JP2007500722A5 - - Google Patents
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- JP2007500722A5 JP2007500722A5 JP2006522105A JP2006522105A JP2007500722A5 JP 2007500722 A5 JP2007500722 A5 JP 2007500722A5 JP 2006522105 A JP2006522105 A JP 2006522105A JP 2006522105 A JP2006522105 A JP 2006522105A JP 2007500722 A5 JP2007500722 A5 JP 2007500722A5
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- 150000001875 compounds Chemical class 0.000 claims 49
- -1 homopiperazinyl Chemical group 0.000 claims 41
- 229910052739 hydrogen Inorganic materials 0.000 claims 37
- 239000001257 hydrogen Substances 0.000 claims 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims 12
- 125000006239 protecting group Chemical group 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 11
- 208000023275 Autoimmune disease Diseases 0.000 claims 10
- 125000000172 C5-C10 aryl group Chemical group 0.000 claims 10
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 10
- 150000004677 hydrates Chemical class 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 9
- 125000004404 heteroalkyl group Chemical group 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 125000002757 morpholinyl group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 125000004193 piperazinyl group Chemical group 0.000 claims 9
- 125000003386 piperidinyl group Chemical group 0.000 claims 9
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 150000001204 N-oxides Chemical class 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 4
- 230000001363 autoimmune Effects 0.000 claims 3
- 230000009885 systemic effect Effects 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- OHZRGCZMBRSLMF-GFCCVEGCSA-N (2r)-6-[[5-fluoro-2-[3-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound O([C@@H](C(NC1=C2)=O)C)C1=CC=C2NC(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1C1=NC=CO1 OHZRGCZMBRSLMF-GFCCVEGCSA-N 0.000 claims 1
- NJTWMUPUIMAMDX-LBPRGKRZSA-N (2s)-6-[[5-fluoro-2-[3-(1,3-oxazol-5-yl)anilino]pyrimidin-4-yl]amino]-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound O([C@H](C(NC1=C2)=O)C)C1=CC=C2NC(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1C1=CN=CO1 NJTWMUPUIMAMDX-LBPRGKRZSA-N 0.000 claims 1
- RDFMUZFVBOQSPI-LBPRGKRZSA-N (2s)-6-[[5-fluoro-2-[4-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound O([C@H](C(NC1=C2)=O)C)C1=CC=C2NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C1=NC=CO1 RDFMUZFVBOQSPI-LBPRGKRZSA-N 0.000 claims 1
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims 1
- HIUHGBNOJGRQPB-UHFFFAOYSA-N 2,2-difluoro-6-[[5-fluoro-2-[3-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3NC(=O)C(F)(F)OC3=CC=2)C(F)=CN=C1NC(C=1)=CC=CC=1C1=NC=CO1 HIUHGBNOJGRQPB-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- DVUDFHPWEIGBEU-UHFFFAOYSA-N 4-n-(4-amino-3,4-dihydro-2h-chromen-6-yl)-5-fluoro-2-n-[3-(1,3-oxazol-2-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C1=C2C(N)CCOC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1C1=NC=CO1 DVUDFHPWEIGBEU-UHFFFAOYSA-N 0.000 claims 1
- CBUNLOCAKOHTLP-UHFFFAOYSA-N 5-fluoro-4-n-(4-methyl-2,3-dihydro-1,4-benzoxazin-6-yl)-2-n-[3-(1,3-oxazol-5-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C1=C2N(C)CCOC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1C1=CN=CO1 CBUNLOCAKOHTLP-UHFFFAOYSA-N 0.000 claims 1
- UKDSBSBNVOTGFY-UHFFFAOYSA-N 5-fluoro-4-n-(4-methyl-2,3-dihydro-1,4-benzoxazin-6-yl)-2-n-[4-(1,3-oxazol-5-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C1=C2N(C)CCOC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C1=CN=CO1 UKDSBSBNVOTGFY-UHFFFAOYSA-N 0.000 claims 1
- SZRSQWRYBRNWJP-UHFFFAOYSA-N 5-fluoro-4-n-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)-2-n-[3-(1,3-oxazol-5-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C=C2N(C)CCOC2=CC=1NC(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1C1=CN=CO1 SZRSQWRYBRNWJP-UHFFFAOYSA-N 0.000 claims 1
- IYKAPYGWZRKSKC-UHFFFAOYSA-N 5-fluoro-4-n-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)-2-n-[4-(1,3-oxazol-5-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C=C2N(C)CCOC2=CC=1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C1=CN=CO1 IYKAPYGWZRKSKC-UHFFFAOYSA-N 0.000 claims 1
- RMTFEZUZAHJEFW-UHFFFAOYSA-N 5-fluoropyrimidine-2,4-diamine Chemical compound NC1=NC=C(F)C(N)=N1 RMTFEZUZAHJEFW-UHFFFAOYSA-N 0.000 claims 1
- XNPOLGRSXVKAOB-UHFFFAOYSA-N 6-[[5-fluoro-2-[3-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-2,2-dimethyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C2NC(=O)C(C)(C)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1C1=NC=CO1 XNPOLGRSXVKAOB-UHFFFAOYSA-N 0.000 claims 1
- MLXXMVOGIKQTBD-UHFFFAOYSA-N 6-[[5-fluoro-2-[3-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-2-(2-hydroxyethyl)-4h-1,4-benzoxazin-3-one Chemical compound C1=C2NC(=O)C(CCO)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1C1=NC=CO1 MLXXMVOGIKQTBD-UHFFFAOYSA-N 0.000 claims 1
- ZVNJNOPAKDKMAL-UHFFFAOYSA-N 6-[[5-fluoro-2-[3-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3NC(=O)COC3=CC=2)C(F)=CN=C1NC(C=1)=CC=CC=1C1=NC=CO1 ZVNJNOPAKDKMAL-UHFFFAOYSA-N 0.000 claims 1
- ZDVGUFBRQOIEFJ-UHFFFAOYSA-N 6-[[5-fluoro-2-[3-(1,3-oxazol-5-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3NC(=O)COC3=CC=2)C(F)=CN=C1NC(C=1)=CC=CC=1C1=CN=CO1 ZDVGUFBRQOIEFJ-UHFFFAOYSA-N 0.000 claims 1
- IGPJKARGMHZUIB-UHFFFAOYSA-N 6-[[5-fluoro-2-[4-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-2-(2-hydroxyethyl)-4H-1,4-benzoxazin-3-one Chemical compound FC=1C(=NC(=NC1)NC1=CC=C(C=C1)C=1OC=CN1)NC=1C=CC2=C(NC(C(O2)CCO)=O)C1 IGPJKARGMHZUIB-UHFFFAOYSA-N 0.000 claims 1
- AROZEXWACDPSKK-UHFFFAOYSA-N 6-[[5-fluoro-2-[4-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-3,4-dihydro-2h-chromen-4-ol Chemical compound C1=C2C(O)CCOC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C1=NC=CO1 AROZEXWACDPSKK-UHFFFAOYSA-N 0.000 claims 1
- SLNHDTFVYMYHAQ-UHFFFAOYSA-N 6-[[5-fluoro-2-[4-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3NC(=O)COC3=CC=2)C(F)=CN=C1NC(C=C1)=CC=C1C1=NC=CO1 SLNHDTFVYMYHAQ-UHFFFAOYSA-N 0.000 claims 1
- DFYDQEQHRBVZIU-UHFFFAOYSA-N 6-[[5-fluoro-2-[4-(1,3-oxazol-5-yl)anilino]pyrimidin-4-yl]amino]-2-(2-hydroxyethyl)-4h-1,4-benzoxazin-3-one Chemical compound C1=C2NC(=O)C(CCO)OC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C1=CN=CO1 DFYDQEQHRBVZIU-UHFFFAOYSA-N 0.000 claims 1
