CH655112A5 - Procedimento per la preparazione degli isomeri ottici e delle forme racemiche della vincamina e di alcaloidi indolici correlati. - Google Patents
Procedimento per la preparazione degli isomeri ottici e delle forme racemiche della vincamina e di alcaloidi indolici correlati. Download PDFInfo
- Publication number
- CH655112A5 CH655112A5 CH5000/81A CH500081A CH655112A5 CH 655112 A5 CH655112 A5 CH 655112A5 CH 5000/81 A CH5000/81 A CH 5000/81A CH 500081 A CH500081 A CH 500081A CH 655112 A5 CH655112 A5 CH 655112A5
- Authority
- CH
- Switzerland
- Prior art keywords
- iii
- optical isomers
- process according
- carried out
- cooy
- Prior art date
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- 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 claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 12
- 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 claims abstract description 11
- 230000003287 optical effect Effects 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 7
- WKACQPMBGWZDMR-UHFFFAOYSA-N Vincamin Natural products CC=C1/CN2CCC34CC2C1C(=C3Nc5ccccc45)C=O WKACQPMBGWZDMR-UHFFFAOYSA-N 0.000 title 1
- 229960002726 vincamine Drugs 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 239000002841 Lewis acid Substances 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 5
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 5
- 239000011707 mineral Substances 0.000 claims abstract description 5
- 239000007795 chemical reaction product Substances 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 4
- 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 description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 229930013930 alkaloid Natural products 0.000 claims 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract description 4
- 229930005303 indole alkaloid Natural products 0.000 abstract description 3
- 150000002475 indoles Chemical class 0.000 abstract description 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 abstract description 2
- 229950006936 apovincamine Drugs 0.000 abstract description 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 abstract description 2
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 6
- -1 halogen esters Chemical class 0.000 description 5
- 229960000744 vinpocetine Drugs 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DDNCQMVWWZOMLN-IRLDBZIGSA-N Vinpocetine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OCC)N5C2=C1 DDNCQMVWWZOMLN-IRLDBZIGSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- MPNPJQYCBQXPGW-SRTHRBEQSA-N Burnamine Chemical compound COC(=O)C1(CO)[C@H]2C[C@@H]3N(C\C2=C\C)[C@@H]2C[C@]11c4ccccc4N[C@]31O2 MPNPJQYCBQXPGW-SRTHRBEQSA-N 0.000 description 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- 241001079672 Nascus Species 0.000 description 1
- MPNPJQYCBQXPGW-BASWHVEKSA-N O-deacetylpicraline Natural products COC(=O)C1(CO)C2CC3N(C/C/2=C/C)C4CC15c6ccccc6NC35O4 MPNPJQYCBQXPGW-BASWHVEKSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- YAXGXEOYWAIEER-UHFFFAOYSA-N acetic acid;triethylphosphane Chemical compound CC([O-])=O.CC[PH+](CC)CC YAXGXEOYWAIEER-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- MPNPJQYCBQXPGW-UHFFFAOYSA-N burnamine Natural products C12=CC=CC=C2NC2(O3)C4CC5C(C(=O)OC)(CO)C12CC3N4CC5=CC MPNPJQYCBQXPGW-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000005594 diketone group Chemical group 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
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 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 description 1
- XPYGGHVSFMUHLH-UUSULHAXSA-N falecalcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(O)(C(F)(F)F)C(F)(F)F)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C XPYGGHVSFMUHLH-UUSULHAXSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- HONLKDDLTAZVQV-UHOSZYNNSA-N vincanol Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@H](O)N5C2=C1 HONLKDDLTAZVQV-UHOSZYNNSA-N 0.000 description 1
- 229950002496 vincanol Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23904/80A IT1132307B (it) | 1980-08-04 | 1980-08-04 | Procedimento per la sintesi di vincamina ed alcaloidi indolici correlati |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH655112A5 true CH655112A5 (it) | 1986-03-27 |
Family
ID=11210771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5000/81A CH655112A5 (it) | 1980-08-04 | 1981-08-03 | Procedimento per la preparazione degli isomeri ottici e delle forme racemiche della vincamina e di alcaloidi indolici correlati. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4379935A (en, 2012) |
| EP (1) | EP0045918B1 (en, 2012) |
| JP (1) | JPS5758683A (en, 2012) |
| AT (1) | ATE5142T1 (en, 2012) |
| CH (1) | CH655112A5 (en, 2012) |
| DE (1) | DE3161285D1 (en, 2012) |
| ES (1) | ES505154A0 (en, 2012) |
| IT (1) | IT1132307B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU84664A1 (fr) * | 1983-02-25 | 1984-11-08 | Onmichem S A | Alkyl-4-indolonaphtyridines et leur application therapeutique |
| US20090093513A1 (en) * | 2007-10-09 | 2009-04-09 | Hamann Mark T | Method to Use Compositions Having Antidepressant Anxiolytic and Other Neurological Activity and Compositions of Matter |
| EP2168963A1 (en) * | 2008-09-25 | 2010-03-31 | Linnea S.A. | Process for the preparation of vinpocetine and apovincamine |
| CN103869018A (zh) * | 2014-03-27 | 2014-06-18 | 张家港威胜生物医药有限公司 | 一种高效液相色谱法测定长春胺有关物质的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2121360B1 (en, 2012) * | 1971-01-06 | 1974-03-22 | Roussel Uclaf | |
| HU163143B (en, 2012) * | 1971-05-07 | 1973-06-28 | ||
| GB1429861A (en) * | 1972-03-29 | 1976-03-31 | Sandoz Ltd | Vincamine derivatives |
| CH578001A5 (en, 2012) * | 1972-04-14 | 1976-07-30 | Sandoz Ag | |
| US4033969A (en) * | 1972-06-19 | 1977-07-05 | Agence Nationale De Valorisation De La Recherche (Anvar) | Vincamine derivatives |
| US4146643A (en) * | 1973-12-18 | 1979-03-27 | Sandoz Ltd. | Increasing vigilance or treating cerebral insufficiency with substituted vincamines |
| US4267330A (en) * | 1978-08-24 | 1981-05-12 | Omnium Chimique Societe Anonyme | Process for the synthesis of vincadifformine and related derivatives |
-
1980
- 1980-08-04 IT IT23904/80A patent/IT1132307B/it active
-
1981
- 1981-07-30 US US06/288,419 patent/US4379935A/en not_active Expired - Fee Related
- 1981-07-31 DE DE8181106039T patent/DE3161285D1/de not_active Expired
- 1981-07-31 EP EP81106039A patent/EP0045918B1/en not_active Expired
- 1981-07-31 AT AT81106039T patent/ATE5142T1/de not_active IP Right Cessation
- 1981-08-03 CH CH5000/81A patent/CH655112A5/it not_active IP Right Cessation
- 1981-08-03 ES ES505154A patent/ES505154A0/es active Granted
- 1981-08-04 JP JP56121502A patent/JPS5758683A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0420915B2 (en, 2012) | 1992-04-07 |
| DE3161285D1 (en) | 1983-12-01 |
| IT8023904A0 (it) | 1980-08-04 |
| ATE5142T1 (de) | 1983-11-15 |
| US4379935A (en) | 1983-04-12 |
| ES8204735A1 (es) | 1982-06-01 |
| EP0045918B1 (en) | 1983-10-26 |
| IT1132307B (it) | 1986-07-02 |
| JPS5758683A (en) | 1982-04-08 |
| ES505154A0 (es) | 1982-06-01 |
| EP0045918A1 (en) | 1982-02-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |