UA75086C2 - Quinolinone derivatives - Google Patents
Quinolinone derivatives Download PDFInfo
- Publication number
- UA75086C2 UA75086C2 UA2003031989A UA2003031989A UA75086C2 UA 75086 C2 UA75086 C2 UA 75086C2 UA 2003031989 A UA2003031989 A UA 2003031989A UA 2003031989 A UA2003031989 A UA 2003031989A UA 75086 C2 UA75086 C2 UA 75086C2
- Authority
- UA
- Ukraine
- Prior art keywords
- groups
- substituted
- unsubstituted
- alkyl
- aryl
- Prior art date
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- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title description 295
- 238000000034 method Methods 0.000 abstract description 122
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 36
- 150000003839 salts Chemical class 0.000 abstract description 34
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 17
- 238000002156 mixing Methods 0.000 abstract description 8
- 150000002894 organic compounds Chemical class 0.000 abstract description 5
- 239000003937 drug carrier Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 description 739
- 125000003118 aryl group Chemical group 0.000 description 629
- 125000000623 heterocyclic group Chemical group 0.000 description 577
- 150000001875 compounds Chemical class 0.000 description 320
- 125000004103 aminoalkyl group Chemical group 0.000 description 225
- -1 -OH Chemical group 0.000 description 175
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 110
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 108
- 125000000547 substituted alkyl group Chemical group 0.000 description 85
- 125000005128 aryl amino alkyl group Chemical group 0.000 description 84
- 229910052739 hydrogen Inorganic materials 0.000 description 83
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 82
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 81
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 80
- 239000000047 product Substances 0.000 description 74
- 239000007787 solid Substances 0.000 description 73
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 66
- 239000000203 mixture Substances 0.000 description 66
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 62
- 125000003277 amino group Chemical group 0.000 description 60
- 229910052799 carbon Inorganic materials 0.000 description 59
- 125000003545 alkoxy group Chemical group 0.000 description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 56
- 239000000243 solution Substances 0.000 description 53
- 125000004429 atom Chemical group 0.000 description 50
- 239000001257 hydrogen Substances 0.000 description 48
- 125000004104 aryloxy group Chemical group 0.000 description 38
- 125000003282 alkyl amino group Chemical class 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- 125000000304 alkynyl group Chemical group 0.000 description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 description 31
- 125000001769 aryl amino group Chemical group 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 27
- 125000004663 dialkyl amino group Chemical group 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 238000000746 purification Methods 0.000 description 27
- 150000001721 carbon Chemical group 0.000 description 26
- 125000003107 substituted aryl group Chemical group 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004587 chromatography analysis Methods 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 23
- 125000003342 alkenyl group Chemical group 0.000 description 23
- 239000000126 substance Substances 0.000 description 23
- 125000004122 cyclic group Chemical group 0.000 description 22
- 125000004986 diarylamino group Chemical group 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 21
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 20
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 20
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 238000006264 debenzylation reaction Methods 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 239000007858 starting material Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 18
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 17
- 125000003710 aryl alkyl group Chemical group 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 206010028980 Neoplasm Diseases 0.000 description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 125000004430 oxygen atom Chemical group O* 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 11
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 229930185107 quinolinone Natural products 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 9
- 230000035755 proliferation Effects 0.000 description 9
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 9
- IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 8
- 230000033115 angiogenesis Effects 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 8
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 230000002792 vascular Effects 0.000 description 8
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical class NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000004193 piperazinyl group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000005110 aryl thio group Chemical group 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 239000003102 growth factor Substances 0.000 description 6
- 150000002460 imidazoles Chemical class 0.000 description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
- 150000003233 pyrroles Chemical class 0.000 description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 6
- 239000007790 solid phase Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000003536 tetrazoles Chemical class 0.000 description 6
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 5
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 150000001556 benzimidazoles Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 150000003854 isothiazoles Chemical class 0.000 description 5
- 150000002545 isoxazoles Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000002780 morpholines Chemical class 0.000 description 5
- 150000002916 oxazoles Chemical class 0.000 description 5
- 102000020233 phosphotransferase Human genes 0.000 description 5
- 125000003386 piperidinyl group Chemical group 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 5
- 125000004426 substituted alkynyl group Chemical group 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 150000003557 thiazoles Chemical class 0.000 description 5
- 150000000177 1,2,3-triazoles Chemical class 0.000 description 4
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 4
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 4
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
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- 230000002378 acidificating effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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- 238000007429 general method Methods 0.000 description 4
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- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- AEMXNRIHRLEYAK-UHFFFAOYSA-N pyridin-2-yl acetate Chemical compound CC(=O)OC1=CC=CC=N1 AEMXNRIHRLEYAK-UHFFFAOYSA-N 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- FNLQDVXHDNFXIY-UHFFFAOYSA-N 3h-benzimidazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2NC=NC2=C1 FNLQDVXHDNFXIY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 102100027907 Cytoplasmic tyrosine-protein kinase BMX Human genes 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 101000935548 Homo sapiens Cytoplasmic tyrosine-protein kinase BMX Proteins 0.000 description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US23215900P | 2000-09-11 | 2000-09-11 | |
PCT/US2001/042131 WO2002022598A1 (fr) | 2000-09-11 | 2001-09-11 | Derives de quinolinone |
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UA75086C2 true UA75086C2 (en) | 2006-03-15 |
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EP (3) | EP1317442B1 (fr) |
JP (4) | JP4361727B2 (fr) |
KR (3) | KR100732206B1 (fr) |
CN (1) | CN100351249C (fr) |
AP (1) | AP1666A (fr) |
AT (2) | ATE309996T1 (fr) |
AU (2) | AU2001293275B2 (fr) |
BG (1) | BG66087B1 (fr) |
BR (2) | BRPI0113757B1 (fr) |
CA (1) | CA2421120C (fr) |
CY (2) | CY1108070T1 (fr) |
CZ (1) | CZ304344B6 (fr) |
DE (2) | DE60132937T2 (fr) |
DK (2) | DK1317442T3 (fr) |
DZ (1) | DZ3425A1 (fr) |
EA (1) | EA006711B1 (fr) |
EC (1) | ECSP034548A (fr) |
ES (2) | ES2302106T3 (fr) |
HK (2) | HK1053644A1 (fr) |
HU (1) | HU230787B1 (fr) |
IL (3) | IL154618A0 (fr) |
MA (1) | MA27957A1 (fr) |
MX (1) | MXPA03002032A (fr) |
NO (2) | NO324155B1 (fr) |
NZ (1) | NZ524717A (fr) |
OA (1) | OA12428A (fr) |
PL (1) | PL211125B1 (fr) |
PT (1) | PT1650203E (fr) |
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UA (1) | UA75086C2 (fr) |
WO (1) | WO2002022598A1 (fr) |
ZA (1) | ZA200301578B (fr) |
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ATE448226T1 (de) | 2000-09-01 | 2009-11-15 | Novartis Vaccines & Diagnostic | Aza heterocyclische derivate und ihre therapeutische verwendung |
US20030028018A1 (en) * | 2000-09-11 | 2003-02-06 | Chiron Coporation | Quinolinone derivatives |
PT1650203E (pt) * | 2000-09-11 | 2008-05-13 | Novartis Vaccines & Diagnostic | Processo de preparação de derivados de benzimidazol-2-ilquinolinona |
EP1401831A1 (fr) * | 2001-07-03 | 2004-03-31 | Chiron Corporation | Composes d'indazole benzimidazole utilises comme inhibiteurs de tyrosine et de serine/threonine kinase |
US7642278B2 (en) * | 2001-07-03 | 2010-01-05 | Novartis Vaccines And Diagnostics, Inc. | Indazole benzimidazole compounds |
WO2003045929A1 (fr) | 2001-11-26 | 2003-06-05 | Takeda Chemical Industries, Ltd. | Derive bicyclique, procede de production de ce derive et utilisation correspondante |
US6822097B1 (en) * | 2002-02-07 | 2004-11-23 | Amgen, Inc. | Compounds and methods of uses |
JP2005532368A (ja) * | 2002-06-12 | 2005-10-27 | アボット・ラボラトリーズ | メラニン濃縮ホルモン受容体の拮抗薬 |
DE10238002A1 (de) | 2002-08-20 | 2004-03-04 | Merck Patent Gmbh | Benzimidazolderivate |
US20050256157A1 (en) * | 2002-08-23 | 2005-11-17 | Chiron Corporation | Combination therapy with CHK1 inhibitors |
US7825132B2 (en) | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
BR0313743A (pt) * | 2002-08-23 | 2005-07-05 | Chiron Corp | Benzimidazol quinolinonas e usos destas |
AU2003275282A1 (en) * | 2002-09-30 | 2004-04-23 | Bristol-Myers Squibb Company | Novel tyrosine kinase inhibitors |
AU2003290699B2 (en) * | 2002-11-13 | 2009-08-27 | Novartis Vaccines And Diagnostics, Inc. | Methods of treating cancer and related methods |
CN100377709C (zh) * | 2002-11-13 | 2008-04-02 | 希龙公司 | 受体酪氨酸激酶抑制剂的制药用途及相关检测方法 |
EP1590339A4 (fr) * | 2003-01-28 | 2007-07-25 | Smithkline Beecham Corp | Composes chimiques |
ES2423800T3 (es) | 2003-03-28 | 2013-09-24 | Novartis Vaccines And Diagnostics, Inc. | Uso de compuestos orgánicos para la inmunopotenciación |
US7627675B2 (en) * | 2003-05-01 | 2009-12-01 | Cisco Technology, Inc. | Methods and devices for regulating traffic on a network |
US7326788B2 (en) | 2003-07-22 | 2008-02-05 | Janssen Pharmaceutica N.V. | Quinolinone derivatives as inhibitors of c-fms kinase |
CA2532800C (fr) | 2003-07-23 | 2013-06-18 | Exelixis, Inc. | Modulateurs de la proteine alk (anaplastic lymphoma kinase) et leurs methodes d'utilisation |
KR101167573B1 (ko) * | 2003-11-07 | 2012-07-30 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 개선된 약학적 성질을 갖는 퀴놀리논 화합물의 약학적으로허용가능한 염 |
CN1976706B (zh) * | 2003-11-07 | 2012-01-18 | 诺华疫苗和诊断公司 | 抑制fgfr3及治疗多发性骨髓瘤 |
CA2545711A1 (fr) * | 2003-11-13 | 2005-06-02 | Ambit Biosciences Corporation | Derives d'uree en tant que modulateurs de la kinase |
WO2005054183A2 (fr) * | 2003-12-01 | 2005-06-16 | The Scripps Research Institute | Inhibiteurs de proteines kinases a base de quinolinone |
RU2377988C2 (ru) * | 2004-02-20 | 2010-01-10 | Новартис Вэксинес Энд Дайэгностикс, Инк. | Модуляция воспалительных и метастатических процессов |
GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
US7521446B2 (en) | 2005-01-13 | 2009-04-21 | Signal Pharmaceuticals, Llc | Haloaryl substituted aminopurines, compositions thereof, and methods of treatment therewith |
US7723340B2 (en) | 2005-01-13 | 2010-05-25 | Signal Pharmaceuticals, Llc | Haloaryl substituted aminopurines, compositions thereof, and methods of treatment therewith |
US7759342B2 (en) | 2005-01-13 | 2010-07-20 | Signal Pharmaceuticals, Llc | Methods of treatment and prevention using haloaryl substituted aminopurines |
ATE526025T1 (de) * | 2005-01-27 | 2011-10-15 | Novartis Vaccines & Diagnostic | Behandlung metastasierter tumore |
ES2385045T3 (es) | 2005-02-18 | 2012-07-17 | Novartis Vaccines And Diagnostics, Inc. | Inmunógenos de Escherichia coli uropatogénica |
HUE027400T2 (en) | 2005-02-18 | 2016-10-28 | Glaxosmithkline Biologicals Sa | Proteins and nucleic acids from meningitis / sepsis with Escherichia coli |
ES2440799T3 (es) * | 2005-05-13 | 2014-01-30 | Novartis Ag | Métodos para tratar cáncer resistente a los fármacos |
JP5545925B2 (ja) | 2005-05-17 | 2014-07-09 | ノバルティス アーゲー | ヘテロ環化合物の合成方法 |
CA2609353C (fr) * | 2005-05-23 | 2015-04-28 | Novartis Ag | Formes cristalline et autres de sels d'acide lactique 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]-1h-quinolin-2-one |
WO2007011777A2 (fr) | 2005-07-18 | 2007-01-25 | Novartis Ag | Modele petit animal pour une replication hcv |
CA2624025A1 (fr) * | 2005-10-14 | 2007-04-19 | F. Hoffmann-La Roche Ag | Regime d'administration de la 5-(2-chlorophenyl)-1,2-dihydro-7-fluoro-8-methoxy-3-methyl-pyrazolo [3,4.-b] [1,4] benzodiazepine |
NZ567978A (en) | 2005-11-04 | 2011-09-30 | Novartis Vaccines & Diagnostic | Influenza vaccine with reduced amount of oil-in-water emulsion as adjuvant |
EP1951299B1 (fr) | 2005-11-04 | 2012-01-04 | Novartis Vaccines and Diagnostics S.r.l. | Vaccins influenza comprenant des combinaisons d'adjuvants particulaires et d'immunopotentiateurs |
AU2006310337B9 (en) | 2005-11-04 | 2013-11-28 | Novartis Ag | Adjuvanted influenza vaccines including cytokine-inducing agents |
CA2628152C (fr) | 2005-11-04 | 2016-02-02 | Novartis Vaccines And Diagnostics S.R.L. | Vaccins avec adjuvant comprenant des antigenes sans virions prepares a partir de virus influenza eleves en culture cellulaire |
DE102005054904A1 (de) * | 2005-11-17 | 2007-05-24 | Wacker Polymer Systems Gmbh & Co. Kg | Verfahren zur Herstellung polyvinylalkoholstabilisierter Latices |
PT1957074E (pt) | 2005-11-29 | 2014-06-25 | Novartis Ag | Formulações de quinolinonas |
KR20080080525A (ko) | 2005-12-08 | 2008-09-04 | 노파르티스 아게 | 유전자 전사에 대한 fgfr3의 억제제의 효과 |
JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
PL1976559T6 (pl) | 2006-01-27 | 2020-08-10 | Novartis Influenza Vaccines Marburg Gmbh | Szczepionki przeciw grypie zawierające hemaglutyninę i białka macierzy |
PE20070978A1 (es) * | 2006-02-14 | 2007-11-15 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE FOSFATIDILINOSITOL 3-QUINASAS (PI3Ks) |
TW200803855A (en) * | 2006-02-24 | 2008-01-16 | Kalypsys Inc | Quinolones useful as inducible nitric oxide synthase inhibitors |
AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
CA2647100A1 (fr) * | 2006-03-23 | 2007-09-27 | Novartis Ag | Procedes de preparation de composes contenant de l'imidazole |
CA2646891A1 (fr) * | 2006-03-23 | 2007-09-27 | Novartis Ag | Composes de potentialisation immunitaire |
EP2357184B1 (fr) | 2006-03-23 | 2015-02-25 | Novartis AG | Composés d'imidazoquinoxaline en tant qu'immunomodulateurs |
JP2009534303A (ja) | 2006-03-24 | 2009-09-24 | ノバルティス ヴァクシンズ アンド ダイアグノスティクス ゲーエムベーハー アンド カンパニー カーゲー | 冷蔵しないインフルエンザワクチンの保存 |
US20100285062A1 (en) | 2006-03-31 | 2010-11-11 | Novartis Ag | Combined mucosal and parenteral immunization against hiv |
TW200808739A (en) * | 2006-04-06 | 2008-02-16 | Novartis Vaccines & Diagnostic | Quinazolines for PDK1 inhibition |
US20070293491A1 (en) | 2006-04-19 | 2007-12-20 | Novartis Vaccines And Diagnostics, Inc. | Indazole compounds and methods for inhibition of cdc7 |
US20110206692A1 (en) | 2006-06-09 | 2011-08-25 | Novartis Ag | Conformers of bacterial adhesins |
US7745646B2 (en) | 2006-07-07 | 2010-06-29 | Kalypsys, Inc. | Bicyclic heteroaryl inhibitors of PDE4 |
US8138205B2 (en) | 2006-07-07 | 2012-03-20 | Kalypsys, Inc. | Heteroarylalkoxy-substituted quinolone inhibitors of PDE4 |
GB0614460D0 (en) | 2006-07-20 | 2006-08-30 | Novartis Ag | Vaccines |
EP2586790A3 (fr) | 2006-08-16 | 2013-08-14 | Novartis AG | Immunogènes d'Escherischia coli pathogènes des voies urinaires |
CA2663196A1 (fr) | 2006-09-11 | 2008-03-20 | Novartis Ag | Fabrication de vaccins contre le virus grippal sans utiliser d'oeufs |
WO2008044045A1 (fr) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Combinaisons pharmaceutiques |
US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
JP2011506264A (ja) | 2006-12-06 | 2011-03-03 | ノバルティス アーゲー | インフルエンザウイルスの4つの株に由来する抗原を含むワクチン |
GB0700562D0 (en) | 2007-01-11 | 2007-02-21 | Novartis Vaccines & Diagnostic | Modified Saccharides |
TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
UA101611C2 (ru) * | 2007-04-03 | 2013-04-25 | Аррей Байофарма Инк. | СОЕДИНЕНИЯ ИМИДАЗО[1,2-а]ПИРИДИНА КАК ИНГИБИТОРЫ ТИРОЗИНКИНАЗЫ РЕЦЕПТОРОВ |
MX2009012117A (es) * | 2007-05-09 | 2009-11-23 | Pfizer | Composiciones y derivados heterociclicos sustituidos y su uso farmaceutico como antibacterianos. |
SI2185191T1 (sl) | 2007-06-27 | 2012-12-31 | Novartis Ag | Cepiva proti influenci z majhnimi dodatki |
GB0713880D0 (en) * | 2007-07-17 | 2007-08-29 | Novartis Ag | Conjugate purification |
GB0714963D0 (en) | 2007-08-01 | 2007-09-12 | Novartis Ag | Compositions comprising antigens |
NZ584145A (en) | 2007-09-14 | 2012-03-30 | Ortho Mcneil Janssen Pharm | 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h, 1'h-[1,4'] bipyridinyl-2'-ones |
EA019085B1 (ru) | 2007-09-14 | 2014-01-30 | Янссен Фармасьютикалз, Инк. | 1',3-двузамещенные 4-(арил-х-фенил)-1н-пиридин-2-оны |
GB0810305D0 (en) | 2008-06-05 | 2008-07-09 | Novartis Ag | Influenza vaccination |
GB0818453D0 (en) | 2008-10-08 | 2008-11-12 | Novartis Ag | Fermentation processes for cultivating streptococci and purification processes for obtaining cps therefrom |
PA8809001A1 (es) | 2007-12-20 | 2009-07-23 | Novartis Ag | Compuestos organicos |
EP2268309B1 (fr) | 2008-03-18 | 2015-01-21 | Novartis AG | Améliorations dans la préparation des antigènes pour le vaccin contre le virus de la grippe |
PE20091628A1 (es) * | 2008-03-19 | 2009-11-19 | Novartis Ag | Formas cristalinas y dos formas solvatadas de sales de acido lactico de 4-amino-5-fluoro-3-[5-(4-metilpiperazin-1-il)-1h-benzimidazol-2-il]quinolin-2(1h)-ona |
ES2439291T3 (es) | 2008-09-02 | 2014-01-22 | Janssen Pharmaceuticals, Inc. | Derivados de 3-azabiciclo[3.1.0]hexilo como moduladores de receptores de glutamato metabotrópicos |
MX2011005242A (es) | 2008-11-28 | 2011-09-06 | Ortho Mcneil Janssen Pharm | Derivados de indol y benzoxazina como moduladores de los receptores de glutamato metabotropicos. |
US8568732B2 (en) | 2009-03-06 | 2013-10-29 | Novartis Ag | Chlamydia antigens |
SG175092A1 (en) | 2009-04-14 | 2011-11-28 | Novartis Ag | Compositions for immunising against staphylococcus aerus |
EP2424565A1 (fr) | 2009-04-27 | 2012-03-07 | Novartis AG | Vaccins avec adjuvants pour protéger du virus de la grippe |
TWI410418B (zh) | 2009-04-29 | 2013-10-01 | Ind Tech Res Inst | 氮雜薁化合物、藥學組合物與抑制一細胞中蛋白質激酶之活性的方法 |
JO2860B1 (en) | 2009-05-07 | 2015-03-15 | ايلي ليلي اند كومباني | Phenylendazolyl compounds |
CA2760259C (fr) | 2009-05-12 | 2018-05-01 | Janssen Pharmaceuticals, Inc. | Derives de la 1,2,4-triazolo [4,3-a] pyridine et leur utilisation en tant que modulateurs allosteriques positifs des recepteurs mglur2 |
MY161325A (en) | 2009-05-12 | 2017-04-14 | Janssen Pharmaceuticals Inc | 1, 2, 4-triazolo[4,3-a]pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
US8293753B2 (en) | 2009-07-02 | 2012-10-23 | Novartis Ag | Substituted 2-carboxamide cycloamino ureas |
SG177533A1 (en) | 2009-07-07 | 2012-02-28 | Novartis Ag | Conserved escherichia coli immunogens |
HRP20220756T1 (hr) | 2009-07-15 | 2022-09-02 | Glaxosmithkline Biologicals S.A. | Proteinski pripravci rsv f i postupci za izradu istih |
SG178035A1 (en) | 2009-07-16 | 2012-03-29 | Novartis Ag | Detoxified escherichia coli immunogens |
US8554514B2 (en) * | 2009-09-18 | 2013-10-08 | Advantest Corporation | Test apparatus and test method |
GB0918392D0 (en) | 2009-10-20 | 2009-12-02 | Novartis Ag | Diagnostic and therapeutic methods |
GB0919690D0 (en) | 2009-11-10 | 2009-12-23 | Guy S And St Thomas S Nhs Foun | compositions for immunising against staphylococcus aureus |
EP2512476A1 (fr) | 2009-12-18 | 2012-10-24 | Novartis AG | Procédé pour le traitement de cancers hématologiques |
EP2519265B1 (fr) | 2009-12-30 | 2018-11-14 | GlaxoSmithKline Biologicals SA | Immunogènes de polysaccharide conjugués à des protéines porteuses de e. coli |
EP2558082A1 (fr) | 2010-04-16 | 2013-02-20 | Novartis AG | Combinaison de composés organiques |
PL2558095T3 (pl) | 2010-04-16 | 2019-06-28 | Novartis Ag | Związek organiczny, przeznaczony do stosowania w leczeniu raka wątroby |
JP2013532008A (ja) | 2010-05-28 | 2013-08-15 | テトリス オンライン インコーポレイテッド | 対話式ハイブリッド非同期コンピュータ・ゲーム・インフラストラクチャ |
GB201009861D0 (en) | 2010-06-11 | 2010-07-21 | Novartis Ag | OMV vaccines |
