CZ297354B6 - Prípravek pro aplikaci v ústní dutine s filmem nebo fólií s okamzitou smácitelností - Google Patents
Prípravek pro aplikaci v ústní dutine s filmem nebo fólií s okamzitou smácitelností Download PDFInfo
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- CZ297354B6 CZ297354B6 CZ0164799A CZ164799A CZ297354B6 CZ 297354 B6 CZ297354 B6 CZ 297354B6 CZ 0164799 A CZ0164799 A CZ 0164799A CZ 164799 A CZ164799 A CZ 164799A CZ 297354 B6 CZ297354 B6 CZ 297354B6
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Classifications
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Abstract
Prípravek pro aplikaci v ústní dutine s vrstvou nebo filmem pevne ulpívající(m) na sliznici, kde pevne ulpívající vrstva nebo pevne ulpívající film obsahuje homogenní smes sestávající z vodorozpustného polymeru, smesi neionogenních povrchove aktivních látek, polyalkoholu, kosmeticky nebo farmaceuticky úcinné látky a ochucovací nebo aromatické látky. Smes neionogenních povrchove aktivních látek sestává ze dvou slozek, pricemz první slozkou je polyethoxysorbitanový ester mastné kyseliny nebo blokový kopolymer .alfa.-hydro-.omega.-hydroxypoly(ethoxy)-poly-(propoxy)-poly(ethoxy) a druhou slozkou je polyethoxyalkylether nebo polyethoxyderivát ricinového oleje, pricemz pomer mezi první a druhou slozkou binární povrchove aktivní smesi je udrzovánmezi 1:10 a 1:1.
Description
Přípravek pro aplikaci v ústní dutině s filmem nebo fólií s okamžitou smáčitelností
Oblast techniky
Předložený vynález se týká přípravku, který obsahuje farmaceuticky účinné látky a/nebo dech osvěžující látky pro použití v ústní dutině. Nosič obsahuje ve vodě rozpustné polymery obsahující kombinaci určitých látek a má terapeutický a/nebo kosmetický účinek. Film se natírá za použití běžných technologií pro nanášení, vysuší se a vykazuje okamžitou smáčitelnost, následovanou rychlým rozpuštěním/rozkladem při aplikaci v ústní dutině.
Dosavadní stav techniky
Podle dosavadního stavu techniky jsou známy na sliznici ulpívající (mukoadhesivní) dávkovači systémy do ústní dutiny, pomocí nichž mají být dávkovány terapeuticky a/nebo kosmeticky účinné látky na ústní sliznici. Patent US 5 047 224 popisuje na ústní sliznici ulpívající nosič pro kontrolované dávkování terapeuticky účinné látky do tkáně sliznice, který obsahuje bezvodou, ale hydratizovatelnou polymemí matrici a amorfní oxid křemičitý. Může být případně připojen ve vodě nerozpustný film, aby se vytvořil neadhesivní povrch. Mezinárodní patentová přihláška WO 91/06 270 od stejného původce publikuje třívrstvý film k prodlouženému dávkování aktivní účinné látky v ústní dutině. Stejným způsobem uvádí patent US 4 876 092 plošně působící adhesivní přípravek, který obsahuje adhesivní vrstvu, jež obsahuje určité vodorozpustné a ve vodě nerozpustné polymery a ve vodě nerozpustný nosič, který ulpívá na ústní sliznici a při tom dávkuje v ústní dutině účinnou látku.
Všechna tato shora uvedená zařízení nejsou zcela ve vodě rozpustná a setrvávají v ústní dutině i po dosažení terapeutického cíle a způsobují pacientovi v ústech jisté potíže, způsobené hlavně nosnou vrstvou, která v ústech zanechává nerozpustný zbytek.
