NO300132B1 - Analogifremgangsmåte for fremstilling av terapeutisk aktive 1-(substituerte pyridinylamino)-1H-indol-5-yl substituerte karbamater - Google Patents
Analogifremgangsmåte for fremstilling av terapeutisk aktive 1-(substituerte pyridinylamino)-1H-indol-5-yl substituerte karbamater Download PDFInfo
- Publication number
- NO300132B1 NO300132B1 NO912866A NO912866A NO300132B1 NO 300132 B1 NO300132 B1 NO 300132B1 NO 912866 A NO912866 A NO 912866A NO 912866 A NO912866 A NO 912866A NO 300132 B1 NO300132 B1 NO 300132B1
- Authority
- NO
- Norway
- Prior art keywords
- give
- indol
- pyridinylamino
- hydrogen
- added
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 1- (Substituted Pyridinylamino) -1H-Indol-5-Yl Chemical group 0.000 title abstract description 21
- 150000004657 carbamic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- QIVRYRSQPYRTSY-IBGZPJMESA-N [1-[propyl(pyridin-4-yl)amino]indol-5-yl] n-[(1s)-1-phenylethyl]carbamate Chemical compound C1=CC2=CC(OC(=O)N[C@@H](C)C=3C=CC=CC=3)=CC=C2N1N(CCC)C1=CC=NC=C1 QIVRYRSQPYRTSY-IBGZPJMESA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 1
- 230000001713 cholinergic effect Effects 0.000 abstract description 4
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 3
- 230000007074 memory dysfunction Effects 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000006735 deficit Effects 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
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- 239000007787 solid Substances 0.000 description 61
- 239000000243 solution Substances 0.000 description 58
- 235000019439 ethyl acetate Nutrition 0.000 description 55
- 238000004458 analytical method Methods 0.000 description 50
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- 239000000741 silica gel Substances 0.000 description 38
- 229910002027 silica gel Inorganic materials 0.000 description 38
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
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- 238000003756 stirring Methods 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
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- 238000004128 high performance liquid chromatography Methods 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000000706 filtrate Substances 0.000 description 20
- 238000001914 filtration Methods 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
- BNEURMPRVSVUQI-UHFFFAOYSA-N 1-[propyl(pyridin-4-yl)amino]indol-5-ol Chemical compound C1=CC2=CC(O)=CC=C2N1N(CCC)C1=CC=NC=C1 BNEURMPRVSVUQI-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 235000011181 potassium carbonates Nutrition 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
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- 108010022752 Acetylcholinesterase Proteins 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 229940022698 acetylcholinesterase Drugs 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 239000008363 phosphate buffer Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
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- 235000015320 potassium carbonate Nutrition 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
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- LNARDFSTZJMTFN-UHFFFAOYSA-N 1-[methyl(pyridin-4-yl)amino]indol-5-ol Chemical compound C1=CC2=CC(O)=CC=C2N1N(C)C1=CC=NC=C1 LNARDFSTZJMTFN-UHFFFAOYSA-N 0.000 description 4
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- WHQULUBXRZWECQ-UHFFFAOYSA-N 1-[3-(3-fluoropyridin-4-yl)propylamino]-3-methylindol-5-ol Chemical compound C12=CC=C(O)C=C2C(C)=CN1NCCCC1=CC=NC=C1F WHQULUBXRZWECQ-UHFFFAOYSA-N 0.000 description 3
- IHMSBOIANJQTTO-UHFFFAOYSA-N 3-methyl-1-[propyl(pyridin-4-yl)amino]indol-5-ol Chemical compound C1=C(C)C2=CC(O)=CC=C2N1N(CCC)C1=CC=NC=C1 IHMSBOIANJQTTO-UHFFFAOYSA-N 0.000 description 3
