WO2002005745A2 - The process of manufacturing pharmaceutical grade tannates - Google Patents
The process of manufacturing pharmaceutical grade tannates Download PDFInfo
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- WO2002005745A2 WO2002005745A2 PCT/IB2001/001250 IB0101250W WO0205745A2 WO 2002005745 A2 WO2002005745 A2 WO 2002005745A2 IB 0101250 W IB0101250 W IB 0101250W WO 0205745 A2 WO0205745 A2 WO 0205745A2
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- WIPO (PCT)
- Prior art keywords
- isopropanol
- tannate
- tannates
- tannic acid
- base
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
- C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C07C215/60—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
- C07C217/10—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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 hexane 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%.
- Phenylephrine base 20 gms
- Tannic acid 39.4 gms in 400 ml isopropanol
- Hexane 1000 ml 1200 ml of isopropanol is charged to which 20 gms base is added. Tannic acid is prepared by dissolving 39.4 gms in 400 ml isopropanol, which is then added to base solution. The solution is stirred for 3 hours, cooled and filtered. This then washed with hexane and dried.
- Phenylephrine base 34.39% w/w
- Chlorpheniramine base 43.3 gms
- Tannic acid 40.7 gms in 450ml Isopropanol
- Tannic acid is prepared by dissolving 40.7 gms in 450 ml isopropanol, 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 reveals the following, with a yield of 45 gms:
- Tannic acid 55.38% w/w
- Chlorpheniramine base 40.50% w/w
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Antihistamines are available in the form of free bases as well as salts i.e. hydrocholoride, 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, presently manufactured commercially, 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. According to present invention, isopropanol is removed by using a solvent for isopropanol which I highly volatile, which does not dissolve tannates but disperses the wet cake of tannate. The solvent, hexane, is added to wet cake while stirring it and the it is filtered. This results in residue of tannates with lower isopropanol content. The drying results into pharmaceutical grade tannate.
Description
1. THE PROCESS OF MANUFACTURING PHARMACEUTICAL GRADE TANNATES
2. Cadila Pharmaceuticals Limited, IRM House, Off CG. Road, Navrangpura, Ahmedabad- 380009, Gujarat, India, an Indian company.
3. The following specification particularly describes and ascertains the nature of this invention and the manner in which it has to be performed.
FIELD OF THE INVENTION
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 hexane 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.
BACKGROUND OF THE INVENTION
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, presently manufactured commercially, 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. Accordingly, even if the solvent utilized in its preparation has relatively high vapour pressure e.g. as in isopropanol, it is impossible to reduce the solvent content below 6% based on the weight of antihistamine tannate even at reduced pressures and very mild elevated temperatures. Morever from environment point of view, it would be desirable if antihistamine tannates would be manufactured such that use of volatile solvents like isopropanol would be avoided.
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.
Similarly, in US patent 5599846, phenyleherine tannate was synthesized by isopropanol route. The resulting antihistamine tannate had isopropanol 8%. and 2% degradation products.
REFERENCES:
1. U.S. Patent No. 5663415.
Process for preparing antihistamine tannates.
Chopdekar VM et al.
Jame Fine Chemicals, Inc. -
2. US Patent no. 5599846. Phenylehedrine tannates composition. Chopdekar VM et al.
Jame Fine Chemicals, Inc.
SUMMARY OF THE INVENTION
It has now been found that it is possible to reduce the content of isopropanol to around 3% during the manufacture of pharmaceutical grade tannates. This is possible by using hexane as a solvent.
According to the present invention, the content of isopropanol has been found to be around 3%.
DESCRIPTION OF THE INVENTION
According to the present invention is described a method to manufacture pharmaceutical grade tannates, using hexane as a solvent.
Isopropanol is charged. 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 40-50°C. This is then cooled to 20-25°C The material is centrifuged and washed with a solvent, hexane. The material is then unloaded. The product is dried.
EXAMPLE 1- PHENYLEPHRINE TANNATE:
Isopropanol : 1200 ml
Phenylephrine base: 20 gms
Tannic acid: 39.4 gms in 400 ml isopropanol
Hexane: 1000 ml
1200 ml of isopropanol is charged to which 20 gms base is added. Tannic acid is prepared by dissolving 39.4 gms in 400 ml isopropanol, 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 reveals the following, with a yield of 30 gms :
1. Description: pale yellow, tan fine powder
2. Water: 3.32% w/w
3. Residue on ignition: 0.15%
4. Heavy metals: Less than 5 ppm 5. . Tannic acid: 62.93% w/w
6. Phenylephrine base: 34.39% w/w
7. Assay: 99.50% w/w
8. Residual solvents: Isopropanol: 6088 ppm
EXAMPLE 2- CHLORPHENIRAMINE TANNATE
Isopropanol: 850 ml
Chlorpheniramine base: 43.3 gms
Tannic acid: 40.7 gms in 450ml Isopropanol
Hexane: 1000 ml
850 ml of isopropanol is charged to which 43.3 gms base is added. Tannic acid is prepared by dissolving 40.7 gms in 450 ml isopropanol, 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 reveals the following, with a yield of 45 gms:
Description: Yellowish, Tan, fine powder
Water: 3.92% w/w
Residue on ignition: 0.13% w/w
Heavy metals: Less than 5ppm
Tannic acid: 55.38% w/w
Chlorpheniramine base: 40.50% w/w
Assay: 99.80% w/w
Residual solvents: Isopropanol: 828 ppm
Claims
1. The process for manufacturing pharmaceutical grade tannates, wherein a) Isopropanol is charged. b) Tannate base is added to this isopropanol. c) Tannic acid solution is prepared by dissolving in isopropanol. d) The above Tannic acid prepared is added into Tannate base solution. e) The solution as in (d) is stirred for a period of time at the said maximum temperature and then cooled. f) The material is centrifuged and washed with a volatile organic solvent. g) The material is then unloaded and dried.
2. The process, as claimed in claim 1 wherein the tannate base is selected from the group consisting of phenylephrine, carbetapentane, pyrilamine, chlorpheniramine, ephedrine, pseudoephedrine, brompheniramine, bromodiphenhydramine, diphenhydramine, pheniramine, Phenyltoxamine, clemastine, tripelennamine, cyproheptadine, phenindamine and phenyltoloxamine as a single ingredient or a combination of more than one.
3. The process, as claimed in claim 1 and 2 wherein the tannate base is Phenylephrine.
4. The process, as claimed in claim 1 and 2, wherein the tannate base is Chlorpheniramine.
5. The process as claimed in claim 1 wherein the step (e) is carried out for 3 hours.
6. The process as claimed in claim 6 wherein the process is carried out at temperature of 40-50°C.
7. The process as claimed in claim 1 wherein the volatile organic solvent used for washing in step (f) is hexane.
8. The process as claimed in claim 1 wherein the dried material contains isopropanol less than or equal to 0.5%.
9. The process as claimed in claim 1 and herein described in examples 1 to 2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN660MU2000 | 2000-07-14 | ||
| IN660/MUM/2000 | 2000-07-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2002005745A2 true WO2002005745A2 (en) | 2002-01-24 |
| WO2002005745A3 WO2002005745A3 (en) | 2002-10-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2001/001250 WO2002005745A2 (en) | 2000-07-14 | 2001-07-13 | The process of manufacturing pharmaceutical grade tannates |
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| Country | Link |
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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 |
| EP2101570A1 (en) * | 2006-12-14 | 2009-09-23 | Teva Pharmaceutical Industries Ltd. | Tannate salt of rasagiline |
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/IB2001/001250 patent/WO2002005745A2/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 (8)
| 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 |
| EP2101570A1 (en) * | 2006-12-14 | 2009-09-23 | Teva Pharmaceutical Industries Ltd. | Tannate salt of rasagiline |
| JP2010513280A (en) * | 2006-12-14 | 2010-04-30 | テバ ファーマシューティカル インダストリーズ リミティド | Rasagiline tannate |
| EP2101570A4 (en) * | 2006-12-14 | 2011-04-06 | Teva Pharma | Tannate salt of rasagiline |
| KR101077835B1 (en) | 2006-12-14 | 2011-10-28 | 테바 파마슈티컬 인더스트리즈 리미티드 | Tannate salt of rasagiline |
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| Publication number | Publication date |
|---|---|
| WO2002005745A3 (en) | 2002-10-10 |
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