HUE033277T2 - N - ((1H-Indol-3-yl) alkyl) -4-benzyl) benzamide and N - ((1H-pyrrolo [2,3-b] pyridin-3-yl) alkyl) -4-benzyl ) Benzamide derivatives as alpha-synuclein aggregation inhibitors for the treatment of neurodegenerative disorders - Google Patents

Info

Publication number

HUE033277T2

HUE033277T2 HUE11805450A HUE11805450A HUE033277T2 HU E033277 T2 HUE033277 T2 HU E033277T2 HU E11805450 A HUE11805450 A HU E11805450A HU E11805450 A HUE11805450 A HU E11805450A HU E033277 T2 HUE033277 T2 HU E033277T2

Authority

HU

Hungary

Prior art keywords

alkyl

mmol

heterocycle

indol

chloro

Prior art date

2010-12-13

Links

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• -1 1H-pyrrolo[2,3-b]pyridin-3-yl Chemical group 0.000 title claims description 204
• 238000011282 treatment Methods 0.000 title claims description 28
• 230000002776 aggregation Effects 0.000 title claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title description 123
• 108090000185 alpha-Synuclein Proteins 0.000 title description 22
• 208000015122 neurodegenerative disease Diseases 0.000 title description 22
• 102000003802 alpha-Synuclein Human genes 0.000 title description 20
• 238000004220 aggregation Methods 0.000 title description 8
• 239000003112 inhibitor Substances 0.000 title description 2
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 225
• 150000001875 compounds Chemical class 0.000 claims description 194
• 229910052717 sulfur Inorganic materials 0.000 claims description 184
• 125000003342 alkenyl group Chemical group 0.000 claims description 179
• 125000000304 alkynyl group Chemical group 0.000 claims description 174
• 229910052739 hydrogen Inorganic materials 0.000 claims description 161
• 239000001257 hydrogen Substances 0.000 claims description 160
• 125000000623 heterocyclic group Chemical group 0.000 claims description 151
• 125000005842 heteroatom Chemical group 0.000 claims description 138
• 238000002360 preparation method Methods 0.000 claims description 136
• 229910052736 halogen Inorganic materials 0.000 claims description 124
• 125000003118 aryl group Chemical group 0.000 claims description 116
• 150000002367 halogens Chemical class 0.000 claims description 103
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 102
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 101
• 229910052757 nitrogen Inorganic materials 0.000 claims description 97
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 74
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 64
• 238000000034 method Methods 0.000 claims description 63
• 229910052799 carbon Inorganic materials 0.000 claims description 59
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 59
• 229910052760 oxygen Inorganic materials 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 42
• 125000004432 carbon atom Chemical group C* 0.000 claims description 37
• 125000004429 atom Chemical group 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
• 125000005843 halogen group Chemical group 0.000 claims description 24
• 125000004122 cyclic group Chemical group 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 239000012453 solvate Substances 0.000 claims description 17
• 201000010099 disease Diseases 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 150000004677 hydrates Chemical class 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 229910052740 iodine Inorganic materials 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 208000001089 Multiple system atrophy Diseases 0.000 claims description 7
• 208000014060 Niemann-Pick disease Diseases 0.000 claims description 7
• 150000001298 alcohols Chemical class 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 230000015572 biosynthetic process Effects 0.000 claims description 6
• 125000004450 alkenylene group Chemical group 0.000 claims description 5
• 125000004419 alkynylene group Chemical group 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 5
• 230000007850 degeneration Effects 0.000 claims description 5
• 230000014509 gene expression Effects 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 239000002904 solvent Substances 0.000 claims description 5
• 239000000178 monomer Substances 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 230000000750 progressive effect Effects 0.000 claims description 3
• 108090000623 proteins and genes Proteins 0.000 claims description 3
• 206010044565 Tremor Diseases 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• 125000000524 functional group Chemical group 0.000 claims description 2
• 229910052744 lithium Inorganic materials 0.000 claims description 2
• 230000000626 neurodegenerative effect Effects 0.000 claims description 2
• 229940095064 tartrate Drugs 0.000 claims description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 3
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 2
• 125000005741 alkyl alkenyl group Chemical group 0.000 claims 2
• 125000005025 alkynylaryl group Chemical group 0.000 claims 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
• 208000011580 syndromic disease Diseases 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 241000238876 Acari Species 0.000 claims 1
• 239000002126 C01EB10 - Adenosine Substances 0.000 claims 1
• 206010011878 Deafness Diseases 0.000 claims 1
• 239000004593 Epoxy Substances 0.000 claims 1
• 206010028372 Muscular weakness Diseases 0.000 claims 1
• 229920005372 Plexiglas® Polymers 0.000 claims 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 1
• 230000005856 abnormality Effects 0.000 claims 1
• 229960005305 adenosine Drugs 0.000 claims 1
• 238000005054 agglomeration Methods 0.000 claims 1
• 150000001336 alkenes Chemical class 0.000 claims 1
• 150000001345 alkine derivatives Chemical class 0.000 claims 1
• 125000006193 alkinyl group Chemical group 0.000 claims 1
• 229910052785 arsenic Inorganic materials 0.000 claims 1
• RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
• 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
• 150000002081 enamines Chemical class 0.000 claims 1
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
• 239000006260 foam Substances 0.000 claims 1
• 210000000245 forearm Anatomy 0.000 claims 1
• 150000004820 halides Chemical class 0.000 claims 1
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
• 229910052742 iron Inorganic materials 0.000 claims 1
• 230000036473 myasthenia Effects 0.000 claims 1
• 229910052759 nickel Inorganic materials 0.000 claims 1
• 238000005204 segregation Methods 0.000 claims 1
• 238000007920 subcutaneous administration Methods 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 312
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 264
• 239000000203 mixture Substances 0.000 description 137
• 230000002829 reductive effect Effects 0.000 description 115
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 111
• 239000000543 intermediate Substances 0.000 description 106
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 103
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 95
• 238000003818 flash chromatography Methods 0.000 description 88
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 87
• 239000000243 solution Substances 0.000 description 86
• 239000003480 eluent Substances 0.000 description 85
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 84
• 239000000741 silica gel Substances 0.000 description 84
• 229910002027 silica gel Inorganic materials 0.000 description 84
• 229960001866 silicon dioxide Drugs 0.000 description 84
• 239000007787 solid Substances 0.000 description 75
• 125000006270 aryl alkenylene group Chemical group 0.000 description 70
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 54
• 150000001721 carbon Chemical group 0.000 description 53
• 239000012044 organic layer Substances 0.000 description 46
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
• 239000011541 reaction mixture Substances 0.000 description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 33
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
• 235000009518 sodium iodide Nutrition 0.000 description 29
• 229910000029 sodium carbonate Inorganic materials 0.000 description 27
• 125000002541 furyl group Chemical group 0.000 description 26
• 125000001544 thienyl group Chemical group 0.000 description 26
• 238000005160 1H NMR spectroscopy Methods 0.000 description 25
• 239000012267 brine Substances 0.000 description 25
• 239000013058 crude material Substances 0.000 description 25
• 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 25
• 238000000746 purification Methods 0.000 description 25
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
• 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 24
• 239000011734 sodium Substances 0.000 description 23
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 23
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
• 125000004076 pyridyl group Chemical group 0.000 description 22
• 239000007864 aqueous solution Substances 0.000 description 21
• 150000002430 hydrocarbons Chemical group 0.000 description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
• 239000003921 oil Substances 0.000 description 20
• 125000002883 imidazolyl group Chemical group 0.000 description 19
• 125000003226 pyrazolyl group Chemical group 0.000 description 19
• 201000011240 Frontotemporal dementia Diseases 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 125000002757 morpholinyl group Chemical group 0.000 description 18
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 18
• FREIFKXNRYUNEV-UHFFFAOYSA-N n-[2-(5-chloro-1h-indol-3-yl)ethyl]-4-(chloromethyl)benzamide Chemical compound C1=CC(CCl)=CC=C1C(=O)NCCC1=CNC2=CC=C(Cl)C=C12 FREIFKXNRYUNEV-UHFFFAOYSA-N 0.000 description 17
• 125000005936 piperidyl group Chemical group 0.000 description 17
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
• 208000024827 Alzheimer disease Diseases 0.000 description 16
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 16
• KUNOGJRORGEGLW-UHFFFAOYSA-N n-[2-(5-chloro-1h-indol-3-yl)ethyl]-3-(chloromethyl)benzamide Chemical compound ClCC1=CC=CC(C(=O)NCCC=2C3=CC(Cl)=CC=C3NC=2)=C1 KUNOGJRORGEGLW-UHFFFAOYSA-N 0.000 description 16
• 125000003373 pyrazinyl group Chemical group 0.000 description 16
• 125000000714 pyrimidinyl group Chemical group 0.000 description 16
• 125000006591 (C2-C6) alkynylene group Chemical group 0.000 description 15
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
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• 125000001309 chloro group Chemical group Cl* 0.000 description 14
• 125000000753 cycloalkyl group Chemical group 0.000 description 14
• 125000001153 fluoro group Chemical group F* 0.000 description 14
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 14
• 125000000168 pyrrolyl group Chemical group 0.000 description 14
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 14
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 14
• 235000019345 sodium thiosulphate Nutrition 0.000 description 14
• 125000000335 thiazolyl group Chemical group 0.000 description 14
• 125000005986 4-piperidonyl group Chemical group 0.000 description 13
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 13
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 13
• 229930195733 hydrocarbon Natural products 0.000 description 13
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 13
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
• 125000003386 piperidinyl group Chemical group 0.000 description 13
• 230000002265 prevention Effects 0.000 description 13
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 13
• 125000002098 pyridazinyl group Chemical group 0.000 description 13
• 125000001422 pyrrolinyl group Chemical group 0.000 description 13
• 125000003831 tetrazolyl group Chemical group 0.000 description 13
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• 101150070547 MAPT gene Proteins 0.000 description 12
• 102100040243 Microtubule-associated protein tau Human genes 0.000 description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
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• 125000001041 indolyl group Chemical group 0.000 description 12
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
• 235000019341 magnesium sulphate Nutrition 0.000 description 12
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 12
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 12
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 229910052763 palladium Inorganic materials 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• 125000004927 thianaphthalenyl group Chemical group S1C(C=CC2=CC=CC=C12)* 0.000 description 11
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
• 230000004770 neurodegeneration Effects 0.000 description 10
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
• 239000011593 sulfur Chemical group 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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• 125000001786 isothiazolyl group Chemical group 0.000 description 9
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• KNXQDJCZSVHEIW-UHFFFAOYSA-N (3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(F)=C1 KNXQDJCZSVHEIW-UHFFFAOYSA-N 0.000 description 8
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 8
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• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 8
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 8
• 125000004935 benzoxazolinyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
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• 125000003838 furazanyl group Chemical group 0.000 description 8
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• 125000002755 pyrazolinyl group Chemical group 0.000 description 8
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• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
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• 239000004215 Carbon black (E152) Substances 0.000 description 7
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
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