CS250692B2 - Method of 9- or 11- substituted apovincamine acid's racemic and optically active derivatives preparation - Google Patents
Method of 9- or 11- substituted apovincamine acid's racemic and optically active derivatives preparation Download PDFInfo
- Publication number
- CS250692B2 CS250692B2 CS855185A CS518585A CS250692B2 CS 250692 B2 CS250692 B2 CS 250692B2 CS 855185 A CS855185 A CS 855185A CS 518585 A CS518585 A CS 518585A CS 250692 B2 CS250692 B2 CS 250692B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- salts
- substituted
- apovincamic
- general formula
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims description 9
- OZDNDGXASTWERN-CTNGQTDRSA-N Apovincamine Chemical class C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-CTNGQTDRSA-N 0.000 title description 4
- 229950006936 apovincamine Drugs 0.000 title description 4
- 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 description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
- 229960000583 acetic acid Drugs 0.000 claims description 12
- 239000012362 glacial acetic acid Substances 0.000 claims description 11
- 238000006396 nitration reaction Methods 0.000 claims description 10
- 150000002823 nitrates Chemical class 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 229910052751 metal Chemical class 0.000 abstract description 4
- 239000002184 metal Chemical class 0.000 abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- 239000011541 reaction mixture Substances 0.000 abstract description 3
- 150000003863 ammonium salts Chemical class 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 2
- 230000003287 optical effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 14
- 229910002651 NO3 Inorganic materials 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- 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 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- -1 hydrohalic acids Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 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 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 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 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 229960002726 vincamine Drugs 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 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 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HXFOXFJUNFFYMO-BYPYZUCNSA-N N-alpha-acetyl-L-asparagine Chemical compound CC(=O)N[C@H](C(O)=O)CC(N)=O HXFOXFJUNFFYMO-BYPYZUCNSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000005406 washing Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Slide Fasteners, Snap Fasteners, And Hook Fasteners (AREA)
- Reinforced Plastic Materials (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859904A CS250700B2 (cs) | 1984-07-11 | 1985-12-27 | Způsob přípravy racemických a cpticky aktivních derivátů S- nebo 11-substituované apovincaminové kyseliny |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU842702A HU191693B (en) | 1984-07-11 | 1984-07-11 | Process for production of derivatives of 9-or-11 substituated apovincamin acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS250692B2 true CS250692B2 (en) | 1987-05-14 |
Family
ID=10960711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS855185A CS250692B2 (en) | 1984-07-11 | 1985-07-11 | Method of 9- or 11- substituted apovincamine acid's racemic and optically active derivatives preparation |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0173824B1 (en]) |
| JP (1) | JPS61118385A (en]) |
| KR (1) | KR910010080B1 (en]) |
| CN (2) | CN85105334A (en]) |
| AT (1) | ATE47855T1 (en]) |
| AU (1) | AU580787B2 (en]) |
| CA (1) | CA1266658A (en]) |
| CS (1) | CS250692B2 (en]) |
| DD (1) | DD236094A5 (en]) |
| DE (1) | DE3574141D1 (en]) |
