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Sauron
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The 3-carbon in the quinuclidine cage is also chiral. So it's more complex than would be the case with a single chiral center.
Lots of advances though in chiral chromatography.
Best approach would be to prepare the isomers of 3-quinuclidinol (which has already been done) and of the glycollic acid, and then esterify by a
method that does not racemize the alcohol. You'd be able to prepare all four stereoisomers with very high EE.
[Edited on 15-7-2008 by Sauron]
Sic gorgeamus a los subjectatus nunc.
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Ritter
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FMC filed a total of 3 patents on BZ-analog anticholinergic 'drugs'. Attached is a ChemDraw of the 3 most potent compounds found in US4467095.
Interestingly, the 2 specific compounds claimed in this patent do not include these structures.
[Edited on 15-7-2008 by Ritter]
Ritter
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\"The production of too many useful things results in too many useless people.\"
Karl Marx
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Ritter
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Here is a ChemDraw showing the structures & toxicity/potency data for the 2 compounds chosen to be specifically claimed out of the 46+ compounds
that were prepared in this series. It can only be concluded that these 2 had properties that singled them out to be agents of a particularly nasty
effect.
Ritter
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\"The production of too many useful things results in too many useless people.\"
Karl Marx
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Ritter
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The third FMC anti-cholinergic 'drug' patent is US4584378, which claims the 4 specific compounds shown in the ChemDraw attachment.
Ritter
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\"The production of too many useful things results in too many useless people.\"
Karl Marx
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Sauron
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Some of those might conceivably be of interest to the pharm boys. Those patents were issued long after the BZ program was scrapped as a military
failre, though they might have been filed much earlier. And by now they are expired, and in the public domain.
Military failures, street drug failures, and marginally interesting pharmaceutically. I do find the chemistry interesting, though.
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Ritter
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| Quote: | Originally posted by Ritter
Here is a ChemDraw showing the structures & toxicity/potency data for the 2 compounds chosen to be specifically claimed out of the 46+ compounds
that were prepared in this series. It can only be concluded that these 2 had properties that singled them out to be agents of a particularly nasty
effect. |
Compound 13 has the assigned code of 302,668.
Ritter
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\"The production of too many useful things results in too many useless people.\"
Karl Marx
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