ES2315703T3 - Inhibidores de la quinasa p-38. - Google Patents
Inhibidores de la quinasa p-38. Download PDFInfo
- Publication number
- ES2315703T3 ES2315703T3 ES04778988T ES04778988T ES2315703T3 ES 2315703 T3 ES2315703 T3 ES 2315703T3 ES 04778988 T ES04778988 T ES 04778988T ES 04778988 T ES04778988 T ES 04778988T ES 2315703 T3 ES2315703 T3 ES 2315703T3
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- Prior art keywords
- alkyl
- substituted
- baselineskip
- aryl
- methyl
- 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.)
- Expired - Lifetime
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- 239000003112 inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 51
- 201000010099 disease Diseases 0.000 claims abstract description 31
- 208000035475 disorder Diseases 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- -1 sulfonamido, sulfonamido Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 65
- 239000002253 acid Substances 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- 125000001769 aryl amino group Chemical group 0.000 claims description 10
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- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 8
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
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- 125000005518 carboxamido group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
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- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
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- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005239 aroylamino group Chemical group 0.000 claims description 4
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 3
- ZQDKOTPZLQHPBR-UHFFFAOYSA-N 3-(3-benzyl-4-oxoquinazolin-7-yl)-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1C(C=1)=CC=C(C2=O)C=1N=CN2CC1=CC=CC=C1 ZQDKOTPZLQHPBR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
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- KGPJPLBEAMXAEJ-UHFFFAOYSA-N n-cyclopropyl-3-[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-7-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1C(C=1)=CC=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C(Cl)=C1 KGPJPLBEAMXAEJ-UHFFFAOYSA-N 0.000 claims description 3
- QPZAZKMAJLIKAX-UHFFFAOYSA-N n-cyclopropyl-3-[3-[(4-methoxyphenyl)methyl]-4-oxoquinazolin-7-yl]-4-methylbenzamide Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C2=CC=C(C=3C(=CC=C(C=3)C(=O)NC3CC3)C)C=C2N=C1 QPZAZKMAJLIKAX-UHFFFAOYSA-N 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- GLBORQOWZPWKSD-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-(2-oxo-4-phenyl-1h-quinazolin-7-yl)benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1C(C=C1NC(=O)N=2)=CC=C1C=2C1=CC=CC=C1 GLBORQOWZPWKSD-UHFFFAOYSA-N 0.000 claims description 2
- LDFYACGKGVSHAE-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-(4-oxo-1h-quinazolin-7-yl)benzamide Chemical compound C1=C(C=2C=C3C(C(NC=N3)=O)=CC=2)C(C)=CC=C1C(=O)NC1CC1 LDFYACGKGVSHAE-UHFFFAOYSA-N 0.000 claims description 2
- YOEPYRRTMCNYCD-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-(4-phenylquinazolin-7-yl)benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1C(C=C1N=CN=2)=CC=C1C=2C1=CC=CC=C1 YOEPYRRTMCNYCD-UHFFFAOYSA-N 0.000 claims description 2
- IGADKXNUGPMKMO-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[5-(5-methyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl]benzamide Chemical compound O1C(C)=NN=C1C1=CC=C(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)N=C1 IGADKXNUGPMKMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 56
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 abstract description 51
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 abstract description 51
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- 239000002904 solvent Substances 0.000 description 57
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000004128 high performance liquid chromatography Methods 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
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- 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 20
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
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Classifications
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- 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
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| US490096P | 2003-07-25 |
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| ES2315703T3 true ES2315703T3 (es) | 2009-04-01 |
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| EP (3) | EP1687284B1 (enExample) |
| JP (1) | JP2007500129A (enExample) |
| CN (2) | CN100447137C (enExample) |
| AT (2) | ATE412642T1 (enExample) |
| AU (2) | AU2004261589B2 (enExample) |
| BR (1) | BRPI0412918A (enExample) |
| CA (1) | CA2534990A1 (enExample) |
| DE (2) | DE602004017494D1 (enExample) |
| ES (1) | ES2315703T3 (enExample) |
| MX (1) | MXPA06000915A (enExample) |
| PL (1) | PL1687284T3 (enExample) |
| PT (1) | PT1687284E (enExample) |
| WO (1) | WO2005012241A2 (enExample) |
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| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| GB0124936D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124941D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124931D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124939D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124934D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124933D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124938D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| ATE485275T1 (de) * | 2002-02-12 | 2010-11-15 | Glaxosmithkline Llc | Nicotinamide und deren verwendung als p38 inhibitoren |
| GB0217757D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
| GB0308201D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| GB0308186D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| GB0308185D0 (en) * | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
| US7932272B2 (en) * | 2003-09-30 | 2011-04-26 | Eisai R&D Management Co., Ltd. | Antifungal agent containing heterocyclic compound |
| GB0324790D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Amide derivatives |
| GB0402143D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
| JPWO2006016548A1 (ja) * | 2004-08-09 | 2008-05-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環化合物を含有する新規な抗マラリア剤 |
| US20070054916A1 (en) * | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| US20080051416A1 (en) * | 2004-10-05 | 2008-02-28 | Smithkline Beecham Corporation | Novel Compounds |
| EP1802606B1 (en) * | 2004-10-19 | 2011-03-16 | Compass Pharmaceuticals LLC | Arylcarboxamides and their use as anti-tumor agents |
| US7759337B2 (en) * | 2005-03-03 | 2010-07-20 | Amgen Inc. | Phthalazine compounds and methods of use |
| WO2006106711A1 (ja) * | 2005-03-30 | 2006-10-12 | Eisai R & D Management Co., Ltd. | ピリジン誘導体を含有する抗真菌剤 |
| GB0512429D0 (en) * | 2005-06-17 | 2005-07-27 | Smithkline Beecham Corp | Novel compound |
| RU2452729C2 (ru) * | 2005-09-16 | 2012-06-10 | Арроу Терапьютикс Лимитед | Бифенильные производные и их применение при лечении гепатита с |
