Deeper Knowledge, Faster

  • Identify first generic entrants
  • Obtain formulation and manufacturing information
  • Drug patents in 130+ countries
➤ Start Trial

or, See Plans & Pricing

Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

Serving leading biopharmaceutical companies globally:

Boehringer Ingelheim
Covington
McKesson
Chubb
Novartis
Cerilliant
Cantor Fitzgerald
Mallinckrodt
Cipla
Queensland Health

Generated: January 20, 2018

DrugPatentWatch Database Preview

Claims for Patent: 5,731,327

« Back to Dashboard

Summary 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.

For more information try a trial or see the plans and pricing

Serving leading biopharmaceutical companies globally:

Deloitte
AstraZeneca
Mallinckrodt
McKesson
Chinese Patent Office
Moodys
Citi
Cerilliant
Boehringer Ingelheim

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.

botpot