http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1345934-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_73ee0bacab5a7576a6a3244747f6ea99 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C51-367 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F9-4006 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D307-935 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D309-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C405-0016 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C405-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C405-0025 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C51-09 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C51-60 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C51-09 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C405-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C51-60 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C51-367 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D307-935 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D309-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F9-40 |
| filingDate | 1971-07-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1974-02-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1345934-A |
| titleOfInvention | Cyclopentane derivatives |
| abstract | 1345934 Prosteglandin derivatives; phosphoric acid esters IMPERIAL CHEMICAL INDUSTRIES Ltd 13 June 1972 [14 July 1971] 33048/71 Headings C2C and C2P [Also in Divisions A5 and C3] The invention comprise prosteglandin derivatives of the formula wherein R<SP>1</SP> is hydroxymethyl, carboxyl or alkoxycarbonyl of up to 11 carbon atoms; either R<SP>2</SP> is OH or C 1-4 alkanoyloxy and R<SP>3</SP> is H, or R<SP>2</SP> and R<SP>3</SP> together form an oxo radical; A is -CH 2 CH 2 - or trans-CH=CH-; X is C 1-9 alkylene, and R<SP>4</SP> is C 1-9 alkyl or C 5-7 cycloalkyl provided that X and R<SP>4</SP> together contain not more than 10 carbon atoms, and for those compounds wherein R<SP>1</SP> is carboxy, pharmaceutically acceptable salts. Compounds of the above formula in which R<SP>1</SP> is carboxy are obtained by hydrolysing compounds of the formula or mixed anhydrides thereof, wherein R<SP>5</SP> and R<SP>6</SP> each are a tetrahydropyren-2-yloxy radical. The acids thus obtained may be converted to the corresponding esters by reacting them with diazoalkanes of the formula R<SP>7</SP>.N. 2 , wherein R<SP>7</SP> is C 1-10 alkyl, or reacting salts thereof with C 1-10 alkyl halides, and the esters reduced to compounds of the Formula I above in which R<SP>1</SP> is hydroxymethyl. 9α - Hydroxy - 16 - pentyloxy - 11α,15 - bis- (tetrahydropyran - 2 - yloxy) - 17,18,19,20- tetranor - 5 - cis,13 - trans - prostadienoic acid is prepared by reacting (4-carboxybutyl)triphenylphosphonium bromide with 3,3a#,4,5, 6,6a# - hexahydro - 2 - hydroxy - 4# - [4- pentyloxy - 3 - (tetrahydropyran - 2 - yloxy) - 1 - transbutenyl] - 5α - (tetrahydropyran - 2 - yloxy) 2H - cyclopenta[b]furan, obtained by reducing 3,3a#,4,5,6,6a# - hexahydro - 2 - oxo - 4# - [4- pentyloxy - 3 - (tetrahydropyran - 2 - yloxy) - 1- trans - butenyl] - 5α - (tetrahydropyran - 2 - yloxy)- 2H - cyclopenta[b]furan, resulting from the reaction between dihydropyran and 3,3a#,4,5,6, 6a# - hexahydro - 5α - hydroxy - 2 - oxo - 4#- (4 - pentyloxy - 3 - hydroxy - 1 - trans - butenyl)- 2H-cyclopenta[b]furan, which is made by hydrolysing 3,3a#,4,5,6,6a# - hexahydro - 2 - oxo - 4#- (4 - pentyloxy - 3 - hydroxy - 1 - trans - butenyl)- 5α - (4 - phenylbenzoyloxy) - 2H - cyclopenta[b]- furan obtained by reducing 3,3a,4,5,6,6a#- hexahydro - 2 - oxo - 4# - (3 - oxo - 4 - pentyloxy- 1 - trans - butenyl) - 5α - (4 - phenylbenzoyloxy)- 2H - cyclopenta[b]furan, resulting from the reaction between dimethyl 2-oxo-3-pentyloxypropylphosphonate and 5α - (4 - phenylbenzoyloxy) - 4# - formyl - 3,3a#,4,5,6,6a#- hexahydro - 2H - cyclopenta[b]furan - 2 one. The following compounds are prepared by reacting the appropriate phosphonate with 5α - (4 - phenylbenzoyloxy) - 4# - formyl- 3,3a#,4,5,6,6a# - hexahydrocyclo - 2H - penteno- [b]furan: 3,3a#,4,5,6,6a# - hexahydro - 5α - (4- phenylbenzoyloxy) - 4# - [3 - oxo - 4 - propoxy (or butoxy or isobutoxy, or hexyloxy) - 1 - transbutenyl], 2H-cyclopenteno[b]furan-2-one. 3,3a#,4,5,6,6a# - Hexahydro - 4# - (3 - oxo - 4- pentyloxybutyl) - 5α - (4 - phenylbenzoyloxy) - 2H- cyclopenteno[b]furan-2-one is obtained by hydrogenerating the corresponding unsaturated ketone. Butyl 3-butoxypropionate is prepared by reacting ethyl acrylate with a solution of sodium dissolved in n-butanol. Methyl 4-propoxybutyrate is obtained by esterifying 4-propoxybutyric acid, made by reacting 4- bromobutyric acid with a solution of sodium in n-propanol. Ethyl 5-ethoxypentanoate is made by hydrogenating ethyl 5-ethoxy-2-pentenoate obtained by reacting triethyl phosphonoacetate with 3- ethoxypropionaldehyde resulting from the hydrolysis of the corresponding diethyl acetal 6- methoxyhexanoyl chloride is prepared by reacting thionyl chloride with 6-methoxyhexanoic acid, resulting from the hydrolysis of ethyl 6-methoxyhexanoate, obtained by reacting ethyl 6-bromohexanoate and a solution of sodium in methanol. Phosphonates of the formula are prepared by reacting dimethyl methylphosphonate with compounds of the formula R<SP>4</SP>.O.XCOR<SP>5</SP>, where R<SP>5</SP> is alkoxy or halogen, in the presence of butyl-lithium. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4191774-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4113766-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4061671-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4169895-A |
| priorityDate | 1971-07-14-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 92.