ES2913803T3 - Derivados de GLP-1 diacilados - Google Patents
Derivados de GLP-1 diacilados Download PDFInfo
- Publication number
- ES2913803T3 ES2913803T3 ES11779456T ES11779456T ES2913803T3 ES 2913803 T3 ES2913803 T3 ES 2913803T3 ES 11779456 T ES11779456 T ES 11779456T ES 11779456 T ES11779456 T ES 11779456T ES 2913803 T3 ES2913803 T3 ES 2913803T3
- Authority
- ES
- Spain
- Prior art keywords
- ethoxy
- amino
- acetyl
- carboxy
- butanoyl
- 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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Links
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical class 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 title claims abstract description 83
- 229940024606 amino acid Drugs 0.000 claims abstract description 61
- 150000001413 amino acids Chemical class 0.000 claims abstract description 55
- -1 imidazopropionyl Chemical compound 0.000 claims abstract description 54
- 125000005647 linker group Chemical group 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 101800004266 Glucagon-like peptide 1(7-37) Proteins 0.000 claims abstract description 26
- 150000001408 amides Chemical class 0.000 claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 24
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- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims abstract description 10
- ZCKYOWGFRHAZIQ-UHFFFAOYSA-N dihydrourocanic acid Chemical compound OC(=O)CCC1=CNC=N1 ZCKYOWGFRHAZIQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 3
- 229960002885 histidine Drugs 0.000 claims abstract 3
- 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 abstract 2
- 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 abstract 2
- 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 abstract 2
- 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 abstract 2
- 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 abstract 2
- FVTVMQPGKVHSEY-UHFFFAOYSA-N 1-AMINOCYCLOBUTANE CARBOXYLIC ACID Chemical compound OC(=O)C1(N)CCC1 FVTVMQPGKVHSEY-UHFFFAOYSA-N 0.000 claims abstract 2
- IINRZEIPFQHEAP-UHFFFAOYSA-N 1-aminocycloheptane-1-carboxylic acid Chemical compound OC(=O)C1(N)CCCCCC1 IINRZEIPFQHEAP-UHFFFAOYSA-N 0.000 claims abstract 2
- NILQLFBWTXNUOE-UHFFFAOYSA-N 1-aminocyclopentanecarboxylic acid Chemical compound OC(=O)C1(N)CCCC1 NILQLFBWTXNUOE-UHFFFAOYSA-N 0.000 claims abstract 2
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 claims abstract 2
- PJSQECUPWDUIBT-UHFFFAOYSA-N 1-azaniumylcyclooctane-1-carboxylate Chemical compound OC(=O)C1(N)CCCCCCC1 PJSQECUPWDUIBT-UHFFFAOYSA-N 0.000 claims abstract 2
- HNDVDQJCIGZPNO-RXMQYKEDSA-N D-histidine Chemical compound OC(=O)[C@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-RXMQYKEDSA-N 0.000 claims abstract 2
- 229930195721 D-histidine Natural products 0.000 claims abstract 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2202
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 1142
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 520
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 83
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 53
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- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 597
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 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 abstract 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 abstract 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 abstract 1
- HRRYYCWYCMJNGA-ZETCQYMHSA-N alpha-methyl-L-histidine Chemical compound OC(=O)[C@](N)(C)CC1=CN=CN1 HRRYYCWYCMJNGA-ZETCQYMHSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 383