Byla podniknuta řada pokusů zmenšit v ústní dutině tento nedobrý pocit, který byl způsoben tuhostí a chybějící flexibilitou nosné vrstvy tak, že se zaváděly měkké nosiče filmu. Patenty EP 0 200 508 a EP 0 381 194 navrhují používat jako měkké nosiče polyethylenové filmy, polyvinylacetát, kopolymery ethylen-vinylacetát, kovové fólie, látkové nebo papírové lamináty s plastikovým filmem a podobné materiály, při čemž přednost se dává materiálům ze syntetických pryskyřic jako jsou polyethylen, homopolymery vinylacetátu a kopolymery ethylen-vinylacetát. Stejně tak se v CA 1263 312 pro měkké nosiče publikuje používání polyolefínů jako polyethylenu a polypropylenu, polyesterů. PVC a také roun. Ty však přesto zanechávají u pacienta podstatné množství zbytků ve vodě nerozpustných filmů nosičů a jsou proto stále ještě příčinou nepříjemného pocitu. K překonání tohoto problému bylo nasnadě řešit vývoj filmů ulpívajících na sliznici, které se rozpadnou úplně anebo se rozpustí ve slinách. Fuchs a Hilmann (DE 24 49 865.5) vyrobili ve vodě rozpustné filmy pro ústní podávání hormonů. Pro vytvoření filmu navrhli používat deriváty celulózy jako je hydroxyethylcelulóza, hydroxypropylcelulóza nebo methylhydroxypropylcelulóza. V obou patentech DE 36 30 603 a EP 0 219 762 je na vytvoření filmu popisováno použití bobtnatelných polymerů jako je želatina nebo kukuřičný škrob, které se po aplikaci v ústní dutině pomalu rozpadají a přitom uvolňují aktivně působící látku, která je ve filmu obsažena. Podle popisu v EP 0 452 446 mohou být rovněž použity stejné polymery pro vytvoření filmů, které mají sloužit pro zubní péči. Avšak i tyto přípravky rovněž vyvolávají v ústech nedobrý pocit působený jejich počáteční tuhostí a prodlužovaným změkčováním. Z toho vyplývá poptávka po takové komposici pro použití v ústní dutině, která splní požadavek dobrého pocitu v ústech.
Podstata vynálezu
Předložený vynález popisuje způsob a přípravky, pomocí nichž se lze vyhnout nepříjemnému pocitu, a to poskytnutím jednoho/jedné okamžitou smáčitelnost vykazujícího/vykazující filmu/
-1 CZ 297354 B6 vrstvy pro aplikaci na ústní sliznici a u volného filmu dosažením takové pevnosti v tahu, že bez problémů umožňuje nanášení, další zpracování a balení produktu přitažlivého pro spotřebitele.
Předložený vynález se týká přípravku pro aplikaci v ústní dutině s rychle se rozpouštěj ícím/rozpouštějící filmem/vrstvou, který/á ulpívá v ústní dutině a přitom uvolňuje farmaceuticky nebo kosmeticky účinnou látku a film/vrstva přitom obsahuje jeden nebo více polyalkoholů a jednu nebo více farmaceuticky nebo kosmeticky účinných látek. Volitelně může formulace obsahovat kombinaci určitých změkčovadel nebo povrchově aktivních látek, barviv, sladidel, chuťových přísad, chuť zlepšujících látek nebo jiných korigencií, které u formulací pro aplikaci v ústní dutině mají obvykle použití pro modifikaci chuti. Resultující film se vyznačuje okamžitou smáčitelností, která způsobí, že film bezprostředně po aplikaci na tkáni sliznice změkne, čímž se zabrání delší dobu přetrvávajícímu nepříjemnému pocitu u pacienta, a právě tak se vyznačuje vhodnou pevností v tahu při normálních operacích jako je nanášení, řezání, rozstřihávání a balení.
