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Claims for Patent: 5,731,327

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Claims for Patent: 5,731,327

Title: Synthesis of 3-[4-(2-aminoethoxy)benzoyl]-2-aryl-6-hydroxybenzo [b]thiophenes
Abstract:The present invention is directed to chemical processes for preparing 2-aryl-6-hydroxy-3-[4-(2-aminoethoxy)benzoyl]benzo[b]-thiophenes. The present invention is also directed to crystalline solvates and a non-solvated crystalline form of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]-benzo[b]th iophene hydrochloride, as well as processes for their preparation.
Inventor(s): Luke; Wayne Douglas (West Lafayette, IN)
Assignee: Eli Lilly and Company (Indianapolis, IN)
Application Number:08/467,485
Patent Claims: 1. Non-solvated crystalline 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thi ophene hydrochloride, having substantially the following X-ray diffraction pattern obtained with copper radiation:

2. The crystalline 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thi ophene hydrochloride of claim 1 wherein the amount of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-Piperidinoethoxy)benzoyl]benzo[b]thi ophene hydrochloride present is at least 95% by weight.

3. A process for preparing non-solvated crystalline 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]-benzo[b]th iophene hydrochloride comprising

(a) reacting a solvated form of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thi ophene hydrochloride in methanol or in a mixture of methanol and water with about one equivalent of base,

(b) extracting the solution from step (a) with an aliphatic hydrocarbon solvent,

(c) adding about one equivalent of hydrochloric acid to the methanolic solution from step (b), and

(d) isolating the crystalline compound.

4. The process of claim 3 wherein the aliphatic hydrocarbon solvent is hexane or heptane.

5. The process of claim 3 wherein the base is sodium hydroxide.

6. The process of claim 3 wherein the hydrochloric acid is a 2 N aqueous solution.

7. A process for preparing non-solvated crystalline 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]-benzo[b]th iophene hydrochloride comprising

(a) reacting a solvated form of 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thi ophene hydrochloride in methanol or in a mixture of methanol and water with about one equivalent of base, and

(b) adding about one equivalent of hydrochloric acid to the methanolic solution from step (a), and

(c) isolating the crystalline compound.

8. The process of claim 7 wherein the base is sodium hydroxide.

9. The process of claim 7 wherein the hydrochloric acid is a 2 N aqueous solution.

10. Crystalline 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thi ophene hydrochloride when prepared by the process of claim 3.

11. Crystalline 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thi ophene hydrochloride when prepared by the process of claim 7.

12. A pharmaceutical formulation comprising the crystalline compound of any one of claims 3-4 and one or more pharmaceutically-acceptable carriers, diluents, or excipients.
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