- XFOPAXYBLQTMBH-UHFFFAOYSA-N 6-[[5-fluoro-2-[4-(1,3-oxazol-5-yl)anilino]pyrimidin-4-yl]amino]-3,4-dihydro-2h-chromen-4-ol Chemical compound C1=C2C(O)CCOC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C1=CN=CO1 XFOPAXYBLQTMBH-UHFFFAOYSA-N 0.000 claims 1
- PZOBTLFVFNXKMU-UHFFFAOYSA-N 6-[[5-fluoro-2-[4-(1,3-oxazol-5-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3NC(=O)COC3=CC=2)C(F)=CN=C1NC(C=C1)=CC=C1C1=CN=CO1 PZOBTLFVFNXKMU-UHFFFAOYSA-N 0.000 claims 1
- WBZBUUUCCGZIEC-UHFFFAOYSA-N 7-[[5-fluoro-2-[3-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3OCC(=O)NC3=CC=2)C(F)=CN=C1NC(C=1)=CC=CC=1C1=NC=CO1 WBZBUUUCCGZIEC-UHFFFAOYSA-N 0.000 claims 1
- SGGUTFLQPILCPA-UHFFFAOYSA-N 7-[[5-fluoro-2-[3-(1,3-oxazol-5-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3OCC(=O)NC3=CC=2)C(F)=CN=C1NC(C=1)=CC=CC=1C1=CN=CO1 SGGUTFLQPILCPA-UHFFFAOYSA-N 0.000 claims 1
- MSPVKUCFZBBUHC-UHFFFAOYSA-N 7-[[5-fluoro-2-[4-(1,3-oxazol-2-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3OCC(=O)NC3=CC=2)C(F)=CN=C1NC(C=C1)=CC=C1C1=NC=CO1 MSPVKUCFZBBUHC-UHFFFAOYSA-N 0.000 claims 1
- WGNISZHMVKDJBC-UHFFFAOYSA-N 7-[[5-fluoro-2-[4-(1,3-oxazol-5-yl)anilino]pyrimidin-4-yl]amino]-4h-1,4-benzoxazin-3-one Chemical compound N1=C(NC=2C=C3OCC(=O)NC3=CC=2)C(F)=CN=C1NC(C=C1)=CC=C1C1=CN=CO1 WGNISZHMVKDJBC-UHFFFAOYSA-N 0.000 claims 1
- 208000004300 Atrophic Gastritis Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 208000036495 Gastritis atrophic Diseases 0.000 claims 1
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 1
- 206010034277 Pemphigoid Diseases 0.000 claims 1
- 208000031845 Pernicious anaemia Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 208000033464 Reiter syndrome Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 206010042742 Sympathetic ophthalmia Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 1
- 230000005784 autoimmunity Effects 0.000 claims 1
- 208000000594 bullous pemphigoid Diseases 0.000 claims 1
- 208000016644 chronic atrophic gastritis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000001981 dermatomyositis Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000002491 encephalomyelitis Diseases 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 201000008350 membranous glomerulonephritis Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 201000005737 orchitis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000006292 polyarteritis nodosa Diseases 0.000 claims 1
- 208000002574 reactive arthritis Diseases 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 206010043554 thrombocytopenia Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 Cc1cc(*)c(*)c(*)c1 Chemical compound Cc1cc(*)c(*)c(*)c1 0.000 description 10
- OPFZOCAMAVOMPV-UHFFFAOYSA-N CC12C(C[n]3c(cc(C)cc4)c4nc3)CC1C2 Chemical compound CC12C(C[n]3c(cc(C)cc4)c4nc3)CC1C2 OPFZOCAMAVOMPV-UHFFFAOYSA-N 0.000 description 1
- SQWABMDMZKCMRY-UHFFFAOYSA-N Cc1ccc(Cc2ncc[o]2)cc1 Chemical compound Cc1ccc(Cc2ncc[o]2)cc1 SQWABMDMZKCMRY-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49164103P | 2003-07-30 | 2003-07-30 | |
| US60/491,641 | 2003-07-30 | ||
| US53159803P | 2003-12-19 | 2003-12-19 | |
| US60/531,598 | 2003-12-19 | ||
| US57224604P | 2004-05-18 | 2004-05-18 | |
| US60/572,246 | 2004-05-18 | ||
