KR102378288B1 - Pet-영상화 면역조정제 - Google Patents
Pet-영상화 면역조정제 Download PDFInfo
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- KR102378288B1 KR102378288B1 KR1020187036396A KR20187036396A KR102378288B1 KR 102378288 B1 KR102378288 B1 KR 102378288B1 KR 1020187036396 A KR1020187036396 A KR 1020187036396A KR 20187036396 A KR20187036396 A KR 20187036396A KR 102378288 B1 KR102378288 B1 KR 102378288B1
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Family Cites Families (44)
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|---|---|---|---|---|
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| US5374548A (en) | 1986-05-02 | 1994-12-20 | Genentech, Inc. | Methods and compositions for the attachment of proteins to liposomes using a glycophospholipid anchor |
| MX9203291A (es) | 1985-06-26 | 1992-08-01 | Liposome Co Inc | Metodo para acoplamiento de liposomas. |
| US5101827A (en) | 1985-07-05 | 1992-04-07 | Immunomedics, Inc. | Lymphographic and organ imaging method and kit |
| US5776093A (en) | 1985-07-05 | 1998-07-07 | Immunomedics, Inc. | Method for imaging and treating organs and tissues |
| US4735210A (en) | 1985-07-05 | 1988-04-05 | Immunomedics, Inc. | Lymphographic and organ imaging method and kit |
| US5328679A (en) | 1988-04-01 | 1994-07-12 | Immunomedics, Inc. | Methods for technetium/rhenium labeling of proteins |
| US5128119A (en) | 1989-06-12 | 1992-07-07 | Immunomedics, Inc. | Methods for technetium/rhenium labeling of f(ab1)2 fragments |
| US5108921A (en) | 1989-04-03 | 1992-04-28 | Purdue Research Foundation | Method for enhanced transmembrane transport of exogenous molecules |
| US5746996A (en) | 1994-06-03 | 1998-05-05 | Immunomedics, Inc. | Thiolation of peptides for radionuclide-based radiodetection and radiotherapy |
| IL113610A0 (en) | 1994-06-03 | 1995-08-31 | Immunomedics Inc | A method of radiolabeling a protein, radiolabeled proteins prepared thereby and diagnostic kits containing the same |
| US5753206A (en) | 1995-06-07 | 1998-05-19 | Immunomedics, Inc. | Radiometal-binding analogues of luteinizing hormone releasing hormone |
| US5869451A (en) | 1995-06-07 | 1999-02-09 | Glaxo Group Limited | Peptides and compounds that bind to a receptor |
| DE69737867T2 (de) | 1996-05-03 | 2007-10-18 | Immunomedics, Inc. | Zielgerichtete kombinations-immuntherapie für krebs |
| WO1998002192A1 (en) | 1996-07-12 | 1998-01-22 | Immunomedics, Inc. | Radiometal-binding peptide analogues |
| US6277818B1 (en) | 1998-10-29 | 2001-08-21 | Angstrom Pharmaceuticals, Inc. | Cyclic peptide ligands that target urokinase plasminogen activator receptor |
| US6187284B1 (en) | 1997-09-03 | 2001-02-13 | Immunomedics, Inc. | Fluorination of proteins and peptides for F-18 positron emission tomography |
| EP2141175B1 (en) | 2007-03-26 | 2016-07-27 | The University of Tokyo | Process for synthesizing cyclic peptide compound |
| MX2011002250A (es) | 2008-08-25 | 2011-08-17 | Amplimmune Inc | Antagonistas de muerte celular programada-1 y métodos de uso de los mismos. |
| US8907053B2 (en) | 2010-06-25 | 2014-12-09 | Aurigene Discovery Technologies Limited | Immunosuppression modulating compounds |
| JP5818237B2 (ja) | 2010-09-09 | 2015-11-18 | 国立大学法人 東京大学 | Ｎ−メチルアミノ酸およびその他の特殊アミノ酸を含む特殊ペプチド化合物ライブラリーの翻訳構築と活性種探索法 |
| EP2647720B1 (en) | 2010-12-03 | 2019-06-19 | The University of Tokyo | Peptide library production method, peptide library, and screening method |
| CN103732238A (zh) | 2011-06-08 | 2014-04-16 | 奥瑞基尼探索技术有限公司 | 用于免疫调节的治疗性化合物 |
| JP2015512910A (ja) | 2012-03-29 | 2015-04-30 | 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 | ヒトｐｄ１のｂｃループに由来する免疫調節性環状化合物 |
| JP2013253842A (ja) | 2012-06-06 | 2013-12-19 | Univ Of Tokyo | ｐＨ依存的に標的分子に結合するペプチドのスクリーニング方法 |
| WO2013182240A1 (en) | 2012-06-06 | 2013-12-12 | Polyphor Ag | Beta-hairpin peptidomimetics |
| KR20150131269A (ko) | 2013-03-15 | 2015-11-24 | 제넨테크, 인크. | Pd-1 및 pd-l1 관련 상태를 치료하기 위한 바이오마커 및 방법 |
| SG11201601685TA (en) | 2013-09-06 | 2016-04-28 | Aurigene Discovery Tech Ltd | Cyclic peptidomimetic compounds as immunomodulators |
| WO2015044900A1 (en) | 2013-09-27 | 2015-04-02 | Aurigene Discovery Technologies Limited | Therapeutic immunomodulating compounds |
| MX380553B (es) | 2014-09-11 | 2025-03-12 | Bristol Myers Squibb Co | Inhibidores macrocíclicos de las interacciones proteína/proteína de muerte programada 1 (pd-1)/pd-l1 y cd80(b7-1)/pd-l1. |
| US9732119B2 (en) | 2014-10-10 | 2017-08-15 | Bristol-Myers Squibb Company | Immunomodulators |
| US9856292B2 (en) | 2014-11-14 | 2018-01-02 | Bristol-Myers Squibb Company | Immunomodulators |
| JP6701217B2 (ja) | 2014-11-25 | 2020-05-27 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 生物学的製剤の１８ｆ−放射性標識方法および組成物 |
| KR102632418B1 (ko) * | 2014-11-25 | 2024-01-31 | 브리스톨-마이어스 스큅 컴퍼니 | 영상화를 위한 신규 pd-l1 결합 폴리펩티드 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013010573A1 (en) | 2011-07-18 | 2013-01-24 | Universitaet Muenster | Compounds with matrix-metalloproteinase inhibitory activity |
| WO2014151634A1 (en) | 2013-03-15 | 2014-09-25 | Bristol-Myers Squibb Company | Macrocyclic inhibitors of the pd-1/pd-l1 and cd80(b7-1)/pd-l1 protein/protein interactions |
Non-Patent Citations (1)
| Title |
|---|
| Maute Roy 외. Proceeding of the National Academy of Sciences of the United States of America. Vol. 112(47), 2015, pp. E6506-6514 |
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