CA2265900C - Improved solid-phase peptide synthesis and agent for use in such synthesis - Google Patents
Improved solid-phase peptide synthesis and agent for use in such synthesis Download PDFInfo
- Publication number
- CA2265900C CA2265900C CA002265900A CA2265900A CA2265900C CA 2265900 C CA2265900 C CA 2265900C CA 002265900 A CA002265900 A CA 002265900A CA 2265900 A CA2265900 A CA 2265900A CA 2265900 C CA2265900 C CA 2265900C
- Authority
- CA
- Canada
- Prior art keywords
- peptide
- sequence
- acid
- amino acid
- synthesis
- 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
Links
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- 238000003786 synthesis reaction Methods 0.000 title claims description 66
- 239000007790 solid phase Substances 0.000 title abstract description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 63
- 150000001413 amino acids Chemical class 0.000 claims description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 40
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Classifications
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- C—CHEMISTRY; METALLURGY
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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
- C07K1/042—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
- C07K1/04—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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Prostheses (AREA)
Applications Claiming Priority (3)
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| DK97196 | 1996-09-09 | ||
| DK0971/96 | 1996-09-09 | ||
| PCT/DK1997/000375 WO1998011125A1 (en) | 1996-09-09 | 1997-09-09 | Improved solid-phase peptide synthesis and agent for use in such synthesis |
Publications (2)
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| CA2265900A1 CA2265900A1 (en) | 1998-03-19 |
| CA2265900C true CA2265900C (en) | 2007-07-31 |
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| CA002265900A Expired - Lifetime CA2265900C (en) | 1996-09-09 | 1997-09-09 | Improved solid-phase peptide synthesis and agent for use in such synthesis |
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| EP (1) | EP0929567B1 (enExample) |
| JP (1) | JP4405594B2 (enExample) |
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| DK (1) | DK0929567T3 (enExample) |
| ES (1) | ES2239364T3 (enExample) |
| HU (1) | HU230354B1 (enExample) |
| IL (1) | IL128829A (enExample) |
| PT (1) | PT929567E (enExample) |
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| IL138214A0 (en) * | 1998-03-09 | 2001-10-31 | Zealand Pharmaceuticals As | Pharmacolgically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
| US6528486B1 (en) | 1999-07-12 | 2003-03-04 | Zealand Pharma A/S | Peptide agonists of GLP-1 activity |
| US7550425B2 (en) | 2000-06-16 | 2009-06-23 | Zealand Pharma A/S | Diuretic peptide conjugates |
| PT1737889E (pt) | 2004-10-19 | 2010-12-13 | Lonza Ag | Método para síntese de péptidos em fase sólida |
| AU2006242998B2 (en) | 2005-05-04 | 2012-03-22 | Zealand Pharma A/S | Glucagon-like-peptide-2 (GLP-2) analogues |
| GB0514071D0 (en) | 2005-07-07 | 2005-08-17 | Zealand Pharma As | N- or C- terminally modified small peptides |
| US20090171097A1 (en) * | 2005-11-22 | 2009-07-02 | Hiroshi Sugiyama | Automated solid phase synthesis of pyrrole-imidazole polyamide |
| PT1966130E (pt) | 2005-12-23 | 2014-01-30 | Zealand Pharma As | Compostos miméticos de lisina modificados |
| EP1991560B1 (en) * | 2006-02-20 | 2018-04-04 | Ewha University-Industry Collaboration Foundation | Peptide having cell membrane penetrating activity |
| CN101437836B (zh) * | 2006-03-29 | 2013-07-24 | 株式会社糖锁工学研究所 | 肽的硫酯化合物的制造方法 |
| WO2008056155A1 (en) | 2006-11-08 | 2008-05-15 | Zealand Pharma A/S | Selective glucagon-like-peptide-2 (glp-2) analogues |
| DK2158214T3 (da) | 2007-06-15 | 2011-12-05 | Zealand Pharma As | Glukagonanaloger |
| EA020537B1 (ru) | 2008-12-15 | 2014-11-28 | Зилэнд Фарма А/С | Аналоги глюкагона |
| WO2010070255A1 (en) | 2008-12-15 | 2010-06-24 | Zealand Pharma A/S | Glucagon analogues |
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| HUE026255T2 (en) | 2009-07-13 | 2016-06-28 | Zealand Pharma As | Acylated glucagon analogues |
| US9089538B2 (en) | 2010-04-27 | 2015-07-28 | Zealand Pharma A/S | Peptide conjugates of GLP-1 receptor agonists and gastrin and their use |
| UY33462A (es) | 2010-06-23 | 2012-01-31 | Zealand Pharma As | Analogos de glucagon |
| AP2013006671A0 (en) | 2010-06-24 | 2013-01-31 | Zealand Pharma As | Glucagon analogues |
| SG192038A1 (en) | 2011-01-20 | 2013-08-30 | Zealand Pharma As | Combination of acylated glucagon analogues with insulin analogues |
| AU2012331053A1 (en) | 2011-11-03 | 2014-05-29 | Zealand Pharma A/S | GLP-1 receptor agonist peptide gastrin conjugates |
| US20130316941A1 (en) | 2011-12-23 | 2013-11-28 | Boehringer Ingelheim International Gmbh | Glucagon analogues |
| WO2013098408A1 (en) | 2011-12-30 | 2013-07-04 | Zealand Pharma A/S | Glucagon and cck receptor agonist peptide conjugates |
| AR089860A1 (es) | 2012-02-03 | 2014-09-24 | Zealand Pharma As | Analogos de la grelina |
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| EP2844669B1 (en) | 2012-05-03 | 2018-08-01 | Zealand Pharma A/S | Gip-glp-1 dual agonist compounds and methods |
| SG11201500375PA (en) | 2012-07-23 | 2015-02-27 | Zealand Pharma As | Glucagon analogues |
| TWI608013B (zh) | 2012-09-17 | 2017-12-11 | 西蘭製藥公司 | 升糖素類似物 |
| CA2902432A1 (en) | 2013-03-12 | 2014-10-09 | Molecular Templates, Inc. | Cytotoxic proteins comprising cell-targeting binding regions and shiga toxin a subunit regions for selective killing of specific cell types |
| 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 |
| EP2976331B1 (en) | 2013-03-21 | 2017-03-01 | Sanofi-Aventis Deutschland GmbH | Synthesis of hydantoin containing peptide products |
| CA2907521C (en) | 2013-03-21 | 2021-04-13 | Sanofi-Aventis Deutschland Gmbh | Synthesis of cyclic imide containing peptide products |
| CN119119235A (zh) | 2013-10-17 | 2024-12-13 | 西兰制药公司 | 酰化胰高血糖素类似物 |
| US9988429B2 (en) | 2013-10-17 | 2018-06-05 | Zealand Pharma A/S | Glucagon analogues |
| EA035688B1 (ru) | 2013-11-06 | 2020-07-27 | Зилэнд Фарма А/С | Соединения, которые представляют собой тройные агонисты глюкагона, glp-1 и gip |
| EP3065767B1 (en) | 2013-11-06 | 2020-12-30 | Zealand Pharma A/S | Gip-glp-1 dual agonist compounds and methods |
| WO2015100246A1 (en) | 2013-12-24 | 2015-07-02 | Ossianix, Inc. | Baff selective binding compounds and related methods |
| ES2877356T3 (es) | 2014-01-27 | 2021-11-16 | Molecular Templates Inc | Epítopo de MHC de clase I que suministra polipéptidos |
| JP6935195B2 (ja) | 2014-03-11 | 2021-09-15 | モレキュラー テンプレーツ, インク.Molecular Templates, Inc. | 結合領域、志賀毒素ａサブユニットのエフェクター領域、及びカルボキシ末端小胞体局在化シグナルモチーフを含むタンパク質 |
| DK3604333T3 (da) | 2014-03-11 | 2021-06-21 | Molecular Templates Inc | Proteiner omfattende amino-terminale proksimale Shiga toksin A-underenhed-effektorregioner og cellemålrettede bindingsregioner af immunglobulin-typen, der er i stand til specifikt at binde CD38 |
| AU2015274647C1 (en) | 2014-06-11 | 2020-01-30 | Molecular Templates, Inc. | Protease-cleavage resistant, Shiga toxin a subunit effector polypeptides and cell-targeted molecules comprising the same |
| US10479990B2 (en) | 2014-06-26 | 2019-11-19 | Ossianix, Inc. | Semi-synthetic nurse shark VNAR libraries for making and using selective binding compounds |
| AU2015340586B2 (en) | 2014-10-29 | 2020-04-30 | Zealand Pharma A/S | GIP agonist compounds and methods |
| WO2016077840A2 (en) | 2014-11-14 | 2016-05-19 | Ossianix, Inc. | TfR SELECTIVE BINDING COMPOUNDS AND RELATED METHODS |
| MX2017010072A (es) | 2015-02-05 | 2017-11-09 | Molecular Templates Inc | Moleculas multivalentes que se enlazan a cd20, las cuales comprenden regiones efectoras de la subunidad a de la toxina shiga, y composiciones enriquecidas de las mismas. |
| WO2016146739A1 (en) | 2015-03-18 | 2016-09-22 | Zealand Pharma A/S | Amylin analogues |
| GB201506380D0 (en) | 2015-04-15 | 2015-05-27 | Serodus Asa | Materials and methods for treatment of pulmonary hypertension |
| KR20170137198A (ko) | 2015-04-16 | 2017-12-12 | 질랜드 파마 에이/에스 | 아실화된 글루카곤 유사체 |
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| EP3325510A2 (en) | 2015-07-26 | 2018-05-30 | Molecular Templates, Inc. | Cell-targeting molecules comprising shiga toxin a subunit effectors and cd8+ t-cell epitopes |
| 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 |
| US11097010B2 (en) | 2016-08-06 | 2021-08-24 | Ossianix, Inc. | In vivo methods for selecting peptides that cross the blood brain barrier, related compositions and methods of use |
| AR109514A1 (es) | 2016-09-09 | 2018-12-19 | Zealand Pharma As | Análogos de amilina |
| KR102502040B1 (ko) | 2016-12-09 | 2023-02-24 | 질랜드 파마 에이/에스 | 아실화 glp-1/glp-2 이중 효능제 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5116666A (enExample) | 1974-07-30 | 1976-02-10 | Shionogi Seiyaku Kk | |
| US5021550A (en) * | 1986-10-07 | 1991-06-04 | Thomas Jefferson University | Method for preventing deletion sequences in solid phase synthesis |
| JP2807287B2 (ja) | 1989-10-13 | 1998-10-08 | 株式会社医学生物学研究所 | ペプチドおよびその用途 |
| EP0719334A1 (en) | 1993-09-14 | 1996-07-03 | Genentech, Inc. | Pharmaceutical compositions containing ecotin and homologs thereof |
| US7176282B1 (en) | 1996-09-09 | 2007-02-13 | Zealand Pharma A/S | Solid-phase peptide synthesis and agent for use in such synthesis |
| IL138214A0 (en) | 1998-03-09 | 2001-10-31 | Zealand Pharmaceuticals As | Pharmacolgically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
-
1997
- 1997-09-09 HU HU0102900A patent/HU230354B1/hu not_active IP Right Cessation
- 1997-09-09 CA CA002265900A patent/CA2265900C/en not_active Expired - Lifetime
- 1997-09-09 DK DK97939974T patent/DK0929567T3/da active
- 1997-09-09 EP EP97939974A patent/EP0929567B1/en not_active Expired - Lifetime
- 1997-09-09 IL IL12882997A patent/IL128829A/xx not_active IP Right Cessation
- 1997-09-09 ES ES97939974T patent/ES2239364T3/es not_active Expired - Lifetime
- 1997-09-09 DE DE69732640T patent/DE69732640T2/de not_active Expired - Lifetime
- 1997-09-09 WO PCT/DK1997/000375 patent/WO1998011125A1/en not_active Ceased
- 1997-09-09 PT PT97939974T patent/PT929567E/pt unknown
- 1997-09-09 AU AU41993/97A patent/AU723268B2/en not_active Ceased
- 1997-09-09 AT AT97939974T patent/ATE290014T1/de active
- 1997-09-09 JP JP51316698A patent/JP4405594B2/ja not_active Expired - Fee Related
- 1997-09-09 CZ CZ1999803A patent/CZ295838B6/cs not_active IP Right Cessation
-
2006
- 2006-06-19 US US11/455,388 patent/US7348404B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69732640D1 (de) | 2005-04-07 |
| HU230354B1 (hu) | 2016-02-29 |
| CA2265900A1 (en) | 1998-03-19 |
| AU723268B2 (en) | 2000-08-24 |
| ATE290014T1 (de) | 2005-03-15 |
| JP2001500134A (ja) | 2001-01-09 |
| JP4405594B2 (ja) | 2010-01-27 |
| AU4199397A (en) | 1998-04-02 |
| EP0929567A1 (en) | 1999-07-21 |
| HUP0102900A2 (hu) | 2002-01-28 |
| DK0929567T3 (da) | 2005-06-27 |
| WO1998011125A1 (en) | 1998-03-19 |
| CZ80399A3 (cs) | 1999-08-11 |
| ES2239364T3 (es) | 2005-09-16 |
| DE69732640T2 (de) | 2006-01-12 |
| US20070004905A1 (en) | 2007-01-04 |
| US7348404B2 (en) | 2008-03-25 |
| PT929567E (pt) | 2005-07-29 |
| IL128829A0 (en) | 2000-01-31 |
| EP0929567B1 (en) | 2005-03-02 |
| CZ295838B6 (cs) | 2005-11-16 |
| HUP0102900A3 (en) | 2002-02-28 |
| IL128829A (en) | 2005-08-31 |
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