CA2519107A1 - Novel fused triazolones and the uses thereof - Google Patents

Info

Publication number

CA2519107A1

CA2519107A1 CA002519107A CA2519107A CA2519107A1 CA 2519107 A1 CA2519107 A1 CA 2519107A1 CA 002519107 A CA002519107 A CA 002519107A CA 2519107 A CA2519107 A CA 2519107A CA 2519107 A1 CA2519107 A1 CA 2519107A1

Authority

CA

Canada

Prior art keywords

triazolo

methyl

quinolin

phenyl

amino

Prior art date

2003-03-14

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 claims abstract description 161
• 238000000034 method Methods 0.000 claims abstract description 59
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 32
• 238000011282 treatment Methods 0.000 claims abstract description 29
• 201000011510 cancer Diseases 0.000 claims abstract description 11
• -1 NHCH3 Chemical group 0.000 claims description 97
• 239000000203 mixture Substances 0.000 claims description 73
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 69
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 63
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
• 239000007787 solid Substances 0.000 claims description 56
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 42
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 38
• OGRIQXCIIAIROA-UHFFFAOYSA-N 2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=CC=C2N3C(=O)NN=C3C=CC2=C1 OGRIQXCIIAIROA-UHFFFAOYSA-N 0.000 claims description 37
• 238000006243 chemical reaction Methods 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
• 239000011541 reaction mixture Substances 0.000 claims description 32
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 241000282414 Homo sapiens Species 0.000 claims description 20
• 241001465754 Metazoa Species 0.000 claims description 20
• 238000001816 cooling Methods 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
• 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 claims description 19
• 125000004429 atom Chemical group 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 239000000725 suspension Substances 0.000 claims description 18
• 239000012043 crude product Substances 0.000 claims description 17
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 229910000024 caesium carbonate Inorganic materials 0.000 claims description 16
• 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 claims description 15
• 229910052740 iodine Inorganic materials 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 14
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000003107 substituted aryl group Chemical group 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 238000004128 high performance liquid chromatography Methods 0.000 claims description 13
• 238000010992 reflux Methods 0.000 claims description 13
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
• VKVVHUCKBYHGFK-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound C1=NN=C2N1C1=CC=CC=C1C(=C2)C(=O)N VKVVHUCKBYHGFK-UHFFFAOYSA-N 0.000 claims description 11
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
• VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 claims description 11
• 229910052763 palladium Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 10
• 238000006467 substitution reaction Methods 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 9
• 239000011593 sulfur Substances 0.000 claims description 9
• 210000001519 tissue Anatomy 0.000 claims description 9
• 208000023275 Autoimmune disease Diseases 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 8
• 229910003204 NH2 Inorganic materials 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 230000001613 neoplastic effect Effects 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 8
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 8
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
• 206010025323 Lymphomas Diseases 0.000 claims description 7
• 208000012902 Nervous system disease Diseases 0.000 claims description 7
• 208000025966 Neurological disease Diseases 0.000 claims description 7
• 206010033128 Ovarian cancer Diseases 0.000 claims description 7
• 230000001363 autoimmune Effects 0.000 claims description 7
• 201000008275 breast carcinoma Diseases 0.000 claims description 7
• 210000003169 central nervous system Anatomy 0.000 claims description 7
• 210000001072 colon Anatomy 0.000 claims description 7
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• 230000002757 inflammatory effect Effects 0.000 claims description 7
• 210000004072 lung Anatomy 0.000 claims description 7
• 201000005296 lung carcinoma Diseases 0.000 claims description 7
• 201000001441 melanoma Diseases 0.000 claims description 7
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
• 230000000926 neurological effect Effects 0.000 claims description 7
• 201000008968 osteosarcoma Diseases 0.000 claims description 7
• 210000001672 ovary Anatomy 0.000 claims description 7
• 210000001428 peripheral nervous system Anatomy 0.000 claims description 7
• 230000002062 proliferating effect Effects 0.000 claims description 7
• 210000002307 prostate Anatomy 0.000 claims description 7
• 201000001514 prostate carcinoma Diseases 0.000 claims description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• 201000008808 Fibrosarcoma Diseases 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
• FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 238000001727 in vivo Methods 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 229930192474 thiophene Natural products 0.000 claims description 5
• MMMAUNAGFRKDPU-UHFFFAOYSA-N 4-(hydroxymethyl)-8-thiophen-2-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=C2N(C(NN=3)=O)C=3C(CO)=CC2=CC=C1C1=CC=CS1 MMMAUNAGFRKDPU-UHFFFAOYSA-N 0.000 claims description 4
• UBKDDRZJUKPMSU-UHFFFAOYSA-N 4-amino-8-[3-(hydroxymethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=C2N(C(NN=3)=O)C=3C(N)=CC2=CC=C1C1=CC=CC(CO)=C1 UBKDDRZJUKPMSU-UHFFFAOYSA-N 0.000 claims description 4
• AOLKZDJPMBJJBV-UHFFFAOYSA-N 4-amino-8-thiophen-2-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=C2N(C(NN=3)=O)C=3C(N)=CC2=CC=C1C1=CC=CS1 AOLKZDJPMBJJBV-UHFFFAOYSA-N 0.000 claims description 4
• FEKDFTQZRBQDGS-UHFFFAOYSA-N 5-(hydroxymethyl)-8-(1h-pyrrol-2-yl)-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(CO)=CC3=NNC(=O)N3C2=CC=1C1=CC=CN1 FEKDFTQZRBQDGS-UHFFFAOYSA-N 0.000 claims description 4
• DOWPPYBKBCYNMD-UHFFFAOYSA-N 5-[2-[[2-(4-benzylpiperazin-1-yl)ethylamino]methyl]-6-hydroxyphenyl]-2H-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C2=NNC(=O)N2C2=CC=CC=C2C=1C=1C(O)=CC=CC=1CNCCN(CC1)CCN1CC1=CC=CC=C1 DOWPPYBKBCYNMD-UHFFFAOYSA-N 0.000 claims description 4
• AOFKHDAFIBWWIS-UHFFFAOYSA-N 5-[2-hydroxy-6-[(4-pyridin-2-ylpiperazin-1-yl)methyl]phenyl]-2H-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C2=NNC(=O)N2C2=CC=CC=C2C=1C=1C(O)=CC=CC=1CN(CC1)CCN1C1=CC=CC=N1 AOFKHDAFIBWWIS-UHFFFAOYSA-N 0.000 claims description 4
• AZRPHILLLLTFMN-OAHLLOKOSA-N 5-[[(3r)-3-hydroxypyrrolidin-1-yl]methyl]-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1[C@H](O)CCN1CC1=CC2=NNC(=O)N2C2=CC(C3=CSC=C3)=CC=C12 AZRPHILLLLTFMN-OAHLLOKOSA-N 0.000 claims description 4
• KVXCXEGCBRWKTH-UHFFFAOYSA-N 5-amino-7-hydroxy-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(N)=CC3=NNC(=O)N3C2=CC=1C=1C=CSC=1 KVXCXEGCBRWKTH-UHFFFAOYSA-N 0.000 claims description 4
• IZUPGASFHSZLHL-UHFFFAOYSA-N 5-amino-8-(1h-pyrazol-4-yl)-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(N)=CC3=NNC(=O)N3C2=CC=1C=1C=NNC=1 IZUPGASFHSZLHL-UHFFFAOYSA-N 0.000 claims description 4
