WO1995000133A1 - Suspensions d'acetaminophene a gout masque et procedes de fabrication de celles-ci - Google Patents

Suspensions d'acetaminophene a gout masque et procedes de fabrication de celles-ci Download PDF

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Publication number
WO1995000133A1
WO1995000133A1 PCT/US1994/007037 US9407037W WO9500133A1 WO 1995000133 A1 WO1995000133 A1 WO 1995000133A1 US 9407037 W US9407037 W US 9407037W WO 9500133 A1 WO9500133 A1 WO 9500133A1
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WIPO (PCT)
Prior art keywords
acetaminophen
composition
agent
weight
amount
Prior art date
Application number
PCT/US1994/007037
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English (en)
Inventor
Seang H. Yiv
Alex Tustian
Original Assignee
Ibah, Inc.
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 Ibah, Inc. filed Critical Ibah, Inc.
Priority to AU71769/94A priority Critical patent/AU7176994A/en
Publication of WO1995000133A1 publication Critical patent/WO1995000133A1/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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide

Definitions

  • the present invention relates to acetaminophen compositions in which the acetaminophen is presented in taste- masked form. More particularly, the present invention relates to an acetaminophen composition wherein the acetaminophen solubility is limited by the presence of additive agents, such as sweetening agents.
  • Acetaminophen is a widely used over-the-counter drug which has beneficial pain relieving and fever relieving properties.
  • Acetaminophen is commonly taken as a tablet by the vast portion of the population. However, the tablet form is hard to administer in treating the elderly and the young. Therefore, liquid formulations of acetaminophen are commonly administered for these patients. However, in liquid form such as in an elixir formulation, the acetaminophen is dissolved into solution. Once dissolved, the strongly unpalatable taste of acetaminophen is found to be objectionable. Therefore, noncompliance among liquid acetaminophen patients is commonplace.
  • the invention provides an acetaminophen composition in taste-masked form, suitable for oral administration, containing acetaminophen in an aqueous medium.
  • the acetaminophen composition contains acetaminophen in an amount of up to about 10% by weight, preferably from about 2 to about
  • the aqueous medium contains suspension agent for dispersing the acetaminophen and additive agent for decreasing the solubility of the acetaminophen in the aqueous medium to below 1.3% wt .
  • the additive agent is preferably comprised of sweetening agents which are preferably present in an amount of at least about 25% by weight of the acetaminophen composition.
  • the suspension agent is preferably present in an amount of from about 0.03 to about 0.3% by weight and a preservative agent is also preferred to be present in the composition.
  • the sweetening agent preferably comprises at least one agent selected from the group consisting of sucrose, glucose, fructose, lactose, maltose, sorbitol, mannitol, and maltitol, and can consist of mixtures of these.
  • the acetaminophen composition of the present invention is characterized by having a palatable taste and with only a slight gritty feel.
  • the composition is a liquid formulation in which the acetaminophen is suspended, and slightly dissolved, in an aqueous medium containing a suspension agent for dispersing the acetaminophen and an additive agent that decreases the solubility of the acetaminophen in the aqueous solution.
  • the additive agent is preferably a sweetening agent. It has been surprisingly found that when the concentration of additive agent and suspension agent are properly adjusted, the taste of the acetaminophen can be masked effectively.
  • the acetaminophen which is useful in the present invention is particulate acetaminophen of pharmaceutical grade. It is preferred to use acetaminophen with a small average particle size to decrease the gritty feel of the drug. Generally the particle size of the acetaminophen is such that about 99% wt. is below about 420 microns and about 97% wt . is below about 250 microns. In a preferred embodiment, about 90% wt . is below about 150 microns and about 35% wt. is below about 40 microns, such acetaminophen is commercially available as acetaminophen Powder grade from Mallinckrodt, Inc., St. Louis, Mo.
  • a more preferred embodiment contains acetaminophen having about 70% wt . below about 40 microns such as the Fine Powder grade available from Mallinckrodt, Inc. In certain applications, a very fine acetaminophen is preferred having about 90% wt . below about 40 microns such as the Micronized acetaminophen from Mallinckrodt, Inc.
  • the acetaminophen is administered in dosages that effect the desired therapeutic result, "therapeutically effective amount", and the acetaminophen is generally present in the inventive compositions up to about 10% by weight, preferably from about 2 to about 8% by weight, and most preferably from 2 to 5% by weight of the final composition.
  • Common dosage forms are in 5- 10 ml quantities.
  • the acetaminophen compositions of the present invention contain a suspension agent or mixtures of suspension agents.
  • Suitable suspension agents are well known in the art and include, but are not limited to, xanthan gum, sodium alginate, carrageenan, carboxylmethylcellulose, algin, guar gum, propylene glycol alginate, and mixtures thereof; xanthan gum being preferred.
  • the suspension agent is useful to keep the particulate acetaminophen concentration uniform in the composition.
  • the suspension agent is preferably present in an amount of from about 0.03 to about 0.3% by weight of the composition, more preferably about 0.05 to about 0.2% by weight .
  • the weight ratio of acetaminophen to suspension agent is typically about 1:0.01 to about 1:0.08.
  • the suspension agent is preferably accompanied by a dispersant.
  • the dispersant acts to aid in making the aqueous solution containing the suspension agent homogeneous. If the dispersant is not employed, vigorous agitation is usually necessary to suspend the suspension agent in the aqueous medium.
  • Dispersants which can be used in the present invention are well known and include, for example, glycerin, propylene glycol, ethanol and combinations thereof. Typically, the dispersant is present from about 0.15 to about 0.5% by weight of the composition.
  • the additive agent is present in the composition in a relatively high concentration.
  • the high concentration of additive agent acts to limit the solubility of the acetaminophen in the liquid composition.
  • the unpalatable taste of the liquid acetaminophen composition is thereby reduced due to the decreased solubility of the acetaminophen.
  • the amount of solubilized acetaminophen in the compositions of this invention is generally below 1.3% by weight, preferably below 1.1% by weight, more preferably below 0.95% by weight, and most preferably below 0.85% by weight.
  • the additive agent is preferably comprised of a sweetening agent or mixtures of sweetening agents so that not only is the bitter taste of the acetaminophen in solution limited, but it is replaced by the pleasant tasting sweetener.
  • Other agents can also be used to limit the solubility of the acetaminophen. These agents include such compounds as salts or polyol compounds such as propylene glycol and polyethylene glycol . These agents are preferably taste-neutral, and the amount of these agents is preferably limited so that they do not significantly alter the taste of the final composition as being unpalatable.
  • the additive agent is at least 75% wt . , more preferably at least 90% wt . , and most preferably 100% wt . sweetening agent.
  • Sweetening agents which can be used in the present invention to limit the solubility of the acetaminophen in aqueous solution are those of the polyol type, particularly those which are highly soluble in water. Sweetening agents of this type include the sugars such as sucrose (C 12 H 22 0 11 ) , glucose (C 6 H 12 0 6 ) , fructose (C 6 H 12 0 6 ) , lactose ( ⁇ H ⁇ On) , and maltose (C 12 H 22 0 11 ) , preferably in pharmaceutical grades.
  • Natural and semi-refined sweetening agents such as honey and corn syrups, which are mixtures of sugars with other related compounds, can be used, as well as polymers of sugars such as maltodextrins. Low levels of artificial sweetners such as aspartame and saccharin can also be used.
  • the sweetening agent can also be a mixture of any of the above-mentioned compounds.
  • the additive agent concentration is at least 25% wt. , preferably at least 50% wt . , more preferably at least 55% wt. , and in some cases at least 60% wt .
  • the amount of additive agent will generally not exceed about 85% wt . of the composition, and is limited by its solubility.
  • the drug to additive agent weight ratio is generally about 1:5 to about 1:40, preferably about 1:10 to about 1:30.
  • Various flavors such as mint, cherry, punch, spearmint, grape and the like can also be added to the composition. If present, such flavoring agents are preferably provided in an amount of up to about 0.2% wt . of the composition. The amount of flavoring agent is limited by taste considerations at higher concentrations.
  • the acetaminophen composition can also contain preservatives.
  • the preservatives which can be used are well known in the art as common food preservatives. Examples are set forth in the CTFA Cosmetic Ingredient Handbook, published by Cosmetic, Toiletry, and Fragrance Assoc. , Wash. D.C. (1988) , which is incorporated herein in its entirety.
  • Preferred preservatives include methylparaben, sodium benzoate, isopropylparaben, sorbic acid and mixtures thereof, preferably sodium benzoate.
  • Antioxidants, such as BHT can also be used.
  • the pH of the acetaminophen composition is held below about 6, and most preferably between about 3.5 and 5.
  • the pH is preferably maintained at these levels to sustain a long shelf life since the preservatives usually do not work well in a high pH system.
  • Any appropriate ingestible acid may be used to modify the pH of the acetaminophen composition, including hydrochloric, citric, and acetic acid.
  • the final density of the acetaminophen composition generally ranges from about 1.1 to about 1.35 g/ml, preferably about 1.25 to about 1.32 g/ml.
  • the viscosity of the acetaminophen composition generally ranges from about 200-900 centipoise, preferably from about 300-700 centipoise.
  • compositions of the present invention contain 2-5% wt . , preferably 2-3% wt . acetaminophen; 30-40% wt., preferably 33-37% water; 0.15-0.2% wt . dispersant; 0.03- 0.1% wt . , preferably 0.05-0.1% wt. suspension agent; and 55-65% wt . sweetener.
  • the composition can also contain 0.05-0.1% wt. preservative.
  • the acetaminophen compositions of the present invention can be prepared by providing particulate acetaminophen and admixing it into an aqueous solution containing the suspension agent and the additive agent, the pH of the aqueous solution having been adjusted using an ingestible acid.
  • the aqueous solution can also contain preservatives, dispersants, and flavoring agents.
  • the acetaminophen compositions of the present invention can also be prepared by first preparing a suspension agent solution containing the suspension agent in an aqueous medium. It is preferred that the aqueous solution contain about 1 to about 5, most preferably about 2 weight percent suspension agent.
  • the suspension agent solution can also contain dispersant and preservative.
  • the particulate acetaminophen is then mixed into the suspension agent solution.
  • An aqueous solution containing the additive agent is then added to the mixture; this solution typically contains a preservative.
  • Example 1 The invention is further illustrated by the following non-limiting examples.
  • Example 1 The invention is further illustrated by the following non-limiting examples.
  • An acetaminophen composition was produced which effectively masked the taste of the acetaminophen.
  • a 3.2 g sample of acetaminophen was placed in a container.
  • the drug and polymer solution was mixed and rubbed thoroughly with a pestle.
  • 119.9 g of a sweetening solution containing 65 wt.% sucrose, 0.08% wt. sodium benzoate with a pH adjusted to 4.3 using hydrochloric acid was incrementally added to the drug/polymer mixture. Pestle rubbing was continued throughout the addition.
  • 0.2 g of fruit punch flavor was added to the suspension.
  • the final composition had a suspension agent concentration of 0.08% wt. , and a sweetening agent concentration of 61% wt .
  • An acetaminophen composition was produced which effectively masked the taste of the acetaminophen.
  • a 6.5 g sample of acetaminophen was placed in a container.
  • the drug and polymer solution was mixed and rubbed thoroughly with a pestle.
  • 109 g of a sweetening solution containing 65 wt.% sucrose, 0.08% wt. sodium benzoate with a pH adjusted to 4.3 using acetic acid was incrementally added to the drug/polymer mixture. Pestle rubbing was continued throughout the addition. Finally, 45 mg of mint flavor was added to the suspension.
  • the final composition had a suspension agent concentration of 0.16% wt . , and a sweetening agent concentration of 56.5% wt .
  • Example 3 An acetaminophen composition was prepared containing
  • Example 4 An acetaminophen composition was prepared containing
  • Example 5 5.1% wt . acetaminophen, 0.05% wt . xanthan gum, 0.3% wt. sodium carboxymethylcellulose and about 57% wt . sucrose.
  • the composition was prepared by adding 0.9 g of the xanthan gum solution of Example 3 to 1.95 g acetaminophen. Additionally, 1.5 g of an 8% wt. aqueous solution of sodium carboxymethyl cellulose was added. The mixture was thoroughly mixed in a ceramic vessel until the drug was wetted and dispersed homogeneously. Next, 33.5 g of the aqueous syrup of Example 3 was incrementally admixed to the vessel . The final mixture had a volume of 30 ml.
  • Example 5 Example 5
  • An acetaminophen composition was prepared containing 5.1% wt. acetaminophen, 0.05% wt . xanthan gum, and about 60% wt . sucrose.
  • the composition was prepared by adding 0.9 g of the 2% wt. xanthan gum solution of Example 3 to 1.95 g acetaminophen.
  • the mixture was thoroughly mixed in a ceramic vessel until the drug was wetted and dispersed homogeneously.
  • 35.4 g of the aqueous syrup of Example 3 was incrementally admixed to the vessel .
  • the final mixture had a volume of 30 ml.
  • An acetaminophen composition was prepared containing 5.1% wt. acetaminophen, 0.16% wt. xanthan gum, and about 56% wt . sucrose.
  • 65 g acetaminophen and 100 g of the xanthan gum solution of Example 3 were added and mixed to form a homogeneous mixture.
  • 1090 g of the syrup of Example 3. The final mixture had a volume of 1000 ml.
  • acetaminophen composition was prepared containing 2.5% wt . acetaminophen, 0.16% wt . algin, and about 58% wt. sucrose.
  • the composition was prepared by adding 3 g of a 2% wt . aqueous algin solution to 0.96 g acetaminophen. The mixture was thoroughly mixed in a ceramic vessel until the drug was wetted and dispersed homogeneously. Next 34 g of the syrup of Example 3 was incrementally admixed to the vessel . The final mixture had a volume of 30 ml.
  • An acetaminophen composition was prepared containing 2.5% wt. acetaminophen, 0.08% wt . guar gum, and about 58% wt. sucrose.
  • the composition was prepared by adding 3 g of a 1% wt . aqueous guar gum solution to 0.96 g acetaminophen. The mixture was thoroughly mixed in a ceramic vessel until the drug was wetted and dispersed homogensouly. Next 34 g of the syrup of Example 3 was incrementally admixed to the vessel . The final mixture had a volume of 30 ml.
  • Example 9 An acetaminophen composition was prepared containing
  • Example 10 2.5% wt. acetaminophen, 0.16% wt. propylene glycol alginate, and about 58% wt. sucrose.
  • the composition was prepared by adding 3 g of a 0.2% wt . aqueous propylene glycol alginate to 0.96 g acetaminophen. The mixture was thoroughly mixed in a ceramic vessel until the drug was wetted and dispersed homogeneously. Next 34 g of the syrup of Example 3 was incrementally added to the vessel. The final mixture had a volume of 30 ml.
  • Example 10 Example 10
  • a suspension of 2.5% w/v acetaminophen was prepared using sucrose and sorbitol as sweetening agents.
  • 15 g of the aqueous polymer solution of Example 3 (2% Xanthan gum solution) , 121.4 g of a 70% wt . sorbitol solution (pH adjusted to 4.2 with HCl preserved with sodium benzoate) , and 493.8 g of the sucrose sweetening solution of Example 3 were mixed in a 1 liter beaker until a homogeneous solution was obtained. Stirring was continued and 16 g of acetaminophen was added to the solution. Stirring was continued for 15 minutes. 500 ml (646.2 g) of the final composition was produced.
  • a suspension of 2.5% wt. acetaminophen was prepared using sucrose and sorbitol as sweetening agents.
  • 15 g of the aqueous polymer solution of Example 3 (2% Xanthan gum solution) , 242.9 g of a 70% wt. sorbitol solution (pH adjusted to 4.2 with HCl preserved with sodium benzoate) , and 370.3 g of the sucrose sweetening solution of Example 3 were mixed in a 1 liter beaker until a homogeneous solution was obtained. Stirring was continued and 16 g of acetaminophen was added to the solution. Stirring was continued for 15 minutes. 500 ml (644.2 g) of the final composition was produced.
  • Suspensions of 2.5% wt . acetaminophen containing various amounts of water and sucrose were made by mixing in a mortar and pestle. In each sample, 0.96 g acetaminophen was weighed and added to the mortar, 1.5 g of polymer solution (2% wt . xanthan gum, 6% wt . glycerine, 0.2% wt . methyl paraben) was added, and then mixed and rubbed thoroughly with a pestle. In the case of Sample 1, 36.00 g of syrup (65% wt . sucrose, 0.08% wt.
  • Na benzoate with pH adjusted to 4.2 +/- 0.1 using hydrochloride acid
  • Samples 3, 4 and 5 were prepared in the same way, except the amounts of low pH syrup added were 28.13 g, 18.46 g, and 9.23 g, respectively; and the amounts of low pH water added were 6.00 g, 13.40 g, and 20.47 g, respectively. Sample 6 was also prepared in this manner, but no syrup was added; 27.5 g low pH water was added to the polymer/drug mixture directly, in increments, with mixing action in between the increments. Suspensions were tasted for bitterness level at this point.
  • a 2380 kg (490 gallon) batch of the acetaminophen suspension of the present invention was prepared. To a cleaned sanitized stainless steel vessel was added 222.5 gallons of USP water and heated to 115°F. 4.17 kg of glycerin was added and mixed thoroughly for about 30 minutes. Xanthan Gum, 1111 g (Keltrol T) was slowly added with mixing continued for 30 minutes. The temperature was maintained and the mixing was continued and 1019 g artificial cherry flavor was added over a 15 minute period followed by the addition of 1470 kg sucrose and 1854 g USP sodium benzoate over a 25 minute period. The temperature was then lowered to 75°F.
  • hydrochloric acid 37%) was admixed (15 min.) and the pH of the mixture was found to be about 4.5. To this was admixed 224 g FD&C Red dye #40 and stirring was continued for about 2.5 hours. 59.31 kg of USP micronized acetaminophen from Mallinckrodt, Inc. was admixed with continued stirring over a period of 1 hour. The mixture was passed through a 20 mesh screen into 50 gallon drums. The final composition had about 2.5 wt .% acetaminophen, 62 wt . % sucrose, 0.05 wt.
  • Example 14 % xanthan gum, 0.2 wt.% glycerin, 35 wt.% water, 0.08 wt .% sodium benzoate, 0.02 wt.% HCl (37%) , 0.04 wt.% cherry flavor, and 0.01 wt.% coloring.
  • Example 14
  • a 2380 kg (490 gallon) batch of the acetaminophen suspension of the present invention was prepared. To a cleaned sanitized stainless vessel was added 222.5 gallons of USP water and heated to 115°F. 4.17 Kg of glycerin was added and mixed with constant stirring for 35 minutes. Xanthan Gum (1.111 Kg) was slowly educted with mixing for 30 minutes. While maintaining a temperature of 115°F and mixing to create a vortex, sucrose (1,470 Kg) was added over a 25 minute period. Mixing was maintained and the mixture was cooled to 75°F. 450g of 37% HCl was added slowly with mixing continued for 15 minutes. The pH of a sample was measured to be 4.5.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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Abstract

L'invention concerne une composition à base d'acétaminophène dans laquelle le goût de l'acétaminophène est effectivement masqué par la mise en suspension du médicament dans un milieu contenant un agent de suspension et des additifs qui diminuent la solubilité de l'acétaminophène dans une solution aqueuse. Les additifs sont de préférence des édulcorants. La concentration de ces édulcorants est, de préférence, d'au moins 25 % en poids de la composition d'acétaminophène.
