HU194176B - Process for production of derivatives of new 7-phormildekahydridinoline - Google Patents
Process for production of derivatives of new 7-phormildekahydridinoline Download PDFInfo
- Publication number
- HU194176B HU194176B HU86814A HU81483A HU194176B HU 194176 B HU194176 B HU 194176B HU 86814 A HU86814 A HU 86814A HU 81483 A HU81483 A HU 81483A HU 194176 B HU194176 B HU 194176B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- substituted
- ivb
- phormildekahydridinoline
- derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 6
- -1 alkyl formate Chemical compound 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 claims 1
- ZRLDSAGKNYDEHN-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline-7-carbaldehyde Chemical class C1CCNC2CC(C=O)CCC21 ZRLDSAGKNYDEHN-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003512 Claisen condensation reaction Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GEKISUNTQZGQPY-UHFFFAOYSA-N 3,4,4a,5,6,7,8,8a-octahydro-2h-quinoline-1-carbaldehyde Chemical compound C1CCCC2N(C=O)CCCC21 GEKISUNTQZGQPY-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Extraction Or Liquid Replacement (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
A találmány tárgya eljárás új formildekahidrokinolln kürtitermékek előállítására.
E vegyületek a T/32111 sz. magyar közzétételi irat szerinti vegyületek előállításánál alkalmazhatók köztitermékként.
A találmány szerinti (IVb) általános képletü vegyületeket és sóikat állítjuk elő, ahol
R jelentése 1 —3 szénatomoe alkilcsoport, Olymódon, hogy (I) általános képletü transz-dl-1szubsztituált-3 -adott esetben szubsztituált-6-oxo-dekahidrokinolint 1 —6 szénatomos alkil-formiáttal formílezünk bázis jelenlétében. A reakciót az I. reakcióvázlat szemlélteti.
• A formilezett termék, melyet az 1. reakcióvázlatban négy tautomer szerkezettel (IVa~d) írtunk le, vizes oldatban túlnyomórészt ikerionos szerkezetű (IVb). Azonban a négy tautomer forma dinamikus egyensúlyban van, és e leírásban, amikor egyetlen szerkezetet ábrázolunk vagy írunk le, értelemszerűen a többi három formáról is szó van. A különböző fenti általános képleteknek a rezonancia-elmélet szerinti határszerkezetei szintén beleértendők a tennék szerkezetébe, így a IVb és a VIb’ általános képletü rezonanciahibridek.
A találmány szerinti reakció módosított Claisen•kondenzáció, ahol egy szomszédos karbonilcsoport által aktivált metiléncsoportot acilezünk bázis jelenlétében. Bázisként általában nátrium-etilátot használunk. Azonban a szakember számára nyilvánvaló módon más bázisokat, mint alkálifém-terc-alkoxidokat és -hidrideket, különösen kálium-lere-butoxidot. kálium-terc-amil-alkoxidot, vagy nátrium-hidridet is használhatunk. A Claisen-kondenzációt (I-ÍV) szokásosan etanolos oldatban hajtjuk végre. Az is nyilvánvaló, hogy reakcióközegként más kisszénatomszámú alkanolokat is hasonló poláris vízmentes oldószereket is alkalmazhatunk. Alkalmas oldószer például a tetrahidrofurán (THF), dietil-éter, dimetoxí-etán, dioxán, dimetil-szulfoxid (DMSO), dimetil-formamid (DMF) és terc-butanol. Az 1. reakcióvártat egész folyamatához előnyben lészesítjük a THF-t. Bár a reakcióhőmérsékiet nem kritikus, mintegy -20 C és visszafolyatás közötti tartómén) alkalmazhatunk, előnyben részesítve a 0 *C ét szobi hőmérséklet közötti tartományt.
- A találmányt ismertető alábbi példákban a köve 3 kező rövidítéseket használjuk:
THF=tetrahidrofurán, TLC=vékonyréteg-kromatográfia,
1. példa
3,6 g kálium-terc-butoxidot 50 ml THF-bán ol dunk és az oldathoz 0 C-on, 5,0 g transz-dl-1 -n-prc pfl-6-oxo-dekahidrokinolin és 2,36 g etil-formiát 2í ml THF-nal készült oldatát adjuk. Az oldatot 0 °C-or 15 percig, majd szobahőmérsékleten 17 óráig kever jük. A képződött sárga csapadékot vákuumban le szűrve, THF-nal mosva és vákuumban megszárftvs transz-dl-1-n-propil-ó-oxo-7-formil - dekahidrokinolin -káliumsót Icapunk. Kitermelés 90%.
NMR (mágneses magrezonancia spektrum) _Λ (Da0): delta 9,00 (s, IH, CHO), 3,02-0,99 (m, 16H), 20 0,84 [t, J=7, 3H, -CHj (n-C3 H? -ból)].
Claims (2)
- SZABADALMI IGÉNYPONTOK1. Eljárás (IVa), (IVb), (IVc) és (IVd) általános je képletü 7-formildekahldro-kinolin-származék - aholR jelentése 1 -3 szénatomos alkilcsoport, és sóik előállítására, azzal jellemezve, hogy egy (I) általános képletü dekahidro-kinolint ahol R jelentése a fenti -1-6 szénatomos alkil-formiáttal reagáltatunk bázis jelenlétében, és kívánt eset30 ben egy keletkezett szabad vegyületet sóvá alakítunk.