• KXKMGDIODQOGBS-UHFFFAOYSA-N 5-amino-8-(furan-3-yl)-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(N)=CC3=NNC(=O)N3C2=CC=1C=1C=COC=1 KXKMGDIODQOGBS-UHFFFAOYSA-N 0.000 claims description 4
• GFYGOPHFJJDPOL-UHFFFAOYSA-N 5-methyl-8-(1h-pyrazol-4-yl)-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C=1C=NNC=1 GFYGOPHFJJDPOL-UHFFFAOYSA-N 0.000 claims description 4
• XEVVVGBZFPTGEN-UHFFFAOYSA-N 5-methyl-8-(4-methylthiophen-2-yl)-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound CC1=CSC(C=2C=C3N4C(=O)NN=C4C=C(C)C3=CC=2)=C1 XEVVVGBZFPTGEN-UHFFFAOYSA-N 0.000 claims description 4
• LVOFPVMDPPUJMM-UHFFFAOYSA-N 5-methyl-8-thiophen-2-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CS1 LVOFPVMDPPUJMM-UHFFFAOYSA-N 0.000 claims description 4
• NSTVAVLNOIGABS-UHFFFAOYSA-N 6-[3-(aminomethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound NCC1=CC=CC(C=2C3=C(N4C(=O)NN=C4C=C3)C=CC=2)=C1 NSTVAVLNOIGABS-UHFFFAOYSA-N 0.000 claims description 4
• GFCKJFGHHSDFLP-UHFFFAOYSA-N 6-[3-[(cyclopentylamino)methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=CC=C2N3C(=O)NN=C3C=CC2=C1C(C=1)=CC=CC=1CNC1CCCC1 GFCKJFGHHSDFLP-UHFFFAOYSA-N 0.000 claims description 4
• VRCFQXOVCWJXFU-UHFFFAOYSA-N 6-[3-[[4-(2-hydroxyethyl)-1,4-diazepan-1-yl]methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1CN(CCO)CCCN1CC1=CC=CC(C=2C3=C(N4C(=O)NN=C4C=C3)C=CC=2)=C1 VRCFQXOVCWJXFU-UHFFFAOYSA-N 0.000 claims description 4
• KUQKQVQEWOCHHG-UHFFFAOYSA-N 6-[3-[[4-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1CC(CO)CCN1CC1=CC=CC(C=2C3=C(N4C(=O)NN=C4C=C3)C=CC=2)=C1 KUQKQVQEWOCHHG-UHFFFAOYSA-N 0.000 claims description 4
• JPTJUVNGMNWDBD-UHFFFAOYSA-N 6-[4-hydroxy-3-[(2-methylpropylamino)methyl]phenyl]-2H-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=C(O)C(CNCC(C)C)=CC(C=2C3=C(N4C(=O)NN=C4C=C3)C=CC=2)=C1 JPTJUVNGMNWDBD-UHFFFAOYSA-N 0.000 claims description 4
• HXUJFZQHHOOKRN-UHFFFAOYSA-N 7-hydroxy-5-(hydroxymethyl)-8-[2-(hydroxymethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OCC1=CC=CC=C1C1=CC(N2C(=O)NN=C2C=C2CO)=C2C=C1O HXUJFZQHHOOKRN-UHFFFAOYSA-N 0.000 claims description 4
• AXEUNJUFWIQQED-UHFFFAOYSA-N 7-hydroxy-5-(hydroxymethyl)-8-[3-(hydroxymethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OCC1=CC=CC(C=2C(=CC3=C(N4C(=O)NN=C4C=C3CO)C=2)O)=C1 AXEUNJUFWIQQED-UHFFFAOYSA-N 0.000 claims description 4
• JODJCISKIGOPTH-UHFFFAOYSA-N 7-hydroxy-5-methyl-8-[3-[(pyridin-4-ylmethylamino)methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C(C=1)=CC=CC=1CNCC1=CC=NC=C1 JODJCISKIGOPTH-UHFFFAOYSA-N 0.000 claims description 4
• FHNDVAAAMNWGCV-UHFFFAOYSA-N 7-hydroxy-5-methyl-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C=1C=CSC=1 FHNDVAAAMNWGCV-UHFFFAOYSA-N 0.000 claims description 4
• ZANNTOIFCOLYBU-UHFFFAOYSA-N 7-hydroxy-8-(2-methoxypyridin-4-yl)-5-methyl-2H-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=NC(OC)=CC(C=2C(=CC3=C(N4C(=O)NN=C4C=C3C)C=2)O)=C1 ZANNTOIFCOLYBU-UHFFFAOYSA-N 0.000 claims description 4
• AEZSFCCTKRNNRD-UHFFFAOYSA-N 7-hydroxy-8-(3-hydroxyphenyl)-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CC(O)=C1 AEZSFCCTKRNNRD-UHFFFAOYSA-N 0.000 claims description 4
• CPFXXSZJHQCOGA-UHFFFAOYSA-N 7-hydroxy-8-[2-[(2-hydroxypropylamino)methyl]phenyl]-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound CC(O)CNCC1=CC=CC=C1C1=CC(N2C(=O)NN=C2C=C2C)=C2C=C1O CPFXXSZJHQCOGA-UHFFFAOYSA-N 0.000 claims description 4
• ADOTXZXVNDBWFH-UHFFFAOYSA-N 7-hydroxy-8-[3-[(3-imidazol-1-ylpropylamino)methyl]phenyl]-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C(C=1)=CC=CC=1CNCCCN1C=CN=C1 ADOTXZXVNDBWFH-UHFFFAOYSA-N 0.000 claims description 4
• IPPVBKSZTJUEJS-UHFFFAOYSA-N 7-methoxy-5-methyl-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C=1C=CSC=1 IPPVBKSZTJUEJS-UHFFFAOYSA-N 0.000 claims description 4
• YYAJZHIEGXTKJC-UHFFFAOYSA-N 8-(2-aminophenyl)-7-hydroxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CC=C1N YYAJZHIEGXTKJC-UHFFFAOYSA-N 0.000 claims description 4
• WEFRYBUHEOYJFC-UHFFFAOYSA-N 8-(3-aminophenyl)-5-(hydroxymethyl)-7-methoxy-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(CO)=CC3=NNC(=O)N3C=2C=C1C1=CC=CC(N)=C1 WEFRYBUHEOYJFC-UHFFFAOYSA-N 0.000 claims description 4
• JAFIHUNKABPTIC-UHFFFAOYSA-N 8-(3-aminophenyl)-7-hydroxy-5-(hydroxymethyl)-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound NC1=CC=CC(C=2C(=CC3=C(N4C(=O)NN=C4C=C3CO)C=2)O)=C1 JAFIHUNKABPTIC-UHFFFAOYSA-N 0.000 claims description 4
• FRNQEFIHCIMWFD-UHFFFAOYSA-N 8-(3-aminophenyl)-7-hydroxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CC(N)=C1 FRNQEFIHCIMWFD-UHFFFAOYSA-N 0.000 claims description 4
• CJIZVYSZDITSQL-UHFFFAOYSA-N 8-(4-chlorophenyl)-7-hydroxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=C(Cl)C=C1 CJIZVYSZDITSQL-UHFFFAOYSA-N 0.000 claims description 4
• KQBBQYZIFJXZLF-UHFFFAOYSA-N 8-[2-[(cyclopentylamino)methyl]phenyl]-7-hydroxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CC=C1CNC1CCCC1 KQBBQYZIFJXZLF-UHFFFAOYSA-N 0.000 claims description 4
• TYQJRXMFDVGNJK-UHFFFAOYSA-N 8-[2-[[4-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C1=CC=CC=C1CN1CCC(CO)CC1 TYQJRXMFDVGNJK-UHFFFAOYSA-N 0.000 claims description 4
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• PVABMSKSGGLIQQ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-8-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound C=1C=C2C(C(=O)NCCN(C)C)=CC3=NNC(=O)N3C2=CC=1C(C=C1)=CC=C1CN1CCN(C)CC1 PVABMSKSGGLIQQ-UHFFFAOYSA-N 0.000 claims description 2
• RWMJBBHCGVCOFJ-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-8-[5-[(4-methylpiperazin-1-yl)methyl]thiophen-2-yl]-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound C=1C=C2C(C(=O)NCCN(C)C)=CC3=NNC(=O)N3C2=CC=1C(S1)=CC=C1CN1CCN(C)CC1 RWMJBBHCGVCOFJ-UHFFFAOYSA-N 0.000 claims description 2
• FRVQLJMGNAVROK-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-8-[5-[(4-methylpiperazin-1-yl)methyl]thiophen-3-yl]-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound C=1C=C2C(C(=O)NCCN(C)C)=CC3=NNC(=O)N3C2=CC=1C(C=1)=CSC=1CN1CCN(C)CC1 FRVQLJMGNAVROK-UHFFFAOYSA-N 0.000 claims description 2
• ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 claims description 2
• LZHJFZLHEGJWAU-UHFFFAOYSA-N quinoline-5-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=N1 LZHJFZLHEGJWAU-UHFFFAOYSA-N 0.000 claims description 2
• RAYMXZBXQCGRGX-UHFFFAOYSA-N quinoline-5-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=N1 RAYMXZBXQCGRGX-UHFFFAOYSA-N 0.000 claims description 2
• 230000010076 replication Effects 0.000 claims description 2
• VENUGRJSSLOZIN-INIZCTEOSA-N tert-butyl (3s)-3-[[1-oxo-8-(1h-pyrrol-2-yl)-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carbonyl]amino]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC[C@@H]1NC(=O)C1=CC2=NNC(=O)N2C2=CC(C=3NC=CC=3)=CC=C12 VENUGRJSSLOZIN-INIZCTEOSA-N 0.000 claims description 2
• FVXZTLUYZFZLPT-UHFFFAOYSA-N tert-butyl 4-[[4-(1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-5-yl)phenyl]methylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NCC1=CC=C(C=2C3=CC=CC=C3N3C(=O)NN=C3C=2)C=C1 FVXZTLUYZFZLPT-UHFFFAOYSA-N 0.000 claims description 2
• MSGAKCCDZAGKKT-UHFFFAOYSA-N tert-butyl 4-[[4-(5-methyl-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-8-yl)thiophen-2-yl]methyl]piperazine-1-carboxylate Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C(C=1)=CSC=1CN1CCN(C(=O)OC(C)(C)C)CC1 MSGAKCCDZAGKKT-UHFFFAOYSA-N 0.000 claims description 2
• IJGDZUQREFGMRY-UHFFFAOYSA-N tert-butyl n-(7-bromo-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-5-yl)carbamate Chemical compound C1=C(Br)C=C2C(NC(=O)OC(C)(C)C)=CC3=NNC(=O)N3C2=C1 IJGDZUQREFGMRY-UHFFFAOYSA-N 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
• VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims 4
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
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• BZMXMTHQVLJTNF-UHFFFAOYSA-N (1-oxo-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-5-yl)methyl 2-(methylamino)acetate Chemical compound C=1C=C2C(COC(=O)CNC)=CC3=NNC(=O)N3C2=CC=1C=1C=CSC=1 BZMXMTHQVLJTNF-UHFFFAOYSA-N 0.000 claims 1
• RXGMMOQLULZAFT-UHFFFAOYSA-N (5-methyl-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-8-yl)boronic acid Chemical compound OB(O)C1=CC=C2C(C)=CC3=NNC(=O)N3C2=C1 RXGMMOQLULZAFT-UHFFFAOYSA-N 0.000 claims 1
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• RISGDPZHROSWOU-UHFFFAOYSA-N 3-(dimethylamino)-n-(1-oxo-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-5-yl)propanamide Chemical compound C=1C=C2C(NC(=O)CCN(C)C)=CC3=NNC(=O)N3C2=CC=1C=1C=CSC=1 RISGDPZHROSWOU-UHFFFAOYSA-N 0.000 claims 1
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• KCPYLAMMAJERJG-UHFFFAOYSA-N 4-methyl-n-(1-oxo-8-thiophen-2-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-4-yl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC2=CC=C(C=3SC=CC=3)C=C2N2C(=O)NN=C12 KCPYLAMMAJERJG-UHFFFAOYSA-N 0.000 claims 1
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• HSTOQAFRLZCLEN-CYBMUJFWSA-N 5-[(3r)-3-hydroxypyrrolidine-1-carbonyl]-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1[C@H](O)CCN1C(=O)C1=CC2=NNC(=O)N2C2=CC(C3=CSC=C3)=CC=C12 HSTOQAFRLZCLEN-CYBMUJFWSA-N 0.000 claims 1
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• QENPKDNCSBOKIO-UHFFFAOYSA-N 5-[4-[[4-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1CC(CO)CCN1CC1=CC=C(C=2C3=CC=CC=C3N3C(=O)NN=C3C=2)C=C1 QENPKDNCSBOKIO-UHFFFAOYSA-N 0.000 claims 1
• STBNAEMYJWQVGD-UHFFFAOYSA-N 5-[4-methoxy-3-[(4-pyridin-2-ylpiperazin-1-yl)methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=C(C=2C3=CC=CC=C3N3C(=O)NN=C3C=2)C=C1CN(CC1)CCN1C1=CC=CC=N1 STBNAEMYJWQVGD-UHFFFAOYSA-N 0.000 claims 1
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• DDORPXIICGGQHS-OAHLLOKOSA-N 5-[[(3r)-3-aminopyrrolidin-1-yl]methyl]-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1[C@H](N)CCN1CC1=CC2=NNC(=O)N2C2=CC(C3=CSC=C3)=CC=C12 DDORPXIICGGQHS-OAHLLOKOSA-N 0.000 claims 1
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• JDGCDJQWTPKDAE-UHFFFAOYSA-N 5-[[2-(propan-2-ylamino)ethylamino]methyl]-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(CNCCNC(C)C)=CC3=NNC(=O)N3C2=CC=1C=1C=CSC=1 JDGCDJQWTPKDAE-UHFFFAOYSA-N 0.000 claims 1
• JASSKKNNEWNCPS-UHFFFAOYSA-N 5-[[2-hydroxyethyl(methyl)amino]methyl]-8-[5-(methylaminomethyl)thiophen-3-yl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound S1C(CNC)=CC(C=2C=C3N4C(=O)NN=C4C=C(CN(C)CCO)C3=CC=2)=C1 JASSKKNNEWNCPS-UHFFFAOYSA-N 0.000 claims 1
• XZQHGEQIUIMUOB-UHFFFAOYSA-N 5-[[2-methoxyethyl(methyl)amino]methyl]-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(CN(C)CCOC)=CC3=NNC(=O)N3C2=CC=1C=1C=CSC=1 XZQHGEQIUIMUOB-UHFFFAOYSA-N 0.000 claims 1
• MJRDQBBBTINMDF-UHFFFAOYSA-N 5-[[3-(dimethylamino)propylamino]methyl]-8-(1h-pyrrol-2-yl)-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(CNCCCN(C)C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CN1 MJRDQBBBTINMDF-UHFFFAOYSA-N 0.000 claims 1
• LVWWLOZIPRHWKL-OAHLLOKOSA-N 5-[[[(3r)-pyrrolidin-3-yl]amino]methyl]-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C12=CC=C(C3=CSC=C3)C=C2N2C(=O)NN=C2C=C1CN[C@@H]1CCNC1 LVWWLOZIPRHWKL-OAHLLOKOSA-N 0.000 claims 1
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• OOJBJQUQEZPXMG-UHFFFAOYSA-N 5-methyl-8-[4-(piperazin-1-ylmethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C(C=C1)=CC=C1CN1CCNCC1 OOJBJQUQEZPXMG-UHFFFAOYSA-N 0.000 claims 1
• NRSFIYPUCAXIGY-UHFFFAOYSA-N 5-methyl-8-[5-(piperazin-1-ylmethyl)thiophen-3-yl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C(C=1)=CSC=1CN1CCNCC1 NRSFIYPUCAXIGY-UHFFFAOYSA-N 0.000 claims 1
• JNOBZBVAOKITPI-AWEZNQCLSA-N 5-methyl-8-[5-[[[(3s)-pyrrolidin-3-yl]amino]methyl]thiophen-2-yl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C(S1)=CC=C1CN[C@H]1CCNC1 JNOBZBVAOKITPI-AWEZNQCLSA-N 0.000 claims 1
• MZMCWYKOCNWNJK-UHFFFAOYSA-N 5-methyl-8-pyridin-3-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CN=C1 MZMCWYKOCNWNJK-UHFFFAOYSA-N 0.000 claims 1
• PJIXXMREXFGWBU-UHFFFAOYSA-N 6-[4-(aminomethyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=CC(CN)=CC=C1C1=CC=CC2=C1C=CC1=NNC(=O)N21 PJIXXMREXFGWBU-UHFFFAOYSA-N 0.000 claims 1
• QCBHFYOCWWXGMJ-IBGZPJMESA-N 7-[4-[[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]methyl]phenyl]-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=C2C(C)=CC3=NNC(=O)N3C2=CC=C1C(C=C1)=CC=C1CN1CCC[C@H]1CO QCBHFYOCWWXGMJ-IBGZPJMESA-N 0.000 claims 1
• CAYDSCDUTHACEN-UHFFFAOYSA-N 7-bromo-5-thiophen-2-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one;ethyl 8-chloro-7-methoxy-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxylate Chemical compound C=1C(Br)=CC=C(N2C(=O)NN=C2C=2)C=1C=2C1=CC=CS1.ClC1=C(OC)C=C2C(C(=O)OCC)=CC3=NNC(=O)N3C2=C1 CAYDSCDUTHACEN-UHFFFAOYSA-N 0.000 claims 1
• YJDFNBYWSWUMOT-UHFFFAOYSA-N 7-hydroxy-8-[2-[[4-(hydroxymethyl)piperidin-1-yl]methyl]phenyl]-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CC=C1CN1CCC(CO)CC1 YJDFNBYWSWUMOT-UHFFFAOYSA-N 0.000 claims 1
• ANFGQOJRXJNUKA-UHFFFAOYSA-N 7-methoxy-5-methyl-8-[3-[(2-methylpropylamino)methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C1=CC=CC(CNCC(C)C)=C1 ANFGQOJRXJNUKA-UHFFFAOYSA-N 0.000 claims 1
• UONDDPKEINWQSW-UHFFFAOYSA-N 7-methoxy-5-methyl-8-[3-[(pyridin-4-ylmethylamino)methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C(C=1)=CC=CC=1CNCC1=CC=NC=C1 UONDDPKEINWQSW-UHFFFAOYSA-N 0.000 claims 1
• SZMDQMYUSSXNAJ-UHFFFAOYSA-N 7-methoxy-5-methyl-8-[3-[[(1-methylpyrrol-2-yl)methylamino]methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C(C=1)=CC=CC=1CNCC1=CC=CN1C SZMDQMYUSSXNAJ-UHFFFAOYSA-N 0.000 claims 1
• ZYIUOVZTNPNIFY-UHFFFAOYSA-N 7-methoxy-5-methyl-8-[4-(morpholine-4-carbonyl)phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C(C=C1)=CC=C1C(=O)N1CCOCC1 ZYIUOVZTNPNIFY-UHFFFAOYSA-N 0.000 claims 1
• DODPNQSSJVCLAD-UHFFFAOYSA-N 7-methoxy-8-[3-[(2-methoxyethylamino)methyl]phenyl]-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COCCNCC1=CC=CC(C=2C(=CC3=C(N4C(=O)NN=C4C=C3C)C=2)OC)=C1 DODPNQSSJVCLAD-UHFFFAOYSA-N 0.000 claims 1
• NJCLIYNGLCJTTG-UHFFFAOYSA-N 7-methoxy-8-[4-methoxy-3-[(2-methoxyethylamino)methyl]phenyl]-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=C(OC)C(CNCCOC)=CC(C=2C(=CC3=C(N4C(=O)NN=C4C=C3C)C=2)OC)=C1 NJCLIYNGLCJTTG-UHFFFAOYSA-N 0.000 claims 1
• BCGKPWYQZZNJBK-UHFFFAOYSA-N 7-piperazin-1-yl-5-thiophen-2-yl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C12=CC(N3CCNCC3)=CC=C2N2C(=O)NN=C2C=C1C1=CC=CS1 BCGKPWYQZZNJBK-UHFFFAOYSA-N 0.000 claims 1
• SCPIHIARIJSIHX-UHFFFAOYSA-N 8-(3-hydroxyphenyl)-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CC(O)=C1 SCPIHIARIJSIHX-UHFFFAOYSA-N 0.000 claims 1
• PZXXJIFQPOXWJV-UHFFFAOYSA-N 8-(furan-2-yl)-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CO1 PZXXJIFQPOXWJV-UHFFFAOYSA-N 0.000 claims 1
• AKJJUOFBVLTGDA-UHFFFAOYSA-N 8-(furan-2-yl)-5-phenyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C12=CC=C(C=3OC=CC=3)C=C2N2C(=O)NN=C2C=C1C1=CC=CC=C1 AKJJUOFBVLTGDA-UHFFFAOYSA-N 0.000 claims 1
• QVZQIFQHMVFTMA-UHFFFAOYSA-N 8-[2-(hydroxymethyl)phenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C1=CC=CC=C1CO QVZQIFQHMVFTMA-UHFFFAOYSA-N 0.000 claims 1
