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WO2006072878A1 - Formes posologiques orales de sertraline possedant une taille de particule controlee, et leurs procedes de preparation - Google Patents

Formes posologiques orales de sertraline possedant une taille de particule controlee, et leurs procedes de preparation Download PDF

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Publication number
WO2006072878A1
WO2006072878A1 PCT/IB2006/000015 IB2006000015W WO2006072878A1 WO 2006072878 A1 WO2006072878 A1 WO 2006072878A1 IB 2006000015 W IB2006000015 W IB 2006000015W WO 2006072878 A1 WO2006072878 A1 WO 2006072878A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
pharmaceutical composition
sertraline
cellulose
pharmaceutically acceptable
Prior art date
Application number
PCT/IB2006/000015
Other languages
English (en)
Inventor
Nidhi Singh
Romi Barat Singh
Vishnubhotla Nagaprasad
Original Assignee
Ranbaxy Laboratories 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 Ranbaxy Laboratories Limited filed Critical Ranbaxy Laboratories Limited
Publication of WO2006072878A1 publication Critical patent/WO2006072878A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants

Definitions

  • the present invention relates to pharmaceutical compositions for oral administration that include sertraline or its pharmaceutically acceptable salts having a particle size of d 90 ranging from about 20 ⁇ m to about 40 ⁇ m and d 50 ranging from about 5 ⁇ m to about 15 ⁇ m and wherein the composition is bioequivalent to a reference composition.
  • the present invention also relates to processes for their preparation.
  • Sertraline or (lS-cis)-4-(3,4-dichlorophenyl)-l,2,3,4-tetrahydro-N-methyl-l- naphthylenamine, is a therapeutically potent selective serotonin reuptake inhibitor.
  • Sertraline is commercially sold as its hydrochloride salt under the trademark Zoloft ® and is approved by the U.S. Food and Drug Administration for the treatment of depression, obsessive-compulsive disorder, posttraumatic stress disorder and panic disorder.
  • Sertraline is disclosed in U.S. 4,536,518 which describes the synthesis of certain cis-
  • the sertraline hydrochloride produced by the method of the U.S. 4,536,518 has a crystalline form denominated "Form II.” It discloses four other polymorphs of sertraline hydrochloride designated as Forms I, III, IV, and V, and characterizes them by single crystal x-ray analysis, powder x-ray diffraction, infra-red spectroscopy, and differential scanning calorimetry. Both of the above patents also disclose certain dry solid pharmaceutical composition prepared by blending sertraline with conventional ingredients used in tablet and capsule manufacturing.
  • PCT application WO 03/93217 discloses a tablet of sertraline hydrochloride and the following excipients, in weight to weight percentages, wherein the tablet is prepared from an industrial sized batch of sertraline hydrochloride Form II substantially free of sertraline hydrochloride Form I: about 20% to about 35% sertraline hydrochloride Form II, about 25% to about 40% lactose monohydrate, about 5% to about 12% croscarmellose sodium NF, about 1% to about 3% povidone, about 20% to about 40% microcrystalline cellulose and about 0.5% to about 2.5% magnesium stearate.
  • the highly pure sertraline hydrochloride Form II used for preparing a tablet has a particle size distribution such that 100% of the particles are below 200 microns, more preferably below 100 microns and most preferably below about 50 microns.
  • compositions comprising sertraline or its pharmaceutically acceptable salts, which are bioequivalent to the marketed preparation, may be prepared by controlling the particle size of sertraline, more particularly by using a finer particle size.
  • a pharmaceutical composition for oral administration includes sertraline or pharmaceutically acceptable salts, the sertraline having a particle size distribution of dg 0 of about 20 ⁇ m to about 40 ⁇ m and d 5 o of about 5 ⁇ m to about 15 ⁇ m, and one or more pharmaceutically acceptable excipients.
  • Embodiments of the pharmaceutical composition may include one or more of the following features.
  • the one or more pharmaceutically acceptable excipients may be one or more of diluents, disintegrants, binders, glidants, and lubricants.
  • the diluent may be one or more of powdered cellulose, microcrystalline cellulose, microfine cellulose, lactose, starch, pregelatinized starch, sugar alcohols, dextrates, dextrin, dextrose, and inorganic diluents.
  • the sugar alcohol may be one or more of mannitol, sorbitol, and erythritol.
  • the inorganic diluent may be one or more of calcium carbonate, calcium sulphate, dibasic calcium phosphate dihydrate, tribasic calcium phosphate, magnesium carbonate, magnesium oxide, potassium chloride, sodium chloride and talc.
  • the disintegrant may be one or more of carboxymethylcellulose calcium, carboxymethylcellulose sodium, cross-linked carboxymethylcellulose sodium, cross-linked polyvinyl pyrrolidone, sodium starch glycolate, magnesium aluminum silicate, powdered cellulose, microcrystalline cellulose, low-substituted hydroxypropyl cellulose, polacrilin potassium, starch, pregelatinized starch, alginic acid and sodium alginate.
  • the binder may be one or more of gum acacia, guar gum, alginic acid, sodium alginate; carbomer, dextrin, gelatin, ethyl cellulose, methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, polymethacrylates, polyvinylpyrrolidone and pregelatinized starch.
  • the glidant may be one or more of talc, colloidal silicon dioxide, magnesium trisilicate, powdered cellulose, starch and tribasic calcium phosphate.
  • the lubricant may be one or more of magnesium stearate, calcium stearate, glyceryl monostearate, glycerylpalmitostearate, hydrogenated castor oil, hydrogenated vegetable oil, mineral oil, polyethylene glycol, sodium benzoate, sodium lauryl sulfate, sodium stearyl fumarate, stearic acid, talc and zinc stearate.
  • the pharmaceutical composition may include (a) about 5% to about 70% by weight of sertraline hydrochloride, (b) about 20% to 80% by weight of a diluent, (c) about 2% to 20% by weight of a disintegrant, (d) about 1% to 20% by weight of a binder, and (e) about 0.5 % to 5% by weight of a lubricant.
  • the pharmaceutical composition may be a tablet. In another general aspect there is provided a process for preparing a tablet of sertraline hydrochloride.
  • the process includes: (a) providing sertraline hydrochloride, wherein the sertraline has a particle size distribution of dg 0 of about 20 ⁇ m to about 40 ⁇ m and d 5 o of about 5 ⁇ m to about 15 ⁇ m; (b) preparing a blend comprising the sertraline hydrochloride and one or more pharmaceutically acceptable excipients; (c) optionally granulating the blend; and (d) processing the blend into a composition.
  • Embodiments of the process may include one or more of the following features or those described above.
  • the one or more pharmaceutically acceptable excipients may be about 20% to 80% by weight of a diluent, about 2% to 20% by weight of a disintegrant, about 1% to 20% by weight of a binder, and about 0.5 % to 5% by weight of a lubricant.
  • the sertraline hydrochloride may be about 5% to about 70% by weight of the pharmaceutical composition.
  • the blend may be granulated by a granulating fluid.
  • the granulation may be roller compaction.
  • the blend of step (b) may be directly compressed into tablets.
  • a method for treating a disorder selected from major depressive disorder, obsessive-compulsive disorder, panic disorder, posttraumatic stress disorder, premenstrual dysphoric disorder and social anxiety disorder in a patient includes administering to the patient a pharmaceutical composition comprising sertraline or pharmaceutically acceptable salts thereof.
  • the sertraline hydrochloride has a particle size distribution of dgo of about 20 ⁇ m to about 40 ⁇ m and d 50 of about 5 ⁇ m to about 15 ⁇ m.
  • Embodiments of the process may include one o more of the following features or those described above.
  • the pharmaceutical composition may further include one or more pharmaceutically acceptable excipients.
  • the one or more pharmaceutically acceptable excipients may be about 20% to 80% by weight of a diluent, about 2% to 20% by weight of a disintegrant, about 1% to 20% by weight of a binder, and about 0.5 % to 5% by weight of a lubricant and the sertraline hydrochloride comprises about 5% to about 70% by weight of the pharmaceutical composition.
