ES2715611T3 - Compuestos novedosos de 3H-imidazo[4,5-b]piridina-3,5-disustituida y 3H-[1,2,3]triazolo[4,5-b]piridina 3,5-disustituida como moduladores de proteína cinasas - Google Patents

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Publication number

ES2715611T3

ES2715611T3 ES11730442T ES11730442T ES2715611T3 ES 2715611 T3 ES2715611 T3 ES 2715611T3 ES 11730442 T ES11730442 T ES 11730442T ES 11730442 T ES11730442 T ES 11730442T ES 2715611 T3 ES2715611 T3 ES 2715611T3

Authority

ES

Spain

Prior art keywords

triazolo

pyridin

quinolin

ylmethyl

benzamide

Prior art date

2010-05-17

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.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 327
• 102000001253 Protein Kinase Human genes 0.000 title description 24
• 108060006633 protein kinase Proteins 0.000 title description 24
• VQNDBXJTIJKJPV-UHFFFAOYSA-N 2h-triazolo[4,5-b]pyridine Chemical compound C1=CC=NC2=NNN=C21 VQNDBXJTIJKJPV-UHFFFAOYSA-N 0.000 title description 2
• -1 nitro, hydroxy Chemical group 0.000 claims abstract description 237
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
• 239000001257 hydrogen Substances 0.000 claims abstract description 40
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 31
• 150000002367 halogens Chemical class 0.000 claims abstract description 31
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 23
• 125000001424 substituent group Chemical group 0.000 claims abstract description 20
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 17
• 125000003118 aryl group Chemical group 0.000 claims abstract description 16
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
• 125000004429 atom Chemical group 0.000 claims abstract description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 12
• 229910052701 rubidium Inorganic materials 0.000 claims abstract description 12
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 11
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 11
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
• 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 91
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 79
• 238000011282 treatment Methods 0.000 claims description 54
• 201000010099 disease Diseases 0.000 claims description 51
• 239000008194 pharmaceutical composition Substances 0.000 claims description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 28
• 208000035475 disorder Diseases 0.000 claims description 27
• QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 23
• 229940095102 methyl benzoate Drugs 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 239000002253 acid Substances 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 230000008901 benefit Effects 0.000 claims description 12
• 125000004122 cyclic group Chemical group 0.000 claims description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• TZNHZJFZKIFROV-UHFFFAOYSA-N 2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)N)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 TZNHZJFZKIFROV-UHFFFAOYSA-N 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 230000005764 inhibitory process Effects 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 229910052731 fluorine Chemical group 0.000 claims description 7
• 239000011737 fluorine Chemical group 0.000 claims description 7
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
• ZAWDHPLYSGNQPJ-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound FC1=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=CC=C1C(=O)NC1CC1 ZAWDHPLYSGNQPJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• MTIDWGWNSVAORH-UHFFFAOYSA-N 2-fluoro-n-methyl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 MTIDWGWNSVAORH-UHFFFAOYSA-N 0.000 claims description 5
• CZABKGHEWRBDIQ-UHFFFAOYSA-N [2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenyl]methanol Chemical compound C1=C(F)C(CO)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 CZABKGHEWRBDIQ-UHFFFAOYSA-N 0.000 claims description 5
• ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• RFVWMJIOMXCJSM-UHFFFAOYSA-N n-(3-aminopropyl)-2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)NCCCN)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 RFVWMJIOMXCJSM-UHFFFAOYSA-N 0.000 claims description 5
• IRDHQXZRAAXURD-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)C=C1 IRDHQXZRAAXURD-UHFFFAOYSA-N 0.000 claims description 4
• PECUCZBHODUZEU-UHFFFAOYSA-N 2-[2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenyl]propan-2-ol Chemical compound C1=C(F)C(C(C)(O)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 PECUCZBHODUZEU-UHFFFAOYSA-N 0.000 claims description 4
• DGJCOGLLWQCOBZ-UHFFFAOYSA-N 2-[[2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoyl]amino]acetic acid Chemical compound C1=C(F)C(C(=O)NCC(=O)O)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 DGJCOGLLWQCOBZ-UHFFFAOYSA-N 0.000 claims description 4
• FRPPERRANDHEEB-UHFFFAOYSA-N 2-chloro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(Cl)C(C(=O)N)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 FRPPERRANDHEEB-UHFFFAOYSA-N 0.000 claims description 4
• NRZOHMBDOKRKHP-UHFFFAOYSA-N 2-chloro-n-cyclopropyl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound ClC1=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=CC=C1C(=O)NC1CC1 NRZOHMBDOKRKHP-UHFFFAOYSA-N 0.000 claims description 4
• QGVJLONSPHODQQ-UHFFFAOYSA-N 2-chloro-n-ethyl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide;hydrochloride Chemical compound Cl.C1=C(Cl)C(C(=O)NCC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 QGVJLONSPHODQQ-UHFFFAOYSA-N 0.000 claims description 4
• YDGKORPGKZRXNG-UHFFFAOYSA-N 2-chloro-n-propyl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(Cl)C(C(=O)NCCC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 YDGKORPGKZRXNG-UHFFFAOYSA-N 0.000 claims description 4
• IJMULKKMKPVYMI-UHFFFAOYSA-N 2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]-n-(1h-1,2,4-triazol-5-yl)benzamide Chemical compound FC1=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=CC=C1C(=O)NC=1N=CNN=1 IJMULKKMKPVYMI-UHFFFAOYSA-N 0.000 claims description 4
• RHCFEXDMWLNGCG-UHFFFAOYSA-N 2-fluoro-n-methoxy-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)NOC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 RHCFEXDMWLNGCG-UHFFFAOYSA-N 0.000 claims description 4
• LSBYLTPYDTUMTI-UHFFFAOYSA-N 2-fluoro-n-methoxy-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide;hydrochloride Chemical compound Cl.C1=C(F)C(C(=O)NOC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 LSBYLTPYDTUMTI-UHFFFAOYSA-N 0.000 claims description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
• BEFJGKLOHGNCPU-UHFFFAOYSA-N 2-methyl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(C(N)=O)C(C)=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 BEFJGKLOHGNCPU-UHFFFAOYSA-N 0.000 claims description 4
• SNSSDXYDPBFOOK-UHFFFAOYSA-N 4-[3-(1,3-benzothiazol-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]-2-chlorobenzamide Chemical compound C1=C(Cl)C(C(=O)N)=CC=C1C1=CC=C(N=NN2CC=3C=C4SC=NC4=CC=3)C2=N1 SNSSDXYDPBFOOK-UHFFFAOYSA-N 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
• MBRDVWHDMGIEAF-UHFFFAOYSA-N 6-[(5-chlorotriazolo[4,5-b]pyridin-3-yl)methyl]quinoline Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)Cl)=CC=C21 MBRDVWHDMGIEAF-UHFFFAOYSA-N 0.000 claims description 4
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
• GGBDGITTXGEJIQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=CC(C(=O)NCCO)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 GGBDGITTXGEJIQ-UHFFFAOYSA-N 0.000 claims description 4
• ZJNPQKYMEWCRIH-UHFFFAOYSA-N n-(2-piperidin-1-ylethyl)-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C=1C=C(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)C=CC=1C(=O)NCCN1CCCCC1 ZJNPQKYMEWCRIH-UHFFFAOYSA-N 0.000 claims description 4
• QYASGYIRJUBHTN-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=CC(C(=O)NCCN(C)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 QYASGYIRJUBHTN-UHFFFAOYSA-N 0.000 claims description 4
• VHHLEOBFSRVUCS-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide;hydrochloride Chemical compound Cl.FC1=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=CC=C1C(=O)NC1CC1 VHHLEOBFSRVUCS-UHFFFAOYSA-N 0.000 claims description 4
• OHNYPCCIADQGKG-UHFFFAOYSA-N n-ethyl-2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)NCC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 OHNYPCCIADQGKG-UHFFFAOYSA-N 0.000 claims description 4
• LUZAVOJYFRFTIU-UHFFFAOYSA-N n-propan-2-yl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 LUZAVOJYFRFTIU-UHFFFAOYSA-N 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
• YSZHICGRUSTSKO-UHFFFAOYSA-N 2,6-difluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide;hydrochloride Chemical compound Cl.C1=C(F)C(C(=O)N)=C(F)C=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 YSZHICGRUSTSKO-UHFFFAOYSA-N 0.000 claims description 3
• OZECUDOLQNIRSC-UHFFFAOYSA-N 2-chloro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]-n-(1h-1,2,4-triazol-5-yl)benzamide Chemical compound ClC1=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=CC=C1C(=O)NC=1N=CNN=1 OZECUDOLQNIRSC-UHFFFAOYSA-N 0.000 claims description 3
• 229910004679 ONO2 Inorganic materials 0.000 claims description 3
• NQTZXLZXXUQMOA-SANMLTNESA-N [(2s)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-[4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenyl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C=1C=CC(=CC=1)C=1N=C2N(CC=3C=C4C=CC=NC4=CC=3)N=NC2=CC=1)N1CCCC1 NQTZXLZXXUQMOA-SANMLTNESA-N 0.000 claims description 3
• 230000003197 catalytic effect Effects 0.000 claims description 3
• 150000002357 guanidines Chemical class 0.000 claims description 3
• PIKJMYAHJUMBAC-UHFFFAOYSA-N 2,6-difluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)N)=C(F)C=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 PIKJMYAHJUMBAC-UHFFFAOYSA-N 0.000 claims description 2
• PVAQYFOADYRDHE-UHFFFAOYSA-N 2-chloro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide;hydrochloride Chemical compound Cl.C1=C(Cl)C(C(=O)N)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 PVAQYFOADYRDHE-UHFFFAOYSA-N 0.000 claims description 2
• GMQSNFKIKCLVGL-UHFFFAOYSA-N 2-chloro-n-ethyl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(Cl)C(C(=O)NCC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 GMQSNFKIKCLVGL-UHFFFAOYSA-N 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• VXRKSKHBSGWQAD-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide Chemical compound C1=C(F)C(C(=O)NCCCN(C)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 VXRKSKHBSGWQAD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 8
• 239000005711 Benzoic acid Substances 0.000 claims 6
• 235000010233 benzoic acid Nutrition 0.000 claims 6
• FUGZBBHUBLYHQL-UHFFFAOYSA-N 6-(triazolo[4,5-b]pyridin-3-ylmethyl)quinoline Chemical compound N1=CC=CC2=CC(=CC=C12)CN1N=NC=2C1=NC=CC=2 FUGZBBHUBLYHQL-UHFFFAOYSA-N 0.000 claims 4
• CGWOEOXQHIMZEQ-UHFFFAOYSA-N 3-[1-[[4-(2-phenylquinolin-3-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound OC1=NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=CC2=CC=CC=C2N=C1C1=CC=CC=C1 CGWOEOXQHIMZEQ-UHFFFAOYSA-N 0.000 claims 3
• PVTSKCPMMQTBBF-OAQYLSRUSA-N [(3r)-3-hydroxypyrrolidin-1-yl]-[4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenyl]methanone Chemical compound C1[C@H](O)CCN1C(=O)C1=CC=C(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)C=C1 PVTSKCPMMQTBBF-OAQYLSRUSA-N 0.000 claims 3
• FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 claims 3
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 3
• PBZOJLDUWZQLIV-UHFFFAOYSA-N methyl 3-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 PBZOJLDUWZQLIV-UHFFFAOYSA-N 0.000 claims 3
• FGVXKWQRBSXXSX-UHFFFAOYSA-N methyl 4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 FGVXKWQRBSXXSX-UHFFFAOYSA-N 0.000 claims 3
• VUODLWVIEYLYSW-UHFFFAOYSA-N n,n-bis(2-methoxyethyl)-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)N(CCOC)CCOC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 VUODLWVIEYLYSW-UHFFFAOYSA-N 0.000 claims 3
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