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DK166564B1 - Temazepam composition, and process for producing it - Google Patents

Temazepam composition, and process for producing it Download PDF

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DK166564B1
DK166564B1 DK69287A DK69287A DK166564B1 DK 166564 B1 DK166564 B1 DK 166564B1 DK 69287 A DK69287 A DK 69287A DK 69287 A DK69287 A DK 69287A DK 166564 B1 DK166564 B1 DK 166564B1
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composition
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temazepam
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DK69287A (en
DK69287D0 (en
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Terry Way
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Farmitalia Carlo Erba Ltd
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Description

i DK 166564 B1in DK 166564 B1

Opfindelsen angår en temazepam-(3-hydroxydiazepam)~komposition og en fremgangsmåde til fremstilling af samme.The invention relates to a temazepam (3-hydroxydiazepam) composition and a process for preparing the same.

Opfindelsen angår navnlig et væskeformigt temazepampræparat, der er egnet til oral indgivelse. Der kendes allerede kapsler, som 5 indeholder temazepam, til oral indgivelse, og formålet med at udvikle et væskeformigt præparat af medikamentet er at fremme hurtigere absorption og således hurtigere søvnfremkaldelse såvel som at give udøvere og patienter et brugbart valg.In particular, the invention relates to a liquid temazepam composition suitable for oral administration. Capsules containing temazepam are already known for oral administration, and the purpose of developing a liquid formulation of the drug is to promote faster absorption and thus faster sleep induction as well as to give practitioners and patients a useful choice.

Temazepam er kun svagt opløseligt i vand og er ustabil i vandig 10 opløsning. Ved henstand har temazepam i sig selv og dets sønder del ingsprodukter således en tendens til at udfældes fra den vandige opløsning. På den anden side er ikke-vandige opløsningsmidler almindeligvis uacceptable til human indtagelse.Temazepam is only slightly soluble in water and is unstable in aqueous solution. Thus, upon standing, temazepam itself and its disintegrating products tend to precipitate from the aqueous solution. On the other hand, non-aqueous solvents are generally unacceptable for human consumption.

Det er et formål med opfindelsen at tilvejebringe et væskefor-15 migt temazepampræparat, der er egnet til oral indgivelse og er velsmagende samtidig med, at den besidder en acceptabel opbevaringsstabilitet og viscositet.It is an object of the invention to provide a liquid temazepam preparation which is suitable for oral administration and is palatable while possessing an acceptable storage stability and viscosity.

Der tilvejebringes følgelig ifølge opfindelsen en temazepam-komposition, der ikke omfatter mere end ca. 0,2% vægt/volumen 20 temazepam, ikke mere end ca. 15% vægt/volumen af mindst en polymer alkohol, ikke mindre end ca. 8% vægt/volumen af en lavtkogende alkohol, fortrinsvis en monovalent alkohol, såsom ethanol eller iso-propanol, fortrinsvis ethanol, ikke mindre end ca. 40% vægt/ volumen glycerol, ikke mere end ca. 45% af en vandig opløsning af mindst en 25 hexavalent alkohol, et sol ubi li seringsmiddel, mindst et smagsstof og mindst én puffer til opretholdelse af kompositionens pH på mellem 7,3 og 8,3 samt en fremgangsmåde til fremstilling af kompositionen.Accordingly, according to the invention, a temazepam composition is provided which comprises no more than ca. 0.2% w / v 20 temazepam, not more than approx. 15% w / v of at least one polymeric alcohol, not less than approx. 8% w / v of a low boiling alcohol, preferably a monovalent alcohol such as ethanol or iso-propanol, preferably ethanol, not less than about 10%. 40% w / v glycerol, not more than approx. 45% of an aqueous solution of at least one hexavalent alcohol, one solubilizing agent, at least one flavor and at least one buffer to maintain the pH of the composition between 7.3 and 8.3 and a process for preparing the composition.

Temazepamkoncentrationen er fortrinsvis ca. 0,2%, idet dette svarer til en koncentration på 10 mg/5 ml, dvs. én normal dosis pr.The temazepam concentration is preferably ca. 0.2%, which corresponds to a concentration of 10 mg / 5 ml, ie. one normal dose per day.

30 teskefuld.30 teaspoons.

Sol ubi li seringsmidl et anvendes for at stabilisere, dispergere og danne kompleks med temazepam og smagsbestanddel en(-delene) (der almindeligvis er uopløselig i vand) og omfatter fortrinsvis polyvi-nylpyrrolidon (Povidon), som udgør op til mindst ca. 2% vægt/volumen 35 af kompositionen.The solubilizing agent is used to stabilize, disperse, and complex with temazepam and flavor constituent one (s) (which are generally insoluble in water) and preferably comprise polyvinylpyrrolidone (Povidone) which is up to at least approx. 2% w / v of the composition.

Kompositionen omfatter et opløsningsmiddel system, som almindeligvis udgøres af vandfri ethanol, glycerol, en polyethylenglycol og en hexavalent alkohol, såsom mannitol eller sorbitol. Der kræves ethanol som opløsningsmiddel til temazepam for at holde DK 166564 B1 2 kompositionens viskositet på et acceptabelt lavt niveau under fremstilling og anvendelse og som konserveringsmiddel til hæmning af mikrobiel vækst. Ethanol mængden bør fortrinsvis ikke overstige ca.The composition comprises a solvent system which is generally composed of anhydrous ethanol, glycerol, a polyethylene glycol and a hexavalent alcohol such as mannitol or sorbitol. Ethanol as solvent for temazepam is required to maintain the viscosity of the composition at an acceptable low level during preparation and use and as a preservative for inhibiting microbial growth. The ethanol amount should preferably not exceed about

10%.10%.

5 Polyethylenglycolen kan være polyethylenglycol 100, men er fortrinsvis polyethylenglycol 400. Den hexavalente alkohol er fortrinsvis sorbitol, som er mere lettilgængelig og har en bedre opløselighed i vand end mannitol. Glycerolmængden er fortrinsvis mindst ca. 50% vægt/volumen; denne mængde bør ikke øges for meget, 10 idet dette vil øge kompositionens osmotiske tryk og føre til en "brændende" smag, medens nedsættelse af glycerol indholdet til under ca. 40% vil reducere dets virkning som et konserveringsmiddel.The polyethylene glycol may be polyethylene glycol 100, but is preferably polyethylene glycol 400. The hexavalent alcohol is preferably sorbitol, which is more readily available and has a better solubility in water than mannitol. The amount of glycerol is preferably at least approx. 50% w / v; this amount should not be increased too much, 10 as this will increase the osmotic pressure of the composition and lead to a "burning" taste, while reducing the glycerol content to below approx. 40% will reduce its effect as a preservative.

.Temazepam er følsom over for pH, og dets sønderdeling kan også ændre kompositionens pH med tiden. Der kræves derfor en puffer, og 15 det initielle pH er fortrinsvis ca. 7,8. Egnede puffere indbefatter di natriumhydrogenphosphat (natriumphosphat BP, vandfrit) og citron-syremonohydrat (den tilstedeværende vandmængde i den anvendte lille citronsyremængde er ubetydelig).Temazepam is sensitive to pH and its decomposition can also change the pH of the composition over time. Therefore, a buffer is required and the initial pH is preferably approx. 7.8. Suitable buffers include di sodium hydrogen phosphate (sodium phosphate BP, anhydrous) and citric acid monohydrate (the amount of water present in the small amount of citric acid used is negligible).

Smagsstoffet(-stofferne) kan omfatte pebermynteolie BP og/eller 20 citronolie. Citronolien er fortrinsvis fri for terpener for at forbedre dets vandbiandbarhed.The flavoring agent (s) may comprise peppermint oil BP and / or lemon oil. The lemon oil is preferably free of terpenes to improve its water compatibility.

Kompositionen omfatter almindeligvis yderligere et farvestof, såsom chlorophyl, for at forbedre det æstetiske udseende.The composition generally further comprises a dye, such as chlorophyll, to enhance the aesthetic appearance.

Den rækkefølge, hvori kompositionens bestanddele blandes, er 25 uvæsentlig. Fremgangsmåden omfatter fortrinsvis, at den vandige opløsning og mindst noget af pufferen (pufferne) kombineres til opnåelse af en første opløsning A, af mindst nogle af al kohol bestanddelene, sol ubil i seringsmidlet og temazepam kombineres til opnåelse af en anden opløsning B, at opløsningerne A og B kombine-30 res, og at smagsstoffet(-stofferne) tilsættes.The order in which the constituents of the composition are mixed is insignificant. Preferably, the process comprises combining the aqueous solution and at least some of the buffer (s) to obtain a first solution A, of at least some of all the alcohol components, soluble in the lubricant, and temazepam to obtain a second solution B A and B are combined and the flavor (s) added.

Opfindelsen vil nu blive beskrevet i form af et eksempel.The invention will now be described by way of example.

EksempelExample

Der fremstilles en komposition i overensstemmelse med opfin-35 del sen ud fra de bestanddele, som er anført i nedenstående tabel.A composition according to the invention is prepared from the constituents listed in the table below.

5 DK 166564 B1 35 DK 166564 B1 3

Tabel % vægt/vol urnen mg/5 ml (g/100ml)Table% w / v urn mg / 5 ml (g / 100ml)

Temazepam 0,206 10Temazepam 0.206 10

Povidon (Kollidon 25) BP 2,000 100Povidon (Kollidon 25) BP 2,000 100

Polyethylenglycol 400 BP 5,000 250Polyethylene glycol 400 BP 5,000 250

Ethanol, absolut (vandfrit) BP 8,800 440 10 Glycerol BP 50,000 2500Ethanol, absolute (anhydrous) BP 8,800 440 10 Glycerol BP 50,000 2500

Natriumphosphat (vandfrit) BP 2,500 125Sodium Phosphate (Anhydrous) BP 2,500 125

Citronsyre 0,125 6,25Citric Acid 0.125 6.25

ChlorophyT 'JJ' 0,012 0,60ChlorophyT 'JJ' 0.012 0.60

Sorbitolopløsning (70%) BP 45,000 2250 15 Pebermynteolie BP 0,035 1,75Sorbitol Solution (70%) BP 45,000 2250 Peppermint Oil BP 0.035 1.75

Citronsmag Supara SL 2300 0,060 3Lemon flavor Supara SL 2300 0.060 3

Glycerol BP Op til 100.000 volumer/5 ml *Glycerol BP Up to 100,000 volumes / 5 ml *

Der inkluderes et overskud på 3%. Beslutningen om at inkludere 20 dette er baseret på analyseresultater fra partier fremstillet ved pilotforsøg, hvor der forekom tab på mellem 2 og 7%. Det menes, at tabene skyldes den høje viscositet af temazepamopløsningen, som tilsættes glycerolen.A surplus of 3% is included. The decision to include this is based on analysis results from batches produced by pilot trials where losses of between 2 and 7% occurred. It is believed that the losses are due to the high viscosity of the temazepam solution added to the glycerol.