| PCT/US2004/024716 WO2005016893A2 (en) | 2003-07-30 | 2004-07-30 | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011179459A Division JP2011256198A (ja) | 2003-07-30 | 2011-08-19 | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療または予防方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007500722A JP2007500722A (ja) | 2007-01-18 |
| JP2007500722A5 true JP2007500722A5 (enExample) | 2010-01-14 |
| JP4886511B2 JP4886511B2 (ja) | 2012-02-29 |
Family
ID=34119815
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006522105A Expired - Lifetime JP4886511B2 (ja) | 2003-07-30 | 2004-07-30 | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療または予防方法 |
| JP2011179459A Pending JP2011256198A (ja) | 2003-07-30 | 2011-08-19 | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療または予防方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011179459A Pending JP2011256198A (ja) | 2003-07-30 | 2011-08-19 | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療または予防方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (10) | US8178671B2 (enExample) |
| EP (1) | EP1656372B1 (enExample) |
| JP (2) | JP4886511B2 (enExample) |
| KR (2) | KR101201603B1 (enExample) |
| CN (2) | CN1849318B (enExample) |
| AU (2) | AU2004265288A1 (enExample) |
| BR (1) | BRPI0413018B8 (enExample) |
| CA (1) | CA2533377C (enExample) |
| CY (1) | CY1114445T1 (enExample) |
| DK (1) | DK1656372T3 (enExample) |
| ES (1) | ES2421139T3 (enExample) |
| HR (1) | HRP20130602T1 (enExample) |
| IL (1) | IL173299A (enExample) |
| NO (1) | NO333771B1 (enExample) |
| NZ (1) | NZ545270A (enExample) |
| PL (1) | PL1656372T3 (enExample) |
| PT (1) | PT1656372E (enExample) |
| RS (1) | RS53109B (enExample) |
| SG (1) | SG145698A1 (enExample) |
| WO (2) | WO2005012294A1 (enExample) |
| ZA (1) | ZA200601460B (enExample) |
Families Citing this family (181)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| ATE451104T1 (de) | 2002-07-29 | 2009-12-15 | Rigel Pharmaceuticals Inc | Verfahren zur behandlung oder pruvention von autoimmunkrankheiten mit 2,4-pyrimidindiamin- verbindungen |
| ES2421139T3 (es) | 2003-07-30 | 2013-08-29 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidindiamina para su uso en el tratamiento o la prevención de enfermedades autoinmunitarias |
| EP1663242B1 (en) * | 2003-08-07 | 2011-04-27 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents |
| CA2566531A1 (en) | 2004-05-18 | 2005-12-15 | Rigel Pharmaceuticals, Inc. | Cycloalkyl substituted pyrimidinediamine compounds and their uses |
| MXPA06013918A (es) * | 2004-06-18 | 2007-03-07 | Neurosearch As | Nuevos derivados de piperidina sustituidos con alquilo como inhidibores de la recaptacion del neurotransmisor de monoamina. |
| WO2006004776A1 (en) | 2004-06-29 | 2006-01-12 | Rigel Pharmaceuticals, Inc. | 4-pyrimidineamine compounds and their uses as anti-proliferative agents |
| JP2008511659A (ja) * | 2004-09-01 | 2008-04-17 | ライジェル ファーマシューティカルズ， インコーポレイテッド | ２，４−ピリミジンジアミン化合物の合成 |
| CA2580838A1 (en) * | 2004-09-27 | 2006-04-06 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
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| WO2009012421A1 (en) * | 2007-07-17 | 2009-01-22 | Rigel Pharmaceuticals, Inc. | Cyclic amine substituted pyrimidinediamines as pkc inhibitors |
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2004
- 2004-07-30 ES ES04786150T patent/ES2421139T3/es not_active Expired - Lifetime
- 2004-07-30 WO PCT/US2004/024920 patent/WO2005012294A1/en not_active Ceased
- 2004-07-30 RS YU20060073A patent/RS53109B/sr unknown
- 2004-07-30 SG SG200805659-0A patent/SG145698A1/en unknown
- 2004-07-30 WO PCT/US2004/024716 patent/WO2005016893A2/en not_active Ceased
- 2004-07-30 NZ NZ545270A patent/NZ545270A/en not_active IP Right Cessation
- 2004-07-30 CA CA2533377A patent/CA2533377C/en not_active Expired - Lifetime
- 2004-07-30 CN CN2004800222355A patent/CN1849318B/zh not_active Expired - Lifetime
- 2004-07-30 JP JP2006522105A patent/JP4886511B2/ja not_active Expired - Lifetime
- 2004-07-30 BR BRPI0413018A patent/BRPI0413018B8/pt not_active IP Right Cessation
- 2004-07-30 AU AU2004265288A patent/AU2004265288A1/en not_active Abandoned
- 2004-07-30 US US10/903,263 patent/US8178671B2/en active Active
- 2004-07-30 US US10/903,870 patent/US7122542B2/en not_active Expired - Lifetime
- 2004-07-30 CN CN2011102453252A patent/CN102358738A/zh active Pending
- 2004-07-30 DK DK04786150.5T patent/DK1656372T3/da active
- 2004-07-30 HR HRP20130602TT patent/HRP20130602T1/hr unknown
- 2004-07-30 PL PL04786150T patent/PL1656372T3/pl unknown
- 2004-07-30 PT PT47861505T patent/PT1656372E/pt unknown
- 2004-07-30 KR KR1020067001947A patent/KR101201603B1/ko not_active Expired - Lifetime
- 2004-07-30 KR KR1020127008531A patent/KR20120062863A/ko not_active Ceased
- 2004-07-30 EP EP04786150.5A patent/EP1656372B1/en not_active Expired - Lifetime
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2006
- 2006-01-23 IL IL173299A patent/IL173299A/en active IP Right Grant
- 2006-02-23 ZA ZA2006/01460A patent/ZA200601460B/en unknown
- 2006-02-28 NO NO20060992A patent/NO333771B1/no unknown
- 2006-10-05 US US11/539,142 patent/US7582648B2/en not_active Expired - Lifetime
- 2006-10-05 US US11/539,147 patent/US7452879B2/en not_active Expired - Lifetime
- 2006-10-06 US US11/539,520 patent/US7560466B2/en not_active Expired - Lifetime
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2009
- 2009-06-18 US US12/487,486 patent/US9751893B2/en not_active Expired - Fee Related
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2011
- 2011-01-28 AU AU2011200367A patent/AU2011200367B2/en not_active Expired
- 2011-08-19 JP JP2011179459A patent/JP2011256198A/ja active Pending
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2012
- 2012-04-09 US US13/442,480 patent/US20120253039A1/en not_active Abandoned
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2013
- 2013-07-09 CY CY20131100580T patent/CY1114445T1/el unknown
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2017
- 2017-03-24 US US15/468,467 patent/US10259826B2/en not_active Expired - Lifetime
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2019
- 2019-03-21 US US16/360,958 patent/US11230554B2/en not_active Expired - Lifetime
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2021
- 2021-11-19 US US17/531,092 patent/US20220073536A1/en not_active Abandoned
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