- 2. Az 1. igénypont szerinti eljárás olyan (IVb) általános képletü vegyületek előállítására, ahol R n-propil-csoportot jelent, azzal jellemezve, hogy olyan (Ϊ) általános képletü vegyületből indulunk ki, ahol R a fenti.35 3. Az 1. Igénypont szerinti eljárás, azzal jellemezve, hogy 4aR, 8aR konfigurációjú enantiomer l-n-propil-6-oxo-dekahídro-kinoliit kiindulási anyagot használunk.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43883482A | 1982-11-03 | 1982-11-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU194176B true HU194176B (en) | 1988-01-28 |
Family
ID=23742220
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU832646A HU190728B (en) | 1982-11-03 | 1983-07-27 | Process for preparing pyrazolo/3,4-b/quinoline derivatives |
| HU86814A HU194176B (en) | 1982-11-03 | 1983-07-27 | Process for production of derivatives of new 7-phormildekahydridinoline |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU832646A HU190728B (en) | 1982-11-03 | 1983-07-27 | Process for preparing pyrazolo/3,4-b/quinoline derivatives |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0110496B1 (hu) |
| JP (3) | JPS5982366A (hu) |
| KR (1) | KR870000234B1 (hu) |
| AT (1) | ATE29252T1 (hu) |
| AU (1) | AU551687B2 (hu) |
| CA (1) | CA1259313A (hu) |
| DD (1) | DD210047A5 (hu) |
| DE (1) | DE3373303D1 (hu) |
| DK (1) | DK343283A (hu) |
| ES (1) | ES524453A0 (hu) |
| FI (1) | FI832719A (hu) |
| GB (1) | GB2130576B (hu) |
| GR (1) | GR77559B (hu) |
| HU (2) | HU190728B (hu) |
| IE (1) | IE55668B1 (hu) |
| IL (1) | IL69358A (hu) |
| NZ (1) | NZ205031A (hu) |
| PL (2) | PL250137A1 (hu) |
| PT (1) | PT77111B (hu) |
| RO (1) | RO86894B (hu) |
| ZA (1) | ZA835501B (hu) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL75992A0 (en) * | 1984-08-03 | 1985-12-31 | Lilly Co Eli | Improvements in or relating to tricyclic quinoline derivatives |
| US4764609A (en) * | 1986-03-31 | 1988-08-16 | Eli Lilly And Company | Synthesis of 2-aminopyrimido[4,5-g]quinolines |
| US4826986A (en) * | 1986-06-16 | 1989-05-02 | Eli Lilly And Company | 6-Oxo-trans-octa- and decahydroquinolines |
| US7249161B2 (en) * | 2002-12-27 | 2007-07-24 | Nokia Corporation | Method and system for facilitating instant messaging transactions between disparate service providers |
Family Cites Families (1)
| 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 |
-
1983
- 1983-07-26 ES ES524453A patent/ES524453A0/es active Granted
- 1983-07-27 RO RO111743A patent/RO86894B/ro unknown
- 1983-07-27 HU HU832646A patent/HU190728B/hu not_active IP Right Cessation
- 1983-07-27 ZA ZA835501A patent/ZA835501B/xx unknown
- 1983-07-27 GB GB08320248A patent/GB2130576B/en not_active Expired
- 1983-07-27 EP EP83304340A patent/EP0110496B1/en not_active Expired
- 1983-07-27 IL IL69358A patent/IL69358A/xx not_active IP Right Cessation
- 1983-07-27 IE IE1773/83A patent/IE55668B1/en not_active IP Right Cessation
- 1983-07-27 GR GR72055A patent/GR77559B/el unknown
- 1983-07-27 PL PL25013783A patent/PL250137A1/xx unknown
- 1983-07-27 PL PL24320083A patent/PL243200A1/xx unknown
- 1983-07-27 FI FI832719A patent/FI832719A/fi not_active Application Discontinuation
- 1983-07-27 NZ NZ205031A patent/NZ205031A/en unknown
- 1983-07-27 AT AT83304340T patent/ATE29252T1/de not_active IP Right Cessation
- 1983-07-27 DD DD83253428A patent/DD210047A5/de unknown
- 1983-07-27 PT PT77111A patent/PT77111B/pt unknown
- 1983-07-27 KR KR1019830003503A patent/KR870000234B1/ko not_active IP Right Cessation
- 1983-07-27 JP JP58138681A patent/JPS5982366A/ja active Granted
- 1983-07-27 CA CA000433331A patent/CA1259313A/en not_active Expired
- 1983-07-27 HU HU86814A patent/HU194176B/hu unknown
- 1983-07-27 AU AU17339/83A patent/AU551687B2/en not_active Ceased
- 1983-07-27 DE DE8383304340T patent/DE3373303D1/de not_active Expired
- 1983-07-27 DK DK343283A patent/DK343283A/da unknown
-
1991
- 1991-03-27 JP JP3089660A patent/JPH04217979A/ja active Granted
- 1991-03-27 JP JP3089661A patent/JPH0662618B2/ja not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |