JP2016138090A5 - - Google Patents
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- Publication number
- JP2016138090A5 JP2016138090A5 JP2015247553A JP2015247553A JP2016138090A5 JP 2016138090 A5 JP2016138090 A5 JP 2016138090A5 JP 2015247553 A JP2015247553 A JP 2015247553A JP 2015247553 A JP2015247553 A JP 2015247553A JP 2016138090 A5 JP2016138090 A5 JP 2016138090A5
- Authority
- JP
- Japan
- Prior art keywords
- coupling
- amount
- base
- less
- temperature
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 67
- 238000010168 coupling process Methods 0.000 claims description 35
- 230000008878 coupling Effects 0.000 claims description 33
- 238000005859 coupling reaction Methods 0.000 claims description 33
- 150000001413 amino acids Chemical class 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 150000001718 carbodiimides Chemical class 0.000 claims description 12
- 230000003213 activating effect Effects 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 claims description 11
- 230000004913 activation Effects 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- -1 NHS Substances 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 6
- 239000003930 superacid Substances 0.000 claims description 5
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims description 4
- TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 claims description 4
- KPFBUSLHFFWMAI-HYRPPVSQSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-6-formyl-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1C[C@@H]2[C@](CCC(OC)=C3)(C)C3=C(C=O)C[C@H]2[C@@H]2CC[C@](OC(C)=O)(C(C)=O)[C@]21C KPFBUSLHFFWMAI-HYRPPVSQSA-N 0.000 claims description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 3
- 238000010647 peptide synthesis reaction Methods 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000010532 solid phase synthesis reaction Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462094420P | 2014-12-19 | 2014-12-19 | |
| US62/094,420 | 2014-12-19 | ||
| US201562111817P | 2015-02-04 | 2015-02-04 | |
| US62/111,817 | 2015-02-04 | ||
| US201562132847P | 2015-03-13 | 2015-03-13 | |
| US62/132,847 | 2015-03-13 | ||
| US14/969,004 US10308677B2 (en) | 2014-12-19 | 2015-12-15 | Coupling method for peptide synthesis at elevated temperatures |
| US14/969,004 | 2015-12-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016138090A JP2016138090A (ja) | 2016-08-04 |
| JP2016138090A5 true JP2016138090A5 (enExample) | 2017-02-02 |
| JP6348102B2 JP6348102B2 (ja) | 2018-06-27 |
Family
ID=55310608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015247553A Active JP6348102B2 (ja) | 2014-12-19 | 2015-12-18 | 高温でのペプチド合成のための改良されたカップリング法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10308677B2 (enExample) |
| EP (1) | EP3037430B1 (enExample) |
| JP (1) | JP6348102B2 (enExample) |
| CN (1) | CN105713066A (enExample) |
| AU (2) | AU2015271886B2 (enExample) |
| CA (1) | CA2915484C (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE034308T2 (en) | 2013-03-21 | 2018-02-28 | Sanofi Aventis Deutschland | Preparation of hydantoin-containing peptide products |
| CN105102427B (zh) | 2013-03-21 | 2018-09-07 | 赛诺菲-安万特德国有限公司 | 含有环状酰亚胺的肽产物的合成 |
| US9969769B2 (en) | 2014-12-19 | 2018-05-15 | Cem Corporation | Coupling method for peptide synthesis at elevated temperatures |
| US10858390B2 (en) * | 2016-09-02 | 2020-12-08 | Cem Corporation | Use of excess carbodiimide for peptide synthesis at elevated temperatures |
| AU2017221772B2 (en) * | 2016-09-02 | 2018-07-05 | Cem Corporation | Use of excess carbodiimide for peptide synthesis at elevated temperatures |
| CN113655133B (zh) * | 2021-06-29 | 2023-03-10 | 北京诺康达医药科技股份有限公司 | 一种检测n,n-二异丙基碳二酰亚胺的方法及应用 |
| CN114736286B (zh) * | 2021-12-27 | 2024-09-13 | 江苏诺泰澳赛诺生物制药股份有限公司 | 一种多肽杂质单硫化物的合成方法 |
| WO2023195516A1 (ja) * | 2022-04-08 | 2023-10-12 | 中外製薬株式会社 | ペプチド化合物の製造方法 |
| CN118812623A (zh) * | 2024-07-02 | 2024-10-22 | 中肽生化有限公司 | 一种alpha取代氨基酸和氮烷基类甘氨酸相连多肽序列的固相合成方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB673639A (en) | 1948-07-02 | 1952-06-11 | Ward Blenkinsop & Co Ltd | Process for the production of acyl derivatives of amino hydroxybenzene carboxylic acids |
| GB812543A (en) | 1954-12-06 | 1959-04-29 | Roussel Uclaf | Improvements in or relating to ª‡-amino acids and peptides derived therefrom |
| US4507230A (en) | 1982-05-12 | 1985-03-26 | Research Corporation | Peptide synthesis reagents and method of use |
| JPS6393796A (ja) | 1986-10-09 | 1988-04-25 | Shin Etsu Chem Co Ltd | ペプチド合成の脱保護基用薬剤 |
| EP0322348B1 (de) | 1987-12-22 | 1994-02-02 | Hoechst Aktiengesellschaft | Säurelabile Ankergruppen zur Synthese von Peptidamiden mittels Festphasenmethode |
| DE4124283A1 (de) | 1991-07-15 | 1993-01-21 | Degussa | Umesterung von peptiden |
| HUP0003921A3 (en) | 1997-07-31 | 2001-03-28 | Wyeth Corp | Sulfonylated dipeptide compounds which inhibit leukocyte adhesion mediated by vla-4, pharmaceutical compositions comprising thereof and their use |
| HUP0204281A3 (en) | 2000-01-27 | 2007-03-28 | Lilly Co Eli | Process for sulubilizing glucagon-like peptide 1 (glp-1) compounds |
| ATE339442T1 (de) | 2000-12-22 | 2006-10-15 | Ipsen Mfg Ireland Ltd | Verfahren für die synthese eines lhrh peptides |
| GB0227876D0 (en) | 2002-11-29 | 2003-01-08 | Avecia Ltd | Process and supports |
| US7393920B2 (en) * | 2003-06-23 | 2008-07-01 | Cem Corporation | Microwave-assisted peptide synthesis |
| ATE376556T1 (de) | 2003-12-31 | 2007-11-15 | Hoffmann La Roche | Verfahren zur peptidsynthese unter verwendung einer reduzierten menge an entschützungsmittel |
| DE102004053410A1 (de) | 2004-11-05 | 2006-05-11 | Bayer Healthcare Ag | Cyclische Nonadepsipeptidamide |
| EP2716650A1 (en) | 2011-05-31 | 2014-04-09 | Ajinomoto Co., Inc. | Method for producing peptide |
| US20140206841A1 (en) | 2013-01-18 | 2014-07-24 | Protein Technologies, Inc. | Peptide Synthesis Apparatus and Methods Using Infrared Energy |
-
2015
- 2015-12-15 US US14/969,004 patent/US10308677B2/en active Active
- 2015-12-17 AU AU2015271886A patent/AU2015271886B2/en active Active
- 2015-12-17 CA CA2915484A patent/CA2915484C/en active Active
- 2015-12-18 EP EP15201155.7A patent/EP3037430B1/en active Active
- 2015-12-18 CN CN201510959243.2A patent/CN105713066A/zh active Pending
- 2015-12-18 JP JP2015247553A patent/JP6348102B2/ja active Active
-
2017
- 2017-06-20 AU AU2017204172A patent/AU2017204172B2/en active Active
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