JP2002522452A - 蛋白質キナーゼの調節剤3−メチリデニル−2−インドリノン - Google Patents
蛋白質キナーゼの調節剤3−メチリデニル−2−インドリノンInfo
- Publication number
- JP2002522452A JP2002522452A JP2000563824A JP2000563824A JP2002522452A JP 2002522452 A JP2002522452 A JP 2002522452A JP 2000563824 A JP2000563824 A JP 2000563824A JP 2000563824 A JP2000563824 A JP 2000563824A JP 2002522452 A JP2002522452 A JP 2002522452A
- Authority
- JP
- Japan
- Prior art keywords
- dihydroindol
- group
- hydrogen
- indole
- methoxybenzylidene
- 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.)
- Withdrawn
Links
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- 125000000217 alkyl group Chemical group 0.000 claims description 199
- 229910052739 hydrogen Inorganic materials 0.000 claims description 174
- 150000001875 compounds Chemical class 0.000 claims description 166
- 239000001257 hydrogen Substances 0.000 claims description 164
- -1 -C (O) OH Chemical group 0.000 claims description 160
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 119
- 229910001868 water Inorganic materials 0.000 claims description 106
- 150000002431 hydrogen Chemical class 0.000 claims description 96
- 125000003545 alkoxy group Chemical group 0.000 claims description 83
- 125000005843 halogen group Chemical group 0.000 claims description 83
- 125000003118 aryl group Chemical group 0.000 claims description 82
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 65
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 63
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 48
- 230000033115 angiogenesis Effects 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 230000003197 catalytic effect Effects 0.000 claims description 28
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 26
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- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 16
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 16
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- 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 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
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- 125000004953 trihalomethyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 7
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- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
- ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 claims description 6
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 5
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- FUTBDFIZQCZJHB-UHFFFAOYSA-N 3-[(2,2-dimethyl-3,4-dihydrochromen-6-yl)methylidene]-4-methyl-1h-indol-2-one Chemical compound O1C(C)(C)CCC2=CC(C=C3C(=O)NC=4C=CC=C(C3=4)C)=CC=C21 FUTBDFIZQCZJHB-UHFFFAOYSA-N 0.000 claims description 4
- VQJIIADJLDOIDP-UHFFFAOYSA-N 3-[(2,2-dimethyl-3,4-dihydrochromen-6-yl)methylidene]-5-fluoro-1h-indol-2-one Chemical compound O=C1NC2=CC=C(F)C=C2C1=CC1=CC=C(OC(C)(C)CC2)C2=C1 VQJIIADJLDOIDP-UHFFFAOYSA-N 0.000 claims description 4
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- 206010018338 Glioma Diseases 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
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- LAAZYIXDYKODRJ-UHFFFAOYSA-N 3-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-5-fluoro-1h-indol-2-one Chemical compound C1=C2OCCC2=CC(C=C2C(=O)NC3=CC=C(C=C32)F)=C1 LAAZYIXDYKODRJ-UHFFFAOYSA-N 0.000 claims description 3
- QBQMWXPZQHKOCS-UHFFFAOYSA-N 3-[(3-cyclopentyl-4-methoxyphenyl)methylidene]-1h-pyrrolo[2,3-b]pyridin-2-one Chemical compound COC1=CC=C(C=C2C3=CC=CN=C3NC2=O)C=C1C1CCCC1 QBQMWXPZQHKOCS-UHFFFAOYSA-N 0.000 claims description 3
- CYAHZYMXHMNAHN-UHFFFAOYSA-N 3-[(3-cyclopentyl-4-methoxyphenyl)methylidene]-4-methyl-1h-indol-2-one Chemical compound COC1=CC=C(C=C2C3=C(C)C=CC=C3NC2=O)C=C1C1CCCC1 CYAHZYMXHMNAHN-UHFFFAOYSA-N 0.000 claims description 3
- FYVHQVGNQTUUQX-UHFFFAOYSA-N 3-[(3-cyclopentyl-4-methoxyphenyl)methylidene]-5-fluoro-1h-indol-2-one Chemical compound COC1=CC=C(C=C2C3=CC(F)=CC=C3NC2=O)C=C1C1CCCC1 FYVHQVGNQTUUQX-UHFFFAOYSA-N 0.000 claims description 3
- UGYJYHZSRGMFCW-UHFFFAOYSA-N 3-[(4,5-dimethoxy-2-thiophen-2-ylphenyl)methylidene]-1h-indol-2-one Chemical compound C1=C(OC)C(OC)=CC(C=C2C3=CC=CC=C3NC2=O)=C1C1=CC=CS1 UGYJYHZSRGMFCW-UHFFFAOYSA-N 0.000 claims description 3
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- AMRQVMDXZYYISD-UHFFFAOYSA-N 3-[(4-methoxy-3,5-dimethylphenyl)methylidene]-1h-pyrrolo[2,3-b]pyridin-2-one Chemical compound C1=C(C)C(OC)=C(C)C=C1C=C1C2=CC=CN=C2NC1=O AMRQVMDXZYYISD-UHFFFAOYSA-N 0.000 claims description 3
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- SATXCEOJASSLIS-UHFFFAOYSA-N 3-[[4-methoxy-3,5-di(propan-2-yl)phenyl]methylidene]-4-methyl-1h-indol-2-one Chemical compound C1=C(C(C)C)C(OC)=C(C(C)C)C=C1C=C1C2=C(C)C=CC=C2NC1=O SATXCEOJASSLIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- WKPQDFYHBOATID-UHFFFAOYSA-N 5-amino-3-[[4-methoxy-3,5-di(propan-2-yl)phenyl]methylidene]-1h-indol-2-one Chemical compound C1=C(C(C)C)C(OC)=C(C(C)C)C=C1C=C1C2=CC(N)=CC=C2NC1=O WKPQDFYHBOATID-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- 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
- C07D401/10—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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- 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
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D409/10—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 linked by a carbon chain containing aromatic rings
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
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US12925698A | 1998-08-04 | 1998-08-04 | |
US09/129,256 | 1998-08-04 | ||
US9547098P | 1998-08-05 | 1998-08-05 | |
US60/095,470 | 1998-08-05 | ||
US10217898P | 1998-09-28 | 1998-09-28 | |
US60/102,178 | 1998-09-28 | ||
US11610799P | 1999-01-15 | 1999-01-15 | |
US60/116,107 | 1999-01-15 | ||
PCT/US1999/017845 WO2000008202A2 (fr) | 1998-08-04 | 1999-08-04 | Modulateurs 3-methylidenyl-2-indolinone de proteine kinase |
Publications (2)
Publication Number | Publication Date |
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JP2002522452A true JP2002522452A (ja) | 2002-07-23 |
JP2002522452A5 JP2002522452A5 (fr) | 2006-09-14 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2000563824A Withdrawn JP2002522452A (ja) | 1998-08-04 | 1999-08-04 | 蛋白質キナーゼの調節剤3−メチリデニル−2−インドリノン |
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Country | Link |
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JP (1) | JP2002522452A (fr) |
AU (1) | AU5468499A (fr) |
CA (1) | CA2383623A1 (fr) |
WO (1) | WO2000008202A2 (fr) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2006512400A (ja) * | 2002-11-27 | 2006-04-13 | 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 |
JP2011037848A (ja) * | 2009-08-04 | 2011-02-24 | Lab Servier | 新規なジヒドロインドロン化合物、それらの調製方法及びそれらを含む薬学的組成物 |
JP2012522729A (ja) * | 2009-04-06 | 2012-09-27 | ユニバーシティ・ヘルス・ネットワーク | キナーゼインヒビターおよびこれを用いた癌の治療方法 |
US9139563B2 (en) | 2010-04-06 | 2015-09-22 | University Health Network | Kinase inhibitors and method of treating cancer |
US20160250220A1 (en) | 2013-10-18 | 2016-09-01 | University Health Network | Treatment for pancreatic cancer |
JP2018533600A (ja) * | 2015-11-12 | 2018-11-15 | エルジー・ケム・リミテッド | 7−アザインドリン−2−オン誘導体又はその薬学的に許容される塩を有効成分として含有する医薬組成物 |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6569868B2 (en) | 1998-04-16 | 2003-05-27 | Sugen, Inc. | 2-indolinone derivatives as modulators of protein kinase activity |
KR20010101266A (ko) | 1998-12-17 | 2001-11-14 | 프리돌린 클라우스너, 롤란드 비. 보레르 | Jnk 단백질 키나제의 억제제로서의 4-아릴옥신돌 |
US6153634A (en) | 1998-12-17 | 2000-11-28 | Hoffmann-La Roche Inc. | 4,5-azolo-oxindoles |
BR9916324A (pt) | 1998-12-17 | 2001-10-02 | Hoffmann La Roche | 4,5-pirazinoxindóis como inibidores de proteìna quinase |
ES2192877T3 (es) * | 1998-12-17 | 2003-10-16 | Hoffmann La Roche | 4-alquenil (y alquinil) oxindoles como inhibidores de kinasas ciclina-dependientes, en particular cdk2. |
US6878733B1 (en) | 1999-11-24 | 2005-04-12 | Sugen, Inc. | Formulations for pharmaceutical agents ionizable as free acids or free bases |
AU1928501A (en) * | 1999-11-24 | 2001-06-04 | Sugen, Inc. | Formulations for pharmaceutical agents ionizable as free acids or free bases |
US6313310B1 (en) | 1999-12-15 | 2001-11-06 | Hoffmann-La Roche Inc. | 4-and 5-alkynyloxindoles and 4-and 5-alkenyloxindoles |
US20020028828A1 (en) | 2000-05-02 | 2002-03-07 | Chung-Chen Wei | (2-oxindol-3-ylidenyl)acetic acid derivatives and their use as protein kinase inhibitors |
MY128450A (en) | 2000-05-24 | 2007-02-28 | Upjohn Co | 1-(pyrrolidin-1-ylmethyl)-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives |
CA2410509A1 (fr) | 2000-06-02 | 2001-12-13 | Sugen, Inc. | Derives d'indolinone comme inhibiteurs de phosphatase/proteine kinase |
JP2004518669A (ja) | 2000-12-20 | 2004-06-24 | スージェン・インコーポレーテッド | 4−アリール置換インドリノン |
JP2004529110A (ja) | 2001-03-06 | 2004-09-24 | アストラゼネカ アクチボラグ | 脈管損傷活性を有するインドール誘導体 |
US7081454B2 (en) | 2001-03-28 | 2006-07-25 | Bristol-Myers Squibb Co. | Tyrosine kinase inhibitors |
US6797725B2 (en) | 2001-04-09 | 2004-09-28 | Sugen, Inc. | Prodrugs of a 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives |
CA2448076A1 (fr) * | 2001-05-24 | 2002-11-28 | Masahiko Hayakawa | Derives de 3-quinoleine-2-(1h)-ylideneindoline-2-one |
US6599902B2 (en) | 2001-05-30 | 2003-07-29 | Sugen, Inc. | 5-aralkysufonyl-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives as kinase inhibitors |
CA2459879A1 (fr) | 2001-09-10 | 2003-03-20 | Sugen, Inc. | Derives de 3-(4,5,6,7-tetrahydroindol-2-ylmethylidene)-2-indolinone comme inhibiteurs de kinases |
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US9296730B2 (en) | 2012-10-26 | 2016-03-29 | Regents Of The University Of Minnesota | Aurora kinase inhibitors |
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GB9004483D0 (en) * | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
FR2678911A1 (fr) * | 1991-07-10 | 1993-01-15 | Prospection & Inventions | Cartouche tubulaire de stockage et d'application d'un produit non solide et ensemble d'entrainement et de poussee pour la cartouche. |
GB9115160D0 (en) * | 1991-07-12 | 1991-08-28 | Erba Carlo Spa | Methylen-oxindole derivatives and process for their preparation |
FR2694004B1 (fr) * | 1992-07-21 | 1994-08-26 | Adir | Nouvelles 3-(Hydroxybenzylidényl)-indoline-2-ones et 3-(hydroxybenzylidényl)-indoline-2-thiones, leurs procédés de préparation, et les compositions pharmaceutiques qui les contiennent. |
US5650415A (en) * | 1995-06-07 | 1997-07-22 | Sugen, Inc. | Quinoline compounds |
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1999
- 1999-08-04 CA CA002383623A patent/CA2383623A1/fr not_active Abandoned
- 1999-08-04 AU AU54684/99A patent/AU5468499A/en not_active Abandoned
- 1999-08-04 WO PCT/US1999/017845 patent/WO2000008202A2/fr active Application Filing
- 1999-08-04 JP JP2000563824A patent/JP2002522452A/ja not_active Withdrawn
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Also Published As
Publication number | Publication date |
---|---|
AU5468499A (en) | 2000-02-28 |
WO2000008202A2 (fr) | 2000-02-17 |
WO2000008202A3 (fr) | 2000-05-18 |
WO2000008202A9 (fr) | 2000-07-27 |
CA2383623A1 (fr) | 2000-02-17 |
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