SK286921B6 - Spôsob syntézy perindoprilu a jeho farmaceuticky prijateľných solí - Google Patents

Spôsob syntézy perindoprilu a jeho farmaceuticky prijateľných solí Download PDF

Info

Publication number: SK286921B6
Authority: SK; Slovakia
Prior art keywords: formula; compound; perindopril; amount; less
Prior art date: 2000-04-06

Application number

SK1418-2002A

Other languages

English (en)

Slovak (sk)

Other versions

SK14182002A3 (sk

Inventor

Pascal Langlois

Hugues Turbe

Original Assignee

Les Laboratoires Servier

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.)

2000-04-06

Filing date

2001-04-05

Publication date

2009-07-06

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8848925&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK286921(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2001-04-05 Application filed by Les Laboratoires Servier filed Critical Les Laboratoires Servier

2003-02-04 Publication of SK14182002A3 publication Critical patent/SK14182002A3/sk

2009-07-06 Publication of SK286921B6 publication Critical patent/SK286921B6/sk

Links

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 abstract description 20
229960002582 perindopril Drugs 0.000 title claims abstract description 20
238000000034 method Methods 0.000 title claims abstract description 12
150000003839 salts Chemical class 0.000 title claims abstract description 7
230000015572 biosynthetic process Effects 0.000 title abstract 2
238000003786 synthesis reaction Methods 0.000 title abstract 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
238000005859 coupling reaction Methods 0.000 claims description 7
239000012535 impurity Substances 0.000 claims description 7
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
238000009776 industrial production Methods 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 4
-1 benzyl ester Chemical class 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
101800000734 Angiotensin-1 Proteins 0.000 description 2
102400000344 Angiotensin-1 Human genes 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
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 2
238000006243 chemical reaction Methods 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
AUVAVXHAOCLQBF-YUMQZZPRSA-N (2s)-2-[[(2s)-1-ethoxy-1-oxopentan-2-yl]azaniumyl]propanoate Chemical compound OC(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC AUVAVXHAOCLQBF-YUMQZZPRSA-N 0.000 description 1
102000005862 Angiotensin II 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
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
229950006323 angiotensin ii Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
208000037849 arterial hypertension Diseases 0.000 description 1
ARGCRCXTJMQKNA-KKUMJFAQSA-N benzyl (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indole-2-carboxylate Chemical compound O=C([C@H]1N[C@H]2CCCC[C@H]2C1)OCC1=CC=CC=C1 ARGCRCXTJMQKNA-KKUMJFAQSA-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
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Peptides Or Proteins (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

SK1418-2002A 2000-04-06 2001-04-05 Spôsob syntézy perindoprilu a jeho farmaceuticky prijateľných solí SK286921B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0004379A FR2807431B1 (fr)	2000-04-06	2000-04-06	Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables
PCT/FR2001/001026 WO2001058868A1 (fr)	2000-04-06	2001-04-05	Procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables

Publications (2)

Publication Number	Publication Date
SK14182002A3 SK14182002A3 (sk)	2003-02-04
SK286921B6 true SK286921B6 (sk)	2009-07-06

Family

ID=8848925

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1418-2002A SK286921B6 (sk)	2000-04-06	2001-04-05	Spôsob syntézy perindoprilu a jeho farmaceuticky prijateľných solí

Country Status (34)

Country	Link
US (1)	US6835843B2 (cs)
EP (1)	EP1268424B1 (cs)
JP (1)	JP3939553B2 (cs)
KR (1)	KR100507616B1 (cs)
CN (1)	CN1296355C (cs)
AP (1)	AP1385A (cs)
AT (1)	ATE369338T1 (cs)
AU (2)	AU4847001A (cs)
BG (1)	BG65984B1 (cs)
BR (1)	BRPI0109836B1 (cs)
CA (1)	CA2405486C (cs)
CY (1)	CY1108522T1 (cs)
CZ (1)	CZ302575B6 (cs)
DE (1)	DE60129800T2 (cs)
DK (1)	DK1268424T3 (cs)
EA (1)	EA005079B1 (cs)
EE (1)	EE05032B1 (cs)
ES (1)	ES2291307T3 (cs)
FR (1)	FR2807431B1 (cs)
GE (1)	GEP20063797B (cs)
HR (1)	HRP20020876B1 (cs)
HU (1)	HU227674B1 (cs)
ME (1)	ME00441B (cs)
MX (1)	MXPA02009706A (cs)
NO (1)	NO324174B1 (cs)
NZ (1)	NZ521454A (cs)
OA (1)	OA12242A (cs)
PL (1)	PL204471B1 (cs)
PT (1)	PT1268424E (cs)
RS (1)	RS50808B (cs)
SK (1)	SK286921B6 (cs)
UA (1)	UA75070C2 (cs)
WO (1)	WO2001058868A1 (cs)
ZA (1)	ZA200207419B (cs)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
ATE365714T1 (de) *	2002-01-30	2007-07-15	Servier Lab	Verfahren zur herstellung von hochreinem perindopril und zwischenverbindungen nützlich in der synthese
JP2005256847A (ja) *	2002-02-28	2005-09-22	Nsk Ltd	車輪用軸受ユニット
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
ATE307801T1 (de) *	2003-02-28	2005-11-15	Servier Lab	Verfahren zur synthese des (2s,3as,7as)- perhydroindol-2-carbonsäures und seiner estern, verwendung in der synthese von perindopril
EP1603558B1 (en)	2003-02-28	2008-05-21	Les Laboratoires Servier S.A.	Process for preparation of perindopril and salts thereof
DE60301774T2 (de) *	2003-02-28	2006-07-20	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
SI1403275T1 (sl) *	2003-02-28	2006-02-28	Servier Lab	Nov postopek sinteze perindoprila in njegovih farmacevtsko sprejemljivih soli
EP1319668B1 (fr) *	2003-03-12	2004-10-27	Les Laboratoires Servier	Nouveau procédé de synthèse de dérivés de l'acide (2S, 3aS, 7aS)-1-[(S)]-alanyl]-octahydro-1H-indole-2-carboxylique et application à la synthèse du perindopril
EP1323729B1 (fr) *	2003-03-12	2004-11-03	Les Laboratoires Servier	Nouveau procédé de synthèse de l'acide (2S, 3aS, 7aS)-perhydroindole-2-carboxylique et de ses esters, et application à la synthèse du perindopril
DK1321471T3 (da) *	2003-03-12	2005-08-29	Servier Lab	Ny syntesefremgangsmåde til perindopril og farmaceutisk acceptable salte heraf
WO2004099138A2 (en) *	2003-05-12	2004-11-18	Cipla Limited	Process for the preparation of perindopril
DK1636185T3 (da)	2003-06-24	2012-05-07	Servier Lab	Nye krystalformer af Perindopril erbumin
SI1367063T1 (sl) *	2003-07-31	2006-10-31	Servier Lab	Nov postopek sinteze perindoprila in njegovih farmacevtsko sprejemljivih soli
ES2271497T3 (es) *	2003-07-31	2007-04-16	Les Laboratoires Servier	Nuevo procedimiento de sintesis de perindopril y de sus sales farmaceuticamente aceptables.
DK1675827T3 (da) *	2003-10-21	2010-04-19	Servier Lab	Ny fremgangsmåde til fremstilling af krystallint perindopril erbumin
SI1420029T1 (sl) *	2003-12-10	2008-08-31	Servier Lab	Postopek za sintezo perindoprila in njegovih farmacevtsko sprejemljivih soli
PT1729739T (pt) *	2004-03-29	2016-12-01	Servier Lab	Processo para a preparação de uma composição farmacêutica sólida
GB2413128A (en) *	2004-04-13	2005-10-19	Neopharma Ltd	Process for the preparation of perindopril
SI21800A (sl) *	2004-05-14	2005-12-31	Krka, Tovarna Zdravil, D.D., Novo Mesto	Nov postopek sinteze perindoprila
ES2255872B1 (es) *	2004-12-31	2007-08-16	Quimica Sintetica, S.A.	Procedimiento para la preparacion de perindopril erbumina.
PT1679072E (pt) *	2005-01-06	2008-12-22	Ipca Lab Ltd	Processo para a síntese de derivados de ácido (2s,3as,7as)-1-(s)-alanil-octa-hidro-1h-indole-2-carboxílico e utilização na síntese de perindopril
US7291745B2 (en) *	2005-03-21	2007-11-06	Glenmark Pharmaceuticals Limited	Process for the preparation of perindopril
JP2006290825A (ja) *	2005-04-13	2006-10-26	Shiono Chemical Co Ltd	アルファ型ペリンドプリルエルブミンの製造法
DE102005058166A1 (de) *	2005-12-05	2007-06-06	Hexal Ag	Matrixkontrolliertes transdermales System mit Amin-Salzen der ACE-Hemmer-Dicarbonsäuren
WO2007085933A2 (en) *	2006-01-25	2007-08-02	Glenmark Pharmaceuticals Limited	Process for the preparation of n-[1-(s)-ethoxycarbonyl-1-butyl]-(s)-alanine-dmt complex and its use in the preparation of perindopril
WO2008114270A1 (en) *	2007-03-22	2008-09-25	Aarti Healthcare Limited	Process for the preparation of perindopril erbumine salt and novel polymorph (s) thereof
FR2961105B1 (fr) *	2010-06-15	2013-02-08	Servier Lab	Utilisation de l'association d'un inhibiteur du courant if sinusal et d'un inhibiteur de l'enzyme de conversion de l'angiotensine pour le traitement de l'insuffisance cardiaque
EP2906536B1 (en) *	2012-10-10	2018-03-14	Piramal Enterprises Limited	An improved process for preparation of perindopril intermediate
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
CN107098949B (zh) *	2017-04-20	2021-03-16	上药东英（江苏）药业有限公司	一种制备培哚普利叔丁胺盐的绿色合成新工艺

