JP2012511564A5 - - Google Patents
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- Publication number
- JP2012511564A5 JP2012511564A5 JP2011540219A JP2011540219A JP2012511564A5 JP 2012511564 A5 JP2012511564 A5 JP 2012511564A5 JP 2011540219 A JP2011540219 A JP 2011540219A JP 2011540219 A JP2011540219 A JP 2011540219A JP 2012511564 A5 JP2012511564 A5 JP 2012511564A5
- Authority
- JP
- Japan
- Prior art keywords
- tert
- butyl
- pyrazol
- tolyl
- naphthalen
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 20
- -1 4- (3- (3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl) ureido) naphthalen-1-yloxy Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 230000000155 isotopic effect Effects 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- QGSYUMLGCMFTKN-HSZRJFAPSA-N (2r)-n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-methoxypropanamide Chemical compound C1=NC(NC(=O)[C@@H](C)OC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 QGSYUMLGCMFTKN-HSZRJFAPSA-N 0.000 claims 1
- QGSYUMLGCMFTKN-QHCPKHFHSA-N (2s)-n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-methoxypropanamide Chemical compound C1=NC(NC(=O)[C@H](C)OC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 QGSYUMLGCMFTKN-QHCPKHFHSA-N 0.000 claims 1
- LJMGRXNLZNVURM-GDLZYMKVSA-N (3r)-n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]morpholine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)[C@@H]4NCCOC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 LJMGRXNLZNVURM-GDLZYMKVSA-N 0.000 claims 1
- LJMGRXNLZNVURM-LJAQVGFWSA-N (3s)-n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]morpholine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)[C@H]4NCCOC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 LJMGRXNLZNVURM-LJAQVGFWSA-N 0.000 claims 1
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- FBPBSLVHEURFAU-UHFFFAOYSA-N 1-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-1-methylurea Chemical compound C1=NC(N(C(N)=O)C)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 FBPBSLVHEURFAU-UHFFFAOYSA-N 0.000 claims 1
- GRXPDPAENZUFKQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[[2-(methylcarbamoylamino)pyridin-4-yl]methoxy]naphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 GRXPDPAENZUFKQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010012434 Dermatitis allergic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 208000029771 childhood onset asthma Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- IZVDYFCDVQANSW-UHFFFAOYSA-N n-[4-[1-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(C(C)OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 IZVDYFCDVQANSW-UHFFFAOYSA-N 0.000 claims 1
- HIVWBOCXSUYQQN-UHFFFAOYSA-N n-[4-[1-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypropan-2-yl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(C(C)COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 HIVWBOCXSUYQQN-UHFFFAOYSA-N 0.000 claims 1
- DMPPZLQPLPCJQQ-UHFFFAOYSA-N n-[4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]ethoxy]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OCCC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 DMPPZLQPLPCJQQ-UHFFFAOYSA-N 0.000 claims 1
- KXYSWSCUTMYNEX-UHFFFAOYSA-N n-[4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxy-2-methylpropyl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(CC(C)(C)OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 KXYSWSCUTMYNEX-UHFFFAOYSA-N 0.000 claims 1
- JXPFBRYPSJLQII-UHFFFAOYSA-N n-[4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(CCOC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 JXPFBRYPSJLQII-UHFFFAOYSA-N 0.000 claims 1
- SNEANVKQJYWEHG-UHFFFAOYSA-N n-[4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]pyridin-3-yl]-2-(2-methoxyethoxy)acetamide Chemical compound COCCOCC(=O)NC1=CN=CC=C1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 SNEANVKQJYWEHG-UHFFFAOYSA-N 0.000 claims 1
- OSYGDWRURYLVIZ-UHFFFAOYSA-N n-[4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxyethyl]pyridin-3-yl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=CN=CC=C1CCOC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 OSYGDWRURYLVIZ-UHFFFAOYSA-N 0.000 claims 1
- IVRDSPUIDOLQKR-UHFFFAOYSA-N n-[4-[2-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypropyl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(CC(C)OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 IVRDSPUIDOLQKR-UHFFFAOYSA-N 0.000 claims 1
- RKEMWDQHGMKDCM-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-(2-methoxyethylamino)acetamide Chemical compound C1=NC(NC(=O)CNCCOC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 RKEMWDQHGMKDCM-UHFFFAOYSA-N 0.000 claims 1
- HSAUVTQDPJVUSH-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C1CN(C)CCN1CC(=O)NC1=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=CC=N1 HSAUVTQDPJVUSH-UHFFFAOYSA-N 0.000 claims 1
- LSPOFOIAYVFYPY-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-(methylamino)acetamide Chemical compound C1=NC(NC(=O)CNC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 LSPOFOIAYVFYPY-UHFFFAOYSA-N 0.000 claims 1
- HNSNMKWKSZCKCZ-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-[(4-methoxyphenyl)methyl-methylamino]acetamide Chemical compound C1=CC(OC)=CC=C1CN(C)CC(=O)NC1=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=CC=N1 HNSNMKWKSZCKCZ-UHFFFAOYSA-N 0.000 claims 1
- APQQQTYZTVYEGV-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-[4-(2-methoxyethyl)piperazin-1-yl]acetamide Chemical compound C1CN(CCOC)CCN1CC(=O)NC1=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=CC=N1 APQQQTYZTVYEGV-UHFFFAOYSA-N 0.000 claims 1
- HZMXEQDABFTNOS-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-hydroxyacetamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)CO)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 HZMXEQDABFTNOS-UHFFFAOYSA-N 0.000 claims 1
- XMBOYOLYVHKXOL-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-methyl-2-(methylamino)propanamide Chemical compound C1=NC(NC(=O)C(C)(C)NC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 XMBOYOLYVHKXOL-UHFFFAOYSA-N 0.000 claims 1
- IXWAAWQRRFJLQU-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-methylsulfanylacetamide Chemical compound C1=NC(NC(=O)CSC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 IXWAAWQRRFJLQU-UHFFFAOYSA-N 0.000 claims 1
- NHZOGUOTZAGGRM-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-methylsulfinylacetamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)CS(C)=O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 NHZOGUOTZAGGRM-UHFFFAOYSA-N 0.000 claims 1
- UBWALTPIDHCQBF-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-morpholin-4-ylacetamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)CN4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 UBWALTPIDHCQBF-UHFFFAOYSA-N 0.000 claims 1
- WFJLURLWTCHRMQ-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-2-pyrrolidin-1-ylacetamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)CN4CCCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 WFJLURLWTCHRMQ-UHFFFAOYSA-N 0.000 claims 1
- HDCPXJGHIXMQRE-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-3-methoxypropanamide Chemical compound C1=NC(NC(=O)CCOC)=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=C1 HDCPXJGHIXMQRE-UHFFFAOYSA-N 0.000 claims 1
- RVRBIRJDPKWHFW-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-3-methylsulfonyl-2-oxoimidazolidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)N4C(N(CC4)S(C)(=O)=O)=O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 RVRBIRJDPKWHFW-UHFFFAOYSA-N 0.000 claims 1
- QMYOLTHWRAVWHD-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-3-methylsulfonylpropanamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)CCS(C)(=O)=O)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 QMYOLTHWRAVWHD-UHFFFAOYSA-N 0.000 claims 1
- PLYNOQRDVZFNRR-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC(COC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(C)=CC=3)=CC=2)=CC=N1 PLYNOQRDVZFNRR-UHFFFAOYSA-N 0.000 claims 1
- WQJBZQGFGJVAEK-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]morpholine-4-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)N4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 WQJBZQGFGJVAEK-UHFFFAOYSA-N 0.000 claims 1
- UTKDGEYLIRNNON-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-2-yl]oxane-4-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OCC=3C=C(NC(=O)C4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 UTKDGEYLIRNNON-UHFFFAOYSA-N 0.000 claims 1
- PVBNMOSWYWSNHS-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-3-yl]-2-(2-methoxyethoxy)acetamide Chemical compound COCCOCC(=O)NC1=CN=CC=C1COC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 PVBNMOSWYWSNHS-UHFFFAOYSA-N 0.000 claims 1
- DQTZMOTXLGCWQY-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxymethyl]pyridin-3-yl]-2-methoxyacetamide Chemical compound COCC(=O)NC1=CN=CC=C1COC(C1=CC=CC=C11)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=C(C)C=C1 DQTZMOTXLGCWQY-UHFFFAOYSA-N 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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| DK2531502T3 (da) | 2010-02-01 | 2014-05-19 | Cancer Rec Tech Ltd | 1-(5-tert-butyl-2-phenyl-2h-pyrazol-3-yl)-3-[2-fluoro-4-(1-methyl-2-oxo-2,3-dihydro-1h-imidazo[4,5-b]pyridin-7-yloxy)-phenyl]-urea og associerede forbindelser og ders anvendelse i terapi |
| GB201005589D0 (en) | 2010-04-01 | 2010-05-19 | Respivert Ltd | Novel compounds |
| EP2556068B1 (en) * | 2010-04-08 | 2019-01-23 | Respivert Limited | P38 map kinase inhibitors |
| JP5787976B2 (ja) | 2010-04-08 | 2015-09-30 | レスピバート・リミテツド | Ｐ３８ｍａｐキナーゼ阻害剤としてのピラゾリルウレア |
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| GB201010193D0 (en) * | 2010-06-17 | 2010-07-21 | Respivert Ltd | Medicinal use |
| US8933228B2 (en) | 2010-06-17 | 2015-01-13 | Respivert, Ltd. | Respiratory formulations and compounds for use therein |
| EP2578582A1 (en) | 2011-10-03 | 2013-04-10 | Respivert Limited | 1-Pyrazolyl-3-(4-((2-anilinopyrimidin-4-yl)oxy)napththalen-1-yl)ureas as p38 MAP kinase inhibitors |
| PL2763984T3 (pl) | 2011-10-03 | 2016-10-31 | 1-pirazolilo-3-(4-((2-anilinopirymidyno-4-ilo)oksy)naftaleno-1-ilo)moczniki jako inhibitory kinazy p38 MAP | |
| SG11201402985VA (en) * | 2011-12-09 | 2014-08-28 | Chiesi Farma Spa | Kinase inhibitors |
| GB201214750D0 (en) * | 2012-08-17 | 2012-10-03 | Respivert Ltd | Compounds |
| EP2890460B1 (en) | 2012-08-29 | 2017-02-22 | Respivert Limited | Kinase inhibitors |
| WO2014033447A2 (en) | 2012-08-29 | 2014-03-06 | Respivert Limited | Kinase inhibitors |
| GB201215357D0 (en) * | 2012-08-29 | 2012-10-10 | Respivert Ltd | Compounds |
| US9783556B2 (en) | 2012-08-29 | 2017-10-10 | Respivert Limited | Kinase inhibitors |
| US11052202B2 (en) * | 2012-11-07 | 2021-07-06 | Chiesi Farmaceutici S.P.A. | Drug delivery device for the treatment of patients with respiratory diseases |
| EP2925742B1 (en) | 2012-11-16 | 2016-10-26 | Respivert Limited | Kinase inhibitors |
| EP2970190A1 (en) | 2013-03-14 | 2016-01-20 | Respivert Limited | Kinase inhibitors |
| EP2981534B1 (en) | 2013-04-02 | 2017-07-19 | Topivert Pharma Limited | Kinase inhibitors based upon n-alkyl pyrazoles |
| EP2981535B8 (en) | 2013-04-02 | 2021-03-10 | Oxular Acquisitions Limited | Urea derivatives useful as kinase inhibitors |
| GB201320729D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
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| JP6514703B2 (ja) | 2013-12-20 | 2019-05-15 | トピバート ファーマ リミテッド | キナーゼインヒビターとして有用な尿素誘導体 |
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| MA40775A (fr) | 2014-10-01 | 2017-08-08 | Respivert Ltd | Dérivé d'acide 4-(4-(4-phényluréido-naphtalén -1-yl) oxy-pyridin-2-yl) amino-benzoïque utilisé en tant qu'inhibiteur de la kinase p38 |
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| CA3142097A1 (en) | 2018-05-30 | 2019-12-05 | Washington University | Mitogen-activated protein kinase inhibitors, methods of making, and methods of use thereof |
| US12636290B2 (en) | 2018-12-20 | 2026-05-26 | Saint Louis University | BET inhibitors for modulating DUX4 expression in FSHD |
| CN114144410A (zh) * | 2019-07-19 | 2022-03-04 | 阿纳格纳斯生物技术股份有限公司 | 多芳基脲衍生物及其在治疗肌肉疾病中的用途 |
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2014
- 2014-09-16 JP JP2014187591A patent/JP5959587B2/ja active Active
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