JP2012515206A5 - - Google Patents
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- Publication number
- JP2012515206A5 JP2012515206A5 JP2011546310A JP2011546310A JP2012515206A5 JP 2012515206 A5 JP2012515206 A5 JP 2012515206A5 JP 2011546310 A JP2011546310 A JP 2011546310A JP 2011546310 A JP2011546310 A JP 2011546310A JP 2012515206 A5 JP2012515206 A5 JP 2012515206A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- benzo
- pyrimidine
- diamine
- 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
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 238000000034 method Methods 0.000 claims 9
- 125000005309 thioalkoxy group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- -1 amino, substituted amino Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 5
- 102000003923 Protein Kinase C Human genes 0.000 claims 4
- 108090000315 Protein Kinase C Proteins 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000004442 acylamino group Chemical group 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims 4
- 150000001540 azides Chemical class 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 4
- 150000003573 thiols Chemical class 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000022873 Ocular disease Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000033 alkoxyamino group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 239000012472 biological sample Substances 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000005255 oxyaminoacyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000005323 thioketone group Chemical group 0.000 claims 2
- LTUVCCLUHBJWCT-UHFFFAOYSA-N 2-n-(4,4-difluorotetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoro-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1=NC(NC=2C=C3N4N=NN=C4C(F)(F)OC3=CC=2)=NC=C1F LTUVCCLUHBJWCT-UHFFFAOYSA-N 0.000 claims 1
- AJLYVTYOGIMHBE-UHFFFAOYSA-N 2-n-(4,4-dimethyltetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoro-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1=NC(NC=2C=C3N4N=NN=C4C(C)(C)OC3=CC=2)=NC=C1F AJLYVTYOGIMHBE-UHFFFAOYSA-N 0.000 claims 1
- RYRJESRMDKUMCP-UHFFFAOYSA-N 2-n-(4,4-dimethyltetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoro-4-n-[(1,2,2,5,5-pentamethylpyrrolidin-3-yl)methyl]pyrimidine-2,4-diamine Chemical compound CC1(C)N(C)C(C)(C)CC1CNC1=NC(NC=2C=C3N4N=NN=C4C(C)(C)OC3=CC=2)=NC=C1F RYRJESRMDKUMCP-UHFFFAOYSA-N 0.000 claims 1
- VZHILUJEISCFMV-UHFFFAOYSA-N 2-n-(4,4-dimethyltetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoro-4-n-[(2,2,5,5-tetramethylpyrrolidin-3-yl)methyl]pyrimidine-2,4-diamine Chemical compound CC1(C)NC(C)(C)CC1CNC1=NC(NC=2C=C3N4N=NN=C4C(C)(C)OC3=CC=2)=NC=C1F VZHILUJEISCFMV-UHFFFAOYSA-N 0.000 claims 1
- OLWHZFWPBCZFLE-ZGTCLIOFSA-N 2-n-(4,4-dimethyltetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoro-4-n-[[(3r)-2,2,5-trimethylpyrrolidin-3-yl]methyl]pyrimidine-2,4-diamine Chemical compound CC1(C)NC(C)C[C@@H]1CNC1=NC(NC=2C=C3N4N=NN=C4C(C)(C)OC3=CC=2)=NC=C1F OLWHZFWPBCZFLE-ZGTCLIOFSA-N 0.000 claims 1
- OLWHZFWPBCZFLE-ABLWVSNPSA-N 2-n-(4,4-dimethyltetrazolo[5,1-c][1,4]benzoxazin-8-yl)-5-fluoro-4-n-[[(3s)-2,2,5-trimethylpyrrolidin-3-yl]methyl]pyrimidine-2,4-diamine Chemical compound CC1(C)NC(C)C[C@H]1CNC1=NC(NC=2C=C3N4N=NN=C4C(C)(C)OC3=CC=2)=NC=C1F OLWHZFWPBCZFLE-ABLWVSNPSA-N 0.000 claims 1
- PSLAQLYMLSXBSN-UHFFFAOYSA-N 2-n-(5,5-dimethyltetrazolo[1,5-c][1,3]benzoxazin-9-yl)-5-fluoro-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC1=NC(NC=2C=C3C4=NN=NN4C(C)(C)OC3=CC=2)=NC=C1F PSLAQLYMLSXBSN-UHFFFAOYSA-N 0.000 claims 1
- UUJVZPSLUNRRFW-UHFFFAOYSA-N 2-n-(5,5-dimethyltetrazolo[1,5-c][1,3]benzoxazin-9-yl)-5-fluoro-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1=NC(NC=2C=C3C4=NN=NN4C(C)(C)OC3=CC=2)=NC=C1F UUJVZPSLUNRRFW-UHFFFAOYSA-N 0.000 claims 1
- HAVXZLJBBINFQG-UHFFFAOYSA-N 5-fluoro-2-n-(4-methyl-8,9-dihydro-4h-tetrazolo[5,1-c][1,4]benzoxazin-8-yl)-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound N12N=NN=C2C(C)OC(C=C2)=C1CC2NC(N=1)=NC=C(F)C=1NC1CC(C)(C)N(C)C(C)(C)C1 HAVXZLJBBINFQG-UHFFFAOYSA-N 0.000 claims 1
- PVTQVFPZFZGQIT-UHFFFAOYSA-N 5-fluoro-2-n-(4-methyl-8,9-dihydro-4h-tetrazolo[5,1-c][1,4]benzoxazin-8-yl)-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound N12N=NN=C2C(C)OC(C=C2)=C1CC2NC(N=1)=NC=C(F)C=1NC1CC(C)(C)NC(C)(C)C1 PVTQVFPZFZGQIT-UHFFFAOYSA-N 0.000 claims 1
- PGRXJRINWODFNC-UHFFFAOYSA-N 5-fluoro-2-n-(4h-pyrrolo[2,1-c][1,4]benzoxazin-8-yl)-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1=NC(NC=2C=C3N4C=CC=C4COC3=CC=2)=NC=C1F PGRXJRINWODFNC-UHFFFAOYSA-N 0.000 claims 1
- YWICUEIGLYHVPU-UHFFFAOYSA-N 5-fluoro-2-n-spiro[8,9-dihydrotetrazolo[5,1-c][1,4]benzoxazine-4,1'-cyclobutane]-8-yl-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1=NC(NC2C=CC3=C(N4N=NN=C4C4(CCC4)O3)C2)=NC=C1F YWICUEIGLYHVPU-UHFFFAOYSA-N 0.000 claims 1
- CSTBCRKOEOXJEQ-UHFFFAOYSA-N 5-fluoro-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)-2-n-(4h-pyrrolo[2,1-c][1,4]benzoxazin-8-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC1=NC(NC=2C=C3N4C=CC=C4COC3=CC=2)=NC=C1F CSTBCRKOEOXJEQ-UHFFFAOYSA-N 0.000 claims 1
- QENQYQWCUUXRLZ-UHFFFAOYSA-N 5-fluoro-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)-2-n-(4h-tetrazolo[5,1-c][1,4]benzoxazin-8-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC1=NC(NC=2C=C3N4N=NN=C4COC3=CC=2)=NC=C1F QENQYQWCUUXRLZ-UHFFFAOYSA-N 0.000 claims 1
- TUYVAPMHYIQKFZ-UHFFFAOYSA-N 5-fluoro-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)-2-n-spiro[8,9-dihydrotetrazolo[5,1-c][1,4]benzoxazine-4,1'-cyclobutane]-8-ylpyrimidine-2,4-diamine Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC1=NC(NC2C=CC3=C(N4N=NN=C4C4(CCC4)O3)C2)=NC=C1F TUYVAPMHYIQKFZ-UHFFFAOYSA-N 0.000 claims 1
- YFTWMQCFOKVFNN-UHFFFAOYSA-N 5-fluoro-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)-2-n-(4h-tetrazolo[5,1-c][1,4]benzoxazin-8-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1=NC(NC=2C=C3N4N=NN=C4COC3=CC=2)=NC=C1F YFTWMQCFOKVFNN-UHFFFAOYSA-N 0.000 claims 1
- ORWZEDUXBCRHIG-UHFFFAOYSA-N 5-fluoro-4-n-[(1,2,2,5,5-pentamethylpyrrolidin-3-yl)methyl]-2-n-(4h-tetrazolo[5,1-c][1,4]benzoxazin-8-yl)pyrimidine-2,4-diamine Chemical compound CC1(C)N(C)C(C)(C)CC1CNC1=NC(NC=2C=C3N4N=NN=C4COC3=CC=2)=NC=C1F ORWZEDUXBCRHIG-UHFFFAOYSA-N 0.000 claims 1
- LIDVYEPHWJGKMQ-UHFFFAOYSA-N 5-fluoro-4-n-[(2,2,5,5-tetramethylpyrrolidin-3-yl)methyl]-2-n-(4h-tetrazolo[5,1-c][1,4]benzoxazin-8-yl)pyrimidine-2,4-diamine Chemical compound CC1(C)NC(C)(C)CC1CNC1=NC(NC=2C=C3N4N=NN=C4COC3=CC=2)=NC=C1F LIDVYEPHWJGKMQ-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 102000000551 Syk Kinase Human genes 0.000 claims 1
- 108010016672 Syk Kinase Proteins 0.000 claims 1
- 230000006044 T cell activation Effects 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 230000002459 sustained effect Effects 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14502109P | 2009-01-15 | 2009-01-15 | |
| US61/145,021 | 2009-01-15 | ||
| US14735309P | 2009-01-26 | 2009-01-26 | |
| US61/147,353 | 2009-01-26 | ||
| PCT/US2010/020888 WO2010083207A2 (en) | 2009-01-15 | 2010-01-13 | Protein kinase c inhibitors and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012515206A JP2012515206A (ja) | 2012-07-05 |
| JP2012515206A5 true JP2012515206A5 (https=) | 2013-02-28 |
| JP5603881B2 JP5603881B2 (ja) | 2014-10-08 |
Family
ID=42337453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011546310A Expired - Fee Related JP5603881B2 (ja) | 2009-01-15 | 2010-01-13 | プロテインキナーゼｃ阻害剤とその使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US8394951B2 (https=) |
| EP (1) | EP2387572B1 (https=) |
| JP (1) | JP5603881B2 (https=) |
| CN (1) | CN102292333B (https=) |
| CA (1) | CA2749195C (https=) |
| ES (1) | ES2555982T3 (https=) |
| WO (1) | WO2010083207A2 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6035238B2 (ja) | 2010-07-21 | 2016-11-30 | 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 | プロテインキナーゼｃ阻害剤およびその使用 |
| CN104169272A (zh) | 2011-12-23 | 2014-11-26 | 赛尔佐姆有限公司 | 作为激酶抑制剂的嘧啶-2,4-二胺衍生物 |
| ES2658395T3 (es) | 2012-04-04 | 2018-03-09 | Rigel Pharmaceuticals, Inc. | Inhibidores de proteína cinasa C y usos de los mismos |
| EP2928891B1 (en) | 2012-12-04 | 2019-02-20 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| CA2904610A1 (en) | 2013-03-14 | 2014-09-25 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| ES2851724T3 (es) | 2013-09-18 | 2021-09-08 | Epiaxis Therapeutics Pty Ltd | Modulación de células madre |
| CA2958704A1 (en) | 2014-08-25 | 2016-03-03 | University Of Canberra | Compositions for modulating cancer stem cells and uses therefor |
| WO2017038552A1 (ja) * | 2015-09-04 | 2017-03-09 | Dic株式会社 | 安定剤化合物、液晶組成物および表示素子 |
| US10633590B2 (en) | 2015-09-04 | 2020-04-28 | Dic Corporation | Liquid crystal composition and liquid crystal display device including the same |
| CN108913655B (zh) * | 2018-07-16 | 2022-07-15 | 浙江大学 | 基于多能干细胞技术建立“人源性”心肌肥大模型的方法 |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| US11384083B2 (en) | 2019-02-15 | 2022-07-12 | Incyte Corporation | Substituted spiro[cyclopropane-1,5′-pyrrolo[2,3-d]pyrimidin]-6′(7′h)-ones as CDK2 inhibitors |
| TW202100520A (zh) | 2019-03-05 | 2021-01-01 | 美商英塞特公司 | 作為cdk2 抑制劑之吡唑基嘧啶基胺化合物 |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| US11447494B2 (en) | 2019-05-01 | 2022-09-20 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| WO2020223469A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | N-(1-(methylsulfonyl)piperidin-4-yl)-4,5-di hydro-1h-imidazo[4,5-h]quinazolin-8-amine derivatives and related compounds as cyclin-dependent kinase 2 (cdk2) inhibitors for treating cancer |
| CA3150681A1 (en) | 2019-08-14 | 2021-02-18 | Incyte Corporation | Imidazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| US11851426B2 (en) | 2019-10-11 | 2023-12-26 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| CN117015543A (zh) * | 2020-09-14 | 2023-11-07 | 高德美控股有限公司 | 新型jak抑制剂化合物、其合成方法及其用途 |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9523675D0 (en) * | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| DK1242382T3 (da) * | 1999-12-29 | 2007-05-07 | Wyeth Corp | Tricycliske proteinkinaseinhibitorer |
| TWI329105B (en) * | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| WO2003095448A1 (en) * | 2002-05-06 | 2003-11-20 | Bayer Pharmaceuticals Corporation | Pyridinyl amino pyrimidine derivatives useful for treating hyper-proliferative disorders |
| CN1798748A (zh) * | 2003-04-07 | 2006-07-05 | Gpc生物科技公司 | 依赖细胞周期蛋白的激酶抑制剂及其组合物和相关用途 |
| WO2005012294A1 (en) * | 2003-07-30 | 2005-02-10 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| ATE506953T1 (de) * | 2003-08-07 | 2011-05-15 | Rigel Pharmaceuticals Inc | 2,4-pyrimidindiamin-verbindungen und verwendungen als antiproliferative mittel |
| JP2008505910A (ja) * | 2004-07-08 | 2008-02-28 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | Ｐｋｃ−シータのインヒビターとして有用なピリミジン誘導体 |
| CN1998221A (zh) | 2004-08-03 | 2007-07-11 | 诺基亚公司 | 移动通信和/或游戏终端 |
| ATE485042T1 (de) * | 2004-10-21 | 2010-11-15 | Vertex Pharma | Triazole als hemmer von proteinkinasen |
| US8227455B2 (en) * | 2005-04-18 | 2012-07-24 | Rigel Pharmaceuticals, Inc. | Methods of treating cell proliferative disorders |
| WO2006129100A1 (en) * | 2005-06-03 | 2006-12-07 | Glaxo Group Limited | Novel compounds |
| BRPI0610876B8 (pt) * | 2005-06-08 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, formulação farmacêutica, e métodos de inibir uma atividade de uma jak cinase, e de inibir uma cascata de transdução de sinal em que jak3 cinase desempenha um papel |
| WO2007002847A2 (en) | 2005-06-28 | 2007-01-04 | Community Power Corporation | Method and apparatus for a self-cleaning filter |
| WO2007028445A1 (en) * | 2005-07-15 | 2007-03-15 | Glaxo Group Limited | 6-indolyl-4-yl-amino-5-halogeno-2-pyrimidinyl-amino derivatives |
| RU2008152195A (ru) * | 2006-06-15 | 2010-07-20 | БЕРИНГЕР ИНГЕЛЬХАЙМ ИНТЕРНАЦИОНАЛЬ ГмбХ (DE) | 2-анилино-4-(гетероциклил)аминопиримидины, как ингибиторы протеинкиназы с-альфа |
| US20100269694A1 (en) | 2006-06-28 | 2010-10-28 | The Governors Of The University Of Alberta | Silicate Materials, Method For Their Manufacture, And Method For Using Such Silicate Materials For Adsorptive Fluid Separations |
| WO2008024634A1 (en) * | 2006-08-25 | 2008-02-28 | Smithkline Beecham Corporation | Pyrimdine compounds useful as kinase inhibitors |
| ITVI20070184A1 (it) | 2007-06-27 | 2008-12-28 | Simec Spa | Puleggia per macchine utensili multifilo. |
| CN101903357A (zh) * | 2007-07-17 | 2010-12-01 | 里格尔药品股份有限公司 | 作为pkc抑制剂的环状胺取代的嘧啶二胺 |
| JP5781942B2 (ja) * | 2009-01-14 | 2015-09-24 | 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を用いた炎症性障害の治療法 |
-
2010
- 2010-01-13 JP JP2011546310A patent/JP5603881B2/ja not_active Expired - Fee Related
- 2010-01-13 WO PCT/US2010/020888 patent/WO2010083207A2/en not_active Ceased
- 2010-01-13 US US12/687,054 patent/US8394951B2/en not_active Expired - Fee Related
- 2010-01-13 CA CA2749195A patent/CA2749195C/en active Active
- 2010-01-13 ES ES10732030.1T patent/ES2555982T3/es active Active
- 2010-01-13 EP EP10732030.1A patent/EP2387572B1/en not_active Not-in-force
- 2010-01-13 CN CN201080005581.8A patent/CN102292333B/zh not_active Expired - Fee Related
-
2013
- 2013-02-06 US US13/760,666 patent/US9095593B2/en active Active
-
2015
- 2015-06-29 US US14/754,415 patent/US9453028B2/en not_active Expired - Fee Related
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