http://rdf.ncbi.nlm.nih.gov/pubchem/patent/NZ-335212-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_634715a790f7ef0163a61e9f364bebcd |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D491-18 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D489-09 |
| filingDate | 1996-11-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_ccce17aaab793536e467f17c8b90ad9c http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_25fb3d52e5c7e5522e5419bfe1f108d8 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_4c91ae83af4410073c87ea17cc546b8e |
| publicationDate | 2003-12-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | NZ-335212-A |
| titleOfInvention | Process for the preparation of 14- alkoxyindolomorphinans and 14-alkoxybenzofuranomorphinans |
| abstract | A process for preparing a compound of the formula (I) comprises: ia) reacting naloxone of formula (II), naltrexone of formula (III) or oxymorphone of formula (IIIa) with phenylhydrazine hydrochloride in the presence of acid producing naloxindole of formula (NLI), naltrindole of formula (NTI) or oxymorphindole of formula (OMI) or ib) naloxone of formula (II), naltrexone of formula (III) or oxymorphone of formula (IIIa) is reacted with O-phenyl- hydroxyl amine hydrochloride in the presence of acid, producing the benzofurane derivatives of formula (NLB), naltriben of formula (NTB) or OMB of the formula (OMB); ii) protecting the 3-hydroxy group present in the products of step ia) or ib) by alkylation with benzyl bromide, methoxymethyl bromide, ethoxymethyl bromide, trityl chloride, or a silylating agent, in the presence of a solvent and a base, producing a compound of the formula (IV) iii) treating a compound of the formula (IV) with dialkyl sulphates, alkyl halides, alkenyl halides, aralkyl halides, arylalkenyl halides, alkanoyl halides, or arylalkanoyl halides in a solvent such as N,N dimethyl formamide or tetrahydrofurane, using a base, producing a compound of the formula (V) or iv) optionally hydrolyzing in diluted acids a compound of formula (V) optionally in the presence of a solvent, producing a compound of the formula (VI) and v) alkylating or acylating the compound of the formula (VI) to produce a compound of the formula (I) wherein: R1 is allyl, cyclopropylmethyl or methyl; R2 is alkoxy, alkenyloxy, arylalkyloxy, arylalkenyloxy alkanoyloxy or arylalkanoyloxy; R3 is hydroxy, alkoxy, arylalkyloxy, alkenyloxy, alkanoyloxy, arylalkanoyloxy or alkyloxyalkoxy; X is O, NH or NR4 and R4 is alkoxy, alkenyloxy, arylalkyloxy, arylalkenyloxy, alkanoyloxy or arylalkanoyloxy provided that when R1 is cyclopropylmethyl and R2 is methoxymethyl X is not O or N-methoxymethyl. In formula (IV) R2 is benzyl, methoxymethyl, ethoxymethyl, trityl or silyl; and X is NH, O, N-benzyl, N-methoxymethyl, N-ethoxymethyl, N-trityl or N-silyl. In formula (V) R2 is benzyl, methoxymethyl, ethoxymethyl, trityl or silyl and X is NH, O, N-benzyl, N-methoxymethyl, N-ethoxymethyl, N-trityl or N-silyl. In formula (VI) X is NH, O or N-benzyl. |
| priorityDate | 1996-11-19-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 129.