Formation and utility of sulfonic acid protecting groups

Details Formation and utility of sulfonic acid protecting groups Formation and utility of sulfonic acid protecting groups

1995-05-12

1997-01-21

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540224, 540225, 540342, 544238, 546324, 5483691, 549 72, 549408, 552540, 552544, 558 46, 558 47, 558 49, 558 50, C07D50160, A61K 31545

Patent

active

055960952

ABSTRACT:
The present invention is a method of protecting a sulfonic acid functional group in an organic molecule as a substituted or unsubstituted neopentyl sulfonate ester. The method allows the conversion of R--SO.sub.3 --H to R'--SO.sub.3 --H, wherein R and R' are different organic radicals. Also disclosed is a method of increasing the bioavailability of drugs with a sulfonic acid functional group by protecting the sulfonic acid functional group as a substituted neopentyl sulfonate ester which has a masked heteroatom nucleophile. The masked nucleophile can be liberated in vivo, resulting in removal of the neopentyl protecting group and regeneration of the parent drug.

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