GB2192790A - Acetylcysteine compositions - Google Patents
Acetylcysteine compositions Download PDFInfo
- Publication number
- GB2192790A GB2192790A GB08717582A GB8717582A GB2192790A GB 2192790 A GB2192790 A GB 2192790A GB 08717582 A GB08717582 A GB 08717582A GB 8717582 A GB8717582 A GB 8717582A GB 2192790 A GB2192790 A GB 2192790A
- Authority
- GB
- United Kingdom
- Prior art keywords
- weight
- composition according
- pharmaceutical composition
- acetylcysteine
- citric acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 title claims description 41
- 239000000203 mixture Substances 0.000 title claims description 24
- 229960004308 acetylcysteine Drugs 0.000 title claims description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 75
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 36
- 108010011485 Aspartame Proteins 0.000 claims description 21
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 21
- 239000000605 aspartame Substances 0.000 claims description 21
- 229960003438 aspartame Drugs 0.000 claims description 21
- 235000010357 aspartame Nutrition 0.000 claims description 21
- 239000008187 granular material Substances 0.000 claims description 19
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 239000000796 flavoring agent Substances 0.000 claims description 13
- 235000013355 food flavoring agent Nutrition 0.000 claims description 12
- 239000003826 tablet Substances 0.000 claims description 11
- 239000007938 effervescent tablet Substances 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 description 7
- 235000003599 food sweetener Nutrition 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 244000248349 Citrus limon Species 0.000 description 4
- 235000005979 Citrus limon Nutrition 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001398 aluminium Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000001013 cariogenic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- HWPKGOGLCKPRLZ-UHFFFAOYSA-M monosodium citrate Chemical compound [Na+].OC(=O)CC(O)(C([O-])=O)CC(O)=O HWPKGOGLCKPRLZ-UHFFFAOYSA-M 0.000 description 1
- 235000018342 monosodium citrate Nutrition 0.000 description 1
- 239000002524 monosodium citrate Substances 0.000 description 1
- 230000000510 mucolytic effect Effects 0.000 description 1
- 229940066491 mucolytics Drugs 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000185 sucrose group Chemical class 0.000 description 1
- 239000004173 sunset yellow FCF Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0007—Effervescent
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
GB2192790A 1
SPECIFICATION
Pharmaceutical compositions The invention relates to pharmaceutical compositions containing N- acetylcysteine. 5 Wacetylcysteine (hereinafter designated NAC) is a medicament with diverse favourable proper ties, one of which is mucolytic activity. For use in practice as a mucolytic agent, NAC can be taken orally in the form of an aqueous solution obtained by dissolving effervescent granules or an effervescent tablet. The organoleptic properties of the medicament can, however, be subjec tively unpleasant. It is therefore necessary to lessen the typical taste of NAC in the case of oral 10 administration.
In the pharmaceutical forms currently available commercially this is accomplished by an addi tion of sucrose. However, the use of sucrose can have disadvantages, especially for persons who suffer from diabetes. In addition, sucrose is a cariogenic sugar. It is therefore necessary to be able to provide, as an alternative to the already existing pharmaceutical forms, novel pharma- 15 ceutical preparations of NAC for oral use, which are indicated for subjects to whom sucrose can be harmful. The substitution of sucrose by an artificial sweetener or a non-cariogenic sweetening agent in a pharmaceutical form containing NAC is a problem which at first sight would appear easy to solve. In reality, there are manifold problems which are difficult to solve.
For example, it is necessary that the NAC and the sweetener are chemically compatible, that 20 the sweetener or sweetening agent is capable of effectively masking or lessening the typical flavour of NAC, that the resulting taste is pleasant anyhow, that the sweetener or sweetening agent is suitable for preparing the desired pharmaceutical form and is compatible with the associated operations.
The invention provides a water-soluble effervescent pharmaceutical composition comprising 25 from 6 to 32% by weight of Wacetylcysteine, from 35 to 50% by weight of citric acid, from 26 to 37% by weight of sodium bicarbonate, from 1 to 1.5% by weight of aspartame and from 5 to 7% by weight of a pharmaceutically acceptable flavouring agent, the weight ratio of citric acid to sodium bicarbonate being from 1.2:1 to 1.4A.
The higher values for NAC correspond to the lower values for citric acid and bicarbonate. If 30 desired, the citric acid can also be used partially in the form of a salt, for example as monosodium citrate.
The compositions according to the invention serve for preparing pharmaceutical forms as effervescent granules or tablets. Both the resulting pharmaceutical forms are readily soluble in water. 35 Having regard to the acceptability by the consumer of the medicament, the use of a flavouring agent may demand the presence of a colourant which is normally associated with a particular taste. For example, the use of mint flavouring can demand the addition of a colourant which imparts a green colour to the solution. In such cases, it can be useful to combine the compo sition with a quantity of a pharmaceutical ly acceptable colourant, for example in a quantity 40 between 0.5 and 1 % by weight.
Examples of compositions according to the invention are given in the Table which follows.
N) -A B c D E F G -4 (mg) (mg) (M9) (mg) (M9) (M9) (mg) cor NAC. 100 10 200 20 100 6.67 150 10.200 13.33 400 23.53 600 31. 58 1 Citric acid '470 47 412 41.2 738 49'.20 708 47.20 680 45.34 680 40.00 680 35.79 Sodium 345 34.5 303 30.3 542 36.13 522 34.80 500 33.33 500 29.41 500 26. 32 (P Bicarbonate Aspartame 15 1.5 15 1.5 20 1.33 20 1.33 20 1.33 20 1.18 20 1.05 0 Flavouring 70 7 70 7 100 6.67 100 6.67 100 6.67 100 5.88 100 5.26 c Agent cr r (P Total. 1000 100 1000 100 1500 100 1500 100 1500 100 1700 100 1900 100 (D -f. -h 0 -I D 0 0 (P:3 r+ n 0 a D 0 In 1. G) rf. W 0. r-i 3 (D U) hi 3 GB2192790A 3 Amongst flavouring agents it is preferred to use lemon flavouring, the colour of the resulting solution being readily associated with the lemon taste. Alternatively, it is possible to use other agents, such as orange flavouring, which, however, is preferably combined with a suitable orange colourant, for example fl-carotene.
By procedures usual in pharmaceuitcal operations, the compositions illustrated above may be 5 prepared in the form of effervescent granules or tablets. Before packaging, the effervescent tablets are subjected to heating for a period of time determined as a function of the weight of the tablets. The granules are distributed in suitable sachets each containing from 1 to 2 g of the composition. Alternatively, tablets of a weight of 1, 1.2, 1.5, 1.7 or 1. 9 9 each are prepared.
If desired, for higher dosages of NAC (for example 600 mg per single dose), effervescent 10 tablets of 3 g weight or sachets containing 3 g of effervescent composition can be prepared (see Example 5 below). A typical example of such a composition is as follows:
Composition H ( mg 15 NAC 600 20 Citric Acid 1211 40.36 NaHCO 3 1009 33.64 20 Aspartame 30 1 Citrus fruit flavouring 150 5 25 Total 3000 100 Both the effervescent granules and tablets according to the invention dissolve rapidly in water, 30 giving an aqueous NAC solution of pleasant palatability.
The following Examples illustrate the invention.
Example 1
Granules consisting of 35 NAC 20 kg Citric Acid 41.2 kg Sodium bicarbonate 30.3 kg 40 Aspartame 1.5 kg Lemon flavouring 7 kg are prepared by the following procedure. 45 Granules consisting of NAC and citric acid are sieved through a screen of 1.07 mm mesh width and mixed after adding aspartame. The mixture is granulated with water in a fluid-bed granulator.
Sodium bicarbonate and dried lemon flavouring are added to the granules obtained and mixed in.
The mixture is distributed over blisters in a laminatedaluminium/polyethylene sheet in a dose of 50 1 9 per blister.
Alternatively, aliquots of 1 9 of the mixture can be compressed to tablets and be distributed over the blisters instead.
4 GB2192790A 4 Example 2
Granules consisting of NAC 60 kg 5 Citric acid 68 kg Sodium bicarbonate 50 kg Aspartame 2 kg 10 1 Orange flavouring 10 kg are prepared by the following procedure.
NAC and citric acid are sieved through a screen of 1.07 mm mesh width and mixed after 15 adding aspartame. The mixture is granulated in a fluid-bed granulator with an aqueous solution of colourant E 110. Sodium bicarbonate and dried orange flavouring are added to the granules obtained and mixed in. Portions of 1.9 g of the mixture are then compressed in circular moulds of 18 mm diameter; giving effervescent tablets which each contain 600 mg of NAC. Before packaging in blisters, the tablets are heated on trays in a drying oven for 2 hours at 700C. 20 Alternatively, the mixture can be distributed over blisters in a laminated aluminium/polyethylene sheet in a dose of 1.9 g per blister.
Effervescent granules or effervescent tablets of compositions corresponding to those described in the table given above are prepared by an analogous procedure.
25 Example 3
Granules consisting of:
NAC 40 kg 30 Citric acid 68 kg Sodium bicarbonate 50 kg Aspartame 2 kg 35 Citrus fruit flavouring 10 kg are prepared by the procedure described in Example 1.
The dried mixture is then compressed in doses of 1.7 g each on a rotary tablet press fitted with moulds of 18 mm diameter. Alternatively, aliquots of 1.7 g are distributed over blisters in a 40 laminated aluminium/polyethylene sheet. Both the tablets and blisters contain 400 mg of NAC per single dose.
Example 4
Granules consisting of: 45 NAC 10 kg citric acid 73.8 kg Sodium bicarbonate 54.2 kg 50 Aspartame 2 kg Orange flavouring - 10 kg 55 are preparing by the following procedure.
NAC, citric acid and aspartame are sieved through a screen of 1.07 mm mesh width and mixed. The mixture is then granulated in a conventional granulator with an aqueous: alcoholic solution (water:alcohol = 1:1 by volume).
The granules obtained are dried in an oven and sieved on a vibrating granulator fitted with a 60 screen of 0.9 mm mesh width. Sodium bicarbonate and orange flavouring are added to the granules obtained and mixed in.
Portions of 1.5 g of the mixture are then compressed in circular moulds of 15 mm diameter, forming efferv escent tablets each containing 150 mg of NAC.
Alternatively, the effervescent mixture can be distributed over blisters in a laminated alumini- 65 GB2192790A 5 um/polyethylene sheet in a dose of 3 g per blister, each containing 300 mg of NAC.
Example 5
Granules consisting of: 5 NAC 30 kg Citric acid 60.55 kg Sodium bicarbonate 50.45 kg 10 Aspartame 1.5 kg Orange flavouring 7.5 kg are prepared by the following procedure. 15 NAC and citric acid are sieved through a screen of 1.07 mm mesh width and mixed after adding aspartame. The mixture is then granulated with water in a conventional granulator. The granules obtained are dried in an oven and sieved in a vibrating granulator fitted with a screen of 0.9 mm mesh width. Sodium bicarbonate and orange flavouring are added to the granules obtained and mixed in. 20 Portions of 3 g of the mixture are then compressed in circular moulds of 25 mm diameter, forming effervescent tablets which each contain 600 mg of NAC.
Alternatively, the effervescent mixture can be distributed over blisters in a laminatedaluminium/polyethylene sheet in a dose of 3 g per blister, each containing 600 mg of NAC.
25
Claims (16)
1. A water-soluble effervescent pharmaceutical composition comprising from 6 to 32% by weight of N-acetylcysteine, from 35 to 50% by weight of citric acid, from 26 to 37% by weight of sodium bicarbonate, from 1 to 1.5% by weight of aspartame and from 5 to 7% by weight of a pharmaceutically acceptable flavouring agent, the weight ratio of citric acid to sodium bicarbo- 30 nate being from 1.2:1 to 1.4:1.
