NO327813B1 - Pyridazinoner og triazinoner og deres anvendelse, samt farmasoytisk preparat - Google Patents
Pyridazinoner og triazinoner og deres anvendelse, samt farmasoytisk preparat Download PDFInfo
- Publication number
- NO327813B1 NO327813B1 NO20031232A NO20031232A NO327813B1 NO 327813 B1 NO327813 B1 NO 327813B1 NO 20031232 A NO20031232 A NO 20031232A NO 20031232 A NO20031232 A NO 20031232A NO 327813 B1 NO327813 B1 NO 327813B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- pyridyl
- dihydro
- pyridazinone
- phenyl
- Prior art date
Links
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 21
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 102000003678 AMPA Receptors Human genes 0.000 claims abstract description 29
- 108090000078 AMPA Receptors Proteins 0.000 claims abstract description 29
- 102000000079 Kainic Acid Receptors Human genes 0.000 claims abstract description 18
- 108010069902 Kainic Acid Receptors Proteins 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
- 125000004429 atom Chemical group 0.000 claims abstract description 7
- -1 N-oxypyridinyl group Chemical group 0.000 claims description 83
- 125000001424 substituent group Chemical group 0.000 claims description 37
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 102000005962 receptors Human genes 0.000 claims description 7
- 108020003175 receptors Proteins 0.000 claims description 7
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- TVPRCLHSULCNLV-UHFFFAOYSA-N pyridazin-3-one Chemical compound O=C1C=CC=N[N]1 TVPRCLHSULCNLV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- LQHWAPLDYPZETA-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2-hydroxyphenyl)-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound OC1=CC=CC=C1C1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 LQHWAPLDYPZETA-UHFFFAOYSA-N 0.000 claims description 4
- JSPRICIZLIUCOL-UHFFFAOYSA-N 2-(3-oxo-6-pyridin-2-yl-4-pyridin-3-yl-5h-1,2,4-triazin-2-yl)benzonitrile Chemical compound O=C1N(C=2C=NC=CC=2)CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N JSPRICIZLIUCOL-UHFFFAOYSA-N 0.000 claims description 4
- QYDGHZTXJKYKKM-UHFFFAOYSA-N 2-(2-bromophenyl)-4-phenyl-6-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)N(C=2C=CC=CC=2)CC(C=2N=CC=CC=2)=N1 QYDGHZTXJKYKKM-UHFFFAOYSA-N 0.000 claims description 3
- FNIFYFAAHGUWBW-UHFFFAOYSA-N 2-(2-bromophenyl)-6-pyridin-2-yl-4-pyridin-3-yl-5h-1,2,4-triazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)N(C=2C=NC=CC=2)CC(C=2N=CC=CC=2)=N1 FNIFYFAAHGUWBW-UHFFFAOYSA-N 0.000 claims description 3
- HMMNPXCRCZPJKL-UHFFFAOYSA-N 4-(2-hydroxyphenyl)-2-phenyl-6-pyridin-2-ylpyridazin-3-one Chemical compound OC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1 HMMNPXCRCZPJKL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005972 dihydrochromenyl group Chemical group 0.000 claims description 2
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 claims 1
- 108091006082 receptor inhibitors Proteins 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 12
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 abstract 1
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 abstract 1
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- 238000006243 chemical reaction Methods 0.000 description 108
- 238000005160 1H NMR spectroscopy Methods 0.000 description 100
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 100
- 238000000034 method Methods 0.000 description 59
- 239000002904 solvent Substances 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000007858 starting material Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- 238000005481 NMR spectroscopy Methods 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 238000003756 stirring Methods 0.000 description 38
- 239000003153 chemical reaction reagent Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 35
- 239000012044 organic layer Substances 0.000 description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 28
- 238000010898 silica gel chromatography Methods 0.000 description 27
- 101150041968 CDC13 gene Proteins 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 238000001816 cooling Methods 0.000 description 23
- 239000000126 substance Substances 0.000 description 22
- 201000010099 disease Diseases 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- 239000002274 desiccant Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 17
- 239000002585 base Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 13
- 230000001154 acute effect Effects 0.000 description 13
- 229930195712 glutamate Natural products 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 208000016192 Demyelinating disease Diseases 0.000 description 12
- 241000699666 Mus <mouse, genus> Species 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 210000005036 nerve Anatomy 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 150000002429 hydrazines Chemical class 0.000 description 9
- 230000004770 neurodegeneration Effects 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 241000725303 Human immunodeficiency virus Species 0.000 description 8
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 8
- 210000002569 neuron Anatomy 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 206010028570 Myelopathy Diseases 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 206010047700 Vomiting Diseases 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 238000006482 condensation reaction Methods 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 208000015122 neurodegenerative disease Diseases 0.000 description 7
- 208000008795 neuromyelitis optica Diseases 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical class O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 6
- 239000005749 Copper compound Substances 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 6
- 208000018737 Parkinson disease Diseases 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000001880 copper compounds Chemical class 0.000 description 6
- 230000002964 excitative effect Effects 0.000 description 6
- 229920000609 methyl cellulose Polymers 0.000 description 6
- 235000010981 methylcellulose Nutrition 0.000 description 6
- 239000001923 methylcellulose Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 6
- 230000008673 vomiting Effects 0.000 description 6
- 208000024827 Alzheimer disease Diseases 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 206010019196 Head injury Diseases 0.000 description 5
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 206010029350 Neurotoxicity Diseases 0.000 description 5
- 206010044221 Toxic encephalopathy Diseases 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001543 aryl boronic acids Chemical class 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 206010008118 cerebral infarction Diseases 0.000 description 5
- 208000026106 cerebrovascular disease Diseases 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 201000002491 encephalomyelitis Diseases 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000002366 halogen compounds Chemical class 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 230000033001 locomotion Effects 0.000 description 5
- 201000001119 neuropathy Diseases 0.000 description 5
- 230000007823 neuropathy Effects 0.000 description 5
- 230000007135 neurotoxicity Effects 0.000 description 5
- 231100000228 neurotoxicity Toxicity 0.000 description 5
- 239000002858 neurotransmitter agent Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 208000020431 spinal cord injury Diseases 0.000 description 5
- ZWMQVBSLMQSMDH-UHFFFAOYSA-N (2-bromophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Br ZWMQVBSLMQSMDH-UHFFFAOYSA-N 0.000 description 4
