HRP20140487T1 - Postupak dobivanja perindoprila i njegovih soli - Google Patents
Postupak dobivanja perindoprila i njegovih soli Download PDFInfo
- Publication number
- HRP20140487T1 HRP20140487T1 HRP20140487TT HRP20140487T HRP20140487T1 HR P20140487 T1 HRP20140487 T1 HR P20140487T1 HR P20140487T T HRP20140487T T HR P20140487TT HR P20140487 T HRP20140487 T HR P20140487T HR P20140487 T1 HRP20140487 T1 HR P20140487T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- perindopril
- image
- salt
- acid chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 title claims 6
- 229960002582 perindopril Drugs 0.000 title claims 5
- 150000003839 salts Chemical class 0.000 title claims 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 238000006664 bond formation reaction Methods 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (6)
1. Postupak dobivanja perindoprila formule I, ili njegovih farmaceutski prihvatljivih soli:
[image]
,
naznačen time što sol kiselinskog klorida formule III
[image]
reagira s (2S,3aS,7aS)-oktahidroindol-2-karboksilnom kiselinom formule IV
[image]
,
gdje R predstavlja trimetilsililnu skupinu, a R1 predstavlja vodik ili zaštitnu skupinu, poput trimetilsililne skupine,
u spoj formule V:
[image]
,
gdje R ima gore navedeno značenje,
kojeg se hidrolizom prevodi u perindopril formule I,
gdje se reakciju tvorbe peptidne veze provodi u organskim otapalima, poput acetona, acetonitrila, dioksana, kloroforma, metilen-klorida, tetrahidrofurana, ili u njihovoj smjesi s vodom, u prisutnosti baze.
2. Postupak u skladu s patentnim zahtjevom 1 naznačen time što se kiselinski klorid formule III:
[image]
dobiva prevođenjem N-((S)-1-(etoksikarbonil)butil)-1-alanina formule II:
[image]
.
3. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se upotrebljava hidrokloridna sol kiselinskog klorida III.
4. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što se reakcija tvorbe peptidne veze provodi u rasponu temperatura od –20 °C do +20 °C, po mogućnosti na temperaturi od 0 °C do –20 °C.
5. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što se nakon reakcije hidrolize dobiveni perindopril formule I prevodi u sol perindoprila.
6. Postupak u skladu s patentnim zahtjevom 5, naznačen time što je sol perindoprila sol s t-butilaminom.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200400143A SI21800A (sl) | 2004-05-14 | 2004-05-14 | Nov postopek sinteze perindoprila |
| SI200400235A SI21852A (sl) | 2004-05-14 | 2004-08-05 | Nov postopek sinteze perindoprila |
| PCT/EP2005/005048 WO2005113500A1 (en) | 2004-05-14 | 2005-05-10 | Process for the preparation of perindopril and salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20140487T1 true HRP20140487T1 (hr) | 2014-07-04 |
Family
ID=34969318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20140487TT HRP20140487T1 (hr) | 2004-05-14 | 2014-05-29 | Postupak dobivanja perindoprila i njegovih soli |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7674814B2 (hr) |
| EP (1) | EP1753720B1 (hr) |
| JP (1) | JP5032983B2 (hr) |
| AU (1) | AU2005245087B2 (hr) |
| CA (1) | CA2566754C (hr) |
| CY (1) | CY1115222T1 (hr) |
| DK (1) | DK1753720T3 (hr) |
| EA (1) | EA011322B1 (hr) |
| ES (1) | ES2466248T3 (hr) |
| HR (1) | HRP20140487T1 (hr) |
| NO (1) | NO337892B1 (hr) |
| PL (1) | PL1753720T3 (hr) |
| PT (1) | PT1753720E (hr) |
| SI (3) | SI21800A (hr) |
| UA (1) | UA83139C2 (hr) |
| WO (1) | WO2005113500A1 (hr) |
| ZA (1) | ZA200609915B (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA011712B1 (ru) * | 2004-03-29 | 2009-04-28 | Ле Лаборатуар Сервье | Способ производства твёрдой фармацевтической композиции |
| US7291745B2 (en) | 2005-03-21 | 2007-11-06 | Glenmark Pharmaceuticals Limited | Process for the preparation of perindopril |
| JP2006290825A (ja) * | 2005-04-13 | 2006-10-26 | Shiono Chemical Co Ltd | アルファ型ペリンドプリルエルブミンの製造法 |
| SI22543A (sl) | 2007-06-27 | 2008-12-31 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Nove soli perindoprila |
| WO2016178591A2 (en) | 2015-05-05 | 2016-11-10 | Gene Predit, Sa | Genetic markers and treatment of male obesity |
| FR3050380B1 (fr) | 2016-04-20 | 2020-07-10 | Les Laboratoires Servier | Composition pharmaceutique comprenant un betabloquant, un inhibiteur de l'enzyme de conversion et un antihypertenseur ou un ains. |
| JP7070831B2 (ja) | 2018-05-31 | 2022-05-18 | 株式会社富士通ゼネラル | 天井埋込型空気調和機 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2503155A2 (fr) | 1980-10-02 | 1982-10-08 | Science Union & Cie | Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme |
| US4508729A (en) | 1979-12-07 | 1985-04-02 | Adir | Substituted iminodiacids, their preparation and pharmaceutical compositions containing them |
| US4350704A (en) | 1980-10-06 | 1982-09-21 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids |
| IE52663B1 (en) | 1980-04-02 | 1988-01-20 | Warner Lambert Co | Substituted acyl derivatives of octahydro-1h-indole-2-carboxylic acids |
| US4425355A (en) | 1981-02-17 | 1984-01-10 | Warner-Lambert Company | Substituted acyl derivatives of chair form of octahydro-1H-indole-2-carboxylic acids |
| US4743450A (en) | 1987-02-24 | 1988-05-10 | Warner-Lambert Company | Stabilized compositions |
| FR2620700B1 (fr) | 1987-09-17 | 1990-06-01 | Adir | Procede de synthese d'alpha amino acides n alkyles et leurs esters. application a la synthese de carboxyalkyl dipeptides |
| FR2620699B1 (fr) | 1987-09-17 | 1990-06-01 | Adir | Procede de synthese d'alpha amino acides n alkyles et de leurs esters. application a la synthese de carboxyalkyl dipeptides |
| FR2620703B1 (fr) | 1987-09-17 | 1991-10-04 | Adir | Procede de synthese industrielle de l'acide perhydroindole carboxylique - 2(2s, 3as, 7as). application a la synthese de carboxyalkyl dipeptides |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| US5258525A (en) | 1991-03-27 | 1993-11-02 | Mcneilab, Inc. | Processes for preparing [2S-(2α,3aβ,7aβ)]octahydro-1H-indole-2-carboxylic acid and esters |
| SI9111842A (sl) | 1991-11-25 | 1998-04-30 | Krka | Stabilna formulacija soli enalaprila, postopek za njeno pripravo in njena uporaba |
| SI9600169A (en) * | 1996-05-22 | 1997-12-31 | Krka Tovarna Zdravil | Process for preparation of compounds with ace inhibitory effect |
| FR2771010B1 (fr) | 1997-11-19 | 2003-08-15 | Adir | Utilisation d'une combinaison d'un inhibiteur de l'enzyme de conversion de l'angiotensine et d'un diuretique pour le traitement des desordres microcirculatoires |
