ZA200603675B - Method for synthesis of perindopril and the pharmaceutically-acceptable salts thereof - Google Patents

Method for synthesis of perindopril and the pharmaceutically-acceptable salts thereof Download PDF

Info

Publication number: ZA200603675B
Authority: ZA; South Africa
Prior art keywords: compound; formula; process according; dba; synthesis process
Prior art date: 2003-11-19

Application number

ZA200603675A

Other languages

English (en)

Inventor

Dubuffet Thierry

Langlois Pascal

Original Assignee

Servier Lab

Priority date (The priority date 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 date listed.)

2003-11-19

Filing date

2004-11-18

Publication date

2007-09-26

2004-11-18 Application filed by Servier Lab filed Critical Servier Lab

2007-09-26 Publication of ZA200603675B publication Critical patent/ZA200603675B/en

Links

230000015572 biosynthetic process Effects 0.000 title claims description 19
238000003786 synthesis reaction Methods 0.000 title claims description 19
238000000034 method Methods 0.000 title claims description 18
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 description 11
229960002582 perindopril Drugs 0.000 title claims description 11
150000003839 salts Chemical class 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 33
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 32
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
229910052763 palladium Inorganic materials 0.000 claims description 13
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 10
238000005859 coupling reaction Methods 0.000 claims description 9
-1 hydroxy, p-toluenesulphonyloxy, methanesulphonyloxy Chemical group 0.000 claims description 9
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 8
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
238000010511 deprotection reaction Methods 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
SAYKZWPCENNSDR-UHFFFAOYSA-M (n-methylanilino)-triphenylphosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)N(C)C1=CC=CC=C1 SAYKZWPCENNSDR-UHFFFAOYSA-M 0.000 claims description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 2
229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 2
238000006751 Mitsunobu reaction Methods 0.000 claims description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 2
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 2
WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
229910000104 sodium hydride Inorganic materials 0.000 claims description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
OZGMODDEIHYPRY-UWTATZPHSA-N (2r)-2-bromopropanoyl chloride Chemical compound C[C@@H](Br)C(Cl)=O OZGMODDEIHYPRY-UWTATZPHSA-N 0.000 description 2
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000002265 prevention Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
JFVLNTLXEZDFHW-QMMMGPOBSA-N (2s)-2-amino-3-(2-bromophenyl)propanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1Br JFVLNTLXEZDFHW-QMMMGPOBSA-N 0.000 description 1
GLRPCSZNOXRMNE-XCBNKYQSSA-N (2s)-3-(2-bromophenyl)-2-[[(2r)-2-bromopropanoyl]amino]propanoic acid Chemical compound C[C@@H](Br)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1Br GLRPCSZNOXRMNE-XCBNKYQSSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
102000005862 Angiotensin II Human genes 0.000 description 1
101800000734 Angiotensin-1 Proteins 0.000 description 1
102400000344 Angiotensin-1 Human genes 0.000 description 1
101800000733 Angiotensin-2 Proteins 0.000 description 1
101800004538 Bradykinin Proteins 0.000 description 1
102400000967 Bradykinin Human genes 0.000 description 1
YZIUFMWCSXAWSG-OGFXRTJISA-N C[C@H](CC(C=C1)=CC=C1S(O)(=O)=O)C(Cl)=O.Cl Chemical compound C[C@H](CC(C=C1)=CC=C1S(O)(=O)=O)C(Cl)=O.Cl YZIUFMWCSXAWSG-OGFXRTJISA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 1
101150003085 Pdcl gene Proteins 0.000 description 1
239000007825 activation reagent Substances 0.000 description 1
229960003767 alanine Drugs 0.000 description 1
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
229950006323 angiotensin ii Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
208000037849 arterial hypertension Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
FRQLGTRLYODUDR-OAHLLOKOSA-N benzyl (2R)-2-amino-3-(2-bromophenyl)propanoate Chemical compound C([C@@H](N)C(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1Br FRQLGTRLYODUDR-OAHLLOKOSA-N 0.000 description 1
UTFHYNIGTOXSGU-DYVFJYSZSA-N benzyl (2s)-1-[(2r)-2-bromopropanoyl]-2,3-dihydroindole-2-carboxylate Chemical compound O=C([C@H]1N(C2=CC=CC=C2C1)C(=O)[C@H](Br)C)OCC1=CC=CC=C1 UTFHYNIGTOXSGU-DYVFJYSZSA-N 0.000 description 1
FRQLGTRLYODUDR-HNNXBMFYSA-N benzyl (2s)-2-amino-3-(2-bromophenyl)propanoate Chemical compound C([C@H](N)C(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1Br FRQLGTRLYODUDR-HNNXBMFYSA-N 0.000 description 1
QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical compound CC(C)(C)N.C1CCC[C@@H]2N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(O)=O)C[C@@H]21 IYNMDWMQHSMDDE-MHXJNQAMSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

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
- 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
- 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
- A61P9/04—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Bioinformatics & Cheminformatics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

ZA200603675A 2003-11-19 2004-11-18 Method for synthesis of perindopril and the pharmaceutically-acceptable salts thereof ZA200603675B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP03292864A EP1420028B1 (fr)	2003-11-19	2003-11-19	Pocédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables

Publications (1)

Publication Number	Publication Date
ZA200603675B true ZA200603675B (en)	2007-09-26

Family

ID=32116380

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200603675A ZA200603675B (en)	2003-11-19	2004-11-18	Method for synthesis of perindopril and the pharmaceutically-acceptable salts thereof

Country Status (28)

Country	Link
US (1)	US7208607B1 (pl)
EP (1)	EP1420028B1 (pl)
JP (1)	JP4377412B2 (pl)
KR (1)	KR100863394B1 (pl)
CN (1)	CN100447152C (pl)
AR (1)	AR047312A1 (pl)
AT (1)	ATE354586T1 (pl)
AU (1)	AU2004295132B2 (pl)
BR (1)	BRPI0416746B1 (pl)
CA (1)	CA2546506C (pl)
CY (1)	CY1106544T1 (pl)
DE (1)	DE60311942T2 (pl)
DK (1)	DK1420028T3 (pl)
EA (1)	EA010102B1 (pl)
EG (1)	EG26629A (pl)
ES (1)	ES2282586T3 (pl)
GE (1)	GEP20084547B (pl)
MA (1)	MA28144A1 (pl)
MX (1)	MXPA06005607A (pl)
MY (1)	MY138550A (pl)
NO (1)	NO336349B1 (pl)
NZ (1)	NZ546931A (pl)
PL (1)	PL210769B1 (pl)
PT (1)	PT1420028E (pl)
SI (1)	SI1420028T1 (pl)
UA (1)	UA83269C2 (pl)
WO (1)	WO2005054276A1 (pl)
ZA (1)	ZA200603675B (pl)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE310012T1 (de) *	2003-08-29	2005-12-15	Servier Lab	Verfahren für die synthese von perindopril und seiner pharmazeutisch annehmbaren salzen
CN1922149A (zh)	2003-12-29	2007-02-28	塞普拉科公司	吡咯和吡唑daao抑制剂
CA2614282A1 (en)	2005-07-06	2007-01-11	Sepracor Inc.	Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders
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2003
- 2003-11-19 EP EP03292864A patent/EP1420028B1/fr not_active Expired - Lifetime
- 2003-11-19 DK DK03292864T patent/DK1420028T3/da active
- 2003-11-19 ES ES03292864T patent/ES2282586T3/es not_active Expired - Lifetime
- 2003-11-19 DE DE60311942T patent/DE60311942T2/de not_active Expired - Lifetime
- 2003-11-19 PT PT03292864T patent/PT1420028E/pt unknown
- 2003-11-19 AT AT03292864T patent/ATE354586T1/de active
- 2003-11-19 SI SI200330702T patent/SI1420028T1/sl unknown
2004
- 2004-11-18 ZA ZA200603675A patent/ZA200603675B/en unknown
- 2004-11-18 AR ARP040104252A patent/AR047312A1/es not_active Application Discontinuation
- 2004-11-18 GE GEAP20049463A patent/GEP20084547B/en unknown
- 2004-11-18 JP JP2006540515A patent/JP4377412B2/ja not_active Expired - Fee Related
- 2004-11-18 AU AU2004295132A patent/AU2004295132B2/en not_active Ceased
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- 2004-11-18 PL PL380409A patent/PL210769B1/pl unknown
- 2004-11-18 UA UAA200606747A patent/UA83269C2/uk unknown
- 2004-11-18 MX MXPA06005607A patent/MXPA06005607A/es active IP Right Grant
- 2004-11-18 BR BRPI0416746-5A patent/BRPI0416746B1/pt not_active IP Right Cessation
- 2004-11-18 US US10/580,148 patent/US7208607B1/en not_active Expired - Fee Related
- 2004-11-18 WO PCT/FR2004/002936 patent/WO2005054276A1/fr not_active Ceased
- 2004-11-18 EA EA200600898A patent/EA010102B1/ru not_active IP Right Cessation
- 2004-11-18 CN CNB2004800336869A patent/CN100447152C/zh not_active Expired - Fee Related
- 2004-11-18 KR KR1020067011929A patent/KR100863394B1/ko not_active Expired - Fee Related
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- 2004-11-18 NZ NZ546931A patent/NZ546931A/en not_active IP Right Cessation
2006
- 2006-05-02 MA MA28993A patent/MA28144A1/fr unknown
- 2006-05-16 EG EGPCTNA2006000459A patent/EG26629A/en active
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Also Published As

