TWI496779B - 作為ｐｉｍ激酶抑制劑之三唑吡啶化合物 - Google Patents

Info

Publication number

TWI496779B

TWI496779B TW098127485A TW98127485A TWI496779B TW I496779 B TWI496779 B TW I496779B TW 098127485 A TW098127485 A TW 098127485A TW 98127485 A TW98127485 A TW 98127485A TW I496779 B TWI496779 B TW I496779B

Authority

TW

Taiwan

Prior art keywords

triazolo

pyridin

quinoline

yloxy

alkyl

Prior art date

2008-08-19

Links

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• 150000008523 triazolopyridines Chemical class 0.000 title description 4
• 229940043355 kinase inhibitor Drugs 0.000 title description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 242
• 150000001875 compounds Chemical class 0.000 claims description 217
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 209
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 175
• 238000002360 preparation method Methods 0.000 claims description 134
• 201000006417 multiple sclerosis Diseases 0.000 claims description 84
• -1 3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ylamino)propyl Tri-butyl carbamic acid Chemical compound 0.000 claims description 81
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 69
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 65
• 238000006243 chemical reaction Methods 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• 238000011282 treatment Methods 0.000 claims description 55
• 229910052731 fluorine Inorganic materials 0.000 claims description 53
• 150000003839 salts Chemical class 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
• 229910052757 nitrogen Inorganic materials 0.000 claims description 39
• 101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 claims description 38
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 206010028980 Neoplasm Diseases 0.000 claims description 33
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 32
• 229910052794 bromium Inorganic materials 0.000 claims description 31
• 229910052801 chlorine Inorganic materials 0.000 claims description 31
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 30
• 208000023275 Autoimmune disease Diseases 0.000 claims description 26
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 26
• 235000019441 ethanol Nutrition 0.000 claims description 26
• 101100297651 Mus musculus Pim2 gene Proteins 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 201000011510 cancer Diseases 0.000 claims description 21
• 239000002904 solvent Substances 0.000 claims description 21
• 206010025135 lupus erythematosus Diseases 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 16
• 125000001424 substituent group Chemical group 0.000 claims description 16
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
• 238000004519 manufacturing process Methods 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 230000001404 mediated effect Effects 0.000 claims description 14
• 230000003287 optical effect Effects 0.000 claims description 14
• 208000027866 inflammatory disease Diseases 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 241000124008 Mammalia Species 0.000 claims description 12
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 241000156724 Antirhea Species 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
• 230000002757 inflammatory effect Effects 0.000 claims description 11
• 101100297652 Coturnix japonica PIM3 gene Proteins 0.000 claims description 10
• 108091000080 Phosphotransferase Proteins 0.000 claims description 10
• 102000020233 phosphotransferase Human genes 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 239000002585 base Substances 0.000 claims description 9
• 239000003153 chemical reaction reagent Substances 0.000 claims description 9
• 208000024891 symptom Diseases 0.000 claims description 9
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 229910052740 iodine Inorganic materials 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 6
