JP2013527178A5 - - Google Patents
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- JP2013527178A5 JP2013527178A5 JP2013510465A JP2013510465A JP2013527178A5 JP 2013527178 A5 JP2013527178 A5 JP 2013527178A5 JP 2013510465 A JP2013510465 A JP 2013510465A JP 2013510465 A JP2013510465 A JP 2013510465A JP 2013527178 A5 JP2013527178 A5 JP 2013527178A5
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- JP
- Japan
- Prior art keywords
- xaa
- amino acid
- naturally occurring
- carbon atoms
- group
- 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
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- 235000001014 amino acid Nutrition 0.000 claims description 264
- 150000001413 amino acids Chemical class 0.000 claims description 264
- 125000000217 alkyl group Chemical group 0.000 claims description 113
- 125000004432 carbon atom Chemical group C* 0.000 claims description 102
- 229910052739 hydrogen Inorganic materials 0.000 claims description 79
- 239000001257 hydrogen Substances 0.000 claims description 79
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 75
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 59
- 239000004472 Lysine Substances 0.000 claims description 59
- 239000004471 Glycine Substances 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 239000004220 glutamic acid Substances 0.000 claims description 37
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 34
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 34
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 33
- 239000004475 Arginine Substances 0.000 claims description 32
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 32
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 32
- 239000011737 fluorine Chemical group 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Chemical group 0.000 claims description 24
- 239000001301 oxygen Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 235000018417 cysteine Nutrition 0.000 claims description 21
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 21
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 20
- 235000013922 glutamic acid Nutrition 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 18
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 17
- 229940000635 beta-alanine Drugs 0.000 claims description 17
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 17
- 229960002989 glutamic acid Drugs 0.000 claims description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 13
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 13
- 239000004474 valine Substances 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 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 description 11
- 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 description 11
- 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 description 11
- 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 description 11
- HNDVDQJCIGZPNO-RXMQYKEDSA-N D-histidine Chemical compound OC(=O)[C@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-RXMQYKEDSA-N 0.000 claims description 11
- 229930195721 D-histidine Natural products 0.000 claims description 11
- 150000001408 amides Chemical group 0.000 claims description 11
- ZCKYOWGFRHAZIQ-UHFFFAOYSA-N dihydrourocanic acid Chemical compound OC(=O)CCC1=CNC=N1 ZCKYOWGFRHAZIQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 11
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- HRRYYCWYCMJNGA-ZETCQYMHSA-N alpha-methyl-L-histidine Chemical compound OC(=O)[C@](N)(C)CC1=CN=CN1 HRRYYCWYCMJNGA-ZETCQYMHSA-N 0.000 claims description 9
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 9
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 8
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 7
- OLIFSFOFKGKIRH-WUJLRWPWSA-N Gly-Thr Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)CN OLIFSFOFKGKIRH-WUJLRWPWSA-N 0.000 claims description 6
- 108010089804 glycyl-threonine Proteins 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims 21
- 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 claims 20
- 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 14
- 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 14
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 7
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 7
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 claims 7
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 7
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 claims 7
- 101800004266 Glucagon-like peptide 1(7-37) Proteins 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims 6
- 229930195729 fatty acid Natural products 0.000 claims 6
- 239000000194 fatty acid Substances 0.000 claims 6
- 150000004665 fatty acids Chemical class 0.000 claims 6
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims 6
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010061818 Disease progression Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000007107 Stomach Ulcer Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 230000005750 disease progression Effects 0.000 claims 1
- 201000006549 dyspepsia Diseases 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- 229940024606 amino acid Drugs 0.000 description 84
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 42
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 24
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 18
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 18
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 18
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 12
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 12
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 12
- 235000009582 asparagine Nutrition 0.000 description 12
- 229960001230 asparagine Drugs 0.000 description 12
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 0 C**N[C@@](*)[C@]([*+](C)[C@@](C)C(*C)=O)C(F)(F)F Chemical compound C**N[C@@](*)[C@]([*+](C)[C@@](C)C(*C)=O)C(F)(F)F 0.000 description 3
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2010/000692 WO2011143788A1 (en) | 2010-05-17 | 2010-05-17 | Novel glucagon like peptide analogs, composition, and method of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013527178A JP2013527178A (ja) | 2013-06-27 |
| JP2013527178A5 true JP2013527178A5 (enExample) | 2015-01-15 |
| JP5819946B2 JP5819946B2 (ja) | 2015-11-24 |
Family
ID=44991143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013510465A Expired - Fee Related JP5819946B2 (ja) | 2010-05-17 | 2010-05-17 | 新規のグルカゴン様ペプチド類似体、組成物、および使用方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9487570B2 (enExample) |
| EP (1) | EP2571897B1 (enExample) |
| JP (1) | JP5819946B2 (enExample) |
| KR (1) | KR101609302B1 (enExample) |
| CN (1) | CN103124739B (enExample) |
| AU (1) | AU2010353685B2 (enExample) |
| BR (1) | BR112012029248B1 (enExample) |
| CA (1) | CA2802931C (enExample) |
| ES (1) | ES2528496T3 (enExample) |
| RU (1) | RU2557301C2 (enExample) |
| SG (1) | SG185604A1 (enExample) |
| WO (1) | WO2011143788A1 (enExample) |
| ZA (1) | ZA201209566B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011134284A1 (zh) * | 2010-04-27 | 2011-11-03 | 浙江贝达药业有限公司 | 胰高血糖素样肽-1类似物及其应用 |
| EP2820424B1 (en) | 2012-01-24 | 2016-12-07 | University of Massachusetts | Soluble manf in pancreatic beta-cell disorders |
| WO2019082138A1 (en) * | 2017-10-27 | 2019-05-02 | Lorven Biologics Private Limited | PROCESS FOR THE PREPARATION OF LIRAGLUTIDE USING RECOMBINANT SACCHAROMYCES CEREVISIAE |
| WO2020118843A1 (zh) * | 2018-12-12 | 2020-06-18 | 四川利通科创生物医药科技有限公司 | 一种glp-1突变体及其制备方法和用途 |
| CN112898406B (zh) * | 2019-10-12 | 2023-11-10 | 深圳纳福生物医药有限公司 | 不同构型的glp-1类似肽修饰二聚体及其制备方法在治疗ii型糖尿病中的应用 |
| CN110862448A (zh) * | 2019-11-21 | 2020-03-06 | 浙江大学 | 两性离子多肽修饰的glp-1衍生物及其制备方法和应用 |
| CN111253475B (zh) * | 2020-02-18 | 2021-03-09 | 江苏诺泰澳赛诺生物制药股份有限公司 | Glp-1激动多肽化合物及其盐与合成方法及用途 |
