DK176247B1 - Syrup containing N-acetylcysteine - Google Patents
Syrup containing N-acetylcysteine Download PDFInfo
- Publication number
- DK176247B1 DK176247B1 DK199500614A DK61495A DK176247B1 DK 176247 B1 DK176247 B1 DK 176247B1 DK 199500614 A DK199500614 A DK 199500614A DK 61495 A DK61495 A DK 61495A DK 176247 B1 DK176247 B1 DK 176247B1
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- DK
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- sodium
- nac
- solution
- syrup
- water
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- 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
- A61K31/185—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/12—Mucolytics
-
- 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
- A61P11/14—Antitussive agents
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- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Jellies, Jams, And Syrups (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Description
i DK 176247 B1in DK 176247 B1
Den foreliggende opfindelse angår en sammensætning i form af en sirup indeholdende N-acetylcystein som aktiv bestanddel.The present invention relates to a composition in the form of a syrup containing N-acetylcysteine as an active ingredient.
N-acetylcystein (herefter henvist til som NAC) er en 5 forbindelse, som er udstyret med adskillige anvendelige farmakologiske egenskaber, hvilket gør det til et bredt anvendt medikament.N-acetylcysteine (hereinafter referred to as NAC) is a compound which has several useful pharmacological properties, making it a widely used drug.
I behandlingen af forkølelsessygdomme viser NAC sig at være anvendeligt takket være dets mukolytiske egen-10 skaber.In the treatment of colds, NAC proves to be useful thanks to its mucolytic properties.
En af de farmaceutiske former, som i stor udstrækning anvendes i behandlingen af forkølelsessygdomme, er sirup, hvilken også er særlig egnet til pædiatrisk anvendelse .One of the pharmaceutical forms that is widely used in the treatment of colds is syrup, which is also particularly suitable for pediatric use.
15 NAC er tilgængelig i adskillige farmaceutiske former, den store reaktivitet af molekylet, den relative ustabilitet og den karakteristiske svovllugt og smag gør dog opnåelsen af væskeformige former til oral anvendelse, som er tidsstabile og som er velsmagende, yderst vanske-20 lig.NAC is available in several pharmaceutical forms, the great reactivity of the molecule, the relative instability and the characteristic sulfur odor and taste, however, the achievement of liquid forms for oral use which are time-stable and which are tasty, extremely difficult.
Fremstillingen af en sirup tilvejebringer, faktisk i alle tilfælde, anvendelsen af et disaccharid (sucrose) eller af et simpelt sukkerstof som et sødemiddel og tykkelsesmiddel i en vandig opløsning af medikamentet.The preparation of a syrup provides, in fact in all cases, the use of a disaccharide (sucrose) or of a simple sugar as a sweetening and thickening agent in an aqueous solution of the drug.
25 Vekselvirkningen mellem NAC og sukkerstoffer giver dog opløsningen en uacceptabel brun farve og titeren af NAC formindskes.25 However, the interaction between NAC and sugars gives the solution an unacceptable brown color and the titre of NAC decreases.
Det er således ikke muligt at lade NAC være i opløsning for en lang periode i nærvær af sucrose.Thus, it is not possible to leave the NAC in solution for a long period in the presence of sucrose.
2 DK 176247 B12 DK 176247 B1
Reaktionerne, som giver brun farve og forårsager dårlig lugt, finder også sted mellem NAC og monosacchariderne, hvis anvendelse er beskrevet i fransk patentansøgning nr. 2 631 831 i navnet Calco Anstalt.The reactions, which give brown color and cause bad odor, also take place between the NAC and the monosaccharides, the use of which is described in French patent application No. 2,631,831 in the name of Calco Anstalt.
5 Så vidt det vides, består den eneste sirupformulering på markedet, som indeholder NAC, i en sammensætning, der skal fremstilles lige før brug ved opløsning af et granulat i vand.5 To the best of our knowledge, the only syrup formulation on the market containing NAC consists of a composition to be prepared just before use in dissolving a granulate in water.
Efter fremstillingen skal siruppen anvendes inden for 3 10 uger.After preparation, the syrup should be used within 3 10 weeks.