UY33472A (es) | 2010-06-30 | 2012-01-31 | Novartis Ag | ?composiciones farmacéuticas que comprenden monohidrato de lactato de 4-amino-5-fluoro-3-[6-(4-metil-piperazin-1-il)-1hbencimidazol-2-il]-1h-quinolin-2-ona?. |
US9192661B2 (en) | 2010-07-06 | 2015-11-24 | Novartis Ag | Delivery of self-replicating RNA using biodegradable polymer particles |
AR082418A1 (es) | 2010-08-02 | 2012-12-05 | Novartis Ag | Formas cristalinas de 1-(4-metil-5-[2-(2,2,2-trifluoro-1,1-dimetil-etil)-piridin-4-il]-tiazol-2-il)-amida de 2-amida del acido (s)-pirrolidin-1,2-dicarboxilico |
WO2012028243A1 (fr) | 2010-09-02 | 2012-03-08 | Merck Patent Gmbh | Dérivés de pyrazolopyridinone en tant qu'antagonistes de récepteur de lpa |
JO3062B1 (ar) * | 2010-10-05 | 2017-03-15 | Lilly Co Eli | R)-(e)-2-(4-(2-(5-(1-(3، 5-داي كلورو بيريدين-4-يل)إيثوكسي)-1h-إندازول-3-يل)?ينيل)-1h-بيرازول-1-يل)إيثانول بلوري |
CN103298809B (zh) | 2010-11-08 | 2016-08-31 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
ES2536433T3 (es) | 2010-11-08 | 2015-05-25 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
JP5852664B2 (ja) | 2010-11-08 | 2016-02-03 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | 1,2,4−トリアゾロ[4,3−a]ピリジン誘導体およびmGluR2受容体のポジティブアロステリックモジュレーターとしてのそれらの使用 |
TR201908715T4 (tr) | 2011-01-26 | 2019-07-22 | Glaxosmithkline Biologicals Sa | Rsv immünizasyon rejimi. |
KR101928116B1 (ko) | 2011-01-31 | 2018-12-11 | 노파르티스 아게 | 신규 헤테로시클릭 유도체 |
KR20140012137A (ko) | 2011-03-17 | 2014-01-29 | 노파르티스 아게 | Hr 양성 대상체에서의 유방암용 바이오마커로서의 fgfr 및 이의 리간드 |
PL2707385T3 (pl) | 2011-05-13 | 2018-03-30 | Glaxosmithkline Biologicals Sa | Prefuzyjne antygeny RSV F |
WO2012158994A1 (fr) | 2011-05-19 | 2012-11-22 | Novartis Ag | 4-amino-5-fluoro-3-[6-(4-méthylpipérazin-1-yl)-1h-benzimidazol-2-yl]-1h-quinoléin-2-one destinée à être utilisée dans le traitement du carcinome adénoïde kystique |
EP2554662A1 (fr) | 2011-08-05 | 2013-02-06 | M Maria Pia Cosma | Procédés pour le traitement de maladies rétiniennes dégénératives |
CA2848210A1 (fr) | 2011-09-15 | 2013-03-21 | Novartis Ag | Utilisation de la 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1h-benzimidazol-2-yl]-1h-quinolin-2-one dans le traitement du cancer chez des patients atteints d'une insuffisancehepatique moderee |
CA2853256C (fr) | 2011-10-28 | 2019-05-14 | Novartis Ag | Nouveaux derives de purine et utilisation de ceux-ci dans le traitement d'une maladie |
WO2013063003A1 (fr) | 2011-10-28 | 2013-05-02 | Novartis Ag | Méthode de traitement des tumeurs stromales gastro-intestinales |
CA2854934A1 (fr) | 2011-11-07 | 2013-05-16 | Novartis Ag | Molecule porteuse comprenant un antigene spr0096 et un antigene spr2021 |
EP2809312A1 (fr) | 2012-01-31 | 2014-12-10 | Novartis AG | Combinaison d'un inhibiteur de rtk avec un anti- strogène et son utilisation pour traiter le cancer |
SG11201406550QA (en) | 2012-05-16 | 2014-11-27 | Novartis Ag | Dosage regimen for a pi-3 kinase inhibitor |
JP2015522070A (ja) | 2012-07-11 | 2015-08-03 | ノバルティス アーゲー | 消化管間質腫瘍を治療する方法 |
EA201590427A1 (ru) | 2012-10-02 | 2015-09-30 | Глаксосмитклайн Байолоджикалс С.А. | Нелинейные сахаридные конъюгаты |
WO2014058785A1 (fr) | 2012-10-10 | 2014-04-17 | Novartis Ag | Polythérapie |
CN103804353A (zh) * | 2012-11-01 | 2014-05-21 | 常辉 | 一类治疗精神分裂症的化合物及其用途 |
US9987344B2 (en) | 2012-11-30 | 2018-06-05 | Glaxosmithkline Biologicals Sa | Pseudomonas antigens and antigen combinations |
EP2764866A1 (fr) | 2013-02-07 | 2014-08-13 | IP Gesellschaft für Management mbH | Inhibiteurs de l'enzyme activant nedd8 |
EP2956138B1 (fr) | 2013-02-15 | 2022-06-22 | Kala Pharmaceuticals, Inc. | Composés thérapeutiques et utilisations de ceux-ci |
US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
ES2831625T3 (es) | 2013-02-20 | 2021-06-09 | Kala Pharmaceuticals Inc | Compuestos terapéuticos y sus usos |
WO2014191938A1 (fr) | 2013-05-31 | 2014-12-04 | Novartis Ag | Polythérapie comprenant un inhibiteur pi3k-alpha et un inhibiteur de kinase fgfr pour traiter le cancer |
JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
KR102103256B1 (ko) | 2013-10-14 | 2020-04-23 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 선택적으로 치환된 퀴놀린 화합물 |
KR102365952B1 (ko) | 2013-10-14 | 2022-02-22 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 선택적으로 치환된 퀴놀린 화합물 |
MX355330B (es) | 2013-11-01 | 2018-04-16 | Kala Pharmaceuticals Inc | Formas cristalinas de compuestos terapeuticos y sus usos. |
US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
EP2870974A1 (fr) | 2013-11-08 | 2015-05-13 | Novartis AG | Vaccins conjugués de salmonelle |
KR20160095035A (ko) | 2013-12-06 | 2016-08-10 | 노파르티스 아게 | 알파-이소형 선택성 포스파티딜이노시톨 3-키나제 억제제를 위한 투여 요법 |
WO2015110435A1 (fr) | 2014-01-21 | 2015-07-30 | Janssen Pharmaceutica Nv | Combinaisons comprenant des modulateurs allostériques positifs ou des agonistes orthostériques de sous-type 2 de récepteur glutamatergique métabotrope, et leur utilisation |
ME03518B (fr) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Combinaisons comprenant des modulateurs allostériques positifs de sous-type 2 de récepteurs glutamatergiques métabotropes et leur utilisation |
WO2015155738A2 (fr) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Utilisation d'inhibiteurs ou d'activateurs de gsk -3 qui modulent l'expression de pd -1 ou de t-bet pour moduler l'immunité due aux lymphocytes t |
CA2950780C (fr) | 2014-06-17 | 2023-05-16 | Vertex Pharmaceuticals Incorporated | Methode de traitement anticancereux utilisant une association d'inhibiteurs de chk1 et d'atr |
KR20170045205A (ko) | 2014-07-09 | 2017-04-26 | 티씨 바이오팜 리미티드 | 감마 델타 t 세포 및 이의 용도 |
GB201506423D0 (en) | 2015-04-15 | 2015-05-27 | Tc Biopharm Ltd | Gamma delta T cells and uses thereof |
WO2016055916A1 (fr) | 2014-10-06 | 2016-04-14 | Novartis Ag | Combinaison thérapeutique pour le traitement du cancer |
KR101693781B1 (ko) * | 2014-10-06 | 2017-01-09 | 한양대학교 에리카산학협력단 | 다이플루오로알킬기가 도입된 방향족 화합물의 제조 방법 |
CN104774221B (zh) * | 2015-03-19 | 2017-02-08 | 广西师范大学 | 喹啉酮衍生物的金属配合物及其合成方法及应用 |
CN104725431B (zh) * | 2015-03-19 | 2017-05-17 | 广西师范大学 | 喹啉酮衍生物的钴(ⅱ)配合物及其合成方法及应用 |
CN104817535A (zh) * | 2015-03-19 | 2015-08-05 | 广西师范大学 | 一种喹啉酮衍生物及其合成方法及应用 |
CN107922349B (zh) | 2015-08-07 | 2021-05-07 | 哈尔滨珍宝制药有限公司 | 作为fgfr和vegfr抑制剂的乙烯基化合物 |
WO2017040963A1 (fr) | 2015-09-03 | 2017-03-09 | Forma Therapeutics, Inc. | Inhibiteurs de hdac8 bicyclique [6,6] fusionnée |
AU2016331955B2 (en) | 2015-09-30 | 2022-07-21 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
CA3002954A1 (fr) | 2015-11-02 | 2017-05-11 | Novartis Ag | Schema posologique pour un inhibiteur de la phosphatidylinositol 3-kinase |
EP3231434A1 (fr) | 2016-04-14 | 2017-10-18 | Fundacio Centre de Regulacio Genomica | Procédé de traitement de la maladie de parkinson |
JP2019533641A (ja) | 2016-09-08 | 2019-11-21 | カラ ファーマシューティカルズ インコーポレイテッド | 治療用化合物の結晶形態およびその使用 |
EP3509423A4 (fr) | 2016-09-08 | 2020-05-13 | Kala Pharmaceuticals, Inc. | Formes cristallines de composés thérapeutiques et leurs utilisations |
WO2018048747A1 (fr) | 2016-09-08 | 2018-03-15 | Kala Pharmaceuticals, Inc. | Formes cristallines de composés thérapeutiques et leurs utilisations |
WO2018060833A1 (fr) | 2016-09-27 | 2018-04-05 | Novartis Ag | Schéma posologique pour l'alpelisib, un inhibiteur de la phosphatidylinositol 3-kinase spécifique de l'isoforme alpha |
CN107935858B (zh) * | 2016-10-12 | 2020-09-08 | 利尔化学股份有限公司 | 5-氟-2-硝基苯酚的制备方法 |
BR112019027676A2 (pt) | 2017-06-27 | 2020-09-15 | Janssen Pharmaceutica Nv | compostos de quinolinona |
BR112020010004A2 (pt) | 2017-11-24 | 2020-10-13 | Janssen Pharmaceutica Nv | compostos de pirazolopiridinona |
JP7312171B2 (ja) | 2017-11-24 | 2023-07-20 | ヤンセン ファーマシューティカ エヌ.ベー. | ピラゾロピリジノン化合物 |
US11078194B2 (en) | 2017-12-07 | 2021-08-03 | Harbin Zhenbao Pharmaceutical Co., Ltd. | Salt form and crystal form serving as FGFR and VEGFR inhibitor compounds, and preparation method therefor |
CN109553534A (zh) * | 2018-11-27 | 2019-04-02 | 常州大学 | 一种2-硝基-4-甲氧基苯甲酸的制备方法 |
US10835531B1 (en) | 2019-06-18 | 2020-11-17 | Oncology Venture ApS | Methods for predicting drug responsiveness in cancer patients |
GB201909191D0 (en) | 2019-06-26 | 2019-08-07 | Ucb Biopharma Sprl | Therapeutic agents |
WO2023081923A1 (fr) | 2021-11-08 | 2023-05-11 | Frequency Therapeutics, Inc. | Inhibiteurs du récepteur du facteur de croissance dérivé des plaquettes (pdgfr) alpha et leurs utilisations |
Family Cites Families (94)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US158224A (en) * | 1874-12-29 | Improvement in eye-cups | ||
DE236459C (fr) | ||||
US207883A (en) * | 1878-09-10 | Improvement in drafting-pencils | ||
US3663606A (en) * | 1966-06-21 | 1972-05-16 | Mitsui Toatsu Chemicals | Organic imino-compounds |
DE2363459A1 (de) | 1973-12-20 | 1975-06-26 | Basf Ag | Neue fluoreszierende chinolinverbindungen |
DE3248043A1 (de) | 1982-12-24 | 1984-06-28 | Bayer Ag, 5090 Leverkusen | Fluorogene phosphorsaeureester, verfahren zu deren herstellung sowie verfahren und mittel zum nachweis und zur fluorometrischen bestimmung von phosphaten |
US4659657A (en) * | 1982-12-24 | 1987-04-21 | Bayer Aktiengesellschaft | Chromogenic and fluorogenic esters for photometric or fluorimetric determination of phosphatases or sulphatases |
DE3634066A1 (de) * | 1986-10-07 | 1988-04-21 | Boehringer Mannheim Gmbh | Neue 5-alkylbenzimidazole, verfahren zu ihrer herstellung sowie arzneimittel |
US5073492A (en) | 1987-01-09 | 1991-12-17 | The Johns Hopkins University | Synergistic composition for endothelial cell growth |
JPH07121937B2 (ja) * | 1987-03-18 | 1995-12-25 | 大塚製薬株式会社 | カルボスチリル誘導体 |
JPH0699497B2 (ja) | 1987-04-16 | 1994-12-07 | 富士写真フイルム株式会社 | 光重合性組成物 |
GB8709448D0 (en) * | 1987-04-21 | 1987-05-28 | Pfizer Ltd | Heterobicyclic quinoline derivatives |
CA1300918C (fr) * | 1987-06-12 | 1992-05-19 | Masataka Kamitani | Tuile en ciment arme de fibres et methode de fabrication de ladite tuile |
DE3932953A1 (de) * | 1989-10-03 | 1991-04-11 | Boehringer Mannheim Gmbh | Neue 2-bicyclo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
US5151360A (en) * | 1990-12-31 | 1992-09-29 | Biomembrane Institute | Effect of n,n,n-trimethylsphingosine on protein kinase-c activity, melanoma cell growth in vitro, metastatic potential in vivo and human platelet aggregation |
GB9107742D0 (en) | 1991-04-11 | 1991-05-29 | Rhone Poulenc Agriculture | New compositions of matter |
GB9108369D0 (en) | 1991-04-18 | 1991-06-05 | Rhone Poulenc Agriculture | Compositions of matter |
GB9108547D0 (en) | 1991-04-22 | 1991-06-05 | Fujisawa Pharmaceutical Co | Quinoline derivatives |
WO1992020642A1 (fr) | 1991-05-10 | 1992-11-26 | Rhone-Poulenc Rorer International (Holdings) Inc. | Composes aryle et heteroaryle bis monocycliques et/ou bicycliques qui inhibent la tyrosine kinase d'un recepteur du egf et/ou du pdgf |
USRE37650E1 (en) | 1991-05-10 | 2002-04-09 | Aventis Pharmacetical Products, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
US5480883A (en) | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
US5856115A (en) | 1991-05-24 | 1999-01-05 | Fred Hutchinson Cancer Research Center | Assay for identification therapeutic agents |
CA2452130A1 (fr) | 1992-03-05 | 1993-09-16 | Francis J. Burrows | Agents diagnostiques et/ou therapeutiques cibles pour les cellules endotheliales neovasculaires |
JP3142378B2 (ja) | 1992-06-22 | 2001-03-07 | ティーディーケイ株式会社 | 有機el素子 |
US5330992A (en) * | 1992-10-23 | 1994-07-19 | Sterling Winthrop Inc. | 1-cyclopropyl-4-pyridyl-quinolinones |
US5646163A (en) * | 1992-10-30 | 1997-07-08 | The Procter & Gamble Company | Quinolone 5-(N-heterosubstituted amino) antimicrobials |
US5981569A (en) | 1992-11-13 | 1999-11-09 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Substituted phenylacrylonitrile compounds and compositions thereof for the treatment of disease |
US5792771A (en) | 1992-11-13 | 1998-08-11 | Sugen, Inc. | Quinazoline compounds and compositions thereof for the treatment of disease |
US5763441A (en) | 1992-11-13 | 1998-06-09 | Sugen, Inc. | Compounds for the treatment of disorders related to vasculogenesis and/or angiogenesis |
JPH0743896A (ja) | 1993-07-28 | 1995-02-14 | Toyobo Co Ltd | 光重合性組成物 |
AU5881394A (en) | 1994-01-08 | 1995-08-01 | Rhone-Poulenc Agriculture Limited | Benzimidazolyl quinoline-3-carboxylate derivatives, intermediates thereto, and their use as herbicides |
JPH0829973A (ja) | 1994-07-11 | 1996-02-02 | Toyobo Co Ltd | 光重合性組成物 |
JP3441246B2 (ja) | 1995-06-07 | 2003-08-25 | 富士写真フイルム株式会社 | 光重合性組成物 |
GB9514265D0 (en) * | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
EP0888310B1 (fr) | 1996-03-15 | 2005-09-07 | AstraZeneca AB | Derives de cinnoline et leur emploi comme medicaments |
DE19610723A1 (de) | 1996-03-19 | 1997-09-25 | Bayer Ag | Elektrolumineszierende Anordnungen unter Verwendung von Blendsystemen |
US5942385A (en) | 1996-03-21 | 1999-08-24 | Sugen, Inc. | Method for molecular diagnosis of tumor angiogenesis and metastasis |
EP2223920A3 (fr) | 1996-06-19 | 2011-09-28 | Aventis Pharma Limited | Composes azabicycliques substitues |
CA2258822A1 (fr) | 1996-06-20 | 1997-12-24 | Sean Kerwin | Composes et procedes d'obtention de preparations pharmacologiquement actives et leurs utilisations |
ATE300521T1 (de) * | 1996-09-25 | 2005-08-15 | Astrazeneca Ab | Chinolin-derivate die den effekt von wachstumsfaktoren wie vegf vezögern |
US6111110A (en) * | 1996-10-30 | 2000-08-29 | Eli Lilly And Company | Synthesis of benzo[f]quinolinones |
US6245760B1 (en) | 1997-05-28 | 2001-06-12 | Aventis Pharmaceuticals Products, Inc | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
DE69807222T2 (de) | 1997-06-02 | 2003-04-17 | Janssen Pharmaceutica N.V., Beerse | (imidazol-5-yl)methyl-2-quinolinone derivativen als inhibitoren von proliferation der glatten muskelzellen |
WO1999010349A1 (fr) | 1997-08-22 | 1999-03-04 | Zeneca Limited | Derives d'oxindolylquinazoline utiles comme inhibiteurs d'angiogenese |
DE19756235A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue piperidinylsubstituierte Pyridylalkan- alken- und -alkincarbonsäureamide |
JP2002509928A (ja) * | 1998-03-31 | 2002-04-02 | ワーナー−ランバート・カンパニー | セリンプロテアーゼ阻害剤としてのキノロン |
CA2328893A1 (fr) | 1998-05-20 | 1999-11-25 | Kyowa Hakko Kogyo Co., Ltd. | Inhibiteurs de l'activite du facteur de croissance endothelial vasculaire (vegf) |
JP4533534B2 (ja) | 1998-06-19 | 2010-09-01 | ノバルティス バクシンズ アンド ダイアグノスティックス,インコーポレーテッド | グリコーゲンシンターゼキナーゼ3のインヒビター |
CA2333647A1 (fr) | 1998-06-29 | 2000-01-06 | Dupont Pharmaceuticals Company | Isoxazolidines et carbamates cycliques utilises comme antagonistes de iib/iiia |
FR2781218B1 (fr) | 1998-07-15 | 2001-09-07 | Lafon Labor | Compositions pharmaceutiques comprenant des 2-quinolones |
US6174912B1 (en) * | 1998-08-21 | 2001-01-16 | Dupont Pharmaceuticals Company | Nitrogen substituted imidazo[4,5-C]pyrazoles as corticotropin releasing hormone antagonists |
DE19841985A1 (de) | 1998-09-03 | 2000-03-09 | Schering Ag | Dialkylsulfonsäure- und Dialkylcarbonsäure-Derivate |
WO2000020400A1 (fr) * | 1998-10-05 | 2000-04-13 | Axys Pharmaceuticals, Inc. | Nouveaux composes et compositions pour le traitement de l'hepatite c |
IL126953A0 (en) | 1998-11-08 | 1999-09-22 | Yeda Res & Dev | Pharmaceutical compositions comprising porphyrins and some novel porphyrin derivatives |
US20030087854A1 (en) * | 2001-09-10 | 2003-05-08 | Isis Pharmaceuticals Inc. | Antisense modulation of fibroblast growth factor receptor 3 expression |
KR100373203B1 (ko) * | 1999-03-31 | 2003-02-25 | 주식회사 엘지화학 | 새로운 큐마린계 착물 및 이를 이용한 유기 발광 소자 |
MXPA01011832A (es) | 1999-05-21 | 2002-06-21 | Squibb Bristol Myers Co | Inhibidores de cinasas, de pirrolotriazina. |
JP2003171280A (ja) | 1999-06-07 | 2003-06-17 | Fujisawa Pharmaceut Co Ltd | 抗腫瘍効果増強剤 |
PE20010306A1 (es) | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
US6423734B1 (en) | 1999-08-13 | 2002-07-23 | The Procter & Gamble Company | Method of preventing cancer |
KR100298572B1 (ko) * | 1999-08-19 | 2001-09-22 | 박찬구 | 카바아닐라이드로부터 4-니트로디페닐아민과 4-니트로소디페닐아민의 제조방법 |
AU778588B2 (en) | 1999-10-19 | 2004-12-09 | Merck Sharp & Dohme Corp. | Tyrosine kinase inhibitors |
ES2235970T3 (es) * | 1999-10-19 | 2005-07-16 | MERCK & CO. INC. | Inhibidores de tirosina quinasa. |
US7045133B2 (en) | 2000-01-18 | 2006-05-16 | Ludwig Institute For Cancer Research | VEGF-D/VEGF-C/VEGF peptidomimetic inhibitor |
YU54202A (sh) | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
CN101053573A (zh) | 2000-01-19 | 2007-10-17 | 帕卡什·S·吉尔 | 针对反义vegf寡核苷酸的方法和组合物 |
GB0001930D0 (en) | 2000-01-27 | 2000-03-22 | Novartis Ag | Organic compounds |
US6313138B1 (en) | 2000-02-25 | 2001-11-06 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
EP1259236A4 (fr) | 2000-02-25 | 2004-11-03 | Merck & Co Inc | Inhibiteurs de tyrosine-kinase |
US6420382B2 (en) | 2000-02-25 | 2002-07-16 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
CZ20023518A3 (cs) | 2000-03-31 | 2004-04-14 | Imclone Systems Incorporated | Léčivo pro inhibici růstu buněk non-solidních nádorů |
ATE448226T1 (de) * | 2000-09-01 | 2009-11-15 | Novartis Vaccines & Diagnostic | Aza heterocyclische derivate und ihre therapeutische verwendung |
WO2002020500A2 (fr) * | 2000-09-01 | 2002-03-14 | Icos Corporation | Substances potentialisant un traitement anticancereux et methodes a cet effet |
PT1650203E (pt) | 2000-09-11 | 2008-05-13 | Novartis Vaccines & Diagnostic | Processo de preparação de derivados de benzimidazol-2-ilquinolinona |
US20030028018A1 (en) * | 2000-09-11 | 2003-02-06 | Chiron Coporation | Quinolinone derivatives |
AU9279601A (en) | 2000-09-26 | 2002-04-08 | Procter & Gamble | Compounds and methods for use thereof in the treatment of cancer or viral infections |
EP1328519B1 (fr) | 2000-10-17 | 2005-09-07 | Merck & Co., Inc. | Sels oralement actifs a activite tyrosine kinase |
US6693125B2 (en) | 2001-01-24 | 2004-02-17 | Combinatorx Incorporated | Combinations of drugs (e.g., a benzimidazole and pentamidine) for the treatment of neoplastic disorders |
US7081454B2 (en) | 2001-03-28 | 2006-07-25 | Bristol-Myers Squibb Co. | Tyrosine kinase inhibitors |
EP1401831A1 (fr) * | 2001-07-03 | 2004-03-31 | Chiron Corporation | Composes d'indazole benzimidazole utilises comme inhibiteurs de tyrosine et de serine/threonine kinase |
EP1447405A4 (fr) | 2001-10-17 | 2005-01-12 | Kirin Brewery | Derives de quinoline ou de quinazoline inhibant l'autophosphorylation de recepteurs du facteur de croissance des fibroblastes |
US7825132B2 (en) * | 2002-08-23 | 2010-11-02 | Novartis Vaccines And Diagnostics, Inc. | Inhibition of FGFR3 and treatment of multiple myeloma |
BR0313743A (pt) | 2002-08-23 | 2005-07-05 | Chiron Corp | Benzimidazol quinolinonas e usos destas |
US20050256157A1 (en) * | 2002-08-23 | 2005-11-17 | Chiron Corporation | Combination therapy with CHK1 inhibitors |
AU2003275282A1 (en) | 2002-09-30 | 2004-04-23 | Bristol-Myers Squibb Company | Novel tyrosine kinase inhibitors |
AU2003290699B2 (en) * | 2002-11-13 | 2009-08-27 | Novartis Vaccines And Diagnostics, Inc. | Methods of treating cancer and related methods |
US7189716B2 (en) | 2003-01-03 | 2007-03-13 | Bristol-Myers Squibb Company | Tyrosine kinase inhibitors |
EP1590332B1 (fr) | 2003-01-09 | 2011-04-27 | University of Delhi | Procédé pour la synthèse des bisbenzimidazoles et leurs dérivés. |
ES2423800T3 (es) | 2003-03-28 | 2013-09-24 | Novartis Vaccines And Diagnostics, Inc. | Uso de compuestos orgánicos para la inmunopotenciación |
US6774327B1 (en) * | 2003-09-24 | 2004-08-10 | Agilent Technologies, Inc. | Hermetic seals for electronic components |
KR101167573B1 (ko) | 2003-11-07 | 2012-07-30 | 노바티스 백신즈 앤드 다이아그노스틱스 인코포레이티드 | 개선된 약학적 성질을 갖는 퀴놀리논 화합물의 약학적으로허용가능한 염 |
WO2005054183A2 (fr) | 2003-12-01 | 2005-06-16 | The Scripps Research Institute | Inhibiteurs de proteines kinases a base de quinolinone |
-
2001
- 2001-09-11 PT PT05017665T patent/PT1650203E/pt unknown
- 2001-09-11 KR KR1020037003558A patent/KR100732206B1/ko active IP Right Grant
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- 2001-09-11 AP APAP/P/2003/002781A patent/AP1666A/en active
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- 2002-10-30 US US10/284,017 patent/US6774237B2/en not_active Expired - Lifetime
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- 2003-03-04 MA MA27064A patent/MA27957A1/fr unknown
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2004
- 2004-07-08 US US10/886,950 patent/US7598268B2/en not_active Expired - Fee Related
- 2004-09-14 HK HK04106977A patent/HK1064368A1/xx not_active IP Right Cessation
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2005
- 2005-03-29 US US11/092,137 patent/US7335774B2/en not_active Expired - Lifetime
- 2005-12-22 CY CY20051101584T patent/CY1108070T1/el unknown
-
2007
- 2007-03-12 JP JP2007062683A patent/JP2007191486A/ja not_active Withdrawn
- 2007-04-12 NO NO20071888A patent/NO328723B1/no not_active IP Right Cessation
-
2008
- 2008-05-19 CY CY20081100516T patent/CY1108931T1/el unknown
-
2009
- 2009-08-27 IL IL200606A patent/IL200606A/en not_active IP Right Cessation
-
2013
- 2013-01-29 JP JP2013013940A patent/JP5649672B2/ja not_active Expired - Lifetime
-
2014
- 2014-02-24 JP JP2014032859A patent/JP2014129378A/ja not_active Withdrawn
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