JP2005508336A - キナーゼ阻害物質としての３−（アリールアミノ）メチレン−１，３−ジヒドロ−２ｈ−インドール−２−オン類 - Google Patents
キナーゼ阻害物質としての３−（アリールアミノ）メチレン−１，３−ジヒドロ−２ｈ−インドール−２−オン類 Download PDFInfo
- Publication number
- JP2005508336A JP2005508336A JP2003530690A JP2003530690A JP2005508336A JP 2005508336 A JP2005508336 A JP 2005508336A JP 2003530690 A JP2003530690 A JP 2003530690A JP 2003530690 A JP2003530690 A JP 2003530690A JP 2005508336 A JP2005508336 A JP 2005508336A
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- JP
- Japan
- Prior art keywords
- dihydro
- indol
- methylene
- phenylamino
- fluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- IGXUUWYVUGBMFT-UHFFFAOYSA-N 3-methyleneoxindole Chemical class C1=CC=C2C(=C)C(=O)NC2=C1 IGXUUWYVUGBMFT-UHFFFAOYSA-N 0.000 title 1
- 125000001769 aryl amino group Chemical group 0.000 title 1
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 22
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 22
- 230000011664 signaling Effects 0.000 claims abstract description 15
- -1 3-fluoropyrrolidinyl Chemical group 0.000 claims description 594
- 150000001875 compounds Chemical class 0.000 claims description 203
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000002757 morpholinyl group Chemical group 0.000 claims description 21
- 208000035475 disorder Diseases 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000004193 piperazinyl group Chemical group 0.000 claims description 17
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 13
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 230000002062 proliferating effect Effects 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 206010016654 Fibrosis Diseases 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 208000030159 metabolic disease Diseases 0.000 claims description 8
- 150000003568 thioethers Chemical class 0.000 claims description 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 230000002792 vascular Effects 0.000 claims description 7
- ZCCPVTVGEQLONB-UHFFFAOYSA-N 1-(1,3-dioxolan-2-yl)-n-methylmethanamine Chemical compound CNCC1OCCO1 ZCCPVTVGEQLONB-UHFFFAOYSA-N 0.000 claims description 6
- QAFODUGVXFNLBE-UHFFFAOYSA-N 1-methoxybutan-2-amine Chemical compound CCC(N)COC QAFODUGVXFNLBE-UHFFFAOYSA-N 0.000 claims description 6
- ZUUQKDDUUOFCNP-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)-n-methylethanamine Chemical compound CNCCC1OCCO1 ZUUQKDDUUOFCNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 claims description 6
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 6
- 230000004761 fibrosis Effects 0.000 claims description 6
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 6
- RZVWBASHHLFBJF-UHFFFAOYSA-N methyl piperidine-4-carboxylate Chemical compound COC(=O)C1CCNCC1 RZVWBASHHLFBJF-UHFFFAOYSA-N 0.000 claims description 6
- AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 206010003246 arthritis Diseases 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 208000002780 macular degeneration Diseases 0.000 claims description 5
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 claims description 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- IPBPLHNLRKRLPJ-UHFFFAOYSA-N oxan-4-ylmethanamine Chemical compound NCC1CCOCC1 IPBPLHNLRKRLPJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims 10
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 4
- 210000003584 mesangial cell Anatomy 0.000 claims 4
- 125000006309 butyl amino group Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 206010063209 Chronic allograft nephropathy Diseases 0.000 claims 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000034841 Thrombotic Microangiopathies Diseases 0.000 claims 2
- 208000031737 Tissue Adhesions Diseases 0.000 claims 2
- 230000007882 cirrhosis Effects 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 208000016097 disease of metabolism Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 201000009925 nephrosclerosis Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 abstract description 6
- 230000010261 cell growth Effects 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 133
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 101
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 90
- 239000007787 solid Substances 0.000 description 87
- 239000011541 reaction mixture Substances 0.000 description 83
- 239000000243 solution Substances 0.000 description 54
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 48
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 40
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 37
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 37
- 230000002829 reductive effect Effects 0.000 description 37
- 239000003921 oil Substances 0.000 description 32
- 239000012074 organic phase Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 238000010992 reflux Methods 0.000 description 25
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 22
- 102000005962 receptors Human genes 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 20
- 108020003175 receptors Proteins 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000000725 suspension Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 13
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- JVUCUNQXFYLSJI-UHFFFAOYSA-N 2-hydroxy-1H-indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(O)NC2=C1 JVUCUNQXFYLSJI-UHFFFAOYSA-N 0.000 description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 229910052796 boron Inorganic materials 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 239000007868 Raney catalyst Substances 0.000 description 11
- 229910000564 Raney nickel Inorganic materials 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 238000003556 assay Methods 0.000 description 10
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 10
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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- 239000012043 crude product Substances 0.000 description 8
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
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- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 7
- UALFVGAUFYTZSV-UHFFFAOYSA-N 3-(hydroxymethylidene)-4-methyl-1h-indol-2-one Chemical compound CC1=CC=CC2=C1C(=CO)C(=O)N2 UALFVGAUFYTZSV-UHFFFAOYSA-N 0.000 description 7
- SHBOEOYGYJZCNX-UHFFFAOYSA-N 3-[[4-(3-iodopropoxy)anilino]methylidene]-1h-indol-2-one Chemical compound C1=CC(OCCCI)=CC=C1NC=C1C2=CC=CC=C2NC1=O SHBOEOYGYJZCNX-UHFFFAOYSA-N 0.000 description 7
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- VTBHKDHFDNLZNG-UHFFFAOYSA-N 4-(2-piperidin-1-ylethoxy)aniline Chemical compound C1=CC(N)=CC=C1OCCN1CCCCC1 VTBHKDHFDNLZNG-UHFFFAOYSA-N 0.000 description 7
- ROPJHTWQKBBFTF-UHFFFAOYSA-N 4-(3-piperidin-1-ylpropoxy)aniline Chemical compound C1=CC(N)=CC=C1OCCCN1CCCCC1 ROPJHTWQKBBFTF-UHFFFAOYSA-N 0.000 description 7
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- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 6
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- YBADLXQNJCMBKR-UHFFFAOYSA-N (4-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
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Classifications
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D209/04—Indoles; Hydrogenated indoles
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D401/10—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 carbon chain containing aromatic rings
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| PCT/US2002/030882 WO2003027102A1 (en) | 2001-09-27 | 2002-09-27 | 3-(arylamino)methylene-1, 3-dihydro-2h-indol-2-ones as kinase inhibitors |
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| JP2010013326A Pending JP2010116411A (ja) | 2001-09-27 | 2010-01-25 | キナーゼ阻害物質としての３−（アリールアミノ）メチレン−１，３−ジヒドロ−２ｈ−インドール−２−オン類 |
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| JP2010530401A (ja) * | 2007-06-21 | 2010-09-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | インドリン−２−オンおよびアザ−インドリン−２−オン |
| JP2016505549A (ja) * | 2012-12-06 | 2016-02-25 | 山東亨利醫藥科技有限責任公司 | チロシンキナーゼ阻害剤としてのインドリノン誘導体 |
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| WO1999015500A1 (en) * | 1997-09-05 | 1999-04-01 | Glaxo Group Limited | Substituted oxindole derivatives as protein tyrosine kinase and as protein serine/threonine kinase inhibitors |
| WO2000056710A1 (en) * | 1999-03-04 | 2000-09-28 | Glaxo Group Limited | 3-(anilinomethylene) oxindoles as protein tyrosine kinase and protein serine/threonine kinase inhibitors |
| WO2001016130A1 (de) * | 1999-08-27 | 2001-03-08 | Boehringer Ingelheim Pharma Kg | Substituierte indolinone als tyrosinkinase inhibitoren |
| WO2001027081A1 (de) * | 1999-10-13 | 2001-04-19 | Boehringer Ingelheim Pharma Kg | In 6-stellung substituierte indolinone, ihre herstellung und ihre verwendung als arzneimittel |
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- 2002-09-27 CA CA2461812A patent/CA2461812C/en not_active Expired - Fee Related
- 2002-09-27 JP JP2003530690A patent/JP2005508336A/ja active Pending
- 2002-09-27 AU AU2002341881A patent/AU2002341881B2/en not_active Ceased
- 2002-09-27 EP EP02776036A patent/EP1430048A1/en not_active Withdrawn
- 2002-09-27 US US10/256,879 patent/US6765012B2/en not_active Expired - Fee Related
- 2002-09-27 WO PCT/US2002/030882 patent/WO2003027102A1/en not_active Ceased
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2004
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- 2004-07-06 US US10/886,213 patent/US7098236B2/en not_active Expired - Lifetime
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2005
- 2005-09-16 US US11/228,780 patent/US20060025413A1/en not_active Abandoned
- 2005-11-15 US US11/274,681 patent/US7414054B2/en not_active Expired - Lifetime
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- 2006-03-31 US US11/396,036 patent/US20060194863A1/en not_active Abandoned
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| WO1999015500A1 (en) * | 1997-09-05 | 1999-04-01 | Glaxo Group Limited | Substituted oxindole derivatives as protein tyrosine kinase and as protein serine/threonine kinase inhibitors |
| WO2000056710A1 (en) * | 1999-03-04 | 2000-09-28 | Glaxo Group Limited | 3-(anilinomethylene) oxindoles as protein tyrosine kinase and protein serine/threonine kinase inhibitors |
| WO2001016130A1 (de) * | 1999-08-27 | 2001-03-08 | Boehringer Ingelheim Pharma Kg | Substituierte indolinone als tyrosinkinase inhibitoren |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010530401A (ja) * | 2007-06-21 | 2010-09-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | インドリン−２−オンおよびアザ−インドリン−２−オン |
| JP2009057299A (ja) * | 2007-08-30 | 2009-03-19 | Nippon Soda Co Ltd | 置換フェノキシアザビシクロオクタン誘導体およびその製造方法 |
| JP2016505549A (ja) * | 2012-12-06 | 2016-02-25 | 山東亨利醫藥科技有限責任公司 | チロシンキナーゼ阻害剤としてのインドリノン誘導体 |
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| Publication number | Publication date |
|---|---|
| WO2003027102A1 (en) | 2003-04-03 |
| US20030225152A1 (en) | 2003-12-04 |
| US20030199478A1 (en) | 2003-10-23 |
| CA2461812C (en) | 2011-09-20 |
| US7098236B2 (en) | 2006-08-29 |
| US20050228036A1 (en) | 2005-10-13 |
| AU2002341881B2 (en) | 2008-05-08 |
| US7414054B2 (en) | 2008-08-19 |
| CA2461812A1 (en) | 2003-04-03 |
| EP1430048A1 (en) | 2004-06-23 |
| US6765012B2 (en) | 2004-07-20 |
| US20040198720A1 (en) | 2004-10-07 |
| US20060063940A1 (en) | 2006-03-23 |
| US7015220B2 (en) | 2006-03-21 |
| US20060025413A1 (en) | 2006-02-02 |
| US20060194863A1 (en) | 2006-08-31 |
| JP2010116411A (ja) | 2010-05-27 |
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