Benzothiophene compounds, intermediates, compositions and methods
AssigneeEli Lilly and Company
InventorsAlan David Palkowitz, Kenneth Jeff Thrasher
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Abstract
The present invention provides compounds and processes for the preparation of compounds of formula I ##STR1## wherein R.sup.1a is --H or --OR.sup.7a in which R.sup.7a is --H or a hydroxy protecting group; R.sup.2a is --H, halo, or --OR.sup.8a in which R.sup.8a is --H or a hydroxy protecting group; R.sup.3 is 1-piperidinyl, 1-pyrrolidino, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, duisopropylamino, or 1-hexamethyleneimino; n is 2 or 3; and Z is --O-- or --S--; or a pharmaceutically acceptable salt thereof, through reduction of an intermediate of formula XVI ##STR2##
Claims3
A process for preparing compounds of fomula I ##STR111## wherein R.sup.1a is --H or --OR.sup.7a in which R.sup.7a is --H or a hydroxy protecting group;
- R.sup.2a is --H, halo, or --OR.sup.8a in which R.sup.8a is --H or a hydroxy protecting group;
- R.sup.3 is 1-piperidinyl, 1-pyrrolidino, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino;
- n is 2 or 3;
- and
- Z is --O-- or --S--;
- or a pharmaceutically acceptable salt thereof, comprising
- a) oxidizing the sulfur atom of a formula IV compound ##STR112## wherein R.sup.1a and R.sup.2a are as previously defined;
- and
- R.sup.9 is a leaving group;
- b) reacting the product of step a), a compound of formula XIV ##STR113## with a nucleophilic group of the formula ##STR114## wherein R.sup.12 is --OH or --SH;
- c) reducing the product of step b), a compound of formula XVI ##STR115## to provide a compound of the formula ##STR116## d) optionally removing the R.sup.1a and/or R.sup.2a hydroxy protecting groups, when present, of the product of step c);
- and
- e) optionally forming a salt of the product of step c) or step d).
Dependencies are inferred from the claim text.