Předložený vynález se tedy týká přípravku pro aplikaci v ústní dutině s filmem nebo fólií, ulpívající na sliznici s okamžitou smáčitelností, kde film nebo fólie zahrnuje homogenní směs sestávající z
- alespoň jednoho vodorozpustného polymeru,
- směsi neionogenních povrchově aktivních látek,
- alespoň jednoho polylakoholu,
- alespoň jednoho kosmeticky nebo farmaceuticky účinného prostředku a - popřípadě alespoň jedné aromatické přísady, přičemž podle vynálezu směs neionogenních povrchově aktivních látek sestává ze dvou složek, kde první složkou je polyethoxysorbitanový ester mastné kyseliny nebo blokový kopolymer a-hydro-ro-hydroxypoly(ethoxy)-poly-(propoxy)-poly(ethoxy) a druhou složkou je polyethoxyalkylether nebo polyethoxyderivát ricinového oleje a poměr mezi první a druhou složkou binární povrchově aktivní směsi je udržován mezi 1:10 a 1:1.
Mukoadhesivní film podle předkládaného vynálezu obsahuje jako podstatnou část vodorozpustný polymer nebo kombinaci vodorozpustných polymerů, jedno nebo více změkčovadel nebo povrchově aktivních látek, jeden nebo více polyalkoholů a farmaceuticky nebo kosmeticky účinnou látku. Polymery pro mukoadhesivní film zahrnují hydrofilní a/nebo ve vodě dispergovatelné polymery. Preferovanými polymery jsou ve vodě rozpustné deriváty celulózy. Přednost mají zejména hydroxypropylmethylcelulóza, hydroxyethylcelulóza a hydroxypropylcelulóza samotné nebo ve směsi. Aniž by to omezovalo vynález, lze jako příklady pro další případné polymery následovně uvést: polyvinylpyrrolidon, karboxymethylcelulózu, polyvinylalkohol, alginát sodný, polyethylenglykol, přírodní kaučukovité hmoty jako xanthanovou pryskyřici, tragant, guarovou pryskyřici, akaciovou pryskyřici, arabskou gumu, ve vodě dispergovatelné polyakryláty jako kyselinu polyakrylovou, kopolymery methylmethakrylátu, karboxyvinylové kopolymery. Koncentrace vodorozpustného polymeru v hotovém filmu může být mezi 20 a 75 % hmotnostními. Preferovaná koncentrace je mezi 50 a 75 % hmotnostními.
Povrchově aktivními látkami používanými pro mukoadhesivní film může být jedna nebo více neionogenních povrchově aktivních látek. Při použití kombinace povrchově aktivních látek může být první komponentou polyethoxysorbitanový ester mastné kyseliny nebo blokový kopolymer a-hydro-m-hydroxypoly(ethoxy)-poly(propoxy)-poly(ethoxy), zatímco druhou komponentou může být polyethoxyalkylether nebo polyethoxyderivát ricinového oleje.
HLB hodnota polyethoxysorbitanového esteru mastné kyseliny má být nejlépe mezi 10 a 20, přičemž se zvláště dává přednost rozsahu mezi 13 a 17. Blokový kopolymer a-hydro-ro-hydroxypoly(ethoxy)-poly-(propoxy)-poly(ethoxy) má obsahovat nejméně 35 jednotek propoxy, přednost
-2CZ 297354 B6 se dává nejméně 50 jednotkám propoxy. Polyethoxyalkylether by měl mít HLB hodnotu mezi 10 a 20, nejlépe ne méně než 15. Polyethoxyderivát ricinového oleje má mít HLB hodnotu mezi 14 a 16. Aby se dosáhlo požadované okamžité smáčitelnosti, má být poměr mezi první a druhou komponentou binární povrchově aktivní směsi udržován mezi 1:10a 1:1 a přednost se dává mezi 1:5 a 1:3. Celková koncentrace povrchově aktivních látek v hotovém filmu záleží na vlastnostech ostatních ingrediencí, má však obyčejně být mezi 0,1 a 5 % hmotnostními. Polyalkohol je zapotřebí, aby se dosáhl požadovaný stupeň měkkosti. Příklady polyalkoholů zahrnují glycerol, polyethylenglykol, propylenglykol, monoestery glycerolu s mastnými kyselinami nebo jiné, farmaceuticky používané polyalkoholy. Koncentrace polyalkoholů v suché hmotě filmu obvykle obnáší 0,1 až 5 % hmotnostních.
