DK161963B - 2-phenyl-imidazooe1,2-aaaquinolinderivater samt fremgangsmaade til fremstilling heraf og et farmaceutisk praeparat indeholdende saadanne forbindelser - Google Patents
2-phenyl-imidazooe1,2-aaaquinolinderivater samt fremgangsmaade til fremstilling heraf og et farmaceutisk praeparat indeholdende saadanne forbindelser Download PDFInfo
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- DK161963B DK161963B DK356985A DK356985A DK161963B DK 161963 B DK161963 B DK 161963B DK 356985 A DK356985 A DK 356985A DK 356985 A DK356985 A DK 356985A DK 161963 B DK161963 B DK 161963B
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- 150000001875 compounds Chemical class 0.000 title claims description 50
- 238000000034 method Methods 0.000 title description 7
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 2-Aminoquinoline Natural products C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- -1 2-aminoquinoline compound Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- FQJSDLFCFOISBV-UHFFFAOYSA-N 2-phenylimidazo[1,2-a]quinoline Chemical class N1=C2C=CC3=CC=CC=C3N2C=C1C1=CC=CC=C1 FQJSDLFCFOISBV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
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- 238000006170 formylation reaction Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- 241000699670 Mus sp. Species 0.000 description 6
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
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- 238000000354 decomposition reaction Methods 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
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- 239000007924 injection Substances 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
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- VOWUNKDRZFLGGI-UHFFFAOYSA-N 2-(4-chlorophenyl)imidazo[1,2-a]quinoline Chemical compound C1=CC(Cl)=CC=C1C1=CN2C3=CC=CC=C3C=CC2=N1 VOWUNKDRZFLGGI-UHFFFAOYSA-N 0.000 description 2
- OWMDVXXXAJDNKC-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imidazo[1,2-a]quinolin-1-yl]-n-methylacetamide Chemical compound N1=C2C=CC3=CC=CC=C3N2C(CC(=O)NC)=C1C1=CC=C(Cl)C=C1 OWMDVXXXAJDNKC-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- 229940043376 ammonium acetate Drugs 0.000 description 2
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- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GUCOHALGSMFJNM-UHFFFAOYSA-N 2-(2h-quinolin-1-yl)acetamide Chemical compound C1=CC=C2N(CC(=O)N)CC=CC2=C1 GUCOHALGSMFJNM-UHFFFAOYSA-N 0.000 description 1
- UQGWINZWPAEFFB-UHFFFAOYSA-N 2-(4-chlorophenyl)imidazo[1,2-a]quinoline-1-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1C1=C(C=O)N2C3=CC=CC=C3C=CC2=N1 UQGWINZWPAEFFB-UHFFFAOYSA-N 0.000 description 1
- PBYRQOOLDMKCDX-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imidazo[1,2-a]quinolin-1-yl]acetic acid Chemical compound N1=C2C=CC3=CC=CC=C3N2C(CC(=O)O)=C1C1=CC=C(Cl)C=C1 PBYRQOOLDMKCDX-UHFFFAOYSA-N 0.000 description 1
- KPFXQXAJZOHZDQ-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imidazo[1,2-a]quinolin-1-yl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C1=C(CC#N)N2C3=CC=CC=C3C=CC2=N1 KPFXQXAJZOHZDQ-UHFFFAOYSA-N 0.000 description 1
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 1
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- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
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- 206010043994 Tonic convulsion Diseases 0.000 description 1
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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Classifications
-
- 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
- C07D471/12—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 three hetero rings
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8412446A FR2568879B1 (fr) | 1984-08-07 | 1984-08-07 | Imidazo(1,2-a)quinolines, leur preparation et leur application en therapeutique |
| FR8412446 | 1984-08-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK356985D0 DK356985D0 (da) | 1985-08-06 |
| DK356985A DK356985A (da) | 1986-02-08 |
| DK161963B true DK161963B (da) | 1991-09-02 |
Family
