http://rdf.ncbi.nlm.nih.gov/pubchem/patent/PL-211506-B1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_6572ff5df928fd17340eb2a8cb6d8502 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y02P20-55 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07K5-06026 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07K5-0222 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P43-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-42 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07K5-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07K5-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-42 |
| filingDate | 2004-02-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_5a0c70dd32466b232c55b736c15671c3 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_ee05a0a67b678fe97313f18171e8555d |
| publicationDate | 2012-05-31-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | PL-211506-B1 |
| titleOfInvention | The method of obtaining (2S, 3aS, 7aS) -1 - [(S) -alanil] -octahydro-1H-indole-2-carboxylic acid compounds and their use in the synthesis of perindopril and the intermediate |
| abstract | Synthesis of 1-alanyl-octahydroindole derivatives (I) involves reacting 1-(1-cyclohexen-1-yl)-pyrrolidine (III) with an iodo-serine derivative (IV); deprotecting the product (V), cyclizing and dehydrating; reacting the obtained hexahydroindole derivative (VI) with alanine derivative (VII); and hydrogenating the obtained 1-alanyl-hexahydroindole derivative (VIII). Industrial synthesis of (2S,3aS,7aS)-1-((S)-alanyl)-octahydro-1H-indole-2-carboxylic derivatives of formula (I) involves: (1) reacting 1-(1-cyclohexen-1-yl)-pyrrolidine (III) with an iodo-serine derivative of formula (IV); (2) deprotecting the obtained cyclohexyl-serine derivative of formula (V) then cyclizing and dehydrating; (3) reacting the obtained hexahydroindole derivative of formula (VI) with an alanine derivative of formula (VII) in an organic solvent (e.g. tetrahydrofuran or ethyl acetate) at 20-50degreesC in presence of 1-1.2 moles (based on (V)) of each of dicyclohexyl carbodiimide and triethylamine; and (4) subjecting the obtained 1-alanyl-hexahydroindole derivative of formula (VIII) (after isolation and recrystallization) to hydrogenation under a pressure of 1-30 (preferably 1-10) bars in presence of a catalyst (e.g. palladium, platinum, rhodium or nickel), optionally followed by deprotection and reprotection of the acid function, to give (I). R1 = H, 1-6C alkyl or benzyl; R2, R3 = amino-protecting groups. An Independent claim is also included for the praparation of perindopril or it salt from (I). |
| priorityDate | 2003-02-28-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 88.