ES2254238T3 - Compuestos de tiazol e imidazo(4,5-b)piridina y su uso farmaceutico. - Google Patents
Compuestos de tiazol e imidazo(4,5-b)piridina y su uso farmaceutico.Info
- Publication number
- ES2254238T3 ES2254238T3 ES00969551T ES00969551T ES2254238T3 ES 2254238 T3 ES2254238 T3 ES 2254238T3 ES 00969551 T ES00969551 T ES 00969551T ES 00969551 T ES00969551 T ES 00969551T ES 2254238 T3 ES2254238 T3 ES 2254238T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- amino
- alkyl
- formula
- substituted
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 39
- -1 piperazyl Chemical group 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 13
- 150000002148 esters Chemical class 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 239000000651 prodrug Substances 0.000 claims abstract description 6
- 229940002612 prodrug Drugs 0.000 claims abstract description 6
- 238000010494 dissociation reaction Methods 0.000 claims abstract description 5
- 230000005593 dissociations Effects 0.000 claims abstract description 5
- 238000003797 solvolysis reaction Methods 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000005936 piperidyl group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- 201000010099 disease Diseases 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 14
- 230000002757 inflammatory effect Effects 0.000 claims description 10
- 230000001363 autoimmune Effects 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 5
- 239000003018 immunosuppressive agent Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 4
- 230000001861 immunosuppressant effect Effects 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- MJMDLUIORMBKHA-IBGZPJMESA-N 4-[4-(4-fluorophenyl)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C=1SC(N2CCC(C)CC2)=NC=1C1=CC=C(F)C=C1 MJMDLUIORMBKHA-IBGZPJMESA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- OONDROKXCHJESN-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-[4-(4-fluorophenyl)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-5-yl]pyridin-2-amine Chemical compound C1CC(C)CCN1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=C(NCC3CC3)N=CC=2)S1 OONDROKXCHJESN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 229940125721 immunosuppressive agent Drugs 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000011734 sodium Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000007832 Na2SO4 Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 150000001540 azides Chemical class 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 229910052681 coesite Inorganic materials 0.000 description 8
- 229910052906 cristobalite Inorganic materials 0.000 description 8
- 239000002158 endotoxin Substances 0.000 description 8
- 229920006008 lipopolysaccharide Polymers 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 235000012239 silicon dioxide Nutrition 0.000 description 8
- 229910052682 stishovite Inorganic materials 0.000 description 8
- 229910052905 tridymite Inorganic materials 0.000 description 8
- 102100040247 Tumor necrosis factor Human genes 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 108091000080 Phosphotransferase Proteins 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 102000020233 phosphotransferase Human genes 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 206010003246 arthritis Diseases 0.000 description 4
- 239000006196 drop Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 4
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CGEYWOCSYFPNQC-SFHVURJKSA-N 4-[4-(4-fluorophenyl)-2-piperidin-4-yl-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyridin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=CC=1)=CC=1C=1SC(C2CCNCC2)=NC=1C1=CC=C(F)C=C1 CGEYWOCSYFPNQC-SFHVURJKSA-N 0.000 description 3
- QCNCMKGQOCQRNB-KRWDZBQOSA-N 4-[4-(4-fluorophenyl)-2-piperidin-4-yl-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C=1SC(C2CCNCC2)=NC=1C1=CC=C(F)C=C1 QCNCMKGQOCQRNB-KRWDZBQOSA-N 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108010002352 Interleukin-1 Proteins 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- UTZCWVSFOGAZLW-UHFFFAOYSA-N ethyl n-(piperidine-4-carbothioyl)carbamate Chemical compound CCOC(=O)NC(=S)C1CCNCC1 UTZCWVSFOGAZLW-UHFFFAOYSA-N 0.000 description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 description 3
- 230000004968 inflammatory condition Effects 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 201000006417 multiple sclerosis Diseases 0.000 description 3
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 150000003557 thiazoles Chemical class 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 2
- UWNDUYAKSCWHDG-UHFFFAOYSA-N 2-(2,4-difluoro-3h-pyridin-4-yl)-1-phenylethanone Chemical compound C1C(F)=NC=CC1(F)CC(=O)C1=CC=CC=C1 UWNDUYAKSCWHDG-UHFFFAOYSA-N 0.000 description 2
- HEAHTFNRCPDZFZ-UHFFFAOYSA-N 2-(4-fluoro-2-methylsulfanyl-1h-pyrimidin-4-yl)-1-phenylethanone Chemical compound C1=CNC(SC)=NC1(F)CC(=O)C1=CC=CC=C1 HEAHTFNRCPDZFZ-UHFFFAOYSA-N 0.000 description 2
- DSUFRPVVBZLHPI-UHFFFAOYSA-N 4-fluoro-n-methoxy-n-methylbenzamide Chemical compound CON(C)C(=O)C1=CC=C(F)C=C1 DSUFRPVVBZLHPI-UHFFFAOYSA-N 0.000 description 2
- UCERVHYBSTYCQS-UHFFFAOYSA-N 4-methyl-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(C)=N1 UCERVHYBSTYCQS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- AFFTZDYHTGEWFH-UHFFFAOYSA-N CSC1=NC=CC(C=2SC=CN=2)=N1 Chemical compound CSC1=NC=CC(C=2SC=CN=2)=N1 AFFTZDYHTGEWFH-UHFFFAOYSA-N 0.000 description 2
- 206010006895 Cachexia Diseases 0.000 description 2
- 101100026251 Caenorhabditis elegans atf-2 gene Proteins 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- DHCLVCXQIBBOPH-UHFFFAOYSA-N Glycerol 2-phosphate Chemical compound OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FYRVEFPNRHDRRT-UHFFFAOYSA-N ethyl 4-[4-(4-fluorophenyl)-5-(2-fluoropyridin-4-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=C(F)N=CC=2)S1 FYRVEFPNRHDRRT-UHFFFAOYSA-N 0.000 description 2
- YADBJAFZFKRMAF-FQEVSTJZSA-N ethyl 4-[4-(4-fluorophenyl)-5-[2-[[(1s)-1-phenylethyl]amino]pyridin-4-yl]-1,3-thiazol-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1C1=NC(C=2C=CC(F)=CC=2)=C(C=2C=C(N[C@@H](C)C=3C=CC=CC=3)N=CC=2)S1 YADBJAFZFKRMAF-FQEVSTJZSA-N 0.000 description 2
- WYBUJWLYYDAQAJ-IBGZPJMESA-N ethyl 4-[4-(4-fluorophenyl)-5-[2-[[(1s)-1-phenylethyl]amino]pyrimidin-4-yl]-1,3-thiazol-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1C1=NC(C=2C=CC(F)=CC=2)=C(C=2N=C(N[C@@H](C)C=3C=CC=CC=3)N=CC=2)S1 WYBUJWLYYDAQAJ-IBGZPJMESA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 108020001507 fusion proteins Proteins 0.000 description 2
- 102000037865 fusion proteins Human genes 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RERFOTMKOSGPFE-UHFFFAOYSA-N 2-(2-methylsulfanylpyrimidin-4-yl)-1-phenylethanone Chemical compound CSC1=NC=CC(CC(=O)C=2C=CC=CC=2)=N1 RERFOTMKOSGPFE-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- QSIBNTMXHTWXMV-UHFFFAOYSA-N 2-bromo-1-(4-fluorophenyl)-2-(2-fluoropyridin-4-yl)ethanone Chemical compound C1=CC(F)=CC=C1C(=O)C(Br)C1=CC=NC(F)=C1 QSIBNTMXHTWXMV-UHFFFAOYSA-N 0.000 description 1
- YDIGVDUIMDDIRI-UHFFFAOYSA-N 2-bromo-2-(2,4-difluoro-3h-pyridin-4-yl)-1-phenylethanone Chemical compound C1C(F)=NC=CC1(F)C(Br)C(=O)C1=CC=CC=C1 YDIGVDUIMDDIRI-UHFFFAOYSA-N 0.000 description 1
- CQUDIDJBJLLTLY-UHFFFAOYSA-N 2-bromo-2-(4-fluoro-2-methylsulfanyl-1h-pyrimidin-4-yl)-1-phenylethanone Chemical compound C1=CNC(SC)=NC1(F)C(Br)C(=O)C1=CC=CC=C1 CQUDIDJBJLLTLY-UHFFFAOYSA-N 0.000 description 1
- ZBFAXMKJADVOGH-UHFFFAOYSA-N 2-fluoro-4-methylpyridine Chemical compound CC1=CC=NC(F)=C1 ZBFAXMKJADVOGH-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- HJEPFPDXSFKWQH-IBGZPJMESA-N 4-[4-(4-fluorophenyl)-2-(1-methylpiperidin-4-yl)-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyridin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=CC=1)=CC=1C=1SC(C2CCN(C)CC2)=NC=1C1=CC=C(F)C=C1 HJEPFPDXSFKWQH-IBGZPJMESA-N 0.000 description 1
- KFKODKNJGWITBQ-SFHVURJKSA-N 4-[4-(4-fluorophenyl)-2-(1-methylpiperidin-4-yl)-1,3-thiazol-5-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C=1SC(C2CCN(C)CC2)=NC=1C1=CC=C(F)C=C1 KFKODKNJGWITBQ-SFHVURJKSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- CNTXFFPMUCWRKW-UHFFFAOYSA-N 5-(2-methylsulfanylpyrimidin-4-yl)-4-phenyl-1,3-thiazole Chemical compound CSC1=NC=CC(C2=C(N=CS2)C=2C=CC=CC=2)=N1 CNTXFFPMUCWRKW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000032467 Aplastic anaemia Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 description 1
- 208000018083 Bone metabolism disease Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- XOXCFWMBFDUFRD-UHFFFAOYSA-N CS(=O)C1=NC=CC(C=2SC=CN=2)=N1 Chemical compound CS(=O)C1=NC=CC(C=2SC=CN=2)=N1 XOXCFWMBFDUFRD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 206010060742 Endocrine ophthalmopathy Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 description 1
- 208000003807 Graves Disease Diseases 0.000 description 1
- 208000015023 Graves' disease Diseases 0.000 description 1
- 206010019755 Hepatitis chronic active Diseases 0.000 description 1
- 101150106931 IFNG gene Proteins 0.000 description 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 208000004883 Lipoid Nephrosis Diseases 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- 229940122696 MAP kinase inhibitor Drugs 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- UKERDACREYXSIV-UHFFFAOYSA-N N-methoxy-N-methylbenzamide Chemical compound CON(C)C(=O)C1=CC=CC=C1 UKERDACREYXSIV-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 238000011795 OF1 mouse Methods 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010065159 Polychondritis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 206010068733 Respiratory fatigue Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 108700012920 TNF Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 208000016807 X-linked intellectual disability-macrocephaly-macroorchidism syndrome Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 208000002205 allergic conjunctivitis Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 230000004097 bone metabolism Effects 0.000 description 1
- 230000006931 brain damage Effects 0.000 description 1
- 231100000874 brain damage Toxicity 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000010523 cascade reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- KAKKHKRHCKCAGH-UHFFFAOYSA-L disodium;(4-nitrophenyl) phosphate;hexahydrate Chemical compound O.O.O.O.O.O.[Na+].[Na+].[O-][N+](=O)C1=CC=C(OP([O-])([O-])=O)C=C1 KAKKHKRHCKCAGH-UHFFFAOYSA-L 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 231100000284 endotoxic Toxicity 0.000 description 1
- 230000002346 endotoxic effect Effects 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- MDHWSNVTHKVSCU-UHFFFAOYSA-N ethyl n-(piperidine-4-carbonyl)carbamate Chemical compound CCOC(=O)NC(=O)C1CCNCC1 MDHWSNVTHKVSCU-UHFFFAOYSA-N 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 208000007475 hemolytic anemia Diseases 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 150000005232 imidazopyridines Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 201000010666 keratoconjunctivitis Diseases 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000000021 kinase assay Methods 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000002314 neuroinflammatory effect Effects 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 206010035653 pneumoconiosis Diseases 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 230000006433 tumor necrosis factor production Effects 0.000 description 1
- 208000018464 vernal keratoconjunctivitis Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9925441 | 1999-10-27 | ||
| GBGB9925441.9A GB9925441D0 (en) | 1999-10-27 | 1999-10-27 | Organic compounds |
| GB9926173 | 1999-11-04 | ||
| GBGB9926173.7A GB9926173D0 (en) | 1999-11-04 | 1999-11-04 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2254238T3 true ES2254238T3 (es) | 2006-06-16 |
Family
ID=26316029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00969551T Expired - Lifetime ES2254238T3 (es) | 1999-10-27 | 2000-10-25 | Compuestos de tiazol e imidazo(4,5-b)piridina y su uso farmaceutico. |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6608072B1 (https=) |
| EP (1) | EP1224185B1 (https=) |
| JP (1) | JP2003512467A (https=) |
| AR (1) | AR029011A1 (https=) |
| AT (1) | ATE311385T1 (https=) |
| AU (1) | AU7922900A (https=) |
| CO (1) | CO5251463A1 (https=) |
| DE (1) | DE60024480T2 (https=) |
| ES (1) | ES2254238T3 (https=) |
| PE (1) | PE20011039A1 (https=) |
| WO (1) | WO2001030778A1 (https=) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE342892T1 (de) | 1998-08-29 | 2006-11-15 | Astrazeneca Ab | Pyrimidine verbindungen |
| US6632820B1 (en) | 1998-08-29 | 2003-10-14 | Astrazeneca Ab | Pyrimidine compounds |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| GB9907658D0 (en) | 1999-04-06 | 1999-05-26 | Zeneca Ltd | Chemical compounds |
| GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004888D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004886D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0007371D0 (en) | 2000-03-28 | 2000-05-17 | Astrazeneca Uk Ltd | Chemical compounds |
| JP2004503553A (ja) * | 2000-06-14 | 2004-02-05 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | ６，５−縮合二環式複素環 |
| GB0016877D0 (en) | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
| GB0021726D0 (en) | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| US7199124B2 (en) | 2001-02-02 | 2007-04-03 | Takeda Pharmaceutical Company Limited | JNK inhibitor |
| GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| GB0113041D0 (en) | 2001-05-30 | 2001-07-18 | Astrazeneca Ab | Chemical compounds |
| ATE325608T1 (de) | 2001-08-13 | 2006-06-15 | Janssen Pharmaceutica Nv | 2,4,5-trisubstituted thiazolyl derivative und deren antiinflammatorische wirkung |
| TWI322807B (en) * | 2002-01-07 | 2010-04-01 | Eisai R&D Man Co Ltd | Novel deazapurines and uses thereof |
| DK1474425T3 (da) | 2002-01-07 | 2006-09-25 | Eisai Co Ltd | Deazapuriner og anvendelser deraf |
| GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| US7442697B2 (en) | 2002-03-09 | 2008-10-28 | Astrazeneca Ab | 4-imidazolyl substituted pyrimidine derivatives with CDK inhibitory activity |
| GB0205693D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| GB0205688D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| US7361665B2 (en) | 2002-07-09 | 2008-04-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases |
| JP2006500365A (ja) | 2002-08-14 | 2006-01-05 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | ｐ３８ＭＡＰキナーゼインヒビターを用いた抗凝固及び線維素溶解療法 |
| GB0226583D0 (en) * | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| US7468376B2 (en) | 2003-02-27 | 2008-12-23 | Palau Pharma, S.A. | Pyrazolopyridine derivates |
| GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| TWI334868B (en) * | 2003-06-03 | 2010-12-21 | Nippon Kayaku Kk | [1,2,4] triazoro [1,5-a] pyrimidine-2-ylurea derivative and use thereof |
| JP2007500178A (ja) * | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | プロテインキナーゼ阻害剤としてのピリジニルアミノ−ピリミジン誘導体 |
| WO2005016910A1 (ja) * | 2003-08-18 | 2005-02-24 | Sankio Chemical Co., Ltd. | ピリジルテトラヒドロピリジン類およびピリジルピペリジン類とそれらの製造方法 |
| GB0401336D0 (en) * | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| WO2005070932A2 (en) * | 2004-01-22 | 2005-08-04 | Amgen Inc. | Substituted heterocyclic compounds and methods of use |
| TWI332003B (en) * | 2004-01-30 | 2010-10-21 | Lilly Co Eli | Kinase inhibitors |
| TW200528101A (en) | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
| US7713998B2 (en) | 2004-11-10 | 2010-05-11 | Ono Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic compound and pharmaceutical use thereof |
| KR100848205B1 (ko) * | 2005-06-20 | 2008-07-24 | 주식회사 동부하이텍 | 면역 억제 및 염증 억제 활성을 갖는 신규한 치환된1,3-티아졸 유도체 또는 이의 약학적으로 허용가능한 염,중간체 화합물 또는 이의 약학적으로 허용가능한 염, 이의제조방법, 및 이를 포함하는 약학적 조성물 |
| WO2007034278A2 (en) * | 2005-09-19 | 2007-03-29 | Pfizer Products Inc. | Fused imidazole derivatives as c3a receptor antagonists |
| AR056556A1 (es) | 2005-09-30 | 2007-10-10 | Astrazeneca Ab | Imidazo(1,2-a)piridina con actividad antiproliferacion celular |
| US7968572B2 (en) | 2005-10-03 | 2011-06-28 | Ono Pharmaceuticals Co., Ltd. | Nitrogen-containing heterocyclic compound and pharmaceutical application thereof |
| ES2424214T3 (es) | 2007-08-27 | 2013-09-30 | Siga Technologies, Inc. | Medicamentos antivirales para el tratamiento de una infección por Arenavirus |
| WO2009076140A1 (en) * | 2007-12-13 | 2009-06-18 | Smithkline Beecham Corporation | Thiazole and oxazole kinase inhibitors |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| KR101324804B1 (ko) * | 2008-05-13 | 2013-11-01 | 아이알엠 엘엘씨 | 키나제 억제제로서의 질소 함유 융합 헤테로사이클 및 그의 조성물 |
| EP3623374B1 (en) | 2008-12-03 | 2021-09-08 | The Scripps Research Institute | Stem cell cultures |
| EP2198710A1 (de) | 2008-12-19 | 2010-06-23 | Bayer CropScience AG | Verwendung von 5-Pyridin-4yl-(1,3)Thiazole zur Bekämpfung phytopathogener Pilze |
| MX2011012343A (es) * | 2009-05-19 | 2011-12-14 | Dow Agrosciences Llc | Compuestos y metodos para controlar hongos. |
| SG192941A1 (en) * | 2011-02-25 | 2013-09-30 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| CN103145706B (zh) * | 2012-11-16 | 2015-11-25 | 温州医学院 | 一类具有抗炎作用的咪唑并吡啶类化合物及其在制备抗炎药物中的应用 |
| NZ746607A (en) | 2012-11-21 | 2019-11-29 | Ptc Therapeutics Inc | Substituted reverse pyrimidine bmi-1 inhibitors |
| WO2014172639A1 (en) * | 2013-04-19 | 2014-10-23 | Ruga Corporation | Raf kinase inhibitors |
| EA034866B1 (ru) | 2013-08-30 | 2020-03-31 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Замещенные пиримидиновые ингибиторы bmi-1 |
| WO2015076800A1 (en) | 2013-11-21 | 2015-05-28 | Ptc Therapeutics, Inc. | Substituted pyridine and pyrazine bmi-1 inhibitors |
| GB201321739D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| CR20170077A (es) | 2014-08-04 | 2017-06-26 | Nuevolution As | Derivados de heterociclilo opcionalmente condensados de pirimidina útiles para el tratamiento de enfermedades inflamatorias, metabólicas, oncológicas y autoinmunitarias |
| AU2016233288A1 (en) * | 2015-03-18 | 2017-11-09 | Bristol-Myers Squibb Company | Substituted tricyclic heterocyclic compounds |
| CA2982446A1 (en) * | 2015-03-18 | 2016-09-22 | Bristol-Myers Squibb Company | Tricyclic heterocyclic compounds useful as inhibitors of tnf |
| US20190060286A1 (en) | 2016-02-29 | 2019-02-28 | University Of Florida Research Foundation, Incorpo | Chemotherapeutic Methods |
| WO2019142128A1 (en) * | 2018-01-18 | 2019-07-25 | Integral Biosciences Private Limited | Dual inhibitors of alk5 and p38α map kinase |
| EP3836932A2 (en) | 2018-08-17 | 2021-06-23 | PTC Therapeutics, Inc. | Method for treating pancreatic cancer |
| MX2021003904A (es) | 2018-10-05 | 2021-10-26 | Annapurna Bio Inc | Compuestos y composiciones para el tratamiento de afecciones asociadas con la actividad del receptor apj. |
| MX2022007265A (es) | 2019-12-20 | 2022-09-09 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| UY38994A (es) | 2019-12-20 | 2021-07-30 | Nuevolution As | Compuestos activos frente a receptores nucleares |
| WO2021198956A1 (en) | 2020-03-31 | 2021-10-07 | Nuevolution A/S | Compounds active towards nuclear receptors |
| AU2021245397A1 (en) | 2020-03-31 | 2022-10-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
| CA3261365A1 (en) * | 2022-07-28 | 2024-02-01 | Ac Immune Sa | NEW COMPOUNDS |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6058981A (ja) * | 1983-09-09 | 1985-04-05 | Takeda Chem Ind Ltd | ５−ピリジル−１，３−チアゾ−ル誘導体，その製造法およびそれを含んでなる医薬組成物 |
| AU3592493A (en) * | 1992-01-13 | 1993-08-03 | Smithkline Beecham Corporation | Pyridyl substituted imidazoles |
| EP0727998B1 (en) * | 1993-11-08 | 2004-01-21 | Smithkline Beecham Corporation | Oxazoles for treating cytokine mediated diseases |
| IL118544A (en) * | 1995-06-07 | 2001-08-08 | Smithkline Beecham Corp | History of imidazole, the process for their preparation and the pharmaceutical preparations containing them |
| US5739143A (en) * | 1995-06-07 | 1998-04-14 | Smithkline Beecham Corporation | Imidazole compounds and compositions |
| WO1997005878A1 (en) | 1995-08-10 | 1997-02-20 | Merck & Co., Inc. | 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use |
| KR20000057137A (ko) * | 1996-11-19 | 2000-09-15 | 스티븐 엠. 오드레 | 아릴 및 헤테로아릴로 치환된 융합 피롤 항염증제 |
| ZA9711092B (en) * | 1996-12-11 | 1999-07-22 | Smithkline Beecham Corp | Novel compounds. |
| WO1998047899A1 (en) * | 1997-04-24 | 1998-10-29 | Ortho-Mcneil Corporation, Inc. | Substituted pyrrolopyridines useful in the treatment of inflammatory diseases |
| GB9713726D0 (en) * | 1997-06-30 | 1997-09-03 | Ciba Geigy Ag | Organic compounds |
| BR9812944A (pt) * | 1997-10-20 | 2000-08-08 | Hoffmann La Roche | Inibidores bicìclicos da cinase |
| US6436966B1 (en) * | 1997-10-27 | 2002-08-20 | Takeda Chemical Ind., Ltd. | Adenosine A3 receptor antagonists |
| JP3990061B2 (ja) * | 1998-01-05 | 2007-10-10 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | プリン誘導体および糖尿病の予防・治療剤としてのアデノシンａ２受容体拮抗剤 |
| AU4506399A (en) * | 1998-06-05 | 1999-12-30 | Novartis Ag | Aryl pyridinyl thiazoles |
| JP2000119271A (ja) * | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| CO5170501A1 (es) * | 1999-04-14 | 2002-06-27 | Novartis Ag | AZOLES SUSTITUIDOS UTILES PARA EL TRATAMIENTO DE ENFERMEDADES MEDIADAS POR TNFa eIL-1 Y ENFERMEDADES DEL METABOLISMO OSEO |
| DE60033028T2 (de) * | 1999-04-23 | 2007-11-15 | Takeda Pharmaceutical Co. Ltd. | 5-pyridyl-1,3-azol-derivate, verfahren zu ihrer herstellung und ihre verwendung |
| JP3333774B2 (ja) * | 1999-04-23 | 2002-10-15 | 武田薬品工業株式会社 | ５−ピリジル−１，３−アゾール化合物、その製造法及び用途 |
