NO323374B1 - Steroidforbindelser, anvendelse og farmasoytisk formulering omfattende slike. - Google Patents
Steroidforbindelser, anvendelse og farmasoytisk formulering omfattende slike. Download PDFInfo
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- NO323374B1 NO323374B1 NO20014925A NO20014925A NO323374B1 NO 323374 B1 NO323374 B1 NO 323374B1 NO 20014925 A NO20014925 A NO 20014925A NO 20014925 A NO20014925 A NO 20014925A NO 323374 B1 NO323374 B1 NO 323374B1
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- compound
- acid
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- steroid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
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- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| IT1999MI000751A IT1311922B1 (it) | 1999-04-13 | 1999-04-13 | Composti farmaceutici. |
| PCT/EP2000/003238 WO2000061604A2 (en) | 1999-04-13 | 2000-04-11 | Pharmaceutical compounds |
Publications (3)
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| NO20014925D0 NO20014925D0 (no) | 2001-10-10 |
| NO20014925L NO20014925L (no) | 2001-12-13 |
| NO323374B1 true NO323374B1 (no) | 2007-04-16 |
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| NO20014925A NO323374B1 (no) | 1999-04-13 | 2001-10-10 | Steroidforbindelser, anvendelse og farmasoytisk formulering omfattende slike. |
| NO20065784A NO20065784L (no) | 1999-04-13 | 2006-12-13 | Steroidforbindelser og anvendelse av slike |
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| NO20065784A NO20065784L (no) | 1999-04-13 | 2006-12-13 | Steroidforbindelser og anvendelse av slike |
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| EP (2) | EP1475386A3 (da) |
| JP (1) | JP2002542162A (da) |
| KR (2) | KR100687821B1 (da) |
| CN (2) | CN1916013A (da) |
| AT (1) | ATE274521T1 (da) |
| AU (2) | AU766798B2 (da) |
| BR (1) | BR0009696A (da) |
| CA (2) | CA2370446C (da) |
| DE (1) | DE60013266T2 (da) |
| DK (1) | DK1169337T3 (da) |
| ES (1) | ES2226805T3 (da) |
| HU (1) | HUP0201872A3 (da) |
| IL (2) | IL145633A0 (da) |
| IT (1) | IT1311922B1 (da) |
| MX (1) | MXPA01010212A (da) |
| NO (2) | NO323374B1 (da) |
| NZ (1) | NZ514572A (da) |
| PL (1) | PL199579B1 (da) |
| PT (1) | PT1169337E (da) |
| RU (1) | RU2240325C2 (da) |
| SI (1) | SI1169337T1 (da) |
| TR (2) | TR200102929T2 (da) |
| WO (1) | WO2000061604A2 (da) |
| ZA (1) | ZA200108124B (da) |
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| CA2393724A1 (en) | 1999-12-23 | 2001-06-28 | Nitromed, Inc. | Nitrosated and nitrosylated cyclooxygenase-2 inhibitors, compositions and methods of use |
| DE60122939T2 (de) | 2000-12-21 | 2007-01-11 | Nitromed, Inc., Bedford | Substituierte arylverbindungen als neue, cyclooxygenase-2-selektive inhibitoren, zusammensetzungen und verwendungsverfahren |
| IT1320176B1 (it) * | 2000-12-22 | 2003-11-26 | Nicox Sa | Dispersioni solide di principi attivi nitrati. |
| EP1219306A1 (en) * | 2000-12-29 | 2002-07-03 | Nicox S.A. | Compositions comprising cyclodextrins and NO- releasing drugs |
| US6696592B2 (en) | 2001-05-22 | 2004-02-24 | Nicox-S.A. | Methods of making 21-[4′-(nitrooxyalkyl)benzoate] corticosteroid derivatives and intermediates useful in the synthesis thereof |
| ITMI20011307A1 (it) * | 2001-06-21 | 2002-12-21 | Nicox Sa | Farmaci per l'epilessia |
| ITMI20020148A1 (it) | 2002-01-29 | 2003-07-29 | Nicox Sa | Nuovi corticosteroidi |
| ITMI20021025A1 (it) * | 2002-05-14 | 2003-11-14 | Nicox Sa | Farmaci per il trattamento acuto di disfunzioni del circolo venoso epatico e portale |
| AU2003248642A1 (en) | 2002-06-11 | 2003-12-22 | Nitromed, Inc. | Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| CA2491127A1 (en) | 2002-07-03 | 2004-01-15 | Nitromed, Inc. | Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use |
| CA2493156A1 (en) | 2002-07-29 | 2004-02-05 | Nitromed, Inc. | Cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| CN100513415C (zh) * | 2005-08-03 | 2009-07-15 | 中国人民解放军军事医学科学院毒物药物研究所 | 胆汁酸衍生物及其医药用途 |
