JP2007509130A5 - - Google Patents
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- 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
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- 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
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-
2004
- 2004-10-22 CA CA2542909A patent/CA2542909C/en not_active Expired - Fee Related
- 2004-10-22 AT AT04791783T patent/ATE465731T1/de active
- 2004-10-22 BR BRPI0415467-3A patent/BRPI0415467A/pt not_active IP Right Cessation
- 2004-10-22 CN CN2004800371595A patent/CN1950347B/zh not_active Expired - Fee Related
- 2004-10-22 EP EP04791783A patent/EP1684750B1/en not_active Expired - Lifetime
- 2004-10-22 NZ NZ546645A patent/NZ546645A/en not_active IP Right Cessation
- 2004-10-22 PL PL04791783T patent/PL1684750T3/pl unknown
- 2004-10-22 JP JP2006536215A patent/JP4971797B2/ja not_active Expired - Fee Related
- 2004-10-22 WO PCT/IB2004/003698 patent/WO2005040139A2/en not_active Ceased
- 2004-10-22 HR HR20100326T patent/HRP20100326T1/hr unknown
- 2004-10-22 AU AU2004283162A patent/AU2004283162B2/en not_active Ceased
- 2004-10-22 DK DK04791783.6T patent/DK1684750T3/da active
- 2004-10-22 US US10/576,267 patent/US7718676B2/en not_active Expired - Fee Related
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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
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2010
- 2010-01-11 US US12/654,957 patent/US8110591B2/en not_active Expired - Fee Related
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