JP2018507306A - 低い中和度を有する水溶性エステル化セルロースエーテル - Google Patents
低い中和度を有する水溶性エステル化セルロースエーテル Download PDFInfo
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- JP2018507306A JP2018507306A JP2017545912A JP2017545912A JP2018507306A JP 2018507306 A JP2018507306 A JP 2018507306A JP 2017545912 A JP2017545912 A JP 2017545912A JP 2017545912 A JP2017545912 A JP 2017545912A JP 2018507306 A JP2018507306 A JP 2018507306A
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- Prior art keywords
- esterified cellulose
- cellulose ether
- weight
- group
- hpmcas
- 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
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- 229920003086 cellulose ether Polymers 0.000 title claims abstract description 146
- 238000006386 neutralization reaction Methods 0.000 title claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000006467 substitution reaction Methods 0.000 claims abstract description 45
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 30
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 19
- 150000002148 esters Chemical group 0.000 claims abstract description 19
- 125000002252 acyl group Chemical group 0.000 claims abstract description 15
- 239000002775 capsule Substances 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 55
- 239000007788 liquid Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 26
- 239000003085 diluting agent Substances 0.000 claims description 20
- 239000002552 dosage form Substances 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 229920002678 cellulose Polymers 0.000 claims description 9
- 239000001913 cellulose Substances 0.000 claims description 9
- 239000007962 solid dispersion Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 235000015872 dietary supplement Nutrition 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 description 85
- ZUAAPNNKRHMPKG-UHFFFAOYSA-N acetic acid;butanedioic acid;methanol;propane-1,2-diol Chemical compound OC.CC(O)=O.CC(O)CO.OC(=O)CCC(O)=O ZUAAPNNKRHMPKG-UHFFFAOYSA-N 0.000 description 84
- -1 succinoyl groups Chemical group 0.000 description 38
- 239000000243 solution Substances 0.000 description 37
- 239000007864 aqueous solution Substances 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000012634 fragment Substances 0.000 description 24
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000008186 active pharmaceutical agent Substances 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 239000000499 gel Substances 0.000 description 13
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 12
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 12
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 12
