JP3880067B2 - 新規化合物並びに抗炎症及び抗血栓活性を有する組成物 - Google Patents
新規化合物並びに抗炎症及び抗血栓活性を有する組成物 Download PDFInfo
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- JP3880067B2 JP3880067B2 JP51706097A JP51706097A JP3880067B2 JP 3880067 B2 JP3880067 B2 JP 3880067B2 JP 51706097 A JP51706097 A JP 51706097A JP 51706097 A JP51706097 A JP 51706097A JP 3880067 B2 JP3880067 B2 JP 3880067B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
- C07C203/02—Esters of nitric acid
- C07C203/04—Esters of nitric acid having nitrate groups bound to acyclic carbon atoms
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- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
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| IT95A002263 | 1995-10-31 | ||
| IT95MI002263A IT1276071B1 (it) | 1995-10-31 | 1995-10-31 | Compositi ad attivita' anti-infiammatoria |
| PCT/EP1996/004696 WO1997016405A1 (en) | 1995-10-31 | 1996-10-29 | New compounds and their compositions having anti-inflammatory and anti-thrombotic activities |
Publications (3)
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| JPH11514636A JPH11514636A (ja) | 1999-12-14 |
| JPH11514636A5 JPH11514636A5 (enExample) | 2004-10-21 |
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| EP (1) | EP0871606B1 (enExample) |
| JP (1) | JP3880067B2 (enExample) |
| KR (1) | KR100546038B1 (enExample) |
| AT (1) | ATE193883T1 (enExample) |
| AU (1) | AU709338B2 (enExample) |
| BR (1) | BR9611175B1 (enExample) |
| CA (1) | CA2235996C (enExample) |
| DE (1) | DE69608916T2 (enExample) |
| DK (1) | DK0871606T3 (enExample) |
| ES (1) | ES2148808T3 (enExample) |
| GR (1) | GR3033827T3 (enExample) |
| HU (1) | HUP9802986A3 (enExample) |
| IT (1) | IT1276071B1 (enExample) |
| PT (1) | PT871606E (enExample) |
| RU (1) | RU2165921C2 (enExample) |
| SI (1) | SI0871606T1 (enExample) |
| WO (1) | WO1997016405A1 (enExample) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5703073A (en) | 1995-04-19 | 1997-12-30 | Nitromed, Inc. | Compositions and methods to prevent toxicity induced by nonsteroidal antiinflammatory drugs |
| US6043232A (en) * | 1997-07-23 | 2000-03-28 | Nitromed, Inc. | Nitroso esters of beta-oxo-amides and aryl propionic acid derivatives of non-steroidal antiinflammatory drugs |
| IT1276071B1 (it) * | 1995-10-31 | 1997-10-24 | Nicox Ltd | Compositi ad attivita' anti-infiammatoria |
| US7115661B1 (en) | 1999-12-29 | 2006-10-03 | Queen's University At Kingston | Methods and compositions for mitigating pain |
| US20050137191A1 (en) * | 1996-06-04 | 2005-06-23 | Thatcher Gregory R. | Nitrate esters and their use for mitigating cellular damage |
| IT1288123B1 (it) * | 1996-09-04 | 1998-09-10 | Nicox Sa | Uso di nitroderivati per l'incontinenza urinaria |
| US20040082652A1 (en) * | 1996-09-04 | 2004-04-29 | Nicox S.A. | Nitric ester derivatives and their use in treating gastrointestinal tumors |
| GB9801398D0 (en) | 1998-01-22 | 1998-03-18 | Anggard Erik E | Chemical compounds |
| US6136804A (en) | 1998-03-13 | 2000-10-24 | Merck & Co., Inc. | Combination therapy for treating, preventing, or reducing the risks associated with acute coronary ischemic syndrome and related conditions |
| WO1999045913A1 (en) * | 1998-03-13 | 1999-09-16 | Merck & Co., Inc. | Combination therapy and composition for acute coronary ischemic syndrome and related conditions |
| ES2136581B1 (es) * | 1998-05-27 | 2000-09-16 | Uriach & Cia Sa J | Uso de derivados del acido-2-hidroxi-4-trifluorometilbenzoico para la preparacion de medicamentos utiles para inhibir el factor de transcripcion nuclear nf-kb. |
| US6395724B1 (en) | 1998-06-08 | 2002-05-28 | Advanced Medicine, Inc. | Multibinding inhibitors of cyclooxygenase-2 |
| JP2002525298A (ja) * | 1998-09-28 | 2002-08-13 | メルク エンド カムパニー インコーポレーテッド | トロンビン阻害剤の投与による炎症疾患の処置法 |
| WO2000025776A1 (en) | 1998-10-30 | 2000-05-11 | Nitromed, Inc. | Nitrosated and nitrosylated nonsteroidal antiinflammatory compounds, compositions and methods of use |
| IT1307928B1 (it) * | 1999-01-26 | 2001-11-29 | Nicox Sa | Metodo di sintesi di nitrossimetilfenil esteri di derivatidell'aspirina. |
| IT1308633B1 (it) * | 1999-03-02 | 2002-01-09 | Nicox Sa | Nitrossiderivati. |
| IT1311924B1 (it) * | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| US6509377B1 (en) * | 1999-05-26 | 2003-01-21 | J. Uriach & Cia, S.A. | Use of a 2-hydroxy-4-trifluoromethylbenzoic acid derivatives as inhibitors of the activation of the nuclear transcription factor NF-κB |
| IT1312115B1 (it) | 1999-06-24 | 2002-04-04 | Nicox Sa | Composti amorfi e relative composizioni farmaceutiche |
| ITMI991517A1 (it) | 1999-07-09 | 2001-01-09 | Nicox Sa | Procedimento per ottenere nitrossimetil fenil esterni di derivati dell'acido salicilico |
| IT1313596B1 (it) * | 1999-08-04 | 2002-09-09 | Nicox Sa | Processo per la preparazione di nitrossialchil esteri del naproxene |
| CN100486573C (zh) * | 1999-12-23 | 2009-05-13 | 硝化医药股份有限公司 | 硝基化的和亚硝基化的环加氧酶-2抑制剂、组合物及其用途 |
| US6538033B2 (en) * | 2000-08-29 | 2003-03-25 | Huntington Medical Research Institutes | Nitric oxide donor compounds |
| IT1319202B1 (it) * | 2000-10-12 | 2003-09-26 | Nicox Sa | Farmaci per le malattie a base infiammatoria. |
| IT1319201B1 (it) * | 2000-10-12 | 2003-09-26 | Nicox Sa | Farmaci per il diabete. |
| ATE338544T1 (de) * | 2000-12-21 | 2006-09-15 | Nitromed Inc | Substituierte arylverbindungen als neue, cyclooxygenase-2-selektive inhibitoren, zusammensetzungen und verwendungsverfahren |
| GB0111872D0 (en) * | 2001-05-15 | 2001-07-04 | Northwick Park Inst For Medica | Therapeutic agents and methods |
| 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 |
| ITMI20011240A1 (it) * | 2001-06-13 | 2002-12-13 | Nicox Sa | Farmaci per le vasculopatie |
| ITMI20011307A1 (it) * | 2001-06-21 | 2002-12-21 | Nicox Sa | Farmaci per l'epilessia |
| ITMI20011308A1 (it) | 2001-06-21 | 2002-12-21 | Nicox Sa | Farmaci per il dolore cronico |
| CA2475209A1 (en) * | 2002-02-04 | 2003-08-14 | Alfama - Investigacao E Desenvolvimento De Produtos Farmaceuticos Lda. | Use of co-releasing compounds for the manufacture of a medicament for the treatment of inflammatory diseases |
| US20080026984A1 (en) * | 2002-02-04 | 2008-01-31 | Alfama - Investigacao E Desenvolvimento De Productos Farmaceuticos Lda | Methods for treating inflammatory disease by administering aldehydes and derivatives thereof |
| US7968605B2 (en) * | 2002-02-04 | 2011-06-28 | ALFAMA—Investigação e Desenvolvimento de Produtos Farmacêuticos, Lda. | Methods for treating inflammatory disease by administering aldehydes and derivatives thereof |
| WO2003094924A1 (en) * | 2002-05-10 | 2003-11-20 | Merck & Co., Inc. | Combination therapy for treating cyclooxygenase-2 mediated diseases in patients at risk of thrombotic cardiovascular events |
| US20050215611A1 (en) * | 2002-05-10 | 2005-09-29 | Hunt Richard H | Combination therapy for treating cyclooxygenase-2 mediated diseases in patients at risk of thrombotic cardiovascular events |
| US7220749B2 (en) | 2002-06-11 | 2007-05-22 | Nitromed, Inc. | Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| CA2489428A1 (en) | 2002-06-27 | 2004-01-08 | Nitromed, Inc. | Cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| US7211598B2 (en) * | 2002-06-28 | 2007-05-01 | Nitromed, Inc. | Oxime and/or hydrozone containing 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 |
