KR960701057A - [1,2,4] 트리아졸로 [4, 3-a] 퀴녹살린 유도체, 이의 제조방법 및 용도([1,2,4]Triazolo[4, 3-a]quinoxaline derivatives, their preparation and use) - Google Patents
[1,2,4] 트리아졸로 [4, 3-a] 퀴녹살린 유도체, 이의 제조방법 및 용도([1,2,4]Triazolo[4, 3-a]quinoxaline derivatives, their preparation and use) Download PDFInfo
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- KR960701057A KR960701057A KR1019950703970A KR19950703970A KR960701057A KR 960701057 A KR960701057 A KR 960701057A KR 1019950703970 A KR1019950703970 A KR 1019950703970A KR 19950703970 A KR19950703970 A KR 19950703970A KR 960701057 A KR960701057 A KR 960701057A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- triazolo
- quinoxaline
- formula
- trifluoromethyl
- Prior art date
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- QNSRYVDGWDXBHV-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoxaline Chemical class C1=CC=C2N3C=NN=C3C=NC2=C1 QNSRYVDGWDXBHV-UHFFFAOYSA-N 0.000 title 2
- 238000002360 preparation method Methods 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 6
- 208000024891 symptom Diseases 0.000 claims abstract 6
- 208000013403 hyperactivity Diseases 0.000 claims abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 230000002964 excitative effect Effects 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 239000002858 neurotransmitter agent Substances 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 3
- 125000001425 triazolyl group Chemical group 0.000 claims abstract 3
- -1 2- Ethoxycarbonylethyl Chemical group 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- 150000001263 acyl chlorides Chemical class 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052709 silver Inorganic materials 0.000 claims 4
- 239000004332 silver Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- NPVOJIUIIYMCKF-UHFFFAOYSA-N 5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound O=C1NC2=CC=CC=C2N2C1=NN=C2 NPVOJIUIIYMCKF-UHFFFAOYSA-N 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- WEQYBMHJHXRZKK-UHFFFAOYSA-N (7-cyano-4-oxo-5h-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)methylphosphonic acid Chemical compound C1=C(C#N)C=C2NC(=O)C3=NN=C(CP(O)(=O)O)N3C2=C1 WEQYBMHJHXRZKK-UHFFFAOYSA-N 0.000 claims 1
- RYJVPEAORJJXLQ-UHFFFAOYSA-N (7-nitro-4-oxo-5h-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)methylphosphonic acid Chemical compound C1=C([N+]([O-])=O)C=C2NC(=O)C3=NN=C(CP(O)(=O)O)N3C2=C1 RYJVPEAORJJXLQ-UHFFFAOYSA-N 0.000 claims 1
- BWOYJOPSMGDEFE-UHFFFAOYSA-N (8-chloro-4-oxo-5h-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)methylphosphonic acid Chemical compound ClC1=CC=C2NC(=O)C3=NN=C(CP(O)(=O)O)N3C2=C1 BWOYJOPSMGDEFE-UHFFFAOYSA-N 0.000 claims 1
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims 1
- KBSXHFLWZBRDJO-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-7-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound C1=C(C(F)(F)F)C=C2NC(=O)C3=NN=C(CP(=O)(OCC)OCC)N3C2=C1 KBSXHFLWZBRDJO-UHFFFAOYSA-N 0.000 claims 1
- WJDRDHPEAWVUFY-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-8-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound FC(F)(F)C1=CC=C2NC(=O)C3=NN=C(CP(=O)(OCC)OCC)N3C2=C1 WJDRDHPEAWVUFY-UHFFFAOYSA-N 0.000 claims 1
