NO324174B1 - Fremgangsmate ved syntesen av perindopril og farmasoytisk akseptable salter derav - Google Patents
Fremgangsmate ved syntesen av perindopril og farmasoytisk akseptable salter derav Download PDFInfo
- Publication number
- NO324174B1 NO324174B1 NO20024808A NO20024808A NO324174B1 NO 324174 B1 NO324174 B1 NO 324174B1 NO 20024808 A NO20024808 A NO 20024808A NO 20024808 A NO20024808 A NO 20024808A NO 324174 B1 NO324174 B1 NO 324174B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- perindopril
- mol
- triethylamine
- Prior art date
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 description 20
- 229960002582 perindopril Drugs 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 10
- 230000015572 biosynthetic process Effects 0.000 title claims description 8
- 238000003786 synthesis reaction Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 title claims description 6
- 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 23
- 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
- 238000001308 synthesis method Methods 0.000 claims description 6
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 238000009903 catalytic hydrogenation reaction 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
- 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
- 238000003756 stirring Methods 0.000 description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 101800000734 Angiotensin-1 Proteins 0.000 description 2
- 102400000344 Angiotensin-1 Human genes 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
- 239000000706 filtrate Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- NRAMCLOSUDJHAH-YUMQZZPRSA-N (2s)-2-[[(2s)-1-ethoxy-1-oxopropan-2-yl]amino]pentanoic acid Chemical compound CCC[C@@H](C(O)=O)N[C@@H](C)C(=O)OCC NRAMCLOSUDJHAH-YUMQZZPRSA-N 0.000 description 1
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-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
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- ZNAYHAPFFQRGES-SVXFZJLFSA-N benzyl (2s,3as,7as)-1-[(2s)-2-[[(2s)-1-ethoxy-1-oxopentan-2-yl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylate Chemical compound O=C([C@@H]1C[C@@H]2CCCC[C@@H]2N1C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)OCC1=CC=CC=C1 ZNAYHAPFFQRGES-SVXFZJLFSA-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
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 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
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000203 mixture 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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)
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 (3)
| Publication Number | Publication Date |
|---|---|
| NO20024808L NO20024808L (no) | 2002-10-04 |
| NO20024808D0 NO20024808D0 (no) | 2002-10-04 |
| NO324174B1 true NO324174B1 (no) | 2007-09-03 |
Family
ID=8848925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20024808A NO324174B1 (no) | 2000-04-06 | 2002-10-04 | Fremgangsmate ved syntesen av perindopril og farmasoytisk akseptable salter derav |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6835843B2 (zh) |
| EP (1) | EP1268424B1 (zh) |
| JP (1) | JP3939553B2 (zh) |
| KR (1) | KR100507616B1 (zh) |
| CN (1) | CN1296355C (zh) |
| AP (1) | AP1385A (zh) |
| AT (1) | ATE369338T1 (zh) |
| AU (2) | AU4847001A (zh) |
| BG (1) | BG65984B1 (zh) |
| BR (1) | BRPI0109836B1 (zh) |
| CA (1) | CA2405486C (zh) |
| CY (1) | CY1108522T1 (zh) |
| CZ (1) | CZ302575B6 (zh) |
| DE (1) | DE60129800T2 (zh) |
| DK (1) | DK1268424T3 (zh) |
| EA (1) | EA005079B1 (zh) |
| EE (1) | EE05032B1 (zh) |
| ES (1) | ES2291307T3 (zh) |
| FR (1) | FR2807431B1 (zh) |
| GE (1) | GEP20063797B (zh) |
| HK (1) | HK1053309A1 (zh) |
| HR (1) | HRP20020876B1 (zh) |
| HU (1) | HU227674B1 (zh) |
| ME (1) | ME00441B (zh) |
| MX (1) | MXPA02009706A (zh) |
| NO (1) | NO324174B1 (zh) |
| NZ (1) | NZ521454A (zh) |
| OA (1) | OA12242A (zh) |
| PL (1) | PL204471B1 (zh) |
| PT (1) | PT1268424E (zh) |
| RS (1) | RS50808B (zh) |
| SK (1) | SK286921B6 (zh) |
| UA (1) | UA75070C2 (zh) |
| WO (1) | WO2001058868A1 (zh) |
| ZA (1) | ZA200207419B (zh) |
Families Citing this family (32)
| 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 |
| EP1333026B1 (en) * | 2002-01-30 | 2007-06-27 | Les Laboratoires Servier | Process for the preparation of high purity perindopril and intermediates useful in the synthesis |
| 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 |
| ATE307139T1 (de) * | 2003-02-28 | 2005-11-15 | Servier Lab | Verfahren für die synthese von perindopril und seiner pharmazeutisch annehmbaren salze |
