NZ544463A - Nitrooxy derivatives of losartan, valsartan, candesartan, telmisartan, eprosartan and olmesartan as angiotensin-II receptor blockers for the treatment of cardiovascular diseases - Google Patents
Nitrooxy derivatives of losartan, valsartan, candesartan, telmisartan, eprosartan and olmesartan as angiotensin-II receptor blockers for the treatment of cardiovascular diseasesInfo
- Publication number
- NZ544463A NZ544463A NZ544463A NZ54446304A NZ544463A NZ 544463 A NZ544463 A NZ 544463A NZ 544463 A NZ544463 A NZ 544463A NZ 54446304 A NZ54446304 A NZ 54446304A NZ 544463 A NZ544463 A NZ 544463A
- Authority
- NZ
- New Zealand
- Prior art keywords
- pct
- ono
- compound
- group
- formula
- Prior art date
Links
- 208000024172 Cardiovascular disease Diseases 0.000 title claims abstract description 13
- 238000011282 treatment Methods 0.000 title claims abstract description 11
- 102000008873 Angiotensin II receptor Human genes 0.000 title claims abstract description 10
- 108050000824 Angiotensin II receptor Proteins 0.000 title claims abstract description 10
- 239000002083 C09CA01 - Losartan Substances 0.000 title claims description 17
- 229960004773 losartan Drugs 0.000 title claims description 17
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 title description 6
- 239000002080 C09CA02 - Eprosartan Substances 0.000 title description 3
- 239000004072 C09CA03 - Valsartan Substances 0.000 title description 3
- 239000002053 C09CA06 - Candesartan Substances 0.000 title description 3
- 239000005537 C09CA07 - Telmisartan Substances 0.000 title description 3
- 239000005480 Olmesartan Substances 0.000 title description 3
- 229960000932 candesartan Drugs 0.000 title description 3
- SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 title description 3
- OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 title description 3
- 229960004563 eprosartan Drugs 0.000 title description 3
- VTRAEEWXHOVJFV-UHFFFAOYSA-N olmesartan Chemical compound CCCC1=NC(C(C)(C)O)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 VTRAEEWXHOVJFV-UHFFFAOYSA-N 0.000 title description 3
- 229960005117 olmesartan Drugs 0.000 title description 3
- 229960005187 telmisartan Drugs 0.000 title description 3
- 229960004699 valsartan Drugs 0.000 title description 3
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 title 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 141
- 229910004679 ONO2 Inorganic materials 0.000 claims abstract description 9
- 239000003087 receptor blocking agent Substances 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- -1 losartan nitroderivative Chemical class 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 14
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- 150000002828 nitro derivatives Chemical class 0.000 claims description 9
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- 230000002785 anti-thrombosis Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
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- 238000002360 preparation method Methods 0.000 claims description 7
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
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- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003118 aryl group Chemical group 0.000 claims description 2
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 208000007232 portal hypertension Diseases 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 claims description 2
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- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 claims 3
- 238000011699 spontaneously hypertensive rat Methods 0.000 claims 3
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- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 1
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- 239000011593 sulfur Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
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- 150000007530 organic bases Chemical class 0.000 description 10
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- PSIFNNKUMBGKDQ-UHFFFAOYSA-N losartan Chemical class CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2NN=NN=2)C=C1 PSIFNNKUMBGKDQ-UHFFFAOYSA-N 0.000 description 9
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- ZKJNVODQIYQUNQ-UHFFFAOYSA-N [2-butyl-5-chloro-3-[[4-[2-(1-trityltetrazol-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2N(N=NN=2)C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 ZKJNVODQIYQUNQ-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03102379 | 2003-07-31 | ||
| PCT/EP2004/051550 WO2005011646A2 (en) | 2003-07-31 | 2004-07-20 | Nitrooxy derivatives of losartan, valsatan, candesartan, telmisartan, eprosartan and olmesartan as angiotensin-ii receptor blockers for the treatment of cardiovascular diseases |
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| NZ544463A true NZ544463A (en) | 2009-10-30 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2006008196A1 (en) * | 2004-07-20 | 2006-01-26 | Nicox S.A. | Process for preparing nitrooxy esters, nitrooxy thioesters, nitrooxy carbonates and nitrooxy thiocarbonates, intermediates useful in said process and preparation thereof |
| WO2006079610A1 (en) * | 2005-01-31 | 2006-08-03 | Nicox S.A. | Nitrooxy sartan derivatives as angiotensin ii receptor blockers for the treatment of cardiovascular and inflammatory diseases |
| RU2306930C1 (ru) * | 2005-12-28 | 2007-09-27 | Михаил Владимирович Покровский | Способ коррекции эндотелиальной дисфункции комбинацией лозартана и l-аргинина при l-name-индуцированном дефиците оксида азота |
| CN101024643A (zh) | 2006-02-20 | 2007-08-29 | 上海艾力斯医药科技有限公司 | 咪唑－5－羧酸类衍生物、制备方法及其应用 |
| TW200821303A (en) * | 2006-08-08 | 2008-05-16 | Speedel Experimenta Ag | Organic compounds |
| CA2668744C (en) | 2006-11-17 | 2015-09-15 | Queen's University At Kingston | Compounds and methods for treating protein folding disorders |
| EP2103610B1 (en) * | 2006-12-06 | 2011-09-21 | Shanghai Allist Pharmaceutical., Inc. | Salts of imidazol-5-carboxylic acid derivatives, preparation methods and use thereof |
| CA2671421A1 (en) * | 2006-12-13 | 2008-06-26 | Merck & Co., Inc. | Nitroderivatives as angiotensin ii receptor antagonists |
| TW200831079A (en) * | 2006-12-13 | 2008-08-01 | Merck & Co Inc | Angiotensin II receptor antagonists |
| CN101214242A (zh) * | 2007-01-05 | 2008-07-09 | 上海艾力斯医药科技有限公司 | 新的药用组合物 |
| EP1980559A1 (en) * | 2007-04-10 | 2008-10-15 | CTG Pharma S.r.l. | Cardiovascular agents |
| CN101317842A (zh) | 2007-06-07 | 2008-12-10 | 上海艾力斯医药科技有限公司 | 一种咪唑-5-羧酸衍生物的治疗用途 |
| CN101407511B (zh) * | 2007-10-11 | 2013-01-09 | 上海艾力斯生物医药有限公司 | 一种结晶型的咪唑-5-羧酸衍生物 |
| AR069340A1 (es) | 2007-11-26 | 2010-01-13 | Merck & Co Inc | Antagonistas del receptor de angiotensina ii |
| EP2534957B1 (en) | 2007-12-14 | 2015-05-27 | AeroDesigns, Inc | Delivering aerosolizable products |
| CA2711134A1 (en) * | 2008-01-24 | 2009-07-30 | Merck Sharp & Dohme Corp. | Angiotensin ii receptor antagonists |
| CA2711461A1 (en) | 2008-02-08 | 2009-08-13 | Merck Sharp & Dohme Corp. | Angiotensin ii receptor antagonists |
| WO2009106471A2 (en) * | 2008-02-26 | 2009-09-03 | Nicox S.A. | New angiotensin ii receptor blocker derivatives |
| CA2712689A1 (en) * | 2008-02-26 | 2009-09-03 | Nicoletta Almirante | Angiotensin ii receptor antagonists |
| JP2011523941A (ja) * | 2008-05-15 | 2011-08-25 | メルク・シャープ・エンド・ドーム・コーポレイション | アンギオテンシンｉｉ受容体アンタゴニスト |
| CN101596189A (zh) * | 2008-06-05 | 2009-12-09 | 上海艾力斯生物医药有限公司 | 含有咪唑-5-羧酸类衍生物的药用组合物 |
| AU2009256822A1 (en) * | 2008-06-09 | 2009-12-17 | Nicox S.A. | Angiotensin II receptor antagonists |
| AR073259A1 (es) * | 2008-07-29 | 2010-10-28 | Merck & Co Inc | Derivados de furosemida utiles como diureticos |
| WO2010015447A1 (en) * | 2008-08-08 | 2010-02-11 | Nicox S.A. | Angiotensin ii receptor antagonists |
| EP2194048A1 (en) | 2008-12-02 | 2010-06-09 | Dirk Sartor | Nitrate esters for the treatment of vascular and metabolic diseases |
| JP2012511002A (ja) * | 2008-12-05 | 2012-05-17 | メルク・シャープ・エンド・ドーム・コーポレイション | アンジオテンシンｉｉ受容体アンタゴニストとしてのニトロオキシ誘導体 |
| SG173044A1 (en) | 2009-01-23 | 2011-08-29 | Hanmi Holdings Co Ltd | Solid pharmaceutical composition comprising amlodipine and losartan and process for producing same |
| AR080925A1 (es) | 2010-04-19 | 2012-05-16 | Cardiolynx Ag | Derivados de valsartan que portan donadores de no para el tratamiento de las enfermedades vasculares y metabolicas |
| AU2011243947A1 (en) * | 2010-04-23 | 2012-12-06 | Piramal Enterprises Limited | Nitric oxide releasing prodrugs of therapeutic agents |
