JP2013531660A5 - - Google Patents
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- JP2013531660A5 JP2013531660A5 JP2013516766A JP2013516766A JP2013531660A5 JP 2013531660 A5 JP2013531660 A5 JP 2013531660A5 JP 2013516766 A JP2013516766 A JP 2013516766A JP 2013516766 A JP2013516766 A JP 2013516766A JP 2013531660 A5 JP2013531660 A5 JP 2013531660A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hexyl
- group
- gly
- prodrug
- 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.)
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 24
- 239000000651 prodrug Substances 0.000 claims 19
- 229940002612 prodrug Drugs 0.000 claims 19
- 239000004471 Glycine Substances 0.000 claims 12
- 229960002449 glycine Drugs 0.000 claims 12
- 108010016626 Dipeptides Proteins 0.000 claims 8
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 7
- 229940024606 amino acid Drugs 0.000 claims 7
- 235000001014 amino acid Nutrition 0.000 claims 7
- 150000001413 amino acids Chemical class 0.000 claims 7
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 5
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 4
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 4
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 4
- 239000004473 Threonine Substances 0.000 claims 4
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 4
- 235000014304 histidine Nutrition 0.000 claims 4
- 229960002898 threonine Drugs 0.000 claims 4
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 3
- 235000009582 asparagine Nutrition 0.000 claims 3
- 229960001230 asparagine Drugs 0.000 claims 3
- 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 claims 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 229960003767 alanine Drugs 0.000 claims 2
- XVOYSCVBGLVSOL-UHFFFAOYSA-N cysteic acid Chemical compound OC(=O)C(N)CS(O)(=O)=O XVOYSCVBGLVSOL-UHFFFAOYSA-N 0.000 claims 2
- 229960003104 ornithine Drugs 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 229960001153 serine Drugs 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 1
- XUJNEKJLAYXESH-UWTATZPHSA-N D-Cysteine Chemical compound SC[C@@H](N)C(O)=O XUJNEKJLAYXESH-UWTATZPHSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-RFZPGFLSSA-N D-Isoleucine Chemical compound CC[C@@H](C)[C@@H](N)C(O)=O AGPKZVBTJJNPAG-RFZPGFLSSA-N 0.000 claims 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 claims 1
- 102000004877 Insulin Human genes 0.000 claims 1
- 108090001061 Insulin Proteins 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- VBOQYPQEPHKASR-VKHMYHEASA-N L-homocysteic acid Chemical compound OC(=O)[C@@H](N)CCS(O)(=O)=O VBOQYPQEPHKASR-VKHMYHEASA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 210000004899 c-terminal region Anatomy 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229940125396 insulin Drugs 0.000 claims 1
- 239000004026 insulin derivative Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35819210P | 2010-06-24 | 2010-06-24 | |
| US61/358,192 | 2010-06-24 | ||
| PCT/US2011/041603 WO2011163462A2 (en) | 2010-06-24 | 2011-06-23 | Amide-based insulin prodrugs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013531660A JP2013531660A (ja) | 2013-08-08 |
| JP2013531660A5 true JP2013531660A5 (enExample) | 2014-08-14 |
| JP5912112B2 JP5912112B2 (ja) | 2016-04-27 |
Family
ID=45372102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013516766A Active JP5912112B2 (ja) | 2010-06-24 | 2011-06-23 | アミド系インスリンプロドラッグ |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8946147B2 (enExample) |
| EP (1) | EP2585102B1 (enExample) |
| JP (1) | JP5912112B2 (enExample) |
| CN (1) | CN103119057B (enExample) |
| AU (1) | AU2011270832B2 (enExample) |
| CA (1) | CA2803164C (enExample) |
| WO (1) | WO2011163462A2 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2249853A4 (en) | 2008-01-30 | 2012-12-26 | Univ Indiana Res & Tech Corp | ESTER BASED PEPTIDE PRODRUGS |
| WO2011159895A2 (en) | 2010-06-16 | 2011-12-22 | Indiana University Research And Technology Corporation | Single chain insulin agonists exhibiting high activity at the insulin receptor |
| US8946147B2 (en) | 2010-06-24 | 2015-02-03 | Indiana University Research And Technology Corporation | Amide-based insulin prodrugs |
