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Generated: December 13, 2017

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Claims for Patent: 5,466,810

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Claims for Patent: 5,466,810

Title: 2-amino-3-aroyl-benzo[.beta.]thiophenes and methods for preparing and using same to produce 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-aminoethoxy)-benzoyl]benzo[.beta.] thiophenes
Abstract:A group of 2-amino-3-aroyl-benzo[.beta.]thiophenes are prepared by treating an aldehyde with an anion of dimethylamino thioformamide, cyclizing the .alpha.-hydroxy thioamide, and subsequently acylating the benzo[.beta.]thiophene to yield the 2-amino-3-aryl derivative. These compounds may be treated with suitable phenyl Grignard reagents, and after deprotection, yield 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[.beta .]thiophene.
Inventor(s): Godfrey; Alexander G. (Greenwood, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Application Number:08/257,859
Patent Claims: 1. A compound of the formula: ##STR8## or pharmaceutically acceptable salts thereof; wherein R represents C.sub.1 -C.sub.6 alkyl;

R" represents C.sub.1 -C.sub.6 alkyl or --(CH.sub.2).sub.n N(R.sub.1)(R.sub.2) where n is an integer of 1 to 4, and R.sub.1 and R.sub.2 are independently C.sub.1 -C.sub.6 alkyl, or R.sub.1 and R.sub.2 combine to form C.sub.4 -C.sub.6 polymethylene or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; and

R.sub.3 and R.sub.4 are independently C.sub.1 -C.sub.6 alkyl or combine to form C.sub.4 -C.sub.6 polymethylene.

2. A compound according to claim 1, wherein R represents methyl.

3. A compound according to claim 1, wherein R" is --(CH.sub.2).sub.n NR.sub.1 R.sub.2 and n is 2.

4. A compound according to claim 1, wherein R.sub.3 and R.sub.4 are methyl.

5. A compound according to claim 3, wherein R.sub.1 and R.sub.2 together represent pentamethylene.

6. A compound according to claim 5, wherein R.sub.3 and R.sub.4 are methyl.

7. A compound according to claim 1, which is 6-methoxy-2-dimethylamino-3-[4-(2-piperidinoethoxy)benzoyl]benzo[.beta.]th iophene.
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