JPWO2011025035A1 - コーティング用組成物 - Google Patents
コーティング用組成物 Download PDFInfo
- Publication number
- JPWO2011025035A1 JPWO2011025035A1 JP2011528906A JP2011528906A JPWO2011025035A1 JP WO2011025035 A1 JPWO2011025035 A1 JP WO2011025035A1 JP 2011528906 A JP2011528906 A JP 2011528906A JP 2011528906 A JP2011528906 A JP 2011528906A JP WO2011025035 A1 JPWO2011025035 A1 JP WO2011025035A1
- Authority
- JP
- Japan
- Prior art keywords
- coating
- coating composition
- polyvinyl alcohol
- polymer
- composition according
- 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
- 239000008199 coating composition Substances 0.000 title claims abstract description 62
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 102
- 238000000576 coating method Methods 0.000 claims abstract description 91
- 239000011248 coating agent Substances 0.000 claims abstract description 90
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 79
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 39
- 239000000178 monomer Substances 0.000 claims abstract description 36
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 35
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- 229920001577 copolymer Polymers 0.000 claims abstract description 15
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims description 42
- 239000007787 solid Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 19
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 19
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 18
- -1 alkylamine salts Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 15
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims description 11
- 229920002678 cellulose Polymers 0.000 claims description 11
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- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 7
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 6
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 6
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
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- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 5
- 159000000001 potassium salts Chemical class 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 4
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
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- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
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- 229920000609 methyl cellulose Polymers 0.000 claims description 3
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- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 3
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 3
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- 235000019422 polyvinyl alcohol Nutrition 0.000 description 78
- 239000003826 tablet Substances 0.000 description 35
- 239000003814 drug Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 13
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- 235000019645 odor Nutrition 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000003905 agrochemical Substances 0.000 description 4
- 239000003337 fertilizer Substances 0.000 description 4
- 230000000873 masking effect Effects 0.000 description 4
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- 239000003505 polymerization initiator Substances 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
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- 238000005507 spraying Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
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- 235000019658 bitter taste Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 238000011156 evaluation Methods 0.000 description 3
- 239000007941 film coated tablet Substances 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
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- 239000002994 raw material Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- 239000004129 EU approved improving agent Substances 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
項1.
(A)ポリビニルアルコール及び/又はその誘導体の存在下、少なくとも1種の重合性ビニル単量体を重合又は共重合した重合体又は共重合体、及び、
(B)セルロース系高分子
を含むことを特徴とするコーティング用組成物。
項2.
重合性ビニル単量体が、不飽和カルボン酸類又はその塩類、及び不飽和カルボン酸のエステル類からなる群より選択されるものである、項1に記載のコーティング用組成物。
項3.
重合性ビニル単量体が、下記一般式[1]
H2C=C(R1)−COOR2 [1]
〔式中、R1は水素原子またはメチル基を示し、R2は水素原子または1〜4個の炭素原子を有するアルキル基を示す。〕
で表される化合物又はその塩である、
項1に記載のコーティング用組成物。
項4.
(A)の重合体又は共重合体が、
ポリビニルアルコール及び/又はその誘導体の存在下、
(I)アクリル酸、メタクリル酸、これらのナトリウム塩、カリウム塩、アンモニウム塩、及びアルキルアミン塩からなる群より選択される少なくとも1種、並びに(II)メチルメタクリレート、メチルアクリレート、エチルメタクリレート、エチルアクリレート、ブチルメタクリレート、ブチルアクリレート、イソブチルメタクリレート、及びイソブチルアクリレートからなる群より選択される少なくとも1種の重合性ビニル単量体を重合又は共重合した重合体又は共重合体である、
項1に記載のコーティング用組成物。
項5.
(II)がメチルメタクリレートである、項5に記載のコーティング用組成物。
項6.
セルロース系高分子が、ヒドロキシプロピルメチルセルロース、ヒドロキシプロピルセルロース、メチルセルロース、及びヒドロキシエチルセルロースからなる群より選ばれる少なくとも1種であることを特徴とする項1〜5のいずれかに記載のコーティング用組成物。
項7.
