ES2122941B1 - Procedimiento para la obtencion de quinapril clorhidrato y solvatos utiles para el aislamiento y purificacion de quinapril clorhidrato. - Google Patents
Procedimiento para la obtencion de quinapril clorhidrato y solvatos utiles para el aislamiento y purificacion de quinapril clorhidrato.Info
- Publication number
- ES2122941B1 ES2122941B1 ES09701169A ES9701169A ES2122941B1 ES 2122941 B1 ES2122941 B1 ES 2122941B1 ES 09701169 A ES09701169 A ES 09701169A ES 9701169 A ES9701169 A ES 9701169A ES 2122941 B1 ES2122941 B1 ES 2122941B1
- Authority
- ES
- Spain
- Prior art keywords
- quinapril
- chlorhydrate
- solvate
- obtaining
- isolation
- 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.)
- Expired - Fee Related
Links
- 239000012453 solvate Substances 0.000 title abstract 5
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 title abstract 4
- 229960001455 quinapril Drugs 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 238000002955 isolation Methods 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 229960003042 quinapril hydrochloride Drugs 0.000 abstract 4
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- -1 benzyl ester Chemical class 0.000 abstract 1
- 230000000593 degrading effect Effects 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCEDIMIENTO PARA LA OBTENCION DE QUINAPRIL CLORHIDRATO Y SOLVATOS UTILES PARA EL AISLAMIENTO Y PURIFICACION DE QUINAPRIL CLORHIDRATO. EL PROCEDIMIENTO PARA OBTENER QUINAPRIL CLORHIDRATO (I) COMPRENDE LAS ETAPAS DE: A) HIDROGENOLISIS DEL ESTER BENCILICO DEL QUINAPRIL (II) POR TRATAMIENTO EN UN DISOLVENTE ALCOHOLICO, CON ACIDO CLORHIDICO O CON UNA DISOLUCION DE CLORURO DE HIDROGENO EN ISOPROPANOL E HIDROGENACION; B) RETIRADA DEL DISOLVENTE; C) ADICION DE TOLUENO PARA PRECIPITAR EL QUINAPRIL CLORHIDRATO COMO SOLVATO DE TOLUENO; D) TRATAMIENTO DE DICHO SOLVATO CON UN DISOLVENTE DE LA CLASE 3 QUE FORMA UN SOLVATO DE QUINAPRIL CLORHIDRATO DEL QUE SE PUEDE ELIMINAR POR SECADO SIN DEGRADARLO; Y E) SECADO DEL SOLVATO DE LA ETAPA D) PARA RENDIR (I). ESTOS SOLVATOS SON UTILES PARA AISLAR Y PURIFICAR (I), UN AGENTE ANTIHIPERTENSIVO.
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES09701169A ES2122941B1 (es) | 1997-05-29 | 1997-05-29 | Procedimiento para la obtencion de quinapril clorhidrato y solvatos utiles para el aislamiento y purificacion de quinapril clorhidrato. |
| EP98920547A EP0992495B1 (en) | 1997-05-29 | 1998-05-25 | Process for obtaining quinapryl hydrochloride and solvates useful for isolating and purifying quinapryl hydrochloride |
| PCT/ES1998/000145 WO1998054149A1 (es) | 1997-05-29 | 1998-05-25 | Procedimiento para la obtención de quinapril clorhidrato y solvatos utiles para el aislamiento y purificación de quinapril clorhidrato |
| KR10-1999-7011151A KR100477713B1 (ko) | 1997-05-29 | 1998-05-25 | 퀸아프릴 하이드로클로라이드와 퀸아프릴하이드로클로라이드 분리 및 정제용 용매화합물 제조방법 |
| DE1998621483 DE69821483T2 (de) | 1997-05-29 | 1998-05-25 | Verfahren zur gewinnung von chinaprylhydrochlorid und solvaten, die bei der isolierung und reinigung von chinaprylhydrochlorid nützlich sind |
| AT98920547T ATE258920T1 (de) | 1997-05-29 | 1998-05-25 | Verfahren zur gewinnung von chinaprylhydrochlorid und solvaten, die bei der isolierung und reinigung von chinaprylhydrochlorid nützlich sind |
