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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- C07K1/00—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
- C07K1/04—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
Landscapes
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- Organic Chemistry (AREA)
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- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Prostheses (AREA)
- Preparation Of Compounds By Using Micro-Organisms (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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| US (1) | US7348404B2 (https=) |
| EP (1) | EP0929567B1 (https=) |
| JP (1) | JP4405594B2 (https=) |
| AT (1) | ATE290014T1 (https=) |
| AU (1) | AU723268B2 (https=) |
| CA (1) | CA2265900C (https=) |
| CZ (1) | CZ295838B6 (https=) |
| DE (1) | DE69732640T2 (https=) |
| DK (1) | DK0929567T3 (https=) |
| ES (1) | ES2239364T3 (https=) |
| HU (1) | HU230354B1 (https=) |
| IL (1) | IL128829A (https=) |
| PT (1) | PT929567E (https=) |
| WO (1) | WO1998011125A1 (https=) |
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| JP4394279B2 (ja) * | 1998-03-09 | 2010-01-06 | ジーランド ファーマ アクティーゼルスカブ | 酵素加水分解に対する傾向が減少した薬理学的に活性なペプチド複合体 |
| 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 |
| DK1737889T3 (da) | 2004-10-19 | 2011-01-03 | Lonza Ag | Fremgangsmåde til fastfase-peptidsyntese |
| DE602006020123D1 (de) | 2005-05-04 | 2011-03-31 | Zealand Pharma As | Glucagon-like-peptide-2- (glp-2-) analoga |
| 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 |
| UA96283C2 (uk) | 2005-12-23 | 2011-10-25 | Зіланд Фарма А/С | Модифіковані міметики лізину |
| KR100859972B1 (ko) | 2006-02-20 | 2008-09-25 | 이화여자대학교 산학협력단 | 막투과 단백질 도메인 펩타이드 |
| JP5328345B2 (ja) * | 2006-03-29 | 2013-10-30 | 株式会社糖鎖工学研究所 | ペプチドのチオエステル化合物の製造方法 |
| AU2007319066B2 (en) | 2006-11-08 | 2013-09-19 | Zealand Pharma A/S | Selective glucagon-like-peptide-2 (GLP-2) analogues |
| JP5385266B2 (ja) | 2007-06-15 | 2014-01-08 | ジーランド ファーマ アクティーゼルスカブ | グルカゴン類似体 |
| US8685919B2 (en) | 2008-12-15 | 2014-04-01 | Zealand Pharma A/S | Glucagon analogues |
| WO2010070255A1 (en) | 2008-12-15 | 2010-06-24 | Zealand Pharma A/S | Glucagon analogues |
| KR20110126592A (ko) | 2008-12-15 | 2011-11-23 | 질랜드 파마 에이/에스 | 글루카곤 유사체 |
| JP5635531B2 (ja) | 2008-12-15 | 2014-12-03 | ジーランド ファーマ アクティーゼルスカブ | グルカゴン類似体 |
| AP3329A (en) | 2009-07-13 | 2015-06-30 | Zealand Pharma As | Acylated glucagon analogues |
| EA023925B1 (ru) | 2010-04-27 | 2016-07-29 | Зилэнд Фарма А/С | Пептидные конъюгаты агонистов рецептора glp-1 и их применение |
| UY33462A (es) | 2010-06-23 | 2012-01-31 | Zealand Pharma As | Analogos de glucagon |
| PH12012502472A1 (en) | 2010-06-24 | 2013-03-25 | Zealand Pharma As | Glucagon analogues |
| KR20140043709A (ko) | 2011-01-20 | 2014-04-10 | 질랜드 파마 에이/에스 | 아실화 글루카곤 유사체와 인슐린 유사체의 조합 |
| MX2014005351A (es) | 2011-11-03 | 2014-05-28 | Zealand Pharma As | Conjugados de gastrina peptidicos de agonistas de receptor glp-1. |
| WO2013092703A2 (en) | 2011-12-23 | 2013-06-27 | Zealand Pharma A/S | Glucagon analogues |
| WO2013098408A1 (en) | 2011-12-30 | 2013-07-04 | Zealand Pharma A/S | Glucagon and cck receptor agonist peptide conjugates |
| TW201336864A (zh) | 2012-02-03 | 2013-09-16 | Zealand Pharma As | 胃飢餓素（ｇｈｒｅｌｉｎ）類似物 |
| JP6228187B2 (ja) | 2012-05-03 | 2017-11-08 | ジーランド ファーマ アクティーゼルスカブ | Ｇｉｐ−ｇｌｐ−１デュアルアゴニスト化合物及び方法 |
| AU2013255752B2 (en) | 2012-05-03 | 2017-11-09 | Zealand Pharma A/S | Glucagon-like-peptide-2 (GLP-2) analogues |
| AU2013295035B2 (en) | 2012-07-23 | 2017-08-03 | Zealand Pharma A/S | Glucagon analogues |
| TWI608013B (zh) | 2012-09-17 | 2017-12-11 | 西蘭製藥公司 | 升糖素類似物 |
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| US9695214B2 (en) | 2013-03-15 | 2017-07-04 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| US9169287B2 (en) | 2013-03-15 | 2015-10-27 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
| WO2014147129A1 (en) | 2013-03-21 | 2014-09-25 | Sanofi-Aventis Deutschland Gmbh | Synthesis of cyclic imide containing peptide products |
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| US9988429B2 (en) | 2013-10-17 | 2018-06-05 | Zealand Pharma A/S | Glucagon analogues |
| WO2015055801A1 (en) | 2013-10-17 | 2015-04-23 | Zealand Pharma A/S | Acylated glucagon analogues |
| MX2016005556A (es) | 2013-11-06 | 2016-07-15 | Zealand Pharma As | Compuestos agonistas duales de gip-glp-1 y procedimientos. |
| AU2014345570B2 (en) | 2013-11-06 | 2019-01-24 | Zealand Pharma A/S | Glucagon-GLP-1-GIP triple agonist compounds |
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| AR103954A1 (es) | 2015-03-18 | 2017-06-14 | Zealand Pharma As | Análogos de amilina |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5116666A (https=) * | 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 |
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| CA2170030A1 (en) * | 1993-09-14 | 1995-03-23 | Robert A. Lazarus | 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 |
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1997
- 1997-09-09 CZ CZ1999803A patent/CZ295838B6/cs not_active IP Right Cessation
- 1997-09-09 DK DK97939974T patent/DK0929567T3/da active
- 1997-09-09 AT AT97939974T patent/ATE290014T1/de active
- 1997-09-09 AU AU41993/97A patent/AU723268B2/en not_active Ceased
- 1997-09-09 EP EP97939974A patent/EP0929567B1/en not_active Expired - Lifetime
- 1997-09-09 PT PT97939974T patent/PT929567E/pt unknown
- 1997-09-09 DE DE69732640T patent/DE69732640T2/de not_active Expired - Lifetime
- 1997-09-09 ES ES97939974T patent/ES2239364T3/es not_active Expired - Lifetime
- 1997-09-09 IL IL12882997A patent/IL128829A/xx not_active IP Right Cessation
- 1997-09-09 CA CA002265900A patent/CA2265900C/en not_active Expired - Lifetime
- 1997-09-09 HU HU0102900A patent/HU230354B1/hu not_active IP Right Cessation
- 1997-09-09 JP JP51316698A patent/JP4405594B2/ja not_active Expired - Fee Related
- 1997-09-09 WO PCT/DK1997/000375 patent/WO1998011125A1/en not_active Ceased
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2006
- 2006-06-19 US US11/455,388 patent/US7348404B2/en not_active Expired - Fee Related
Also Published As
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| DE69732640T2 (de) | 2006-01-12 |
| AU723268B2 (en) | 2000-08-24 |
| JP2001500134A (ja) | 2001-01-09 |
| JP4405594B2 (ja) | 2010-01-27 |
| WO1998011125A1 (en) | 1998-03-19 |
| ATE290014T1 (de) | 2005-03-15 |
| US20070004905A1 (en) | 2007-01-04 |
| EP0929567B1 (en) | 2005-03-02 |
| ES2239364T3 (es) | 2005-09-16 |
| CZ295838B6 (cs) | 2005-11-16 |
| PT929567E (pt) | 2005-07-29 |
| HUP0102900A3 (en) | 2002-02-28 |
| DE69732640D1 (de) | 2005-04-07 |
| IL128829A0 (en) | 2000-01-31 |
| CA2265900A1 (en) | 1998-03-19 |
| IL128829A (en) | 2005-08-31 |
| US7348404B2 (en) | 2008-03-25 |
| DK0929567T3 (da) | 2005-06-27 |
| HU230354B1 (hu) | 2016-02-29 |
| CZ80399A3 (cs) | 1999-08-11 |
| AU4199397A (en) | 1998-04-02 |
| EP0929567A1 (en) | 1999-07-21 |
| HUP0102900A2 (hu) | 2002-01-28 |
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