GB2552728A - Non-effervescent granulates containing N-acetylcysteine - Google Patents

Non-effervescent granulates containing N-acetylcysteine Download PDF

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GB2552728A
GB2552728A GB1701787.2A GB201701787A GB2552728A GB 2552728 A GB2552728 A GB 2552728A GB 201701787 A GB201701787 A GB 201701787A GB 2552728 A GB2552728 A GB 2552728A
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Prior art keywords
flavour
acetylcysteine
effervescent
maltodextrin
granulate
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GB2552728B (en
GB2552728A9 (en
GB201701787D0 (en
Inventor
Stroppolo Federico
Granata Gabriele
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Alpex Pharma SA
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Alpex Pharma SA
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    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/12—Mucolytics

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biophysics (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pulmonology (AREA)
  • Biochemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A non-effervescent granulate containing N-acetylcysteine and maltodextrin is disclosed. The composition also comprises a gliding agent selected from fumed colloidal silicon dioxide, precipitated silica, and talc; a flavouring agent selected from orange, lemon, peppermint, anise, apricot or strawberry; and a sweetener chosen from aspartame, saccharin, acesulfame potassium, sucralose, stevia, advantame or neotame. A polyalcohol may also be included and is selected from sorbitol, xylitol, mannitol, maltitol and lactitol. In a preferred embodiment, the composition comprises at least 30 wt% N-acetylcysteine, at least 30 wt% maltodextrin, orange flavouring, sucralose (as sweetener), colloidal silicon dioxide (as gliding agent) and mannitol (as polyol).

Description

(54) Title of the Invention: Non-effervescent granulates containing N-acetylcysteine
Abstract Title: N-acetylcysteine and maltodextrin in non-effervescent granulate composition (57) A non-effervescent granulate containing N-acetylcysteine and maltodextrin is disclosed. The composition also comprises a gliding agent selected from fumed colloidal silicon dioxide, precipitated silica, and talc; a flavouring agent selected from orange, lemon, peppermint, anise, apricot or strawberry; and a sweetener chosen from aspartame, saccharin, acesulfame potassium, sucralose, stevia, advantame or neotame. A polyalcohol may also be included and is selected from sorbitol, xylitol, mannitol, maltitol and lactitol. In a preferred embodiment, the composition comprises at least 30 wt% N-acetylcysteine, at least 30 wt% maltodextrin, orange flavouring, sucralose (as sweetener), colloidal silicon dioxide (as gliding agent) and mannitol (as polyol).
TITLE
Non-effervescent granulates containing N-acetylcysteine
DESCRIPTION
The present invention relates to a pharmaceutical composition in the form of a noneffervescent granulate containing N-acetylcysteine and, more in particular, a pharmaceutical composition in the form of a non-effervescent granulate containing N-acetylcysteine and maltodextrin.
N-acetylcysteine, commonly known as NAC, is a synthetic modified N-acetylated aminoacid, used for years as mucolytic active ingredient.
NAC is also used in different doses and formulations for treating paracetamol poisoning, amanita and other mushrooms poisoning, muco-viscidosis, dry eye syndrome, dental plaque, skin diseases and other pathologies.
EP 2 558 065 A1, in the name of the applicant, discloses stable effervescent formulations containing NAC and sucralose.
One of the main problem bound to the formulation of NAC, in particular as a granulate, is to provide a composition that is stable, both from a chemical and physical point of view.
The problem of stability is more evident when effervescent granulates of NAC are stored for a long time especially at high room temperatures, as often happens in summer, or in regions where the climate is constantly warm.
In fact in effervescent granulates when heated over 40 eC, the sodium bicarbonate present in the formulation starts to react, releasing CO2 and water. In these conditions, the stabilities of the effervescent granulate and of NAC decrease. Moreover, effervescent granulates contain a lot of sodium or potassium sourced from the carbonate or bicarbonate used for effervescence, that is not indicated for some patients affected by renal or cardiovascular diseases.
Another problem in the formulation of NAC as a granulate is to provide a granulate that has a good flowability and which is in particular free flowing, allowing to prepare sachets containing the granulate, showing a regularity of weight.
Moreover, there is the need of a granulate containing NAC having a reduced volume (i.e. bulk and tapped density), so as to be easily filled in sachets.
There is therefore the need of a stable granulate containing NAC that solves all the above mentioned technical problems.
-2The inventors of the present application have surprisingly found that noneffervescent granulates containing N-acetylcysteine and maltodextrin are very stable both from a physical and chemical point of view, have a good flowability and reduced volume and present therefore many advantages from a pharmaceutical technology formulation point of view.
It is therefore object of the present invention a non-effervescent granulate comprising:
- at least 30% by weight of N-acetylcysteine,
- at least 30% by weight of maltodextrin,
- a gliding agent
- a sweetener,
- a flavouring agent wherein the weight ratio between N-acetylcysteine and maltodextrin is from about 0.8 to about 1.2.
The non-effervescent granulates of the present invention can contain 600 mg of NAC with a total weight of about 1.3 - 2.0 g and have an increased stability compared to the effervescent granulates containing the same amount of NAC known in the art, as it can be appreciated in the experimental part.
The characterizing feature of the non-effervescent granulate according to the present invention is the weight ratio between N-acetylcysteine and maltodextrin which is from about 0.8 to about 1.2.
Preferably the weight ratio between N-acetylcysteine and maltodextrin is from about 0.9 to about 1 and it is more preferably 0.9.
A gliding agent according to the present invention can be fumed colloidal silicon dioxide, known with the trade name of Aerosih 200, or precipitated silica known with the trade name of Syloidy or talc, preferably the gliding agent is fumed colloidal silicon dioxide.
A sweetener according to the present invention can be any artificial or natural sweetener conventionally used in pharmaceutical technology, such as aspartame, saccharin, acesulfame potassium, sucralose, stevia, advantame, neotame, preferably the sweetener is sucralose.
A flavouring agent according to the present invention can be any flavouring agent conventionally used in pharmaceutical technology, such as orange flavour, lemon flavour, peppermint flavour, anise flavour, apricot flavour, strawberry flavour,
-3preferably the flavouring agent is orange flavour, in particular Orange flavor Sensient 00285.
According to another embodiment of the present invention, the non-effervescent granulate can optionally further comprise a polyalcohol preferably selected among sorbitol, xylitol, mannitol, maltitol, lactitol, more preferably mannitol.
According to a preferred embodiment of the present invention the non-effervescent granulate comprises N-acetylcysteine in an amount of about 30-45% by weight and maltodextrin in an amount of about 33-50% by weight.
A non-effervescent granulate comprising:
- 30-45% by weight of N-acetylcysteine,
- 33-50% by weight of maltodextrin,
- 0.1-0.5% by weight of a gliding agent,
- 2-6% by weight of a flavouring agent
- 0.7-2% by weight of a sweetener is a further preferred object of the present invention.
The non-effervescent granulate according to the present invention can be prepared according to conventional techniques of granulation that will be illustrated in detail in the experimental section.
Specific examples of particularly preferred non-effervescent granulate have the following quantitative composition (in brackets percentages by weight):
N-acetylcysteine 600 mg (44.78%)
Maltodextrin 660 mg (49.25%)
Orange flavour 60 mg (4.48%)
S ucralose 18 mg (1.34%)
Colloidal silicon dioxide 2 mg (0.15%)
TotaI weight 1340 mg
N-acetylcysteine 600 mg (30.00%)
Maltodextrin 660 mg (33.00%)
Mannitol 660 mg (33.00%)
Orange flavour 60 mg (3.00%)
S ucralose 18 mg (0.90%)
Colloidal silicon dioxide 2 mg (0.10%)
T ota I weight 2000 mg
-4In order to better illustrate the invention, without however limiting it; the following examples are now given.
Example 1
Preparation of a non-effervescent granulate
Components Composition per sachet mg Composition per batch of Kg 134 Kg
N-Acetylcysteine 600 60
Maltodextrin 660 66
Orange flavor Sensient 00285 60 6
S ucralose 18 1.8
Aerosil 200 2 0.2
TotaI weight 1340 134
In a fluid bed granulator as Aeromatic S6 Kg 60 of N-acetylcysteine, Kg 66 of maltodextrin, Kg 1.8 of sucralose and Kg 6 of orange flavour were placed.
The mixture was granulated with Kg 6 of purified water and then dried at 60 eC until the granulate relative humidity (RH) was below 0.5%.
At the end of process, the granulate was blended for 15 minutes in a cube mixer as a Zanchetta bin blender together with Kg 0.2 of Aerosyl 200.
Using an industrial equipment as Marchesini RC 600 filing machine, sachets were filled with mg 1340 of granulate in order to get mg 600 of N-acetylcysteine in each sachet
Non-effervescent granulate characteristics:
Granulate appearance White to yellowish granules without foreign bodies
Particle size 90% less than 500 i m 50% less than 250 i m
Bulk density 0.7
Tapped density 0.8
Flowability as angle of repose 34e
Comparative example 2
Preparation of an effervescent granulate
Components Composition per sachet mg Composition per batch of Kg 150 Kg
N-Acetylcysteine 600 60
Sodium Bicarbonate 420 42
Citric acid 400 40
Orange flavor Sensient 00285 70 7
S ucralose 10 1.0
TotaI weight 1500 150
In a fluid bed granulator Aeromatic S6, Kg 60 of N-acetylcysteine, Kg 40 of citric acid, Kg 42 of sodium bicarbonate, Kg 7 of orange flavour and Kg 1 of sucralose were placed.
The mixture was granulated with Kg 6 of purified water and then dried at 60 eC until the granulate relative humidity (RH) was below 0.5%.
At the end of process, the granulate was blended for 15 minutes in a cube mixer as a Zanchetta bin blender.
Using an industrial equipment as Marchesini RC 600 filing machine, sachets were filled with mg 1500 of granulate in order to get mg 600 of N-acetylcysteine in each sachet
Effervescent granulate characteristics:
Granulate appearance White to yellowish granules without foreign bodies
Particle size 90% less than 530 i m 50% less than 250 i m
Bulk density 0.87
Tapped density 0.96
Flowability as angle of repose 34e
-6Example 3
Preparation of a non-effervescent granulate
Components Composition per sachet mg Composition per batch of Kg 134 Kg
N-Acetylcysteine 600 60
Maltodextrin 660 66
Mannitol 660 66
Orange flavor Sensient 00285 60 6
S ucralose 18 1.8
Aerosil 200 2 0.2
TotaI weight 2000 200
In a fluid bed granulator Aeromatic S6, Kg 60 of N-acetylcysteine, Kg 66 of maltodextrin, Kg 66 of mannitol DC, 400 Kg 6 of orange flavour, Kg 1.8 ofsucralose Kg 0.2 of Aerosyl 200 were placed.
The mixture was granulated with Kg 6 of purified water and then dried at 60 eC until the granulate relative humidity (RH) was below 0.5%.
At the end of process, the granulate was blended for 15 minutes in a cube mixer as a Zanchetta bin blender.
Using and industrial equipment as Marchesini RC 600 filing machine, sachets were filled with mg 2000 of granulate in order to get mg 600 of N-acetylcysteine in each sachet
Non-effervescent granulate characteristics:
Granulate appearance White to yellowish granules without foreign bodies
Particle size 90% less than 530 ι m 50% less than 250 ι m
Bulk density 0.70
Tapped density 0.8
Flowability as angle of repose 35e
-Ί Example 4
Comparison of the CV (variation coefficient) of the weight of the granulate filled in the sachets
Example 1 Comparative Example 2 Example 3
Target weight mg 1340 1500 2000
CV 1.2 1.3 1.5
The example 1, despite the reduced weight of sachets and the presence of more than 40 % of N-Acetylcysteine in the composition shows a regularity of the weight similar or superior to the other compositions.
Example 5
Stability comparison between Example 1, Comparative example 2 and Example 3
Example 1 Comparative example 2 Example 3
Assay N-Acetylcysteine 3 months at40eC-75%RH 100% 80% 100%
Assay N-Acetylcysteine 6 months at40eC-75%RH 100% 50% 100%
As it can be appreciated by the results reported above, the non-effervescent granulates of the present invention (examples 1 and 3) have:
Lower bulk density compared to the effervescent granulate of comparative example 2;
Lower tapped density compared to the effervescent granulate of comparative 20 example 2;
Lower coefficient of variation (in particular example 1) compared to the effervescent granulate of comparative example 2;
Better stability (assay N-acetylcysteine) compared to the effervescent granulate of comparative example 2.
C LAIMS
1) A non-effervescent granulate comprising:
- at least 30% by weight of N-acetylcysteine,
- at least 30% by weight of maltodextrin,
- a gliding agent
- a flavouring agent
- a sweetener, wherein the weight ratio between N-acetylcysteine and maltodextrin is from about 0.8 to about 1.2.
2) A non-effervescent granulate according to claim 1 comprising Nacetylcysteine in an amount of about 30'45% by weight and maltodextrin in an amount of about 33-50% by weight.
3) A non-effervescent granulate according to claim 1 or 2 comprising
- 30-45% by weight of N-acetylcysteine,
- 33-50% by weight of maltodextrin,
- 0.1-0.5% by weight of a gliding agent,
- 2-6% by weight of a flavouring agent
- 0.7-2% by weight of a sweetener.
4) A non-effervescent granulate according to claims from 1 to 3 wherein the gliding agent is fumed colloidal silicon dioxide or precipitated silica or talc, preferably the gliding agent is fumed colloidal silicon dioxide.

Claims (1)

  1. 5) A non-effervescent granulate according to claims from 1 to 4 wherein the flavouring agent is orange flavour, lemon flavour, peppermint flavour, anise flavour, apricot flavour, strawberry flavour, preferably the flavouring agent is orange flavour.
    6) A non-effervescent granulate according to claims from 1 to 5 wherein the sweetener is an artificial or natural sweetener selected from aspartame, saccharin, acesulfame potassium, sucralose, stevia, advantame, neotame, preferably the sweetener is sucralose.
    7) A non-effervescent granulate according to claims from 1 to 6 further comprising a polyalcohol.
    8) A non-effervescent granulate according to claim 7 wherein the polyalcohol is selected among sorbitol, xylitol, mannitol, maltitol, lactitol, preferably the polyalcohol is mannitol.
    9) A non-effervescent granulate according to claim 1 having the following
    quantitative composition: N-acetylcysteine 600 mg Maltodextrin 660 mg Orange flavour 60 mg S ucralose 18 mg Colloidal silicon dioxide 2 mg T ota I weight 1340 mg
    10) A non-effervescent granulate according to claim 1 having the following quantitative composition:
    N-acetylcysteine 600 mg
    Maltodextrin 660 mg
    Mannitol 660 mg
    Orange flavour 60 mg
    Sucralose 18 mg
    Colloidal silicon dioxide 2 mg
    TotaI weight 2000 mg
    Intellectual
    Property
    Office
    Miss Anna Crosby
    November 2017
    GB1701787.2
    1-10
    Application No: Claims searched:
    Examiner: Date of search:
    Patents Act 1977: Search Report under Section 17
    Documents considered to be relevant:
    Category Relevant to claims Identity of document and passage or figure of particular relevance X 1-6 EP1449525 Al CROSS CHEMLLC. See especially example 1 X 1-6 WO2011/146031 Al BILGIC MAHMUT. See especially Example 2, line 30 pg 6, lines 5-23 pg 7, lines 12-19 pg 8 and lines 3-9 page 9. X 1-6 WO2010/090611 A2 BILGIC MAHMUT. See examples, line 30 pg 5- line 2 pg 6, lines 4-10 pg 6 and lines 31-34 page 6.
    Categories:
    X Document indicating lack of novelty or inventive step A Document indicating technological background and/or state of the art. Y Document indicating lack of inventive step if combined with one or more other documents of same category. P Document published on or after the declared priority date but before the filing date of this invention. & Member of the same patent family E Patent document published on or after, but with priority date earlier than, the filing date of this application.
    Field of Search:
    Search of GB, EP, WO & US patent documents classified in the following areas of the UKCX :
    International Classification:
    Subclass Subgroup Valid From A61K 0031/197 01/01/2006 A61K 0009/16 01/01/2006 A61K 0047/26 01/01/2006 A61K 0047/36 01/01/2006
    Intellectual Property Office is an operating name of the Patent Office www.gov.uk/ipo
GB1701787.2A 2016-02-23 2017-02-03 Non-effervescent granulates containing N-acetylcysteine Active GB2552728B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1651458A FR3047898B1 (en) 2016-02-23 2016-02-23 NON-EFFERVESCENT GRANULES CONTAINING N-ACETYLCYSTEINE.

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GB201701787D0 GB201701787D0 (en) 2017-03-22
GB2552728A true GB2552728A (en) 2018-02-07
GB2552728A9 GB2552728A9 (en) 2019-07-17
GB2552728B GB2552728B (en) 2019-11-20

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CH (1) CH712181B1 (en)
DE (1) DE102017103033A1 (en)
FR (1) FR3047898B1 (en)
GB (1) GB2552728B (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1449525A1 (en) * 2003-02-20 2004-08-25 Cross Chem Llc chewing gum in the form of multi-layer tablets
WO2010090611A2 (en) * 2009-02-05 2010-08-12 Bilgic Mahmut Taste and odor masked pharmaceutical compositions with high bioavailability
WO2011146031A1 (en) * 2010-05-18 2011-11-24 Bilgic Mahmut Pharmaceutical composition comprising n- acetylcysteine and a xanthine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19931708A1 (en) * 1999-07-08 2001-01-18 Bayer Ag Process for the preparation of rapidly disintegrating solid pharmaceutical preparations
IT1399492B1 (en) 2010-04-13 2013-04-19 Alpex Pharma Sa EFFERVESCENT PHARMACEUTICAL COMPOSITIONS CONTAINING N-ACETYLCISTEIN.
US8747894B2 (en) * 2012-05-08 2014-06-10 Alpex Pharma S.A. Effervescent compositions containing N-acetylcysteine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1449525A1 (en) * 2003-02-20 2004-08-25 Cross Chem Llc chewing gum in the form of multi-layer tablets
WO2010090611A2 (en) * 2009-02-05 2010-08-12 Bilgic Mahmut Taste and odor masked pharmaceutical compositions with high bioavailability
WO2011146031A1 (en) * 2010-05-18 2011-11-24 Bilgic Mahmut Pharmaceutical composition comprising n- acetylcysteine and a xanthine

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GB2552728B (en) 2019-11-20
FR3047898B1 (en) 2020-09-18
FR3047898A1 (en) 2017-08-25
GB2552728A9 (en) 2019-07-17
GB201701787D0 (en) 2017-03-22
CH712181A2 (en) 2017-08-31
DE102017103033A1 (en) 2017-08-24
CH712181B1 (en) 2020-09-30

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