Film se zvlášť dobře hodí k podávání široké škály farmaceuticky aktivních účinných látek prostřednictvím membrán sliznic pacienta, zejména prostřednictvím ústních sliznic. Zvlášť dobře se hodí terapeuticky účinné látky, u kterých jsou problémy s absorpcí vlivem omezené rozpustnosti, s odbouráváním v gastrointestinálním traktu nebo vlivem extensivního metabolismu. Jako příklady použitelných terapeuticky aktivních látek lze jmenovat: hypnotika, sedativa, antiepileptika, stimulační aminy, psychoneurotropika, svalové neuroblokátory, antispasmodika, antihistaminika, antialergika, kardiotonika, antiarhytmika, diuretika, hypotenziva, vasopressory, antitussiva, expektorancia, thyroidní hormony, sexuální hormony, antidiabetika, přípravky účinné proti nádorům, antibiotika a také chemoterapeutika a narkotika. Do filmu uložené množství účinné látky závisí na jejím druhu a obvykle obnáší mezi 0,01 a 20 % hmotnostními, avšak pokud je to pro docílení požadovaného účinku nutné, může být i vyšší.
Kosmeticky účinné látky zahrnují osvěžovače dechu jako menthol, jiné chuťové, aromatické nebo vonné látky, které se obvykle používají v ústní hygieně, a/nebo účinné látky pro zubní péči a/nebo ústní hygienu, na příklad kvartémí amoniové zásady. Působení chuťových a aromatických látek se zesiluje látkami, které zdůrazňují chuť jako je kyselina vinná, kyselina citrónová, vanilin nebojím podobné. Barviva, která mohou být případně do filmu přimíšena, musí být bezpečná z hlediska toxicity a musí být příslušnými úřady schválena pro použití v kosmetice.
Mukoadhesivní film podle vynálezu může být zhotoven následujícím způsobem:
Polyalkohol, povrchově aktivní látky, změkčovadla a jiné případné složky mimo vodorozpustného(ných) nebo ve vodě dispergovatelného (ných) polymeru(ů) se rozpustí v dostatečném množství kompatibilního rozpouštědla. Příklady kompatibilního rozpouštědla zahrnují vodu, alkoholy nebo jejich směsi. Po vzniku čirého roztoku se pomalu, za stálého míchání a pokud je to nutné za zahřívání, přidává ve vodě dispergovatelný polymer nebo směs ve vodě dispergovatelných polymerů až se vytvoří čirý a homogenní roztok. Ten se nanese na nosič a vysuší na film. Materiál nosiče musí mít takové povrchové napětí, aby umožnilo rovnoměrně rozvrstvit roztok polymeru po celé předpokládané šířce, aniž by se roztok vsákl a tím vzniklo destruktivní spojení mezi nosičem a nanášenou vrstvou.
Mezi příklady pro vhodné materiály nosičů patří nesilikonizované filmy polyethylen-tereftalát, nesilikonizovaný sulfátový „kraft” papír, sulfátový „kraft” papír impregnovaný polyethylenem nebo nesilikonisovaný polyethylenový film. Nanesení roztoku na nosný materiál je možné provádět každým běžným zařízením. Speciálně oblíbená nanášecí technika se týká natíracího stroje s válcovou stěrkou. Tloušťka vzniklé filmové vrstvy závisí na koncentraci pevných látek v nanášeném roztoku a také na šířce štěrbiny natíracího stroje a může se pohybovat mezi 5 a 200 pm. Sušení se provádí za použití sušárny, sušícího tunelu, vakuové sušičky nebo jiných vhodných sušicích zařízení, které negativně neovlivňují působení účinné(ných) látky(látek) nebo chuťových látek. Aby se spolehlivě vyvaroval nepříjemný pocit v ústech, nemá tloušťka filmové vrstvy překročit 70 pm. Pro lepší usnadnění používání může být film nařezán na kousky vhodné velikostí a formy a zabalen. Vynález je názorně popisován v následujících příkladech.
