HRP20110757T1 - Inhibitori kinaze p38 bazirani na 5-članom heterociklu - Google Patents
Inhibitori kinaze p38 bazirani na 5-članom heterociklu Download PDFInfo
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- HRP20110757T1 HRP20110757T1 HR20110757T HRP20110757T HRP20110757T1 HR P20110757 T1 HRP20110757 T1 HR P20110757T1 HR 20110757 T HR20110757 T HR 20110757T HR P20110757 T HRP20110757 T HR P20110757T HR P20110757 T1 HRP20110757 T1 HR P20110757T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- amino
- benzamide
- benzoyl
- cyclopropyl
- Prior art date
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- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract 63
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 title claims abstract 9
- 229940043355 kinase inhibitor Drugs 0.000 title abstract 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 131
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract 7
- 230000001404 mediated effect Effects 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims abstract 5
- 208000024891 symptom Diseases 0.000 claims abstract 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims abstract 4
- 208000027866 inflammatory disease Diseases 0.000 claims abstract 3
- 239000003112 inhibitor Substances 0.000 claims abstract 2
- 230000002265 prevention Effects 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 122
- 239000001257 hydrogen Substances 0.000 claims 122
- 125000000217 alkyl group Chemical group 0.000 claims 112
- 125000001072 heteroaryl group Chemical group 0.000 claims 95
- 150000002431 hydrogen Chemical class 0.000 claims 83
- -1 2-methylcyclohexyl Chemical group 0.000 claims 72
- 125000004404 heteroalkyl group Chemical group 0.000 claims 52
- 125000003118 aryl group Chemical group 0.000 claims 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 33
- 125000003342 alkenyl group Chemical group 0.000 claims 24
- 125000000304 alkynyl group Chemical group 0.000 claims 23
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 23
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- 125000001475 halogen functional group Chemical group 0.000 claims 17
- 125000002947 alkylene group Chemical group 0.000 claims 13
- 125000004474 heteroalkylene group Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims 12
- 125000004450 alkenylene group Chemical group 0.000 claims 11
- 125000004419 alkynylene group Chemical group 0.000 claims 11
- 208000035475 disorder Diseases 0.000 claims 11
- 229910020008 S(O) Inorganic materials 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims 8
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- CAZKPJSLYJYCFJ-UHFFFAOYSA-N 3-[5-amino-4-[3-(morpholin-4-ylmethyl)benzoyl]pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C(C=1)=CC=CC=1CN1CCOCC1 CAZKPJSLYJYCFJ-UHFFFAOYSA-N 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000004405 heteroalkoxy group Chemical group 0.000 claims 5
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- BPJJMPRXNWUAIA-UHFFFAOYSA-N 3-(5-amino-4-benzoylimidazol-1-yl)-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)C=NC=1C(=O)C1=CC=CC=C1 BPJJMPRXNWUAIA-UHFFFAOYSA-N 0.000 claims 4