2. A pharmaceutical composition according to Claim 1 in the form of effervescent granules.
3. A pharmceutical composition according to Claim 2 and containing a quantity selected from 150, 200, 300 400 and 600 mg of N-acetylcysteine per single dose.
4. A pharmaceutical composition according to Claim 1 in the form of effervescent tablets. 35
5. A pharmaceutical composition according to Claim 4 and containing a quantity select,ed from 150, 200, 300, 400 and 600 mg of N-acetylcysteine per single tablet.
6. A pharmaceutical composition according to any preceding Claim further comprising a phar maceutically acceptable colourant.
7. A pharmaceutical composition according to any of Claims 1 to 5 and comprising: 40 N-Acetylcysteine 13.33% by weight Citric acid 45.34% by weight Sodium bicarbonate 33.33% by weight 45' Aspartame 1.40% by weight Flavouring agent 6.60% by weight 50
8. A pharmaceutipal composition according to any of Claims 1 to 5 and comprising:
N-Acetylcysteine 31.58% by weight Citric acid 35.79% by weight 55 Sodium bicarbonate 26.32% by weight Aspartame 1.05% by weight Flavouring agent 5.26% by weight 60
9. A pharmaceutical composition according to Claim 7 and containing 200 mg of N acetylcysteine per single dose.
10. A pharmaceutical composition according to Claim 8 and containing 600 mg of N acetylcysteine per single dose. 65 6 GB2192790A 6
11. A pharmaceutical composition according to any of Claims 1 to 5 and comprising:
N-Acetylcysteine 10% by weight Citric acid 47% by weight 5 Sodium bicarbonate 34.5% by weight Aspartame 1.5% by weight Flavouring agent 7% by weight 10
12. A pharmaceutical composition according to any of Claims 1 to 5 and comprisig:
N-Acetylcysteine 20% by weight Citric acid 41.2% by weight 15 Sodium bicarbonate 30.3% by weight Aspartame 1.5% by weight 20 Flavouring agent 7% by weight
13. A pharmaceutical composition according to any of Claims 1 to 5 and comprising:
N-Acetylcysteine 10% by weight 25 Citric acid 47.20% by weight Sodium bicarbonate 34.80% by weight Aspartame 1.33% by weight 30 Flavouring agent 6.67% by weight
14. A pharmaceutical composition according to any of Claims 1 to 5 and comprising:
N-Actylcysteine 6.67% by weight 35 Citric Acid 49.20% by weight Sodium bicarbonate 36.13% by weight Aspartame 1.33% by weight 40 Flavouring agent 6.67% by weight
15. A pharmaceutical composition according to any of Claims 1 to 5 and comprising: 45 N-Acetylcysteine 23.53% by weight Citric acid 40.00% by weight Sodium bicarbonate 29.41% by weight 50 Aspartame 1.18% by weight Flavouring agent 5.88% by weight 55
16. A pharmaceutical composition according to any of Claims 1 to 5 and comprising:
7 GB2192790A 7 N-acetylcysteine 20% by weight Citric acid 40.36% by weight 5:Sodium bicarbonate 33.64% by weight 5 Aspartame 1% by weight Flavouring agent 5% by weight 10 Published 1988 at The Patent Office, State House, 66/71 High Holborn, London WC 1 R 4TP. Further copies may be obtained from The Patent Office, Sales Branch, St Mary Cray, Orpington, Kent BR5 3RD. Printed by Burgess & Son (Abingdon) Ltd. Con; 1/87.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2975/86A CH667590A5 (en) | 1986-07-24 | 1986-07-24 | WATER-SOLUBLE EFFERVESCENT PHARMACEUTICAL COMPOSITION CONTAINING N-ACETYL-CISTEIN. . |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8717582D0 GB8717582D0 (en) | 1987-09-03 |