| WO2011160974A2 (en) | 2010-06-21 | 2011-12-29 | Nicox S.A. | Statin derivatives |
| JO3350B1 (ar) | 2011-03-07 | 2019-03-13 | Merck Sharp & Dohme | مشتقات حلقية غير متجانسة محتوية على مجموعات أمينو أولية ومركبات داي أزينيومديولات |
| US9844599B2 (en) | 2013-01-21 | 2017-12-19 | Apparao Satyam | Nitric oxide releasing produgs of therapeutic agents |
| CN103275074B (zh) * | 2013-06-21 | 2016-08-10 | 黄冈鲁班药业股份有限公司 | 一种奥美沙坦衍生物及其制备方法 |
| CN105820125B (zh) * | 2015-01-09 | 2018-12-07 | 北京中医药大学 | 一种用于治疗高血压的化合物及其制备方法和用途 |
| WO2017041701A1 (zh) | 2015-09-07 | 2017-03-16 | 浙江华海药业股份有限公司 | 可释放一氧化氮的前药分子 |
| CN106800537B (zh) | 2017-01-18 | 2019-02-01 | 广东隆赋药业股份有限公司 | 丁苯酞-替米沙坦杂合物及其制备方法和用途 |
| CN108892624B (zh) * | 2018-06-20 | 2020-12-15 | 重庆威鹏药业有限公司 | 沙库巴曲硝基氧衍生物及其制备方法和应用 |
| CN114105881B (zh) * | 2020-08-31 | 2024-01-26 | 沈阳海诺威医药科技有限公司 | 血小板聚集抑制剂及其制备方法和用途 |
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| CA1338238C (en) * | 1988-01-07 | 1996-04-09 | David John Carini | Angiotensin ii receptor blocking imidazoles and combinations thereof with diuretics and nsaids |
| SG52330A1 (en) * | 1989-06-14 | 1998-09-28 | Smithkline Beecham Corp | Imidazolyl-alkenoic acids |
| RU2067581C1 (ru) * | 1989-06-30 | 1996-10-10 | Е.И.Дюпон Де Немур Энд Компани | Аралкилзамещенные имидазолы, обладающие противогипертоническим действием, способ их получения и фармацевтический состав, обладающий ингибирующей активностью в отношении ангиотензина ii |
| KR0163595B1 (ko) * | 1989-06-30 | 1998-12-01 | 미리암디, 메코너헤이 | 치환된 이미다졸 |
| AT398202B (de) * | 1991-10-04 | 1994-10-25 | Chem Pharm Forsch Gmbh | Neue imidazolderivate, verfahren zu ihrer herstellung und ihre verwendung |
| FR2725987B1 (fr) * | 1994-10-19 | 1997-01-10 | Sanofi Sa | Procede pour la preparation d'un derive de tetrazole sous deux formes cristallines et nouvelle forme cristalline de ce derive |
| IT1311924B1 (it) * | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| US20030187038A1 (en) * | 2000-08-25 | 2003-10-02 | Yoshimi Imura | Fibrinogen-lowering agents |
| ITMI20011744A1 (it) * | 2001-08-09 | 2003-02-09 | Nicox Sa | Farmaci per le vasculopatie |
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2004
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- 2004-07-20 AU AU2004260830A patent/AU2004260830B2/en not_active Ceased
- 2004-07-20 EP EP04766269A patent/EP1653950B1/en not_active Expired - Lifetime
- 2004-07-20 DE DE602004011230T patent/DE602004011230T2/de not_active Expired - Lifetime
- 2004-07-20 JP JP2006521571A patent/JP2007500684A/ja active Pending
- 2004-07-20 SI SI200430655T patent/SI1653950T1/sl unknown
- 2004-07-20 ES ES04766269T patent/ES2299861T3/es not_active Expired - Lifetime
- 2004-07-20 HR HR20060084A patent/HRP20060084A2/hr not_active Application Discontinuation
- 2004-07-20 PT PT04766269T patent/PT1653950E/pt unknown
- 2004-07-20 WO PCT/EP2004/051550 patent/WO2005011646A2/en not_active Ceased
- 2004-07-20 CN CNB200480022483XA patent/CN100496490C/zh not_active Expired - Fee Related
- 2004-07-20 KR KR1020067001893A patent/KR20060056352A/ko not_active Ceased
- 2004-07-20 NZ NZ544463A patent/NZ544463A/en unknown
- 2004-07-20 PL PL04766269T patent/PL1653950T3/pl unknown
- 2004-07-20 RU RU2006105804/04A patent/RU2374240C2/ru not_active IP Right Cessation
- 2004-07-20 MX MXPA06001263A patent/MXPA06001263A/es active IP Right Grant
- 2004-07-20 AT AT04766269T patent/ATE383155T1/de not_active IP Right Cessation
- 2004-07-20 UA UAA200600273A patent/UA87983C2/ru unknown
- 2004-07-20 PL PL379420A patent/PL379420A1/pl not_active Application Discontinuation
- 2004-07-20 CA CA002534451A patent/CA2534451A1/en not_active Abandoned
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2006
- 2006-01-30 ZA ZA200600856A patent/ZA200600856B/en unknown
- 2006-01-30 EC EC2006006334A patent/ECSP066334A/es unknown
- 2006-02-13 MA MA28789A patent/MA27987A1/fr unknown
- 2006-02-24 NO NO20060900A patent/NO20060900L/no not_active Application Discontinuation
- 2006-02-27 IS IS8332A patent/IS2534B/is unknown
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2008
- 2008-04-07 CY CY20081100385T patent/CY1110447T1/el unknown
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