| HRP20100542T1 (hr) * | 2005-09-16 | 2010-11-30 | Arrow Therapeutics Limited | Derivati bifenila i njihova uporaba za liječenje hepatitisa c |
| TWI385169B (zh) * | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| ES2432361T3 (es) * | 2005-12-02 | 2013-12-03 | Bayer Healthcare, Llc | Derivados de pirrolotriazina útiles para el tratamiento de cáncer por inhibición de cinasa Aurora |
| EP1991531A1 (en) * | 2006-02-28 | 2008-11-19 | Amgen Inc. | Cinnoline and quinoxaline derivates as phosphodiesterase 10 inhibitors |
| WO2007138242A1 (en) * | 2006-05-30 | 2007-12-06 | Arrow Therapeutics Limited | Biphenyl derivatives and their use in treating hepatitis c |
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| US20090258882A1 (en) * | 2006-07-28 | 2009-10-15 | Novartis Ag | 2,4-Substituted Quinazolines as Lipid Kinase Inhibitors |
| US8183264B2 (en) * | 2006-09-21 | 2012-05-22 | Eisai R&D Managment Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| WO2008050808A1 (fr) * | 2006-10-24 | 2008-05-02 | Kyowa Hakko Kirin Co., Ltd. | Dérivé de 2-aminoquinazoline |
| EP2097085A4 (en) * | 2006-11-27 | 2010-02-10 | Ariad Pharma Inc | THERAPEUTIC MATERIALS AND METHOD |
| WO2008124614A1 (en) | 2007-04-06 | 2008-10-16 | Neurocrine Biosciences, Inc. | Gonadotropin-releasing hormone receptor antagonists and methods relating thereto |
| AR065948A1 (es) | 2007-04-06 | 2009-07-15 | Neurocrine Biosciences Inc | Antagonistas del receptor de la hormona liberadora de gonadotropina y procedimientos relacionados con los mismos |
| AU2008246798A1 (en) | 2007-04-27 | 2008-11-13 | Eisai R&D Management Co., Ltd. | Salt of heterocycle-substituted pyridine derivative or crystal thereof |
| TW200841879A (en) * | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
| EP1992344A1 (en) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 alpha as a therapeutic target in pathologies linked to FGFR3 mutation |
| US20090047243A1 (en) * | 2007-07-17 | 2009-02-19 | Richard Rickles | Combinations for the treatment of b-cell proliferative disorders |
| CA2694983A1 (en) * | 2007-07-17 | 2009-01-22 | Combinatorx, Incorporated | Treatments of b-cell proliferative disorders |
| WO2009034390A1 (en) * | 2007-09-14 | 2009-03-19 | Arrow Therapeutics Limited | Heterocyclic derivatives and their use in treating hepatitis c |
| KR100916716B1 (ko) * | 2007-09-27 | 2009-09-10 | 한국화학연구원 | 3-클로로-5-치환-퀴녹살린-2-아민 유도체 및 약제학적으로허용 가능한 그의 염, 그의 제조방법 및 그를 유효성분으로함유하는 spc 수용체 활성으로 유발되는 염증관련 질환치료제 |
| US8513287B2 (en) * | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| US20100009934A1 (en) * | 2008-06-09 | 2010-01-14 | Combinatorx, Incorporated | Beta adrenergic receptor agonists for the treatment of b-cell proliferative disorders |
| US8188119B2 (en) * | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
| JP2012176900A (ja) * | 2009-06-24 | 2012-09-13 | Eisai R & D Management Co Ltd | ((ホスホノオキシ)メチル)ピリジニウム環を有するピリジン誘導体およびそれらを含有する抗真菌剤 |
| CN102120990A (zh) * | 2010-03-15 | 2011-07-13 | 中国人民解放军军事医学科学院基础医学研究所 | 人p38α与TAB1新功能表位以及用途 |
| TWI532742B (zh) | 2011-02-28 | 2016-05-11 | 艾伯維有限公司 | 激酶之三環抑制劑 |
| CN103524431B (zh) * | 2013-09-24 | 2016-01-13 | 西安交通大学 | 3-苄基-4-喹唑啉酮类化合物及其合成方法和应用 |
| KR20160073413A (ko) * | 2013-10-23 | 2016-06-24 | 추가이 세이야쿠 가부시키가이샤 | 퀴나졸리논 및 이소퀴놀리논 유도체 |
| CN104961804B (zh) * | 2015-07-08 | 2017-12-01 | 中国人民解放军军事医学科学院基础医学研究所 | p38α拮抗肽突变体及其应用 |
| CN104961803B (zh) * | 2015-07-08 | 2017-11-28 | 中国人民解放军军事医学科学院基础医学研究所 | 一种治疗心肌缺血再灌注损伤的多肽药物 |
| KR101879481B1 (ko) * | 2015-08-31 | 2018-07-17 | 경희대학교 산학협력단 | 벤조페논 유도체, 이의 제조방법 및 이를 포함하는 항염증 약학적 조성물 |
| JP7028780B2 (ja) * | 2015-09-30 | 2022-03-02 | シイエスピイシイ・チョンチ・ファーマシューティカル・テクノロジー・(シーチアチョワン)・カンパニー・リミテッド | ベンズアミド誘導体 |
| WO2018109667A1 (en) | 2016-12-15 | 2018-06-21 | Nestec Sa | Compositions and methods that modulate white blood cells or neutrophils in a companion animal |
| KR102114394B1 (ko) * | 2017-08-30 | 2020-05-22 | 경희대학교 산학협력단 | 벤조페논 유도체, 이의 제조방법 및 이를 포함하는 b형간염 치료용 약학적 조성물 |
| CN111183957A (zh) * | 2020-02-19 | 2020-05-22 | 中国医科大学附属第一医院 | 一种减轻自身免疫甲状腺炎模型的构建方法及其应用 |
| KR102624481B1 (ko) * | 2020-03-20 | 2024-01-16 | (주)프레이저테라퓨틱스 | p38 제거능을 갖는 화합물, 이의 제조방법 및 이를 포함하는 만성 염증성 질환 치료용 조성물 |
| KR102298450B1 (ko) * | 2021-01-29 | 2021-09-08 | (주)프레이저테라퓨틱스 | p38 MAP 키나아제 억제제로 항염증 활성을 나타내는 신규 화합물 |
| KR102314026B1 (ko) * | 2021-07-06 | 2021-10-19 | (주)프레이저테라퓨틱스 | p38 MAP 키나아제 억제제로 염증성 질환의 치료 효과를 나타내는 신규 화합물 |
| CN115317612A (zh) * | 2022-07-29 | 2022-11-11 | 中南大学 | 高表达热休克蛋白的巨噬细胞作为靶点在制备肝细胞癌药物中的应用 |
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2004
- 2004-07-23 WO PCT/US2004/023726 patent/WO2005012241A2/en not_active Ceased
- 2004-07-23 EP EP04778988A patent/EP1687284B1/en not_active Expired - Lifetime
- 2004-07-23 US US10/898,581 patent/US7700622B2/en not_active Expired - Fee Related
- 2004-07-23 BR BRPI0412918-0A patent/BRPI0412918A/pt not_active IP Right Cessation
- 2004-07-23 EP EP08158865A patent/EP1990338B1/en not_active Expired - Lifetime
- 2004-07-23 PT PT04778988T patent/PT1687284E/pt unknown
- 2004-07-23 PL PL04778988T patent/PL1687284T3/pl unknown
- 2004-07-23 DE DE602004017494T patent/DE602004017494D1/de not_active Expired - Lifetime
- 2004-07-23 JP JP2006521269A patent/JP2007500129A/ja not_active Ceased
- 2004-07-23 AT AT04778988T patent/ATE412642T1/de not_active IP Right Cessation
- 2004-07-23 MX MXPA06000915A patent/MXPA06000915A/es active IP Right Grant
- 2004-07-23 CA CA002534990A patent/CA2534990A1/en not_active Abandoned
- 2004-07-23 DE DE602004029293T patent/DE602004029293D1/de not_active Expired - Lifetime
- 2004-07-23 ES ES04778988T patent/ES2315703T3/es not_active Expired - Lifetime
- 2004-07-23 CN CNB2004800277979A patent/CN100447137C/zh not_active Expired - Fee Related
- 2004-07-23 AU AU2004261589A patent/AU2004261589B2/en not_active Ceased
- 2004-07-23 CN CNA2008101343893A patent/CN101337944A/zh active Pending
- 2004-07-23 AT AT08158865T patent/ATE482205T1/de not_active IP Right Cessation
- 2004-07-23 US US10/565,452 patent/US7754726B2/en not_active Expired - Fee Related
- 2004-07-23 EP EP10164753A patent/EP2251333A1/en not_active Withdrawn
-
2008
- 2008-06-13 AU AU2008202641A patent/AU2008202641A1/en not_active Abandoned
-
2010
- 2010-05-28 US US12/789,949 patent/US20100234404A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE412642T1 (de) | 2008-11-15 |
| AU2008202641A1 (en) | 2008-07-03 |
| CN101337944A (zh) | 2009-01-07 |
| DE602004017494D1 (de) | 2008-12-11 |
| PL1687284T3 (pl) | 2009-04-30 |
| PT1687284E (pt) | 2009-01-30 |
| CN1856480A (zh) | 2006-11-01 |
| ATE482205T1 (de) | 2010-10-15 |
| US7700622B2 (en) | 2010-04-20 |
| EP1990338A2 (en) | 2008-11-12 |
| EP1990338B1 (en) | 2010-09-22 |
| CA2534990A1 (en) | 2005-02-10 |
| AU2004261589A1 (en) | 2005-02-10 |
| EP2251333A1 (en) | 2010-11-17 |
| DE602004029293D1 (de) | 2010-11-04 |
| EP1990338A3 (en) | 2009-01-21 |
| EP1687284A2 (en) | 2006-08-09 |
| CN100447137C (zh) | 2008-12-31 |
| AU2004261589B2 (en) | 2008-05-22 |
| US20050020590A1 (en) | 2005-01-27 |
| EP1687284B1 (en) | 2008-10-29 |
| US20070111999A1 (en) | 2007-05-17 |
| WO2005012241A3 (en) | 2005-04-14 |
| WO2005012241A2 (en) | 2005-02-10 |
| US20100234404A1 (en) | 2010-09-16 |
| JP2007500129A (ja) | 2007-01-11 |
| US7754726B2 (en) | 2010-07-13 |
| BRPI0412918A (pt) | 2006-09-26 |
| MXPA06000915A (es) | 2006-03-30 |
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