CA2719118C - Derives polysubstitues de 6-heteroaryle-imidazo[1,2-.alpha.]pyridines, leur preparation et leur application en therapeutique - Google Patents

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Publication number

CA2719118C

CA2719118C CA2719118A CA2719118A CA2719118C CA 2719118 C CA2719118 C CA 2719118C CA 2719118 A CA2719118 A CA 2719118A CA 2719118 A CA2719118 A CA 2719118A CA 2719118 C CA2719118 C CA 2719118C

Authority

CA

Canada

Prior art keywords

pyridin

cndot

methanol

imidazo

thien

Prior art date

2008-03-21

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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• 238000002360 preparation method Methods 0.000 title claims description 21
• 230000001225 therapeutic effect Effects 0.000 title description 4
• 150000003222 pyridines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 242
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 77
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 72
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 125000001424 substituent group Chemical group 0.000 claims abstract description 36
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
• 150000002367 halogens Chemical class 0.000 claims abstract description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
• 239000001257 hydrogen Substances 0.000 claims abstract description 31
• 238000000034 method Methods 0.000 claims abstract description 31
• 125000004429 atom Chemical group 0.000 claims abstract description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
• 239000002253 acid Substances 0.000 claims abstract description 21
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract description 17
• 125000005843 halogen group Chemical group 0.000 claims abstract description 16
• 238000003786 synthesis reaction Methods 0.000 claims abstract description 14
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 303
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 144
• -1 pyrrolopyridinyl Chemical group 0.000 claims description 135
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 52
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 52
• 238000011282 treatment Methods 0.000 claims description 34
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 30
• 238000006243 chemical reaction Methods 0.000 claims description 30
• 230000002265 prevention Effects 0.000 claims description 27
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 27
• 229910003827 NRaRb Inorganic materials 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000002541 furyl group Chemical group 0.000 claims description 20
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000000335 thiazolyl group Chemical group 0.000 claims description 18
• 125000001544 thienyl group Chemical group 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
• 150000001638 boron Chemical class 0.000 claims description 15
• 230000008569 process Effects 0.000 claims description 14
• XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 13
• 229910052763 palladium Inorganic materials 0.000 claims description 13
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 12
• 229910052701 rubidium Inorganic materials 0.000 claims description 12
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 10
• 125000001041 indolyl group Chemical group 0.000 claims description 10
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 150000003927 aminopyridines Chemical class 0.000 claims description 8
• 125000006239 protecting group Chemical group 0.000 claims description 8
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 7
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• 125000004001 thioalkyl group Chemical group 0.000 claims description 7
• IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 claims description 6
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 5
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 5
• 208000001132 Osteoporosis Diseases 0.000 claims description 5
• 208000034799 Tauopathies Diseases 0.000 claims description 5
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 5
• 239000000460 chlorine Substances 0.000 claims description 5
• 238000010511 deprotection reaction Methods 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 206010015037 epilepsy Diseases 0.000 claims description 5
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims description 5
• 201000000980 schizophrenia Diseases 0.000 claims description 5
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 208000018737 Parkinson disease Diseases 0.000 claims description 4
• WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 4
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 4
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
• 229910052796 boron Inorganic materials 0.000 claims description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 230000006806 disease prevention Effects 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 229940047889 isobutyramide Drugs 0.000 claims description 4
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 230000001012 protector Effects 0.000 claims description 4
• 208000020016 psychiatric disease Diseases 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 3
• 230000006735 deficit Effects 0.000 claims description 3
• 208000013403 hyperactivity Diseases 0.000 claims description 3
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 3
• 230000004770 neurodegeneration Effects 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 3
• UQTBWLPEAMWCEO-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[4-(methoxymethyl)furan-2-yl]imidazo[1,2-a]pyridine Chemical compound COCC1=COC(C2=CN3C=C(N=C3C=C2)C=2C=CC(Cl)=CC=2)=C1 UQTBWLPEAMWCEO-UHFFFAOYSA-N 0.000 claims description 2
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
• FVYSBNPBDZYSTM-UHFFFAOYSA-N [4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2N=CC=CC=2)=C1 FVYSBNPBDZYSTM-UHFFFAOYSA-N 0.000 claims description 2
• VBXYXPHCTUDMFY-UHFFFAOYSA-N [4-[2-(1-benzofuran-2-yl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2OC3=CC=CC=C3C=2)=C1 VBXYXPHCTUDMFY-UHFFFAOYSA-N 0.000 claims description 2
• YGKBIXNWLOAQDP-UHFFFAOYSA-N [4-[2-(1-benzofuran-5-yl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2C=C3C=COC3=CC=2)=C1 YGKBIXNWLOAQDP-UHFFFAOYSA-N 0.000 claims description 2
• GNZVZQJAQAAFET-UHFFFAOYSA-N [4-[2-(furan-2-yl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2OC=CC=2)=C1 GNZVZQJAQAAFET-UHFFFAOYSA-N 0.000 claims description 2
• YSHPYEFOKURILH-UHFFFAOYSA-N [5-(2-phenylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C1=CN2C=C(C=3C=CC=CC=3)N=C2C=C1 YSHPYEFOKURILH-UHFFFAOYSA-N 0.000 claims description 2
• ZJSNESWDRQMLIO-UHFFFAOYSA-N [5-[2-(1,3-benzothiazol-2-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C1=CN2C=C(C=3SC4=CC=CC=C4N=3)N=C2C=C1 ZJSNESWDRQMLIO-UHFFFAOYSA-N 0.000 claims description 2
• PZHGHYOYMKZINF-UHFFFAOYSA-N [5-[2-(1,3-thiazol-2-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C1=CN2C=C(C=3SC=CN=3)N=C2C=C1 PZHGHYOYMKZINF-UHFFFAOYSA-N 0.000 claims description 2
• VGKBGZKFCSCZHL-UHFFFAOYSA-N [5-[2-(1-benzofuran-2-yl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C1=CN2C=C(C=3OC4=CC=CC=C4C=3)N=C2C=C1 VGKBGZKFCSCZHL-UHFFFAOYSA-N 0.000 claims description 2
• QXZLFNGCJOQNGC-UHFFFAOYSA-N [5-[2-(3-bromophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C1=CN2C=C(C=3C=C(Br)C=CC=3)N=C2C=C1 QXZLFNGCJOQNGC-UHFFFAOYSA-N 0.000 claims description 2
• XLCKNQNVIRXUBF-UHFFFAOYSA-N [5-[2-(4-chloro-3-methylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound C1=C(Cl)C(C)=CC(C=2N=C3C=CC(=CN3C=2)C=2OC(CO)=CC=2)=C1 XLCKNQNVIRXUBF-UHFFFAOYSA-N 0.000 claims description 2
• ZSMJCFFINQRBGA-UHFFFAOYSA-N [5-[2-(4-methylphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound C1=CC(C)=CC=C1C1=CN(C=C(C=C2)C=3OC(CO)=CC=3)C2=N1 ZSMJCFFINQRBGA-UHFFFAOYSA-N 0.000 claims description 2
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 2
• 230000000626 neurodegenerative effect Effects 0.000 claims description 2
• 230000009529 traumatic brain injury Effects 0.000 claims description 2
• JAYSSVIRQJHKHU-UHFFFAOYSA-N 2-[2-[2-(1h-indazol-3-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=NC(C2=CN3C=C(N=C3C=C2)C=2C3=CC=CC=C3NN=2)=C1 JAYSSVIRQJHKHU-UHFFFAOYSA-N 0.000 claims 1
• XONOUHCQIIFDES-UHFFFAOYSA-N 2-[2-[2-(1h-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=NC(C2=CN3C=C(N=C3C=C2)C=2C=C3NC=CC3=CC=2)=C1 XONOUHCQIIFDES-UHFFFAOYSA-N 0.000 claims 1
• KJRBISCCZGVXNM-UHFFFAOYSA-N 2-[2-[2-(5-methyl-1,2-oxazol-3-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl]propan-2-ol Chemical compound O1C(C)=CC(C=2N=C3C=CC(=CN3C=2)C=2N=CC=C(C=2)C(C)(C)O)=N1 KJRBISCCZGVXNM-UHFFFAOYSA-N 0.000 claims 1
• ZRBBCMFRKYKXKL-UHFFFAOYSA-N 2-[4-[2-(1h-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]-1h-pyrazol-5-yl]propan-2-ol Chemical compound CC(C)(O)C1=NNC=C1C1=CN2C=C(C=3C=C4NC=CC4=CC=3)N=C2C=C1 ZRBBCMFRKYKXKL-UHFFFAOYSA-N 0.000 claims 1
• IHAFOBVVENYGCE-UHFFFAOYSA-N 2-[5-fluoro-2-[2-(1h-indol-6-yl)imidazo[1,2-a]pyridin-6-yl]pyridin-4-yl]propan-2-ol Chemical compound C1=C(F)C(C(C)(O)C)=CC(C2=CN3C=C(N=C3C=C2)C=2C=C3NC=CC3=CC=2)=N1 IHAFOBVVENYGCE-UHFFFAOYSA-N 0.000 claims 1
• MFHSGEYIGHVTAV-UHFFFAOYSA-N 2-fluoro-4-[6-[5-(hydroxymethyl)thiophen-3-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzamide Chemical compound C1=C(F)C(C(=O)N(C)C)=CC=C1C1=CN(C=C(C=C2)C=3C=C(CO)SC=3)C2=N1 MFHSGEYIGHVTAV-UHFFFAOYSA-N 0.000 claims 1
• JYERWXFXXGLMMU-UHFFFAOYSA-N 3-[6-[2-(hydroxymethyl)-1,3-thiazol-4-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2N=C3C=CC(=CN3C=2)C=2N=C(CO)SC=2)=C1 JYERWXFXXGLMMU-UHFFFAOYSA-N 0.000 claims 1
• BTTLGSZLRNDKSL-UHFFFAOYSA-N 3-[6-[2-(hydroxymethyl)-1,3-thiazol-4-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(C=2N=C3C=CC(=CN3C=2)C=2N=C(CO)SC=2)=C1 BTTLGSZLRNDKSL-UHFFFAOYSA-N 0.000 claims 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
• MHNZGXQSZPSFEL-UHFFFAOYSA-N 4-[6-[2-(hydroxymethyl)-1,3-thiazol-4-yl]imidazo[1,2-a]pyridin-2-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CN(C=C(C=C2)C=3N=C(CO)SC=3)C2=N1 MHNZGXQSZPSFEL-UHFFFAOYSA-N 0.000 claims 1
• ILBUEZVODVGHHT-UHFFFAOYSA-N 4-[6-[5-(hydroxymethyl)furan-2-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=CN(C=C(C=C2)C=3OC(CO)=CC=3)C2=N1 ILBUEZVODVGHHT-UHFFFAOYSA-N 0.000 claims 1
• BPERDCKCFHDFMF-UHFFFAOYSA-N 4-[6-[5-(hydroxymethyl)thiophen-3-yl]imidazo[1,2-a]pyridin-2-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=CN(C=C(C=C2)C=3C=C(CO)SC=3)C2=N1 BPERDCKCFHDFMF-UHFFFAOYSA-N 0.000 claims 1
• RHPYLFTZDRDFOE-UHFFFAOYSA-N [4-(2-thiophen-2-ylimidazo[1,2-a]pyridin-6-yl)-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2SC=CC=2)=C1 RHPYLFTZDRDFOE-UHFFFAOYSA-N 0.000 claims 1
• GZMSJGFLORVLTN-UHFFFAOYSA-N [4-(3-methyl-2-phenylimidazo[1,2-a]pyridin-6-yl)-1,3-thiazol-2-yl]methanol Chemical compound C=1N2C(C)=C(C=3C=CC=CC=3)N=C2C=CC=1C1=CSC(CO)=N1 GZMSJGFLORVLTN-UHFFFAOYSA-N 0.000 claims 1
• KPOYJAFVLNFGIT-UHFFFAOYSA-N [4-(3-methyl-2-thiophen-2-ylimidazo[1,2-a]pyridin-6-yl)-1,3-thiazol-2-yl]methanol Chemical compound C=1N2C(C)=C(C=3SC=CC=3)N=C2C=CC=1C1=CSC(CO)=N1 KPOYJAFVLNFGIT-UHFFFAOYSA-N 0.000 claims 1
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• GPMBXEPYGKYOEA-UHFFFAOYSA-N [4-[2-(1-methylindol-5-yl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound C=1C=C2N(C)C=CC2=CC=1C(N=C1C=C2)=CN1C=C2C1=CSC(CO)=N1 GPMBXEPYGKYOEA-UHFFFAOYSA-N 0.000 claims 1
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• URRHRZAOHFEGMZ-UHFFFAOYSA-N [4-[2-(1h-indol-5-yl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2C=C3C=CNC3=CC=2)=C1 URRHRZAOHFEGMZ-UHFFFAOYSA-N 0.000 claims 1
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• ZMLNYOFVSCYQTD-UHFFFAOYSA-N [4-[2-(2-fluorophenyl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2C(=CC=CC=2)F)=C1 ZMLNYOFVSCYQTD-UHFFFAOYSA-N 0.000 claims 1
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• IRPHLVNAWRHZRW-UHFFFAOYSA-N [4-[2-(3-chlorophenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound C=1N2C(C)=C(C=3C=C(Cl)C=CC=3)N=C2C=CC=1C1=CSC(CO)=N1 IRPHLVNAWRHZRW-UHFFFAOYSA-N 0.000 claims 1
• TVSGWNHDBFYJFA-UHFFFAOYSA-N [4-[2-(4-chloro-3-methylphenyl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound C1=C(Cl)C(C)=CC(C=2N=C3C=CC(=CN3C=2)C=2N=C(CO)SC=2)=C1 TVSGWNHDBFYJFA-UHFFFAOYSA-N 0.000 claims 1
• CNBRRKNBQFSWQW-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound C=1N2C(C)=C(C=3C=CC(Cl)=CC=3)N=C2C=CC=1C1=CSC(CO)=N1 CNBRRKNBQFSWQW-UHFFFAOYSA-N 0.000 claims 1
• XDVWFSGEWLVJJA-UHFFFAOYSA-N [4-[2-(4-fluorophenyl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2C=CC(F)=CC=2)=C1 XDVWFSGEWLVJJA-UHFFFAOYSA-N 0.000 claims 1
• OPRWMWPCGKZGMU-UHFFFAOYSA-N [4-[2-(4-methoxyphenyl)-3-methylimidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=C(C)N2C=C(C=3N=C(CO)SC=3)C=CC2=N1 OPRWMWPCGKZGMU-UHFFFAOYSA-N 0.000 claims 1
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• BLLUJJRWVNLWAS-UHFFFAOYSA-N [4-[2-(4-methylthiophen-3-yl)imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound CC1=CSC=C1C1=CN(C=C(C=C2)C=3N=C(CO)SC=3)C2=N1 BLLUJJRWVNLWAS-UHFFFAOYSA-N 0.000 claims 1
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• MJVLDGUXHXIDRW-UHFFFAOYSA-N [4-[2-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyridin-6-yl]-1,3-thiazol-2-yl]methanol Chemical compound S1C(CO)=NC(C2=CN3C=C(N=C3C=C2)C=2C=CC(=CC=2)C(F)(F)F)=C1 MJVLDGUXHXIDRW-UHFFFAOYSA-N 0.000 claims 1
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• ZDGVEXQUHNYHER-UHFFFAOYSA-N [5-(3-methyl-2-phenylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol Chemical compound C=1N2C(C)=C(C=3C=CC=CC=3)N=C2C=CC=1C1=CC=C(CO)O1 ZDGVEXQUHNYHER-UHFFFAOYSA-N 0.000 claims 1
• SZBKYBBLLDZMBM-UHFFFAOYSA-N [5-(3-methyl-2-thiophen-2-ylimidazo[1,2-a]pyridin-6-yl)furan-2-yl]methanol Chemical compound C=1N2C(C)=C(C=3SC=CC=3)N=C2C=CC=1C1=CC=C(CO)O1 SZBKYBBLLDZMBM-UHFFFAOYSA-N 0.000 claims 1
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• KATRBNLPROCSON-UHFFFAOYSA-N [5-[2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=CN(C=C(C=C2)C=3OC(CO)=CC=3)C2=N1 KATRBNLPROCSON-UHFFFAOYSA-N 0.000 claims 1
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