Det har overraskende vist sig, at det er muligt at fremstille en tidsstabil NAC-sirup med en behagelig smag uden at anvende sukkerstoffer.Surprisingly, it has been found that it is possible to produce a time-stable NAC syrup with a pleasant taste without using sugars.
Den foreliggende opfindelses formål er derfor at til-15 vejebringe en sammensætning i form af en sirup indeholdende (hver 100 ml): - N-acetylcystein 2 -4,2 g/100 ml - et ikke-sukkerstofholdigt sødemiddel 0,02-0,3 g/100 ml - et tykkelsesmiddel valgt blandt: Natriumcarboxymethylcellulose og hydroxypropylmethylcellulose eller blandinger deraf 0,1 -4 g/100 ml og valgfrit: - et smagsstof 0,1 -0,4 g/100 ml - et konserveringsmiddel 0,05-0,5 g/100 ml og yderligere - vand pH sættes inden for intervallet 5-8.The object of the present invention is therefore to provide a composition in the form of a syrup containing (each 100 ml): - N-acetylcysteine 2 -4.2 g / 100 ml - a non-sugary sweetener 0.02-0, 3 g / 100 ml - a thickener selected from: Sodium carboxymethyl cellulose and hydroxypropyl methyl cellulose or mixtures thereof 0.1 -4 g / 100 ml and optional: - a flavoring 0.1 -0.4 g / 100 ml - a preservative 0.05- 0.5 g / 100 ml and further - water pH is set within the range 5-8.
3 DK 176247 B13 DK 176247 B1
Den ovennævnte opløsning viser sig at være stabil i en lukket flaske med en inert gas i mindst 2 år under miljøbetingelser. Når flasken åbnes, viser opløsningen sig at have en behagelig smag og være fri for dårlig 5 lugt; NAC bibeholder den initiale titer, og den åbnede sirup viser sig at være stabil i mindst 5 uger.The above solution is found to be stable in a closed bottle with an inert gas for at least 2 years under environmental conditions. When the bottle is opened, the solution turns out to have a pleasant taste and be free from bad odors; The NAC maintains the initial titre and the syrup opened appears to be stable for at least 5 weeks.
Med sødemiddel menes et stof, som er i stand til at give opløsningen en sød smag, men som ikke indeholder sukkerstoffer. Specifikke eksempler på sødemidler er saccha-10 rin, natriumsaccharin og cyclamat eller blandinger deraf .By sweetener is meant a substance which is capable of giving the solution a sweet taste, but which does not contain sugars. Specific examples of sweeteners are saccharin, sodium saccharin and cyclamate or mixtures thereof.
Mængden af sødemiddel vil være den minimale mængde, som er tilstrækkelig til at give opløsningen en behagelig smag.The amount of sweetener will be the minimum amount sufficient to give the solution a pleasant taste.
15 Tykkelsesmidlet er valgt blandt natriumcarboxymethyl-cellulose, methylcellulose og hydroxypropylmethylcellu-lose eller blandinger deraf. Disse stoffer viser sig overraskende at være forligelige med NAC og at være i stand til at give opløsningen en tykkelse, som er pas-20 sende for den sædvanlige velsmag af en sirup.The thickener is selected from sodium carboxymethyl cellulose, methyl cellulose and hydroxypropyl methyl cellulose or mixtures thereof. Surprisingly, these substances are found to be compatible with NAC and to be capable of giving the solution a thickness suitable for the usual taste of a syrup.
Til disse tre basisbestanddele (NAC, sødemiddel og tykkelsesmiddel) kan vand tilsættes op til et valgt volumen ved valgfrit at rektificere pH af resultanten, sådan at pH holdes inden for intervallet fra 5 til 8. PH 25 vil fortrinsvis være fra 6,5 til 7.To these three basic constituents (NAC, sweetener and thickening agent), water can be added up to a selected volume by optionally rectifying the pH of the resultant such that the pH is kept within the range of 5 to 8. PH 25 will preferably be from 6.5 to 7. .
Siruppen kan også, men ikke nødvendigvis, indeholde et smagsstof for at forbedre velsmagen, især til pædiatrisk anvendelse.The syrup may also, but not necessarily, contain a flavoring to improve the taste, especially for pediatric use.
Siden siruppen almindeligvis fremstilles uden aseptik, 30 kræver farmakopé tvungen tilstedeværelse af et konserveringsmiddel. Konserveringsmidlet kræves yderligere for 4 DK 176247 B1 at sikre den mikrobiologiske· kvalitet under patientens anvendelse.Since the syrup is usually prepared without aseptic, pharmacopoeia requires the presence of a preservative. The preservative is further required for ensuring the microbiological quality of the patient during use.
I dette tilfælde benyttes fortrinsvis konserveringsmidler valgt blandt natriumbenzoat, methyl-4-hydroxy-5 benzoat, propyl-4-hydroxybenzoat og blandinger deraf.In this case, preservatives selected from sodium benzoate, methyl 4-hydroxy-5-benzoate, propyl-4-hydroxybenzoate and mixtures thereof are preferably used.
Med dobbeltfunktionen af konserveringsmiddel og metal-chelerende middel kan også natrium-EDTA anvendes som tilsætning til eller ved partiel udskiftning af de ovennævnte konserveringsmidler.With the dual function of preservative and metal chelating agent, sodium EDTA can also be used as the addition or partial replacement of the above preservatives.
10 Fremstillingen af siruppen ifølge den foreliggende opfindelse udføres under inert gas ved simpel opløsning af stofferne i de forud bestemte mængder i vand.The preparation of the syrup of the present invention is carried out under inert gas by simply dissolving the substances in the predetermined amounts in water.
Resultantopløsningen deles i flerdosisflasker eller i enkeltdosisbeholdere.The resultant solution is divided into multi-dose bottles or in single-dose containers.
15 Pakningen af flerdosisflaskerne kan tilvejebringe den samtidige tilførsel af et inddelt mål for den korrekte dosering af den enkelte dosis til voksne mennesker (f.eks. 10 ml) eller til børn (f.eks. 5 ml).The packing of the multiple dose vials may provide the simultaneous delivery of a divided target for the correct dosage of the single dose to adult humans (eg 10 ml) or to children (eg 5 ml).
For bedre at illustrere den foreliggende opfindelse 20 gives nu følgende eksempler.To better illustrate the present invention 20, the following examples are now given.
Eksempel 1 10 liter af en sirup indeholdende (hver 100 ml): NAC 2,1 gExample 1 10 liters of a syrup containing (each 100 ml): NAC 2.1 g
Saccharin 0,04 gSaccharin 0.04 g
Natriumcarboxymethylcellulose 0,2 gSodium carboxymethyl cellulose 0.2 g
Natriumbenzoat 0,15 gSodium benzoate 0.15 g
Natrium-EDTA 0,1 gSodium EDTA 0.1 g
Hindbær smagsstof 0,25 gRaspberry flavor 0.25 g
Vand til 100 ml 5 DK 176247 B1 blev fremstillet ved simpel opløsning af stofferne i renset og luftet vand i en nitrogenatmosfære.Water to 100 ml B1 was prepared by simply dissolving the substances in purified and aerated water in a nitrogen atmosphere.
Resultantopløsningens pH blev rektificeret til den korrekte værdi 6,5 ved tilsætning af natriumhydroxid. Op-5 løsningen blev delt med en sats på 150 ml/flaske. Flaskerne blev lagret i 2 år ved stuetemperatur. Efter denne periode resulterer titeren af NAC i at være større end 95% af den initiale titer. Sådan en titer resulterer også efter 5 uger fra åbningen af flasken i at være 10 større end 90% af den initiale titer. Også efter 2 års lagring udviser siruppen en behagelig smag og lugt og en generelt god velsmag.The pH of the resultant solution was rectified to the correct value 6.5 by the addition of sodium hydroxide. The solution was divided at a rate of 150 ml / bottle. The bottles were stored for 2 years at room temperature. After this period, the titre of NAC results in greater than 95% of the initial titre. Such a titre also results after 10 weeks from the opening of the bottle being 10 greater than 90% of the initial titre. Also after 2 years of storage, the syrup exhibits a pleasant taste and smell and a generally good taste.
Eksempel 2 10 1 af en sirum med følgende sammensætning (hver 100 15 ml) : NAC 2,1 gExample 2 10 L of a serum of the following composition (100 ml each): NAC 2.1 g
Natriumsaccharin 0,04 gSodium saccharin 0.04 g
Hydroxypropylmethylcellulose 0,2 gHydroxypropyl methyl cellulose 0.2 g
Methyl-4-hydroxybenzoat 0,1 gMethyl 4-hydroxybenzoate 0.1 g
Natrium-EDTA 0,1 gSodium EDTA 0.1 g
Abrikos smagsstof 0,1 gApricot flavor 0.1 g
Vand til 100 ml blev fremstillet ved dispergering af hydroxypropylmethylcellulose i en del kogende vand, som blev afkølet til stuetemperatur. Efter hydratisering af hydroxypropylmethylcellulose, blev det hældt i en opløsning, 20 opnået ved at opløse alle de resterende stoffer i renset og luftet vand i en nitrogenatmosfære. Opløsningens pH blev rektificeret til pH 6,5 med natriumhydroxid. Opløsningen blev delt i enkeltdosis lugteposer på hver 10 ml indeholdende ca. 200 mg NAC.Water to 100 ml was prepared by dispersing hydroxypropyl methylcellulose in some boiling water which was cooled to room temperature. After hydration of hydroxypropyl methyl cellulose, it was poured into a solution obtained by dissolving all the remaining substances in purified and aerated water in a nitrogen atmosphere. The pH of the solution was rectified to pH 6.5 with sodium hydroxide. The solution was divided into single dose odor bags of each 10 ml containing ca. 200 mg of NAC.
25 6 DK 176247 B125 6 DK 176247 B1
Eksempel 3 10 1 af en sirup med følgende sammensætning (hver 100 ml) : NAC 2,1 gExample 3 10 L of a syrup of the following composition (each 100 ml): NAC 2.1 g
Natriumsaccharin 0,04 gSodium saccharin 0.04 g
Hydroxypropylmethylcellulose 0,2 gHydroxypropyl methyl cellulose 0.2 g
Natriumedetat 0,1 gSodium edetate 0.1 g
Abrikos smagsstof 0,1 gApricot flavor 0.1 g
Vand til 100 ml blev fremstillet ved dispergering af hydroxypropyl-5 methylcellulose i en del kogende vand, som blev afkølet til stuetemperatur. Efter hydrering af hydroxypropylmethylcellulose, blev det hældt i en opløsning, opnået ved at opløse alle de resterende stoffer i renset og luftet vand i en nitrogenatmosfære. Opløsningens pH blev 10 rektificeret til pH 6,5 med natriumhydroxid. Opløsningen blev delt i enkeltdosis hætteglas med gummiprop på hver 10 ml indeholdende ca. 200 mg NAC.Water to 100 ml was prepared by dispersing hydroxypropylmethyl cellulose in a portion of boiling water which was cooled to room temperature. After hydration of hydroxypropylmethyl cellulose, it was poured into a solution obtained by dissolving all the remaining substances in purified and aerated water in a nitrogen atmosphere. The pH of the solution was rectified to pH 6.5 with sodium hydroxide. The solution was divided into single dose vials of rubber stopper on each 10 ml containing approx. 200 mg of NAC.
Eksempel 4Example 4
Ved behandling som beskrevet i eksempel 1, blev 10 liter 15 sirup fremstillet med følgende sammensætning (hver 100 ml) : NAC 4,2 gBy treatment as described in Example 1, 10 liters of syrup were prepared with the following composition (each 100 ml): NAC 4.2 g
Natriumsaccharin 0,08 gSodium saccharin 0.08 g
Natriumcarboxymethylcellulose 0,20 gSodium carboxymethyl cellulose 0.20 g
Natriumbenzoat 0,15 gSodium benzoate 0.15 g
Natrium-EDTA 0,10 gSodium EDTA 0.10 g
Hindbær smagsstof 0,4 gRaspberry flavor 0.4 g
Vand til 100 ml 7 DK 176247 B1Water to 100 ml 7 DK 176247 B1
Opløsningens pH blev rektificeret til pH 6,5 med natriumhydroxid. Opløsningen blev delt i flasker med en sats på 150 ml hver flaske.The pH of the solution was rectified to pH 6.5 with sodium hydroxide. The solution was divided into bottles at a rate of 150 ml each bottle.
