Title of Invention	A PROCESS FOR THE ISOLATION AND PURIFICATION OF SESQUITERPENE COMPOUNDS FROM A CURCUMA PLANT
Abstract	The present invention provides a novel speedy and efficient process for the isolation and purification of sesquiterpene compounds from a Curcuma plant. Medicinal plants have contributed enormously to the identification of lead compounds in drug discovery programs. Curcuma longa known as 'Turmeric' in English, 'Ukon' in Japanese and 'Haldi' in Hindi, exhibits a wide array of biological activities and is useful as an antioxidant, anti-inflammatory, wound healing, anticancer and anti-proliferative, anti-fungal and anti-bacterial agent etc. Various sesquiterpenes and curcuminoids have been isolated from the rhizome of Curcuma longa. Turmeric acquires a yellow colour due to the present of Curcuminoids.

Title of Invention

A PROCESS FOR THE ISOLATION AND PURIFICATION OF SESQUITERPENE COMPOUNDS FROM A CURCUMA PLANT

Abstract

The present invention provides a novel speedy and efficient process for the isolation and purification of sesquiterpene compounds from a Curcuma plant. Medicinal plants have contributed enormously to the identification of lead compounds in drug discovery programs. Curcuma longa known as 'Turmeric' in English, 'Ukon' in Japanese and 'Haldi' in Hindi, exhibits a wide array of biological activities and is useful as an antioxidant, anti-inflammatory, wound healing, anticancer and anti-proliferative, anti-fungal and anti-bacterial agent etc. Various sesquiterpenes and curcuminoids have been isolated from the rhizome of Curcuma longa. Turmeric acquires a yellow colour due to the present of Curcuminoids.

Full Text	A-fvariety of methods for the isolation and purification of sesquitepene compounds have been published and reported (Oshiro, M. Kuroyanagi, M and Keno,A. Phytochemistry, 1990,29,22001; Golding, B.T., Pombo, E. and Samuel, C.J. J. Chem. Soc. Chem. Common. 1982, 363-364). Most of these methods employ chromatography. The purification of each compound by multiple column chromatography requires longer stay of compounds onto the column, which leads to decomposition of unstable sesquiterpene compounds and also lowers the yield of the desired compound. Since it is difficult to maintain identical conditions in multiple chromatography procedure, these methods are neither quantitative nor reproducible. Consequently, these processes are not easily scaled upto an efficient commercial process. There is therefore, a need for providing an alternative process for isolation and purification of sesquiterpene compounds from Curcuma sp. in a commercially viable manner, whereby, the compounds can be obtained in higher yield and purity. Objects of the Invention; It is an object of the present invention to provide a novel, speedy and efficient process for the isolation and purification of sesquiterpene compounds from a plant of the Curcuma sp. Description of the accompanying drawings t Fig. 1 represents the structures of a few sesquiterpene compounds. Fig. 2 is a chromatogram of Fraction II. D«tailed Description of the invention: Accordingly, the invention provides a process for the isolation and purification of sesquiterpene compounds from a plant of Curcuma sp., comprising the steps of : (a) Preparing an extract from a Curcuma plant by contacting the plant material with a solvent for a period sufficient to transport essential oil including sesquiterpene compounds into the solvent; (b) Subjecting the extract to reversed phase chromatography using aqueous solution of an extractive solvent whereby sesquiterpene compounds are selectively collected in an eluate. (c) Obtaining desired sesquiterpene compound from the eluate by conventional methods. In general, the present invention provides a highly efficient process for the isolation and purification of sesquiterpene compounds from a Curcuma plant. The process may be applied to any plant of Curcuma sp. such as Curcuma longa, Curcuma domestica, Curcuma aromatica or Curcuma zeodoaria. The list is exemplary and is not meant to limit the scope of plants from which sesquiterpene compounds may be isolated. A few sesquiterpene compounds are shown in figure 1 such as bisacumol (1), bisaculone (2), curlone [beta-turmerone 3], bisacurol (4), curcumene (5), ar-turmerone (6), alpha-turmerone (7) and beta-turmerone (8). The first step of the process involves preparation of an extract from a Curcuma plant material, the extract cafataining essential oils of the plant. Preferably, the plant material may be ground to fine pieces. The degree of comminutation of the plant material should be sufficient to provide enough a particulate area for contact. The plant material is then contacted with a solvent into which essential oil is transported. The solvent may be such that sesquiterpene compounds are carried therein. Such a solvent may be an alcohol such as methanol, propanol, isopropanol, ethanol or a polar solvent such as hexane, petroleum ether, benzene, chloroform, dichloromethane or their mixtures. The preferred solvent is hexane. Preferably, the extract containing essential oil may be prepared by soaking the plant material in an appropriate solvent. A skilled person will recognize that hot or cold extraction, percolation, concurrent-current extraction and other similar methods may also be employed, including steam distillation. The temperature at the time of preparation of the extract may be about 10° to 60°C. The amount of plant material to the solvent may vary from 1:4 to 1: 10. The impurities in the extract may be eliminated, by filteration through silica or extraction. The extract so prepared contains a mixture of compounds, including desired sesquiterpene compounds. After preparation of the extract, desired sesquiterpene compounds are to be separated from the extract. For this purpose, the extract is loaded onto a reversed phase column and the desired Sesquiterpene compounds are separated by eluting the extract containing essential oils with an aqueous solution of an extractive solvent as eluant. The eluate collected contains desired sesquiterpene compounds including other sesquiterpene compounds. As said earlier, sesquiterpene compounds are highly volatile and many are unstable, which means that longer residence of these compounds in the column will cause decomposition and desired compounds cannot be obtained in high yield and purity. An advantage of the present invention is that since the essential oil extract of Curcuma plant is directly subjected to reversed phase chromatography, longer residence of sesquiterpene compounds on the column is avoided, increasing the chances of recovering desired compounds in high yield and purity. In fact, unlike general reversed phase procedures, the essential oil extract is not subjected to absorption on matrix and desorption: they are directly eluted and selectively collected in the eluate. Yet another advantage of this step is that desired sesquiterpene compounds may be eluted with as little extraneous material as possible. This step depends largely on the hydrophobicity of the matrix, and the type of eluant. Hence, an appropriate matrix which is hydrophobic in nature may be used, whereby sesquiterpene compounds are free to flow into the eluate. Further, the matrix may be unreactive to the sample/extract and the solvent. Examples of such a matrix may be polymethylacrylate or C2-C18 hydrocarbon column. The extractive solvent or eluant used may be an alcohol such as ethanol, methanol, butanol, isopropanol or acetonitrile. Usually, an aqueous solution of the extractive solvent is prepared. The ratio of water : extractive solvent may be 60-75 : 40-15, depending on the solvent, the sample extract ami the compounds to be isolated. A skilled person may readily recognize the various combinations of the extraction solvent that would yield desired compounds. The step may be repeated a few times and pools of eluates may be collected for further use and analysis. The eluates so pooled contain a mixture of various sesquiterpene compounds. The desired sesquiterpene compound(s) may be recovered, isolated, and purified by filteration, evaporation, crystallization and so on. Preferably, filteration is done using hexane, ethylacetate or a hexane: ethylacetate combination. For example, for isolation of cc-turmerone, p-turmerone and ar-turmerone, filteration is effected using the ethylacetate-hexane combination. This filterate when purified yields turmerones. The isolated sesquiterpene compounds may be analysed and characterized by IR, NMR and MS spectroscopy. In an embodiment, the eluate may be subjected to high performance liquid chromatography (HPLC) with an aqueous solution of an extractive solvent as eluant like methanol/water. The yield of sesquiterpene compounds by the process of the invention is in the range of 0.3-.05% calculated from lOOg plant material and the purity is about 89-95 %. The invention is now illustrated by the following examples which should not be construed as a limitation on the scope of the invention. Example I (a) Preparing crude extract Fresh rhizome (200 gm) of Curcuma longa was finely ground and soaked in hexane at 20°C. Mild heat was provided with constant stirring. Unwanted impurities were removed by centrifugation at 10,000 rpm per minute. The essential oil fraction obtained in (a) above (0.7 gm, hexane fraction) was subjected chromatographic filteration using hexane; ethyl acetate to yield three factions. Fraction I (0.21 gm) obtained using 100% hexane, Fraction II (0.30 gm) was obtained using 1% ethyl acetate and 99% hexane. Fraction III (0.19 gm) was obtained using 1.5% ethyl acetate and 98.5% hexane. (b) Elution using reversed phase matrix: About 20ul of the Faction II (essential oil) obtained above was loaded onto a well-conditioned CIS column (HYPERSIL) (250 mm x 4.6 mm, 5u) , using methanol/water (70/30) as mobile phase at the flow rate of Iml/min. Fraction II was subjected to preparative HPLC analysis 0.5 gms (CIS reverse phase column, flow rate 8 ml/min) , using a mobile phase methanol: water (70:30) at the flow rate of 8rrtl/min. The eluate was collected in 15 ml fractions from the bottom of the column and analysed for the presence of sesquiterpenes by HPLC [LC 8A, SHIMADZU with photodiode array detector]. This Fraction II exhibited three major peaks PRS I, PRS II and PRS III as shown in the chromatogram in figure 2 and six minor peaks. The three major peaks were observed at : PRS I (Rt 18.8 min) , PRS II (Rt 28.5 min) and PRS III (Rt 29.7 min). This purification lead to the identification of compounds at 3max 238, 244 and 244. The compounds were identified as ar-turmerone, a-turmerone and a-turmerone. The structures of these compounds are depicted in figure I. (Figure Remove) (b) Isolation and Characterization of the compounds: The eluates of step (b) above were concentrated by evaporation to give the final product as oil 0.040 gms of d-turmerone, 0.035 gms of (3-turmerone and 0.050 gms of ar-turmerone (as oil) were recovered. The recovery was nearly 25 % having 90% purity. The compounds were characterised by IR, MS and NMR spectroscopy. 1H NMR (300 MHz, CDC13) for PRS I, II and III TMe XH NMR of the compound obtained from peak PRS-II showed aromatic protons 8 7.07 (s, 4H) and methyl protons S 2.30 (s,3H), where the methyl group is attached to the aromatic ring. The IR peaks at 1690, 1620 cm"1 in CC14 indicated the presence of carbonyl and aromatic a, P- unsaturated groups. Further the m/z at 216 for the PRS-I confirmed this compound as ar- turmerone (5,6,7). The PRS-I and PRS-III showed same IR spectrum and mass spectrum at m/z 218. The ^ NMR spectra of PRS-I peak showed the presence of four singlets at 5 0.87, 1.69,1.89 and 2.14 for four methyl groups present in the compound and these methyl groups are not attached to an aromatic ring system. The presence of two peaks at 8 4.94 (bd) and 4.99 (bs) in PRS-III confirmed the presence of an exo-methylene group which is not attached to an aromatic ring system, therefore, the peaks PRS-Iand PRS-III were identified as a and P- turmerone respectively. PRS-I (a turmerone) 8 0.87 (s, 3H, -CH3) , 8l.69(s, 3H, - CH3) , 81.89 (s, 3H, -CH3) , and 82.14(s, 3H, -CH3), PRS II (ar-turmerone) 8 7.07 (s, 4H, Ar-H) and 8 2.30 (s,3H, CH3-Ar) PRS III (P turmerone) 8 4.94 (bd, 1H, CH2) and 4.99 (bs, 1H, CH2) Source of Biological Material; The Curcuma longa used in the present invention were procured from National Bureau of Plant Genetic Resources, Regional Station, Kerala, India. We claim 1. A process for the isolation and purification of sesquiterpene compounds comprising the steps of : (a) Preparing an extract from a Curcuma plant by contacting the plant material with a solvent for a period sufficient to transport essential oil including sesquiterpene compounds into the solvent; (b) Subjecting the extract to reversed phase chromatography using aqueous solution of an extractive solvent whereby sesquiterpene compounds are selectively collected in an eluate. (c) Obtaining desired sesquiterpene compound from the eluate by conventional methods. (2) A process as claimed in claim 1, wherein the solvent is selected from methanol, propanol, ethanol, isopropyl alcohol, hexane, dichloromethane, petroleum ether, ethylacetate, chloroform, benzene or mixtures thereof. {3} A process as claimed in claim 1, wherein the matrix for reversed phase chromatography is selected from polymethylacrylate and a C2 to CIS column. (4) A process as claimed in claim 1, wherein the plant material is obtained from a Curcuma plant selected from Curcuma domestica. Curcuma aromatica, Curcuma zedoaria and Curcuma longa. (5) A process as claimed in claim 1, wherein the extractive solvent is selected from methanol, ethanol, prepanol, isopropanol,butanol and acetonitrile. (6) A process as claimed in claim 1, wherein desired sesquiterpene compounds are obtained by filteration, evaporation and crystallization. (7) A process for the isolation and purification of sesquiterpene compounds substantially as hereindescribed and illustrated.

Full Text

A-fvariety of methods for the isolation and purification of sesquitepene compounds have been published and reported (Oshiro, M. Kuroyanagi, M and Keno,A. Phytochemistry, 1990,29,22001; Golding, B.T., Pombo, E. and Samuel, C.J. J. Chem. Soc. Chem. Common. 1982, 363-364). Most of these methods employ chromatography. The purification of each compound by multiple column chromatography requires longer stay of compounds onto the column, which leads to decomposition of unstable sesquiterpene compounds and also lowers the yield of the desired compound. Since it is difficult to maintain identical conditions in multiple chromatography procedure, these methods are neither quantitative nor reproducible. Consequently, these processes are not easily scaled upto an efficient commercial process.
There is therefore, a need for providing an alternative process for isolation and purification of sesquiterpene compounds from Curcuma sp. in a commercially viable manner, whereby, the compounds can be obtained in higher yield and purity.
Objects of the Invention;
It is an object of the present invention to provide a novel, speedy and efficient process for the isolation and purification of sesquiterpene compounds from a plant of the Curcuma sp.
Description of the accompanying drawings t
Fig. 1 represents the structures of a few sesquiterpene
compounds.
Fig. 2 is a chromatogram of Fraction II.

D«tailed Description of the invention:
Accordingly, the invention provides a process for the isolation and purification of sesquiterpene compounds from a plant of Curcuma sp., comprising the steps of :
(a) Preparing an extract from a Curcuma plant by
contacting the plant material with a solvent for a
period sufficient to transport essential oil including
sesquiterpene compounds into the solvent;
(b) Subjecting the extract to reversed phase
chromatography using aqueous solution of an extractive
solvent whereby sesquiterpene compounds are
selectively collected in an eluate.
(c) Obtaining desired sesquiterpene compound from the
eluate by conventional methods.
In general, the present invention provides a highly efficient process for the isolation and purification of sesquiterpene compounds from a Curcuma plant. The process may be applied to any plant of Curcuma sp. such as Curcuma longa, Curcuma domestica, Curcuma aromatica or Curcuma zeodoaria. The list is exemplary and is not meant to limit the scope of plants from which sesquiterpene compounds may be isolated. A few sesquiterpene compounds are shown in figure 1 such as bisacumol (1), bisaculone (2), curlone [beta-turmerone 3], bisacurol (4), curcumene (5), ar-turmerone (6), alpha-turmerone (7) and beta-turmerone (8).
The first step of the process involves preparation of an extract from a Curcuma plant material, the extract

cafataining essential oils of the plant. Preferably, the plant material may be ground to fine pieces. The degree of comminutation of the plant material should be sufficient to provide enough a particulate area for contact. The plant material is then contacted with a solvent into which essential oil is transported. The solvent may be such that sesquiterpene compounds are carried therein. Such a solvent may be an alcohol such as methanol, propanol, isopropanol, ethanol or a polar solvent such as hexane, petroleum ether, benzene, chloroform, dichloromethane or their mixtures. The preferred solvent is hexane.
Preferably, the extract containing essential oil may be prepared by soaking the plant material in an appropriate solvent. A skilled person will recognize that hot or cold extraction, percolation, concurrent-current extraction and other similar methods may also be employed, including steam distillation. The temperature at the time of preparation of the extract may be about 10° to 60°C. The amount of plant material to the solvent may vary from 1:4 to 1: 10. The impurities in the extract may be eliminated, by filteration through silica or extraction. The extract so prepared contains a mixture of compounds, including desired sesquiterpene compounds.
After preparation of the extract, desired sesquiterpene compounds are to be separated from the extract. For this purpose, the extract is loaded onto a reversed phase column and the desired Sesquiterpene compounds are separated by eluting the extract containing essential oils with an aqueous solution of an extractive solvent as eluant. The eluate collected contains desired sesquiterpene compounds

including other sesquiterpene compounds. As said earlier, sesquiterpene compounds are highly volatile and many are unstable, which means that longer residence of these compounds in the column will cause decomposition and desired compounds cannot be obtained in high yield and purity.
An advantage of the present invention is that since the essential oil extract of Curcuma plant is directly subjected to reversed phase chromatography, longer residence of sesquiterpene compounds on the column is avoided, increasing the chances of recovering desired compounds in high yield and purity. In fact, unlike general reversed phase procedures, the essential oil extract is not subjected to absorption on matrix and desorption: they are directly eluted and selectively collected in the eluate. Yet another advantage of this step is that desired sesquiterpene compounds may be eluted with as little extraneous material as possible.
This step depends largely on the hydrophobicity of the matrix, and the type of eluant. Hence, an appropriate matrix which is hydrophobic in nature may be used, whereby sesquiterpene compounds are free to flow into the eluate. Further, the matrix may be unreactive to the sample/extract and the solvent. Examples of such a matrix may be polymethylacrylate or C2-C18 hydrocarbon column. The extractive solvent or eluant used may be an alcohol such as ethanol, methanol, butanol, isopropanol or acetonitrile. Usually, an aqueous solution of the extractive solvent is prepared. The ratio of water : extractive solvent may be 60-75 : 40-15, depending on the solvent, the sample extract

ami the compounds to be isolated. A skilled person may readily recognize the various combinations of the extraction solvent that would yield desired compounds.
The step may be repeated a few times and pools of eluates may be collected for further use and analysis. The eluates so pooled contain a mixture of various sesquiterpene compounds.
The desired sesquiterpene compound(s) may be recovered, isolated, and purified by filteration, evaporation, crystallization and so on. Preferably, filteration is done using hexane, ethylacetate or a hexane: ethylacetate
combination.
For example, for isolation of cc-turmerone, p-turmerone and ar-turmerone, filteration is effected using the ethylacetate-hexane combination. This filterate when purified yields turmerones.
The isolated sesquiterpene compounds may be analysed and characterized by IR, NMR and MS spectroscopy.
In an embodiment, the eluate may be subjected to high
performance liquid chromatography (HPLC) with an aqueous
solution of an extractive solvent as eluant like
methanol/water.
The yield of sesquiterpene compounds by the process of the invention is in the range of 0.3-.05% calculated from lOOg plant material and the purity is about 89-95 %.

The invention is now illustrated by the following examples which should not be construed as a limitation on the scope of the invention.
Example I
(a) Preparing crude extract
Fresh rhizome (200 gm) of Curcuma longa was finely ground and soaked in hexane at 20°C. Mild heat was provided with constant stirring. Unwanted impurities were removed by centrifugation at 10,000 rpm per minute.
The essential oil fraction obtained in (a) above (0.7 gm, hexane fraction) was subjected chromatographic filteration using hexane; ethyl acetate to yield three factions. Fraction I (0.21 gm) obtained using 100% hexane, Fraction II (0.30 gm) was obtained using 1% ethyl acetate and 99% hexane. Fraction III (0.19 gm) was obtained using 1.5% ethyl acetate and 98.5% hexane.
(b) Elution using reversed phase matrix:
About 20ul of the Faction II (essential oil) obtained above was loaded onto a well-conditioned CIS column (HYPERSIL) (250 mm x 4.6 mm, 5u) , using methanol/water (70/30) as mobile phase at the flow rate of Iml/min.
Fraction II was subjected to preparative HPLC analysis 0.5 gms (CIS reverse phase column, flow rate 8 ml/min) , using a mobile phase methanol: water (70:30) at the flow rate of

8rrtl/min. The eluate was collected in 15 ml fractions from the bottom of the column and analysed for the presence of sesquiterpenes by HPLC [LC 8A, SHIMADZU with photodiode array detector]. This Fraction II exhibited three major peaks PRS I, PRS II and PRS III as shown in the chromatogram in figure 2 and six minor peaks. The three major peaks were observed at : PRS I (Rt 18.8 min) , PRS II (Rt 28.5 min) and PRS III (Rt 29.7 min).
This purification lead to the identification of compounds at 3max 238, 244 and 244. The compounds were identified as ar-turmerone, a-turmerone and a-turmerone. The structures of these compounds are depicted in figure I.
(Figure Remove) (b) Isolation and Characterization of the compounds: The eluates of step (b) above were concentrated by evaporation to give the final product as oil 0.040 gms of d-turmerone, 0.035 gms of (3-turmerone and 0.050 gms of ar-turmerone (as oil) were recovered. The recovery was nearly 25 % having 90% purity. The compounds were characterised by IR, MS and NMR spectroscopy.
1H NMR (300 MHz, CDC13) for PRS I, II and III
TMe XH NMR of the compound obtained from peak PRS-II showed aromatic protons 8 7.07 (s, 4H) and methyl protons S 2.30 (s,3H), where the methyl group is attached to the aromatic ring. The IR peaks at 1690, 1620 cm"1 in CC14 indicated the presence of carbonyl and aromatic a, P- unsaturated groups. Further the m/z at 216 for the PRS-I confirmed this compound as ar- turmerone (5,6,7). The PRS-I and PRS-III showed same IR spectrum and mass spectrum at m/z 218. The ^ NMR spectra of PRS-I peak showed the presence of four singlets at 5 0.87, 1.69,1.89 and 2.14 for four methyl groups present in the compound and these methyl groups are not attached to an aromatic ring system. The presence of two peaks at 8 4.94 (bd) and 4.99 (bs) in PRS-III confirmed the presence of an exo-methylene group which is not attached to an aromatic ring system, therefore, the peaks PRS-Iand PRS-III were identified as a and P- turmerone respectively. PRS-I (a turmerone) 8 0.87 (s, 3H, -CH3) , 8l.69(s, 3H, -
CH3) , 81.89 (s, 3H, -CH3) , and 82.14(s,
3H, -CH3),
PRS II (ar-turmerone) 8 7.07 (s, 4H, Ar-H) and 8 2.30 (s,3H, CH3-Ar)
PRS III (P turmerone) 8 4.94 (bd, 1H, CH2) and 4.99 (bs,
1H, CH2)
Source of Biological Material;
The Curcuma longa used in the present invention were procured from National Bureau of Plant Genetic Resources, Regional Station, Kerala, India.

We claim
1. A process for the isolation and purification of sesquiterpene compounds comprising the steps of :
(a) Preparing an extract from a Curcuma plant by
contacting the plant material with a solvent for a
period sufficient to transport essential oil
including sesquiterpene compounds into the solvent;
(b) Subjecting the extract to reversed phase
chromatography using aqueous solution of an
extractive solvent whereby sesquiterpene compounds
are selectively collected in an eluate.
(c) Obtaining desired sesquiterpene compound from the
eluate by conventional methods.
(2) A process as claimed in claim 1, wherein the solvent is selected from methanol, propanol, ethanol, isopropyl alcohol, hexane, dichloromethane, petroleum ether, ethylacetate, chloroform, benzene or mixtures
thereof.
{3} A process as claimed in claim 1, wherein the matrix for reversed phase chromatography is selected from polymethylacrylate and a C2 to CIS column.
(4) A process as claimed in claim 1, wherein the plant material is obtained from a Curcuma plant selected

from Curcuma domestica. Curcuma aromatica, Curcuma zedoaria and Curcuma longa.
(5) A process as claimed in claim 1, wherein the
extractive solvent is selected from methanol, ethanol,
prepanol, isopropanol,butanol and acetonitrile.
(6) A process as claimed in claim 1, wherein desired
sesquiterpene compounds are obtained by filteration,
evaporation and crystallization.
(7) A process for the isolation and purification of
sesquiterpene compounds substantially as
hereindescribed and illustrated.

Documents:

977-DEL-2003-Abstract-28-03-2008.pdf

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977-del-2003-claims-03-04-2008.pdf

977-DEL-2003-Claims-28-03-2008.pdf

977-del-2003-claims.pdf

977-del-2003-correspondence-others-03-04-2008.pdf

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977-DEL-2003-Form-3-28-03-2008.pdf

977-del-2003-form-3.pdf

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Patent Number

225387

Indian Patent Application Number

977/DEL/2003

PG Journal Number

48/2008

Publication Date

28-Nov-2008

Grant Date

11-Nov-2008

Date of Filing

07-Aug-2003

Name of Patentee

UNIVERSITY OF DELHI

Applicant Address

SOUTH CAMPUS, BENITO JUAREZ ROAD, NEW DELHI-110021

Inventors:

#	Inventor's Name	Inventor's Address
1	PRATIBHA MEHTA LUTHRA	SOUTH CAMPUS, BENITO JAUREZ ROAD, NEW DELHI-110021
2	RAMBIR SINGH	SOUTH CAMPUS, BENITO JAUREZ ROAD, NEW DELHI-110021

PCT International Classification Number

A61K 35/78

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA