HUP0202437A2 - Új eljárás (2S,3aS,7aS)-1-[(S)-alanil]oktahidro-1H-indol-2-karbonsav vegyületek előállítására és ezek alkalmazása perindopril előállítására - Google Patents
Új eljárás (2S,3aS,7aS)-1-[(S)-alanil]oktahidro-1H-indol-2-karbonsav vegyületek előállítására és ezek alkalmazása perindopril előállításáraInfo
- Publication number
- HUP0202437A2 HUP0202437A2 HU0202437A HUP0202437A HUP0202437A2 HU P0202437 A2 HUP0202437 A2 HU P0202437A2 HU 0202437 A HU0202437 A HU 0202437A HU P0202437 A HUP0202437 A HU P0202437A HU P0202437 A2 HUP0202437 A2 HU P0202437A2
- Authority
- HU
- Hungary
- Prior art keywords
- general formula
- compound
- moles
- perindopril
- mole
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 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 abstract 2
- 229960002582 perindopril Drugs 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910019020 PtO2 Inorganic materials 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical group O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 abstract 1
- 235000004279 alanine Nutrition 0.000 abstract 1
- -1 alanine compound Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052799 carbon Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Peptides Or Proteins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
Abstract
A találmány tárgya az (I) általános képletű vegyületek ipari szintéziseljárása, ahol a képletben R1 jelentése hidrogénatom, lineáris vagyelágazó szénláncú 1-6 szénatomos alkilcsoport vagy benzilcsoport, ésR2 jelentése egy amino funkciós csoportot védő csoport. Az eljárássorán egy (V) általános képletű észtert, ahol R1 jelentése az (I)általános képletnél megadott, reagáltatnak egy (VI) általános képletűalanin vegyülettel, ahol R2 jelentése az (I) általános képletnélmegadott, egy szerves oldószerben, 1-hidroxibenzotriazol távollétébenvagy az alkalmazott (V) általános képletű vegyületek 1 móljáravonatkoztatva 0,6 mólnál kevesebb mennyiségű 1-hidroxibenzotriazoljelenlétében, az alkalmazott (V) általános képletű vegyület 1 móljáravonatkoztatva 1-1,2 mól diciklohexilkarbodiimid jelenlétében és azalkalmazott (V) általános képletű vegyület 1 móljára vonatkoztatva 1-1,2 mól trietilamin jelenlétében 20-50 °C hőmérsékleten, és ily módonizolálás, majd átkristályosítás után (VII) általános képletűvegyületet kapnak, ahol R1 és R2 jelentése a fentiekben megadott, amitazután egy katalizátor jelenlétében, előnyösen PtO2 vagy szénhordozóspalládium, ruténium, platina vagy nikkel jelenlétében 1-40 barhidrogénnyomáson 30-70 °C hőmérsékleten. A találmány tárgya továbbá atalálmány szerinti eljárással előállított vegyületek alkalmazásaperindopril és ennek gyógyászatilag elfogadható sói előállítására. Ó
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0109839A FR2827860B1 (fr) | 2001-07-24 | 2001-07-24 | 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 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| HU0202437D0 HU0202437D0 (hu) | 2002-10-28 |
| HUP0202437A2 true HUP0202437A2 (hu) | 2003-02-28 |
| HUP0202437A3 HUP0202437A3 (en) | 2003-05-28 |
| HU229396B1 HU229396B1 (hu) | 2013-11-28 |
Family
ID=8865826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0202437A HU229396B1 (hu) | 2001-07-24 | 2002-07-24 | Új eljárás (2S,3aS,7aS)-1-[(S)-alanil]oktahidro-1H-indol-2-karbonsav vegyületek elõállítására és ezek alkalmazása perindopril elõállítására |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7060842B2 (hu) |
| EP (1) | EP1256590B1 (hu) |
| JP (1) | JP3868957B2 (hu) |
| KR (1) | KR100607556B1 (hu) |
| CN (1) | CN1533398A (hu) |
| AR (1) | AR035081A1 (hu) |
| AT (1) | ATE318838T1 (hu) |
| AU (1) | AU2002334027B8 (hu) |
| BR (1) | BR0211334A (hu) |
| CA (1) | CA2455706C (hu) |
| DE (1) | DE60209458T2 (hu) |
| DK (1) | DK1256590T3 (hu) |
| EA (1) | EA005490B1 (hu) |
| ES (1) | ES2259071T3 (hu) |
| FR (1) | FR2827860B1 (hu) |
| HU (1) | HU229396B1 (hu) |
| MA (1) | MA27130A1 (hu) |
| MX (1) | MXPA04000443A (hu) |
| NO (1) | NO328234B1 (hu) |
| NZ (1) | NZ530427A (hu) |
| PL (1) | PL212408B1 (hu) |
| PT (1) | PT1256590E (hu) |
| SI (1) | SI1256590T1 (hu) |
| WO (1) | WO2003016336A1 (hu) |
| ZA (1) | ZA200400246B (hu) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1333026T3 (da) * | 2002-01-30 | 2007-10-22 | Servier Lab | Fremgangsmåde til fremstilling af perindopril med höj renhed og nyttige mellemforbindelser til syntesen |
| 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 |
| EP1603558B1 (en) | 2003-02-28 | 2008-05-21 | Les Laboratoires Servier S.A. | Process for preparation of perindopril and salts thereof |
| DE60301930T2 (de) | 2003-02-28 | 2006-07-27 | Les Laboratoires Servier | Verfahren für die Synthese von Perindopril und seiner pharmazeutisch annehmbaren Salze |
| SI1338591T1 (sl) * | 2003-02-28 | 2006-02-28 | Servier Lab | NOV POSTOPEK ZA SINTEZO (2S,3aS,7aS)-PERHIDROINDOL-2-KARBOKSILNE KISLINE IN NJENIH ESTROV TER UPORABA PRI SINTEZI PERINDOPRILA |
| DK1321471T3 (da) * | 2003-03-12 | 2005-08-29 | Servier Lab | Ny syntesefremgangsmåde til perindopril og farmaceutisk acceptable salte heraf |
| 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 |
| ES2231760T3 (es) * | 2003-03-12 | 2005-05-16 | Les Laboratoires Servier | Nuevo procedimiento de sintesis del acido(2s, 3as,7as)perhidroindol-2-carboxilico y de sus esteres, y su aplicacion a la sintesis de perindopril. |
| MXPA05013811A (es) | 2003-06-24 | 2006-06-27 | Servier Lab | Novedosas formas cristalinas de perindopril erbumina. |
| ATE337332T1 (de) * | 2003-07-31 | 2006-09-15 | Servier Lab | Verfahren für die synthese von perindopril und seiner pharmazeutischen annehmbaren salzen |
| JP4720132B2 (ja) * | 2003-10-30 | 2011-07-13 | 住友化学株式会社 | 光学活性なｎ−保護−オクタヒドロ−１ｈ−インドール−２−カルボン酸の製造方法 |
| EP1420030A3 (fr) * | 2003-12-10 | 2004-05-26 | Les Laboratoires Servier | 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 |
| GB2413128A (en) * | 2004-04-13 | 2005-10-19 | Neopharma Ltd | Process for the preparation of perindopril |
| ITFI20040174A1 (it) * | 2004-08-03 | 2004-11-03 | Protera S R L | Derivati arilsolfonammidici dell'acido idrossammico ad azione inibitoria di metalloproteinasi |
| KR101329457B1 (ko) | 2006-12-19 | 2013-11-15 | 에스케이바이오팜 주식회사 | 옥타하이드로인돌-2-카르복시산의 제조방법 |
| 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. |
Family Cites Families (5)
| 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 |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| FR2807037B1 (fr) * | 2000-03-31 | 2002-05-10 | Adir | NOUVEAU PROCEDE DE SYNTHESE DES ESTERS DE LA N-[(s)-1- CARBOXYBUTYL]-(S)-ALANINE ET APPLICATION A LA SYNTHESE DU PERINDOPRIL |
| FR2807431B1 (fr) * | 2000-04-06 | 2002-07-19 | Adir | Nouveau procede de synthese du perindopril et de ses sels pharmaceutiquement acceptables |
| FR2807430B1 (fr) | 2000-04-11 | 2002-05-17 | Adir | Nouveau procede de synthese des esters de la n-[(s)-1- carboxybutyl]-(s)-alanine et application a la synthese du perindopril |
-
2001
- 2001-07-24 FR FR0109839A patent/FR2827860B1/fr not_active Expired - Fee Related
-
2002
- 2002-07-23 CA CA2455706A patent/CA2455706C/fr not_active Expired - Fee Related
- 2002-07-23 SI SI200230292T patent/SI1256590T1/sl unknown
- 2002-07-23 EP EP02291853A patent/EP1256590B1/fr not_active Expired - Lifetime
- 2002-07-23 DK DK02291853T patent/DK1256590T3/da active
- 2002-07-23 WO PCT/FR2002/002627 patent/WO2003016336A1/fr active IP Right Grant
- 2002-07-23 ES ES02291853T patent/ES2259071T3/es not_active Expired - Lifetime
- 2002-07-23 AT AT02291853T patent/ATE318838T1/de active
- 2002-07-23 AR ARP020102757A patent/AR035081A1/es not_active Application Discontinuation
- 2002-07-23 KR KR1020047001052A patent/KR100607556B1/ko not_active IP Right Cessation
- 2002-07-23 DE DE60209458T patent/DE60209458T2/de not_active Expired - Lifetime
- 2002-07-23 CN CNA028146093A patent/CN1533398A/zh active Pending
- 2002-07-23 MX MXPA04000443A patent/MXPA04000443A/es active IP Right Grant
- 2002-07-23 AU AU2002334027A patent/AU2002334027B8/en not_active Ceased
- 2002-07-23 NZ NZ530427A patent/NZ530427A/en not_active IP Right Cessation
- 2002-07-23 EA EA200400110A patent/EA005490B1/ru not_active IP Right Cessation
- 2002-07-23 PT PT02291853T patent/PT1256590E/pt unknown
- 2002-07-23 BR BR0211334-1A patent/BR0211334A/pt not_active IP Right Cessation
- 2002-07-23 US US10/484,022 patent/US7060842B2/en not_active Expired - Lifetime
- 2002-07-23 JP JP2003521258A patent/JP3868957B2/ja not_active Expired - Fee Related
- 2002-07-24 PL PL355159A patent/PL212408B1/pl unknown
- 2002-07-24 HU HU0202437A patent/HU229396B1/hu not_active IP Right Cessation
-
2004
- 2004-01-08 MA MA27474A patent/MA27130A1/fr unknown
- 2004-01-13 NO NO20040151A patent/NO328234B1/no not_active IP Right Cessation
- 2004-01-13 ZA ZA200400246A patent/ZA200400246B/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HUP0202437A2 (hu) | Új eljárás (2S,3aS,7aS)-1-[(S)-alanil]oktahidro-1H-indol-2-karbonsav vegyületek előállítására és ezek alkalmazása perindopril előállítására | |
| CY1109882T1 (el) | Νεα αλατα ατορβαστατινης και φαρμακευτικες συνθεσεις που τα περιεχουν | |
| CS70091A2 (en) | Method of aspartame production | |
| JPH07503942A (ja) | ペプチド合成に使用するための保護されたホスホノアルキルフェニルアラニン化合物 | |
| TR200100286T2 (tr) | (1H)-Benzo[C]kuinolizin-3-on türevlerinin sentezi için proses. | |
| HUP0101337A2 (hu) | Új eljárás N-[(S)-1-karboxibutil]-(S)-alanin-észterek előállítására, és a perindopril szintézisnél történő alkalmazása | |
| JP4331207B2 (ja) | 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 | |
| NO20055257L (no) | Ny fremgangsmate for syntesen av s-indolin-2-karboksylsyre og anvendelse derav i syntesen av perindopril | |
| ES2249691T3 (es) | Procedimiento de sintesis de derivados del acido (2s,3as,7as)-1-(s)-alanil)-octahidro-1h-indol-2-carboxilico y su utilizacion en la sintesis de perindopril. | |
| Radau et al. | New Cyanopeptide‐Derived Low MolecularWeight Thrombin Inhibitors | |
| HUP0103309A2 (hu) | N-(terc-Butil)-hidroxil-amin új sói és előállításuk | |
| NO20061152L (no) | Ny fremgangsmate for syntese av N-(S)-1-karboksybuty)-(S)-alanin og anvendelse derav for a syntetisere perindopril | |
| WO2004078707A3 (fr) | Nouveau procede de synthese de lacide (2s, 3as, 7as)-perhydroindole-2-carboxylique et de ses esters et application a la synthese du perindopril | |
| MY135652A (en) | NEW PROCESS FOR THE SYNTHESIS OF (2S, 3aS, 7aS)-PERHYDROINDOLE-2-CARBOXYLIC ACID AND ESTERS THEREOF, AND APPLICATION IN THE SYNTHESIS OF PERINDOPRIL | |
| JP2006513243A5 (hu) | ||
| ES2240926T3 (es) | Procedimiento de sintesis de n-((s)-1-(etoxicarbonil)butil)-(s)-alanina y su utilizacion en la sintesis de perindopril. | |
| KR950009316B1 (ko) | 피롤리딘카르복실산 유도체의 제조방법 | |
| HUP0202331A2 (hu) | Eljárás 5- és/vagy 6-helyzetben szubsztituált 2-hidroxi-benzoesav-észterek előállítására | |
| JPWO2003042237A1 (ja) | ペプチド誘導体及びその薬学的に許容される塩、その製造法並びにその用途 | |
| NO20063027L (no) | Fremgangsmaten for syntesen av derivater av (2S,3aS,7aS)-1-[(S)-alkanyl]-oktahydro-lH-indol-2-karboksylsyre og anvendelse derav i syntesen av perindopril | |
| MY136549A (en) | NEW PROCESS FOR THE SYNTHESIS OF (2S, 3aS, 7aS)-PERHYDROINDOLE-2-CARBOXYLIC ACID AND ESTERS THEREOF, AND APPLICATION IN THE SYNTHESIS OF PERINDOPRIL | |
| JPH04356482A (ja) | 加水分解活性を有する環状ジペプチド誘導体 | |
| KR960007616A (ko) | 안지오 텐신 변환효소의 작용을 억제하는 트리펩티드 유사체 화합물 및 그 제조방법 | |
| FR2850383A1 (fr) | Procede de synthese ameliore de derives diamides du tripeptide kpv |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of definitive patent protection due to non-payment of fees |