- 239000012062 aqueous buffer Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000001879 gelation Methods 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- 238000004519 manufacturing process Methods 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 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 description 5
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 5
- 238000000518 rheometry Methods 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IYKJEILNJZQJPU-UHFFFAOYSA-N acetic acid;butanedioic acid Chemical compound CC(O)=O.OC(=O)CCC(O)=O IYKJEILNJZQJPU-UHFFFAOYSA-N 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229920013820 alkyl cellulose Polymers 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 230000001419 dependent effect Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RPZANUYHRMRTTE-UHFFFAOYSA-N 2,3,4-trimethoxy-6-(methoxymethyl)-5-[3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxyoxane;1-[[3,4,5-tris(2-hydroxybutoxy)-6-[4,5,6-tris(2-hydroxybutoxy)-2-(2-hydroxybutoxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]butan-2-ol Chemical compound COC1C(OC)C(OC)C(COC)OC1OC1C(OC)C(OC)C(OC)OC1COC.CCC(O)COC1C(OCC(O)CC)C(OCC(O)CC)C(COCC(O)CC)OC1OC1C(OCC(O)CC)C(OCC(O)CC)C(OCC(O)CC)OC1COCC(O)CC RPZANUYHRMRTTE-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- JEJBBWQXAMSBQT-UHFFFAOYSA-N butanedioic acid;propanoic acid Chemical compound CCC(O)=O.OC(=O)CCC(O)=O JEJBBWQXAMSBQT-UHFFFAOYSA-N 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 210000000813 small intestine Anatomy 0.000 description 2
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- 239000001069 triethyl citrate Substances 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000003535 D-glucopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000006169 McIlvaine's buffer solution Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920003097 Methocel™ E3 LV Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
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- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
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- 238000012377 drug delivery Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
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- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
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- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B13/00—Preparation of cellulose ether-esters
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
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Abstract
Description
i)基−C(O)−R−COOHの中和度が0.4以下であり、
ii)総エステル置換度が0.10〜0.70であり、
iii)エステル化セルロースエーテルが、2℃において少なくとも2.0重量パーセントの、水への溶解性を有する、エステル化セルロースエーテルである。
エステル化セルロースエーテルにおけるエーテル基の含有量は、「Hypromellose」、United States Pharmacopeia and National Formulary、USP35、3467−3469頁に記載されているものと同じ手法で決定される。
特に明記しない限り、Mw及びMnは、Journal of Pharmaceutical and Biomedical Analysis 56(2011)743に従って測定される。移動相は、アセトニトリル40体積部と、50mMのNaH2PO4及び0.1MのNaNO3を含有する水性緩衝液60体積部との混合物であった。移動相を8.0のpHに調整した。セルロースエーテルエステルの溶液を、0.45μmの孔径のシリンジフィルターを通してHPLCバイアルに濾過した。Mw及びMnの測定の正確な詳細は、国際特許出願第WO2014/137777号でセクション「Examples」において「Determination of Mw,Mn and Mz」の表題で開示されている。本発明の全ての実施例において、回収率は少なくとも96%であった。比較例では、回収率は少なくとも89%であった。
定性的決定:その乾燥重量を基準として2.0gのHPMCASを98.0gの水と激しい攪拌下で0.5℃において16時間混合することによって2重量パーセントのHPMCASと水との混合物を調製した。次いで、HPMCASと水との混合物の温度を5℃に上げた。エステル化セルロースエーテルの水溶解性を視覚的検査により決定した。HPMCASが5℃において2%で水溶性であるかどうかの決定を以下のように行った。「2%で水溶性−有」は、沈殿物のない溶液が上記の手順に従って得られたことを意味する。「2%で水溶性−無」は、その乾燥重量を基準として2.0gのHPMCASを98.0gの水と上記の手順に従って混合したときに、HPMCASの少なくともかなりの部分が溶解しないままであり沈殿物を形成したことを意味する。「2%で水溶性−部分的」は、その乾燥重量を基準として2.0gのHPMCASを98.0gの水と上記の手順に従って混合したときに、HPMCASのごく一部だけが溶解しないままであり沈殿物を形成したことを意味する。
0.43重量%の水性NaOH中2.0重量%のHPMCASの溶液を「Hypromellose Acetate Succinate、United States Pharmacopia and National Formulary、NF29、1548−1550頁」に記載されているように調製した。DIN51562−1:1999−01(1999年1月)に従ったウベローデ粘度測定を実施した。測定は20℃で行った。0.43重量%の水性NaOH中2.0重量%のHPMCASの溶液を、この性質が測定されたそれらの実施例及び比較例について、以下の表2に「NaOH中2.0%粘度」として列挙する。
挽き(milled)、粉末にし(ground)、乾燥した3gのHPMCAS(HPMCASの水含有量を考慮)を、3翼(翼=2cm)ブレードスターラーを用いて750rpmでオーバーヘッドラボスターラーを用いて攪拌しながら室温で147gの水(温度20〜25℃)に添加することによりHPMCASの2%水溶液を生成した。次いで、溶液を約1.5℃に冷却した。1.5℃の温度に達した後、溶液を500rpmで120分間攪拌した。各溶液を特性評価の前に冷蔵庫内に保存した。
コハク酸無水物及び酢酸無水物を70℃で氷酢酸に溶解した。次いで、ヒドロキシプロピルメチルセルロース(HPMC、水を含まない)を攪拌しながら添加した。その量は以下の表1に列挙されている。HPMCの量は乾燥ベースで計算される。いかなる量の酢酸ナトリウムも添加しなかった。
酢酸ナトリウムを他の反応物と以下の表1に列挙された量で混合したことを除いて、比較例A〜Eを実施例1〜27について記載したように生成した。比較例A〜Eは比較目的のものであるが、先行技術に記載されていない。
比較例CE−H〜CE−Jは、国際特許出願第WO2014/137777号の比較例H〜Jに相当する。WO2014/137777の24頁及び国際特許出願第WO2011/159626号の1及び2頁に開示されているように、HPMCASは現在、Shin−Etsu Chemical Co.,Ltd.(Tokyo、Japan)から商業的に入手可能であり、商品名「AQOAT」で知られている。Shin−Etsuは、種々のpHレベルの腸溶性保護を提供するために、置換基レベルの異なる組み合わせを有する、3つの等級のAQOATポリマー、典型的には、AS−LFまたはAS−LGなど、良好(fine)に対して記号表示「F」または「G」が後に続く、AS−L、AS−M、及びAS−Hを製造している。それらの販売仕様は、WO2011/159626の2頁の表1及びWO2014/137777の24頁に列挙されている。Shin−Etsuの技術パンフレット「Shin−Etsu AQOAT Enteric Coating Agent」の04.9 05.2/500版によれば、AQOATポリマーの全ての等級は10%NaOHに可溶性であるが、精製水には不溶性である。WO2011/159626の13頁の表2に開示されているAQOATポリマーの全ての等級の分析されたサンプルのデータを以下に列挙する。
DSM=DS(メトキシル):メトキシル基での置換度、
MSHP=MS(ヒドロキシプロポキシル):ヒドロキシプロポキシル基でのモル置換、
DSAc:アセチル基の置換度、
DSS:スクシノイル基の置換度。
0.10〜0.65、特に0.20〜0.65の総エステル置換度を有するHPMCASの水溶液は、わずかに上昇した温度、典型的には30〜55℃でゲル化する。図2は、実施例23の2重量%のHPMCASの水溶液が40℃においてゲル化しているプロセスにある間のその溶液の写真描写である。図3は、実施例18の5.45重量%のHPMCASの溶液が40℃においてゲル化した後のその溶液の写真描写である。ゲル化したHPMCASを含有するガラスボトルは、ゲル化したHPMCASを流動させることなく、逆さにすることができる。その5.45重量%の溶液は、5℃において低い粘度(233mPa・s、カップ及びボブジオメトリ(CC−25)において10秒−1でHaake RS600レオメーターを使用して測定)を有し、これで都合の良い処理が可能である。レオロジー測定を実施して、上記に更に記載されているように実施例1及び3〜27の2重量%のHPMCASの水溶液の55℃における貯蔵弾性率G’によるゲル化温度及びゲル強度を測定した。結果を以下の表3に列挙する。
