JP2010523576A5 - - Google Patents
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- Publication number
- JP2010523576A5 JP2010523576A5 JP2010502204A JP2010502204A JP2010523576A5 JP 2010523576 A5 JP2010523576 A5 JP 2010523576A5 JP 2010502204 A JP2010502204 A JP 2010502204A JP 2010502204 A JP2010502204 A JP 2010502204A JP 2010523576 A5 JP2010523576 A5 JP 2010523576A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hetcyc
- pyridin
- imidazo
- compound
- Prior art date
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 202
- 150000001875 compounds Chemical class 0.000 claims description 125
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- -1 2-pyrimidyl Chemical group 0.000 claims description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 206010016654 Fibrosis Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 230000004761 fibrosis Effects 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000006242 amine protecting group Chemical group 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 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 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003003 spiro group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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
- 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 1
- 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 1
- 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 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
- 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 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
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- TZIXXHVIMUUDMH-UHFFFAOYSA-N 2-[[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=C2OCC1CNCCO1 TZIXXHVIMUUDMH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- CLMAUZOFRUHCNR-UHFFFAOYSA-N 7-[2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinolin-8-yl]oxy-3-oxa-9-azabicyclo[3.3.1]nonane Chemical compound C1C(N2)COCC2CC1OC(C1=N2)=CC=CC1=CC=C2C1=CN=C2N1C=CC(OCCOC)=C2 CLMAUZOFRUHCNR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BZRLFTGHSYBAQK-UHFFFAOYSA-N 8-(8-azabicyclo[3.2.1]octan-3-yloxy)-2-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound C1C(N2)CCC2CC1OC(C1=N2)=CC=CC1=CC=C2C1=CN=C2N1C=CC(OCCOC)=C2 BZRLFTGHSYBAQK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZUGZUUGLXILHNZ-NFBKMPQASA-N 8-[(3r,4r)-3-fluoropiperidin-4-yl]oxy-2-[7-(oxan-4-yloxy)imidazo[1,2-a]pyridin-3-yl]quinoline Chemical compound F[C@@H]1CNCC[C@H]1OC1=CC=CC2=CC=C(C=3N4C=CC(OC5CCOCC5)=CC4=NC=3)N=C12 ZUGZUUGLXILHNZ-NFBKMPQASA-N 0.000 claims 1
- 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 1
- 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 1
- PPPOUAQYRUUFNJ-NQIIRXRSSA-N 8-[(3r,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-NQIIRXRSSA-N 0.000 claims 1
- 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 1
- SXFXTYDCDKSPCU-LAUBAEHRSA-N 8-[(3r,4s)-4-fluoropyrrolidin-3-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]1CNC[C@@H]1F SXFXTYDCDKSPCU-LAUBAEHRSA-N 0.000 claims 1
- 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 1
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| US20050256309A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
| CN101083985A (zh) | 2004-09-21 | 2007-12-05 | 幸讬制药公司 | 用于炎症及免疫相关用途的化合物 |
| WO2006038111A1 (en) | 2004-10-07 | 2006-04-13 | Pfizer Products Inc. | Benzoimidazole derivatives useful as antiproliferative agents |
| CN102861338A (zh) | 2006-04-05 | 2013-01-09 | 诺瓦提斯公司 | 用于治疗癌症、包含bcr-abl/c-kit/pdgf-r tk抑制剂的组合 |
| CN101679422A (zh) * | 2007-03-28 | 2010-03-24 | 阵列生物制药公司 | 作为受体酪氨酸激酶抑制剂的咪唑并[1,2-a]吡啶化合物 |
| US20110184013A1 (en) * | 2008-10-01 | 2011-07-28 | Shelley Allen | Imidazo[1,2-a]Pyridine Compounds As Receptor Tyrosine Kinase Inhibitors |
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