CA2493980A1 - Gelatin capsule exhibiting reduced cross-linking - Google Patents
Gelatin capsule exhibiting reduced cross-linking Download PDFInfo
- Publication number
- CA2493980A1 CA2493980A1 CA002493980A CA2493980A CA2493980A1 CA 2493980 A1 CA2493980 A1 CA 2493980A1 CA 002493980 A CA002493980 A CA 002493980A CA 2493980 A CA2493980 A CA 2493980A CA 2493980 A1 CA2493980 A1 CA 2493980A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- dosage form
- gelatin
- drug
- capsule
- 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.)
- Abandoned
Links
- 238000004132 cross linking Methods 0.000 title claims abstract description 52
- 239000007903 gelatin capsule Substances 0.000 title claims abstract description 40
- 230000002829 reductive effect Effects 0.000 title abstract description 10
- 230000001747 exhibiting effect Effects 0.000 title abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 151
- 239000002775 capsule Substances 0.000 claims description 107
- -1 sulfite compound Chemical class 0.000 claims description 87
- 239000003814 drug Substances 0.000 claims description 80
- 229940079593 drug Drugs 0.000 claims description 78
- 108010010803 Gelatin Proteins 0.000 claims description 58
- 229920000159 gelatin Polymers 0.000 claims description 58
- 239000008273 gelatin Substances 0.000 claims description 58
- 235000019322 gelatine Nutrition 0.000 claims description 58
- 235000011852 gelatine desserts Nutrition 0.000 claims description 58
- 239000000463 material Substances 0.000 claims description 53
- 239000002552 dosage form Substances 0.000 claims description 42
- 238000003860 storage Methods 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 230000015572 biosynthetic process Effects 0.000 claims description 33
- 238000004090 dissolution Methods 0.000 claims description 31
- 229960000590 celecoxib Drugs 0.000 claims description 26
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 13
- 229940001584 sodium metabisulfite Drugs 0.000 claims description 13
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 11
- 229920001223 polyethylene glycol Polymers 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
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- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 235000011187 glycerol Nutrition 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 8
- 238000003556 assay Methods 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 238000000338 in vitro Methods 0.000 claims description 8
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000000600 sorbitol Substances 0.000 claims description 8
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 239000004014 plasticizer Substances 0.000 claims description 7
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- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 5
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 5
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- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 230000002496 gastric effect Effects 0.000 claims description 4
- 150000002334 glycols Chemical class 0.000 claims description 4
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 claims description 3
- 229960003314 deracoxib Drugs 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229960004945 etoricoxib Drugs 0.000 claims description 3
- MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 3
- 229960000371 rofecoxib Drugs 0.000 claims description 3
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229960002004 valdecoxib Drugs 0.000 claims description 3
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 3
- XNTLXAUHLBBEKP-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-4-(3-hydroxy-3-methylbutoxy)-5-(4-methylsulfonylphenyl)pyridazin-3-one Chemical compound O=C1C(OCCC(C)(O)C)=C(C=2C=CC(=CC=2)S(C)(=O)=O)C=NN1C1=CC=C(F)C(F)=C1 XNTLXAUHLBBEKP-UHFFFAOYSA-N 0.000 claims description 2
- ULFYMTMZNITFSB-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-3-(4-methylsulfonylphenyl)cyclopent-2-en-1-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C=C(F)C=2)C(=O)CC1 ULFYMTMZNITFSB-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
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- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
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- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
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- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
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- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003844 furanonyl group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 150000007965 phenolic acids Chemical class 0.000 claims description 2
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- 239000010695 polyglycol Substances 0.000 claims description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 229960003656 ricinoleic acid Drugs 0.000 claims description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000126 substance Substances 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 4
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- 150000002314 glycerols Chemical class 0.000 claims 2
- 235000013772 propylene glycol Nutrition 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
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- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 23
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Landscapes
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Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39986202P | 2002-07-31 | 2002-07-31 | |
| US39977602P | 2002-07-31 | 2002-07-31 | |
| US39986302P | 2002-07-31 | 2002-07-31 | |
| US39980802P | 2002-07-31 | 2002-07-31 | |
| US60/399,863 | 2002-07-31 | ||
| US60/399,776 | 2002-07-31 | ||
| US60/399,808 | 2002-07-31 | ||
| US60/399,862 | 2002-07-31 | ||
| PCT/US2003/024045 WO2004010974A2 (en) | 2002-07-31 | 2003-07-31 | Gelatin capsule exhibiting reduced cross-linking |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2493980A1 true CA2493980A1 (en) | 2004-02-05 |
Family
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Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002493980A Abandoned CA2493980A1 (en) | 2002-07-31 | 2003-07-31 | Gelatin capsule exhibiting reduced cross-linking |
| CA002494358A Abandoned CA2494358A1 (en) | 2002-07-31 | 2003-07-31 | Pharmaceutical dosage form capable of maintaining stable dissolution profile upon storage |
| CA002493974A Abandoned CA2493974A1 (en) | 2002-07-31 | 2003-07-31 | Pharmaceutical dosage form comprising a sulfite compound |
| CA002494069A Abandoned CA2494069A1 (en) | 2002-07-31 | 2003-07-31 | Pellicle-resistant gelatin capsule |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002494358A Abandoned CA2494358A1 (en) | 2002-07-31 | 2003-07-31 | Pharmaceutical dosage form capable of maintaining stable dissolution profile upon storage |
| CA002493974A Abandoned CA2493974A1 (en) | 2002-07-31 | 2003-07-31 | Pharmaceutical dosage form comprising a sulfite compound |
| CA002494069A Abandoned CA2494069A1 (en) | 2002-07-31 | 2003-07-31 | Pellicle-resistant gelatin capsule |
Country Status (7)
| Country | Link |
|---|---|
| EP (4) | EP1526847A2 (cg-RX-API-DMAC7.html) |
| JP (4) | JP2005538102A (cg-RX-API-DMAC7.html) |
| AU (4) | AU2003257981A1 (cg-RX-API-DMAC7.html) |
| BR (4) | BR0313150A (cg-RX-API-DMAC7.html) |
| CA (4) | CA2493980A1 (cg-RX-API-DMAC7.html) |
| MX (4) | MXPA05000862A (cg-RX-API-DMAC7.html) |
| WO (4) | WO2004022032A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2524000T3 (es) | 2002-06-05 | 2014-12-03 | Teva Czech Industries S.R.O. | Reducción de la reticulación de la gelatina |
| NZ560712A (en) | 2005-02-17 | 2010-12-24 | Synta Pharmaceuticals Corp | (3,4,5-trisubstituted-phenyl)isoxazole combretastin derivatives for the treatment of disorders |
| US7485323B2 (en) | 2005-05-31 | 2009-02-03 | Gelita Ag | Process for making a low molecular weight gelatine hydrolysate and gelatine hydrolysate compositions |
| SI1906938T1 (sl) | 2005-07-26 | 2011-02-28 | Nicox Sa | Farmacevtska formulacija nitrooksiderivatov od NSAID |
| JP5503939B2 (ja) * | 2009-10-16 | 2014-05-28 | 東洋カプセル株式会社 | アゼラスチン塩酸塩含有カプセル剤 |
| JP6887456B2 (ja) | 2018-07-04 | 2021-06-16 | キャプシュゲル・ベルジウム・エヌ・ヴィ | 白色化剤として界面活性剤又は界面活性剤と塩を含有する皮膜形成性組成物 |
| US11364478B2 (en) * | 2019-05-22 | 2022-06-21 | Mezzimatic, LLC | Method of manufacturing throwable paintballs and paintballs made therefrom |
| KR20220077091A (ko) * | 2020-12-01 | 2022-06-08 | 주식회사 엘지화학 | 1-(3-시아노-1-아이소프로필-인돌-5-일)피라졸-4-카르복실산을 포함하는 안정한 경구용 제제 |
| CN113230241A (zh) * | 2021-06-11 | 2021-08-10 | 北京畅盛医药科技有限公司 | 三羟甲基氨基甲烷盐在治疗心脑血管病的药物中的应用 |
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| JPS5115094B2 (cg-RX-API-DMAC7.html) * | 1972-11-01 | 1976-05-14 | ||
| US4349529A (en) * | 1980-04-14 | 1982-09-14 | E. R. Squibb & Sons, Inc. | Diagnostic and therapeutic capsules and method of producing |
| US4590183A (en) * | 1985-04-22 | 1986-05-20 | Sterling Drug Inc. | Gastric cytoprotection with sodium thiosulfate in oral administration of aspirin |
| FR2617047B1 (fr) * | 1987-06-23 | 1991-05-10 | Sanofi Sa | Composition de gelatine resistant au tannage, capsules a base de cette composition et leur application pharmaceutique, notamment au fenofibrate |
| JP2790659B2 (ja) * | 1989-06-30 | 1998-08-27 | 帝国臓器製薬株式会社 | ゼラチンカプセル剤 |
| DE69534258T2 (de) * | 1994-03-15 | 2006-05-04 | Mitsubishi Pharma Corp. | Verfahren zur Stabilisierung von Pranoprofen und stabile flüssige Zubereitung von Pranoprofen |
| IT1269583B (it) * | 1994-04-26 | 1997-04-08 | Bayer Italia Spa | Preparazioni farmaceutiche a base di una soluzione di ketoprofene in capsule di gelatina molle e metodo per la loro produzione |
| ATE197399T1 (de) * | 1994-08-05 | 2000-11-11 | Shionogi & Co | Gegen denaturierung beständige hartgelatine- kapseln und verfahren zu ihrer herstellung |
| US5620704A (en) * | 1994-11-07 | 1997-04-15 | Warner-Lambert Company | Process for stabilizing gelatin products |
| US7115565B2 (en) * | 2001-01-18 | 2006-10-03 | Pharmacia & Upjohn Company | Chemotherapeutic microemulsion compositions of paclitaxel with improved oral bioavailability |
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2003
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- 2003-07-31 BR BR0313064-9A patent/BR0313064A/pt not_active IP Right Cessation
- 2003-07-31 EP EP03772160A patent/EP1526845A2/en not_active Withdrawn
- 2003-07-31 WO PCT/US2003/024042 patent/WO2004010972A2/en not_active Ceased
- 2003-07-31 AU AU2003257982A patent/AU2003257982A1/en not_active Abandoned
- 2003-07-31 AU AU2003257103A patent/AU2003257103A1/en not_active Abandoned
- 2003-07-31 MX MXPA05001167A patent/MXPA05001167A/es unknown
- 2003-07-31 JP JP2004534259A patent/JP2006500389A/ja not_active Withdrawn
- 2003-07-31 WO PCT/US2003/024045 patent/WO2004010974A2/en not_active Ceased
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| FZDE | Dead |