SU1282815A3 - Способ получени оптически активных транс-1Н-пропил-6-оксо-гидрохинолинов - Google Patents
Способ получени оптически активных транс-1Н-пропил-6-оксо-гидрохинолинов Download PDFInfo
- Publication number
- SU1282815A3 SU1282815A3 SU833622809A SU3622809A SU1282815A3 SU 1282815 A3 SU1282815 A3 SU 1282815A3 SU 833622809 A SU833622809 A SU 833622809A SU 3622809 A SU3622809 A SU 3622809A SU 1282815 A3 SU1282815 A3 SU 1282815A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- propyl
- methanol
- solution
- mixture
- optically active
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 138
- 239000000243 solution Substances 0.000 claims description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 230000003287 optical effect Effects 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 229940095064 tartrate Drugs 0.000 claims description 8
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 3
- UXYHZIYEDDINQH-UHFFFAOYSA-N C1=CNC2=C3C=NN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=NN=C3C=CC2=C1 UXYHZIYEDDINQH-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000002027 dichloromethane extract Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003495 polar organic solvent Substances 0.000 claims 2
- FWHLCAXBTREMQT-ZYHUDNBSSA-N (4ar,8ar)-1-propyl-2,3,4,4a,5,7,8,8a-octahydroquinolin-6-one Chemical compound C1C(=O)CC[C@H]2N(CCC)CCC[C@@H]21 FWHLCAXBTREMQT-ZYHUDNBSSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- OGODKNYCTJYXFF-UHFFFAOYSA-N bis(4-methylbenzoyl) 2,3-dihydroxybutanedioate Chemical compound C1=CC(C)=CC=C1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=C(C)C=C1 OGODKNYCTJYXFF-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- FWHLCAXBTREMQT-UHFFFAOYSA-N 1-propyl-2,3,4,4a,5,7,8,8a-octahydroquinolin-6-one Chemical compound C1C(=O)CCC2N(CCC)CCCC21 FWHLCAXBTREMQT-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- -1 toluoyl tartrate Chemical compound 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ICQNCHSXWNQIHC-UHFFFAOYSA-N 2-oxopropanedial Chemical compound O=CC(=O)C=O ICQNCHSXWNQIHC-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 241000220304 Prunus dulcis Species 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
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)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/439,107 US4471121A (en) | 1982-11-03 | 1982-11-03 | Method of resolving trans-d alpha-1-n-propyl-6-oxodecahydroquinoline and di-p-toluoyltartaric acid salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1282815A3 true SU1282815A3 (ru) | 1987-01-07 |
Family
ID=23743321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833622809A SU1282815A3 (ru) | 1982-11-03 | 1983-07-27 | Способ получени оптически активных транс-1Н-пропил-6-оксо-гидрохинолинов |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4471121A (enExample) |
| EP (1) | EP0112604A1 (enExample) |
| JP (1) | JPS5982365A (enExample) |
| KR (1) | KR860001506B1 (enExample) |
| AU (1) | AU557306B2 (enExample) |
| CA (1) | CA1198115A (enExample) |
| CS (1) | CS234050B2 (enExample) |
| DD (1) | DD210045A5 (enExample) |
| DK (1) | DK343183A (enExample) |
| ES (1) | ES8502092A1 (enExample) |
| FI (1) | FI832720A7 (enExample) |
| GB (1) | GB2129422B (enExample) |
| GR (1) | GR79600B (enExample) |
| HU (1) | HU189311B (enExample) |
| IL (1) | IL69360A (enExample) |
| NZ (1) | NZ205030A (enExample) |
| PH (1) | PH20193A (enExample) |
| PL (1) | PL243198A1 (enExample) |
| PT (1) | PT77113B (enExample) |
| RO (1) | RO86512B (enExample) |
| SU (1) | SU1282815A3 (enExample) |
| ZA (1) | ZA835502B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73001A0 (en) * | 1983-09-26 | 1984-12-31 | Lilly Co Eli | Improvements in and relating to 6-oxodecahydroquinolines |