| DK (1) | DK317885A (en]) |
| ES (1) | ES8603875A1 (en]) |
| FI (1) | FI81799C (en]) |
| GR (1) | GR851724B (en]) |
| HU (1) | HU191693B (en]) |
| IL (1) | IL75772A (en]) |
| IN (1) | IN163913B (en]) |
| NO (1) | NO852794L (en]) |
| NZ (1) | NZ212714A (en]) |
| PH (1) | PH22159A (en]) |
| PL (1) | PL144791B1 (en]) |
| PT (1) | PT80798B (en]) |
| SU (1) | SU1398775A3 (en]) |
| YU (1) | YU115285A (en]) |
| ZA (1) | ZA855246B (en]) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU193772B (en) * | 1985-06-12 | 1987-11-30 | Richter Gedeon Vegyeszet | Process for producing new nitro-bis-indole derivatives |
| CN1042492C (zh) * | 1991-10-31 | 1999-03-17 | 东北制药总厂 | 阿扑长春胺酸乙酯制剂的制备方法 |
| CA2238488A1 (en) * | 1994-07-07 | 1997-06-05 | Hiroyoshi Hidaka | Apovincaminic acid derivatives and drugs containing the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2320302A1 (fr) * | 1975-08-05 | 1977-03-04 | Omnium Chimique Sa | Procede de preparation de 11-aminovincamine dextrogyre, de 11-aminovincamine levogyre, de 11-aminovincamine racemique et derives indoliques nouveaux |
| FR2341585A2 (fr) * | 1976-02-20 | 1977-09-16 | Omnium Chimique Sa | Procede de preparation de 9-aminovincamine dextrogyre, de 9-aminovincamine levogyre, de 9-aminovincamine racemique et derives indoliques nouveaux |
| FR2342980A1 (fr) * | 1976-03-01 | 1977-09-30 | Omnium Chimique Sa | Procede de preparation de 9 et 11-aminoapovincamines dextrogyres, de 9 et 11-aminoapovincamines levogyres, de 9 et 11-aminoapovincamines racemiques et nouveaux derives de l'apovincamine |
| HU187733B (en) * | 1982-06-30 | 1986-02-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing apovincaminic acid derivatives |
| HU191694B (en) * | 1984-07-11 | 1987-03-30 | Richter Gedeon Vegyeszet | Process for production of new derivatives of amineburnan carbonic acid |
| HU191938B (en) * | 1984-07-11 | 1987-04-28 | Andras Vedres | Process for production of new derivatives of 9 and 11 nitro-apovincamin acid |
-
1984
- 1984-07-11 HU HU842702A patent/HU191693B/hu not_active IP Right Cessation
-
1985
- 1985-07-10 AU AU44772/85A patent/AU580787B2/en not_active Ceased
- 1985-07-11 DD DD85278515A patent/DD236094A5/de not_active IP Right Cessation
- 1985-07-11 AT AT85108625T patent/ATE47855T1/de not_active IP Right Cessation
- 1985-07-11 YU YU01152/85A patent/YU115285A/xx unknown
- 1985-07-11 IN IN545/DEL/85A patent/IN163913B/en unknown
- 1985-07-11 NO NO852794A patent/NO852794L/no unknown
- 1985-07-11 PT PT80798A patent/PT80798B/pt not_active IP Right Cessation
- 1985-07-11 ZA ZA855246A patent/ZA855246B/xx unknown
- 1985-07-11 CA CA000486674A patent/CA1266658A/en not_active Expired - Lifetime
- 1985-07-11 SU SU853920150A patent/SU1398775A3/ru active
- 1985-07-11 DE DE8585108625T patent/DE3574141D1/de not_active Expired
- 1985-07-11 KR KR1019850004953A patent/KR910010080B1/ko not_active Expired
- 1985-07-11 GR GR851724A patent/GR851724B/el unknown
- 1985-07-11 FI FI852749A patent/FI81799C/fi not_active IP Right Cessation
- 1985-07-11 JP JP60151429A patent/JPS61118385A/ja active Granted
- 1985-07-11 NZ NZ212714A patent/NZ212714A/xx unknown
- 1985-07-11 EP EP85108625A patent/EP0173824B1/de not_active Expired
- 1985-07-11 CS CS855185A patent/CS250692B2/cs unknown
- 1985-07-11 PH PH32511A patent/PH22159A/en unknown
- 1985-07-11 DK DK317885A patent/DK317885A/da not_active Application Discontinuation
- 1985-07-11 ES ES545115A patent/ES8603875A1/es not_active Expired
- 1985-07-11 IL IL75772A patent/IL75772A/xx not_active IP Right Cessation
- 1985-07-11 PL PL1985254498A patent/PL144791B1/pl unknown
- 1985-07-12 CN CN85105334A patent/CN85105334A/zh active Pending
- 1985-08-10 CN CN85106058A patent/CN85106058A/zh active Pending
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