ES2623979T3 - Síntesis de productos peptídicos que contienen hidantoína - Google Patents
Síntesis de productos peptídicos que contienen hidantoína Download PDFInfo
- Publication number
- ES2623979T3 ES2623979T3 ES14710915.1T ES14710915T ES2623979T3 ES 2623979 T3 ES2623979 T3 ES 2623979T3 ES 14710915 T ES14710915 T ES 14710915T ES 2623979 T3 ES2623979 T3 ES 2623979T3
- Authority
- ES
- Spain
- Prior art keywords
- optionally
- formula
- amino acid
- acid side
- hydantoin
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Un método para sintetizar un producto peptídico que comprende un grupo hidantoína N-terminal de fórmula (I) o una sal o solvato del mismo:**Fórmula** en el que: R1 y R2 son cadenas laterales de aminoácidos, P es un resto peptídico y (*) en cada caso indica independientemente un átomo de C opcionalmente asimétrico, que comprende las etapas: (a) acoplar un bloque de construcción de hidantoína de fórmula (II)**Fórmula*+ en la que R1' es una cadena lateral de aminoácidos opcionalmente protegida, R2' es una cadena lateral de aminoácidos opcionalmente protegida, Z es un grupo carboxi y (*) en cada caso indica independientemente un átomo de C opcionalmente asimétrico a un producto peptídico de fórmula (III)**Fórmula** H2N-P' en la que P' es un resto peptídico que comprende opcionalmente cadenas laterales de aminoácidos protegidas, preferiblemente acopladas a un portador de fase sólida, (b) opcionalmente escindir grupos protectores de cadenas laterales de aminoácidos protegidas y (c) aislar y opcionalmente purificar el producto peptídico (I).
Description
DMF).
Después, se acoplaron 709,4 mg de ácido (S)-2-{(S)-2,5-dioxo-4-[2-(tritil-carbamoil)-etil]-imidazolidin-1-il}-4-metilsulfanil-butírico (cf. 1.1) sobre el material de partida en presencia de 503 mg de HBTU, 62,8 mg de HOBT y 603 µl de DIPEA.
5 Se succionó la resina seca y lavada con 3 x 30 ml de DMF, 3 x 30 ml de diclorometano, 3 x 30 ml de metanol y 3 x 30 ml de diisopropil éter. Después de secado durante la noche, se obtuvieron 9,225 g de resina Des(1-12)-hidantoín(13)-AVE-0010.
La escisión del péptido de la resina se llevó a cabo en condiciones clásicas con 2,5 g de fenol/2,5 ml de H2O/2,5 ml de tioanisol/1,25 ml de etanoditiol/41 ml de ácido trifluoroacético. El rendimiento fue 1,49 g de producto bruto Des[1
10 12]-hidantoín-(15-44)-AVE0010.
2. Purificación cromatográfica de Des[1-12]-hidantoín-(15-44)-AVE 0010
Se llevó a cabo purificación mediante dos etapas de RP-HPLC (cromatografía líquida de alta resolución de fase inversa, por sus siglas en inglés) y posterior liofilización. Las etapas de RP-HPLC se realizaron con un dispositivo Varian PrepStar. Se usaron como fase estacionaria columnas de acero inoxidable empaquetadas con material de
15 fase inversa C18 (por ej., Daisogel C18). Se usaron H2O + ácido trifluoroacético al 0,1% como fase A móvil y acetonitrilo + ácido trifluoroacético al 0,1% como fase B móvil. El gradiente se realizó a 21-90% de fase B móvil.
Se obtuvieron 0,36 g de Des [1-12] hidantoín-(15-44)-AVE0010 con una pureza de 92,15% (% área cuando se mide mediante HPLC). Se muestra un cromatograma analítico del producto purificado en la Figura 3.
3. Caracterización analítica
20 El producto purificado se caracterizó mediante espectrometría de masas. Se usó AVE0010 purificada como patrón de referencia.
Esta caracterización analítica mostró el producto correcto Des [1-12] hidantoín-(15-44)-AVE0010 con un peso molecular (M+H)+ = 3.623,014. El patrón de AVE0010 mostró un peso molecular de 4.856,544. La diferencia de masa de Des[1-12]-hidantoín(13)-AVE0010 a AVE0010 de 1.233,53 corresponde a los aminoácidos (His-Gly-Gln
25 Gly-Thr-Phe-Thr-Ser-Asp-Leu-Ser-Lys-12 H2O + CO). El peso molecular monoisotópico teórico de Des (1-12) hidantoín-(15-44)-AVE0010 es 3.621,95.
<110> Sanofi-Aventis Deutschland GmbH
<120> Síntesis de productos peptídicos que contienen hidantoína. 30 <130> 55131P EP
<160> 1
<170> PatentIn versión 3.5
<210> 1
< 211> 44 35 < 212> PRT
< 213> Secuencia artificial
<220>
< 223> Lixisenatida agonista de GLP-1
<400> 1 40
10
11
Claims (1)
-
imagen1 imagen2
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13160384 | 2013-03-21 | ||
EP13160384 | 2013-03-21 | ||
PCT/EP2014/055506 WO2014147124A1 (en) | 2013-03-21 | 2014-03-19 | Synthesis of hydantoin containing peptide products |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2623979T3 true ES2623979T3 (es) | 2017-07-12 |
Family
ID=47900954
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES14710915.1T Active ES2623979T3 (es) | 2013-03-21 | 2014-03-19 | Síntesis de productos peptídicos que contienen hidantoína |
Country Status (11)
Country | Link |
---|---|
US (1) | US10087221B2 (es) |
EP (1) | EP2976331B1 (es) |
CN (1) | CN105189465B (es) |
AU (1) | AU2014234400B2 (es) |
CA (1) | CA2907454C (es) |
ES (1) | ES2623979T3 (es) |
HK (1) | HK1219477A1 (es) |
HU (1) | HUE034308T2 (es) |
MX (1) | MX363522B (es) |
SG (1) | SG11201506804VA (es) |
WO (1) | WO2014147124A1 (es) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR102981A1 (es) | 2014-12-11 | 2017-04-05 | Harvard College | Inhibidores de la necrosis celular y métodos de preparación de los mismos |
CN106928340A (zh) * | 2015-12-31 | 2017-07-07 | 深圳翰宇药业股份有限公司 | 一种利西拉来的制备方法 |
Family Cites Families (223)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3835175A (en) | 1971-03-15 | 1974-09-10 | Research Corp | 9-fluorenylmethanol haloformates, carbonates and thiocarbonates |
US3906031A (en) | 1971-03-15 | 1975-09-16 | Research Corp | Novel 9-fluorenylmethoxycarbonyl compounds |
US4108846A (en) | 1977-02-01 | 1978-08-22 | Hoffmann-La Roche Inc. | Solid phase synthesis with base N alpha-protecting group cleavage |
DE3542442A1 (de) | 1985-11-30 | 1987-06-04 | Hoechst Ag | Verfahren zur herstellung von peptiden unter der verwendung von perchloraten |
US5175254A (en) | 1988-09-24 | 1992-12-29 | Societe D'expansion Scientifque Expansia | Solid phase peptide synthesis using a polyacrylic support in aqueous solution |
GB8913089D0 (en) | 1989-06-07 | 1989-07-26 | Ciba Geigy Japan Ltd | Novel endothelin derivative |
US5296468A (en) | 1989-10-30 | 1994-03-22 | The Salk Institute For Biological Studies | GnRH analogs |
US5580957A (en) | 1989-10-30 | 1996-12-03 | The Salk Institute For Biological Studies | GnRH analogs |
US5169932A (en) | 1989-10-30 | 1992-12-08 | The Salk Institute For Biological Studies | Gnrh analogs |
US5352796A (en) | 1989-10-30 | 1994-10-04 | The Salk Institute For Biological Studies | Amino acids useful in making GnRH analogs |
EP0445801A3 (en) | 1990-03-08 | 1992-07-01 | Kuraray Co., Ltd. | Peptide and its use |
IT1241395B (it) | 1990-04-02 | 1994-01-10 | Eniricerche Spa | Composti immunogenici,il procedimento per la loro sintesi e loro impiego per la preparazione di vaccini antimalaria |
DE4014655A1 (de) | 1990-05-08 | 1991-11-14 | Behringwerke Ag | Peptidamide, verfahren zu deren herstellung und diese enthaltende mittel als fibrin/thrombin-gerinnungsinhibitoren |
TW295589B (es) | 1990-08-30 | 1997-01-11 | Hoechst Ag | |
US6040423A (en) | 1990-08-31 | 2000-03-21 | Gsellschaft Fur Biotechnologische Forschung Mbh (Gbf) | Process for synthesis of peptides |
US5744450A (en) | 1991-03-14 | 1998-04-28 | The Salk Institute For Biological Studies | GnRH analogs |
IL101074A (en) | 1991-03-14 | 1997-09-30 | Salk Inst For Biological Studi | GnRH ANALOGS AND THEIR PREPARATION |
US5576296A (en) | 1991-05-15 | 1996-11-19 | Aktiebolaget Astra | Galanin antagonist |
SE9101472D0 (sv) | 1991-05-15 | 1991-05-15 | Trion Forskning & Utveckling | Galanin antagonist |
GB9112825D0 (en) | 1991-06-14 | 1991-07-31 | Ici Plc | Process for making peptides |
US6028168A (en) | 1991-08-09 | 2000-02-22 | Winfried Kolbeck | Lanthionine bridged peptides |
AU664855B2 (en) | 1991-08-09 | 1995-12-07 | Winfried Kolbeck | Lanthionine bridged peptides |
US5639603A (en) | 1991-09-18 | 1997-06-17 | Affymax Technologies N.V. | Synthesizing and screening molecular diversity |
DE69217497T2 (de) | 1991-09-18 | 1997-06-12 | Affymax Tech Nv | Verfahren zur synthese der verschiedenen sammlungen von oligomeren |
WO1994004568A1 (en) | 1991-12-18 | 1994-03-03 | Centocor, Inc. | Peptide inhibitors of inflammation mediated by selectins |
US6667387B1 (en) | 1996-09-30 | 2003-12-23 | N.V. Innogenetics S.A. | HCV core peptides |
ES2133392T5 (es) | 1992-03-06 | 2004-12-16 | N.V. Innogenetics S.A. | Procedimiento para la determinacion de peptidos que correspondan a epitopos hcv importantes desde el punto de vista inmunologico. |
