JP2016500682A5 - - Google Patents
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- JP2016500682A5 JP2016500682A5 JP2015537240A JP2015537240A JP2016500682A5 JP 2016500682 A5 JP2016500682 A5 JP 2016500682A5 JP 2015537240 A JP2015537240 A JP 2015537240A JP 2015537240 A JP2015537240 A JP 2015537240A JP 2016500682 A5 JP2016500682 A5 JP 2016500682A5
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- Prior art keywords
- amino acid
- pharmaceutical composition
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- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 125000000539 amino acid group Chemical group 0.000 claims 7
- 150000001413 amino acids Chemical class 0.000 claims 7
- 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 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims 5
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 4
- 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 claims 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 235000001014 amino acid Nutrition 0.000 claims 3
- 229940024606 amino acid Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical group C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 230000002209 hydrophobic effect Effects 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 101500028773 Homo sapiens Glucagon-like peptide 1(7-37) Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 claims 1
- GQCSFCKGCIEEJN-INIZCTEOSA-N N-myristoyl glutamine Chemical compound CCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(N)=O GQCSFCKGCIEEJN-INIZCTEOSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- 108010077895 Sarcosine Proteins 0.000 claims 1
- DLSWIYLPEUIQAV-UHFFFAOYSA-N Semaglutide Chemical compound CCC(C)C(NC(=O)C(Cc1ccccc1)NC(=O)C(CCC(O)=O)NC(=O)C(CCCCNC(=O)COCCOCCNC(=O)COCCOCCNC(=O)CCC(NC(=O)CCCCCCCCCCCCCCCCC(O)=O)C(O)=O)NC(=O)C(C)NC(=O)C(C)NC(=O)C(CCC(N)=O)NC(=O)CNC(=O)C(CCC(O)=O)NC(=O)C(CC(C)C)NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C(CO)NC(=O)C(NC(=O)C(CC(O)=O)NC(=O)C(CO)NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)C(NC(=O)CNC(=O)C(CCC(O)=O)NC(=O)C(C)(C)NC(=O)C(N)Cc1cnc[nH]1)C(C)O)C(C)O)C(C)C)C(=O)NC(C)C(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(CC(C)C)C(=O)NC(C(C)C)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CCCNC(N)=N)C(=O)NCC(O)=O DLSWIYLPEUIQAV-UHFFFAOYSA-N 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 1
- 239000004473 Threonine Substances 0.000 claims 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 229960001230 asparagine Drugs 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
- 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
- 230000037430 deletion Effects 0.000 claims 1
- 238000012217 deletion Methods 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- -1 fatty acid amino acid Chemical class 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000003780 insertion Methods 0.000 claims 1
- 230000037431 insertion Effects 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008203 oral pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229940043230 sarcosine Drugs 0.000 claims 1
- 229950011186 semaglutide Drugs 0.000 claims 1
- 108010060325 semaglutide Proteins 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- 0 *C(C(O*)=O)N(*)C(*)=O Chemical compound *C(C(O*)=O)N(*)C(*)=O 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12188872 | 2012-10-17 | ||
| EP12188872.1 | 2012-10-17 | ||
| US201261715416P | 2012-10-18 | 2012-10-18 | |
| US61/715,416 | 2012-10-18 | ||
| PCT/EP2013/071618 WO2014060472A1 (en) | 2012-10-17 | 2013-10-16 | Fatty acid acylated amino acids for oral peptide delivery |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016500682A JP2016500682A (ja) | 2016-01-14 |
| JP2016500682A5 true JP2016500682A5 (https=) | 2016-12-08 |
Family
ID=47049065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015537240A Withdrawn JP2016500682A (ja) | 2012-10-17 | 2013-10-16 | 経口ペプチドデリバリーのための脂肪酸アシル化アミノ酸 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20150273069A1 (https=) |
| EP (1) | EP2908844A1 (https=) |
| JP (1) | JP2016500682A (https=) |
| CN (1) | CN104717972A (https=) |
| WO (1) | WO2014060472A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015162195A1 (en) * | 2014-04-23 | 2015-10-29 | Novo Nordisk A/S | Fatty acid acylated amino acids for oral peptide delivery |
| US9833411B2 (en) | 2015-01-12 | 2017-12-05 | Enteris Biopharma, Inc. | Solid oral dosage forms |
| CN107205949A (zh) * | 2015-01-29 | 2017-09-26 | 诺和诺德股份有限公司 | 包含片芯和立即释放包衣的用于口服glp‑1给药的药物组合物 |
| US10265384B2 (en) | 2015-01-29 | 2019-04-23 | Novo Nordisk A/S | Tablets comprising GLP-1 agonist and enteric coating |
| EP3928776B1 (en) | 2016-04-22 | 2025-11-12 | Spoke Sciences, Inc. | Fast-acting plant-based medicinal compounds and nutritional supplements |
| EA201892396A1 (ru) | 2016-12-02 | 2019-04-30 | Ресептор Лайф Сайенсиз, Инк. | Быстродействующие растительные лекарственные соединения и биологически активные добавки |
| HRP20240485T1 (hr) * | 2017-08-24 | 2024-07-05 | Novo Nordisk A/S | Pripravci glp-1 i njihova upotreba |
| HRP20230929T1 (hr) * | 2018-10-26 | 2023-11-24 | Novo Nordisk A/S | Stabilni pripravci semaglutida i njihova upotreba |
| AU2019385420A1 (en) | 2018-11-19 | 2021-07-08 | Spoke Sciences, Inc. | N-acylated fatty amino acids to reduce absorption variability in cannabinoid based compositions |
| PE20230819A1 (es) | 2020-02-18 | 2023-05-19 | Novo Nordisk As | Composiciones y usos de glp-1 |
| WO2022049310A1 (en) * | 2020-09-07 | 2022-03-10 | Cyprumed Gmbh | Improved pharmaceutical formulations of glp-1 receptor agonists |
| CN114729060B (zh) | 2020-09-30 | 2022-11-25 | 北京质肽生物医药科技有限公司 | 多肽缀合物和使用方法 |
| CN114272511B (zh) * | 2021-01-12 | 2023-08-01 | 广州新济药业科技有限公司 | 司美格鲁肽可溶性微针贴片及其制备方法 |
| EP4299057A1 (en) | 2022-06-30 | 2024-01-03 | Adocia | Solid compositions comprising a peptide or a protein and an acylated amino acid |
| US20250000948A1 (en) | 2021-11-15 | 2025-01-02 | Adocia | Solid compositions comprising a peptide or a protein and an acylated amino acid |
| EP4180060A1 (en) | 2021-11-15 | 2023-05-17 | Adocia | Solid compositions comprising a peptide or a protein and an acylated amino acid |
| EP4486366A1 (en) * | 2022-03-03 | 2025-01-08 | Cyprumed GmbH | Improved oral pharmaceutical formulations of therapeutic peptides and proteins |
| EP4323413A4 (en) | 2022-03-30 | 2025-10-15 | Beijing Ql Biopharmaceutical Co Ltd | LIQUID PHARMACEUTICAL COMPOSITIONS OF POLYPEPTIDE CONJUGATES AND METHODS OF USE THEREOF |
| KR20250144708A (ko) * | 2024-03-27 | 2025-10-13 | 한국과학기술연구원 | 올리고감마글루탐산 유도체 기반의 신규한 지질 및 이를 포함하는 지질나노입자와 이의 용도 |
| US12544349B1 (en) | 2024-12-30 | 2026-02-10 | Adocia | Compositions comprising pemvidutide and an acylated amino acid |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629020A (en) * | 1994-04-22 | 1997-05-13 | Emisphere Technologies, Inc. | Modified amino acids for drug delivery |
| DK39892D0 (da) | 1992-03-25 | 1992-03-25 | Bernard Thorens | Peptid |
| US5869602A (en) | 1995-03-17 | 1999-02-09 | Novo Nordisk A/S | Peptide derivatives |
| IL128332A0 (en) | 1996-08-30 | 2000-01-31 | Novo Nordisk As | GLP-1 derivatives |
| JP2002512175A (ja) | 1998-02-27 | 2002-04-23 | ノボ ノルディスク アクティーゼルスカブ | Ｇｌｐ−１類似体の誘導体類 |
| JP2003522099A (ja) | 1998-02-27 | 2003-07-22 | ノボ ノルディスク アクティーゼルスカブ | 遅延作用プロファイルを有するｇｌｐ−１のｇｌｐ−１誘導体及びエキセンジン |
| EP1062240B1 (en) | 1998-02-27 | 2010-04-28 | Novo Nordisk A/S | N-terminally modified glp-1 derivatives |
| EP1061946B1 (en) | 1998-02-27 | 2004-04-28 | Novo Nordisk A/S | Glp-1 derivatives with helix-content exceeding 25 %, forming partially structured micellar-like aggregates |
| US6656499B1 (en) * | 1999-11-12 | 2003-12-02 | Pharmaderm Laboratories, Ltd. | Composition for transdermal and dermal administration of interferon-α |
| FR2828102B1 (fr) * | 2001-03-28 | 2004-07-09 | Ifc Sa | Utilisation des lipoaminoacides dans une composition pharmaceutique comme promoteur et systeme disperse a usage pharmaceutique contenant de tels composes |
| KR101241862B1 (ko) | 2003-09-19 | 2013-03-13 | 노보 노르디스크 에이/에스 | 신규 ｇｌｐ-1 유도체 |
| MXPA06006745A (es) | 2003-12-18 | 2006-08-18 | Novo Nordisk As | Compuestos glp-1 novedosos. |
| JP2007537142A (ja) | 2003-12-18 | 2007-12-20 | ノボ ノルディスク アクティーゼルスカブ | アルブミン様物質に結合した新規のｇｌｐ−１類似物 |
| US20060286129A1 (en) * | 2003-12-19 | 2006-12-21 | Emisphere Technologies, Inc. | Oral GLP-1 formulations |
| WO2006003781A1 (ja) | 2004-06-30 | 2006-01-12 | Pioneer Corporation | バックアップ装置および車載機器 |
| MXPA06015049A (es) | 2004-07-08 | 2007-02-08 | Novo Nordisk As | Marcadores prolongadores de polipeptidos que comprenden una porcion tetrazol. |
| US7544714B2 (en) * | 2004-07-16 | 2009-06-09 | University Of Massachusetts | Lipid-amino acid conjugates and methods of use |
| US8030273B2 (en) | 2004-10-07 | 2011-10-04 | Novo Nordisk A/S | Protracted exendin-4 compounds |
| JP5755398B2 (ja) | 2005-03-18 | 2015-07-29 | ノヴォ ノルディスク アー／エス | 伸長されたｇｌｐ−１化合物 |
| TWI372629B (en) | 2005-03-18 | 2012-09-21 | Novo Nordisk As | Acylated glp-1 compounds |
| US20090318353A1 (en) | 2006-08-25 | 2009-12-24 | Novo Nordisk A/S | Acylated Exendin-4 Compounds |
| WO2009030774A1 (en) | 2007-09-05 | 2009-03-12 | Novo Nordisk A/S | Truncated glp-1 derivatives and their therapeutical use |
| US20100261637A1 (en) | 2007-09-05 | 2010-10-14 | Novo Nordisk A/S | Peptides derivatized with a-b-c-d- and their therapeutical use |
| EP2190872B1 (en) | 2007-09-05 | 2018-03-14 | Novo Nordisk A/S | Glucagon-like peptide-1 derivatives and their pharmaceutical use |
| US20100317057A1 (en) | 2007-12-28 | 2010-12-16 | Novo Nordisk A/S | Semi-recombinant preparation of glp-1 analogues |
| WO2012140155A1 (en) * | 2011-04-14 | 2012-10-18 | Novo Nordisk A/S | Fatty acid acylated amino acids for oral peptide delivery |
-
2013
- 2013-10-16 US US14/436,126 patent/US20150273069A1/en not_active Abandoned
- 2013-10-16 EP EP13776830.5A patent/EP2908844A1/en not_active Withdrawn
- 2013-10-16 CN CN201380054130.7A patent/CN104717972A/zh not_active Withdrawn
- 2013-10-16 WO PCT/EP2013/071618 patent/WO2014060472A1/en not_active Ceased
- 2013-10-16 JP JP2015537240A patent/JP2016500682A/ja not_active Withdrawn
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