Back to results
US 4,906,766 AGranted
N-(6-methoxy-5-(trifluoromethyl)-1-naphthalenyl)-substituted imino)methyl)-N-methylglycines
AssigneeAmerican Home Products Corporation
InventorsJay E. Wrobel, Kazimir Sestanj
Life of this patent
Estimating the term…
Abstract
Disclosed herein are N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl][substituted imino]methyl]-N-methylglycines and methods for their preparation. The N-methylglycines are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
Claims1
The process for the production of compounds of formula (I) ##STR3## wherein R is --CN, --SO.sub.2 CF.sub.3, or --SO.sub.2p --BrC.sub.6 H.sub.4 which comprises
- (a) reacting a thioamidoester of formula (II) ##STR4## wherein R.sup.1 is lower alkyl or Ar(lower) alkyl with triethyloxonium tetrafluoroborate to give the corresponding ethylthioimidate tetrafluoroborate salt of formula (III) ##STR5## wherein R.sup.1 is defined as above;
- (b) reacting an amide of formula (IV)
- R--NH.sub.2 (IV)
- wherein R is --CN, --SO.sub.2 CF.sub.3, or --SO.sub.2p --BrC.sub.6 H.sub.4 with a base to give the corresponding amide anion of formula (V)
- [R--N.sup..crclbar. H] (V)
- wherein R is defined as above;
- (c) reacting the salt of formula (III) wherein R.sup.1 is defined as above with the amide anion of formula (V) wherein R is defined as above to give corresponding amidine ester of formula (VI) ##STR6## wherein R and R.sup.1 are defined as above.
4 more elements
Dependencies are inferred from the claim text.