- RGKYHHGPQQXTHO-UHFFFAOYSA-N 3-(5-amino-4-benzoylpyrazol-1-yl)-n-methoxy-4-methylbenzamide Chemical compound CONC(=O)C1=CC=C(C)C(N2C(=C(C(=O)C=3C=CC=CC=3)C=N2)N)=C1 RGKYHHGPQQXTHO-UHFFFAOYSA-N 0.000 claims 4
- ACDYVZWXLZVGKZ-UHFFFAOYSA-N 3-[5-amino-4-(3-formylbenzoyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC(C=O)=C1 ACDYVZWXLZVGKZ-UHFFFAOYSA-N 0.000 claims 4
- DKDNHRIIFVRZJH-UHFFFAOYSA-N 3-[5-amino-4-(3-hydroxybenzoyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC(O)=C1 DKDNHRIIFVRZJH-UHFFFAOYSA-N 0.000 claims 4
- OKCYOLQZTMDRPD-UHFFFAOYSA-N 3-[5-amino-4-(3-iodobenzoyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC(I)=C1 OKCYOLQZTMDRPD-UHFFFAOYSA-N 0.000 claims 4
- QYVPOKVLADAONJ-UHFFFAOYSA-N 3-[5-amino-4-(3-iodobenzoyl)pyrazol-1-yl]-n-methoxy-4-methylbenzamide Chemical compound CONC(=O)C1=CC=C(C)C(N2C(=C(C(=O)C=3C=C(I)C=CC=3)C=N2)N)=C1 QYVPOKVLADAONJ-UHFFFAOYSA-N 0.000 claims 4
- PBHVNTIQHGFUCT-UHFFFAOYSA-N 3-[5-amino-4-(3-phenylmethoxybenzoyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C(C=1)=CC=CC=1OCC1=CC=CC=C1 PBHVNTIQHGFUCT-UHFFFAOYSA-N 0.000 claims 4
- IJWYKDHNLGMUKF-UHFFFAOYSA-N 3-[5-amino-4-(4-methylbenzoyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)C1=C(N)N(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)N=C1 IJWYKDHNLGMUKF-UHFFFAOYSA-N 0.000 claims 4
- QIZLEKIZUYDILF-UHFFFAOYSA-N 3-[5-amino-4-[3-(1,3-dioxolan-2-yl)benzoyl]pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C(C=1)=CC=CC=1C1OCCO1 QIZLEKIZUYDILF-UHFFFAOYSA-N 0.000 claims 4
- QBCXJPAVGCSFQD-UHFFFAOYSA-N 3-[5-amino-4-[3-(hydroxymethyl)benzoyl]pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC(CO)=C1 QBCXJPAVGCSFQD-UHFFFAOYSA-N 0.000 claims 4
- CGIARXZERAUCBG-UHFFFAOYSA-N 3-[5-amino-4-[3-[(4-methylpiperazin-1-yl)methyl]benzoyl]pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound C1CN(C)CCN1CC1=CC=CC(C(=O)C2=C(N(N=C2)C=2C(=CC=C(C=2)C(=O)NC2CC2)C)N)=C1 CGIARXZERAUCBG-UHFFFAOYSA-N 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- QBXUCRNTPWWBJY-UHFFFAOYSA-N [5-amino-1-[2-methyl-5-(1h-1,2,4-triazol-5-yl)phenyl]pyrazol-4-yl]-phenylmethanone Chemical compound CC1=CC=C(C=2NC=NN=2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC=C1 QBXUCRNTPWWBJY-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000004442 acylamino group Chemical group 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 150000001412 amines Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 4
- 125000004001 thioalkyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- RVFOYWCXKPKCPB-UHFFFAOYSA-N 3-(5-amino-4-benzoyl-3-methoxypyrazol-1-yl)-n-cyclopropyl-4-methylbenzamide Chemical compound COC1=NN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C(N)=C1C(=O)C1=CC=CC=C1 RVFOYWCXKPKCPB-UHFFFAOYSA-N 0.000 claims 3
- VTWKMMRTCFYHHB-UHFFFAOYSA-N 3-(5-amino-4-benzoylpyrazol-1-yl)-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N1C(N)=C(C(=O)C=2C=CC=CC=2)C=N1 VTWKMMRTCFYHHB-UHFFFAOYSA-N 0.000 claims 3
- YKRHGHVJNYCHEN-UHFFFAOYSA-N 3-(5-amino-4-benzoylpyrazol-1-yl)-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC=C1 YKRHGHVJNYCHEN-UHFFFAOYSA-N 0.000 claims 3
- DDIILOABHXYXGH-UHFFFAOYSA-N 3-(5-amino-4-benzoylpyrazol-1-yl)-n-cyclopropyl-4-methylbenzamide;3-[5-amino-4-(3-iodobenzoyl)pyrazol-1-yl]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N1C(N)=C(C(=O)C=2C=C(I)C=CC=2)C=N1.CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC=C1 DDIILOABHXYXGH-UHFFFAOYSA-N 0.000 claims 3
- VGUSQKZDZHAAEE-UHFFFAOYSA-N 3-[5-amino-4-(3-cyanobenzoyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=CC(C#N)=C1 VGUSQKZDZHAAEE-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 108091000080 Phosphotransferase Proteins 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 102000020233 phosphotransferase Human genes 0.000 claims 3
- 125000002577 pseudohalo group Chemical group 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 3
- SJSSFUMSAFMFNM-NSHDSACASA-N (2s)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 SJSSFUMSAFMFNM-NSHDSACASA-N 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- ZWWMSWCLDWRNLU-UHFFFAOYSA-N 3-(5-amino-4-benzoyl-3-methylsulfanylpyrazol-1-yl)-n-cyclopropyl-4-methylbenzamide Chemical compound CSC1=NN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C(N)=C1C(=O)C1=CC=CC=C1 ZWWMSWCLDWRNLU-UHFFFAOYSA-N 0.000 claims 2
- MRDFLILXEIMYNW-UHFFFAOYSA-N 3-(5-amino-4-benzoyl-3-methylsulfonylpyrazol-1-yl)-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=C(S(C)(=O)=O)C=1C(=O)C1=CC=CC=C1 MRDFLILXEIMYNW-UHFFFAOYSA-N 0.000 claims 2
- FWAMSEZFYAFSPS-UHFFFAOYSA-N 3-[5-amino-4-(2-phenylacetyl)imidazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)C=NC=1C(=O)CC1=CC=CC=C1 FWAMSEZFYAFSPS-UHFFFAOYSA-N 0.000 claims 2
- LPWHASBJQWRCFT-UHFFFAOYSA-N 3-[5-amino-4-(3-pyrimidin-5-ylbenzoyl)imidazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)C=NC=1C(=O)C(C=1)=CC=CC=1C1=CN=CN=C1 LPWHASBJQWRCFT-UHFFFAOYSA-N 0.000 claims 2
- LGTPWUQCBVABOR-UHFFFAOYSA-N 3-[5-amino-4-(4-fluorobenzoyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1=CC=C(F)C=C1 LGTPWUQCBVABOR-UHFFFAOYSA-N 0.000 claims 2
- FBVHNJPDTLHFEQ-UHFFFAOYSA-N 3-[5-amino-4-(cyclohexanecarbonyl)imidazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)C=NC=1C(=O)C1CCCCC1 FBVHNJPDTLHFEQ-UHFFFAOYSA-N 0.000 claims 2
- JAYMLUJZZYSBGD-UHFFFAOYSA-N 3-[5-amino-4-(cyclohexanecarbonyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1CCCCC1 JAYMLUJZZYSBGD-UHFFFAOYSA-N 0.000 claims 2
- CUVLMQVWIMVXBC-UHFFFAOYSA-N 3-[5-amino-4-(cyclopentanecarbonyl)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C1CCCC1 CUVLMQVWIMVXBC-UHFFFAOYSA-N 0.000 claims 2
- MEZFBVYCVSYZBY-UHFFFAOYSA-N 3-[5-amino-4-(oxane-4-carbonyl)imidazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)C=NC=1C(=O)C1CCOCC1 MEZFBVYCVSYZBY-UHFFFAOYSA-N 0.000 claims 2
- FIUNUUPXUJXOHT-UHFFFAOYSA-N 3-[5-amino-4-[3-(1h-1,2,4-triazol-5-yl)benzoyl]pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)C(C=1)=CC=CC=1C1=NN=CN1 FIUNUUPXUJXOHT-UHFFFAOYSA-N 0.000 claims 2
- GWHQURVCNJLILJ-UHFFFAOYSA-N 3-[5-amino-4-[3-(cyclopropylcarbamoyl)benzoyl]imidazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)C=NC=1C(=O)C(C=1)=CC=CC=1C(=O)NC1CC1 GWHQURVCNJLILJ-UHFFFAOYSA-N 0.000 claims 2
- JJGUJEGHJRHSGU-UHFFFAOYSA-N 3-[5-amino-4-[3-(ethylcarbamoyl)benzoyl]imidazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CCNC(=O)C1=CC=CC(C(=O)C2=C(N(C=N2)C=2C(=CC=C(C=2)C(=O)NC2CC2)C)N)=C1 JJGUJEGHJRHSGU-UHFFFAOYSA-N 0.000 claims 2
