SU793404A3 - Способ получени производных винциновой кислоты или их солей или их четвертичных солей - Google Patents
Способ получени производных винциновой кислоты или их солей или их четвертичных солей Download PDFInfo
- Publication number
- SU793404A3 SU793404A3 SU782640249A SU2640249A SU793404A3 SU 793404 A3 SU793404 A3 SU 793404A3 SU 782640249 A SU782640249 A SU 782640249A SU 2640249 A SU2640249 A SU 2640249A SU 793404 A3 SU793404 A3 SU 793404A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- ethyl ester
- salts
- apovincine
- ethyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 29
- 150000003839 salts Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 6
- QMSXPSURJTUZMP-UHFFFAOYSA-N vincine Chemical compound COC1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 QMSXPSURJTUZMP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 230000000304 vasodilatating effect Effects 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004494 ethyl ester group Chemical group 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 7
- 235000019441 ethanol Nutrition 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 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 description 6
- 239000003463 adsorbent Substances 0.000 claims description 5
- 230000000144 pharmacologic effect Effects 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- -1 chlorazourethan Chemical compound 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000002329 infrared spectrum Methods 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 230000036770 blood supply Effects 0.000 claims 6
- 239000013543 active substance Substances 0.000 claims 4
- 230000002490 cerebral effect Effects 0.000 claims 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 claims 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- 230000017531 blood circulation Effects 0.000 claims 2
- 230000036772 blood pressure Effects 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 claims 2
- 229940095064 tartrate Drugs 0.000 claims 2
- 229960002726 vincamine Drugs 0.000 claims 2
- ZUDZWKJBYZAGBS-UHFFFAOYSA-N 4-ethoxy-2,3-dihydroxy-4-oxobutanoic acid Chemical compound CCOC(=O)C(O)C(O)C(O)=O ZUDZWKJBYZAGBS-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 241000282472 Canis lupus familiaris Species 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- WKACQPMBGWZDMR-UHFFFAOYSA-N Vincamin Natural products CC=C1/CN2CCC34CC2C1C(=C3Nc5ccccc45)C=O WKACQPMBGWZDMR-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004004 carotid artery internal Anatomy 0.000 claims 1
- 230000004087 circulation Effects 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 210000001105 femoral artery Anatomy 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 210000002385 vertebral artery Anatomy 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000032050 esterification Effects 0.000 abstract description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000000047 product Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007787 solid Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77RI642A HU177498B (en) | 1977-07-27 | 1977-07-27 | Process for preparing new vincinic acid and apovincinic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU793404A3 true SU793404A3 (ru) | 1980-12-30 |
Family
ID=11001039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782640249A SU793404A3 (ru) | 1977-07-27 | 1978-07-26 | Способ получени производных винциновой кислоты или их солей или их четвертичных солей |
Country Status (10)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829570Y2 (ja) * | 1979-11-19 | 1983-06-29 | 日本航空電子工業株式会社 | ソケツト |
| JPH065634B2 (ja) * | 1983-09-12 | 1994-01-19 | 株式会社東芝 | ハイブリツドｉｃ |
| CN114249721B (zh) * | 2021-11-29 | 2023-10-17 | 南京中医药大学 | 长春胺peg衍生物与在制备治疗糖尿病周围神经病变、糖尿病足及肺纤维化药物中的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE422798B (sv) * | 1973-12-18 | 1982-03-29 | Sandoz Ag | Analogiforfarande for framstellning av vincaminderivat |
-
1977
- 1977-07-27 HU HU77RI642A patent/HU177498B/hu unknown
-
1978
- 1978-07-21 SE SE7808072A patent/SE7808072L/xx unknown
- 1978-07-25 GB GB7831093A patent/GB2001974B/en not_active Expired
- 1978-07-25 DE DE19782832645 patent/DE2832645A1/de not_active Withdrawn
- 1978-07-25 FR FR7821948A patent/FR2398747A1/fr active Granted
- 1978-07-26 SU SU782640249A patent/SU793404A3/ru active
- 1978-07-26 NL NL7807948A patent/NL7807948A/xx not_active Application Discontinuation
- 1978-07-26 BE BE189505A patent/BE869274A/xx not_active IP Right Cessation
- 1978-07-27 IT IT26172/78A patent/IT1097445B/it active
- 1978-07-27 JP JP9104278A patent/JPS5436297A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5436297A (en) | 1979-03-16 |
| GB2001974B (en) | 1982-02-10 |
| HU177498B (en) | 1981-10-28 |
| IT1097445B (it) | 1985-08-31 |
| GB2001974A (en) | 1979-02-14 |
| SE7808072L (sv) | 1979-01-28 |
| IT7826172A0 (it) | 1978-07-27 |
| FR2398747A1 (fr) | 1979-02-23 |
| BE869274A (fr) | 1978-11-16 |
| FR2398747B1 (enrdf_load_stackoverflow) | 1981-12-11 |
| DE2832645A1 (de) | 1979-02-08 |
| NL7807948A (nl) | 1979-01-30 |
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