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
DE3302125A1 (de) *	1983-01-22	1984-07-26	Boehringer Ingelheim KG, 6507 Ingelheim	Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung
FR2620709B1 (fr) *	1987-09-17	1990-09-07	Adir	Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese
FR2620700B1 (fr) *	1987-09-17	1990-06-01	Adir	Procede de synthese d'alpha amino acides n alkyles et leurs esters. application a la synthese de carboxyalkyl dipeptides

2000
- 2000-04-06 FR FR0004379A patent/FR2807431B1/fr not_active Expired - Fee Related
2001
- 2001-03-20 PL PL346555A patent/PL204471B1/pl unknown
- 2001-03-30 HU HU0101336A patent/HU227674B1/hu not_active IP Right Cessation
- 2001-04-05 AT AT01921486T patent/ATE369338T1/de active
- 2001-04-05 GE GEAP20016679A patent/GEP20063797B/en unknown
- 2001-04-05 AU AU4847001A patent/AU4847001A/xx active Pending
- 2001-04-05 BR BRPI0109836-5A patent/BRPI0109836B1/pt not_active IP Right Cessation
- 2001-04-05 ES ES01921486T patent/ES2291307T3/es not_active Expired - Lifetime
- 2001-04-05 NZ NZ52145401A patent/NZ521454A/en not_active IP Right Cessation
- 2001-04-05 HR HR20020876A patent/HRP20020876B1/xx not_active IP Right Cessation
- 2001-04-05 US US10/239,129 patent/US6835843B2/en not_active Expired - Lifetime
- 2001-04-05 WO PCT/FR2001/001026 patent/WO2001058868A1/fr not_active Ceased
- 2001-04-05 OA OA1200200306A patent/OA12242A/en unknown
- 2001-04-05 KR KR10-2002-7013376A patent/KR100507616B1/ko not_active Expired - Fee Related
- 2001-04-05 DK DK01921486T patent/DK1268424T3/da active
- 2001-04-05 AP APAP/P/2002/002630A patent/AP1385A/en active
- 2001-04-05 ME MEP-2008-670A patent/ME00441B/me unknown
- 2001-04-05 SK SK1418-2002A patent/SK286921B6/sk not_active IP Right Cessation
- 2001-04-05 RS YUP-738/02A patent/RS50808B/sr unknown
- 2001-04-05 CN CNB018073727A patent/CN1296355C/zh not_active Expired - Fee Related
- 2001-04-05 CZ CZ20023291A patent/CZ302575B6/cs not_active IP Right Cessation
- 2001-04-05 JP JP2001558419A patent/JP3939553B2/ja not_active Expired - Fee Related
- 2001-04-05 AU AU2001248470A patent/AU2001248470B2/en not_active Ceased
- 2001-04-05 EE EEP200200575A patent/EE05032B1/xx not_active IP Right Cessation
- 2001-04-05 EP EP01921486A patent/EP1268424B1/fr not_active Expired - Lifetime
- 2001-04-05 PT PT01921486T patent/PT1268424E/pt unknown
- 2001-04-05 CA CA002405486A patent/CA2405486C/fr not_active Expired - Fee Related
- 2001-04-05 DE DE60129800T patent/DE60129800T2/de not_active Expired - Lifetime
- 2001-04-05 EA EA200201057A patent/EA005079B1/ru not_active IP Right Cessation
- 2001-04-05 MX MXPA02009706A patent/MXPA02009706A/es active IP Right Grant
- 2001-05-04 UA UA2002118786A patent/UA75070C2/uk unknown
2002
- 2002-09-16 ZA ZA200207419A patent/ZA200207419B/en unknown
- 2002-10-04 NO NO20024808A patent/NO324174B1/no not_active IP Right Cessation
- 2002-11-04 BG BG107249A patent/BG65984B1/bg unknown
2007
- 2007-10-16 CY CY20071101338T patent/CY1108522T1/el unknown

