WO2002005747A2 - The process of manufacturing pharmaceutical grade tannates - Google Patents
The process of manufacturing pharmaceutical grade tannates Download PDFInfo
- Publication number
- WO2002005747A2 WO2002005747A2 PCT/IB2001/001254 IB0101254W WO0205747A2 WO 2002005747 A2 WO2002005747 A2 WO 2002005747A2 IB 0101254 W IB0101254 W IB 0101254W WO 0205747 A2 WO0205747 A2 WO 0205747A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- tannate
- tannates
- tannic acid
- base
- isopropanol
- Prior art date
Links
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
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
Definitions
- the objective of the present invention is to manufacture pharmaceutical grade tannates without the use of isopropanol (IPA).
- IPA isopropanol
- the further objective of the present invention is to manufacture pharmaceutical grade tannates, using mixture of solvents.
- 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.
- 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 method gives tannates which are lighter in colour.
- Tannate base is added to this chloroform.
- Tannic acid solution is prepared by dissolving in ethyl acetate. 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. The material is centrifuged and washed with hexane. The material is then unloaded. The product is dried.
- Ephedrine base 10 gms
- Tannic acid 20 gms in 230 ml ethyl acetate
- Hexane 800 ml 330 ml of chloroform is charged to which 10 gms base is added. Tannic acid is prepared by dissolving 20 gms in 230 ml ethyl acetate, which is then added to base solution. The solution is stirred for 3 hours, cooled and filtered. This then washed with hexane and dried.
- Tannic acid 64.30% w/w
- Ephedrine base 30.44% w/w
- Pseudoephedrine base 10 gms
- Tannic acid 21.4 gms in 400ml ethyl acetate
- Tannic acid is prepared by dissolving 21.4 gms in 400 ml ethyl acetate, which is then added to base solution. The solution is stirred for 3 hours, cooled and filtered. This then washed with hexane and dried.
- the above tannate prepared revealed the following, with a yield of 23 gms:
- Tannic acid 63.35% w/w
- Carbetapentane base 50 gms
- Tannic acid 75 gms in 920 ml ethyl acetate
- Tannic acid is prepared by dissolving 75 gms in 920 ml ethyl acetate, which is then added to base solution. The solution is stirred for 3 hours, cooled and filtered. This then washed with hexane and dried.
- Tannic acid 61.98% w/w
- Carbetpentane base 36.12% w/w
Landscapes
- 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
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN661/MUM/2000 | 2000-07-14 | ||
IN661MU2000 | 2000-07-14 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2002005747A2 true WO2002005747A2 (en) | 2002-01-24 |
WO2002005747A3 WO2002005747A3 (en) | 2002-10-10 |
Family
ID=11097264
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2001/001254 WO2002005747A2 (en) | 2000-07-14 | 2001-07-13 | The process of manufacturing pharmaceutical grade tannates |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2002005747A2 (en) |
Cited By (4)
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 |
US6939856B2 (en) | 2001-12-14 | 2005-09-06 | Jame Fine Chemicals, Inc. | Method for preparing dexchlor tannate |
US7611872B2 (en) | 2001-02-21 | 2009-11-03 | Basf Aktiengesellschaft | Method for the production of D-pantothenic acid and/or salts thereof via purification by nanofiltration as adjunct for animal feedstuffs |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3282789A (en) * | 1963-05-17 | 1966-11-01 | Neisler Lab Inc | Stable liquid colloidal tannate compositions |
US5599846A (en) * | 1996-06-28 | 1997-02-04 | Jame Fine Chemicals, Inc. | Phenylephrine tannate compositions |
US5663415A (en) * | 1996-06-28 | 1997-09-02 | Jame Fine Chemicals, Inc. | Process for preparing antihistamine tannates |
-
2001
- 2001-07-13 WO PCT/IB2001/001254 patent/WO2002005747A2/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3282789A (en) * | 1963-05-17 | 1966-11-01 | Neisler Lab Inc | Stable liquid colloidal tannate compositions |
US5599846A (en) * | 1996-06-28 | 1997-02-04 | Jame Fine Chemicals, Inc. | Phenylephrine tannate compositions |
US5663415A (en) * | 1996-06-28 | 1997-09-02 | Jame Fine Chemicals, Inc. | Process for preparing antihistamine tannates |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7611872B2 (en) | 2001-02-21 | 2009-11-03 | Basf Aktiengesellschaft | Method for the production of D-pantothenic acid and/or salts thereof via purification by nanofiltration as adjunct for animal feedstuffs |
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 |
Also Published As
Publication number | Publication date |
---|---|
WO2002005747A3 (en) | 2002-10-10 |
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