ZA200601428B - Novel method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof - Google Patents

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

Info

Publication number: ZA200601428B
Authority: ZA; South Africa
Prior art keywords: formula; process according; compound; synthesis; synthesis process
Prior art date: 2003-08-29

Application number

ZA200601428A

Other languages

English (en)

Inventor

Dubuffet Thierry

Lecouve Jean-Pierre

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.)

2003-08-29

Filing date

2004-08-27

Publication date

2007-05-30

2004-08-27 Application filed by Servier Lab filed Critical Servier Lab

2007-05-30 Publication of ZA200601428B publication Critical patent/ZA200601428B/en

Links

230000015572 biosynthetic process Effects 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 15
238000003786 synthesis reaction Methods 0.000 title claims description 15
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 10
150000003839 salts Chemical class 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
238000010511 deprotection reaction Methods 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
-1 p-toluenesulphonyloxy, methanesulphonyloxy Chemical group 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
239000010948 rhodium Substances 0.000 claims description 2
229910052703 rhodium Inorganic materials 0.000 claims description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
125000006309 butyl amino group Chemical group 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
239000002904 solvent Substances 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
UCASZFYRYYFGHP-HARLFGEKSA-N benzyl (2s)-1-[(2s)-2-[[(2s)-1-ethoxy-1-oxopentan-2-yl]amino]propanoyl]-2,3,4,5,6,7-hexahydroindole-2-carboxylate Chemical compound O=C([C@H]1N(C2=C(CCCC2)C1)C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)OCC1=CC=CC=C1 UCASZFYRYYFGHP-HARLFGEKSA-N 0.000 description 2
230000002265 prevention Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
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
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
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
108090000882 Peptidyl-Dipeptidase A Proteins 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
208000037849 arterial hypertension Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
PKOSSINKGUYOOH-JXFKEZNVSA-N benzyl (2s)-1-[(2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-2,3,4,5,6,7-hexahydroindole-2-carboxylate Chemical compound O=C([C@H]1N(C2=C(CCCC2)C1)C(=O)[C@@H](NC(=O)OC(C)(C)C)C)OCC1=CC=CC=C1 PKOSSINKGUYOOH-JXFKEZNVSA-N 0.000 description 1
HDCVJBXIISZAHS-GUYCJALGSA-N benzyl (2s)-1-[(2s)-2-aminopropanoyl]-2,3,4,5,6,7-hexahydroindole-2-carboxylate Chemical compound O=C([C@H]1N(C2=C(CCCC2)C1)C(=O)[C@@H](N)C)OCC1=CC=CC=C1 HDCVJBXIISZAHS-GUYCJALGSA-N 0.000 description 1
FDMGPVBOWQRJCK-HNNXBMFYSA-N benzyl (2s)-2,3,4,5,6,7-hexahydro-1h-indole-2-carboxylate Chemical compound O=C([C@H]1NC2=C(CCCC2)C1)OCC1=CC=CC=C1 FDMGPVBOWQRJCK-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
230000015556 catabolic process Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
VLDADOIBISWPAB-CYBMUJFWSA-N ethyl (2r)-2-(4-methylphenyl)sulfonyloxypentanoate Chemical compound CCOC(=O)[C@@H](CCC)OS(=O)(=O)C1=CC=C(C)C=C1 VLDADOIBISWPAB-CYBMUJFWSA-N 0.000 description 1
ZAOIIUSDMKVQJW-ZCFIWIBFSA-N ethyl (2r)-2-chloropentanoate Chemical compound CCC[C@@H](Cl)C(=O)OCC ZAOIIUSDMKVQJW-ZCFIWIBFSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
SDBQPOCLUYDXKE-YFKPBYRVSA-N tert-butyl n-[(2s)-1-chloro-1-oxopropan-2-yl]carbamate Chemical compound ClC(=O)[C@H](C)NC(=O)OC(C)(C)C SDBQPOCLUYDXKE-YFKPBYRVSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 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
- A61P9/10—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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Indole Compounds (AREA)
Peptides Or Proteins (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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ZA200601428A 2003-08-29 2004-08-27 Novel method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof ZA200601428B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP03292131A EP1380590B1 (fr)	2003-08-29	2003-08-29	Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables

Publications (1)

Publication Number	Publication Date
ZA200601428B true ZA200601428B (en)	2007-05-30

Family

ID=29724623

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200601428A ZA200601428B (en)	2003-08-29	2004-08-27	Novel method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof

Country Status (19)

Country	Link
US (1)	US7183308B1 (da)
EP (1)	EP1380590B1 (da)
JP (1)	JP4331205B2 (da)
CN (1)	CN100395264C (da)
AR (1)	AR045515A1 (da)
AT (1)	ATE338766T1 (da)
AU (1)	AU2004270427B2 (da)
CY (1)	CY1105790T1 (da)
DE (1)	DE60308102T2 (da)
DK (1)	DK1380590T3 (da)
EA (1)	EA008485B1 (da)
ES (1)	ES2272922T3 (da)
MY (1)	MY139348A (da)
NZ (1)	NZ545335A (da)
PL (1)	PL211509B1 (da)
PT (1)	PT1380590E (da)
SI (1)	SI1380590T1 (da)
WO (1)	WO2005023841A1 (da)
ZA (1)	ZA200601428B (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1380591B1 (fr) *	2003-08-29	2005-11-16	Les Laboratoires Servier	Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables
WO2005108365A1 (en) *	2004-05-07	2005-11-17	Glenmark Pharmaceuticals Limited	Processes for the preparation of alpha polymorph of perindopril erbumine
DK1679072T5 (da)	2005-01-06	2009-04-20	Ipca Lab Ltd	Fremgangsmåde til syntese af (2S,3aS,7aS)-1-(S)-alanyl-octahydro-1H-indol-2-carboxylsyrederivater og anvendelse i syntesen af perindopril
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
CN108752259A (zh) *	2018-07-04	2018-11-06	南京方生和医药科技有限公司	培哚普利消旋体及其中间体的制备方法
CN112047998B (zh) *	2020-09-07	2024-01-09	上海阿达玛斯试剂有限公司	一种培哚普利的制备方法
CN113980096A (zh) *	2021-11-29	2022-01-28	绍兴市上虞区武汉理工大学高等研究院	一种吨级培哚普利叔丁胺的合成工艺方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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
PT1321471E (pt) *	2003-03-12	2005-07-29	Servier Lab	Novo processo de sintese do perindopril e dos seus sais aceitaveis sob o ponto de vista farmaceutico
DE60300106T2 (de) *	2003-03-12	2005-10-13	Les Laboratoires Servier	Verfahren zur Synthese von (2S,3aS,7aS)-1-((S)-Alanyl)-octahydro-1H-indol-2-carbonsäurederivaten und Verwendung in der Synthese von Perindopril
ES2250853T3 (es) *	2003-08-29	2006-04-16	Les Laboratoires Servier	Procedimiento para la sintesis de perindopril y de sus sales farmaceuticamente aceptables.

2003
- 2003-08-29 DE DE60308102T patent/DE60308102T2/de not_active Expired - Lifetime
- 2003-08-29 SI SI200330457T patent/SI1380590T1/sl unknown
- 2003-08-29 EP EP03292131A patent/EP1380590B1/fr not_active Expired - Lifetime
- 2003-08-29 PT PT03292131T patent/PT1380590E/pt unknown
- 2003-08-29 ES ES03292131T patent/ES2272922T3/es not_active Expired - Lifetime
- 2003-08-29 AT AT03292131T patent/ATE338766T1/de active
- 2003-08-29 DK DK03292131T patent/DK1380590T3/da active
2004
- 2004-08-26 MY MYPI20043493A patent/MY139348A/en unknown
- 2004-08-27 JP JP2006524394A patent/JP4331205B2/ja not_active Expired - Fee Related
- 2004-08-27 ZA ZA200601428A patent/ZA200601428B/en unknown
- 2004-08-27 AU AU2004270427A patent/AU2004270427B2/en not_active Ceased
- 2004-08-27 US US10/570,566 patent/US7183308B1/en not_active Expired - Fee Related
- 2004-08-27 EA EA200600456A patent/EA008485B1/ru not_active IP Right Cessation
- 2004-08-27 PL PL379629A patent/PL211509B1/pl unknown
- 2004-08-27 CN CNB2004800241924A patent/CN100395264C/zh not_active Expired - Fee Related
- 2004-08-27 WO PCT/FR2004/002196 patent/WO2005023841A1/fr not_active Ceased
- 2004-08-27 NZ NZ545335A patent/NZ545335A/en not_active IP Right Cessation
- 2004-08-27 AR ARP040103078A patent/AR045515A1/es not_active Application Discontinuation
2006
- 2006-11-16 CY CY20061101672T patent/CY1105790T1/el unknown

Also Published As

Publication number	Publication date
US7183308B1 (en)	2007-02-27
AU2004270427A1 (en)	2005-03-17
DK1380590T3 (da)	2007-01-08
DE60308102T2 (de)	2007-06-21
PL379629A1 (pl)	2006-10-30
CN100395264C (zh)	2008-06-18
HK1096409A1 (en)	2007-06-01
EA008485B1 (ru)	2007-06-29
NZ545335A (en)	2009-08-28
AU2004270427B2 (en)	2008-08-21
ES2272922T3 (es)	2007-05-01
DE60308102D1 (de)	2006-10-19
ATE338766T1 (de)	2006-09-15
JP2007526901A (ja)	2007-09-20
WO2005023841A1 (fr)	2005-03-17
JP4331205B2 (ja)	2009-09-16
CN1839147A (zh)	2006-09-27
PT1380590E (pt)	2006-12-29
PL211509B1 (pl)	2012-05-31
EA200600456A1 (ru)	2006-08-25
EP1380590A1 (fr)	2004-01-14
MY139348A (en)	2009-09-30
SI1380590T1 (sl)	2006-12-31
CY1105790T1 (el)	2011-02-02
EP1380590B1 (fr)	2006-09-06
US20070043103A1 (en)	2007-02-22
AR045515A1 (es)	2005-11-02

Publication	Publication Date	Title
EA005490B1 (ru)	2005-02-24	НОВЫЙ СПОСОБ СИНТЕЗА СОЕДИНЕНИЙ (2S, 3aS, 7aS)-1-[(S)-АЛАНИЛ]ОКТАГИДРО -1H-ИНДОЛ-2-КАРБОНОВОЙ КИСЛОТЫ И ПРИМЕНЕНИЕ В СИНТЕЗЕ ПЕРИНДОПРИЛА
NZ544003A (en)	2009-03-31	Novel method of synthesising perindopril and pharmaceutically-acceptable salts thereof
ZA200601428B (en)	2007-05-30	Novel method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof
JP4331207B2 (ja)	2009-09-16	ペリンドプリルおよびその薬学的に許容され得る塩の、新規な合成方法
AU2004270428B2 (en)	2008-08-21	Novel method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof
JP4279871B2 (ja)	2009-06-17	（２ｓ，３ａｓ，７ａｓ）−１−［（ｓ）−アラニル］−オクタヒドロ−１ｈ−インドール−２−カルボン酸誘導体類を合成する新規な方法およびペリンドプリル合成におけるその使用
AU2004261440B2 (en)	2008-07-31	Novel method for the synthesis of perindopril and the pharmaceutically acceptable salts thereof
NZ544879A (en)	2009-03-31	Novel method for the synthesis of perindopril and the pharmaceutically acceptable salts thereof
HK1096407B (en)	2009-06-05	Novel method for the synthesis of perindopril and the pharmaceutically acceptable salts thereof
HK1097852B (en)	2008-06-06	Novel method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof
ZA200604368B (en)	2007-10-31	Method for the synthesis of derivatives of (2S, 3AS, 7AS)-1-[(S)-alanyl]-octahydro-1H-indole-2-carboxylic acid and use thereof for the synthesis of perindopril
HK1096409B (en)	2009-01-23	Novel method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof