DE69833684T2 - Antioxidierende stabilisierungssysteme für pharmazeutische formulierungen - Google Patents
Antioxidierende stabilisierungssysteme für pharmazeutische formulierungen Download PDFInfo
- Publication number
- DE69833684T2 DE69833684T2 DE69833684T DE69833684T DE69833684T2 DE 69833684 T2 DE69833684 T2 DE 69833684T2 DE 69833684 T DE69833684 T DE 69833684T DE 69833684 T DE69833684 T DE 69833684T DE 69833684 T2 DE69833684 T2 DE 69833684T2
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- Germany
- Prior art keywords
- acid
- alkyl
- hydrogen
- alkylthio
- alkoxy
- 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.)
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 24
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 15
- 230000006641 stabilisation Effects 0.000 title description 4
- 238000011105 stabilization Methods 0.000 title description 4
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- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 30
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 29
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims abstract description 20
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- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000005176 gastrointestinal motility Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000009481 moist granulation Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 230000002635 muscarinergic effect Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57260 | 1998-04-08 | ||
| US09/057,260 US5962488A (en) | 1998-04-08 | 1998-04-08 | Stable pharmaceutical formulations for treating internal bowel syndrome containing isoxazole derivatives |
| PCT/US1998/024471 WO1999052529A1 (en) | 1998-04-08 | 1998-11-16 | Antioxidant stabilizer system for pharmaceutical formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69833684D1 DE69833684D1 (de) | 2006-04-27 |
| DE69833684T2 true DE69833684T2 (de) | 2006-11-16 |
Family
ID=22009506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69833684T Expired - Fee Related DE69833684T2 (de) | 1998-04-08 | 1998-11-16 | Antioxidierende stabilisierungssysteme für pharmazeutische formulierungen |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5962488A (https=) |
| EP (1) | EP1067927B1 (https=) |
| JP (1) | JP2003522724A (https=) |
| AT (1) | ATE318598T1 (https=) |
| CA (1) | CA2327708A1 (https=) |
| DE (1) | DE69833684T2 (https=) |
| WO (1) | WO1999052529A1 (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962488A (en) * | 1998-04-08 | 1999-10-05 | Roberts Laboratories, Inc. | Stable pharmaceutical formulations for treating internal bowel syndrome containing isoxazole derivatives |
| WO2000042997A1 (en) * | 1999-01-21 | 2000-07-27 | Shionogi & Co., Ltd. | Medicinal compositions retarded in the discoloration of phenolic hydroxyl compounds |
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102005005449A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| WO2007046411A1 (ja) * | 2005-10-19 | 2007-04-26 | Dainippon Sumitomo Pharma Co., Ltd. | イソキサゾール化合物の安定化方法 |
| DE102007025275A1 (de) * | 2007-05-31 | 2008-12-04 | Qiagen Gmbh | Butendisäure oder deren Derivate zur Behandlung einer biologischen Probe |
| KR101616246B1 (ko) | 2008-01-25 | 2016-05-02 | 그뤼넨탈 게엠베하 | 약제학적 투여형 |
| AU2009243681B2 (en) | 2008-05-09 | 2013-12-19 | Grunenthal Gmbh | Process for the preparation of an intermediate powder formulation and a final solid dosage form under usage of a spray congealing step |
| EP2309985B1 (en) * | 2008-07-28 | 2018-03-14 | Takeda Pharmaceutical Company Limited | Pharmaceutical composition |
| WO2011009602A1 (en) | 2009-07-22 | 2011-01-27 | Grünenthal GmbH | Hot-melt extruded controlled release dosage form |
| TWI473628B (zh) * | 2009-07-22 | 2015-02-21 | 用於對氧化敏感之類鴉片藥劑之抗破壞劑型 | |
| WO2012028318A1 (en) | 2010-09-02 | 2012-03-08 | Grünenthal GmbH | Tamper resistant dosage form comprising an anionic polymer |
| CA2808219C (en) | 2010-09-02 | 2019-05-14 | Gruenenthal Gmbh | Tamper resistant dosage form comprising inorganic salt |
| AU2012289764B2 (en) | 2011-07-29 | 2017-03-02 | Grünenthal GmbH | Tamper-resistant tablet providing immediate drug release |
| ES2648129T3 (es) | 2011-07-29 | 2017-12-28 | Grünenthal GmbH | Pastilla a prueba de manipulación que proporciona una liberación inmediata de un medicamento |
| US20130225697A1 (en) | 2012-02-28 | 2013-08-29 | Grunenthal Gmbh | Tamper-resistant dosage form comprising pharmacologically active compound and anionic polymer |
| PL2838512T3 (pl) | 2012-04-18 | 2018-12-31 | Grünenthal GmbH | Farmaceutyczna postać dawkowania odporna na niewłaściwe użycie i odporna na uderzeniowe uwalnianie dawki |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| JP6466417B2 (ja) | 2013-05-29 | 2019-02-06 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 二峰性放出プロファイルを有する改変防止（ｔａｍｐｅｒ−ｒｅｓｉｓｔａｎｔ）剤形 |