- UQNIVQSJUREHAC-UHFFFAOYSA-N 3-methyl-5-phenylmethoxyindol-1-amine Chemical compound C1=C2C(C)=CN(N)C2=CC=C1OCC1=CC=CC=C1 UQNIVQSJUREHAC-UHFFFAOYSA-N 0.000 description 3
- XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 3
- UJFQGXBJOUSPIL-UHFFFAOYSA-N 5-phenylmethoxy-n-pyridin-4-ylindol-1-amine Chemical compound C=1C=CC=CC=1COC(C=C1C=C2)=CC=C1N2NC1=CC=NC=C1 UJFQGXBJOUSPIL-UHFFFAOYSA-N 0.000 description 3
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- BITIAQKIIFTBQZ-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-5-phenylmethoxyindol-1-amine Chemical compound FC1=CN=CC=C1NN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C=C1 BITIAQKIIFTBQZ-UHFFFAOYSA-N 0.000 description 3
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- YSAFCQXCCPCUDY-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-1h-indole Chemical compound C1=C2C(C)=CNC2=CC=C1OCC1=CC=CC=C1 YSAFCQXCCPCUDY-UHFFFAOYSA-N 0.000 description 2
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OVNUPJXMCMTQCN-UHFFFAOYSA-N hydron;(4-phenylmethoxyphenyl)hydrazine;chloride Chemical compound Cl.C1=CC(NN)=CC=C1OCC1=CC=CC=C1 OVNUPJXMCMTQCN-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000006308 propyl amino group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
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- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/555,890 US5102891A (en) | 1990-07-23 | 1990-07-23 | 1-(substituted pyridinylamino)-1H-indol-5-yl substituted carbamates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO912866D0 NO912866D0 (no) | 1991-07-22 |
| NO912866L NO912866L (no) | 1992-01-24 |
| NO300132B1 true NO300132B1 (no) | 1997-04-14 |
Family
ID=24218998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO912866A NO300132B1 (no) | 1990-07-23 | 1991-07-22 | Analogifremgangsmåte for fremstilling av terapeutisk aktive 1-(substituerte pyridinylamino)-1H-indol-5-yl substituerte karbamater |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5102891A (xx) |
| EP (1) | EP0468401B1 (xx) |
| JP (1) | JP2564714B2 (xx) |
| KR (1) | KR100201515B1 (xx) |
| AT (1) | ATE171176T1 (xx) |
| AU (1) | AU639581B2 (xx) |
| BR (1) | BR1100534A (xx) |
| CA (1) | CA2047531C (xx) |
| CZ (1) | CZ283253B6 (xx) |
| DE (1) | DE69130196T2 (xx) |
| DK (1) | DK0468401T3 (xx) |
| ES (1) | ES2121761T3 (xx) |
| FI (1) | FI102067B1 (xx) |
| HU (1) | HUT58317A (xx) |
| IE (1) | IE912567A1 (xx) |
| IL (1) | IL98920A (xx) |
| MX (1) | MX9100342A (xx) |
| NO (1) | NO300132B1 (xx) |
| NZ (1) | NZ239038A (xx) |
| PL (1) | PL291185A1 (xx) |
| PT (1) | PT98413B (xx) |
| SG (1) | SG48059A1 (xx) |
| ZA (1) | ZA915723B (xx) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264442A (en) * | 1990-08-13 | 1993-11-23 | Hoechst-Roussel Pharmaceuticals Incorporated | Carbamoyl-1-(pyridinylalkyl)-1H-indoles, indolines and related analogs |
| CZ284437B6 (cs) * | 1991-04-17 | 1998-11-11 | Hoechst Marion Roussel, Inc. | Substituované (pyridinylamino)-benzisoxazoly a -benzo[b]thiofeny, způsob jejich přípravy farmaceutický prostředek obsahující tyto sloučeniny a použití těchto sloučenin |
| US5319096A (en) * | 1992-04-03 | 1994-06-07 | Hoechst-Roussel Pharmaceuticals Inc. | (1H-indol-1-yl)-2-(amino) acetamides and related (1H-indol-1-yl)-(aminoalkyl)amides, pharmaceutical composition and use |
| US5459274A (en) * | 1994-05-13 | 1995-10-17 | Hoechst-Roussel Pharmaceuticals Inc. | Preparation of N-alkyl-N-pyridinyl-1H-indol-1-amines |
| BR9714189A (pt) * | 1996-12-27 | 2000-02-29 | Hoechst Marion Roussel Inc | N-(piridinilamino) isoindolinas e compostos relacionados |
| US6004977A (en) * | 1996-12-27 | 1999-12-21 | Hoechst Marion Roussel, Inc. | N-(pyridinylamino) isoindolines and related compounds |