| FR2807037B1 (fr) | 2000-03-31 | 2002-05-10 | Adir | NOUVEAU PROCEDE DE SYNTHESE DES ESTERS DE LA N-[(s)-1- CARBOXYBUTYL]-(S)-ALANINE ET APPLICATION A LA SYNTHESE DU PERINDOPRIL |
| FR2807431B1 (fr) | 2000-04-06 | 2002-07-19 | Adir | Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables |
| FR2807430B1 (fr) | 2000-04-11 | 2002-05-17 | Adir | Nouveau procede de synthese des esters de la n-[(s)-1- carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
| FR2811319B1 (fr) | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline beta du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811318B1 (fr) | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2811320B1 (fr) | 2000-07-06 | 2002-08-23 | Adir | Nouvelle forme cristalline alpha du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| DE10131217A1 (de) | 2001-06-28 | 2003-01-09 | Solvay Pharm Gmbh | 3-Phenyl-3,7-diazabicyclo 3,3,1 nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| AU2002334939A1 (en) | 2001-10-12 | 2003-04-22 | Eugene R. Cooper | Compositions having a combination of particles for immediate release and for controlled release |
| DE60312857T2 (de) | 2002-01-15 | 2008-01-17 | Actavis Group Hf. | Formulierungen von quinapril und verwandte ace-hemmer |
| EP1333026B1 (en) | 2002-01-30 | 2007-06-27 | Les Laboratoires Servier | Process for the preparation of high purity perindopril and intermediates useful in the synthesis |
| AU2003217916A1 (en) | 2002-03-08 | 2003-09-22 | Teva Pharmeceuticals Usa, Inc. | Stable formulations of angiotensin converting enzyme (ace) inhibitors |
| FR2838648B1 (fr) | 2002-04-18 | 2004-05-21 | Servier Lab | Nouveau sel de perindopril et les compositions pharmaceutiques qui le contiennent |
| WO2003103632A1 (en) | 2002-06-10 | 2003-12-18 | Elan Pharma International, Ltd. | Nanoparticulate polycosanol formulations and novel polycosanol combinations |
| CA2511004C (en) * | 2002-12-23 | 2015-07-21 | Power Measurement Ltd. | Power monitoring integrated circuit with communication interface |
| ES2307923T3 (es) * | 2003-02-28 | 2008-12-01 | Les Laboratoires Servier S.A. | Procedimiento de preparacion de perindopril y sales del mismo. |
| DK1338591T3 (da) | 2003-02-28 | 2006-01-23 | Servier Lab | Fremgangsmåde til syntese af (2S,3aS,7aS)-perhydroindol-2-carboxylsyre og estere heraf samt anvendelse heraf ved syntese af perindopril |
| ATE281465T1 (de) | 2003-03-12 | 2004-11-15 | Servier Lab | Verfahren zur synthese von (2s,3as,7as)- perhydroindol-2-carbonsäure und seiner estern, und verwendung in der synthese von perindopril |
| SI1367061T1 (sl) * | 2003-06-30 | 2006-04-30 | Servier Lab | Nov postopek za sintezo perindoprila in njegovih farmacevtsko sprejemljivih soli |
| US6869963B2 (en) | 2003-07-11 | 2005-03-22 | Sandoz Ag | Stable pharmaceutical compositions containing an ACE inhibitor |
| GB2404336A (en) | 2003-07-30 | 2005-02-02 | Cipla Ltd | Stabilisation of therapeutic agents using a carbonate salt of an amino acid, preferably in the presence of a saccharide, & pharmaceutical compositions thereof |
| ATE338058T1 (de) * | 2003-07-31 | 2006-09-15 | Servier Lab | Verfahren für die synthese von perindopril und seiner pharmazeutischen annehmbaren salzen |
| ATE337332T1 (de) * | 2003-07-31 | 2006-09-15 | Servier Lab | Verfahren für die synthese von perindopril und seiner pharmazeutischen annehmbaren salzen |
| PT1362845E (pt) | 2003-09-01 | 2009-11-05 | Servier Lab | Novo processo de síntese dos ésteres da n-((s)-1- carboxibutil)-(s)-alanina e aplicação à síntese do perindopril |
| EP1403278B1 (fr) | 2003-09-30 | 2005-06-08 | Les Laboratoires Servier | Procédé de synthèse de la N-((S)-1-carbéthoxybutyl)-(S)-alanine et application à la synthèse du perindopril |
| EP1400531B1 (fr) | 2003-09-30 | 2006-01-04 | Les Laboratoires Servier | Procédé de synthèse de la N-[(S)-1-carbéthoxybutyl]-(S)-alanine et application à la synthèse du perindopril |
| GB2394660A (en) | 2003-12-17 | 2004-05-05 | Niche Generics Ltd | Stabilisation of pharmaceutical compositions comprising ACE inhibitor by absence of acidic excipients having large specific surface area, eg silicon dioxide |
| EA011712B1 (ru) | 2004-03-29 | 2009-04-28 | Ле Лаборатуар Сервье | Способ производства твёрдой фармацевтической композиции |
-
2004
- 2004-05-14 SI SI200400143A patent/SI21800A/sl not_active IP Right Cessation
- 2004-08-05 SI SI200400235A patent/SI21852A/sl not_active IP Right Cessation
-
2005
- 2005-05-10 JP JP2007512069A patent/JP5032983B2/ja not_active Expired - Fee Related
- 2005-05-10 UA UAA200613250A patent/UA83139C2/uk unknown
- 2005-05-10 US US11/568,908 patent/US7674814B2/en not_active Expired - Fee Related
- 2005-05-10 EP EP05748048.5A patent/EP1753720B1/en active Active
- 2005-05-10 PT PT57480485T patent/PT1753720E/pt unknown
- 2005-05-10 AU AU2005245087A patent/AU2005245087B2/en not_active Ceased
- 2005-05-10 CA CA2566754A patent/CA2566754C/en not_active Expired - Fee Related
- 2005-05-10 DK DK05748048.5T patent/DK1753720T3/da active
- 2005-05-10 PL PL05748048T patent/PL1753720T3/pl unknown
- 2005-05-10 WO PCT/EP2005/005048 patent/WO2005113500A1/en active Application Filing
- 2005-05-10 SI SI200531867T patent/SI1753720T1/sl unknown
- 2005-05-10 EA EA200602117A patent/EA011322B1/ru not_active IP Right Cessation
- 2005-05-10 ES ES05748048.5T patent/ES2466248T3/es active Active
-
2006
- 2006-11-28 ZA ZA200609915A patent/ZA200609915B/en unknown
- 2006-12-11 NO NO20065695A patent/NO337892B1/no not_active IP Right Cessation
-
2014
- 2014-05-29 HR HRP20140487TT patent/HRP20140487T1/hr unknown
- 2014-07-01 CY CY20141100483T patent/CY1115222T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007537189A (ja) | 2007-12-20 |
| CA2566754A1 (en) | 2005-12-01 |
| SI1753720T1 (sl) | 2014-08-29 |
| SI21852A (sl) | 2006-02-28 |
| ES2466248T3 (es) | 2014-06-09 |
| EP1753720B1 (en) | 2014-05-07 |
| WO2005113500A1 (en) | 2005-12-01 |
| DK1753720T3 (da) | 2014-06-30 |
| NO20065695L (no) | 2006-12-11 |
| AU2005245087B2 (en) | 2010-12-16 |
| PT1753720E (pt) | 2014-08-04 |
| US7674814B2 (en) | 2010-03-09 |
| JP5032983B2 (ja) | 2012-09-26 |
| CA2566754C (en) | 2012-09-18 |
| EA011322B1 (ru) | 2009-02-27 |
| AU2005245087A1 (en) | 2005-12-01 |
| EA200602117A1 (ru) | 2007-04-27 |
| CY1115222T1 (el) | 2017-01-04 |
| SI21800A (sl) | 2005-12-31 |
| EP1753720A1 (en) | 2007-02-21 |
| ZA200609915B (en) | 2008-05-28 |
| US20080051584A1 (en) | 2008-02-28 |
| NO337892B1 (no) | 2016-07-04 |
| UA83139C2 (uk) | 2008-06-10 |
| PL1753720T3 (pl) | 2014-09-30 |
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