| US6492516B1 (en) | 1999-05-14 | 2002-12-10 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
-
2000
- 2000-10-25 AU AU79229/00A patent/AU7922900A/en not_active Abandoned
- 2000-10-25 WO PCT/EP2000/010528 patent/WO2001030778A1/en not_active Ceased
- 2000-10-25 AT AT00969551T patent/ATE311385T1/de not_active IP Right Cessation
- 2000-10-25 DE DE60024480T patent/DE60024480T2/de not_active Expired - Lifetime
- 2000-10-25 JP JP2001533132A patent/JP2003512467A/ja active Pending
- 2000-10-25 EP EP00969551A patent/EP1224185B1/en not_active Expired - Lifetime
- 2000-10-25 US US10/111,233 patent/US6608072B1/en not_active Expired - Fee Related
- 2000-10-25 ES ES00969551T patent/ES2254238T3/es not_active Expired - Lifetime
- 2000-10-26 AR ARP000105643A patent/AR029011A1/es unknown
- 2000-10-26 PE PE2000001147A patent/PE20011039A1/es not_active Application Discontinuation
- 2000-10-27 CO CO00082019A patent/CO5251463A1/es not_active Application Discontinuation
-
2003
- 2003-06-23 US US10/601,690 patent/US6891039B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001030778A1 (en) | 2001-05-03 |
| US6608072B1 (en) | 2003-08-19 |
| JP2003512467A (ja) | 2003-04-02 |
| US6891039B2 (en) | 2005-05-10 |
| CO5251463A1 (es) | 2003-02-28 |
| EP1224185B1 (en) | 2005-11-30 |
| AU7922900A (en) | 2001-05-08 |
| DE60024480T2 (de) | 2006-07-27 |
| EP1224185A1 (en) | 2002-07-24 |
| US20040082604A1 (en) | 2004-04-29 |
| PE20011039A1 (es) | 2001-10-30 |
| AR029011A1 (es) | 2003-06-04 |
| ATE311385T1 (de) | 2005-12-15 |
| DE60024480D1 (de) | 2006-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2254238T3 (es) | Compuestos de tiazol e imidazo(4,5-b)piridina y su uso farmaceutico. | |
| ES2226164T3 (es) | 4,5-diarilimidazoles substituidos en 2. | |
| ES2202114T3 (es) | Azoles substituidos. | |
| CA2176255C (en) | Isoxazoline compounds as antiinflammatory agents | |
| AU628913B2 (en) | Pyrazolopyridine compound and processes for preparation thereof | |
| US6903117B2 (en) | Indole derivatives for the treatment of osteoporosis | |
| KR20040087335A (ko) | 질소 함유 복소환 화합물 | |
| MX2011008308A (es) | Derivados de azaspiranil-alquilcarbamatos de heterociclos de 5 eslabones, su preparacion y su aplicacion en terapeutica. | |
| SK287597B6 (sk) | Heterocyklické zlúčeniny, ich príprava a použitie ako liečiva, najmä ako antibakteriálne činidlá | |
| EP1200415A1 (en) | Diamino-1,2,4-triazole-carboxylic acid derivatives as gsk-3 inhibitors | |
| EP1209158A1 (en) | Substituted beta-carbolines | |
| JP4166991B2 (ja) | ピリドピリミジンまたはナフチリジン誘導体 | |
| CN110872285A (zh) | 作为受体相互作用蛋白1(rip1)激酶抑制剂的杂环化合物 | |
| KR20180002729A (ko) | 히스톤 탈아세틸효소 억제제 및 그것의 조성물 및 사용 방법 | |
| ES2345207T3 (es) | Compuestos pirazolo-heteroarilicos utiles para tratar enfermedades mediadas por tnf-alfa e il-1. | |
| CZ282002B6 (cs) | Substituované 4-amino-3-pyridinoly, způsob jejich přípravy a jejich použití jako léčiv | |
| CS276785B6 (en) | PROCESS FOR PREPARING NOVEL DERIVATIVES OF 1H,3H-PYRROLO-(1,2-c)THIAZOLE-7-CARBOXAMIDE | |
| TWI469982B (zh) | 環狀（氮雜）吲甲醯胺、其製備及其作為藥劑之用途 | |
| WO2004017968A1 (de) | Substituierte isoxazolderivate und ihre verwendung in der pharmazie | |
| ES2259704T3 (es) | Compuestos benzoilicos. | |
| CN101107248A (zh) | 作为用于治疗高血压的肾素抑制剂的7－{4－[2－(2,6－二氯－4－甲基苯氧基)乙氧基]苯基}－3,9－二氮杂双环[3.3.1]壬－6－烯－6－羧酸环丙基－(2,3－二甲基苄基)酰胺 | |
| JPH09510992A (ja) | ブラジキニンアンタゴニストとしてのジヒドロピリジン誘導体 | |
| EP0661274A1 (en) | Indane derivatives, processes for preparing the same and synthetic intermediate of the same | |
| JP2004083587A (ja) | 医薬組成物 | |
| KR101577314B1 (ko) | 키나제 억제제로서의 접합된 티아졸 유도체 |