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)
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- 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 (cg-RX-API-DMAC7.html) | 2010-12-24 |
| JP5211063B2 true JP5211063B2 (ja) | 2013-06-12 |
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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 |
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Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2297070A2 (en) * | 2008-07-03 | 2011-03-23 | Bayer Schering Pharma Aktiengesellschaft | Compounds and processes for production of radiopharmaceuticals |
| EP2370568B1 (en) | 2008-12-10 | 2017-07-19 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| MX340392B (es) | 2010-02-25 | 2016-07-06 | Dana Farber Cancer Inst Inc | Mutaciones del protooncogen de serina/treonina-proteina cinasa b-raf (braf) que confieren resistencia a los inhibidores del protooncogen de serina/treonina-proteina cinasa b-raf. |
| JP5985401B2 (ja) | 2010-03-09 | 2016-09-06 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | 第一の癌療法に対する耐性を現に有するか、または、そのような耐性を生じる患者において癌を診断および治療する方法 |
| CN103153063B (zh) | 2010-07-30 | 2016-02-17 | 肿瘤疗法科学股份有限公司 | 喹啉衍生物及含有其的melk抑制剂 |
| 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 |
| TW201414734A (zh) | 2012-07-10 | 2014-04-16 | Takeda Pharmaceutical | 氮雜吲哚衍生物 |
| EP2916859B1 (en) | 2012-11-02 | 2017-06-28 | The U.S.A. 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 |
| CN109072311A (zh) | 2016-04-15 | 2018-12-21 | 豪夫迈·罗氏有限公司 | 用于癌症的诊断和治疗方法 |
| PL3624796T3 (pl) | 2017-05-19 | 2025-06-30 | Nflection Therapeutics, Inc. | Związki pirolopirydyno-anilinowe do leczenia zaburzeń skórnych |
| DK3624795T3 (da) | 2017-05-19 | 2022-05-23 | Nflection Therapeutics Inc | Kondenserede, heteroaromatiske anilinforbindelser til behandling af hudforstyrrelser |
| US11859252B2 (en) | 2017-09-08 | 2024-01-02 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| WO2019158579A1 (en) | 2018-02-13 | 2019-08-22 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| US11572344B2 (en) | 2018-11-20 | 2023-02-07 | Nflection Therapeutics, Inc. | Cyanoaryl-aniline compounds for treatment of dermal disorders |
| CA3120352A1 (en) | 2018-11-20 | 2020-05-28 | Nflection Therapeutics, Inc. | Thienyl-aniline compounds for treatment of dermal disorders |
| US12378240B2 (en) | 2018-11-20 | 2025-08-05 | Nflection Therapeutics, Inc. | Naphthyridinone-aniline compounds for treatment of dermal disorders |
| US12371667B2 (en) | 2021-05-13 | 2025-07-29 | Washington University | Enhanced methods for inducing and maintaining naive human pluripotent stem cells |
| US12310950B2 (en) | 2021-11-23 | 2025-05-27 | Nflection Therapeutics, Inc. | Formulations of pyrrolopyridine-aniline compounds |
| CA3247162A1 (en) * | 2022-01-28 | 2023-08-03 | Insilico Medicine Ip Limited | Ectunocleotide pyrophosphatase-phosphodiesterase 1 (ENPP1) inhibitors and their uses |
| WO2023166450A1 (ko) * | 2022-03-04 | 2023-09-07 | 삼진제약주식회사 | 신규한 헤테로 고리 화합물 및 이를 포함하는 약학적 조성물 |
| WO2024033381A1 (en) | 2022-08-10 | 2024-02-15 | Vib Vzw | Inhibition of tcf4/itf2 in the treatment of cancer |
| WO2025026383A1 (en) * | 2023-08-02 | 2025-02-06 | Insilico Medicine Ip Limited | Crytsalline forms of ectonucleotide pyrophosphatase-phosphodiesterase 1 (enpp1) inhibitors and uses thereof |
| KR20250067072A (ko) * | 2023-11-07 | 2025-05-14 | 보로노이 주식회사 | 헤테로아릴 유도체 화합물 및 이의 용도 |
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 |
| ES2330628T3 (es) * | 2002-04-23 | 2009-12-14 | Aventis Pharmaceuticals Inc. | Ester del acido 3-(amino sustituido)-1h-indol-2-carboxilico y derivados del ester del acido 3-(amino sustituido)-benzo(b)tiofeno-2-carboxilico como imhibidores de expresion del gen de interleucina-4. |
| 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 |
| US7598259B2 (en) * | 2004-06-15 | 2009-10-06 | Schering Corporation | mGluR1 antagonists as therapeutic agents |
| AR049300A1 (es) * | 2004-06-15 | 2006-07-12 | Schering Corp | Compuestos triciclicos antagonistas de mglur1 como agentes terapeuticos |
| 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 |
-
2007
- 2007-11-29 AU AU2007325123A patent/AU2007325123B2/en not_active Ceased
- 2007-11-29 DK DK07854844.3T patent/DK2099796T3/da active
- 2007-11-29 WO PCT/US2007/085962 patent/WO2008067481A1/en not_active Ceased
- 2007-11-29 PT PT07854844T patent/PT2099796E/pt unknown
- 2007-11-29 CA CA002672327A patent/CA2672327A1/en not_active Abandoned
- 2007-11-29 JP JP2009539490A patent/JP5211063B2/ja not_active Expired - Fee Related
- 2007-11-29 PE PE2007001679A patent/PE20081354A1/es not_active Application Discontinuation
- 2007-11-29 AR ARP070105307A patent/AR064031A1/es unknown
- 2007-11-29 EP EP07854844A patent/EP2099796B1/en active Active
- 2007-11-29 CL CL200703444A patent/CL2007003444A1/es unknown
- 2007-11-29 AT AT07854844T patent/ATE511509T1/de active
- 2007-11-29 PL PL07854844T patent/PL2099796T3/pl unknown
- 2007-11-29 US US11/947,656 patent/US7855216B2/en not_active Expired - Fee Related
- 2007-11-29 TW TW096145474A patent/TW200829586A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008067481A1 (en) | 2008-06-05 |
| PE20081354A1 (es) | 2008-11-14 |
| EP2099796B1 (en) | 2011-06-01 |
| PT2099796E (pt) | 2011-09-06 |
| CA2672327A1 (en) | 2008-06-05 |
| PL2099796T3 (pl) | 2011-10-31 |
| DK2099796T3 (da) | 2011-09-05 |
| AU2007325123B2 (en) | 2012-12-13 |
| ATE511509T1 (de) | 2011-06-15 |
| CL2007003444A1 (es) | 2008-06-27 |
| JP2010511626A (ja) | 2010-04-15 |
| US7855216B2 (en) | 2010-12-21 |
| AR064031A1 (es) | 2009-03-04 |
| HK1135099A1 (en) | 2010-05-28 |
| EP2099796A1 (en) | 2009-09-16 |
| TW200829586A (en) | 2008-07-16 |
| AU2007325123A1 (en) | 2008-06-05 |
| US20080242655A1 (en) | 2008-10-02 |
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