WO1995011227B1 - Nouveaux phenols empeches a nitronyles substitues et pieges de spin - Google Patents
Nouveaux phenols empeches a nitronyles substitues et pieges de spinInfo
- Publication number
- WO1995011227B1 WO1995011227B1 PCT/US1994/012107 US9412107W WO9511227B1 WO 1995011227 B1 WO1995011227 B1 WO 1995011227B1 US 9412107 W US9412107 W US 9412107W WO 9511227 B1 WO9511227 B1 WO 9511227B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- alkyl
- tert
- nitronyl
- butyl
- Prior art date
Links
- 150000002989 phenols Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- DCNIQKYXZZLGFL-UHFFFAOYSA-N 1-phenyl-n-(2,4,4-trimethylpentan-2-yl)methanimine oxide Chemical compound CC(C)(C)CC(C)(C)[N+]([O-])=CC1=CC=CC=C1 DCNIQKYXZZLGFL-UHFFFAOYSA-N 0.000 claims abstract 2
- 230000037396 body weight Effects 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 238000001727 in vivo Methods 0.000 claims 2
- 230000003859 lipid peroxidation Effects 0.000 claims 2
- 150000007523 nucleic acids Chemical class 0.000 claims 2
- 102000039446 nucleic acids Human genes 0.000 claims 2
- 108020004707 nucleic acids Proteins 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Abstract
L'invention concerne l'utilisation de phénols empêchés à nitronyles substitués comme anti-oxydants dans des applications thérapeutiques. Dans la variante préférée, ces compositions présentent la formule générale (I), où R1 représente hydrogène, alkyle ou aryle et R2 représente alkyle ou aryle. L'invention concerne aussi des compositions nouvelles, utilisées comme anti-oxydants, qui incluent: 2,6-di-tert-butyl-4-(N-tert-octyle) nitronyle phénol (DBONP); 2,6-diméthyl-4-(N-tert-octyle) nitronyl phénol (DMONP); N-tert-octyl-C-phényle nitrone (OPN).
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU80869/94A AU696451B2 (en) | 1993-10-22 | 1994-10-20 | Novel spin trap nitronyl hindered phenols |
| DE69420146T DE69420146T2 (de) | 1993-10-22 | 1994-10-20 | Neue sterisch gehinderte nitronylphenole als radikalfänger ("spintraps") |
| EP94931977A EP0724565B1 (fr) | 1993-10-22 | 1994-10-20 | Nouveaux phenols empeches a nitronyles substitues et pieges de spin |
| CA002174628A CA2174628C (fr) | 1993-10-22 | 1994-10-20 | Nouveaux phenols empeches a nitronyles substitues et pieges de spin |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/141,241 | 1993-10-22 | ||
| US08/141,241 US5455272A (en) | 1993-10-22 | 1993-10-22 | Spin trap nitronyl hindered phenols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1995011227A1 WO1995011227A1 (fr) | 1995-04-27 |
| WO1995011227B1 true WO1995011227B1 (fr) | 1995-05-18 |
Family
ID=22494820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/012107 WO1995011227A1 (fr) | 1993-10-22 | 1994-10-20 | Nouveaux phenols empeches a nitronyles substitues et pieges de spin |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US5455272A (fr) |
| EP (1) | EP0724565B1 (fr) |
| AU (1) | AU696451B2 (fr) |
| DE (1) | DE69420146T2 (fr) |
| ES (1) | ES2136209T3 (fr) |
| WO (1) | WO1995011227A1 (fr) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5723502A (en) * | 1985-07-18 | 1998-03-03 | Proctor; Peter H. | Topical spin trap composition and method |
| NZ316288A (en) * | 1995-09-11 | 2000-01-28 | Hoechst Marion Roussel Inc | 3,4-dihydro-isoquinoline, 4,5-3H-benzo[c]azepin-7-ol and 1H-isoindole derivatives and pharmaceutical compositions containing them |
| ATE263559T1 (de) * | 1996-04-23 | 2004-04-15 | Centaur Pharmaceuticals Inc | Zubereitungen enhaltend eine nitroneverbindung für die verwendung bei der behandlung von uveitis |
| JP2000514822A (ja) | 1996-07-19 | 2000-11-07 | センター ファーマシューティカルズ，インコーポレイテッド | フランニトロン化合物 |
| TW429241B (en) * | 1996-09-26 | 2001-04-11 | Sumitomo Pharma | Nitrone derivatives |
| MA26553A1 (fr) | 1997-10-17 | 2004-12-20 | Centaur Pharmaceuticals Inc | Alpha-aryl-n-alkylnitrones et compositions pharmaceutiques contenant ceux-la |
| DE69904018D1 (en) * | 1998-01-16 | 2003-01-02 | Centaur Pharmaceuticals Inc | Thiophennitronderivate |
| CN1291980A (zh) * | 1998-01-16 | 2001-04-18 | 桑道药品有限公司 | 硫醚呋喃硝酮化合物 |
| PT1077694E (pt) * | 1998-05-19 | 2004-12-31 | Renovis Inc | Produtos terapeuticos de arilnitrona para o tratamento da doenca inflamatoria dointestino |
| EP1077696A1 (fr) * | 1998-05-19 | 2001-02-28 | Centaur Pharmaceuticals, Inc. | Medicament a base de nitrone furanique, destine au traitement des affections inflammatoires de l'intestin |
| US6083989A (en) * | 1999-05-18 | 2000-07-04 | Centaur Pharmaceuticals, Inc. | Aryl nitrone therapeutics for the treatment of inflammatory bowel disease |
| WO1999059569A1 (fr) | 1998-05-19 | 1999-11-25 | Centaur Pharmaceuticals, Inc. | Medicament a base de benzamide, destine au traitement des affections inflammatoires de l'intestin |
| FR2780404B1 (fr) * | 1998-06-26 | 2001-04-13 | Adir | Nouveaux derives de nitrone, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ATE267804T1 (de) | 1998-07-17 | 2004-06-15 | Renovis Inc | Alpha-(2-hydroxyphenyl)nitrone, diese enthaltenden pharmazeutische zubereitungen sowie deren verwendung zur behandlung von entzündungen |
| UA66401C2 (en) | 1998-12-02 | 2004-05-17 | Sentor Pharmaceuticals Inc | 3,4,5-trisubstituted aryl nitrone compounds and pharmaceutical composition containing the same |
| US6730700B2 (en) | 1998-12-02 | 2004-05-04 | Renovis, Inc. | 3,4,5,-trisubstituted aryl nitrone compounds and pharmaceutical compositions containing the same |
| IT1312537B1 (it) * | 1999-04-16 | 2002-04-22 | Euphar Group Srl | Derivati del (-)- verbenone. |
| WO2002065993A2 (fr) * | 2001-01-08 | 2002-08-29 | Centaur Pharmaceuticals, Inc. | Utilisation de composes d'arylnitrone dans des methodes de traitement des douleurs neuropathiques |
| FR2846968B1 (fr) * | 2002-11-08 | 2005-02-04 | Salles Jean Pierre | Nouveaux derives amphiphiles de l'alpha-c-phenyl-n-tert- butyl nitrone |
| US20050059638A1 (en) * | 2003-08-04 | 2005-03-17 | Kelly Michael G. | Aryl, heteroaromatic and bicyclic aryl nitrone compounds, prodrugs and pharmaceutical compositions of the same to treat human disorders |
| US20050182060A1 (en) * | 2004-02-13 | 2005-08-18 | Kelly Michael G. | 2-Substituted and 4-substituted aryl nitrone compounds |
| US20050215646A1 (en) * | 2004-03-09 | 2005-09-29 | Renovis, Inc. | Methods for treating multiple sclerosis and pharmaceutical compositions therefor |
| JP4996575B2 (ja) * | 2007-11-15 | 2012-08-08 | ローム アンド ハース カンパニー | ニトロンの製造 |
| ES2367330T3 (es) * | 2007-11-15 | 2011-11-02 | Rohm And Haas Company | Preparación de nitronas. |
| US9034926B2 (en) | 2010-12-30 | 2015-05-19 | Nicholas V. Perricone | Topical nitrone spin trap compositions for psoriasis |
| US8986739B2 (en) | 2011-02-28 | 2015-03-24 | Nicholas V. Perricone | Treatment of urinary incontinence using nitrone spin traps |
| WO2013081778A2 (fr) * | 2011-11-30 | 2013-06-06 | Angus Chemical Company | Composés nitrones et leur utilisation dans le soin personnel |
| CN106061941B (zh) | 2014-03-07 | 2018-05-08 | 陶氏环球技术有限责任公司 | 硝酮化合物及其在个人护理中的使用 |
| US9730874B2 (en) | 2014-05-12 | 2017-08-15 | Dow Global Technologies Llc | Nitrone compounds and their use in personal care |
| JP6734204B2 (ja) | 2014-06-30 | 2020-08-05 | ダウ グローバル テクノロジーズ エルエルシー | ポリマーニトロン及びパーソナルケアにおけるそれらの使用 |
| JP6734295B2 (ja) * | 2015-03-20 | 2020-08-05 | ダウ グローバル テクノロジーズ エルエルシー | 不飽和脂肪の酸化のニトロン抑制 |
| EP3270875B1 (fr) * | 2015-03-20 | 2019-05-01 | Dow Global Technologies LLC | Inhibition, à base de nitrone, de l'oxydation de matières grasses insaturées |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3903049A (en) * | 1974-01-30 | 1975-09-02 | Goodyear Tire & Rubber | Oxidation resistant sulfur curable rubbery polymers |
| GB2137619A (en) * | 1983-03-30 | 1984-10-10 | Gerald Scott | Nitrone compounds and stabilised rubber compositions containing them |
| US5036097A (en) * | 1989-10-17 | 1991-07-30 | Oklahoma Medical Research Foundation | Phenylbutyl nitrone compositions and methods for prevention of gastric ulceration |
| US5025032A (en) * | 1989-10-17 | 1991-06-18 | Oklahoma Medical Research Foundation | Phenyl butyl nitrone compositions and methods for treatment of oxidative tissue damage |
| JP2797559B2 (ja) * | 1989-11-30 | 1998-09-17 | 住友化学工業株式会社 | ニトロン化合物およびその製造法 |
| DE69232263T2 (de) * | 1991-06-18 | 2003-06-18 | Oklahoma Medical Research Foundation, Oklahoma | Radikalfänger ("spin traps") zur behandlung von mit oxidation von lipiden und proteinen verbundenen erkrankungen |
-
1993
- 1993-10-22 US US08/141,241 patent/US5455272A/en not_active Ceased
-
1994
- 1994-10-20 ES ES94931977T patent/ES2136209T3/es not_active Expired - Lifetime
- 1994-10-20 AU AU80869/94A patent/AU696451B2/en not_active Ceased
- 1994-10-20 DE DE69420146T patent/DE69420146T2/de not_active Expired - Fee Related
- 1994-10-20 EP EP94931977A patent/EP0724565B1/fr not_active Expired - Lifetime
- 1994-10-20 WO PCT/US1994/012107 patent/WO1995011227A1/fr active IP Right Grant
-
1995
- 1995-04-10 US US08/419,159 patent/US5532277A/en not_active Expired - Lifetime
- 1995-04-10 US US08/419,157 patent/US5527828A/en not_active Expired - Lifetime
-
1997
- 1997-10-02 US US08/942,494 patent/USRE36594E/en not_active Expired - Lifetime
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