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)
- Extraction Or Liquid Replacement (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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 |
|---|---|---|---|
| HU86814A HU194176B (en) | 1982-11-03 | 1983-07-27 | Process for production of derivatives of new 7-phormildekahydridinoline |
| HU832646A HU190728B (en) | 1982-11-03 | 1983-07-27 | Process for preparing pyrazolo/3,4-b/quinoline derivatives |
Family Applications After (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 (en, 2012) |
| JP (3) | JPS5982366A (en, 2012) |
| KR (1) | KR870000234B1 (en, 2012) |
| AT (1) | ATE29252T1 (en, 2012) |
| AU (1) | AU551687B2 (en, 2012) |
| CA (1) | CA1259313A (en, 2012) |
| DD (1) | DD210047A5 (en, 2012) |
| DE (1) | DE3373303D1 (en, 2012) |
| DK (1) | DK343283A (en, 2012) |
| ES (1) | ES8501395A1 (en, 2012) |
| FI (1) | FI832719A7 (en, 2012) |
| GB (1) | GB2130576B (en, 2012) |
| GR (1) | GR77559B (en, 2012) |
| HU (2) | HU194176B (en, 2012) |
| IE (1) | IE55668B1 (en, 2012) |
| IL (1) | IL69358A (en, 2012) |
| NZ (1) | NZ205031A (en, 2012) |
| PL (2) | PL243200A1 (en, 2012) |
| PT (1) | PT77111B (en, 2012) |
| RO (1) | RO86894B (en, 2012) |
| ZA (1) | ZA835501B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT40656A (en) * | 1984-08-03 | 1987-01-28 | Lilly Co Eli | Process for producing 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/ES8501395A1/es not_active Expired
- 1983-07-27 PL PL24320083A patent/PL243200A1/xx unknown
- 1983-07-27 FI FI832719A patent/FI832719A7/fi not_active Application Discontinuation
- 1983-07-27 EP EP83304340A patent/EP0110496B1/en not_active Expired
- 1983-07-27 PL PL25013783A patent/PL250137A1/xx unknown
- 1983-07-27 HU HU86814A patent/HU194176B/hu unknown
- 1983-07-27 PT PT77111A patent/PT77111B/pt unknown
- 1983-07-27 KR KR1019830003503A patent/KR870000234B1/ko not_active Expired
- 1983-07-27 IL IL69358A patent/IL69358A/xx not_active IP Right Cessation
- 1983-07-27 RO RO111743A patent/RO86894B/ro unknown
- 1983-07-27 DK DK343283A patent/DK343283A/da unknown
- 1983-07-27 ZA ZA835501A patent/ZA835501B/xx unknown
- 1983-07-27 HU HU832646A patent/HU190728B/hu not_active IP Right Cessation
- 1983-07-27 AU AU17339/83A patent/AU551687B2/en not_active Ceased
- 1983-07-27 GB GB08320248A patent/GB2130576B/en not_active Expired
- 1983-07-27 DE DE8383304340T patent/DE3373303D1/de not_active Expired
- 1983-07-27 NZ NZ205031A patent/NZ205031A/en unknown
- 1983-07-27 CA CA000433331A patent/CA1259313A/en not_active Expired
- 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 GR GR72055A patent/GR77559B/el unknown
- 1983-07-27 JP JP58138681A patent/JPS5982366A/ja active Granted
- 1983-07-27 IE IE1773/83A patent/IE55668B1/en not_active IP Right Cessation
-
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 |