  • a pharmaceutical composition for oral administration comprising sertraline or pharmaceutically acceptable salts thereof, having a particle size distribution as follows dgo: about 20 ⁇ m to about 40 ⁇ m d 50 : about 5 ⁇ m to about 15 ⁇ m d 10 : about 1 ⁇ m to 7 ⁇ m; wherein the composition is bioequivalent to a reference composition.
  • d 10 may range from about 1 ⁇ m to about 7 ⁇ m.
  • sertraline or pharmaceutically acceptable salts includes non-salt, non-hydrated free base as well as pharmaceutically acceptable acid addition salts and polymorphs thereof.
  • the pharmaceutically acceptable acid addition salts may be present in the form of a hydrate or polymorph, more particularly in the form of sertraline hydrochloride form II.
  • Sertraline or its pharmaceutically acceptable acid addition salt may be present in an amount ranging from 5% to 70% by weight of the composition.
  • reference composition refers to the marketed preparation of sertraline hydrochloride which is sold under the trade name ZOLOFT ® by Pfizer.
  • bioequivalent as used herein is intended to illustrate bioequivalence of the compositions of the present invention in comparison to the reference composition. Bioequivalence studies are conducted to demonstrate equivalence in the bioavailability of the active ingredient in different formulations.
  • Bioequivalence study involves statistical analysis for pharmacokinetic measures, such as area under the curve (AUC) and peak concentration (C max ) for a test (T) and reference (R) drug product, where T and R can vary, depending on the comparison to be performed (e.g., to-be-marketed dosage form versus clinical trial material, generic drug versus reference listed drug, drug product changed after approval versus drug product before the change).
  • AUC area under the curve
  • C max peak concentration
  • Bioequivalence comparisons normally rely on (1) a criterion, (2) a confidence interval for the criterion, and (3) a predetermined bioequivalence limit.
  • a criterion a confidence interval for the criterion
  • a predetermined bioequivalence limit a bioequivalence limit.
  • the calculated confidence interval should fall within a limit of 80-125% for the ratio of the product averages.
  • a bioequivalence limit of 80 to 125% for the ratio of the product averages has been adopted for use of a bioequivalence criterion.
  • the bioequivalence limit of 80 to 125% is based on a clinical judgment that a test product with bioavailability measures outside this range should be denied market access.
  • d 90 denotes that 90%, 50% and 10%, respectively, of the particles are smaller than the specified size.
  • the particle size of the drug may be reduced by conventional size-reduction methods known in the art, such as the various milling techniques, more particularly air jet milling.
  • Air jet milling is a well-proven technique that consistently produces particles in the 1-30 micron range, hi such a technique the particles of sertraline to be comminuted are accelerated in a stream of compressed air and micronized in a grinding chamber by their impact against each other.
  • the primary advantage of such a procedure is that the particle reduction occurs via particle to particle collisions with limited reduction from metal to product contact and no generation of heat.
  • compositions as described herein include powders, granulates, tablets and capsules.
  • Sertraline and pharmaceutically acceptable excipients may be formulated into compositions according to methods known in the art.
  • a composition for tableting or capsule filling may be prepared by wet granulation.
  • sertraline and pharmaceutically acceptable excipients such as diluents, disintegrants and binders are blended and then further mixed in the presence of a granulating fluid that causes the powders to clump into granules.
  • the granulate is screened and/or milled, dried and then screened and/or milled.
  • the granulate may then be mixed with other excipients such as a glidant and/or a lubricant, and compressed to form tablets or filled into hard gelatin capsules.
  • Diluents may be selected from cellulose-derived materials such as powdered cellulose, microcrystalline cellulose, microfine cellulose, and the like; lactose, starch, pregelatinized starch, sugars and sugar alcohols such as mannitol, sorbitol, erythritol and the like; dextrates, dextrin, dextrose, inorganic diluents such as calcium carbonate, calcium sulphate, dibasic calcium phosphate dihydrate, tribasic calcium phosphate, magnesium carbonate, magnesium oxide, potassium chloride, sodium chloride, talc and such other diluents known to the pharmaceutical industry.
  • cellulose-derived materials such as powdered cellulose, microcrystalline cellulose, microfine cellulose, and the like
  • the diluent may be present in an amount ranging from 20% to 80% by weight of the composition.
  • Disintegrants which may be used include alginic acid, carboxymethylcellulose calcium, carboxymethylcellulose sodium, cross-linked carboxymethylcellulose sodium, cross-linked polyvinyl pyrrolidone, sodium starch glycolate, magnesium aluminum silicate, powdered cellulose, microcrystalline cellulose, low-substituted hydroxypropyl cellulose, polacrilin potassium, pregelatinized starch, sodium alginate, starch and the like.
  • the disintegrant may be present in an amount ranging from 2% to 20% by weight of the composition.
  • Binders which may be used include gums such as acacia, guar gum, alginic acid, sodium alginate; carbomer, dextrin, gelatin, ethyl cellulose, methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, polymethacrylates, polyvinylpyrrolidone, pregelatinized starch, and the like.
  • the binder may be present in an amount ranging from 1% to 20% by weight of the composition.
  • Glidants which may be used include talc, colloidal silicon dioxide, magnesium trisilicate, powdered cellulose, starch, tribasic calcium phosphate and the like. The glidant may be present in an amount ranging from 0.5% to 5% by weight of the composition.
  • Lubricants which may be used include magnesium stearate, calcium stearate, glyceryl monostearate, glycerylpalmitostearate, hydrogenated castor oil, hydrogenated vegetable oil, mineral oil, polyethylene glycol, sodium benzoate, sodium lauryl sulfate, sodium stearyl fumarate, stearic acid, talc, zinc stearate and the like.
  • the lubricant may be present in an amount ranging from 0.5% to 5% by weight of the composition.
  • compositions may also include additional excipients such as flavoring agents, colors, and the like.
  • Flavoring agents may be selected from common flavor enhancers for pharmaceutical compositions such as vanillin, ethyl vanillin, menthol, citric acid, fumaric acid, ethyl maltol, tartaric acid and the like.
  • Colors may be selected from the group of ferric oxide, titanium dioxide, F.D. & C. and D. & C. dyes and the like.
  • a tableting composition may also be prepared by dry granulation.
  • the blended composition of the sertraline and excipients, as described above maybe compacted into a sheet by a roller compactor and then comminuted into granules. The compacted granules may subsequently be compressed into tablets.
  • a blended composition may be compressed directly into a compacted dosage form using direct compression techniques.
  • the pharmaceutical composition as described herein may be a capsule containing the composition, preferably a powdered or granulated composition as described above, within either a hard or soft shell. Tablets and granules may be coated.
  • the coating may be an enteric coating or non-functional coating. Suitable coatings for enteric-coated compositions include cellulose acetate phthalate, hydroxypropylmethyl cellulose phthalate, polyvinyl alcohol phthalate, carboxymethylethylcellulose, a copolymer of methacrylic acid and methyl methacrylate, and like materials. If desired, the coating may be employed with suitable plasticizers and/or extending agents. Non-functional coatings include coating compositions like Opadry® or Lustreclear® sold by Colorcon.
  • compositions for oral administration of sertraline hydrochloride having a particle size dgo ranging from about 20 ⁇ m to about 40 ⁇ m and d 50 ranging from about 5 ⁇ m to about 15 ⁇ m may be prepared by a) blending sertraline hydrochloride, diluent and disintegrant; b) granulating the blend obtained in step (a) with a binder solution; c) drying and sizing the granules; d) blending the granules obtained in step (c) with one or more of diluents, disintegrants, lubricants and glidants; e) compressing the blend to form tablets; and f) optionally coating the tablets with a non-functional coating.