| US9573987B2 (en) | 2011-12-20 | 2017-02-21 | Indiana University Research And Technology Corporation | CTP-based insulin analogs for treatment of diabetes |
| CN108383902A (zh) | 2012-09-26 | 2018-08-10 | 印第安纳大学研究及科技有限公司 | 胰岛素类似物二聚体 |
| WO2014158900A1 (en) | 2013-03-14 | 2014-10-02 | Indiana University Research And Technology Corporation | Insulin-incretin conjugates |
| EP3197912B1 (en) * | 2014-09-24 | 2023-01-04 | Indiana University Research & Technology Corporation | Lipidated amide-based insulin prodrugs |
| ES2822994T3 (es) | 2014-09-24 | 2021-05-05 | Univ Indiana Res & Tech Corp | Conjugados de incretina-insulina |
| CN107108715A (zh) | 2014-10-24 | 2017-08-29 | 默沙东公司 | 胰高血糖素和glp‑1受体的共激动剂 |
| PE20211264A1 (es) | 2017-08-17 | 2021-07-15 | Novo Nordisk As | Analogos de insulina acilados novedosos y usos de estos |
| SG11202106168VA (en) | 2018-12-11 | 2021-07-29 | Sanofi Sa | Insulin analogs having reduced insulin receptor binding affinity |
| US12263192B2 (en) | 2019-02-26 | 2025-04-01 | Pantheryx, Inc. | Compositions for management of disorders of the gastrointestinal tract |
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| US20090098130A1 (en) | 2007-01-05 | 2009-04-16 | Bradshaw Curt W | Glucagon-like protein-1 receptor (glp-1r) agonist compounds |
| JP6017754B2 (ja) | 2007-02-15 | 2016-11-02 | インディアナ ユニバーシティー リサーチ アンド テクノロジー コーポレーションIndiana University Research And Technology Corporation | グルカゴン/glp−1受容体コアゴニスト |
| CN103298935A (zh) | 2007-08-15 | 2013-09-11 | 阿穆尼克斯公司 | 用于改善生物活性多肽性能的组合物和方法 |
| EP2036923A1 (en) | 2007-09-11 | 2009-03-18 | Novo Nordisk A/S | Improved derivates of amylin |
| EP2036539A1 (en) | 2007-09-11 | 2009-03-18 | Novo Nordisk A/S | Stable formulations of amylin and its analogues |
| US8946148B2 (en) | 2007-11-20 | 2015-02-03 | Ambrx, Inc. | Modified insulin polypeptides and their uses |
| EP2249853A4 (en) * | 2008-01-30 | 2012-12-26 | Univ Indiana Res & Tech Corp | ESTER BASED PEPTIDE PRODRUGS |
| CN101980725B (zh) | 2008-02-01 | 2013-06-12 | 阿森迪斯药物股份有限公司 | 包含可自裂解的连接体的前药 |
| EP2356139A4 (en) | 2008-07-23 | 2013-01-09 | Harvard College | LIGURE COMBINED POLYPEPTIDES |
| AU2009327418A1 (en) | 2008-12-19 | 2010-06-24 | Indiana University Research And Technology Corporation | Amide based glucagon superfamily peptide prodrugs |
| CN102245624B (zh) | 2008-12-19 | 2016-08-10 | 印第安纳大学研究及科技有限公司 | 基于酰胺的胰岛素前药 |
| KR20110114568A (ko) | 2008-12-19 | 2011-10-19 | 인디애나 유니버시티 리서치 앤드 테크놀로지 코퍼레이션 | 디펩티드 링크된 약효 물질 |
| WO2010080606A1 (en) | 2008-12-19 | 2010-07-15 | Indiana University Research And Technology Corporation | Insulin analogs |
| EP2408470A4 (en) | 2009-03-20 | 2012-08-29 | Smartcells Inc | SOLUBLE NONDEPOT INSULIN CONJUGATE AND ITS USE |
| AU2010277559B2 (en) | 2009-07-31 | 2016-08-11 | Sanofi-Aventis Deutschland Gmbh | Prodrugs comprising an insulin linker conjugate |
| WO2011159895A2 (en) | 2010-06-16 | 2011-12-22 | Indiana University Research And Technology Corporation | Single chain insulin agonists exhibiting high activity at the insulin receptor |
| US8946147B2 (en) | 2010-06-24 | 2015-02-03 | Indiana University Research And Technology Corporation | Amide-based insulin prodrugs |
| EP2588126A4 (en) | 2010-06-24 | 2015-07-08 | Univ Indiana Res & Tech Corp | AMID-BASED GLUCAGON SUPERFAMILY PEPTIDE PRODRUGS |
| WO2011163460A1 (en) | 2010-06-24 | 2011-12-29 | Indiana University Research And Technology Corporation | Yl-based insulin-like growth factors exhibiting high activity at the insulin receptor |
-
2011
- 2011-06-23 US US13/702,197 patent/US8946147B2/en not_active Expired - Fee Related
- 2011-06-23 CN CN201180040875.9A patent/CN103119057B/zh not_active Expired - Fee Related
- 2011-06-23 JP JP2013516766A patent/JP5912112B2/ja active Active
- 2011-06-23 EP EP20110798912 patent/EP2585102B1/en not_active Not-in-force
- 2011-06-23 WO PCT/US2011/041603 patent/WO2011163462A2/en not_active Ceased
- 2011-06-23 AU AU2011270832A patent/AU2011270832B2/en not_active Ceased
- 2011-06-23 CA CA2803164A patent/CA2803164C/en not_active Expired - Fee Related
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