| US11/022,424 USRE39888E1 (en) | 1997-05-29 | 1998-05-25 | Process for obtaining quinapryl hydrochloride and solvates useful for isolating and purifying quinapryl hydrochloride |
| CA002293705A CA2293705C (en) | 1997-05-29 | 1998-05-25 | Process for obtaining quinapryl hydrochloride and solvates useful for isolating and purifying quinapryl hydrochloride |
| US09/424,673 US6617457B1 (en) | 1997-05-29 | 1998-05-25 | Process for obtaining quinapryl hydrochloride and solvates useful for isolating and purifying quinapryl hydrochloride |
| DK98920547T DK0992495T3 (da) | 1997-05-29 | 1998-05-25 | Fremgangsmåde til opnåelse af quinaprilhydrochlorid og solvater, der er nyttige ved isolation og rensning af quinaprilhydrochlorid |
| PT98920547T PT992495E (pt) | 1997-05-29 | 1998-05-25 | Processo pata obter cloridrato de quinapril e solvatos uteis para isolar e purificar o cloridrato de quinapril |
| JP50027999A JP2002502386A (ja) | 1997-05-29 | 1998-05-25 | 塩酸キナプリルの製法並びに塩酸キナプリルの単離および精製に有用な溶媒和物 |
| AU73365/98A AU730140B2 (en) | 1997-05-29 | 1998-05-25 | Process for obtaining quinapril hydrochloride and solvates useful for the isolation and purification of quinapril hydrochloride |
| ZA984466A ZA984466B (en) | 1997-05-29 | 1998-05-26 | Process for obtaining quinapril hydrochloride and solvates useful for the isolation and purification of quinapril hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES09701169A ES2122941B1 (es) | 1997-05-29 | 1997-05-29 | Procedimiento para la obtencion de quinapril clorhidrato y solvatos utiles para el aislamiento y purificacion de quinapril clorhidrato. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2122941A1 ES2122941A1 (es) | 1998-12-16 |
| ES2122941B1 true ES2122941B1 (es) | 1999-07-01 |
Family
ID=8299498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09701169A Expired - Fee Related ES2122941B1 (es) | 1997-05-29 | 1997-05-29 | Procedimiento para la obtencion de quinapril clorhidrato y solvatos utiles para el aislamiento y purificacion de quinapril clorhidrato. |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | USRE39888E1 (es) |
| EP (1) | EP0992495B1 (es) |
| JP (1) | JP2002502386A (es) |
| KR (1) | KR100477713B1 (es) |
| AT (1) | ATE258920T1 (es) |
| AU (1) | AU730140B2 (es) |
| CA (1) | CA2293705C (es) |
| DE (1) | DE69821483T2 (es) |
| DK (1) | DK0992495T3 (es) |
| ES (1) | ES2122941B1 (es) |
| PT (1) | PT992495E (es) |
| WO (1) | WO1998054149A1 (es) |
| ZA (1) | ZA984466B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030225124A1 (en) * | 1999-08-31 | 2003-12-04 | Spiridon Spireas | Stable formulations of ACE inhibitors, and methods for preparation thereof |
| AU2002361494A1 (en) * | 2002-12-16 | 2004-07-09 | Lupin Limited | Crystalline form of quinapril hydrochloride and process for preparing the same |
| CL2004000541A1 (es) | 2003-03-31 | 2005-02-04 | Warner Lambert Co | Procedimiento de preparacion de clorhidrato de quinapril por reaccion entre una 2,5-dioxo-oxazolidina y un ester terbutilico de una tetrahidro isoquinolina, util como principio activo para tratar la hipertension y la insuficiencia cardiaca congestiva |
| WO2007054966A2 (en) * | 2005-09-13 | 2007-05-18 | Aarti Healthcare Limited | A process for the preparation of highly pure crystalline quinapril hydrochloride |
| WO2007069268A2 (en) * | 2005-10-14 | 2007-06-21 | Sun Pharmaceutical Industries Limited | A process for the preparation of substantially pure 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives |
| WO2009053994A1 (en) * | 2007-10-26 | 2009-04-30 | Matrix Laboratories Limited | Process for preparing pure amorphous quinapril hydrochloride |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4344949A (en) * | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| IN156096B (es) * | 1981-03-19 | 1985-05-11 | Usv Pharma Corp | |
| JPS58188857A (ja) * | 1982-04-26 | 1983-11-04 | Takeda Chem Ind Ltd | テトラヒドロイソキノリン誘導体 |
| DE3333454A1 (de) * | 1983-09-16 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von n-alkylierten dipeptiden und deren estern |
| DE3333455A1 (de) * | 1983-09-16 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung n-alkylierter dipeptide und deren estern |
| US4761479A (en) * | 1987-03-30 | 1988-08-02 | Warner-Lambert Company | Crystalline quinapril and a process for producing the same |
| JPH01275546A (ja) * | 1988-04-26 | 1989-11-06 | Nisso Yuka Kogyo Kk | 安息香酸ソーダの単離方法 |
| DE4206697A1 (de) * | 1992-03-04 | 1993-09-09 | Hoechst Ag | Verfahren zur herstellung von modifizierten phenolharzen |
| JP3211396B2 (ja) * | 1992-08-26 | 2001-09-25 | 住友化学工業株式会社 | アクリル酸及び酢酸の回収方法 |
-
1997
- 1997-05-29 ES ES09701169A patent/ES2122941B1/es not_active Expired - Fee Related
-
1998
- 1998-05-25 AT AT98920547T patent/ATE258920T1/de not_active IP Right Cessation
- 1998-05-25 PT PT98920547T patent/PT992495E/pt unknown
- 1998-05-25 CA CA002293705A patent/CA2293705C/en not_active Expired - Fee Related
- 1998-05-25 WO PCT/ES1998/000145 patent/WO1998054149A1/es not_active Ceased
- 1998-05-25 DK DK98920547T patent/DK0992495T3/da active
- 1998-05-25 DE DE1998621483 patent/DE69821483T2/de not_active Expired - Lifetime
- 1998-05-25 EP EP98920547A patent/EP0992495B1/en not_active Expired - Lifetime
- 1998-05-25 JP JP50027999A patent/JP2002502386A/ja active Pending
- 1998-05-25 US US11/022,424 patent/USRE39888E1/en not_active Expired - Fee Related
- 1998-05-25 KR KR10-1999-7011151A patent/KR100477713B1/ko not_active Expired - Fee Related
- 1998-05-25 AU AU73365/98A patent/AU730140B2/en not_active Ceased
- 1998-05-25 US US09/424,673 patent/US6617457B1/en not_active Ceased
- 1998-05-26 ZA ZA984466A patent/ZA984466B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2293705A1 (en) | 1998-12-03 |
| ATE258920T1 (de) | 2004-02-15 |
| USRE39888E1 (en) | 2007-10-16 |
| KR100477713B1 (ko) | 2005-03-18 |
| WO1998054149A1 (es) | 1998-12-03 |
| DE69821483T2 (de) | 2005-01-13 |
| ZA984466B (en) | 1998-12-01 |
| AU7336598A (en) | 1998-12-30 |
| ES2122941A1 (es) | 1998-12-16 |
| EP0992495A1 (en) | 2000-04-12 |
| PT992495E (pt) | 2004-06-30 |
| DE69821483D1 (de) | 2004-03-11 |
| US6617457B1 (en) | 2003-09-09 |
| EP0992495B1 (en) | 2004-02-04 |
| JP2002502386A (ja) | 2002-01-22 |
| DK0992495T3 (da) | 2004-06-01 |
| CA2293705C (en) | 2008-03-18 |
| KR20010013167A (ko) | 2001-02-26 |
| AU730140B2 (en) | 2001-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 19981216 Kind code of ref document: A1 Effective date: 19981216 |
|
| GC2A | Exploitation certificate registered application with search report |
Effective date: 20000229 |
|
| FD2A | Announcement of lapse in spain |
Effective date: 20180807 |