HRP20010216A2 - New substituted indolinones, their preparation and their use as medicaments - Google Patents
New substituted indolinones, their preparation and their use as medicaments Download PDFInfo
- Publication number
- HRP20010216A2 HRP20010216A2 HR20010216A HRP20010216A HRP20010216A2 HR P20010216 A2 HRP20010216 A2 HR P20010216A2 HR 20010216 A HR20010216 A HR 20010216A HR P20010216 A HRP20010216 A HR P20010216A HR P20010216 A2 HRP20010216 A2 HR P20010216A2
- Authority
- HR
- Croatia
- Prior art keywords
- group
- alkyl
- amino
- phenyl
- substituted
- Prior art date
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- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 3
- 239000003814 drug Substances 0.000 title 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 255
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 239000000651 prodrug Chemical group 0.000 claims abstract description 9
- 229940002612 prodrug Drugs 0.000 claims abstract description 9
- -1 nitro, amino Chemical group 0.000 claims description 340
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 86
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 71
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 70
- 238000011282 treatment Methods 0.000 claims description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 46
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 239000000460 chlorine Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 37
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 33
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 29
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 28
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 239000011737 fluorine Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 229910052740 iodine Chemical group 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 19
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 19
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 9
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000007790 solid phase Substances 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 150000003951 lactams Chemical group 0.000 claims description 5
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000005544 phthalimido group Chemical group 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- JBCFFAZDUBFGQW-QPLCGJKRSA-N (3z)-5-nitro-3-[phenyl-[4-(piperidin-1-ylmethyl)anilino]methylidene]-1h-indol-2-one Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)\C1=C(C=1C=CC=CC=1)/NC(C=C1)=CC=C1CN1CCCCC1 JBCFFAZDUBFGQW-QPLCGJKRSA-N 0.000 claims description 4
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- YZQYLXVWTQKHNY-QPLCGJKRSA-N (3z)-3-[[4-(2-morpholin-4-ylethyl)anilino]-phenylmethylidene]-5-nitro-1h-indol-2-one Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)\C1=C(C=1C=CC=CC=1)/NC(C=C1)=CC=C1CCN1CCOCC1 YZQYLXVWTQKHNY-QPLCGJKRSA-N 0.000 claims description 3
- HNCRQCVXZXSJRP-FCQUAONHSA-N (3z)-3-[[4-[(dimethylamino)methyl]anilino]-phenylmethylidene]-5-nitro-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O HNCRQCVXZXSJRP-FCQUAONHSA-N 0.000 claims description 3
- JUXFRGURUWQIRC-VHXPQNKSSA-N (3z)-3-[[4-[2-(dimethylamino)ethyl]anilino]-phenylmethylidene]-5-nitro-1h-indol-2-one Chemical compound C1=CC(CCN(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O JUXFRGURUWQIRC-VHXPQNKSSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 230000009435 amidation Effects 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 230000004663 cell proliferation Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- SGVAUCIEUYKEQF-IZHYLOQSSA-N n-[2-(dimethylamino)ethyl]-n-[4-[[(z)-(2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(N(CCN(C)C)S(C)(=O)=O)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=CC=C2NC\1=O SGVAUCIEUYKEQF-IZHYLOQSSA-N 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 3
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 2
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 150000003855 acyl compounds Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 108050006400 Cyclin Proteins 0.000 abstract description 7
- 102000016736 Cyclin Human genes 0.000 abstract description 7
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
- 102000001253 Protein Kinase Human genes 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 108060006633 protein kinase Proteins 0.000 abstract description 3
- 108091008598 receptor tyrosine kinases Proteins 0.000 abstract description 3
- 102000027426 receptor tyrosine kinases Human genes 0.000 abstract description 3
- 230000003612 virological effect Effects 0.000 abstract description 3
- 239000013067 intermediate product Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 690
- 238000001819 mass spectrum Methods 0.000 description 471
- 238000002844 melting Methods 0.000 description 461
- 230000008018 melting Effects 0.000 description 461
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 441
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 363
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 299
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 228
- 239000000243 solution Substances 0.000 description 169
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 126
- 239000000741 silica gel Substances 0.000 description 124
- 229910002027 silica gel Inorganic materials 0.000 description 124
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 115
- 229910001868 water Inorganic materials 0.000 description 114
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 92
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- 239000002904 solvent Substances 0.000 description 55
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 238000000354 decomposition reaction Methods 0.000 description 45
- 235000011114 ammonium hydroxide Nutrition 0.000 description 43
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- QNWGMJXVSLRFMR-UHFFFAOYSA-N 1-acetyl-3-[ethoxy(phenyl)methylidene]indol-2-one Chemical compound O=C1N(C(C)=O)C2=CC=CC=C2C1=C(OCC)C1=CC=CC=C1 QNWGMJXVSLRFMR-UHFFFAOYSA-N 0.000 description 31
- RQFHATRKMMVQPC-UHFFFAOYSA-N 1-acetyl-3-[ethoxy(phenyl)methylidene]-5-nitroindol-2-one Chemical compound O=C1N(C(C)=O)C2=CC=C([N+]([O-])=O)C=C2C1=C(OCC)C1=CC=CC=C1 RQFHATRKMMVQPC-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- CQMHZLKNXHIIOT-UHFFFAOYSA-N 3-[ethoxy(phenyl)methylidene]-5-nitro-1h-indol-2-one Chemical compound O=C1NC2=CC=C([N+]([O-])=O)C=C2C1=C(OCC)C1=CC=CC=C1 CQMHZLKNXHIIOT-UHFFFAOYSA-N 0.000 description 29
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 26
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 25
- 239000012317 TBTU Substances 0.000 description 19
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 18
- 239000012362 glacial acetic acid Substances 0.000 description 18
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 14
- NNCCQALFJIMRKB-UHFFFAOYSA-N 4-[(dimethylamino)methyl]aniline Chemical compound CN(C)CC1=CC=C(N)C=C1 NNCCQALFJIMRKB-UHFFFAOYSA-N 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 11
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 11
- OANCBHUMQGJXQG-UHFFFAOYSA-N 1-acetyl-3-[methoxy(phenyl)methylidene]-5-nitroindol-2-one Chemical compound O=C1N(C(C)=O)C2=CC=C([N+]([O-])=O)C=C2C1=C(OC)C1=CC=CC=C1 OANCBHUMQGJXQG-UHFFFAOYSA-N 0.000 description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- UWUHCQWBMCWQIO-CFRCJOIHSA-N (3z)-3-[[4-(aminomethyl)anilino]-phenylmethylidene]-5-nitro-1h-indol-2-one;hydrochloride Chemical compound Cl.C1=CC(CN)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O UWUHCQWBMCWQIO-CFRCJOIHSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- GSIBTIUXYYFCPU-UHFFFAOYSA-N tert-butyl 4-(bromomethyl)benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(CBr)C=C1 GSIBTIUXYYFCPU-UHFFFAOYSA-N 0.000 description 1
- COSXQRGJLFEFGJ-SECBINFHSA-N tert-butyl n-[(1r)-1-(4-aminophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C)C1=CC=C(N)C=C1 COSXQRGJLFEFGJ-SECBINFHSA-N 0.000 description 1
- COSXQRGJLFEFGJ-VIFPVBQESA-N tert-butyl n-[(1s)-1-(4-aminophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C)C1=CC=C(N)C=C1 COSXQRGJLFEFGJ-VIFPVBQESA-N 0.000 description 1
- LSOZALWRNWQPLK-UHFFFAOYSA-N tert-butyl n-[(3-aminophenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(N)=C1 LSOZALWRNWQPLK-UHFFFAOYSA-N 0.000 description 1
- COSXQRGJLFEFGJ-UHFFFAOYSA-N tert-butyl n-[1-(4-aminophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1=CC=C(N)C=C1 COSXQRGJLFEFGJ-UHFFFAOYSA-N 0.000 description 1
- TVBOFJDVRPYTSQ-YHZPTAEISA-N tert-butyl n-[2-[4-[[(z)-(1-acetyl-5-nitro-2-oxoindol-3-ylidene)-[4-[(1,3-dioxoisoindol-2-yl)methyl]phenyl]methyl]amino]phenyl]ethyl]carbamate Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C(=O)C)C(=O)\C1=C(C=1C=CC(CN2C(C3=CC=CC=C3C2=O)=O)=CC=1)/NC1=CC=C(CCNC(=O)OC(C)(C)C)C=C1 TVBOFJDVRPYTSQ-YHZPTAEISA-N 0.000 description 1
- BNPIUVCHCGXKAY-IZHYLOQSSA-N tert-butyl n-[2-[4-[[(z)-(5-nitro-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]ethyl]carbamate Chemical compound C1=CC(CCNC(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O BNPIUVCHCGXKAY-IZHYLOQSSA-N 0.000 description 1
- YHYHFEIWDXKDLH-DQSJHHFOSA-N tert-butyl n-[2-[4-[[(z)-[4-(acetamidomethyl)phenyl]-(5-nitro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]ethyl]carbamate Chemical compound C1=CC(CNC(=O)C)=CC=C1C(\NC=1C=CC(CCNC(=O)OC(C)(C)C)=CC=1)=C\1C2=CC([N+]([O-])=O)=CC=C2NC/1=O YHYHFEIWDXKDLH-DQSJHHFOSA-N 0.000 description 1
- FTRZBMDCTHWEPN-QPLCGJKRSA-N tert-butyl n-[2-[4-[[(z)-[4-(aminomethyl)phenyl]-(5-nitro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]ethyl]carbamate Chemical compound C1=CC(CCNC(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC(CN)=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O FTRZBMDCTHWEPN-QPLCGJKRSA-N 0.000 description 1
- SUZDGHMOOQUVTI-QPLCGJKRSA-N tert-butyl n-[2-[[4-[[(z)-(5-nitro-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]methylamino]-2-oxoethyl]carbamate Chemical compound C1=CC(CNC(=O)CNC(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O SUZDGHMOOQUVTI-QPLCGJKRSA-N 0.000 description 1
- ANWKSMCOWOZHDM-QPLCGJKRSA-N tert-butyl n-[2-oxo-2-[[4-[[(z)-(2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]methylamino]ethyl]carbamate Chemical compound C1=CC(CNC(=O)CNC(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=CC=C2NC\1=O ANWKSMCOWOZHDM-QPLCGJKRSA-N 0.000 description 1
- OZRNWYAQPKPVKZ-UHFFFAOYSA-N tert-butyl n-[4-(propan-2-ylsulfonylamino)phenyl]carbamate Chemical compound CC(C)S(=O)(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 OZRNWYAQPKPVKZ-UHFFFAOYSA-N 0.000 description 1
- IRYKZPYNYRQHFX-FCQUAONHSA-N tert-butyl n-[4-[[(z)-(2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC=CC=C2NC\1=O IRYKZPYNYRQHFX-FCQUAONHSA-N 0.000 description 1
- LCMFRTYCPVYGPB-VHXPQNKSSA-N tert-butyl n-[[3-[[(z)-(2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(N\C(=C/2C3=CC=CC=C3NC\2=O)C=2C=CC=CC=2)=C1 LCMFRTYCPVYGPB-VHXPQNKSSA-N 0.000 description 1
- SEQFKABCLHFBCZ-VHXPQNKSSA-N tert-butyl n-[[4-[[(z)-(5-nitro-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O SEQFKABCLHFBCZ-VHXPQNKSSA-N 0.000 description 1
- VLTANDNRKJWNKJ-RQZHXJHFSA-N tert-butyl n-methyl-n-[2-[[4-[[(z)-(5-nitro-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]methylamino]-2-oxoethyl]carbamate Chemical compound C1=CC(CNC(=O)CN(C)C(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O VLTANDNRKJWNKJ-RQZHXJHFSA-N 0.000 description 1
- YNLVHFWAZBPMOQ-IZHYLOQSSA-N tert-butyl n-methyl-n-[[4-[[(z)-(5-nitro-2-oxo-1h-indol-3-ylidene)-phenylmethyl]amino]phenyl]methyl]carbamate Chemical compound C1=CC(CN(C)C(=O)OC(C)(C)C)=CC=C1N\C(C=1C=CC=CC=1)=C/1C2=CC([N+]([O-])=O)=CC=C2NC\1=O YNLVHFWAZBPMOQ-IZHYLOQSSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- CWLNAJYDRSIKJS-UHFFFAOYSA-N triethoxymethoxyethane Chemical compound CCOC(OCC)(OCC)OCC CWLNAJYDRSIKJS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- IECKAVQTURBPON-UHFFFAOYSA-N trimethoxymethylbenzene Chemical compound COC(OC)(OC)C1=CC=CC=C1 IECKAVQTURBPON-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19844003A DE19844003A1 (de) | 1998-09-25 | 1998-09-25 | Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
DE19937496A DE19937496A1 (de) | 1999-08-07 | 1999-08-07 | Neue substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
PCT/EP1999/007040 WO2000018734A1 (de) | 1998-09-25 | 1999-09-22 | Neue substituierte indolinone mit inhibierender wirkung auf verschiedene kinasen und cyclin/cdk-komplexe |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20010216A2 true HRP20010216A2 (en) | 2002-04-30 |
Family
ID=26049076
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20010216A HRP20010216A2 (en) | 1998-09-25 | 2001-03-21 | New substituted indolinones, their preparation and their use as medicaments |
Country Status (28)
Country | Link |
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US (1) | US6855710B2 (no) |
EP (1) | EP1115704B1 (no) |
JP (1) | JP2002525356A (no) |
KR (1) | KR20010085841A (no) |
CN (1) | CN1319090A (no) |
AT (1) | ATE243195T1 (no) |
AU (1) | AU763361B2 (no) |
BG (1) | BG105327A (no) |
BR (1) | BR9914065A (no) |
CA (1) | CA2342622A1 (no) |
DE (1) | DE59906030D1 (no) |
DK (1) | DK1115704T3 (no) |
EA (1) | EA200100320A1 (no) |
EE (1) | EE200100184A (no) |
ES (1) | ES2196860T3 (no) |
HR (1) | HRP20010216A2 (no) |
HU (1) | HUP0104973A3 (no) |
ID (1) | ID27757A (no) |
IL (1) | IL141622A0 (no) |
NO (1) | NO20011477D0 (no) |
NZ (1) | NZ510845A (no) |
PL (1) | PL346898A1 (no) |
PT (1) | PT1115704E (no) |
SI (1) | SI1115704T1 (no) |
SK (1) | SK4032001A3 (no) |
TR (1) | TR200100854T2 (no) |
WO (1) | WO2000018734A1 (no) |
YU (1) | YU21301A (no) |
Families Citing this family (35)
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GB9904933D0 (en) | 1999-03-04 | 1999-04-28 | Glaxo Group Ltd | Compounds |
CA2461812C (en) * | 2001-09-27 | 2011-09-20 | Allergan, Inc. | 3-(arylamino)methylene-1,3-dihydro-2h-indol-2-ones as kinase inhibitors |
US6797825B2 (en) | 2001-12-13 | 2004-09-28 | Abbott Laboratories | Protein kinase inhibitors |
US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
MXPA04009329A (es) | 2002-03-26 | 2005-01-25 | Boehringer Ingelheim Pharma | Mimeticos de glucocorticoides, metodos para su preparacion, composiciones farmaceuticas y usos de los mismos. |
US7169936B2 (en) | 2002-07-23 | 2007-01-30 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Indolinone derivatives substituted in the 6-position, their preparation and their use as medicaments |
US7514468B2 (en) | 2002-07-23 | 2009-04-07 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Indolinone derivatives substituted in the 6 position, the preparation thereof and their use as pharmaceutical compositions |
DE10233366A1 (de) * | 2002-07-23 | 2004-02-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | In 6-Stellung substituierte Indolinonderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
PE20040701A1 (es) * | 2002-07-23 | 2004-11-30 | Boehringer Ingelheim Pharma | Derivados de indolinona sustituidos en posicion 6 y su preparacion como medicamentos |
DE10237423A1 (de) * | 2002-08-16 | 2004-02-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von LCK-Inhibitoren für die Behandlung von immunologischen Erkrankungen |
US20040204458A1 (en) | 2002-08-16 | 2004-10-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Use of Lck inhibitors for treatment of immunologic diseases |
RS20050174A (en) * | 2002-08-29 | 2007-06-04 | Boehringer Ingelheim Pharmaceuticals Inc., | -3(sulfonamidoethyl)-indole derivatives for use as glucocorticoid mimetics in the treatment of inflammatory, allergic and proliferative diseases |
US7148249B2 (en) * | 2002-09-12 | 2006-12-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Indolinones substituted by heterocycles, the preparation thereof and their use as medicaments |
JP4879492B2 (ja) * | 2002-11-27 | 2012-02-22 | アラーガン、インコーポレイテッド | 疾患の治療のためのキナーゼ阻害剤 |
US20050043233A1 (en) | 2003-04-29 | 2005-02-24 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation, migration or apoptosis of myeloma cells or angiogenesis |
UY28526A1 (es) | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
DE602004017884D1 (de) | 2003-10-03 | 2009-01-02 | Boehringer Ingelheim Pharma | Fluoreszenzsonden zur verwendung bei einem bindungsassay auf proteinkinaseinhibitoren |
KR101165863B1 (ko) | 2004-03-11 | 2012-07-13 | 액테리온 파마슈티칼 리미티드 | 인돌-1-일-아세트산 유도체 |
US7795272B2 (en) | 2004-03-13 | 2010-09-14 | Boehringer Ingelheim Pharmaceutical, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof |
PE20061155A1 (es) * | 2004-12-24 | 2006-12-16 | Boehringer Ingelheim Int | Derivados de indolinona como agentes para el tratamiento o la prevencion de enfermedades fibroticas |
PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
US7741361B2 (en) | 2004-12-27 | 2010-06-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
CA2605688A1 (en) | 2005-04-28 | 2006-11-02 | Boehringer Ingelheim International Gmbh | Compounds for treating inflammatory diseases |
WO2008070507A2 (en) | 2006-12-06 | 2008-06-12 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
RU2482877C2 (ru) * | 2006-12-11 | 2013-05-27 | Дженентек, Инк. | Композиции и способы для лечения опухоли |
CN101273991B (zh) * | 2007-03-28 | 2010-05-26 | 广东同德药业有限公司 | 四氢吲哚酮/四氢吲唑酮/四氢咔唑衍生物及其盐在制备抗病毒药物中的应用 |
NZ585799A (en) * | 2007-12-03 | 2012-04-27 | Boehringer Ingelheim Int | Process for the manufacture of an indolinone derivative in particular 3-z-[1-(4-(n-((4-methyl-piperazin-1-yl)-methylcarbonyl)-n-methyl-amino)-anilino)-1-phenyl-methylene]-6-methoxycarbonyl-2-indolinone |
UY31506A1 (es) | 2007-12-03 | 2009-08-03 | Derivados de indolinona y procedimiento para su preparacion | |
DK2238108T3 (da) * | 2008-01-25 | 2012-10-15 | Boehringer Ingelheim Int | Saltformer af et 6-fluor-1,2-dihydro-2-oxo-3h-indol-3-yliden-derivat, fremgangsmåde til fremstilling deraf og farmaceutiske sammensætninger indeholdende de samme |
AU2009256289A1 (en) | 2008-06-06 | 2009-12-10 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
TW201011002A (en) | 2008-07-29 | 2010-03-16 | Boehringer Ingelheim Int | New compounds |
JPWO2013137371A1 (ja) * | 2012-03-15 | 2015-08-03 | 興和株式会社 | 新規ピリミジン化合物及びそれらを含有する医薬 |
CN103664737A (zh) * | 2012-09-25 | 2014-03-26 | 杨子娇 | 一类治疗房角狭窄的化合物及其用途 |
WO2019152977A2 (en) | 2018-02-05 | 2019-08-08 | Bio-Rad Laboratories, Inc. | Chromatography resin having an anionic exchange-hydrophobic mixed mode ligand |
CN114957084B (zh) * | 2022-01-21 | 2023-05-09 | 九江学院 | 一种吲哚酮类化合物及其制备方法和应用 |
Family Cites Families (2)
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GB9501567D0 (en) * | 1995-01-26 | 1995-03-15 | Pharmacia Spa | Hydrosoluble 3-arylidene-2-oxindole derivatives as tyrosine kinase inhibitors |
US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
-
1999
- 1999-09-22 AT AT99947404T patent/ATE243195T1/de not_active IP Right Cessation
- 1999-09-22 ID IDW20010688A patent/ID27757A/id unknown
- 1999-09-22 AU AU60863/99A patent/AU763361B2/en not_active Ceased
- 1999-09-22 IL IL14162299A patent/IL141622A0/xx unknown
- 1999-09-22 EP EP99947404A patent/EP1115704B1/de not_active Expired - Lifetime
- 1999-09-22 WO PCT/EP1999/007040 patent/WO2000018734A1/de not_active Application Discontinuation
- 1999-09-22 SK SK403-2001A patent/SK4032001A3/sk unknown
- 1999-09-22 CN CN99811297A patent/CN1319090A/zh active Pending
- 1999-09-22 HU HU0104973A patent/HUP0104973A3/hu unknown
- 1999-09-22 EE EEP200100184A patent/EE200100184A/xx unknown
- 1999-09-22 JP JP2000572194A patent/JP2002525356A/ja active Pending
- 1999-09-22 CA CA002342622A patent/CA2342622A1/en not_active Abandoned
- 1999-09-22 DK DK99947404T patent/DK1115704T3/da active
- 1999-09-22 NZ NZ510845A patent/NZ510845A/en unknown
- 1999-09-22 PT PT99947404T patent/PT1115704E/pt unknown
- 1999-09-22 DE DE59906030T patent/DE59906030D1/de not_active Expired - Fee Related
- 1999-09-22 EA EA200100320A patent/EA200100320A1/ru unknown
- 1999-09-22 YU YU21301A patent/YU21301A/sh unknown
- 1999-09-22 PL PL99346898A patent/PL346898A1/xx not_active Application Discontinuation
- 1999-09-22 TR TR2001/00854T patent/TR200100854T2/xx unknown
- 1999-09-22 BR BR9914065-9A patent/BR9914065A/pt unknown
- 1999-09-22 SI SI9930391T patent/SI1115704T1/xx unknown
- 1999-09-22 ES ES99947404T patent/ES2196860T3/es not_active Expired - Lifetime
- 1999-09-22 KR KR1020017003773A patent/KR20010085841A/ko not_active Application Discontinuation
-
2001
- 2001-03-09 BG BG105327A patent/BG105327A/xx active Pending
- 2001-03-21 HR HR20010216A patent/HRP20010216A2/hr not_active Application Discontinuation
- 2001-03-22 NO NO20011477A patent/NO20011477D0/no not_active Application Discontinuation
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2003
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Also Published As
Publication number | Publication date |
---|---|
US6855710B2 (en) | 2005-02-15 |
CN1319090A (zh) | 2001-10-24 |
DE59906030D1 (de) | 2003-07-24 |
ID27757A (id) | 2001-04-26 |
BR9914065A (pt) | 2001-06-19 |
AU6086399A (en) | 2000-04-17 |
SK4032001A3 (en) | 2001-11-06 |
JP2002525356A (ja) | 2002-08-13 |
EP1115704A1 (de) | 2001-07-18 |
ES2196860T3 (es) | 2003-12-16 |
IL141622A0 (en) | 2002-03-10 |
SI1115704T1 (en) | 2003-12-31 |
YU21301A (sh) | 2003-04-30 |
EE200100184A (et) | 2002-08-15 |
TR200100854T2 (tr) | 2001-12-21 |
PL346898A1 (en) | 2002-03-11 |
EP1115704B1 (de) | 2003-06-18 |
PT1115704E (pt) | 2003-11-28 |
HUP0104973A3 (en) | 2002-06-28 |
BG105327A (en) | 2001-12-29 |
WO2000018734A1 (de) | 2000-04-06 |
NO20011477L (no) | 2001-03-22 |
CA2342622A1 (en) | 2000-04-06 |
KR20010085841A (ko) | 2001-09-07 |
US20040058978A1 (en) | 2004-03-25 |
HUP0104973A2 (hu) | 2002-04-29 |
AU763361B2 (en) | 2003-07-17 |
NZ510845A (en) | 2003-10-31 |
NO20011477D0 (no) | 2001-03-22 |
EA200100320A1 (ru) | 2001-10-22 |
ATE243195T1 (de) | 2003-07-15 |
DK1115704T3 (da) | 2003-09-29 |
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