TW446561B - Improved stabilization of prostaglandin drug - Google Patents

Improved stabilization of prostaglandin drug Download PDF

Info

Publication number: TW446561B
Authority: TW; Taiwan
Prior art keywords: eudragit; patent application; item; solid; copolymer
Prior art date: 1997-06-30

Application number

TW86109178A

Other languages

English (en)

Chinese (zh)

Inventor

Cheng-Gung Chen

Rung-Je Tsai

Huei-Ying Lin

Shu-Bin Liu

Original Assignee

Dev Center Biotechnology

Priority date (The priority date 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 date listed.)

1997-06-30

Filing date

1997-06-30

Publication date

2001-07-21

1997-06-30 Application filed by Dev Center Biotechnology filed Critical Dev Center Biotechnology

1997-06-30 Priority to TW86109178A priority Critical patent/TW446561B/zh

1997-08-29 Priority to JP23496697A priority patent/JPH1135488A/ja

2001-07-21 Application granted granted Critical

2001-07-21 Publication of TW446561B publication Critical patent/TW446561B/zh

Links

150000003180 prostaglandins Chemical class 0.000 title claims abstract description 24
239000003814 drug Substances 0.000 title claims abstract description 21
229940079593 drug Drugs 0.000 title claims abstract description 18
230000006641 stabilisation Effects 0.000 title description 3
238000011105 stabilization Methods 0.000 title description 3
OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 claims abstract description 73
229960005249 misoprostol Drugs 0.000 claims abstract description 73
239000007787 solid Substances 0.000 claims abstract description 71
229920001577 copolymer Polymers 0.000 claims abstract description 46
239000000203 mixture Substances 0.000 claims abstract description 39
229920003136 Eudragit® L polymer Polymers 0.000 claims abstract description 8
229920003137 Eudragit® S polymer Polymers 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
239000003381 stabilizer Substances 0.000 claims description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
FSXVSUSRJXIJHB-UHFFFAOYSA-M ethyl prop-2-enoate;methyl 2-methylprop-2-enoate;trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical class [Cl-].CCOC(=O)C=C.COC(=O)C(C)=C.CC(=C)C(=O)OCC[N+](C)(C)C FSXVSUSRJXIJHB-UHFFFAOYSA-M 0.000 claims description 35
238000000034 method Methods 0.000 claims description 34
229920003152 Eudragit® RS polymer Polymers 0.000 claims description 30
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 27
229920003134 Eudragit® polymer Polymers 0.000 claims description 25
-1 (±) methyl Chemical group 0.000 claims description 18
229940075534 amino methacrylate copolymer Drugs 0.000 claims description 16
239000003960 organic solvent Substances 0.000 claims description 16
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 14
DNKKLDKIFMDAPT-UHFFFAOYSA-N n,n-dimethylmethanamine;2-methylprop-2-enoic acid Chemical compound CN(C)C.CC(=C)C(O)=O.CC(=C)C(O)=O DNKKLDKIFMDAPT-UHFFFAOYSA-N 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 14
238000011049 filling Methods 0.000 claims description 11
229920003151 Eudragit® RL polymer Polymers 0.000 claims description 10
238000003756 stirring Methods 0.000 claims description 6
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical group CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 5
230000002079 cooperative effect Effects 0.000 claims description 5
229920003145 methacrylic acid copolymer Polymers 0.000 claims description 5
235000015170 shellfish Nutrition 0.000 claims description 5
229920003159 Eudragit® RS 100 Polymers 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
239000012467 final product Substances 0.000 claims description 3
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
229940117841 methacrylic acid copolymer Drugs 0.000 claims description 3
229920006243 acrylic copolymer Polymers 0.000 claims description 2
238000004898 kneading Methods 0.000 claims description 2
238000007873 sieving Methods 0.000 claims description 2
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims 3
229960003529 diazepam Drugs 0.000 claims 3
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 2
229920003155 Eudragit® RL 100 Polymers 0.000 claims 2
238000001035 drying Methods 0.000 claims 2
102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 claims 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical group [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
241000282376 Panthera tigris Species 0.000 claims 1
NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
238000000227 grinding Methods 0.000 claims 1
210000002307 prostate Anatomy 0.000 claims 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 abstract description 3
239000002245 particle Substances 0.000 description 20
239000008187 granular material Substances 0.000 description 18
230000000694 effects Effects 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000003826 tablet Substances 0.000 description 10
239000002775 capsule Substances 0.000 description 9
238000004090 dissolution Methods 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
239000000546 pharmaceutical excipient Substances 0.000 description 8
239000002552 dosage form Substances 0.000 description 7
239000007937 lozenge Substances 0.000 description 6
238000003860 storage Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000013268 sustained release Methods 0.000 description 5
239000012730 sustained-release form Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229940017219 methyl propionate Drugs 0.000 description 3
239000000843 powder Substances 0.000 description 3
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
229920003084 Avicel® PH-102 Polymers 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
229940016286 microcrystalline cellulose Drugs 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
239000008108 microcrystalline cellulose Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920001296 polysiloxane Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000005070 sampling Methods 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229940032147 starch Drugs 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
229920001897 terpolymer Polymers 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 description 1
SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
108091071247 Beta family Proteins 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
241000255925 Diptera Species 0.000 description 1
241000237858 Gastropoda Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
244000294411 Mirabilis expansa Species 0.000 description 1
235000015429 Mirabilis expansa Nutrition 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000009858 acid secretion Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000012937 correction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000007922 dissolution test Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000013265 extended release Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
235000003642 hunger Nutrition 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
235000013536 miso Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000004033 plastic Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001012 protector Effects 0.000 description 1
238000004445 quantitative analysis Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
230000037351 starvation Effects 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940098465 tincture Drugs 0.000 description 1

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Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

TW86109178A 1997-06-30 1997-06-30 Improved stabilization of prostaglandin drug TW446561B (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
TW86109178A TW446561B (en)	1997-06-30	1997-06-30	Improved stabilization of prostaglandin drug
JP23496697A JPH1135488A (ja)	1997-06-30	1997-08-29	安定性の改善されたプロスタグランジン薬

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
TW86109178A TW446561B (en)	1997-06-30	1997-06-30	Improved stabilization of prostaglandin drug

Publications (1)

Publication Number	Publication Date
TW446561B true TW446561B (en)	2001-07-21

Family

ID=21626757

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW86109178A TW446561B (en)	1997-06-30	1997-06-30	Improved stabilization of prostaglandin drug

Country Status (2)

Country	Link
JP (1)	JPH1135488A (ja)
TW (1)	TW446561B (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0417401D0 (en) *	2004-08-05	2004-09-08	Controlled Therapeutics Sct	Stabilised prostaglandin composition
US8481565B2 (en) *	2004-12-27	2013-07-09	Eisai R&D Management Co., Ltd.	Method for stabilizing anti-dementia drug

1997
- 1997-06-30 TW TW86109178A patent/TW446561B/zh not_active IP Right Cessation
- 1997-08-29 JP JP23496697A patent/JPH1135488A/ja active Pending

Also Published As

Publication number	Publication date
JPH1135488A (ja)	1999-02-09

Legal Events

Date	Code	Title	Description
2001-12-20	GD4A	Issue of patent certificate for granted invention patent
2017-08-11	MK4A	Expiration of patent term of an invention patent

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