Prenalterol
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| Trade names | Hyprenan |
| Other names | CGP-7760B; CGP-7760/B; H-133/22; IHP |
| Routes of administration | Oral, IV |
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| E number | {{#property:P628}} |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C12H19NO3 |
| Molar mass | 225.288 g·mol−1 |
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Prenalterol, sold under the brand name Hyprenan, is a sympathomimetic agent and cardiac stimulant which acts as a β1-adrenergic receptor partial agonist and is used in the treatment of heart failure.[1][2][3][4][5] It has selectivity for the β1-adrenergic receptor.[1][2][3][4] Its partial agonist activity or intrinsic sympathomimetic activity is about 60%.[6] It is said to have much greater impact on myocardial contractility than on heart rate.[4] The drug has been marketed in Denmark, Norway, and Sweden.[2]
Chemistry
[edit | edit source]Synthesis
[edit | edit source]Stereospecific
[edit | edit source]Prenalterol exhibits adrenergic agonist activity in spite of an interposed oxymethylene group. The stereospecific synthesis devised for this molecule relies on the fact that the side chain is very similar in oxidation state to that of a sugar.[7][8]
Condensation of monobenzone (2) with the epoxide derived from α-D-glucofuranose[9] affords the glycosylated derivative (3). Hydrolytic removal of the acetonide protecting groups[10] followed by cleavage of the sugar with periodate gives aldehyde (4). This is reduced to the glycol by means of NaBH4 and the terminal alcohol is converted to the mesylate (5). Displacement of the leaving group with isopropylamine followed by hydrogenolytic removal of the O-benzyl ether affords the β1-adrenergic selective adrenergic agonist prenalterol (6).
Racemic
[edit | edit source]Several preparations of the racemic mixture have been reported.[11][12][13][14][15]
See also
[edit | edit source]References
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- ^ DE 2503968, Jaeggi KA, Schröter H, Ostermayer F, "Optisch aktive Derivate des 1-Phenoxy-2-hydroxy-3-aminopropan und Verfahren zu ihrer Herstellung [Optically active derivatives of 1-phenoxy-2-hydroxy-3-aminopropane and the process for their production]", published Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)., assigned to Ciba-Geigy AG Chem. Abstr. 84, 5322 (1976).
- ^ corresp to U.S. patent 3,978,041 and U.S. patent 4,049,797 (1975, 1976, 1977, all to Ciba-Geigy)
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- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ NL 6409883 H. Köppe et al.
- ^ U.S. patent 3,637,852 (1965, 1972 both to Boehringer Ingelheim)
- ^ NL 301580 A. F. Crowther, L. H. Smith
- ^ U.S. patent 3,501,769 (1965, 1970 both to ICI)
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
Further reading
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