JP2009515984A5 - - Google Patents
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- JP2009515984A5 JP2009515984A5 JP2008541312A JP2008541312A JP2009515984A5 JP 2009515984 A5 JP2009515984 A5 JP 2009515984A5 JP 2008541312 A JP2008541312 A JP 2008541312A JP 2008541312 A JP2008541312 A JP 2008541312A JP 2009515984 A5 JP2009515984 A5 JP 2009515984A5
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- JP
- Japan
- Prior art keywords
- hydrogen
- compound
- aliphatic
- composition
- formula
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 39
- 125000001931 aliphatic group Chemical group 0.000 claims 33
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 26
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 239000000203 mixture Substances 0.000 claims 18
- 125000005843 halogen group Chemical group 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000001118 alkylidene group Chemical group 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 9
- 229940124597 therapeutic agent Drugs 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 239000011593 sulfur Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- 102000001253 Protein Kinase Human genes 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 108060006633 protein kinase Proteins 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 102100031463 Serine/threonine-protein kinase PLK1 Human genes 0.000 claims 2
- 125000002723 alicyclic group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 239000012472 biological sample Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 108010056274 polo-like kinase 1 Proteins 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 208000019838 Blood disease Diseases 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010061598 Immunodeficiency Diseases 0.000 claims 1
- 208000029462 Immunodeficiency disease Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 230000001066 destructive effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 208000014951 hematologic disease Diseases 0.000 claims 1
- 208000018706 hematopoietic system disease Diseases 0.000 claims 1
- -1 hydrogen compound Chemical class 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 230000007813 immunodeficiency Effects 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 229960003444 immunosuppressant agent Drugs 0.000 claims 1
- 230000001861 immunosuppressant effect Effects 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 210000000944 nerve tissue Anatomy 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 230000001228 trophic effect Effects 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
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| CA2711614A1 (en) | 2008-01-08 | 2009-07-16 | Array Biopharma Inc. | Pyrrolopyridines as kinase inhibitors |
| CA2711741A1 (en) | 2008-01-09 | 2009-07-16 | Array Biopharma Inc. | Pyrazolopyridines as kinase inhibitors |
| JP2011515072A (ja) * | 2008-02-13 | 2011-05-19 | エラン ファーマ インターナショナル リミテッド | α−シヌクレインキナーゼ |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| JP6618901B2 (ja) | 2013-11-13 | 2019-12-11 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | インフルエンザウイルスの複製の阻害剤を調製する方法 |
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| JP2019532054A (ja) * | 2016-09-20 | 2019-11-07 | グラクソスミスクライン、インテレクチュアル、プロパティー、（ナンバー２）、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ （Ｎｏ．２） Ｌｉｍｉｔｅｄ | Ｔｒｐｖ４拮抗薬 |
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Family Cites Families (45)
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| JP3485198B2 (ja) | 1993-11-10 | 2004-01-13 | 富士写真フイルム株式会社 | ヒドラジン化合物及び該化合物を含むハロゲン化銀写真感光材料 |
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| US5932737A (en) | 1994-12-02 | 1999-08-03 | Fujisawa Pharmaceutical Co., Ltd. | Peptide compounds for treatment of no-mediated diseases |
| US5837704A (en) | 1995-02-17 | 1998-11-17 | Boehringer Ingelheim Pharmaceuticals, Inc. | 2-heteroaryl-5,11-dihydro-6H-dipyrido 3,2-B:2',3'-E! 1,4!diazepines and their use in the prevention or treatment of HIV infection |
| US5804585A (en) | 1996-04-15 | 1998-09-08 | Texas Biotechnology Corporation | Thieno-pyridine sulfonamides derivatives thereof and related compounds that modulate the activity of endothelin |
| US6537999B2 (en) | 1996-06-06 | 2003-03-25 | Duquesne University Of The Holy Ghost | Pyrimidine derivatives and methods of making and using these derivatives |
| JP4028607B2 (ja) | 1996-07-24 | 2007-12-26 | 富山化学工業株式会社 | 新規なセファロスポリン誘導体またはその塩 |
| US6040321A (en) * | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| AU3117899A (en) | 1998-04-02 | 1999-10-25 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| US6025366A (en) | 1998-04-02 | 2000-02-15 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| US6110931A (en) | 1998-04-02 | 2000-08-29 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| JP2002510631A (ja) | 1998-04-02 | 2002-04-09 | メルク エンド カムパニー インコーポレーテッド | 性腺刺激ホルモン放出ホルモン拮抗薬 |
| MXPA01002173A (es) * | 1998-08-28 | 2003-07-14 | Scios Inc | Inhibidores de p38-alfa cinasa. |
| US6319660B1 (en) | 1998-12-28 | 2001-11-20 | Eastman Kodak Company | Color photographic element containing speed improving compound |
| CZ27399A3 (cs) | 1999-01-26 | 2000-08-16 | Ústav Experimentální Botaniky Av Čr | Substituované dusíkaté heterocyklické deriváty, způsob jejich přípravy, tyto deriváty pro použití jako léčiva, farmaceutická kompozice a kombinovaný farmaceutický přípravek tyto deriváty obsahující a použití těchto derivátů pro výrobu léčiv |
| CO5170498A1 (es) * | 1999-05-28 | 2002-06-27 | Abbott Lab | Biaril sulfonamidas son utiles como inhibidores de proliferacion celular |
| US6309811B2 (en) | 1999-07-21 | 2001-10-30 | Eastman Kodak Company | Color photographic element containing nitrogen heterocycle derivative and inhibitor releasing coupler |
| EA200401099A1 (ru) | 2000-02-04 | 2005-02-24 | Пфайзер Продактс Инк. | Производные гетероциклического амида |
| GB0021670D0 (en) | 2000-09-04 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| US6770645B2 (en) | 2001-03-16 | 2004-08-03 | Pfizer Inc. | Pharmaceutically active compounds |
| GB0106661D0 (en) | 2001-03-16 | 2001-05-09 | Pfizer Ltd | Pharmaceutically active compounds |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| WO2003000690A1 (en) | 2001-06-25 | 2003-01-03 | Aventis Pharmaceuticals Inc. | Synthesis of heterocyclic compounds employing microwave technology |
| GB0128287D0 (en) * | 2001-11-26 | 2002-01-16 | Smithkline Beecham Plc | Novel method and compounds |
| TW200403243A (en) | 2002-07-18 | 2004-03-01 | Wyeth Corp | 1-Heterocyclylalkyl-3-sulfonylazaindole or-azaindazole derivatives as 5-hydroxytryptamine-6 ligands |
| EP1526852A1 (en) * | 2002-07-25 | 2005-05-04 | Pharmacia Italia S.p.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| GB0218800D0 (en) | 2002-08-13 | 2002-09-18 | Celltech R&D Ltd | Chemical compounds |
| GB0226583D0 (en) | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| US7468376B2 (en) * | 2003-02-27 | 2008-12-23 | Palau Pharma, S.A. | Pyrazolopyridine derivates |
| US7521447B2 (en) * | 2003-03-03 | 2009-04-21 | Array Biopharma Inc. | P38 inhibitors and methods of use thereof |
| US7381825B2 (en) | 2003-03-17 | 2008-06-03 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
| EP1631568A1 (en) | 2003-04-18 | 2006-03-08 | Memory Pharmaceuticals Corporation | Pyrazole derivatives as phosphodiesterase 4 inhibitors |
| EP1620095A4 (en) | 2003-04-24 | 2009-04-01 | Merck & Co Inc | HEMMER OF ACT ACTIVITY |
| EP1648455A4 (en) | 2003-07-23 | 2009-03-04 | Exelixis Inc | MODULATORS OF ALK PROTEIN (ANAPLASTIC LYMPHOMA KINASE) AND METHODS OF USE |
| US7132435B2 (en) | 2003-07-25 | 2006-11-07 | Pfizer Inc. | Compounds |
| GB0317482D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as pde4 inhibitors |
| GB0317471D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Novel compounds |
| WO2005023818A2 (en) | 2003-09-10 | 2005-03-17 | Gpc Biotech Ag | Heterobicyclic compounds as pharmaceutically active agents |
| JP5164380B2 (ja) * | 2003-10-21 | 2013-03-21 | サイクラセル リミテッド | ピリミジン−４−イル−３，４−チオン化合物及び治療におけるその使用 |
| WO2005085249A1 (en) * | 2004-02-27 | 2005-09-15 | F. Hoffmann-La Roche Ag | Fused derivatives of pyrazole |
| CA2573573A1 (en) * | 2004-07-27 | 2006-02-09 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
-
2006
- 2006-11-15 WO PCT/US2006/044361 patent/WO2007059219A1/en not_active Ceased
- 2006-11-15 US US11/600,311 patent/US8017781B2/en not_active Expired - Fee Related
- 2006-11-15 AU AU2006315436A patent/AU2006315436A1/en not_active Abandoned
- 2006-11-15 JP JP2008541312A patent/JP2009515984A/ja active Pending
- 2006-11-15 CN CNA2006800507344A patent/CN101365700A/zh active Pending
- 2006-11-15 EP EP06837683A patent/EP1948657A1/en not_active Withdrawn
- 2006-11-15 CA CA002628179A patent/CA2628179A1/en not_active Abandoned
- 2006-11-15 EP EP11191099A patent/EP2514751A1/en not_active Withdrawn
-
2011
- 2011-07-29 US US13/193,739 patent/US8445681B2/en not_active Expired - Fee Related
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