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 376
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 290
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 102
- 235000001014 amino acid Nutrition 0.000 description 55
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 45
- 102000009027 Albumins Human genes 0.000 description 38
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- 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 37
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
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- 239000000203 mixture Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- 102400000322 Glucagon-like peptide 1 Human genes 0.000 description 29
- 235000018977 lysine Nutrition 0.000 description 28
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- 229910052739 hydrogen Inorganic materials 0.000 description 23
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- 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 description 20
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 19
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 16
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- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 14
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- 108010086246 Glucagon-Like Peptide-1 Receptor Proteins 0.000 description 13
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- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 13
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Child & Adolescent Psychology (AREA)
- Cardiology (AREA)
- Nutrition Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10190515 | 2010-11-09 | ||
| US41422110P | 2010-11-16 | 2010-11-16 | |
| EP11169276 | 2011-06-09 | ||
| US201161497123P | 2011-06-15 | 2011-06-15 | |
| PCT/EP2011/069738 WO2012062803A1 (en) | 2010-11-09 | 2011-11-09 | Double-acylated glp-1 derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2913803T3 true ES2913803T3 (es) | 2022-06-06 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11779456T Active ES2913803T3 (es) | 2010-11-09 | 2011-11-09 | Derivados de GLP-1 diacilados |
| ES11779674T Active ES2683372T3 (es) | 2010-11-09 | 2011-11-09 | Derivados de GLP-1 acilados con un conector nuevo |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11779674T Active ES2683372T3 (es) | 2010-11-09 | 2011-11-09 | Derivados de GLP-1 acilados con un conector nuevo |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US9006178B2 (OSRAM) |
| EP (2) | EP2637698B1 (OSRAM) |
| JP (3) | JP6231386B2 (OSRAM) |
| CN (3) | CN103209711B (OSRAM) |
| ES (2) | ES2913803T3 (OSRAM) |
| WO (2) | WO2012062804A1 (OSRAM) |
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| JP6054742B2 (ja) | 2009-07-13 | 2016-12-27 | ジーランド ファーマ アクティーゼルスカブ | アシル化グルカゴン類似体 |
| JP6231386B2 (ja) * | 2010-11-09 | 2017-11-15 | ノヴォ ノルディスク アー／エス | リンカーを有する二重アシル化されたｇｌｐ−１誘導体 |
| CN104039822A (zh) | 2011-09-06 | 2014-09-10 | 诺沃—诺迪斯克有限公司 | Glp-1衍生物 |
| JP6228187B2 (ja) | 2012-05-03 | 2017-11-08 | ジーランド ファーマ アクティーゼルスカブ | Ｇｉｐ−ｇｌｐ−１デュアルアゴニスト化合物及び方法 |
| 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 |
| EP2846824B1 (en) * | 2012-05-08 | 2017-04-05 | Novo Nordisk A/S | Double-acylated glp-1 derivatives |
| MX356957B (es) | 2012-07-23 | 2018-06-20 | Zealand Pharma As | Analogos del glucagon. |
| TWI608013B (zh) | 2012-09-17 | 2017-12-11 | 西蘭製藥公司 | 升糖素類似物 |
| WO2014199397A2 (en) * | 2013-06-11 | 2014-12-18 | Mylan Laboratories Ltd | Process for the preparation of liraglutide |
| MX2015016564A (es) | 2013-06-20 | 2016-04-15 | Novo Nordisk As | Derivados de peptido similar al glucaton tipo 1 (glp-1) y uso de los mismos. |
| KR20160029079A (ko) | 2013-07-04 | 2016-03-14 | 노보 노르디스크 에이/에스 | Glp-1 유사 펩티드의 유도체 및 그것의 사용 |
| CN105451776B (zh) * | 2013-08-15 | 2020-04-17 | 诺和诺德股份有限公司 | Glp-1衍生物及其用途 |
| CA2926314C (en) | 2013-10-17 | 2023-08-29 | Zealand Pharma A/S | Acylated glucagon analogues |
| US9988429B2 (en) | 2013-10-17 | 2018-06-05 | Zealand Pharma A/S | Glucagon analogues |
| AU2014345569B2 (en) | 2013-11-06 | 2020-08-13 | Zealand Pharma A/S | GIP-GLP-1 dual agonist compounds and methods |
| CN105829339B (zh) | 2013-11-06 | 2021-03-12 | 西兰制药公司 | 胰高血糖素-glp-1-gip三重激动剂化合物 |
| US10221315B2 (en) * | 2013-11-08 | 2019-03-05 | Ppg Industries Ohio, Inc. | Curable film-forming composition comprising catalyst associated with a carrier |
| EP3129041B1 (en) * | 2014-04-07 | 2019-06-12 | Novo Nordisk A/S | Double-acylated glp-1 compounds |
| EP3212218B1 (en) | 2014-10-29 | 2021-06-30 | Zealand Pharma A/S | Gip agonist compounds and methods |
| CN106999602B (zh) * | 2014-11-27 | 2022-02-01 | 诺和诺德股份有限公司 | Glp-1衍生物及其用途 |
| US10392428B2 (en) | 2014-12-17 | 2019-08-27 | Novo Nordisk A/S | GLP-1 derivatives and uses thereof |
| CA2980978A1 (en) | 2015-04-16 | 2016-10-20 | Zealand Pharma A/S | Acylated glucagon analogue |
| AU2016270373A1 (en) | 2015-06-05 | 2018-01-04 | Vertex Pharmaceuticals Incorporated | Triazoles for the treatment of demyelinating diseases |
| WO2018106641A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Pyrazoles for the treatment of demyelinating diseases |
| WO2018106646A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Aminotriazoles for the treatment of demyelinating diseases |
| WO2018106643A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Heterocyclic azoles for the treatment of demyelinating diseases |
| WO2019023295A1 (en) * | 2017-07-27 | 2019-01-31 | Saint Louis University | Fatty acid modified human epidermal growth factor |
| JP6633777B2 (ja) | 2017-08-24 | 2020-01-22 | ノヴォ ノルディスク アー／エス | Ｇｌｐ−１組成物及びその使用 |
| DK3774862T3 (da) | 2018-04-05 | 2022-09-05 | Sun Pharmaceutical Ind Ltd | Nye GLP-1-analoger |
| CN113214382B (zh) * | 2018-04-19 | 2024-01-19 | 杭州先为达生物科技股份有限公司 | 酰化的glp-1衍生物 |
| TWI829687B (zh) | 2018-05-07 | 2024-01-21 | 丹麥商諾佛 儂迪克股份有限公司 | 包含glp-1促效劑與n-(8-(2-羥基苯甲醯基)胺基)辛酸之鹽的固體組成物 |
| GB201813678D0 (en) * | 2018-08-22 | 2018-10-03 | Keybioscience Ag | Acylated calcitonin mimetics |
| WO2021136223A1 (en) | 2019-12-31 | 2021-07-08 | Beijing Ql Biopharmaceutical Co., Ltd. | Fusion proteins of glp-1 and gdf15 and conjugates thereof |
| AU2021208601B2 (en) | 2020-02-18 | 2025-06-05 | Novo Nordisk A/S | Glp-1 compositions and uses thereof |
| KR20230083294A (ko) | 2020-09-30 | 2023-06-09 | 베이징 큐엘 바이오파마슈티컬 컴퍼니 리미티드 | 폴리펩타이드 접합체 및 사용 방법 |
| WO2022096636A1 (en) * | 2020-11-06 | 2022-05-12 | Novo Nordisk A/S | Glp-1 prodrugs and uses hereof |
| CN117279657A (zh) | 2021-05-18 | 2023-12-22 | 日本株式会社Ltt生物医药 | 用于治疗或预防伴随抗癌剂给药的障碍的医药组合物 |
| WO2022266927A1 (zh) * | 2021-06-24 | 2022-12-29 | 深圳翰宇药业股份有限公司 | 一种利拉鲁肽变构体及其制备方法、应用 |
| CA3252113A1 (en) | 2022-03-30 | 2023-10-05 | Beijing Ql Biopharmaceutical Co., Ltd. | Liquid pharmaceutical compositions of polypeptide conjugates and their methods of use |
| CN119173275A (zh) | 2022-05-10 | 2024-12-20 | 诺和诺德股份有限公司 | Glp-1多肽的前药及其用途 |
| CN121001710A (zh) | 2022-12-30 | 2025-11-21 | 阿尔吉法玛公司 | 提高口服多肽治疗剂的全身生物利用度的组合物和方法 |
| CN120676965A (zh) * | 2023-11-07 | 2025-09-19 | 深圳信立泰药业股份有限公司 | 多重受体共激动剂化合物及其制备方法与应用 |
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| US5336782A (en) | 1991-04-24 | 1994-08-09 | Kuraray Co., Ltd. | Long chain carboxylic acid imide ester |