| AU2014273227B2 (en) | 2013-05-29 | 2019-08-15 | Grunenthal Gmbh | Tamper-resistant dosage form containing one or more particles |
| JP6449871B2 (ja) | 2013-07-12 | 2019-01-09 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | エチレン−酢酸ビニルポリマーを含有する改変防止剤形 |
| EP3073994A1 (en) | 2013-11-26 | 2016-10-05 | Grünenthal GmbH | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
| EP3142646A1 (en) | 2014-05-12 | 2017-03-22 | Grünenthal GmbH | Tamper resistant immediate release capsule formulation comprising tapentadol |
| EA201692388A1 (ru) | 2014-05-26 | 2017-05-31 | Грюненталь Гмбх | Лекарственная форма в виде множества частиц, защищенная от вызываемого этанолом сброса дозы |
| BR112017021475A2 (pt) | 2015-04-24 | 2018-07-10 | Gruenenthal Gmbh | forma de dosagem resistente à adulteração (tamper) com liberação imediata e resistência contra extração de solvente |
| BR112017027855B1 (pt) * | 2015-06-23 | 2022-11-16 | Intervet International B.V. | Composição farmacêutica, seu uso, água potável medicamentosa e método para sua preparação |
| WO2017042325A1 (en) | 2015-09-10 | 2017-03-16 | Grünenthal GmbH | Protecting oral overdose with abuse deterrent immediate release formulations |
| EP4221704B1 (en) * | 2020-10-01 | 2025-09-24 | Imago Biosciences Inc. | Pharmaceutical formulations for treating diseases mediated by kdm1a |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB679192A (en) * | 1948-07-09 | 1952-09-17 | Eastman Kodak Co | Method of stabilizing fats and fatty oils against oxidation |
| GB682205A (en) * | 1949-03-16 | 1952-11-05 | Eastman Kodak Co | Improvements in and relating to anti-oxidants for oils and fats |
| US4091091A (en) * | 1973-11-08 | 1978-05-23 | Eli Lilly And Company | Stabilized nitroglycerin tablets |
| JPS5299242A (en) * | 1976-02-12 | 1977-08-19 | Tanabe Seiyaku Co | Antiioxidant |
| JPS62153385A (ja) * | 1985-12-27 | 1987-07-08 | Riken Vitamin Co Ltd | 酸化防止剤 |
| US4837031A (en) * | 1987-09-17 | 1989-06-06 | Mallinckrodt, Inc. | Compositions containing ibuprofen |
| CA1335106C (en) * | 1989-02-27 | 1995-04-04 | John Mehnert Schaus | Ring-substituted 2-amino-1,2,3,4-tetra-hydronaphthalenes |
| US5420151A (en) * | 1989-12-22 | 1995-05-30 | Aktiebolaget Astra | Chroman derivatives |
| DK0471515T3 (da) * | 1990-08-15 | 1997-07-21 | Lilly Co Eli | Ringsubstituerede 2-amino-1,2,3,4-tetrahydronphtalener, 3-aminochromaner og 3-aminothiochromaner |
| US5077069A (en) * | 1991-01-07 | 1991-12-31 | Kabi Pharmacia Ab | Composition of natural antioxidants for the stabilization of polyunsaturated oils |
| JPH06500594A (ja) * | 1991-01-07 | 1994-01-20 | カビ ファルマシア アクチェボラーグ | 多不飽和油の安定化のための天然酸化防止剤の組成物 |
| JPH05339154A (ja) * | 1992-06-03 | 1993-12-21 | Sagami Chem Res Center | 肝機能改善剤 |
| US5434174A (en) * | 1992-07-17 | 1995-07-18 | Eli Lilly And Company | Isoxazole derivatives for the treatment of irritable bowel syndrome |
| JPH0717855A (ja) * | 1992-09-02 | 1995-01-20 | Maruha Corp | 脳機能改善組成物、学習能力増強剤、記憶力増強剤、痴呆予防剤、痴呆治療剤、または脳機能改善効果を有する機能性食品 |
| CA2173467A1 (en) * | 1993-10-25 | 1995-05-04 | Keith D. Ertel | A stable pharmaceutical composition of terfenadine and ibuprofen |
| JPH09194362A (ja) * | 1996-01-19 | 1997-07-29 | Bizen Kasei Kk | ドコサヘキサエン酸及びエイコサペンタエン酸含有リン脂質を含む組成物 |
| JP3941073B2 (ja) * | 1996-03-01 | 2007-07-04 | 日本油脂株式会社 | 油脂組成物及びそれを含む食品 |
| US5962488A (en) * | 1998-04-08 | 1999-10-05 | Roberts Laboratories, Inc. | Stable pharmaceutical formulations for treating internal bowel syndrome containing isoxazole derivatives |
-
1998
- 1998-04-08 US US09/057,260 patent/US5962488A/en not_active Expired - Fee Related
- 1998-11-16 DE DE69833684T patent/DE69833684T2/de not_active Expired - Fee Related
- 1998-11-16 JP JP2000543139A patent/JP2003522724A/ja active Pending
- 1998-11-16 AT AT98958610T patent/ATE318598T1/de not_active IP Right Cessation
- 1998-11-16 WO PCT/US1998/024471 patent/WO1999052529A1/en not_active Ceased
- 1998-11-16 EP EP98958610A patent/EP1067927B1/en not_active Expired - Lifetime
- 1998-11-16 CA CA002327708A patent/CA2327708A1/en not_active Abandoned
-
1999
- 1999-04-12 US US09/290,904 patent/US6479529B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE318598T1 (de) | 2006-03-15 |
| EP1067927A1 (en) | 2001-01-17 |
| US5962488A (en) | 1999-10-05 |
| EP1067927B1 (en) | 2006-03-01 |
| EP1067927A4 (en) | 2003-04-23 |
| JP2003522724A (ja) | 2003-07-29 |
| WO1999052529A1 (en) | 1999-10-21 |
| DE69833684D1 (de) | 2006-04-27 |
| US6479529B1 (en) | 2002-11-12 |
| CA2327708A1 (en) | 1999-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SHIRE US INC., EATONTOWN, N.J., US |
|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SHIRE US INC., FLORENCE, KY., US |
|
| 8339 | Ceased/non-payment of the annual fee |