WO2002005746A2 - Procede de fabrication des tannates de qualite pharmaceutique - Google Patents

Procede de fabrication des tannates de qualite pharmaceutique Download PDF

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Publication number
WO2002005746A2
WO2002005746A2 PCT/IB2001/001252 IB0101252W WO0205746A2 WO 2002005746 A2 WO2002005746 A2 WO 2002005746A2 IB 0101252 W IB0101252 W IB 0101252W WO 0205746 A2 WO0205746 A2 WO 0205746A2
Authority
WO
WIPO (PCT)
Prior art keywords
tannate
tannates
isopropanol
tannic acid
base
Prior art date
Application number
PCT/IB2001/001252
Other languages
English (en)
Other versions
WO2002005746A3 (fr
Inventor
Chidambaram Venkateswaran Srinivasan
Jayati Mitra
Bakulesh Mafatlal Khamar
Original Assignee
Cadila Pharmaceuticals Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cadila Pharmaceuticals Limited filed Critical Cadila Pharmaceuticals Limited
Publication of WO2002005746A2 publication Critical patent/WO2002005746A2/fr
Publication of WO2002005746A3 publication Critical patent/WO2002005746A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof

Definitions

  • the objective of the present invention is to manufacture pharmaceutical grade tannates.
  • the further objective of the present invention is to manufacture pharmaceutical grade tannates using water as a solvent for removing isopropanol, thereby reducing the content of isopropanol.
  • the further objective of present invention is to improve the yield of pharmaceutical grade tannates.
  • Antihistamines are available in the form of free bases as well as salts i.e hydrochloride, maleate, tannate etc. Frequently, it is necessary to utilise antihistamines in the form of tannate salt because such salts are generally quite stable and may be administered in such from without untoward side effects.
  • Tannic acid also known as tannin, is a well known naturally occurring substance. Tannic acid, which is available commercially, usually contain about 5% of water, has a molecular weight of about 1700 and is typically produced from Turkish or Chinese nutgall.
  • Antihistamine tannates are relatively impure. Such tannates are prepared by the reaction of antihistamine free base with tannic acid and using a volatile solvent, isopropanol (IPA). The yield is only fair (around 70%) and decomposition products e.g 2-5% along with significant amount of volatile solvent, isopropanol (6-10%) remains with the product, which cannot be removed. As per guidelines for pharmaceutical agents, the residual solvents should be less than 0.5% or 5000 ppm. Many antihistamine tannates are heat sensitive e.g. phenyleherine tannates and therefore undergo decomposition quite readily upon prolonged exposures to temperatures as low as 50°C.
  • US patent 5663415 describes a method by treating the antihistamine tannate in isopropanol with tannic acid in isopropanol at 60-80°C for 1-2 hours.
  • the resulting antihistamine tannate has isopropanol 8-10% and cannot be removed on prolonged heating under vacumn.
  • the content, of isopropanol has been .found to be around 3%.
  • Tannate base is added to this isopropanol.
  • Tannic acid solution is prepared by dissolving in isopropanol. The above Tannic acid prepared is added into Tannate base solution. The solution is stirred for 3 hours at 40-45°C. This is then cooled to 20-25°C and again stirred for 1 hour at 20-25°C The material is centrifuged and washed with a solvent, water. The material is then unloaded. The product is dried.
  • Chlorpheniramine base 43.3 gms
  • Tannic acid 40.7 gms in 450ml Isopropanol
  • Tannic acid 54.20% w/w
  • Chlorpheniramine base 41.65% w/w
  • Tannic acid 43.2 gms in 430 ml isopropanol
  • Tannic acid is prepared by dissolving 43.2 gms in 430 ml isopropanol, which is then added to base solution. The solution is stirred for 3 hours, cooled and filtered. This then washed with 100 ml hexane, then followed by 1000 ml of water and dried.
  • the above tannate prepared reveals the following, with a yield of 55 gms:
  • Tannic acid 53.66% w/w

