JP2003522724A5 - - Google Patents
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- Publication number
- JP2003522724A5 JP2003522724A5 JP2000543139A JP2000543139A JP2003522724A5 JP 2003522724 A5 JP2003522724 A5 JP 2003522724A5 JP 2000543139 A JP2000543139 A JP 2000543139A JP 2000543139 A JP2000543139 A JP 2000543139A JP 2003522724 A5 JP2003522724 A5 JP 2003522724A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- carboxylic acid
- group
- hydrogen
- alkyl
- 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.)
- Pending
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 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 description 16
- 150000001735 carboxylic acids Chemical class 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 235000006708 antioxidants Nutrition 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000003381 stabilizer Substances 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- -1 C 1 -C 3 alkyl Chemical group 0.000 description 8
- 235000010323 ascorbic acid Nutrition 0.000 description 8
- 239000011668 ascorbic acid Substances 0.000 description 8
- 229960005070 ascorbic acid Drugs 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 7
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 6
- 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 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- 235000002906 tartaric acid Nutrition 0.000 description 5
- 239000002253 acid Substances 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000000996 L-ascorbic acids Chemical class 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/057,260 | 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 |
|---|---|
| JP2003522724A JP2003522724A (ja) | 2003-07-29 |
| JP2003522724A5 true JP2003522724A5 (enExample) | 2006-01-05 |
Family
ID=22009506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000543139A Pending JP2003522724A (ja) | 1998-04-08 | 1998-11-16 | 医薬製剤のための酸化防止剤−安定剤系 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5962488A (enExample) |
| EP (1) | EP1067927B1 (enExample) |
| JP (1) | JP2003522724A (enExample) |
| AT (1) | ATE318598T1 (enExample) |
| CA (1) | CA2327708A1 (enExample) |
| DE (1) | DE69833684T2 (enExample) |
| WO (1) | WO1999052529A1 (enExample) |
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 |
| KR20010101631A (ko) * | 1999-01-21 | 2001-11-14 | 시오노 요시히코 | 페놀성 히드록시 화합물의 변색이 저해되는 의약 조성물 |
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| 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 |
| JPWO2007046411A1 (ja) * | 2005-10-19 | 2009-04-23 | 大日本住友製薬株式会社 | 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 |
| AU2009207796B2 (en) | 2008-01-25 | 2014-03-27 | Grunenthal Gmbh | Pharmaceutical dosage form |
| KR101690094B1 (ko) | 2008-05-09 | 2016-12-27 | 그뤼넨탈 게엠베하 | 분무 응결 단계의 사용하에 중간 분말 제형 및 최종 고체 제형을 제조하는 방법 |
| UY32008A (es) * | 2008-07-28 | 2010-02-26 | Takeda Pharmaceutical | Composición farmacéutica |
| CA2765971C (en) | 2009-07-22 | 2017-08-22 | Gruenenthal Gmbh | Hot-melt extruded controlled release dosage form |
| ES2428938T3 (es) * | 2009-07-22 | 2013-11-12 | Grünenthal GmbH | Forma de dosificación resistente a la manipulación y estabilizada frente a la oxidación |
| RU2604676C2 (ru) | 2010-09-02 | 2016-12-10 | Грюненталь Гмбх | Устойчивая к разрушению лекарственная форма, содержащая неорганическую соль |
| PL2611425T3 (pl) | 2010-09-02 | 2014-09-30 | Gruenenthal Gmbh | Odporna na ingerencję postać dawki zawierająca polimer anionowy |
| HRP20171458T1 (hr) | 2011-07-29 | 2017-11-17 | Grünenthal GmbH | Tableta otporna na mijenjanje koja pruža neposredno oslobađanje lijeka |
| PL2736495T3 (pl) | 2011-07-29 | 2018-01-31 | Gruenenthal Gmbh | Tabletka odporna na ingerencję, zapewniająca natychmiastowe uwalnianie leku |
| WO2013127831A1 (en) | 2012-02-28 | 2013-09-06 | Grünenthal GmbH | Tamper-resistant dosage form comprising pharmacologically active compound and anionic polymer |
| LT2838512T (lt) | 2012-04-18 | 2018-11-12 | GrĆ¼nenthal GmbH | Pažeidimui atspari ir dozės atpalaidavimo nuokrypiui atspari farmacinė vaisto forma |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| AR096438A1 (es) | 2013-05-29 | 2015-12-30 | Gruenenthal Gmbh | Forma de dosificación resistente al uso indebido con perfil de liberación bimodal, proceso |
| JP6445537B2 (ja) | 2013-05-29 | 2018-12-26 | 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 | １個または複数の粒子を含有する改変防止（ｔａｍｐｅｒ−ｒｅｓｉｓｔａｎｔ）剤形 |
| US10624862B2 (en) | 2013-07-12 | 2020-04-21 | Grünenthal GmbH | Tamper-resistant dosage form containing ethylene-vinyl acetate polymer |
| JP6480936B2 (ja) | 2013-11-26 | 2019-03-13 | 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 | クライオミリングによる粉末状医薬組成物の調製 |
| JP2017518980A (ja) | 2014-05-12 | 2017-07-13 | 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 | タペンタドールを含む、改変防止即時放出カプセル製剤 |
| CN106456550A (zh) | 2014-05-26 | 2017-02-22 | 格吕伦塔尔有限公司 | 避免乙醇剂量倾泻的多颗粒 |
| KR20170139158A (ko) | 2015-04-24 | 2017-12-18 | 그뤼넨탈 게엠베하 | 즉시 방출되고 용매 추출 방지된 변조 방지된 투여 형태 |
| CN107750159B (zh) * | 2015-06-23 | 2021-10-29 | 英特维特国际股份有限公司 | 用于消毒的饮用水的含有维生素的异噁唑啉溶液 |
| WO2017042325A1 (en) | 2015-09-10 | 2017-03-16 | Grünenthal GmbH | Protecting oral overdose with abuse deterrent immediate release formulations |
| MX2023003783A (es) * | 2020-10-01 | 2023-04-26 | Imago Biosciences Inc | Formulaciones farmaceuticas para tratar enfermedades mediadas por 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 |
| 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 |
| US5077069A (en) * | 1991-01-07 | 1991-12-31 | Kabi Pharmacia Ab | Composition of natural antioxidants for the stabilization of polyunsaturated oils |
| 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 |
| PT725639E (pt) * | 1993-10-25 | 2001-02-28 | Merrell Pharma Inc | Composicao farmaceutica estavel de terfenadina e ibuprofeno |
| 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 CA CA002327708A patent/CA2327708A1/en not_active Abandoned
- 1998-11-16 AT AT98958610T patent/ATE318598T1/de not_active IP Right Cessation
- 1998-11-16 EP EP98958610A patent/EP1067927B1/en not_active Expired - Lifetime
- 1998-11-16 JP JP2000543139A patent/JP2003522724A/ja active Pending
- 1998-11-16 WO PCT/US1998/024471 patent/WO1999052529A1/en not_active Ceased
-
1999
- 1999-04-12 US US09/290,904 patent/US6479529B1/en not_active Expired - Fee Related
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