- YIAMQQAJAKAVCB-UHFFFAOYSA-N 3-[5-amino-4-[3-(propan-2-ylcarbamoyl)benzoyl]imidazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC(C(=O)C2=C(N(C=N2)C=2C(=CC=C(C=2)C(=O)NC2CC2)C)N)=C1 YIAMQQAJAKAVCB-UHFFFAOYSA-N 0.000 claims 2
- XTUYGCBHIIZRNF-UHFFFAOYSA-N 3-[5-amino-4-[3-(propan-2-ylcarbamoyl)benzoyl]pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC(C)NC(=O)C1=CC=CC(C(=O)C2=C(N(N=C2)C=2C(=CC=C(C=2)C(=O)NC2CC2)C)N)=C1 XTUYGCBHIIZRNF-UHFFFAOYSA-N 0.000 claims 2
- WMNKBSHDXQFQMA-UHFFFAOYSA-N 3-[5-amino-4-[3-[2-(dimethylamino)ethylcarbamoyl]benzoyl]imidazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CN(C)CCNC(=O)C1=CC=CC(C(=O)C2=C(N(C=N2)C=2C(=CC=C(C=2)C(=O)NC2CC2)C)N)=C1 WMNKBSHDXQFQMA-UHFFFAOYSA-N 0.000 claims 2
- IBRNCFMZIGAEQJ-UHFFFAOYSA-N 3-[5-amino-4-benzoyl-3-(2-methoxyethoxy)pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound COCCOC1=NN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C(N)=C1C(=O)C1=CC=CC=C1 IBRNCFMZIGAEQJ-UHFFFAOYSA-N 0.000 claims 2
- MMJUGAZRKMWPQW-UHFFFAOYSA-N 5-amino-1-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-n-(2,2-dimethylpropyl)pyrazole-4-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N1N=CC(C(=O)NCC(C)(C)C)=C1N MMJUGAZRKMWPQW-UHFFFAOYSA-N 0.000 claims 2
- FQZXHPIHEOQTOG-UHFFFAOYSA-N 5-amino-1-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-n-[(1-ethylpyrrolidin-2-yl)methyl]pyrazole-4-carboxamide Chemical compound CCN1CCCC1CNC(=O)C1=C(N)N(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)N=C1 FQZXHPIHEOQTOG-UHFFFAOYSA-N 0.000 claims 2
- WRRVAIKMBNAKHW-UHFFFAOYSA-N 5-amino-n-benzyl-1-[5-(cyclopropylcarbamoyl)-2-methylphenyl]pyrazole-4-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)NCC1=CC=CC=C1 WRRVAIKMBNAKHW-UHFFFAOYSA-N 0.000 claims 2
- JNQRGPZAWRBTLS-UHFFFAOYSA-N 5-amino-n-cyclohexyl-1-[5-(cyclopropylcarbamoyl)-2-methylphenyl]pyrazole-4-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C=1N)N=CC=1C(=O)NC1CCCCC1 JNQRGPZAWRBTLS-UHFFFAOYSA-N 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 101100096664 Drosophila melanogaster B52 gene Proteins 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 230000002491 angiogenic effect Effects 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 2
- NDIUEJJIWYDFLI-UHFFFAOYSA-N ethyl 5-amino-1-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-3-methylpyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C(C)=NN1C1=CC(C(=O)NC2CC2)=CC=C1C NDIUEJJIWYDFLI-UHFFFAOYSA-N 0.000 claims 2
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- HNWJFUGNOHOOSC-UHFFFAOYSA-N ethyl 5-amino-1-[5-(cyclopropylcarbamoyl)-2-methylphenyl]pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC(C(=O)NC2CC2)=CC=C1C HNWJFUGNOHOOSC-UHFFFAOYSA-N 0.000 claims 2
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- 238000005755 formation reaction Methods 0.000 claims 2
- 239000012458 free base Substances 0.000 claims 2
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- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
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- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 125000002524 organometallic group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- SOIIHESTBYNJRH-PMPSAXMXSA-N (3r,6r,8as)-6-(benzylsulfonylamino)-n-[3-(diaminomethylideneamino)propyl]-5-oxo-2,3,6,7,8,8a-hexahydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxamide Chemical compound N([C@@H]1CC[C@@H]2SC[C@H](N2C1=O)C(=O)NCCCN=C(N)N)S(=O)(=O)CC1=CC=CC=C1 SOIIHESTBYNJRH-PMPSAXMXSA-N 0.000 claims 1
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PCT/US2004/020384 WO2005009973A1 (en) | 2003-06-26 | 2004-06-24 | 5-membered heterocycle-based p38 kinase inhibitors |
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Families Citing this family (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7485657B2 (en) | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
WO2006116716A2 (en) * | 2005-04-27 | 2006-11-02 | University Of Florida | Materials and methods for enhanced degradation of mutant proteins associated with human disease |
DE102005031580A1 (de) * | 2005-07-06 | 2007-01-11 | Aicuris Gmbh & Co. Kg | Substituierte Sulfolanylpyrazole und ihre Verwendung |
GB0603684D0 (en) * | 2006-02-23 | 2006-04-05 | Novartis Ag | Organic compounds |
MY149622A (en) | 2006-03-22 | 2013-09-13 | Hoffmann La Roche | Pyrazoles as 11-beta-hsd-1 |
JP2009532495A (ja) * | 2006-04-03 | 2009-09-10 | ストワーズ インスティテュート フォー メディカル リサーチ | 多発性嚢胞腎の治療用の組成物及び治療方法 |
CA2667927A1 (en) * | 2006-10-30 | 2008-05-08 | Novartis Ag | 3-amino-pyrazole-4-carboxamide derivatives useful as inhibitors of protein kinases |
GB0621978D0 (en) * | 2006-11-03 | 2006-12-13 | Chroma Therapeutics Ltd | Inhibitors of p38 mitogen-activated protein kinase |
EP1992344A1 (en) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 alpha as a therapeutic target in pathologies linked to FGFR3 mutation |
AU2008276451A1 (en) * | 2007-07-17 | 2009-01-22 | Zalicus Inc. | Treatments of B-cell proliferative disorders |
US20090047243A1 (en) * | 2007-07-17 | 2009-02-19 | Richard Rickles | Combinations for the treatment of b-cell proliferative disorders |
NZ582057A (en) | 2007-07-19 | 2012-03-30 | Lundbeck & Co As H | 5-membered heterocyclic amides and related compounds |
WO2009085797A1 (en) * | 2007-12-21 | 2009-07-09 | Gilead Sciences, Inc. | Processes for preparing hiv reverse transcriptase inhibitors |
DE102008015033A1 (de) * | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
US20090281150A1 (en) * | 2008-04-09 | 2009-11-12 | Nicola Frances Bateman | Compound 249 |
WO2009151569A2 (en) * | 2008-06-09 | 2009-12-17 | Combinatorx, Incorporated | Beta adrenergic receptor agonists for the treatment of b-cell proliferative disorders |
CA2732437C (en) | 2008-08-01 | 2017-11-21 | Ventirx Pharmaceuticals, Inc. | Toll-like receptor agonist formulations and their use |
WO2010054215A1 (en) | 2008-11-06 | 2010-05-14 | Ventirx Pharmaceuticals, Inc. | Methods of synthesis of benzazepine derivatives |
CN102574836B (zh) * | 2009-08-07 | 2014-04-16 | 中外制药株式会社 | 氨基吡唑衍生物 |
DK2467377T3 (en) | 2009-08-18 | 2017-04-03 | Ventirx Pharmaceuticals Inc | SUBSTITUTED BENZOAZEPINS AS MODULATORS OF TOLL-LIKE RECEPTORS |
AU2010284241B2 (en) | 2009-08-18 | 2016-11-10 | Array Biopharma, Inc. | Substituted benzoazepines as Toll-like receptor modulators |
WO2011038261A1 (en) * | 2009-09-24 | 2011-03-31 | Selexagen Therapeutics, Inc. | Heterocyclic kinase inhibitors |
CA2789847A1 (en) | 2010-02-15 | 2011-08-18 | Synovo Gmbh | Kinase modulators for the treatment of cancer |
CA2806121C (en) * | 2010-09-21 | 2018-10-09 | Eisai R&D Management Co., Ltd. | Pharmaceutical composition |
US8993631B2 (en) | 2010-11-16 | 2015-03-31 | Novartis Ag | Method of treating contrast-induced nephropathy |
EP2460519A1 (en) * | 2010-12-03 | 2012-06-06 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in bone cancer pain |
JP5620417B2 (ja) * | 2011-02-07 | 2014-11-05 | 中外製薬株式会社 | アミノピラゾール誘導体を含む医薬 |
LT2827860T (lt) * | 2012-03-20 | 2016-12-12 | Mereo Biopharma 1 Limited | Pirazolo darinio panaudojimas stiprių lėtinės obstrukcinės plaučių ligos paūmėjimų gydymui |
EP3076789A4 (en) * | 2013-12-04 | 2017-11-22 | The Scripps Research Institute | Novel compounds as jnk kinase inhibitors |
US11104668B2 (en) | 2013-12-13 | 2021-08-31 | Hoffmann-La Roche Inc. | Inhibitors of bruton's tyrosine kinase |
US9802920B2 (en) | 2013-12-13 | 2017-10-31 | Hoffman-La Roche Inc. | Inhibitors of bruton's tyrosine kinase |
WO2015099127A1 (ja) | 2013-12-27 | 2015-07-02 | 中外製薬株式会社 | Fgfrゲートキーパー変異遺伝子およびそれを標的とする医薬 |
EP3312172B1 (en) | 2015-06-17 | 2020-05-06 | Chugai Seiyaku Kabushiki Kaisha | Aminopyrazole derivatives useful as src kinase inhibitors |
WO2017028816A1 (zh) * | 2015-08-20 | 2017-02-23 | 浙江海正药业股份有限公司 | 吲哚类衍生物及其制备方法和其在医药上的用途 |
JP6741773B2 (ja) * | 2016-03-08 | 2020-08-19 | メレオ バイオファーマ 1 リミテッド | 炎症状態の急性増悪の治療のための投与レジメン |
CA3016488C (en) * | 2016-03-08 | 2023-04-11 | Mereo Biopharma 1 Limited | Dosage regimen for the treatment of acute exacerbations of chronic obstructive pulmonary disease |
GB201612240D0 (en) | 2016-07-14 | 2016-08-31 | Mereo Biopharma 1 Ltd | Method for producing a polymorphic form of 3-[5-amino-4-(3-cyanobenzoyl)-pyrazol-1-yl]-n-cyclopropyl-4-methylbenzamide |
GB201612238D0 (en) * | 2016-07-14 | 2016-08-31 | Mereo Biopharma 1 Ltd | Method for producing a polymorphic form of 3-[5-amino-4-(3-cyanobenzoyl)-pyrazol-1-Yl]-n-cyclopropyl-4-methylbenzamide |
WO2018059533A1 (zh) * | 2016-09-29 | 2018-04-05 | 南京明德新药研发股份有限公司 | p38αMAPK激酶抑制剂及其制备方法和应用 |
ES2952744T3 (es) | 2016-12-15 | 2023-11-03 | Nestle Sa | Composiciones y procedimientos que modulan los glóbulos blancos o los neutrófilos en un animal de compañía |
HRP20221196T1 (hr) | 2017-10-05 | 2022-12-09 | Fulcrum Therapeutics, Inc. | Inhibitori p38 kinaze smanjuju ekspresiju dux4 i nizvodnih gena u cilju liječenja fshd |
US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
HUE054266T2 (hu) | 2017-12-11 | 2021-08-30 | Mereo Biopharma 1 Ltd | 3-[5-amino-4-(3-cianobenzoil)-pirazol-1-il]-N-ciklopropil-4-metilbenzamid alkalmazása krónikus obstruktív tüdõbetegség akut megjelenésének megelõzésében |
JP7280627B2 (ja) | 2017-12-11 | 2023-05-24 | メレオ バイオファーマ 1 リミテッド | 慢性閉塞性肺疾患の急性増悪の処置における3-[5-アミノ-4-(3-シアノベンゾイル)-ピラゾール-1-イル]-n-シクロプロピル-4-メチルベンズアミドの使用 |
JP2021519334A (ja) | 2018-03-26 | 2021-08-10 | クリア クリーク バイオ, インコーポレイテッド | ジヒドロオロト酸デヒドロゲナーゼを阻害するための組成物および方法 |
EP3563848A1 (en) * | 2018-04-30 | 2019-11-06 | S.I.S.S.A. Scuola Internazionale Superiore di Studi Avanzati | Serpin inhibitors for the treatment of prion and prion-like diseases |