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Des antihistamines sont disponibles sous forme de bases libres ainsi que sous forme de sels, comme du chlorhydrate, du maléate, tannate, etc.. Il est souvent nécessaire d'utiliser des antihistamines sous forme de sel de tannate car ces sels sont généralement stables et peuvent être administrés sous ces formes sans effets secondaires défavorables. L'acide tannique, également connu sous le nom du tanin, est une substance naturelle. L'acide tannique, qui est commercialisé, contient généralement environ 5 % d'eau, présente un poids moléculaire de 1700 environ, et est généralement produit à partir de la noix de galle turque ou chinoise. Les tannates d'antihistamines, actuellement fabriqués, sont relativement impurs. Ces tannates sont obtenus en faisant réagir une base libre d'antihistamine avec de l'acide tannique et en utilisant un solvant volatile, de l'isopropanol (IPA), on obtient ainsi un rendement d'environ 70 % avec des produits de décomposition, par exemple, de 2 à 5 % avec une quantité significative de solvant volatile, l'isopropanol (6 10%) restant avec le produit qui ne peuvent pas être extraits. Selon la présente invention, pour des types spécifiques de tannates, l'isopropanol (IPA) est extrait en ajoutant de l'eau tout en mélangeant et dispersant le gateau mouillé de tannate. Il est ensuite filtré et le résidu de tannate est séché pour obtenir un tannate de qualité pharmaceutique. Les tannates comme le tannate de chlorphéniramine et les tannates de pyrilamine ont été préparés par ce procédé.
PCT/IB2001/001252 2000-07-14 2001-07-13 Procede de fabrication des tannates de qualite pharmaceutique WO2002005746A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN662MU2000 2000-07-14
IN662/MUM/2000 2000-07-14

Publications (2)

Publication Number Publication Date
WO2002005746A2 true WO2002005746A2 (fr) 2002-01-24
WO2002005746A3 WO2002005746A3 (fr) 2002-05-02

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Family Applications (1)

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PCT/IB2001/001252 WO2002005746A2 (fr) 2000-07-14 2001-07-13 Procede de fabrication des tannates de qualite pharmaceutique

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WO (1) WO2002005746A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6670370B1 (en) 2001-12-14 2003-12-30 Jame Fine Chemicals, Inc. Dextromethorphan tannate
US6833360B2 (en) 2001-12-14 2004-12-21 Jame Fine Chemicals, Inc. Process for preparing pseudoephedrine tannate
WO2005023236A1 (fr) * 2003-08-22 2005-03-17 Pediamed Pharmaceuticals, Inc. Sels de phenylephrine tannate, pyrilamine tannate, et dextromethorphan tannate utilises dans des compositions pharmaceutiques
US6939856B2 (en) 2001-12-14 2005-09-06 Jame Fine Chemicals, Inc. Method for preparing dexchlor tannate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3282789A (en) * 1963-05-17 1966-11-01 Neisler Lab Inc Stable liquid colloidal tannate compositions
US5663415A (en) * 1996-06-28 1997-09-02 Jame Fine Chemicals, Inc. Process for preparing antihistamine tannates

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3282789A (en) * 1963-05-17 1966-11-01 Neisler Lab Inc Stable liquid colloidal tannate compositions
US5663415A (en) * 1996-06-28 1997-09-02 Jame Fine Chemicals, Inc. Process for preparing antihistamine tannates

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6670370B1 (en) 2001-12-14 2003-12-30 Jame Fine Chemicals, Inc. Dextromethorphan tannate
US6833360B2 (en) 2001-12-14 2004-12-21 Jame Fine Chemicals, Inc. Process for preparing pseudoephedrine tannate
US6881744B2 (en) 2001-12-14 2005-04-19 Jame Fine Chemicals, Inc. Carbinoxamine tannate
US6939856B2 (en) 2001-12-14 2005-09-06 Jame Fine Chemicals, Inc. Method for preparing dexchlor tannate
WO2005023236A1 (fr) * 2003-08-22 2005-03-17 Pediamed Pharmaceuticals, Inc. Sels de phenylephrine tannate, pyrilamine tannate, et dextromethorphan tannate utilises dans des compositions pharmaceutiques

Also Published As

Publication number Publication date
WO2002005746A3 (fr) 2002-05-02

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