Publication number	Publication date
KR20060121202A (ko)	2006-11-28
PT1420028E (pt)	2007-05-31
CA2546506A1 (fr)	2005-06-16
US20070083052A1 (en)	2007-04-12
KR100863394B1 (ko)	2008-10-14
CN1882607A (zh)	2006-12-20
US7208607B1 (en)	2007-04-24
AU2004295132A1 (en)	2005-06-16
EP1420028A3 (fr)	2004-05-26
JP4377412B2 (ja)	2009-12-02
CN100447152C (zh)	2008-12-31
NZ546931A (en)	2010-01-29
CY1106544T1 (el)	2012-01-25
BRPI0416746B1 (pt)	2018-02-14
BRPI0416746A (pt)	2007-01-16
ATE354586T1 (de)	2007-03-15
EA010102B1 (ru)	2008-06-30
MY138550A (en)	2009-06-30
CA2546506C (fr)	2010-04-06
MXPA06005607A (es)	2006-08-17
EG26629A (en)	2014-04-13
NO336349B1 (no)	2015-08-03
EP1420028B1 (fr)	2007-02-21
DK1420028T3 (da)	2007-06-18
EA200600898A1 (ru)	2006-10-27
AR047312A1 (es)	2006-01-18
DE60311942T2 (de)	2007-12-06
NO20062599L (no)	2006-06-06
EP1420028A2 (fr)	2004-05-19
WO2005054276A1 (fr)	2005-06-16
SI1420028T1 (sl)	2007-06-30
PL210769B1 (pl)	2012-02-29
PL380409A1 (pl)	2007-01-22
ES2282586T3 (es)	2007-10-16
AU2004295132B2 (en)	2010-07-15
DE60311942D1 (de)	2007-04-05
MA28144A1 (fr)	2006-09-01
HK1096689A1 (en)	2007-06-08
GEP20084547B (en)	2008-11-25
UA83269C2 (uk)	2008-06-25
JP2008502587A (ja)	2008-01-31

Publication	Publication Date	Title
US7208607B1 (en)	2007-04-24	Process for synthesis of perindopril and pharmaceutically acceptable salts thereof
US7223872B2 (en)	2007-05-29	Process for the synthesis of perindopril and its pharmaceutically acceptable salts
US7183308B1 (en)	2007-02-27	Metod for the synthesis of perindopril and the pharmaceutically acceptable salts thereof
US7534896B2 (en)	2009-05-19	Process for the synthesis of perindopril and its pharmaceutically acceptable salts
AU2004261440B2 (en)	2008-07-31	Novel method for the synthesis of perindopril and the pharmaceutically acceptable salts thereof
US7358372B2 (en)	2008-04-15	Method for the synthesis of perindopril and the pharmaceutically acceptable salts thereof
ES2282587T3 (es)	2007-10-16	Procedimiento de sintesis de perindopril y de sus sales farmaceuticamente aceptables.
HK1096689B (en)	2009-05-22	New process for the synthesis of perindopril and pharmaceutically-acceptable salts thereof