JP2007509130A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2007509130A5 JP2007509130A5 JP2006536215A JP2006536215A JP2007509130A5 JP 2007509130 A5 JP2007509130 A5 JP 2007509130A5 JP 2006536215 A JP2006536215 A JP 2006536215A JP 2006536215 A JP2006536215 A JP 2006536215A JP 2007509130 A5 JP2007509130 A5 JP 2007509130A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- oxazol
- methyl
- pyridin
- ylamino
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 45
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 229910052794 bromium Inorganic materials 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 229910052740 iodine Inorganic materials 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- -1 amino, carboxyl Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 125000004355 nitrogen functional group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 3
- 229910052705 radium Inorganic materials 0.000 claims 3
- 229910052701 rubidium Inorganic materials 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 2
- 229910003827 NRaRb Inorganic materials 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 210000001185 bone marrow Anatomy 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- YJTHDZOOFLIDAH-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=CC=C1F YJTHDZOOFLIDAH-UHFFFAOYSA-N 0.000 claims 1
- LLKMLSXETYSLPE-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 LLKMLSXETYSLPE-UHFFFAOYSA-N 0.000 claims 1
- BGQHVFBHLADCQZ-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]thiourea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=S)NC1=CC=C(C#N)C=C1 BGQHVFBHLADCQZ-UHFFFAOYSA-N 0.000 claims 1
- BAVXBJWGPLEKED-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=C(C#N)C=C1 BAVXBJWGPLEKED-UHFFFAOYSA-N 0.000 claims 1
- PLQYBDZYCAXEDV-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]thiourea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(=S)NC1=CC=C(C#N)C=C1 PLQYBDZYCAXEDV-UHFFFAOYSA-N 0.000 claims 1
- NTOGTTYFZKYUPA-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 NTOGTTYFZKYUPA-UHFFFAOYSA-N 0.000 claims 1
- KZFOFDORPQTDHN-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 KZFOFDORPQTDHN-UHFFFAOYSA-N 0.000 claims 1
- MQERDMHSJBACBG-UHFFFAOYSA-N 1-[4-methyl-3-[(5-phenyl-1,3-oxazol-2-yl)amino]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 MQERDMHSJBACBG-UHFFFAOYSA-N 0.000 claims 1
- XXCYDEXIHBWQBC-UHFFFAOYSA-N 1-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 XXCYDEXIHBWQBC-UHFFFAOYSA-N 0.000 claims 1
- CGCLXYGIXNAGFW-UHFFFAOYSA-N 1-benzyl-3-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]thiourea Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(=S)NCC1=CC=CC=C1 CGCLXYGIXNAGFW-UHFFFAOYSA-N 0.000 claims 1
- YSUBMVSDUMNSNS-UHFFFAOYSA-N 1-n-(1,3-benzoxazol-2-yl)-4-methyl-3-n-(5-pyridin-4-yl-1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound CC1=CC=C(NC=2OC3=CC=CC=C3N=2)C=C1NC(O1)=NC=C1C1=CC=NC=C1 YSUBMVSDUMNSNS-UHFFFAOYSA-N 0.000 claims 1
- AJWYELFDOXLJJR-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-n-[4-methyl-3-[(5-phenyl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CC=CC=2)C(C)=CC=C1NC(=O)CC1=CC=C(F)C=C1F AJWYELFDOXLJJR-UHFFFAOYSA-N 0.000 claims 1
- LBOHDXZQUHPFSL-UHFFFAOYSA-N 2-(3-bromophenyl)-n-[4-methyl-3-[(5-pyridin-2-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2N=CC=CC=2)C(C)=CC=C1NC(=O)CC1=CC=CC(Br)=C1 LBOHDXZQUHPFSL-UHFFFAOYSA-N 0.000 claims 1
- KEEBUCPGLVETKH-UHFFFAOYSA-N 2-(3-methylphenyl)-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound CC1=CC=CC(CC(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=CN=CC=3)C(C)=CC=2)=C1 KEEBUCPGLVETKH-UHFFFAOYSA-N 0.000 claims 1
- JXPUQFYLPGOUHE-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-methoxy-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(OC)=CC=C1NC(=O)CC1=CC=C(F)C=C1 JXPUQFYLPGOUHE-UHFFFAOYSA-N 0.000 claims 1
- NHNPJUHHBDTXMQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)CC1=CC=C(F)C=C1 NHNPJUHHBDTXMQ-UHFFFAOYSA-N 0.000 claims 1
- CLLCSCDTYOIJHO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=CN=CC=2)=C1 CLLCSCDTYOIJHO-UHFFFAOYSA-N 0.000 claims 1
- MTDSANYYCBYFOZ-UHFFFAOYSA-N 2-cyano-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound CC1=CC=C(NC(=O)CC#N)C=C1NC1=NC=C(C=2C=CN=CC=2)O1 MTDSANYYCBYFOZ-UHFFFAOYSA-N 0.000 claims 1
- CBRSXJFHARVENS-UHFFFAOYSA-N 2-ethoxy-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound CCOCC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 CBRSXJFHARVENS-UHFFFAOYSA-N 0.000 claims 1
- IGLZHUHGTKHGHJ-UHFFFAOYSA-N 2-methylpropyl n-[2-methyl-5-(2-methylpropoxycarbonylamino)phenyl]-n-(5-pyridin-3-yl-1,3-oxazol-2-yl)carbamate Chemical compound CC(C)COC(=O)NC1=CC=C(C)C(N(C(=O)OCC(C)C)C=2OC(=CN=2)C=2C=NC=CC=2)=C1 IGLZHUHGTKHGHJ-UHFFFAOYSA-N 0.000 claims 1
- VMHVHLSOHUQGSO-UHFFFAOYSA-N 2-methylpropyl n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]carbamate Chemical compound CC(C)COC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 VMHVHLSOHUQGSO-UHFFFAOYSA-N 0.000 claims 1
- VCQMPUPEARTEGT-UHFFFAOYSA-N 2-methylpropyl n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]carbamate Chemical compound CC(C)COC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=CN=CC=2)=C1 VCQMPUPEARTEGT-UHFFFAOYSA-N 0.000 claims 1
- ONZFPAUTTVNGRO-UHFFFAOYSA-N 3,5-dimethoxy-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound COC1=CC(OC)=CC(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=CN=CC=3)C(C)=CC=2)=C1 ONZFPAUTTVNGRO-UHFFFAOYSA-N 0.000 claims 1
- VBUDIOJRHSRDNE-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]propanamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(=O)CCC1=CC=C(F)C=C1 VBUDIOJRHSRDNE-UHFFFAOYSA-N 0.000 claims 1
- QQGKEUWTCWSWIM-UHFFFAOYSA-N 3-(dimethylamino)-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound CN(C)C1=CC=CC(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=C1 QQGKEUWTCWSWIM-UHFFFAOYSA-N 0.000 claims 1
- CFSOZHKOFYGOJX-UHFFFAOYSA-N 3-bromo-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(Br)=C1 CFSOZHKOFYGOJX-UHFFFAOYSA-N 0.000 claims 1
- IFZBJUUFHJRIQE-UHFFFAOYSA-N 3-fluoro-4-[(4-methylpiperazin-1-yl)methyl]-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1F IFZBJUUFHJRIQE-UHFFFAOYSA-N 0.000 claims 1
- IDXSLYWMIDHQFU-UHFFFAOYSA-N 3-methoxy-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]propanamide Chemical compound COCCC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 IDXSLYWMIDHQFU-UHFFFAOYSA-N 0.000 claims 1
- FLSOCFCHSDCSMM-UHFFFAOYSA-N 4-[(4-methylpiperazin-1-yl)methyl]-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 FLSOCFCHSDCSMM-UHFFFAOYSA-N 0.000 claims 1
- QHAQNXJCRZHKRZ-UHFFFAOYSA-N 4-[3-(dimethylamino)propylamino]-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(NCCCN(C)C)=CC=C1C(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 QHAQNXJCRZHKRZ-UHFFFAOYSA-N 0.000 claims 1
- GQGBFHDLMSEMFF-UHFFFAOYSA-N 4-cyano-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]benzamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(=O)C1=CC=C(C#N)C=C1 GQGBFHDLMSEMFF-UHFFFAOYSA-N 0.000 claims 1
- LLRWNDWHVNPUMJ-UHFFFAOYSA-N 4-methyl-1-n-(5-phenyl-1,3-oxazol-2-yl)-3-n-(5-pyridin-4-yl-1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(O1)=NC=C1C1=CC=CC=C1 LLRWNDWHVNPUMJ-UHFFFAOYSA-N 0.000 claims 1
- CBOXAKYSTSFXTD-UHFFFAOYSA-N 4-methyl-1-n-(5-pyridin-3-yl-1,3-oxazol-2-yl)-3-n-(5-pyridin-4-yl-1,3-oxazol-2-yl)benzene-1,3-diamine Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NC(O1)=NC=C1C1=CC=CN=C1 CBOXAKYSTSFXTD-UHFFFAOYSA-N 0.000 claims 1
- TXHCAUUNNPYFJD-UHFFFAOYSA-N 4-methyl-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]pentanamide Chemical compound CC(C)CCC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 TXHCAUUNNPYFJD-UHFFFAOYSA-N 0.000 claims 1
- CEUWQPLATDRHEL-UHFFFAOYSA-N 4-n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]benzene-1,4-dicarboxamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C1=CC=C(C(N)=O)C=C1 CEUWQPLATDRHEL-UHFFFAOYSA-N 0.000 claims 1
- LGZSXFUMYWZFGV-UHFFFAOYSA-N 5-methyl-n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=CN=CC=3)C(C)=CC=2)=C1C LGZSXFUMYWZFGV-UHFFFAOYSA-N 0.000 claims 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 206010049153 Allergic sinusitis Diseases 0.000 claims 1
- 206010002198 Anaphylactic reaction Diseases 0.000 claims 1
