JP2015517478A5 - - Google Patents
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- Publication number
- JP2015517478A5 JP2015517478A5 JP2015510744A JP2015510744A JP2015517478A5 JP 2015517478 A5 JP2015517478 A5 JP 2015517478A5 JP 2015510744 A JP2015510744 A JP 2015510744A JP 2015510744 A JP2015510744 A JP 2015510744A JP 2015517478 A5 JP2015517478 A5 JP 2015517478A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- ethoxy
- hexanoyl
- acetyl
- carboxyphenoxy
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 99
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 80
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 56
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 40
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 36
- -1 4-carboxyphenoxy Chemical group 0.000 claims 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims 6
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 5
- 101800004266 Glucagon-like peptide 1(7-37) Proteins 0.000 claims 5
- GCYXWQUSHADNBF-AAEALURTSA-N preproglucagon 78-108 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 GCYXWQUSHADNBF-AAEALURTSA-N 0.000 claims 5
- 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 claims 4
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 239000013067 intermediate product Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- WLNMZODBWIWRGN-SSDOTTSWSA-N (2R)-2-amino-2-formyl-3-(1H-imidazol-5-yl)propanoic acid Chemical compound C(=O)[C@](N)(CC1=CNC=N1)C(=O)O WLNMZODBWIWRGN-SSDOTTSWSA-N 0.000 claims 1
- OQQDUMSNEFAJOO-MRVPVSSYSA-N (2r)-2-amino-2-(1h-imidazol-5-ylmethyl)-3-oxobutanoic acid Chemical compound CC(=O)[C@@](N)(C(O)=O)CC1=CN=CN1 OQQDUMSNEFAJOO-MRVPVSSYSA-N 0.000 claims 1
- HSFOBLRKJTWQRO-ZCFIWIBFSA-N (2r)-2-amino-2-hydroxy-3-(1h-imidazol-5-yl)propanoic acid Chemical compound OC(=O)[C@@](O)(N)CC1=CN=CN1 HSFOBLRKJTWQRO-ZCFIWIBFSA-N 0.000 claims 1
- UWBZDVGFOHDWHA-NRFANRHFSA-N (2s)-2-(dimethylamino)-6-(9h-fluoren-9-ylmethoxycarbonylamino)hexanoic acid Chemical compound C1=CC=C2C(COC(=O)NCCCC[C@H](N(C)C)C(O)=O)C3=CC=CC=C3C2=C1 UWBZDVGFOHDWHA-NRFANRHFSA-N 0.000 claims 1
- CNMAQBJBWQQZFZ-LURJTMIESA-N (2s)-2-(pyridin-2-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CC=N1 CNMAQBJBWQQZFZ-LURJTMIESA-N 0.000 claims 1
- WTKYBFQVZPCGAO-LURJTMIESA-N (2s)-2-(pyridin-3-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CN=C1 WTKYBFQVZPCGAO-LURJTMIESA-N 0.000 claims 1
- SAAQPSNNIOGFSQ-LURJTMIESA-N (2s)-2-(pyridin-4-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=NC=C1 SAAQPSNNIOGFSQ-LURJTMIESA-N 0.000 claims 1
- KQMBIBBJWXGSEI-ROLXFIACSA-N (2s)-2-amino-3-hydroxy-3-(1h-imidazol-5-yl)propanoic acid Chemical compound OC(=O)[C@@H](N)C(O)C1=CNC=N1 KQMBIBBJWXGSEI-ROLXFIACSA-N 0.000 claims 1
- AJFGLTPLWPTALJ-SSDOTTSWSA-N (2s)-2-azaniumyl-2-(fluoromethyl)-3-(1h-imidazol-5-yl)propanoate Chemical compound FC[C@@](N)(C(O)=O)CC1=CN=CN1 AJFGLTPLWPTALJ-SSDOTTSWSA-N 0.000 claims 1
- MSECZMWQBBVGEN-LURJTMIESA-N (2s)-2-azaniumyl-4-(1h-imidazol-5-yl)butanoate Chemical compound OC(=O)[C@@H](N)CCC1=CN=CN1 MSECZMWQBBVGEN-LURJTMIESA-N 0.000 claims 1
- UYEGXSNFZXWSDV-BYPYZUCNSA-N (2s)-3-(2-amino-1h-imidazol-5-yl)-2-azaniumylpropanoate Chemical compound OC(=O)[C@@H](N)CC1=CNC(N)=N1 UYEGXSNFZXWSDV-BYPYZUCNSA-N 0.000 claims 1
- FVTVMQPGKVHSEY-UHFFFAOYSA-N 1-AMINOCYCLOBUTANE CARBOXYLIC ACID Chemical compound OC(=O)C1(N)CCC1 FVTVMQPGKVHSEY-UHFFFAOYSA-N 0.000 claims 1
- WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical compound OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 claims 1
- IINRZEIPFQHEAP-UHFFFAOYSA-N 1-aminocycloheptane-1-carboxylic acid Chemical compound OC(=O)C1(N)CCCCCC1 IINRZEIPFQHEAP-UHFFFAOYSA-N 0.000 claims 1
- NILQLFBWTXNUOE-UHFFFAOYSA-N 1-aminocyclopentanecarboxylic acid Chemical compound OC(=O)C1(N)CCCC1 NILQLFBWTXNUOE-UHFFFAOYSA-N 0.000 claims 1
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 claims 1
- PJSQECUPWDUIBT-UHFFFAOYSA-N 1-azaniumylcyclooctane-1-carboxylate Chemical compound OC(=O)C1(N)CCCCCCC1 PJSQECUPWDUIBT-UHFFFAOYSA-N 0.000 claims 1
- HNDVDQJCIGZPNO-RXMQYKEDSA-N D-histidine Chemical compound OC(=O)[C@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-RXMQYKEDSA-N 0.000 claims 1
- 229930195721 D-histidine Natural products 0.000 claims 1
- HRRYYCWYCMJNGA-ZETCQYMHSA-N alpha-methyl-L-histidine Chemical compound OC(=O)[C@](N)(C)CC1=CN=CN1 HRRYYCWYCMJNGA-ZETCQYMHSA-N 0.000 claims 1
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims 1
- 230000003915 cell function Effects 0.000 claims 1
- ZCKYOWGFRHAZIQ-UHFFFAOYSA-N dihydrourocanic acid Chemical compound OC(=O)CCC1=CNC=N1 ZCKYOWGFRHAZIQ-UHFFFAOYSA-N 0.000 claims 1
- 230000006870 function Effects 0.000 claims 1
- 229960002885 histidine Drugs 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12167093 | 2012-05-08 | ||
| EP12167093.9 | 2012-05-08 | ||
| US201261646469P | 2012-05-14 | 2012-05-14 | |
| US61/646,469 | 2012-05-14 | ||
| PCT/EP2013/059113 WO2013167455A1 (en) | 2012-05-08 | 2013-05-02 | Double-acylated glp-1 derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015517478A JP2015517478A (ja) | 2015-06-22 |
| JP2015517478A5 true JP2015517478A5 (enExample) | 2016-06-09 |
| JP6366575B2 JP6366575B2 (ja) | 2018-08-01 |
Family
ID=49550173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015510744A Active JP6366575B2 (ja) | 2012-05-08 | 2013-05-02 | 二重アシル化されたｇｌｐ−１誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11274135B2 (enExample) |
| EP (1) | EP2846824B1 (enExample) |
| JP (1) | JP6366575B2 (enExample) |
| CN (1) | CN104411322B (enExample) |
| ES (1) | ES2629735T3 (enExample) |
| WO (1) | WO2013167455A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6126097B2 (ja) | 2011-09-06 | 2017-05-10 | ノヴォ ノルディスク アー／エス | Ｇｌｐ−１誘導体 |
| JP6250034B2 (ja) | 2012-05-08 | 2017-12-20 | ノヴォ ノルディスク アー／エス | 二重アシル化されたｇｌｐ−１誘導体 |
| ES2741507T3 (es) * | 2014-04-07 | 2020-02-11 | Novo Nordisk As | Compuestos de glp-1 acilados doblemente |
| MA46780A (fr) * | 2016-11-07 | 2019-09-11 | Novo Nordisk As | Esters à dchbs actif de composés peg et leur utilisation |
| CN109248323B (zh) * | 2017-07-14 | 2023-09-08 | 杭州先为达生物科技有限公司 | 酰化的glp-1衍生物 |
| TWI847306B (zh) | 2017-08-24 | 2024-07-01 | 丹麥商諾佛 儂迪克股份有限公司 | Ｇｌｐ-１組成物及其用途 |
| ES2980707T3 (es) | 2018-04-05 | 2024-10-02 | Sun Pharmaceutical Ind Ltd | Nuevos análogos de GLP-1 |
| WO2019200594A1 (zh) | 2018-04-19 | 2019-10-24 | 杭州先为达生物科技有限公司 | 酰化的glp-1衍生物 |
| WO2021136223A1 (en) | 2019-12-31 | 2021-07-08 | Beijing Ql Biopharmaceutical Co., Ltd. | Fusion proteins of glp-1 and gdf15 and conjugates thereof |
| BR112022013795A2 (pt) | 2020-02-18 | 2022-09-13 | Novo Nordisk As | Composição farmacêutica líquida, e, kit |
| JP2023545684A (ja) * | 2020-09-30 | 2023-10-31 | ベイジン キューエル バイオファーマシューティカル カンパニー，リミテッド | ポリペプチドコンジュゲートおよび使用の方法 |
| EP4323413A4 (en) | 2022-03-30 | 2025-10-15 | Beijing Ql Biopharmaceutical Co Ltd | LIQUID PHARMACEUTICAL COMPOSITIONS OF POLYPEPTIDE CONJUGATES AND METHODS OF USE THEREOF |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5336782A (en) | 1991-04-24 | 1994-08-09 | Kuraray Co., Ltd. | Long chain carboxylic acid imide ester |
| US6268343B1 (en) | 1996-08-30 | 2001-07-31 | Novo Nordisk A/S | Derivatives of GLP-1 analogs |
| IL128332A0 (en) * | 1996-08-30 | 2000-01-31 | Novo Nordisk As | GLP-1 derivatives |
| WO1999043706A1 (en) | 1998-02-27 | 1999-09-02 | Novo Nordisk A/S | Derivatives of glp-1 analogs |
| US6589503B1 (en) | 1998-06-20 | 2003-07-08 | Washington University | Membrane-permeant peptide complexes for medical imaging, diagnostics, and pharmaceutical therapy |
| EP1100530B1 (en) | 1998-07-31 | 2003-10-08 | Novo Nordisk A/S | In-vitro stimulation of beta cell proliferation |
| US20040121941A1 (en) * | 1999-09-28 | 2004-06-24 | Burm Brigitte Elisa Anna | Novel inhibitors of prenylated pyrophosphate consuming enzymes |
| AU2353701A (en) | 2000-01-11 | 2001-07-24 | Novo Nordisk A/S | Transepithelial delivery of glp-1 derivatives |
| US7595172B2 (en) * | 2001-07-24 | 2009-09-29 | Novo Nordisk A/S | Method for making acylated polypeptides |
| CA2539253A1 (en) * | 2003-09-19 | 2005-03-31 | Novo Nordisk A/S | Albumin-binding derivatives of therapeutic peptides |
| BRPI0417684A (pt) * | 2003-12-18 | 2007-03-20 | Novo Nordisk As | composto, composição farmacêutica, e, uso de um composto |
| AU2004298424A1 (en) | 2003-12-18 | 2005-06-30 | Novo Nordisk A/S | Novel GLP-1 compounds |
| ES2575984T3 (es) | 2004-11-12 | 2016-07-04 | Novo Nordisk A/S | Formulaciones estables de péptidos que contienen un análogo de GLP-1 acilado y una insulina basal |
| EP2256130B1 (en) | 2005-02-02 | 2013-09-25 | Novo Nordisk A/S | Novel insulin derivatives |
| TWI372629B (en) * | 2005-03-18 | 2012-09-21 | Novo Nordisk As | Acylated glp-1 compounds |
| BRPI0608516A2 (pt) * | 2005-03-18 | 2010-11-16 | Novo Nordisk As | análogo de glp-1, método para aumentar o tempo de ação em um paciente de um análogo de glp-1, composição farmacêutica, e, uso de um composto |
| EP2164466A1 (en) | 2007-06-01 | 2010-03-24 | Novo Nordisk A/S | Spontaneously dispersible preconcentrates including a peptide drug in a solid or semisolid carrier |
| ES2672770T3 (es) | 2007-09-05 | 2018-06-18 | Novo Nordisk A/S | Derivados del péptido-1 similar al glucagón y su uso farmacéutico |
| US20100317057A1 (en) | 2007-12-28 | 2010-12-16 | Novo Nordisk A/S | Semi-recombinant preparation of glp-1 analogues |
| MX2011000847A (es) * | 2008-08-06 | 2011-02-25 | Novo Nordisk Healthcare Ag | Proteinas conjugadas con eficacia prolongada in vivo. |
| CN104327182B (zh) * | 2009-12-16 | 2020-04-17 | 诺沃—诺迪斯克有限公司 | 双酰化glp-1衍生物 |
| CN105601729A (zh) * | 2010-11-09 | 2016-05-25 | 诺沃—诺迪斯克有限公司 | 双-酰化的glp-1衍生物 |
| JP6126097B2 (ja) | 2011-09-06 | 2017-05-10 | ノヴォ ノルディスク アー／エス | Ｇｌｐ−１誘導体 |
| JP6250034B2 (ja) * | 2012-05-08 | 2017-12-20 | ノヴォ ノルディスク アー／エス | 二重アシル化されたｇｌｐ−１誘導体 |
-
2013
- 2013-05-02 JP JP2015510744A patent/JP6366575B2/ja active Active
- 2013-05-02 WO PCT/EP2013/059113 patent/WO2013167455A1/en not_active Ceased
- 2013-05-02 ES ES13723444.9T patent/ES2629735T3/es active Active
- 2013-05-02 EP EP13723444.9A patent/EP2846824B1/en active Active
- 2013-05-02 US US14/399,086 patent/US11274135B2/en active Active
- 2013-05-02 CN CN201380024284.1A patent/CN104411322B/zh active Active