前記(A)と(B)の比率が、重量比で、(A):(B)=1:0.02〜2.5程度である項1〜6のいずれかに記載のコーティング用組成物。
項8.
項1〜7のいずれかに記載のコーティング用組成物を固形製剤にコーティングしたコーティング製剤。
項9−1.
項1〜7のいずれかに記載のコーティング用組成物を固形製剤に塗布する工程を含む、コーティング製剤を製造する方法。
項9−2.
項1〜7のいずれかに記載のコーティング用組成物を固形製剤に塗布することによりコーティング製剤を製造する方法。
項10−1.
項1〜7のいずれかに記載のコーティング用組成物を固形製剤に塗布する工程を含む、固形製剤をコーティングする方法。
項10−2.
項1〜7のいずれかに記載のコーティング用組成物を固形製剤に塗布することによりコーティングする方法。
項11.固形製剤コーティング用である、項1〜7のいずれかに記載のコーティング用組成物。
項12.スプレーコーティング用である、項1〜7及び11のいずれかに記載のコーティング用組成物。
また、臭いや苦みのマスキング効果、酸素透過防止効果も有する。
本発明のコーティング組成物における成分の一つであるポリビニルアルコール重合体は、ポリビニルアルコールまたはその誘導体の存在下、少なくとも1種の重合性ビニル単量体を公知の重合方法で重合又は共重合させることにより製造することができる。公知の重合方法としては、例えばラジカル重合を挙げることができ、またその具体的な方法として、例えば溶液重合法、懸濁重合法、乳化重合法および塊状重合などを挙げることができる。
一般式[1]
H2C=C(R1)−COOR2 [1]
〔式中、R1は水素原子またはメチル基を示し、R2は水素原子または1〜4個の炭素原子を有するアルキル基を示す。〕
で表される化合物である。具体的には、アクリル酸、メタクリル酸、メチルメタクリレート、メチルアクリレート、エチルメタクリレート、エチルアクリレート、プロピルメタクリレート、プロピルアクリレート、ブチルメタクリレート、ブチルアクリレート、イソブチルメタクリレート、イソブチルアクリレートが挙げられる。アクリル酸及びメタクリル酸は、これらの塩を用いることもできる。例えば、これらのナトリウム塩、カリウム塩、アンモニウム塩、又はアルキルアミン塩等を用いてもよい。
セルロース系高分子としては、セルロースの水酸基をエステル化又はエーテル化した高分子が好ましく用いられる。
本発明のコーティング用組成物は、上記(A)ポリビニルアルコール及び/又はその誘導体の存在下、少なくとも1種の重合性ビニル単量体を重合又は共重合した重合体又は共重合体(ポリビニルアルコール重合体)、及び、上記(B)セルロース系高分子、を含むことを特徴とする。
さらにまた、本発明のコ−テイング組成物は、酸素透過防止効果をも有するので、酸化分解を受けやすい医薬(例えばアスコルビン酸、ビタミンA、ビタミンEなど)、動物薬、農薬、肥料、食品のコーティングに有用である。
本発明のコーティング製剤は、固形製剤等の表面に上記本発明のコーティング用組成物が被覆された製剤である。
実施例A
冷却還流管、滴下ロート、温度計、窒素導入管及び攪拌装置を取り付けたセパラブルフラスコにポリビニルアルコール(EG05、平均重合度500、けん化度88%、日本合成化学製)175.8g、イオン交換水582.3gを仕込み、常温で分散させた後95℃で完全溶解させた。次いでアクリル酸5.4g、メチルメタクリレート37.3gを添加し、窒素置換後50℃まで昇温した後、ターシャリーブチルハイドロパーオキサイド8.5g、エリソルビン酸ナトリウム8.5gを添加し4時間で反応を終了させた。これを乾燥・粉砕してポリビニルアルコール共重合体(粉末)を得た。以下、当該ポリビニルアルコール共重合体をPVA共重合体とも標記する。当該PVA共重合体は、(ポリビニルアルコール:メチルメタクリレート:アクリル酸)の重量比がおよそ(80:17.5:2.5)である。当該PVA共重合体4.75gとヒドロキシプロピルメチルセルロース(TC−5R(登録商標)、信越化学工業(株)製、重量平均分子量35600g/mol)0.25gを62.5gの精製水に溶解させてコーティング液を作製した。なお、用いた当該ヒドロキシプロピルセルロースは、導入されている置換基の割合が、セルロースの全水酸基を100%とした場合、メトキシ基約29%、ヒドロキシプロポキシ基約10%である。