-3 CZ 297354 B6
Příklad provedení vynálezu
Příklad 1 g sorbitolu, 6g glycerolu, 0,5 g polysorbátu (Tween 80 = polyoxymethylen[20] sorbitan monooleát), 2 g Brij 35 (= polyoxyethylen[23] lauryl ether), 25 g aroma máty citrónové, 3 g Aspartamu, 15 g 1-mentholu a 3 g kyseliny citrónové bylo při 60 °C ve směsi 250 g vody a 250 g ethanolu mícháno tak dlouho, až vznikl čirý roztok. K roztoku bylo pomalu za míchání přidáváno 30 g hydroxypropylmethylcelulózy, až se vytvořil čirý a homogenní roztok. Vzniklý roztok se potom nechal ochladit na teplotu místnosti a za použití obvyklého nanášecího/sušícího zařízení byl nanesen na vhodný nosný materiál, například na nesilikonizovaný sulfátový „krafit” papír potažený polyethylenem. Štěrbina pro nanášení a rychlost po dráze musí být nařízeny tak, aby se dosáhlo u suchého filmu tloušťky mezi 20 a 50 pm. Teplota při sušení je závislá na délce sušicí pece rychlosti pohybu materiálu a má být nastavena tak, aby se z filmu rozpouštědlo odstranilo úplně nebo alespoň z největší části. Vzniklý film se sejme z nosiče a pro použití se rozdělí na kousky vhodné velikosti a tvaru.
Příklad 2 g sorbitolu, 1,5 g Kollidonu 30 (dodavatel BASF), 5 g glycerolu, 5 g propylenglykolu, 4 g polysorbátu (Tween 80 - polyoxymethylen[20] sorbitan monooleát), 8 g Brij 35 (= polyoxyethylen[23] lauryl ether), 12 g aroma máty pepmé, 0,8 g Aspartamu, bylo při 60 °C za míchání rozpuštěno ve směsi 400 g vody a 400 g ethanolu. K čirému roztoku bylo pomalu za míchání přidáváno 28 g hydroxypropylmethylcelulózy. Po úplném rozpuštění polymeru se roztok ochladil na teplotu místnosti a byl nanesen na nosič za stejných podmínek při nanášení a sušení jako v příkladu 1. Suchý film byl opět rozdělen na kousky vhodné velikosti a tvaru.
Příklad 3 g sorbitolu, 22,5 g glycerolu, 2,5 g propylenglykolu, 2,5 g Brij 35 (= polyoxyethylen[23] lauryl ether), 2,5 g Poloxameru 407, 3,5 g Cremophoru RH 40, 9,5 g aroma máty klasnaté, 0,5 g Aspartamu, bylo při 60 °C za stálého míchání rozpuštěno ve směsi 250 g vody a 250 g ethanolu. K čirému roztoku bylo pomalu za míchání přidáváno 75 g hydroxypropylcelulózy. Čirý roztok byl jako v příkladu 1 nanesen a vysušen; vysušený film byl opět rozdělen na kousky vhodné velikosti a tvaru.
Příklad 4
3,6 g Tween 80 (= polyoxymethylen[20] sorbitan monooleát), 3,6 g glycerolu, 39 g mentholu a 171 g Kollidonu 30 bylo za míchání při teplotě místnosti rozpuštěno v roztoku 600 ml vody a 2800 ml ethanolu. Potom bylo při 50 až 55 °C pomalu po dávkách přidáno 247,5 g hydroxypropylmethylcelulózy; mícháno bylo až do úplného rozpuštění. Po ochlazení směsi bylo za míchání přidáno postupně 90 g aroma máty citrónové, následovaných roztokem/suspensí 27,13 g Aspartamu, 18 g kyseliny citrónové a 0,17 g FD&C žlutě # 5 ve 120 ml vody. Čirý roztok byl za podmínek popsaných v příkladu 1 nanesen na nosič a vysušen; suchý film byl rozdělen na kousky vhodné velikosti a tvaru pro zamýšlené použití.
Příklad 5
165,4 g Kollidonu 30 bylo za míchání při teplotě místnosti rozpuštěno v roztoku 720 ml vody a 2660 ml ethanolu. Potom bylo při 55 až 60 °C přidáno 220,5 g hydroxypropylmethylcelulózy a tak dlouho intensivně mícháno, až byl roztok čirý a homogenní. Po ochlazení bylo do směsi po
-4CZ 297354 B6 řadě za míchání přidáno 78,75 g ochucovací látky následované směsí 26,88 g salicylátu nikotinu a 31,5 g kapalného karamelu ve 120 ml vody. Čirá, žlutohnědá kapalina byla za podmínek popsaných v příkladu 1 natřena a usušena a suchý film byl rozdělen na kousky vhodného tvaru a velikosti pro podávání nikotinové dávky 1 až 2 mg v jednom kousku.
Claims (10)
- PATENTOVÉ NÁROKY1. Přípravek pro aplikaci v ústní dutině s filmem nebo fólií, ulpívající na sliznici s okamžitou smáčitelností, kde film nebo fólie zahrnuje homogenní směs sestávající z- alespoň jednoho vodorozpustného polymeru,- směsi neionogenních povrchově aktivních látek,- alespoň jednoho polylakoholu,- alespoň jednoho kosmeticky nebo farmaceuticky účinného prostředku a- popřípadě alespoň jedné aromatické přísady, vyznačující se tím, že směs neionogenních povrchově aktivních látek sestává ze dvou složek, přičemž první složkou je polyethoxysorbitanový ester mastné kyseliny nebo blokový kopolymer a-hydro-ro-hydroxypoly(ethoxy)-poly-(propoxy)-poly(ethoxy) a druhou složkou je polyethoxyalkylether nebo polyethoxyderivát ricinového oleje, přičemž poměr mezi první a druhou složkou binární povrchově aktivní směsi je udržován mezi 1:10 a 1:1.
- 2. Přípravek podle nároku 1, vyznačující se tím, že poměr mezi první a druhou složkou binární směsi je mezi 1:5 a 1:3.
- 3. Přípravek podle nároku 1 nebo 2, vyznačující se tím, že HLB hodnota polyethoxysorbitanového esteru mastné kyseliny je mezi 10 a 20.
- 4. Přípravek podle kteréhokoli z předcházejících nároků, vyznačující se tím, žeHLB hodnota polyethoxyalkylether je mezi 10 a 20.
- 5. Přípravek podle kteréhokoli z předcházejících nároků, vyznačující se tím, že polyethoxyderivát ricinového oleje má HLB hodnotu 14 až 16.
- 6. Přípravek podle kteréhokoli z předcházejících nároků, vyznačující se tím, že blokový kopolymer a-hydro-ro-hydroxypoly(ethoxy)-poly-(propoxy)-poly(ethoxy) obsahuje alespoň 35 propoxy jednotek.
- 7. Přípravek podle kteréhokoli z předcházejících nároků, vyznačující se tím, že vodorozpustný polymer je vybrán ze skupiny sestávající z hydroxypropylmethylcelulózy, hydroxyethylcelulózy, hydroxypropylcelulózy, polyvinylpyrrolidonu, karboxymethylcelulózy, polyvinylakoholu, alginátu sodného, polyethylenglykolu, xanthanové pryskyřice, tragantu, guarové gumy, akaciové gumy, arabské gumy, polyakrylové kyseliny, methylmethakrylátového kopolymeru, karboxyvinylových kopolymerů nebo jejich směsí.
