AR043567A1 - Procedimiento para la sintesis de perindopril y sales farmaceuticamente aceptables del mismo - Google Patents
Procedimiento para la sintesis de perindopril y sales farmaceuticamente aceptables del mismoInfo
- Publication number
- AR043567A1 AR043567A1 ARP040100804A ARP040100804A AR043567A1 AR 043567 A1 AR043567 A1 AR 043567A1 AR P040100804 A ARP040100804 A AR P040100804A AR P040100804 A ARP040100804 A AR P040100804A AR 043567 A1 AR043567 A1 AR 043567A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- defined above
- perindopril
- synthesis
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Hospice & Palliative Care (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Procedimiento para la síntesis de perindopril y sales farmacéuiticas aceptables del mismo. Reivindicación 1: Procedimiento para la síntesis del compuesto de fórmula (1), y sales farmacéuticamente aceptables del mismo, caracterizado porque 2,7-oxepandiona de fórmula (2), se somete a reacción con el compuesto de fórmula (3), donde Bn representa un grupo bencilo, BOC representa un grupo terc-butoxicarbonilo y X representa un átomo de bromo o yodo, en presencia de zinc o amalgama de zinc/cobre, para obtener, después de la desprotección de la función amina, el compuesto de fórmula (4), donde Bn es tal como se ha definido anteriormente, que se cicliza por reacción con un reactivo de cloración, como ser cloruro de tionilo o cloruro de oxalilo, o con un agente de acoplamiento peptídico para obtener el compuesto de fórmula (5), donde Bn es tal como se ha definido anteriormente, que se somete a una reacción de acoplamiento en presencia de titanio para obtener el compuesto de fórmula (6), donde Bn es tal como se ha definido anteriormente, que se comete a reacción con el compuesto de fórmula (7), en acetato de etilo, en presencia de una cantidad de 1-hidroxibenzotriazol que oscila entre 0,4 y 0,6 mol por mol de compuesto de fórmula (6) utilizado, y una cantidad de diciclohexilcarbodiimida que oscila entre 1 y 1,2 mol por mol de compuesto de fórmula (6) utilizado, en presencia de una cantidad de trietilamina que oscila entre 0,25 y 1,2 mol por mol del compuesto de fórmula (6) utilizado, a una temperatura que oscila entre 20 y 77° C, para obtener, después del aislamiento, el compuesto de fórmula (8), donde Bn es tal como se ha definido anteriormente, que se hidrogena en presencia de un catalizador como ser paladio, platino, rodio o níquel, bajo una presión de hidrógeno que oscila entre 1 y 30 bares, para obtener perindopril de fórmula (2), que se convierte, si se desea, en una sal farmacéuticamente aceptable como ser la sal de terc-butilamina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03290605A EP1321471B1 (fr) | 2003-03-12 | 2003-03-12 | Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR043567A1 true AR043567A1 (es) | 2005-08-03 |
Family
ID=8185877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040100804A AR043567A1 (es) | 2003-03-12 | 2004-03-12 | Procedimiento para la sintesis de perindopril y sales farmaceuticamente aceptables del mismo |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1321471B1 (es) |
| AR (1) | AR043567A1 (es) |
| AT (1) | ATE294814T1 (es) |
| DE (1) | DE60300581T2 (es) |
| DK (1) | DK1321471T3 (es) |
| ES (1) | ES2240919T3 (es) |
| MY (1) | MY135359A (es) |
| PT (1) | PT1321471E (es) |
| SI (1) | SI1321471T1 (es) |
| WO (1) | WO2004083238A1 (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1367061T1 (sl) * | 2003-06-30 | 2006-04-30 | Servier Lab | Nov postopek za sintezo perindoprila in njegovih farmacevtsko sprejemljivih soli |
| ATE360638T1 (de) * | 2003-06-30 | 2007-05-15 | Servier Lab | Verfahren für die synthese von perindopril und seiner pharmazeutisch geeigneten salze |
| DK1367062T3 (da) * | 2003-07-31 | 2007-01-02 | Servier Lab | Ny fremgangsmåde til syntese af perindopril og farmaceutisk acceptable salte heraf |
| DK1380590T3 (da) * | 2003-08-29 | 2007-01-08 | Servier Lab | Ny fremgangsmåde til syntese af perindopril og farmaceutisk acceptable salte heraf |
| SI1380591T1 (sl) | 2003-08-29 | 2006-02-28 | Servier Lab | Nov postopek sinteze perindoprila in njegovih farmacevtsko sprejemljivih soli |
| CA2618561C (en) * | 2005-08-12 | 2014-04-29 | Lek Pharmaceuticals D.D. | A process for the preparation of perindopril erbumine |
| WO2016178591A2 (en) | 2015-05-05 | 2016-11-10 | Gene Predit, Sa | Genetic markers and treatment of male obesity |
| PH12018502155B1 (en) | 2016-04-20 | 2024-03-27 | Servier Lab | Pharmaceutical composition comprising a beta blocker, a converting enzyme inhibitor and an antihypertensive or an nsaid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1341296C (en) * | 1981-12-29 | 2001-09-25 | Hansjorg Urbach | 2-azabicycloalkane-3-carboxylic acid derivatives, processes for their preparation, agents containing these compounds and their use |
| FR2807431B1 (fr) * | 2000-04-06 | 2002-07-19 | Adir | Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables |
| FR2827860B1 (fr) * | 2001-07-24 | 2004-12-10 | Servier Lab | Nouveau procede de synthese de derives de l'acide (2s, 3as, 7as)-1-[(s)-alanyl]-octahydro-1h-indole-2-carboxyline et application a la synthese du perindopril |
-
2003
- 2003-03-12 DK DK03290605T patent/DK1321471T3/da active
- 2003-03-12 AT AT03290605T patent/ATE294814T1/de active
- 2003-03-12 EP EP03290605A patent/EP1321471B1/fr not_active Expired - Lifetime
- 2003-03-12 SI SI200330035T patent/SI1321471T1/xx unknown
- 2003-03-12 ES ES03290605T patent/ES2240919T3/es not_active Expired - Lifetime
- 2003-03-12 PT PT03290605T patent/PT1321471E/pt unknown
- 2003-03-12 DE DE60300581T patent/DE60300581T2/de not_active Expired - Lifetime
-
2004
- 2004-03-12 AR ARP040100804A patent/AR043567A1/es not_active Application Discontinuation
- 2004-03-12 WO PCT/FR2004/000594 patent/WO2004083238A1/fr not_active Ceased
- 2004-03-12 MY MYPI20040880A patent/MY135359A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1321471B1 (fr) | 2005-05-04 |
| DE60300581D1 (de) | 2005-06-09 |
| SI1321471T1 (es) | 2005-08-31 |
| PT1321471E (pt) | 2005-07-29 |
| DE60300581T2 (de) | 2006-01-19 |
| DK1321471T3 (da) | 2005-08-29 |
| MY135359A (en) | 2008-03-31 |
| EP1321471A1 (fr) | 2003-06-25 |
| ES2240919T3 (es) | 2005-10-16 |
| WO2004083238A1 (fr) | 2004-09-30 |
| ATE294814T1 (de) | 2005-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |