JP2012512901A5 - - Google Patents
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- JP2012512901A5 JP2012512901A5 JP2011542484A JP2011542484A JP2012512901A5 JP 2012512901 A5 JP2012512901 A5 JP 2012512901A5 JP 2011542484 A JP2011542484 A JP 2011542484A JP 2011542484 A JP2011542484 A JP 2011542484A JP 2012512901 A5 JP2012512901 A5 JP 2012512901A5
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical class 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 34
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 108010016626 Dipeptides Proteins 0.000 claims 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 235000014304 histidine Nutrition 0.000 claims 23
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 23
- 125000004429 atom Chemical group 0.000 claims 22
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 21
- 239000004026 insulin derivative Substances 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 17
- 235000001014 amino acid Nutrition 0.000 claims 17
- 150000001413 amino acids Chemical group 0.000 claims 17
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 15
- 239000004473 Threonine Substances 0.000 claims 15
- 229940024606 amino acid Drugs 0.000 claims 15
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 14
- XVOYSCVBGLVSOL-UHFFFAOYSA-N cysteic acid Chemical compound OC(=O)C(N)CS(O)(=O)=O XVOYSCVBGLVSOL-UHFFFAOYSA-N 0.000 claims 14
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 11
- 235000004279 alanine Nutrition 0.000 claims 11
- 239000004471 Glycine Substances 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 9
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 9
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 7
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 7
- VBOQYPQEPHKASR-VKHMYHEASA-N L-homocysteic acid Chemical compound OC(=O)[C@@H](N)CCS(O)(=O)=O VBOQYPQEPHKASR-VKHMYHEASA-N 0.000 claims 7
- 235000003704 aspartic acid Nutrition 0.000 claims 7
- 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 7
- 235000013922 glutamic acid Nutrition 0.000 claims 7
- 239000004220 glutamic acid Substances 0.000 claims 7
- 239000004472 Lysine Substances 0.000 claims 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 6
- 239000002202 Polyethylene glycol Substances 0.000 claims 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 229920001223 polyethylene glycol Polymers 0.000 claims 5
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
- 102000004877 Insulin Human genes 0.000 claims 4
- 108090001061 Insulin Proteins 0.000 claims 4
- 235000009582 asparagine Nutrition 0.000 claims 4
- 229960001230 asparagine Drugs 0.000 claims 4
- 229940125396 insulin Drugs 0.000 claims 4
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims 4
- 239000004475 Arginine Substances 0.000 claims 3
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 3
- 239000000539 dimer Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- AIXUQKMMBQJZCU-IUCAKERBSA-N Lys-Pro Chemical compound NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O AIXUQKMMBQJZCU-IUCAKERBSA-N 0.000 claims 2
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- OAMLVOVXNKILLQ-UHFFFAOYSA-N aspartyl-lysine Chemical compound NCCCCC(C(O)=O)NC(=O)C(N)CC(O)=O OAMLVOVXNKILLQ-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000003827 glycol group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 238000012986 modification Methods 0.000 claims 2
- 230000004048 modification Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229960002449 glycine Drugs 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 229920002521 macromolecule Polymers 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 0 CC(C(*c1ccc(*)cc1)NC)=O Chemical compound CC(C(*c1ccc(*)cc1)NC)=O 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13921808P | 2008-12-19 | 2008-12-19 | |
| US61/139,218 | 2008-12-19 | ||
| PCT/US2009/068716 WO2010080609A1 (en) | 2008-12-19 | 2009-12-18 | Amide-based insulin prodrugs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012512901A JP2012512901A (ja) | 2012-06-07 |
| JP2012512901A5 true JP2012512901A5 (enExample) | 2013-02-21 |
| JP5755566B2 JP5755566B2 (ja) | 2015-07-29 |
Family
ID=42316748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011542484A Expired - Fee Related JP5755566B2 (ja) | 2008-12-19 | 2009-12-18 | アミド系インスリンプロドラッグ |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8697632B2 (enExample) |
| EP (1) | EP2376521B1 (enExample) |
| JP (1) | JP5755566B2 (enExample) |
| CN (1) | CN102245624B (enExample) |
| AU (1) | AU2009335715B2 (enExample) |
| CA (1) | CA2744558A1 (enExample) |
| WO (1) | WO2010080609A1 (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009099763A1 (en) | 2008-01-30 | 2009-08-13 | Indiana University Research And Technology Corporation | Ester-based peptide prodrugs |
| EP2676673B1 (en) | 2008-06-17 | 2016-11-16 | Indiana University Research and Technology Corporation | Glucagon/glp-1 receptor co-agonists |
| KR20150116912A (ko) | 2008-12-15 | 2015-10-16 | 질랜드 파마 에이/에스 | 글루카곤 유사체 |
| AU2008365559B2 (en) | 2008-12-15 | 2016-02-25 | Zealand Pharma A/S | Glucagon analogues |
| MX2011006314A (es) | 2008-12-15 | 2011-09-22 | Zealand Pharma As | Analogos de glucagon. |
| BRPI0823379A2 (pt) | 2008-12-15 | 2015-07-14 | Zealand Pharma As | Análogos de glucagon |
| WO2010071807A1 (en) | 2008-12-19 | 2010-06-24 | Indiana University Research And Technology Corporation | Amide based glucagon superfamily peptide prodrugs |
| IN2012DN00377A (enExample) | 2009-06-16 | 2015-08-21 | Univ Indiana Res & Tech Corp | |
| AP3329A (en) | 2009-07-13 | 2015-06-30 | Zealand Pharma As | Acylated glucagon analogues |
| UY33462A (es) | 2010-06-23 | 2012-01-31 | Zealand Pharma As | Analogos de glucagon |
| RU2013102991A (ru) * | 2010-06-24 | 2014-08-10 | Индиана Юниверсити Рисерч Энд Текнолоджи Корпорейшн | Связанные с дипептидом лекарственные средства |
| SG186764A1 (en) | 2010-06-24 | 2013-02-28 | Zealand Pharma As | Glucagon analogues |
| WO2011163462A2 (en) | 2010-06-24 | 2011-12-29 | Indiana University Research And Technology Corporation | Amide-based insulin prodrugs |
| KR20140043709A (ko) | 2011-01-20 | 2014-04-10 | 질랜드 파마 에이/에스 | 아실화 글루카곤 유사체와 인슐린 유사체의 조합 |
| JP2014509603A (ja) * | 2011-03-15 | 2014-04-21 | ノヴォ ノルディスク アー／エス | システイン置換を含むヒトインスリン類似体およびヒトインスリン誘導体 |
| US9260503B2 (en) | 2011-06-15 | 2016-02-16 | Novo Nordisk A/S | Multi-substituted insulins |
| SI2723367T1 (sl) | 2011-06-22 | 2017-08-31 | Indiana University Research And Technology Corporation | Koagonisti receptorja glukanona/GLP-1 |
| CN104114183A (zh) | 2011-12-20 | 2014-10-22 | 印第安纳大学研究及科技有限公司 | 用于治疗糖尿病的基于ctp的胰岛素类似物 |
| TWI689515B (zh) | 2012-05-03 | 2020-04-01 | 丹麥商西蘭製藥公司 | Ｇｉｐ-ｇｌｐ-１雙重促效劑化合物及方法 |
| KR102129235B1 (ko) | 2012-07-23 | 2020-07-06 | 질랜드 파마 에이/에스 | 글루카곤 유사체 |
| TWI608013B (zh) | 2012-09-17 | 2017-12-11 | 西蘭製藥公司 | 升糖素類似物 |
| WO2014052451A2 (en) | 2012-09-26 | 2014-04-03 | Indiana University Research And Technology Corporation | Insulin analog dimers |
| CA2890048C (en) | 2012-12-03 | 2022-05-03 | Merck Sharp & Dohme Corp. | O-glycosylated carboxy terminal portion (ctp) peptide-based insulin and insulin analogues |
| US10421795B2 (en) | 2012-12-17 | 2019-09-24 | Merck Sharp & Dohme Corp. | Process for purifying insulin and analogues thereof |
| BR112015023071A2 (pt) | 2013-03-14 | 2017-07-18 | Univ Indiana Res & Tech Corp | conjugados de insulina-incretina |
| MX366852B (es) | 2013-10-04 | 2019-07-25 | Merck Sharp & Dohme | Conjugados de insulina sensibles a glucosa. |
| US9896495B2 (en) | 2013-10-17 | 2018-02-20 | Zealand Pharma A/S | Acylated glucagon analogues |
| 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 |
| WO2015067715A2 (en) | 2013-11-06 | 2015-05-14 | Zealand Pharma A/S | Gip-glp-1 dual agonist compounds and methods |
| WO2015084694A2 (en) | 2013-12-04 | 2015-06-11 | Merck Sharp & Dohme Corp. | Method for preparing crystalline insulin |
| EP3077008B1 (en) | 2013-12-06 | 2023-10-04 | Jie Han | Bioreversable promoieties for nitrogen-containing and hydroxyl-containing drugs |
| MY186251A (en) | 2014-01-20 | 2021-06-30 | Hanmi Pharm Ind Co Ltd | Long-acting insulin and use thereof |
| AR099569A1 (es) | 2014-02-28 | 2016-08-03 | Novo Nordisk As | Derivados de insulina y los usos médicos de estos |
| US10407483B2 (en) | 2014-03-14 | 2019-09-10 | Merck Sharp & Dohme Corp. | Purifying insulin using cation exchange and reverse phase chromatography in the presence of an organic modifier and elevated temperature |
| AR100639A1 (es) | 2014-05-29 | 2016-10-19 | Hanmi Pharm Ind Co Ltd | Composición para tratar diabetes que comprende conjugados de análogos de insulina de acción prolongada y conjugados de péptidos insulinotrópicos de acción prolongada |
| AR100695A1 (es) | 2014-05-30 | 2016-10-26 | Hanmi Pharm Ind Co Ltd | Composición para el tratamiento de diabetes mellitus que comprende insulina y un agonista dual glp-1 / glucagón |
| EP3171888B1 (en) | 2014-07-21 | 2022-12-28 | Merck Sharp & Dohme LLC | Chromatography process for purification of inlsulin and insulin analogs |
| CN108271356A (zh) * | 2014-09-24 | 2018-07-10 | 印第安纳大学研究及科技有限公司 | 肠降血糖素-胰岛素缀合物 |
| ES2947409T3 (es) * | 2014-09-24 | 2023-08-08 | Univ Indiana Res & Tech Corp | Profármacos de insulina a base de amida lipídica |
| EP3212218B1 (en) | 2014-10-29 | 2021-06-30 | Zealand Pharma A/S | Gip agonist compounds and methods |
| CR20170208A (es) | 2014-11-21 | 2017-07-17 | Merck Sharp & Dohme | Agonistas parciales del receptor de insulina |
| US10562951B2 (en) | 2015-03-10 | 2020-02-18 | Merck Sharp & Dohme Corp. | Process for preparing recombinant insulin using microfiltration |
| TWI707867B (zh) | 2015-04-16 | 2020-10-21 | 丹麥商西蘭製藥公司 | 醯化之昇糖素類似物 |
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| US10745457B2 (en) | 2015-09-02 | 2020-08-18 | Merck Sharp & Dohme Corp. | Process for obtaining insulin with correctly formed disulfide bonds |
| WO2017180988A2 (en) | 2016-04-15 | 2017-10-19 | Indiana University Research And Technology Corporation | Fgf21 c-terminal peptide optimization |
| EP3448417B1 (en) | 2016-04-26 | 2025-11-12 | Merck Sharp & Dohme LLC | Insulin dimer-incretin conjugates |
| WO2017205191A1 (en) | 2016-05-24 | 2017-11-30 | Merck Sharp & Dohme Corp. | Insulin receptor partial agonists and glp-1 analogues |
| EP3463413A4 (en) | 2016-05-25 | 2020-03-04 | Merck Sharp & Dohme Corp. | INSULIN RECEPTOR PART AGONISTS |
| HRP20220479T1 (hr) | 2016-06-01 | 2022-05-27 | Athira Pharma, Inc. | Spojevi |
| WO2017210168A1 (en) * | 2016-06-02 | 2017-12-07 | Indiana University Research And Technology Corporation | Aqueously soluble and chemically stable depsi glucagon agonists |
| EP3272877A1 (en) | 2016-07-18 | 2018-01-24 | ETH Zurich | B-cell-mimetic cells |
| WO2018015330A1 (en) | 2016-07-18 | 2018-01-25 | Eth Zurich | B-cell-mimetic cells |
| EP3517544B1 (en) | 2016-09-23 | 2025-01-08 | Hanmi Pharm. Co., Ltd. | Insulin analog having reduced binding force to insulin receptor, and use thereof |
| WO2018165290A1 (en) * | 2017-03-07 | 2018-09-13 | Case Western Reserve University | Single-chain insulin analogues stabilized by a fourth disulfide bridge |
| EP3604328A4 (en) | 2017-03-23 | 2021-01-06 | Hanmi Pharm. Co., Ltd. | INSULIN ANALOGUE COMPLEX WITH REDUCED AFFINITY FOR THE INSULIN RECEPTOR AND USE OF IT |
| US11041009B2 (en) | 2017-03-23 | 2021-06-22 | Merck Sharp & Dohme Corp. | Glucose responsive insulin comprising a tri-valent sugar cluster for treatment of diabetes |
| EP3624828B1 (en) | 2017-05-18 | 2024-08-07 | Merck Sharp & Dohme LLC | Pharmaceutical formulation comprising incretin-insulin conjugates |
| AU2018317810A1 (en) | 2017-08-17 | 2020-03-19 | Novo Nordisk A/S | Novel acylated insulin analogues and uses thereof |
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- 2009-12-18 CN CN200980151543.0A patent/CN102245624B/zh not_active Expired - Fee Related
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- 2009-12-18 WO PCT/US2009/068716 patent/WO2010080609A1/en not_active Ceased
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