US20040029813A1 - Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same - Google Patents
Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same Download PDFInfo
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- US20040029813A1 US20040029813A1 US10/312,902 US31290202A US2004029813A1 US 20040029813 A1 US20040029813 A1 US 20040029813A1 US 31290202 A US31290202 A US 31290202A US 2004029813 A1 US2004029813 A1 US 2004029813A1
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- XVEVFLNZMLBCJQ-MXLIJYGISA-N C.C.[H][C@@]12CCCC[C@]1([H])N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(=O)O)C2 Chemical compound C.C.[H][C@@]12CCCC[C@]1([H])N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(=O)O)C2 XVEVFLNZMLBCJQ-MXLIJYGISA-N 0.000 description 3
Classifications
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- A61P9/04—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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
Definitions
- the present invention relates to a new ⁇ crystalline form of perindopril tert-butylamine salt of formula (I:
- the present invention relates to the ⁇ crystalline form of the compound of formula (I), characterised by the following powder X-ray diffraction diagram, measured using a Siemens D5005 diffractometer (copper anticathode) and expressed in terms of inter-planar distance d, Bragg's angle 2 theta, intensity and relative intensity (expressed as a percentage of the most intense ray): Angle 2 theta Inter-planar Relative intensity (°) distance d ( ⁇ ) Intensity (%) 5.169 17.08 523 16.5 8.379 10.54 1001 31.5 9.350 9.45 3175 100 14.746 6.00 236 7.4 15.411 5.74 753 23.7 15.931 5.56 279 8.8 16.711 5.30 113 3.6 18.161 4.88 122 3.8 20.564 4.32 1198 37.7 21.285 4.17 330 10.4 21.781 4.08 317 10 22.632 3.93 190 6 23.308 3.81 133 4.2 23.797 3.74 427 13.
- the invention relates also to a process for the preparation of the ⁇ crystalline form of the compound of formula (I), which process is characterised in that:
- a solution of perindoprtil tert-butylamine salt in ethyl acetate is heated at reflux and is then rapidly cooled to 5° C. and the solid obtained is collected by filtration.
- the concentration of the compound of formula (I) in the dichloromethane is preferably from 100 to 200 g/litre.
- the concentration of the compound of formula (I) in the ethyl acetate is preferably from 70 to 90 g/litre.
- the invention relates also to pharmaceutical compositions comprising as active ingredient the ⁇ crystalline form of the compound of formula (1) together with one or more appropriate, inert, non-toxic excipients.
- pharmaceutical compositions according to the invention there may be mentioned more especially those that are suitable for oral, parenteral (intravenous or subcutaneous) or nasal administration, tablets or drages, sublingual tablets, gelatin capsules, lozenges, suppositories, creams, ointments, dermal gels, injectable preparations, drinkable suspensions etc.
- the useful dosage can be varied according to the nature and severity of the disorder, the administration route and the age and weight of the patient. It varies from 1 to 500 mg per day in one or more administrations.
- compositions according to the invention may also comprise a diuretic such as indapamide.
- variable slits v6
- Preparation formula for 1000 tablets each containing 4 mg of active ingredient Preparation formula for 1000 tablets each containing 4 mg of active ingredient: Compound of Example 1 4 g Hydroxypropylcellulose 2 g Wheat starch 10 g Lactose 100 g Magnesium stearate 3 g Talc 3 g
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
-
- to a process for its preparation and to pharmaceutical compositions containing it.
- Perindopril and its pharmaceutically acceptable salts, and more especially its tert-butylamine salt, have valuable pharmacological properties.
- Their principal property is that of inhibiting angiotensin I converting enzyme (or kininase II), which prevents, on the one hand, conversion of the decapeptide angiotensin I to the octapeptide angiotensin It (a vasoconstrictor) and, on the other hand, degradation of bradyldnin (a vasodilator) to an inactive peptide.
- Those two actions contribute to the beneficial effects of perindopril in cardiovascular diseases, more especially in arterial hypertension and heart failure.
