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A Granular Composition Comprising Fenugreek Extract

Abstract: A granular composition is disclosed. Said granular composition comprises: - from about 0.1 to 15 percent by weight of fenugreek extract; - from about 85 to 99.9 percent by weight of fructo-oligosaccharide; wherein fenugreek extract is homogenously dispersed in fructo-oligosaccharide such that the taste of fenugreek extract is at least partially masked by fructo-oligosaccharide. Fig. 2

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
28 February 2019
Publication Number
36/2020
Publication Type
INA
Invention Field
FOOD
Status
Email
email@obhans.com
Parent Application

Applicants

TATA CHEMICALS LIMITED
BOMBAY HOUSE, 24 HOMI MODI STREET, MUMBAI – 400001, INDIA

Inventors

1. ROY, SAIKAT
TATA CHEMICALS LIMITED, INNOVATION CENTRE, SURVEY NO. 315, HISSA NO. 1-14, AMBEDVETH (V), PAUD ROAD, MULSHI, PUNE – 412111, MAHARASHTRA, INDIA
2. BANERJEE, GAUTAM
TATA CHEMICALS LIMITED, INNOVATION CENTRE, SURVEY NO 315, HISSA NO 1-14, AMBEDVETH (V), PAUD ROAD, MULSHI, PUNE – 412111, MAHARASHTRA, INDIA

Specification

Claims:1. A granular composition comprising:
- from about 0.1 to 15 percent by weight of fenugreek extract;
- from about 85 to 99.9 percent by weight of fructo-oligosaccharide;
wherein fenugreek extract is homogenously dispersed in fructo-oligosaccharide such that the taste of fenugreek extract is at least partially masked by fructo-oligosaccharide.

2. The granular composition as claimed in claim 1, wherein the composition comprises from about 0.1 to 10 percent by weight of fenugreek extract.

3. The granular composition as claimed in claim 1, wherein the composition comprises from about 90 to 99.9 percent by weight of fructo-oligosaccharide.

4. The granular composition as claimed in claim 1 or 3, wherein fructo-oligosaccharide has a degree of polymerization ranging between 2 to 10.

5. The granular composition as claimed in claim 1, further comprising one or more ingredient selected from a group consisting of glucose, fructose, sucrose, galacto-oligosaccharides, maltitol, xylitol, sorbitol, mannitol, glycerol, iso-maltooligosaccharides, trehalose, lactose, maltose, erythritol, maltodextrin, starch, cellulose and polydextrose.

6. The granular composition as claimed in claim 1, wherein the composition has granules having a particle size ranging between 0.1 to 1000 micron.

7. The granular composition as claimed in claim 1, wherein the composition is in powder form.

8. A food matrix comprising from about 0.1 to 10 percent by weight of the granular composition as claimed in any of the preceding claims.

9. A process of preparing a granular composition, the process comprising:
co-processing from about 0.1 to 15 percent by weight of fenugreek extract and from about 85 to 99.9 percent by weight of fructo-oligosaccharide, by blending fenugreek extract and fructo-oligosaccharide with a solvent, followed by granulation of co-processed fenugreek extract and fructo-oligosaccharide such that the granular composition comprising of fenugreek extract homogenously dispersed in fructo-oligosaccharide is obtained.

10. The process as claimed in claim 9, wherein the granulation of co-processed fenugreek extract and fructo-oligosaccharide is carried out subjecting slurry of the co-processed fenugreek extract and fructo-oligosaccharide to reduced pressure and temperature to cause evaporation of the solvent.

11. The process as claimed in claim 9, wherein the solvent is a polar protic solvent selected from a group consisting of water and ethanol.

12. The process as claimed in claim 9, wherein the evaporation is carried out at the temperature ranging between 40 - 800C, and the pressure ranging between 10 to 500 millibar.
, Description:Field of Invention

The present disclosure relates to a composition comprising fenugreek extract, which effectively masks the bitter taste of fenugreek extract. Particularly, the present disclosure relates to a granular composition comprising co-processed fenugreek extract and fructo-oligosaccharide.

Background

Plants provide an excellent source of drugs and a large proportion of currently-available drugs have been either derived directly or indirectly from plant sources. One such plant is fenugreek (Trigonella foenum graecum). The seeds of fenugreek plant have been reported to have antidiabetic and hypocholesterolaemic properties in both animal models and humans. The use of fenugreek seed in combating diabetic disorder, in particular, is well documented. There is thus a growing global interest in Fenugreek seeds to lower blood glucose in patients with diabetes. In addition to aforesaid, fenugreek seed extracts have other medical uses. Studies show that fenugreek may reduce the amounts of calcium oxalate in the kidneys, often a contributing factor in kidney stones. In animal studies, fenugreek appeared to lessen the chance of developing colon cancer by blocking the action of certain enzymes. However, bitter taste of fenugreek has become a potential limitation for its use in medicine, food and beverage formulations.

Researchers have been working to develop different methods to mask the bitter taste of fenugreek. One of the known techniques is by isolation of biologically active components or production of a debitterized extract. WO1999025197A1 discloses fenugreek seed material having reduced odor and taste by removing the components contributing to the odor and taste of the fenugreek. WO2005009453A1 discloses a process for debitterisation and defatting of fenugreek seed. US 5658571 describes a process for preparing a debitterized powder of the seeds of fenugreek in which the fenugreek does not come in direct contact with steam and alcohols are used to extract the bitter compounds. US 5997877 describes a process for the fractionation of fenugreek seeds, resulting in fractions that include a soluble dietary fiber fraction, de-flavored fenugreek seeds, high-protein fenugreek meal, saponins, and oleoresins. US 7645466 describes a process to extract amino acid compositions from fenugreek seed. US20100266665A1 discloses a process for obtaining fenugreek flour from seeds, and incorporating the flour into baked or other food products. This process uses only water and boiling to decrease the bitter flavor from the fenugreek seeds. No alcohol or petroleum-based solvents were used. These methods are expensive to carry out and pose a threat to health when used in food grade materials.
Alternatively, other taste masking methods have been developed wherein bitter substrates are coated with taste-masking agents to reduce the bitterness of fenugreek. The bitter substrate is coated such that it does not come into contact with the taste buds to impart any taste. This method however has a limitation of further use in any formulation application. Such a coated composition, when granulated, will lose the coating and the bitter substrate will become exposed and impart bitter taste.

US 5489436 discloses a chewable medicament tablet comprising a medicament coated with a taste-masking amount of a polymer blend of dimethylaminoethyl methacrylate and neutral methacrylic acid esters and a polymer selected from cellulose acetate and cellulose triacetate. WO2017221268A1 discloses a method for masking of the bitter taste of extracts, fractions and pure phytochemicals derived from plant raw materials by formulating the same in combination with a cationic synthetic polymer based on dimethylaminoethyl methacrylate, butyl methacrylate, and methyl methacrylate or a natural polymer selected from different grades of chitosan, different grades of shellac.

Summary

A granular composition is disclosed. Said granular composition comprises:
- from about 0.1 to 15 percent by weight of fenugreek extract;
- from about 85 to 99.9 percent by weight of fructo-oligosaccharide;
wherein fenugreek extract is homogenously dispersed in fructo-oligosaccharide such that the taste of fenugreek extract is at least partially masked by fructo-oligosaccharide.

A process of preparing said granular composition is also disclosed. Said process comprises co-processing from about 0.1 to 15 percent by weight of fenugreek extract and from about 85 to 99.9 percent by weight of fructo-oligosaccharide, by blending said fenugreek extract and fructo-oligosaccharide with a solvent, followed by granulation of co-processed fenugreek extract and fructo-oligosaccharide such that the granular composition comprising of fenugreek extract homogenously dispersed in fructo-oligosaccharide is obtained.

Brief Description of Drawings

Figure 1a shows the microscopic image of fructo-oligosaccharide at 40X scale.

Figure 1b shows the microscopic image of Fenugreek extract at 40X scale.

Figure 1c shows the microscopic image of a blend of fructo-oligosaccharide and fenugreek extract at 40X scale.

Figure 1d shows microscopic image of granular composition obtained in accordance with an embodiment of the present invention, at 40X scale.

Figure 2 shows the results of comparative sensory analysis, in accordance with Example 3.

Detailed Description

For the purpose of promoting an understanding of the principles of the disclosure, reference will now be made to embodiments and specific language will be used to describe the same. It will nevertheless be understood that no limitation of the scope of the disclosure is thereby intended, such alterations and further modifications in the disclosed composition and method, and such further applications of the principles of the disclosure therein being contemplated as would normally occur to one skilled in the art to which the disclosure relates.

It will be understood by those skilled in the art that the foregoing general description and the following detailed description are exemplary and explanatory of the disclosure and are not intended to be restrictive thereof.

Reference throughout this specification to “one embodiment” “an embodiment” or similar language means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one embodiment of the present disclosure. Thus, appearances of the phrase “in one embodiment”, “in an embodiment” and similar language throughout this specification may, but do not necessarily, all refer to the same embodiment.

In its broadest scope, the present disclosure relates to a composition comprising fenugreek extract, which effectively masks the bitter taste of fenugreek extract. Particularly, the present disclosure relates to a granular composition comprising:
- from about 0.1 to 15 percent by weight of fenugreek extract;
- from about 85 to 99.9 percent by weight of fructo-oligosaccharide;
wherein fenugreek extract is homogenously dispersed in fructo-oligosaccharide such that the taste of fenugreek extract is at least partially masked by fructo-oligosaccharide.

The granular composition comprising co-processed fenugreek extract and fructo-oligosaccharide provides uniform taste-masking of fenugreek extract. Figure 1a shows that spray-dried fructo-oligosaccharide powder is spherical amorphous powder. Figure 1b shows that fenugreek extract used for the formulation is also amorphous brown powder with diverse particle size. Figure 1c shows the microscopic image of fructo-oligosaccharide and fenugreek extract powder taken in 12:1 weight ratio and geometrically blended to get uniform mixture. This microscopic image shows that it is a heterogeneous powder mixture. Figure 1d shows the microscopic image of the granular composition prepared in Example 1 below. This microscopic image shows that the composition is uniform in nature with varied particle size and amorphous glass in nature.

Fenugreek extract herein refers to extract obtained from fenugreek seeds. Fenugreek seeds contains a number of chemical constituents. In accordance with an embodiment, the fenugreek extract in context of the present invention comprises of one or more constituents obtained from fenugreek seeds. Said constituents are selected from a group consisting of alkaloids, amino acids, saponins, steroidal sapinogens, flavonoids, fibers and lipids. The fenugreek extract comprising of one or more said constituents may be obtained using any known processes. In accordance with an embodiment, the composition comprises from about 0.1 to 10 percent by weight of fenugreek extract, and preferably 0.1- 7 percent by weight of fenugreek extract. The applicant has obtained the fenugreek extract from commercial sources, namely, Vidya Herbs Private Ltd. Said fenugreek extract comprises 50-70% Furostanolic saponins extracted from the dried seeds of Trigonella foenum graecum.

In accordance with an embodiment, the composition comprises from about 80 to 99.9 percent by weight of fructo-oligosaccharide, and preferably about 90 percent by weight of fructo-oligosaccharide. In accordance with an embodiment, fructo-oligosaccharide has a degree of polymerization ranging between 2 to 10, and preferably 2 to 4. The fructo-oligosaccharide may be obtained using any known processes. The applicant has obtained the fructo-oligosaccharide from commercial available brands, namely, Fossence (by Tata Chemicals Ltd.). The ratio of the fenugreek extract and fructo-oligosaccharide range between 1: 6 to 1: 1000, and preferably 1:20 to 1:120.

In accordance with an embodiment, the composition has granules having a particle size ranging between 0.1 to 1000 microns, and preferably 10 to 800 microns. In accordance with yet another embodiment, the composition is in powder form. In accordance with an embodiment, the granules are processed to form tablets.

In accordance with an embodiment, the composition further comprises one or more ingredient selected from a group consisting of glucose, fructose, sucrose, galacto-oligosaccharides, maltitol, xylitol, sorbitol, mannitol, glycerol, iso-maltooligosaccharides, trehalose, lactose, maltose, erythritol, maltodextrin, starch, cellulose and polydextrose. In accordance with an embodiment, the composition may further comprise of additives including but not limited to lubricant, binder, filler, flavoring agent, vitamin, mineral, active agent other than fenugreek, herbal extract other than fenugreek, a carrier and mixtures thereof.

A process of preparing aforesaid granular composition is also disclosed. Said process comprises co-processing from about 0.1 to 15 percent by weight of fenugreek extract and from about 85 to 99.9 percent by weight of fructo-oligosaccharide, by blending fenugreek extract and fructo-oligosaccharide with a solvent, followed by granulation of co-processed fenugreek extract and fructo-oligosaccharide such that the granular composition comprising of fenugreek extract homogenously dispersed in fructo-oligosaccharide is obtained. In accordance with an embodiment, the granulation of co-processed fenugreek extract and fructo-oligosaccharide is carried out by subjecting slurry of the co-processed fenugreek extract and fructo-oligosaccharide to reduced pressure and temperature to cause evaporation of the solvent and obtain the granular composition.

In accordance with an embodiment, said solvent is a polar protic solvent, and is preferably selected from a group consisting of water and ethanol.

In accordance with an embodiment, the evaporation is carried out at temperature ranging between 40-800C, and preferably between 50-700C. In accordance with an embodiment, the evaporation is carried out at a pressure ranging between 10 to 500 millibar, and preferably between 20 to 100 millibar.

The granulated co-processed fenugreek extract and fructo-oligosaccharide is then ground to obtain the desired granule size. The grinding may be carried out using any known technique.

In accordance with an embodiment, fenugreek extract and fructo-oligosaccharide are co-processed with an ingredient selected from a group consisting of glucose, fructose, sucrose, galacto-oligosaccharides, maltitol, xylitol, sorbitol, mannitol, glycerol, iso-maltooligosaccharides, trehalose, lactose, maltose, erythritol, maltodextrin, starch, cellulose and polydextrose.

A food matrix comprising from about 0.1 to 10 percent by weight of said granular composition is also disclosed. Such food matrix includes but are not limited to cereals, cookies, crackers, doughnuts, biscuits, pizza dough, pasta, bread, other baked goods, juices, salads, sauces, and candies.

In order that this invention may be better understood, the following examples are set forth. These examples are for the purpose of illustration only and the exact compositions, methods of preparation and embodiments shown are not limiting of the invention, and any obvious modifications will be apparent to one skilled in the art.

Specific Embodiments are Described Below

A granular composition comprising:
- from about 0.1 to 15 percent by weight of fenugreek extract;
- from about 85 to 99.9 percent by weight of fructo-oligosaccharide;
wherein fenugreek extract is homogenously dispersed in fructo-oligosaccharide such that the taste of fenugreek extract is at least partially masked by fructo-oligosaccharide.

Such granular composition(s), wherein the composition comprises from about 0.1 to 10 percent by weight of fenugreek extract.

Such granular composition(s), wherein the composition comprises from about 90 to 99.9 percent by weight of fructo-oligosaccharide.
Such granular composition(s), wherein fructo-oligosaccharide has a degree of polymerization ranging between 2 to 10.

Such granular composition(s), further comprising one or more ingredient selected from a group consisting of glucose, fructose, sucrose, galacto-oligosaccharides, maltitol, xylitol, sorbitol, mannitol, glycerol, iso-maltooligosaccharides, trehalose, lactose, maltose, erythritol, maltodextrin, starch, cellulose and polydextrose.

Such granular composition(s), wherein the composition has granules having a particle size ranging between 0.1 to 1000 micron.

Such granular composition(s), wherein the composition is in powder form.

A food matrix comprising from about 0.1 to 10 percent by weight of said granular composition.

A process of preparing a granular composition, the process comprising:
co-processing from about 0.1 to 15 percent by weight of fenugreek extract and from about 85 to 99.9 percent by weight of fructo-oligosaccharide, by blending fenugreek extract and fructo-oligosaccharide with a solvent, followed by granulation of co-processed fenugreek extract and fructo-oligosaccharide such that the granular composition comprising of fenugreek extract homogenously dispersed in fructo-oligosaccharide is obtained.

Such process, wherein the granulation of co-processed fenugreek extract and fructo-oligosaccharide is carried out subjecting slurry of the co-processed fenugreek extract and fructo-oligosaccharide to reduced pressure and temperature to cause evaporation of the solvent.

Such process, wherein the solvent is a polar protic solvent selected from a group consisting of water and ethanol.

Such process, wherein the evaporation is carried out at the temperature ranging between 40 - 800C, and the pressure ranging between 10 to 500 millibar.
Examples

Example 1: Process of preparing granular composition, as provided in Table 1.

Sr. No Ingredients Std. Formula Qnt. (6.1 g) Qnt for 30.5 g Batch
1 Fenugreek extract 0.1 g 0.5 g
2 Fructo-oligosaccharide 6.0 g 30.0 g
Total 6.1 g 30.5 g
Table 1: Composition of Granular Composition
Process: 0.5 grams of Fenugreek extract and 30.0 grams of fructo-oligosaccharide was geometrically blended to form an admixture. This mixture was taken in a round bottom flask. 10 ml (~10 grams) of water was added to the mixture in the flask. This mixture was first mixed in a rotatory evaporator for few minutes at 50 °C. After it became slurry and was mixed completely, water of this syrup like slurry material was evaporated at 55-60 °C at reduced pressure of ~50 millibar. After evaporation of water, this co-processed solid mass was taken out from flask with help of spatula and was ground for further process.

Example 2: Process of preparing granular composition, as provided in Table 2.
Sr. No Ingredients Std. Formula Qnt. (6.5 g) Qnt for 32.5 g Batch
1 Fenugreek extract 0.5 g 2.5 g
2 Fructo-oligosaccharide 6.0 g 30.0 g
Total 6.5 g 32.5 g
Table 2: Composition of Granular Composition
Process: 2.5 grams of Fenugreek extract and 30.0 grams of fructo-oligosaccharide was geometrically blended to form an admixture. This mixture was taken in a round bottom flask. 10 ml (~10 gm) of water was added to the mixture in the flask. This mixture was first mixed in a rotatory evaporator for few minutes at 50 °C. After it became slurry and was mixed completely, water of this syrup like slurry material was evaporated at 55-60 °C at reduced pressure of ~50 millibar. After evaporation of water, this co-processed solid mass was taken out from flask with help of spatula and was ground for further process.
Example 3: Comparative sensory analysis of cookies comprising (i) Fenugreek extract (Control) (ii) admixture of Fenugreek extract and fructo-oligosaccharide, and (iii) granular composition prepared in Example 1, as provided in Table 3.
Composition Control
% (w/w) Admixture
% (w/w) Granular Composition % (w/w)
S. No
1 Whole Wheat Flours 52.4 49.4 49.4
2 Fat (Marvo) 22.0 22.0 22.0
3 Sugar 24.0 21.0 21.0
4 Skim Milk Powder 0.87 0.87 0.87
5 Baking powder 0.1 0.1 0.1
6 Ammonium Bicarb 0.35 0.35 0.35
7 Salt 0.06 0.06 0.06
8 Vanilla 0.12 0.12 0.12
9 Fenugreek Extract 0.1 0.1 0
10 fructo-oligosaccharide 0 6.0 0
11 Granular Composition 0 0 6.1
100 100 100
Table 3: Cookie Formulation
Cookies were prepared according to process given below:
1. All the ingredients were weighed accurately.
2. Salt was dissolved in little amount of water.
3. Fat, fructo-oligosaccharide, Milk powder and Sugar were added.
4. The ingredients were blended for 1 minute at low speed.
5. The ingredients were blended for 3 minutes at high speed.
6. After 3 minutes, water was added slowly.
7. The ingredients were blended for another 4 minutes at high speed.
8. All dry ingredients were added and further mixed for 1 to 2 minutes.
9. Cookies were cut as per required size.
10. Wet cookie weight was found to be 16 grams.
11. Cookies were baked at 160 0C for 15 to 20 minutes.
12. Cookies were packed in laminated aluminum packaging and sealed.
Sensory Analysis: Sensory analysis was done by 11 member semi trained panelist with 5 point hedonic scale in terms of by Bitterness taste “not detectable” and “very unpleasant” (Scale: 1 = not detectable to 5 = very unpleasant). Table 4 and Figure 2 shows the results of sensory analysis.
C1F A1C M1F
Trained Panel Member Control Admixture Granular Composition
Member 1 2 3 1
Member 2 2 2 1
Member 3 3 2 1
Member 4 4 3 1
Member 5 2 3 1
Member 6 4 3 2
Member 7 5 4 3
Member 8 3 2 1
Member 9 2 3 1
Member 10 4 4 2
Member 11 4 3 1
Total 35 32 15
Average 3.18 2.91 1.36
Standard Error 0.33 0.21 0.20

Table 4: Result of Sensory Analysis

Results of sensory analysis show that disclosed granular composition effectively masked the bitter taste of fenugreek extract, as compared to the Control Sample and Admixture Sample. Simply adding the mix of Fenugreek extract and fructo-oligosaccharide does not provide any bitterness masking.
Industrial Applicability

The disclosed granular composition is easy to make and is inexpensive. The disclosed granular composition facilitates oral administration of fenugreek extract by effectively masking the bitter taste of fenugreek. The disclosed granular composition exhibits substantial bitterness masking as compared to a mere admixture of Fenugreek extract and fructo-oligosaccharide. Also, said granular composition has advantages over such taste masking techniques where the bitter substrate is coated with taste-masking agents. Such coated compositions fail to effectively mask the bitter taste of substrate upon granulation. On the other hand, the disclosed granular composition masks the taste of fenugreek extract even upon granulation.

Fructo-oligosaccharide in the disclosed granular composition provides added advantages of dietary fibre. Also, fructo-oligosaccharide acts as a prebiotic that beneficially affect the host by selectively stimulating the growth and activity of beneficial bacteria in the colon.

The disclosed granular composition can be used in food matrix including but not limited to cereals, cookies, crackers, doughnuts, biscuits, pizza dough, pasta, bread, other baked goods, juices, salads, sauces, and candies. The disclosed granular composition can also be used as dietary supplements and nutraceuticals. The composition may be used for lowering blood sugar, weight management, vitality and immunity.

Documents

Application Documents

# Name Date
1 201921007853-FORM 18 [20-02-2023(online)].pdf 2023-02-20
1 201921007853-STATEMENT OF UNDERTAKING (FORM 3) [28-02-2019(online)].pdf 2019-02-28
2 201921007853-FORM 1 [28-02-2019(online)].pdf 2019-02-28
2 201921007853-CORRESPONDENCE(IPO)-(CERTIFIED COPY OF WIPO DAS)-(25-2-2020).pdf 2020-02-29
3 201921007853-Form 1 (Submitted on date of filing) [25-02-2020(online)].pdf 2020-02-25
3 201921007853-FIGURE OF ABSTRACT [28-02-2019(online)].pdf 2019-02-28
4 201921007853-Power of Attorney [25-02-2020(online)].pdf 2020-02-25
4 201921007853-DRAWINGS [28-02-2019(online)].pdf 2019-02-28
5 201921007853-Request Letter-Correspondence [25-02-2020(online)].pdf 2020-02-25
5 201921007853-DECLARATION OF INVENTORSHIP (FORM 5) [28-02-2019(online)].pdf 2019-02-28
6 201921007853-ORIGINAL UR 6(1A) FORM 1 & FORM 26-200519.pdf 2019-08-01
6 201921007853-COMPLETE SPECIFICATION [28-02-2019(online)].pdf 2019-02-28
7 Abstract1.jpg 2019-05-25
7 201921007853-Proof of Right (MANDATORY) [15-05-2019(online)].pdf 2019-05-15
8 201921007853-FORM-26 [15-05-2019(online)].pdf 2019-05-15
9 Abstract1.jpg 2019-05-25
9 201921007853-Proof of Right (MANDATORY) [15-05-2019(online)].pdf 2019-05-15
10 201921007853-COMPLETE SPECIFICATION [28-02-2019(online)].pdf 2019-02-28
10 201921007853-ORIGINAL UR 6(1A) FORM 1 & FORM 26-200519.pdf 2019-08-01
11 201921007853-Request Letter-Correspondence [25-02-2020(online)].pdf 2020-02-25
11 201921007853-DECLARATION OF INVENTORSHIP (FORM 5) [28-02-2019(online)].pdf 2019-02-28
12 201921007853-Power of Attorney [25-02-2020(online)].pdf 2020-02-25
12 201921007853-DRAWINGS [28-02-2019(online)].pdf 2019-02-28
13 201921007853-Form 1 (Submitted on date of filing) [25-02-2020(online)].pdf 2020-02-25
13 201921007853-FIGURE OF ABSTRACT [28-02-2019(online)].pdf 2019-02-28
14 201921007853-FORM 1 [28-02-2019(online)].pdf 2019-02-28
14 201921007853-CORRESPONDENCE(IPO)-(CERTIFIED COPY OF WIPO DAS)-(25-2-2020).pdf 2020-02-29
15 201921007853-STATEMENT OF UNDERTAKING (FORM 3) [28-02-2019(online)].pdf 2019-02-28
15 201921007853-FORM 18 [20-02-2023(online)].pdf 2023-02-20