NO310236B1 - Nye 2,3-diokso-1,2,3,4-tetrahydro-quinoksalinylderivater og farmasöytisk sammensetning omfattende samme - Google Patents
Nye 2,3-diokso-1,2,3,4-tetrahydro-quinoksalinylderivater og farmasöytisk sammensetning omfattende samme Download PDFInfo
- Publication number
- NO310236B1 NO310236B1 NO19980814A NO980814A NO310236B1 NO 310236 B1 NO310236 B1 NO 310236B1 NO 19980814 A NO19980814 A NO 19980814A NO 980814 A NO980814 A NO 980814A NO 310236 B1 NO310236 B1 NO 310236B1
- Authority
- NO
- Norway
- Prior art keywords
- dioxo
- tetrahydroquinoxalin
- ylmethyl
- nitro
- acid
- Prior art date
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- -1 2,3-dioxo-1,2,3,4-tetrahydroquinoxalinyl Chemical class 0.000 title claims description 72
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 208
- 150000003839 salts Chemical class 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000001118 alkylidene group Chemical group 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- XGUOQIARSDZLAZ-UHFFFAOYSA-N 2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methoxy]acetic acid Chemical compound OC1=C(O)N=C2C(COCC(=O)O)=CC(Br)=CC2=N1 XGUOQIARSDZLAZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000004471 Glycine Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 102000005962 receptors Human genes 0.000 claims description 4
- 108020003175 receptors Proteins 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 102000000079 Kainic Acid Receptors Human genes 0.000 claims description 3
- 108010069902 Kainic Acid Receptors Proteins 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- NVQLTEKPZZTDBI-UHFFFAOYSA-N [(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]methylphosphonic acid Chemical compound BrC1=CC(CNCP(O)(O)=O)=C2N=C(O)C(O)=NC2=C1 NVQLTEKPZZTDBI-UHFFFAOYSA-N 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- DPFHVUSPVHRVFL-UHFFFAOYSA-N 1-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNC(C)P(O)(O)=O DPFHVUSPVHRVFL-UHFFFAOYSA-N 0.000 claims 1
- VGCLKYODUBTNNY-UHFFFAOYSA-N 1-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C=C2CNC(C)P(O)(O)=O VGCLKYODUBTNNY-UHFFFAOYSA-N 0.000 claims 1
- NCFGQCDRYNURBV-UHFFFAOYSA-N 2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]acetic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNCC(=O)O NCFGQCDRYNURBV-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 190
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
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- 238000001704 evaporation Methods 0.000 description 39
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- 239000007858 starting material Substances 0.000 description 39
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
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- 239000004480 active ingredient Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 239000002585 base Substances 0.000 description 18
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- 125000006239 protecting group Chemical group 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 239000013078 crystal Substances 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- WIQNHLFZBWOETQ-UHFFFAOYSA-N 5-(bromomethyl)-2,3-dimethoxy-7-nitroquinoxaline Chemical compound [O-][N+](=O)C1=CC(CBr)=C2N=C(OC)C(OC)=NC2=C1 WIQNHLFZBWOETQ-UHFFFAOYSA-N 0.000 description 15
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- 159000000001 potassium salts Chemical class 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical compound C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
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- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- QNZVAJAEXIYEKC-UHFFFAOYSA-N tert-butyl 1-[(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methyl]pyrrole-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=CN1CC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 QNZVAJAEXIYEKC-UHFFFAOYSA-N 0.000 description 1
- WQWVPKRSNYVMQO-UHFFFAOYSA-N tert-butyl 1-[2-(7-nitro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC(C)(C)C)CCN1CCC1=CC([N+]([O-])=O)=CC2=C1NC(=O)C(=O)N2 WQWVPKRSNYVMQO-UHFFFAOYSA-N 0.000 description 1
- XROHVGYAJUNRJG-UHFFFAOYSA-N tert-butyl 2-[(7-bromo-2,3-dimethoxyquinoxalin-5-yl)methylamino]acetate Chemical compound BrC1=CC(CNCC(=O)OC(C)(C)C)=C2N=C(OC)C(OC)=NC2=C1 XROHVGYAJUNRJG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TWQLHXSOTFRECS-UHFFFAOYSA-N tert-butyl n-[2-[(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)methylamino]-2-oxoethyl]carbamate Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CNC(=O)CNC(=O)OC(C)(C)C TWQLHXSOTFRECS-UHFFFAOYSA-N 0.000 description 1
- FUYBPBOHNIHCHM-UHFFFAOYSA-N tert-butyl piperidine-4-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCNCC1 FUYBPBOHNIHCHM-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
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- 230000009466 transformation Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
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- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
-
- 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
- A61P25/28—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
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
- C07F9/650994—Six-membered rings having the nitrogen atoms in the positions 1 and 4 condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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CH247995 | 1995-08-31 | ||
CH273495 | 1995-09-27 | ||
CH274795 | 1995-09-28 | ||
CH121396 | 1996-05-10 | ||
CH163096 | 1996-06-28 | ||
PCT/EP1996/003644 WO1997008155A1 (en) | 1995-08-31 | 1996-08-19 | Novel 2,3-dioxo-1,2,3,4-tetrahydro-quinoyxalinyl derivatives |
Publications (3)
Publication Number | Publication Date |
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NO980814D0 NO980814D0 (no) | 1998-02-26 |
NO980814L NO980814L (no) | 1998-04-21 |
NO310236B1 true NO310236B1 (no) | 2001-06-11 |
Family
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Application Number | Title | Priority Date | Filing Date |
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NO19980814A NO310236B1 (no) | 1995-08-31 | 1998-02-26 | Nye 2,3-diokso-1,2,3,4-tetrahydro-quinoksalinylderivater og farmasöytisk sammensetning omfattende samme |
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US (1) | US6080743A (cs) |
EP (1) | EP0853617B1 (cs) |
JP (1) | JP3159711B2 (cs) |
KR (1) | KR100462337B1 (cs) |
CN (1) | CN1137886C (cs) |
AR (1) | AR005229A1 (cs) |
AT (1) | ATE260902T1 (cs) |
AU (1) | AU705871B2 (cs) |
BR (1) | BRPI9603626B8 (cs) |
CA (1) | CA2227851C (cs) |
CZ (1) | CZ56298A3 (cs) |
DE (1) | DE69631774T2 (cs) |
DK (1) | DK0853617T3 (cs) |
ES (1) | ES2217324T3 (cs) |
HK (1) | HK1010196A1 (cs) |
HU (1) | HUP9801676A3 (cs) |
IL (1) | IL122987A (cs) |
MY (1) | MY132385A (cs) |
NO (1) | NO310236B1 (cs) |
NZ (1) | NZ316497A (cs) |
PL (1) | PL189637B1 (cs) |
PT (1) | PT853617E (cs) |
SI (1) | SI0853617T1 (cs) |
SK (1) | SK25298A3 (cs) |
TR (1) | TR199800349T2 (cs) |
WO (1) | WO1997008155A1 (cs) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1997046539A1 (en) * | 1996-06-05 | 1997-12-11 | Warner-Lambert Company | Amide derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
WO1998017672A1 (de) * | 1996-10-24 | 1998-04-30 | Novartis Ag | Substituierte aminoalkanphosphonsäuren |
WO1998023599A1 (en) * | 1996-11-25 | 1998-06-04 | Warner-Lambert Company | Urea and thiourea derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
GB9702194D0 (en) | 1997-02-04 | 1997-03-26 | Lilly Co Eli | Sulphonide derivatives |
US6172065B1 (en) * | 1997-03-04 | 2001-01-09 | Warner-Lambert Company | Urea and thiourea derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
US6340758B1 (en) | 1997-05-16 | 2002-01-22 | Warner-Lambert Company | Conformationally semi-constrained quinoxaline 2,3-diones as neuroprotective agents |
US6096744A (en) * | 1998-05-04 | 2000-08-01 | Warner-Lambert Company | Sulfonamide derivatives of substituted quinoxaline 2,3-diones as glutamate receptor antagonists |
US6677332B1 (en) | 1999-05-25 | 2004-01-13 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US6635661B2 (en) | 2000-05-25 | 2003-10-21 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
US7361666B2 (en) | 1999-05-25 | 2008-04-22 | Sepracor, Inc. | Heterocyclic analgesic compounds and methods of use thereof |
WO2001092226A1 (en) * | 2000-05-25 | 2001-12-06 | Sepracor, Inc. | Heterocyclic analgesic compounds and method of use thereof |
AU2002250256B2 (en) * | 2001-03-08 | 2008-04-03 | Emory University | pH-dependent NMDA receptor antagonists |
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JP2007507514A (ja) * | 2003-09-30 | 2007-03-29 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | キノキサリン化合物 |
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US4156734A (en) * | 1976-02-13 | 1979-05-29 | Merck & Co., Inc. | Antihypertensive compositions containing an aryl-substituted alanine azo and an arylhydrazino-propionic acid |
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US5631373A (en) * | 1993-11-05 | 1997-05-20 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon, Eugene Oregon | Alkyl, azido, alkoxy, and fluoro-substituted and fused quinoxalinediones |
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GB9419318D0 (en) * | 1994-09-24 | 1994-11-09 | Pfizer Ltd | Therapeutic agents |
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1996
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- 1996-08-19 US US09/029,525 patent/US6080743A/en not_active Expired - Lifetime
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- 1996-08-19 CA CA002227851A patent/CA2227851C/en not_active Expired - Fee Related
- 1996-08-19 EP EP96929275A patent/EP0853617B1/en not_active Expired - Lifetime
- 1996-08-19 DK DK96929275T patent/DK0853617T3/da active
- 1996-08-19 TR TR1998/00349T patent/TR199800349T2/xx unknown
- 1996-08-19 KR KR10-1998-0701511A patent/KR100462337B1/ko not_active IP Right Cessation
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- 1996-08-19 WO PCT/EP1996/003644 patent/WO1997008155A1/en not_active Application Discontinuation
- 1996-08-19 CZ CZ98562A patent/CZ56298A3/cs unknown
- 1996-08-19 DE DE69631774T patent/DE69631774T2/de not_active Expired - Lifetime
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- 1996-08-19 CN CNB961965819A patent/CN1137886C/zh not_active Expired - Fee Related
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1998
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