ID=9306855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK356985A DK161963B (da) | 1984-08-07 | 1985-08-06 | 2-phenyl-imidazooe1,2-aaaquinolinderivater samt fremgangsmaade til fremstilling heraf og et farmaceutisk praeparat indeholdende saadanne forbindelser |
Country Status (20)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2593179B1 (fr) * | 1986-01-22 | 1988-04-01 | Synthelabo | Derives d'imidazo(1,2-a)quinoleines, leur preparation et leur application en therapeutique |
| FR2606410B1 (fr) * | 1986-11-07 | 1989-02-24 | Synthelabo | Imidazopyridines, leur preparation et leur application en therapeutique |
| EP0607076A1 (fr) * | 1993-01-15 | 1994-07-20 | Synthelabo | Dérivés de 9h-imidazo 1,2-a benzimidazole-3-acétamide à activité GABA |
| FR2700544B1 (fr) * | 1993-01-15 | 1995-02-17 | Synthelabo | Dérivés de 9H-imidazo[1,2-a]benzimidazole-3-acétamide, leur préparation et leur application en thérapeutique. |
| FR2700547B1 (fr) * | 1993-01-15 | 1995-02-17 | Synthelabo | Dérivés d'imidazo[2,1-b]benzosélénazole-3-acétamide, leur préparation et leur application en thérapeutique. |
| FR2707987B1 (fr) * | 1993-07-22 | 1995-09-08 | Synthelabo | Dérivés de 9H-imidazo[1,2-a]benzimidazole-3-acétamide, leur préparation et leur application en thérapeutique . |
| FR2719843B1 (fr) * | 1994-05-10 | 1996-06-07 | Synthelabo | Dérivés de 5,6-dihydro-4h-imidazo [2',1':2,3] imidazo-[4,5,1-ij] quinoléine et de 4,5-dihydroimidazo [1,2-a] pyrrolo-[1,2,3-cd] benzimidazole, leur préparation et leur application en thérapeutique. |
| FR2722501B1 (fr) * | 1994-07-13 | 1996-08-09 | Synthelabo | Derives de 9h-imidazo(1,2-a)benzimidazole-3-acetamide, leur preparation et leur application en therapeutique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2492382A1 (fr) * | 1980-10-22 | 1982-04-23 | Synthelabo | Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique |
-
1984
- 1984-08-07 FR FR8412446A patent/FR2568879B1/fr not_active Expired
-
1985
- 1985-07-30 AT AT85401555T patent/ATE41001T1/de not_active IP Right Cessation
- 1985-07-30 DE DE8585401555T patent/DE3568430D1/de not_active Expired
- 1985-07-30 EP EP85401555A patent/EP0172097B1/fr not_active Expired
- 1985-08-06 JP JP60173976A patent/JPS6147484A/ja active Pending
- 1985-08-06 AR AR30120285A patent/AR240674A1/es active
- 1985-08-06 FI FI853027A patent/FI79314C/fi not_active IP Right Cessation
- 1985-08-06 DK DK356985A patent/DK161963B/da not_active IP Right Cessation
- 1985-08-06 HU HU852992A patent/HU199838B/hu not_active IP Right Cessation
- 1985-08-06 IL IL76019A patent/IL76019A0/xx not_active IP Right Cessation
- 1985-08-06 PT PT80920A patent/PT80920B/pt not_active IP Right Cessation
- 1985-08-06 ZA ZA855937A patent/ZA855937B/xx unknown
- 1985-08-06 CA CA000488164A patent/CA1263389A/en not_active Expired
- 1985-08-06 KR KR1019850005659A patent/KR860001814A/ko not_active Ceased
- 1985-08-06 AU AU45814/85A patent/AU573880B2/en not_active Ceased
- 1985-08-06 NZ NZ213014A patent/NZ213014A/en unknown
- 1985-08-06 ES ES545929A patent/ES8604593A1/es not_active Expired
- 1985-08-06 GR GR851929A patent/GR851929B/el unknown
- 1985-08-06 NO NO853099A patent/NO162188C/no unknown
- 1985-08-06 MX MX206216A patent/MX161035A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU573880B2 (en) | 1988-06-23 |
| ES8604593A1 (es) | 1986-02-01 |
| JPS6147484A (ja) | 1986-03-07 |
| DK356985D0 (da) | 1985-08-06 |
| HU199838B (en) | 1990-03-28 |
| IL76019A0 (en) | 1985-12-31 |
| FI853027A0 (fi) | 1985-08-06 |
| ES545929A0 (es) | 1986-02-01 |
| CA1263389A (en) | 1989-11-28 |
| FR2568879B1 (fr) | 1986-12-12 |
| NO162188B (no) | 1989-08-14 |
| FI853027L (fi) | 1986-02-08 |
| FI79314C (fi) | 1989-12-11 |
| FI79314B (fi) | 1989-08-31 |
| AR240674A1 (es) | 1990-08-31 |
| AU4581485A (en) | 1986-02-13 |
| EP0172097A1 (fr) | 1986-02-19 |
| HUT38636A (en) | 1986-06-30 |
| PT80920B (pt) | 1987-12-30 |
| MX161035A (es) | 1990-07-11 |
| KR860001814A (ko) | 1986-03-22 |
| EP0172097B1 (fr) | 1989-03-01 |
| NO853099L (no) | 1986-02-10 |
| FR2568879A1 (fr) | 1986-02-14 |
| DK356985A (da) | 1986-02-08 |
| NO162188C (no) | 1989-11-29 |
| GR851929B (enrdf_load_stackoverflow) | 1985-12-09 |
| ZA855937B (en) | 1986-03-26 |
| DE3568430D1 (en) | 1989-04-06 |
| PT80920A (fr) | 1985-09-01 |
| ATE41001T1 (de) | 1989-03-15 |
| NZ213014A (en) | 1988-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |