JP2013527842A5 - - Google Patents
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- Publication number
- JP2013527842A5 JP2013527842A5 JP2013505470A JP2013505470A JP2013527842A5 JP 2013527842 A5 JP2013527842 A5 JP 2013527842A5 JP 2013505470 A JP2013505470 A JP 2013505470A JP 2013505470 A JP2013505470 A JP 2013505470A JP 2013527842 A5 JP2013527842 A5 JP 2013527842A5
- Authority
- JP
- Japan
- Prior art keywords
- methylsulfonamido
- pyridine
- methyl
- carboxamide
- furo
- 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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- -1 morpholino, piperidino, piperazino Chemical group 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 150000002367 halogens Chemical class 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 5
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 3
- FRTNXIFDMHQBAU-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-3-(dimethylamino)pentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCC(CC(O)=O)N(C)C)S(C)(=O)=O)=C1C1CC1 FRTNXIFDMHQBAU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- 239000002253 acid Substances 0.000 claims 12
- 150000003857 carboxamides Chemical class 0.000 claims 10
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 239000005973 Carvone Substances 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 235000005152 nicotinamide Nutrition 0.000 claims 5
- 239000011570 nicotinamide Substances 0.000 claims 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- 208000019425 cirrhosis of liver Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 4
- 208000015181 infectious disease Diseases 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- QOEMALSCTNIUIA-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-methylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC(C)C(O)=O)S(C)(=O)=O)=C1C1CC1 QOEMALSCTNIUIA-UHFFFAOYSA-N 0.000 claims 3
- XMSXZBZVTXNDGB-UHFFFAOYSA-N 5-cyclopropyl-6-[3-(1,1-dioxothiolan-2-yl)propyl-methylsulfonylamino]-2-(4-fluorophenyl)-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC1CCCS1(=O)=O XMSXZBZVTXNDGB-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- SNYCNNKDEUDLIU-UHFFFAOYSA-N 2-[2-[2-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]ethoxy]ethyl]-4-methoxybutanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCOCCC(CCOC)C(O)=O)S(C)(=O)=O)=C1C1CC1 SNYCNNKDEUDLIU-UHFFFAOYSA-N 0.000 claims 2
- LNWWOLRTASASCN-UHFFFAOYSA-N 5-[[2-(4-ethylphenyl)-5-iodo-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentyl-methylphosphinic acid Chemical compound C1=CC(CC)=CC=C1C1=C(C(=O)NC)C2=CC(I)=C(N(CCCCCP(C)(O)=O)S(C)(=O)=O)N=C2O1 LNWWOLRTASASCN-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 230000007882 cirrhosis Effects 0.000 claims 2
- 201000003278 cryoglobulinemia Diseases 0.000 claims 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 2
- 230000015788 innate immune response Effects 0.000 claims 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 230000001629 suppression Effects 0.000 claims 2
- DSQRAYCAIWKYLW-IEBWSBKVSA-N (1r,2s)-2-[2-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]ethyl]cyclopropane-1-carboxylic acid Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CC[C@@H]1C[C@H]1C(O)=O DSQRAYCAIWKYLW-IEBWSBKVSA-N 0.000 claims 1
- DSQRAYCAIWKYLW-HKUYNNGSSA-N (1s,2r)-2-[2-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]ethyl]cyclopropane-1-carboxylic acid Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CC[C@H]1C[C@@H]1C(O)=O DSQRAYCAIWKYLW-HKUYNNGSSA-N 0.000 claims 1
- GFTSWYRAOGYXGP-HXUWFJFHSA-N (2R)-6-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-(methoxymethyl)hexanoic acid Chemical compound C1(CC1)C=1C=C2C(=NC1N(S(=O)(=O)C)CCCC[C@@H](C(=O)O)COC)OC(=C2C(NC)=O)C2=CC=C(C=C2)C GFTSWYRAOGYXGP-HXUWFJFHSA-N 0.000 claims 1
- GJQROHMXOJDOME-LJQANCHMSA-N (2r)-5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-(methoxymethyl)pentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCC[C@H](COC)C(O)=O)S(C)(=O)=O)=C1C1CC1 GJQROHMXOJDOME-LJQANCHMSA-N 0.000 claims 1
- QOEMALSCTNIUIA-MRXNPFEDSA-N (2r)-5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-methylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCC[C@@H](C)C(O)=O)S(C)(=O)=O)=C1C1CC1 QOEMALSCTNIUIA-MRXNPFEDSA-N 0.000 claims 1
- FRVPIRKWDGYIDH-FQEVSTJZSA-N (2s)-1-[5-[2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-[methyl(methylsulfonyl)amino]furo[2,3-b]pyridin-5-yl]pentanoyl]pyrrolidine-2-carboxylic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC(N(C)S(C)(=O)=O)=C1CCCCC(=O)N1CCC[C@H]1C(O)=O FRVPIRKWDGYIDH-FQEVSTJZSA-N 0.000 claims 1
- QOEMALSCTNIUIA-INIZCTEOSA-N (2s)-5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-methylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCC[C@H](C)C(O)=O)S(C)(=O)=O)=C1C1CC1 QOEMALSCTNIUIA-INIZCTEOSA-N 0.000 claims 1
- ZMHBQPIMLHJSGI-JZJYNLBNSA-N (2z)-6-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-(1-hydroxyethylidene)hexanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC\C(=C(/C)O)C(O)=O)S(C)(=O)=O)=C1C1CC1 ZMHBQPIMLHJSGI-JZJYNLBNSA-N 0.000 claims 1
- INIHUUZKYVUKSR-RISCZKNCSA-N (5r,7s)-2-(4-fluorophenyl)-7-hydroxy-n,5-dimethyl-9-methylsulfonyl-5,6,7,8-tetrahydrofuro[3,4]pyrido[3,5-b]azepine-3-carboxamide Chemical compound C=1([C@H](C)C[C@H](O)CN(C=1N=C1O2)S(C)(=O)=O)C=C1C(C(=O)NC)=C2C1=CC=C(F)C=C1 INIHUUZKYVUKSR-RISCZKNCSA-N 0.000 claims 1
- INIHUUZKYVUKSR-FZMZJTMJSA-N (5s,7s)-2-(4-fluorophenyl)-7-hydroxy-n,5-dimethyl-9-methylsulfonyl-5,6,7,8-tetrahydrofuro[3,4]pyrido[3,5-b]azepine-3-carboxamide Chemical compound C=1([C@@H](C)C[C@H](O)CN(C=1N=C1O2)S(C)(=O)=O)C=C1C(C(=O)NC)=C2C1=CC=C(F)C=C1 INIHUUZKYVUKSR-FZMZJTMJSA-N 0.000 claims 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims 1
- PCFPUIOAHJOVAY-UHFFFAOYSA-N 1-[3-[[5-cyclopropyl-2-(4-ethylphenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]propyl]cyclobutane-1-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C1=C(C(=O)NC)C2=CC(C3CC3)=C(N(CCCC3(CCC3)C(O)=O)S(C)(=O)=O)N=C2O1 PCFPUIOAHJOVAY-UHFFFAOYSA-N 0.000 claims 1
- GXPJQLQCWPHJRY-UHFFFAOYSA-N 1-[3-[[5-cyclopropyl-2-(4-ethylphenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]propyl]cyclopropane-1-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C1=C(C(=O)NC)C2=CC(C3CC3)=C(N(CCCC3(CC3)C(O)=O)S(C)(=O)=O)N=C2O1 GXPJQLQCWPHJRY-UHFFFAOYSA-N 0.000 claims 1
- FQIHDCQBYBVNES-UHFFFAOYSA-N 1-[3-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]propyl]cyclopentane-1-carboxylic acid Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC1(C(O)=O)CCCC1 FQIHDCQBYBVNES-UHFFFAOYSA-N 0.000 claims 1
- SEFQEQAOQYASOB-UHFFFAOYSA-N 1-[3-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]propyl]cyclopropane-1-carboxylic acid Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC1(C(O)=O)CC1 SEFQEQAOQYASOB-UHFFFAOYSA-N 0.000 claims 1
- RASDLEXTMFQJDT-UHFFFAOYSA-N 1-acetyl-4-[3-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]propyl]piperidine-4-carboxylic acid Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC1(C(O)=O)CCN(C(C)=O)CC1 RASDLEXTMFQJDT-UHFFFAOYSA-N 0.000 claims 1
- WVVAUDQOSKJKRH-UHFFFAOYSA-N 10-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]decanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCCCCCCC(O)=O)S(C)(=O)=O)=C1C1CC1 WVVAUDQOSKJKRH-UHFFFAOYSA-N 0.000 claims 1
- XWHDJAIZRLEVKQ-UHFFFAOYSA-N 15-(4-fluorophenyl)-N-methyl-2,6-bis(methylsulfonyl)-16-oxa-2,6,18-triazatricyclo[9.7.0.013,17]octadeca-1(18),11,13(17),14-tetraene-14-carboxamide Chemical compound O1C2=NC=3N(S(C)(=O)=O)CCCN(S(C)(=O)=O)CCCCC=3C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 XWHDJAIZRLEVKQ-UHFFFAOYSA-N 0.000 claims 1
- WUUNZGWIKDXLHC-LJQANCHMSA-N 2-(4-chlorophenyl)-5-cyclopropyl-6-[3-[(2r)-1,1-dioxothiolan-2-yl]propyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(Cl)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCC[C@@H]1CCCS1(=O)=O WUUNZGWIKDXLHC-LJQANCHMSA-N 0.000 claims 1
- MZRRKGGAZYQTOC-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[3-(1,1-dioxothiolan-2-yl)propyl-methylsulfonylamino]-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound IC=1C=C2C(C(=O)NC)=C(C=3C=CC(Cl)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC1CCCS1(=O)=O MZRRKGGAZYQTOC-UHFFFAOYSA-N 0.000 claims 1
- USGYNJNGCXWECB-UHFFFAOYSA-N 2-(4-ethylphenyl)-6-[5-hydroxypentyl(methylsulfonyl)amino]-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C1=CC(CC)=CC=C1C1=C(C(=O)NC)C2=CC(I)=C(N(CCCCCO)S(C)(=O)=O)N=C2O1 USGYNJNGCXWECB-UHFFFAOYSA-N 0.000 claims 1
- WMTRWODOUNXOCV-UHFFFAOYSA-N 2-(4-fluoro-phenyl)-7,10-bis-methanesulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide Chemical compound O1C2=NC=3N(S(C)(=O)=O)CCN(S(C)(=O)=O)CC(C)C=3C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 WMTRWODOUNXOCV-UHFFFAOYSA-N 0.000 claims 1
- ITMYQNXYDLGMSJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(1-hydroxyethyl)-n-methyl-6-[methyl(methylsulfonyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(C)S(C)(=O)=O)=C(C(C)O)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 ITMYQNXYDLGMSJ-UHFFFAOYSA-N 0.000 claims 1
- JNPHZBZMBQWYBV-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-hydroxy-n,5-dimethyl-9-methylsulfonyl-7,8-dihydro-6h-furo[3,4]pyrido[3,5-c]azepine-3-carboxamide Chemical compound O1C2=NC=3N(S(C)(=O)=O)CCCC(C)(O)C=3C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 JNPHZBZMBQWYBV-UHFFFAOYSA-N 0.000 claims 1
- FPAMTRLUTSLMGO-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-iodo-6-[2-(2-methoxyphenyl)ethyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound IC=1C=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCC1=CC=CC=C1OC FPAMTRLUTSLMGO-UHFFFAOYSA-N 0.000 claims 1
- ICGAQYGLEQLBKF-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-iodo-6-[3-(2-methoxyethoxy)propyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCCOCCOC)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 ICGAQYGLEQLBKF-UHFFFAOYSA-N 0.000 claims 1
- UGQMZWYZGRLUKF-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-iodo-n-methyl-6-[methyl(methylsulfonyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(C)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 UGQMZWYZGRLUKF-UHFFFAOYSA-N 0.000 claims 1
- MFCDBEIQBZGEFT-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-[2-hydroxyethyl(methylsulfonyl)amino]-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCO)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 MFCDBEIQBZGEFT-UHFFFAOYSA-N 0.000 claims 1
- ARAXOULOKOFRQC-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-[4-hydroxyhex-5-enyl(methylsulfonyl)amino]-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCCC(O)C=C)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 ARAXOULOKOFRQC-UHFFFAOYSA-N 0.000 claims 1
- MYHOBLALRJVCMI-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-[4-hydroxypentyl(methylsulfonyl)amino]-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCCC(C)O)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 MYHOBLALRJVCMI-UHFFFAOYSA-N 0.000 claims 1
- WRRWWBRQCMFZTL-UHFFFAOYSA-N 2-(4-fluorophenyl)-6-hydroxy-n,5-dimethyl-9-methylsulfonyl-5,6,7,8-tetrahydrofuro[3,4]pyrido[3,5-b]azepine-3-carboxamide Chemical compound O1C2=NC=3N(S(C)(=O)=O)CCC(O)C(C)C=3C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 WRRWWBRQCMFZTL-UHFFFAOYSA-N 0.000 claims 1
- PQWKJKZRCKBBSE-UHFFFAOYSA-N 2-(4-fluorophenyl)-n,5-dimethyl-9-methylsulfonyl-5,6,7,8-tetrahydrofuro[3,4]pyrido[3,5-b]azepine-3-carboxamide Chemical compound O1C2=NC=3N(S(C)(=O)=O)CCCC(C)C=3C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 PQWKJKZRCKBBSE-UHFFFAOYSA-N 0.000 claims 1
- XFNBFSMYVSZOMT-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-methyl-6-[methyl(methylsulfonyl)amino]-5-(oxiran-2-ylmethyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC(N(C)S(C)(=O)=O)=C1CC1CO1 XFNBFSMYVSZOMT-UHFFFAOYSA-N 0.000 claims 1
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- CGYGYZPRMNUFKQ-UHFFFAOYSA-N 2-[3-[[5-iodo-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]propyl]cyclopentane-1-carboxylic acid Chemical compound IC=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC1CCCC1C(O)=O CGYGYZPRMNUFKQ-UHFFFAOYSA-N 0.000 claims 1
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- HEGKYLVYHUOSGV-UHFFFAOYSA-N 5-[[5-cyclopropyl-2-(4-ethylphenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-methylpentanoic acid Chemical compound C1=CC(CC)=CC=C1C1=C(C(=O)NC)C2=CC(C3CC3)=C(N(CCCC(C)C(O)=O)S(C)(=O)=O)N=C2O1 HEGKYLVYHUOSGV-UHFFFAOYSA-N 0.000 claims 1
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- AGQOWWURBCXDCL-UHFFFAOYSA-N 5-[[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2,2-dimethylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC(N(CCCC(C)(C)C(O)=O)S(C)(=O)=O)=C1C1CC1 AGQOWWURBCXDCL-UHFFFAOYSA-N 0.000 claims 1
- MIVUGWIORUEXBA-UHFFFAOYSA-N 5-[[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC(N(CCCCC(O)=O)S(C)(=O)=O)=C1C1CC1 MIVUGWIORUEXBA-UHFFFAOYSA-N 0.000 claims 1
- OEQVLXGNVRPLGA-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2,2-dimethylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC(C)(C)C(O)=O)S(C)(=O)=O)=C1C1CC1 OEQVLXGNVRPLGA-UHFFFAOYSA-N 0.000 claims 1
- DFXOBDIJEXUVDO-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-(2-methoxyethyl)-2-methylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC(C)(CCOC)C(O)=O)S(C)(=O)=O)=C1C1CC1 DFXOBDIJEXUVDO-UHFFFAOYSA-N 0.000 claims 1
- RDFADLLLOGHMQQ-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-(methoxymethyl)-2-methylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC(C)(COC)C(O)=O)S(C)(=O)=O)=C1C1CC1 RDFADLLLOGHMQQ-UHFFFAOYSA-N 0.000 claims 1
- JBRDRDRGBCIKBV-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-methoxy-2-methylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC(C)(OC)C(O)=O)S(C)(=O)=O)=C1C1CC1 JBRDRDRGBCIKBV-UHFFFAOYSA-N 0.000 claims 1
- BZUOTVYEWHZJGD-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-4-hydroxypentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CC(O)CCC(O)=O)S(C)(=O)=O)=C1C1CC1 BZUOTVYEWHZJGD-UHFFFAOYSA-N 0.000 claims 1
- DJAQYMZRMHFAFB-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCC(O)=O)S(C)(=O)=O)=C1C1CC1 DJAQYMZRMHFAFB-UHFFFAOYSA-N 0.000 claims 1
- BXFRLWGSHWDADR-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentyl-methylphosphinic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCCP(C)(O)=O)S(C)(=O)=O)=C1C1CC1 BXFRLWGSHWDADR-UHFFFAOYSA-N 0.000 claims 1
- RXTUGRHRBMJANC-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-phenoxyphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2,2-dimethylpentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(OC=4C=CC=CC=4)=CC=3)OC2=NC(N(CCCC(C)(C)C(O)=O)S(C)(=O)=O)=C1C1CC1 RXTUGRHRBMJANC-UHFFFAOYSA-N 0.000 claims 1
- NIUYYPSZGCKTMX-UHFFFAOYSA-N 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-phenoxyphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(OC=4C=CC=CC=4)=CC=3)OC2=NC(N(CCCCC(O)=O)S(C)(=O)=O)=C1C1CC1 NIUYYPSZGCKTMX-UHFFFAOYSA-N 0.000 claims 1
- LTYYDNSLQAYAAU-UHFFFAOYSA-N 5-[[5-ethenyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentanoic acid Chemical compound O1C2=NC(N(CCCCC(O)=O)S(C)(=O)=O)=C(C=C)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 LTYYDNSLQAYAAU-UHFFFAOYSA-N 0.000 claims 1
- AXSKRXNOIAISHY-UHFFFAOYSA-N 5-[[5-ethyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentanoic acid Chemical compound O1C=2N=C(N(CCCCC(O)=O)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 AXSKRXNOIAISHY-UHFFFAOYSA-N 0.000 claims 1
- VBUGPNYCQZRKEL-UHFFFAOYSA-N 5-[[5-iodo-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentyl-methylphosphinic acid Chemical compound O1C2=NC(N(CCCCCP(C)(O)=O)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(C)C=C1 VBUGPNYCQZRKEL-UHFFFAOYSA-N 0.000 claims 1
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- JZENMNICPVCZQT-UHFFFAOYSA-N 5-cyclopropyl-2-(4-fluorophenyl)-6-[2-hydroxyethyl(methylsulfonyl)amino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC(N(CCO)S(C)(=O)=O)=C1C1CC1 JZENMNICPVCZQT-UHFFFAOYSA-N 0.000 claims 1
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- WWZDKPJZISNHDB-UHFFFAOYSA-N 5-cyclopropyl-2-(4-fluorophenyl)-6-[3-hydroxybutyl(methylsulfonyl)amino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC(N(CCC(C)O)S(C)(=O)=O)=C1C1CC1 WWZDKPJZISNHDB-UHFFFAOYSA-N 0.000 claims 1
- KTTWJISYLNNJLM-UHFFFAOYSA-N 5-cyclopropyl-2-(4-fluorophenyl)-6-[4-hydroxypentyl(methylsulfonyl)amino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC(N(CCCC(C)O)S(C)(=O)=O)=C1C1CC1 KTTWJISYLNNJLM-UHFFFAOYSA-N 0.000 claims 1
- JYQLHZAAZNIWIU-UHFFFAOYSA-N 5-cyclopropyl-2-[4-(2-fluorophenoxy)phenyl]-N-methyl-6-[methylsulfonyl(pentyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1(CC1)C=1C=C2C(=NC=1N(S(=O)(=O)C)CCCCC)OC(=C2C(NC)=O)C1=CC=C(C=C1)OC1=C(C=CC=C1)F JYQLHZAAZNIWIU-UHFFFAOYSA-N 0.000 claims 1
- SNSHNVUAEUDBKL-UHFFFAOYSA-N 5-cyclopropyl-2-[4-(4-fluorophenoxy)phenyl]-N-methyl-6-[methylsulfonyl(pentyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1(CC1)C=1C=C2C(=NC=1N(S(=O)(=O)C)CCCCC)OC(=C2C(NC)=O)C1=CC=C(C=C1)OC1=CC=C(C=C1)F SNSHNVUAEUDBKL-UHFFFAOYSA-N 0.000 claims 1
- ZHCHYXFNJRORHN-UHFFFAOYSA-N 5-cyclopropyl-6-[2-(1,1-dioxothiolan-3-yl)ethyl-methylsulfonylamino]-2-(4-fluorophenyl)-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCC1CCS(=O)(=O)C1 ZHCHYXFNJRORHN-UHFFFAOYSA-N 0.000 claims 1
- CRTGKKQPNOEJLU-UHFFFAOYSA-N 5-cyclopropyl-6-[2-(1,1-dioxothiolan-3-yl)ethyl-methylsulfonylamino]-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCC1CCS(=O)(=O)C1 CRTGKKQPNOEJLU-UHFFFAOYSA-N 0.000 claims 1
- NVCJWGBREXXBPG-HXUWFJFHSA-N 5-cyclopropyl-6-[3-[(2r)-1,1-dioxothiolan-2-yl]propyl-methylsulfonylamino]-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCC[C@@H]1CCCS1(=O)=O NVCJWGBREXXBPG-HXUWFJFHSA-N 0.000 claims 1
- XXYRWFCLHQQRJI-UHFFFAOYSA-N 5-cyclopropyl-6-[3-hydroxybutyl(methylsulfonyl)amino]-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCC(C)O)S(C)(=O)=O)=C1C1CC1 XXYRWFCLHQQRJI-UHFFFAOYSA-N 0.000 claims 1
- RRLURJRCESHLJV-UHFFFAOYSA-N 5-cyclopropyl-6-[3-hydroxypropyl(methylsulfonyl)amino]-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCO)S(C)(=O)=O)=C1C1CC1 RRLURJRCESHLJV-UHFFFAOYSA-N 0.000 claims 1
- QVHDGTKRVGMSCV-UHFFFAOYSA-N 5-cyclopropyl-6-[4-hydroxybutyl(methylsulfonyl)amino]-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCO)S(C)(=O)=O)=C1C1CC1 QVHDGTKRVGMSCV-UHFFFAOYSA-N 0.000 claims 1
- OEPKVZFECXHQJC-UHFFFAOYSA-N 5-cyclopropyl-6-[5-hydroxypentyl(methylsulfonyl)amino]-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCCO)S(C)(=O)=O)=C1C1CC1 OEPKVZFECXHQJC-UHFFFAOYSA-N 0.000 claims 1
- RXANCFTWVPGFRL-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-2-(4-methylphenyl)-6-[methylsulfonyl(3-methylsulfonylpropyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCS(C)(=O)=O)S(C)(=O)=O)=C1C1CC1 RXANCFTWVPGFRL-UHFFFAOYSA-N 0.000 claims 1
- IXONLEJUCDYTID-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-2-(4-methylphenyl)-6-[methylsulfonyl(4-methylsulfonylbutyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCS(C)(=O)=O)S(C)(=O)=O)=C1C1CC1 IXONLEJUCDYTID-UHFFFAOYSA-N 0.000 claims 1
- YUZMGUVYXQOQOZ-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-2-(4-methylphenyl)-6-[methylsulfonyl(pent-4-enyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC=C)S(C)(=O)=O)=C1C1CC1 YUZMGUVYXQOQOZ-UHFFFAOYSA-N 0.000 claims 1
- YEFYLOPSWMQYSC-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-2-(4-methylphenyl)-6-[methylsulfonyl-[(5-oxooxolan-2-yl)methyl]amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CC1CCC(=O)O1 YEFYLOPSWMQYSC-UHFFFAOYSA-N 0.000 claims 1
- NYPZVCXIJLQQBS-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-2-(4-methylphenyl)-6-[methylsulfonyl-[3-(2-oxopyrrolidin-1-yl)propyl]amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCN1CCCC1=O NYPZVCXIJLQQBS-UHFFFAOYSA-N 0.000 claims 1
- DVTZKDBFSKWNTM-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-2-(4-methylphenyl)-6-[methylsulfonyl-[3-(2h-tetrazol-5-yl)propyl]amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC=1N=NNN=1 DVTZKDBFSKWNTM-UHFFFAOYSA-N 0.000 claims 1
- MPBJLSDKWQYMHS-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-2-(4-methylphenyl)-6-[methylsulfonyl-[4-(2h-tetrazol-5-yl)butyl]amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound C1CC1C=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCCC=1N=NNN=1 MPBJLSDKWQYMHS-UHFFFAOYSA-N 0.000 claims 1
- ZIMBLNAQBVSMMC-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-6-[methyl(methylsulfonyl)amino]-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(C)S(C)(=O)=O)=C1C1CC1 ZIMBLNAQBVSMMC-UHFFFAOYSA-N 0.000 claims 1
- APKSWHNYIRMGIY-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-6-[methyl(methylsulfonyl)amino]-2-phenylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC=CC=3)OC2=NC(N(C)S(C)(=O)=O)=C1C1CC1 APKSWHNYIRMGIY-UHFFFAOYSA-N 0.000 claims 1
- GLROIEHXGMKXPA-UHFFFAOYSA-N 5-ethenyl-2-(4-fluorophenyl)-n-methyl-6-[methyl(methylsulfonyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(C)S(C)(=O)=O)=C(C=C)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 GLROIEHXGMKXPA-UHFFFAOYSA-N 0.000 claims 1
- WTFQQMNCVHNERJ-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[(4-hydroxy-4-methylpentyl)-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCCC(C)(C)O)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 WTFQQMNCVHNERJ-UHFFFAOYSA-N 0.000 claims 1
- RHFNHGODPWXVID-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[(5-hydroxy-5-methylhexyl)-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCCCC(C)(C)O)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 RHFNHGODPWXVID-UHFFFAOYSA-N 0.000 claims 1
- KSAGKNDPUUPWQH-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[2-(2-methoxyethoxy)ethyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCOCCOC)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 KSAGKNDPUUPWQH-UHFFFAOYSA-N 0.000 claims 1
- VIGPBWJRUHBEFH-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[2-(2-methoxyphenoxy)ethyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCOC1=CC=CC=C1OC VIGPBWJRUHBEFH-UHFFFAOYSA-N 0.000 claims 1
- NSRXNSPIXSEZMM-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[2-(3-methoxyphenyl)ethyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCC1=CC=CC(OC)=C1 NSRXNSPIXSEZMM-UHFFFAOYSA-N 0.000 claims 1
- CMEYEXSUCCIYOU-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[2-(4-methoxyphenyl)ethyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCC1=CC=C(OC)C=C1 CMEYEXSUCCIYOU-UHFFFAOYSA-N 0.000 claims 1
- YUUUWRFTXUKYQM-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[3-(2-methoxyphenoxy)propyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCCOC1=CC=CC=C1OC YUUUWRFTXUKYQM-UHFFFAOYSA-N 0.000 claims 1
- FURFJCWGIVBVDJ-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[3-hydroxypropyl(methylsulfonyl)amino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCCO)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 FURFJCWGIVBVDJ-UHFFFAOYSA-N 0.000 claims 1
- BPPJOKLXZKUGMT-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[4-(2-hydroxy-5-oxocyclopenten-1-yl)butyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCCCC1=C(O)CCC1=O BPPJOKLXZKUGMT-UHFFFAOYSA-N 0.000 claims 1
- UXCCYLFCEPXHAA-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[4-(2-methoxyphenoxy)butyl-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCCCOC1=CC=CC=C1OC UXCCYLFCEPXHAA-UHFFFAOYSA-N 0.000 claims 1
- WBGCMHDPIDDUJV-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-6-[5-hydroxyhexyl(methylsulfonyl)amino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCCCC(C)O)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 WBGCMHDPIDDUJV-UHFFFAOYSA-N 0.000 claims 1
- IWXICVYLXIXTDH-QGZVFWFLSA-N 5-ethyl-2-(4-fluorophenyl)-6-[[(2r)-3-(6-methoxypyridin-3-yl)-2-methylpropyl]-methylsulfonylamino]-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound C([C@@H](C)CN(C1=NC=2OC(=C(C(=O)NC)C=2C=C1CC)C=1C=CC(F)=CC=1)S(C)(=O)=O)C1=CC=C(OC)N=C1 IWXICVYLXIXTDH-QGZVFWFLSA-N 0.000 claims 1
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- MGPZGPFRHLNDFB-UHFFFAOYSA-N 5-ethyl-2-(4-fluorophenyl)-n-methyl-6-[methylsulfonyl-[3-(1,1,3-trioxothiolan-2-yl)propyl]amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCCC1C(=O)CCS1(=O)=O MGPZGPFRHLNDFB-UHFFFAOYSA-N 0.000 claims 1
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- WBMLMYPZKGPHPE-UHFFFAOYSA-N 5-iodo-n-methyl-2-(4-methylphenyl)-6-[methylsulfonyl(3-methylsulfonylpropyl)amino]furo[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCCS(C)(=O)=O)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(C)C=C1 WBMLMYPZKGPHPE-UHFFFAOYSA-N 0.000 claims 1
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- WHRPWEIYIQVDRL-UHFFFAOYSA-N 6-[3-(1,1-dioxothiolan-2-yl)propyl-methylsulfonylamino]-2-(4-fluorophenyl)-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound IC=1C=C2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC1CCCS1(=O)=O WHRPWEIYIQVDRL-UHFFFAOYSA-N 0.000 claims 1
- JQENNCMCADEEBI-UHFFFAOYSA-N 6-[3-(1,1-dioxothiolan-2-yl)propyl-methylsulfonylamino]-5-iodo-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound IC=1C=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC=1N(S(C)(=O)=O)CCCC1CCCS1(=O)=O JQENNCMCADEEBI-UHFFFAOYSA-N 0.000 claims 1
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- JKMRSBLUBIOFHT-UHFFFAOYSA-N 6-[3-bromopropyl(methylsulfonyl)amino]-5-cyclopropyl-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCBr)S(C)(=O)=O)=C1C1CC1 JKMRSBLUBIOFHT-UHFFFAOYSA-N 0.000 claims 1
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- XTXXLDFCVHFSKO-UHFFFAOYSA-N 6-[3-cyanopropyl(methylsulfonyl)amino]-5-cyclopropyl-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC#N)S(C)(=O)=O)=C1C1CC1 XTXXLDFCVHFSKO-UHFFFAOYSA-N 0.000 claims 1
- PPMKGERYYYCLBJ-UHFFFAOYSA-N 6-[3-cyanopropyl(methylsulfonyl)amino]-5-ethyl-2-(4-fluorophenyl)-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCCC#N)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 PPMKGERYYYCLBJ-UHFFFAOYSA-N 0.000 claims 1
- JDQGFJWHBQHPKG-UHFFFAOYSA-N 6-[3-cyclopropylsulfonylpropyl(methylsulfonyl)amino]-5-ethyl-2-(4-fluorophenyl)-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCCS(=O)(=O)C1CC1 JDQGFJWHBQHPKG-UHFFFAOYSA-N 0.000 claims 1
- BFOYDNICIAFTNH-UHFFFAOYSA-N 6-[3-tert-butylsulfonylpropyl(methylsulfonyl)amino]-5-ethyl-2-(4-fluorophenyl)-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCCS(=O)(=O)C(C)(C)C)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 BFOYDNICIAFTNH-UHFFFAOYSA-N 0.000 claims 1
- ZXHLHKORSBAEFK-UHFFFAOYSA-N 6-[4,5-dihydroxypentyl(methylsulfonyl)amino]-2-(4-fluorophenyl)-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCCC(O)CO)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 ZXHLHKORSBAEFK-UHFFFAOYSA-N 0.000 claims 1
- UXEASTSSSNCHKB-UHFFFAOYSA-N 6-[4-(2-cyanophenoxy)butyl-methylsulfonylamino]-5-ethyl-2-(4-fluorophenyl)-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound CCC1=CC=2C(C(=O)NC)=C(C=3C=CC(F)=CC=3)OC=2N=C1N(S(C)(=O)=O)CCCCOC1=CC=CC=C1C#N UXEASTSSSNCHKB-UHFFFAOYSA-N 0.000 claims 1
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- ORHLWUGQGFMQGW-UHFFFAOYSA-N 6-[4-cyanobutyl(methylsulfonyl)amino]-2-(4-fluorophenyl)-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCCCC#N)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 ORHLWUGQGFMQGW-UHFFFAOYSA-N 0.000 claims 1
- RUEBCAXPZUPRLG-UHFFFAOYSA-N 6-[4-cyanobutyl(methylsulfonyl)amino]-5-cyclopropyl-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCC#N)S(C)(=O)=O)=C1C1CC1 RUEBCAXPZUPRLG-UHFFFAOYSA-N 0.000 claims 1
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- QTKPUQLIGTUKGX-UHFFFAOYSA-N 6-[5-bromopentyl(methylsulfonyl)amino]-5-cyclopropyl-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCCBr)S(C)(=O)=O)=C1C1CC1 QTKPUQLIGTUKGX-UHFFFAOYSA-N 0.000 claims 1
- DMKKUHMYQUJJFP-UHFFFAOYSA-N 6-[5-hydroxypentyl(methylsulfonyl)amino]-5-iodo-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCCCCO)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(C)C=C1 DMKKUHMYQUJJFP-UHFFFAOYSA-N 0.000 claims 1
- KIEPJOVAPLEKAX-UHFFFAOYSA-N 6-[[4-(dimethylamino)-4-oxobutyl]-methylsulfonylamino]-5-ethyl-2-(4-fluorophenyl)-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCCC(=O)N(C)C)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 KIEPJOVAPLEKAX-UHFFFAOYSA-N 0.000 claims 1
- XEVAZCWJPOITGS-UHFFFAOYSA-N 6-[[5-(dimethylamino)-5-oxopentyl]-methylsulfonylamino]-5-ethyl-2-(4-fluorophenyl)-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C=2N=C(N(CCCCC(=O)N(C)C)S(C)(=O)=O)C(CC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 XEVAZCWJPOITGS-UHFFFAOYSA-N 0.000 claims 1
- AGXNMBKAFSFPEQ-UHFFFAOYSA-N 6-[[5-cyclopropyl-2-(4-ethylphenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]hexanoic acid Chemical compound C1=CC(CC)=CC=C1C1=C(C(=O)NC)C2=CC(C3CC3)=C(N(CCCCCC(O)=O)S(C)(=O)=O)N=C2O1 AGXNMBKAFSFPEQ-UHFFFAOYSA-N 0.000 claims 1
- OVDLHYOTHKWGMC-UHFFFAOYSA-N 6-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2,2-dimethylhexanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCC(C)(C)C(O)=O)S(C)(=O)=O)=C1C1CC1 OVDLHYOTHKWGMC-UHFFFAOYSA-N 0.000 claims 1
- AUPNDAMDCOJQNW-UHFFFAOYSA-N 6-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-methylsulfonylhexanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCC(C(O)=O)S(C)(=O)=O)S(C)(=O)=O)=C1C1CC1 AUPNDAMDCOJQNW-UHFFFAOYSA-N 0.000 claims 1
- VUMDFSHQKKODCG-UHFFFAOYSA-N 6-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-3-hydroxy-2,2-dimethylhexanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC(O)C(C)(C)C(O)=O)S(C)(=O)=O)=C1C1CC1 VUMDFSHQKKODCG-UHFFFAOYSA-N 0.000 claims 1
- UANWNOSBONLGOA-UHFFFAOYSA-N 6-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-3-methoxyhexanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC(CC(O)=O)OC)S(C)(=O)=O)=C1C1CC1 UANWNOSBONLGOA-UHFFFAOYSA-N 0.000 claims 1
- PJEXUWJNVBGGRP-UHFFFAOYSA-N 6-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]hexanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCCC(O)=O)S(C)(=O)=O)=C1C1CC1 PJEXUWJNVBGGRP-UHFFFAOYSA-N 0.000 claims 1
- LOHQLFYMIWMKAW-UHFFFAOYSA-N 6-[but-3-enyl(methylsulfonyl)amino]-2-(4-fluorophenyl)-5-iodo-n-methylfuro[2,3-b]pyridine-3-carboxamide Chemical compound O1C2=NC(N(CCC=C)S(C)(=O)=O)=C(I)C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 LOHQLFYMIWMKAW-UHFFFAOYSA-N 0.000 claims 1
- YPKCZGWIYGZUKH-UHFFFAOYSA-N 6-[but-3-enyl(methylsulfonyl)amino]-5-cyclopropyl-n-methyl-2-(4-methylphenyl)furo[2,3-b]pyridine-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCC=C)S(C)(=O)=O)=C1C1CC1 YPKCZGWIYGZUKH-UHFFFAOYSA-N 0.000 claims 1
- LRGHZCGNDZKYAO-UHFFFAOYSA-N 7-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]heptanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCCCC(O)=O)S(C)(=O)=O)=C1C1CC1 LRGHZCGNDZKYAO-UHFFFAOYSA-N 0.000 claims 1
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- CYIIDOHZGBZNHK-UHFFFAOYSA-N 9-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]nonanoic acid Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCCCCCC(O)=O)S(C)(=O)=O)=C1C1CC1 CYIIDOHZGBZNHK-UHFFFAOYSA-N 0.000 claims 1
- PBBKJJWVLPTIPO-UHFFFAOYSA-N CC(C)(C)CCCN(C1=C(C=C2C(=C(OC2=N1)C3=CC=C(C=C3)Cl)C(=O)NC)C4CC4)S(=O)(=O)C Chemical compound CC(C)(C)CCCN(C1=C(C=C2C(=C(OC2=N1)C3=CC=C(C=C3)Cl)C(=O)NC)C4CC4)S(=O)(=O)C PBBKJJWVLPTIPO-UHFFFAOYSA-N 0.000 claims 1
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- IFRHMNADUYOJMC-UHFFFAOYSA-N CCC(CCCN(C1=C(C=C2C(=C(OC2=N1)C3=CC=C(C=C3)C)C(=O)NC)C4CC4)S(=O)(=O)C)OCCOC Chemical compound CCC(CCCN(C1=C(C=C2C(=C(OC2=N1)C3=CC=C(C=C3)C)C(=O)NC)C4CC4)S(=O)(=O)C)OCCOC IFRHMNADUYOJMC-UHFFFAOYSA-N 0.000 claims 1
- UFFCBAAUTWHOJR-UHFFFAOYSA-N CCC1=CC2=C(N=C1N(CCCC(C)(C)C)S(=O)(=O)C)OC(=C2C(=O)NC)C3=CC=C(C=C3)F Chemical compound CCC1=CC2=C(N=C1N(CCCC(C)(C)C)S(=O)(=O)C)OC(=C2C(=O)NC)C3=CC=C(C=C3)F UFFCBAAUTWHOJR-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- XYPGNBUTPCSJGJ-UHFFFAOYSA-N ethyl 5-[2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-[methyl(methylsulfonyl)amino]furo[2,3-b]pyridin-5-yl]pentanoate Chemical compound O1C=2N=C(N(C)S(C)(=O)=O)C(CCCCC(=O)OCC)=CC=2C(C(=O)NC)=C1C1=CC=C(F)C=C1 XYPGNBUTPCSJGJ-UHFFFAOYSA-N 0.000 claims 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- CGPGOTGPGQIBDK-UHFFFAOYSA-N methyl 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]-2-methylidenepentanoate Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCC(=C)C(=O)OC)S(C)(=O)=O)=C1C1CC1 CGPGOTGPGQIBDK-UHFFFAOYSA-N 0.000 claims 1
- ZYNLVZYDZVXBMV-UHFFFAOYSA-N methyl 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pentanoate Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCCCC(=O)OC)S(C)(=O)=O)=C1C1CC1 ZYNLVZYDZVXBMV-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
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- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HPLGHESIHRZEKX-UHFFFAOYSA-N 2-(4-fluoro-phenyl)-7,10-bis-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide Chemical compound O1C2=NC=3N(S(C)(=O)=O)CCN(S(C)(=O)=O)CC(=C)C=3C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 HPLGHESIHRZEKX-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
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- 230000003612 virological effect Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VXJGNYQIEQGVAL-UHFFFAOYSA-N 2-(4-fluoro-phenyl)-10-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide Chemical compound O1C2=NC=3N(S(C)(=O)=O)CCNCC(=C)C=3C=C2C(C(=O)NC)=C1C1=CC=C(F)C=C1 VXJGNYQIEQGVAL-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000711549 Hepacivirus C Species 0.000 description 1
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- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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- KSYLONOCVNCFKX-UHFFFAOYSA-N methyl 5-[[5-cyclopropyl-3-(methylcarbamoyl)-2-(4-methylphenyl)furo[2,3-b]pyridin-6-yl]-methylsulfonylamino]pent-2-enoate Chemical compound C1=C2C(C(=O)NC)=C(C=3C=CC(C)=CC=3)OC2=NC(N(CCC=CC(=O)OC)S(C)(=O)=O)=C1C1CC1 KSYLONOCVNCFKX-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
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| US61/326,491 | 2010-04-21 | ||
| PCT/EP2011/056304 WO2011131709A1 (en) | 2010-04-21 | 2011-04-20 | Furopyridine compounds and uses thereof |
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| JP2013527842A JP2013527842A (ja) | 2013-07-04 |
| JP2013527842A5 true JP2013527842A5 (https=) | 2014-05-08 |
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| SG189985A1 (en) | 2010-10-26 | 2013-06-28 | Presidio Pharmaceuticals Inc | Inhibitors of hepatitis c virus |
| WO2013163466A1 (en) * | 2012-04-25 | 2013-10-31 | Presidio Pharmaceuticals, Inc. | Inhibitors of hepatitis c virus |
| TWI731854B (zh) * | 2015-03-23 | 2021-07-01 | 美商共結晶製藥公司 | Ｃ型肝炎病毒聚合酶之抑制劑 |
| AU2016258192B2 (en) | 2015-05-06 | 2021-07-29 | Leidos Biomedical Research, Inc. | K-Ras modulators |
| EP3612526A2 (en) | 2017-04-20 | 2020-02-26 | The Regents of the University of California | K-ras modulators |
| JP7237941B2 (ja) * | 2017-05-19 | 2023-03-13 | エヌフレクション セラピューティクス インコーポレイテッド | 皮膚障害の処置用の融合複素環式芳香族アニリン化合物 |
| WO2019204449A1 (en) * | 2018-04-18 | 2019-10-24 | Theras, Inc. | K-ras modulators with a vinyl sulfone moiety |
| CN108727309B (zh) * | 2018-06-20 | 2023-04-07 | 天津全和诚科技有限责任公司 | 一种3-氧杂环丁烷羧酸的合成方法 |
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- 2011-04-20 JP JP2013505470A patent/JP5756850B2/ja not_active Expired - Fee Related
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- 2011-04-20 EP EP11715244.7A patent/EP2560976B9/en not_active Not-in-force
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- 2011-04-20 WO PCT/EP2011/056304 patent/WO2011131709A1/en not_active Ceased
- 2011-04-20 TW TW100113755A patent/TW201139446A/zh unknown
- 2011-04-25 UY UY0001033348A patent/UY33348A/es not_active Application Discontinuation
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