  • compositions for oral administration of sertraline hydrochloride having a particle size dg 0 ranging from about 20 ⁇ m to about 40 ⁇ m and d 50 ranging from about 5 ⁇ m to about 15 ⁇ m may be prepared by a) blending sertraline hydrochloride, diluent and disintegrant; b) granulating the blend obtained in step (a) with water; c) drying and sizing the granules; d) blending the granules obtained in step (c) with one or more of diluents, disintegrants, lubricants and glidants; e) compressing the blend to form tablets; and f) optionally coating the tablets with a non-functional coating.
  • compositions for oral administration of sertraline hydrochloride having a particle size dg 0 ranging from about 20 ⁇ m to about 40 ⁇ m and d 50 ranging from about 5 ⁇ m to about 15 ⁇ m may be prepared by: a) blending sertraline hydrochloride and one or more of diluents, disintegrants and binders; b) compacting the blend obtained in step (a) with a roller compactor; c) sizing the compacts to form granules; d) blending the granules obtained in step (c) with one or more of diluents, disintegrants, binders, glidants and lubricants; and e) compressing the blend to form tablets.
  • compositions for oral administration of sertraline hydrochloride having a particle size dgo ranging from about 20 ⁇ m to about 40 ⁇ m and d 50 ranging from about 5 ⁇ m to about 15 ⁇ m may be prepared by: a) blending sertraline hydrochloride and one or more of diluents, disintegrants, binders, lubricants and glidants; and b) compressing the blend to form tablets.
  • Sertraline HCl, microcrystalline cellulose, dicalcium phosphate, and sodium starch glycolate are mixed in high shear mixer.
  • the blend obtained above is granulated using an aqueous solution of hydroxypropyl cellulose.
  • the granules are dried and milled.
  • the dried granules are blended with microcrystalline cellulose, sodium starch glycolate (only in example 1), magnesium stearate and compressed using appropriate tooling.
  • the tablets are coated using an Opadry coating mixture.
  • AUCiast Area under the plasma concentration vs. time curve from 0 hours to the time of last sample collected
  • AUC ⁇ Area under the plasma concentration vs. time curve from 0 hours to infinity
  • the composition of Example 1 is bioequivalent to the reference composition. This demonstrates the significance of using a particle size distribution of sertraline having dg 0 ranging from about 20 ⁇ m to about 40 ⁇ m and d 50 ranging from about 5 ⁇ m to about 15 ⁇ m in the preparation of pharmaceutical compositions.

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Abstract

La présente invention se rapporte à une composition pharmaceutique destinée à une administration orale et contenant de la sertraline ou des sels pharmaceutiquement acceptables de cette dernière, le chloryhdrate de sertraline possédant une taille de particule de d90 comprise entre environ 20 µm et environ 40 µm, et de d50 comprise entre environ 5 µm et environ 15 µm. La composition selon l'invention est bioéquivalente à une composition pharmaceutique de référence.
PCT/IB2006/000015 2005-01-07 2006-01-06 Formes posologiques orales de sertraline possedant une taille de particule controlee, et leurs procedes de preparation WO2006072878A1 (fr)

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IN39DE2005 2005-01-07
IN39/DEL/2005 2005-01-07

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WO2006072878A1 true WO2006072878A1 (fr) 2006-07-13

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WO2008018086A1 (fr) * 2006-08-10 2008-02-14 Bajaj Healthcare Limited Composition pharmaceutique ou nutraceutique se dissolvant dans la bouche
US8911971B2 (en) 2011-02-17 2014-12-16 Purecircle Usa Inc. Glucosyl stevia composition
US8981081B2 (en) 2010-03-12 2015-03-17 Purecircle Usa Inc. High-purity steviol glycosides
US8993269B2 (en) 2011-02-17 2015-03-31 Purecircle Usa Inc. Glucosyl stevia composition
US9029426B2 (en) 2010-12-13 2015-05-12 Purecircle Sdn Bhd Highly soluble Rebaudioside D
US9107436B2 (en) 2011-02-17 2015-08-18 Purecircle Sdn Bhd Glucosylated steviol glycoside as a flavor modifier
US9243273B2 (en) 2012-05-22 2016-01-26 Purecircle Sdn Bhd Method for making rebaudioside X
WO2016020936A3 (fr) * 2014-07-21 2016-05-26 Patel Jayendrakumar Dasharathlal Nouvelle forme posologique pharmaceutique orale de rétention gastrique
US9386797B2 (en) 2011-02-17 2016-07-12 Purecircle Sdn Bhd Glucosyl stevia composition
US9392799B2 (en) 2011-02-17 2016-07-19 Purecircle Sdn Bhd Glucosyl stevia composition
US9427006B2 (en) 2011-02-10 2016-08-30 Purecircle Sdn Bhd Highly soluble Stevia sweetener
US9474296B2 (en) 2011-02-17 2016-10-25 Purecircle Sdn Bhd Glucosyl stevia composition
US9510611B2 (en) 2010-12-13 2016-12-06 Purecircle Sdn Bhd Stevia composition to improve sweetness and flavor profile
US20170049774A1 (en) * 2015-08-19 2017-02-23 Sun Pharmaceutical Industries Limited Sustained release oral pharmaceutical compositions of tofacitinib
EP2056832B1 (fr) 2006-08-21 2017-03-22 AstraZeneca AB Compositions pour administration orale comprenant un dérivé de triazolo [4, 5]pyrimidine
US9752174B2 (en) 2013-05-28 2017-09-05 Purecircle Sdn Bhd High-purity steviol glycosides
US9771434B2 (en) 2011-06-23 2017-09-26 Purecircle Sdn Bhd Products from stevia rebaudiana
US9877501B2 (en) 2011-06-03 2018-01-30 Purecircle Sdn Bhd Stevia composition
US9894922B2 (en) 2011-05-18 2018-02-20 Purecircle Sdn Bhd Glucosyl rebaudioside C
US10004245B2 (en) 2009-11-12 2018-06-26 Purecircle Sdn Bhd Granulation of a stevia sweetener
US10021899B2 (en) 2011-05-31 2018-07-17 Purecircle Sdn Bhd Stevia composition
US10480019B2 (en) 2011-08-10 2019-11-19 Purecircle Sdn Bhd Process for producing high-purity rubusoside
US10531683B2 (en) 2005-10-11 2020-01-14 Purecircle Sdn Bhd Process for manufacturing a sweetener and use thereof
US10696706B2 (en) 2010-03-12 2020-06-30 Purecircle Usa Inc. Methods of preparing steviol glycosides and uses of the same
US10780170B2 (en) 2013-06-07 2020-09-22 Purecircle Sdn Bhd Stevia extract containing selected steviol glycosides as flavor, salty and sweetness profile modifier
US10952458B2 (en) 2013-06-07 2021-03-23 Purecircle Usa Inc Stevia extract containing selected steviol glycosides as flavor, salty and sweetness profile modifier
US11202461B2 (en) 2014-09-02 2021-12-21 Purecircle Sdn Bhd Stevia extracts
US11464246B2 (en) 2011-09-07 2022-10-11 Purecircle Sdn Bhd Highly soluble Stevia sweetener
CN115518049A (zh) * 2022-11-03 2022-12-27 则正(济南)生物科技有限公司 一种盐酸雷尼替丁胶囊及其制备方法
US11647771B2 (en) 2015-10-26 2023-05-16 Purecircle Usa Inc. Steviol glycoside compositions
US11653686B2 (en) 2015-12-15 2023-05-23 Purecircle Usa Inc. Steviol glycoside compositions
US11690391B2 (en) 2011-02-17 2023-07-04 Purecircle Sdn Bhd Glucosylated steviol glycoside as a flavor modifier
US11871771B2 (en) 2011-02-17 2024-01-16 Purecircle Sdn Bhd Glucosyl Stevia composition
US12016355B2 (en) 2011-02-10 2024-06-25 Purecircle Sdn Bhd Stevia composition

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Cited By (61)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10531683B2 (en) 2005-10-11 2020-01-14 Purecircle Sdn Bhd Process for manufacturing a sweetener and use thereof
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