TWI868068B - 氮雜苯並咪唑化合物及醫藥 - Google Patents

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Publication number

TWI868068B

TWI868068B TW108115846A TW108115846A TWI868068B TW I868068 B TWI868068 B TW I868068B TW 108115846 A TW108115846 A TW 108115846A TW 108115846 A TW108115846 A TW 108115846A TW I868068 B TWI868068 B TW I868068B

Authority

TW

Taiwan

Prior art keywords

pyridin

methyl

imidazo

trifluoromethyl

amino

Prior art date

2018-05-08

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• 239000003814 drug Substances 0.000 title claims abstract description 13
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract 2
• 229940079593 drug Drugs 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 479
• 150000003839 salts Chemical class 0.000 claims abstract description 43
• 210000002700 urine Anatomy 0.000 claims abstract description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 208000028938 Urination disease Diseases 0.000 claims abstract description 14
• 238000003860 storage Methods 0.000 claims abstract description 14
• 208000035475 disorder Diseases 0.000 claims abstract description 12
• 208000004168 Underactive Urinary Bladder Diseases 0.000 claims abstract description 10
• 230000003449 preventive effect Effects 0.000 claims abstract description 7
• 229940124597 therapeutic agent Drugs 0.000 claims abstract description 7
• 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims abstract description 5
• 206010029279 Neurogenic bladder Diseases 0.000 claims abstract description 5
• -1 benzimidazole compound Chemical class 0.000 claims description 235
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 231
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 132
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 113
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 105
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 103
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 81
• 235000019260 propionic acid Nutrition 0.000 claims description 78
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 61
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 59
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 53
• 229910052757 nitrogen Inorganic materials 0.000 claims description 49
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound 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 48
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 37
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 33
• SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 101150060249 CHRM3 gene Proteins 0.000 claims description 26
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
• 102000017925 CHRM3 Human genes 0.000 claims description 25
• 229940126027 positive allosteric modulator Drugs 0.000 claims description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 14
• WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 208000012931 Urologic disease Diseases 0.000 claims description 7
• 239000004480 active ingredient Substances 0.000 claims description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims description 7
• 208000026533 urinary bladder disease Diseases 0.000 claims description 7
• 208000014001 urinary system disease Diseases 0.000 claims description 7
• BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical group FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 claims description 6
• 208000010412 Glaucoma Diseases 0.000 claims description 6
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
• XQAHVIOVBIDSOF-UHFFFAOYSA-N 2-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)C1CCN(CC1)CC(=O)O)N(C)CC1(CCC1)COC XQAHVIOVBIDSOF-UHFFFAOYSA-N 0.000 claims description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
• UAVRGQXGRGLHMT-UHFFFAOYSA-N 1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]benzoyl]piperidine-4-carboxylic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C(=O)N2CCC(CC2)C(=O)O)C=C1)N(C)CC1(CCC1)COC UAVRGQXGRGLHMT-UHFFFAOYSA-N 0.000 claims description 3
• KYMLQNYIFNEFTO-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F KYMLQNYIFNEFTO-UHFFFAOYSA-N 0.000 claims description 3
• IHTORGBKEIAMBN-UHFFFAOYSA-N 2-[4-[6-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyridin-3-yl]-4-hydroxypiperidin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=N1)C1(CCN(CC1)CC(=O)O)O)N(C)CC1(CCC1)COC IHTORGBKEIAMBN-UHFFFAOYSA-N 0.000 claims description 3
• 239000004471 Glycine Substances 0.000 claims description 3
• 229910005965 SO 2 Inorganic materials 0.000 claims description 3
• 210000005070 sphincter Anatomy 0.000 claims description 3
• UEVVSYWKTRTCED-UHFFFAOYSA-N 1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C UEVVSYWKTRTCED-UHFFFAOYSA-N 0.000 claims description 2
• DBDOVVKPNHHTJT-UHFFFAOYSA-N 2-[4-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]piperidin-1-yl]acetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(OC2CCN(CC2)CC(=O)O)C=C1)N(C)CC1(CCC1)COC DBDOVVKPNHHTJT-UHFFFAOYSA-N 0.000 claims description 2
• JJJLKCQSOLLLJC-UHFFFAOYSA-N 3-[4-fluoro-4-[6-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyridin-3-yl]piperidin-1-yl]propanoic acid Chemical compound FC1(CCN(CC1)CCC(=O)O)C=1C=NC(=CC=1)C=1NC=2C(=NC(=CC=2N(C)CC2(CCC2)COC)C2=CC(=CC(=C2)C(F)(F)F)F)N=1 JJJLKCQSOLLLJC-UHFFFAOYSA-N 0.000 claims description 2
• SCVVOESKIIMTJD-UHFFFAOYSA-N 8-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-2,8-diazaspiro[4.5]decan-3-one Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC2(CC(NC2)=O)CC1)N(C)CC1(CCC1)COC SCVVOESKIIMTJD-UHFFFAOYSA-N 0.000 claims description 2
• 206010003591 Ataxia Diseases 0.000 claims description 2
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 24
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 4
• SKCGYHOXVGOCBE-UHFFFAOYSA-N CCOC1=NC(C(F)(F)F)=CC(C2=CC(N(C)CC(C)(C)COC)=C3NC(C(C=C4)=CN=C4N(CC4)CCC4C(O)=O)=NC3=N2)=C1 Chemical compound CCOC1=NC(C(F)(F)F)=CC(C2=CC(N(C)CC(C)(C)COC)=C3NC(C(C=C4)=CN=C4N(CC4)CCC4C(O)=O)=NC3=N2)=C1 SKCGYHOXVGOCBE-UHFFFAOYSA-N 0.000 claims 3
• CXNKIDAVPDUDAY-UHFFFAOYSA-N CCOC1=NC(C(F)(F)F)=CC(C2=CC(N(C)CC3(COC)CCC3)=C3NC(C(C=C4)=CN=C4N(CC4)CCC4C(O)=O)=NC3=N2)=C1 Chemical compound CCOC1=NC(C(F)(F)F)=CC(C2=CC(N(C)CC3(COC)CCC3)=C3NC(C(C=C4)=CN=C4N(CC4)CCC4C(O)=O)=NC3=N2)=C1 CXNKIDAVPDUDAY-UHFFFAOYSA-N 0.000 claims 3
• ZTWNNYCKSFVZIV-UHFFFAOYSA-N 1-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C)C(F)(F)F ZTWNNYCKSFVZIV-UHFFFAOYSA-N 0.000 claims 1
• YDKDEOQNUMAHOV-UHFFFAOYSA-N 1-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F YDKDEOQNUMAHOV-UHFFFAOYSA-N 0.000 claims 1
• ZUDMLKJZPPCJII-UHFFFAOYSA-N 1-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclohexyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCCC1)COC)C(F)(F)F ZUDMLKJZPPCJII-UHFFFAOYSA-N 0.000 claims 1
• OIQXUDNGOOXBFF-UHFFFAOYSA-N 1-[4-[5-[2-cyclopropyl-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F OIQXUDNGOOXBFF-UHFFFAOYSA-N 0.000 claims 1
• WZQTWAGZCXFSST-UHFFFAOYSA-N 1-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[(3-methoxy-2,2-dimethylpropyl)-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC(COC)(C)C)C(F)(F)F WZQTWAGZCXFSST-UHFFFAOYSA-N 0.000 claims 1
• FLPJVYKMIWBQJZ-UHFFFAOYSA-N 1-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluorophenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(C=C1)N1CCC(CC1)C(=O)O)F)N(C)CC1(CCCC1)COC)C(F)(F)F FLPJVYKMIWBQJZ-UHFFFAOYSA-N 0.000 claims 1
• FSUZLBQVSZGSBU-UHFFFAOYSA-N 1-[4-[5-[2-ethoxy-6-(trifluoromethyl)pyridin-4-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=NC(=CC(=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F FSUZLBQVSZGSBU-UHFFFAOYSA-N 0.000 claims 1
• WCBQIHUULCLGDH-UHFFFAOYSA-N 1-[4-[5-[4-ethoxy-3-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=C1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F WCBQIHUULCLGDH-UHFFFAOYSA-N 0.000 claims 1
• OJEQJNIOSXMLRM-UHFFFAOYSA-N 1-[4-[5-[5,6-bis(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound FC(C=1C=C(C=NC=1C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)(F)F OJEQJNIOSXMLRM-UHFFFAOYSA-N 0.000 claims 1
• LXKSIXPJMNIEIE-UHFFFAOYSA-N 1-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(ethoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COCC)C(F)(F)F LXKSIXPJMNIEIE-UHFFFAOYSA-N 0.000 claims 1
• OJWJSFDGPNURKA-UHFFFAOYSA-N 1-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCC1)COC)C(F)(F)F OJWJSFDGPNURKA-UHFFFAOYSA-N 0.000 claims 1
• YXPSLQCCVMWPSC-UHFFFAOYSA-N 1-[4-[5-[6-cyclopropyl-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C1(CC1)C1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F YXPSLQCCVMWPSC-UHFFFAOYSA-N 0.000 claims 1
• XOSORTQIEGQCSX-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluorophenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(C=C1)N1CCC(CC1)C(=O)O)F)N(C)CC1(CCC1)COC)C(F)(F)F XOSORTQIEGQCSX-UHFFFAOYSA-N 0.000 claims 1
• MLMUVCNVJNSERI-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(C=C1)N1CCC(CC1)C(=O)O)C)N(C)CC1(CCC1)COC)C(F)(F)F MLMUVCNVJNSERI-UHFFFAOYSA-N 0.000 claims 1
• RWZVPQQCEUZINH-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-fluorophenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=C(C=C(C=C1)N1CCC(CC1)C(=O)O)F)N(C)CC1(CCCC1)COC)C(F)(F)F RWZVPQQCEUZINH-UHFFFAOYSA-N 0.000 claims 1
• NBNGWKWPYBKCHQ-UHFFFAOYSA-N 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclopentyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylic acid Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)O)N(C)CC1(CCCC1)COC)C(F)(F)F NBNGWKWPYBKCHQ-UHFFFAOYSA-N 0.000 claims 1
• IXFPOCDBBXKFNK-UHFFFAOYSA-N 2-[1-[4-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidin-4-yl]oxyacetic acid Chemical compound FC=1C=C(C=C(C=1)C(F)(F)F)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)OCC(=O)O)N(C)CC1(CCC1)COC IXFPOCDBBXKFNK-UHFFFAOYSA-N 0.000 claims 1
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• QDRHPSKBHXCPJX-UHFFFAOYSA-N ethyl 1-[4-[5-[6-ethoxy-5-(trifluoromethyl)pyridin-3-yl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]piperidine-4-carboxylate Chemical compound C(C)OC1=C(C=C(C=N1)C1=CC(=C2C(=N1)N=C(N2)C1=CC=C(C=C1)N1CCC(CC1)C(=O)OCC)N(C)CC1(CCC1)COC)C(F)(F)F QDRHPSKBHXCPJX-UHFFFAOYSA-N 0.000 description 2
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• KZROLDPOPRPTJY-UHFFFAOYSA-N ethyl 3-[4-fluoro-4-[6-[5-[3-fluoro-5-(trifluoromethyl)phenyl]-7-[[1-(methoxymethyl)cyclobutyl]methyl-methylamino]-1H-imidazo[4,5-b]pyridin-2-yl]pyridin-3-yl]piperidin-1-yl]propanoate Chemical compound FC1(CCN(CC1)CCC(=O)OCC)C=1C=NC(=CC=1)C=1NC=2C(=NC(=CC=2N(C)CC2(CCC2)COC)C2=CC(=CC(=C2)C(F)(F)F)F)N=1 KZROLDPOPRPTJY-UHFFFAOYSA-N 0.000 description 2
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