CN101108875A - 生长激素释放肽 - Google Patents
生长激素释放肽 Download PDFInfo
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- CN101108875A CN101108875A CNA2007101279712A CN200710127971A CN101108875A CN 101108875 A CN101108875 A CN 101108875A CN A2007101279712 A CNA2007101279712 A CN A2007101279712A CN 200710127971 A CN200710127971 A CN 200710127971A CN 101108875 A CN101108875 A CN 101108875A
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Classifications
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40226302P | 2002-08-09 | 2002-08-09 | |
| US60/402,263 | 2002-08-09 |
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|---|---|---|---|
| CNA038186810A Division CN1674927A (zh) | 2002-08-09 | 2003-08-08 | 生长激素释放肽 |
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| Publication Number | Publication Date |
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| CN101108875A true CN101108875A (zh) | 2008-01-23 |
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| CNA038186810A Pending CN1674927A (zh) | 2002-08-09 | 2003-08-08 | 生长激素释放肽 |
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| TW (1) | TWI331922B (https=) |
| WO (1) | WO2004014415A1 (https=) |
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|---|---|---|---|---|
| CN104487049A (zh) * | 2012-06-08 | 2015-04-01 | 益普生制药股份有限公司 | 提供改良释放的可溶性活性药物肽的水性胶凝组合物 |
| CN114805487A (zh) * | 2022-06-07 | 2022-07-29 | 成都诺和晟泰生物科技有限公司 | 一种多肽化合物及其应用 |
| WO2022206587A1 (zh) * | 2021-03-30 | 2022-10-06 | 成都诺和晟泰生物科技有限公司 | 一种多肽化合物及其应用 |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI331922B (en) * | 2002-08-09 | 2010-10-21 | Ipsen Pharma Sas | Growth hormone releasing peptides |
| WO2004027064A2 (en) * | 2002-09-18 | 2004-04-01 | Centre Hospitalier De L'universite De Montreal (Chum) | Ghrh analogues |
| WO2004071448A2 (en) * | 2003-02-12 | 2004-08-26 | Transtech Pharma Inc. | Substituted azole derivatives as inhibitors of protein tyrosine phosphatases |
| WO2006045314A2 (en) * | 2004-10-27 | 2006-05-04 | Gastrotech Pharma A/S | Use of a growth hormone secretatogue for increasing or maintaining lean body mass and/or for treatment of chronic obstructive pulmonary disease |
| JP2008521840A (ja) * | 2004-11-30 | 2008-06-26 | ガストロテック・ファルマ・アクティーゼルスカブ | 成長ホルモン分泌促進物質レセプター１ａリガンド |
| US8138218B2 (en) | 2005-07-22 | 2012-03-20 | Ipsen Pharma S.A.S. | Growth hormone secretagogues |
| ES2740108T3 (es) * | 2005-09-29 | 2020-02-05 | Ipsen Pharma | Composición para uso en el tratamiento de dismotilidad gastrointestinal |
| EP1818061A1 (en) * | 2005-12-02 | 2007-08-15 | Charite-Universitätsmedizin Berlin | Use of ghrelin for stimulating hair growth |
| CU23592A1 (es) * | 2006-02-28 | 2010-11-11 | Ct Ingenieria Genetica Biotech | Método para prevenir y eliminar las fibrosis y otras formas de depósito patológico en los tejidos aplicando el péptido secretagogo ghrp-6 |
| EP2012809B1 (en) * | 2006-03-10 | 2013-05-22 | Ipsen Pharma | Use of a ghrelin agonist to improve the catabolic effects of glucocorticoid treatment |
| WO2007127457A2 (en) * | 2006-04-28 | 2007-11-08 | The Administrators Of The Tulane Educational Fund | Ghrelin/growth hormone releasing peptide/growth hormone secretatogue receptor antagonists and uses thereof |
| AU2007300526B2 (en) * | 2006-09-27 | 2011-07-21 | Ipsen Pharma S.A.S. | Analogs of ghrelin substituted at the N-terminal |
| KR20090119785A (ko) | 2007-03-12 | 2009-11-19 | 유키지루시 뉴교 가부시키가이샤 | 성장 호르몬 분비 촉진제 |
| TW200916113A (en) * | 2007-08-08 | 2009-04-16 | Sod Conseils Rech Applic | Method for inhibiting inflammation and pro-inflammatory cytokine/chemokine expression using a ghrelin analogue |
| WO2009108364A2 (en) * | 2008-02-27 | 2009-09-03 | Ipsen Pharma S.A.S. | Antagonistic analogues of ghrh |
| US9724381B2 (en) | 2009-05-12 | 2017-08-08 | The Administrators Of The Tulane Educational Fund | Methods of inhibiting the ghrelin/growth hormone secretatogue receptor pathway and uses thereof |
| MX343499B (es) * | 2010-03-15 | 2016-11-08 | Ipsen Pharma Sas | Composiciones farmaceuticas de ligandos receptores de secretagoga de la hormona de crecimiento. |
| AR088392A1 (es) * | 2011-10-18 | 2014-05-28 | Aileron Therapeutics Inc | Macrociclos peptidomimeticos |
| UA115542C2 (uk) * | 2011-12-23 | 2017-11-27 | Іпсен Мануфекчерінг Айрленд Лімітед | Процес синтезу терапевтичних пептидів |
| US10039813B2 (en) | 2012-02-07 | 2018-08-07 | Massachusetts Institute Of Technology | Use of antagonists of ghrelin or ghrelin receptor to prevent or treat stress-sensitive psychiatric illness |
| WO2014144231A1 (en) | 2013-03-15 | 2014-09-18 | Massachusetts Institute Of Technology | Use of antagonists of growth hormone or growth hormone receptor to prevent or treat stress-sensitive psychiatric illness |
| US9119832B2 (en) | 2014-02-05 | 2015-09-01 | The Regents Of The University Of California | Methods of treating mild brain injury |
| AU2015227278A1 (en) | 2014-03-04 | 2016-10-06 | Allergan Gi Corp. | Process for the liquid phase synthesis of H-Inp-(D)Bal-(D)Trp-Phe-Apc-NH2, and pharmaceutically acceptable salts thereof |
| WO2016138099A1 (en) | 2015-02-24 | 2016-09-01 | Massachusetts Institute Of Technology | Use of ghrelin or functional ghrelin receptor agonists to prevent and treat stress-sensitive psychiatric illness |
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| US10111929B1 (en) * | 2017-04-07 | 2018-10-30 | Ez Ip, Llc | Growth hormone releasing factor analogs and uses |
| CN113045625B (zh) * | 2021-03-30 | 2023-11-07 | 成都诺和晟泰生物科技有限公司 | 作为生长激素促分泌素受体激动剂的多肽及其应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264565A (en) | 1991-01-22 | 1993-11-23 | Affymax Technologies, N.V. | Nucleic acid encoding the D2 /Ml chimeric receptor |
| JP3131049B2 (ja) * | 1992-09-30 | 2001-01-31 | マツダ株式会社 | 車両のサスペンション装置 |
| HU224345B1 (hu) | 1993-12-23 | 2005-08-29 | Novo Nordisk A/S. | Növekedési hormont felszabadító tulajdonságú peptidek, ezeket hatóanyagként tartalmazó gyógyszerkészítmények és alkalmazásuk |
| US7067326B2 (en) * | 1994-01-13 | 2006-06-27 | The Trustees Of Columbia University In The City Of New York | Synthetic receptors, libraries and uses thereof |
| RU2110275C1 (ru) * | 1994-09-09 | 1998-05-10 | Дейгин Владислав Исакович | Способ получения пептида, обладающего анаболической активностью, стимулирующего увеличение массы тела, развитие эпидермального слоя и роста волосяного покрова |
| JP3810083B2 (ja) * | 1994-09-27 | 2006-08-16 | アーダナ・バイオサイエンス・リミテツド | 成長因子の放出を促進し得る２−アルキルトリプトファン含有ペプチド化合物 |
| US20020111461A1 (en) * | 1999-05-21 | 2002-08-15 | Todd C. Somers | Low molecular weight peptidomimetic growth hormone secretagogues |
| US5798337A (en) | 1994-11-16 | 1998-08-25 | Genentech, Inc. | Low molecular weight peptidomimetic growth hormone secretagogues |
| US5776718A (en) * | 1995-03-24 | 1998-07-07 | Arris Pharmaceutical Corporation | Reversible protease inhibitors |
| BR9608909A (pt) | 1995-06-22 | 1999-03-02 | Novo Nordisk As | Composto composição farmacêutica processos para estimular a liberação do hormônio do crescimento da patuitária e aumentar a velocidade e extensão do crescimento dos animais para aumentar a produção de leite ou lã de animais ou para para doenças e uso do composto |
| DE69637587D1 (de) | 1995-07-26 | 2008-08-21 | Astrazeneca Ab | Chimäre rezeptoren und verfahren zur identifizieren verbindungen mit einem aktivität als metabotropischen glutamatrezeptoren sowie verwendung solcher verbindungen in der behandlung von neurologischer erkrankungen und neurologischenstörrungen |
| US6124263A (en) * | 1998-11-16 | 2000-09-26 | Asta Medica Ag | Treatment of tumors by administration of growth hormone releasing compounds and their antagonists |
| US5932548A (en) * | 1998-06-03 | 1999-08-03 | Deghenghi; Romano | Lysine containing peptides for treatment of heart disease |
| AU5671099A (en) * | 1998-08-14 | 2000-03-06 | The Administrators Of The Tulane Eductional Fund | Compounds having growth hormone releasing activity |
| KR100827973B1 (ko) | 1999-07-23 | 2008-05-21 | 겐지 간가와 | 신규 펩티드 |
| US20020187938A1 (en) | 2000-07-24 | 2002-12-12 | Romano Deghenghi | Ghrelin antagonists |
| TWI331922B (en) * | 2002-08-09 | 2010-10-21 | Ipsen Pharma Sas | Growth hormone releasing peptides |
| WO2006045314A2 (en) | 2004-10-27 | 2006-05-04 | Gastrotech Pharma A/S | Use of a growth hormone secretatogue for increasing or maintaining lean body mass and/or for treatment of chronic obstructive pulmonary disease |
| ES2740108T3 (es) * | 2005-09-29 | 2020-02-05 | Ipsen Pharma | Composición para uso en el tratamiento de dismotilidad gastrointestinal |
| EP2012809B1 (en) * | 2006-03-10 | 2013-05-22 | Ipsen Pharma | Use of a ghrelin agonist to improve the catabolic effects of glucocorticoid treatment |
| TW200916113A (en) * | 2007-08-08 | 2009-04-16 | Sod Conseils Rech Applic | Method for inhibiting inflammation and pro-inflammatory cytokine/chemokine expression using a ghrelin analogue |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104487049A (zh) * | 2012-06-08 | 2015-04-01 | 益普生制药股份有限公司 | 提供改良释放的可溶性活性药物肽的水性胶凝组合物 |
| WO2022206587A1 (zh) * | 2021-03-30 | 2022-10-06 | 成都诺和晟泰生物科技有限公司 | 一种多肽化合物及其应用 |
| CN114805487A (zh) * | 2022-06-07 | 2022-07-29 | 成都诺和晟泰生物科技有限公司 | 一种多肽化合物及其应用 |
| CN114805487B (zh) * | 2022-06-07 | 2024-03-12 | 成都诺和晟泰生物科技有限公司 | 一种多肽化合物及其应用 |
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