Also Published As

Publication number	Publication date
BG107249A (bg)	2003-07-31
PT1268424E (pt)	2007-10-16
ES2291307T3 (es)	2008-03-01
BR0109836A (pt)	2003-06-24
CA2405486A1 (fr)	2001-08-16
EP1268424A1 (fr)	2003-01-02
CA2405486C (fr)	2008-07-29
WO2001058868A1 (fr)	2001-08-16
DK1268424T3 (da)	2007-12-17
AP2002002630A0 (en)	2002-09-30
FR2807431A1 (fr)	2001-10-12
HRP20020876A2 (en)	2004-02-29
UA75070C2 (uk)	2006-03-15
CN1296355C (zh)	2007-01-24
HRP20020876B1 (en)	2010-10-31
YU73802A (sh)	2006-01-16
OA12242A (en)	2003-12-08
MXPA02009706A (es)	2004-09-06
AU2001248470B2 (en)	2005-01-20
EA200201057A1 (ru)	2003-06-26
ATE369338T1 (de)	2007-08-15
DE60129800T2 (de)	2008-06-05
EA005079B1 (ru)	2004-10-28
HK1053309A1 (en)	2003-10-17
HU0101336D0 (en)	2001-06-28
US20030069431A1 (en)	2003-04-10
JP3939553B2 (ja)	2007-07-04
NO20024808L (no)	2002-10-04
HUP0101336A2 (hu)	2002-02-28
NZ521454A (en)	2004-03-26
BRPI0109836B1 (pt)	2015-08-04
AU4847001A (en)	2001-08-20
AP1385A (en)	2005-04-08
ZA200207419B (en)	2003-09-16
PL346555A1 (en)	2001-09-10
SK14182002A3 (sk)	2003-02-04
HUP0101336A3 (en)	2003-03-28
ME00441B (me)	2011-10-10
NO20024808D0 (no)	2002-10-04
HU227674B1 (hu)	2011-11-28
EE05032B1 (et)	2008-06-16
DE60129800D1 (de)	2007-09-20
CZ20023291A3 (cs)	2003-02-12
CY1108522T1 (el)	2014-04-09
US6835843B2 (en)	2004-12-28
EP1268424B1 (fr)	2007-08-08
CZ302575B6 (cs)	2011-07-20
BG65984B1 (bg)	2010-08-31
CN1420867A (zh)	2003-05-28
NO324174B1 (no)	2007-09-03
GEP20063797B (en)	2006-04-25
FR2807431B1 (fr)	2002-07-19
KR20030013381A (ko)	2003-02-14
KR100507616B1 (ko)	2005-08-10
RS50808B (sr)	2010-08-31
JP2003531825A (ja)	2003-10-28
EE200200575A (et)	2004-04-15
PL204471B1 (pl)	2010-01-29

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Publication	Publication Date	Title
SK14182002A3 (sk)	2003-02-04	Spôsob syntézy perindoprilu a jeho farmaceuticky prijateľných solí
US20040198988A1 (en)	2004-10-07	Novel method for synthesis of (2s, 3as, 7as)-1-{(s)-alanyl}-octahydro-1h-indole-2-carboxylic acid derivatives and use for synthesis of perindopril
SK287067B6 (sk)	2009-11-05	Spôsob syntézy esterov N-[(S)-1-karboxybutyl]-(S)-alanínu a ich použitie pri syntéze perindoprilu
KR100825537B1 (ko)	2008-04-25	페린도프릴 및 이의 약학적으로 허용되는 염의 합성 방법
CN1326871C (zh)	2007-07-18	培哚普利和其可药用盐的新合成方法
EA008668B1 (ru)	2007-06-29	Новый способ синтеза периндоприла и его фармацевтически приемлемых солей
HK1095840A1 (en)	2007-05-18	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
HK1053309B (en)	2007-05-11	Method for synthesis of perindopril and its pharmaceutically acceptable salts
HK1095840B (en)	2009-07-24	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
HK1095839B (en)	2009-06-26	Method for the synthesis of perindopril and the pharmaceutically-acceptable salts thereof