JP2012515724A5 - - Google Patents
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- JP2012515724A5 JP2012515724A5 JP2011546451A JP2011546451A JP2012515724A5 JP 2012515724 A5 JP2012515724 A5 JP 2012515724A5 JP 2011546451 A JP2011546451 A JP 2011546451A JP 2011546451 A JP2011546451 A JP 2011546451A JP 2012515724 A5 JP2012515724 A5 JP 2012515724A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- fluoro
- cycloalkyl
- disease
- 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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- -1 amino, substituted amino, carboxyl Chemical group 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 125000000547 substituted alkyl group Chemical group 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 125000002252 acyl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 230000002757 inflammatory effect Effects 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004442 acylamino group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 5
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 5
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- 201000004624 Dermatitis Diseases 0.000 claims 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- TVNUWQIRTYYTNN-UHFFFAOYSA-N 5-fluoro-4-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-6-phenylpyrimidine-2,4-diamine Chemical compound C1(=CC=CC=C1)C1=C(C(=NC(=N1)N)NC1CC(N(C(C1)(C)C)C)(C)C)F TVNUWQIRTYYTNN-UHFFFAOYSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000030090 Acute Disease Diseases 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- 208000022461 Glomerular disease Diseases 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010022680 Intestinal ischaemia Diseases 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 2
- 206010028289 Muscle atrophy Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000013901 Nephropathies and tubular disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 206010049771 Shock haemorrhagic Diseases 0.000 claims 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 2
- 208000031709 Skin Manifestations Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 206010044541 Traumatic shock Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 208000024248 Vascular System injury Diseases 0.000 claims 2
- 208000012339 Vascular injury Diseases 0.000 claims 2
- 206010053648 Vascular occlusion Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 208000002029 allergic contact dermatitis Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 230000002491 angiogenic effect Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 208000037976 chronic inflammation Diseases 0.000 claims 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 208000024908 graft versus host disease Diseases 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000001875 irritant dermatitis Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 206010023332 keratitis Diseases 0.000 claims 2
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 2
- 201000006370 kidney failure Diseases 0.000 claims 2
- 201000010901 lateral sclerosis Diseases 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 208000005264 motor neuron disease Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000020763 muscle atrophy Effects 0.000 claims 2
- 201000000585 muscular atrophy Diseases 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 208000021331 vascular occlusion disease Diseases 0.000 claims 2
- SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- BFMGOJBQXYYXLG-UHFFFAOYSA-N 2-n-[3-(2,5-dimethylpyrrol-1-yl)-4-(2-morpholin-4-ylethoxy)phenyl]-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=C(C(OCCN3CCOCC3)=CC=2)N2C(=CC=C2C)C)=NC=C1F BFMGOJBQXYYXLG-UHFFFAOYSA-N 0.000 claims 1
- YKFGBWVAVVOOQP-UHFFFAOYSA-N 2-n-[3-(2,5-dimethylpyrrol-1-yl)-4-(2-morpholin-4-ylethoxy)phenyl]-5-fluoro-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound CC1=CC=C(C)N1C1=CC(NC=2N=C(NC3CC(C)(C)NC(C)(C)C3)C(F)=CN=2)=CC=C1OCCN1CCOCC1 YKFGBWVAVVOOQP-UHFFFAOYSA-N 0.000 claims 1
- RQHZHEIDLQGEFL-UHFFFAOYSA-N 2-n-[3-(2,5-dimethylpyrrol-1-yl)-4-(2-pyrrolidin-1-ylethoxy)phenyl]-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=C(C(OCCN3CCCC3)=CC=2)N2C(=CC=C2C)C)=NC=C1F RQHZHEIDLQGEFL-UHFFFAOYSA-N 0.000 claims 1
- QIPDYHFWFMMPQM-UHFFFAOYSA-N 2-n-[3-(2,5-dimethylpyrrol-1-yl)-4-(2-pyrrolidin-1-ylethoxy)phenyl]-5-fluoro-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound CC1=CC=C(C)N1C1=CC(NC=2N=C(NC3CC(C)(C)NC(C)(C)C3)C(F)=CN=2)=CC=C1OCCN1CCCC1 QIPDYHFWFMMPQM-UHFFFAOYSA-N 0.000 claims 1
- PCJSQXQRMJJBBS-UHFFFAOYSA-N 4-N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-5-phenylpyrimidine-2,4-diamine Chemical compound C1(=CC=CC=C1)C=1C(=NC(=NC=1)N)NC1CC(N(C(C1)(C)C)C)(C)C PCJSQXQRMJJBBS-UHFFFAOYSA-N 0.000 claims 1
- DFVSXLDAJLVVLH-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-morpholin-4-ylethoxy)phenyl]-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)N(C)C(C)(C)C1 DFVSXLDAJLVVLH-UHFFFAOYSA-N 0.000 claims 1
- JAUBLXVJBSZVSH-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-morpholin-4-ylethoxy)phenyl]-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)NC(C)(C)C1 JAUBLXVJBSZVSH-UHFFFAOYSA-N 0.000 claims 1
- VTKJXOMDTPRGOL-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-pyrrol-1-ylethoxy)phenyl]-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2C=CC=C2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)N(C)C(C)(C)C1 VTKJXOMDTPRGOL-UHFFFAOYSA-N 0.000 claims 1
- BUUNPQCCBUNUSR-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-pyrrol-1-ylethoxy)phenyl]-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2C=CC=C2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)NC(C)(C)C1 BUUNPQCCBUNUSR-UHFFFAOYSA-N 0.000 claims 1
- HTGWTCFYVDIVPK-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-pyrrolidin-1-ylethoxy)phenyl]-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2CCCC2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)N(C)C(C)(C)C1 HTGWTCFYVDIVPK-UHFFFAOYSA-N 0.000 claims 1
- BFCNQMNRCLSWEV-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-pyrrolidin-1-ylethoxy)phenyl]-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2CCCC2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)NC(C)(C)C1 BFCNQMNRCLSWEV-UHFFFAOYSA-N 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14627309P | 2009-01-21 | 2009-01-21 | |
| US61/146,273 | 2009-01-21 | ||
| US26416509P | 2009-11-24 | 2009-11-24 | |
| US61/264,165 | 2009-11-24 | ||
| PCT/US2010/021662 WO2010090875A1 (en) | 2009-01-21 | 2010-01-21 | Derivatives of n2-(3-pyridil or phenyl)-n4-(4-piperidyl)-2,4-pyrimidinediamine useful in the treatment of inflammatory, autoimmune or proliferative diseases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015018931A Division JP2015110629A (ja) | 2009-01-21 | 2015-02-03 | 炎症性疾患、自己免疫疾患または増殖性疾患の治療に有用なｎ２−（３−ピリジルまたはフェニル）−ｎ４−（４−ピペリジル）−２，４−ピリミジンジアミン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012515724A JP2012515724A (ja) | 2012-07-12 |
| JP2012515724A5 true JP2012515724A5 (enExample) | 2013-03-07 |
| JP5781943B2 JP5781943B2 (ja) | 2015-09-24 |
Family
ID=42272042
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011546451A Expired - Fee Related JP5781943B2 (ja) | 2009-01-21 | 2010-01-21 | 炎症性疾患、自己免疫疾患または増殖性疾患の治療に有用なｎ２−（３−ピリジルまたはフェニル）−ｎ４−（４−ピペリジル）−２，４−ピリミジンジアミン誘導体 |
| JP2015018931A Withdrawn JP2015110629A (ja) | 2009-01-21 | 2015-02-03 | 炎症性疾患、自己免疫疾患または増殖性疾患の治療に有用なｎ２−（３−ピリジルまたはフェニル）−ｎ４−（４−ピペリジル）−２，４−ピリミジンジアミン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015018931A Withdrawn JP2015110629A (ja) | 2009-01-21 | 2015-02-03 | 炎症性疾患、自己免疫疾患または増殖性疾患の治療に有用なｎ２−（３−ピリジルまたはフェニル）−ｎ４−（４−ピペリジル）−２，４−ピリミジンジアミン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8377924B2 (enExample) |
| EP (1) | EP2389373B1 (enExample) |
| JP (2) | JP5781943B2 (enExample) |
| CA (1) | CA2749837C (enExample) |
| ES (1) | ES2635504T3 (enExample) |
| WO (1) | WO2010090875A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1663242T3 (da) * | 2003-08-07 | 2011-08-01 | Rigel Pharmaceuticals Inc | 2,4-Pyrimidindiamin-forbindelser og anvendelse som antiproliferative midler |
| US20110130415A1 (en) * | 2009-12-01 | 2011-06-02 | Rajinder Singh | Protein kinase c inhibitors and uses thereof |
| CA2801781C (en) * | 2010-07-21 | 2018-02-27 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| EP2638036B1 (en) * | 2010-11-09 | 2017-08-16 | Betta Pharmaceuticals Co., Ltd. | Compound for increasing kinase active and application thereof |
| TWI548621B (zh) * | 2011-04-22 | 2016-09-11 | 標誌製藥公司 | 經取代之二胺基甲醯胺及二胺基甲腈嘧啶、其組合物、及以該等治療之方法 |
| US9321763B2 (en) | 2012-04-04 | 2016-04-26 | Rigel Pharmaceuticals, Inc. | Protein kinase C inhibitors and uses thereof |
| EP2928891B1 (en) | 2012-12-04 | 2019-02-20 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| US9169249B2 (en) | 2013-03-14 | 2015-10-27 | Rigel Pharmaceuticals, Inc. | Protein kinase C inhibitors and uses thereof |
| RU2016129380A (ru) | 2013-12-20 | 2018-01-25 | СИГНАЛ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Замещенные диаминопиримидильные соединения, их композиции и способы лечения с их участием |
| NZ715903A (en) | 2014-01-30 | 2017-06-30 | Signal Pharm Llc | Solid forms of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide, compositions thereof and methods of their use |
| US9399637B2 (en) | 2014-03-28 | 2016-07-26 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| US10059689B2 (en) | 2014-10-14 | 2018-08-28 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| US9513297B2 (en) | 2014-12-16 | 2016-12-06 | Signal Pharmaceuticals, Llc | Methods for measurement of inhibition of c-Jun N-terminal kinase in skin |
| EP3712134B1 (en) | 2014-12-16 | 2023-11-29 | Signal Pharmaceuticals, LLC | Salts of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methycyclohexylamino)-pyrimidine-5-carboxamide |
| EP3250557B1 (en) | 2015-01-29 | 2024-11-20 | Signal Pharmaceuticals, LLC | Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide |
| JP6853234B2 (ja) * | 2015-07-09 | 2021-03-31 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Ｂｔｋ阻害剤としてのピリミジン誘導体及びその使用 |
| EP3325432B1 (en) | 2015-07-24 | 2020-09-02 | Celgene Corporation | Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein |
| EP3347097B1 (en) | 2015-09-11 | 2021-02-24 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine derivatives as modulators of the kinases jak, flt3 and aurora |
| WO2017075418A1 (en) | 2015-10-30 | 2017-05-04 | Board Of Trustees Of The University Of Arkansas | Inhibitors of oxidized low-density lipoprotein receptor 1 and methods of use thereof |
| WO2018195450A1 (en) | 2017-04-21 | 2018-10-25 | Epizyme, Inc. | Combination therapies with ehmt2 inhibitors |
| PL3621615T3 (pl) | 2017-05-12 | 2024-03-25 | Enanta Pharmaceuticals, Inc. | Inhibitory regulujące sygnał apoptozy kinazy 1 i sposoby ich stosowania |
| WO2018218044A2 (en) | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals Inc | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10450301B2 (en) | 2017-05-25 | 2019-10-22 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2018218042A1 (en) | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10597382B2 (en) | 2017-08-28 | 2020-03-24 | Enanta Pharmaceuticals, Inc. | Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| JP7425724B2 (ja) * | 2017-10-17 | 2024-01-31 | エピザイム，インコーポレイティド | Ｅｈｍｔ２阻害剤としてのアミン置換複素環化合物及びその誘導体 |
| WO2019099311A1 (en) | 2017-11-19 | 2019-05-23 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
| WO2019213239A1 (en) | 2018-05-02 | 2019-11-07 | Enanta Pharmaceuticals Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| IL278368B2 (en) | 2018-05-02 | 2024-06-01 | Enanta Pharm Inc | Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10968199B2 (en) | 2018-08-22 | 2021-04-06 | Enanta Pharmaceuticals, Inc. | Cycloalkyl-containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2020106707A1 (en) | 2018-11-19 | 2020-05-28 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2020198214A1 (en) | 2019-03-25 | 2020-10-01 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US12643886B2 (en) | 2021-01-07 | 2026-06-02 | Ontario Institute for Cancer Research (OICR), The Governing Council of the University of Toronto, Sinai Health System | Isoindolinone aminopyrimidine compounds as inhibitors of NUAK kinases, compositions and uses thereof |
| EP4401735A4 (en) * | 2021-09-16 | 2025-07-16 | Lomond Therapeutics Inc | COMPOUNDS COMPRISING N-ARYLPYRIMIDIN-2-AMINE DERIVATIVES AS THERAPEUTIC AGENTS |
| CN119462522A (zh) * | 2023-08-08 | 2025-02-18 | 浙江大学 | N2-3-氟-5-取代苯基-2-氨基嘧啶类衍生物、其制备方法及医药用途 |
| WO2026108771A2 (en) * | 2024-11-19 | 2026-05-28 | Groovy Medicine (Hangzhou) Ltd. | Substituted heteroaromatic compounds as inhibitors of checkpoint kinase 1 and notch signaling pathway and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| JP4460292B2 (ja) * | 2001-10-17 | 2010-05-12 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | ピリミジン誘導体、これらの化合物を含む医薬組成物、その使用及びその調製方法 |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| IL166241A0 (en) | 2002-07-29 | 2006-01-15 | Rigel Pharmaceuticals Inc | Method of treating or preventing autoimmune diseases with 2,4-pyrimidinedinediamine compounds |
| WO2004043386A2 (en) | 2002-11-08 | 2004-05-27 | Tolerrx, Inc. | Molecules preferentially associated with effector t cells and methods of their use |
| UA80767C2 (en) * | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| JP4665760B2 (ja) | 2003-06-25 | 2011-04-06 | 日本電気株式会社 | 電子計算機、半導体集積回路、制御方法、プログラムの生成方法、及びプログラム |
| 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 |
| DK1663242T3 (da) * | 2003-08-07 | 2011-08-01 | Rigel Pharmaceuticals Inc | 2,4-Pyrimidindiamin-forbindelser og anvendelse som antiproliferative midler |
| CN1863773A (zh) | 2003-10-09 | 2006-11-15 | 埃科特莱茵药品有限公司 | 四氢吡啶衍生物 |
| KR20060127415A (ko) | 2003-12-24 | 2006-12-12 | 와이어쓰 | 천식의 치료방법 |
| US20070232658A1 (en) * | 2004-04-08 | 2007-10-04 | Jurgen Wagner | Protein Kinase C Inhibitors for the Treatment of Autoimmune Diseases and of Transplant Rejiction |
| JP2008540436A (ja) * | 2005-05-03 | 2008-11-20 | 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 | Ｊａｋキナーゼインヒビターおよびそれらの使用 |
| JP2010522765A (ja) | 2007-03-28 | 2010-07-08 | アレイ バイオファーマ、インコーポレイテッド | 受容体チロシンキナーゼとしてのイミダゾ［１，２−ａ］ピリジン化合物 |
| 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 |
| AU2009262068C1 (en) * | 2008-06-27 | 2015-07-02 | Celgene Car Llc | Heteroaryl compounds and uses thereof |
| CA2801781C (en) * | 2010-07-21 | 2018-02-27 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
-
2010
- 2010-01-21 WO PCT/US2010/021662 patent/WO2010090875A1/en not_active Ceased
- 2010-01-21 JP JP2011546451A patent/JP5781943B2/ja not_active Expired - Fee Related
- 2010-01-21 CA CA2749837A patent/CA2749837C/en active Active
- 2010-01-21 US US12/691,607 patent/US8377924B2/en not_active Expired - Fee Related
- 2010-01-21 EP EP10701773.3A patent/EP2389373B1/en not_active Not-in-force
- 2010-01-21 ES ES10701773.3T patent/ES2635504T3/es active Active
-
2012
- 2012-12-18 US US13/718,632 patent/US9149475B2/en not_active Expired - Fee Related
-
2015
- 2015-02-03 JP JP2015018931A patent/JP2015110629A/ja not_active Withdrawn
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