JP2009542235A5 - - Google Patents
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- Publication number
- JP2009542235A5 JP2009542235A5 JP2009518756A JP2009518756A JP2009542235A5 JP 2009542235 A5 JP2009542235 A5 JP 2009542235A5 JP 2009518756 A JP2009518756 A JP 2009518756A JP 2009518756 A JP2009518756 A JP 2009518756A JP 2009542235 A5 JP2009542235 A5 JP 2009542235A5
- Authority
- JP
- Japan
- Prior art keywords
- insulin
- arg
- gly
- lys
- trypsin
- 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
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 21
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 17
- 229940125396 insulin Drugs 0.000 description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 7
- 102000004877 Insulin Human genes 0.000 description 7
- 108090001061 Insulin Proteins 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 101000976075 Homo sapiens Insulin Proteins 0.000 description 6
- PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 6
- ULEBESPCVWBNIF-BYPYZUCNSA-N L-arginine amide Chemical compound NC(=O)[C@@H](N)CCCNC(N)=N ULEBESPCVWBNIF-BYPYZUCNSA-N 0.000 description 4
- 102000004142 Trypsin Human genes 0.000 description 4
- 108090000631 Trypsin Proteins 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007974 sodium acetate buffer Substances 0.000 description 4
- 239000012588 trypsin Substances 0.000 description 4
- 101710162629 Trypsin inhibitor Proteins 0.000 description 3
- 229940122618 Trypsin inhibitor Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000002753 trypsin inhibitor Substances 0.000 description 3
- 239000004026 insulin derivative Substances 0.000 description 2
- 102000007625 Hirudins Human genes 0.000 description 1
- 108010007267 Hirudins Proteins 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 1
- 229940006607 hirudin Drugs 0.000 description 1
- 235000014304 histidine Nutrition 0.000 description 1
- 150000002411 histidines Chemical class 0.000 description 1
- 229940124280 l-arginine Drugs 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006031955.9 | 2006-07-11 | ||
| DE102006031955A DE102006031955A1 (de) | 2006-07-11 | 2006-07-11 | Verfahren zur Herstellung von Insulinanaloga mit dibasischem B-Kettenende |
| PCT/EP2007/005933 WO2008006497A1 (de) | 2006-07-11 | 2007-07-05 | Verfahren zur herstellung von insulinanaloga mit dibasischem b-kettenende |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009542235A JP2009542235A (ja) | 2009-12-03 |
| JP2009542235A5 true JP2009542235A5 (enExample) | 2010-08-12 |
| JP5331685B2 JP5331685B2 (ja) | 2013-10-30 |
Family
ID=38468893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009518756A Expired - Fee Related JP5331685B2 (ja) | 2006-07-11 | 2007-07-05 | 二塩基性ｂ鎖末端を有するインスリン類似体の生産方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8410048B2 (enExample) |
| EP (1) | EP2041170B1 (enExample) |
| JP (1) | JP5331685B2 (enExample) |
| KR (1) | KR101439110B1 (enExample) |
| CN (1) | CN101490082B (enExample) |
| AR (1) | AR061865A1 (enExample) |
| AU (1) | AU2007272057B2 (enExample) |
| BR (1) | BRPI0714297A2 (enExample) |
| CA (1) | CA2657041C (enExample) |
| DE (1) | DE102006031955A1 (enExample) |
| DK (1) | DK2041170T3 (enExample) |
| ES (1) | ES2423684T3 (enExample) |
| IL (1) | IL196360A (enExample) |
| MX (1) | MX2009000275A (enExample) |
| MY (1) | MY148984A (enExample) |
| NO (1) | NO20090663L (enExample) |
| PT (1) | PT2041170E (enExample) |
| TW (1) | TWI440717B (enExample) |
| WO (1) | WO2008006497A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005046113A1 (de) * | 2005-09-27 | 2007-03-29 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Amidierung von Polypetiden mit C-terminalen basischen Aminosäuren unter Verwendung spezifischer Endoproteasen |
| CA2705821A1 (en) | 2007-11-16 | 2009-05-22 | Novo Nordisk A/S | Pharmaceutical compositions containing insulin and an insulinotropic peptide |
| MY161892A (en) * | 2008-02-19 | 2017-05-15 | Biocon Ltd | A method of obtaining a purified, biologically active heterologous protein |
| WO2012015692A2 (en) * | 2010-07-28 | 2012-02-02 | Smartcells, Inc. | Recombinantly expressed insulin polypeptides and uses thereof |
| WO2013015697A1 (en) | 2011-07-28 | 2013-01-31 | Mabion S.A. | A recombinant protein, a polynucleotide encoding it as well as a method of obtaining insulin or its an analogue |
| CN102504022A (zh) * | 2011-11-30 | 2012-06-20 | 苏州元基生物技术有限公司 | 含有保护赖氨酸的胰岛素原及使用其制备胰岛素的方法 |
| PL233560B1 (pl) | 2014-12-05 | 2019-10-31 | Mabion Spolka Akcyjna | Sposób otrzymywania insuliny lub analogu insuliny z prekursora rekombinowanego białka |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55138393A (en) * | 1979-04-13 | 1980-10-29 | Shionogi & Co Ltd | Semisynthesis of insulin |
| DE3326473A1 (de) | 1983-07-22 | 1985-01-31 | Hoechst Ag, 6230 Frankfurt | Pharmazeutisches mittel zur behandlung des diabetes mellitus |
| DE3333640A1 (de) * | 1983-09-17 | 1985-04-25 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von insulin-derivaten, deren b-kette c-terminal verlaengert ist, neue basisch modifizierte insulin-derivate diese enthaltende mittel und ihre verwendung |
| DK113585D0 (da) * | 1985-03-12 | 1985-03-12 | Novo Industri As | Nye peptider |
| DK347086D0 (da) * | 1986-07-21 | 1986-07-21 | Novo Industri As | Novel peptides |
| PH25772A (en) * | 1985-08-30 | 1991-10-18 | Novo Industri As | Insulin analogues, process for their preparation |
| DE3636903A1 (de) | 1985-12-21 | 1987-07-02 | Hoechst Ag | Fusionsproteine mit eukaryotischem ballastanteil |
| GB8618152D0 (en) * | 1986-07-25 | 1986-09-03 | Renishaw Plc | Co-ordinate measuring |
| EP0294851A3 (de) * | 1987-06-12 | 1990-05-09 | Berlin-Chemie Ag | Verfahren zur Herstellung von Humaninsulin und seinen Derivaten |
| US6875589B1 (en) * | 1988-06-23 | 2005-04-05 | Hoechst Aktiengesellschaft | Mini-proinsulin, its preparation and use |
| DE3837825A1 (de) * | 1988-11-08 | 1990-05-10 | Hoechst Ag | Neue insulinderivate, ihre verwendung und eine sie enthaltende pharmazeutische zubereitung |
| DE3844211A1 (de) | 1988-12-29 | 1990-07-05 | Hoechst Ag | Neue insulinderivate, verfahren zu deren herstellung, ihre verwendung und eine sie enthaltende pharmazeutische zubereitung |
| US5227293A (en) | 1989-08-29 | 1993-07-13 | The General Hospital Corporation | Fusion proteins, their preparation and use |
| DE4405179A1 (de) | 1994-02-18 | 1995-08-24 | Hoechst Ag | Verfahren zur Gewinnung von Insulin mit korrekt verbundenen Cystinbrücken |
| EP1076066A1 (en) | 1999-07-12 | 2001-02-14 | Zealand Pharmaceuticals A/S | Peptides for lowering blood glucose levels |
| AR025646A1 (es) * | 2000-09-13 | 2002-12-04 | Beta Lab Sa | Cepa de levaduras metilotroficas recombinantes productoras de un precursor de insulina, construcciones de adn y metodo para obtener la cepa. |
| DE10108211A1 (de) | 2001-02-20 | 2002-08-22 | Aventis Pharma Gmbh | Verwendung von Fusionsproteinen, deren N-terminaler Anteil aus einem Hirudinderivat besteht, zur Herstellung rekombinanter Proteine über Sekretion durch Hefen |
| DE10108100A1 (de) | 2001-02-20 | 2002-08-29 | Aventis Pharma Gmbh | Verwendung supersekretierbarer Peptide in Verfahren zu deren Herstellung und paralleler Verbesserung der Exportate eines oder mehrerer anderer Polypeptide von Interesse |
| DE10108212A1 (de) | 2001-02-20 | 2002-08-22 | Aventis Pharma Gmbh | Fusionsprotein zur Sekretion von Wertprotein in bakterielle Überstände |
| IL161358A0 (en) * | 2001-11-19 | 2004-09-27 | Novo Nordisk As | Process for preparing insulin compounds |
| DE10227232A1 (de) | 2002-06-18 | 2004-01-15 | Aventis Pharma Deutschland Gmbh | Saure Insulinzubereitungen mit verbesserter Stabilität |
| ES2327328T3 (es) | 2002-07-04 | 2009-10-28 | Zealand Pharma A/S | Glp-1 y procedimientos para el tratamiento de la diabetes. |
| EP1778839B1 (en) | 2004-08-13 | 2008-07-09 | Roche Diagniostics GMBH | C-terminal modification of polypeptides |
| DE102004058306A1 (de) | 2004-12-01 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung von Carboxy-terminal amidierten Peptiden |
| DE102005046113A1 (de) * | 2005-09-27 | 2007-03-29 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Amidierung von Polypetiden mit C-terminalen basischen Aminosäuren unter Verwendung spezifischer Endoproteasen |
-
2006
- 2006-07-11 DE DE102006031955A patent/DE102006031955A1/de not_active Withdrawn
-
2007
- 2007-07-05 KR KR1020097000429A patent/KR101439110B1/ko not_active Expired - Fee Related
- 2007-07-05 ES ES07785903T patent/ES2423684T3/es active Active
- 2007-07-05 AU AU2007272057A patent/AU2007272057B2/en not_active Ceased
- 2007-07-05 DK DK07785903.1T patent/DK2041170T3/da active
- 2007-07-05 WO PCT/EP2007/005933 patent/WO2008006497A1/de not_active Ceased
- 2007-07-05 JP JP2009518756A patent/JP5331685B2/ja not_active Expired - Fee Related
- 2007-07-05 CN CN2007800261387A patent/CN101490082B/zh not_active Expired - Fee Related
- 2007-07-05 PT PT77859031T patent/PT2041170E/pt unknown
- 2007-07-05 BR BRPI0714297-8A patent/BRPI0714297A2/pt not_active IP Right Cessation
- 2007-07-05 MY MYPI20085343A patent/MY148984A/en unknown
- 2007-07-05 MX MX2009000275A patent/MX2009000275A/es active IP Right Grant
- 2007-07-05 EP EP07785903.1A patent/EP2041170B1/de not_active Not-in-force
- 2007-07-05 CA CA2657041A patent/CA2657041C/en not_active Expired - Fee Related
- 2007-07-09 TW TW096124845A patent/TWI440717B/zh not_active IP Right Cessation
- 2007-07-10 AR ARP070103059A patent/AR061865A1/es unknown
-
2009
- 2009-01-05 IL IL196360A patent/IL196360A/en not_active IP Right Cessation
- 2009-01-07 US US12/349,854 patent/US8410048B2/en not_active Expired - Fee Related
- 2009-02-11 NO NO20090663A patent/NO20090663L/no not_active Application Discontinuation
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