| US6218383B1 (en) | 1998-08-07 | 2001-04-17 | Targacept, Inc. | Pharmaceutical compositions for the prevention and treatment of central nervous system disorders |
| GT200500063A (es) * | 2004-04-01 | 2005-10-14 | Metodo para tratar la esquizofrenia y/o anormalidades glucoregulatorias | |
| FR2888238B1 (fr) * | 2005-07-07 | 2007-09-07 | Servier Lab | Nouveaux derives 1h-indole-pyridinecarboxamides et 1h-indole-piperidinecarboxamide, leur procede de preparation et les compositions pharceumatiques qui les contiennent. |
| CA2789014C (en) | 2010-02-09 | 2019-01-15 | Michela Gallagher | Methods and compositions for improving cognitive function |
| WO2014078568A1 (en) | 2012-11-14 | 2014-05-22 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| US11160785B2 (en) | 2013-03-15 | 2021-11-02 | Agenebio Inc. | Methods and compositions for improving cognitive function |
| EP3827820A1 (en) | 2013-03-15 | 2021-06-02 | The Johns Hopkins University | Brivaracetam for improving cognitive function |
| BR112017025031B1 (pt) | 2015-05-22 | 2023-03-21 | Agenebio, Inc | Composições farmacêuticas de liberação prolongada de levetiracetam |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4791107A (en) * | 1986-07-16 | 1988-12-13 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use |
| US4970218A (en) * | 1987-04-24 | 1990-11-13 | Hoechst-Roussel Pharmaceuticals Inc. | N-(pyridinyl)-1H-indol-1-amines |
| DE3852335T2 (de) * | 1987-04-24 | 1995-05-11 | Hoechst Roussel Pharma | N-(Pyridinyl)-1H-indol-1-amine, Verfahren zu deren Herstellung und ihre Verwendung als Arzneimittel. |
| US4983615A (en) * | 1989-06-28 | 1991-01-08 | Hoechst-Roussel Pharmaceuticals Inc. | Heteroarylamino- and heteroaryloxypyridinamine compounds which are useful in treating skin disorders |
| US5006537A (en) * | 1989-08-02 | 1991-04-09 | Hoechst-Roussel Pharmaceuticals, Inc. | 1,3-dihydro-1-(pyridinylamino)-2H-indol-2-ones |
| US4992448A (en) * | 1989-10-24 | 1991-02-12 | Hoechst-Roussel Pharmaceuticals Inc. | Benzocycloalkylaminopyridinamines and related compounds as topical antiinflammatory agents for the treatment of skin disorders |
-
1990
- 1990-07-23 US US07/555,890 patent/US5102891A/en not_active Expired - Fee Related
-
1991
- 1991-07-19 FI FI913502A patent/FI102067B1/fi active IP Right Grant
- 1991-07-19 NZ NZ239038A patent/NZ239038A/en unknown
- 1991-07-22 SG SG1996006744A patent/SG48059A1/en unknown
- 1991-07-22 ES ES91112237T patent/ES2121761T3/es not_active Expired - Lifetime
- 1991-07-22 NO NO912866A patent/NO300132B1/no unknown
- 1991-07-22 PT PT98413A patent/PT98413B/pt not_active IP Right Cessation
- 1991-07-22 PL PL29118591A patent/PL291185A1/xx unknown
- 1991-07-22 AT AT91112237T patent/ATE171176T1/de not_active IP Right Cessation
- 1991-07-22 IL IL9892091A patent/IL98920A/en not_active IP Right Cessation
- 1991-07-22 AU AU81216/91A patent/AU639581B2/en not_active Expired - Fee Related
- 1991-07-22 CA CA002047531A patent/CA2047531C/en not_active Expired - Fee Related
- 1991-07-22 IE IE256791A patent/IE912567A1/en not_active IP Right Cessation
- 1991-07-22 DE DE69130196T patent/DE69130196T2/de not_active Expired - Fee Related
- 1991-07-22 ZA ZA915723A patent/ZA915723B/xx unknown
- 1991-07-22 CZ CS912281A patent/CZ283253B6/cs not_active IP Right Cessation
- 1991-07-22 DK DK91112237T patent/DK0468401T3/da active
- 1991-07-22 HU HU912450A patent/HUT58317A/hu unknown
- 1991-07-22 JP JP3181210A patent/JP2564714B2/ja not_active Expired - Fee Related
- 1991-07-22 EP EP91112237A patent/EP0468401B1/en not_active Expired - Lifetime
- 1991-07-23 MX MX9100342A patent/MX9100342A/es not_active IP Right Cessation
- 1991-07-23 KR KR1019910012579A patent/KR100201515B1/ko not_active IP Right Cessation
-
1997
- 1997-04-13 BR BR1100534-3A patent/BR1100534A/pt active IP Right Grant
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