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• ZXQIHLJIAWEHOF-ZBFHGGJFSA-N 8-[(3r,4s)-3-fluoropiperidin-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 ZXQIHLJIAWEHOF-ZBFHGGJFSA-N 0.000 claims description 5
• 239000011630 iodine Substances 0.000 claims description 5
• 150000004032 porphyrins Chemical class 0.000 claims description 5
• XQTDEFZROIJVJH-UHFFFAOYSA-N 8-[(4-fluoropiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(F)CCNCC1 XQTDEFZROIJVJH-UHFFFAOYSA-N 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
• AVHYIXDAOCBQIU-UHFFFAOYSA-N 2,2-difluoro-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(F)(F)CN)=NN=C21 AVHYIXDAOCBQIU-UHFFFAOYSA-N 0.000 claims description 3
• WEOAONDYUSMONB-UHFFFAOYSA-N 2,2-dimethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(CN)C)=NN=C21 WEOAONDYUSMONB-UHFFFAOYSA-N 0.000 claims description 3
• QYVMBCOLWIDSKD-UHFFFAOYSA-N 2-(7-methoxy-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C=3N4C=CC(=CC4=NN=3)OC)=CC=C21 QYVMBCOLWIDSKD-UHFFFAOYSA-N 0.000 claims description 3
• LHKDWQFFBVATPU-UHFFFAOYSA-N 2-[[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxymethyl]morpholine Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1CNCCO1 LHKDWQFFBVATPU-UHFFFAOYSA-N 0.000 claims description 3
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 3
• CUWBXIFJTGMJHU-UHFFFAOYSA-N 8-(2,2-dimethylpropoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(C)C)=NN=C21 CUWBXIFJTGMJHU-UHFFFAOYSA-N 0.000 claims description 3
• ZXQIHLJIAWEHOF-GDBMZVCRSA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 ZXQIHLJIAWEHOF-GDBMZVCRSA-N 0.000 claims description 3
• HETPKWYRMKCRBF-UHFFFAOYSA-N 8-[(4-ethylpiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(CC)CCNCC1 HETPKWYRMKCRBF-UHFFFAOYSA-N 0.000 claims description 3
• WCCKDZCVLHRLGN-UHFFFAOYSA-N N-piperidin-4-yl-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-amine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CNCCC1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 WCCKDZCVLHRLGN-UHFFFAOYSA-N 0.000 claims description 3
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
• 239000003054 catalyst Substances 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 239000003446 ligand Substances 0.000 claims description 3
• BNRNYCUKAUITIW-AWEZNQCLSA-N n-[(3s)-pyrrolidin-3-yl]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-amine Chemical compound C1NCC[C@@H]1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 BNRNYCUKAUITIW-AWEZNQCLSA-N 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
• LIVUQZJIYLMRNO-YSSOQSIOSA-N (2r)-2-ethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxybutan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OC(C)[C@@H](CN)CC)=NN=C21 LIVUQZJIYLMRNO-YSSOQSIOSA-N 0.000 claims description 2
• KRBNQISTMITIOJ-UHFFFAOYSA-N 2,2-dimethyl-3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-n-(2,2,2-trifluoroethyl)propan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(C)(CNCC(F)(F)F)C)=NN=C21 KRBNQISTMITIOJ-UHFFFAOYSA-N 0.000 claims description 2
• LUTLMEWAYGPCHC-UHFFFAOYSA-N 2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-[(4-fluoropiperidin-4-yl)methoxy]quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=C(C=CC4=NN=3)C3CC3)N=C2C=1OCC1(F)CCNCC1 LUTLMEWAYGPCHC-UHFFFAOYSA-N 0.000 claims description 2
• DPNYLXBQKCMOTA-UHFFFAOYSA-N 3-[2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-2,2-dimethylpropan-1-amine Chemical compound N1=C2C(OCC(C)(CN)C)=CC=CC2=CC=C1C(N1C=2)=NN=C1C=CC=2C1CC1 DPNYLXBQKCMOTA-UHFFFAOYSA-N 0.000 claims description 2
• QROPNMPPKCMQAY-UHFFFAOYSA-N 3-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypropane-1,2-diol Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)OCC(O)CO)=NN=C21 QROPNMPPKCMQAY-UHFFFAOYSA-N 0.000 claims description 2
• NQMGIRXTZPKONK-UHFFFAOYSA-N 3-[5-fluoro-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxy-2,2-dimethylpropan-1-amine Chemical compound C1=CC=CN2C(C3=CC=C4C(F)=CC=C(C4=N3)OCC(C)(CN)C)=NN=C21 NQMGIRXTZPKONK-UHFFFAOYSA-N 0.000 claims description 2
• KXDUVJWVGXIEPX-ZBFHGGJFSA-N 6-fluoro-8-[(3r,4s)-3-fluoropiperidin-4-yl]oxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC(F)=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 KXDUVJWVGXIEPX-ZBFHGGJFSA-N 0.000 claims description 2
• NQXPYPBIBFFEAE-UHFFFAOYSA-N 6-fluoro-8-[(4-fluoropiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=12N=C(C=3N4C=CC=CC4=NN=3)C=CC2=CC(F)=CC=1OCC1(F)CCNCC1 NQXPYPBIBFFEAE-UHFFFAOYSA-N 0.000 claims description 2
• QBGRDZKWELBKAA-AWEZNQCLSA-N 6-fluoro-8-[[(3s)-piperidin-3-yl]methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=12N=C(C=3N4C=CC=CC4=NN=3)C=CC2=CC(F)=CC=1OC[C@H]1CCCNC1 QBGRDZKWELBKAA-AWEZNQCLSA-N 0.000 claims description 2
• DIIUODQRBMKWMI-UHFFFAOYSA-N 8-(2-piperidin-2-ylethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCCC1CCCCN1 DIIUODQRBMKWMI-UHFFFAOYSA-N 0.000 claims description 2
• INYRWBVCPQQSGE-UHFFFAOYSA-N 8-(3,3-difluoropiperidin-4-yl)oxy-6-fluoro-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=12N=C(C=3N4C=CC=CC4=NN=3)C=CC2=CC(F)=CC=1OC1CCNCC1(F)F INYRWBVCPQQSGE-UHFFFAOYSA-N 0.000 claims description 2
• CAZNIOSROXHNKZ-UHFFFAOYSA-N 8-(piperidin-4-ylmethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1CCNCC1 CAZNIOSROXHNKZ-UHFFFAOYSA-N 0.000 claims description 2
• UDUHUPMKTQPDJW-UHFFFAOYSA-N 8-(pyridin-3-ylmethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1=CC=CN=C1 UDUHUPMKTQPDJW-UHFFFAOYSA-N 0.000 claims description 2
• BRKBEUWDJQDKTM-UHFFFAOYSA-N 8-(pyridin-4-ylmethoxy)-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1=CC=NC=C1 BRKBEUWDJQDKTM-UHFFFAOYSA-N 0.000 claims description 2
• NLZJFVXOFCFQHC-IRLDBZIGSA-N 8-[(3r,4s)-3-fluoropiperidin-4-yl]oxy-2-(6-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@@H]1OC1=CC=CC2=CC=C(C=3N4C=C(C=CC4=NN=3)C=3C=CC=CC=3)N=C12 NLZJFVXOFCFQHC-IRLDBZIGSA-N 0.000 claims description 2
• LIKKMSJYXQMOCX-UHFFFAOYSA-N 8-[(4-methylpiperidin-4-yl)methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(C)CCNCC1 LIKKMSJYXQMOCX-UHFFFAOYSA-N 0.000 claims description 2
• ORWFEWSJBCTIST-HNNXBMFYSA-N 8-[[(2s)-pyrrolidin-2-yl]methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OC[C@@H]1CCCN1 ORWFEWSJBCTIST-HNNXBMFYSA-N 0.000 claims description 2
• QJCCGCRBXGFEOI-UHFFFAOYSA-N 8-[[4-(cyclopropylmethyl)piperidin-4-yl]methoxy]-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OCC1(CC2CC2)CCNCC1 QJCCGCRBXGFEOI-UHFFFAOYSA-N 0.000 claims description 2
• URCZAWFHBYABKR-UHFFFAOYSA-N 8-piperidin-4-yloxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C1CNCCC1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 URCZAWFHBYABKR-UHFFFAOYSA-N 0.000 claims description 2
• LHYMZRAAHMXXAW-UHFFFAOYSA-N 8-pyridin-4-yloxy-2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline Chemical compound C=1C=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C2C=1OC1=CC=NC=C1 LHYMZRAAHMXXAW-UHFFFAOYSA-N 0.000 claims description 2
• QFYWUMPWXIJTRE-IYBDPMFKSA-N C1C[C@@H](N)CC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 Chemical compound C1C[C@@H](N)CC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 QFYWUMPWXIJTRE-IYBDPMFKSA-N 0.000 claims description 2
• UGCCFJQVUHNGIM-WKILWMFISA-N C1C[C@@H](O)CC[C@@H]1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 UGCCFJQVUHNGIM-WKILWMFISA-N 0.000 claims description 2
• 239000007822 coupling agent Substances 0.000 claims description 2
• SAVPCTYZGZDSSO-ZBFHGGJFSA-N methyl (2s,4r)-4-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]oxypyrrolidine-2-carboxylate Chemical compound C1N[C@H](C(=O)OC)C[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC=CC4=NN=3)N=C12 SAVPCTYZGZDSSO-ZBFHGGJFSA-N 0.000 claims description 2
• JVJPYYIBTFDZRE-UHFFFAOYSA-N n'-(3-methylbutyl)-n'-[2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl]propane-1,3-diamine Chemical compound C1=CC=CN2C(C3=CC=C4C=CC=C(C4=N3)N(CCCN)CCC(C)C)=NN=C21 JVJPYYIBTFDZRE-UHFFFAOYSA-N 0.000 claims description 2
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