- 8. Přípravek podle kteréhokoli z předcházejících nároků, vyznačující se tím, že polyalkohol je vybrán ze skupiny sestávající z glycerolu, polyethylenglykolu, propylenglykolu a monoesterů glycerolu s mastnými kyselinami.-5CZ 297354 B6
- 9. Přípravek podle kteréhokoli z předcházejících nároků, vyznačující se tím, že farmaceuticky účinný prostředek je vybrán ze skupiny sestávající z hypnotik, sedativ, antiepileptik, psychostimulačních aminů, psychoneurotropních prostředků, neuromuskulámích blokátorů, antispasmodik, antihistaminik, antialergik, kardiotonik, antiarytmik, diuretik, hypotenziv,5 vasopresorů, antitusiv, expektorancií, protinádorově účinných látek, thyroidních hormonů, pohlavních hormonů, antidiabetik, antibiotik, chemoterapeutik nebo narkotik.
- 10. Přípravek podle nároku 1, vyznačující se tím, že kosmeticky účinná látka je vybrána ze skupiny sestávající z osvěžovačů dechu jako je menthol, chuťových, aromatických ío nebo vonných látek používaných v ústní hygieně a/nebo účinných látek pro zubní péči a ústní hygienu jako jsou kvartemí amoniové zásady.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19646392A DE19646392A1 (de) | 1996-11-11 | 1996-11-11 | Zubereitung zur Anwendung in der Mundhöhle mit einer an der Schleimhaut haftklebenden, Pharmazeutika oder Kosmetika zur dosierten Abgabe enthaltenden Schicht |
| PCT/EP1997/005820 WO1998020862A1 (de) | 1996-11-11 | 1997-10-22 | Sofortige benetzbarkeit aufweisende(r) wasserlöslicher film oder wasserlösliche schicht zur oralen applikation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ164799A3 CZ164799A3 (cs) | 1999-08-11 |
| CZ297354B6 true CZ297354B6 (cs) | 2006-11-15 |
Family
ID=7811214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ0164799A CZ297354B6 (cs) | 1996-11-11 | 1997-10-22 | Prípravek pro aplikaci v ústní dutine s filmem nebo fólií s okamzitou smácitelností |
Country Status (25)
| Country | Link |
|---|---|
| US (8) | US5948430A (cs) |
| EP (2) | EP0936905B1 (cs) |
| JP (3) | JP4063331B2 (cs) |
| KR (2) | KR100569847B1 (cs) |
| AT (2) | ATE422157T1 (cs) |
| AU (1) | AU739698B2 (cs) |
| CA (1) | CA2265651C (cs) |
| CZ (1) | CZ297354B6 (cs) |
| DE (4) | DE19646392A1 (cs) |
| DK (2) | DK0936905T3 (cs) |
| ES (2) | ES2322699T3 (cs) |
| HU (2) | HU228464B1 (cs) |
| ID (1) | ID22526A (cs) |
| IL (2) | IL129819A0 (cs) |
| MY (1) | MY125548A (cs) |
| NO (2) | NO325073B1 (cs) |
| NZ (1) | NZ335063A (cs) |
| PL (1) | PL190376B1 (cs) |
| PT (2) | PT1362584E (cs) |
| SI (1) | SI0936905T1 (cs) |
| SK (2) | SK285100B6 (cs) |
| TR (1) | TR199901633T2 (cs) |
| TW (2) | TWI250029B (cs) |
| WO (1) | WO1998020862A1 (cs) |
| ZA (1) | ZA9710093B (cs) |
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1996
- 1996-11-11 DE DE19646392A patent/DE19646392A1/de not_active Withdrawn
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1997
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- 1997-10-21 TW TW092105140A patent/TWI250029B/zh not_active IP Right Cessation
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- 1997-10-22 SI SI9730590T patent/SI0936905T1/xx unknown
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- 1997-10-22 AU AU48682/97A patent/AU739698B2/en not_active Ceased
- 1997-10-22 HU HU9904207A patent/HU228464B1/hu not_active IP Right Cessation
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- 1997-10-22 DK DK03014213T patent/DK1362584T3/da active
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- 1997-10-22 KR KR1020057014063A patent/KR100569847B1/ko not_active Expired - Fee Related
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1999
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2000
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2001
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2002
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2004
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20161022 |