- QTOYCVKORUSALI-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2-methoxyphenyl)-6-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound COC1=CC=CC=C1N1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 QTOYCVKORUSALI-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 description 4
- 206010010904 Convulsion Diseases 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
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 4
- 241000598436 Human T-cell lymphotropic virus Species 0.000 description 4
- 208000023105 Huntington disease Diseases 0.000 description 4
- 206010021143 Hypoxia Diseases 0.000 description 4
- 201000009906 Meningitis Diseases 0.000 description 4
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 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 4
- 206010069350 Osmotic demyelination syndrome Diseases 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 208000021386 Sjogren Syndrome Diseases 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 210000001015 abdomen Anatomy 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 208000002552 acute disseminated encephalomyelitis Diseases 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 210000001130 astrocyte Anatomy 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 208000011235 central nervous system lupus Diseases 0.000 description 4
- 208000009885 central pontine myelinolysis Diseases 0.000 description 4
- 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 description 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 4
- 206010061811 demyelinating polyneuropathy Diseases 0.000 description 4
- 206010014599 encephalitis Diseases 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000007954 hypoxia Effects 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 230000002458 infectious effect Effects 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 208000033808 peripheral neuropathy Diseases 0.000 description 4
- 239000008177 pharmaceutical agent Substances 0.000 description 4
- 201000006292 polyarteritis nodosa Diseases 0.000 description 4
- 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 description 4
- 201000000306 sarcoidosis Diseases 0.000 description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- OHEZPKARGJQEAD-UHFFFAOYSA-N 2,4-diphenyl-6-pyrimidin-2-yl-5h-1,2,4-triazin-3-one Chemical compound O=C1N(C=2C=CC=CC=2)CC(C=2N=CC=CN=2)=NN1C1=CC=CC=C1 OHEZPKARGJQEAD-UHFFFAOYSA-N 0.000 description 3
- GKPFPDRHFJQWDB-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2-methoxyphenyl)-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=CC=C1C1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 GKPFPDRHFJQWDB-UHFFFAOYSA-N 0.000 description 3
- IFDVQABODWWPTP-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(3-hydroxyphenyl)-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound OC1=CC=CC(C2C(N(N=C(C2)C=2N=CC=CC=2)C=2C(=CC=CC=2)Br)=O)=C1 IFDVQABODWWPTP-UHFFFAOYSA-N 0.000 description 3
- BRUYQBYIUHMRTP-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(3-methoxyphenyl)-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=CC(C2C(N(N=C(C2)C=2N=CC=CC=2)C=2C(=CC=CC=2)Br)=O)=C1 BRUYQBYIUHMRTP-UHFFFAOYSA-N 0.000 description 3
- JUAKSFXOINYRHP-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(3-nitrophenyl)-6-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound [O-][N+](=O)C1=CC=CC(N2C(N(N=C(C2)C=2N=CC=CC=2)C=2C(=CC=CC=2)Br)=O)=C1 JUAKSFXOINYRHP-UHFFFAOYSA-N 0.000 description 3
- RXEYNKMQYAJVDR-UHFFFAOYSA-N 2-(2-bromophenyl)-4-[3-(2-hydroxyethoxy)phenyl]-6-pyridin-2-ylpyridazin-3-one Chemical compound OCCOC1=CC=CC(C=2C(N(C=3C(=CC=CC=3)Br)N=C(C=2)C=2N=CC=CC=2)=O)=C1 RXEYNKMQYAJVDR-UHFFFAOYSA-N 0.000 description 3
- ZTUXFCDRNFLBGE-UHFFFAOYSA-N 2-(2-bromophenyl)-6-(2-hydroxyphenyl)-4-phenyl-5H-1,2,4-triazin-3-one Chemical compound OC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)N(C=2C=CC=CC=2)C1 ZTUXFCDRNFLBGE-UHFFFAOYSA-N 0.000 description 3
- XHMXEBUFDWGTTE-UHFFFAOYSA-N 2-(2-bromophenyl)-6-pyridin-2-yl-4,5-dihydro-1,2,4-triazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)NCC(C=2N=CC=CC=2)=N1 XHMXEBUFDWGTTE-UHFFFAOYSA-N 0.000 description 3
- ABALQBCFKNCRBK-UHFFFAOYSA-N 2-(2-bromophenyl)-6-pyridin-2-yl-4-pyridin-3-ylpyridazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)C(C=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=N1 ABALQBCFKNCRBK-UHFFFAOYSA-N 0.000 description 3
- NSMXWIBVWJWRAA-UHFFFAOYSA-N 2-(2-cyanophenyl)-4H-1,3,2-dioxaborinine-4-carboxylic acid Chemical compound O1C=CC(C(=O)O)OB1C1=CC=CC=C1C#N NSMXWIBVWJWRAA-UHFFFAOYSA-N 0.000 description 3
- UYGONENNGRZMPI-UHFFFAOYSA-N 2-(2-iodophenyl)-4-pyridin-3-yl-4a,5-dihydro-4h-chromeno[4,3-c]pyridazin-3-one Chemical compound IC1=CC=CC=C1N1C(=O)C(C=2C=NC=CC=2)C(COC=2C3=CC=CC=2)C3=N1 UYGONENNGRZMPI-UHFFFAOYSA-N 0.000 description 3
- DCHJJSZVIIYTFQ-UHFFFAOYSA-N 2-(3-methylphenyl)-6-pyridin-2-yl-4-pyridin-3-ylpyridazin-3-one Chemical compound CC1=CC=CC(N2C(C(C=3C=NC=CC=3)=CC(=N2)C=2N=CC=CC=2)=O)=C1 DCHJJSZVIIYTFQ-UHFFFAOYSA-N 0.000 description 3
- LKENQPKIWLWVPA-UHFFFAOYSA-N 2-(3-oxo-2-phenyl-6-pyridin-2-yl-5h-1,2,4-triazin-4-yl)benzonitrile Chemical compound O=C1N(C=2C(=CC=CC=2)C#N)CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1 LKENQPKIWLWVPA-UHFFFAOYSA-N 0.000 description 3
- JFWGVXPHWWJQIK-UHFFFAOYSA-N 2-(3-oxo-4,6-dipyridin-2-yl-5h-1,2,4-triazin-2-yl)benzonitrile Chemical compound O=C1N(C=2N=CC=CC=2)CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N JFWGVXPHWWJQIK-UHFFFAOYSA-N 0.000 description 3
- JSSINMWIXHFMFQ-UHFFFAOYSA-N 2-(3-oxo-4-phenyl-4a,5-dihydro-4h-chromeno[4,3-c]pyridazin-2-yl)benzonitrile Chemical compound O=C1C(C=2C=CC=CC=2)C2COC3=CC=CC=C3C2=NN1C1=CC=CC=C1C#N JSSINMWIXHFMFQ-UHFFFAOYSA-N 0.000 description 3
- JNZPVGCWGREADO-UHFFFAOYSA-N 2-[2-(2-cyanophenyl)-3-oxo-6-pyridin-2-ylpyridazin-4-yl]benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N JNZPVGCWGREADO-UHFFFAOYSA-N 0.000 description 3
- MRIBYNAJRDWBCE-UHFFFAOYSA-N 2-[4-(3-nitrophenyl)-3-oxo-6-pyridin-2-yl-5h-1,2,4-triazin-2-yl]benzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(N2C(N(N=C(C2)C=2N=CC=CC=2)C=2C(=CC=CC=2)C#N)=O)=C1 MRIBYNAJRDWBCE-UHFFFAOYSA-N 0.000 description 3
- XSFVIQRTXVPFDV-UHFFFAOYSA-N 3-(6-oxo-5-phenyl-3-pyridin-2-ylpyridazin-1-yl)pyridine-2-carbonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=NN1C1=CC=CN=C1C#N XSFVIQRTXVPFDV-UHFFFAOYSA-N 0.000 description 3
- ARDMVQMTYJOQRW-UHFFFAOYSA-N 3-(6-oxo-5-phenyl-3-pyrimidin-2-ylpyridazin-1-yl)pyridine-2-carbonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CN=2)=NN1C1=CC=CN=C1C#N ARDMVQMTYJOQRW-UHFFFAOYSA-N 0.000 description 3
- AVRDERICICSKDO-UHFFFAOYSA-N 5-(6-oxo-5-phenyl-3-pyridin-2-ylpyridazin-1-yl)pyridine-2-carbonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=NN1C1=CC=C(C#N)N=C1 AVRDERICICSKDO-UHFFFAOYSA-N 0.000 description 3
- IXOFDXRIVXNXLB-UHFFFAOYSA-N 5-(6-oxo-5-phenyl-3-pyrimidin-2-ylpyridazin-1-yl)pyridine-2-carbonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CN=2)=NN1C1=CC=C(C#N)N=C1 IXOFDXRIVXNXLB-UHFFFAOYSA-N 0.000 description 3
- LAKGGRBFYHMPGV-UHFFFAOYSA-N 6-chloro-3-methoxy-4-phenylpyridazine Chemical compound COC1=NN=C(Cl)C=C1C1=CC=CC=C1 LAKGGRBFYHMPGV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 206010008025 Cerebellar ataxia Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- 206010012305 Demyelination Diseases 0.000 description 3
- 206010013654 Drug abuse Diseases 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000013016 Hypoglycemia Diseases 0.000 description 3
- 208000008238 Muscle Spasticity Diseases 0.000 description 3
- 241000282341 Mustela putorius furo Species 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 3
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 208000010112 Spinocerebellar Degenerations Diseases 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 230000000049 anti-anxiety effect Effects 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 230000009460 calcium influx Effects 0.000 description 3
- 230000006315 carbonylation Effects 0.000 description 3
- 238000005810 carbonylation reaction Methods 0.000 description 3
- 208000010353 central nervous system vasculitis Diseases 0.000 description 3
- 210000003710 cerebral cortex Anatomy 0.000 description 3
- 230000002490 cerebral effect Effects 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 229940014259 gelatin Drugs 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 125000003106 haloaryl group Chemical group 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 3
- 210000003141 lower extremity Anatomy 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229960001252 methamphetamine Drugs 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000006606 n-butoxy group Chemical group 0.000 description 3
- 230000036963 noncompetitive effect Effects 0.000 description 3
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 3
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical class OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 201000000980 schizophrenia Diseases 0.000 description 3
- 125000005920 sec-butoxy group Chemical group 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 208000018198 spasticity Diseases 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 208000011117 substance-related disease Diseases 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
- UQNAFPHGVPVTAL-UHFFFAOYSA-N 2,3-Dihydroxy-6-nitro-7-sulfamoyl-benzo(f)quinoxaline Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C1=C2C=CC=C1S(=O)(=O)N UQNAFPHGVPVTAL-UHFFFAOYSA-N 0.000 description 2
- JFYGBOGSHXEWJQ-UHFFFAOYSA-N 2,4-bis(2-bromophenyl)-6-phenyl-5h-1,2,4-triazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2C=CC=CC=2)C1 JFYGBOGSHXEWJQ-UHFFFAOYSA-N 0.000 description 2
- AKFGDZFPBVYSFM-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-6-pyridin-2-yl-4-pyridin-3-ylpyridazin-3-one Chemical compound N=1N(C=2C=C3OCOC3=CC=2)C(=O)C(C=2C=NC=CC=2)=CC=1C1=CC=CC=N1 AKFGDZFPBVYSFM-UHFFFAOYSA-N 0.000 description 2
- OBIAUVXYGFQAAX-UHFFFAOYSA-N 2-(2-bromophenyl)-4,6-diphenyl-5h-1,2,4-triazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)N(C=2C=CC=CC=2)CC(C=2C=CC=CC=2)=N1 OBIAUVXYGFQAAX-UHFFFAOYSA-N 0.000 description 2
- FTGUIBBTAABTLZ-UHFFFAOYSA-N 2-(2-bromophenyl)-4,6-dipyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)N(C=2N=CC=CC=2)CC(C=2N=CC=CC=2)=N1 FTGUIBBTAABTLZ-UHFFFAOYSA-N 0.000 description 2
- SGRRHZHEHOBYAG-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2,5-dihydroxyphenyl)-6-(2-hydroxyphenyl)-5H-1,2,4-triazin-3-one Chemical compound OC1=CC=C(O)C(N2C(N(N=C(C2)C=2C(=CC=CC=2)O)C=2C(=CC=CC=2)Br)=O)=C1 SGRRHZHEHOBYAG-UHFFFAOYSA-N 0.000 description 2
- BDEMXNQMXSCFPF-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2,5-dimethoxyphenyl)-6-(2-methoxyphenyl)-5h-1,2,4-triazin-3-one Chemical compound COC1=CC=C(OC)C(N2C(N(N=C(C2)C=2C(=CC=CC=2)OC)C=2C(=CC=CC=2)Br)=O)=C1 BDEMXNQMXSCFPF-UHFFFAOYSA-N 0.000 description 2
- RRNUYWMDDAECQQ-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2-hydroxyphenyl)-6-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound OC1=CC=CC=C1N1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 RRNUYWMDDAECQQ-UHFFFAOYSA-N 0.000 description 2
- PMHJZHTXNGXXHH-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2-hydroxyphenyl)-6-pyridin-2-ylpyridazin-3-one Chemical compound OC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1Br PMHJZHTXNGXXHH-UHFFFAOYSA-N 0.000 description 2
- BXTBUHUZOOJXNW-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2-hydroxyphenyl)-6-pyridin-3-yl-4,5-dihydropyridazin-3-one Chemical compound OC1=CC=CC=C1C1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2C=NC=CC=2)C1 BXTBUHUZOOJXNW-UHFFFAOYSA-N 0.000 description 2
- SWTLDTDTDNQNOF-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(2-methoxyphenyl)-6-pyridin-3-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=CC=C1C1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2C=NC=CC=2)C1 SWTLDTDTDNQNOF-UHFFFAOYSA-N 0.000 description 2
- BSRAUWBNYZHVRB-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(3-methoxyphenyl)-6-pyridin-2-ylpyridazin-3-one Chemical compound COC1=CC=CC(C=2C(N(C=3C(=CC=CC=3)Br)N=C(C=2)C=2N=CC=CC=2)=O)=C1 BSRAUWBNYZHVRB-UHFFFAOYSA-N 0.000 description 2
- KWNIWEFCAQMERN-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(3-methylphenyl)-6-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound CC1=CC=CC(N2C(N(N=C(C2)C=2N=CC=CC=2)C=2C(=CC=CC=2)Br)=O)=C1 KWNIWEFCAQMERN-UHFFFAOYSA-N 0.000 description 2
- MBIXIEATXPXSBH-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(4-fluorophenyl)-6-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound C1=CC(F)=CC=C1N1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 MBIXIEATXPXSBH-UHFFFAOYSA-N 0.000 description 2
- KORRPYMSCPQPSY-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(4-hydroxyphenyl)-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound C1=CC(O)=CC=C1C1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 KORRPYMSCPQPSY-UHFFFAOYSA-N 0.000 description 2
- LCGIQQQRVPGSFY-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(4-methoxyphenyl)-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound C1=CC(OC)=CC=C1C1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 LCGIQQQRVPGSFY-UHFFFAOYSA-N 0.000 description 2
- PSPWTOYNIPLKLW-UHFFFAOYSA-N 2-(2-bromophenyl)-4-[2-[2-(dimethylamino)ethoxy]phenyl]-6-pyridin-2-ylpyridazin-3-one Chemical compound CN(C)CCOC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1Br PSPWTOYNIPLKLW-UHFFFAOYSA-N 0.000 description 2
- CZFTTYSOAYKAML-UHFFFAOYSA-N 2-(2-bromophenyl)-4-phenyl-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)C(C=2C=CC=CC=2)CC(C=2N=CC=CC=2)=N1 CZFTTYSOAYKAML-UHFFFAOYSA-N 0.000 description 2
- PRHRWOJLAUFPEN-UHFFFAOYSA-N 2-(2-bromophenyl)-4-phenyl-6-pyridin-2-ylpyridazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=N1 PRHRWOJLAUFPEN-UHFFFAOYSA-N 0.000 description 2
- NDNULXNKTKWWEI-UHFFFAOYSA-N 2-(2-bromophenyl)-4-phenyl-6-pyridin-3-yl-4,5-dihydropyridazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)C(C=2C=CC=CC=2)CC(C=2C=NC=CC=2)=N1 NDNULXNKTKWWEI-UHFFFAOYSA-N 0.000 description 2
- CZSRTMADENBWLD-UHFFFAOYSA-N 2-(2-bromophenyl)-4-pyridin-3-yl-4a,5-dihydro-4h-chromeno[4,3-c]pyridazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)C(C=2C=NC=CC=2)C(COC=2C3=CC=CC=2)C3=N1 CZSRTMADENBWLD-UHFFFAOYSA-N 0.000 description 2
- KSPXGYMYWUADDK-UHFFFAOYSA-N 2-(2-bromophenyl)-6-(2-hydroxyphenyl)-4-pyridin-2-ylpyridazin-3-one Chemical compound OC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)C(C=2N=CC=CC=2)=C1 KSPXGYMYWUADDK-UHFFFAOYSA-N 0.000 description 2
- FBVGPGQXIRABMB-UHFFFAOYSA-N 2-(2-bromophenyl)-6-(2-methoxyphenyl)-4-phenyl-5h-1,2,4-triazin-3-one Chemical compound COC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)N(C=2C=CC=CC=2)C1 FBVGPGQXIRABMB-UHFFFAOYSA-N 0.000 description 2
- RGVVQIAWFNYZBE-UHFFFAOYSA-N 2-(2-bromophenyl)-6-(2-methoxyphenyl)-4-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound COC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)N(C=2N=CC=CC=2)C1 RGVVQIAWFNYZBE-UHFFFAOYSA-N 0.000 description 2
- SCRBOHOCDMUCNI-UHFFFAOYSA-N 2-(2-bromophenyl)-6-(2-methoxyphenyl)-4-pyridin-2-ylpyridazin-3-one Chemical compound COC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)C(C=2N=CC=CC=2)=C1 SCRBOHOCDMUCNI-UHFFFAOYSA-N 0.000 description 2