PCT/US1994/007037 1993-06-25 1994-06-21 Suspensions d'acetaminophene a gout masque et procedes de fabrication de celles-ci WO1995000133A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU71769/94A AU7176994A (en) 1993-06-25 1994-06-21 Taste-masked acetaminophen suspensions and methods of making the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8365193A 1993-06-25 1993-06-25
US08/083,651 1993-06-25

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WO1995000133A1 true WO1995000133A1 (fr) 1995-01-05

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003032973A2 (fr) * 2001-10-18 2003-04-24 Reckitt Benckiser Healthcare (Uk) Limited Composition contenant paracetamol et un constituant masquant l'amertume
US7101572B2 (en) 2001-12-07 2006-09-05 Unilab Pharmatech, Ltd. Taste masked aqueous liquid pharmaceutical composition
WO2006050302A3 (fr) * 2004-10-29 2007-02-15 Mcneil Ppc Inc Suspensions pharmaceutiques sans colorant et methodes connexes
EP1911454A1 (fr) * 2005-04-27 2008-04-16 HK Phlora Health Sci. & Tech. Limited Composition et procédé de régulation et de maintien de la flore bactérienne vaginale et de l'acidité normale dans le vagin
WO2016024928A1 (fr) 2014-08-14 2016-02-18 Bi̇ofarma İlaç Sanayi̇ Ve Ti̇caret A.Ş. Formulations de paracétamol au goût masqué
WO2019174755A1 (fr) 2018-03-14 2019-09-19 Laboserve Pharmaceutical Company S.A. Solutions orales comprenant du tramadol et de l'acétaminophène
US11931413B2 (en) 2017-11-02 2024-03-19 Genexa Inc. Dextromethorphan and guaifenesin syrup formulation or suspension

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3142621A (en) * 1961-11-02 1964-07-28 Ciba Geigy Corp Alginate suspensions of oral pharmaceutical compositions with improved taste qualities
US3317377A (en) * 1966-04-19 1967-05-02 Squibb & Sons Inc Sedative-analgesic compositions
US5272137A (en) * 1992-02-14 1993-12-21 Mcneil-Pfc, Inc. Aqueous pharmaceutical suspension for pharmaceutical actives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3142621A (en) * 1961-11-02 1964-07-28 Ciba Geigy Corp Alginate suspensions of oral pharmaceutical compositions with improved taste qualities
US3317377A (en) * 1966-04-19 1967-05-02 Squibb & Sons Inc Sedative-analgesic compositions
US5272137A (en) * 1992-02-14 1993-12-21 Mcneil-Pfc, Inc. Aqueous pharmaceutical suspension for pharmaceutical actives

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003032973A2 (fr) * 2001-10-18 2003-04-24 Reckitt Benckiser Healthcare (Uk) Limited Composition contenant paracetamol et un constituant masquant l'amertume
WO2003032973A3 (fr) * 2001-10-18 2003-08-14 Reckitt Benckiser Healthcare Composition contenant paracetamol et un constituant masquant l'amertume
US7101572B2 (en) 2001-12-07 2006-09-05 Unilab Pharmatech, Ltd. Taste masked aqueous liquid pharmaceutical composition
WO2006050302A3 (fr) * 2004-10-29 2007-02-15 Mcneil Ppc Inc Suspensions pharmaceutiques sans colorant et methodes connexes
JP2008518948A (ja) * 2004-10-29 2008-06-05 マクニール−ピーピーシー・インコーポレイテッド 無染料薬剤懸濁液および関連する方法
EP1911454A1 (fr) * 2005-04-27 2008-04-16 HK Phlora Health Sci. & Tech. Limited Composition et procédé de régulation et de maintien de la flore bactérienne vaginale et de l'acidité normale dans le vagin
EP1911454A4 (fr) * 2005-04-27 2009-07-29 Hk Phlora Health Sci & Tech Lt Composition et procédé de régulation et de maintien de la flore bactérienne vaginale et de l'acidité normale dans le vagin
US8586549B2 (en) 2005-04-27 2013-11-19 Shenzhen Phlora Biotechnology Limited Composition and method for modulating and maintaining vaginal bacterial flora and vaginal acidity
WO2016024928A1 (fr) 2014-08-14 2016-02-18 Bi̇ofarma İlaç Sanayi̇ Ve Ti̇caret A.Ş. Formulations de paracétamol au goût masqué
US11931413B2 (en) 2017-11-02 2024-03-19 Genexa Inc. Dextromethorphan and guaifenesin syrup formulation or suspension
WO2019174755A1 (fr) 2018-03-14 2019-09-19 Laboserve Pharmaceutical Company S.A. Solutions orales comprenant du tramadol et de l'acétaminophène

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