25 Sorbitol sirup udhældes i en beholder af rustfrit stål og opvarmes til 60°C. Der tilsættes vandfrit natriumphosphat, og der blandes med et blandeapparat med høj forskydning indtil opløsning. Blandingen får lov til at afkøle til ca. 40°C, og der tilsættes citronsyre og blandes med et blandeapparat med høj forskydning, 30 indtil det er opløst. Der tilsættes Chlorophyll JJ, og der blandes med et bl andeapparat med høj forskydning, indtil der opnås en ensartet grøn opløsning. Blandingen får lov til at afkøle til stuetemperatur (dvs. ca. 20°C) i løbet af ca. 24 timer til opnåelse af opløsning A.25 Sorbitol syrup is poured into a stainless steel container and heated to 60 ° C. Anhydrous sodium phosphate is added and mixed with a high shear mixer until dissolved. The mixture is allowed to cool to ca. 40 ° C and citric acid is added and mixed with a high shear mixer until dissolved. Chlorophyll JJ is added and mixed with a high shear blender until a uniform green solution is obtained. The mixture is allowed to cool to room temperature (i.e., about 20 ° C) over approx. 24 hours to obtain solution A.

35 I en anden beholder af rustfrit stål afvejes glycerolen, og polyethylenglycol 400 og 90% af ethanol en tilsættes og blandes med et blandeapparat med høj forskydning. Under fortsat blanding blev povidon langsomt tilsat, og der blev blandet indtil det var opløst.In another stainless steel container, the glycerol is weighed and polyethylene glycol 400 and 90% of ethanol are added and mixed with a high shear mixer. With continued mixing, povidone was slowly added and mixed until dissolved.

Der blev tilsat temazepam, og der blev blandet, indtil det var DK 166564 B1 4 opløst, til opnåelse af opløsning B.Temazepam was added and mixed until dissolved to obtain solution B.

Den afkølede opløsning A blev langsomt sat til opløsning B ved blanding med en rørerarm. Der blev derpå tilsat og iblandet pebermynte- og citronsmagsstoffer. Beholderne til smagsstoffet blev 5 skyllet med resten af ethanol en, og skylleopløsningerne blev sat til præparationen og blandet. Præparationen blev tilsat glycerol op til volumen og blandet, og pH blev justeret til mellem 7,6 og 8,0 under anvendelse af citronsyre eller koncentreret natriumhydroxidopiøsing.The cooled solution A was slowly added to solution B by mixing with a stirring arm. Peppermint and lemon flavors were then added and mixed. The flavors containers were rinsed with the remainder of ethanol one and the rinsing solutions were added to the preparation and mixed. The preparation was added glycerol up to volume and mixed and the pH was adjusted to between 7.6 and 8.0 using citric acid or concentrated sodium hydroxide solution.

Det opnåede produkt var en klar, lys, viskøs, grøn væske med en 10 lugt og smag af citron og pebermynte. pH var på fra 7,3 til 8,3 ved 20°C, og vægten pr. ml var fra 1,20 til 1,26 g ved 20°C. Absorpti-onsspektrummet viste tilstedeværelse af temazepam og chlorophyl, og HPLC viste tilstedeværelse af fra 1,96 til 2,2 mg/ml (fra 98 til 110%) temazepam. HPLC og spectrophotofluorometrisk analyse viste 15 tilstedeværelse af ikke mere end 2,5% organiske urenheder, herunder ikke mere end 0,5% 2-methylamino-5-chlorbenzophenon og fluorescerende nedbrydningsprodukter under ét. GLC viste, at ethanol indholdet var fra 7,4 til 9% vægt/volumen.The product obtained was a clear, light, viscous, green liquid with a 10 odor and taste of lemon and peppermint. The pH was from 7.3 to 8.3 at 20 ° C, and the weight per ml was from 1.20 to 1.26 g at 20 ° C. The absorption spectrum showed the presence of temazepam and chlorophyll, and HPLC showed the presence of 1.96 to 2.2 mg / ml (from 98 to 110%) of temazepam. HPLC and spectrophotofluorometric analysis showed the presence of no more than 2.5% organic impurities, including no more than 0.5% 2-methylamino-5-chlorobenzophenone and fluorescent degradation products together. The GLC showed that the ethanol content was from 7.4 to 9% w / v.

Ved henstand forblev produktets specifikation som anført oven 20 for med undtagelse af, at temazepamindholdet faldt til ikke under 1,8 mg/ml (90%), og andelen af organiske urenheder steg til ikke over 5%, herunder ikke mere end 2,5% 2-methylamino-5-chlorbenzophe-non og ikke mere end 1,5% fluorescerende nedbrydningsprodukter. Produktet forblev inden for disse (acceptable) grænser i ikke under t\ 25 år.On standing, the product specification remained above 20 except that the temazepam content dropped to not less than 1.8 mg / ml (90%) and the proportion of organic impurities increased to no more than 5%, including not more than 2.5 % 2-methylamino-5-chlorobenzopheone and no more than 1.5% fluorescent degradation products. The product remained within these (acceptable) limits for not less than 25 years.

Produktet viste sig ydermere at besidde en acceptabel smag og at fremme hurtig absorption, idet de terapeutiske plasmaniveauer af temazepam blev nået ca. 15 min efter indgivelse i sammenligning med de tidligere opnåede 30 min med kapsler.Furthermore, the product was found to possess an acceptable taste and to promote rapid absorption, with the therapeutic plasma levels of temazepam being reached approx. 15 min after administration compared to the previously obtained 30 min with capsules.

30 3530 35

Claims (14)

1. Temazepamkomposition, kendetegnet ved, at den indeholder ikke mere end ca. 0,2% vægt/volumen temazepam, ikke mere 5 end ca. 15% vægt/volumen af mindst en polymer alkohol, ikke mindre end ca. 8% vægt/volumen af en lavtkogende alkohol, ikke mindre end ca. 40% vægt/vol umen glycerol, ikke mere end ca. 45% af en vandig opløsning af mindst en hexavalent alkohol, et sol ubiliseringsmiddel, mindst et smagsstof og mindst en puffer til opretholdelse af kompo-10 sitionens pH på fra 7,3 til 8,3.1. Temazepam composition, characterized in that it contains no more than approx. 0.2% w / v temazepam, not more than 5 15% w / v of at least one polymeric alcohol, not less than approx. 8% w / v of a low-boiling alcohol, not less than approx. 40% w / v glycerol, not more than approx. 45% of an aqueous solution of at least one hexavalent alcohol, one solar immobilizer, at least one flavor and at least one buffer to maintain the pH of the composition from 7.3 to 8.3. 2. Komposition ifølge krav 1, kendetegnet ved, at sol ubil i seringsmidlet er polyvinyl pyrrol idon og udgør mindst ca. 2% vægt/volumen af kompositionen.Composition according to claim 1, characterized in that the sol ubil in the lubricant is polyvinyl pyrrole idon and constitutes at least approx. 2% w / v of the composition. 3. Komposition ifølge krav 1 eller 2, kendetegnet 15 ved, at den polymere alkohol er opnået ved polymerisering af en glycol.Composition according to claim 1 or 2, characterized in that the polymeric alcohol is obtained by polymerization of a glycol. 4. Komposition ifølge et hvilket som helst af de foregående krav, kendetegnet ved, at den omfatter fra 5% til 15% vægt/volumen af mindst en polymer alkohol.Composition according to any one of the preceding claims, characterized in that it comprises from 5% to 15% w / v of at least one polymeric alcohol. 5. Komposition ifølge et hvilket som helst af de foregående krav, kendetegnet ved, at den omfatter fra 8 til 10% ethanol.Composition according to any one of the preceding claims, characterized in that it comprises from 8 to 10% ethanol. 6. Komposition ifølge et hvilket som helst af de foregående krav, kendetegnet ved, den vandige opløsning er en 70% 25 opløsning af sorbitol.Composition according to any one of the preceding claims, characterized in that the aqueous solution is a 70% solution of sorbitol. 7. Komposition ifølge et hvilket som helst af de foregående krav, kendetegnet ved, at kompositionens initielle pH er på fra 7,5 til 8.Composition according to any one of the preceding claims, characterized in that the initial pH of the composition is from 7.5 to 8. 8. Komposition ifølge et hvilket som helst af de foregående 30 krav, kendetegnet ved, at mindst en af pufferne omfatter natriumphosphat og/eller citronsyre.Composition according to any one of the preceding claims, characterized in that at least one of the buffers comprises sodium phosphate and / or citric acid. 9. Komposition ifølge et hvilket som helst af de foregående krav, kendetegnet ved, at den yderligere omfatter et farvestof.Composition according to any one of the preceding claims, characterized in that it further comprises a dye. 10. Fremgangsmåde til fremstilling af en temazepamkomposition, kendetegnet ved, at ikke mere end ca. 0,2% vægt/vol umen temazepam, ikke mere end ca. 15% vægt/volumen af mindst en polymer alkohol, ikke mindre end ca. 8% vægt/volumen ethanol, ikke mindre end ca. 40% vægt/volumen glycerol, ikke mere end ca. 45% af en DK 166564 B1 vandig opløsning af mindst en hexavalent alkohol, et sol ubil i seri ngsmiddel, mindst et smagsstof og mindst en puffer til opretholdelse af kompositionens pH fra 7,3 til 8,3 blandes.Process for the preparation of a temazepam composition, characterized in that no more than approx. 0.2% w / v temazepam, not more than approx. 15% w / v of at least one polymeric alcohol, not less than approx. 8% w / v ethanol, not less than ca. 40% w / v glycerol, not more than approx. 45% of a DK 166564 B1 aqueous solution of at least one hexavalent alcohol, one sol ubil in serial, at least one flavor and at least one buffer to maintain the pH of the composition from 7.3 to 8.3 is mixed. 11. Fremgangsmåde ifølge krav 10, kendetegnet ved, 5 at den vandige opløsning og mindst noget af pufferen (pufferne) blandes til opnåelse af en første opløsning A, at mindst noget af al kohol bestanddel ene, sol ubili seringsmidl et og temazepam blandes til opnåelse af en anden opløsning B, at opløsningerne A og B blandes, og at smagsstoffet(-stofferne) tilsættes.Process according to claim 10, characterized in that the aqueous solution and at least some of the buffer (s) are mixed to obtain a first solution A, that at least some of all the alcoholic components, solubilizing agent and temazepam are mixed to obtain of another solution B, mixing solutions A and B and adding the flavor (s). 12. Fremgangsmåde ifølge krav 11, kendetegnet ved, at den vandige opløsning opvarmes før tilsætning af pufferen (pufferne), og at opløsning A afkøles til stuetemperatur før blanding af opløsningerne A og B.Process according to claim 11, characterized in that the aqueous solution is heated before the addition of the buffer (s) and that solution A is cooled to room temperature before mixing of solutions A and B. 13. Fremgangsmåde ifølge krav 12, kendetegnet ved, 15 at mindst et farvestof sættes til opløsning A, medens temperaturen af opløsning A er over stuetemperatur.Process according to claim 12, characterized in that at least one dye is added to solution A while the temperature of solution A is above room temperature. 14. Fremgangsmåde ifølge et hvilket som helst af kravene 10-13, kendetegnet ved, at den yderligere omfatter, at kompositionens pH justeres til fra 7,6 til 8,0. 20 . 25 30 35Process according to any one of claims 10-13, characterized in that it further comprises adjusting the pH of the composition to from 7.6 to 8.0. 20. 25 30 35
DK69287A 1987-02-11 1987-02-11 Temazepam composition, and process for producing it DK166564B1 (en)

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DK69287A DK166564B1 (en) 1987-02-11 1987-02-11 Temazepam composition, and process for producing it

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DK69287A DK69287A (en) 1988-08-12
DK166564B1 true DK166564B1 (en) 1993-06-14

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B1 Patent granted (law 1993)
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