KR20150129011A - 고체상 펩티드 합성 방법 및 연관 시스템 - Google Patents
고체상 펩티드 합성 방법 및 연관 시스템 Download PDFInfo
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- KR20150129011A KR20150129011A KR1020157029308A KR20157029308A KR20150129011A KR 20150129011 A KR20150129011 A KR 20150129011A KR 1020157029308 A KR1020157029308 A KR 1020157029308A KR 20157029308 A KR20157029308 A KR 20157029308A KR 20150129011 A KR20150129011 A KR 20150129011A
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- amino acid
- peptide
- immobilized peptide
- immobilized
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- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/045—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers using devices to improve synthesis, e.g. reactors, special vessels
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- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/08—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents
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| US9695214B2 (en) | 2013-03-15 | 2017-07-04 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| EP4240110A3 (en) * | 2015-06-19 | 2023-11-08 | Protein Technologies, Inc. | Chemical reaction vessel and synthesis systems and methods |
| EP3334750B1 (en) | 2015-08-11 | 2022-10-05 | Anie Philip | Peptidic tgf-beta antagonists |
| CN108289925A (zh) * | 2015-09-17 | 2018-07-17 | 麻省理工学院 | 固相肽合成方法和相关系统 |
| CN108290923A (zh) | 2015-09-17 | 2018-07-17 | 麻省理工学院 | 用于固相肽合成的方法和系统 |
| US10239914B2 (en) | 2015-10-23 | 2019-03-26 | Cem Corporation | In-situ solvent recycling process for solid phase peptide synthesis at elevated temperatures |
| WO2017070512A1 (en) * | 2015-10-23 | 2017-04-27 | Cem Corporation | Improvements in solid phase peptide synthesis |
| EP3365352A4 (en) * | 2015-10-23 | 2019-06-05 | CEM Corporation | IMPROVEMENTS OF SOLID PHASE PEPTIDE SYNTHESIS |
| EP3507299B1 (en) * | 2016-09-03 | 2022-07-27 | CEM Corporation | In-situ solvent recycling process for solid phase peptide synthesis at elevated temperatures |
| USRE49961E1 (en) | 2016-10-21 | 2024-05-07 | Cem Corporation | Solid phase peptide syntheses |
| IL293956A (en) | 2017-04-12 | 2022-08-01 | Magenta Therapeutics Inc | Aryl hydrocarbon receptor antagonist and its uses |
| JP7412341B2 (ja) | 2017-10-31 | 2024-01-12 | エディジーン バイオテクノロジー インコーポレイテッド | 造血幹細胞および前駆細胞の増幅のための組成物および方法 |
| EP3703715A1 (en) | 2017-10-31 | 2020-09-09 | Magenta Therapeutics, Inc. | Compositions and methods for hematopoietic stem and progenitor cell transplant therapy |
| KR20200096942A (ko) | 2017-12-06 | 2020-08-14 | 마젠타 테라퓨틱스 인코포레이티드 | 조혈 줄기 및 자손 세포의 동원을 위한 투여 요법 |
| CN111902411A (zh) | 2018-01-03 | 2020-11-06 | 美真达治疗公司 | 用于扩增造血干细胞和祖细胞以及治疗遗传性代谢紊乱的组合物和方法 |
| CN112020508A (zh) | 2018-05-04 | 2020-12-01 | 法国多肽实验室 | 具有再循环回路的自动合成反应器系统 |
| EP3807292A4 (en) * | 2018-06-14 | 2022-03-16 | CEM Corporation | Solvent system for solid phase peptide synthesis |
| CN111217891B (zh) * | 2018-11-27 | 2023-11-14 | 深圳翰宇药业股份有限公司 | 一种特利加压素的合成方法 |
| CN112111001B (zh) * | 2019-06-19 | 2021-10-29 | 翰宇药业(武汉)有限公司 | 胸腺肽Tα-1的合成方法 |
| CN110343147B (zh) * | 2019-08-22 | 2021-07-02 | 凯莱英医药集团(天津)股份有限公司 | 艾替班特的合成方法 |
| US20220401481A1 (en) | 2019-11-01 | 2022-12-22 | Magenta Therapeutics, Inc. | Dosing regimens for the mobilization of hematopoietic stem and progenitor cells |
| CA3167047A1 (en) | 2020-02-05 | 2021-08-12 | Martin D. Johnson | Three resin reactors in series peptide synthesizer |
| US11049590B1 (en) | 2020-02-12 | 2021-06-29 | Peptilogics, Inc. | Artificial intelligence engine architecture for generating candidate drugs |
| SE2050293A1 (en) * | 2020-03-17 | 2021-09-18 | Peptisystems Ab | Peptide synthesis and system thereof |
| US11834480B2 (en) | 2020-08-03 | 2023-12-05 | Amide Technologies | Protein inhibitors with reduced immunogenicity and resistance to degradation, and methods for their preparation and use |
| EP4247830A1 (en) * | 2020-11-17 | 2023-09-27 | Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. | Extremely fast solid phase synthesis |
| US20220165359A1 (en) | 2020-11-23 | 2022-05-26 | Peptilogics, Inc. | Generating anti-infective design spaces for selecting drug candidates |
| EP4308694A1 (en) | 2021-03-16 | 2024-01-24 | Magenta Therapeutics, Inc. | Dosing regimens for hematopoietic stem cell mobilization for stem cell transplants in multiple myeloma patients |
| US11512345B1 (en) | 2021-05-07 | 2022-11-29 | Peptilogics, Inc. | Methods and apparatuses for generating peptides by synthesizing a portion of a design space to identify peptides having non-canonical amino acids |
| US11587643B2 (en) | 2021-05-07 | 2023-02-21 | Peptilogics, Inc. | Methods and apparatuses for a unified artificial intelligence platform to synthesize diverse sets of peptides and peptidomimetics |
| WO2023068987A1 (en) | 2021-10-18 | 2023-04-27 | Polypeptide Laboratories Holding (Ppl) Ab | Intermittent percolation washing |
| CN115669843A (zh) * | 2022-10-26 | 2023-02-03 | 中国农业大学 | 一种采用高压微射流结合混合肽有效杀灭芽孢的方法 |
| WO2025071365A1 (ko) * | 2023-09-27 | 2025-04-03 | 에스피투티엑스주식회사 | 흐름 반응기 및 이를 포함하는 생물학적 고분자 합성 시스템 |
| US12399112B2 (en) | 2023-10-23 | 2025-08-26 | Protein Technologies, Inc. | On-line monitoring of synthesis reactions |
| WO2025090409A1 (en) * | 2023-10-23 | 2025-05-01 | Protein Technologies, Inc. | On-line monitoring of synthesis reactions of peptides |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093550A (en) | 1975-06-04 | 1978-06-06 | Riedel-De Haen Aktiengesellschaft | Column for high pressure liquid chromatography |
| US4192798A (en) | 1978-11-20 | 1980-03-11 | Bioresearch, Inc. | Rapid, large scale, automatable high pressure peptide synthesis |
| US4192796A (en) * | 1979-03-26 | 1980-03-11 | American Cyanamid Company | Polymers stabilized with organo-phosphorus compounds |
| WO1982003077A1 (en) | 1981-03-10 | 1982-09-16 | Inc Bioresearch | High performance peptide synthesis |
| US4598049A (en) | 1983-08-31 | 1986-07-01 | Systec Inc. | General purpose gene synthesizer |
| US4746490A (en) * | 1983-09-22 | 1988-05-24 | Saneii Hossain H | Solid phase peptide synthesizer |
| EP0156875A4 (en) * | 1983-09-22 | 1986-02-13 | Hossain H Saneii | PEPTIDE SYNTHETIZING DEVICE IN SOLID PHASE. |
| US4668476A (en) | 1984-03-23 | 1987-05-26 | Applied Biosystems, Inc. | Automated polypeptide synthesis apparatus |
| US5061635A (en) | 1987-07-13 | 1991-10-29 | City Of Hope | Protein or peptide sequencing method |
| US4861866A (en) | 1987-01-21 | 1989-08-29 | Eldex Laboratories, Inc. | Continuous flow peptide synthesizer |
| US5807525A (en) | 1995-08-17 | 1998-09-15 | Hybridon, Inc. | Apparatus and process for multi stage solid phase synthesis of long chained organic molecules |
| IL128829A (en) | 1996-09-09 | 2005-08-31 | Zealand Pharma As | Solid phase sythesis of peptides with pre-sequences |
| WO1998034633A1 (en) | 1997-02-11 | 1998-08-13 | Mallinckrodt Chemical, Inc. | Reactor and method for solid phase peptide synthesis |
| ES2329955T3 (es) | 1997-04-28 | 2009-12-02 | Novartis Vaccines And Diagnostics, Inc. | Aparato para la sintesis de oligomeros, especialmente peptoides, con reciclado de reactivos. |
| AUPP616498A0 (en) | 1998-09-25 | 1998-10-15 | University Of Queensland, The | Synthesis of cyclic peptides |
| AU2003280206A1 (en) | 2002-06-10 | 2004-02-02 | Geneprot, Inc. | Carboxy protection strategies for acidic c-terminal amino acids in chemical ligation of oligopeptides |
| US7902488B2 (en) * | 2003-06-23 | 2011-03-08 | Cem Corporation | Microwave-assisted peptide synthesis |
| US7393920B2 (en) | 2003-06-23 | 2008-07-01 | Cem Corporation | Microwave-assisted peptide synthesis |
| WO2006071470A2 (en) | 2004-12-03 | 2006-07-06 | California Institute Of Technology | Microfluidic devices with chemical reaction circuits |
| KR101014799B1 (ko) | 2008-06-05 | 2011-02-15 | 애니젠 주식회사 | 펩타이드 합성 제조 장치 |
| CN101665528A (zh) * | 2009-09-17 | 2010-03-10 | 中国药科大学 | 微波促进固相合成苦瓜mc-jj2多肽类似物及其应用 |
| US8535947B2 (en) | 2010-09-30 | 2013-09-17 | Protein Technologies, Inc. | On-line monitoring of deprotection reaction in peptide automated synthesizer comprising UV detector |
| TWI510781B (zh) | 2010-10-29 | 2015-12-01 | Scinopharm Taiwan Ltd | 即時監測固相胜肽合成反應之質譜系統 |
| US20150217254A1 (en) | 2012-09-10 | 2015-08-06 | Mohammad Boroomand | Automated peptide synthesizer |
| WO2014042591A1 (en) | 2012-09-11 | 2014-03-20 | Heptagon Micro Optics Pte. Ltd. | Manufacture of truncated lenses, of pairs of truncated lenses and of corresponding devices |
| CN102924568A (zh) * | 2012-11-20 | 2013-02-13 | 天津铭恒科技发展有限公司 | 一种合成多肽及其制备方法和用途 |
| US9169287B2 (en) | 2013-03-15 | 2015-10-27 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| US9695214B2 (en) | 2013-03-15 | 2017-07-04 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| CN108289925A (zh) | 2015-09-17 | 2018-07-17 | 麻省理工学院 | 固相肽合成方法和相关系统 |
| CN108290923A (zh) | 2015-09-17 | 2018-07-17 | 麻省理工学院 | 用于固相肽合成的方法和系统 |
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