JP2007509130A5 - - Google Patents

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Publication number: JP2007509130A5
Authority: JP; Japan
Prior art keywords: phenyl; oxazol; methyl; pyridin; ylamino
Prior art date: 2004-10-22
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

Application number

JP2006536215A

Other languages

English (en)

Japanese (ja)

Other versions

JP4971797B2 (ja

JP2007509130A (ja

Filing date

2004-10-22

Publication date

2011-07-28

2004-10-22 Application filed filed Critical

2004-10-22 Priority claimed from PCT/IB2004/003698 external-priority patent/WO2005040139A2/en

2007-04-12 Publication of JP2007509130A publication Critical patent/JP2007509130A/ja

2011-07-28 Publication of JP2007509130A5 publication Critical patent/JP2007509130A5/ja

2012-07-11 Application granted granted Critical

2012-07-11 Publication of JP4971797B2 publication Critical patent/JP4971797B2/ja

2024-10-22 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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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
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
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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
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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
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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
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JP2006536215A 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 Expired - Fee Related JP4971797B2 (ja)

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- 2004-10-22 BR BRPI0415467-3A patent/BRPI0415467A/pt not_active IP Right Cessation
- 2004-10-22 PL PL04791783T patent/PL1684750T3/pl unknown
- 2004-10-22 HR HR20100326T patent/HRP20100326T1/hr unknown
- 2004-10-22 NZ NZ546645A patent/NZ546645A/en not_active IP Right Cessation
- 2004-10-22 DK DK04791783.6T patent/DK1684750T3/da active
- 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 WO PCT/IB2004/003698 patent/WO2005040139A2/en not_active Ceased
- 2004-10-22 US US10/576,267 patent/US7718676B2/en not_active Expired - Fee Related
- 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 CN CN2004800371595A patent/CN1950347B/zh not_active Expired - Fee Related
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

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JP2007509130A5 (2)	2011-07-28
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