JP5374492B2 - 受容体チロシンキナーゼ阻害薬としてのイミダゾ［１，２−ａ］ピリジン化合物 - Google Patents

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Publication number

JP5374492B2

JP5374492B2 JP2010502204A JP2010502204A JP5374492B2 JP 5374492 B2 JP5374492 B2 JP 5374492B2 JP 2010502204 A JP2010502204 A JP 2010502204A JP 2010502204 A JP2010502204 A JP 2010502204A JP 5374492 B2 JP5374492 B2 JP 5374492B2

Authority

JP

Japan

Prior art keywords

alkyl

pyridin

imidazo

hetcyc

methoxyethoxy

Prior art date

2007-04-03

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.)

Expired - Fee Related

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• 229940127361 Receptor Tyrosine Kinase Inhibitors Drugs 0.000 title description 3
• 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 227
• 125000000217 alkyl group Chemical group 0.000 claims description 370
• -1 2-pyrimidyl Chemical group 0.000 claims description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims description 63
• 150000003839 salts Chemical class 0.000 claims description 62
• 238000000034 method Methods 0.000 claims description 60
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 47
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
• 229910052731 fluorine Inorganic materials 0.000 claims description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims description 33
• 239000002585 base Substances 0.000 claims description 30
• 229910052801 chlorine Inorganic materials 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 23
• 125000004429 atom Chemical group 0.000 claims description 23
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 150000002367 halogens Chemical class 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
• 239000002904 solvent Substances 0.000 claims description 16
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 229910052763 palladium Inorganic materials 0.000 claims description 11
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000006242 amine protecting group Chemical group 0.000 claims description 9
• 239000003054 catalyst Substances 0.000 claims description 9
• 239000003153 chemical reaction reagent Substances 0.000 claims description 9
• 230000008878 coupling Effects 0.000 claims description 9
• 238000010168 coupling process Methods 0.000 claims description 9
• 238000005859 coupling reaction Methods 0.000 claims description 9
• 239000003446 ligand Substances 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 125000003003 spiro group Chemical group 0.000 claims description 6
• 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 6
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• LHOJRSNEPLRYJS-TZIWHRDSSA-N (3r,4r)-4-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]oxypyrrolidin-3-ol Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CNC[C@H]1O LHOJRSNEPLRYJS-TZIWHRDSSA-N 0.000 claims description 4
• 239000003638 chemical reducing agent Substances 0.000 claims description 4
• 239000007822 coupling agent Substances 0.000 claims description 4
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
• 239000003444 phase transfer catalyst Substances 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• LJSSJGXMPSLSIR-RTWAWAEBSA-N (3r,4s)-4-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]oxypiperidin-3-ol Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@H]1CCNC[C@H]1O LJSSJGXMPSLSIR-RTWAWAEBSA-N 0.000 claims description 3
• MTEYLRHKRPYBCB-YLJYHZDGSA-N 2-(7-ethylimidazo[1,2-a]pyridin-3-yl)-8-[(3r,4r)-3-fluoropiperidin-4-yl]oxyquinoline Chemical compound C=1N=C2C=C(CC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CCNC[C@H]1F MTEYLRHKRPYBCB-YLJYHZDGSA-N 0.000 claims description 3
• NQOAYTFDSNONAL-FGZHOGPDSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-[(3r,4r)-4-methoxypyrrolidin-3-yl]oxyquinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CNC[C@H]1OC NQOAYTFDSNONAL-FGZHOGPDSA-N 0.000 claims description 3
• IXABGGXDRTVRCC-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-n-(4-methylpiperidin-4-yl)quinolin-8-amine Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2NC1(C)CCNCC1 IXABGGXDRTVRCC-UHFFFAOYSA-N 0.000 claims description 3
• KHQNCCQHMLMRSX-QGZVFWFLSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-n-[(3r)-pyrrolidin-3-yl]quinolin-8-amine Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2N[C@@H]1CCNC1 KHQNCCQHMLMRSX-QGZVFWFLSA-N 0.000 claims description 3