| SI1403277T1 (sl) * | 2003-02-28 | 2005-12-31 | Servier Lab | NOV POSTOPEK ZA SINTEZO DERIVATOV (2S, 3aS, 7aS)-1-((S)-ALANIL)-OKTAHIDRO-1H-INDOL-2-KARBOKSILNE KISLINE IN UPORABA PRI SINTEZI PERINDOPRILA |
| ATE395913T1 (de) | 2003-02-28 | 2008-06-15 | Servier S A Lab | Verfahren zur herstellung von perindopril |
| ES2250847T3 (es) * | 2003-02-28 | 2006-04-16 | Les Laboratoires Servier | Nuevo procedimiento de sintesis del acido (2s,3as,7as)-perhidroindol-2-carboxilico y sus eteres y su aplicacion a la sintesis de perindropil. |
| ATE280775T1 (de) * | 2003-03-12 | 2004-11-15 | Servier Lab | Verfahren zur synthese von (2s,3as,7as)-1-((s)- |
| 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 |
| JP2007507418A (ja) | 2003-06-24 | 2007-03-29 | レ・ラボラトワール・セルヴィエ | ペリンドプリルエルブミンの新しい結晶型 |
| DE60307721T2 (de) * | 2003-07-31 | 2007-10-18 | Les Laboratoires Servier | Verfahren für die Synthese von Perindopril und seiner pharmazeutischen annehmbaren Salzen |
| EP1367062B1 (fr) * | 2003-07-31 | 2006-08-30 | Les Laboratoires Servier | Nouveau procédé de synthèse du perindopril et de ses sels pharmaceutiquement acceptables |
| SI1675827T1 (sl) * | 2003-10-21 | 2010-04-30 | Servier Lab | Nov postopek za pripravo kristaliniŽŤnega perindopril erbumina |
| EP1420029B9 (fr) * | 2003-12-10 | 2008-11-12 | Les Laboratoires Servier | Procédé de synthèse du perindopril et ses sels pharmaceutiquement acceptables |
| PL1729739T3 (pl) * | 2004-03-29 | 2017-04-28 | Les Laboratoires Servier | Sposób wytwarzania stałej kompozycji farmaceutycznej |
| 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. |
| PL1679072T3 (pl) * | 2005-01-06 | 2009-03-31 | Ipca Laboratories Ltd | Sposób syntezy pochodnych kwasu (2S, 3aS, 7aS)-1-(S)-alanylo- oktahydro-1H-indolo-2-karboksylowego i zastosowanie w syntezie perindoprilu |
| 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 |
| EP2137148A1 (en) * | 2007-03-22 | 2009-12-30 | 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 |
| FR3050380B1 (fr) | 2016-04-20 | 2020-07-10 | Les Laboratoires Servier | Composition pharmaceutique comprenant un betabloquant, un inhibiteur de l'enzyme de conversion et un antihypertenseur ou un ains. |
| 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)
| 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 KR KR10-2002-7013376A patent/KR100507616B1/ko not_active IP Right Cessation
- 2001-04-05 GE GEAP20016679A patent/GEP20063797B/en unknown
- 2001-04-05 ES ES01921486T patent/ES2291307T3/es not_active Expired - Lifetime
- 2001-04-05 RS YUP-738/02A patent/RS50808B/sr unknown
- 2001-04-05 DK DK01921486T patent/DK1268424T3/da active
- 2001-04-05 MX MXPA02009706A patent/MXPA02009706A/es active IP Right Grant
- 2001-04-05 JP JP2001558419A patent/JP3939553B2/ja not_active Expired - Fee Related
- 2001-04-05 BR BRPI0109836-5A patent/BRPI0109836B1/pt not_active IP Right Cessation
- 2001-04-05 EP EP01921486A patent/EP1268424B1/fr not_active Expired - Lifetime
- 2001-04-05 US US10/239,129 patent/US6835843B2/en not_active Expired - Lifetime
- 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 AU AU4847001A patent/AU4847001A/xx active Pending
- 2001-04-05 NZ NZ52145401A patent/NZ521454A/en not_active IP Right Cessation
- 2001-04-05 OA OA1200200306A patent/OA12242A/en unknown
- 2001-04-05 AU AU2001248470A patent/AU2001248470B2/en not_active Ceased
- 2001-04-05 DE DE60129800T patent/DE60129800T2/de not_active Expired - Lifetime
- 2001-04-05 CZ CZ20023291A patent/CZ302575B6/cs not_active IP Right Cessation
- 2001-04-05 EA EA200201057A patent/EA005079B1/ru not_active IP Right Cessation
- 2001-04-05 CN CNB018073727A patent/CN1296355C/zh not_active Expired - Fee Related
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- 2001-04-05 CA CA002405486A patent/CA2405486C/fr not_active Expired - Fee Related
- 2001-04-05 PT PT01921486T patent/PT1268424E/pt unknown
- 2001-04-05 AT AT01921486T patent/ATE369338T1/de active
- 2001-04-05 EE EEP200200575A patent/EE05032B1/xx not_active IP Right Cessation
- 2001-04-05 AP APAP/P/2002/002630A patent/AP1385A/en active
- 2001-05-04 UA UA2002118786A patent/UA75070C2/uk unknown
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2002
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- 2002-10-04 NO NO20024808A patent/NO324174B1/no not_active IP Right Cessation
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- 2002-11-06 HR HR20020876A patent/HRP20020876B1/xx not_active IP Right Cessation
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2003
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