# US 5,347,007 A · Method of preparing 7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,347,007 A
- Document ID: US5347007A
- Status: Granted
- Kind: A
- Application number: 08/131,189
- Filed: 1993-10-04
- Granted: 1994-09-13
- Earliest claimed: 1992-03-06
- Assignees: E. R. Squibb & Sons, Inc.
- Inventors: Jagabandhu Das; David Kronenthal
- Web page: https://patentgrep.com/patent/US5347007A

## CPC

- C07D 493/08: Bridged systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A method is provided for preparing 7-oxabicycloheptyl substituted heterocyclic aide prostaglandin analogs which are thromboxane A.sub.2 (TXA.sub.2) receptor antagonists or combined thromboxane A.sub.2 receptor antagonists/thromboxane synthetase inhibitors useful, for example, in the treatment of thrombotic and/or vasospastic disease, wherein a vinyl bromide of the formula, for example, ##STR1## wherein m, n, R.sup.1 and R.sup.2 are as defined herein is treated with a cyclizing agent to forth the corresponding oxazole.

## Claims

### Claim 1

A method for preparing a chloromethylamide of the structure ##STR38## wherein m is 1, 2or 3; n is 0, 1, 2, 3 or 4;
(CH.sub.2).sub.n is unsubstituted or is substituted with one or two alkyl groups;
R.sup.1 is lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, saturated heterocycle, or aromatic heterocycle; and
R.sup.2 is hydrogen, lower alkyl, aryl, or aralkyl, or R.sup.1 and R.sup.2 together with the N to which they are linked form a 5- to 8- membered ring; and which comprises treating a hydroxymethyl compound of the structure ##STR39## with a methanesulfonyl chloride in the presence of an organic base to form the mesylated compound of the structure ##STR40## and treating the mesylated compound with an alkali metal chloride or a quanternary ammonium chloride salt in the presence of dimethylformamide or dichloromethane to form the desired chloromethylamide compound.