SK283678B6 - Substituované indánové a dihydroindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Info

Publication number

SK283678B6

SK283678B6 SK813-99A SK81399A SK283678B6 SK 283678 B6 SK283678 B6 SK 283678B6 SK 81399 A SK81399 A SK 81399A SK 283678 B6 SK283678 B6 SK 283678B6

Authority

SK

Slovakia

Prior art keywords

dihydroindole

compound

indane

indole

substituted

Prior art date

1996-12-20

Links

• Espacenet
• Global Dossier
• Discuss

• PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 title claims abstract description 88
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 title claims abstract description 55
• 239000008194 pharmaceutical composition Chemical class 0.000 title claims abstract description 8
• 125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 0.000 title claims abstract description 5
• 238000011282 treatment Methods 0.000 claims abstract description 23
• 230000000694 effects Effects 0.000 claims abstract description 20
• 208000019901 Anxiety disease Diseases 0.000 claims abstract description 16
• 208000024891 symptom Diseases 0.000 claims abstract description 11
• 208000028017 Psychotic disease Diseases 0.000 claims abstract description 9
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 8
• 208000019695 Migraine disease Diseases 0.000 claims abstract description 7
• 206010027599 migraine Diseases 0.000 claims abstract description 7
• 208000007848 Alcoholism Diseases 0.000 claims abstract description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 6
• 206010039966 Senile dementia Diseases 0.000 claims abstract description 6
• 230000016571 aggressive behavior Effects 0.000 claims abstract description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
• 201000007930 alcohol dependence Diseases 0.000 claims abstract description 5
• 208000035475 disorder Diseases 0.000 claims abstract description 5
• 230000000302 ischemic effect Effects 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 280
• -1 methyl-substituted phenyl Chemical group 0.000 claims description 136
• 229910052739 hydrogen Inorganic materials 0.000 claims description 91
• 150000002468 indanes Chemical class 0.000 claims description 66
• 239000001257 hydrogen Substances 0.000 claims description 47
• 150000002431 hydrogen Chemical group 0.000 claims description 31
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 230000036506 anxiety Effects 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 125000001624 naphthyl group Chemical group 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 10
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 230000001502 supplementing effect Effects 0.000 claims description 8
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
• PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical group [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
• 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 5
• 239000000164 antipsychotic agent Substances 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000003441 thioacyl group Chemical group 0.000 claims description 5
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims description 4
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 150000002430 hydrocarbons Chemical group 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 2
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
• 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 2
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
• 125000001424 substituent group Chemical group 0.000 claims description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
• 208000020764 Sensation disease Diseases 0.000 claims 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
• 230000000295 complement effect Effects 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 46
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 38
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 38
• 239000000126 substance Substances 0.000 abstract description 14
• 230000000561 anti-psychotic effect Effects 0.000 abstract description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 137
• 239000000203 mixture Substances 0.000 description 137
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 135
• 239000000243 solution Substances 0.000 description 117
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 89
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 64
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 47
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 46
• 235000019439 ethyl acetate Nutrition 0.000 description 46
• 239000000047 product Substances 0.000 description 43
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
• 102000005962 receptors Human genes 0.000 description 38
• 108020003175 receptors Proteins 0.000 description 38
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
• 239000000741 silica gel Substances 0.000 description 32
• 229910002027 silica gel Inorganic materials 0.000 description 32
• 239000011541 reaction mixture Substances 0.000 description 31
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
• 239000003480 eluent Substances 0.000 description 24
• 239000000543 intermediate Substances 0.000 description 24
• 238000000034 method Methods 0.000 description 24
• 229960003638 dopamine Drugs 0.000 description 23
• 238000010992 reflux Methods 0.000 description 23
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 238000002844 melting Methods 0.000 description 20
• 230000008018 melting Effects 0.000 description 20
• 239000012043 crude product Substances 0.000 description 19
• 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 description 19
• 239000003921 oil Substances 0.000 description 19
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
• 239000011347 resin Substances 0.000 description 17
• 229920005989 resin Polymers 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• 238000007630 basic procedure Methods 0.000 description 16
• 239000012074 organic phase Substances 0.000 description 16
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
• 229960000583 acetic acid Drugs 0.000 description 15
• 235000011054 acetic acid Nutrition 0.000 description 14
• DQGWEDRPBNHZDE-UHFFFAOYSA-N 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1C1=CCNCC1 DQGWEDRPBNHZDE-UHFFFAOYSA-N 0.000 description 13
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
• 239000008346 aqueous phase Substances 0.000 description 13
• 238000000746 purification Methods 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• 229910010082 LiAlH Inorganic materials 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• 239000000908 ammonium hydroxide Substances 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• 238000004440 column chromatography Methods 0.000 description 10
• 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 description 10
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 10
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
• 229940079593 drug Drugs 0.000 description 9
• 239000000284 extract Substances 0.000 description 9
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
• 230000009467 reduction Effects 0.000 description 9
• 238000003556 assay Methods 0.000 description 8
• 239000012267 brine Substances 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• 230000005764 inhibitory process Effects 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• AEVBPXDFDKBGLT-YOUFYPILSA-N (2s,3s,4r,5r)-n-[2-[4-(diethoxyphosphorylmethyl)anilino]-2-oxoethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolane-2-carboxamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NC(=O)CNC(=O)[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 AEVBPXDFDKBGLT-YOUFYPILSA-N 0.000 description 7
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 7
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 7
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 7
• VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 6
• GATUUSFIQPRJQV-UHFFFAOYSA-N 2-(2-iodoethyl)-2,3-dihydro-1h-indene Chemical compound C1=CC=C2CC(CCI)CC2=C1 GATUUSFIQPRJQV-UHFFFAOYSA-N 0.000 description 6
• NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
• UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
• 239000012346 acetyl chloride Substances 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• 230000008020 evaporation Effects 0.000 description 6
• 238000000338 in vitro Methods 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 210000004515 ventral tegmental area Anatomy 0.000 description 6
• PPVKBEWRGPFIIJ-UHFFFAOYSA-N 2-[1-[(2-methylpropan-2-yl)oxycarbonyl]-2,3-dihydroindol-3-yl]acetic acid Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)CC(CC(O)=O)C2=C1 PPVKBEWRGPFIIJ-UHFFFAOYSA-N 0.000 description 5
• MZILCLREQQTZJP-UHFFFAOYSA-N 5-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=C(NC=C2)C2=C1 MZILCLREQQTZJP-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
• 239000000654 additive Substances 0.000 description 5
• 239000012458 free base Substances 0.000 description 5
• 230000002401 inhibitory effect Effects 0.000 description 5
• 239000003446 ligand Substances 0.000 description 5
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• HBOBUTXJMIXYPE-UHFFFAOYSA-N 1,2-bis(chloromethyl)-4,5-dimethoxybenzene Chemical compound COC1=CC(CCl)=C(CCl)C=C1OC HBOBUTXJMIXYPE-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• USKLUPUZMZMEOL-UHFFFAOYSA-N 1h-indole;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC=C2NC=CC2=C1 USKLUPUZMZMEOL-UHFFFAOYSA-N 0.000 description 4
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
• VGOALPIDEXVYQI-UHFFFAOYSA-N 3-(2-imidazo[1,2-b]pyridazin-3-ylethynyl)-n-[3-imidazol-1-yl-5-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound C1=C(C#CC=2N3N=CC=CC3=NC=2)C(C)=CC=C1C(=O)NC(C=C(C=1)C(F)(F)F)=CC=1N1C=CN=C1 VGOALPIDEXVYQI-UHFFFAOYSA-N 0.000 description 4
• LDVBLBAOCVFWSU-UHFFFAOYSA-N 3-(2-methylsulfonylethyl)-2,3-dihydroindole-1-carbaldehyde Chemical compound C1=CC=C2C(CCS(=O)(=O)C)CN(C=O)C2=C1 LDVBLBAOCVFWSU-UHFFFAOYSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
• GLWNXNSNQZKAMK-UHFFFAOYSA-N 4-propan-2-yloxy-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound CC(C)OC1=CC=CC2=C1CC(C(O)=O)C2 GLWNXNSNQZKAMK-UHFFFAOYSA-N 0.000 description 4
• PTNSNQYSLLPWPH-UHFFFAOYSA-N 5-chloro-1-pyridin-4-ylindole Chemical compound C1=CC2=CC(Cl)=CC=C2N1C1=CC=NC=C1 PTNSNQYSLLPWPH-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• IDBWRKSBFSAKQM-UHFFFAOYSA-N C1CC2=C(C1CCO)C=CC=C2N Chemical compound C1CC2=C(C1CCO)C=CC=C2N IDBWRKSBFSAKQM-UHFFFAOYSA-N 0.000 description 4
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