JP4718445B2 - 鼻副鼻腔炎治療のための製剤 - Google Patents
鼻副鼻腔炎治療のための製剤 Download PDFInfo
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- JP4718445B2 JP4718445B2 JP2006504903A JP2006504903A JP4718445B2 JP 4718445 B2 JP4718445 B2 JP 4718445B2 JP 2006504903 A JP2006504903 A JP 2006504903A JP 2006504903 A JP2006504903 A JP 2006504903A JP 4718445 B2 JP4718445 B2 JP 4718445B2
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- 235000010408 potassium alginate Nutrition 0.000 description 1
- 239000000737 potassium alginate Substances 0.000 description 1
- MZYRDLHIWXQJCQ-YZOKENDUSA-L potassium alginate Chemical compound [K+].[K+].O1[C@@H](C([O-])=O)[C@@H](OC)[C@H](O)[C@H](O)[C@@H]1O[C@@H]1[C@@H](C([O-])=O)O[C@@H](O)[C@@H](O)[C@H]1O MZYRDLHIWXQJCQ-YZOKENDUSA-L 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
- 239000001300 quillaia extract Substances 0.000 description 1
- 235000013852 quillaia extract Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 229950005137 saperconazole Drugs 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000002398 sedimentation field-flow fractionation Methods 0.000 description 1
- 238000009589 serological test Methods 0.000 description 1
- 238000010181 skin prick test Methods 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000003718 sphenoid sinus Anatomy 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002607 sulconazole Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960000699 terbinafine hydrochloride Drugs 0.000 description 1
- 229960000580 terconazole Drugs 0.000 description 1
- 150000005672 tetraenes Chemical class 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229960004880 tolnaftate Drugs 0.000 description 1
- FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 229960005294 triamcinolone Drugs 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 210000001944 turbinate Anatomy 0.000 description 1