- Perindopril, its preparation and its use in therapeutics have been described in European Patent specification EP 0 049 658.
- In view of the pharmaceutical value of this compound, it has been of prime importance to obtain it with excellent purity. It has also been important to be able to synthesise it by means of a process that can readily be converted to he industrial scale, especially in a form that allows rapid filtration and drying. Finally, that form had to be perfectly reproducible, easily formulated and sufficiently stable to allow its storage for long periods without particular requirements for temperature, light, humidity or oxygen level.
- The patent specification EP 0 308 341 describes an industrial synthesis process for perindopril. However, that document does not specify the conditions for obtaining perindopril in a form that exhibits those characteristics in a reproducible manner.
- The Applicant has now found that a particular salt of perindopril, the tert-butylamine salt, can be obtained in a well defined, perfectly reproducible crystalline form that especially exhibits valuable characteristics for formulation.
- More specifically, the present invention relates to the β crystalline form of the compound of formula (I), characterised by the following powder X-ray diffraction diagram, measured using a Siemens D5005 diffractometer (copper anticathode) and expressed in terms of inter-planar distance d, Bragg's angle 2 theta, intensity and relative intensity (expressed as a percentage of the most intense ray):
Angle 2 theta Inter-planar Relative intensity (°) distance d (Å) Intensity (%) 5.169 17.08 523 16.5 8.379 10.54 1001 31.5 9.350 9.45 3175 100 14.746 6.00 236 7.4 15.411 5.74 753 23.7 15.931 5.56 279 8.8 16.711 5.30 113 3.6 18.161 4.88 122 3.8 20.564 4.32 1198 37.7 21.285 4.17 330 10.4 21.781 4.08 317 10 22.632 3.93 190 6 23.308 3.81 133 4.2 23.797 3.74 427 13.4 24.276 3.66 118 3.7 25.190 3.53 92 2.9 25.924 3.43 251 7.9 26.646 3.34 250 7.9 27.620 3.23 96 3 28.306 3.15 133 4.2 - The invention relates also to a process for the preparation of the β crystalline form of the compound of formula (I), which process is characterised in that:
- either, according to a first embodiment, a solution of perindopril tert-butylamine salt in dichloromethane is heated at reflux and is then rapidly cooled to 0° C. and the solid obtained is collected by filtration,
- or, according to a second embodiment, a solution of perindoprtil tert-butylamine salt in ethyl acetate is heated at reflux and is then rapidly cooled to 5° C. and the solid obtained is collected by filtration.
- In the crystallisation process according to the invention it is possible to use the compound of formula a) obtained by any process. Advantageously, the compound of formula a) obtained by the preparation process described in patent specification EP 0 308 341 is used.
- In the first embodiment of the process according to the invention, the concentration of the compound of formula (I) in the dichloromethane is preferably from 100 to 200 g/litre.
- In the second embodiment of the process according to the invention, the concentration of the compound of formula (I) in the ethyl acetate is preferably from 70 to 90 g/litre.
- The invention relates also to pharmaceutical compositions comprising as active ingredient the β crystalline form of the compound of formula (1) together with one or more appropriate, inert, non-toxic excipients. Among the pharmaceutical compositions according to the invention, there may be mentioned more especially those that are suitable for oral, parenteral (intravenous or subcutaneous) or nasal administration, tablets or drages, sublingual tablets, gelatin capsules, lozenges, suppositories, creams, ointments, dermal gels, injectable preparations, drinkable suspensions etc.
- The useful dosage can be varied according to the nature and severity of the disorder, the administration route and the age and weight of the patient. It varies from 1 to 500 mg per day in one or more administrations.
- The pharmaceutical compositions according to the invention may also comprise a diuretic such as indapamide.
- The following Examples illustrate the invention but do not limit it in any way.
- The powder X-ray diffraction spectrum was measured under the following experimental conditions:
- Siemens D5005 diffractometer, scintillation detector,
- copper anticathode (λ=1.5405 Å), voltage 40 kV, intensity 40 mA,
- mounting θ-θ,
- measurement range: 5° to 30°,
- increment between each measurement : 0.02°,
- measurement time per step: 2 s,
- variable slits: v6,
- filter Kβ (Ni),
- no internal reference,
- zeroing procedure with the Siemens slits,
- experimental data processed using EVA software (version 5.0).
- 135 g of perindopril tert-butylamine salt obtained according to the process described in patent specification EP 0 308 341 are dissolved in 1100 ml of dichloromemane heated at reflux.
- The solution is then cooled to 0° C. and the solid obtained is collected by filtration.
- Powder X-Ray Diffraction Diagram:
- The powder X-ray diffraction profile (diffraction angles) of the β form of perindopril tert-butylamine salt is given by the significant rays collated in the following table together with the intensity and relative intensity (expressed as a percentage of the most intense ray):
Angle 2 theta Inter-planar Relative intensity (°) distance d (Å) Intensity (%) 5.169 17.08 523 16.5 8.379 10.54 1001 31.5 9.350 9.45 3175 100 14.746 6.00 236 7.4 15.411 5.74 753 23.7 15.931 5.56 279 8.8 16.711 5.30 113 3.6 18.161 4.88 122 3.8 20.564 4.32 1198 37.7 21.285 4.17 330 10.4 21.781 4.08 317 10 22.632 3.93 190 6 23.308 3.81 133 4.2 23.797 3.74 427 13.4 24.276 3.66 118 3.7 25.190 3.53 92 2.9 25.924 3.43 251 7.9 26.646 3.34 250 7.9 27.620 3.23 96 3 28.306 3.15 133 4.2 - 125 g of perindopril tert-butylamine salt obtained according to the process described in patent specification EP 0 308 341 are dissolved in 1.5 litres of ethyl acetate heated at reflux.
- The solution is then cooled rapidly to 5° C. and the solid obtained is collected by filtration
- Preparation formula for 1000 tablets each containing 4 mg of active ingredient:
Preparation formula for 1000 tablets each containing 4 mg of active ingredient: Compound of Example 1 4 g Hydroxypropylcellulose 2 g Wheat starch 10 g Lactose 100 g Magnesium stearate 3 g Talc 3 g
Claims (11)
1. β Crystalline Form of the Compound of Formula (I):
characterised by the following powder x-ray diffraction diagram measured using a diffractometer (copper anticathode) and expressed in terms of inter-planar distance d, Bragg's angle 2 theta, intensity and relative intensity (expressed as a percentage with respect to the most intense ray):
2. Process for the preparation of the β crystalline form of the compound of formula (1) according to claim 1 , characterised in that a solution of perindopril tert-butylamine salt in dichloromethane is heated at reflux, the solution is then cooled to 0° C. and the solid obtained is collected by filtration.
3. Process for the preparation of the β crystalline form of the compound of formula (I) according to claim 1 , characterised in that a solution of perindopril tert-butylamine salt in ethyl acetate is heated at reflux, the solution is rapidly cooled to 5° C. and the solid obtained is then collected by filtration.
4. Process according to either claim 2 or claim 3 , characterised in tat the compound of formula (I) obtained by the preparation process described in patent specification EP 0 308 341 is used.
5. Process according to claim 2 , characterised in that the concentration of the compound of formula (I) in the dichloromethane is from 100 to 200 g/litre.
6. Process according to claim 3 , characterised in that the concentration of the compound of formula (I) in the ethyl acetate is from 70 to 90 g/litre.
7. Pharmaceutical composition comprising as active ingredient the compound according to claim 1 , in combination with one or more pharmaceutically acceptable, inert, non-toxic carriers.
8. Pharmaceutical composition according to claim 7 for use in the manufacture of medicaments for use as inhibitors of angiotensin I converting enzyme.
9. Pharmaceutical composition according to claim 8 for use in the manufacture of medicaments for use in the treatment of cardiovascular diseases.
10. Pharmaceutical composition according to any one of claims 7 to 9 , characterised in that it also comprises a diuretic.
11. Pharmaceutical composition according to claim 10 , characterised in tat the diuretic is indapamide.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/052,489 US7259181B2 (en) | 2000-07-06 | 2005-02-04 | β crystalline form of perindopril tert-butylamine salt |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0008792A FR2811319B1 (en) | 2000-07-06 | 2000-07-06 | NOVEL BETA CRYSTALLINE FORM OF TERT-BUTYLAMINE SALT OF PERINDOPRIL, ITS PREPARATION METHOD AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
FR0008792 | 2000-07-06 | ||
PCT/FR2001/002168 WO2001087836A1 (en) | 2000-07-06 | 2001-07-06 | Novel $g(b crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US11/052,489 Continuation US7259181B2 (en) | 2000-07-06 | 2005-02-04 | β crystalline form of perindopril tert-butylamine salt |
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US20040029813A1 true US20040029813A1 (en) | 2004-02-12 |
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US10/312,902 Abandoned US20040029813A1 (en) | 2000-07-06 | 2001-07-06 | Novel $g(beta crystalline form of perindopril tert-butylamine salt, preparation method, and pharmaceutical compositions containing same |
US11/052,489 Expired - Fee Related US7259181B2 (en) | 2000-07-06 | 2005-02-04 | β crystalline form of perindopril tert-butylamine salt |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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US11/052,489 Expired - Fee Related US7259181B2 (en) | 2000-07-06 | 2005-02-04 | β crystalline form of perindopril tert-butylamine salt |
Country Status (36)
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US (2) | US20040029813A1 (en) |
EP (2) | EP1294689B1 (en) |
JP (2) | JP3592297B2 (en) |
KR (1) | KR100513571B1 (en) |
CN (1) | CN1328260C (en) |
AP (1) | AP1407A (en) |
AR (1) | AR029571A1 (en) |
AT (1) | ATE324367T1 (en) |
AU (2) | AU2001276419B2 (en) |
BG (1) | BG66131B1 (en) |
BR (1) | BR0112244A (en) |
CA (1) | CA2415442C (en) |
CZ (1) | CZ301765B6 (en) |
DE (1) | DE60119107T2 (en) |
DK (1) | DK1294689T3 (en) |
EA (1) | EA004874B1 (en) |
EE (1) | EE05285B1 (en) |
ES (1) | ES2262666T3 (en) |
FR (1) | FR2811319B1 (en) |
GE (1) | GEP20043360B (en) |
HK (1) | HK1058200A1 (en) |
HR (2) | HRP20030079B8 (en) |
HU (1) | HU227673B1 (en) |
ME (1) | ME00440B (en) |
MX (1) | MXPA02012921A (en) |
NO (1) | NO323446B1 (en) |
NZ (1) | NZ523234A (en) |
OA (1) | OA12305A (en) |
PL (1) | PL348493A1 (en) |
PT (1) | PT1294689E (en) |
RS (1) | RS51717B (en) |
SI (1) | SI1294689T1 (en) |
SK (1) | SK286918B6 (en) |
UA (1) | UA57189C2 (en) |
WO (1) | WO2001087836A1 (en) |
ZA (1) | ZA200300024B (en) |
Cited By (10)
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US20040248817A1 (en) * | 2000-07-06 | 2004-12-09 | Bruno Pfeiffer | Gamma crystalline form of perindopril tert-butylamine salt |
US20050059609A1 (en) * | 2000-07-06 | 2005-03-17 | Bruno Pfeiffer | New alpha crystalline form of perindopril tert-butylamine salt |
US20070135512A1 (en) * | 2003-06-24 | 2007-06-14 | Christoph Strassler | Novel crystalline forms of perindopril erbumine |
US20070172524A1 (en) * | 2004-03-29 | 2007-07-26 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Process for preparing a solid pharmaceutical composition |
WO2007092758A2 (en) * | 2006-02-03 | 2007-08-16 | Dr. Reddy's Laboratories Ltd. | Crystalline forms of perindopril erbumine |