| GB2192790A true GB2192790A (en) | 1988-01-27 |
| GB2192790B GB2192790B (en) | 1990-01-31 |
Family
ID=4245841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8717582A Expired - Lifetime GB2192790B (en) | 1986-07-24 | 1987-07-27 | Effervescent n-acetyl cysteine compositions. |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE1000355A3 (en) |
| CH (1) | CH667590A5 (en) |
| DE (1) | DE3723735A1 (en) |
| FR (1) | FR2601876B1 (en) |
| GB (1) | GB2192790B (en) |
| IT (1) | IT1222104B (en) |
| NL (1) | NL194067C (en) |
| SE (1) | SE500494C2 (en) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0339508A1 (en) * | 1988-04-29 | 1989-11-02 | Altergon S.A. | Mouth-soluble pharmaceutical compositions containing acetylcysteine |
| DE3822096A1 (en) * | 1988-06-30 | 1990-01-04 | Klinge Co Chem Pharm Fab | STABILIZED DRUG PREPARATION |
| FR2650503A1 (en) * | 1989-07-27 | 1991-02-08 | Zambon Spa | PHARMACEUTICAL COMPOSITION FOR ORAL ADMINISTRATION CONTAINING N-ACETYL-CYSTEINE AND ITS APPLICATION |
| EP0451431A1 (en) * | 1988-10-10 | 1991-10-16 | Lejus Medical Aktiebolag | Pharmaceutical composition |
| EP0497724A1 (en) * | 1991-01-26 | 1992-08-05 | Senju Pharmaceutical Co., Ltd. | An agent for disintegrating gallstones |
| US5296500A (en) * | 1991-08-30 | 1994-03-22 | The Procter & Gamble Company | Use of N-acetyl-cysteine and derivatives for regulating skin wrinkles and/or skin atrophy |
| FR2698545A1 (en) * | 1992-12-02 | 1994-06-03 | Zambon Spa | Syrup containing N-acetyl-cysteine. |
| GB2285923A (en) * | 1994-01-31 | 1995-08-02 | Zambon Int Pharma | Pharmaceutical powder containing N-acetyl-cysteine |
| US5451405A (en) * | 1994-04-25 | 1995-09-19 | Chesebrough-Pond's Usa Co. | Skin treatment composition |
| WO2000018392A1 (en) * | 1998-09-25 | 2000-04-06 | Glycox Corporation Limited | Fructosamine oxidase: antagonists and inhibitors |
| US6855511B2 (en) | 1998-09-25 | 2005-02-15 | Protemix Corporation Limited | Fructosamine oxidase assay: methods and materials |
| US7582796B2 (en) | 2004-07-19 | 2009-09-01 | Protemix Corporation Limited | Synthesis of triethylenetetramines |
| WO2010090612A1 (en) * | 2009-02-05 | 2010-08-12 | Bilgic Mahmut | Stable, taste and odor masked pharmaceutical compositions comprising acetylcystein and vitamin c |
| CN101947211A (en) * | 2010-08-28 | 2011-01-19 | 浙江金华康恩贝生物制药有限公司 | Method for preparing acetylcysteine effervescent tablet |
| US8034799B2 (en) | 2002-03-08 | 2011-10-11 | Philera New Zealand Limited | Preventing and/or treating cardiovascular disease and/or associated heart failure |
| ITMI20100615A1 (en) * | 2010-04-13 | 2011-10-14 | Alpex Pharma Sa | EFFERVESCENT PHARMACEUTICAL COMPOSITIONS CONTAINING N-ACETYLCISTEIN |
| CN102233139A (en) * | 2010-04-21 | 2011-11-09 | 重庆健能医药开发有限公司 | Acetylcysteine effervescent tablet and preparation method and application thereof |
| WO2011146031A1 (en) * | 2010-05-18 | 2011-11-24 | Bilgic Mahmut | Pharmaceutical composition comprising n- acetylcysteine and a xanthine |
| WO2013055302A1 (en) * | 2011-05-16 | 2013-04-18 | Mahmut Bilgic | Effervescent composition comprising n- acetylcysteine and doxophylline or theophylline |
| EP2662077A1 (en) * | 2012-05-08 | 2013-11-13 | Alpex Pharma SA | Effervescent compositions containing N-acetylcysteine |
| EP2393478B1 (en) * | 2009-02-05 | 2015-06-17 | Mahmut Bilgic | Taste and odor masked pharmaceutical compositions with high bioavailability |
| EP2905020A1 (en) * | 2014-02-05 | 2015-08-12 | Sanovel Ilac Sanayi ve Ticaret A.S. | Effervescent formulations comprising ibuprofen and N-acetylcystein |
| US9339479B2 (en) | 2002-08-20 | 2016-05-17 | Philera New Zealand Limited | Dosage forms and related therapies |
| CN113559078A (en) * | 2021-07-02 | 2021-10-29 | 安徽省先锋制药有限公司 | Preparation method of acetylcysteine effervescent tablets |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3909049A1 (en) * | 1989-03-18 | 1990-09-20 | Arthur Boskamp | PREPARATION AND THEIR USE |
| DE4103360A1 (en) * | 1991-02-05 | 1992-08-06 | Koehler Peter | Use of acetyl-cysteine and isotonic sodium chloride (0.9 per cent) - for treating bronchial asthma and bronchitis-induced spasms |
| DE4406261C2 (en) * | 1993-08-31 | 1996-07-04 | Deutsches Krebsforsch | Use of thiol compounds to reduce body fat |
| DE19509856C2 (en) * | 1995-03-17 | 1997-09-11 | Schwabe Willmar Gmbh & Co | Use of an effervescent composition with Ginkgo biloba dry extract for the treatment of peripheral and cerebral circulatory disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2470M (en) * | 1962-03-13 | 1964-04-20 | Mead Johnson & Co | Therapeutic composition. |
| ZA723683B (en) * | 1971-07-12 | 1973-06-27 | Hoffmann La Roche | Improved effervescent preparations |
| DE3317530A1 (en) * | 1983-05-13 | 1984-11-15 | Dietrich Dr.med. Sta. Eulalia Ibiza Reichert | Antisnoring composition |
| DE3317558A1 (en) * | 1983-05-13 | 1984-11-15 | Dietrich Dr.med. Sta. Eulalia Ibiza Reichert | Oral antisnoring composition |
| IT1170268B (en) * | 1983-12-21 | 1987-06-03 | Zambon Spa | USE OF ACETYLCISTEIN TO REDUCE THE INCREASE IN THE PROLIEFERATION OF THE BASAL CELLS OF THE RESPIRATORY THRACHEO-BRONCHIAL EPITHELIUM INDUCED BY TOBACCO SMOKE IN MAMMALS |
| DE3514995A1 (en) * | 1985-04-25 | 1986-10-30 | Protopharma Ltd., 7831 Malterdingen | Use of sulfhydryl pharmaceuticals for combating damage to the gastric mucosa |
-
1986
- 1986-07-24 CH CH2975/86A patent/CH667590A5/en not_active IP Right Cessation
-
1987
- 1987-07-17 DE DE19873723735 patent/DE3723735A1/en active Granted
- 1987-07-22 FR FR878710368A patent/FR2601876B1/en not_active Expired
- 1987-07-23 NL NL8701743A patent/NL194067C/en not_active IP Right Cessation
- 1987-07-23 BE BE8700816A patent/BE1000355A3/en not_active IP Right Cessation
- 1987-07-23 SE SE8702940A patent/SE500494C2/en not_active IP Right Cessation
- 1987-07-23 IT IT21411/87A patent/IT1222104B/en active