PVA共重合体の量を4.75gに代えて4.5gとし、HPMCの量を0.25gに代えて0.5gとする以外は、実施例Aと同様にしてコーティング液を作製した。
PVA共重合体の量を4.75gに代えて4.25gとし、HPMCの量を0.25gに代えて0.75gとする以外は、実施例Aと同様にしてコーティング液を作製した。
PVA共重合体の量を4.75gに代えて4.0gとし、HPMCの量を0.25gに代えて1.0gとする以外は、実施例Aと同様にしてコーティング液を作製した。
PVA共重合体の量を4.75gに代えて3.5gとし、HPMCの量を0.25gに代えて1.5gとする以外は、実施例Aと同様にしてコーティング液を作製した。
PVA共重合体の量を4.75gに代えて2.5gとし、HPMCの量を0.25gに代えて2.5gとする以外は、実施例Aと同様にしてコーティング液を作製した。
PVA共重合体の量を4.75gに代えて1.5gとし、HPMCの量を0.25gに代えて3.5gとする以外は、実施例Aと同様にしてコーティング液を作製した。
PVA共重合体4.0gとヒドロキシプロピルセルロース(NISSO HPC−L(登録商標)、日本曹達(株)製)1.0gを62.5gの精製水に溶解させてコーティング液を作製した。
PVA共重合体5.0gを62.5gの精製水に溶解してコーティング液を作製した。
HPMC(TC−5R(登録商標)、信越化学工業(株)製、重量平均分子量35600g/mol)5.0gを62.5gの精製水に溶解して、コーティング液を作製した。
ドラフトチューブ付き噴流層コーティング装置(Grow Max 140 不二パウダル(株)製)を用いて、錠剤径Φ8.1mm、重量195mgの素錠50gにコーティングを行った。
実施例A〜Gおよび比較例Aのコーティング液を用いて、上記錠剤にコーティングする際の速度の比較検討を行った。結果を表1に示す。なお、コーティング液が無くなった時点でコーティング終了とした。
上記実施例A〜H及び比較例A〜Bのコーティング液を用いてコーティングしたコーティング錠について、40℃の乾燥機で2日間乾燥させた後、25℃75%RH(相対湿度)の条件下で保存し、各時間経過後の錠剤の含水率の増加を重量変化より算出した。
Claims (10)
- (A)ポリビニルアルコール及び/又はその誘導体の存在下、少なくとも1種の重合性ビニル単量体を重合又は共重合した重合体又は共重合体、及び、
(B)セルロース系高分子
を含むことを特徴とするコーティング用組成物。 - 重合性ビニル単量体が、不飽和カルボン酸類又はその塩類、及び不飽和カルボン酸のエステル類からなる群より選択されるものである、請求項1に記載のコーティング用組成物。
- 重合性ビニル単量体が、下記一般式[1]
H2C=C(R1)−COOR2 [1]
〔式中、R1は水素原子またはメチル基を示し、R2は水素原子または1〜4個の炭素原子を有するアルキル基を示す。〕
で表される化合物又はその塩である、
請求項1に記載のコーティング用組成物。 - (A)の重合体又は共重合体が、
ポリビニルアルコール及び/又はその誘導体の存在下、
(I)アクリル酸、メタクリル酸、これらのナトリウム塩、カリウム塩、アンモニウム塩、及びアルキルアミン塩からなる群より選択される少なくとも1種、並びに
(II)メチルメタクリレート、メチルアクリレート、エチルメタクリレート、エチルアクリレート、プロピルメタクリレート、プロピルアクリレート、ブチルメタクリレート、ブチルアクリレート、イソブチルメタクリレート、及びイソブチルアクリレートからなる群より選択される少なくとも1種の重合性ビニル単量体
を重合又は共重合した重合体又は共重合体である、請求項1に記載のコーティング用組成物。 - (II)がメチルメタクリレートである、請求項5に記載のコーティング用組成物。
- セルロース系高分子が、ヒドロキシプロピルメチルセルロース、ヒドロキシプロピルセルロース、メチルセルロース、及びヒドロキシエチルセルロースからなる群より選ばれる少なくとも1種であることを特徴とする請求項1〜5のいずれかに記載のコーティング用組成物。
- 前記(A)と(B)の比率が、重量比で、(A):(B)=1:0.02〜2.5程度である請求項1〜6のいずれかに記載のコーティング用組成物。
- 請求項1〜7のいずれかに記載のコーティング用組成物を固形製剤にコーティングしたコーティング製剤。
- 項1〜7のいずれかに記載のコーティング用組成物を固形製剤に塗布する工程を含む、コーティング製剤を製造する方法。
- 項1〜7のいずれかに記載のコーティング用組成物を固形製剤に塗布する工程を含む、固形製剤をコーティングする方法。
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JP2002316928A (ja) * | 2001-04-17 | 2002-10-31 | Lion Corp | コーティング錠及びコーティング錠のはがれを防止する方法 |
KR100439156B1 (ko) * | 2001-07-05 | 2004-07-05 | 주식회사 에스앤지바이오텍 | 약물 방출 스텐트용 코팅 조성물 및 이의 제조 방법 |
ES2395724T3 (es) * | 2003-08-20 | 2013-02-14 | Shionogi & Co., Ltd. | Nueva composición de recubrimiento |
US20080014271A1 (en) * | 2006-07-13 | 2008-01-17 | Ucb, S.A. | Novel pharmaceutical compositions comprising levetiracetam |
JP5047572B2 (ja) * | 2006-09-21 | 2012-10-10 | 京都薬品工業株式会社 | 臭いの防止された固形医薬製剤の製造方法、及びそれにより得られる固形医薬製剤 |
EP2140883B1 (en) * | 2007-04-20 | 2012-10-31 | Daido Chemical Corporation | Novel base for dry solid dispersion, solid dispersion containing the base, and composition containing the dispersion |
JP2009023943A (ja) * | 2007-07-19 | 2009-02-05 | Kyoto Pharmaceutical Industries Ltd | フィルムコーティング方法 |
TW200927197A (en) * | 2007-10-29 | 2009-07-01 | Daiichi Sankyo Co Ltd | Film coated preparation |
-
2010
- 2010-08-31 US US13/392,252 patent/US20120157580A1/en not_active Abandoned
- 2010-08-31 EP EP10812081.7A patent/EP2474324A4/en not_active Withdrawn
- 2010-08-31 JP JP2011528906A patent/JP5730205B2/ja active Active
- 2010-08-31 WO PCT/JP2010/064815 patent/WO2011025035A1/ja active Application Filing
- 2010-08-31 KR KR1020127008187A patent/KR20120083364A/ko not_active Application Discontinuation
- 2010-08-31 CN CN201080036911XA patent/CN102470177A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
WO2011025035A9 (ja) | 2011-06-23 |
JP5730205B2 (ja) | 2015-06-03 |
CN102470177A (zh) | 2012-05-23 |
KR20120083364A (ko) | 2012-07-25 |
US20120157580A1 (en) | 2012-06-21 |
WO2011025035A1 (ja) | 2011-03-03 |
EP2474324A4 (en) | 2013-08-28 |
EP2474324A1 (en) | 2012-07-11 |
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