CA2729745A1 - Oxindole compounds - Google Patents
Oxindole compounds Download PDFInfo
- Publication number
- CA2729745A1 CA2729745A1 CA2729745A CA2729745A CA2729745A1 CA 2729745 A1 CA2729745 A1 CA 2729745A1 CA 2729745 A CA2729745 A CA 2729745A CA 2729745 A CA2729745 A CA 2729745A CA 2729745 A1 CA2729745 A1 CA 2729745A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- substituted
- alkyl
- mmol
- nrz
- 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.)
- Abandoned
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- 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 283
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- 201000011510 cancer Diseases 0.000 claims abstract description 50
- 206010061218 Inflammation Diseases 0.000 claims abstract description 25
- 230000004054 inflammatory process Effects 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 79
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 238000011282 treatment Methods 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 24
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 206010060862 Prostate cancer Diseases 0.000 claims description 18
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 15
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 14
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 14
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 14
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 13
- 201000002528 pancreatic cancer Diseases 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims description 4
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- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
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- 125000001424 substituent group Chemical group 0.000 description 41
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
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- 125000005647 linker group Chemical group 0.000 description 12
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- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 11
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 9
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- 229940117013 triethanolamine oleate Drugs 0.000 description 1
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- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 229960001099 trimetrexate Drugs 0.000 description 1
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
- VXKHXGOKWPXYNA-PGBVPBMZSA-N triptorelin Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 VXKHXGOKWPXYNA-PGBVPBMZSA-N 0.000 description 1
- 229960004824 triptorelin Drugs 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- RXRGZNYSEHTMHC-BQBZGAKWSA-N troxacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)OC1 RXRGZNYSEHTMHC-BQBZGAKWSA-N 0.000 description 1
- 229950010147 troxacitabine Drugs 0.000 description 1
- 208000022271 tubular adenoma Diseases 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
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- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
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- 229960000653 valrubicin Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
- 229960002166 vinorelbine tartrate Drugs 0.000 description 1
- GBABOYUKABKIAF-IWWDSPBFSA-N vinorelbinetartrate Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC(C23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IWWDSPBFSA-N 0.000 description 1
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- 229960004276 zoledronic acid Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
- C07D417/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7709108P | 2008-06-30 | 2008-06-30 | |
| US61/077,091 | 2008-06-30 | ||
| US15642609P | 2009-02-27 | 2009-02-27 | |
| US61/156,426 | 2009-02-27 | ||
| US18009509P | 2009-05-20 | 2009-05-20 | |
| US61/180,095 | 2009-05-20 | ||
| PCT/US2009/049318 WO2010002933A1 (en) | 2008-06-30 | 2009-06-30 | Oxindole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2729745A1 true CA2729745A1 (en) | 2010-01-07 |
Family
ID=41466309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2729745A Abandoned CA2729745A1 (en) | 2008-06-30 | 2009-06-30 | Oxindole compounds |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8124649B2 (enExample) |
| EP (1) | EP2307421A4 (enExample) |
| JP (1) | JP2011526917A (enExample) |
| KR (1) | KR20110025996A (enExample) |
| CN (1) | CN102137866A (enExample) |
| AU (1) | AU2009267048A1 (enExample) |
| BR (1) | BRPI0914942A2 (enExample) |
| CA (1) | CA2729745A1 (enExample) |
| IL (1) | IL210355A0 (enExample) |
| MX (1) | MX2011000150A (enExample) |
| WO (1) | WO2010002933A1 (enExample) |
| ZA (1) | ZA201100539B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2011338389A1 (en) | 2010-12-09 | 2013-06-13 | Amgen Inc. | Bicyclic compounds as Pim inhibitors |
| CN102688234B (zh) * | 2011-03-21 | 2015-07-29 | 华东理工大学 | 吲哚酮衍生物作为rsk2抑制剂的合成与应用 |
| AU2012230890A1 (en) | 2011-03-22 | 2013-09-26 | Amgen Inc. | Azole compounds as Pim inhibitors |
| CN103509009A (zh) * | 2012-06-21 | 2014-01-15 | 中国科学院上海药物研究所 | 2-取代-5-苯基呋喃类化合物、其制备方法、药物组合物及其用途 |
| EP2943485B1 (en) | 2013-01-14 | 2017-09-20 | Incyte Holdings Corporation | Bicyclic aromatic carboxamide compounds useful as pim kinase inhibitors |
| HUE050215T2 (hu) | 2013-01-15 | 2020-11-30 | Incyte Holdings Corp | Pim kináz inhibitorokként hasznos tiazolkarboxamid és piridinkarboxamid vegyületek |
| TW201605866A (zh) | 2013-08-23 | 2016-02-16 | 英塞特公司 | 可用作ｐｉｍ激酶抑制劑之呋喃并－及噻吩并－吡啶甲醯胺化合物 |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| WO2016010897A1 (en) | 2014-07-14 | 2016-01-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as pim kinase inhibitors |
| US9540347B2 (en) | 2015-05-29 | 2017-01-10 | Incyte Corporation | Pyridineamine compounds useful as Pim kinase inhibitors |
| MY189453A (en) | 2015-06-03 | 2022-02-14 | Bristol Myers Squibb Co | 4-hydroxy-3-(heteroaryl)pyridine-2-one apj agonists for use in the treatment of cardiovascular disorders |
| TWI734699B (zh) | 2015-09-09 | 2021-08-01 | 美商英塞特公司 | Ｐｉｍ激酶抑制劑之鹽 |
| WO2017059251A1 (en) | 2015-10-02 | 2017-04-06 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| EP3187496A1 (de) * | 2015-12-30 | 2017-07-05 | Heliatek GmbH | Verbindung für fotoaktive organische elektronische bauelemente und fotoaktives organisches elektronisches bauelement enthaltend die verbindung |
| WO2019113487A1 (en) | 2017-12-08 | 2019-06-13 | Incyte Corporation | Low dose combination therapy for treatment of myeloproliferative neoplasms |
| US11071727B2 (en) | 2018-01-26 | 2021-07-27 | Northwestern University | Therapeutic targeting of proteolytic cleavage of the mixed lineage leukemia gene product (MLL1) by taspase1 using kinase inhibitors |
| WO2025085819A1 (en) * | 2023-10-18 | 2025-04-24 | Washington University | Kinase inhibitor compositions and related methods for the treatment of a disease |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6846839B1 (en) * | 1995-06-07 | 2005-01-25 | Sugen, Inc. | Methods for treating diseases and disorders related to unregulated angiogenesis and/or vasculogenesis |
| US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US20030119895A1 (en) * | 1998-12-23 | 2003-06-26 | Pharmacia Corporation | Methods using a combination of a 3-heteroaryl-2-indolinone and a cyclooxygenase-2 inhibitor for the treatment of neoplasia |
| BRPI0117360B8 (pt) * | 2000-02-15 | 2021-07-06 | Upjohn Co | inibidores de proteína de quinase de 2-indolinona de pirrol substituído, seus sais e composições farmacêuticas compreendendo os mesmos |
| AR042586A1 (es) * | 2001-02-15 | 2005-06-29 | Sugen Inc | 3-(4-amidopirrol-2-ilmetiliden)-2-indolinona como inhibidores de la protein quinasa; sus composiciones farmaceuticas; un metodo para la modulacion de la actividad catalitica de la proteinquinasa; un metodo para tratar o prevenir una afeccion relacionada con la proteinquinasa |
| AR036042A1 (es) * | 2001-05-30 | 2004-08-04 | Sugen Inc | Derivados aralquilsufonil-3-(pirrol-2-ilmetiliden)-2-indolinona, sus composiciones farmaceuticas y metodo para la modulacion de la actividad catalitica de una proteina quinasa |
| EP1680401A2 (en) * | 2003-10-24 | 2006-07-19 | Schering Aktiengesellschaft | Indolinone derivatives and their use in treating disease-states such as cancer |
| JP2007084494A (ja) * | 2005-09-22 | 2007-04-05 | Oncorex Inc | Ｐｉｍ−１活性阻害剤 |
| WO2007087419A2 (en) * | 2006-01-24 | 2007-08-02 | Allergan, Inc. | Substituted 3-(5-membered unsaturated heterocyclyl) -1, 3-dihydro-indol-2-one derivatives as tyrosine kinase inhibitors for the treatment of cancer |
| CA2639913A1 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceutical Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| KR101452520B1 (ko) | 2006-01-27 | 2014-10-21 | 샹하이 헨그루이 파마수티컬 컴퍼니 리미티드 | 피롤로[3,2-ｃ]피리딘-4-온 2-인돌린온 단백질 키나제 억제제 |
-
2009
- 2009-06-30 BR BRPI0914942-2A patent/BRPI0914942A2/pt not_active IP Right Cessation
- 2009-06-30 WO PCT/US2009/049318 patent/WO2010002933A1/en not_active Ceased
- 2009-06-30 AU AU2009267048A patent/AU2009267048A1/en not_active Withdrawn
- 2009-06-30 MX MX2011000150A patent/MX2011000150A/es not_active Application Discontinuation
- 2009-06-30 EP EP09774383A patent/EP2307421A4/en not_active Withdrawn
- 2009-06-30 CN CN2009801336712A patent/CN102137866A/zh active Pending
- 2009-06-30 US US12/495,666 patent/US8124649B2/en not_active Expired - Fee Related
- 2009-06-30 KR KR1020117002316A patent/KR20110025996A/ko not_active Withdrawn
- 2009-06-30 JP JP2011516831A patent/JP2011526917A/ja active Pending
- 2009-06-30 CA CA2729745A patent/CA2729745A1/en not_active Abandoned
-
2010
- 2010-12-29 IL IL210355A patent/IL210355A0/en unknown
-
2011
- 2011-01-20 ZA ZA2011/00539A patent/ZA201100539B/en unknown
-
2012
- 2012-01-20 US US13/354,563 patent/US20120190669A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0914942A2 (pt) | 2015-08-11 |
| IL210355A0 (en) | 2011-03-31 |
| AU2009267048A1 (en) | 2010-01-07 |
| JP2011526917A (ja) | 2011-10-20 |
| EP2307421A1 (en) | 2011-04-13 |
| US8124649B2 (en) | 2012-02-28 |
| CN102137866A (zh) | 2011-07-27 |
| MX2011000150A (es) | 2011-04-05 |
| US20120190669A1 (en) | 2012-07-26 |
| US20100041635A1 (en) | 2010-02-18 |
| WO2010002933A1 (en) | 2010-01-07 |
| EP2307421A4 (en) | 2011-07-13 |
| KR20110025996A (ko) | 2011-03-14 |
| ZA201100539B (en) | 2011-11-30 |
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Effective date: 20140702 |