| CN115124596A (zh) * | 2021-12-24 | 2022-09-30 | 浙江和泽医药科技股份有限公司 | 一种全固相合成醋酸亮丙瑞林的方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5118666A (en) | 1986-05-05 | 1992-06-02 | The General Hospital Corporation | Insulinotropic hormone |
| ES2113879T3 (es) | 1990-01-24 | 1998-05-16 | Douglas I Buckley | Analogos de glp-1 utiles para el tratamiento de diabetes. |
| US5705483A (en) | 1993-12-09 | 1998-01-06 | Eli Lilly And Company | Glucagon-like insulinotropic peptides, compositions and methods |
| US5512549A (en) * | 1994-10-18 | 1996-04-30 | Eli Lilly And Company | Glucagon-like insulinotropic peptide analogs, compositions, and methods of use |
| DE60137876D1 (de) * | 2000-06-16 | 2009-04-16 | Lilly Co Eli | Analoge des Glucagon-ähnlichen Peptids-1 |
| GEP20063908B (en) | 2001-10-18 | 2006-08-25 | Bristol Myers Squibb Co | Human glucagon-like-peptide-1 mimics and their use in the treatment of diabetes and related conditions |
| US20050153287A1 (en) * | 2001-10-19 | 2005-07-14 | Yasunori Hayashi | Nr3b nmda receptor subunit compositions and related methods |
| EP1494704A1 (en) * | 2002-04-04 | 2005-01-12 | Novo Nordisk A/S | Glp-1 agonist and cardiovascular complications |
| US7772188B2 (en) * | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US7557183B2 (en) * | 2003-03-19 | 2009-07-07 | Eli Lilly And Company | Polyethylene glycol linked GLP-1 compounds |
| KR101308912B1 (ko) * | 2003-06-03 | 2013-09-23 | 노보 노르디스크 에이/에스 | 안정화된 약학적 펩티드 조성물 |
| EP1709071A4 (en) * | 2004-01-08 | 2007-05-30 | Theratechnologies Inc | GLUCAGON LIKE PEPTIDE-1 ANALOGS WITH LONG PERFORMANCE |
| CN100503637C (zh) * | 2004-04-14 | 2009-06-24 | 浙江贝达药业有限公司 | 胰高血糖素样肽类似物、其组合物及其使用方法 |
| CN100535006C (zh) * | 2004-09-06 | 2009-09-02 | 上海华谊生物技术有限公司 | Glp-1类似物 |
| JP2008525452A (ja) * | 2004-12-22 | 2008-07-17 | イーライ リリー アンド カンパニー | Ｇｌｐ−１類似体融合蛋白質製剤 |
| TWI362392B (en) * | 2005-03-18 | 2012-04-21 | Novo Nordisk As | Acylated glp-1 compounds |
| SI1881850T1 (sl) * | 2005-05-13 | 2011-01-31 | Lilly Co Eli | Glp-1 pegilirane spojine |
| CA2621699A1 (en) * | 2005-09-08 | 2007-03-15 | Trustees Of Tufts College | Stabilized glp-1 analogs |
| DE102005063375A1 (de) * | 2005-09-15 | 2007-04-19 | Schülke & Mayr GmbH | Antimikrobielle Zubereitungen mit einem Gehalt an Octenidindihydrochlorid verkapselt in Liposomen |
| EP2007804B1 (en) * | 2006-04-20 | 2014-06-18 | Amgen, Inc | Glp-1 compounds |
| CN101668535B (zh) * | 2006-12-29 | 2017-07-28 | 益普生制药股份有限公司 | Glp‑1药物组合物 |
| ATE515943T1 (de) * | 2007-09-07 | 2011-07-15 | Janssen Pharmaceutica Nv | Kombinationen aus pyrimethanil und silberverbindungen |
| GB0717399D0 (en) * | 2007-09-07 | 2007-10-17 | Uutech Ltd | Use of GLP-1 analogues for the treatment of disorders associated with dysfunctional synaptic transmission |
| US20100317057A1 (en) * | 2007-12-28 | 2010-12-16 | Novo Nordisk A/S | Semi-recombinant preparation of glp-1 analogues |
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2010
- 2010-05-17 WO PCT/CN2010/000692 patent/WO2011143788A1/en not_active Ceased
- 2010-05-17 CA CA2802931A patent/CA2802931C/en active Active
- 2010-05-17 RU RU2012154322/10A patent/RU2557301C2/ru active
- 2010-05-17 CN CN201080066828.7A patent/CN103124739B/zh active Active
- 2010-05-17 SG SG2012084323A patent/SG185604A1/en unknown
- 2010-05-17 KR KR1020127033002A patent/KR101609302B1/ko not_active Expired - Fee Related
- 2010-05-17 ES ES10851547.9T patent/ES2528496T3/es active Active
- 2010-05-17 AU AU2010353685A patent/AU2010353685B2/en not_active Ceased
- 2010-05-17 EP EP10851547.9A patent/EP2571897B1/en not_active Not-in-force
- 2010-05-17 JP JP2013510465A patent/JP5819946B2/ja not_active Expired - Fee Related
- 2010-05-17 US US13/698,819 patent/US9487570B2/en not_active Expired - Fee Related
- 2010-05-17 BR BR112012029248-0A patent/BR112012029248B1/pt not_active IP Right Cessation
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2012
- 2012-12-14 ZA ZA2012/09566A patent/ZA201209566B/en unknown
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