- GTTLIPQWHGKADQ-UHFFFAOYSA-N 1-[4-oxo-7-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl]propylphosphonic acid Chemical compound C1=C(C(F)(F)F)C=C2NC(=O)C3=NN=C(C(CC)P(O)(O)=O)N3C2=C1 GTTLIPQWHGKADQ-UHFFFAOYSA-N 0.000 claims 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 claims 1
- AKWLSQRZBIOAGM-UHFFFAOYSA-N 3-[(diethoxyphosphoryl)methyl]benzo[f]-1,2,4-triazolo[4,3-a]quinoxalin-12(11h)-one Chemical compound C1=CC=CC2=C(NC(C3=NN=C(N33)CP(=O)(OCC)OCC)=O)C3=CC=C21 AKWLSQRZBIOAGM-UHFFFAOYSA-N 0.000 claims 1
- KZAQTVQJVOALDK-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-1,2,4-triazole Chemical compound FC(F)(F)C=1N=CNN=1 KZAQTVQJVOALDK-UHFFFAOYSA-N 0.000 claims 1
- ZHRYYFRNMKYZIO-UHFFFAOYSA-N 8-amino-1-(diethoxyphosphorylmethyl)-7-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound NC1=C(C(F)(F)F)C=C2NC(=O)C3=NN=C(CP(=O)(OCC)OCC)N3C2=C1 ZHRYYFRNMKYZIO-UHFFFAOYSA-N 0.000 claims 1
- HCZRUVIRQBDTDO-UHFFFAOYSA-N 8-chloro-1-(diethoxyphosphorylmethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-4-one Chemical compound ClC1=CC=C2NC(=O)C3=NN=C(CP(=O)(OCC)OCC)N3C2=C1 HCZRUVIRQBDTDO-UHFFFAOYSA-N 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- WTOXKFARMGZFTA-UHFFFAOYSA-N C1=CC=CC2=C(NC(C3=NN=C(N33)CP(O)(=O)O)=O)C3=CC=C21 Chemical compound C1=CC=CC2=C(NC(C3=NN=C(N33)CP(O)(=O)O)=O)C3=CC=C21 WTOXKFARMGZFTA-UHFFFAOYSA-N 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- VXJWLIMUJPJRDW-UHFFFAOYSA-N [4-oxo-8-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl]methylphosphonic acid Chemical compound FC(F)(F)C1=CC=C2NC(=O)C3=NN=C(CP(O)(=O)O)N3C2=C1 VXJWLIMUJPJRDW-UHFFFAOYSA-N 0.000 claims 1
- YONXPMGUWFQIMU-UHFFFAOYSA-N [7-cyano-4-oxo-8-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl]methylphosphonic acid Chemical compound FC(F)(F)C1=C(C#N)C=C2NC(=O)C3=NN=C(CP(O)(=O)O)N3C2=C1 YONXPMGUWFQIMU-UHFFFAOYSA-N 0.000 claims 1
- HWKBXSGVLUFORX-UHFFFAOYSA-N [8-nitro-4-oxo-7-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl]methylphosphonic acid Chemical compound [O-][N+](=O)C1=C(C(F)(F)F)C=C2NC(=O)C3=NN=C(CP(O)(=O)O)N3C2=C1 HWKBXSGVLUFORX-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 150000003939 benzylamines Chemical class 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000006392 deoxygenation reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- GQLQDOAJXFSDEP-UHFFFAOYSA-N ethoxy-[[4-oxo-7-(trifluoromethyl)-5h-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl]methyl]phosphinic acid Chemical compound C1=C(C(F)(F)F)C=C2NC(=O)C3=NN=C(CP(O)(=O)OCC)N3C2=C1 GQLQDOAJXFSDEP-UHFFFAOYSA-N 0.000 claims 1
- GSMBUYNBVVIEDY-UHFFFAOYSA-N ethyl 7-nitro-4-oxo-5h-[1,2,4]triazolo[4,3-a]quinoxaline-1-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2NC(=O)C3=NN=C(C(=O)OCC)N3C2=C1 GSMBUYNBVVIEDY-UHFFFAOYSA-N 0.000 claims 1
- 230000009540 excitatory neurotransmission Effects 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000005462 imide group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Classifications
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- 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
-
- 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
- A61P25/28—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
- 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
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Abstract
다음 일반식(I)의 퀴놀살린 화합물은 흥분성 신경 전달물질의 활동 항진에 으해 발생한 증상을 치료하는데 유용하다.
