IL40457A - Esters and salts of vincaminic and apovincaminic acid their preparation and pharmaceutical compositions containing them - Google Patents
Esters and salts of vincaminic and apovincaminic acid their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL40457A IL40457A IL40457A IL4045772A IL40457A IL 40457 A IL40457 A IL 40457A IL 40457 A IL40457 A IL 40457A IL 4045772 A IL4045772 A IL 4045772A IL 40457 A IL40457 A IL 40457A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- group
- salts
- vincaminic
- general formula
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract 13
- UXMCFEBDJVHVNH-HOJAQTOUSA-N ac1l52id Chemical class C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(O)=O)N5C2=C1 UXMCFEBDJVHVNH-HOJAQTOUSA-N 0.000 title claims abstract 5
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- ZFCQLDAGNBFMJQ-QUCCMNQESA-N apovincaminic acid Chemical class C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(O)=O)N5C2=C1 ZFCQLDAGNBFMJQ-QUCCMNQESA-N 0.000 title claims 4
- 150000002148 esters Chemical class 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 10
- -1 alkaloid esters Chemical class 0.000 claims abstract 9
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 239000002253 acid Substances 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 150000001350 alkyl halides Chemical class 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract 3
- 239000011707 mineral Substances 0.000 claims abstract 3
- 150000007522 mineralic acids Chemical class 0.000 claims abstract 3
- 150000007524 organic acids Chemical class 0.000 claims abstract 3
- 229930013930 alkaloid Natural products 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 238000009835 boiling Methods 0.000 claims 4
- 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 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 229940127557 pharmaceutical product Drugs 0.000 claims 3
- 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 2
- 239000013543 active substance Substances 0.000 claims 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 229950006936 apovincamine Drugs 0.000 claims 2
- 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 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 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 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 229960002726 vincamine Drugs 0.000 claims 2
- DDNCQMVWWZOMLN-RBBKRZOGSA-N (-)-ethyl apovincaminate Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@H]3[C@@]4(CC)C=C(C(=O)OCC)N5C2=C1 DDNCQMVWWZOMLN-RBBKRZOGSA-N 0.000 claims 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 claims 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- XRMLLVHAALNSGZ-HJNYFJLDSA-N ethylvincaminate Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@@](C(=O)OCC)(O)N5C2=C1 XRMLLVHAALNSGZ-HJNYFJLDSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 claims 1
- 229960003147 reserpine Drugs 0.000 claims 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI454A HU163434B (enrdf_load_stackoverflow) | 1971-11-03 | 1971-11-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40457A0 IL40457A0 (en) | 1972-11-28 |
| IL40457A true IL40457A (en) | 1976-11-30 |
Family
ID=11000880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40457A IL40457A (en) | 1971-11-03 | 1972-09-28 | Esters and salts of vincaminic and apovincaminic acid their preparation and pharmaceutical compositions containing them |
Country Status (28)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2259612B1 (enrdf_load_stackoverflow) * | 1974-01-31 | 1977-09-09 | Synthelabo | |