HPMCASを2℃の温度において脱イオン水に溶解させることによって実施例15の水溶性HPMCASの9.0重量%の水溶液を調製した。クエン酸トリエチルを可塑剤としてHPMCASの重量を基準として33重量%の量で添加した。21℃、30℃、及び55℃の温度をそれぞれ有する金属ピンを8℃の温度を有するHPMCAS溶液に浸漬することによってカプセルシェルを生成した。次いで、ピンをHPMCAS水溶液から引き抜き、フィルムを成形ピン上に形成させた。良好な品質のカプセルシェルがこれらの温度のそれぞれでピン上に形成した。図4A、5A、及び6Aは、21℃、30℃、及び55℃の温度をそれぞれ有する金属ピン上のカプセルシェルの写真描写である。室温(21℃)を有するピン上に形成されたカプセルシェルを室温で乾燥させ、30℃の温度を有するピン上に形成されたカプセルシェルを30℃で乾燥させ、55℃の温度を有するピン上に形成されたカプセルシェルを55℃で乾燥させた。図4B、図5B、及び図6Bは、カプセルシェルが浸漬ピンから取り除かれた後、21℃、30℃、及び55℃の温度をそれぞれ有する金属ピン上に形成されたカプセルシェルの断片の写真描写である。
HPMCASを2℃の温度において脱イオン水に溶解させることによって実施例23の水溶性HPMCASの7.5重量%の水溶液を調製した。クエン酸トリエチルを可塑剤としてHPMCASの重量を基準として20重量%の量で添加した。80℃の温度を有する金属ピンを10℃の温度を有するHPMCAS溶液に浸漬することによってカプセルシェルを生成した。ピン上に形成したカプセルを80℃で乾燥させた。調製したカプセルシェルは、実施例15のHPMCASから調製されたカプセルと同じ外観を有しており、0.1NのHCL及びpH6.8の水性緩衝溶液において同じ溶解性質を示した。
Claims (15)
- 脂肪族一価アシル基及び式−C(O)−R−COOH(Rは二価の炭化水素基である)の基を含む、エステル化セルロースエーテルであって、
i)前記基−C(O)−R−COOHの中和度が0.4以下であり、
ii)総エステル置換度が0.10〜0.70であり、
iii)前記エステル化セルロースエーテルが、2℃において少なくとも2.0重量パーセントの、水への溶解性を有する、エステル化セルロースエーテル。 - 前記総エステル置換度が0.20〜0.60である、請求項1に記載のエステル化セルロースエーテル。
- 0.25〜0.69の脂肪族一価アシル基の置換度または0.05〜0.45の式−C(O)−R−COOHの基の置換度を有する、請求項1または請求項2に記載のエステル化セルロースエーテル。
- 前記脂肪族一価アシル基がアセチル、プロピオニル、またはブチリル基であり、前記式−C(O)−R−COOHの前記基が−C(O)−CH2−CH2−COOHである、請求項1〜3のいずれか1項に記載のエステル化セルロースエーテル。
- 前記エステル化セルロースエーテルの少なくとも85重量%が、2℃において2.5重量部の前記エステル化セルロースエーテルと97.5重量部の水との混合物に可溶性である、請求項1〜4のいずれか1項に記載のエステル化セルロースエーテル。
- 前記エステル化セルロースエーテルの少なくとも90重量%が、2℃において2.5重量部のエステル化セルロースエーテルと97.5重量部の水との混合物に可溶性である、請求項5に記載のエステル化セルロースエーテル。
- 水性液体に溶解した請求項1〜6のいずれか1項に記載のエステル化セルロースエーテルを含む水性組成物。
- 前記水性組成物の総重量を基準として、少なくとも10重量パーセントの溶解したエステル化セルロースエーテルを含む、請求項7に記載の水性組成物。
- 請求項1〜6のいずれか1項に記載の少なくとも1種のエステル化セルロースエーテルと、有機希釈剤とを含む、液体組成物。
- 請求項7〜9のいずれか1項に記載の組成物を前記剤形と接触させる工程を含む、剤形をコーティングするためのプロセス。
- 請求項7〜9のいずれか1項に記載の組成物を浸漬ピンと接触させる工程を含む、カプセルシェルを製造するためのプロセス。
- コーティングされた剤形であって、前記コーティングが、請求項1〜6のいずれか1項に記載の少なくとも1種のエステル化セルロースエーテルを含む、コーティングされた剤形。
- 請求項1〜6のいずれか1項に記載の少なくとも1種のエステル化セルロースエーテルを含む、ポリマーのカプセルシェル。
- 請求項13に記載のカプセルシェルを含み、薬物もしくは栄養補助剤もしくは食品補助剤、またはそれらの組み合わせを更に含む、カプセル。
- 請求項1〜7のいずれか1項に記載の少なくとも1種のエステル化セルロースエーテル中の少なくとも1種の活性成分の固体分散体。
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US10214594B2 (en) | 2019-02-26 |
CN107428847A (zh) | 2017-12-01 |
BR112017018260A2 (pt) | 2018-04-10 |
EP3270971B1 (en) | 2019-01-09 |
US20180072819A1 (en) | 2018-03-15 |
EP3270971A1 (en) | 2018-01-24 |
MX2017011095A (es) | 2017-11-10 |
JP6356922B2 (ja) | 2018-07-11 |
KR20170128358A (ko) | 2017-11-22 |
CO2017010191A2 (es) | 2018-01-05 |
WO2016148977A1 (en) | 2016-09-22 |
CN107428847B (zh) | 2018-11-16 |
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