- 229940075466 undecylenate Drugs 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 229940032699 vistide Drugs 0.000 description 1
- 229940053728 vitrasert Drugs 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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Description
1つの別の実施形態では、本発明は鼻副鼻腔炎の治療用製剤を対象とする。一実施形態では、製剤は、ステロイド系抗炎症剤を単独で、または抗真菌剤、抗生物質、もしくは抗ウィルス剤と組み合わせて含む。本明細書で用いられる治療とは、鼻副鼻腔炎の予防、防止、または鼻副鼻腔炎の、もしくは鼻副鼻腔炎に付随した1つもしくは複数の症状の改善、または鼻副鼻腔炎の、もしくは鼻副鼻腔炎に付随した、1つもしくは複数の症状を良い方向に変えるか、もしくは悪化するのを防ぐあらゆる手段を意味する。本明細書で用いられる改善とは、永続的でも一時的でも、持続的でも一過性でも、真菌誘導性鼻副鼻腔炎を含むがこれに限定されない鼻副鼻腔炎の1つまたは複数の症状のどのような軽減も意味する。
本明細書で使用する抗真菌剤は、真菌誘導性鼻副鼻腔炎を含む鼻副鼻腔炎を治療する上で有効なあらゆる物質を含む。好ましくは、本製剤の抗真菌剤は、真菌誘導性鼻副鼻腔炎に付随する特徴的な炎症反応および結果として生じる損傷を、永続的でも一時的でも、持続的でも一過性でも減少させるか、止めるか、治療するか、または予防するレベルまで、粘液中の真菌生物体の存在を減少させる。
本明細書で用いるステロイド性抗炎症剤は、フルチカゾン、ベクロメタゾン、薬学的に許容されるそれらのあらゆる誘導体、およびそれらのあらゆる組合せを含む。本明細書で使用されるように、薬学的に許容される誘導体には、それらのあらゆる塩、エステル、エノールエーテル、エノールエステル、酸、塩基、溶媒和物、または水和物が含まれる。これらの誘導体は、知られているこれらの誘導体化方法を用いて当業者が調製することができる。
本製剤の鼻腔内用ステロイドは、プロピオン酸フルチカゾンが好ましい。プロピオン酸フルチカゾンは、合成コルチコステロイドであり、実験式はC25H31F3O5Sである。化学名は、S−(フルオロメチル)6α,9−ジフルオロ−11β−17−ジヒドロキシ−16α−メチル−3−オキソアンドロスタ−1,4−ジエン−17β−カルボチオエート,17−プロピオン酸である。プロピオン酸フルチカゾンは、分子量500.6の白色からオフホワイトの粉末であり、水にほとんど溶けず、ジメチルスルホキシドおよびジメチルホルムアミドに溶けやすく、メタノールおよび95%エタノールに溶けにくい。
また、好ましくは、本製剤のステロイド性抗炎症剤は、ジプロピオン酸ベクロメタゾンまたはその一水和物である。ジプロピオン酸ベクロメタゾンの化学名は、9−クロロ−11b,17,21−トリヒドロキシ−16b−メチルプレグナ−1,4−ジエン−3,20−ジオン17,21−ジプロピオン酸である。化合物は、分子量521.25の白色粉末であってよく、水に溶けにくく(医師用卓上参考書(Physicians’ Desk Reference.RTM))、クロロホルムに極めて溶けやすく、アセトンおよびアルコールに溶けやすい。
本発明の製剤は、抗生物質をさらに含むことができる。さらに、2種以上の細菌生物が鼻−副鼻部の細菌感染に関わることがあるため、本製剤は、アモキシリン、エリスロマイシン、またはセファドロキシルのような広域スペクトルの抗生物質を含むことができる。あるいは、活性スペクトルの異なる抗菌物質の組合せもまた、使用できる。本発明で用いる抗生物質の例を、下記の表3に示す。
本発明の製剤は、治療上有効な量の抗ウィルス剤を1つまたは複数含むことができる。これらの物質は、単独に、または本発明のステロイド性物質と同時に投与することができる。抗ウィルス剤は、また、アシクロビル、ファムシクロビル、バラシクロビル、エドクスジン(edoxudine)、ガンシクロビル、フォスカーネット、シドビル(cidovir)(ビスタイド)、ビトラサート(Vitrasert)、フォーミビルセン(Formivirsen)、HPMPA(9−(3−ヒドロキシ−2−ホスホノメトキシプロピル)アデニン)、PMEA(9−(2−ホスホノメトキシエチル)アデニン)、HPMPG(9−(3−ヒドロキシ−2−(ホスホノメトキシ)プロピル)グアニン)、PMEG(9−[2−(ホスホノメトキシ)エチル]グアニン)、HPMPC(1−(2−ホスホノメトキシ−3−ヒドロキシプロピル)−シトシン)、リバビリン、EICAR(5−エチニル−1−β−D−リボフラノシルイミダゾール−4−カルボキサミン)、ピラゾフリン(3−[β−D−リボフラノシル]−4−ヒドロキシピラゾール−5−カルボキサミン)、3−デアザグアニン(Deazaguanine)、GR−92938X(1−β−D−リボフラノシルピラゾール−3,4−ジカルボキサミド)、LY253963(1,3,4−チアジアゾール−2−イル−シアナミド)、RD3−0028(1,4−ジヒドロ−2,3−ベンゾジチイン(Benzodithiin))、CL387626(4,4’−ビス[4,6−ジ[3−アミノフェニル−N,N−ビス(2−カルバモイルエチル)−スルホニルイミノ]−1,3,5−トリアジン−2−イルアミノ−ビフェニル−2,2’−二スルホン酸二ナトリウム塩、BABIM(ビス[5−アミジノ−2−ベンズイミダゾリル]メタン)、およびNIH351を含むことができる。
本発明の製剤を、真菌誘導性鼻副鼻腔炎を含む鼻副鼻腔炎に付随する1つまたは複数の症状を、予防するか、軽減させるか、または除去するのに有効な量を、有効な頻度で、および有効な期間、哺乳動物に投与することができるならば、製剤はあらゆる形態であることができる。例えば、本発明の範囲内の製剤は、固体、液体、および/またはエアロゾルの形態であることができ、散剤、結晶性物質、ゲル剤、パスタ剤、軟膏、塗剤、クリーム、溶液、懸濁液、部分溶液、スプレー剤、噴霧剤、ミスト剤、噴霧吸入剤、チンキ剤、丸剤、カプセル剤、錠剤、およびゲルカプセル剤を含むが、これらに限定されない。さらに、製剤は、その他の成分、特に本明細書に記載された成分の混合物を含むことができる。例えば、本発明の範囲内の製剤は、1、2、3、4、5、またはそれ以上の異なる抗真菌剤、抗生物質、抗ウィルス剤、または本明細書に記載されたその他の成分を含むことができるが、これらに限定されない。さらに、本発明の範囲内の製剤は、薬学的に許容される水性賦形剤、薬学的に許容される固形賦形剤、ステロイド、粘液溶解剤、抗細菌剤、抗炎症剤、免疫抑制剤、血管拡張剤、血管収縮剤、うっ血除去剤、ロイコトリエン阻害剤、抗コリン作用剤、抗ヒスタミン剤、治療用化合物、およびこれらの組合せを含むがこれらに限定されない、さらなる成分を含むことができる。このような抗ウィルス剤は、IMPDH阻害剤、ウィルス吸着侵入阻害剤、宿主細胞への融合阻害剤、アンチセンスオリゴヌクレオチド、およびヌクレオシド類似体を含むことができる。
本製剤の投与は、本製剤を鼻−副鼻粘膜と接触させるあらゆるタイプの投与であることができる。直接鼻腔内投与は、投与された物質が表皮を通りぬける前に鼻−副鼻粘膜と接触するという条件で、鼻灌注、鼻噴霧、鼻吸入、および浸潤させたガーゼなどによる鼻湿布などを含むが、これらに限定されない。さらに、例えば、針またはカテーテル管を用いて鼻−副鼻腔中に注入することも、投与される物質が針またはカテーテル管を除いた後、および表皮を通りぬける前に鼻−副鼻粘膜と接触するという条件であれば、直接鼻腔内投与であると考えられる。本製剤を鼻腔内に直接投与するためにあらゆる装置を用いることができ、シリンジ、バルブ、吸入器、キャニスター、スプレー缶、ネブライザー、およびマスクが含まれるが、これらに限定されない。
本発明はまた、真菌誘導性鼻副鼻腔炎を含む、鼻副鼻腔炎を治療する方法を目的としたものである。一実施形態では、本発明による鼻副鼻腔炎治療方法は、それを必要とする哺乳動物に本発明の製剤の治療上有効な量を投与するステップを含む。製剤は、本発明のステロイド性物質の単独、または抗真菌剤、抗生物質、もしくは抗ウィルス剤との組合せを含むことができる。製剤は、鼻腔内投与をするのが好ましい。一実施形態では、製剤は鼻−副鼻粘膜に直接投与される。別の実施形態では、製剤は定量噴射式ポンプにより鼻腔内投与される。一般的には、本明細書に記載されたあらゆる活性成分に関する、あらゆる個体の治療方針は、その医師が速やかに決定できる。
実施例1
実施例2
実施例3
実施例4
実施例5
Claims (20)
- 哺乳動物における真菌誘導性鼻副鼻腔炎の治療用の鼻用の製剤であって、
前記鼻用の製剤は、
(a)1から700mcg(μg)の懸濁した固体ステロイド性抗炎症剤、
ここでステロイド性抗炎症剤がフルチカゾンを含み、前記ステロイド性抗炎症剤が以下の粒度分布プロファイルを有し、
i.ステロイド性抗炎症剤粒子の10%が、0.90ミクロン未満の粒子サイズを有し;
ii.ステロイド性抗炎症剤粒子の25%が、1.6ミクロン未満の粒子サイズを有し;
iii.ステロイド性抗炎症剤粒子の50%が、3.2ミクロン未満の粒子サイズを有し;
iv.ステロイド性抗炎症剤粒子の75%が、6.2ミクロン未満の粒子サイズを有し;
v.ステロイド性抗炎症剤粒子の90%が、10.0ミクロン未満の粒子サイズを有する;
および
(b)0.5から150mgの抗真菌剤
を含有する水性懸濁液を含み、
前記鼻用の製剤は、鼻から副鼻の粘膜への投与に適している
ことを特徴とする鼻用の製剤。 - 哺乳動物における真菌誘導性鼻副鼻腔炎の治療用の鼻用の製剤であって、
前記鼻用の製剤は、
(a)1から700mcg(μg)の懸濁した固体ステロイド性抗炎症剤、
ここでステロイド性抗炎症剤がベクロメタゾンを含み、前記ステロイド性抗炎症剤が以下の粒度分布プロファイルを有し、
i.ステロイド性抗炎症剤粒子の10%が、0.75ミクロン未満の粒子サイズを有し;
ii.ステロイド性抗炎症剤粒子の25%が、1.5ミクロン未満の粒子サイズを有し;
iii.ステロイド性抗炎症剤粒子の50%が、2.0ミクロン未満の粒子サイズを有し;
iv.ステロイド性抗炎症剤粒子の75%が、3.5ミクロン未満の粒子サイズを有し;
および
v.ステロイド性抗炎症剤粒子の90%が、5.0ミクロン未満の粒子サイズを有する;
および
(b)0.5から150mgの抗真菌剤
を含有する水性懸濁液を含み、
前記鼻用の製剤は、鼻から副鼻の粘膜への投与に適している
ことを特徴とする鼻用の製剤。 - エチレンジアミンテトラ酢酸、クエン酸、ニトリロトリ酢酸、これらの塩、およびエデト酸ナトリウムからなる群から選択される少なくとも1種の錯化剤を更に含む、請求項1または2に記載の鼻用の製剤。
- 前記鼻用の製剤がアムホテリシンβを7.5から15mg含む、請求項3に記載の鼻用の製剤。
- 前記鼻用の製剤がフルコナゾールまたはイトラコナゾールを20から70mg含む、請求項3に記載の鼻用の製剤。
- 前記鼻用の製剤がフルコナゾールまたはイトラコナゾールを30mg、およびアシクロビル、ファムシクロビル、バラシクロビル、エドクスジン、ガンシクロビル、フォスカーネット、シドビル(ビスタイド)、ビトラサートおよびフォーミビルセンからなる群から選択される抗ウイルス剤の治療上の有効量を含む、請求項3に記載の鼻用の製剤。
- 前記ステロイド性抗炎症剤を25から400mcg(μg)含む、請求項1に記載の鼻用の製剤。
- 前記鼻用の製剤が、ステロイド性抗炎症剤を0.2から3mg含む、請求項2に記載の鼻用の製剤。
- 前記鼻用の製剤が無菌である、請求項1に記載の鼻用の製剤。
- 前記鼻用の製剤が保存剤をさらに含む、請求項1に記載の鼻用の製剤。
- 前記保存剤が塩化ベンザルコニウムである、請求項10に記載の鼻用の製剤。
- 前記鼻用の製剤が安定である、請求項1に記載の鼻用の製剤。
- 前記鼻用の製剤が定量噴射式ポンプボトル入りである、請求項3に記載の鼻用の製剤。
- 以下の化合物:
(a)微晶質セルロース;
(b)カルボキシメチルセルロースナトリウム;
(c)デキストロース;
(d)塩化ベンザルコニウム;
(e)ポリソルベート80;および、
(g)フェニルエチルアルコール;
の1つまたは複数を、乾燥重量ベースで0.01重量%から90重量%さらに含む、請求項3に記載の鼻用の製剤。 - 抗生物質をさらに含む、請求項1に記載の鼻用の製剤。
- 抗生物質が、アミカシン、アジスロマイシン、アズトレオナン、セファゾリン、セフェピン、セフォニシド、セファペラゾン(Cefaperazone)、セフォタキシム、セフォテタン、セフォキシチン、セフタジジム、セフチゾキシム、セフトリアキソン、セフロキシム、セファピリン、シプロフロキサシン、クリンダマイシン、ドキシサイクリン、ラクトビオン酸エリスロマイシン、ゲンタマイシン、カナマイシン、リネゾリド、メズロシリン、ムピロシン、ナフシリン、ネチルマイシン、ネオマイシン、オキサシリン、パロモマイシン、ピペラシリン、ストレプトマイシン、チカルシリン、トブラマイシン、およびバンコマイシンからなる群から選択される1つまたは複数である、請求項15に記載の鼻用の製剤。
- 前記鼻用の製剤が硫酸ネオマイシンを1から800mg含む、請求項15に記載の鼻用の製剤。
- 前記鼻用の製剤が硫酸ネオマイシンを5から500mg含む、請求項15に記載の鼻用の製剤。
- 前記鼻用の製剤が硫酸ネオマイシンを50から300mg含む、請求項15に記載の鼻用の製剤。
- 前記鼻用の製剤が硫酸ネオマイシンを150mg含む、請求項15に記載の鼻用の製剤。
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US10/657,550 US8912174B2 (en) | 2003-04-16 | 2003-09-04 | Formulations and methods for treating rhinosinusitis |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8912174B2 (en) | 2003-04-16 | 2014-12-16 | Mylan Pharmaceuticals Inc. | Formulations and methods for treating rhinosinusitis |
US9180126B2 (en) | 2003-04-16 | 2015-11-10 | Mylan Specialty L.P. | Formulations and methods for treating rhinosinusitis |
US9808471B2 (en) | 2003-04-16 | 2017-11-07 | Mylan Specialty Lp | Nasal pharmaceutical formulations and methods of using the same |
Also Published As
Publication number | Publication date |
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US8309061B2 (en) | 2012-11-13 |
BRPI0409348A (pt) | 2006-04-25 |
US8129364B2 (en) | 2012-03-06 |
US20080058296A1 (en) | 2008-03-06 |
KR101396262B1 (ko) | 2014-05-19 |
RU2410083C2 (ru) | 2011-01-27 |
CA2522294C (en) | 2014-05-06 |
US8912174B2 (en) | 2014-12-16 |
US20040209852A1 (en) | 2004-10-21 |
WO2004091576A1 (en) | 2004-10-28 |
EP1613282B1 (en) | 2018-05-02 |
AU2004229149A1 (en) | 2004-10-28 |
US20060051300A1 (en) | 2006-03-09 |
EP1613282A1 (en) | 2006-01-11 |
MXPA05011106A (es) | 2005-12-12 |
CA2522294A1 (en) | 2004-10-28 |
US20120237559A1 (en) | 2012-09-20 |
JP2006523631A (ja) | 2006-10-19 |
US20050180925A1 (en) | 2005-08-18 |
KR20060003019A (ko) | 2006-01-09 |
MX364708B (es) | 2019-05-06 |
BRPI0409348B1 (pt) | 2019-04-24 |
US9180126B2 (en) | 2015-11-10 |
PL377855A1 (pl) | 2006-02-20 |
RU2005135333A (ru) | 2006-03-20 |
BRPI0409348B8 (pt) | 2021-05-25 |
US8663695B2 (en) | 2014-03-04 |
HK1089676A1 (en) | 2006-12-08 |
PL222059B1 (pl) | 2016-06-30 |
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