GB201815699D0 (en) * | 2018-09-26 | 2018-11-07 | Mereo Biopharma 1 Ltd | Synthetic method |
GB201815695D0 (en) * | 2018-09-26 | 2018-11-07 | Mereo Biopharma 1 Ltd | Synthetic method |
GB201815696D0 (en) * | 2018-09-26 | 2018-11-07 | Mereo Biopharma 1 Ltd | Synthetic method |
CN110950848B (zh) * | 2018-09-27 | 2024-03-26 | 徐诺药业 | 新型氨基吡唑类衍生物的合成与应用 |
EP3880673B1 (en) * | 2018-11-13 | 2024-01-03 | Novartis AG | Compounds and compositions for treating conditions associated with nlrp activity |
CN112778333B (zh) * | 2021-01-23 | 2022-07-05 | 中国科学院新疆理化技术研究所 | 一种四氢噁唑并吡啶并氮氧杂酮类衍生物及其用途 |
Family Cites Families (53)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1152421B (de) | 1961-03-21 | 1963-08-08 | Bayer Ag | Verfahren zur Herstellung von 4-Hydroxy-pyrazolo[3, 4-b]chinolinen |
JPS5111499Y2 (zh) | 1971-04-22 | 1976-03-27 | ||
USRE28819E (en) * | 1972-12-08 | 1976-05-18 | Syntex (U.S.A.) Inc. | Dialkylated glycol compositions and medicament preparations containing same |
JPS5527916B2 (zh) | 1973-02-05 | 1980-07-24 | ||
JPS51112341A (en) | 1975-02-24 | 1976-10-04 | Konishiroku Photo Ind Co Ltd | Magenta dye image formation |
US4200750A (en) | 1977-01-07 | 1980-04-29 | Westwood Pharmaceuticals Inc. | 4-Substituted imidazo [1,2-a]quinoxalines |
US6005109A (en) | 1997-10-30 | 1999-12-21 | Pflizer Inc. | Pyrazoles and pyrazolopyrimidines having CRF antagonistic activity |
AU690527B2 (en) | 1992-12-17 | 1998-04-30 | Pfizer Inc. | Pyrazoles having CRF antagonist activity |
US6103900A (en) | 1992-12-17 | 2000-08-15 | Pfizer Inc | Pyrazoles and pyrazolopyrimidines having CRF antagonistic activity |
US5514643A (en) | 1993-08-16 | 1996-05-07 | Lucky Ltd. | 2-aminothiazolecarboxamide derivatives, processes for preparing the same and use thereof for controlling phytopathogenic organisms |
US5646152A (en) | 1994-06-15 | 1997-07-08 | Pfizer Inc. | Methods of administering CRF antagonists |
CA2163399A1 (en) | 1994-11-24 | 1996-05-25 | Katsuhiro Kawano | Triazine derivative, chymase activity inhibitor and nitric oxide production inhibitor |
DE19518054A1 (de) | 1995-03-08 | 1996-09-12 | Hoechst Schering Agrevo Gmbh | N-Arylpyrazolketone und deren Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
US5658903A (en) | 1995-06-07 | 1997-08-19 | Smithkline Beecham Corporation | Imidazole compounds, compositions and use |
JP2000503302A (ja) | 1996-01-11 | 2000-03-21 | スミスクライン・ビーチャム・コーポレイション | 新規置換イミダゾール化合物 |
US6147080A (en) | 1996-12-18 | 2000-11-14 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
US5945418A (en) | 1996-12-18 | 1999-08-31 | Vertex Pharmaceuticals Incorporated | Inhibitors of p38 |
CA2275796A1 (en) | 1996-12-23 | 1998-07-02 | Donald Joseph Phillip Pinto | Nitrogen containing heteroaromatics as factor xa inhibitors |
US6087496A (en) | 1998-05-22 | 2000-07-11 | G. D. Searle & Co. | Substituted pyrazoles suitable as p38 kinase inhibitors |
EP0983260A2 (en) | 1997-05-22 | 2000-03-08 | G.D. Searle & Co. | 3(5)-HETEROARYL SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS |
CA2295762A1 (en) | 1997-07-02 | 1999-01-14 | Ravi Shanker Garigipati | Novel cycloalkyl substituted imidazoles |