| HU171662B (hu) * | 1975-07-18 | 1978-02-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh, opticheski aktivnykh proizvodnykh apovinkaminola i ikh kislotnykh adduktov |
| US4122179A (en) * | 1976-06-03 | 1978-10-24 | Enrico Corvi Mora | Acid addition salts of vincamine and apovincamine |
| HU177370B (en) * | 1977-07-27 | 1981-09-28 | Richter Gedeon Vegyeszet | Process for producing new bracket-cross-bracket-vincaminol-esters |
| JPS55100383A (en) * | 1979-01-25 | 1980-07-31 | Sumitomo Chem Co Ltd | Preparation of novel nitrogen-containing polycyclic compound |
| AU532001B2 (en) * | 1978-11-20 | 1983-09-15 | Sumitomo Chemical Company, Limited | Polycyclic indole derivatives |
| CH645269A5 (en) * | 1979-08-16 | 1984-09-28 | Richter Gedeon Vegyeszet | Medicine for the skin, and process for its production |
| JPS56161388A (en) | 1980-05-16 | 1981-12-11 | Nippon Zoki Pharmaceut Co Ltd | Novel vincamine derivative |
| IT1148733B (it) * | 1980-11-14 | 1986-12-03 | Medea Res Srl | Derivati della vincamina,metodo per la sua preparazione e composizione farmaceutiche che lo contengono |
| HU192013B (en) * | 1984-04-25 | 1987-04-28 | Richter Gedeon Vegyeszet | Process for production of new aporincavinol esther derivatives |
| HU191938B (en) * | 1984-07-11 | 1987-04-28 | Andras Vedres | Process for production of new derivatives of 9 and 11 nitro-apovincamin acid |
| ES8604956A1 (es) * | 1985-11-20 | 1986-03-16 | Covex Sa | Procedimiento de obtencion del ester etilico del acido apo- vincaminico |
-
0
- BE BE790837D patent/BE790837A/xx not_active IP Right Cessation
-
1971
- 1971-11-03 HU HURI454A patent/HU163434B/hu unknown
-
1972
- 1972-09-25 AT AT821872A patent/AT322118B/de not_active IP Right Cessation
- 1972-09-27 ZA ZA726619A patent/ZA726619B/xx unknown
- 1972-09-28 AU AU47179/72A patent/AU469544B2/en not_active Expired
- 1972-09-28 IL IL40457A patent/IL40457A/en unknown
- 1972-09-28 GB GB4489272A patent/GB1405127A/en not_active Expired
- 1972-09-28 NO NO3470/72A patent/NO136714C/no unknown
- 1972-10-02 DD DD165983A patent/DD101895A5/xx unknown
- 1972-10-17 FR FR7236735A patent/FR2158229B1/fr not_active Expired
- 1972-10-18 PL PL1972173980A patent/PL84613B1/pl unknown
- 1972-10-18 PL PL1972158330A patent/PL83604B1/pl unknown
- 1972-10-20 RO RO7272589A patent/RO62453A/ro unknown
- 1972-10-20 RO RO7200080703A patent/RO63055A/ro unknown
- 1972-10-20 CH CH1537172A patent/CH580628A5/xx not_active IP Right Cessation
- 1972-10-21 EG EG439/72A patent/EG10707A/xx active
- 1972-10-23 FI FI2929/72A patent/FI56687C/fi active
- 1972-10-27 IN IN1758/72A patent/IN138719B/en unknown
- 1972-10-27 SE SE7213934A patent/SE402460B/xx unknown
- 1972-10-30 JP JP47108028A patent/JPS5132640B2/ja not_active Expired
- 1972-10-30 NL NLAANVRAGE7214672,A patent/NL171584C/xx not_active IP Right Cessation
- 1972-11-01 BG BG021764A patent/BG20602A3/xx unknown
- 1972-11-01 BG BG023710A patent/BG22830A3/xx unknown
- 1972-11-01 DK DK540472AA patent/DK140552B/da not_active IP Right Cessation
- 1972-11-01 BG BG023711A patent/BG25515A3/xx unknown
- 1972-11-02 DE DE2265138A patent/DE2265138C3/de not_active Expired
- 1972-11-02 DE DE2253750A patent/DE2253750C3/de not_active Expired
- 1972-11-02 SU SU7201845297A patent/SU578005A3/ru active
- 1972-11-02 ES ES408180A patent/ES408180A1/es not_active Expired
- 1972-11-02 DE DE2265169A patent/DE2265169C3/de not_active Expired
- 1972-11-02 CA CA155,420A patent/CA991187A/en not_active Expired
- 1972-11-03 YU YU2735/72A patent/YU36738B/xx unknown
- 1972-11-03 CS CS727419A patent/CS191208B2/cs unknown
-
1979
- 1979-01-04 KE KE2912A patent/KE2912A/xx unknown
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