- 1987-07-27 GB GB8717582A patent/GB2192790B/en not_active Expired - Lifetime
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| EP0339508A1 (en) * | 1988-04-29 | 1989-11-02 | Altergon S.A. | Mouth-soluble pharmaceutical compositions containing acetylcysteine |
| US4970236A (en) * | 1988-04-29 | 1990-11-13 | Altergon S.A. | Mouth-soluble pharmaceutical compositions containing acetyl-cysteine |
| DE3822096A1 (en) * | 1988-06-30 | 1990-01-04 | Klinge Co Chem Pharm Fab | STABILIZED DRUG PREPARATION |
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| FR2650503A1 (en) * | 1989-07-27 | 1991-02-08 | Zambon Spa | PHARMACEUTICAL COMPOSITION FOR ORAL ADMINISTRATION CONTAINING N-ACETYL-CYSTEINE AND ITS APPLICATION |
| GR900100569A (en) * | 1989-07-27 | 1991-12-10 | Zambon Spa | Method for preparing oral composition comprising nac |
| BE1003188A4 (en) * | 1989-07-27 | 1992-01-07 | Zambon Spa | PHARMACEUTICAL COMPOSITION FOR ORAL ADMINISTRATION CONTAINING N-ACETYL-CYSTEINE, AND ITS APPLICATION. |
| EP0497724A1 (en) * | 1991-01-26 | 1992-08-05 | Senju Pharmaceutical Co., Ltd. | An agent for disintegrating gallstones |
| US5441748A (en) * | 1991-01-26 | 1995-08-15 | Senju Pharmaceutical Co., Ltd. | Agents for distributing gallstones |
| US5296500A (en) * | 1991-08-30 | 1994-03-22 | The Procter & Gamble Company | Use of N-acetyl-cysteine and derivatives for regulating skin wrinkles and/or skin atrophy |
| BE1006799A3 (en) * | 1992-12-02 | 1994-12-13 | Zambon Spa | Syrup containing n-acetyl-cysteine. |
| DE4396086B3 (en) * | 1992-12-02 | 2013-02-28 | Zambon S.P.A. | Syrup with N-acetylcysteine |
| FR2698545A1 (en) * | 1992-12-02 | 1994-06-03 | Zambon Spa | Syrup containing N-acetyl-cysteine. |
| ES2070806A1 (en) * | 1992-12-02 | 1995-06-01 | Zambon Spa | Syrup containing n-acetyl-cysteine |
| GB2288977A (en) * | 1992-12-02 | 1995-11-08 | Zambon Spa | Syrup containing n-acetyl-cysteine |
| GB2288977B (en) * | 1992-12-02 | 1996-09-04 | Zambon Spa | Stable sweetened solutions of N-acetyl-cysteine |
| AT407113B (en) * | 1992-12-02 | 2000-12-27 | Zambon Spa | COMPOSITION IN THE FORM OF AN AQUEOUS THICKENED PREPARATION FOR PERORAL ADMINISTRATION WITH N-ACETYLCYSTONE |
| WO1994012168A1 (en) * | 1992-12-02 | 1994-06-09 | Zambon Group S.P.A. | Syrup containing n-acetyl-cysteine |
| FR2715564A1 (en) * | 1994-01-31 | 1995-08-04 | Inpharzam Int Sa | Pharmaceutical composition containing N-acetyl-cysteine |
| GB2285923B (en) * | 1994-01-31 | 1997-11-19 | Zambon Int Pharma | Pharmaceutical compositions containing N-acetal-cysteine |
| BE1007926A3 (en) * | 1994-01-31 | 1995-11-21 | Zambon Int Pharma | Pharmaceutical composition containing n-acetyl-cysteine. |
| GB2285923A (en) * | 1994-01-31 | 1995-08-02 | Zambon Int Pharma | Pharmaceutical powder containing N-acetyl-cysteine |
| US5451405A (en) * | 1994-04-25 | 1995-09-19 | Chesebrough-Pond's Usa Co. | Skin treatment composition |
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| US7459446B2 (en) | 1998-09-25 | 2008-12-02 | John Richard Baker | Treatment of diabetes with copper binding compounds |
| US7928094B2 (en) | 1998-09-25 | 2011-04-19 | Philera New Zealand Limited | Treatment of diabetes with copper binding compounds |
| US6855511B2 (en) | 1998-09-25 | 2005-02-15 | Protemix Corporation Limited | Fructosamine oxidase assay: methods and materials |
| US8034799B2 (en) | 2002-03-08 | 2011-10-11 | Philera New Zealand Limited | Preventing and/or treating cardiovascular disease and/or associated heart failure |
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| US11795150B2 (en) | 2004-07-19 | 2023-10-24 | Philera New Zealand Limited | Synthesis of triethylenetetramines |
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| WO2010090612A1 (en) * | 2009-02-05 | 2010-08-12 | Bilgic Mahmut | Stable, taste and odor masked pharmaceutical compositions comprising acetylcystein and vitamin c |
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| WO2011128230A1 (en) | 2010-04-13 | 2011-10-20 | Alpex Pharma Sa | Effervescent pharmaceutical compositions containing n-acetylcysteine |
| ITMI20100615A1 (en) * | 2010-04-13 | 2011-10-14 | Alpex Pharma Sa | EFFERVESCENT PHARMACEUTICAL COMPOSITIONS CONTAINING N-ACETYLCISTEIN |
| CN102233139B (en) * | 2010-04-21 | 2012-09-05 | 重庆健能医药开发有限公司 | Acetylcysteine effervescent tablet and preparation method and application thereof |
| CN102233139A (en) * | 2010-04-21 | 2011-11-09 | 重庆健能医药开发有限公司 | Acetylcysteine effervescent tablet and preparation method and application thereof |
| WO2011146031A1 (en) * | 2010-05-18 | 2011-11-24 | Bilgic Mahmut | Pharmaceutical composition comprising n- acetylcysteine and a xanthine |
| CN101947211A (en) * | 2010-08-28 | 2011-01-19 | 浙江金华康恩贝生物制药有限公司 | Method for preparing acetylcysteine effervescent tablet |
| WO2013055302A1 (en) * | 2011-05-16 | 2013-04-18 | Mahmut Bilgic | Effervescent composition comprising n- acetylcysteine and doxophylline or theophylline |
| EP2662077A1 (en) * | 2012-05-08 | 2013-11-13 | Alpex Pharma SA | Effervescent compositions containing N-acetylcysteine |
| WO2015117987A1 (en) * | 2014-02-05 | 2015-08-13 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Effervescent formulations comprising ibuprofen and n-acetylcystein |
| EP2905020A1 (en) * | 2014-02-05 | 2015-08-12 | Sanovel Ilac Sanayi ve Ticaret A.S. | Effervescent formulations comprising ibuprofen and N-acetylcystein |
| CN113559078A (en) * | 2021-07-02 | 2021-10-29 | 安徽省先锋制药有限公司 | Preparation method of acetylcysteine effervescent tablets |
Also Published As
| Publication number | Publication date |
|---|---|
| BE1000355A3 (en) | 1988-11-08 |
| SE500494C2 (en) | 1994-07-04 |
| GB2192790B (en) | 1990-01-31 |
| SE8702940D0 (en) | 1987-07-23 |
| IT1222104B (en) | 1990-08-31 |
| GB8717582D0 (en) | 1987-09-03 |
| DE3723735C2 (en) | 1992-05-21 |
| NL8701743A (en) | 1988-02-16 |
| FR2601876B1 (en) | 1989-10-13 |
| CH667590A5 (en) | 1988-10-31 |
| SE8702940L (en) | 1988-01-25 |
| FR2601876A1 (en) | 1988-01-29 |
| NL194067B (en) | 2001-02-01 |
| NL194067C (en) | 2001-06-05 |
| DE3723735A1 (en) | 1988-02-04 |
| IT8721411A0 (en) | 1987-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 20070726 |