * | 1982-06-30 | 1985-11-28 | Richter Gedeon Vegyeszet | Process for preparing new eburnan derivatives |
| EP3495361B1 (en) * | 2016-08-04 | 2020-10-28 | Harbin Pharmaceutical Group Co., Ltd. General Pharmaceutical Factory | Salt and crystal of diaza-benzofluorane compound |
-
1971
- 1971-11-03 HU HURI455A patent/HU166474B/hu unknown
-
1972
- 1972-10-16 CH CH1320575A patent/CH577504A5/xx not_active IP Right Cessation
- 1972-10-16 CH CH1510372A patent/CH586702A5/xx not_active IP Right Cessation
- 1972-10-16 CA CA153,943A patent/CA982585A/en not_active Expired
- 1972-10-17 ZA ZA727382A patent/ZA727382B/xx unknown
- 1972-10-17 NO NO3716/72A patent/NO136198C/no unknown
- 1972-10-19 BG BG021668A patent/BG20601A3/xx unknown
- 1972-10-19 IL IL40623A patent/IL40623A/xx unknown
- 1972-10-19 BG BG023693A patent/BG20379A3/xx unknown
- 1972-10-20 AU AU47984/72A patent/AU470084B2/en not_active Expired
- 1972-10-21 EG EG440/72A patent/EG10720A/xx active
- 1972-10-25 AT AT910372A patent/AT318823B/de not_active IP Right Cessation
- 1972-10-25 AT AT978773*7A patent/AT328624B/de not_active IP Right Cessation
- 1972-10-31 BE BE790842D patent/BE790842A/xx unknown
- 1972-10-31 DD DD166591A patent/DD101405A5/xx unknown
- 1972-10-31 FR FR7238529A patent/FR2158371B1/fr not_active Expired
- 1972-11-01 NL NL7214768A patent/NL7214768A/xx unknown
- 1972-11-01 JP JP47108965A patent/JPS515400B2/ja not_active Expired
- 1972-11-02 DE DE2253778A patent/DE2253778A1/de active Pending
- 1972-11-02 PL PL1972158592A patent/PL71069B1/pl unknown
- 1972-11-02 ES ES408184A patent/ES408184A1/es not_active Expired
- 1972-11-02 AR AR244942A patent/AR196498A1/es active
- 1972-11-02 SU SU1843735A patent/SU438183A3/ru active
- 1972-11-02 GB GB810074A patent/GB1402085A/en not_active Expired
- 1972-11-03 RO RO7200080514A patent/RO63053A/ro unknown
- 1972-11-03 RO RO72721A patent/RO62345A/ro unknown
-
1975
- 1975-07-25 SE SE7508516A patent/SE7508516L/xx not_active Application Discontinuation
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