| WO2004011421A1 (en) | 2002-07-26 | 2004-02-05 | Merck Frosst Canada & Co. | Nitric oxide releasing prodrugs of diaryl-2-(5h)-furanones as cyclooxygenase-2 inhibitors |
| CA2493156A1 (en) * | 2002-07-29 | 2004-02-05 | Nitromed, Inc. | Cyclooxygenase-2 selective inhibitors, compositions and methods of use |
| ITMI20021861A1 (it) * | 2002-08-29 | 2004-02-29 | Nicox Sa | Procedimento di sintesi di nitrossialchilesteri di acidi carbossilici, intermedi impiegabili in detto procedimento e loro preparazione. |
| KR20050057496A (ko) * | 2002-09-20 | 2005-06-16 | 니콕스 에스. 에이. | Ｎｏ-공여 디클로페낙과 같은 ｎｏ-공여 화합물의제조방법 |
| EP1562975A2 (en) * | 2002-10-25 | 2005-08-17 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Steroid compounds comprising superoxide dismutase mimic groups and nitric oxide donor groups, and their use in the preparation of medicaments |
| GB2395432B (en) * | 2002-11-20 | 2005-09-14 | Northwick Park Inst For Medica | Therapeutic delivery of carbon monoxide to extracorporeal and isolated organs |
| ITMI20022658A1 (it) | 2002-12-17 | 2004-06-18 | Nicox Sa | Farmaci per il dolore cronico. |
| US7166638B2 (en) * | 2003-05-27 | 2007-01-23 | Nicox S.A. | Statin derivatives |
| US7169805B2 (en) | 2003-05-28 | 2007-01-30 | Nicox S.A. | Captopril derivatives |
| ES2322263T3 (es) | 2003-06-19 | 2009-06-18 | Nicox S.A. | Mitroxiderivados de enalapril y compuestos relacionados con inhibidores de ace, para el tratamiento de enfermedades cardiovasculares. |
| EP1709155B1 (en) * | 2003-12-31 | 2013-10-02 | Chesterford Enterprises Limited | Compounds and compositions for treating dysproliferative diseases, and methods of use thereof |
| TW200616604A (en) | 2004-08-26 | 2006-06-01 | Nicholas Piramal India Ltd | Nitric oxide releasing prodrugs containing bio-cleavable linker |
| AU2005281359A1 (en) | 2004-08-26 | 2006-03-16 | Apparao Satyam | Prodrugs and codrugs containing novel bio-cleavable disulfide linkers |
| US7521435B2 (en) * | 2005-02-18 | 2009-04-21 | Pharma Diagnostics, N.V. | Silicon containing compounds having selective COX-2 inhibitory activity and methods of making and using the same |
| EP1951653B1 (en) | 2005-11-23 | 2010-10-20 | NicOx S.A. | Salicylic acid derivatives |
| WO2007073226A1 (en) * | 2005-12-20 | 2007-06-28 | Alfama - Investigação E Desenvolvimento De Produtos Farmacêuticos Lda | Method for treating a mammal by administration of a compound having the ability to release co |
| GB0601394D0 (en) | 2006-01-24 | 2006-03-01 | Hemocorm Ltd | Therapeutic delivery of carbon monoxide |
| JP2007275193A (ja) * | 2006-04-04 | 2007-10-25 | Fujifilm Corp | 光プローブおよび光断層画像化装置 |
| CA2705463C (en) * | 2007-08-10 | 2014-10-07 | Basil Rigas | Anti-inflammatory compounds and uses thereof |
| WO2010118968A1 (en) | 2009-04-16 | 2010-10-21 | Nicox S.A. | No-donor aspirin derivatives |
| WO2011160974A2 (en) | 2010-06-21 | 2011-12-29 | Nicox S.A. | Statin derivatives |
| WO2012145520A2 (en) | 2011-04-19 | 2012-10-26 | Alfama, Inc. | Carbon monoxide releasing molecules and uses thereof |
| EP2734235B1 (en) | 2011-07-21 | 2017-03-22 | Alfama, Inc. | Ruthenium carbon monoxide releasing molecules and uses thereof |
| US9844599B2 (en) | 2013-01-21 | 2017-12-19 | Apparao Satyam | Nitric oxide releasing produgs of therapeutic agents |