• FHXPVNRMPDDKFR-UHFFFAOYSA-N 8-[2-[(cyclopentylamino)methyl]phenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C1=CC=CC=C1CNC1CCCC1 FHXPVNRMPDDKFR-UHFFFAOYSA-N 0.000 claims 1
• GEKXEJIENSUCJT-UHFFFAOYSA-N 8-[2-[[(4-fluorophenyl)methylamino]methyl]phenyl]-7-hydroxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CC=C1CNCC1=CC=C(F)C=C1 GEKXEJIENSUCJT-UHFFFAOYSA-N 0.000 claims 1
• QTSDUYTYGCIKAY-UHFFFAOYSA-N 8-[3-[(2-hydroxyethylamino)methyl]phenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C1=CC=CC(CNCCO)=C1 QTSDUYTYGCIKAY-UHFFFAOYSA-N 0.000 claims 1
• GHRPINQEPDIHTH-UHFFFAOYSA-N 8-[3-[(cyclohexylamino)methyl]-4-methoxyphenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=C(C=2C(=CC3=C(N4C(=O)NN=C4C=C3C)C=2)OC)C=C1CNC1CCCCC1 GHRPINQEPDIHTH-UHFFFAOYSA-N 0.000 claims 1
• XCPTWAWCBCGHHY-UHFFFAOYSA-N 8-[3-[(cyclopentylamino)methyl]phenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C(C=1)=CC=CC=1CNC1CCCC1 XCPTWAWCBCGHHY-UHFFFAOYSA-N 0.000 claims 1
• KYHBDXBRVAIFOL-UHFFFAOYSA-N 8-[3-[[3-(dimethylamino)propylamino]methyl]-4-methoxyphenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=C(CNCCCN(C)C)C(OC)=CC=C1C1=CC(N2C(=O)NN=C2C=C2C)=C2C=C1OC KYHBDXBRVAIFOL-UHFFFAOYSA-N 0.000 claims 1
• BOMNGWWDEDTYAU-UHFFFAOYSA-N 8-[3-[[4-(2-hydroxyethyl)piperidin-1-yl]methyl]-4-methoxyphenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=C(C=2C(=CC3=C(N4C(=O)NN=C4C=C3C)C=2)OC)C=C1CN1CCC(CCO)CC1 BOMNGWWDEDTYAU-UHFFFAOYSA-N 0.000 claims 1
• CCFXPPRCVWBFKJ-UHFFFAOYSA-N 8-[3-[[4-(2-hydroxyethyl)piperidin-1-yl]methyl]phenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C(C=1)=CC=CC=1CN1CCC(CCO)CC1 CCFXPPRCVWBFKJ-UHFFFAOYSA-N 0.000 claims 1
• JWUJMLDXIXLQEV-UHFFFAOYSA-N 8-[3-[[4-(hydroxymethyl)piperidin-1-yl]methyl]-4-methoxyphenyl]-7-methoxy-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound COC1=CC=C(C=2C(=CC3=C(N4C(=O)NN=C4C=C3C)C=2)OC)C=C1CN1CCC(CO)CC1 JWUJMLDXIXLQEV-UHFFFAOYSA-N 0.000 claims 1
• YAZUBHJIBBURKG-UHFFFAOYSA-N 8-[5-(methylaminomethyl)thiophen-3-yl]-5-[[methyl-[2-(methylamino)ethyl]amino]methyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C=1C=C2C(CN(C)CCNC)=CC3=NNC(=O)N3C2=CC=1C1=CSC(CNC)=C1 YAZUBHJIBBURKG-UHFFFAOYSA-N 0.000 claims 1
• XIDVXQFOKZKBNH-UHFFFAOYSA-N 8-bromo-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxylic acid;5-[4-[(2-hydroxyethylamino)methyl]phenyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound BrC1=CC=C2C(C(=O)O)=CC3=NNC(=O)N3C2=C1.C1=CC(CNCCO)=CC=C1C1=CC2=NNC(=O)N2C2=CC=CC=C12 XIDVXQFOKZKBNH-UHFFFAOYSA-N 0.000 claims 1
• OLSXQJSUQRHYEE-UHFFFAOYSA-N 8-bromo-5-[2-(dimethylamino)ethoxymethyl]-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound BrC1=CC=C2C(COCCN(C)C)=CC3=NNC(=O)N3C2=C1 OLSXQJSUQRHYEE-UHFFFAOYSA-N 0.000 claims 1
• AOCCQMFIIYNHRX-UHFFFAOYSA-N 8-fluoro-5-methyl-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound FC1=CC=C2C(C)=CC3=NNC(=O)N3C2=C1 AOCCQMFIIYNHRX-UHFFFAOYSA-N 0.000 claims 1
• HKWLVXCJONXVEY-UHFFFAOYSA-N 9-hydroxy-2h-[1,2,4]triazolo[4,3-a]quinolin-1-one Chemical compound C1=CC2=NNC(=O)N2C2=C1C=CC=C2O HKWLVXCJONXVEY-UHFFFAOYSA-N 0.000 claims 1
• DUSJNYRBTQQLJQ-UHFFFAOYSA-N OC=1C=C2C(=CC=3N(C2=CC1C1=CC=CC=C1)C(NN3)=O)C.C3(CCC3)NCC=3C=1N(C2=CC=C(C=C2C3)O)C(NN1)=O Chemical compound OC=1C=C2C(=CC=3N(C2=CC1C1=CC=CC=C1)C(NN3)=O)C.C3(CCC3)NCC=3C=1N(C2=CC=C(C=C2C3)O)C(NN1)=O DUSJNYRBTQQLJQ-UHFFFAOYSA-N 0.000 claims 1
• YHEQRESIOPFJGY-UHFFFAOYSA-N ethyl 1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=CC3=NNC(=O)N3C2=C1 YHEQRESIOPFJGY-UHFFFAOYSA-N 0.000 claims 1
• HAICXVVEDPENEL-UHFFFAOYSA-N ethyl 7-bromo-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxylate Chemical compound C1=C(Br)C=C2C(C(=O)OCC)=CC3=NNC(=O)N3C2=C1 HAICXVVEDPENEL-UHFFFAOYSA-N 0.000 claims 1