- XSSAHVOPLJAPOY-UHFFFAOYSA-N 2-(2-bromophenyl)-6-(2-methoxyphenyl)-4-thiophen-3-yl-5h-1,2,4-triazin-3-one Chemical compound COC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)N(C2=CSC=C2)C1 XSSAHVOPLJAPOY-UHFFFAOYSA-N 0.000 description 2
- DRBZLUTUNILDFX-UHFFFAOYSA-N 2-(2-bromophenyl)-6-[2-[2-(dimethylamino)ethoxy]phenyl]-4-phenyl-5h-1,2,4-triazin-3-one Chemical compound CN(C)CCOC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)N(C=2C=CC=CC=2)C1 DRBZLUTUNILDFX-UHFFFAOYSA-N 0.000 description 2
- OLVGCXKWCSFCQX-UHFFFAOYSA-N 2-(2-bromophenyl)-6-[2-[2-(dimethylamino)ethoxy]phenyl]-4-pyridin-2-ylpyridazin-3-one Chemical compound CN(C)CCOC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)C(C=2N=CC=CC=2)=C1 OLVGCXKWCSFCQX-UHFFFAOYSA-N 0.000 description 2
- CTGICMAZKJVGAA-UHFFFAOYSA-N 2-(2-bromophenyl)-6-pyridin-2-yl-4-thiophen-3-yl-5h-1,2,4-triazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)N(C2=CSC=C2)CC(C=2N=CC=CC=2)=N1 CTGICMAZKJVGAA-UHFFFAOYSA-N 0.000 description 2
- FPPAWYGGRBXDEW-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-phenyl-6-pyrimidin-2-yl-5h-1,2,4-triazin-3-one Chemical compound ClC1=CC=CC=C1N1C(=O)N(C=2C=CC=CC=2)CC(C=2N=CC=CN=2)=N1 FPPAWYGGRBXDEW-UHFFFAOYSA-N 0.000 description 2
- SMIDAWSVUKBKIM-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-phenyl-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound FC1=CC=CC=C1N1C(=O)C(C=2C=CC=CC=2)CC(C=2N=CC=CC=2)=N1 SMIDAWSVUKBKIM-UHFFFAOYSA-N 0.000 description 2
- SEWVFNQJCSIQTM-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4-phenyl-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=CC=C1N1C(=O)C(C=2C=CC=CC=2)CC(C=2N=CC=CC=2)=N1 SEWVFNQJCSIQTM-UHFFFAOYSA-N 0.000 description 2
- UPEBITCZECJWKU-UHFFFAOYSA-N 2-(2-methoxyphenyl)-6-pyridin-2-yl-4-pyridin-3-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=CC=C1N1C(=O)C(C=2C=NC=CC=2)CC(C=2N=CC=CC=2)=N1 UPEBITCZECJWKU-UHFFFAOYSA-N 0.000 description 2
- XPRJAWWTDUTGPG-UHFFFAOYSA-N 2-(2-nitrophenyl)-4-phenyl-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound [O-][N+](=O)C1=CC=CC=C1N1C(=O)C(C=2C=CC=CC=2)CC(C=2N=CC=CC=2)=N1 XPRJAWWTDUTGPG-UHFFFAOYSA-N 0.000 description 2
- QLSZMDWTJXGYNL-UHFFFAOYSA-N 2-(2-nitrophenyl)-6-pyridin-2-yl-4-pyridin-3-ylpyridazin-3-one Chemical compound [O-][N+](=O)C1=CC=CC=C1N1C(=O)C(C=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=N1 QLSZMDWTJXGYNL-UHFFFAOYSA-N 0.000 description 2
- OIFPBWDKHDVPRV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-6-pyridin-2-yl-4-pyridin-3-ylpyridazin-3-one Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)C(C=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=N1 OIFPBWDKHDVPRV-UHFFFAOYSA-N 0.000 description 2
- PXAMOKLMAWSBOA-UHFFFAOYSA-N 2-(3-methoxyphenyl)-4-oxo-4-pyridin-2-ylbutanenitrile Chemical compound COC1=CC=CC(C(CC(=O)C=2N=CC=CC=2)C#N)=C1 PXAMOKLMAWSBOA-UHFFFAOYSA-N 0.000 description 2
- OTUIQLWYYRCHTN-UHFFFAOYSA-N 2-(3-methoxyphenyl)-4-oxo-4-pyridin-2-ylbutanoic acid Chemical compound COC1=CC=CC(C(CC(=O)C=2N=CC=CC=2)C(O)=O)=C1 OTUIQLWYYRCHTN-UHFFFAOYSA-N 0.000 description 2
- BJDYNUBAENZZBS-UHFFFAOYSA-N 2-(3-oxo-2-phenyl-6-pyridin-2-ylpyridazin-4-yl)benzonitrile Chemical compound O=C1C(C=2C(=CC=CC=2)C#N)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1 BJDYNUBAENZZBS-UHFFFAOYSA-N 0.000 description 2
- CPGUZYBPUWGVIP-UHFFFAOYSA-N 2-(3-oxo-4-phenyl-5h-chromeno[4,3-c]pyridazin-2-yl)benzonitrile Chemical compound C=12COC3=CC=CC=C3C2=NN(C=2C(=CC=CC=2)C#N)C(=O)C=1C1=CC=CC=C1 CPGUZYBPUWGVIP-UHFFFAOYSA-N 0.000 description 2
- QNEPEHWLEDQFPO-UHFFFAOYSA-N 2-(3-oxo-4-pyridin-3-yl-4a,5-dihydro-4h-chromeno[4,3-c]pyridazin-2-yl)benzonitrile Chemical compound O=C1C(C=2C=NC=CC=2)C2COC3=CC=CC=C3C2=NN1C1=CC=CC=C1C#N QNEPEHWLEDQFPO-UHFFFAOYSA-N 0.000 description 2
- DMPSSFJELMETKB-UHFFFAOYSA-N 2-(3-oxo-4-pyridin-3-yl-5h-chromeno[4,3-c]pyridazin-2-yl)benzonitrile Chemical compound C=12COC3=CC=CC=C3C2=NN(C=2C(=CC=CC=2)C#N)C(=O)C=1C1=CC=CN=C1 DMPSSFJELMETKB-UHFFFAOYSA-N 0.000 description 2
- MZJXPVCSEVINNJ-UHFFFAOYSA-N 2-(3-oxo-6-pyridin-2-yl-4-thiophen-3-yl-5h-1,2,4-triazin-2-yl)benzonitrile Chemical compound O=C1N(C2=CSC=C2)CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N MZJXPVCSEVINNJ-UHFFFAOYSA-N 0.000 description 2
- BJHSLWUCMGPANV-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-6-pyridin-2-yl-4-pyridin-3-ylpyridazin-3-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(=O)C(C=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=N1 BJHSLWUCMGPANV-UHFFFAOYSA-N 0.000 description 2
- QPSOSQOMXZDLLK-UHFFFAOYSA-N 2-(6-oxo-3-pyridin-2-yl-5-pyridin-3-ylpyridazin-1-yl)benzonitrile Chemical compound O=C1C(C=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N QPSOSQOMXZDLLK-UHFFFAOYSA-N 0.000 description 2
- YIDZBKZJLMWAKW-UHFFFAOYSA-N 2-(6-oxo-5-phenyl-3-pyrazin-2-ylpyridazin-1-yl)benzonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=NC=2)=NN1C1=CC=CC=C1C#N YIDZBKZJLMWAKW-UHFFFAOYSA-N 0.000 description 2
- RJEZHXGMUYLWOU-UHFFFAOYSA-N 2-(6-oxo-5-phenyl-3-pyridin-2-ylpyridazin-1-yl)benzonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N RJEZHXGMUYLWOU-UHFFFAOYSA-N 0.000 description 2
- SRUKRSJFKHSSGA-UHFFFAOYSA-N 2-(6-oxo-5-phenyl-3-pyrimidin-2-ylpyridazin-1-yl)benzonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CN=2)=NN1C1=CC=CC=C1C#N SRUKRSJFKHSSGA-UHFFFAOYSA-N 0.000 description 2
- VNOQAHSUSCDWGT-UHFFFAOYSA-N 2-(9-fluoro-3-oxo-4-phenyl-4a,5-dihydro-4h-chromeno[4,3-c]pyridazin-2-yl)benzonitrile Chemical compound N1=C2C3=CC(F)=CC=C3OCC2C(C=2C=CC=CC=2)C(=O)N1C1=CC=CC=C1C#N VNOQAHSUSCDWGT-UHFFFAOYSA-N 0.000 description 2
- QIVAFORMVCHCHT-UHFFFAOYSA-N 2-(9-fluoro-5-hydroxy-3-oxo-4-phenyl-5h-chromeno[4,3-c]pyridazin-2-yl)benzonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=C2C(O)OC3=CC=C(F)C=C3C2=NN1C1=CC=CC=C1C#N QIVAFORMVCHCHT-UHFFFAOYSA-N 0.000 description 2
- GBNMTGNUYRUYHS-UHFFFAOYSA-N 2-(n-methoxycarbonylanilino)acetic acid Chemical compound COC(=O)N(CC(O)=O)C1=CC=CC=C1 GBNMTGNUYRUYHS-UHFFFAOYSA-N 0.000 description 2
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 2
- UEFUZUNVPLSVST-UHFFFAOYSA-N 2-[2-(2-bromophenyl)-3-oxo-6-pyridin-2-yl-5h-1,2,4-triazin-4-yl]benzonitrile Chemical compound BrC1=CC=CC=C1N1C(=O)N(C=2C(=CC=CC=2)C#N)CC(C=2N=CC=CC=2)=N1 UEFUZUNVPLSVST-UHFFFAOYSA-N 0.000 description 2
- SSHWQNOKIHSLLN-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)-3-oxo-6-pyridin-2-yl-5h-1,2,4-triazin-2-yl]benzonitrile Chemical compound OC1=CC=CC=C1N1C(=O)N(C=2C(=CC=CC=2)C#N)N=C(C=2N=CC=CC=2)C1 SSHWQNOKIHSLLN-UHFFFAOYSA-N 0.000 description 2
- DJRGCQLCZRABRI-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)-3-oxo-6-pyridin-2-yl-5h-1,2,4-triazin-2-yl]benzonitrile Chemical compound COC1=CC=CC=C1N1C(=O)N(C=2C(=CC=CC=2)C#N)N=C(C=2N=CC=CC=2)C1 DJRGCQLCZRABRI-UHFFFAOYSA-N 0.000 description 2
- ORBNOHQTZJOJCK-UHFFFAOYSA-N 2-[4-(3-aminophenyl)-3-oxo-6-pyridin-2-yl-5h-1,2,4-triazin-2-yl]benzonitrile Chemical compound NC1=CC=CC(N2C(N(N=C(C2)C=2N=CC=CC=2)C=2C(=CC=CC=2)C#N)=O)=C1 ORBNOHQTZJOJCK-UHFFFAOYSA-N 0.000 description 2
- IBSWOEJYVNQTGN-UHFFFAOYSA-N 2-[5-(2-bromophenyl)-6-oxo-3-pyridin-2-ylpyridazin-1-yl]benzonitrile Chemical compound BrC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N IBSWOEJYVNQTGN-UHFFFAOYSA-N 0.000 description 2
- NKSQBDGOIRTVNF-UHFFFAOYSA-N 2-[5-(2-hydroxyphenyl)-6-oxo-3-pyridin-2-yl-4,5-dihydropyridazin-1-yl]benzonitrile Chemical compound OC1=CC=CC=C1C1C(=O)N(C=2C(=CC=CC=2)C#N)N=C(C=2N=CC=CC=2)C1 NKSQBDGOIRTVNF-UHFFFAOYSA-N 0.000 description 2
- NXGICQNYZCVZBU-UHFFFAOYSA-N 2-[5-(2-hydroxyphenyl)-6-oxo-3-pyridin-2-ylpyridazin-1-yl]benzonitrile Chemical compound OC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N NXGICQNYZCVZBU-UHFFFAOYSA-N 0.000 description 2
