JP2015522607A5 - - Google Patents
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- Publication number
- JP2015522607A5 JP2015522607A5 JP2015523009A JP2015523009A JP2015522607A5 JP 2015522607 A5 JP2015522607 A5 JP 2015522607A5 JP 2015523009 A JP2015523009 A JP 2015523009A JP 2015523009 A JP2015523009 A JP 2015523009A JP 2015522607 A5 JP2015522607 A5 JP 2015522607A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- isoquinoline
- carboxamide
- amino
- trifluoromethyl
- 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.)
- Withdrawn
Links
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 4
- 230000002159 abnormal effect Effects 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 102000001253 Protein Kinase Human genes 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N alpha-Phenylquinoline Natural products C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 claims 2
- 230000004663 cell proliferation Effects 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 108060006633 protein kinase Proteins 0.000 claims 2
- ZIYOVHCFFWBQJR-UHFFFAOYSA-N 1-(tert-butylamino)-N-[2-methyl-5-(phenylcarbamoyl)phenyl]isoquinoline-5-carboxamide Chemical compound C(C)(C)(C)NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)C(NC1=CC=CC=C1)=O)C ZIYOVHCFFWBQJR-UHFFFAOYSA-N 0.000 claims 1
- MMANGHIETAOBGN-UHFFFAOYSA-N 1-(tert-butylamino)-N-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoyl]phenyl]isoquinoline-5-carboxamide Chemical compound C(C)(C)(C)NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)C(NC1=CC(=CC=C1)C(F)(F)F)=O)C MMANGHIETAOBGN-UHFFFAOYSA-N 0.000 claims 1
- JQCWAZWCJOLFTK-UHFFFAOYSA-N 1-(tert-butylamino)-N-[5-[[2-fluoro-5-(trifluoromethyl)phenyl]carbamoylamino]-2-methylphenyl]isoquinoline-5-carboxamide Chemical compound CC1=C(NC(=O)C2=C3C=CN=C(NC(C)(C)C)C3=CC=C2)C=C(NC(=O)NC2=C(F)C=CC(=C2)C(F)(F)F)C=C1 JQCWAZWCJOLFTK-UHFFFAOYSA-N 0.000 claims 1
- QWHYQPJNCCGSET-UHFFFAOYSA-N 1-(tert-butylamino)-N-[5-[[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]isoquinoline-5-carboxamide Chemical compound C(C)(C)(C)NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)C(NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F)=O)C QWHYQPJNCCGSET-UHFFFAOYSA-N 0.000 claims 1
- DTQJPQBUPSOKAA-UHFFFAOYSA-N 1-(tert-butylamino)-N-[5-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]-2-methylphenyl]isoquinoline-5-carboxamide Chemical compound CC1=C(NC(=O)C2=C3C=CN=C(NC(C)(C)C)C3=CC=C2)C=C(NC(=O)NC2=CC(=C(Cl)C=C2)C(F)(F)F)C=C1 DTQJPQBUPSOKAA-UHFFFAOYSA-N 0.000 claims 1
- PRILLXFTJUYCIA-UHFFFAOYSA-N 1-[(5-methoxypyridin-2-yl)amino]-N-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoyl]phenyl]isoquinoline-5-carboxamide Chemical compound COC=1C=CC(=NC1)NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)C(NC1=CC(=CC=C1)C(F)(F)F)=O)C PRILLXFTJUYCIA-UHFFFAOYSA-N 0.000 claims 1
- NFUUYWBSJZHZKK-UHFFFAOYSA-N 1-[(5-methoxypyridin-2-yl)amino]-N-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]isoquinoline-5-carboxamide Chemical compound COC=1C=CC(=NC1)NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)NC(=O)NC1=CC(=CC=C1)C(F)(F)F)C NFUUYWBSJZHZKK-UHFFFAOYSA-N 0.000 claims 1
- QOXOALUVNITUHC-UHFFFAOYSA-N 1-amino-N-[2-methyl-5-[[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]carbamoyl]phenyl]isoquinoline-5-carboxamide Chemical compound NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)C(NC1=CC(=CC(=C1)C(F)(F)F)N1C=NC(=C1)C)=O)C QOXOALUVNITUHC-UHFFFAOYSA-N 0.000 claims 1
- JETCTCUSGZDEGL-UHFFFAOYSA-N 1-amino-N-[2-methyl-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]isoquinoline-5-carboxamide Chemical compound NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)NC(C1=CC(=CC=C1)C(F)(F)F)=O)C JETCTCUSGZDEGL-UHFFFAOYSA-N 0.000 claims 1
- SZACTJFIRDPPRS-UHFFFAOYSA-N 1-amino-N-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoyl]phenyl]isoquinoline-5-carboxamide Chemical compound CC1=C(NC(=O)C2=C3C=CN=C(N)C3=CC=C2)C=C(C=C1)C(=O)NC1=CC(=CC=C1)C(F)(F)F SZACTJFIRDPPRS-UHFFFAOYSA-N 0.000 claims 1
- GEUOQYOJBPJPJI-UHFFFAOYSA-N 1-amino-N-[2-methyl-5-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]isoquinoline-5-carboxamide Chemical compound NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)NC(=O)NC1=CC(=CC=C1)C(F)(F)F)C GEUOQYOJBPJPJI-UHFFFAOYSA-N 0.000 claims 1
- FGQBBLUSDFYDGN-UHFFFAOYSA-N 1-amino-N-[2-methyl-5-[[4-(trifluoromethyl)pyridin-2-yl]carbamoyl]phenyl]isoquinoline-5-carboxamide Chemical compound CC1=C(NC(=O)C2=C3C=CN=C(N)C3=CC=C2)C=C(C=C1)C(=O)NC1=NC=CC(=C1)C(F)(F)F FGQBBLUSDFYDGN-UHFFFAOYSA-N 0.000 claims 1
- FRTZCTYQLADQFY-UHFFFAOYSA-N 1-amino-N-[3-[[3-(trifluoromethyl)phenyl]carbamoyl]phenyl]isoquinoline-5-carboxamide Chemical compound NC1=NC=CC2=C(C=CC=C12)C(=O)NC1=CC(=CC=C1)C(=O)NC1=CC(=CC=C1)C(F)(F)F FRTZCTYQLADQFY-UHFFFAOYSA-N 0.000 claims 1
- PWTBKWIXSHMHKC-UHFFFAOYSA-N 1-amino-N-[5-[(4,6-dimethylpyridin-2-yl)carbamoyl]-2-methylphenyl]isoquinoline-5-carboxamide Chemical compound NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)C(NC1=NC(=CC(=C1)C)C)=O)C PWTBKWIXSHMHKC-UHFFFAOYSA-N 0.000 claims 1
- WRXUZDBIWSRNAH-UHFFFAOYSA-N 1-amino-N-[5-[[3-(2-cyanopropan-2-yl)phenyl]carbamoyl]-2-methylphenyl]isoquinoline-5-carboxamide Chemical compound NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)C(NC1=CC(=CC=C1)C(C)(C)C#N)=O)C WRXUZDBIWSRNAH-UHFFFAOYSA-N 0.000 claims 1
- OVKXYZFIMKLWCQ-UHFFFAOYSA-N 1-amino-N-[5-[[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]isoquinoline-5-carboxamide Chemical compound NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C(C=CC(=C1)C(NC1=CC(=C(C=C1)CN1CCN(CC1)CC)C(F)(F)F)=O)C OVKXYZFIMKLWCQ-UHFFFAOYSA-N 0.000 claims 1
- JCKIRTKUOKCXTJ-UHFFFAOYSA-N 1-amino-N-[5-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]isoquinoline-5-carboxamide Chemical compound CC1=C(NC(=O)C2=C3C=CN=C(N)C3=CC=C2)C=C(C=C1)C(=O)NC1=CC(=C(Cl)C=C1)C(F)(F)F JCKIRTKUOKCXTJ-UHFFFAOYSA-N 0.000 claims 1
- WHQSMFHBQXZDSS-UHFFFAOYSA-N 1-amino-N-[6-methyl-1-[3-(trifluoromethyl)anilino]isoquinolin-5-yl]isoquinoline-5-carboxamide Chemical compound NC1=NC=CC=2C(=CC=CC12)C(=O)NC1=C2C=CN=C(C2=CC=C1C)NC1=CC(=CC=C1)C(F)(F)F WHQSMFHBQXZDSS-UHFFFAOYSA-N 0.000 claims 1
- 208000030090 Acute Disease Diseases 0.000 claims 1
- 206010001233 Adenoma benign Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 201000000054 Coronary Restenosis Diseases 0.000 claims 1
- 206010056489 Coronary artery restenosis Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 208000007659 Fibroadenoma Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000008771 Lymphadenopathy Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- HIMYDRFOEVDHIA-UHFFFAOYSA-N N-[1-(4-chloroanilino)-6-methylisoquinolin-5-yl]isoquinoline-5-carboxamide Chemical compound ClC1=CC=C(C=C1)NC1=NC=CC2=C(C(=CC=C12)C)NC(=O)C=1C=2C=CN=CC2C=CC1 HIMYDRFOEVDHIA-UHFFFAOYSA-N 0.000 claims 1
- CIOHNSXBIPGISE-UHFFFAOYSA-N N-[2-methyl-5-[[3-(trifluoromethyl)benzoyl]amino]phenyl]isoquinoline-5-carboxamide Chemical compound CC1=C(C=C(C=C1)NC(C1=CC(=CC=C1)C(F)(F)F)=O)NC(=O)C=1C=2C=CN=CC2C=CC1 CIOHNSXBIPGISE-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000022873 Ocular disease Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000000821 Parathyroid Neoplasms Diseases 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 claims 1
- 102000001393 Platelet-Derived Growth Factor alpha Receptor Human genes 0.000 claims 1
- 108010068588 Platelet-Derived Growth Factor alpha Receptor Proteins 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 108010091528 Proto-Oncogene Proteins B-raf Proteins 0.000 claims 1
- 102000018471 Proto-Oncogene Proteins B-raf Human genes 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 101710141955 RAF proto-oncogene serine/threonine-protein kinase Proteins 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 206010046431 Urethral cancer Diseases 0.000 claims 1
- 206010046458 Urethral neoplasms Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000013228 adenopathy Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000003149 breast fibroadenoma Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 201000011066 hemangioma Diseases 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- -1 isomers Chemical class 0.000 claims 1
- SJFXVNZZLJUPCS-UHFFFAOYSA-N isoquinoline-5-carboxamide Chemical class N1=CC=C2C(C(=O)N)=CC=CC2=C1 SJFXVNZZLJUPCS-UHFFFAOYSA-N 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 208000026037 malignant tumor of neck Diseases 0.000 claims 1
- 208000026045 malignant tumor of parathyroid gland Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 102000020233 phosphotransferase Human genes 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000002314 small intestine cancer Diseases 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2012-0078904 | 2012-07-19 | ||
| KR1020120078904A KR20140011780A (ko) | 2012-07-19 | 2012-07-19 | 단백질 키나아제 저해활성을 갖는 이소퀴놀린-5-카복스아미드 유도체 |
| PCT/KR2013/006392 WO2014014270A1 (ko) | 2012-07-19 | 2013-07-17 | 단백질 키나아제 저해활성을 갖는 이소퀴놀린-5-카복스아미드 유도체 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015522607A JP2015522607A (ja) | 2015-08-06 |
| JP2015522607A5 true JP2015522607A5 (https=) | 2016-08-18 |
Family
ID=49949038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015523009A Withdrawn JP2015522607A (ja) | 2012-07-19 | 2013-07-17 | プロテインキナーゼに対する阻害活性を有するイソキノリン−５−カルボキサミド誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9388165B2 (https=) |
| EP (1) | EP2876107A4 (https=) |
| JP (1) | JP2015522607A (https=) |
| KR (1) | KR20140011780A (https=) |
| CN (1) | CN104487420A (https=) |
| WO (1) | WO2014014270A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170273922A1 (en) * | 2014-10-03 | 2017-09-28 | The Royal Institution For The Advacement Of Learning/Mcgill University | Urea and bis-urea based compounds and analogues thereof useful in the treatment of androgen receptor mediated diseases or disorders |
| JP6912667B2 (ja) | 2017-07-29 | 2021-08-04 | ルトリス ファーマ エル ティー ディー． | 新規なｂｒａｆ阻害剤および皮膚反応を治療するためのその使用 |
| MX2020005563A (es) | 2017-11-30 | 2020-10-28 | Hanmi Pharm Ind Co Ltd | Compuesto de tieno[3,2-d]pirimidina que tiene actividad inhibidora para proteina cinasa. |
| US12274703B2 (en) | 2017-12-21 | 2025-04-15 | Gliapharm Sa | Compositions and methods of treatment for neurological disorders comprising a dementia |
| US12310967B2 (en) | 2017-12-21 | 2025-05-27 | Gliapharm Sa | Compositions and methods of treatment for neurological disorders comprising motor neuron diseases |
| CA3104808A1 (en) * | 2018-07-02 | 2020-01-09 | Ecole Polytechnique Federale De Lausanne (Epfl) | Lactate enhancing compounds and uses thereof |
| WO2020132378A2 (en) | 2018-12-22 | 2020-06-25 | Gliapharm Sa | Compositions and methods of treatment for neurological disorders comprising depression |
| KR102534457B1 (ko) | 2019-02-12 | 2023-05-18 | 루트리스 파마 엘티디. | 방사선 피부염의 치료를 위한 국소 BRaF 억제제 조성물의 용도 |
| EP4149917B1 (en) * | 2020-05-12 | 2025-07-30 | Merck Sharp & Dohme LLC | Factor xi activation inhibitors |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1056725E (pt) * | 1997-12-22 | 2006-09-29 | Bayer Pharmaceuticals Corp | Inibicao da raf-quinase usando ureias heterociclicas substituidas com arilo e heteroarilo |
| GB0005357D0 (en) * | 2000-03-06 | 2000-04-26 | Smithkline Beecham Plc | Compounds |
| ATE415162T1 (de) * | 2001-06-11 | 2008-12-15 | Vertex Pharma | Isochinolin-inhibitoren von p38 |
| US20040192689A1 (en) * | 2001-09-05 | 2004-09-30 | Dean David Kenneth | Heterocycle-carboxamide derivatives as raf kinase inhibitors |
| WO2003022832A1 (en) * | 2001-09-05 | 2003-03-20 | Smithkline Beecham P.L.C. | Pyridylfurans and pyrroles as raf kinase inhibitors |
| WO2005105777A1 (en) * | 2004-05-05 | 2005-11-10 | Pharmacia & Upjohn Company Llc | Substituted thiophene amide compounds for the treatment of inflammation |
| SE0401345D0 (sv) * | 2004-05-25 | 2004-05-25 | Astrazeneca Ab | Therapeutic compounds: Pyridine as scaffold |
| SE0401342D0 (sv) * | 2004-05-25 | 2004-05-25 | Astrazeneca Ab | Therapeutic compounds |
| KR101347303B1 (ko) * | 2010-01-29 | 2014-01-06 | 한미사이언스 주식회사 | 단백질 키나아제 저해활성을 갖는 티에노[3,2-ｄ]피리미딘 유도체 |
-
2012
- 2012-07-19 KR KR1020120078904A patent/KR20140011780A/ko not_active Withdrawn
-
2013
- 2013-07-17 JP JP2015523009A patent/JP2015522607A/ja not_active Withdrawn
- 2013-07-17 US US14/413,305 patent/US9388165B2/en not_active Expired - Fee Related
- 2013-07-17 CN CN201380038300.2A patent/CN104487420A/zh active Pending
- 2013-07-17 WO PCT/KR2013/006392 patent/WO2014014270A1/ko not_active Ceased
- 2013-07-17 EP EP13819868.4A patent/EP2876107A4/en not_active Withdrawn
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