• BHTLCFNWNNFOFE-NFBKMPQASA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-(7-pyridin-3-ylimidazo[1,2-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(=CC4=NC=3)C=3C=NC=CC=3)N=C12 BHTLCFNWNNFOFE-NFBKMPQASA-N 0.000 claims description 3
• YYJQBDHSLHYZOC-DENIHFKCSA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-(7-pyrimidin-5-ylimidazo[1,2-a]pyridin-3-yl)quinoline Chemical compound F[C@@H]1CNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(=CC4=NC=3)C=3C=NC=NC=3)N=C12 YYJQBDHSLHYZOC-DENIHFKCSA-N 0.000 claims description 3
• PPPOUAQYRUUFNJ-WIYYLYMNSA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CCNC[C@H]1F PPPOUAQYRUUFNJ-WIYYLYMNSA-N 0.000 claims description 3
• OPAMDWHECZQIBN-ZJSXRUAMSA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-[7-(4-methylpyridin-3-yl)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound CC1=CC=NC=C1C1=CC2=NC=C(C=3N=C4C(O[C@H]5[C@@H](CNCC5)F)=CC=CC4=CC=3)N2C=C1 OPAMDWHECZQIBN-ZJSXRUAMSA-N 0.000 claims description 3
• OUJDQQBZGPBOKT-UHFFFAOYSA-N 8-[(4-fluoropiperidin-4-yl)methoxy]-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OCC1(F)CCNCC1 OUJDQQBZGPBOKT-UHFFFAOYSA-N 0.000 claims description 3
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• HTQYVNDQWIJFQA-MOPGFXCFSA-N n-[(3r,4s)-3-fluoropiperidin-4-yl]-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-amine Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2N[C@H]1CCNC[C@H]1F HTQYVNDQWIJFQA-MOPGFXCFSA-N 0.000 claims description 3
• LJSSJGXMPSLSIR-NHCUHLMSSA-N (3r,4r)-4-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]oxypiperidin-3-ol Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CCNC[C@H]1O LJSSJGXMPSLSIR-NHCUHLMSSA-N 0.000 claims description 2
• PCRCKJQVHCGZFM-SFHVURJKSA-N (3s)-3-[[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]oxymethyl]morpholine Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OC[C@@H]1COCCN1 PCRCKJQVHCGZFM-SFHVURJKSA-N 0.000 claims description 2
• RSFHJWJNNOAZMN-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-(2-piperidin-2-ylethoxy)quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OCCC1CCCCN1 RSFHJWJNNOAZMN-UHFFFAOYSA-N 0.000 claims description 2
• RNDLZUAZVRFLRS-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-(piperidin-3-ylmethoxy)quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OCC1CCCNC1 RNDLZUAZVRFLRS-UHFFFAOYSA-N 0.000 claims description 2
• GQNJNGOQHBAXOL-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-(piperidin-4-ylmethoxy)quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OCC1CCNCC1 GQNJNGOQHBAXOL-UHFFFAOYSA-N 0.000 claims description 2
• KPBBCDRZGUBDOM-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-[(1-methylpyrrolidin-3-yl)methoxy]quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OCC1CCN(C)C1 KPBBCDRZGUBDOM-UHFFFAOYSA-N 0.000 claims description 2
• RROPCZKHYUPTGO-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-piperidin-4-yloxyquinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OC1CCNCC1 RROPCZKHYUPTGO-UHFFFAOYSA-N 0.000 claims description 2
• KHQNCCQHMLMRSX-KRWDZBQOSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-n-[(3s)-pyrrolidin-3-yl]quinolin-8-amine Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2N[C@H]1CCNC1 KHQNCCQHMLMRSX-KRWDZBQOSA-N 0.000 claims description 2
• DDRZDPGSGJJQRD-DENIHFKCSA-N 2-[7-(cyclopropylmethoxy)imidazo[1,2-a]pyridin-3-yl]-8-[(3r,4r)-3-fluoropiperidin-4-yl]oxyquinoline Chemical compound F[C@@H]1CNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(OCC5CC5)=CC4=NC=3)N=C12 DDRZDPGSGJJQRD-DENIHFKCSA-N 0.000 claims description 2
• OEQLYHXNGSLNQN-UHFFFAOYSA-N 3-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]oxy-2,2-dimethylpropan-1-amine Chemical compound C1=CC=C(OCC(C)(C)CN)C2=NC(C=3N4C=CC(=CC4=NC=3)OCCOC)=CC=C21 OEQLYHXNGSLNQN-UHFFFAOYSA-N 0.000 claims description 2
• BVQNLQXIIBXKGV-UHFFFAOYSA-N 3-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]oxy-n,n,2,2-tetramethylpropan-1-amine Chemical compound C1=CC=C(OCC(C)(C)CN(C)C)C2=NC(C=3N4C=CC(=CC4=NC=3)OCCOC)=CC=C21 BVQNLQXIIBXKGV-UHFFFAOYSA-N 0.000 claims description 2
• NRYVSERERSAPDZ-NFBKMPQASA-N 5-[8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-4-yl]-1,3-oxazole Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C1C(O[C@H]2[C@@H](CNCC2)F)=CC=CC1=1)=CC=1C1=CN=CO1 NRYVSERERSAPDZ-NFBKMPQASA-N 0.000 claims description 2
• URCODTVVEBNHBV-WIYYLYMNSA-N 5-fluoro-8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C(F)=CC=C2O[C@@H]1CCNC[C@H]1F URCODTVVEBNHBV-WIYYLYMNSA-N 0.000 claims description 2
• XSEPWAKOMGUUGZ-WIYYLYMNSA-N 6-fluoro-8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=C(F)C=C2O[C@@H]1CCNC[C@H]1F XSEPWAKOMGUUGZ-WIYYLYMNSA-N 0.000 claims description 2
• ALJIWGDXJWSXQV-UHFFFAOYSA-N 8-(1-ethylpiperidin-4-yl)oxy-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound C1CN(CC)CCC1OC1=CC=CC2=CC=C(C=3N4C=CC(OCCOC)=CC4=NC=3)N=C12 ALJIWGDXJWSXQV-UHFFFAOYSA-N 0.000 claims description 2
• AADYTTDFFQOMQO-NFBKMPQASA-N 8-[(3r,4r)-1-ethyl-3-fluoropiperidin-4-yl]oxy-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound F[C@@H]1CN(CC)CC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(OCCOC)=CC4=NC=3)N=C12 AADYTTDFFQOMQO-NFBKMPQASA-N 0.000 claims description 2
• FESXABGGTQSRQZ-DENIHFKCSA-N 8-[(3r,4r)-3-fluoro-1-methylpiperidin-4-yl]oxy-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CCN(C)C[C@H]1F FESXABGGTQSRQZ-DENIHFKCSA-N 0.000 claims description 2
• FREBNXPQQZJEKM-WOIUINJBSA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-[7-[(3r)-oxolan-3-yl]oxyimidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound F[C@@H]1CNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(O[C@H]5COCC5)=CC4=NC=3)N=C12 FREBNXPQQZJEKM-WOIUINJBSA-N 0.000 claims description 2
• FREBNXPQQZJEKM-NNMXDRDESA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-[7-[(3s)-oxolan-3-yl]oxyimidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound F[C@@H]1CNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(O[C@@H]5COCC5)=CC4=NC=3)N=C12 FREBNXPQQZJEKM-NNMXDRDESA-N 0.000 claims description 2
• LWHKFZNLONZVNC-WMZHIEFXSA-N 8-[(3r,4s)-4-fluoropyrrolidin-3-yl]oxy-2-(7-pyridin-3-ylimidazo[1,2-a]pyridin-3-yl)quinoline Chemical compound F[C@H]1CNC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(=CC4=NC=3)C=3C=NC=CC=3)N=C12 LWHKFZNLONZVNC-WMZHIEFXSA-N 0.000 claims description 2
• PPPOUAQYRUUFNJ-RXVVDRJESA-N 8-[(3s,4s)-3-fluoropiperidin-4-yl]oxy-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@H]1CCNC[C@@H]1F PPPOUAQYRUUFNJ-RXVVDRJESA-N 0.000 claims description 2
• CEECEQWHEAERFB-UHFFFAOYSA-N 8-piperidin-4-yloxy-2-(7-pyridin-3-ylimidazo[1,2-a]pyridin-3-yl)quinoline Chemical compound C1CNCCC1OC1=CC=CC2=CC=C(C=3N4C=CC(=CC4=NC=3)C=3C=NC=CC=3)N=C12 CEECEQWHEAERFB-UHFFFAOYSA-N 0.000 claims description 2
• 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 2
• XZOOZZGHEVFMAJ-UHFFFAOYSA-N 2-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]oxyethanamine Chemical compound C1=CC=C(OCCN)C2=NC(C=3N4C=CC(=CC4=NC=3)OCCOC)=CC=C21 XZOOZZGHEVFMAJ-UHFFFAOYSA-N 0.000 claims 1
• CLEYIMMREBBHKP-YLJYHZDGSA-N 2-[3-[8-[(3r,4r)-3-fluoropiperidin-4-yl]oxyquinolin-2-yl]imidazo[1,2-a]pyridin-7-yl]oxyethanol Chemical compound C=1N=C2C=C(OCCO)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CCNC[C@H]1F CLEYIMMREBBHKP-YLJYHZDGSA-N 0.000 claims 1
• XZMAHDRRCQRMHC-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-(1-methylpiperidin-4-yl)oxyquinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OC1CCN(C)CC1 XZMAHDRRCQRMHC-UHFFFAOYSA-N 0.000 claims 1
• IQACVVFBPSXQID-UHFFFAOYSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-(pyrrolidin-3-ylmethoxy)quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OCC1CCNC1 IQACVVFBPSXQID-UHFFFAOYSA-N 0.000 claims 1
• TXAFYFWHBVJGHQ-LJQANCHMSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-[(3r)-piperidin-3-yl]oxyquinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CCCNC1 TXAFYFWHBVJGHQ-LJQANCHMSA-N 0.000 claims 1
• CKGYOCHUFHHZBI-GOSISDBHSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-[(3r)-pyrrolidin-3-yl]oxyquinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@@H]1CCNC1 CKGYOCHUFHHZBI-GOSISDBHSA-N 0.000 claims 1
• TXAFYFWHBVJGHQ-IBGZPJMESA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-[(3s)-piperidin-3-yl]oxyquinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@H]1CCCNC1 TXAFYFWHBVJGHQ-IBGZPJMESA-N 0.000 claims 1
• CKGYOCHUFHHZBI-SFHVURJKSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-[(3s)-pyrrolidin-3-yl]oxyquinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2O[C@H]1CCNC1 CKGYOCHUFHHZBI-SFHVURJKSA-N 0.000 claims 1
• XSWXDGBUKRJVOH-GOSISDBHSA-N 2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-[[(2r)-pyrrolidin-2-yl]methoxy]quinoline Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1C(N=C12)=CC=C1C=CC=C2OC[C@H]1CCCN1 XSWXDGBUKRJVOH-GOSISDBHSA-N 0.000 claims 1
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