JP2015528488A5 - - Google Patents
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- Publication number
- JP2015528488A5 JP2015528488A5 JP2015531648A JP2015531648A JP2015528488A5 JP 2015528488 A5 JP2015528488 A5 JP 2015528488A5 JP 2015531648 A JP2015531648 A JP 2015531648A JP 2015531648 A JP2015531648 A JP 2015531648A JP 2015528488 A5 JP2015528488 A5 JP 2015528488A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- aminocyclohexyl
- pyrimidine
- carboxamide
- indol
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 173
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 51
- -1 phenylthiophenyl Chemical group 0.000 claims 42
- 150000001875 compounds Chemical class 0.000 claims 40
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000012453 solvate Substances 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 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims 4
- 201000008937 atopic dermatitis Diseases 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 3
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims 3
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 3
- 201000010105 allergic rhinitis Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 2
- CSBPQHGADOHBPJ-UHFFFAOYSA-N 6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)NC=CC2=N1 CSBPQHGADOHBPJ-UHFFFAOYSA-N 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 241001303601 Rosacea Species 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 201000004700 rosacea Diseases 0.000 claims 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003816 2-hydroxybenzoyl group Chemical group OC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 206010048962 Brain oedema Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 241000222122 Candida albicans Species 0.000 claims 1
- 206010007134 Candida infections Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010009137 Chronic sinusitis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative 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
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 208000006926 Discoid Lupus Erythematosus Diseases 0.000 claims 1
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 208000010201 Exanthema Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 208000004262 Food Hypersensitivity Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 208000016300 Idiopathic chronic eosinophilic pneumonia Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000000112 Myalgia Diseases 0.000 claims 1
- 206010028735 Nasal congestion Diseases 0.000 claims 1
- 206010028741 Nasal inflammation Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 1
- 208000011191 Pulmonary vascular disease Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
- 208000002200 Respiratory Hypersensitivity Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038910 Retinitis Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010039094 Rhinitis perennial Diseases 0.000 claims 1
- 208000036071 Rhinorrhea Diseases 0.000 claims 1
- 206010039101 Rhinorrhoea Diseases 0.000 claims 1
- 201000010001 Silicosis Diseases 0.000 claims 1
- 206010042496 Sunburn Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046914 Vaginal infection Diseases 0.000 claims 1
- 201000008100 Vaginitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 206010069351 acute lung injury Diseases 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
- 230000010085 airway hyperresponsiveness Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 208000006752 brain edema Diseases 0.000 claims 1
- 210000000621 bronchi Anatomy 0.000 claims 1
- 201000009267 bronchiectasis Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 201000003984 candidiasis Diseases 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 201000009323 chronic eosinophilic pneumonia Diseases 0.000 claims 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims 1
- 230000008602 contraction Effects 0.000 claims 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 claims 1
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims 1
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 230000005713 exacerbation Effects 0.000 claims 1
- 201000005884 exanthem Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 235000020932 food allergy Nutrition 0.000 claims 1
- 150000002475 indoles Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 238000002483 medication Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000006938 muscular dystrophy Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 201000008383 nephritis Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims 1
- 206010037844 rash Diseases 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261702285P | 2012-09-18 | 2012-09-18 | |
| US61/702,285 | 2012-09-18 | ||
| PCT/GB2013/052440 WO2014045029A1 (en) | 2012-09-18 | 2013-09-18 | 2-(2-aminocyclohexyl)amino-pyrimidine-5-carboxamides as spleen tyrosine kinasei(syk) inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018013591A Division JP6602902B2 (ja) | 2012-09-18 | 2018-01-30 | 脾臓チロシンキナーゼｉ（ｓｙｋ）阻害剤としての２−（２−アミノシクロヘキシル）アミノピリミジン−５−カルボキサミド類 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015528488A JP2015528488A (ja) | 2015-09-28 |
| JP2015528488A5 true JP2015528488A5 (enExample) | 2016-11-10 |
| JP6463680B2 JP6463680B2 (ja) | 2019-02-06 |
Family
ID=49263322
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015531648A Expired - Fee Related JP6463680B2 (ja) | 2012-09-18 | 2013-09-18 | 脾臓チロシンキナーゼｉ（ｓｙｋ）阻害剤としての２−（２−アミノシクロヘキシル）アミノピリミジン−５−カルボキサミド類 |
| JP2018013591A Expired - Fee Related JP6602902B2 (ja) | 2012-09-18 | 2018-01-30 | 脾臓チロシンキナーゼｉ（ｓｙｋ）阻害剤としての２−（２−アミノシクロヘキシル）アミノピリミジン−５−カルボキサミド類 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018013591A Expired - Fee Related JP6602902B2 (ja) | 2012-09-18 | 2018-01-30 | 脾臓チロシンキナーゼｉ（ｓｙｋ）阻害剤としての２−（２−アミノシクロヘキシル）アミノピリミジン−５−カルボキサミド類 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9533989B2 (enExample) |
| EP (1) | EP2897950A1 (enExample) |
| JP (2) | JP6463680B2 (enExample) |
| CA (1) | CA2884921A1 (enExample) |
| WO (1) | WO2014045029A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2884921A1 (en) | 2012-09-18 | 2014-03-27 | Ziarco Pharma Ltd | 2-(2-aminocyclohexyl)amino-pyrimidine-5-carboxamides as spleen tyrosine kinasei(syk) inhibitors |
| EP3244893A4 (en) * | 2015-02-18 | 2019-01-09 | Parion Sciences, Inc. | SODIUM CHANNEL BLOCKER FOR SKIN DISEASES |
| CN109715162B (zh) * | 2016-08-12 | 2025-03-21 | 南京盖特医药技术有限公司 | 蛋白激酶调节剂 |
| KR102383561B1 (ko) * | 2017-09-07 | 2022-04-06 | 한국화학연구원 | 테트라히드로이소퀴놀린기로 치환된 피리미딘 유도체 화합물, 이의 광학이성질체, 또는 이의 약학적으로 허용 가능한 염, 및 이를 유효성분으로 포함하는 암 예방 또는 치료용 조성물 |
| WO2019136204A1 (en) * | 2018-01-04 | 2019-07-11 | Rush University Medical Center | Methods for treating neutrophilic dermatoses with syk inhibitors |
| CN119235862A (zh) * | 2018-03-09 | 2025-01-03 | 博尔托拉制药公司 | 选择性syk抑制剂的使用方法及药物组合物 |
| KR102698500B1 (ko) * | 2018-06-27 | 2024-08-26 | 주식회사 오스코텍 | Axl 억제제로 사용하기 위한 피리도피리미디논 유도체 |
| CN114364798A (zh) | 2019-03-21 | 2022-04-15 | 欧恩科斯欧公司 | 用于治疗癌症的Dbait分子与激酶抑制剂的组合 |
| US20220401436A1 (en) | 2019-11-08 | 2022-12-22 | INSERM (Institute National de la Santé et de la Recherche Médicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035296A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Improved release of medicament active agents from a chewing gum coating |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| JP4622047B2 (ja) * | 1999-06-09 | 2011-02-02 | アステラス製薬株式会社 | 新規なヘテロ環カルボキサミド誘導体 |
| WO2000075113A1 (en) | 1999-06-09 | 2000-12-14 | Yamanouchi Pharmaceutical Co., Ltd. | Novel heterocyclic carboxamide derivatives |
| NZ589315A (en) * | 2008-04-16 | 2012-11-30 | Portola Pharm Inc | 2,6-diamino-pyrimidin-5-yl-carboxamides as Spleen tryosine kinase (syk) or Janus kinase (JAK) inhibitors |
| JP5802127B2 (ja) * | 2008-04-16 | 2015-10-28 | ポートラ ファーマシューティカルズ， インコーポレイテッド | Ｓｙｋ又はｊａｋキナーゼ阻害剤としての２，６−ジアミノ−ピリミジン−５−イル−カルボキサミド類 |
| EP2493313B1 (en) * | 2009-10-29 | 2017-12-13 | Genosco | Kinase inhibitors |
| CA2884921A1 (en) | 2012-09-18 | 2014-03-27 | Ziarco Pharma Ltd | 2-(2-aminocyclohexyl)amino-pyrimidine-5-carboxamides as spleen tyrosine kinasei(syk) inhibitors |
-
2013
- 2013-09-18 CA CA2884921A patent/CA2884921A1/en not_active Abandoned
- 2013-09-18 EP EP13770696.6A patent/EP2897950A1/en not_active Withdrawn
- 2013-09-18 US US14/428,808 patent/US9533989B2/en not_active Expired - Fee Related
- 2013-09-18 JP JP2015531648A patent/JP6463680B2/ja not_active Expired - Fee Related
- 2013-09-18 WO PCT/GB2013/052440 patent/WO2014045029A1/en not_active Ceased
-
2016
- 2016-12-13 US US15/377,214 patent/US10065964B2/en not_active Expired - Fee Related
-
2018
- 2018-01-30 JP JP2018013591A patent/JP6602902B2/ja not_active Expired - Fee Related
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