CS214891A3 - Thioxoheterocyclic compounds, process for their preparation and their use as medicaments - Google Patents
Thioxoheterocyclic compounds, process for their preparation and their use as medicaments Download PDFInfo
- Publication number
- CS214891A3 CS214891A3 CS912148A CS214891A CS214891A3 CS 214891 A3 CS214891 A3 CS 214891A3 CS 912148 A CS912148 A CS 912148A CS 214891 A CS214891 A CS 214891A CS 214891 A3 CS214891 A3 CS 214891A3
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- Czechoslovakia
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- group
- formula
- carbon atoms
- methyl
- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 134
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 16
- 230000008569 process Effects 0.000 title claims description 10
- 239000003814 drug Substances 0.000 title claims description 6
- -1 oxy, thio, sulphinyl Chemical group 0.000 claims abstract description 122
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 65
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 28
- 125000006413 ring segment Chemical group 0.000 claims abstract description 19
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 4
- 125000005551 pyridylene group Chemical group 0.000 claims abstract description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 125000006239 protecting group Chemical group 0.000 claims description 33
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 150000001721 carbon Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 19
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 18
- 239000005977 Ethylene Substances 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 150000002617 leukotrienes Chemical class 0.000 claims description 13
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- YLZDFZMVEYNSGR-UHFFFAOYSA-N 6-[[3-fluoro-5-(4-methoxyoxan-4-yl)phenoxy]methyl]-1-methyl-3,4-dihydroquinoline-2-thione Chemical compound C=1C(F)=CC(OCC=2C=C3CCC(=S)N(C)C3=CC=2)=CC=1C1(OC)CCOCC1 YLZDFZMVEYNSGR-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- ZRFKRGQWUVCKFF-UHFFFAOYSA-N 6-[[3-fluoro-5-(4-methoxyoxan-4-yl)phenoxy]methyl]-1-methylquinoline-2-thione Chemical compound C=1C(F)=CC(OCC=2C=C3C=CC(=S)N(C)C3=CC=2)=CC=1C1(OC)CCOCC1 ZRFKRGQWUVCKFF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 150000002373 hemiacetals Chemical class 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- BHNCZRFXNHVDDT-UHFFFAOYSA-N 4-methoxyoxane Chemical compound COC1CCOCC1 BHNCZRFXNHVDDT-UHFFFAOYSA-N 0.000 claims 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 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 1
- 125000000464 thioxo group Chemical group S=* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 8
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 abstract description 2
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000012360 testing method Methods 0.000 description 24
- 102100022364 Polyunsaturated fatty acid 5-lipoxygenase Human genes 0.000 description 23
- 101710156627 Polyunsaturated fatty acid 5-lipoxygenase Proteins 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
- 239000007858 starting material Substances 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 230000002401 inhibitory effect Effects 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000003556 assay Methods 0.000 description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
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- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 7
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 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 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
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- 230000002757 inflammatory effect Effects 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
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- 238000003127 radioimmunoassay Methods 0.000 description 5
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- 239000012312 sodium hydride Substances 0.000 description 5
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- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 4
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
- FMNQRUKVXAQEAZ-JNRFBPFXSA-N (5z,8s,9r,10e,12s)-9,12-dihydroxy-8-[(1s)-1-hydroxy-3-oxopropyl]heptadeca-5,10-dienoic acid Chemical compound CCCCC[C@H](O)\C=C\[C@@H](O)[C@H]([C@@H](O)CC=O)C\C=C/CCCC(O)=O FMNQRUKVXAQEAZ-JNRFBPFXSA-N 0.000 description 3
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- NYCDFHQOYLMAGZ-UHFFFAOYSA-N 1-methyl-6-sulfanyl-3,4-dihydroquinolin-2-one Chemical compound SC1=CC=C2N(C)C(=O)CCC2=C1 NYCDFHQOYLMAGZ-UHFFFAOYSA-N 0.000 description 3
- NBHXLSHYODTEPJ-UHFFFAOYSA-N 3-fluoro-5-(4-methoxyoxan-4-yl)phenol Chemical compound C=1C(O)=CC(F)=CC=1C1(OC)CCOCC1 NBHXLSHYODTEPJ-UHFFFAOYSA-N 0.000 description 3
- HEABCAMWOVYMHZ-UHFFFAOYSA-N 4-(3,5-difluorophenyl)-4-methoxyoxane Chemical compound C=1C(F)=CC(F)=CC=1C1(OC)CCOCC1 HEABCAMWOVYMHZ-UHFFFAOYSA-N 0.000 description 3
- SLZBEPLWGGRZAY-UHFFFAOYSA-N 6-[[3-fluoro-5-(4-methoxyoxan-4-yl)phenoxy]methyl]-1-methylquinolin-2-one Chemical compound C=1C(F)=CC(OCC=2C=C3C=CC(=O)N(C)C3=CC=2)=CC=1C1(OC)CCOCC1 SLZBEPLWGGRZAY-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- 241000282412 Homo Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
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- XNRNNGPBEPRNAR-UHFFFAOYSA-N Thromboxane B2 Natural products CCCCCC(O)C=CC1OC(O)CC(O)C1CC=CCCCC(O)=O XNRNNGPBEPRNAR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229920000392 Zymosan Polymers 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D245/00—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
- Quinoline Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP90402034 | 1990-07-13 | ||
| EP91400079 | 1991-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214891A3 true CS214891A3 (en) | 1992-02-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS912148A CS214891A3 (en) | 1990-07-13 | 1991-07-11 | Thioxoheterocyclic compounds, process for their preparation and their use as medicaments |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5240941A (enExample) |
| EP (1) | EP0466452B1 (enExample) |
| JP (1) | JPH04243877A (enExample) |
| KR (1) | KR920002561A (enExample) |
| AT (1) | ATE128133T1 (enExample) |
| AU (1) | AU638579B2 (enExample) |
| CA (1) | CA2046006A1 (enExample) |
| CS (1) | CS214891A3 (enExample) |
| DE (1) | DE69113148T2 (enExample) |
| DK (1) | DK0466452T3 (enExample) |
| ES (1) | ES2076472T3 (enExample) |
| FI (1) | FI913369A7 (enExample) |
| GB (1) | GB9113137D0 (enExample) |
| GR (1) | GR3017453T3 (enExample) |
| HU (1) | HUT61999A (enExample) |
| IE (1) | IE912138A1 (enExample) |
| IL (1) | IL98603A0 (enExample) |
| MX (1) | MX174406B (enExample) |
| NO (1) | NO912750L (enExample) |
| NZ (1) | NZ238703A (enExample) |
| PT (1) | PT98292A (enExample) |
| TW (1) | TW235918B (enExample) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9018134D0 (en) * | 1989-09-29 | 1990-10-03 | Ici Plc | Heterocyclic derivatives |
| IE911853A1 (en) * | 1990-06-21 | 1992-01-01 | Ici Plc | Heterocyclene derivatives |
| IE914005A1 (en) * | 1990-12-14 | 1992-06-17 | Zeneca Ltd | Novel intermediates |
| GB9122590D0 (en) * | 1991-10-24 | 1991-12-04 | Lilly Industries Ltd | Pharmaceutical compounds |
| AU4444393A (en) * | 1992-09-01 | 1994-03-10 | Zeneca Limited | Pyrrolidine derivatives |
| US5354865A (en) * | 1992-09-10 | 1994-10-11 | Abbott Laboratories | Phenylmethyl derivatives having lipoxygenase inhibitory activity |
| IL109254A (en) * | 1993-04-29 | 1999-03-12 | Zeneca Ltd | Tetrahydropyran and tetrahydrofuran ether derivatives their preparation and pharmaceutical compositions comprising them |
| JPH08511011A (ja) * | 1993-06-07 | 1996-11-19 | ゼネカ・リミテッド | アニリン誘導体 |
| EP0702680A1 (en) * | 1993-06-07 | 1996-03-27 | Zeneca Limited | 2-oxo-1,2,3,4-tetrahydroquinoline derivatives |
| US5459271A (en) * | 1993-07-20 | 1995-10-17 | Merck Frosst Canada, Inc. | Arylbicyclooctanes as inhibitors of leukotriene biosynthesis |
| US5643933A (en) * | 1995-06-02 | 1997-07-01 | G. D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
| US6677364B2 (en) * | 1998-04-20 | 2004-01-13 | G.D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
| AU2004298486A1 (en) | 2003-12-12 | 2005-06-30 | Wyeth | Quinolines useful in treating cardiovascular disease |
| US8158362B2 (en) | 2005-03-30 | 2012-04-17 | Decode Genetics Ehf. | Methods of diagnosing susceptibility to myocardial infarction and screening for an LTA4H haplotype |
| EP1831225A2 (en) | 2004-11-19 | 2007-09-12 | The Regents of the University of California | Anti-inflammatory pyrazolopyrimidines |
| KR20150038395A (ko) | 2006-04-04 | 2015-04-08 | 더 리젠트스 오브 더 유니이버시티 오브 캘리포니아 | 키나제 길항물질 |
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| US8980899B2 (en) | 2009-10-16 | 2015-03-17 | The Regents Of The University Of California | Methods of inhibiting Ire1 |
| JP5951600B2 (ja) | 2010-05-21 | 2016-07-13 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | キナーゼ調節のための、化合物、組成物および方法 |
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| AR084824A1 (es) | 2011-01-10 | 2013-06-26 | Intellikine Inc | Procesos para preparar isoquinolinonas y formas solidas de isoquinolinonas |
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| CA2846496C (en) | 2011-09-02 | 2020-07-14 | The Regents Of The University Of California | Substituted pyrazolo[3,4-d]pyrimidines and uses thereof |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| HUE042374T2 (hu) | 2012-06-13 | 2019-06-28 | Incyte Holdings Corp | Szubsztituált triciklusos vegyületek mint FGFR inhibitorok |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| MX2015003874A (es) | 2012-09-26 | 2015-12-16 | Univ California | Modulacion de ire1. |
| WO2014071109A1 (en) | 2012-11-01 | 2014-05-08 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
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| KR102469849B1 (ko) | 2013-04-19 | 2022-11-23 | 인사이트 홀딩스 코포레이션 | Fgfr 저해제로서 이환식 헤테로사이클 |
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| PE20160685A1 (es) | 2013-10-04 | 2016-07-23 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos y usos de los mismos |
| CN113620958A (zh) | 2014-03-19 | 2021-11-09 | 无限药品股份有限公司 | 用于治疗PI3K-γ介导的障碍的杂环化合物 |
| WO2015160975A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| US9708348B2 (en) | 2014-10-03 | 2017-07-18 | Infinity Pharmaceuticals, Inc. | Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| WO2016134294A1 (en) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Bicyclic heterocycles as fgfr4 inhibitors |
| AU2016219822B2 (en) | 2015-02-20 | 2020-07-09 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US10500178B2 (en) | 2015-03-13 | 2019-12-10 | The Board Of Trustees Of The Leland Stanford Junior University | LTB4 inhibition to prevent and treat human lymphedema |
| PH12018500554B1 (en) | 2015-09-14 | 2024-01-24 | Infinity Pharmaceuticals Inc | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
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| RU2754507C2 (ru) | 2016-06-24 | 2021-09-02 | Инфинити Фармасьютикалз, Инк. | Комбинированная терапия |
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| EP3788046B1 (en) | 2018-05-04 | 2025-12-10 | Incyte Corporation | Salts of an fgfr inhibitor |
| EP4309737A3 (en) | 2018-05-04 | 2024-03-27 | Incyte Corporation | Solid forms of an fgfr inhibitor and processes for preparing the same |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
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| JP7720840B2 (ja) | 2019-12-04 | 2025-08-08 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤としての三環式複素環 |
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| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| CA3215903A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| EP4352059A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| WO2022261159A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| AU2022380979A1 (en) | 2021-11-02 | 2024-06-06 | Flare Therapeutics Inc. | Pparg inverse agonists and uses thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3661917A (en) * | 1970-05-21 | 1972-05-09 | Smith Kline French Lab | 3-sulfonamido-4-hydroxyphenyl-2-piperidylcarbinols |
| US3743737A (en) * | 1970-05-21 | 1973-07-03 | Smith Kline French Lab | 3-sulfonamido-4-hydroxyphenyl-2-piperindinylcarbinol compositions |
| IE56702B1 (en) * | 1982-12-01 | 1991-11-06 | Usv Pharma Corp | Antiinflammatory antiallergic compounds |
| NZ213986A (en) * | 1984-10-30 | 1989-07-27 | Usv Pharma Corp | Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such |
| US4839369A (en) * | 1985-04-16 | 1989-06-13 | Rorer Pharmaceutical Corporation | Aryl and heteroaryl ethers as agents for the treatment of hypersensitive ailments |
| US4876346A (en) * | 1985-05-02 | 1989-10-24 | American Home Products Corporation | Quinoline compounds |
| EP0271287A3 (en) * | 1986-12-11 | 1990-06-13 | Merck Frosst Canada Inc. | Quinoline dioic acids and amides |
| US4920132A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4920133A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4920130A (en) * | 1987-11-02 | 1990-04-24 | Rorer Pharamceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4920131A (en) * | 1987-11-03 | 1990-04-24 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene D4 |
| US4918081A (en) * | 1988-06-20 | 1990-04-17 | Rorer Pharmaceutical Corp. | Quinoline derivatives and use thereof as antagonists of leukotriene d4 |
| EP0349062A1 (en) * | 1988-06-27 | 1990-01-03 | Merck Frosst Canada Inc. | Quinoline ether alkanoic acid |
| GB8926981D0 (en) * | 1988-12-23 | 1990-01-17 | Ici Plc | Heterocyclic derivatives |
| IE70521B1 (en) * | 1989-02-28 | 1996-12-11 | Zeneca Pharma Sa | Heterocycles with inhibitory activity of 5-lipoxygenase |
| GB9018134D0 (en) * | 1989-09-29 | 1990-10-03 | Ici Plc | Heterocyclic derivatives |
-
1991
- 1991-06-18 GB GB919113137A patent/GB9113137D0/en active Pending
- 1991-06-20 IE IE213891A patent/IE912138A1/en unknown
- 1991-06-24 IL IL98603A patent/IL98603A0/xx unknown
- 1991-06-26 AU AU79337/91A patent/AU638579B2/en not_active Ceased
- 1991-06-26 NZ NZ238703A patent/NZ238703A/xx unknown
- 1991-06-28 CA CA002046006A patent/CA2046006A1/en not_active Abandoned
- 1991-07-08 HU HU912295A patent/HUT61999A/hu unknown
- 1991-07-09 EP EP91306213A patent/EP0466452B1/en not_active Expired - Lifetime
- 1991-07-09 DE DE69113148T patent/DE69113148T2/de not_active Expired - Fee Related
- 1991-07-09 AT AT91306213T patent/ATE128133T1/de not_active IP Right Cessation
- 1991-07-09 DK DK91306213.9T patent/DK0466452T3/da active
- 1991-07-09 ES ES91306213T patent/ES2076472T3/es not_active Expired - Lifetime
- 1991-07-11 US US07/728,371 patent/US5240941A/en not_active Expired - Fee Related
- 1991-07-11 CS CS912148A patent/CS214891A3/cs unknown
- 1991-07-11 FI FI913369A patent/FI913369A7/fi not_active Application Discontinuation
- 1991-07-11 PT PT98292A patent/PT98292A/pt not_active Application Discontinuation
- 1991-07-12 JP JP3172295A patent/JPH04243877A/ja active Pending
- 1991-07-12 MX MX9100201A patent/MX174406B/es not_active IP Right Cessation
- 1991-07-12 KR KR1019910012111A patent/KR920002561A/ko not_active Withdrawn
- 1991-07-12 NO NO91912750A patent/NO912750L/no unknown
- 1991-07-24 TW TW080105761A patent/TW235918B/zh active
-
1995
- 1995-09-21 GR GR940403950T patent/GR3017453T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL98603A0 (en) | 1992-07-15 |
| NZ238703A (en) | 1994-01-26 |
| DE69113148D1 (de) | 1995-10-26 |
| ES2076472T3 (es) | 1995-11-01 |
| FI913369A0 (fi) | 1991-07-11 |
| AU7933791A (en) | 1992-01-16 |
| CA2046006A1 (en) | 1992-01-14 |
| ATE128133T1 (de) | 1995-10-15 |
| PT98292A (pt) | 1992-05-29 |
| DK0466452T3 (da) | 1996-01-02 |
| IE912138A1 (en) | 1992-01-15 |
| GR3017453T3 (en) | 1995-12-31 |
| US5240941A (en) | 1993-08-31 |
| HU912295D0 (en) | 1991-12-30 |
| JPH04243877A (ja) | 1992-08-31 |
| HUT61999A (en) | 1993-03-29 |
| NO912750L (no) | 1992-01-14 |
| TW235918B (enExample) | 1994-12-11 |
| AU638579B2 (en) | 1993-07-01 |
| GB9113137D0 (en) | 1991-08-07 |
| FI913369A7 (fi) | 1992-01-14 |
| EP0466452A2 (en) | 1992-01-15 |
| KR920002561A (ko) | 1992-02-28 |
| NO912750D0 (no) | 1991-07-12 |
| MX174406B (es) | 1994-05-13 |
| EP0466452B1 (en) | 1995-09-20 |
| EP0466452A3 (en) | 1992-08-19 |
| DE69113148T2 (de) | 1996-03-28 |
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