- BEJKIKHYZJXMJM-UHFFFAOYSA-N 2-[5-(2-methoxyphenyl)-6-oxo-3-pyridin-2-yl-4,5-dihydropyridazin-1-yl]benzonitrile Chemical compound COC1=CC=CC=C1C1C(=O)N(C=2C(=CC=CC=2)C#N)N=C(C=2N=CC=CC=2)C1 BEJKIKHYZJXMJM-UHFFFAOYSA-N 0.000 description 2
- ROOTXBYZUVZJBB-UHFFFAOYSA-N 2-[5-(5-bromo-2-methoxyphenyl)-6-oxo-3-pyridin-2-ylpyridazin-1-yl]benzonitrile Chemical compound COC1=CC=C(Br)C=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N ROOTXBYZUVZJBB-UHFFFAOYSA-N 0.000 description 2
- GSRQEKJILVGFDU-UHFFFAOYSA-N 2-[5-[3-(2-hydroxyethoxy)phenyl]-6-oxo-3-pyridin-2-ylpyridazin-1-yl]benzonitrile Chemical compound OCCOC1=CC=CC(C=2C(N(C=3C(=CC=CC=3)C#N)N=C(C=2)C=2N=CC=CC=2)=O)=C1 GSRQEKJILVGFDU-UHFFFAOYSA-N 0.000 description 2
- MBFUAGZCSSIGCH-UHFFFAOYSA-N 2-[6-(2-hydroxyphenyl)-3-oxo-4-phenyl-5H-1,2,4-triazin-2-yl]benzonitrile Chemical compound OC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)C#N)C(=O)N(C=2C=CC=CC=2)C1 MBFUAGZCSSIGCH-UHFFFAOYSA-N 0.000 description 2
- AYKYFSKRBHXBEA-UHFFFAOYSA-N 2-[6-(2-methoxyphenyl)-3-oxo-2-phenyl-5h-1,2,4-triazin-4-yl]benzonitrile Chemical compound COC1=CC=CC=C1C1=NN(C=2C=CC=CC=2)C(=O)N(C=2C(=CC=CC=2)C#N)C1 AYKYFSKRBHXBEA-UHFFFAOYSA-N 0.000 description 2
- LYFRHOHYMNOBSK-UHFFFAOYSA-N 2-[6-(2-methoxyphenyl)-3-oxo-4-pyridin-2-yl-5h-1,2,4-triazin-2-yl]benzonitrile Chemical compound COC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)C#N)C(=O)N(C=2N=CC=CC=2)C1 LYFRHOHYMNOBSK-UHFFFAOYSA-N 0.000 description 2
- UNFVOVKYALIGRN-UHFFFAOYSA-N 2-[6-oxo-5-phenyl-3-(1,3-thiazol-2-yl)pyridazin-1-yl]benzonitrile Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2SC=CN=2)=NN1C1=CC=CC=C1C#N UNFVOVKYALIGRN-UHFFFAOYSA-N 0.000 description 2
- 125000003858 2-ethylbutoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])O*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- 125000005924 2-methylpentyloxy group Chemical group 0.000 description 2
- IFQHHMZJYIWAOH-UHFFFAOYSA-N 2-naphthalen-2-yl-6-pyridin-2-yl-4-pyridin-3-ylpyridazin-3-one Chemical compound N=1N(C=2C=C3C=CC=CC3=CC=2)C(=O)C(C=2C=NC=CC=2)=CC=1C1=CC=CC=N1 IFQHHMZJYIWAOH-UHFFFAOYSA-N 0.000 description 2
- FFWSZEOHUXIBRE-UHFFFAOYSA-N 2-phenyl-6-pyridin-2-yl-4-pyridin-3-yl-5h-1,2,4-triazin-3-one Chemical compound O=C1N(C=2C=NC=CC=2)CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1 FFWSZEOHUXIBRE-UHFFFAOYSA-N 0.000 description 2
- JZTXMQBHILRMFR-UHFFFAOYSA-N 2-phenyl-6-pyridin-2-yl-4-pyridin-3-ylpyridazin-3-one Chemical compound O=C1C(C=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1 JZTXMQBHILRMFR-UHFFFAOYSA-N 0.000 description 2
- MOURUFSRRCLKDG-UHFFFAOYSA-N 2-phenyl-6-pyridin-2-yl-4-thiophen-3-yl-5h-1,2,4-triazin-3-one Chemical compound O=C1N(C2=CSC=C2)CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1 MOURUFSRRCLKDG-UHFFFAOYSA-N 0.000 description 2
- NAVCBNMXKUTXLT-UHFFFAOYSA-N 3-(6-oxo-3-pyridin-2-yl-5-pyridin-3-ylpyridazin-1-yl)benzaldehyde Chemical compound O=CC1=CC=CC(N2C(C(C=3C=NC=CC=3)=CC(=N2)C=2N=CC=CC=2)=O)=C1 NAVCBNMXKUTXLT-UHFFFAOYSA-N 0.000 description 2
- JTQKJZHTOPZLPS-UHFFFAOYSA-N 3-[2-(2-bromophenyl)-3-oxo-6-pyridin-2-yl-5h-1,2,4-triazin-4-yl]benzaldehyde Chemical compound BrC1=CC=CC=C1N1C(=O)N(C=2C=C(C=O)C=CC=2)CC(C=2N=CC=CC=2)=N1 JTQKJZHTOPZLPS-UHFFFAOYSA-N 0.000 description 2
- ULGROYWSRHANED-UHFFFAOYSA-N 3-methoxy-4-phenyl-6-pyrimidin-2-ylpyridazine Chemical compound COC1=NN=C(C=2N=CC=CN=2)C=C1C1=CC=CC=C1 ULGROYWSRHANED-UHFFFAOYSA-N 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005917 3-methylpentyl group Chemical group 0.000 description 2
- 125000005925 3-methylpentyloxy group Chemical group 0.000 description 2
- UCYIAXOWEZBFGV-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)-2-phenyl-6-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound COC1=CC(OC)=CC=C1N1C(=O)N(C=2C=CC=CC=2)N=C(C=2N=CC=CC=2)C1 UCYIAXOWEZBFGV-UHFFFAOYSA-N 0.000 description 2
- OKLVBKCJAWOPHL-UHFFFAOYSA-N 4-(2,5-dihydroxyphenyl)-6-(2-hydroxyphenyl)-2-phenyl-5H-1,2,4-triazin-3-one Chemical compound OC1=CC=C(O)C(N2C(N(N=C(C2)C=2C(=CC=CC=2)O)C=2C=CC=CC=2)=O)=C1 OKLVBKCJAWOPHL-UHFFFAOYSA-N 0.000 description 2
- ZFCQIDAMKAZCBF-UHFFFAOYSA-N 4-(2,5-dimethoxyphenyl)-6-(2-methoxyphenyl)-2-phenyl-5h-1,2,4-triazin-3-one Chemical compound COC1=CC=C(OC)C(N2C(N(N=C(C2)C=2C(=CC=CC=2)OC)C=2C=CC=CC=2)=O)=C1 ZFCQIDAMKAZCBF-UHFFFAOYSA-N 0.000 description 2
- FUJCOPAWIBOCTM-UHFFFAOYSA-N 4-(2-bromophenyl)-2,6-diphenyl-5h-1,2,4-triazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)N(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)C1 FUJCOPAWIBOCTM-UHFFFAOYSA-N 0.000 description 2
- WKJAECXZUDEDLI-UHFFFAOYSA-N 4-(2-bromophenyl)-2-phenyl-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound BrC1=CC=CC=C1C1C(=O)N(C=2C=CC=CC=2)N=C(C=2N=CC=CC=2)C1 WKJAECXZUDEDLI-UHFFFAOYSA-N 0.000 description 2
- AOMMRFFGUYCQPE-UHFFFAOYSA-N 4-(2-bromophenyl)-2-phenyl-6-pyridin-2-ylpyridazin-3-one Chemical compound BrC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1 AOMMRFFGUYCQPE-UHFFFAOYSA-N 0.000 description 2
- CHGDPQCHQQCPQM-UHFFFAOYSA-N 4-(2-bromophenyl)-6-(2-methoxyphenyl)-2-phenyl-5h-1,2,4-triazin-3-one Chemical compound COC1=CC=CC=C1C1=NN(C=2C=CC=CC=2)C(=O)N(C=2C(=CC=CC=2)Br)C1 CHGDPQCHQQCPQM-UHFFFAOYSA-N 0.000 description 2
- ISAMKLYODVTVIT-UHFFFAOYSA-N 4-(2-hydroxyphenyl)-2-phenyl-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound OC1=CC=CC=C1C1C(=O)N(C=2C=CC=CC=2)N=C(C=2N=CC=CC=2)C1 ISAMKLYODVTVIT-UHFFFAOYSA-N 0.000 description 2
- DBSJVWISQGYNDF-UHFFFAOYSA-N 4-(2-methoxyphenyl)-2,6-dipyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=CC=C1C1C(=O)N(C=2N=CC=CC=2)N=C(C=2N=CC=CC=2)C1 DBSJVWISQGYNDF-UHFFFAOYSA-N 0.000 description 2
- QTGZMYDFXNXGNM-UHFFFAOYSA-N 4-(2-methoxyphenyl)-2-phenyl-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=CC=C1C1C(=O)N(C=2C=CC=CC=2)N=C(C=2N=CC=CC=2)C1 QTGZMYDFXNXGNM-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- ODXXSBWIRCVJAY-UHFFFAOYSA-N 4-oxo-4-pyridin-2-yl-2-pyridin-3-ylbutanoic acid Chemical compound C=1C=CN=CC=1C(C(=O)O)CC(=O)C1=CC=CC=N1 ODXXSBWIRCVJAY-UHFFFAOYSA-N 0.000 description 2
- UECKJMMZKCIFDG-UHFFFAOYSA-N 4-phenyl-2,4,4a,5-tetrahydrochromeno[4,3-c]pyridazin-3-one Chemical compound O=C1NN=C(C2=CC=CC=C2OC2)C2C1C1=CC=CC=C1 UECKJMMZKCIFDG-UHFFFAOYSA-N 0.000 description 2
- IKGSDMKRUWWSQO-UHFFFAOYSA-N 4-phenyl-2-pyridin-3-yl-6-pyrimidin-2-ylpyridazin-3-one Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CN=2)=NN1C1=CC=CN=C1 IKGSDMKRUWWSQO-UHFFFAOYSA-N 0.000 description 2
- ZRENPMIXWZGVTB-UHFFFAOYSA-N 4-phenyl-6-pyridin-2-yl-2-pyridin-3-ylpyridazin-3-one Chemical compound O=C1C(C=2C=CC=CC=2)=CC(C=2N=CC=CC=2)=NN1C1=CC=CN=C1 ZRENPMIXWZGVTB-UHFFFAOYSA-N 0.000 description 2
- CAKLREUVQRUYDZ-UHFFFAOYSA-N 5-phenyl-3-pyrimidin-2-yl-1h-pyridazin-6-one Chemical compound O=C1NN=C(C=2N=CC=CN=2)C=C1C1=CC=CC=C1 CAKLREUVQRUYDZ-UHFFFAOYSA-N 0.000 description 2
- ZWRYMXWENDLITR-UHFFFAOYSA-N 6-(2-methoxyphenyl)-2,4-dipyridin-2-ylpyridazin-3-one Chemical compound COC1=CC=CC=C1C1=NN(C=2N=CC=CC=2)C(=O)C(C=2N=CC=CC=2)=C1 ZWRYMXWENDLITR-UHFFFAOYSA-N 0.000 description 2
- UGDCUBMARVNLET-UHFFFAOYSA-N 6-pyridin-2-yl-4-pyridin-3-yl-2-thiophen-3-ylpyridazin-3-one Chemical compound O=C1C(C=2C=NC=CC=2)=CC(C=2N=CC=CC=2)=NN1C=1C=CSC=1 UGDCUBMARVNLET-UHFFFAOYSA-N 0.000 description 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010016952 Food poisoning Diseases 0.000 description 2
- 208000019331 Foodborne disease Diseases 0.000 description 2
- LFBZZHVSGAHQPP-UHFFFAOYSA-N GYKI 52466 Chemical compound C12=CC=3OCOC=3C=C2CC(C)=NN=C1C1=CC=C(N)C=C1 LFBZZHVSGAHQPP-UHFFFAOYSA-N 0.000 description 2
- 208000010412 Glaucoma Diseases 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 206010021118 Hypotonia Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VLSMHEGGTFMBBZ-OOZYFLPDSA-M Kainate Chemical compound CC(=C)[C@H]1C[NH2+][C@H](C([O-])=O)[C@H]1CC([O-])=O VLSMHEGGTFMBBZ-OOZYFLPDSA-M 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 206010028813 Nausea Diseases 0.000 description 2
- 208000029067 Neuromyelitis optica spectrum disease Diseases 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 206010034010 Parkinsonism Diseases 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 208000026723 Urinary tract disease Diseases 0.000 description 2
- NJBPHHJOFUNGDR-UHFFFAOYSA-N [2-(3-oxo-2-phenyl-6-pyridin-2-yl-4,5-dihydropyridazin-4-yl)phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1C1C(=O)N(C=2C=CC=CC=2)N=C(C=2N=CC=CC=2)C1 NJBPHHJOFUNGDR-UHFFFAOYSA-N 0.000 description 2
- SYGGHGNMXLJKDA-UHFFFAOYSA-N [2-(3-oxo-2-phenyl-6-pyridin-2-ylpyridazin-4-yl)phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1 SYGGHGNMXLJKDA-UHFFFAOYSA-N 0.000 description 2
- 230000007488 abnormal function Effects 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 229940009098 aspartate Drugs 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000009739 binding Methods 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 2
- 239000001354 calcium citrate Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 210000004004 carotid artery internal Anatomy 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 208000013677 cerebrovascular dementia Diseases 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000002860 competitive effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 208000012997 experimental autoimmune encephalomyelitis Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 208000007386 hepatic encephalopathy Diseases 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 208000010726 hind limb paralysis Diseases 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000005921 isopentoxy group Chemical group 0.000 description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000015654 memory Effects 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- DZNKOAWEHDKBEP-UHFFFAOYSA-N methyl 2-[6-[bis(2-methoxy-2-oxoethyl)amino]-5-[2-[2-[bis(2-methoxy-2-oxoethyl)amino]-5-methylphenoxy]ethoxy]-1-benzofuran-2-yl]-1,3-oxazole-5-carboxylate Chemical compound COC(=O)CN(CC(=O)OC)C1=CC=C(C)C=C1OCCOC(C(=C1)N(CC(=O)OC)CC(=O)OC)=CC2=C1OC(C=1OC(=CN=1)C(=O)OC)=C2 DZNKOAWEHDKBEP-UHFFFAOYSA-N 0.000 description 2
- ACFFVBVTJMQHOW-UHFFFAOYSA-N methyl n-(2-hydroxyethyl)-n-phenylcarbamate Chemical compound COC(=O)N(CCO)C1=CC=CC=C1 ACFFVBVTJMQHOW-UHFFFAOYSA-N 0.000 description 2
- SCSKNEDGGQVGAF-UHFFFAOYSA-N methyl n-(2-oxoethyl)-n-phenylcarbamate Chemical compound COC(=O)N(CC=O)C1=CC=CC=C1 SCSKNEDGGQVGAF-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000008693 nausea Effects 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 230000000324 neuroprotective effect Effects 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- WTFFOOAJSDVASL-UHFFFAOYSA-N tributyl(pyrimidin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CC=N1 WTFFOOAJSDVASL-UHFFFAOYSA-N 0.000 description 2
- 235000013337 tricalcium citrate Nutrition 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 208000014001 urinary system disease Diseases 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- FRBUNLLUASHNDJ-UHFFFAOYSA-N (2-nitrophenyl)hydrazine Chemical compound NNC1=CC=CC=C1[N+]([O-])=O FRBUNLLUASHNDJ-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- KBQNNOCVJFDHSC-UHFFFAOYSA-N (3-methylphenoxy)boronic acid Chemical compound CC1=CC=CC(OB(O)O)=C1 KBQNNOCVJFDHSC-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000005926 1,2-dimethylbutyloxy group Chemical group 0.000 description 1
- 125000005923 1,2-dimethylpropyloxy group Chemical group 0.000 description 1
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 1
- SOVLBASWGBYHTE-UHFFFAOYSA-N 2-(2-bromophenyl)-4-(6-chloropyridin-3-yl)-6-pyridin-2-yl-5h-1,2,4-triazin-3-one Chemical compound C1=NC(Cl)=CC=C1N1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 SOVLBASWGBYHTE-UHFFFAOYSA-N 0.000 description 1
- LMQINRRXRXJNGM-UHFFFAOYSA-N 2-(2-bromophenyl)-4-pyridin-3-yl-5h-chromeno[4,3-c]pyridazin-3-one Chemical compound BrC1=CC=CC=C1N1C(=O)C(C=2C=NC=CC=2)=C(COC=2C3=CC=CC=2)C3=N1 LMQINRRXRXJNGM-UHFFFAOYSA-N 0.000 description 1
- KKXDAJZIZLAXOA-UHFFFAOYSA-N 2-(2-bromophenyl)-6-(2-methoxyphenyl)-4,5-dihydro-1,2,4-triazin-3-one Chemical compound COC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)Br)C(=O)NC1 KKXDAJZIZLAXOA-UHFFFAOYSA-N 0.000 description 1
- FBYPAPKYBXFPJM-UHFFFAOYSA-N 2-(2-iodophenyl)-4-(2-methoxyphenyl)-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=CC=C1C1C(=O)N(C=2C(=CC=CC=2)I)N=C(C=2N=CC=CC=2)C1 FBYPAPKYBXFPJM-UHFFFAOYSA-N 0.000 description 1
- FRKONBNFURRTPT-UHFFFAOYSA-N 2-(2-iodophenyl)-4-pyridin-3-yl-5h-chromeno[4,3-c]pyridazin-3-one Chemical compound IC1=CC=CC=C1N1C(=O)C(C=2C=NC=CC=2)=C(COC=2C3=CC=CC=2)C3=N1 FRKONBNFURRTPT-UHFFFAOYSA-N 0.000 description 1
- MRHSKSNDCVKQSM-UHFFFAOYSA-N 2-(3-chloro-6-oxo-5-phenylpyridazin-1-yl)benzonitrile Chemical compound O=C1N(C=2C(=CC=CC=2)C#N)N=C(Cl)C=C1C1=CC=CC=C1 MRHSKSNDCVKQSM-UHFFFAOYSA-N 0.000 description 1
- FVXGXJHNUOCJNO-UHFFFAOYSA-N 2-(3-oxo-4-phenyl-6-pyridin-2-yl-5h-1,2,4-triazin-2-yl)benzonitrile Chemical compound O=C1N(C=2C=CC=CC=2)CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N FVXGXJHNUOCJNO-UHFFFAOYSA-N 0.000 description 1
- YWOYCJIBGSNNQG-UHFFFAOYSA-N 2-(9-fluoro-3-oxo-4-phenyl-5h-chromeno[4,3-c]pyridazin-2-yl)benzonitrile Chemical compound C12=CC(F)=CC=C2OCC(=C(C2=O)C=3C=CC=CC=3)C1=NN2C1=CC=CC=C1C#N YWOYCJIBGSNNQG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JOBOAWNGHYFWKP-UHFFFAOYSA-N 2-[5-(2-methoxyphenyl)-6-oxo-3-pyridin-2-ylpyridazin-1-yl]benzonitrile Chemical compound COC1=CC=CC=C1C(C1=O)=CC(C=2N=CC=CC=2)=NN1C1=CC=CC=C1C#N JOBOAWNGHYFWKP-UHFFFAOYSA-N 0.000 description 1
- RMQGKCSANRPOEB-UHFFFAOYSA-N 2-[6-(2-methoxyphenyl)-3-oxo-4-phenyl-5h-1,2,4-triazin-2-yl]benzonitrile Chemical compound COC1=CC=CC=C1C1=NN(C=2C(=CC=CC=2)C#N)C(=O)N(C=2C=CC=CC=2)C1 RMQGKCSANRPOEB-UHFFFAOYSA-N 0.000 description 1
- KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 1
- JBKINHFZTVLNEM-UHFFFAOYSA-N 2-bromoethoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCBr JBKINHFZTVLNEM-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical compound COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BGRXBNZMPMGLQI-UHFFFAOYSA-N 2-octyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC BGRXBNZMPMGLQI-UHFFFAOYSA-N 0.000 description 1
- HFBHPHBIBAUDNE-UHFFFAOYSA-N 2h-1,2,4-triazin-3-one Chemical class O=C1N=CC=NN1 HFBHPHBIBAUDNE-UHFFFAOYSA-N 0.000 description 1
- WQEBRZKYXXZALY-UHFFFAOYSA-N 2h-pyrido[2,3-e]thiazine Chemical class C1=CN=C2C=CNSC2=C1 WQEBRZKYXXZALY-UHFFFAOYSA-N 0.000 description 1
- ITGYAJMCQSYXIE-UHFFFAOYSA-N 3-(3-methoxyphenyl)-1-pyridin-2-ylprop-2-en-1-one Chemical compound COC1=CC=CC(C=CC(=O)C=2N=CC=CC=2)=C1 ITGYAJMCQSYXIE-UHFFFAOYSA-N 0.000 description 1
- XBJLKXOOHLLTPG-UHFFFAOYSA-N 3-chloro-6-methoxypyridazine Chemical compound COC1=CC=C(Cl)N=N1 XBJLKXOOHLLTPG-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- RQQAMVUVWBTSOZ-UHFFFAOYSA-N 4-(5-bromo-2-methoxyphenyl)-2-(2-bromophenyl)-6-pyridin-2-yl-4,5-dihydropyridazin-3-one Chemical compound COC1=CC=C(Br)C=C1C1C(=O)N(C=2C(=CC=CC=2)Br)N=C(C=2N=CC=CC=2)C1 RQQAMVUVWBTSOZ-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 206010008089 Cerebral artery occlusion Diseases 0.000 description 1
- 206010008748 Chorea Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 238000005361 D2 NMR spectroscopy Methods 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 208000009881 Decerebrate State Diseases 0.000 description 1