상기 식에서, R1은 COX' 또는 POX'X"이거나, COX' 또는 POX'X"로 치환된 직쇄 또는 측쇄 C1-6알킬이고, X' 및 X"는 독립적으로 하이드록시 또는 C1-6알콕시이고, R6,R7,R8및 R9는 독립적으로 수소, C1-6알킬, 할로겐, NH2, NO2, CN, CF3, SO2NY'Y" 또는 COZ' (여기서, Z'는 NY'Y" 또는 C1-6알킬이고, Y' 및 Y"는 독립적으로 수소 또는 C1-6알킬, 트리아졸릴이 또는 아미다졸릴이거나, 페닐 또는 C1-6알킬로 치환된 이미다졸릴이다)이고, R6과 R7또는 R8과 R9는 함께 추가의 융합된 환을 형성한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 일반식(Ⅰ)의 퀴놀살린 화합물 및 약제학적으로 허용되는 이의 염상기 식에서, R1은 COX′ 또는 POX′X′이거나, COX′ 또는 POX′X″로 치환된 직쇄 또는 측쇄 C1-6알킬이고, X′및 X′는 독립적으로 하이드록시 또는 C1-6알콕시이고, R6,R7,R8및 R9는 독립적으로 수소, C1-6알킬, 할로겐, NH2, NO2, CN, CF3, SO2NY′Y′ 또는 COZ′(여기서, Z′는 NY′Y″는 또는 C1-6알킬이고, Y′및 Y″는 독립적으로 수소 또는 C1-6알킬, 트리아졸릴 또는 이미다졸릴이거나, 페닐 또는 C1-6알킬 로 치환된 이미다졸릴이다)이거나, R6과 R7또는 R8과 R9는 함께 추가의 융합된 환을 형성한다.
- 제1항에 있어서, 융합돈 환이 벤젠 환이 퀴놀살린 화합물.
- 제1항 또는 제2항에 있어서, 1-에톡시카보닐-7-니트로[1,2,4]트리아졸로[4,3-a]퀴녹살린-4(5H)-온;1(2-에톡시카보닐에틸)-7-니트로[1,2,4]트리아졸[4,3a]퀴녹살린-4(5H)-온;1(2-카복시에틸)-7-니트로[1,2,4]트리아졸[4,3a]퀴녹살린-4(5H)-온;7-카바모일-1-(2-카복시에틸)-8-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린-4-(5H)-온; 1-(2-카복시에틸)-7-시아노-8-트리플루오로메틸[1,2,4]트리아졸[4,3a]퀴녹살린-4(5H)-온;1-(2-에톡시카보닐에틸)-7-트리플루오로메틸[1,2,4]트리아졸로-[4,3-a]퀴녹살린-4(5H)-온; 1-(2-카복시에틸)-7-트리플루오로메틸[1,2,4]트리아졸로[4,3,-a]퀴녹살린--4(5H)-온; 1-[2-(디에톡시포스포릴)메틸]-7-트리플루오로메틸[1,2,4]트리아졸로 [4,3,-a]퀴녹살린-4(5H)-온;1-[(디에톡시포스포릴)메틸]-7-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린-4(5H)-온;7-시아노-1-[(디에톡시포스포릴)메틸]-8-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린-4(5H)-은;1-[1-(디에톡시포스포릴)에틸]-7-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린-4(5H)-은;1-[1-(디에톡시포스포릴)프로필]-7-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린-4(5H)-은;7-시아노-1[(디에톡시포스포릴)]메틸][1,2,4]트리아졸로[4,3,-a]퀴녹살린 -4(5H)-온;8-클로로-1-[(디에톡시포스포릴)메틸][1,2,4]트리아졸로[4,3-a]퀴녹살린-4(5H)-온; 1-[(디에톡시포스포릴)메틸]-7-니트로[1,2,4]트리아졸[4,3-a]퀴녹살린-4(5H)-온;1-[(디에톡시포스포릴)메틸]-8-니트로-7트릴플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-은; 8-아미노-1-[(디에톡시포스포릴)메틸]-7-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)--온; 3-[(디에톡시포스포릴)메틸]벤조[f]-1,2,4-트리아졸로[4.3-a]퀴녹살린-12(11H)-온;1-[(디에톡시포스포릴)메틸]-8-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 1-포스포노메틸-7-트리플루오로메틸[1,2,4]트리아졸로[4,3a]퀴녹살린-4(5H)-온: 1-(2-포스포노에틸)-7-트리플 루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 7-시아노-1-포스포노메틸-8-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 7-시아노-1-포스포노메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 1-(1-포스포노에틸)-7-트릴플루오로메틸[]1,2,4트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 8-클로로-1-포스포노메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 8-니트로-1-포스포노메틸-7-ㅡ트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온;1-포스포노메틸-8-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 7-니트로-1포스포노메틸-[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 1-(1-포스포노프로필)-7-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린 -4(5H)-온; 3-포스포노메틸벤조[f]-1,2,4-트리아졸로[4,3-a]퀴녹살린-12(11H)-온; 1-[(에톡시하이드록시포스포릴)메틸]-7-트리플루오로메틸[1,2,4]트리아졸로[4,3-a]퀴녹살린-4(5H)-온;8-브로모-1-[1-(디에톡시포스포릴)에틸]-7-트리플루오로메틸[1,2,4]트리아졸[4,3a]퀴녹살린-4(5H)-온 또는 8-브로모-1-(1-포스포노에틸)-7-|트리플루오로메틸[1,2,4]트리아졸[4,3a]퀴녹살린-4(5H)-온인 화합물.
- 활성 성분으로서의 제1항, 제2항 또는 제3항에 따르는 화합물 또는 약제학적으로 허용되는 이의 염과 약제학적으로 허용되는 담체 또는 희석제를 포함하는 약제학적 조성물.
- 제4항에 있어서, 활성 화합물을 약 10 내지 200mg함유하는 투여 단위의 형태의 약제학적 조성물.
- 활성 성분으로서 제1항, 제2항 또는 제3항에 따르는 화합물 또는 약제학적으로 허용되는 이의 염과 약제학적으로 허용되는 담체 또는 희석제를 포함하는, 흥분성 신경 전달물질의 활동 항진과 관련된 중상을 치료하는데 사용하기에 적합한 약제학적 조성물.
- 흥분성 신경 전달물질의 활동 항진과 관련된 증상을 치료하기 위한 약제를 제조하기 위한, 제1항, 제2항 또는 제3항에 따르는 화합물의 용도.
- 흥분성 신경 전달물질의 활동 항진과 관련된 증상의 치료를 요하는 대상에게 일반식(I)의 화합물 또는 약제학적으로 허용되는 이의 염의 신경학적으로 유효한 AMPA길항량을 투여하는 단계를 포함하여, 흥분성 신경 전달물질의 활동 항진과 관련의 증상의 치료를 요하는 대상의 이러한 증상을 치료하는 방법.상기식에서, R1은 COX′또는 POX′X″이거나, COX′또는 POX′X″로 치환된 직쇄 또는 측쇄 C1-6알킬이고, X′및 X″는 독립적으로 하이드록시 C1-6알콕시이고, R6,R7,R8및 R9는 독립적으로 수소, C1-6알킬, 할로겐, NH2, NO2, CN, CF3, SO2NY′Y″ 또는 COZ′(여기서, Z′는 NY′Y″또는 C1-6알킬이고, Y′및 Y″는 독립적으로 수소 또는 C1-6알킬, 트리아졸릴 또는 이미다졸리이거나, 페닐 또는 C1-6알킬로 치환된 이미다졸릴이다)이고, R6과 R7또는 R8과 R9는 함께 추가의 융합된 환을 형성한다.
- 제8항에 있어서, 중상이 뇌허혈에 관련된 방법.
- 제8항에 있어서, 증상이 파킨슨 증후군에 관련된 방법.
- a)일반식(Ⅱ)의 화합물을 벤질할로게나이드로 알킬화시켜 일반식(Ⅲ)의 호합물을 형성시키고, 이 화합물을 할로겐화시켜 일반식(Ⅳ)의 화합물을 형성시킨 다음, 이 호합물을 히드라진과 반응시켜 일반식(V)의 화합물을 형성시키고, 이 호합물을 일반식(Ⅵ)의 아실 클로라이드로 아실화시켜 일반식(Ⅶ)의 화합물을 형성시킨다음, 이 호합물을 기수소분해시켜 일반식(Ⅷ)의 화합물을 형성시키고, 열 페환과 동시에 탈산소화를 통해 X′및 X″가 C1-6알콕시인 일반식(I)의 화합물을 형성시키거나, b) 일반식 (Ⅸ)의 화합물을 일반식(Ⅵ)의 화합물과 반응시켜 일반식(ⅩI)의 화합물을 형성시킨 다음, 페환시키고, 가수분해하거나 페환과 기수분해를 동시에 수행하여 X′및 X″가 C1-6알콕시인 일반식(I)의 화합물을 형성시키거나, c)일반식(XⅡ)의 화합물을 모노-, 디-또는 트리메톡시 치환된 벤질아민으로 치환시켜 일반식(XⅡ)의 화합물을 형성시키고, 이 화합물을 에틸옥살릴클로라이드와 반응시켜 일반식(ⅩV)의 화합물을 형성시킨다음, 수소화시켜 중간체인 페환된 N-하이드록시 호합물을 형성시키고, 탈산소화시키거나 수소화에 의해 페환시켜 일반식(XV)의 화합물을 형성시키고, 이 화합물을 할로겐화시킨 다음, 수둑한 화합물을 히드라진과 반응시키고, 위에서 정의한 일반식 (Ⅵ)의 아실 클로라이드로 아실화시킨 다음, 페환시켜 일반식(Ⅵ)의 아실 클로라이드로 아실화시킨 다음, 페환시켜 일반식(XⅥ)의 호합물을 형성시키고, 기수분해하여 X′ 및 X″가 C1-6알콕시인 일반식(I)의 화합물을수성염기로 가수분해하여 X′가 하이드록시이고, X″가 C1-6알콕시인 일반식(I)의 화합물을 형성시키거나, e)X′가 하이드록시 또는 C1-6알콕시이고, X″가 C1-6알콕시인 일반식(I)의 화합물을 할로트리메틸실란과 반응시켜 X′ 및 X″가 하이드록시인 일반식(I)의 화합물을 형성시킴을 포함하여, 제1항에 따르는화합물을 제조하는 방법.상기식에서 R1,R6,R7,R8및 R9는 위에서 정의한 바와 동일하고, Q는 Br, Cl 또는 I이고, Z는 할로겐 또는 C1-6알콕시이며, V′및 V″는 독립적으로 수소 또는 메톡시이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| DK93310A DK31093D0 (ko) | 1993-03-19 | 1993-03-19 | |
| DK0310/93 | 1993-03-19 | ||
| PCT/DK1994/000077 WO1994021639A1 (en) | 1993-03-19 | 1994-02-25 | [1,2,4] TRIAZOLO [4,3-a] QUINOXALINE DERIVATIVES, THEIR PREPARATION AND USE |
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| CA2200056A1 (en) * | 1994-09-16 | 1996-03-21 | Novo Nordisk A/S | [1,2,4]triazolo[4,3-a]quinoxalinone derivatives, their preparation and use |
| US5679680A (en) * | 1995-02-16 | 1997-10-21 | Warner-Lambert Company | α-substituted hydrazides having calpain inhibitory activity |
| FR2743363A1 (fr) * | 1996-01-10 | 1997-07-11 | Rhone Poulenc Rorer Sa | 5h,10h-imidazo(1,2-a)indeno(1,2-e)pyrazine-a-ones substituees en position 2, leur preparation et les medicaments les contenant |
| IL125950A0 (en) * | 1997-09-05 | 1999-04-11 | Pfizer Prod Inc | Methods of administering ampa receptor antagonists to treat dyskinesias associated with dopamine agonist therapy |
| AU9651198A (en) | 1997-11-11 | 1999-05-31 | Ono Pharmaceutical Co. Ltd. | Fused pyrazine compounds |
| AU2298399A (en) * | 1998-02-06 | 1999-08-23 | Yoshitomi Pharmaceutical Industries, Ltd. | Novel azapeptide type hydroxamic acid derivatives |
| US20040152694A1 (en) * | 2003-02-04 | 2004-08-05 | Istvan Kurucz | Methods and compositions for treating inflammatory disorders of the airways |
| ES2536906T3 (es) * | 2006-12-13 | 2015-05-29 | Aska Pharmaceutical Co., Ltd. | Derivado de quinoxalina |
| CN102341399A (zh) * | 2009-03-05 | 2012-02-01 | 安斯泰来制药株式会社 | 喹喔啉化合物 |
| EP2338492A1 (en) | 2009-12-24 | 2011-06-29 | Universidad del Pais Vasco | Methods and compositions for the treatment of alzheimer |
| AU2011299936A1 (en) | 2010-09-07 | 2013-03-28 | Astellas Pharma Inc. | Quinoxaline compound |
| BR112013033375B1 (pt) | 2011-06-27 | 2022-05-10 | Janssen Pharmaceutica N.V | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxa-lina, seu uso, composição farmacêutica que os compreende, processo de preparação dos mesmos, solução estéril e composto intermediário |
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|---|---|---|---|---|
| US4354027A (en) * | 1980-05-19 | 1982-10-12 | Usv Pharmaceutical Corporation | Triazoloquinoxalin-4-ones |
| US4547501A (en) * | 1983-09-02 | 1985-10-15 | Pfizer Inc. | Method of using [1,2,4]triazolo[4,3-a]quinoxaline-4-amine derivatives as antidepressant and antifatigue agents |
| US5153196A (en) * | 1991-06-05 | 1992-10-06 | Eli Lilly And Company | Excitatory amino acid receptor antagonists and methods for the use thereof |
| AU3767793A (en) * | 1992-04-03 | 1993-11-08 | Yamanouchi Pharmaceutical Co., Ltd. | Fused quinoxalinone derivative and pharmaceutical composition containing the same |
-
1993
- 1993-03-19 DK DK93310A patent/DK31093D0/da not_active Application Discontinuation
-
1994
- 1994-02-25 AU AU62018/94A patent/AU685783B2/en not_active Ceased
- 1994-02-25 CN CN94191979A patent/CN1041930C/zh not_active Expired - Fee Related
- 1994-02-25 CA CA002158545A patent/CA2158545A1/en not_active Abandoned
- 1994-02-25 NZ NZ262365A patent/NZ262365A/en unknown
- 1994-02-25 JP JP6520538A patent/JPH08507536A/ja active Pending
- 1994-02-25 WO PCT/DK1994/000077 patent/WO1994021639A1/en not_active Application Discontinuation
- 1994-02-25 EP EP94908979A patent/EP0691969A1/en not_active Withdrawn
- 1994-02-25 KR KR1019950703970A patent/KR100313051B1/ko not_active IP Right Cessation
- 1994-02-25 HU HU9502726A patent/HUT73419A/hu unknown
- 1994-02-28 TW TW083101703A patent/TW304195B/zh active
- 1994-03-01 IL IL108800A patent/IL108800A/en active IP Right Grant
- 1994-03-18 ZA ZA941926A patent/ZA941926B/xx unknown
- 1994-12-07 US US08/350,744 patent/US5559106A/en not_active Expired - Fee Related
-
1995
- 1995-09-18 NO NO953673A patent/NO305286B1/no not_active IP Right Cessation
- 1995-09-18 FI FI954386A patent/FI954386A/fi unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1041930C (zh) | 1999-02-03 |
| AU685783B2 (en) | 1998-01-29 |
| IL108800A (en) | 1998-02-22 |
| NO305286B1 (no) | 1999-05-03 |
| HUT73419A (en) | 1996-07-29 |
| FI954386A0 (fi) | 1995-09-18 |
| JPH08507536A (ja) | 1996-08-13 |
| EP0691969A1 (en) | 1996-01-17 |
| KR100313051B1 (ko) | 2002-02-28 |
| TW304195B (ko) | 1997-05-01 |
| NO953673L (no) | 1995-11-17 |
| IL108800A0 (en) | 1994-06-24 |
| NO953673D0 (no) | 1995-09-18 |
| ZA941926B (en) | 1995-09-18 |
| DK31093D0 (ko) | 1993-03-19 |
| HU9502726D0 (en) | 1995-11-28 |
| US5559106A (en) | 1996-09-24 |
| CA2158545A1 (en) | 1994-09-29 |
| FI954386A (fi) | 1995-09-18 |
| AU6201894A (en) | 1994-10-11 |
| CN1122601A (zh) | 1996-05-15 |
| NZ262365A (en) | 1997-05-26 |
| WO1994021639A1 (en) | 1994-09-29 |
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