| SE9102652D0 (sv) * | 1991-09-13 | 1991-09-13 | Kabi Pharmacia Ab | Injection needle arrangement |
| US5512549A (en) * | 1994-10-18 | 1996-04-30 | Eli Lilly And Company | Glucagon-like insulinotropic peptide analogs, compositions, and methods of use |
| JP3149958B2 (ja) | 1996-08-30 | 2001-03-26 | ノボ ノルディスク アクティーゼルスカブ | Ｇｌｐ―１誘導体 |
| AU2610699A (en) * | 1998-02-27 | 1999-09-15 | Novo Nordisk A/S | Derivatives of glp-1 analogs |
| MY155270A (en) * | 1998-09-24 | 2015-09-30 | Lilly Co Eli | Use of glp-1 or analogs in treatment of stroke |
| KR101241862B1 (ko) | 2003-09-19 | 2013-03-13 | 노보 노르디스크 에이/에스 | 신규 ｇｌｐ-1 유도체 |
| 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 |
| JP2011504871A (ja) | 2007-06-01 | 2011-02-17 | ノボ・ノルデイスク・エー／エス | 固体又は半固体担体中にペプチド薬剤を含む自然に分散可能なプレコンセントレイト |
| EP2190872B1 (en) | 2007-09-05 | 2018-03-14 | Novo Nordisk A/S | Glucagon-like peptide-1 derivatives and their pharmaceutical use |
| EP2190460B1 (en) * | 2007-09-05 | 2014-12-17 | Novo Nordisk A/S | Peptides derivatized with a-b-c-d- and their therapeutical use |
| EP2195034A2 (en) * | 2007-09-27 | 2010-06-16 | Amylin Pharmaceuticals, Inc. | Peptide-peptidase inhibitor conjugates and methods of making and using same |
| US20100317057A1 (en) * | 2007-12-28 | 2010-12-16 | Novo Nordisk A/S | Semi-recombinant preparation of glp-1 analogues |
| US8637647B2 (en) | 2008-09-12 | 2014-01-28 | Novo Nordisk A/S | Method of acylating a peptide or protein |
| JP2013514322A (ja) * | 2009-12-16 | 2013-04-25 | ノヴォ ノルディスク アー／エス | 修飾されたｎ末端を有するｇｌｐ−１受容体アゴニスト化合物 |
| JP6231386B2 (ja) * | 2010-11-09 | 2017-11-15 | ノヴォ ノルディスク アー／エス | リンカーを有する二重アシル化されたｇｌｐ−１誘導体 |
-
2011
- 2011-11-09 JP JP2013538180A patent/JP6231386B2/ja active Active
- 2011-11-09 WO PCT/EP2011/069743 patent/WO2012062804A1/en not_active Ceased
- 2011-11-09 CN CN201180054077.1A patent/CN103209711B/zh active Active
- 2011-11-09 US US13/883,946 patent/US9006178B2/en active Active
- 2011-11-09 EP EP11779456.0A patent/EP2637698B1/en active Active
- 2011-11-09 WO PCT/EP2011/069738 patent/WO2012062803A1/en not_active Ceased
- 2011-11-09 CN CN201610182509.1A patent/CN105601729A/zh not_active Withdrawn
- 2011-11-09 ES ES11779456T patent/ES2913803T3/es active Active
- 2011-11-09 EP EP11779674.8A patent/EP2637699B1/en active Active
- 2011-11-09 JP JP2013538179A patent/JP6039569B2/ja active Active
- 2011-11-09 US US13/882,947 patent/US9708383B2/en active Active
- 2011-11-09 ES ES11779674T patent/ES2683372T3/es active Active
- 2011-11-09 CN CN201180054105.XA patent/CN103200966B/zh active Active
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2015
- 2015-01-29 US US14/608,284 patent/US20150210745A1/en not_active Abandoned
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2016
- 2016-08-01 JP JP2016151098A patent/JP2016188246A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP2637699A1 (en) | 2013-09-18 |
| US20130338068A1 (en) | 2013-12-19 |
| CN105601729A (zh) | 2016-05-25 |
| EP2637699B1 (en) | 2018-05-16 |
| CN103200966A (zh) | 2013-07-10 |
| CN103209711A (zh) | 2013-07-17 |
| US9006178B2 (en) | 2015-04-14 |
| US9708383B2 (en) | 2017-07-18 |
| JP2013543853A (ja) | 2013-12-09 |
| JP2016188246A (ja) | 2016-11-04 |
| EP2637698A1 (en) | 2013-09-18 |
| JP6039569B2 (ja) | 2016-12-07 |
| EP2637698B1 (en) | 2022-04-20 |
| JP6231386B2 (ja) | 2017-11-15 |
| US20150210745A1 (en) | 2015-07-30 |
| US20130288960A1 (en) | 2013-10-31 |
| CN103209711B (zh) | 2016-04-13 |
| JP2014501712A (ja) | 2014-01-23 |
| CN103200966B (zh) | 2016-10-12 |
| WO2012062803A1 (en) | 2012-05-18 |
| WO2012062804A1 (en) | 2012-05-18 |
| ES2683372T3 (es) | 2018-09-26 |
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