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Napadisylate salt of 5-(2--1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one as agonist of the beta 2 adrenergic receptor

a technology of napadisylate salt and beta 2 adrenergic receptor, which is applied in the field of crystalline naphthalene1 and 5disulfonic acid salts, can solve problems such as difficult to obtain, and achieve the effect of high melting poin

Active Publication Date: 2010-04-15
ALMIRALL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0007]It has now been found that naphthalene-1,5-disulfonic acid salts of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one can be obtained in a crystalline form which is neither hygroscopic nor deliquescent and which has a relatively high melting point thereby allowing the material to be micronized without significant decomposition or loss of crystallinity.

Problems solved by technology

Although the 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one has shown adequate pharmacological behaviour it has proved difficult to obtain it in the form of a salt which is crystalline, not hygroscopic nor deliquescent and which has a relatively high melting point to enable micronization.

Method used

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  • Napadisylate salt of 5-(2--1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one as agonist of the beta 2 adrenergic receptor
  • Napadisylate salt of 5-(2--1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one as agonist of the beta 2 adrenergic receptor
  • Napadisylate salt of 5-(2--1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one as agonist of the beta 2 adrenergic receptor

Examples

Experimental program
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Effect test

formulation example 1

Gelatin Cartridge for Inhalation

[0104]

IngredientAmount5-(2-{[6-(2,2-difluoro-2-0.2 mgphenylethoxy)hexyl]amino}-1(R)-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one, napadisylate (micronized)Lactose 25 mg

formulation example 2

Formulation for Inhalation with a DPI

[0105]

IngredientAmount5-(2-{[6-(2,2-difluoro-2- 15 mgphenylethoxy)hexyl]amino}-1(R)-hydroxy-ethyl)-8-hydroxyquinolin-2(1H)-one, napadisylate (micronized)Lactose3000 mg

formulation example 3

Formulation for Inhalation with a DPI

[0106]

IngredientAmount5-(2-{[6-(2,2-difluoro-2- 15 mgphenylethoxy)hexyl]amino}-1(R)-hydroxy-ethyl)-8-hydroxyquinolin-2(1H)-one, napadisylate (micronized)3(R)-[2-Hydroxy-2,2-bis(2- 100 mgthienyl)acetoxy]-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromideLactose3000 mg

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PUM

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Abstract

The present disclosure relates to crystalline monoapadisylate and / or heminapadisylate salt of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one, and pharmaceutically acceptable solvates thereof. The present disclosure also relates to pharmaceutical compositions comprising the crystalline monoapadisylate and / or heminapadisylate salt of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one, and to methods of treatment comprising these pharmaceutical compositions.

Description

FIELD OF THE INVENTION[0001]The present invention is directed to novel crystalline naphthalene-1,5-disulfonic acid salts (napadisylates) of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one, its enantiomers and solvates thereof. The invention is also directed to pharmaceutical compositions comprising the crystalline salts, methods of using them to treat respiratory diseases associated with β2 adrenergic receptor activity, and processes and intermediates useful for preparing such salts.BACKGROUND OF THE INVENTION[0002]β2 adrenergic receptor agonists are advantageously administered directly into the respiratory tract by inhalation when used for treating pulmonary or respiratory disorders. Several types of pharmaceutical inhalation devices have been developed for administering therapeutic agents by inhalation including dry powder inhalers (DPI), metered-dose inhalers (MDI) and nebulizer inhalers. It is highly desirable to have a crystalline ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D215/227A61K31/47A61K31/56A61P9/00
CPCC07D215/26A61K45/06A61K31/439A61K31/573A61K9/0075A61K9/008A61K2300/00A61P11/00A61P11/06A61P11/08A61P9/00A61K31/4704
Inventor PUIG DURAN, CARLOSMOYES VALLS, ENRIQUE
Owner ALMIRALL
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