CA2586106C - Sulfamides as endothelin receptor antagonists for the treatment of cardiovascular diseases - Google Patents
Sulfamides as endothelin receptor antagonists for the treatment of cardiovascular diseases Download PDFInfo
- Publication number
- CA2586106C CA2586106C CA2586106A CA2586106A CA2586106C CA 2586106 C CA2586106 C CA 2586106C CA 2586106 A CA2586106 A CA 2586106A CA 2586106 A CA2586106 A CA 2586106A CA 2586106 C CA2586106 C CA 2586106C
- Authority
- CA
- Canada
- Prior art keywords
- treatment
- compound
- endothelin
- role
- active ingredients
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000011282 treatment Methods 0.000 title claims 18
- 229940118365 Endothelin receptor antagonist Drugs 0.000 title abstract description 3
- 239000002308 endothelin receptor antagonist Substances 0.000 title abstract description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 title abstract 2
- 208000024172 Cardiovascular disease Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- 239000004480 active ingredient Substances 0.000 claims abstract 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 10
- 239000000203 mixture Substances 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims abstract 6
- -1 2-methoxyphenoxy, 3-methoxyphenoxy, 2-chloro-5-methoxy-phenoxy Chemical group 0.000 claims abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract 3
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052801 chlorine Chemical group 0.000 claims abstract 2
- 239000000460 chlorine Chemical group 0.000 claims abstract 2
- 102000002045 Endothelin Human genes 0.000 claims 12
- 108050009340 Endothelin Proteins 0.000 claims 12
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 208000035475 disorder Diseases 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 5
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 4
- 201000004569 Blindness Diseases 0.000 claims 4
- 201000006474 Brain Ischemia Diseases 0.000 claims 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 4
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 4
- 229930105110 Cyclosporin A Natural products 0.000 claims 4
- 108010036949 Cyclosporine Proteins 0.000 claims 4
- 206010011878 Deafness Diseases 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 4
- 208000002249 Diabetes Complications Diseases 0.000 claims 4
- 206010012655 Diabetic complications Diseases 0.000 claims 4
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 4
- 208000010412 Glaucoma Diseases 0.000 claims 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims 4
- 206010019280 Heart failures Diseases 0.000 claims 4
- 208000032843 Hemorrhage Diseases 0.000 claims 4
- 206010020772 Hypertension Diseases 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 4
- 208000019695 Migraine disease Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 4
- 208000003782 Raynaud disease Diseases 0.000 claims 4
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 4
- 208000001647 Renal Insufficiency Diseases 0.000 claims 4
- 206010038419 Renal colic Diseases 0.000 claims 4
- 206010063897 Renal ischaemia Diseases 0.000 claims 4
- 206010040047 Sepsis Diseases 0.000 claims 4
- 206010040943 Skin Ulcer Diseases 0.000 claims 4
- 208000007107 Stomach Ulcer Diseases 0.000 claims 4
- 206010001902 amaurosis Diseases 0.000 claims 4
- 238000002399 angioplasty Methods 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 206010006451 bronchitis Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 238000007675 cardiac surgery Methods 0.000 claims 4
- 206010008118 cerebral infarction Diseases 0.000 claims 4
- 208000007451 chronic bronchitis Diseases 0.000 claims 4
- 229960001265 ciclosporin Drugs 0.000 claims 4
- 208000018631 connective tissue disease Diseases 0.000 claims 4
- 208000029078 coronary artery disease Diseases 0.000 claims 4
- 229930182912 cyclosporin Natural products 0.000 claims 4
- 208000000718 duodenal ulcer Diseases 0.000 claims 4
- 201000005917 gastric ulcer Diseases 0.000 claims 4
- 230000010370 hearing loss Effects 0.000 claims 4
- 231100000888 hearing loss Toxicity 0.000 claims 4
- 208000016354 hearing loss disease Diseases 0.000 claims 4
- 201000001881 impotence Diseases 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- 201000006370 kidney failure Diseases 0.000 claims 4
- 206010027599 migraine Diseases 0.000 claims 4
- 208000031225 myocardial ischemia Diseases 0.000 claims 4
- 210000000056 organ Anatomy 0.000 claims 4
- 208000007232 portal hypertension Diseases 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 238000011321 prophylaxis Methods 0.000 claims 4
- 201000004240 prostatic hypertrophy Diseases 0.000 claims 4
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 4
- 208000002815 pulmonary hypertension Diseases 0.000 claims 4
- 208000037803 restenosis Diseases 0.000 claims 4
- 208000013223 septicemia Diseases 0.000 claims 4
- 230000035939 shock Effects 0.000 claims 4
- 208000007056 sickle cell anemia Diseases 0.000 claims 4
- 210000002784 stomach Anatomy 0.000 claims 4
- 238000002560 therapeutic procedure Methods 0.000 claims 4
- 238000002054 transplantation Methods 0.000 claims 4
- 230000002792 vascular Effects 0.000 claims 4
- 238000007631 vascular surgery Methods 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 230000002062 proliferating effect Effects 0.000 claims 3
- NZNJQXHLVGOHMX-UHFFFAOYSA-N 3-(sulfoamino)propanoic acid Chemical compound OC(=O)CCNS(O)(=O)=O NZNJQXHLVGOHMX-UHFFFAOYSA-N 0.000 claims 1
- JIJWAGNGLPTXDB-UHFFFAOYSA-N 3-[[5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yl)oxyethoxy]pyrimidin-4-yl]sulfamoylamino]propan-1-ol Chemical compound C=1C=C(Br)C=CC=1C=1C(NS(=O)(=O)NCCCO)=NC=NC=1OCCOC1=NC=C(Br)C=N1 JIJWAGNGLPTXDB-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Classifications
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Reproductive Health (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP2004/012774 | 2004-11-11 | ||
| EP2004012774 | 2004-11-11 | ||
| PCT/IB2005/053716 WO2006051502A2 (en) | 2004-11-11 | 2005-11-11 | Sulfamides as endothelin receptor antagonists for the treatment of cardiovascular diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2586106A1 CA2586106A1 (en) | 2006-05-18 |
| CA2586106C true CA2586106C (en) | 2014-01-21 |
Family
ID=36177271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2586106A Expired - Fee Related CA2586106C (en) | 2004-11-11 | 2005-11-11 | Sulfamides as endothelin receptor antagonists for the treatment of cardiovascular diseases |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7868012B2 (enExample) |
| EP (1) | EP1833821B1 (enExample) |
| JP (1) | JP5020089B2 (enExample) |
| KR (1) | KR101285463B1 (enExample) |
| CN (1) | CN101056872A (enExample) |
| AR (1) | AR051764A1 (enExample) |
| AT (1) | ATE503752T1 (enExample) |
| AU (1) | AU2005303435A1 (enExample) |
| BR (1) | BRPI0517565A (enExample) |
| CA (1) | CA2586106C (enExample) |
| CY (1) | CY1111578T1 (enExample) |
| DE (1) | DE602005027251D1 (enExample) |
| DK (1) | DK1833821T3 (enExample) |
| ES (1) | ES2362103T3 (enExample) |
| MX (1) | MX2007005566A (enExample) |
| PL (1) | PL1833821T3 (enExample) |
| PT (1) | PT1833821E (enExample) |
| RU (1) | RU2007121842A (enExample) |
| SI (1) | SI1833821T1 (enExample) |
| TW (1) | TW200628467A (enExample) |
| WO (1) | WO2006051502A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008120093A1 (en) * | 2007-04-03 | 2008-10-09 | Pfizer Inc. | Sulfonamides and pharmaceutical compositions thereof |
| WO2010018549A2 (en) * | 2008-08-13 | 2010-02-18 | Actelion Pharmaceuticals Ltd | Therapeutic compositions containing macitentan |
| AR095727A1 (es) * | 2013-03-27 | 2015-11-04 | Actelion Pharmaceuticals Ltd | Preparación de intermediarios de pirimidina |
| US9899745B2 (en) | 2013-09-13 | 2018-02-20 | Raytheon Company | Low profile high efficiency multi-band reflector antennas |
| CN103724281A (zh) * | 2013-12-03 | 2014-04-16 | 镇江圣安医药有限公司 | N-[5-（4-溴苯基）-6-[2-[（5-溴-2-嘧啶基）氧基]乙氧基]-4-嘧啶基]-n′-丙基磺酰胺的新型衍生物及其应用 |
| CN104447572A (zh) * | 2014-12-15 | 2015-03-25 | 南京艾德凯腾生物医药有限责任公司 | 一种马西替坦的制备方法 |
| HRP20230318T1 (hr) * | 2017-11-21 | 2023-05-12 | Wuxi Biocity Biopharmaceutics Co., Ltd. | Derivat pirimidin sulfamida, postupak pripreme i njegova medicinska primjena |
| CN108997223B (zh) * | 2018-08-09 | 2020-06-30 | 浙江先锋科技股份有限公司 | 5-(4-溴苯基)-4，6-二氯嘧啶的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2086544C1 (ru) | 1991-06-13 | 1997-08-10 | Хоффманн-Ля Рош АГ | Бензолсульфонамидные производные пиримидина или их соли, фармацевтическая композиция для лечения заболеваний, связанных с активностью эндотелина |
| TW394761B (en) | 1993-06-28 | 2000-06-21 | Hoffmann La Roche | Novel Sulfonylamino Pyrimidines |
| IL111959A (en) | 1993-12-17 | 2000-07-16 | Tanabe Seiyaku Co | N-(polysubstituted pyrimidin-4-yl) benzenesulfonamide derivatives their preparation and pharmaceutical compositions containing them |
| TW313568B (enExample) | 1994-12-20 | 1997-08-21 | Hoffmann La Roche | |
| US5739333A (en) | 1995-05-16 | 1998-04-14 | Tanabe Seiyaku Co., Ltd. | Sulfonamide derivative and process for preparing the same |
| RU2172735C2 (ru) | 1995-12-20 | 2001-08-27 | Яманоути Фармасьютикал Ко., Лтд. | Арилэтенсульфонамидные производные и фармацевтическая композиция |
| JPH10226649A (ja) * | 1996-12-12 | 1998-08-25 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
| BRPI0116237B8 (pt) * | 2000-12-18 | 2021-05-25 | Actelion Pharmaceuticals Ltd | "composto de sulfamida, composição farmacêutica contendo o mesmo e seu uso como medicamento antagonista de receptor de endotelina". |
| AU2003285321B2 (en) * | 2002-12-02 | 2010-04-08 | Actelion Pharmaceuticals Ltd | Pyrimidine-sulfamides and their use as endothelian receptor antagonist |
-
2005
- 2005-11-10 TW TW094139488A patent/TW200628467A/zh unknown
- 2005-11-11 DE DE602005027251T patent/DE602005027251D1/de not_active Expired - Lifetime
- 2005-11-11 WO PCT/IB2005/053716 patent/WO2006051502A2/en not_active Ceased
- 2005-11-11 ES ES05802290T patent/ES2362103T3/es not_active Expired - Lifetime
- 2005-11-11 AR ARP050104726A patent/AR051764A1/es not_active Application Discontinuation
- 2005-11-11 SI SI200531305T patent/SI1833821T1/sl unknown
- 2005-11-11 KR KR1020077012690A patent/KR101285463B1/ko not_active Expired - Fee Related
- 2005-11-11 PL PL05802290T patent/PL1833821T3/pl unknown
- 2005-11-11 DK DK05802290.6T patent/DK1833821T3/da active
- 2005-11-11 AT AT05802290T patent/ATE503752T1/de active
- 2005-11-11 PT PT05802290T patent/PT1833821E/pt unknown
- 2005-11-11 EP EP05802290A patent/EP1833821B1/en not_active Expired - Lifetime
- 2005-11-11 BR BRPI0517565-8A patent/BRPI0517565A/pt not_active Application Discontinuation
- 2005-11-11 JP JP2007540808A patent/JP5020089B2/ja not_active Expired - Fee Related
- 2005-11-11 CN CNA200580038466XA patent/CN101056872A/zh active Pending
- 2005-11-11 CA CA2586106A patent/CA2586106C/en not_active Expired - Fee Related
- 2005-11-11 MX MX2007005566A patent/MX2007005566A/es not_active Application Discontinuation
- 2005-11-11 AU AU2005303435A patent/AU2005303435A1/en not_active Abandoned
- 2005-11-11 RU RU2007121842/04A patent/RU2007121842A/ru not_active Application Discontinuation
- 2005-11-11 US US11/718,922 patent/US7868012B2/en active Active
-
2011
- 2011-06-16 CY CY20111100575T patent/CY1111578T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1833821E (pt) | 2011-06-06 |
| PL1833821T3 (pl) | 2011-09-30 |
| US7868012B2 (en) | 2011-01-11 |
| ATE503752T1 (de) | 2011-04-15 |
| WO2006051502A2 (en) | 2006-05-18 |
| DE602005027251D1 (de) | 2011-05-12 |
| JP2008519826A (ja) | 2008-06-12 |
| EP1833821B1 (en) | 2011-03-30 |
| BRPI0517565A (pt) | 2008-10-14 |
| AU2005303435A1 (en) | 2006-05-18 |
| CY1111578T1 (el) | 2015-10-07 |
| KR20070085787A (ko) | 2007-08-27 |
| US20080004298A1 (en) | 2008-01-03 |
| DK1833821T3 (da) | 2011-06-06 |
| MX2007005566A (es) | 2007-05-21 |
| RU2007121842A (ru) | 2008-12-20 |
| ES2362103T3 (es) | 2011-06-28 |
| CN101056872A (zh) | 2007-10-17 |
| AR051764A1 (es) | 2007-02-07 |
| CA2586106A1 (en) | 2006-05-18 |
| WO2006051502A3 (en) | 2006-09-08 |
| SI1833821T1 (sl) | 2011-07-29 |
| KR101285463B1 (ko) | 2013-07-12 |
| EP1833821A2 (en) | 2007-09-19 |
| JP5020089B2 (ja) | 2012-09-05 |
| TW200628467A (en) | 2006-08-16 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20211112 |