JP2013523803A5 - - Google Patents
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- Publication number
- JP2013523803A5 JP2013523803A5 JP2013503179A JP2013503179A JP2013523803A5 JP 2013523803 A5 JP2013523803 A5 JP 2013523803A5 JP 2013503179 A JP2013503179 A JP 2013503179A JP 2013503179 A JP2013503179 A JP 2013503179A JP 2013523803 A5 JP2013523803 A5 JP 2013523803A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- ureido
- butyl
- tert
- alkyl
- 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 56
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 229920006395 saturated elastomer Chemical group 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- -1 n- propyl Chemical group 0.000 claims 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- BAAZNQMHGAJUKC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-hydroxyphenyl)pyrazol-3-yl]-3-[4-[2-(methylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(O)=CC=3)=CC=2)=C1 BAAZNQMHGAJUKC-UHFFFAOYSA-N 0.000 claims 1
- UXSYOKKSKHTJCG-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[2-(methylcarbamoylamino)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OC)=CC=3)=CC=2)C)=C1 UXSYOKKSKHTJCG-UHFFFAOYSA-N 0.000 claims 1
- RAJPOWOOQITCKX-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[[2-(methylcarbamoylamino)pyridin-4-yl]methoxy]phenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(COC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OC)=CC=3)=CC=2)C)=C1 RAJPOWOOQITCKX-UHFFFAOYSA-N 0.000 claims 1
- REMRQAOIHZTZTB-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[4-[2-(cyclopropylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)NC4CC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 REMRQAOIHZTZTB-UHFFFAOYSA-N 0.000 claims 1
- HOCYOIBNXANDRC-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]-3-[4-[2-(methylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OC)=CC=3)=CC=2)=C1 HOCYOIBNXANDRC-UHFFFAOYSA-N 0.000 claims 1
- FXHRTJVOUZTXKW-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[2-(ethylcarbamoylamino)pyridine-4-carbonyl]naphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC(C(=O)C=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 FXHRTJVOUZTXKW-UHFFFAOYSA-N 0.000 claims 1
- KNWDOMXCLISYFK-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-[[2-(ethylcarbamoylamino)pyridin-4-yl]methyl]naphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC(CC=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 KNWDOMXCLISYFK-UHFFFAOYSA-N 0.000 claims 1
- QCQFJYFNNAVHMV-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylsulfonylphenyl)pyrazol-3-yl]-3-[4-[2-(carbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC(NC(N)=O)=C1 QCQFJYFNNAVHMV-UHFFFAOYSA-N 0.000 claims 1
- CEDVHDWQBBGGJQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(4-methylsulfonylphenyl)pyrazol-3-yl]-3-[4-[2-(methylcarbamoylamino)pyridin-4-yl]oxynaphthalen-1-yl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(=CC=3)S(C)(=O)=O)=CC=2)=C1 CEDVHDWQBBGGJQ-UHFFFAOYSA-N 0.000 claims 1
- XEWJIUDGHQKAPZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[2-(methylcarbamoylamino)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(OC)=CC=3)=CC=2)C)=C1 XEWJIUDGHQKAPZ-UHFFFAOYSA-N 0.000 claims 1
- ZXPAZNSFKLHNLZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[[2-(methylcarbamoylamino)pyridin-4-yl]methoxy]phenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(COC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(OC)=CC=3)=CC=2)C)=C1 ZXPAZNSFKLHNLZ-UHFFFAOYSA-N 0.000 claims 1
- FUDOCSOWCGXJEP-UHFFFAOYSA-N 1-[5-tert-butyl-2-(6-oxo-1h-pyridin-3-yl)pyrazol-3-yl]-3-[2,3-dimethyl-4-[2-(methylcarbamoylamino)pyridin-4-yl]oxyphenyl]urea Chemical compound C1=NC(NC(=O)NC)=CC(OC=2C(=C(C)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(O)=CC=3)=CC=2)C)=C1 FUDOCSOWCGXJEP-UHFFFAOYSA-N 0.000 claims 1
- TXLZRMRCAWLPKZ-UHFFFAOYSA-N 3-[4-[4-[[5-tert-butyl-2-(4-hydroxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-1,1-dimethylurea Chemical compound C1=NC(NC(=O)N(C)C)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(O)=CC=3)=CC=2)=C1 TXLZRMRCAWLPKZ-UHFFFAOYSA-N 0.000 claims 1
- CGYNVARIYRLGPV-UHFFFAOYSA-N 3-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-1,1-dimethylurea Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N(C)C)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 CGYNVARIYRLGPV-UHFFFAOYSA-N 0.000 claims 1
- QLCOCTLVZFWKRP-UHFFFAOYSA-N 3-[4-[4-[[5-tert-butyl-2-(4-methylsulfonylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-1,1-dimethylurea Chemical compound C1=NC(NC(=O)N(C)C)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(=CC=3)S(C)(=O)=O)=CC=2)=C1 QLCOCTLVZFWKRP-UHFFFAOYSA-N 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
- 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
- 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
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms 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
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 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
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 208000029771 childhood onset asthma Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000000155 isotopic effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims 1
- NOVWYWPZOJAODC-UHFFFAOYSA-N n-[4-[4-[(2,5-diphenylpyrazol-3-yl)carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)=C1 NOVWYWPZOJAODC-UHFFFAOYSA-N 0.000 claims 1
- SPZXTRXIPUADKG-UHFFFAOYSA-N n-[4-[4-[(5-tert-butyl-2-thiophen-2-ylpyrazol-3-yl)carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3SC=CC=3)=CC=2)=C1 SPZXTRXIPUADKG-UHFFFAOYSA-N 0.000 claims 1
- PDUPWPQJHADVSR-UHFFFAOYSA-N n-[4-[4-[[2-(4-aminophenyl)-5-tert-butylpyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(N)=CC=3)=CC=2)=C1 PDUPWPQJHADVSR-UHFFFAOYSA-N 0.000 claims 1
- OOVJKYSJTMRXCK-UHFFFAOYSA-N n-[4-[4-[[5-(1-adamantyl)-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C34CC5CC(CC(C5)C3)C4)C=3C=CC(C)=CC=3)=CC=2)=C1 OOVJKYSJTMRXCK-UHFFFAOYSA-N 0.000 claims 1
- GKDITMSSYMDGEE-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3,4-dichlorophenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(Cl)C(Cl)=CC=3)=CC=2)=C1 GKDITMSSYMDGEE-UHFFFAOYSA-N 0.000 claims 1
- DEORIXCEYCRSSH-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3,4-dimethoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(OC)C(OC)=CC=3)=CC=2)=C1 DEORIXCEYCRSSH-UHFFFAOYSA-N 0.000 claims 1
- YVPZFRVWTNGMDX-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3,5-dimethoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(OC)C=C(OC)C=3)=CC=2)=C1 YVPZFRVWTNGMDX-UHFFFAOYSA-N 0.000 claims 1
- SIEQNPMZCSPWBA-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-chloro-4-hydroxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(Cl)C(O)=CC=3)=CC=2)=C1 SIEQNPMZCSPWBA-UHFFFAOYSA-N 0.000 claims 1
- UDVGHGVLKNJSGE-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-chloro-4-hydroxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]morpholine-4-carboxamide Chemical compound C=1C=C(O)C(Cl)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCOCC1 UDVGHGVLKNJSGE-UHFFFAOYSA-N 0.000 claims 1
- MUXUVQHJDDBLAQ-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-chloro-4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(Cl)C(OC)=CC=3)=CC=2)=C1 MUXUVQHJDDBLAQ-UHFFFAOYSA-N 0.000 claims 1
- SONLMYWONGIPSC-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-hydroxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(O)C=CC=3)=CC=2)=C1 SONLMYWONGIPSC-UHFFFAOYSA-N 0.000 claims 1
- KZHKFNGYOQGDGC-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(3-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(OC)C=CC=3)=CC=2)=C1 KZHKFNGYOQGDGC-UHFFFAOYSA-N 0.000 claims 1
- LNUAWYSLDCYQNG-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-chlorophenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(Cl)=CC=3)=CC=2)=C1 LNUAWYSLDCYQNG-UHFFFAOYSA-N 0.000 claims 1
- XCORBYUCTBFULC-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-hydroxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(O)=CC=3)=CC=2)=C1 XCORBYUCTBFULC-UHFFFAOYSA-N 0.000 claims 1
- GJVOUJIAGSXPAY-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-hydroxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]pyrrolidine-1-carboxamide Chemical compound C=1C=C(O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCCC1 GJVOUJIAGSXPAY-UHFFFAOYSA-N 0.000 claims 1
- YUWFIAFUXFJDSK-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-hydroxyacetamide Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)CO)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 YUWFIAFUXFJDSK-UHFFFAOYSA-N 0.000 claims 1
- ACGOXIBULCMWDN-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OC)=CC=3)=CC=2)=C1 ACGOXIBULCMWDN-UHFFFAOYSA-N 0.000 claims 1
- VYHJIODJURYDIL-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N4CCN(C)CC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 VYHJIODJURYDIL-UHFFFAOYSA-N 0.000 claims 1
- PNELWARZRKUBQR-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]morpholine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 PNELWARZRKUBQR-UHFFFAOYSA-N 0.000 claims 1
- UUSMBDZMBKUGSR-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methoxyphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]pyrrolidine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N4CCCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 UUSMBDZMBKUGSR-UHFFFAOYSA-N 0.000 claims 1
- JWQPLLQYCQUFNM-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalene-1-carbonyl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(C(=O)C=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 JWQPLLQYCQUFNM-UHFFFAOYSA-N 0.000 claims 1
- QEQJMKODCWIMAU-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylsulfanylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(SC)=CC=3)=CC=2)=C1 QEQJMKODCWIMAU-UHFFFAOYSA-N 0.000 claims 1
- ZMVXVIQHVGSSDJ-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylsulfanylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]pyrrolidine-1-carboxamide Chemical compound C1=CC(SC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N4CCCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 ZMVXVIQHVGSSDJ-UHFFFAOYSA-N 0.000 claims 1
- XCJUKXAWFBFKDY-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylsulfonylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-4-methylpiperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(=CC=3)S(C)(=O)=O)=CC=2)=CC=N1 XCJUKXAWFBFKDY-UHFFFAOYSA-N 0.000 claims 1
- MVBMAFBEMMLDKV-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(4-methylthiophen-2-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3SC=C(C)C=3)=CC=2)=C1 MVBMAFBEMMLDKV-UHFFFAOYSA-N 0.000 claims 1
- XCEGLQUWDMQQQX-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(OC)=CC=3)=CC=2)=C1 XCEGLQUWDMQQQX-UHFFFAOYSA-N 0.000 claims 1
- JQHPFXVXGAPMES-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(6-methoxypyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]morpholine-4-carboxamide Chemical compound C1=NC(OC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)N4CCOCC4)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 JQHPFXVXGAPMES-UHFFFAOYSA-N 0.000 claims 1
- SYMPONWHLIDPNN-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(6-methylpyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(C)=CC=3)=CC=2)=C1 SYMPONWHLIDPNN-UHFFFAOYSA-N 0.000 claims 1
- SYVQLNROXIEGOT-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-(6-oxo-1h-pyridin-3-yl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=NC(O)=CC=3)=CC=2)=C1 SYVQLNROXIEGOT-UHFFFAOYSA-N 0.000 claims 1
- DKVWTFUUDJQELK-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-[3-chloro-4-(hydroxymethyl)phenyl]pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(Cl)C(CO)=CC=3)=CC=2)=C1 DKVWTFUUDJQELK-UHFFFAOYSA-N 0.000 claims 1
- PIZQECUMSIAARP-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-[4-(hydroxymethyl)-3-methoxyphenyl]pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(OC)C(CO)=CC=3)=CC=2)=C1 PIZQECUMSIAARP-UHFFFAOYSA-N 0.000 claims 1
- DRJCTBLDJCCETA-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-[4-(methanesulfonamido)phenyl]pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(NS(C)(=O)=O)=CC=3)=CC=2)=C1 DRJCTBLDJCCETA-UHFFFAOYSA-N 0.000 claims 1
- YNQFZXULMNSALD-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-[4-(methylsulfamoylmethyl)phenyl]pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=CC(CS(=O)(=O)NC)=CC=C1N1C(NC(=O)NC=2C3=CC=CC=C3C(OC=3C=C(NC(=O)COC)N=CC=3)=CC=2)=CC(C(C)(C)C)=N1 YNQFZXULMNSALD-UHFFFAOYSA-N 0.000 claims 1
- UMYVLHJHBAEUEE-UHFFFAOYSA-N n-[4-[4-[[5-tert-butyl-2-[4-(trifluoromethoxy)phenyl]pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1 UMYVLHJHBAEUEE-UHFFFAOYSA-N 0.000 claims 1
- SDYDBQWZPWZQSZ-UHFFFAOYSA-N n-[4-[[4-[[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]methyl]pyridin-2-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(CC=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 SDYDBQWZPWZQSZ-UHFFFAOYSA-N 0.000 claims 1
- NXERXVHEQFSTEQ-UHFFFAOYSA-N n-[6-[4-[[5-tert-butyl-2-(4-methylsulfonylphenyl)pyrazol-3-yl]carbamoylamino]naphthalen-1-yl]oxypyrimidin-4-yl]-2-methoxyacetamide Chemical compound C1=NC(NC(=O)COC)=CC(OC=2C3=CC=CC=C3C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(=CC=3)S(C)(=O)=O)=CC=2)=N1 NXERXVHEQFSTEQ-UHFFFAOYSA-N 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 201000001276 rectum malignant melanoma Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
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| EP2229391B1 (en) | 2007-12-19 | 2014-08-06 | Cancer Research Technology Limited | Pyrido[2,3-b]pyrazine-8-substituted compounds and their use |
| GB0905955D0 (en) | 2009-04-06 | 2009-05-20 | Respivert Ltd | Novel compounds |
| CA2786834C (en) | 2010-02-01 | 2018-10-16 | Cancer Research Technology Limited | 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 and related compounds and their use in therapy |
| GB201005589D0 (en) | 2010-04-01 | 2010-05-19 | Respivert Ltd | Novel compounds |
| WO2011124923A2 (en) | 2010-04-08 | 2011-10-13 | Respivert Limited | Novel compounds |
| US8933228B2 (en) | 2010-06-17 | 2015-01-13 | Respivert, Ltd. | Respiratory formulations and compounds for use therein |
| GB201010193D0 (en) | 2010-06-17 | 2010-07-21 | Respivert Ltd | Medicinal use |
| PH12014500547A1 (en) | 2011-10-03 | 2014-04-21 | Respivert Ltd | 1-pyrazolyl-3-(-4-((2-anilinopyrimidin-4-yl)oxy)napththalen-1-yl)ureas as p38 map kinase inhibitors |
| 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 |
| MY170656A (en) * | 2011-12-09 | 2019-08-24 | Chiesi Farm Spa | Kinase inhibitors |
| MY167216A (en) * | 2011-12-09 | 2018-08-14 | Chiesi Farm Spa | Kinase inhibitors |
| GB201214750D0 (en) * | 2012-08-17 | 2012-10-03 | Respivert Ltd | Compounds |
| US20150210722A1 (en) | 2012-08-29 | 2015-07-30 | Respivert Limited | Kinase inhibitors |
| WO2014033449A1 (en) | 2012-08-29 | 2014-03-06 | Respivert Limited | Kinase inhibitors |
| GB201215357D0 (en) * | 2012-08-29 | 2012-10-10 | Respivert Ltd | Compounds |
| EP2890695A2 (en) * | 2012-08-29 | 2015-07-08 | Respivert Limited | Kinase inhibitors |
| WO2014076484A1 (en) * | 2012-11-16 | 2014-05-22 | Respivert Limited | Kinase inhibitors |
| JP6256771B2 (ja) | 2012-12-06 | 2018-01-10 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
| WO2014140582A1 (en) * | 2013-03-14 | 2014-09-18 | Respivert Limited | Kinase inhibitors |
| ES2856902T3 (es) | 2013-04-02 | 2021-09-28 | Oxular Acquisitions Ltd | Derivados de urea útiles como inhibidores de quinasa |
| EP2981534B1 (en) | 2013-04-02 | 2017-07-19 | Topivert Pharma Limited | Kinase inhibitors based upon n-alkyl pyrazoles |
| HRP20191298T1 (hr) | 2013-09-09 | 2019-10-18 | Peloton Therapeutics, Inc. | Arileteri i njihove uporabe |
| GB201320732D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Methods of chemical synthesis |
| GB201320729D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| CN113717162A (zh) | 2013-12-20 | 2021-11-30 | 奥苏拉收购有限公司 | 用作激酶抑制剂的脲衍生物 |
| JP6586098B2 (ja) | 2014-02-14 | 2019-10-02 | レスピバート・リミテツド | キナーゼ阻害剤としてのピラゾリル尿素 |
| MA40774A (fr) | 2014-10-01 | 2017-08-08 | Respivert Ltd | Dérivés de diaryle-urée en tant qu'inhibiteurs de kinase p38 |
| WO2016144826A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Substituted pyridines and uses thereof |
| WO2016144825A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
| WO2016145045A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Compositions for use in treating glioblastoma |
| WO2016145032A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Compositions for use in treating pulmonary arterial hypertension |
| US10335388B2 (en) | 2015-04-17 | 2019-07-02 | Peloton Therapeutics, Inc. | Combination therapy of a HIF-2-alpha inhibitor and an immunotherapeutic agent and uses thereof |
| MA44607A (fr) | 2016-04-06 | 2021-05-19 | Oxular Acquisitions Ltd | Inhibiteurs de kinase |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN110041173A (zh) * | 2019-05-10 | 2019-07-23 | 贵州医科大学 | 一种新的白藜芦醇及其衍生物合成方法及应用 |
| US20230089368A1 (en) | 2019-07-19 | 2023-03-23 | Anagenesis Biotechnologies S.A.S. | Polyaromatic urea derivatives and their use in the treatment of muscle diseases |
| EP4029501A1 (en) | 2021-01-19 | 2022-07-20 | Anagenesis Biotechnologies | Combination of polyaromatic urea derivatives and glucocorticoid or hdac inhibitor for the treatment of diseases or conditions associated with muscle cells and/or satellite cells |
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| US20080300281A1 (en) * | 1997-12-22 | 2008-12-04 | Jacques Dumas | Inhibition of p38 Kinase Activity Using Aryl and Heteroaryl Substituted Heterocyclic Ureas |
| UA73492C2 (en) | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| HUP0202248A3 (en) | 1999-03-12 | 2006-06-28 | Boehringer Ingelheim Pharma | Compounds useful as anti-inflammatory agents |
| AU2003213806A1 (en) | 2002-02-25 | 2003-09-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-disubstituted benzofused cycloalkyl urea compounds useful in treating cytokine mediated diseases |
| CA2489337C (en) | 2002-06-24 | 2010-05-25 | Schering Corporation | Indole derivatives useful as histamine h3 antagonists |
| GB0320244D0 (en) | 2003-05-06 | 2003-10-01 | Aventis Pharma Inc | Pyrazoles as inhibitors of tumour necrosis factor |
| US7838524B2 (en) | 2004-04-30 | 2010-11-23 | Bayer Healthcare Llc | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
| US7829560B2 (en) | 2004-07-08 | 2010-11-09 | Arqule, Inc. | 1,4-disubstituted naphthalenes as inhibitors of P38 MAP kinase |
| PL1778686T3 (pl) | 2004-08-12 | 2009-04-30 | Pfizer | Pochodne triazolopirydynylosulfanylowe jako inhibitory kinazy MAP P38 |
| US20070078121A1 (en) * | 2004-12-23 | 2007-04-05 | Flynn Daniel L | Enzyme modulators and treatments |
| GB0500435D0 (en) | 2005-01-10 | 2005-02-16 | Novartis Ag | Organic compounds |
| AR056582A1 (es) | 2005-10-28 | 2007-10-10 | Lilly Co Eli | COMPUESTOS DE PIRAZOLIL UREA CON ACTIVIDAD INHIBITORIA DE CINASA P38 Y FORMULACIoN FARMACÉUTICA QUE LO COMPRENDE |
| MX2008006979A (es) | 2005-12-01 | 2009-01-14 | Bayer Healthcare Llc | Compuestos de urea utiles en el tratamiento contra el cancer. |
| ATE539748T1 (de) | 2006-01-27 | 2012-01-15 | Array Biopharma Inc | Glucokinaseaktivatoren |
| KR20080081359A (ko) | 2006-01-30 | 2008-09-09 | 아이알엠 엘엘씨 | Ｐｐａｒ 조절제로서의 스피로 이미다졸 유도체 |
| CA2640665A1 (en) | 2006-02-10 | 2007-08-16 | Pfizer Products Inc. | Pyridinone pyrazole urea and pyrimidinone pyrazole urea derivatives |
| AR065858A1 (es) | 2007-03-29 | 2009-07-08 | Sanofi Aventis | Metodo para preparar el inhibidor de triptasa [ 4-(5-aminoetil-2-fluoro-fenil)-piperidin-1-il]-(4-bromo-3-metil-5-propoxi-tiofen-2-il)-metanona. |
| WO2008125014A1 (fr) | 2007-04-13 | 2008-10-23 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. | Composés d'urée, leurs procédés de préparation et leurs utilisations pharmaceutiques |
| EP2229391B1 (en) | 2007-12-19 | 2014-08-06 | Cancer Research Technology Limited | Pyrido[2,3-b]pyrazine-8-substituted compounds and their use |
| HUE025197T2 (en) | 2008-03-17 | 2016-02-29 | Ambit Biosciences Corp | Quinazoline derivatives as RAF kinase modulators and methods for their use |
| US8293748B2 (en) * | 2008-10-02 | 2012-10-23 | Respivert Ltd. | p38 MAP kinase inhibitors |
| GB0818033D0 (en) * | 2008-10-02 | 2008-11-05 | Respivert Ltd | Novel compound |
| JP5670912B2 (ja) * | 2008-12-11 | 2015-02-18 | レスピバート・リミテツド | ｐ３８ＭＡＰキナーゼ阻害剤 |
| GB0905955D0 (en) | 2009-04-06 | 2009-05-20 | Respivert Ltd | Novel compounds |
| GB0921730D0 (en) | 2009-12-11 | 2010-01-27 | Respivert Ltd | Method of treatment |
| GB201005589D0 (en) | 2010-04-01 | 2010-05-19 | Respivert Ltd | Novel compounds |
| WO2011124923A2 (en) | 2010-04-08 | 2011-10-13 | Respivert Limited | Novel compounds |
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