IL135574A0 (en) | 1997-10-27 | 2001-05-20 | Agouron Pharma | Substituted 4-amino-thiazol-2-yl compounds as cdk inhibitors |
US20020156114A1 (en) | 1998-05-05 | 2002-10-24 | Goldstein David Michael | Pyrazole derivatives - p38 MAP kinase inhibitors |
US6316466B1 (en) * | 1998-05-05 | 2001-11-13 | Syntex (U.S.A.) Llc | Pyrazole derivatives P-38 MAP kinase inhibitors |
US6376527B1 (en) | 1998-05-05 | 2002-04-23 | Syntex (U.S.A.) Llc | Pyrazole derivatives-p38 map kinase inhibitors |
CN1147476C (zh) * | 1998-05-05 | 2004-04-28 | 霍夫曼-拉罗奇有限公司 | 作为p-38map激酶抑制剂的吡唑衍生物 |
US6130235A (en) | 1998-05-22 | 2000-10-10 | Scios Inc. | Compounds and methods to treat cardiac failure and other disorders |
MXPA01002173A (es) | 1998-08-28 | 2003-07-14 | Scios Inc | Inhibidores de p38-alfa cinasa. |
US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
WO2000025780A1 (en) | 1998-10-29 | 2000-05-11 | Bristol-Myers Squibb Company | Compounds derived from an amine nucleus that are inhibitors of impdh enzyme |
GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
IL144910A0 (en) | 1999-04-15 | 2002-06-30 | Bristol Myers Squibb Co | Cyclic compounds and pharmaceutical compositions containing the same |
GB9924092D0 (en) | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
KR20010089805A (ko) | 1999-11-10 | 2001-10-08 | 오르토-맥네일 파마슈티칼, 인코퍼레이티드 | 치환된 2-아릴-3-(헤테로아릴)-이미다조[1,2-a]피리미딘,및 관련 약제학적 조성물 및 방법 |
AU2001230026A1 (en) | 2000-02-04 | 2001-08-14 | Novo-Nordisk A/S | 2,4-diaminothiazole derivatives |
JP2004509863A (ja) | 2000-09-21 | 2004-04-02 | ブリストル−マイヤーズ スクイブ カンパニー | コルチコトロピン放出因子のインヒビターとしての置換アゾール誘導体 |
CZ20031370A3 (cs) | 2000-11-17 | 2003-10-15 | Bristol-Myers Squibb Company | Způsob léčení stavů souvisejících s p38 kinázou a pyrrolotriazinové sloučeniny použitelné jako inhibitory kináz |
AU2002219678A1 (en) | 2001-01-17 | 2002-07-30 | Boyean Kim | Sun visor having office work apparatus |
US6756374B2 (en) | 2001-01-22 | 2004-06-29 | Hoffmann-La Roche Inc. | Diaminothiazoles having antiproliferative activity |
MXPA03010269A (es) | 2001-05-11 | 2004-05-05 | Vertex Pharma | Derivados de 2,5-disubstituida piridina, pirimidina, piridazina y 1,2,4-triazina para usarse como inhibidores de p38. |
HN2002000156A (es) | 2001-07-06 | 2003-11-27 | Inc Agouron Pharmaceuticals | Derivados de benzamida tiazol y composiciones farmaceuticas para inhibir la proliferacion de celulas y metodos para su utilización. |
GB0124932D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124938D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124934D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124936D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124931D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124928D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124933D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124939D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0124941D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
AU2004309420B2 (en) * | 2003-12-23 | 2008-10-30 | Novartis Ag | Bicyclic heterocyclic p-38 kinase inhibitors |
JP2007084437A (ja) | 2003-12-26 | 2007-04-05 | Dai Ichi Seiyaku Co Ltd | アミノアルキルピラゾール誘導体 |
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