- 208000028185 Angioedema Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010003571 Astrocytoma Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- PWWVRIBAKATTFH-UHFFFAOYSA-N CC1=C(C=C(C=C1)NC(CCN1CCCC1)=O)NC=1OC(=CN1)C=1C=NC=CC1.ClC1=C(C(=CC=C1)Cl)CC(=O)NC1=CC(=C(C=C1)C)NC=1OC(=CN1)C1=CC=NC=C1 Chemical compound CC1=C(C=C(C=C1)NC(CCN1CCCC1)=O)NC=1OC(=CN1)C=1C=NC=CC1.ClC1=C(C(=CC=C1)Cl)CC(=O)NC1=CC(=C(C=C1)C)NC=1OC(=CN1)C1=CC=NC=C1 PWWVRIBAKATTFH-UHFFFAOYSA-N 0.000 claims 1
- 241000282465 Canis Species 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 208000006926 Discoid Lupus Erythematosus Diseases 0.000 claims 1
- 206010058314 Dysplasia Diseases 0.000 claims 1
- 206010015218 Erythema multiforme Diseases 0.000 claims 1
- 206010015226 Erythema nodosum Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000006877 Insect Bites and Stings Diseases 0.000 claims 1
- 208000000185 Localized scleroderma Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 208000030852 Parasitic disease Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010036030 Polyarthritis Diseases 0.000 claims 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- OYNHMJOHYYXABZ-UHFFFAOYSA-N [4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-morpholin-4-ylmethanone Chemical compound CC1=CC=C(C(=O)N2CCOCC2)C=C1NC(O1)=NC=C1C1=CC=NC=C1 OYNHMJOHYYXABZ-UHFFFAOYSA-N 0.000 claims 1
- SGKCMBLBWJQZDX-UHFFFAOYSA-N [4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-piperazin-1-ylmethanone Chemical compound CC1=CC=C(C(=O)N2CCNCC2)C=C1NC(O1)=NC=C1C1=CC=NC=C1 SGKCMBLBWJQZDX-UHFFFAOYSA-N 0.000 claims 1
- 208000002029 allergic contact dermatitis Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 230000036783 anaphylactic response Effects 0.000 claims 1
- 208000003455 anaphylaxis Diseases 0.000 claims 1
- 206010003230 arteritis Diseases 0.000 claims 1
- 230000002917 arthritic effect Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 claims 1
- 201000001981 dermatomyositis Diseases 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- LDEQXBADOLOWQB-UHFFFAOYSA-N ethyl 2-[2-[2-methyl-5-[[4-(trifluoromethyl)phenyl]carbamoylamino]anilino]-1,3-oxazol-5-yl]acetate Chemical compound O1C(CC(=O)OCC)=CN=C1NC1=CC(NC(=O)NC=2C=CC(=CC=2)C(F)(F)F)=CC=C1C LDEQXBADOLOWQB-UHFFFAOYSA-N 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 210000002216 heart Anatomy 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 201000006512 mast cell neoplasm Diseases 0.000 claims 1
- 208000006971 mastocytoma Diseases 0.000 claims 1
- 208000008585 mastocytosis Diseases 0.000 claims 1
- RIAYRNVHQWZIBD-UHFFFAOYSA-N methyl 4-[[4-methyl-3-[(4-pyridin-3-yl-1,3-oxazol-2-yl)amino]anilino]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CNC1=CC=C(C)C(NC=2OC=C(N=2)C=2C=NC=CC=2)=C1 RIAYRNVHQWZIBD-UHFFFAOYSA-N 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- HOWLHUUPCSMTAZ-UHFFFAOYSA-N n-(3-chlorophenyl)-4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(Cl)C=CC=2)C=C1NC(O1)=NC=C1C1=CC=CN=C1 HOWLHUUPCSMTAZ-UHFFFAOYSA-N 0.000 claims 1
- VZXNYEPZQACYHR-UHFFFAOYSA-N n-(3-fluoro-4-methylphenyl)-4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound C1=C(F)C(C)=CC=C1NC(=O)C1=CC=C(C)C(NC=2OC(=CN=2)C=2C=CN=CC=2)=C1 VZXNYEPZQACYHR-UHFFFAOYSA-N 0.000 claims 1
- BLAFNVLTEJJENP-UHFFFAOYSA-N n-(4-cyanophenyl)-4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=CC(=CC=2)C#N)C=C1NC(O1)=NC=C1C1=CC=CN=C1 BLAFNVLTEJJENP-UHFFFAOYSA-N 0.000 claims 1
- VZYBLENJMIDDAE-UHFFFAOYSA-N n-(4-fluorophenyl)-2-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1CC(=O)NC1=CC=C(F)C=C1 VZYBLENJMIDDAE-UHFFFAOYSA-N 0.000 claims 1
- IPIWTZUPUBHJCL-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CC=C(C)C(NC=2OC(=CN=2)C=2C=CN=CC=2)=C1 IPIWTZUPUBHJCL-UHFFFAOYSA-N 0.000 claims 1
- OVSPCJDMIPJNHX-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CN(C)CCNC(=O)C1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 OVSPCJDMIPJNHX-UHFFFAOYSA-N 0.000 claims 1
- URDAADWEIKUUPU-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]-4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CN(C)C1=CC=CC(NC(=O)C=2C=C(NC=3OC(=CN=3)C=3C=CN=CC=3)C(C)=CC=2)=C1 URDAADWEIKUUPU-UHFFFAOYSA-N 0.000 claims 1
- WHKFRFKKQRZOAM-UHFFFAOYSA-N n-[3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=NC=CC=3)C=CC=2)=C1 WHKFRFKKQRZOAM-UHFFFAOYSA-N 0.000 claims 1
- CEATXLYGLKXKBX-UHFFFAOYSA-N n-[3-[[5-(4-cyanophenyl)-1,3-oxazol-2-yl]amino]-4-methylphenyl]-2-(2,4-difluorophenyl)acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CC(=CC=2)C#N)C(C)=CC=C1NC(=O)CC1=CC=C(F)C=C1F CEATXLYGLKXKBX-UHFFFAOYSA-N 0.000 claims 1
- ODUIXQCTCFZYAW-UHFFFAOYSA-N n-[4-chloro-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=NC=CC=3)C(Cl)=CC=2)=C1 ODUIXQCTCFZYAW-UHFFFAOYSA-N 0.000 claims 1
- RFBZLUWAOIJRQR-UHFFFAOYSA-N n-[4-fluoro-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(F)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 RFBZLUWAOIJRQR-UHFFFAOYSA-N 0.000 claims 1
- MZMBQVYIUHWTHE-UHFFFAOYSA-N n-[4-methoxy-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(OC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 MZMBQVYIUHWTHE-UHFFFAOYSA-N 0.000 claims 1
- XIZNQJMQUBYUJV-UHFFFAOYSA-N n-[4-methoxy-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(OC)=CC=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 XIZNQJMQUBYUJV-UHFFFAOYSA-N 0.000 claims 1
- WLZKZWONUFPREG-UHFFFAOYSA-N n-[4-methyl-3-[(4-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2OC=C(N=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 WLZKZWONUFPREG-UHFFFAOYSA-N 0.000 claims 1
- NTDCCVFLWYRGDH-UHFFFAOYSA-N n-[4-methyl-3-[(5-phenyl-1,3-oxazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CC=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 NTDCCVFLWYRGDH-UHFFFAOYSA-N 0.000 claims 1
- YUENBBXFAOPQMB-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-2-yl-1,3-oxazol-2-yl)amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2OC(=CN=2)C=2N=CC=CC=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 YUENBBXFAOPQMB-UHFFFAOYSA-N 0.000 claims 1
- MBXJCNACGQESRD-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-2-piperazin-1-ylacetamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)CN1CCNCC1 MBXJCNACGQESRD-UHFFFAOYSA-N 0.000 claims 1
- MGFIEQNFVMOMCT-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]-3-piperazin-1-ylpropanamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=NC=CC=2)C(C)=CC=C1NC(=O)CCN1CCNCC1 MGFIEQNFVMOMCT-UHFFFAOYSA-N 0.000 claims 1
- WTHMHBCPQRFUBK-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-3-yl-1,3-oxazol-2-yl)amino]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C(NC=2OC(=CN=2)C=2C=NC=CC=2)=C1 WTHMHBCPQRFUBK-UHFFFAOYSA-N 0.000 claims 1
- PVWWBTNRVDVQIP-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-1-phenylmethanesulfonamide Chemical compound C1=C(NC=2OC(=CN=2)C=2C=CN=CC=2)C(C)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 PVWWBTNRVDVQIP-UHFFFAOYSA-N 0.000 claims 1
- FDAHBOFXYSTPOL-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-1h-indole-6-carboxamide Chemical compound CC1=CC=C(NC(=O)C=2C=C3NC=CC3=CC=2)C=C1NC(O1)=NC=C1C1=CC=NC=C1 FDAHBOFXYSTPOL-UHFFFAOYSA-N 0.000 claims 1
- FOMPQOZSGBLQMX-UHFFFAOYSA-N n-[4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]phenyl]-3-propan-2-yloxybenzamide Chemical compound CC(C)OC1=CC=CC(C(=O)NC=2C=C(NC=3OC(=CN=3)C=3C=CN=CC=3)C(C)=CC=2)=C1 FOMPQOZSGBLQMX-UHFFFAOYSA-N 0.000 claims 1
- HORDAYGVVWNPQO-UHFFFAOYSA-N n-benzyl-4-methyl-3-[(5-pyridin-4-yl-1,3-oxazol-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NCC=2C=CC=CC=2)C=C1NC(O1)=NC=C1C1=CC=NC=C1 HORDAYGVVWNPQO-UHFFFAOYSA-N 0.000 claims 1
- 230000001338 necrotic effect Effects 0.000 claims 1
- 230000002956 necrotizing effect Effects 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 208000030428 polyarticular arthritis Diseases 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 201000008171 proliferative glomerulonephritis Diseases 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 239000002585 base Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 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 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 0 *C(Nc1c(*)c(Nc2nc(*)c(*)[o]2)c(*)c(*)c1*)=* Chemical compound *C(Nc1c(*)c(Nc2nc(*)c(*)[o]2)c(*)c(*)c1*)=* 0.000 description 1
- BGZFLGJHUQVPEY-UHFFFAOYSA-N 2-(1,3-oxazol-2-yl)benzene-1,3-diamine Chemical class NC1=CC=CC(N)=C1C1=NC=CO1 BGZFLGJHUQVPEY-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51321403P | 2003-10-23 | 2003-10-23 | |
| US60/513,214 | 2003-10-23 | ||
| PCT/IB2004/003698 WO2005040139A2 (en) | 2003-10-23 | 2004-10-22 | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007509130A JP2007509130A (ja) | 2007-04-12 |
| JP2007509130A5 true JP2007509130A5 (https=) | 2011-07-28 |
| JP4971797B2 JP4971797B2 (ja) | 2012-07-11 |
Family
ID=42827352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006536215A Expired - Fee Related JP4971797B2 (ja) | 2003-10-23 | 2004-10-22 | チロシンキナーゼ阻害薬としての２−アミノアリールオキサゾール化合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7718676B2 (https=) |
| EP (1) | EP1684750B1 (https=) |
| JP (1) | JP4971797B2 (https=) |
| CN (1) | CN1950347B (https=) |
| AT (1) | ATE465731T1 (https=) |
| AU (1) | AU2004283162B2 (https=) |
| BR (1) | BRPI0415467A (https=) |
| CA (1) | CA2542909C (https=) |
| DK (1) | DK1684750T3 (https=) |
| HR (1) | HRP20100326T1 (https=) |
| IL (1) | IL175028A (https=) |
| NO (1) | NO20062308L (https=) |
| NZ (1) | NZ546645A (https=) |
| PL (1) | PL1684750T3 (https=) |
| WO (1) | WO2005040139A2 (https=) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004019212D1 (de) | 2003-05-31 | 2009-03-12 | Cameron Systems Ireland Ltd | Vorrichtung und verfahren zur rückgewinnung der unterirdischen flüssigkeiten und/oder injizieren von flüssigkeiten in einem bohrloch |
| US7652044B2 (en) * | 2003-06-03 | 2010-01-26 | Novartis A.G. | P-38 inhibitors |
| EP1684750B1 (en) * | 2003-10-23 | 2010-04-28 | AB Science | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
| CA2555403C (en) | 2004-02-26 | 2012-08-21 | Des Enhanced Recovery Limited | Connection system for subsea flow interface equipment |
| WO2005102318A1 (en) * | 2004-04-20 | 2005-11-03 | Ab Science | Use of c-kit inhibitors for treating hiv related diseases |
| CA2564568A1 (en) * | 2004-04-20 | 2005-11-03 | Ab Science | Use of c-kit inhibitors for treating inflammatory muscle disorders including myositis and muscular dystrophy |
| EP1746990A1 (en) * | 2004-05-18 | 2007-01-31 | AB Science | Use of mast cells inhibitors for treating patients exposed to chemical or biological weapons |
| WO2005115385A1 (en) * | 2004-05-24 | 2005-12-08 | Ab Science | Use of c-kit inhibitors for treating acne |
| AU2006231929B2 (en) * | 2005-04-04 | 2012-09-06 | Ab Science | Substituted oxazole derivatives and their use as tyrosine kinase inhibitors |
| US20060281788A1 (en) | 2005-06-10 | 2006-12-14 | Baumann Christian A | Synergistic modulation of flt3 kinase using a flt3 inhibitor and a farnesyl transferase inhibitor |
| EP1904065A2 (en) * | 2005-07-14 | 2008-04-02 | AB Science | Use of dual c-kit/fgfr3 inhibitors for treating multiple myeloma |
| WO2007076460A2 (en) * | 2005-12-23 | 2007-07-05 | Kalypsys, Inc. | Substituted thiazole ureas useful as inhibitors of protein kinases |
| US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| EA016611B1 (ru) * | 2006-04-20 | 2012-06-29 | Янссен Фармацевтика Н.В. | Способ лечения мастоцитоза |
| NZ572073A (en) | 2006-04-20 | 2011-09-30 | Janssen Pharmaceutica Nv | Heterocyclic compounds as inhibitors of c-fms kinase |
| BRPI0710548B8 (pt) | 2006-04-20 | 2021-05-25 | Janssen Pharmaceutica Nv | inibidores de c-fms cinase, composição farmacêutica e forma de dosagem farmacêutica |
| GB0618001D0 (en) | 2006-09-13 | 2006-10-18 | Des Enhanced Recovery Ltd | Method |
| US7790756B2 (en) * | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| GB0625191D0 (en) | 2006-12-18 | 2007-01-24 | Des Enhanced Recovery Ltd | Apparatus and method |
| GB0625526D0 (en) | 2006-12-18 | 2007-01-31 | Des Enhanced Recovery Ltd | Apparatus and method |
| ES2606505T3 (es) * | 2007-01-12 | 2017-03-24 | Ab Science | Tratamiento de combinación de cánceres sólidos con antimetabolitos e inhibidores de tirosina quinasa |
| GB0701426D0 (en) * | 2007-01-25 | 2007-03-07 | Univ Sheffield | Compounds and their use |
| GB0709031D0 (en) * | 2007-05-10 | 2007-06-20 | Sareum Ltd | Pharmaceutical compounds |
| JO3240B1 (ar) | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
| FR2928150A1 (fr) * | 2008-02-29 | 2009-09-04 | Vetoquinol Sa Sa | Nouveaux derives 7-substitues de 3-carboxy-oxadiazino-quinolones, leur preparation et leur application comme anti-bacteriens |
| EP2145891A1 (en) * | 2008-07-09 | 2010-01-20 | Vetoquinol S.A. | 9-substituted-5-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials |
| GB0820819D0 (en) | 2008-11-13 | 2008-12-24 | Sareum Ltd | Pharmaceutical compounds |
| US9180127B2 (en) | 2009-12-29 | 2015-11-10 | Dana-Farber Cancer Institute, Inc. | Type II Raf kinase inhibitors |
| MX2013009961A (es) * | 2011-03-01 | 2013-09-26 | Npharmakon Llc | Uso de n-(4-metoxifenil)-1-fenil-1h-pirazol-3-amina y compuestos relacionados. |
| WO2012166463A2 (en) * | 2011-05-27 | 2012-12-06 | Neosome Life Sciences, LLC | Aminooxazole inhibitors of cyclin dependent kinases |
| EP2736904B1 (en) * | 2011-07-27 | 2016-03-16 | AB Science | Oxazole and thiazole derivatives as selective protein kinase inhibitors (c-kit) |
| GB201202027D0 (en) | 2012-02-06 | 2012-03-21 | Sareum Ltd | Pharmaceutical compounds |
| DK2634185T3 (en) | 2012-03-02 | 2016-03-21 | Sareum Ltd | Tyk2 kinase inhibitors |
| IN2015DN00659A (https=) | 2012-08-07 | 2015-06-26 | Janssen Pharmaceutica Nv | |
| JP6290884B2 (ja) | 2012-08-07 | 2018-03-07 | ヤンセン ファーマシューティカ エヌ．ベー． | ｃ−ＦＭＳキナーゼ阻害剤の調製プロセス |
| US20160175302A1 (en) * | 2014-12-17 | 2016-06-23 | Ab Science | Masitinib for treating gastric cancer |
| AU2015371251B2 (en) | 2014-12-23 | 2020-06-11 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (CDK7) |
| ES2796276T3 (es) * | 2015-02-05 | 2020-11-26 | Ab Science | Compuestos con actividad antitumoral |
| HK1246645A1 (zh) | 2015-03-27 | 2018-09-14 | 达纳-法伯癌症研究所股份有限公司 | 细胞周期蛋白依赖性激酶的抑制剂 |
| EP3347018B1 (en) | 2015-09-09 | 2021-09-01 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| GB201617871D0 (en) | 2016-10-21 | 2016-12-07 | Sareum Limited | Pharmaceutical compounds |
| US12187701B2 (en) | 2018-06-25 | 2025-01-07 | Dana-Farber Cancer Institute, Inc. | Taire family kinase inhibitors and uses thereof |
| GB201816369D0 (en) | 2018-10-08 | 2018-11-28 | Sareum Ltd | Pharmaceutical compounds |
| WO2021047677A1 (zh) * | 2019-09-12 | 2021-03-18 | 中国科学院上海药物研究所 | 一类irak4激酶抑制剂及其制备和应用 |
| GB202005114D0 (en) | 2020-04-07 | 2020-05-20 | Sareum Ltd | Crystalline Forms of a Pharmaceutical Compound |
| WO2022040558A1 (en) * | 2020-08-21 | 2022-02-24 | Pylon Manufacturing Corp. | Windshield wiper blade |
| CN113185511B (zh) * | 2021-05-24 | 2022-04-26 | 中国医学科学院医药生物技术研究所 | 一种嘧啶类化合物及其制备方法和应用 |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3740420A (en) | 1967-11-28 | 1973-06-19 | Crown Zellerbach Corp | Pharmaceutical compositions with dimethyl sulfoxide |
| FR2077803B1 (https=) | 1970-02-16 | 1973-03-16 | Innothera Lab Sa | |
| US3743727A (en) | 1970-11-16 | 1973-07-03 | Crown Zellerbach Corp | Enhancing tissue penetration of certain antimicrobial agents with dimethyl sulfoxide |
| US4405616A (en) | 1975-06-19 | 1983-09-20 | Nelson Research & Development Company | Penetration enhancers for transdermal drug delivery of systemic agents |
| US3989816A (en) | 1975-06-19 | 1976-11-02 | Nelson Research & Development Company | Vehicle composition containing 1-substituted azacycloheptan-2-ones |
| US4343940A (en) | 1979-02-13 | 1982-08-10 | Mead Johnson & Company | Anti-tumor quinazoline compounds |
| CA1163561A (en) | 1979-11-06 | 1984-03-13 | Cyril Boroda | Preparation containing nitroglycerine and optionally other medicaments and preparation thereof |
| US4379454A (en) | 1981-02-17 | 1983-04-12 | Alza Corporation | Dosage for coadministering drug and percutaneous absorption enhancer |
| US4460372A (en) | 1981-02-17 | 1984-07-17 | Alza Corporation | Percutaneous absorption enhancer dispenser for use in coadministering drug and percutaneous absorption enhancer |
| US4411893A (en) | 1981-08-14 | 1983-10-25 | Minnesota Mining And Manufacturing Company | Topical medicament preparations |
| CA1236029A (en) | 1984-05-14 | 1988-05-03 | Edmund Sandborn | Pharmaceutical solutions comprising dimethyl sulfoxide |
| US4615699A (en) | 1985-05-03 | 1986-10-07 | Alza Corporation | Transdermal delivery system for delivering nitroglycerin at high transdermal fluxes |
| US5000775A (en) * | 1985-12-31 | 1991-03-19 | Monsanto Company | 2-amino-4,5-disubstituted-oxazole/thiazole compounds as herbicide antidotes |
| JPH0651679B2 (ja) * | 1986-07-21 | 1994-07-06 | 株式会社大塚製薬工場 | ｐ−アミノフェノ−ル誘導体 |
| US4868183A (en) * | 1986-07-21 | 1989-09-19 | Otsuka Pharmaceutical Factory, Inc. | N-pyrazinyl substituted P-aminophenols |
| US5217999A (en) | 1987-12-24 | 1993-06-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Styryl compounds which inhibit EGF receptor protein tyrosine kinase |
| DE3815221C2 (de) | 1988-05-04 | 1995-06-29 | Gradinger F Hermes Pharma | Verwendung einer Retinol- und/oder Retinsäureester enthaltenden pharmazeutischen Zubereitung zur Inhalation zur Einwirkung auf die Schleimhäute des Tracheo-Bronchialtraktes einschließlich der Lungenalveolen |
| DE69105495T2 (de) | 1990-04-02 | 1995-04-06 | Pfizer | Benzylphosphonsäure-tyrosinkinaseinhibitoren. |
| US5302606A (en) | 1990-04-16 | 1994-04-12 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Styryl-substituted pyridyl compounds which inhibit EGF receptor tyrosine kinase |
| US5721237A (en) | 1991-05-10 | 1998-02-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties |
| US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5409930A (en) | 1991-05-10 | 1995-04-25 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5714493A (en) | 1991-05-10 | 1998-02-03 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| EP0586608A1 (en) | 1991-05-29 | 1994-03-16 | Pfizer Inc. | Tricyclic polyhydroxylic tyrosine kinase inhibitors |
| US5213453A (en) | 1991-06-28 | 1993-05-25 | Tapmatic Corporation | Cooling systems in tapping attachments suitable for high pressure applications |
| GB9121418D0 (en) * | 1991-10-09 | 1991-11-20 | Nader Esfahani Rahim | Imaginograph |
| US5521184A (en) | 1992-04-03 | 1996-05-28 | Ciba-Geigy Corporation | Pyrimidine derivatives and processes for the preparation thereof |
| WO1994003427A1 (en) | 1992-08-06 | 1994-02-17 | Warner-Lambert Company | 2-thioindoles (selenoindoles) and related disulfides (selenides) which inhibit protein tyrosine kinases and which have antitumor properties |
| US5330992A (en) | 1992-10-23 | 1994-07-19 | Sterling Winthrop Inc. | 1-cyclopropyl-4-pyridyl-quinolinones |
| GB9323290D0 (en) | 1992-12-10 | 1994-01-05 | Zeneca Ltd | Quinazoline derivatives |
| GB9226855D0 (en) | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
| US5656643A (en) | 1993-11-08 | 1997-08-12 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US5906202A (en) | 1996-11-21 | 1999-05-25 | Aradigm Corporation | Device and method for directing aerosolized mist to a specific area of the respiratory tract |
| JPH10237028A (ja) * | 1996-12-24 | 1998-09-08 | Chugai Pharmaceut Co Ltd | Ｎｏｓ阻害作用を有する芳香族アミン誘導体 |
| RU2193554C2 (ru) * | 1996-12-24 | 2002-11-27 | Чугаи Сейяку Кабусики Кайся | Производные ароматических аминов, обладающих подавляющим оас действием, способ их получения и ингибитор ноас |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| US6596747B2 (en) * | 1998-10-29 | 2003-07-22 | Bristol-Myers Squibb Company | Compounds derived from an amine nucleus and pharmaceutical compositions comprising same |
| WO2000025780A1 (en) * | 1998-10-29 | 2000-05-11 | Bristol-Myers Squibb Company | Compounds derived from an amine nucleus that are inhibitors of impdh enzyme |
| IL143920A0 (en) | 1998-12-31 | 2002-04-21 | Sugen Inc | 3-heteroarylidenyl-2-indolinone derivatives and pharmaceutical compositions containing the same |
| US20020137755A1 (en) | 2000-12-04 | 2002-09-26 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| JP2005500041A (ja) | 2001-06-29 | 2005-01-06 | アブ サイエンス | 強力で選択的かつ非毒性のｃ−ｋｉｔ阻害剤 |
| EP1401411A2 (en) | 2001-06-29 | 2004-03-31 | AB Science | Use of tyrosine kinase inhibitors for treating bone loss |
| JP2004537536A (ja) | 2001-06-29 | 2004-12-16 | アブ サイエンス | アレルギー疾患を治療するためのチロシンキナーゼ阻害剤の使用方法 |
| JP2005503361A (ja) | 2001-06-29 | 2005-02-03 | アブ サイエンス | 肥満細胞症治療のための強力で選択的かつ非毒性のｃ−ｋｉｔ阻害剤の使用 |
| DE60215648T2 (de) | 2001-06-29 | 2007-08-23 | Ab Science | Die verwendung von c-kit hemmer zur behandlung von entzündlichen darmerkrankungen |
| EP1401412A2 (en) | 2001-06-29 | 2004-03-31 | AB Science | Use of potent, selective and non toxic c-kit inhibitors for treating tumor angiogenesis |
| ES2266553T3 (es) | 2001-06-29 | 2007-03-01 | Ab Science | Utilizacion de derivados de la n-fenil-2-pirimidina-amina para tratar las enfermedades inflamatorias. |
| EP1471907B1 (en) | 2001-06-29 | 2008-07-16 | AB Science | Use of c-kit inhibitors for treating autoimmune diseases |
| US20030091974A1 (en) | 2001-06-29 | 2003-05-15 | Alain Moussy | Method for screening compounds capable of depleting mast cells |
| US20040259892A1 (en) | 2001-06-29 | 2004-12-23 | Alain Moussy | Use of tyrosine kinase inhibitors for treating multiple sclerosis (ms) |
| ATE388711T1 (de) | 2001-09-20 | 2008-03-15 | Ab Science | C-kithemmer zur behandlung von bakteriellen infektionen |
| US20060204459A1 (en) | 2001-09-20 | 2006-09-14 | Alain Moussy | Use of tyrosine inhibitors for whitening human skin and treating melanocyted dysfunction associated diseases |
| DE60227701D1 (de) | 2001-09-20 | 2008-08-28 | Ab Science | Die verwendung von c-kithemmern zur förderung des haarwuchses |
| DE60323613D1 (de) | 2002-02-27 | 2008-10-30 | Ab Science | Verwendung von tyrosinkinase-hemmern zur behandlung von erkrankungen im zusammenhang mit substanzgebrauch |
| DK1478380T3 (da) | 2002-02-27 | 2006-11-27 | Ab Science | Anvendelse af tyrosinkinase-inhibitorer til behandling af CNS-lidelser |
| TW200401638A (en) | 2002-06-20 | 2004-02-01 | Bristol Myers Squibb Co | Heterocyclic inhibitors of kinases |
| EP1551813A4 (en) | 2002-10-10 | 2007-07-11 | Smithkline Beecham Corp | CHEMICAL COMPOUNDS |
| CA2517308A1 (en) | 2003-02-27 | 2004-09-10 | Ab Science | Tailored treatment suitable for different forms of mastocytosis |
| US7652044B2 (en) * | 2003-06-03 | 2010-01-26 | Novartis A.G. | P-38 inhibitors |
| CN1829513A (zh) * | 2003-06-03 | 2006-09-06 | 诺瓦提斯公司 | 基于五元杂环的p－38抑制剂 |
| EP1684750B1 (en) | 2003-10-23 | 2010-04-28 | AB Science | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors |
-
2004
- 2004-10-22 EP EP04791783A patent/EP1684750B1/en not_active Expired - Lifetime
- 2004-10-22 AU AU2004283162A patent/AU2004283162B2/en not_active Ceased
- 2004-10-22 JP JP2006536215A patent/JP4971797B2/ja not_active Expired - Fee Related
- 2004-10-22 DK DK04791783.6T patent/DK1684750T3/da active
- 2004-10-22 HR HR20100326T patent/HRP20100326T1/hr unknown
- 2004-10-22 PL PL04791783T patent/PL1684750T3/pl unknown
- 2004-10-22 CN CN2004800371595A patent/CN1950347B/zh not_active Expired - Fee Related
- 2004-10-22 CA CA2542909A patent/CA2542909C/en not_active Expired - Fee Related
- 2004-10-22 BR BRPI0415467-3A patent/BRPI0415467A/pt not_active IP Right Cessation
- 2004-10-22 US US10/576,267 patent/US7718676B2/en not_active Expired - Fee Related
- 2004-10-22 AT AT04791783T patent/ATE465731T1/de active
- 2004-10-22 NZ NZ546645A patent/NZ546645A/en not_active IP Right Cessation
- 2004-10-22 WO PCT/IB2004/003698 patent/WO2005040139A2/en not_active Ceased
-
2006
- 2006-04-20 IL IL175028A patent/IL175028A/en not_active IP Right Cessation
- 2006-05-22 NO NO20062308A patent/NO20062308L/no not_active Application Discontinuation
-
2010
- 2010-01-11 US US12/654,957 patent/US8110591B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007509130A5 (https=) | ||
| CA2542909A1 (en) | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors | |
| CN100491374C (zh) | 2-(3-氨基芳基)氨基-4-芳基-噻唑及其作为c-kit抑制剂的应用 | |
| KR20060129413A (ko) | 티로신 키나제 억제제로서의2-(3-치환된-아릴)아미노-4-아릴-티아졸 | |
| KR101164754B1 (ko) | 티로신 키나제 억제제로서의 2-아미노아릴옥사졸 화합물 | |
| JP5204643B2 (ja) | 置換オキサゾール誘導体、およびチロシンキナーゼ阻害薬としてのそれらの使用 | |
| WO2006064375A9 (en) | Aminoaryl substituted five-membered ring heterocyclic compounds for the treatment of diseases | |
| JP2007533732A (ja) | 線維症を処置するためのｃ−ｋｉｔ阻害剤の使用法 | |
| US20080039466A1 (en) | 2-(3-Substituted-Aryl) Amino-4-Aryl-Thiazoles As Tyrosine Kinase Inhibitors | |
| HK1091134B (en) | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors | |
| MXPA06004581A (en) | 2-aminoaryloxazole compounds as tyrosine kinase inhibitors | |
| MXPA06008597A (en) | 2-(3-substituted-aryl)amino-4-aryl-thiazoles as tyrosine kinase inhibitors | |
| HK1084382B (en) | 2-(3-aminoaryl) amino-4-aryl-thiazoles and their use as c-kit inhibitors |