AU2002338528B2 - Nitrosated and nitrosylated nebivolol and its metabolites, compositions and methods of use - Google Patents
Nitrosated and nitrosylated nebivolol and its metabolites, compositions and methods of use Download PDFInfo
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- AU2002338528B2 AU2002338528B2 AU2002338528A AU2002338528A AU2002338528B2 AU 2002338528 B2 AU2002338528 B2 AU 2002338528B2 AU 2002338528 A AU2002338528 A AU 2002338528A AU 2002338528 A AU2002338528 A AU 2002338528A AU 2002338528 B2 AU2002338528 B2 AU 2002338528B2
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- Prior art keywords
- nitric oxide
- hypertension
- compound
- nitrosated
- formula
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- KOHIRBRYDXPAMZ-YHBROIRLSA-N (S,R,R,R)-nebivolol Chemical compound C1CC2=CC(F)=CC=C2O[C@H]1[C@H](O)CNC[C@@H](O)[C@H]1OC2=CC=C(F)C=C2CC1 KOHIRBRYDXPAMZ-YHBROIRLSA-N 0.000 title claims abstract description 178
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 229960000619 nebivolol Drugs 0.000 title claims abstract description 105
- 238000000034 method Methods 0.000 title claims abstract description 84
- 239000002207 metabolite Substances 0.000 title description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 519
- 150000001875 compounds Chemical class 0.000 claims abstract description 241
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 61
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 51
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 43
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims abstract description 38
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims abstract description 38
- 239000000066 endothelium dependent relaxing factor Substances 0.000 claims abstract description 38
- 238000012546 transfer Methods 0.000 claims abstract description 38
- 239000000758 substrate Substances 0.000 claims abstract description 35
- 208000019553 vascular disease Diseases 0.000 claims abstract description 23
- 150000002148 esters Chemical class 0.000 claims description 90
- 239000002253 acid Substances 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 206010020772 Hypertension Diseases 0.000 claims description 44
- 229910052702 rhenium Inorganic materials 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 229910002651 NO3 Inorganic materials 0.000 claims description 22
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
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- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 14
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- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 10
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 10
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 230000036542 oxidative stress Effects 0.000 claims description 7
- ICRHORQIUXBEPA-UHFFFAOYSA-N thionitrous acid Chemical compound SN=O ICRHORQIUXBEPA-UHFFFAOYSA-N 0.000 claims description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
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- 206010070538 Gestational hypertension Diseases 0.000 claims description 6
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- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 208000028208 end stage renal disease Diseases 0.000 claims description 6
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- 229910052736 halogen Inorganic materials 0.000 claims description 6
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- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 6
- 208000036335 preeclampsia/eclampsia 1 Diseases 0.000 claims description 6
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- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 5
- 108091034117 Oligonucleotide Proteins 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
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- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 5
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 4
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- 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 4
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 4
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- 235000000346 sugar Nutrition 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
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- 239000002308 endothelin receptor antagonist Substances 0.000 claims description 3
- AZLYZRGJCVQKKK-UHFFFAOYSA-N dioxohydrazine Chemical compound O=NN=O AZLYZRGJCVQKKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 230000002685 pulmonary effect Effects 0.000 claims 2
- -1 hydralazine compound Chemical class 0.000 abstract description 180
- 239000002840 nitric oxide donor Substances 0.000 abstract description 47
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- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 abstract description 19
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 abstract description 17
- RPTUSVTUFVMDQK-UHFFFAOYSA-N hydrallazine Natural products C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 abstract description 16
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| DE10053397A1 (de) | 2000-10-20 | 2002-05-02 | Schering Ag | Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen |
| JP2007502831A (ja) * | 2003-08-20 | 2007-02-15 | ニトロメッド インコーポレーティッド | ニトロソ化およびニトロシル化心血管化合物、組成物、ならびに使用方法 |
| US7754500B2 (en) | 2003-11-21 | 2010-07-13 | Anp Technologies, Inc. | Asymmetrically branched polymer conjugates and microarray assays |
| US20090131342A1 (en) * | 2004-01-22 | 2009-05-21 | Nitromed, Inc. | Nitrosated and/or nitrosylated compounds, compositions and methods of use |
| ES2543836T3 (es) * | 2004-04-23 | 2015-08-24 | Northern Sydney Local Health District | Procedimientos y composiciones para el tratamiento de afecciones miocárdicas |
| DE602005025755D1 (de) | 2004-06-04 | 2011-02-17 | Teva Pharma | Irbesartan enthaltende pharmazeutische zusammensetzung |
| US7803838B2 (en) * | 2004-06-04 | 2010-09-28 | Forest Laboratories Holdings Limited | Compositions comprising nebivolol |
| US7838552B2 (en) * | 2004-06-04 | 2010-11-23 | Forest Laboratories Holdings Limited | Compositions comprising nebivolol |
| EP1741712B1 (en) | 2004-07-30 | 2011-06-15 | Torrent Pharmaceuticals Ltd | amorphous form of nebivolol hydrochloride and its preparation |
| EP1781331A1 (en) * | 2004-08-09 | 2007-05-09 | Université Catholique de Louvain | Use of agonists and antagonists of beta-adrenoceptors for treating arterial diseases |
| JP2008528626A (ja) * | 2005-01-31 | 2008-07-31 | マイラン ラボラトリーズ インク． | ヒドロキシル化されたネビボロールを含む薬学的組成物 |
| KR101390563B1 (ko) * | 2005-01-31 | 2014-04-30 | 밀란 인크. | 글루쿠로니드화된 네비볼롤 |
| US20060222592A1 (en) * | 2005-04-05 | 2006-10-05 | Clemens Burda | Nanoparticles and methods of manufacturing nanoparticles for electronic and non-electronic applications |
| ATE496297T1 (de) | 2005-05-02 | 2011-02-15 | Anp Technologies Inc | Polymerkonjugat-verbesserte bioassays |
| RU2441653C2 (ru) * | 2005-05-31 | 2012-02-10 | Милан Лэборетериз, Инк. | Композиции, содержащие небиволол |
| AU2005332300B2 (en) * | 2005-05-31 | 2011-07-07 | Mylan Laboratories, Inc. | Compositions comprising nebivolol |
| CA2624936A1 (en) * | 2005-10-04 | 2007-04-12 | Nitromed, Inc. | The genetic risk assessment in heart failure: impact of genetic variation of aldosterone synthase promoter polymorphism |
| US20070154466A1 (en) * | 2005-12-30 | 2007-07-05 | Jan Weber | Internal medical devices containing peroxide-converting catalysts |
| US20080193385A1 (en) * | 2007-02-08 | 2008-08-14 | Todd Maibach | Compositions and methods for treating neuropathy |
| CA2599082A1 (en) * | 2007-08-27 | 2009-02-27 | Ping I. Lee | Supramacromolecular polymer complexes providing controlled nitric oxide release for healing wounds |
| WO2009026697A1 (en) * | 2007-08-28 | 2009-03-05 | University Of Manitoba | A method of reducing a vasodilatory response using a guanylate cyclase pathway inhibitor or an h2o2 reducing agent |
| CN101970012A (zh) | 2007-09-14 | 2011-02-09 | 日东电工株式会社 | 药物载体 |
| CA2732513C (en) | 2008-08-01 | 2017-04-25 | Arca Biopharma, Inc. | Methods and compositions involving (s)-bucindolol |
| HUP0800498A2 (en) * | 2008-08-06 | 2010-03-29 | Semmelweis Egyetem | Use of dihydralazine for the preparation of medicaments for treatment of diseases related to ssao level |
| US8579964B2 (en) | 2010-05-05 | 2013-11-12 | Neovasc Inc. | Transcatheter mitral valve prosthesis |
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| US9554897B2 (en) | 2011-04-28 | 2017-01-31 | Neovasc Tiara Inc. | Methods and apparatus for engaging a valve prosthesis with tissue |
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| CN102977068A (zh) * | 2012-05-03 | 2013-03-20 | 中国药科大学 | 一氧化氮供体型异色满酮类衍生物、其制备方法及用途 |
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| EP3946163B1 (en) | 2019-04-01 | 2025-08-20 | Neovasc Tiara Inc. | Controllably deployable prosthetic valve |
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2002
- 2002-05-01 WO PCT/US2002/013667 patent/WO2002087508A2/en not_active Ceased
- 2002-05-01 JP JP2002584860A patent/JP2004528337A/ja not_active Withdrawn
- 2002-05-01 EP EP02766876A patent/EP1406608B1/en not_active Expired - Lifetime
- 2002-05-01 AU AU2002338528A patent/AU2002338528B2/en not_active Ceased
- 2002-05-01 CA CA002446064A patent/CA2446064A1/en not_active Abandoned
- 2002-05-01 DE DE60233140T patent/DE60233140D1/de not_active Expired - Lifetime
- 2002-05-01 AT AT02766876T patent/ATE437637T1/de not_active IP Right Cessation
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2003
- 2003-10-29 US US10/695,644 patent/US7138430B2/en not_active Expired - Fee Related
-
2005
- 2005-07-13 US US11/135,418 patent/US7384976B2/en not_active Expired - Fee Related
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2010
- 2010-06-25 JP JP2010145153A patent/JP2010248226A/ja active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2001012584A2 (en) * | 1999-08-12 | 2001-02-22 | Nicox S.A. | Pharmaceutical compounds |
| US6635273B1 (en) * | 1999-10-29 | 2003-10-21 | Trustees Of Boston University | Methods of treating vascular diseases characterized by nitric oxide insufficiency |
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| Cardiovascular Research, 2001, 49(2), pp 430-9 * |
| Hypertension, 1999, 3(III), pp467-71 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2446064A1 (en) | 2002-11-07 |
| ATE437637T1 (de) | 2009-08-15 |
| US7384976B2 (en) | 2008-06-10 |
| EP1406608B1 (en) | 2009-07-29 |
| WO2002087508A3 (en) | 2003-12-11 |
| WO2002087508A2 (en) | 2002-11-07 |
| US20040132805A1 (en) | 2004-07-08 |
| US20060009513A1 (en) | 2006-01-12 |
| EP1406608A4 (en) | 2004-10-20 |
| EP1406608A2 (en) | 2004-04-14 |
| JP2010248226A (ja) | 2010-11-04 |
| DE60233140D1 (de) | 2009-09-10 |
| JP2004528337A (ja) | 2004-09-16 |
| US7138430B2 (en) | 2006-11-21 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: NICOX S.A. Free format text: FORMER OWNER WAS: NITROMED, INC. |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |