JP5211063B2 - アザ−インドリル化合物及び使用方法 - Google Patents
アザ−インドリル化合物及び使用方法 Download PDFInfo
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- JP5211063B2 JP5211063B2 JP2009539490A JP2009539490A JP5211063B2 JP 5211063 B2 JP5211063 B2 JP 5211063B2 JP 2009539490 A JP2009539490 A JP 2009539490A JP 2009539490 A JP2009539490 A JP 2009539490A JP 5211063 B2 JP5211063 B2 JP 5211063B2
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- alkyl
- mmol
- nhc
- compound
- fluoro
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- 238000000034 method Methods 0.000 title description 177
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 409
- 150000001875 compounds Chemical class 0.000 claims description 287
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 34
- 241000124008 Mammalia Species 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 230000002159 abnormal effect Effects 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 230000010261 cell growth Effects 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 230000003463 hyperproliferative effect Effects 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 9
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 8
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 291
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 245
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 215
- -1 —CH 2 CH 2 CH 3 ) Chemical group 0.000 description 158
- 239000000203 mixture Substances 0.000 description 131
- 239000000243 solution Substances 0.000 description 122
- 239000007787 solid Substances 0.000 description 111
- 235000019439 ethyl acetate Nutrition 0.000 description 107
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 100
- 239000002904 solvent Substances 0.000 description 97
- 239000011541 reaction mixture Substances 0.000 description 90
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 87
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 86
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 75
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 70
- 238000003818 flash chromatography Methods 0.000 description 59
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 50
- 239000003921 oil Substances 0.000 description 49
- 235000019198 oils Nutrition 0.000 description 49
- 239000012044 organic layer Substances 0.000 description 48
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
- 238000005160 1H NMR spectroscopy Methods 0.000 description 41
- 239000011734 sodium Substances 0.000 description 38
- 210000004027 cell Anatomy 0.000 description 37
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 37
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000002585 base Substances 0.000 description 29
- 239000012267 brine Substances 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
- 238000010992 reflux Methods 0.000 description 26
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- 206010028980 Neoplasm Diseases 0.000 description 25
- 239000002253 acid Substances 0.000 description 24
- 238000011282 treatment Methods 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 0 *c(ccc(I)c1)c1F Chemical compound *c(ccc(I)c1)c1F 0.000 description 21
- 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 21
- 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- 201000010099 disease Diseases 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- 208000035475 disorder Diseases 0.000 description 19
- 229940002612 prodrug Drugs 0.000 description 19
- 239000000651 prodrug Substances 0.000 description 19
- 239000000758 substrate Substances 0.000 description 19
- 238000003556 assay Methods 0.000 description 18
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- 239000012453 solvate Substances 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 201000011510 cancer Diseases 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 229910052740 iodine Inorganic materials 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 12
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
- 239000012312 sodium hydride Substances 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 12
- 230000004913 activation Effects 0.000 description 11
- 239000002246 antineoplastic agent Substances 0.000 description 11
- 229940127089 cytotoxic agent Drugs 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
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- 230000000694 effects Effects 0.000 description 10
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 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 10
- 102000043136 MAP kinase family Human genes 0.000 description 9
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86805506P | 2006-11-30 | 2006-11-30 | |
| US60/868,055 | 2006-11-30 | ||
| US91762007P | 2007-05-11 | 2007-05-11 | |
| US60/917,620 | 2007-05-11 | ||
| US94474307P | 2007-06-18 | 2007-06-18 | |
| US60/944,743 | 2007-06-18 | ||
| PCT/US2007/085962 WO2008067481A1 (en) | 2006-11-30 | 2007-11-29 | Aza-indolyl compounds and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010511626A JP2010511626A (ja) | 2010-04-15 |
| JP2010511626A5 JP2010511626A5 (enExample) | 2010-12-24 |
| JP5211063B2 true JP5211063B2 (ja) | 2013-06-12 |
Family
ID=39169665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009539490A Expired - Fee Related JP5211063B2 (ja) | 2006-11-30 | 2007-11-29 | アザ−インドリル化合物及び使用方法 |
Country Status (14)
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| JP2011526267A (ja) * | 2008-07-03 | 2011-10-06 | バイエル ファーマ アクチエンゲゼルシャフト | 化合物および放射性医薬品の製造方法 |
| EP2370568B1 (en) | 2008-12-10 | 2017-07-19 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| CA2789696C (en) | 2010-02-25 | 2017-11-07 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| EP2545187B1 (en) | 2010-03-09 | 2018-09-05 | Dana-Farber Cancer Institute, Inc. | Methods of diagnosing and treating cancer in patients having or developing resistance to a first cancer therapy |
| US9120749B2 (en) | 2010-07-30 | 2015-09-01 | Oncotherapy Science, Inc. | Quinoline derivatives and MELK inhibitors containing the same |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| UY34893A (es) | 2012-07-10 | 2014-02-28 | Takeda Pharmaceutical | Derivados de azaindol |
| WO2014071183A1 (en) | 2012-11-02 | 2014-05-08 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Method of reducing adverse effects in a cancer patient undergoing treatment with a mek inhibitor |
| UA111925C2 (uk) | 2012-12-11 | 2016-06-24 | Федора Фармасьютікалз Інк. | БІЦИКЛІЧНІ СПОЛУКИ ТА ЇХ ВИКОРИСТАННЯ ЯК АНТИБАКТЕРІАЛЬНИХ АГЕНТІВ ТА ІНГІБІТОРІВ β-ЛАКТАМАЗИ |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| US20170114323A1 (en) | 2014-06-19 | 2017-04-27 | Whitehead Institute For Biomedical Research | Uses of kinase inhibitors for inducing and maintaining pluripotency |
| AU2017249229A1 (en) | 2016-04-15 | 2018-10-04 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| JP7212956B2 (ja) | 2017-05-19 | 2023-01-26 | エヌフレクション セラピューティクス インコーポレイテッド | 皮膚障害の処置用のピロロピリジン－アニリン化合物 |
| ES2913213T3 (es) | 2017-05-19 | 2022-06-01 | Nflection Therapeutics Inc | Compuestos heteroaromáticos de anilina condensados para el tratamiento de trastornos dérmicos |
| KR102811888B1 (ko) | 2017-09-08 | 2025-05-27 | 에프. 호프만-라 로슈 아게 | 암의 진단 및 치료 방법 |
| US20210008047A1 (en) | 2018-02-13 | 2021-01-14 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| EP3883552B1 (en) | 2018-11-20 | 2025-04-09 | NFlection Therapeutics, Inc. | Cyanoaryl-aniline compounds for treatment of dermal disorders |
| WO2020106305A1 (en) | 2018-11-20 | 2020-05-28 | Nflection Therapeutics, Inc. | Thienyl-aniline compounds for treatment of dermal disorders |
| CN113473986B (zh) | 2018-11-20 | 2024-10-11 | 恩福莱克逊治疗有限公司 | 用于治疗皮肤疾病萘啶酮苯胺化合物 |
| CN117157065A (zh) | 2021-01-21 | 2023-12-01 | 恩福莱克逊治疗有限公司 | 吡咯并吡啶-苯胺化合物的晶型 |
| US12371667B2 (en) | 2021-05-13 | 2025-07-29 | Washington University | Enhanced methods for inducing and maintaining naive human pluripotent stem cells |
| KR20240125577A (ko) | 2021-11-23 | 2024-08-19 | 엔플렉션 테라퓨틱스, 인코포레이티드 | 피롤로피리딘-아닐린 화합물의 제형 |
| MX2024009216A (es) * | 2022-01-28 | 2024-08-06 | Insilico Medicine Ip Ltd | Inhibidores de ectonucleotido pirofosfatasa-fosfodiesterasa 1 (enpp1) y usos de los mismos. |
| CN119013276A (zh) * | 2022-03-04 | 2024-11-22 | 三进制药株式会社 | 新型杂环化合物和包含该化合物的药物组合物 |
| US20260048075A1 (en) | 2022-08-10 | 2026-02-19 | Vib Vzw | Inhibition of TCF4/ITF2 in the Treatment of Cancer |
| CN121969621A (zh) * | 2023-08-02 | 2026-05-01 | 英矽智能科技知识产权有限公司 | 外核苷酸焦磷酸酶-磷酸二酯酶1 (enpp1)抑制剂的结晶形式及其用途 |
| WO2025100940A1 (ko) * | 2023-11-07 | 2025-05-15 | 보로노이 주식회사 | 헤테로아릴 유도체 화합물 및 이의 용도 |
| WO2026019990A1 (en) | 2024-07-18 | 2026-01-22 | Genentech, Inc. | Methods of treating cancer with anti-ccr8/anti-cd3 bispecific antibodies |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235537B2 (en) * | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| AU2003225131A1 (en) | 2002-04-23 | 2003-11-10 | Aventis Pharmaceuticals Inc. | 3-substituted amino-1h-indole-2-carboxylic acid and 3-substituted amino-benzo' b! thiophene-2-carboxylic acid derivatives as interieukin-4 gene expression inhibitors |
| US6929411B2 (en) * | 2003-09-03 | 2005-08-16 | Hewlett-Packard Development Company, L.P. | Selectable control of raster image processor |
| GB0412914D0 (en) * | 2004-06-10 | 2004-07-14 | Oxagen Ltd | Compounds |
| AR049300A1 (es) * | 2004-06-15 | 2006-07-12 | Schering Corp | Compuestos triciclicos antagonistas de mglur1 como agentes terapeuticos |
| US7598259B2 (en) * | 2004-06-15 | 2009-10-06 | Schering Corporation | mGluR1 antagonists as therapeutic agents |
| DE102005013621A1 (de) * | 2005-03-24 | 2006-09-28 | Curacyte Discovery Gmbh | Substituierte 2-Aryl(Hetaryl)-5-aminothieno[2,3-d]pyrimidin-6-carbonsäureamide, Verfahren zu ihrer Herstellung und Verwendung als Pharmazeutika |
| AR070127A1 (es) * | 2008-01-11 | 2010-03-17 | Novartis Ag | Pirrolo - pirimidinas y pirrolo -piridinas |
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| AU2007325123A1 (en) | 2008-06-05 |
| EP2099796A1 (en) | 2009-09-16 |
| PE20081354A1 (es) | 2008-11-14 |
| EP2099796B1 (en) | 2011-06-01 |
| CA2672327A1 (en) | 2008-06-05 |
| CL2007003444A1 (es) | 2008-06-27 |
| AR064031A1 (es) | 2009-03-04 |
| US7855216B2 (en) | 2010-12-21 |
| TW200829586A (en) | 2008-07-16 |
| AU2007325123B2 (en) | 2012-12-13 |
| WO2008067481A1 (en) | 2008-06-05 |
| PT2099796E (pt) | 2011-09-06 |
| DK2099796T3 (da) | 2011-09-05 |
| ATE511509T1 (de) | 2011-06-15 |
| HK1135099A1 (en) | 2010-05-28 |
| JP2010511626A (ja) | 2010-04-15 |
| PL2099796T3 (pl) | 2011-10-31 |
| US20080242655A1 (en) | 2008-10-02 |
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