| US20140271923A1 (en) | 2013-03-14 | 2014-09-18 | Christopher Brian Reid | Compositions & formulations for preventing and treating chronic diseases that cluster in patients such as cardiovascular disease, diabetes, obesity, polycystic ovary syndrome, hyperlipidemia and hypertension, as well as for preventing and treating other diseases and conditions |
| CN117843491A (zh) * | 2023-12-29 | 2024-04-09 | 陕西中医药大学 | 4-(2-(硝基氧基)乙基)-1,2-亚苯基二乙酸酯及其合成方法、应用和药物 |
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| IT1243367B (it) * | 1990-07-26 | 1994-06-10 | Italfarmaco Spa | Derivati acidi benzoici sostituiti ad attivita' cardiovascolare |
| IT1256450B (it) * | 1992-11-26 | 1995-12-05 | Soldato Piero Del | Esteri nitrici con attivita' farmacologica e procedimento per la loro preparazione |
| AU678063B2 (en) * | 1993-10-06 | 1997-05-15 | Nicox S.A. | Nitric esters having anti-inflammatory and/or analgesic activity and process for their preparation |
| AU702662B2 (en) * | 1994-05-10 | 1999-02-25 | Nicox S.A. | Nitro compounds and their compositions having anti-inflammatory, analgesic and anti-thrombotic acitivities |
| IT1276071B1 (it) * | 1995-10-31 | 1997-10-24 | Nicox Ltd | Compositi ad attivita' anti-infiammatoria |
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1995
- 1995-10-31 IT IT95MI002263A patent/IT1276071B1/it active IP Right Grant
-
1996
- 1996-10-29 WO PCT/EP1996/004696 patent/WO1997016405A1/en not_active Ceased
- 1996-10-29 PT PT96937282T patent/PT871606E/pt unknown
- 1996-10-29 BR BRPI9611175-5A patent/BR9611175B1/pt not_active IP Right Cessation
- 1996-10-29 RU RU98110565/04A patent/RU2165921C2/ru not_active IP Right Cessation
- 1996-10-29 DK DK96937282T patent/DK0871606T3/da active
- 1996-10-29 AT AT96937282T patent/ATE193883T1/de not_active IP Right Cessation
- 1996-10-29 SI SI9630170T patent/SI0871606T1/xx unknown
- 1996-10-29 CA CA002235996A patent/CA2235996C/en not_active Expired - Fee Related
- 1996-10-29 US US09/066,344 patent/US6040341A/en not_active Expired - Fee Related
- 1996-10-29 DE DE69608916T patent/DE69608916T2/de not_active Expired - Fee Related
- 1996-10-29 AU AU74950/96A patent/AU709338B2/en not_active Ceased
- 1996-10-29 HU HU9802986A patent/HUP9802986A3/hu unknown
- 1996-10-29 ES ES96937282T patent/ES2148808T3/es not_active Expired - Lifetime
- 1996-10-29 EP EP96937282A patent/EP0871606B1/en not_active Expired - Lifetime
- 1996-10-29 KR KR1019980703206A patent/KR100546038B1/ko not_active Expired - Fee Related
- 1996-10-29 JP JP51706097A patent/JP3880067B2/ja not_active Expired - Fee Related
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2000
- 2000-06-30 GR GR20000401528T patent/GR3033827T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK0871606T3 (da) | 2000-07-31 |
| WO1997016405A1 (en) | 1997-05-09 |
| BR9611175B1 (pt) | 2009-01-13 |
| AU709338B2 (en) | 1999-08-26 |
| CA2235996C (en) | 2007-01-02 |
| HUP9802986A2 (hu) | 1999-04-28 |
| EP0871606A1 (en) | 1998-10-21 |
| PT871606E (pt) | 2000-11-30 |
| ITMI952263A1 (it) | 1997-05-01 |
| HUP9802986A3 (en) | 1999-12-28 |
| JPH11514636A (ja) | 1999-12-14 |
| RU2165921C2 (ru) | 2001-04-27 |
| ES2148808T3 (es) | 2000-10-16 |
| IT1276071B1 (it) | 1997-10-24 |
| GR3033827T3 (en) | 2000-10-31 |
| SI0871606T1 (en) | 2000-08-31 |
| AU7495096A (en) | 1997-05-22 |
| BR9611175A (pt) | 1999-03-30 |
| US6040341A (en) | 2000-03-21 |
| EP0871606B1 (en) | 2000-06-14 |
| ATE193883T1 (de) | 2000-06-15 |
| DE69608916D1 (de) | 2000-07-20 |
| CA2235996A1 (en) | 1997-05-09 |
| KR19990067247A (ko) | 1999-08-16 |
| DE69608916T2 (de) | 2001-01-11 |
| ITMI952263A0 (enExample) | 1995-10-31 |
| KR100546038B1 (ko) | 2006-10-04 |
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