US20080051584A1 (en) * | 2004-05-14 | 2008-02-28 | Les Laboratoires Servier | Process For The Preparation Of Perindopril And Salts Thereof |
US20100016614A1 (en) * | 2005-08-12 | 2010-01-21 | Lek Pharmaceuticals D.D | Process for the preparation of perindopril erbumine |
AU2007220434B2 (en) * | 2006-02-28 | 2010-10-14 | Les Laboratoires Servier | Beta-crystalline form of perindopril arginine salt, method for making same, and pharmaceutical compositions containing same |
AU2007220435B2 (en) * | 2006-02-28 | 2010-11-04 | Les Laboratoires Servier | Alpha crystalline form of the arginine salt of perindopril, process for preparing it, and pharmaceutical compositions comprising it |
US8470869B2 (en) | 2007-06-27 | 2013-06-25 | Krka, Tovarna Zdravil D.D. Novo Mesto | Salts of perindopril |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2395195A (en) | 2002-11-18 | 2004-05-19 | Cipla Ltd | Preparation of perindopril from carboxy-protected precursor, & perindopril monohydrates for use as angiotensin converting enzyme (ACE) inhibitors |
JP4677611B2 (en) | 2003-10-21 | 2011-04-27 | レ ラボラトワール セルヴィエ | A novel method for the preparation of crystalline perindopril erbumine |
SI21703A (en) | 2004-01-14 | 2005-08-31 | Lek Farmacevtska Druzba Dd | Inclusion complexes of perindopril, procedure of their preparation, pharmaceutical compositions containing these complexes and their application in treatment of hypertensia |
SI21881A (en) | 2004-10-15 | 2006-04-30 | Diagen, Smartno Pri Ljubljani, D.O.O. | New crystal forms of perindopril erbumine hydrates, procedure of their preparation and pharmaceutical forms containing these compounds |
SG125975A1 (en) * | 2005-03-11 | 2006-10-30 | Servier Lab | New alpha crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it |
SG125976A1 (en) * | 2005-03-11 | 2006-10-30 | Servier Lab | New gama crystalline form of perindopril tert-butylamine salt, a process for its preparation and pharmaceutical compositions containing it |
JP2006290825A (en) * | 2005-04-13 | 2006-10-26 | Shiono Chemical Co Ltd | METHOD FOR PRODUCING alpha-TYPE PERINDOPRYL ERBUMINE |
WO2007017894A2 (en) * | 2005-05-05 | 2007-02-15 | Arch Pharmalabs Limited | PREPARATION OF NOVEL CRYSTALLINE η(ETA) FORM OF PERINDOPRIL ERBUMINE |
WO2007020009A1 (en) * | 2005-08-12 | 2007-02-22 | Sandoz Ag | New crystalline form of perindopril erbumine |
EP1815857A1 (en) | 2006-02-02 | 2007-08-08 | LEK Pharmaceuticals D.D. | A pharmaceutical composition comprising perindopril |
WO2008050185A2 (en) * | 2006-10-26 | 2008-05-02 | Glenmark Pharmaceuticals Limited | Novel polymorphs of perindopril erbumine |
WO2008120241A2 (en) * | 2007-03-29 | 2008-10-09 | Ipca Laboratories Limited | Novel alcohol solvates of perindopril erbumine |
EP2318365B1 (en) * | 2008-06-24 | 2015-08-12 | Mylan Laboratories Limited | Novel polymorphic forms of perindopril (l)-arginine and process for the preparation thereof |
SI23149A (en) | 2009-09-21 | 2011-03-31 | Silverstone Pharma | New benzatin salts of ace inhibitors, procedure for their preparationand their application for treatment of cardiovascular diseases |
PT105315B (en) | 2010-09-29 | 2013-01-16 | Inst Superior Tecnico | A NEW CRYSTALIN HYDRATE FORM OF PERINDOPRIL ERBUMINE, METHODS FOR PREPARATION AND USE IN PHARMACEUTICAL PREPARATIONS |
CN106432042A (en) * | 2015-08-13 | 2017-02-22 | 南京华威医药科技开发有限公司 | New medicine crystal form of nintedanib ethanesulfonate hydrate |