| US4778894A (en) * | 1983-09-26 | 1988-10-18 | Eli Lilly And Company | 6 oxo-decahydroquinolines |
| US4764609A (en) * | 1986-03-31 | 1988-08-16 | Eli Lilly And Company | Synthesis of 2-aminopyrimido[4,5-g]quinolines |
| US5134143A (en) * | 1986-06-16 | 1992-07-28 | Eli Lilly And Company | BCD tricyclic ergoline part-structure analogues |
| US4826986A (en) * | 1986-06-16 | 1989-05-02 | Eli Lilly And Company | 6-Oxo-trans-octa- and decahydroquinolines |
| US4977160A (en) * | 1986-06-16 | 1990-12-11 | Eli Lilly And Company | BCD tricyclic ergoline part-structure analogues |
| FR2600649B1 (fr) * | 1986-06-26 | 1989-02-24 | Rhone Poulenc Sante | Procede de preparation du maleate acide de levomepromazine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230861A (en) * | 1979-01-22 | 1980-10-28 | Eli Lilly And Company | 1-And/or 7-substituted-6-hydroxy (or oxo)-3-decahydroquinoline carboxylic acids |
| US4198415A (en) * | 1979-01-22 | 1980-04-15 | Eli Lilly And Company | Prolactin inhibiting octahydro pyrazolo[3,4-g]quinolines |
-
1982
- 1982-11-03 US US06/439,107 patent/US4471121A/en not_active Expired - Fee Related
-
1983
- 1983-07-26 ES ES524454A patent/ES8502092A1/es not_active Expired
- 1983-07-27 JP JP58138680A patent/JPS5982365A/ja active Pending
- 1983-07-27 GR GR72054A patent/GR79600B/el unknown
- 1983-07-27 DK DK343183A patent/DK343183A/da not_active Application Discontinuation
- 1983-07-27 ZA ZA835502A patent/ZA835502B/xx unknown
- 1983-07-27 HU HU832645A patent/HU189311B/hu unknown
- 1983-07-27 PH PH29306A patent/PH20193A/en unknown
- 1983-07-27 PT PT77113A patent/PT77113B/pt unknown
- 1983-07-27 RO RO111745A patent/RO86512B/ro unknown
- 1983-07-27 NZ NZ205030A patent/NZ205030A/en unknown
- 1983-07-27 IL IL69360A patent/IL69360A/xx unknown
- 1983-07-27 AU AU17340/83A patent/AU557306B2/en not_active Ceased
- 1983-07-27 CS CS835634A patent/CS234050B2/cs unknown
- 1983-07-27 FI FI832720A patent/FI832720A7/fi not_active Application Discontinuation
- 1983-07-27 CA CA000433400A patent/CA1198115A/en not_active Expired
- 1983-07-27 EP EP83304342A patent/EP0112604A1/en not_active Ceased
- 1983-07-27 KR KR1019830003504A patent/KR860001506B1/ko not_active Expired
- 1983-07-27 PL PL24319883A patent/PL243198A1/xx unknown
- 1983-07-27 DD DD83253426A patent/DD210045A5/de unknown
- 1983-07-27 GB GB08320249A patent/GB2129422B/en not_active Expired
- 1983-07-27 SU SU833622809A patent/SU1282815A3/ru active
Non-Patent Citations (1)
| Title |
|---|
| Патецт US № 4198415, кл. С 07 D 471/04, опублик.1980. Патент US № 4230861, кл. С 07 D 215/04, опублик.1980. * |
Also Published As
| Publication number | Publication date |
|---|---|
| PH20193A (en) | 1986-10-16 |
| FI832720A7 (fi) | 1984-05-04 |
| DK343183D0 (da) | 1983-07-27 |
| KR860001506B1 (ko) | 1986-09-30 |
| PT77113A (en) | 1983-08-01 |
| CS234050B2 (en) | 1985-03-14 |
| EP0112604A1 (en) | 1984-07-04 |
| GB2129422A (en) | 1984-05-16 |
| KR840006626A (ko) | 1984-12-01 |
| NZ205030A (en) | 1986-03-14 |
| HU189311B (en) | 1986-06-30 |
| US4471121A (en) | 1984-09-11 |
| PL243198A1 (en) | 1984-08-13 |
| PT77113B (en) | 1986-04-11 |
| RO86512B (ro) | 1985-03-31 |
| IL69360A (en) | 1986-10-31 |
| JPS5982365A (ja) | 1984-05-12 |
| RO86512A (ro) | 1985-03-15 |
| DK343183A (da) | 1984-05-04 |
| GR79600B (enExample) | 1984-10-31 |
| DD210045A5 (de) | 1984-05-30 |
| CA1198115A (en) | 1985-12-17 |
| FI832720A0 (fi) | 1983-07-27 |
| AU557306B2 (en) | 1986-12-18 |
| GB8320249D0 (en) | 1983-09-01 |
| ES524454A0 (es) | 1984-12-16 |
| GB2129422B (en) | 1986-08-20 |
| ZA835502B (en) | 1985-03-27 |
| AU1734083A (en) | 1984-05-10 |
| ES8502092A1 (es) | 1984-12-16 |
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