- 102000016911 Deoxyribonucleases Human genes 0.000 description 1
- 108010053770 Deoxyribonucleases Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 208000016621 Hearing disease Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 208000001089 Multiple system atrophy Diseases 0.000 description 1
- 208000007379 Muscle Hypotonia Diseases 0.000 description 1
- 241001049988 Mycobacterium tuberculosis H37Ra Species 0.000 description 1
- 102000047918 Myelin Basic Human genes 0.000 description 1
- 101710107068 Myelin basic protein Proteins 0.000 description 1
- 206010061533 Myotonia Diseases 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 206010060860 Neurological symptom Diseases 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- 102000004108 Neurotransmitter Receptors Human genes 0.000 description 1
- 108090000590 Neurotransmitter Receptors Proteins 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 101100522114 Oryza sativa subsp. japonica PHT1-12 gene Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 206010033892 Paraplegia Diseases 0.000 description 1
- 241000169594 Paropsia Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001944 accentuation Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229940009868 aluminum magnesium silicate Drugs 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- OVBXTKIWZAHFAC-UHFFFAOYSA-N butane;pyrazine;tin Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=CC=N1 OVBXTKIWZAHFAC-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 210000000269 carotid artery external Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 208000012601 choreatic disease Diseases 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229940013361 cresol Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 206010013990 dysuria Diseases 0.000 description 1
- 239000003221 ear drop Substances 0.000 description 1
- 229940047652 ear drops Drugs 0.000 description 1
- 230000000668 effect on calcium Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- IUDKTVXSXWAKJO-UHFFFAOYSA-N ethyl 2-pyridin-2-ylacetate Chemical compound CCOC(=O)CC1=CC=CC=N1 IUDKTVXSXWAKJO-UHFFFAOYSA-N 0.000 description 1
- LYEHLSUOBAIWOK-UHFFFAOYSA-N ethyl 4-(2-methoxyphenyl)-4-oxo-2-pyridin-2-ylbutanoate Chemical compound C=1C=CC=NC=1C(C(=O)OCC)CC(=O)C1=CC=CC=C1OC LYEHLSUOBAIWOK-UHFFFAOYSA-N 0.000 description 1
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 210000003194 forelimb Anatomy 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 210000003552 inferior colliculi Anatomy 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000003140 lateral ventricle Anatomy 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000011694 lewis rat Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 210000004245 medial forebrain bundle Anatomy 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- RZRHCJQPSYXOHV-UHFFFAOYSA-N methyl n-phenyl-n-[2-(phenylhydrazinylidene)ethyl]carbamate Chemical compound C=1C=CC=CC=1N(C(=O)OC)CC=NNC1=CC=CC=C1 RZRHCJQPSYXOHV-UHFFFAOYSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 210000003657 middle cerebral artery Anatomy 0.000 description 1
- 201000007309 middle cerebral artery infarction Diseases 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 230000000978 myorelaxation Effects 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- 125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- 229940037525 nasal preparations Drugs 0.000 description 1
- 210000004498 neuroglial cell Anatomy 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229940073665 octyldodecyl myristate Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 208000031237 olivopontocerebellar atrophy Diseases 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000002901 organomagnesium compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 208000008136 parkinson disease 10 Diseases 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 230000002516 postimmunization Effects 0.000 description 1
- WLLBPSGBADGYST-UHFFFAOYSA-N potassium 3-(3-methoxyphenyl)-1-pyridin-2-ylprop-2-en-1-one 2-methylpropan-2-olate Chemical compound CC(C)([O-])C.[K+].N1=C(C=CC=C1)C(C=CC1=CC(=CC=C1)OC)=O WLLBPSGBADGYST-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- VTJVVTQMBGMYAO-UHFFFAOYSA-N potassium;2-methylpropan-2-olate;potassium Chemical compound [K].[K+].CC(C)(C)[O-] VTJVVTQMBGMYAO-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical group C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000001020 rhythmical effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical class [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 210000003863 superior colliculi Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000006441 vascular event Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
- A61P25/02—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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D237/14—Oxygen atoms
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Psychology (AREA)
- Communicable Diseases (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Heart & Thoracic Surgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Addiction (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000282636 | 2000-09-18 | ||
JP2000289412 | 2000-09-22 | ||
JP2000342614 | 2000-11-09 | ||
GB0102824A GB0102824D0 (en) | 2001-02-05 | 2001-02-05 | Triazinone compounds process for producing the same and pharmaceuticals thereof |
GB0102822A GB0102822D0 (en) | 2001-02-05 | 2001-02-05 | Pyridazinone compounds manufacturing methods thereof and pharmaceuticals thereof |
PCT/JP2001/008058 WO2002022587A1 (fr) | 2000-09-18 | 2001-09-17 | Pyridazinones et triazinones ainsi que leur utilisation medicale |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20031232D0 NO20031232D0 (no) | 2003-03-17 |
NO20031232L NO20031232L (no) | 2003-05-19 |
NO327813B1 true NO327813B1 (no) | 2009-09-28 |
Family
ID=27516005
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20031232A NO327813B1 (no) | 2000-09-18 | 2003-03-17 | Pyridazinoner og triazinoner og deres anvendelse, samt farmasoytisk preparat |
Country Status (16)
Country | Link |
---|---|
US (2) | US20030225081A1 (hu) |
EP (1) | EP1319659B1 (hu) |
JP (2) | JP4233868B2 (hu) |
KR (1) | KR100770327B1 (hu) |
CN (1) | CN100473647C (hu) |
AT (1) | ATE425148T1 (hu) |
AU (2) | AU9022901A (hu) |
CA (2) | CA2422589C (hu) |
DE (1) | DE60137948D1 (hu) |
HU (1) | HU228961B1 (hu) |
IL (2) | IL154709A0 (hu) |
MX (1) | MXPA03002324A (hu) |
NO (1) | NO327813B1 (hu) |
NZ (1) | NZ524745A (hu) |
TW (1) | TWI262915B (hu) |
WO (1) | WO2002022587A1 (hu) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1431293B1 (en) * | 2001-09-26 | 2011-06-08 | Kowa Co., Ltd. | Water-soluble phenylpyridazine derivatives and drugs containing the same |
US6861428B2 (en) * | 2001-09-26 | 2005-03-01 | Kowa Co., Ltd. | Water-soluble phenylpyridazine compounds and compositions containing the same |
US7309701B2 (en) | 2002-11-19 | 2007-12-18 | Sanofi-Aventis Deutschland Gmbh | Pyridazinone derivatives as pharmaceuticals and pharmaceutical compositions containing them |
FR2847253B1 (fr) * | 2002-11-19 | 2007-05-18 | Aventis Pharma Sa | Nouveaux derives de pyridazinones a titre de medicaments et compositions pharmaceutiques les renfermant |
US7462613B2 (en) | 2002-11-19 | 2008-12-09 | Sanofi-Aventis Deutschland Gmbh | Pyridazinone derivatives as pharmaceuticals and pharmaceutical compositions containing them |
WO2006107860A2 (en) * | 2005-04-04 | 2006-10-12 | Eisai Co., Ltd. | Dihydropyridine compounds and compositions for headaches |
SI1928454T1 (sl) | 2005-05-10 | 2015-01-30 | Intermune, Inc. | Piridonski derivati za moduliranje s stresom aktiviranega protein kinaznega sistema |