EP3842035A1 (en) | 2019-12-23 | 2021-06-30 | KRKA, d.d., Novo mesto | Composition for the preparation of perindopril arginine granules, a method for their preparation and pharmaceutical composition comprising the granules |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4914214A (en) * | 1987-09-17 | 1990-04-03 | Adir Et Cie | Process for the industrial synthesis of perindopril |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2771010B1 (en) * | 1997-11-19 | 2003-08-15 | Adir | USE OF A COMBINATION OF AN ANGIOTENSIN CONVERSION ENZYME INHIBITOR AND A DIURETIC FOR THE TREATMENT OF MICROCIRCULATORY DISORDERS |
FR2811320B1 (en) * | 2000-07-06 | 2002-08-23 | Adir | NOVEL ALPHA CRYSTALLINE FORM OF TERT-BUTYLAMINE SALT OF PERINDOPRIL, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
FR2811318B1 (en) * | 2000-07-06 | 2002-08-23 | Adir | NOVEL GAMMA CRYSTALLINE FORM OF TERT-BUTYLAMINE SALT OF PERINDOPRIL, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
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2000
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US20050059609A1 (en) * | 2000-07-06 | 2005-03-17 | Bruno Pfeiffer | New alpha crystalline form of perindopril tert-butylamine salt |
US20040248817A1 (en) * | 2000-07-06 | 2004-12-09 | Bruno Pfeiffer | Gamma crystalline form of perindopril tert-butylamine salt |
US7981921B2 (en) | 2003-06-24 | 2011-07-19 | Les Laboratoires Servier | Crystalline forms of perindopril erbumine |
US20070135512A1 (en) * | 2003-06-24 | 2007-06-14 | Christoph Strassler | Novel crystalline forms of perindopril erbumine |
US7705046B2 (en) | 2003-06-24 | 2010-04-27 | Les Laboratoires Servier | Crystalline forms of perindopril erbumine |
US20100160404A1 (en) * | 2003-06-24 | 2010-06-24 | Christoph Strassler | New crystalline forms of perindopril erbumine |
US20070172524A1 (en) * | 2004-03-29 | 2007-07-26 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Process for preparing a solid pharmaceutical composition |
EP1729739B1 (en) | 2004-03-29 | 2016-09-28 | Les Laboratoires Servier | Process for preparing a solid pharmaceutical composition |
US20100172995A1 (en) * | 2004-03-29 | 2010-07-08 | Les Laboratoires Servier | Process For Preparing A Solid Pharmaceutical Composition |
US20080051584A1 (en) * | 2004-05-14 | 2008-02-28 | Les Laboratoires Servier | Process For The Preparation Of Perindopril And Salts Thereof |
US7674814B2 (en) | 2004-05-14 | 2010-03-09 | Les Laboratoires Servier | Process for the preparation of perindopril and salts thereof |
US20100016614A1 (en) * | 2005-08-12 | 2010-01-21 | Lek Pharmaceuticals D.D | Process for the preparation of perindopril erbumine |
WO2007092758A2 (en) * | 2006-02-03 | 2007-08-16 | Dr. Reddy's Laboratories Ltd. | Crystalline forms of perindopril erbumine |
WO2007092758A3 (en) * | 2006-02-03 | 2008-06-19 | Reddys Lab Ltd Dr | Crystalline forms of perindopril erbumine |
AU2007220435B2 (en) * | 2006-02-28 | 2010-11-04 | Les Laboratoires Servier | Alpha crystalline form of the arginine salt of perindopril, process for preparing it, and pharmaceutical compositions comprising it |
AU2007220434B2 (en) * | 2006-02-28 | 2010-10-14 | Les Laboratoires Servier | Beta-crystalline form of perindopril arginine salt, method for making same, and pharmaceutical compositions containing same |
US8470869B2 (en) | 2007-06-27 | 2013-06-25 | Krka, Tovarna Zdravil D.D. Novo Mesto | Salts of perindopril |
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