SK113399A3 - Quinoxalinediones - Google Patents
Quinoxalinediones Download PDFInfo
- Publication number
- SK113399A3 SK113399A3 SK1133-99A SK113399A SK113399A3 SK 113399 A3 SK113399 A3 SK 113399A3 SK 113399 A SK113399 A SK 113399A SK 113399 A3 SK113399 A3 SK 113399A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- compound
- pharmaceutically acceptable
- solvate
- acceptable salt
- Prior art date
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- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical class C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000012453 solvate Substances 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 12
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 10
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
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- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
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- 229940099433 NMDA receptor antagonist Drugs 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 24
- 239000000543 intermediate Substances 0.000 abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
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- 230000000052 comparative effect Effects 0.000 description 13
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 11
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- 238000005481 NMR spectroscopy Methods 0.000 description 10
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- -1 pyridine compound Chemical class 0.000 description 7
- IEMAQDHGZOPMNI-UHFFFAOYSA-N 6,7-dichloro-5-[3-(methoxymethyl)-5-(1-oxidopyridin-1-ium-3-yl)-1,2,4-triazol-4-yl]-1,4-dihydroquinoxaline-2,3-dione Chemical compound ClC=1C(Cl)=CC=2NC(=O)C(=O)NC=2C=1N1C(COC)=NN=C1C1=CC=C[N+]([O-])=C1 IEMAQDHGZOPMNI-UHFFFAOYSA-N 0.000 description 6
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical class C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
- 239000012425 OXONE® Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
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- 238000000338 in vitro Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
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- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- YDYJCQIIFXPRMI-UHFFFAOYSA-N 6,7-dichloro-5-[3-(methoxymethyl)-5-pyridin-3-yl-1,2,4-triazol-4-yl]-1,4-dihydroquinoxaline-2,3-dione Chemical compound ClC=1C(Cl)=CC=2NC(=O)C(=O)NC=2C=1N1C(COC)=NN=C1C1=CC=CN=C1 YDYJCQIIFXPRMI-UHFFFAOYSA-N 0.000 description 3
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- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
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- 235000013922 glutamic acid Nutrition 0.000 description 3
- 239000004220 glutamic acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- GYQDMMSNDKWZLY-UHFFFAOYSA-N 2,3,6,7-tetrachloro-5-nitroquinoxaline Chemical compound ClC1=C(Cl)N=C2C([N+](=O)[O-])=C(Cl)C(Cl)=CC2=N1 GYQDMMSNDKWZLY-UHFFFAOYSA-N 0.000 description 2
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- JSFLFNPZGIDUBV-UHFFFAOYSA-N 3-(2-amino-3-hydroxy-5-methyl-3h-1,2-oxazol-4-yl)propanoic acid Chemical compound CC1=C(CCC(O)=O)C(O)N(N)O1 JSFLFNPZGIDUBV-UHFFFAOYSA-N 0.000 description 2
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- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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
- C07D401/14—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
-
- 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
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- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1997/000995 WO1997032873A1 (en) | 1996-03-09 | 1997-02-27 | Quinoxalinediones |
| GBGB9715783.8A GB9715783D0 (en) | 1997-02-27 | 1997-07-25 | Quinoxalinediones |
| PCT/EP1998/001275 WO1998038186A1 (en) | 1997-02-27 | 1998-02-24 | Quinoxalinediones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK113399A3 true SK113399A3 (en) | 2001-04-09 |
Family
ID=26070194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1133-99A SK113399A3 (en) | 1997-02-27 | 1998-02-24 | Quinoxalinediones |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0973766B1 (es) |
| JP (2) | JP3588363B2 (es) |
| CN (2) | CN1121403C (es) |
| AT (1) | ATE282608T1 (es) |
| BG (1) | BG103685A (es) |
| BR (1) | BR9808126A (es) |
| CA (1) | CA2281580C (es) |
| DE (1) | DE69827614T2 (es) |
| ES (1) | ES2230685T3 (es) |
| HR (1) | HRP980104A2 (es) |
| HU (1) | HUP0003612A3 (es) |
| NO (1) | NO994135L (es) |
| NZ (1) | NZ336842A (es) |
| SK (1) | SK113399A3 (es) |
| TR (1) | TR199902055T2 (es) |
| WO (1) | WO1998038186A1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9605027D0 (en) * | 1996-03-09 | 1996-05-08 | Pfizer Ltd | Quinoxalinediones |
| GB0310881D0 (en) * | 2003-05-12 | 2003-06-18 | Merck Sharp & Dohme | Pharmaceutical formulation |
| MY145368A (en) | 2004-01-13 | 2012-01-31 | Nissan Chemical Ind Ltd | Aminoquinoxaline compounds and polyaminoquinoxaline compounds, and use thereof |
| WO2005076295A1 (ja) | 2004-02-06 | 2005-08-18 | Yamaguchi University | エネルギー貯蔵デバイス用電極及びその製造方法 |
| JP2009539846A (ja) * | 2006-06-06 | 2009-11-19 | ブリストル−ミエルス スクイッブ カンパニー | Ｎ−［５−［［［５−（１，１−ジメチルエチル）−２−オキサゾリル］メチル］チオ］−２−チアゾリル］−４−ピペリジンカルボキサミドの結晶形 |
| WO2008143019A1 (en) | 2007-05-17 | 2008-11-27 | Semiconductor Energy Laboratory Co., Ltd. | Triazole derivative, and light-emitting element, light-emitting device, and electronic device with the use of triazole derivative |
| JP5806672B2 (ja) * | 2009-10-30 | 2015-11-10 | ドメイン・セラピューティクス | 新規オキシム誘導体及び代謝型グルタミン酸受容体のアロステリック調節因子としての利用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE194985T1 (de) * | 1990-11-06 | 2000-08-15 | Yamanouchi Pharma Co Ltd | Kondensiertes pyrazinderivat |
| DE4217952A1 (de) * | 1992-05-30 | 1993-12-02 | Basf Ag | Chinoxalin-2,3(1H,4H)-dione |
| GB9605027D0 (en) * | 1996-03-09 | 1996-05-08 | Pfizer Ltd | Quinoxalinediones |
-
1998
- 1998-02-24 WO PCT/EP1998/001275 patent/WO1998038186A1/en active IP Right Grant
- 1998-02-24 DE DE69827614T patent/DE69827614T2/de not_active Expired - Fee Related
- 1998-02-24 NZ NZ336842A patent/NZ336842A/xx unknown
- 1998-02-24 EP EP98913660A patent/EP0973766B1/en not_active Expired - Lifetime
- 1998-02-24 TR TR1999/02055T patent/TR199902055T2/xx unknown
- 1998-02-24 CN CN98802879A patent/CN1121403C/zh not_active Expired - Fee Related
- 1998-02-24 HU HU0003612A patent/HUP0003612A3/hu unknown
- 1998-02-24 JP JP53732798A patent/JP3588363B2/ja not_active Expired - Fee Related
- 1998-02-24 CA CA002281580A patent/CA2281580C/en not_active Expired - Fee Related
- 1998-02-24 SK SK1133-99A patent/SK113399A3/sk unknown
- 1998-02-24 BR BR9808126-8A patent/BR9808126A/pt not_active Application Discontinuation
- 1998-02-24 AT AT98913660T patent/ATE282608T1/de not_active IP Right Cessation
- 1998-02-24 ES ES98913660T patent/ES2230685T3/es not_active Expired - Lifetime
- 1998-02-26 HR HR9715783.8A patent/HRP980104A2/hr not_active Application Discontinuation
-
1999
- 1999-08-24 BG BG103685A patent/BG103685A/bg unknown
- 1999-08-26 NO NO994135A patent/NO994135L/no unknown
-
2003
- 2003-03-20 CN CN03107362A patent/CN1443763A/zh active Pending
-
2004
- 2004-07-02 JP JP2004196277A patent/JP2004269547A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| TR199902055T2 (xx) | 2000-07-21 |
| CA2281580A1 (en) | 1998-09-03 |
| NO994135D0 (no) | 1999-08-26 |
| JP2000509730A (ja) | 2000-08-02 |
| NO994135L (no) | 1999-10-22 |
| HUP0003612A3 (en) | 2003-04-28 |
| CN1248971A (zh) | 2000-03-29 |
| CN1121403C (zh) | 2003-09-17 |
| HRP980104A2 (en) | 1999-02-28 |
| JP3588363B2 (ja) | 2004-11-10 |
| JP2004269547A (ja) | 2004-09-30 |
| CA2281580C (en) | 2003-04-22 |
| BG103685A (bg) | 2000-06-30 |
| ATE282608T1 (de) | 2004-12-15 |
| ES2230685T3 (es) | 2005-05-01 |
| DE69827614T2 (de) | 2005-11-10 |
| WO1998038186A1 (en) | 1998-09-03 |
| CN1443763A (zh) | 2003-09-24 |
| NZ336842A (en) | 2000-05-26 |
| DE69827614D1 (de) | 2004-12-23 |
| EP0973766A1 (en) | 2000-01-26 |
| HUP0003612A2 (hu) | 2001-10-28 |
| EP0973766B1 (en) | 2004-11-17 |
| BR9808126A (pt) | 2000-03-08 |
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