• SPAKCWXTECMRHC-UHFFFAOYSA-N ethyl 8-chloro-7-methoxy-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxylate Chemical compound ClC1=C(OC)C=C2C(C(=O)OCC)=CC3=NNC(=O)N3C2=C1 SPAKCWXTECMRHC-UHFFFAOYSA-N 0.000 claims 1
• CSRLBOLKANRXIH-UHFFFAOYSA-N n-(2-aminoethyl)-1-oxo-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound C=1C=C2C(C(=O)NCCN)=CC3=NNC(=O)N3C2=CC=1C=1C=CSC=1 CSRLBOLKANRXIH-UHFFFAOYSA-N 0.000 claims 1
• RYUPBPSSZMZJGM-UHFFFAOYSA-N n-(2-aminoethyl)-8-bromo-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound BrC1=CC=C2C(C(=O)NCCN)=CC3=NNC(=O)N3C2=C1 RYUPBPSSZMZJGM-UHFFFAOYSA-N 0.000 claims 1
• JSGAQXKZVAGVDN-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-1-oxo-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=CC2=NNC(=O)N2C2=CC(C3=CSC=C3)=CC=C12 JSGAQXKZVAGVDN-UHFFFAOYSA-N 0.000 claims 1
• MUMATIMOVUWFQZ-UHFFFAOYSA-N n-[1-(dimethylamino)propan-2-yl]-1-oxo-8-thiophen-3-yl-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound C=1C=C2C(C(=O)NC(CN(C)C)C)=CC3=NNC(=O)N3C2=CC=1C=1C=CSC=1 MUMATIMOVUWFQZ-UHFFFAOYSA-N 0.000 claims 1
• IDAVXXNGZJFXKN-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-8-(furan-3-yl)-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound C=1C=C2C(C(=O)NCCN(C)C)=CC3=NNC(=O)N3C2=CC=1C=1C=COC=1 IDAVXXNGZJFXKN-UHFFFAOYSA-N 0.000 claims 1
• CTGWBKKIOWHBMV-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-8-[5-(methylaminomethyl)thiophen-3-yl]-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound S1C(CNC)=CC(C=2C=C3N4C(=O)NN=C4C=C(C3=CC=2)C(=O)NCCN(C)C)=C1 CTGWBKKIOWHBMV-UHFFFAOYSA-N 0.000 claims 1
• PAFCKMHJISYZPS-UHFFFAOYSA-N n-[2-(methylamino)ethyl]-1-oxo-8-(1h-pyrrol-2-yl)-2h-[1,2,4]triazolo[4,3-a]quinoline-5-carboxamide Chemical compound C=1C=C2C(C(=O)NCCNC)=CC3=NNC(=O)N3C2=CC=1C1=CC=CN1 PAFCKMHJISYZPS-UHFFFAOYSA-N 0.000 claims 1
• YIPRXXBVSCVEGM-UHFFFAOYSA-N n-[4-(5-methyl-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-8-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=C(C(C)=CC=2N3C(=O)NN=2)C3=C1 YIPRXXBVSCVEGM-UHFFFAOYSA-N 0.000 claims 1
• PYVIRTDGURZDBX-UHFFFAOYSA-N n-cyclohexyl-4-(7-hydroxy-5-methyl-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-8-yl)benzamide Chemical compound OC=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C(C=C1)=CC=C1C(=O)NC1CCCCC1 PYVIRTDGURZDBX-UHFFFAOYSA-N 0.000 claims 1
• STVYTUNLGHDBOS-UHFFFAOYSA-N n-cyclohexyl-4-(7-methoxy-5-methyl-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-8-yl)benzamide Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C(C=C1)=CC=C1C(=O)NC1CCCCC1 STVYTUNLGHDBOS-UHFFFAOYSA-N 0.000 claims 1
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• MZZGFBZWHLGLNQ-UHFFFAOYSA-N tert-butyl 4-[[4-(5-methyl-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-8-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C=1C=C2C(C)=CC3=NNC(=O)N3C2=CC=1C(C=C1)=CC=C1CN1CCN(C(=O)OC(C)(C)C)CC1 MZZGFBZWHLGLNQ-UHFFFAOYSA-N 0.000 claims 1
• UJMAQJZAFXXNQN-UHFFFAOYSA-N tert-butyl n-[2-[[1-oxo-8-(1h-pyrrol-2-yl)-2h-[1,2,4]triazolo[4,3-a]quinolin-5-yl]methylamino]ethyl]carbamate Chemical compound C=1C=C2C(CNCCNC(=O)OC(C)(C)C)=CC3=NNC(=O)N3C2=CC=1C1=CC=CN1 UJMAQJZAFXXNQN-UHFFFAOYSA-N 0.000 claims 1
• YQCXIWHFCCAQOY-UHFFFAOYSA-N tert-butyl n-[[3-(7-methoxy-5-methyl-1-oxo-2h-[1,2,4]triazolo[4,3-a]quinolin-8-yl)phenyl]methyl]carbamate Chemical compound COC1=CC=2C(C)=CC3=NNC(=O)N3C=2C=C1C1=CC=CC(CNC(=O)OC(C)(C)C)=C1 YQCXIWHFCCAQOY-UHFFFAOYSA-N 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 9
• 238000011321 prophylaxis Methods 0.000 abstract description 2
• 238000010586 diagram Methods 0.000 abstract 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 71
• 239000000243 solution Substances 0.000 description 39
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