Eksempel 5 5 Ved behandling som beskrevet i eksempel 2, blev 10 1 sirup fremstillet med følgende sammensætning (hver 100 ml) : NAC 2,10 gExample 5 In treatment as described in Example 2, 10 L of syrup was prepared with the following composition (each 100 ml): NAC 2.10 g
Saccharin 0,04 gSaccharin 0.04 g
Natriumcarboxymethylcellulose 0,40 gSodium carboxymethyl cellulose 0.40 g
Methyl-4-hydroxybenzoat 0,10 gMethyl 4-hydroxybenzoate 0.10 g
Banan smagsstof 0,4 gBanana flavor 0.4 g
Vand til 100 mlWater to 100 ml
Opløsningens pH blev rektificeret til pH 7 med natrium-10 hydroxid. Opløsningen blev delt i flasker med en sats på 450 ml per flaske.The pH of the solution was rectified to pH 7 with sodium 10 hydroxide. The solution was divided into bottles at a rate of 450 ml per bottle.
Claims (4)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI922758A IT1256616B (en) | 1992-12-02 | 1992-12-02 | SYRUP CONTAINING N-ACETYL-CISTEIN |
| ITMI922758 | 1992-12-02 | ||
| EP9303280 | 1993-11-23 | ||
| PCT/EP1993/003280 WO1994012168A1 (en) | 1992-12-02 | 1993-11-23 | Syrup containing n-acetyl-cysteine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK61495A DK61495A (en) | 1995-05-31 |
| DK176247B1 true DK176247B1 (en) | 2007-04-16 |
Family
ID=11364395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK199500614A DK176247B1 (en) | 1992-12-02 | 1995-05-31 | Syrup containing N-acetylcysteine |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPH08503703A (en) |
| AT (1) | AT407113B (en) |
| AU (1) | AU667611B2 (en) |
| BE (1) | BE1006799A3 (en) |
| CA (1) | CA2150462C (en) |
| CH (1) | CH685371A5 (en) |
| CZ (1) | CZ282550B6 (en) |
| DE (2) | DE4396086T1 (en) |
| DK (1) | DK176247B1 (en) |
| ES (1) | ES2070806B1 (en) |
| FR (1) | FR2698545B1 (en) |
| GB (1) | GB2288977B (en) |
| HU (2) | HU221484B (en) |
| IT (1) | IT1256616B (en) |
| LU (1) | LU88618A1 (en) |
| MD (1) | MD1714G2 (en) |
| NL (1) | NL194957C (en) |
| NO (1) | NO314018B1 (en) |
| NZ (1) | NZ258544A (en) |
| RU (1) | RU2108777C1 (en) |
| SE (1) | SE520834C2 (en) |
| UA (1) | UA27142C2 (en) |
| WO (1) | WO1994012168A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0766557T3 (en) * | 1994-06-23 | 2002-04-15 | Procter & Gamble | Topical compositions comprising N-acetyl-L-cysteine |
| JP4501024B2 (en) * | 2002-11-14 | 2010-07-14 | 小林製薬株式会社 | Composition with reduced bitterness and odor of cysteines |
| JP4501023B2 (en) * | 2002-11-14 | 2010-07-14 | 小林製薬株式会社 | Composition with reduced bitterness and odor of cysteines |
| US8148356B2 (en) * | 2005-08-24 | 2012-04-03 | Cumberland Pharmaceuticals, Inc. | Acetylcysteine composition and uses therefor |
| 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 |
| RU2611411C1 (en) * | 2016-01-11 | 2017-02-21 | Общество с ограниченной ответственностью "Трейдсервис" | Dispersible in water acetylcysteine tablet and method of manufacturing thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB905197A (en) * | 1960-01-01 | 1962-09-05 | Lab Francais Chimiotherapie | Anti-viral compositions comprising 1-phenyl-2-amino-propane-1,3-diol derivatives |
| CA1239349A (en) * | 1983-10-10 | 1988-07-19 | Eberhard F. Gottwald | Pharmaceutical composition containing cimetidine |
| BE901885A (en) * | 1985-03-06 | 1985-07-01 | Bruschettini Srl | Stable ophthalmic soln. contg. N-acetyl-cysteine - prepd. in nitrogen satd. aq. buffer free of metal ions |
| CH666814A5 (en) * | 1986-07-24 | 1988-08-31 | Inpharzam Int Sa | WATER-SOLUBLE PHARMACEUTICAL COMPOSITION CONTAINING N-ACETYL-CISTEIN. |
| CH667590A5 (en) * | 1986-07-24 | 1988-10-31 | Inpharzam Int Sa | WATER-SOLUBLE EFFERVESCENT PHARMACEUTICAL COMPOSITION CONTAINING N-ACETYL-CISTEIN. . |
| US4861797A (en) * | 1987-10-15 | 1989-08-29 | Oratech Pharmaceutical Development Corporation | Liquid ibuprofen compositions and methods of making them |
| CH674940A5 (en) * | 1988-05-05 | 1990-08-15 | Ibsa Inst Biochimique Sa | |
| IT1234194B (en) * | 1988-05-31 | 1992-05-06 | Magis Farmaceutici | SYRUP PHARMACEUTICAL COMPOSITIONS CONTAINING PENTITLES AS VEHICULATING AGENTS |
| ES2054089T3 (en) * | 1988-11-10 | 1994-08-01 | Ciba Geigy Ag | LIQUID ORAL FORMULATIONS. |
| IT1231012B (en) * | 1989-07-27 | 1991-11-08 | Zambon Spa | PHARMACEUTICAL COMPOSITION FOR ORAL USE CONTAINING NAC. |
| IT1248998B (en) * | 1990-06-26 | 1995-02-11 | Iscofar Sas | COMPOSITION OF RUBBER TO BE CHEWED FOR THE PREVENTION AND TREATMENT OF DENTAL PLATE |
| DK0481294T4 (en) * | 1990-10-19 | 2001-06-18 | Spirig Ag | Solid, fast-soluble drug preparation containing N-acetylcysteine |
-
1992
- 1992-12-02 IT ITMI922758A patent/IT1256616B/en active IP Right Grant
-
1993
- 1993-11-23 HU HU9501586A patent/HU221484B/en unknown
- 1993-11-23 CH CH2423/94A patent/CH685371A5/en not_active IP Right Cessation
- 1993-11-23 ES ES09450021A patent/ES2070806B1/en not_active Expired - Fee Related
- 1993-11-23 DE DE4396086T patent/DE4396086T1/en active Pending
- 1993-11-23 UA UA95062994A patent/UA27142C2/en unknown
- 1993-11-23 GB GB9509822A patent/GB2288977B/en not_active Expired - Lifetime
- 1993-11-23 AT AT0906093A patent/AT407113B/en not_active IP Right Cessation
- 1993-11-23 NZ NZ258544A patent/NZ258544A/en not_active IP Right Cessation
- 1993-11-23 AU AU56266/94A patent/AU667611B2/en not_active Expired
- 1993-11-23 CA CA002150462A patent/CA2150462C/en not_active Expired - Lifetime
- 1993-11-23 WO PCT/EP1993/003280 patent/WO1994012168A1/en active IP Right Grant
- 1993-11-23 MD MD96-0265A patent/MD1714G2/en unknown
- 1993-11-23 JP JP6512747A patent/JPH08503703A/en active Pending
- 1993-11-23 RU RU95114406A patent/RU2108777C1/en active
- 1993-11-23 CZ CZ951367A patent/CZ282550B6/en not_active IP Right Cessation
- 1993-11-23 NL NL9320052A patent/NL194957C/en not_active IP Right Cessation
- 1993-11-23 DE DE4396086A patent/DE4396086B3/en not_active Expired - Lifetime
- 1993-12-01 BE BE9301326A patent/BE1006799A3/en not_active IP Right Cessation
- 1993-12-02 FR FR9314443A patent/FR2698545B1/en not_active Expired - Lifetime
-
1994
- 1994-05-24 LU LU88618A patent/LU88618A1/en unknown
-
1995
- 1995-05-31 DK DK199500614A patent/DK176247B1/en not_active IP Right Cessation
- 1995-06-01 SE SE9502001A patent/SE520834C2/en not_active IP Right Cessation
- 1995-06-01 NO NO19952183A patent/NO314018B1/en not_active IP Right Cessation
- 1995-06-29 HU HU95P/P00579P patent/HU211912A9/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |
Expiry date: 20150531 |