US6709828B1 (en) | 1992-03-06 | 2004-03-23 | N.V. Innogenetics S.A. | Process for the determination of peptides corresponding to immunologically important epitopes and their use in a process for determination of antibodies or biotinylated peptides corresponding to immunologically important epitopes, a process for preparing them and compositions containing them |
CA2136844A1 (en) | 1992-05-28 | 1993-12-09 | George A. Heavner | Peptide inhibitors of selectin binding |
IE921942A1 (en) | 1992-06-16 | 1993-12-29 | Gary A Siwruk John S Eynon | Liquid phase synthesis of peptides and peptide derivatives |
US5516891A (en) | 1992-06-16 | 1996-05-14 | Kinerton, Ltd. | Liquid phase synthesis of peptides and peptide derivatives |
WO1994005314A1 (en) | 1992-09-08 | 1994-03-17 | Centocor, Inc. | Peptide inhibitors of leukocyte adhesion |
US5563032A (en) | 1992-10-21 | 1996-10-08 | The United States Of America As Represented By The Department Of Health And Human Services | Mosaic polypeptide and methods for detecting the hepatitis E virus |
US5736315A (en) | 1992-10-21 | 1998-04-07 | National Institute Of Health | Methods and compositions for detecting anti-hepatitis E virus activity |
WO1994014836A1 (en) | 1992-12-18 | 1994-07-07 | Centocor, Inc. | Peptide inhibitors of selectin binding |
DE4244565A1 (de) | 1992-12-30 | 1994-07-07 | Forssmann Wolf Georg | Verfahren und Anwendung des LPAP (Lymphocytoma Proliferation Activating Peptide |
ES2133428T3 (es) | 1993-02-19 | 1999-09-16 | Hoffmann La Roche | Fabricacion de amidas y peptidos, exenta de racemizacion, en presencia de cantidades cataliticas de un compuesto n-hidroxi. |
JPH06256384A (ja) | 1993-02-26 | 1994-09-13 | Shimadzu Corp | クリーベイジ装置 |
GB9319776D0 (en) | 1993-09-24 | 1993-11-10 | Medical Res Council | Azapeptide synthesis |
NZ276860A (en) | 1993-11-02 | 1997-09-22 | Affymax Tech Nv | Apparatus and its use for synthesising diverse molecular products on substrates |
US6165778A (en) | 1993-11-02 | 2000-12-26 | Affymax Technologies N.V. | Reaction vessel agitation apparatus |
US5503805A (en) | 1993-11-02 | 1996-04-02 | Affymax Technologies N.V. | Apparatus and method for parallel coupling reactions |
WO1995014787A1 (en) | 1993-11-22 | 1995-06-01 | Centocor, Inc. | Peptide inhibitors of selecting binding |
DE4341471A1 (de) | 1993-12-02 | 1995-06-08 | Schering Ag | Tumor-Nekrose-Faktor-alpha-inaktivierende CDR-Peptide |
US5502165A (en) | 1994-04-04 | 1996-03-26 | Merck & Co., Inc. | Process for peptide segment condensation |
US5614608A (en) | 1995-01-20 | 1997-03-25 | Selectide Corporation | Apparatus and method for multiple synthesis of organic compounds on polymer support |
US6136781A (en) | 1995-04-28 | 2000-10-24 | Takeda Chemical Industries, Ltd. | LH-RH receptor antagonists |
GB9511474D0 (en) | 1995-06-07 | 1995-08-02 | Ciba Geigy Ag | Antiviral peptoid compounds |
DE19534988A1 (de) | 1995-09-21 | 1997-03-27 | Forssmann Wolf Georg | Verfahren zur Herstellung und Anwendung synthetischer, biotinylierter Peptide |
DE19543628A1 (de) | 1995-11-24 | 1997-05-28 | Forssmann Wolf Georg | Humanes, im Blut zirkulierendes Peptid mit insulinotroper Wirkung (GCAP-II-(89-112), (Guanylyl Cyclase C Aktivierendes Peptid II) und seine GCAP-Analoga, insbesondere das GCAP-I-(99-115), seine Anwendung als pharmakologischer Wirkstoff und Benutzung seines Wirkungsprinzipes zur Bereitstellung neuer GC-C-abhängiger insulinotroper Wirkstoffe |
TW505654B (en) | 1996-07-30 | 2002-10-11 | Hoffmann La Roche | Synthesis of analogs of PTH and PTHrP |
AU723268B2 (en) | 1996-09-09 | 2000-08-24 | Zealand Pharma A/S | Improved solid-phase peptide synthesis and agent for use in such synthesis |
US7176282B1 (en) | 1996-09-09 | 2007-02-13 | Zealand Pharma A/S | Solid-phase peptide synthesis and agent for use in such synthesis |
CA2265454A1 (en) | 1996-09-09 | 1998-03-19 | Zealand Pharmaceuticals A/S | Peptide prodrugs containing an alpha-hydroxyacid linker |
NZ331968A (en) | 1997-01-21 | 1999-05-28 | Max Planck Gesellschaft | Iga 1 protease fragment as carrier peptide, its conjugation to a polysaccharide derived from neisseria meningitidis</ital> |
IL138214A0 (en) | 1998-03-09 | 2001-10-31 | Zealand Pharmaceuticals As | Pharmacolgically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
JP3786533B2 (ja) | 1998-11-12 | 2006-06-14 | 善彦 西村 | ペプチド及び骨形成促進剤 |
US7425541B2 (en) | 1998-12-11 | 2008-09-16 | Medarex, Inc. | Enzyme-cleavable prodrug compounds |
DE69942128D1 (de) | 1998-12-11 | 2010-04-22 | Coulter Pharm Inc | Prodrugs und verfahren zu deren herstellung |
FR2792631B1 (fr) | 1999-04-21 | 2004-03-19 | Pasteur Institut | Support solide fonctionnalise pour la synthese de composes comportant au moins une fonction alpha oxoaldehyde et ses applications. |
US6469136B1 (en) | 1999-07-07 | 2002-10-22 | Trimeris, Inc. | Methods and composition for peptide synthesis |
US6703480B1 (en) | 1999-11-24 | 2004-03-09 | Palani Balu | Peptide dimers as agonists of the erythropoientin (EPO) receptor, and associated methods of synthesis and use |
FR2803594B1 (fr) | 2000-01-11 | 2002-07-19 | Centre Nat Rech Scient | Oligomeres de mimes contraints non peptidiques de dipeptides ou de tripeptides, et leurs utilisations |
TR200401142T4 (tr) | 2000-01-27 | 2004-07-21 | Eli Lilly And Company | Glükagon-benzeri peptid bileşiklerinin çözündürülmesi için işlem. |
US6476186B1 (en) | 2000-05-23 | 2002-11-05 | Institute Of Nuclear Energy Research | Process for preparing octreotide and derivatives thereof |
AU2001271301B2 (en) | 2000-06-14 | 2006-08-31 | Medarex, Inc. | Prodrug compounds cleavable by thimet oligopeptidase |
US20020058788A1 (en) | 2000-08-25 | 2002-05-16 | Sheppeck James E. | Facile deprotection of Fmoc protected amino groups |
NO314588B1 (no) | 2000-09-04 | 2003-04-14 | Bionor Immuno As | HIV-peptider, antigener, vaksinesammensetning, immunoassay- testsett og en fremgangsmåte for å påvise antistoffer indusert av HIV |
AU2002227925A1 (en) | 2000-11-14 | 2002-05-27 | Ipf Pharmaceuticals Gmbh | Human beta-defensin-3 |
JP2004513191A (ja) | 2001-01-04 | 2004-04-30 | カウンシル・オブ・サイエンティフィック・アンド・インダストリアル・リサーチ | ペプチドおよび小分子有機合成用の新しいリンカーに基づく固相支持体 |
US20090281032A1 (en) | 2001-03-01 | 2009-11-12 | Peter Raymond Flatt | Modified CCK peptides |
GB0105069D0 (en) | 2001-03-01 | 2001-04-18 | Univ Ulster The | Modified peptide |
BR0101088A (pt) | 2001-03-19 | 2003-03-18 | Biolab Sanus Farmaceutica Ltda | Processo de isolamento e purificação de peptìdeos inibidores das vasopeptidases, com especificidade para o sìtio carboxìlico da enzima conversora da angiotensina, secretados pelas glândulas do veneno de serpentes (bpps), particularmente bothrops jararaca, ou produzidos endogenamente (evasins) possuindo ação vasodilatadora e anti-hipertensiva; processo de determinação da sequência de amido-ácidos dos peptìdios inibidores secretados pela glândula de veneno de serpentes (bpps) ou endógenos (evasins); processo de determinação da sequência de aminoácidos dos bpps por dedução do cdna dos precursores dessas moléculas expressos em tecidos de serpentes, especificamente bothrops jararaca. processo de determinação da sequência de aminoácidos dos evasins por dedução do cdna dos precursores dessas moléculas expressos em tecidos de serpentes, especificamente bothrops jararaca, processo de amplificação do cdna a partir das bibliotecas de cdna de pâncreas e/ou cérebro de serpentes, especificamente bothrops jararaca; processo de sìntese em fase sólida de peptìdeos inibidores das vasopeptidases com ação vasodilatadora e anti-hipertensiva, peptìdeos inibidores das vasopeptidases com ação anti-hipertensiva; utilização dos peptìdeos inibidores das vaso peptidases com ação vasodilatadora e anti-hipertensiva na obtenção de composições farmacêuticas; processo de determinação da atividade inibitória sobre as vasopeptidases e de atividade biológica sobre músculo liso, sistema cardiovascular e microcirculatório. |
WO2002083606A1 (en) | 2001-04-17 | 2002-10-24 | University Of Alberta | A linker system for the synthesis and screening of combinatorial libraries of polyamine derivatives on water compatible supports |
CN1162446C (zh) | 2001-05-10 | 2004-08-18 | 上海华谊生物技术有限公司 | 促胰岛素分泌肽衍生物 |
FR2825095B1 (fr) | 2001-05-28 | 2003-09-26 | Dev Des Antigenes Combinatoire | Dispositif de presentation de polypeptides, utilisable comme "puce" pour la detection miniaturisee de molecules |
AU2002326103A1 (en) | 2001-08-24 | 2003-03-10 | University Of British Columbia | Solid-phase synthesis of oligosaccharides and glycopeptides using glycosynthases |
KR101036524B1 (ko) | 2002-04-11 | 2011-05-24 | 간가와 겐지 | 수식 펩티드의 제조 방법 |
US6809190B2 (en) | 2002-04-24 | 2004-10-26 | Credia Japan Co., Ltd. | Functional peptide nucleic acid and its production method |
AU2003227907A1 (en) | 2002-05-03 | 2003-11-17 | Avecia Limited | Process for the synthesis of peptides amides by side-chain attachement to a solid phase |
GB0210183D0 (en) | 2002-05-03 | 2002-06-12 | Avecia Ltd | Process |
GB0210185D0 (en) | 2002-05-03 | 2002-06-12 | Avecia Ltd | Process |
PL374438A1 (en) | 2002-05-10 | 2005-10-17 | Pharmacia Corporation | Peptide compounds and their use as protease substrates |
ES2195787B1 (es) | 2002-05-20 | 2005-06-01 | Diverdrugs, S.L. | Compuestos capaces de bloquear la respuesta a sustancias quimicas o estimulos termicos o mediadores de la inflamacion de los nociceptores, un metodo para su obtencion y composiciones que los continen. |
US20060217294A1 (en) | 2002-08-09 | 2006-09-28 | Yamanouchi Europe B.V. | Compounds binding to p-selectin |
EP1575990B1 (en) | 2002-09-08 | 2009-11-18 | Applera Corporation | Solid phase bound PNA-dimers and their synthesis |
RU2376314C2 (ru) | 2002-10-02 | 2009-12-20 | Зилэнд Фарма А/С | Стабилизированные соединения эксендина-4 |
EP1445260A1 (de) | 2003-02-04 | 2004-08-11 | Jerini AG | Verfahren zur Immobilisierung von chemischen Verbindungen an Festphasen |
CN1771080B (zh) | 2003-04-08 | 2010-12-15 | 诺沃挪第克公司 | 包括至少一个色谱处理步骤的生产治疗用多肽或其前体的方法 |
JP5274771B2 (ja) | 2003-04-08 | 2013-08-28 | ノヴォ ノルディスク アー/エス | クロマトグラフィー固定相の再生 |
WO2004092377A1 (ja) | 2003-04-15 | 2004-10-28 | Credia Japan Co., Ltd. | 新規な機能性ペプチド核酸およびその製法 |
WO2004105685A2 (en) | 2003-05-22 | 2004-12-09 | Gryphon Therapeutics, Inc. | Displaceable linker solid phase chemical ligation |
PL1633391T3 (pl) | 2003-06-03 | 2012-03-30 | Novo Nordisk As | Stabilizowane farmaceutycznie kompozycje peptydowe |
US7414106B2 (en) | 2003-06-19 | 2008-08-19 | Lawrence Livermore National Security, Llc | Synthesis of peptide α-thioesters |
US7902488B2 (en) | 2003-06-23 | 2011-03-08 | Cem Corporation | Microwave-assisted peptide synthesis |
US7393920B2 (en) | 2003-06-23 | 2008-07-01 | Cem Corporation | Microwave-assisted peptide synthesis |
WO2005019262A1 (en) | 2003-08-21 | 2005-03-03 | Novo Nordisk A/S | Purification of glucagon-like peptides |
ES2295961T3 (es) | 2003-12-31 | 2008-04-16 | F. Hoffmann-La Roche Ag | Proceso para la sintesis peptidica utilizacndo una cantidad reducida de agente de desproteccion. |
FR2864830B1 (fr) | 2004-01-06 | 2006-03-10 | Centre Nat Rech Scient | Procede de synthese sur support solide de composes peptidiques, notamment de composes peptidiques comportant un residu arginine |
WO2005080424A2 (en) | 2004-02-23 | 2005-09-01 | Rheoscience A/S | Peptide yy analogues |
CA2458084A1 (en) | 2004-03-12 | 2005-09-12 | Dalton Chemical Laboratories Inc. | Novel process for octreotide synthesis |
TW200611704A (en) | 2004-07-02 | 2006-04-16 | Bristol Myers Squibb Co | Human glucagon-like-peptide-1 modulators and their use in the treatment of diabetes and related conditions |
US7534763B2 (en) | 2004-07-02 | 2009-05-19 | Bristol-Myers Squibb Company | Sustained release GLP-1 receptor modulators |
KR101222837B1 (ko) | 2004-07-16 | 2013-01-15 | 론자 아게 | 펩티드 합성 방법 |
ATE496061T1 (de) | 2004-10-12 | 2011-02-15 | Hoffmann La Roche | Festphasenpeptidsynthese |
EP1814908A4 (en) | 2004-11-22 | 2009-07-01 | Biosight Ltd | Activated labeling reagents and method for their preparation and use |
US7745570B2 (en) | 2004-12-17 | 2010-06-29 | Kansas State University Research Foundation | PH dependent adhesive peptides |
JP4785206B2 (ja) | 2005-01-14 | 2011-10-05 | ウクスィ・グランドチャンプ・ファーマシューティカル・テクノロジー・カンパニー・リミテッド | 修飾されたエキセンディン(Exendins)及びその使用 |
US8716221B2 (en) | 2005-01-14 | 2014-05-06 | Wuxi Grandchamp Pharmaceutical Technology Co., Ltd. | Modified exendins and uses thereof |
JP2008534639A (ja) | 2005-04-08 | 2008-08-28 | ロンザ ア−ゲ− | Peg樹脂上におけるアルファ−ヘリックスのペプチド合成 |
CN101166761A (zh) | 2005-05-04 | 2008-04-23 | 隆萨股份公司 | 肽合成法 |
CN1298732C (zh) | 2005-05-17 | 2007-02-07 | 南京工业大学 | 多肽微波固相合成法 |
PE20061448A1 (es) | 2005-05-26 | 2006-12-17 | Bristol Myers Squibb Co | Compuestos polipeptidos como moduladores del peptido 1 similar al glucagon humano |
EP1805204A2 (en) | 2005-09-14 | 2007-07-11 | Novetide Ltd. | Process for production of bivalirudin |
HUE029798T2 (en) | 2005-11-04 | 2017-03-28 | Glaxosmithkline Llc | Methods of administering hypoglycemic agents |
CN100374462C (zh) | 2005-11-21 | 2008-03-12 | 大连帝恩生物工程有限公司 | 截短胰高血糖素样肽1(sGLP-1)、制法及其应用 |
US20090215025A1 (en) | 2005-12-07 | 2009-08-27 | Technische Universitat Munchen | Small peptidic and peptido-mimetic affinity ligands for factor viii and factor viii-like proteins |
CA2628159A1 (en) * | 2005-12-14 | 2007-06-21 | Medivir Ab | (2,5-dioxoimidazolidin-1-yl)-n-hydroxy-acetamides as metalloproteinase inhibitors |
US8058394B2 (en) | 2006-03-29 | 2011-11-15 | Otsuka Chemical Co., Ltd. | Method for production of peptide thioester compound |
ES2283212B1 (es) | 2006-03-31 | 2008-08-16 | Lipotec S.A. | Peptidos sinteticos utiles en el tratamiento de la piel y su uso en composiciones cosmeticas o dermofarmaceuticas. |
WO2007113386A1 (en) | 2006-03-31 | 2007-10-11 | Karyon-Ctt Ltd | Peptide conjugates |
EP2021014A1 (en) | 2006-05-26 | 2009-02-11 | Brystol-Myers Squibb Company | Sustained release glp-1 receptor modulators |
GB2440388A (en) | 2006-06-30 | 2008-01-30 | Ucl Biomedica Plc | Methods of linking a carbohydrate or polyalkylene oxide to a protein, precursors and the resultant products |
WO2008028974A1 (en) | 2006-09-08 | 2008-03-13 | Novo Nordisk A/S | Methods of optimizing chromatographic separation of polypeptides |
WO2008044890A1 (en) | 2006-10-12 | 2008-04-17 | Dong Kook Pharm. Co., Ltd | A method for preparing peptides using by solid phase synthesis |
ES2322882B1 (es) | 2006-10-25 | 2010-04-22 | Lipotec Sa | Peptidos inhibidores de la exocitosis neuronal. |
EP1923397B1 (en) | 2006-11-14 | 2009-10-28 | NERVIANO MEDICAL SCIENCES S.r.l. | Fluorinated amino acids and peptides |
TWI428346B (zh) | 2006-12-13 | 2014-03-01 | Imp Innovations Ltd | 新穎化合物及其等對進食行為影響 |
AU2007333846B2 (en) | 2006-12-14 | 2014-01-23 | Aileron Therapeutics, Inc. | Bis-sulfhydryl macrocyclization systems |
US7981998B2 (en) | 2006-12-14 | 2011-07-19 | Aileron Therapeutics, Inc. | Bis-sulfhydryl macrocyclization systems |
WO2008101017A2 (en) | 2007-02-15 | 2008-08-21 | Indiana Unversity Research And Technology Corporation | Glucagon/glp-1 receptor co-agonists |
US20080287650A1 (en) | 2007-03-01 | 2008-11-20 | Avi Tovi | High purity peptides |
WO2008137165A1 (en) | 2007-05-07 | 2008-11-13 | President And Fellows Of Harvard College | Anti-glycated cd59 antibodies and uses thereof |
ATE520714T1 (de) | 2007-06-15 | 2011-09-15 | Zealand Pharma As | Glucagonanaloga |
CN101790535A (zh) | 2007-06-29 | 2010-07-28 | 隆萨股份公司 | 制备普兰林肽的方法 |
CN101357937B (zh) | 2007-07-31 | 2012-11-07 | 上海苏豪逸明制药有限公司 | 固相多肽合成阿托西般的制备方法 |
CN101357938B (zh) | 2007-07-31 | 2013-07-03 | 周逸明 | 固相多肽合成Exenatide的制备方法 |
BRPI0820765A2 (pt) | 2007-12-11 | 2015-06-16 | Hoffmann La Roche | Métodos para a produção de um peptídeo insulinotrópico e peptídeos |
MX2010008655A (es) | 2008-02-06 | 2010-10-06 | Biocon Ltd | Un metodo para purificar un peptido. |
ES2330291B1 (es) | 2008-02-29 | 2010-10-18 | Lipotec Sa | Peptidos utiles en el tratamiento de la piel, mucosas y/o cuero cabelludo y su uso en composiciones cosmeticas o farmaceuticas. |
CN101525370A (zh) | 2008-03-06 | 2009-09-09 | 海南建邦制药科技有限公司 | 一种新型高效多肽合成缩合剂 |
CN101525368B (zh) | 2008-03-06 | 2012-05-30 | 海南建邦制药科技有限公司 | 一种多肽合成脱保护剂 |
CN101255191A (zh) | 2008-03-12 | 2008-09-03 | 中国药科大学 | 微波促进固相合成胰高血糖素样肽-1(glp-1)类似物及其应用 |
US9662370B2 (en) | 2008-04-24 | 2017-05-30 | Therimunex Pharmaceuticals, Inc. | Peptidyl diacylglycerides |
WO2009138488A1 (en) | 2008-05-15 | 2009-11-19 | Novo Nordisk A/S | Purification of peptides prepared by solid phase synthesis |
WO2010011439A2 (en) | 2008-06-17 | 2010-01-28 | Indiana University Research And Technology Corporation | Gip-based mixed agonists for treatment of metabolic disorders and obesity |
EP2676673B1 (en) | 2008-06-17 | 2016-11-16 | Indiana University Research and Technology Corporation | Glucagon/glp-1 receptor co-agonists |
WO2010028122A1 (en) | 2008-09-03 | 2010-03-11 | Scinopharm Taiwan Ltd. | Process for making bivalirudin |
EP2342221B1 (en) | 2008-09-22 | 2018-11-07 | Aileron Therapeutics, Inc. | Methods for preparing purified polypeptide compositions |
TW201012829A (en) | 2008-09-22 | 2010-04-01 | Ipsen Mfg Ireland Ltd | Process for the synthesis of (Aib8,35)hGLP-1(7-36)-NH2 |
CN102272163A (zh) | 2008-12-05 | 2011-12-07 | 安吉奥开米公司 | 瘦素和瘦素类似物结合物及其用途 |
CN102307904A (zh) | 2008-12-05 | 2012-01-04 | 安吉奥开米公司 | 神经降压素或神经降压素类似物的缀合物及其用途 |
CA2745499A1 (en) | 2008-12-05 | 2010-06-10 | Angiochem Inc. | Peptide therapeutic conjugates and uses thereof |
BRPI0823378A2 (pt) | 2008-12-15 | 2019-09-24 | Zealand Pharma As | análogos de glucagon |
BRPI0823377A2 (pt) | 2008-12-15 | 2016-09-27 | Zealand Pharma As | análogos de glucagon |
BRPI0823376A2 (pt) | 2008-12-15 | 2015-06-16 | Zealand Pharma As | Análagos de glucagon |
ES2439499T3 (es) | 2008-12-15 | 2014-01-23 | Zealand Pharma A/S | Análogos de glucagón |
CN101463078B (zh) | 2009-01-12 | 2011-07-27 | 华东师范大学 | 一种Exendin-4衍生物及其固相化学合成 |
CN101463081B (zh) | 2009-01-12 | 2012-07-04 | 华东师范大学 | 一种glp-1衍生物 |
CN101538324B (zh) | 2009-01-13 | 2013-01-16 | 深圳翰宇药业股份有限公司 | 一种制备艾塞那肽的方法 |
ES2349972B1 (es) | 2009-02-16 | 2011-11-24 | Lipotec, S.A. | Péptidos útiles en el tratamiento y/o cuidado de la piel, mucosas y/o cuero cabelludo y su uso en composiciones cosméticas o farmacéuticas. |
WO2010096052A1 (en) | 2009-02-19 | 2010-08-26 | Merck Sharp & Dohme Corp. | Oxyntomodulin analogs |
US20120021029A1 (en) | 2009-04-17 | 2012-01-26 | Lipotec, S.A. | Peptides used in the treatment and/or care of the skin and/or hair and their use in cosmetic or pharmaceutical compositions |
CN101555274B (zh) | 2009-05-15 | 2013-08-21 | 海南双成药业股份有限公司 | 一种多肽固相合成比法卢定粗品的制备方法 |
PE20120914A1 (es) | 2009-06-16 | 2012-08-22 | Univ Indiana Res & Tech Corp | Compuestos glucagon activo de receptor de gip |
KR101809024B1 (ko) | 2009-07-13 | 2017-12-14 | 질랜드 파마 에이/에스 | 아실화 글루카곤 유사체 |
JP5782439B2 (ja) | 2009-07-24 | 2015-09-24 | リポテック, エセ.ア.Lipotec, S.A. | 筋肉収縮を抑制する化合物 |
CN101987865B (zh) | 2009-07-29 | 2014-07-30 | 中国人民解放军军事医学科学院毒物药物研究所 | 含有乙内酰脲结构的促***释放激素拮抗剂 |
ES2358829B1 (es) | 2009-10-23 | 2012-06-25 | Lipotec, S.A. | Péptidos útiles en el tratamiento y/o cuidado de la piel, mucosas y/o cabello y su uso en composiciones cosméticas o farmacéuticas. |
WO2011075393A2 (en) | 2009-12-18 | 2011-06-23 | Indiana University Research And Technology Corporation | Glucagon/glp-1 receptor co-agonists |
IN2012DN06437A (es) | 2010-01-27 | 2015-10-09 | Univ Indiana Res & Tech Corp | |
US9422330B2 (en) | 2010-03-01 | 2016-08-23 | Novo Nordisk A/S | Preparative RP-HPLC method for purifying peptides |
US8620595B2 (en) | 2010-03-26 | 2013-12-31 | University Of Manitoba | Methods for determining the retention of peptides in reverse phase chromatography using linear solvent strength theory |
US20130143798A1 (en) | 2010-03-26 | 2013-06-06 | Novo Nordisk A/S | Novel glucagon analogues |
AR080592A1 (es) | 2010-03-26 | 2012-04-18 | Lilly Co Eli | Peptido con actividad para el gip-r y glp-1-r, formulacion famaceutica que lo comprende, su uso para preparar un medicamento util para el tratamiento de diabetes mellitus y para inducir la perdida de peso |
US20130059093A1 (en) | 2010-05-31 | 2013-03-07 | Jtekt Corporation | Method of producing coated member |
EP2579435B1 (en) | 2010-06-01 | 2016-11-30 | Honda Motor Co., Ltd. | Controller for dc/dc converter |
US20110313131A1 (en) | 2010-06-21 | 2011-12-22 | Christelle Carl | Reversed phase hplc purification of a glp-1 analogue |
AR081975A1 (es) | 2010-06-23 | 2012-10-31 | Zealand Pharma As | Analogos de glucagon |
CN101906150B (zh) | 2010-06-28 | 2013-01-09 | 上海昂博生物技术有限公司 | 一种比法卢定的制备方法 |
WO2012057624A1 (en) | 2010-10-25 | 2012-05-03 | Pepscan Systems B.V. | Novel bicyclic peptide mimetics |
SG190066A1 (en) | 2010-10-29 | 2013-06-28 | Lonza Ag | Diketopiperazine forming dipeptidyl linker |
US8507428B2 (en) | 2010-12-22 | 2013-08-13 | Indiana University Research And Technology Corporation | Glucagon analogs exhibiting GIP receptor activity |
WO2012085279A2 (en) | 2010-12-23 | 2012-06-28 | Universiteit Gent | Method for cross-linking peptides |
CN102643339B (zh) | 2011-02-21 | 2014-04-09 | 天津药物研究院 | 一种glp-1类似物、制备方法及其应用 |
CN102174082B (zh) | 2011-02-23 | 2014-08-27 | 上海昂博生物技术有限公司 | 一种艾塞那肽的制备方法 |
ES2397889B1 (es) | 2011-03-25 | 2014-02-07 | Lipotec, S.A. | PÉPTIDOS MODULADORES DE PGC-1Alfa. |
CN102718858B (zh) | 2011-03-29 | 2014-07-02 | 天津药物研究院 | 胰高血糖素样肽-1类似物单体、二聚体及其制备方法与应用 |
EP2694095B1 (en) | 2011-04-05 | 2018-03-07 | Longevity Biotech, Inc. | Compositions comprising glucagon analogs and methods of making and using the same |
CN102786590A (zh) | 2011-05-19 | 2012-11-21 | 江苏豪森药业股份有限公司 | 分枝型peg修饰的glp-1类似物及其可药用盐 |
US8933196B2 (en) | 2011-05-20 | 2015-01-13 | National Central University | Peptide chromatographic purification assisted by combining of solubility parameter and solution conformation energy calculations |
CN102286076B (zh) | 2011-06-23 | 2014-03-12 | 成都圣诺科技发展有限公司 | 比伐卢定的制备方法 |
CN102286092B (zh) | 2011-09-14 | 2014-01-01 | 深圳翰宇药业股份有限公司 | 利拉鲁肽的固相合成方法 |
NL2007536C2 (en) | 2011-10-05 | 2013-04-08 | Academisch Ziekenhuis Leiden Lumc | Adjuvant compound. |
MX350536B (es) | 2011-12-23 | 2017-09-08 | Ipsen Mfg Ireland Limited | Proceso para la sintesis de peptidos terapeuticos. |
CN102584944B (zh) | 2012-02-06 | 2014-12-17 | 成都圣诺生物科技股份有限公司 | 一种依非巴特的制备方法 |
CN103242443A (zh) | 2012-02-06 | 2013-08-14 | 长春百克生物科技股份公司 | 一种胸腺素α1及其类似物的制备方法 |
CN102558338B (zh) | 2012-02-10 | 2014-09-17 | 深圳翰宇药业股份有限公司 | 一种合成利西拉来的方法 |
CN102584982B (zh) | 2012-02-10 | 2014-02-05 | 深圳翰宇药业股份有限公司 | 一种纯化固相合成利拉鲁肽粗肽的方法 |
US9725483B2 (en) | 2012-04-16 | 2017-08-08 | Lipotec, S.A. | Compounds for the treatment and/or care of the skin and/or mucous membranes and their use in cosmetic or pharmaceutical compositions |
US20130289241A1 (en) | 2012-04-26 | 2013-10-31 | Shanghai Ambiopharm, Inc. | Method for preparing exenatide |
JP6522496B2 (ja) | 2012-05-16 | 2019-05-29 | ノクソン ファーマ エージー | L−核酸の酵素性合成 |
CN102875663B (zh) | 2012-09-26 | 2014-06-11 | 深圳翰宇药业股份有限公司 | 利西拉来的纯化方法 |
EP2950904A1 (en) | 2013-01-29 | 2015-12-09 | Neuland Health Sciences Private Limited | Purification of organic compounds using surrogate stationary phases on reversed phase columns |
CN103965285B (zh) | 2013-02-06 | 2016-12-28 | 北京大学 | 一种以超顺磁纳米颗粒为固相进行多肽合成及同步构建多肽磁纳米探针的方法 |
CN103333237B (zh) | 2013-05-07 | 2015-03-11 | 海南双成药业股份有限公司 | 一种固相片段法合成艾塞那肽 |
SG11201600272WA (en) | 2013-07-15 | 2016-02-26 | Univ North Carolina State | Protease-resistant peptide ligands |
US9263194B2 (en) | 2013-09-06 | 2016-02-16 | Gwangju Institute Of Science And Technology | Porphyrin-peptoid conjugate and the preparation process thereof |
WO2015038919A1 (en) | 2013-09-15 | 2015-03-19 | Stc. Unm | Method for atomic layer deposition |
CN103536912B (zh) | 2013-09-30 | 2015-05-13 | 重庆理工大学 | 一种猪圆环病毒2型表位肽疫苗及其制备方法 |
CN103613655B (zh) | 2013-11-20 | 2015-05-13 | 陕西东大生化科技有限责任公司 | 一种低成本纯化艾塞那肽的方法 |
US20160303245A1 (en) | 2013-12-01 | 2016-10-20 | University Of Copenhagen | Fatty acid derivatives of dimeric inhibitors of psd-95 |
HU230584B1 (hu) | 2014-02-28 | 2017-01-30 | Szegedi Tudományegyetem | Eljárás peptidek előállítására |
CN104086631A (zh) | 2014-07-10 | 2014-10-08 | 成都天台山制药有限公司 | 卡贝缩宫素和制法 |
CN104211801A (zh) | 2014-07-25 | 2014-12-17 | 杭州诺泰制药技术有限公司 | 一种制备利西拉来的方法 |
TR201815872T4 (tr) | 2014-08-07 | 2018-11-21 | Hoffmann La Roche | Oksitosin analoglarının hazırlanması için prosesler. |
JP6574257B2 (ja) | 2014-10-07 | 2019-09-11 | アン アンド ロバート エイチ. ルーリー チルドレンズ ホスピタル オブ シカゴ | 新規の抗Nodal抗体及びその使用方法 |
CN105585612B (zh) | 2014-10-20 | 2020-05-05 | 北京益生康华医药技术有限公司 | 八肽修饰的***、制备、纳米结构和应用 |
WO2016067271A1 (en) | 2014-10-31 | 2016-05-06 | Auro Peptides Ltd | A process for the preparation of liraglutide |
WO2016084100A2 (en) | 2014-11-26 | 2016-06-02 | Alaparthi Lakshmi Prasad | Novel and efficient method for large scale synthesis of romidepsin |
US10308677B2 (en) | 2014-12-19 | 2019-06-04 | Cem Corporation | Coupling method for peptide synthesis at elevated temperatures |
CN105111303B (zh) | 2015-06-23 | 2019-07-26 | 济南康和医药科技有限公司 | 一种固液结合制备利拉鲁肽的方法 |
US10690635B2 (en) | 2016-03-23 | 2020-06-23 | Bachem Holding Ag | Purification of glucagon-like peptide 1 analogs |
-
2014
- 2014-03-19 CA CA2907454A patent/CA2907454C/en active Active
- 2014-03-19 CN CN201480016500.2A patent/CN105189465B/zh active Active
- 2014-03-19 HU HUE14710915A patent/HUE034308T2/en unknown
- 2014-03-19 US US14/778,496 patent/US10087221B2/en active Active
- 2014-03-19 WO PCT/EP2014/055506 patent/WO2014147124A1/en active Application Filing
- 2014-03-19 MX MX2015013464A patent/MX363522B/es unknown
- 2014-03-19 SG SG11201506804VA patent/SG11201506804VA/en unknown
- 2014-03-19 ES ES14710915.1T patent/ES2623979T3/es active Active
- 2014-03-19 EP EP14710915.1A patent/EP2976331B1/en active Active
- 2014-03-19 AU AU2014234400A patent/AU2014234400B2/en active Active
-
2016
- 2016-06-27 HK HK16107440.3A patent/HK1219477A1/zh unknown
Also Published As
Publication number | Publication date |
---|---|
WO2014147124A1 (en) | 2014-09-25 |
US10087221B2 (en) | 2018-10-02 |
MX2015013464A (es) | 2016-06-21 |
HK1219477A1 (zh) | 2017-04-07 |
MX363522B (es) | 2019-03-26 |
CA2907454A1 (en) | 2014-09-25 |
CN105189465A (zh) | 2015-12-23 |
HUE034308T2 (en) | 2018-02-28 |
AU2014234400A1 (en) | 2015-10-01 |
SG11201506804VA (en) | 2015-09-29 |
CN105189465B (zh) | 2019-02-26 |
CA2907454C (en) | 2021-05-04 |
AU2014234400B2 (en) | 2017-11-16 |
US20160289282A1 (en) | 2016-10-06 |
EP2976331B1 (en) | 2017-03-01 |
EP2976331A1 (en) | 2016-01-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11759509B2 (en) | WT1 antigen peptide conjugate vaccine | |
EP2849882B1 (en) | Lysin-glutamic acid dipeptide derivatives | |
BR112016009207A8 (pt) | compostos de prostaciclina | |
US8987413B2 (en) | Aldehyde acetal based processes for the manufacture of macrocyclic depsipeptides and new intermediates | |
AR055179A1 (es) | Procedimiento para la amidacion de polipeptidos con aminoacidos de caracter basico c-terminales mediante el uso de endoproteasas especificas | |
ES2828526T3 (es) | Esteres activos DCHBS de compuestos PEG y sus usos | |
US20240033318A1 (en) | Peptidyl inhibitors of calcineurin-nfat interaction | |
ES2623979T3 (es) | Síntesis de productos peptídicos que contienen hidantoína | |
ES2682253T3 (es) | Dipéptido que comprende un aminoácido no proteogénico | |
ES2715082T3 (es) | Método de producción de un pentapéptido sintético | |
ES2410267T3 (es) | Dipéptidos de pseudoprolina | |
Tung et al. | Peptide 2-formylthiophenol esters do not proceed through a Ser/Thr ligation pathway, but participate in a peptide aminolysis to enable peptide condensation and cyclization | |
KR102056257B1 (ko) | 베타-턴 펩티도미메틱 사이클릭 염의 용액상 합성 및 결정화 | |
Seyberth et al. | Lipolanthionine peptides act as inhibitors of TLR2-mediated IL-8 secretion. Synthesis and structure− activity relationships | |
CA2909584C (en) | Synthesis of beta-turn peptidomimetic cyclic compounds | |
ES2957487T3 (es) | Método para la escisión del grupo Fmoc | |
AR246087A1 (es) | Procedimiento para preparar derivados de peptidos ciclicos que son antagonistas de la neuroquinina a y sus sales farmaceuticamente aceptables. | |
HU224571B1 (hu) | Eljárás enantiomerek elválasztására, és enantiomertiszta reagensek | |
Li et al. | A silver-promoted solid-phase guanidylation process enables the first total synthesis of stictamide A | |
Isidro et al. | 1, 2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine | |
KR102092817B1 (ko) | 아마톡신 유도체 및 이의 제조방법 | |
JP2016190813A (ja) | 新規膜透過性ペプチド | |
HUT70189A (en) | Process for producing tachykinin antagonist tricyclic compounds and pharmaceutical compositions containing them | |
Lukowiak et al. | Synthesis and pharmacological properties of a new fluorescent opioid peptide analog | |
Brosseau et al. | Development of an efficient strategy for the synthesis of the ETB receptor antagonist BQ-788 and some related analogues |