KR20090005195A - Mek 저해제로서 신규한 헤테로아릴-치환된 아릴아미노피리딘 유도체 - Google Patents
Mek 저해제로서 신규한 헤테로아릴-치환된 아릴아미노피리딘 유도체 Download PDFInfo
- Publication number
- KR20090005195A KR20090005195A KR1020087028187A KR20087028187A KR20090005195A KR 20090005195 A KR20090005195 A KR 20090005195A KR 1020087028187 A KR1020087028187 A KR 1020087028187A KR 20087028187 A KR20087028187 A KR 20087028187A KR 20090005195 A KR20090005195 A KR 20090005195A
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- KR
- South Korea
- Prior art keywords
- alkyl
- substituted
- hydrogen
- unsubstituted
- fluoro
- Prior art date
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- Withdrawn
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
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- 239000001257 hydrogen Substances 0.000 claims description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims description 105
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- 125000003118 aryl group Chemical group 0.000 claims description 85
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- 229910052736 halogen Inorganic materials 0.000 claims description 34
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
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- 229910052717 sulfur Inorganic materials 0.000 claims description 5
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- BWNCNZBQKKJSPP-UHFFFAOYSA-N 5-[3-(2-fluoro-4-iodoanilino)pyridin-4-yl]-3h-1,3,4-oxadiazole-2-thione Chemical compound FC1=CC(I)=CC=C1NC1=CN=CC=C1C1=NNC(=S)O1 BWNCNZBQKKJSPP-UHFFFAOYSA-N 0.000 claims description 3
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- 239000002244 precipitate Substances 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- LKJJUICFLVYDJQ-UHFFFAOYSA-N 3-(2-fluoro-4-iodoanilino)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=C1NC1=CC=C(I)C=C1F LKJJUICFLVYDJQ-UHFFFAOYSA-N 0.000 description 15
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- 238000002360 preparation method Methods 0.000 description 15
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 13
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- 238000002953 preparative HPLC Methods 0.000 description 13
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
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- 230000003647 oxidation Effects 0.000 description 1
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 229960004063 propylene glycol Drugs 0.000 description 1
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- 210000002307 prostate Anatomy 0.000 description 1
- 208000017497 prostate disease Diseases 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
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- 239000012730 sustained-release form Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 230000009750 upstream signaling Effects 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| CA (1) | CA2644425A1 (https=) |
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| CA2707989A1 (en) * | 2007-12-07 | 2009-06-11 | Novartis Ag | Pyrazole derivatives and use thereof as inhibitors of cyclin dependent kinases |
| EP2370568B1 (en) | 2008-12-10 | 2017-07-19 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| EP3028699B1 (en) | 2010-02-25 | 2018-03-21 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| CN103038364A (zh) | 2010-03-09 | 2013-04-10 | 达纳-法伯癌症研究所公司 | 诊断和治疗具有或发展对于第一种癌症治疗的抗性的患者中的癌症的方法 |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US8759380B2 (en) | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| US20150141470A1 (en) | 2012-05-08 | 2015-05-21 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| WO2014007228A1 (ja) | 2012-07-03 | 2014-01-09 | 小野薬品工業株式会社 | ソマトスタチン受容体作動活性を有する化合物およびその医薬用途 |
| JP2018507884A (ja) * | 2015-03-10 | 2018-03-22 | オーリジーン ディスカバリー テクノロジーズ リミテッドAurigene Discovery Technologies Limited | 免疫調節剤としての3−置換1,3,4−オキサジアゾールおよびチアジアゾール化合物 |
| DK3300500T3 (da) | 2015-05-20 | 2020-05-18 | Amgen Inc | Triazolagonister af apj-receptoren |
| US20190008859A1 (en) | 2015-08-21 | 2019-01-10 | Acerta Pharma B.V. | Therapeutic Combinations of a MEK Inhibitor and a BTK Inhibitor |
| US10150754B2 (en) | 2016-04-19 | 2018-12-11 | Celgene Quanticel Research, Inc. | Histone demethylase inhibitors |
| WO2017192485A1 (en) | 2016-05-03 | 2017-11-09 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| EP3541792B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| WO2018093579A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole phenyl compounds as agonists of the apj receptor |
| WO2018093576A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Alkyl substituted triazole compounds as agonists of the apj receptor |
| EP3541803B1 (en) | 2016-11-16 | 2020-12-23 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| US11020395B2 (en) | 2016-11-16 | 2021-06-01 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the APJ receptor |
| US11046680B1 (en) | 2016-11-16 | 2021-06-29 | Amgen Inc. | Heteroaryl-substituted triazoles as APJ receptor agonists |
| WO2018204532A1 (en) | 2017-05-03 | 2018-11-08 | Vivace Therapeutics, Inc. | Non-fused tricyclic compounds |
| CA3073543A1 (en) | 2017-08-21 | 2019-02-28 | Vivace Therapeutics, Inc. | Benzosulfonyl compounds |
| US11149040B2 (en) | 2017-11-03 | 2021-10-19 | Amgen Inc. | Fused triazole agonists of the APJ receptor |
| US11524943B1 (en) | 2017-12-06 | 2022-12-13 | Vivace Therapeutics, Inc. | Benzocarbonyl compounds |
| PL3720438T3 (pl) * | 2017-12-07 | 2024-03-18 | Amplyx Pharmaceuticals, Inc. | Heterocyklicznie podstawione pochodne pirydyny jako środki przeciwgrzybicze |
| CN110317190A (zh) * | 2018-03-28 | 2019-10-11 | 首都医科大学 | 一种三唑-羧酸酯类衍生物在医药领域的应用 |
| WO2019213006A1 (en) | 2018-05-01 | 2019-11-07 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
| EP3793551A4 (en) | 2018-05-16 | 2022-01-26 | Vivace Therapeutics, Inc. | OXADIAZOLE COMPOUNDS |
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| EP4054579A1 (en) | 2019-11-08 | 2022-09-14 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| CN115279368B (zh) * | 2019-11-20 | 2024-05-24 | 维瓦斯治疗公司 | 杂芳基化合物 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| EP4346826A4 (en) | 2021-05-27 | 2025-04-30 | Mirati Therapeutics, Inc. | COMBINATION THERAPIES |
| WO2025054260A1 (en) * | 2023-09-07 | 2025-03-13 | Kinnate Biopharma Inc. | Inhibitors of mek kinase |
| WO2025073765A1 (en) | 2023-10-03 | 2025-04-10 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from melanoma |
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| HUP0105092A3 (en) | 1999-01-13 | 2003-12-29 | Warner Lambert Co | 1-heterocycle substituted diarylamines and medicaments containing them |
| GB2373245A (en) * | 2001-03-12 | 2002-09-18 | Bayer Ag | Pyridinyl pyrazoles and their use for the treatment of COPD |
| AU2003260472A1 (en) | 2002-09-10 | 2004-04-30 | Pharmacia Italia S.P.A. | Substituted pyridine derivatives as antitumor agent |
| WO2004052280A2 (en) * | 2002-12-10 | 2004-06-24 | Imclone Systems Incorporated | Anti-angiogenic compounds and their use in cancer treatment |
| US20050004186A1 (en) * | 2002-12-20 | 2005-01-06 | Pfizer Inc | MEK inhibiting compounds |
| WO2004091480A2 (en) * | 2003-04-09 | 2004-10-28 | Exelixis, Inc. | Tie-2 modulators and methods of use |
| WO2005000818A1 (en) | 2003-06-27 | 2005-01-06 | Warner-Lambert Company Llc | 5-substituted-4-`(substituted phenyl)!amino!-2-pyridone deviatives for use as mek inhibitors |
| WO2005004818A2 (en) | 2003-07-09 | 2005-01-20 | Imclone Systems Incorporated | Heterocyclic compounds and their use as anticancer agents |
| CA2546353A1 (en) | 2003-11-19 | 2005-06-09 | Array Biopharma Inc. | Bicyclic inhibitors of mek and methods of use thereof |
| MX2007004781A (es) * | 2004-10-20 | 2007-05-11 | Applied Research Systems | Derivados de 3-arilamino piridina. |
-
2007
- 2007-04-18 ZA ZA200807263A patent/ZA200807263B/xx unknown
- 2007-04-18 WO PCT/US2007/009456 patent/WO2007123936A1/en not_active Ceased
- 2007-04-18 MX MX2008013308A patent/MX2008013308A/es not_active Application Discontinuation
- 2007-04-18 JP JP2009506558A patent/JP5525812B2/ja not_active Expired - Fee Related
- 2007-04-18 BR BRPI0711625-0A patent/BRPI0711625A2/pt not_active IP Right Cessation
- 2007-04-18 CN CN200780014073.4A patent/CN101426766B/zh not_active Expired - Fee Related
- 2007-04-18 EA EA200802050A patent/EA200802050A1/ru unknown
- 2007-04-18 AU AU2007240860A patent/AU2007240860A1/en not_active Abandoned
- 2007-04-18 CA CA002644425A patent/CA2644425A1/en not_active Abandoned
- 2007-04-18 US US11/788,032 patent/US8076486B2/en not_active Expired - Fee Related
- 2007-04-18 EP EP07755648A patent/EP2013180A1/en not_active Withdrawn
- 2007-04-18 KR KR1020087028187A patent/KR20090005195A/ko not_active Withdrawn
- 2007-04-18 CN CN201210488042.5A patent/CN103121996B/zh not_active Expired - Fee Related
- 2007-04-19 AR ARP070101677A patent/AR060807A1/es unknown
-
2008
- 2008-10-06 IL IL194546A patent/IL194546A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1127354A1 (en) | 2009-09-25 |
| AU2007240860A1 (en) | 2007-11-01 |
| US20070287737A1 (en) | 2007-12-13 |
| CN101426766B (zh) | 2014-03-26 |
| ZA200807263B (en) | 2009-11-25 |
| WO2007123936A1 (en) | 2007-11-01 |
| CN103121996A (zh) | 2013-05-29 |
| CA2644425A1 (en) | 2007-11-01 |
| JP5525812B2 (ja) | 2014-06-18 |
| CN103121996B (zh) | 2015-10-21 |
| JP2009534386A (ja) | 2009-09-24 |
| US8076486B2 (en) | 2011-12-13 |
| EA200802050A1 (ru) | 2009-04-28 |
| EP2013180A1 (en) | 2009-01-14 |
| IL194546A0 (en) | 2009-08-03 |
| MX2008013308A (es) | 2008-10-27 |
| BRPI0711625A2 (pt) | 2011-12-06 |
| CN101426766A (zh) | 2009-05-06 |
| AR060807A1 (es) | 2008-07-16 |
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