AR057986A1 (es) * | 2005-11-21 | 2008-01-09 | Japan Tobacco Inc | Compuesto heterociclico y su uso farmaceutico |
EP1958946B1 (en) | 2005-12-07 | 2011-02-23 | Sumitomo Chemical Company, Limited | Pyridazine compound and use thereof |
MX2009008059A (es) * | 2007-01-29 | 2009-08-12 | Kowa Co | Agente para tratamiento de esclerosis multiple. |
EP2131828A2 (en) * | 2007-03-05 | 2009-12-16 | Eisai R&D Management Co., Ltd. | Ampa and nmda receptor antagonists for neurodegenerative diseases |
JP2010524844A (ja) * | 2007-04-26 | 2010-07-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 認知症のためのシンナミド化合物 |
JP5627574B2 (ja) | 2008-06-03 | 2014-11-19 | インターミューン, インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
UA103918C2 (en) | 2009-03-02 | 2013-12-10 | Айерем Элелси | N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators |
AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
JP6416125B2 (ja) * | 2013-02-04 | 2018-10-31 | プレクストン・セラピューティクス・ソシエテ・アノニム | mGluR3の正のアロステリックモジュレーター |
US8877766B2 (en) * | 2013-02-15 | 2014-11-04 | Peter F. Kador | Neuroprotective multifunctional antioxidants and their monofunctional analogs |
KR102373700B1 (ko) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | 항섬유성 피리디논 |
WO2016051799A1 (ja) * | 2014-10-01 | 2016-04-07 | 学校法人同志社 | 2-アミノヒドロキノン誘導体及びタウ凝集阻害剤 |
CN111153859B (zh) * | 2015-04-15 | 2021-09-03 | 江苏恩华药业股份有限公司 | 哒嗪酮类衍生物及其应用 |
PE20181008A1 (es) * | 2015-11-13 | 2018-06-26 | Eisai Randd Man Co Ltd | Compuesto piranodipiridinico |
CN109863140B (zh) | 2016-05-25 | 2023-02-21 | 拜耳医药股份有限公司 | 3-氧代-2,6-二苯基-2,3-二氢哒嗪-4-甲酰胺 |
JOP20190193A1 (ar) | 2017-02-09 | 2019-08-08 | Bayer Pharma AG | ممركبات 2-أريل غير متجانس-3-أكسو-2، 3-ثنائي هيدرو بيريدازين-4-كربوكساميد لمعالجة السرطان |
KR20200004792A (ko) | 2017-05-09 | 2020-01-14 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 피라노디피리딘 화합물의 결정 |
EP3713931A1 (en) * | 2017-11-21 | 2020-09-30 | Bayer Aktiengesellschaft | 3-oxo-6-heteroaryl-2-phenyl-2,3-dihydropyridazine-4-carboxamides |
US11459312B2 (en) | 2017-11-21 | 2022-10-04 | Bayer Aktiengesellschaft | Sulphur substituted 3-oxo-2,3-dihydropyridazine-4-carboxamides |
WO2020017587A1 (ja) * | 2018-07-19 | 2020-01-23 | 大日本住友製薬株式会社 | ピリダジノン誘導体 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3014034A (en) * | 1959-01-22 | 1961-12-19 | Ciba Pharm Prod Inc | 1, 3-diaryl, 5-amino-pyridazinones |
US3018034A (en) * | 1959-11-17 | 1962-01-23 | Gen Applied Science Lab Inc | Propulsion device for vertical takeoff aircraft |
IL29949A (en) * | 1967-05-19 | 1971-08-25 | Seperic | Diphenyl-pyridazones and process for preparing same |
DE4134467A1 (de) * | 1991-10-18 | 1993-04-22 | Thomae Gmbh Dr K | Heterobiarylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
ES2131506T3 (es) * | 1990-09-21 | 1999-08-01 | Rohm & Haas | Dihidropiridacinonas y piridacinonas como fungicidas. |
GB9206266D0 (en) * | 1992-03-23 | 1992-05-06 | Merck Sharp & Dohme | Therapeutic agents |
US5356902A (en) * | 1992-11-06 | 1994-10-18 | Eli Lilly And Company | Decahydroisoquinoline compounds as excitatory amino acid receptor antagonists |
AU691673B2 (en) * | 1994-11-14 | 1998-05-21 | Dow Agrosciences Llc | Pyridazinones and their use as fungicides |
DE19643037A1 (de) * | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
IL123340A0 (en) * | 1997-02-20 | 1998-09-24 | Sumitomo Chemical Co | Pyridazin-3-one derivatives and their use |
TWI241295B (en) * | 1998-03-02 | 2005-10-11 | Kowa Co | Pyridazine derivative and medicine containing the same as effect component |
JP2000119257A (ja) * | 1998-08-14 | 2000-04-25 | Nippon Nohyaku Co Ltd | ピリダジノン誘導体 |
US6469003B1 (en) * | 1998-08-14 | 2002-10-22 | Nihon Nohyaku Co., Ltd. | Pyridazinone derivatives |
JP2000247959A (ja) * | 1999-02-26 | 2000-09-12 | Kowa Co | ピリダジン−3−オン誘導体及びこれを含有する医薬 |
KR100344790B1 (ko) * | 1999-10-07 | 2002-07-19 | 엘지전자주식회사 | 마이크로 기계구조를 이용한 주파수 가변 초고주파 필터 |
-
2001
- 2001-09-17 US US10/380,783 patent/US20030225081A1/en not_active Abandoned
- 2001-09-17 CN CNB018158803A patent/CN100473647C/zh not_active Expired - Fee Related
- 2001-09-17 KR KR1020037003807A patent/KR100770327B1/ko not_active IP Right Cessation
- 2001-09-17 MX MXPA03002324A patent/MXPA03002324A/es active IP Right Grant
- 2001-09-17 NZ NZ524745A patent/NZ524745A/en not_active IP Right Cessation
- 2001-09-17 JP JP2002526840A patent/JP4233868B2/ja not_active Expired - Fee Related
- 2001-09-17 AU AU9022901A patent/AU9022901A/xx active Pending
- 2001-09-17 WO PCT/JP2001/008058 patent/WO2002022587A1/ja active Application Filing
- 2001-09-17 AT AT01970120T patent/ATE425148T1/de not_active IP Right Cessation
- 2001-09-17 HU HU0302508A patent/HU228961B1/hu not_active IP Right Cessation
- 2001-09-17 CA CA2422589A patent/CA2422589C/en not_active Expired - Fee Related
- 2001-09-17 AU AU2001290229A patent/AU2001290229B2/en not_active Ceased
- 2001-09-17 CA CA2742411A patent/CA2742411A1/en not_active Abandoned
- 2001-09-17 DE DE60137948T patent/DE60137948D1/de not_active Expired - Lifetime
- 2001-09-17 EP EP01970120A patent/EP1319659B1/en not_active Expired - Lifetime
- 2001-09-17 IL IL15470901A patent/IL154709A0/xx active IP Right Grant
- 2001-09-19 TW TW090123425A patent/TWI262915B/zh not_active IP Right Cessation
-
2003
- 2003-03-03 IL IL154709A patent/IL154709A/en not_active IP Right Cessation
- 2003-03-17 NO NO20031232A patent/NO327813B1/no not_active IP Right Cessation
-
2006
- 2006-04-21 US US11/408,078 patent/US20060189622A1/en not_active Abandoned
-
2008
- 2008-06-13 JP JP2008154986A patent/JP4906790B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
TWI262915B (en) | 2006-10-01 |
IL154709A0 (en) | 2003-10-31 |
US20030225081A1 (en) | 2003-12-04 |
HUP0302508A2 (hu) | 2003-12-29 |
JP2009007356A (ja) | 2009-01-15 |
CN1458924A (zh) | 2003-11-26 |
AU2001290229B2 (en) | 2006-12-07 |
DE60137948D1 (de) | 2009-04-23 |
EP1319659B1 (en) | 2009-03-11 |
HUP0302508A3 (en) | 2007-03-28 |
CA2422589A1 (en) | 2003-03-17 |
MXPA03002324A (es) | 2003-06-06 |
NZ524745A (en) | 2006-01-27 |
JPWO2002022587A1 (ja) | 2004-01-22 |
JP4906790B2 (ja) | 2012-03-28 |
IL154709A (en) | 2007-09-20 |
CA2422589C (en) | 2011-08-09 |
CA2742411A1 (en) | 2002-03-21 |
US20060189622A1 (en) | 2006-08-24 |
KR20030030007A (ko) | 2003-04-16 |
HU228961B1 (en) | 2013-07-29 |
NO20031232L (no) | 2003-05-19 |
EP1319659A4 (en) | 2005-08-10 |
NO20031232D0 (no) | 2003-03-17 |
ATE425148T1 (de) | 2009-03-15 |
WO2002022587A1 (fr) | 2002-03-21 |
CN100473647C (zh) | 2009-04-01 |
AU9022901A (en) | 2002-03-26 |
EP1319659A1 (en) | 2003-06-18 |
JP4233868B2 (ja) | 2009-03-04 |
KR100770327B1 (ko) | 2007-10-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO327813B1 (no) | Pyridazinoner og triazinoner og deres anvendelse, samt farmasoytisk preparat | |
US11447453B2 (en) | Metabotropic glutamate receptor negative allosteric modulators (NAMs) and uses thereof | |
TWI828677B (zh) | 甲基修飾酵素之調節劑、其組成物及用途 | |
JP6693957B2 (ja) | Hdac1/2阻害剤としてのピペリジン誘導体 | |
KR101890442B1 (ko) | P2x4 수용체 길항제 | |
US20030013886A1 (en) | Benzimidazole cyclooxygenase-2 inhibitors | |
WO2007142323A1 (ja) | 側鎖にスピロ環構造を有する新規インダゾール誘導体 | |
KR20010099634A (ko) | 텔로머라제 저해제 및 그 사용 방법 | |
NO325160B1 (no) | 1,2-dihydropyridinforbindelser, fremgangsmate for fremstilling av de samme og anvendelse derav | |
CZ295565B6 (cs) | 2,3-Disubstituované 4(3H)-chinazolinony, jejich použití a farmaceutické kompozice na jejich bázi | |
CN101679392B (zh) | 喹诺酮化合物和药物组合物 | |
JP2021531336A (ja) | ヒストンデアセチラーゼの阻害剤 | |
RU2279428C2 (ru) | Производные пиридазинона и триазинона и их применение в качестве фармацевтических препаратов | |
CN101486683B (zh) | 哒嗪酮和三嗪酮化合物及其作为药物制剂的用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |