JP2010501585A5 - - Google Patents
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- Publication number
- JP2010501585A5 JP2010501585A5 JP2009525720A JP2009525720A JP2010501585A5 JP 2010501585 A5 JP2010501585 A5 JP 2010501585A5 JP 2009525720 A JP2009525720 A JP 2009525720A JP 2009525720 A JP2009525720 A JP 2009525720A JP 2010501585 A5 JP2010501585 A5 JP 2010501585A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyridine
- fluoro
- phenylamino
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 17
- -1 2,2-dimethyl-1,3-dioxolanyl Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- GBJNZGDNTWILNB-UHFFFAOYSA-N furo[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2OC(C(=O)N)=CC2=C1 GBJNZGDNTWILNB-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- ZNGLPDOTLBLTIX-SECBINFHSA-N 7-chloro-n-[(2r)-2,3-dihydroxypropoxy]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=C(Cl)C=NC=C2C=1NC1=CC=C(I)C=C1F ZNGLPDOTLBLTIX-SECBINFHSA-N 0.000 claims 2
- AREKJPKIPLDVQY-UHFFFAOYSA-N 7-fluoro-3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=C(F)C=NC=C2C=1NC1=CC=C(I)C=C1F AREKJPKIPLDVQY-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- GOYLXWIEDLPDLQ-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yloxy)-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCC(CO)ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F GOYLXWIEDLPDLQ-UHFFFAOYSA-N 0.000 claims 2
- MOKOPMFVODBALH-SNVBAGLBSA-N n-[(2r)-2,3-dihydroxypropoxy]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F MOKOPMFVODBALH-SNVBAGLBSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000005976 1-phenylethyloxy group Chemical group 0.000 claims 1
- HIXYMKKKJVOWOY-MRVPVSSYSA-N 3-(2,5-difluoro-4-iodoanilino)-n-[(2r)-2,3-dihydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC(F)=C(I)C=C1F HIXYMKKKJVOWOY-MRVPVSSYSA-N 0.000 claims 1
- YOTPJQSYYZLQTK-SECBINFHSA-N 3-(2,6-difluoro-4-iodoanilino)-n-[(2r)-2,3-dihydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=C(F)C=C(I)C=C1F YOTPJQSYYZLQTK-SECBINFHSA-N 0.000 claims 1
- NSUHKSDBHFLPTJ-SNVBAGLBSA-N 3-(2-chloro-4-iodoanilino)-n-[(2r)-2,3-dihydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1Cl NSUHKSDBHFLPTJ-SNVBAGLBSA-N 0.000 claims 1
- ZSVBLZJTOHYBFS-UHFFFAOYSA-N 3-(2-fluoro-4-iodo-n-methylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC=C2C=1N(C)C1=CC=C(I)C=C1F ZSVBLZJTOHYBFS-UHFFFAOYSA-N 0.000 claims 1
- XCCBPYPWIAZDAS-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(1-hydroxypropan-2-yloxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCC(C)ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F XCCBPYPWIAZDAS-UHFFFAOYSA-N 0.000 claims 1
- ZASFNBPGAMDLGQ-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(1-methylpiperidin-4-yl)oxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound C1CN(C)CCC1ONC(=O)C1=C(NC=2C(=CC(I)=CC=2)F)C2=CN=CC=C2O1 ZASFNBPGAMDLGQ-UHFFFAOYSA-N 0.000 claims 1
- YXSFFGDHEKCEFI-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(1h-imidazol-5-ylmethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCC=2NC=NC=2)OC2=CC=NC=C12 YXSFFGDHEKCEFI-UHFFFAOYSA-N 0.000 claims 1
- BRHYIGCVKINWRY-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-4-methylfuro[3,2-c]pyridine-2-carboxamide Chemical compound C1=2C(C)=NC=CC=2OC(C(=O)NOCCO)=C1NC1=CC=C(I)C=C1F BRHYIGCVKINWRY-UHFFFAOYSA-N 0.000 claims 1
- LFHVPNVFAIRFIX-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-7-methylfuro[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC=2C(C)=CN=CC=2C=1NC1=CC=C(I)C=C1F LFHVPNVFAIRFIX-UHFFFAOYSA-N 0.000 claims 1
- HJPVQFUUZVDHQC-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-7-phenylfuro[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=C(C=3C=CC=CC=3)C=NC=C2C=1NC1=CC=C(I)C=C1F HJPVQFUUZVDHQC-UHFFFAOYSA-N 0.000 claims 1
- OWQKOFHCOAAMTL-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-n-methylfuro[3,2-c]pyridine-2-carboxamide Chemical compound OCCON(C)C(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F OWQKOFHCOAAMTL-UHFFFAOYSA-N 0.000 claims 1
- LVHMCPRJISQGAK-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F LVHMCPRJISQGAK-UHFFFAOYSA-N 0.000 claims 1
- KQFHBRNOZGXYQF-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-hydroxypropoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound CC(O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F KQFHBRNOZGXYQF-UHFFFAOYSA-N 0.000 claims 1
- YMNVIHJYFYSIHE-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-methylpropoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound CC(C)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F YMNVIHJYFYSIHE-UHFFFAOYSA-N 0.000 claims 1
- BIQWLTRWWSVHFH-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-morpholin-4-ylethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCCN2CCOCC2)OC2=CC=NC=C12 BIQWLTRWWSVHFH-UHFFFAOYSA-N 0.000 claims 1
- YHQVEEYIFZLAAL-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(2-piperidin-1-ylethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCCN2CCCCC2)OC2=CC=NC=C12 YHQVEEYIFZLAAL-UHFFFAOYSA-N 0.000 claims 1
- CWSIFJGKWFWQAR-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-(oxan-4-yloxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOC2CCOCC2)OC2=CC=NC=C12 CWSIFJGKWFWQAR-UHFFFAOYSA-N 0.000 claims 1
- VTNSFKMQSHVVFX-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-[(2-methylpropan-2-yl)oxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound CC(C)(C)ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F VTNSFKMQSHVVFX-UHFFFAOYSA-N 0.000 claims 1
- KQFHBRNOZGXYQF-SECBINFHSA-N 3-(2-fluoro-4-iodoanilino)-n-[(2r)-2-hydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound C[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F KQFHBRNOZGXYQF-SECBINFHSA-N 0.000 claims 1
- KQFHBRNOZGXYQF-VIFPVBQESA-N 3-(2-fluoro-4-iodoanilino)-n-[(2s)-2-hydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound C[C@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F KQFHBRNOZGXYQF-VIFPVBQESA-N 0.000 claims 1
- AJZFZFIDJMYVGI-MERQFXBCSA-N 3-(2-fluoro-4-iodoanilino)-n-[(3s)-pyrrolidin-3-yl]oxyfuro[3,2-c]pyridine-2-carboxamide;formic acid Chemical compound OC=O.FC1=CC(I)=CC=C1NC1=C(C(=O)NO[C@@H]2CNCC2)OC2=CC=NC=C12 AJZFZFIDJMYVGI-MERQFXBCSA-N 0.000 claims 1
- RILXIUKJZTVWOR-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-[2-(2-oxopyrrolidin-1-yl)ethoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCCN2C(CCC2)=O)OC2=CC=NC=C12 RILXIUKJZTVWOR-UHFFFAOYSA-N 0.000 claims 1
- JOSPHXYARVDBKV-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-[2-(methanesulfonamido)ethoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound CS(=O)(=O)NCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F JOSPHXYARVDBKV-UHFFFAOYSA-N 0.000 claims 1
- GXPHNPWQZJWDIE-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-[2-(methylamino)ethoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound CNCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F GXPHNPWQZJWDIE-UHFFFAOYSA-N 0.000 claims 1
- GPXSOWYDMXOJSA-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-hydroxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F GPXSOWYDMXOJSA-UHFFFAOYSA-N 0.000 claims 1
- NLSWTNSYKVDGOT-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-methoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F NLSWTNSYKVDGOT-UHFFFAOYSA-N 0.000 claims 1
- YVUGLKUKJPAEAT-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-methylsulfonylfuro[3,2-c]pyridine-2-carboxamide Chemical compound CS(=O)(=O)NC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F YVUGLKUKJPAEAT-UHFFFAOYSA-N 0.000 claims 1
- IQXHJWQCHIFPOH-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-phenoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOC=2C=CC=CC=2)OC2=CC=NC=C12 IQXHJWQCHIFPOH-UHFFFAOYSA-N 0.000 claims 1
- YYSYZXLKBHAFQP-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-phenylmethoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCC=2C=CC=CC=2)OC2=CC=NC=C12 YYSYZXLKBHAFQP-UHFFFAOYSA-N 0.000 claims 1
- PYVXSCSFCDZMET-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-piperidin-4-yloxyfuro[3,2-c]pyridine-2-carboxamide;formic acid Chemical compound OC=O.FC1=CC(I)=CC=C1NC1=C(C(=O)NOC2CCNCC2)OC2=CC=NC=C12 PYVXSCSFCDZMET-UHFFFAOYSA-N 0.000 claims 1
- WDYKHMRALAELNL-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-propan-2-yloxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound CC(C)ONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F WDYKHMRALAELNL-UHFFFAOYSA-N 0.000 claims 1
- GYCNBDSPAUCLMY-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)-n-propoxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound CCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(I)C=C1F GYCNBDSPAUCLMY-UHFFFAOYSA-N 0.000 claims 1
- IDPRSJFPZKEETI-UHFFFAOYSA-N 3-(2-fluoro-4-methoxyanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(OC)=CC=C1NC1=C(C(=O)NOCCO)OC2=CC=NC=C12 IDPRSJFPZKEETI-UHFFFAOYSA-N 0.000 claims 1
- XRJBBHQHSPVSSV-UHFFFAOYSA-N 3-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)OC2=CC=NC=C12 XRJBBHQHSPVSSV-UHFFFAOYSA-N 0.000 claims 1
- MBDVAIXTFKWSIQ-UHFFFAOYSA-N 3-(4-bromo-2-chloroanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(Br)C=C1Cl MBDVAIXTFKWSIQ-UHFFFAOYSA-N 0.000 claims 1
- KFCJJPYOSOKYOC-SNVBAGLBSA-N 3-(4-bromo-2-fluoroanilino)-n-[(2r)-2,3-dihydroxypropoxy]furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(Br)C=C1F KFCJJPYOSOKYOC-SNVBAGLBSA-N 0.000 claims 1
- CYMSZXYMQOWREV-UHFFFAOYSA-N 3-[2-fluoro-4-(hydroxymethyl)anilino]-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC=C2C=1NC1=CC=C(CO)C=C1F CYMSZXYMQOWREV-UHFFFAOYSA-N 0.000 claims 1
- ZHAATOXXOFJKOI-UHFFFAOYSA-N 4-chloro-3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=CC=NC(Cl)=C2C=1NC1=CC=C(I)C=C1F ZHAATOXXOFJKOI-UHFFFAOYSA-N 0.000 claims 1
- DBCSLIDHWJMBTA-SECBINFHSA-N 7-bromo-n-[(2r)-2,3-dihydroxypropoxy]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-2-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C=1OC2=C(Br)C=NC=C2C=1NC1=CC=C(I)C=C1F DBCSLIDHWJMBTA-SECBINFHSA-N 0.000 claims 1
- BLTCPZNAPZCEHZ-UHFFFAOYSA-N 7-chloro-3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=C(Cl)C=NC=C2C=1NC1=CC=C(I)C=C1F BLTCPZNAPZCEHZ-UHFFFAOYSA-N 0.000 claims 1
- MXTXYFYQDUYXJL-JTQLQIEISA-N 7-chloro-3-(2-fluoro-4-iodoanilino)-n-[(3s)-pyrrolidin-3-yl]oxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NO[C@@H]2CNCC2)OC2=C(Cl)C=NC=C12 MXTXYFYQDUYXJL-JTQLQIEISA-N 0.000 claims 1
- GHRBIPYIAHXFCH-UHFFFAOYSA-N 7-chloro-3-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)OC2=C(Cl)C=NC=C12 GHRBIPYIAHXFCH-UHFFFAOYSA-N 0.000 claims 1
- RZJMBERNOWZWPE-UHFFFAOYSA-N 7-cyano-3-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound OCCONC(=O)C=1OC2=C(C#N)C=NC=C2C=1NC1=CC=C(I)C=C1F RZJMBERNOWZWPE-UHFFFAOYSA-N 0.000 claims 1
- SJISFKLIAOHHHQ-UHFFFAOYSA-N 7-fluoro-3-(2-fluoro-4-iodoanilino)-n-(1-hydroxy-2-methylpropan-2-yl)oxyfuro[3,2-c]pyridine-2-carboxamide Chemical compound OCC(C)(C)ONC(=O)C=1OC2=C(F)C=NC=C2C=1NC1=CC=C(I)C=C1F SJISFKLIAOHHHQ-UHFFFAOYSA-N 0.000 claims 1
- KTCIDTVOVGOCMK-UHFFFAOYSA-N 7-fluoro-3-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)furo[3,2-c]pyridine-2-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)OC2=C(F)C=NC=C12 KTCIDTVOVGOCMK-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- SEEBPOKQKKFAJK-UHFFFAOYSA-N C(=O)O.N1CC(CCC1)ONC(=O)C1=C(C=2C=NC=CC2O1)NC1=C(C=C(C=C1)I)F Chemical compound C(=O)O.N1CC(CCC1)ONC(=O)C1=C(C=2C=NC=CC2O1)NC1=C(C=C(C=C1)I)F SEEBPOKQKKFAJK-UHFFFAOYSA-N 0.000 claims 1
- ZEZHPEIEEFTILY-QMMMGPOBSA-N G-573 Chemical compound C[C@H](O)CONC(=O)C=1OC2=C(F)C=NC=C2C=1NC1=CC=C(I)C=C1F ZEZHPEIEEFTILY-QMMMGPOBSA-N 0.000 claims 1
- FZBPBLMUNZUMJG-UHFFFAOYSA-N N-(2-hydroxyethoxy)pyridine-2-carboxamide Chemical compound OCCONC(=O)c1ccccn1 FZBPBLMUNZUMJG-UHFFFAOYSA-N 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- 230000001066 destructive effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZMBOQMSDMSOZDL-LLVKDONJSA-N ethyl 2-[[(2r)-2,3-dihydroxypropoxy]carbamoyl]-3-(2-fluoro-4-iodoanilino)furo[3,2-c]pyridine-7-carboxylate Chemical compound OC[C@@H](O)CONC(=O)C=1OC=2C(C(=O)OCC)=CN=CC=2C=1NC1=CC=C(I)C=C1F ZMBOQMSDMSOZDL-LLVKDONJSA-N 0.000 claims 1
- WWMNKLYZTHPRHY-OAHLLOKOSA-N ethyl 2-[[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxycarbamoyl]-3-(2-fluoro-4-trimethylsilylanilino)furo[3,2-c]pyridine-7-carboxylate Chemical compound C([C@@H]1OC(C)(C)OC1)ONC(=O)C=1OC=2C(C(=O)OCC)=CN=CC=2C=1NC1=CC=C([Si](C)(C)C)C=C1F WWMNKLYZTHPRHY-OAHLLOKOSA-N 0.000 claims 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
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- 2007-08-20 JP JP2009525720A patent/JP5448818B2/ja not_active Expired - Fee Related
- 2007-08-20 CA CA002660546A patent/CA2660546A1/en not_active Abandoned
- 2007-08-20 AT AT07814272T patent/ATE531720T1/de active
- 2007-08-20 WO PCT/US2007/076344 patent/WO2008024725A1/en not_active Ceased
- 2007-08-21 PE PE2007001135A patent/PE20080611A1/es not_active Application Discontinuation
- 2007-08-21 TW TW096130982A patent/TWI411614B/zh not_active IP Right Cessation
- 2007-08-21 AR ARP070103712A patent/AR062468A1/es unknown
-
2009
- 2009-02-09 IL IL196956A patent/IL196956A/en not_active IP Right Cessation
- 2009-03-20 NO NO20091197A patent/NO20091197L/no not_active Application Discontinuation