TWI695002B - 用於治療發炎病症之新穎化合物及彼等之醫藥組合物 - Google Patents

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Publication number

TWI695002B

TWI695002B TW103108497A TW103108497A TWI695002B TW I695002 B TWI695002 B TW I695002B TW 103108497 A TW103108497 A TW 103108497A TW 103108497 A TW103108497 A TW 103108497A TW I695002 B TWI695002 B TW I695002B

Authority

TW

Taiwan

Prior art keywords

pyridin

methyl

ethyl

imidazo

fluorophenyl

Prior art date

2013-03-14

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 421
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 67
• 230000004968 inflammatory condition Effects 0.000 title description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 163
• 201000010099 disease Diseases 0.000 claims abstract description 143
• 238000011282 treatment Methods 0.000 claims abstract description 74
• 230000003176 fibrotic effect Effects 0.000 claims abstract description 39
• 230000002159 abnormal effect Effects 0.000 claims abstract description 38
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 35
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 35
• 230000033115 angiogenesis Effects 0.000 claims abstract description 34
• 230000002062 proliferating effect Effects 0.000 claims abstract description 33
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 31
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 31
• 208000023504 respiratory system disease Diseases 0.000 claims abstract description 30
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 29
• 238000004519 manufacturing process Methods 0.000 claims abstract description 20
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 177
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 147
• 125000000217 alkyl group Chemical group 0.000 claims description 141
• 150000003839 salts Chemical class 0.000 claims description 138
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 128
• -1 2-(4-(2-ethyl-3-((4-(4-fluorophenyl)thiazol-2-yl)(methyl)amino)imidazo[1, 2-a]pyridin-6-yl)piperazin-1-yl)ethyl propionate Chemical compound 0.000 claims description 99
• 229910052717 sulfur Inorganic materials 0.000 claims description 78
• 125000005842 heteroatom Chemical group 0.000 claims description 74
• 229910052757 nitrogen Inorganic materials 0.000 claims description 68
• 229910052760 oxygen Inorganic materials 0.000 claims description 67
• 125000005843 halogen group Chemical group 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 59
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 52
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
• 239000003814 drug Substances 0.000 claims description 48
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 46
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 35
• 229910052731 fluorine Inorganic materials 0.000 claims description 27
• 208000017520 skin disease Diseases 0.000 claims description 27
• 229910052801 chlorine Inorganic materials 0.000 claims description 25
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000002950 monocyclic group Chemical group 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 20
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 20
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 18
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000002619 bicyclic group Chemical group 0.000 claims description 15
• 229940079593 drug Drugs 0.000 claims description 15
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
• 238000006467 substitution reaction Methods 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 8
• XWXPRCDFFCVMNT-UHFFFAOYSA-N 1,3-thiazole-5-carbonitrile Chemical compound N#CC1=CN=CS1 XWXPRCDFFCVMNT-UHFFFAOYSA-N 0.000 claims description 7
• RTOFMMILZZGGNS-UHFFFAOYSA-N imidazo[1,2-a]pyridin-3-amine Chemical compound C1=CC=CN2C(N)=CN=C21 RTOFMMILZZGGNS-UHFFFAOYSA-N 0.000 claims description 7
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 claims description 6
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 4
• RLPZNOABKYSNBQ-UHFFFAOYSA-N 2-[4-[2-ethyl-7-fluoro-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-(3-hydroxypyrrolidin-1-yl)ethanone Chemical compound CCC=1N=C2C=C(F)C(N3CCN(CC(=O)N4CC(O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 RLPZNOABKYSNBQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims description 3
• REQQVBGILUTQNN-UHFFFAOYSA-N ziritaxestat Chemical compound CCC=1N=C2C(C)=CC(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 REQQVBGILUTQNN-UHFFFAOYSA-N 0.000 claims description 3
• UWIMIJQAIGDPRL-UHFFFAOYSA-N (1-aminocyclopropyl)-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]methanone Chemical compound CCC=1N=C2C=CC(N3CCN(CC3)C(=O)C3(N)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 UWIMIJQAIGDPRL-UHFFFAOYSA-N 0.000 claims description 2
• SOWLPNYWLOHUPY-JOCHJYFZSA-N (5r)-5-[[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]methyl]-1,3-oxazolidin-2-one Chemical compound CCC=1N=C2C=CC(C3CCN(C[C@@H]4OC(=O)NC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 SOWLPNYWLOHUPY-JOCHJYFZSA-N 0.000 claims description 2
• 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims description 2
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 2
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 2
• SEYZZTUZQZDEKA-UHFFFAOYSA-N 1-[3-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazine-1-carbonyl]pyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C=CC(N3CCN(CC3)C(=O)C3CN(CC3)C(C)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 SEYZZTUZQZDEKA-UHFFFAOYSA-N 0.000 claims description 2
• PCDNBXRGGMPGNR-UHFFFAOYSA-N 1-[3-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]azetidin-1-yl]ethanone Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)C3CN(C3)C(C)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 PCDNBXRGGMPGNR-UHFFFAOYSA-N 0.000 claims description 2
• AOMBRHMFARUEAH-UHFFFAOYSA-N 1-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-4-hydroxybutan-1-one Chemical compound CCC=1N=C2C=CC(N3CCN(CC3)C(=O)CCCO)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 AOMBRHMFARUEAH-UHFFFAOYSA-N 0.000 claims description 2
• PTMWHHNXRBDPIL-UHFFFAOYSA-N 1-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-2-(3-fluoroazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)C(=O)CN3CC(F)C3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 PTMWHHNXRBDPIL-UHFFFAOYSA-N 0.000 claims description 2
• VSEYSXQFPGQBNE-UHFFFAOYSA-N 1-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-2-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)C(=O)CN3CC(O)C3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 VSEYSXQFPGQBNE-UHFFFAOYSA-N 0.000 claims description 2
• RHXMUBRTNRIDQP-UHFFFAOYSA-N 1-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-3-(methylamino)propan-1-one Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)C(=O)CCNC)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 RHXMUBRTNRIDQP-UHFFFAOYSA-N 0.000 claims description 2
• OYVPEZLNGSLVAM-UHFFFAOYSA-N 1-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCC1C1=CN2C(N(C)C=3SC=C(N=3)C=3C=CC(F)=CC=3)=C(CC)N=C2C=C1 OYVPEZLNGSLVAM-UHFFFAOYSA-N 0.000 claims description 2
• GXUIEVJTBWWWPA-UHFFFAOYSA-N 1-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-5-(hydroxymethyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCC1C1=CN2C(N(C)C=3SC(CO)=C(N=3)C=3C=CC(F)=CC=3)=C(CC)N=C2C=C1 GXUIEVJTBWWWPA-UHFFFAOYSA-N 0.000 claims description 2
• UTYLRZXQSIMWJU-UHFFFAOYSA-N 2-[(2-ethyl-8-methyl-6-piperazin-1-ylimidazo[1,2-a]pyridin-3-yl)-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C(C)=CC(N3CCNCC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 UTYLRZXQSIMWJU-UHFFFAOYSA-N 0.000 claims description 2
• VVRCMCTVUXYZQU-UHFFFAOYSA-N 2-[2-[(2-ethyl-6-piperazin-1-ylimidazo[1,2-a]pyridin-3-yl)-methylamino]-5-methyl-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(N3CCNCC3)=CN2C=1N(C)C(SC=1C)=NC=1C1=CC=C(F)C=C1C#N VVRCMCTVUXYZQU-UHFFFAOYSA-N 0.000 claims description 2
• YXKWLEWSXAFUHE-UHFFFAOYSA-N 2-[2-[[2-ethyl-6-(1-methylsulfonylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl]-methylamino]-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1C#N YXKWLEWSXAFUHE-UHFFFAOYSA-N 0.000 claims description 2
• HAJDFDKWLDMNLT-UHFFFAOYSA-N 2-[2-[[2-ethyl-6-(1-methylsulfonylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl]-methylamino]-1,3-thiazol-4-yl]-5-fluorophenol Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1O HAJDFDKWLDMNLT-UHFFFAOYSA-N 0.000 claims description 2
• BPTUZNYKXWXVNB-UHFFFAOYSA-N 2-[2-[[2-ethyl-6-(1-methylsulfonylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl]-methylamino]-5-methyl-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1C)=NC=1C1=CC=C(F)C=C1C#N BPTUZNYKXWXVNB-UHFFFAOYSA-N 0.000 claims description 2
• VKAMRWHKIOMJPY-UHFFFAOYSA-N 2-[2-[[2-ethyl-6-[1-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperidin-4-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1C#N VKAMRWHKIOMJPY-UHFFFAOYSA-N 0.000 claims description 2
• AFOLTTFKYHEGQQ-UHFFFAOYSA-N 2-[2-[[2-ethyl-6-[1-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperidin-4-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-5-methyl-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1C)=NC=1C1=CC=C(F)C=C1C#N AFOLTTFKYHEGQQ-UHFFFAOYSA-N 0.000 claims description 2
• XDXFZJULGNQFBG-UHFFFAOYSA-N 2-[2-[[2-ethyl-6-[4-[2-(3-fluoroazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CC(F)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1C#N XDXFZJULGNQFBG-UHFFFAOYSA-N 0.000 claims description 2
• RRBPLYHOWVNGTJ-UHFFFAOYSA-N 2-[2-[[2-ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1C#N RRBPLYHOWVNGTJ-UHFFFAOYSA-N 0.000 claims description 2
• AIMDGDOIUVDEQR-UHFFFAOYSA-N 2-[2-[[2-ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-5-methyl-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1C)=NC=1C1=CC=C(F)C=C1C#N AIMDGDOIUVDEQR-UHFFFAOYSA-N 0.000 claims description 2
• ULDYRABGTYOLFP-UHFFFAOYSA-N 2-[2-[[6-[4-[2-(3,3-difluoroazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-2-ethylimidazo[1,2-a]pyridin-3-yl]-methylamino]-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CC(F)(F)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1C#N ULDYRABGTYOLFP-UHFFFAOYSA-N 0.000 claims description 2
• CILREKGZMLVXSQ-UHFFFAOYSA-N 2-[2-[[6-[4-[2-(azetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-2-ethylimidazo[1,2-a]pyridin-3-yl]-methylamino]-1,3-thiazol-4-yl]-5-fluorobenzonitrile Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CCC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1C#N CILREKGZMLVXSQ-UHFFFAOYSA-N 0.000 claims description 2
• VBUZZRDEXJVIEQ-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]-7-methylimidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-1-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=C(C)C(C3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 VBUZZRDEXJVIEQ-UHFFFAOYSA-N 0.000 claims description 2
• PGZHYJGQWOOUAY-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]-8-methylimidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C(C)=CC(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 PGZHYJGQWOOUAY-UHFFFAOYSA-N 0.000 claims description 2
• QFUFZGJGRUUNFG-XMMPIXPASA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]-8-methylimidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-[(3r)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C(C)=CC(N3CCN(CC(=O)N4C[C@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 QFUFZGJGRUUNFG-XMMPIXPASA-N 0.000 claims description 2
• QFUFZGJGRUUNFG-DEOSSOPVSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]-8-methylimidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-[(3s)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C(C)=CC(N3CCN(CC(=O)N4C[C@@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 QFUFZGJGRUUNFG-DEOSSOPVSA-N 0.000 claims description 2
• MJIXUHRNZICEIS-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-(3-fluoroazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CC(F)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 MJIXUHRNZICEIS-UHFFFAOYSA-N 0.000 claims description 2
• KFLNXTSMXZGUQO-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 KFLNXTSMXZGUQO-UHFFFAOYSA-N 0.000 claims description 2
• PDLRHBOQFRLFIO-HSZRJFAPSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-[(3r)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4C[C@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 PDLRHBOQFRLFIO-HSZRJFAPSA-N 0.000 claims description 2
• PDLRHBOQFRLFIO-QHCPKHFHSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-[(3s)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4C[C@@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 PDLRHBOQFRLFIO-QHCPKHFHSA-N 0.000 claims description 2
• RFEGFCJAXDGMOO-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-morpholin-4-ylethanone Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CCOCC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 RFEGFCJAXDGMOO-UHFFFAOYSA-N 0.000 claims description 2
• CUTIUGOTQMGTLQ-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-1-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 CUTIUGOTQMGTLQ-UHFFFAOYSA-N 0.000 claims description 2
• KSVBVIFNBMXBOL-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-1-(3-hydroxypyrrolidin-1-yl)ethanone Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4CC(O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 KSVBVIFNBMXBOL-UHFFFAOYSA-N 0.000 claims description 2
• KSVBVIFNBMXBOL-XMMPIXPASA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-1-[(3r)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4C[C@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 KSVBVIFNBMXBOL-XMMPIXPASA-N 0.000 claims description 2
• KSVBVIFNBMXBOL-DEOSSOPVSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-1-[(3s)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4C[C@@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 KSVBVIFNBMXBOL-DEOSSOPVSA-N 0.000 claims description 2
• VYBHNDNYKYVPBR-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-n-(2-hydroxyethyl)-n-methylacetamide Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N(C)CCO)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 VYBHNDNYKYVPBR-UHFFFAOYSA-N 0.000 claims description 2
• HSNIQTDZZPZEOY-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-n-methoxy-n-methylacetamide Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N(C)OC)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 HSNIQTDZZPZEOY-UHFFFAOYSA-N 0.000 claims description 2
• OLFYWFBYXYXCOH-UHFFFAOYSA-N 2-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-5-(hydroxymethyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]-1-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1CO)=NC=1C1=CC=C(F)C=C1 OLFYWFBYXYXCOH-UHFFFAOYSA-N 0.000 claims description 2
• WQLVQANKBMIVRT-UHFFFAOYSA-N 2-[4-[2-ethyl-7-fluoro-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=C(F)C(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 WQLVQANKBMIVRT-UHFFFAOYSA-N 0.000 claims description 2
• RRMFIGXYKKSOGF-UHFFFAOYSA-N 2-[4-[2-ethyl-8-fluoro-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C(F)=CC(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 RRMFIGXYKKSOGF-UHFFFAOYSA-N 0.000 claims description 2
• YUSSPBPJFJJVCN-JOCHJYFZSA-N 2-[4-[2-ethyl-8-fluoro-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-[(3r)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C(F)=CC(N3CCN(CC(=O)N4C[C@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 YUSSPBPJFJJVCN-JOCHJYFZSA-N 0.000 claims description 2
• YUSSPBPJFJJVCN-QFIPXVFZSA-N 2-[4-[2-ethyl-8-fluoro-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-1-[(3s)-3-hydroxypyrrolidin-1-yl]ethanone Chemical compound CCC=1N=C2C(F)=CC(N3CCN(CC(=O)N4C[C@@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 YUSSPBPJFJJVCN-QFIPXVFZSA-N 0.000 claims description 2
• ZBWCCKDEPNMVJU-UHFFFAOYSA-N 2-[4-[3-[[4-(2-cyano-4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]-2-ethylimidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-n-methylacetamide Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)NC)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1C#N ZBWCCKDEPNMVJU-UHFFFAOYSA-N 0.000 claims description 2
• PTAJGGOANVQKRL-UHFFFAOYSA-N 2-[4-[3-[[4-(2-cyano-4-fluorophenyl)-5-methyl-1,3-thiazol-2-yl]-methylamino]-2-ethylimidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-n-methylacetamide Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)NC)CC3)=CN2C=1N(C)C(SC=1C)=NC=1C1=CC=C(F)C=C1C#N PTAJGGOANVQKRL-UHFFFAOYSA-N 0.000 claims description 2
• QZUUDAYHSPCQPL-UHFFFAOYSA-N 2-[4-[3-[[5-cyano-4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]-2-ethyl-8-fluoroimidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-n-methylacetamide Chemical compound CCC=1N=C2C(F)=CC(N3CCN(CC(=O)NC)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 QZUUDAYHSPCQPL-UHFFFAOYSA-N 0.000 claims description 2
• BSTJDBYCLLQVLJ-UHFFFAOYSA-N 2-[4-[3-[[5-cyano-4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]-2-ethylimidazo[1,2-a]pyridin-6-yl]piperazin-1-yl]-n-methylacetamide Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)NC)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 BSTJDBYCLLQVLJ-UHFFFAOYSA-N 0.000 claims description 2
• OINJZCIRBASATK-UHFFFAOYSA-N 2-[[1-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]azetidin-3-yl]amino]-1-(3-hydroxyazetidin-1-yl)ethanone Chemical compound CCC=1N=C2C=CC(N3CC(C3)NCC(=O)N3CC(O)C3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 OINJZCIRBASATK-UHFFFAOYSA-N 0.000 claims description 2
• UCJMEBRVFBKBSE-UHFFFAOYSA-N 2-[[2-ethyl-6-(1-methylsulfonylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 UCJMEBRVFBKBSE-UHFFFAOYSA-N 0.000 claims description 2
• SLWLOCBCOHDDDJ-UHFFFAOYSA-N 2-[[2-ethyl-6-(1-methylsulfonylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carboxamide Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1C(N)=O)=NC=1C1=CC=C(F)C=C1 SLWLOCBCOHDDDJ-UHFFFAOYSA-N 0.000 claims description 2
• CURUUZHLEFADRH-UHFFFAOYSA-N 2-[[2-ethyl-6-[1-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperidin-4-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C(C)=CC(C3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 CURUUZHLEFADRH-UHFFFAOYSA-N 0.000 claims description 2
• USTXXAKVNIABFI-UHFFFAOYSA-N 2-[[2-ethyl-6-[1-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperidin-4-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 USTXXAKVNIABFI-UHFFFAOYSA-N 0.000 claims description 2
• LUOGCZVRNOALIE-XMMPIXPASA-N 2-[[2-ethyl-6-[1-[2-[(3r)-3-hydroxypyrrolidin-1-yl]-2-oxoethyl]piperidin-4-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4C[C@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 LUOGCZVRNOALIE-XMMPIXPASA-N 0.000 claims description 2
• LUOGCZVRNOALIE-DEOSSOPVSA-N 2-[[2-ethyl-6-[1-[2-[(3s)-3-hydroxypyrrolidin-1-yl]-2-oxoethyl]piperidin-4-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4C[C@@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 LUOGCZVRNOALIE-DEOSSOPVSA-N 0.000 claims description 2
• OGXCDCKTMVUAEJ-UHFFFAOYSA-N 2-[[2-ethyl-6-[1-[2-[3-(hydroxymethyl)azetidin-1-yl]-2-oxoethyl]piperidin-4-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C=CC(C3CCN(CC(=O)N4CC(CO)C4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 OGXCDCKTMVUAEJ-UHFFFAOYSA-N 0.000 claims description 2
• KPMRDQYWRDQDBQ-UHFFFAOYSA-N 2-[[2-ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 KPMRDQYWRDQDBQ-UHFFFAOYSA-N 0.000 claims description 2
• WJFTYZMGNJHJAY-XMMPIXPASA-N 2-[[2-ethyl-6-[4-[2-[(3r)-3-hydroxypyrrolidin-1-yl]-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C(C)=CC(N3CCN(CC(=O)N4C[C@H](O)CC4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 WJFTYZMGNJHJAY-XMMPIXPASA-N 0.000 claims description 2
• QVCVIVHIBXCAGR-UHFFFAOYSA-N 2-[[2-ethyl-6-[4-[2-[3-(hydroxymethyl)azetidin-1-yl]-2-oxoethyl]piperazin-1-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C=CC(N3CCN(CC(=O)N4CC(CO)C4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 QVCVIVHIBXCAGR-UHFFFAOYSA-N 0.000 claims description 2
• DPQQZPUTETUIQM-UHFFFAOYSA-N 2-[[2-ethyl-7-fluoro-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C=C(F)C(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 DPQQZPUTETUIQM-UHFFFAOYSA-N 0.000 claims description 2
• XWIATKKSLBPZTC-UHFFFAOYSA-N 2-[[2-ethyl-8-fluoro-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]imidazo[1,2-a]pyridin-3-yl]-methylamino]-4-(4-fluorophenyl)-1,3-thiazole-5-carbonitrile Chemical compound CCC=1N=C2C(F)=CC(N3CCN(CC(=O)N4CC(O)C4)CC3)=CN2C=1N(C)C(SC=1C#N)=NC=1C1=CC=C(F)C=C1 XWIATKKSLBPZTC-UHFFFAOYSA-N 0.000 claims description 2
• HEQTYIHFHKKUSO-UHFFFAOYSA-N 3-(dimethylamino)-1-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]propan-1-one Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)C(=O)CCN(C)C)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 HEQTYIHFHKKUSO-UHFFFAOYSA-N 0.000 claims description 2
• JMORVPOHPFYVRC-UHFFFAOYSA-N 3-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]sulfonylpropyl acetate Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(=O)(=O)CCCOC(C)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 JMORVPOHPFYVRC-UHFFFAOYSA-N 0.000 claims description 2
• LLIVISWLTFVKCE-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-n-[2-ethyl-6-(1-methylsulfonylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl]-n-methyl-1,3-thiazol-2-amine Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1Cl LLIVISWLTFVKCE-UHFFFAOYSA-N 0.000 claims description 2
• JXUXVLLECYIYMO-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-ethyl-6-(1-methylsulfonyl-2,5-dihydropyrrol-3-yl)imidazo[1,2-a]pyridin-3-yl]-n-methyl-1,3-thiazol-2-amine Chemical compound CCC=1N=C2C=CC(C=3CN(CC=3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(Cl)C=C1 JXUXVLLECYIYMO-UHFFFAOYSA-N 0.000 claims description 2
• WFOTWHSHKRJVIQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[6-(4,5-dihydro-1,3-oxazol-2-yl)-2-ethylimidazo[1,2-a]pyridin-3-yl]-n-methyl-1,3-thiazol-2-amine Chemical compound CCC=1N=C2C=CC(C=3OCCN=3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(Cl)C=C1 WFOTWHSHKRJVIQ-UHFFFAOYSA-N 0.000 claims description 2
• JJPGGJMYVPEZMJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-methyl-n-[6-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-2-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyridin-3-yl]-1,3-thiazol-2-amine Chemical compound FC(F)(F)CC=1N=C2C=CC(C=3CCN(CC=3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(Cl)C=C1 JJPGGJMYVPEZMJ-UHFFFAOYSA-N 0.000 claims description 2
• YTRGQUJFFJUTGS-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-n-[2-ethyl-6-(1-methylsulfonylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl]-n-methyl-1,3-thiazol-2-amine Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(C(C)(C)C)C=C1 YTRGQUJFFJUTGS-UHFFFAOYSA-N 0.000 claims description 2
• QLHNUNGTDZDYOC-UHFFFAOYSA-N 4-[[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]methyl]-1,3-oxazolidin-2-one Chemical compound CCC=1N=C2C=CC(C3CCN(CC4NC(=O)OC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 QLHNUNGTDZDYOC-UHFFFAOYSA-N 0.000 claims description 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• ZJRNOXAQWIRVCB-UHFFFAOYSA-N 5-[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperazine-1-carbonyl]pyrrolidin-2-one Chemical compound CCC=1N=C2C=CC(N3CCN(CC3)C(=O)C3NC(=O)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 ZJRNOXAQWIRVCB-UHFFFAOYSA-N 0.000 claims description 2
• SOWLPNYWLOHUPY-UHFFFAOYSA-N 5-[[4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-a]pyridin-6-yl]piperidin-1-yl]methyl]-1,3-oxazolidin-2-one Chemical compound CCC=1N=C2C=CC(C3CCN(CC4OC(=O)NC4)CC3)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1 SOWLPNYWLOHUPY-UHFFFAOYSA-N 0.000 claims description 2
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• 241000009298 Trigla lyra Species 0.000 claims description 2
• KLESIVUURRNEOC-UHFFFAOYSA-N [2-[2-[[2-ethyl-6-(1-methylsulfonylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl]-methylamino]-1,3-thiazol-4-yl]-5-fluorophenyl]methanol Chemical compound CCC=1N=C2C=CC(C3CCN(CC3)S(C)(=O)=O)=CN2C=1N(C)C(SC=1)=NC=1C1=CC=C(F)C=C1CO KLESIVUURRNEOC-UHFFFAOYSA-N 0.000 claims description 2
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