JP6763948B2 - 固相ペプチド合成における改良 - Google Patents

固相ペプチド合成における改良 Download PDF

Info

Publication number
JP6763948B2
JP6763948B2 JP2018521074A JP2018521074A JP6763948B2 JP 6763948 B2 JP6763948 B2 JP 6763948B2 JP 2018521074 A JP2018521074 A JP 2018521074A JP 2018521074 A JP2018521074 A JP 2018521074A JP 6763948 B2 JP6763948 B2 JP 6763948B2
Authority
JP
Japan
Prior art keywords
coupling
deprotection
volume
solution
reaction vessel
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.)
Active
Application number
JP2018521074A
Other languages
English (en)
Japanese (ja)
Other versions
JP2018533572A (ja
JP2018533572A5 (https=
Inventor
コリンズ，ジョナサン・エム
Original Assignee
シーイーエム・コーポレーション
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by シーイーエム・コーポレーション filed Critical シーイーエム・コーポレーション
Publication of JP2018533572A publication Critical patent/JP2018533572A/ja
Publication of JP2018533572A5 publication Critical patent/JP2018533572A5/ja
Application granted granted Critical
Publication of JP6763948B2 publication Critical patent/JP6763948B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07K1/045—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
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
    • B01J19/122—Incoherent waves
    • B01J19/126—Microwaves
    • 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
    • C07K1/063—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 for alpha-amino functions
    • 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
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
    • C07K1/1075—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of amino acids or peptide residues
    • 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
    • C07K1/14—Extraction; Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/005—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/463—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from amphibians
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • C07K14/4701—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • C07K14/4701—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used
    • C07K14/4723—Cationic antimicrobial peptides, e.g. defensins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/57572—Gastrin releasing peptide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/59—Follicle-stimulating hormone [FSH]; Chorionic gonadotropins, e.g.hCG [human chorionic gonadotropin]; Luteinising hormone [LH]; Thyroid-stimulating hormone [TSH]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/605—Glucagons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/635—Parathyroid hormone, i.e. parathormone; Parathyroid hormone-related peptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/645—Secretins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/705—Receptors; Cell surface antigens; Cell surface determinants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/81—Protease inhibitors
    • C07K14/815—Protease inhibitors from leeches, e.g. hirudin, eglin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/16—Oxytocins; Vasopressins; Related peptides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N7/00—Viruses; Bacteriophages; Compositions thereof; Preparation or purification thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2204/00—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices
    • B01J2204/005—Aspects relating to feed or outlet devices; Regulating devices for feed or outlet devices the outlet side being of particular interest
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00054—Controlling or regulating the heat exchange system
    • B01J2219/00056—Controlling or regulating the heat exchange system involving measured parameters
    • B01J2219/00058—Temperature measurement
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J2219/0873—Materials to be treated
    • B01J2219/0879—Solid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J2219/12—Processes employing electromagnetic waves
    • B01J2219/1203—Incoherent waves
    • B01J2219/1206—Microwaves
    • B01J2219/1248—Features relating to the microwave cavity
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2740/00—Reverse transcribing RNA viruses
    • C12N2740/00011—Details
    • C12N2740/10011—Retroviridae
    • C12N2740/16011—Human Immunodeficiency Virus, HIV
    • C12N2740/16311—Human Immunodeficiency Virus, HIV concerning HIV regulatory proteins
    • C12N2740/16322—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Zoology (AREA)
  • Toxicology (AREA)
  • Endocrinology (AREA)
  • Analytical Chemistry (AREA)
  • Immunology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Virology (AREA)
  • Wood Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Cell Biology (AREA)
  • Reproductive Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Electromagnetism (AREA)
  • Biomedical Technology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Physics & Mathematics (AREA)
  • General Engineering & Computer Science (AREA)
  • Peptides Or Proteins (AREA)
JP2018521074A 2015-10-23 2016-10-21 固相ペプチド合成における改良 Active JP6763948B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201562245484P 2015-10-23 2015-10-23
US62/245,484 2015-10-23
US15/299,931 2016-10-21
PCT/US2016/058181 WO2017070512A1 (en) 2015-10-23 2016-10-21 Improvements in solid phase peptide synthesis
US15/299,931 US10125163B2 (en) 2015-10-23 2016-10-21 Solid phase peptide synthesis

Publications (3)

Publication Number Publication Date
JP2018533572A JP2018533572A (ja) 2018-11-15
JP2018533572A5 JP2018533572A5 (https=) 2020-07-16
JP6763948B2 true JP6763948B2 (ja) 2020-09-30

Family

ID=58558077

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2018521074A Active JP6763948B2 (ja) 2015-10-23 2016-10-21 固相ペプチド合成における改良

Country Status (4)

Country Link
US (2) US10125163B2 (https=)
JP (1) JP6763948B2 (https=)
CA (1) CA3002871C (https=)
WO (1) WO2017070512A1 (https=)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10239914B2 (en) 2015-10-23 2019-03-26 Cem Corporation In-situ solvent recycling process for solid phase peptide synthesis at elevated temperatures
US10125163B2 (en) 2015-10-23 2018-11-13 Cem Corporation Solid phase peptide synthesis
USRE49961E1 (en) 2016-10-21 2024-05-07 Cem Corporation Solid phase peptide syntheses
WO2019241903A1 (en) * 2018-06-19 2019-12-26 Shanghai Space Peptides Pharmaceutical Co., Ltd. Synthetic method of bivalirundin
CN108912208A (zh) * 2018-06-20 2018-11-30 南京肽业生物科技有限公司 一种温度可调的多肽固相合成装置
CN110642936B (zh) * 2018-06-26 2023-01-17 深圳翰宇药业股份有限公司 一种制备特立帕肽的方法
EP4144747A4 (en) 2020-06-03 2024-05-29 Chugai Seiyaku Kabushiki Kaisha EFFICIENT PEPTIDE CONDENSATION PROCESS FOR DIFFICULT SEQUENCES
CA3191819A1 (en) 2020-09-09 2022-03-17 Hazel Szeto Methods and compositions for delivery of biotin to mitochondria
CN117897392A (zh) 2021-07-16 2024-04-16 多肽实验室(Ppl)控股公司 水性固相肽合成
EP4380947A4 (en) * 2021-09-17 2025-10-01 Cem Corp SOLID PHASE PEPTIDE SYNTHESIS (SPPS) PROCESSES AND RELATED SYSTEMS
EP4551587A1 (en) * 2022-09-16 2025-05-14 CEM Corporation Peptide synthesis processes
EP4406652A1 (en) 2023-01-25 2024-07-31 Lizenzia GmbH Suction head

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4065781A (en) * 1974-06-21 1977-12-27 Westinghouse Electric Corporation Insulated-gate thin film transistor with low leakage current
US5614608A (en) * 1995-01-20 1997-03-25 Selectide Corporation Apparatus and method for multiple synthesis of organic compounds on polymer support
US6329139B1 (en) * 1995-04-25 2001-12-11 Discovery Partners International Automated sorting system for matrices with memory
US6890491B1 (en) * 1997-06-10 2005-05-10 Pharmacopeia Drug Discovery, Inc. Method and apparatus for universal fluid exchange
US6084226A (en) 1998-04-21 2000-07-04 Cem Corporation Use of continuously variable power in microwave assisted chemistry
DK1280831T3 (da) * 2000-05-12 2006-11-27 Lonza Ag Fremgangsmåde til fremstilling af polymerbundet 2-chlortritylchlorid
US20040238794A1 (en) * 2003-05-30 2004-12-02 Karandikar Prashant G. Microwave processing of composite bodies made by an infiltration route
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
WO2006026184A2 (en) * 2004-08-20 2006-03-09 Washington University Blood brain barrier permeation peptides
US8314208B2 (en) * 2006-02-10 2012-11-20 Cem Corporation Microwave enhanced N-fmoc deprotection in peptide synthesis
KR101058140B1 (ko) * 2007-05-11 2011-08-24 나그라스타 엘.엘.씨. 보안 환경에서 프로세서 실행을 제어하기 위한 장치
JP2013534247A (ja) * 2010-08-16 2013-09-02 シーイーエム・コーポレーション 水溶性固相ペプチド合成
US8906681B2 (en) * 2011-08-02 2014-12-09 The Scripps Research Institute Reliable stabilization of N-linked polypeptide native states with enhanced aromatic sequons located in polypeptide tight turns
EP2703073A1 (en) * 2012-08-31 2014-03-05 Biotage AB Apparatus and method for solid phase synthesis
US9169287B2 (en) * 2013-03-15 2015-10-27 Massachusetts Institute Of Technology Solid phase peptide synthesis processes and associated systems
WO2015028599A1 (en) 2013-08-30 2015-03-05 Biotage Ab Cleavage of synthetic peptides
US10239914B2 (en) * 2015-10-23 2019-03-26 Cem Corporation In-situ solvent recycling process for solid phase peptide synthesis at elevated temperatures
US10125163B2 (en) * 2015-10-23 2018-11-13 Cem Corporation Solid phase peptide synthesis

Also Published As

Publication number Publication date
JP2018533572A (ja) 2018-11-15
US10125163B2 (en) 2018-11-13
US20190194246A1 (en) 2019-06-27
CA3002871C (en) 2022-10-04
WO2017070512A1 (en) 2017-04-27
CA3002871A1 (en) 2017-04-27
US20170226152A1 (en) 2017-08-10

Similar Documents

Publication Publication Date Title
JP6763948B2 (ja) 固相ペプチド合成における改良
Offer et al. N α-2-Mercaptobenzylamine-assisted chemical ligation
Garsky et al. The synthesis of a prodrug of doxorubicin designed to provide reduced systemic toxicity and greater target efficacy
Hansen et al. Fmoc solid-phase peptide synthesis
Bacsa et al. Rapid solid‐phase peptide synthesis using thermal and controlled microwave irradiation
Loibl et al. Total chemical synthesis of proteins without HPLC purification
Cistrone et al. Native chemical ligation of peptides and proteins
JP2005015483A (ja) マイクロ波利用のペプチド合成
JP2018533572A5 (https=)
KR20150129011A (ko) 고체상 펩티드 합성 방법 및 연관 시스템
Brandt et al. Microwave heating for solid-phase peptide synthesis: general evaluation and application to 15-mer phosphopeptides
EP4488283A1 (en) Production method for peptide compound
Coantic et al. Microwave-assisted solid phase peptide synthesis on high loaded resins
Pedersen et al. Synthesis of peptides using tert-butyloxycarbonyl (Boc) as the α-amino protection group
Tian et al. Automated peptide synthesizers and glycoprotein synthesis
Hansen et al. Fmoc solid-phase peptide synthesis
CN111228508B (zh) 一种多靶点抗肿瘤的多肽药物偶联物及其制备方法与应用
EP3365352A1 (en) Improvements in solid phase peptide synthesis
CN109180800B (zh) 新型生长激素释放激素类似肽二聚体及其应用
Frutos et al. Chemical synthesis of 19F-labeled HIV-1 protease using Fmoc-chemistry and ChemMatrix resin
USRE49961E1 (en) Solid phase peptide syntheses
Monsó et al. Reverse thioether ligation route to multimeric peptide antigens
Spare et al. A continuous flow protocol to generate, regenerate, load, and recycle chlorotrityl functionalised resins
JPS6041697A (ja) 活性蛋白質誘導体の新規合成法
Singh et al. Ultra-Efficient Solid-Phase Peptide Synthesis

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20180629

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20180629

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20190423

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20190508

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190808

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20200127

A524 Written submission of copy of amendment under article 19 pct

Free format text: JAPANESE INTERMEDIATE CODE: A524

Effective date: 20200527

A911 Transfer to examiner for re-examination before appeal (zenchi)

Free format text: JAPANESE INTERMEDIATE CODE: A911

Effective date: 20200605

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20200812

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20200910

R150 Certificate of patent or registration of utility model

Ref document number: 6763948

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250