| ES2393363T3 (es) | 2005-09-02 | 2012-12-20 | Nicox S.A. | Derivados nitrooxi de glucocorticoides |
| US8802726B2 (en) | 2006-02-03 | 2014-08-12 | Nicox S.A. | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies |
| US7645749B2 (en) | 2006-04-03 | 2010-01-12 | Forbes Medi-Tech Inc. | Sterol/stanol nitroderivatives and use thereof |
| US7645748B2 (en) * | 2006-04-03 | 2010-01-12 | Forbes Medi-Tech Inc. | Sterol/stanol phosphorylnitroderivatives and use thereof |
| JP5216782B2 (ja) * | 2007-02-05 | 2013-06-19 | ニコックス エス エイ | 酸化窒素放出性ステロイド |
| JP2011501730A (ja) * | 2007-08-10 | 2011-01-13 | ニコックス エス エイ | 呼吸器系疾患を治療するためのニトロ誘導されたステロイドと気管支拡張剤との組合せ |
| US20090088411A1 (en) * | 2007-08-31 | 2009-04-02 | Topigen Pharmaceuticals Inc. | No-donating corticosteroid with improved pharmacokinetic, anti-inflammatory and vasodilatory properties |
| EP2214674A4 (en) * | 2007-10-19 | 2011-03-30 | Burnham Inst Medical Research | INHIBITORS OF ANTI-APOPTOTIC PROTEINS |
| CA2731520A1 (en) | 2008-08-05 | 2010-02-11 | Nicox S.A. | New no-releasing steroids for the treatment of retina and macula lutea diseases |
| AU2011243947A1 (en) | 2010-04-23 | 2012-12-06 | Piramal Enterprises Limited | Nitric oxide releasing prodrugs of therapeutic agents |
| CU20110244A7 (es) | 2011-12-27 | 2013-08-29 | Ct De Investigación Y Desarrollo De Medicamentos Cidem | Sistemas espiroesteroidales con efectos neuroactivos y anti-inflamatorios |
| WO2014111957A1 (en) | 2013-01-21 | 2014-07-24 | Apparao Satyam | Nitric oxide releasing prodrugs of therapeutic agents |
| KR101711513B1 (ko) * | 2015-06-26 | 2017-03-02 | 주식회사 엘지생활건강 | 피부 개선용 조성물 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2077750B1 (da) | 1970-02-11 | 1973-03-16 | Clin Byla Ets | |
| GB1458372A (en) | 1973-03-05 | 1976-12-15 | Leo Ab | Steroid carbamates and allophanates |
| JPS5845724A (ja) | 1981-09-11 | 1983-03-17 | Oriza Yuka Kk | オリザノ−ル乳化液の製造法 |
| FR2600653B1 (fr) | 1986-06-24 | 1988-12-16 | Pasteur Strasbourg Universite | Composes de synthese associative d'acides amines soufres ou non soufres avec des derives du d-4 pregnene 3,20-dione ou avec des derives du d-1,4 pregnadiene 3,20-dione aux proprietes glucocorticoides et anti-inflammatoires, procedes d'obtention, compositions pharmaceutiques les contenant. proprietes pharmacologiques et applications |
| IT1204571B (it) * | 1987-05-08 | 1989-03-10 | Chiesi Farma Spa | Esteri di 1,4:3,6-dianidrosorbitolo-2-mononitrato e 5-mononitrato,loro procedimento di preparazione e loro composizioni farmaceutiche |
| EP1229123A3 (en) * | 1987-06-29 | 2004-11-03 | Massachusetts Institute Of Technology | Method for producing polyester biopolymers |
| DE4000397A1 (de) * | 1990-01-09 | 1991-07-11 | Hoechst Ag | Lipidselektive antioxidantien sowie deren herstellung und verwendung |
| JPH04273892A (ja) | 1991-02-27 | 1992-09-30 | Kao Corp | 新規な２１−置換ステロイド化合物 |
| JP3108474B2 (ja) | 1991-08-07 | 2000-11-13 | 日清製粉株式会社 | 活性型ビタミンｄ誘導体 |
| IL104201A0 (en) | 1991-12-26 | 1993-05-13 | Wisconsin Alumni Res Found | 26,27-dimethylene-1 alpha-25-dihydroxyvitamin d2 and its 24-epimer and pharmaceutical compositions containing them |
| EP0562497A1 (en) | 1992-03-27 | 1993-09-29 | Nisshin Flour Milling Co., Ltd. | 1 alpha-hydroxy vitamins D7 and D4' processes for the preparation thereof and pharmaceutical compositions |
| US5194431A (en) | 1992-07-08 | 1993-03-16 | Wisconsin Alumni Research Foundation | 24-cyclopropane vitamin D derivatives |
| US5707984A (en) | 1995-12-08 | 1998-01-13 | G. D. Searle & Co. | Steroid nitrite/nitrate ester derivatives useful as anti-inflammatory drugs |
| US5837698A (en) * | 1996-05-02 | 1998-11-17 | G. D. Searle & Co. | Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
| US5985862A (en) * | 1996-05-02 | 1999-11-16 | G.D. Searle & Co. | Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
| DE19634793A1 (de) | 1996-08-29 | 1998-03-05 | Sanol Arznei Schwarz Gmbh | S- und O-Nitratoacylverbindungen |
| IT1285770B1 (it) * | 1996-10-04 | 1998-06-18 | Nicox Sa | Composti corticoidei |
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