UA80579C2 - Imidazopyridine compounds, method of their obtaining and pharmaceutical composition that comprises them - Google Patents
Imidazopyridine compounds, method of their obtaining and pharmaceutical composition that comprises them Download PDFInfo
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- UA80579C2 UA80579C2 UAA200505316A UA2005005316A UA80579C2 UA 80579 C2 UA80579 C2 UA 80579C2 UA A200505316 A UAA200505316 A UA A200505316A UA 2005005316 A UA2005005316 A UA 2005005316A UA 80579 C2 UA80579 C2 UA 80579C2
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- UA
- Ukraine
- Prior art keywords
- formula
- group
- compounds
- alkyl
- pharmaceutically acceptable
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- -1 polyhalogenoalkyl Chemical group 0.000 claims abstract description 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 description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract 5
- 229940079593 drug Drugs 0.000 claims abstract 5
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
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- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- 230000007170 pathology Effects 0.000 description 1
- 229940080469 phosphocellulose Drugs 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0213802A FR2846656B1 (fr) | 2002-11-05 | 2002-11-05 | Nouveaux derives d'imidazopyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2003/003277 WO2004043957A1 (fr) | 2002-11-05 | 2003-11-04 | Derives d’imidazopyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA80579C2 true UA80579C2 (en) | 2007-10-10 |
Family
ID=32104440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200505316A UA80579C2 (en) | 2002-11-05 | 2003-04-11 | Imidazopyridine compounds, method of their obtaining and pharmaceutical composition that comprises them |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7098220B2 (es) |
| EP (1) | EP1558612B1 (es) |
| JP (1) | JP2006508111A (es) |
| KR (1) | KR100717488B1 (es) |
| CN (1) | CN100335480C (es) |
| AR (1) | AR041882A1 (es) |
| AT (1) | ATE337317T1 (es) |
| AU (1) | AU2003292323A1 (es) |
| BR (1) | BR0315800A (es) |
| CA (1) | CA2504008A1 (es) |
| CY (1) | CY1105752T1 (es) |
| DE (1) | DE60307875T2 (es) |
| DK (1) | DK1558612T3 (es) |
| EA (1) | EA008446B1 (es) |
| ES (1) | ES2271653T3 (es) |
| FR (1) | FR2846656B1 (es) |
| HK (1) | HK1081964A1 (es) |
| MA (1) | MA27411A1 (es) |
| MX (1) | MXPA05004791A (es) |
| MY (1) | MY135191A (es) |
| NO (1) | NO20052710L (es) |
| NZ (1) | NZ539599A (es) |
| PL (1) | PL375373A1 (es) |
| PT (1) | PT1558612E (es) |
| UA (1) | UA80579C2 (es) |
| WO (1) | WO2004043957A1 (es) |
| ZA (1) | ZA200503234B (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1754483A1 (en) | 2005-08-18 | 2007-02-21 | Merck Sante | Use of thienopyridone derivatives as AMPK activators and pharmaceutical compositions containing them |
| FR2903695B1 (fr) | 2006-07-13 | 2008-10-24 | Merck Sante Soc Par Actions Si | Utilisation de derives d'imidazole activateurs de l'ampk, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2008016730A2 (en) * | 2006-08-02 | 2008-02-07 | Targeted Molecular Diagnostics, Llc | Compositions and methods for reducing cellular fat |
| US8163505B2 (en) | 2007-05-22 | 2012-04-24 | The Penn State Research Foundation | Methods using PBK1 for identifying agents that treat metabolic disorders |
| US8507473B2 (en) | 2008-09-11 | 2013-08-13 | Arena Pharmaceuticals, Inc. | 3H-imidazo[4,5-b]pyridin-5-ol derivatives useful in the treatment of GPR81 receptor disorders |
| MX2011003239A (es) * | 2008-09-26 | 2011-04-28 | Merck Sharp & Dohme | Nuevos derivados de bencimidazol ciclicos utiles como agentes anti-diabeticos. |
| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CA2741672A1 (en) * | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2010103040A1 (en) | 2009-03-10 | 2010-09-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | 5'-adenosine monophosphate-activated protein kinase (ampk) activators for treating pulmonary hypertension |
| US8765728B2 (en) | 2009-11-16 | 2014-07-01 | Mellitech | [1,5]-diazocin derivatives |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| WO2012033149A1 (ja) | 2010-09-10 | 2012-03-15 | 塩野義製薬株式会社 | Ａｍｐｋ活性化作用を有するヘテロ環縮合イミダゾール誘導体 |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| EP2906040B1 (en) * | 2012-08-22 | 2021-02-17 | Merck Sharp & Dohme Corp. | Novel benzimidazole tetrahydropyran derivatives |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
| US9650376B2 (en) | 2013-03-15 | 2017-05-16 | Knopp Biosciences Llc | Imidazo(4,5-B) pyridin-2-yl amides as KV7 channel activators |
| US9481653B2 (en) | 2014-09-12 | 2016-11-01 | Knopp Biosciences Llc | Benzoimidazol-1,2-yl amides as Kv7 channel activators |
| WO2023044364A1 (en) | 2021-09-15 | 2023-03-23 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2707984B1 (fr) * | 1993-07-23 | 1995-09-01 | Adir | Nouvelles pipérazines substituées, leur procédé de préparation et les compositions les contenant. |
| SI0946550T1 (en) * | 1996-12-11 | 2005-10-31 | Aventis Pharmaceuticals Inc. | PREPARATION OF (1S-(1a,2b,3b,4a(S*)))-4-(7-((1-(3-CHLORO-2-THIENYL)METHYL)PROPYL)AMINO)-3H-IMIDAZO(4,5-b)PYRIDIN-3-yl)-N-ETHYL-2,3-DIHYDROXYCYCLOPENTANECARBOXAMIDE |
| JP2002523459A (ja) * | 1998-08-31 | 2002-07-30 | メルク エンド カムパニー インコーポレーテッド | 新規血管形成阻害剤 |
| US6271241B1 (en) * | 1999-04-02 | 2001-08-07 | Neurogen Corporation | Cycloalkyl and aryl fused aminoalkyl-imidazole derivatives: modulators and GLP-1 receptors |
-
2002
- 2002-11-05 FR FR0213802A patent/FR2846656B1/fr not_active Expired - Fee Related
-
2003
- 2003-04-11 UA UAA200505316A patent/UA80579C2/uk unknown
- 2003-10-09 MY MYPI20033845A patent/MY135191A/en unknown
- 2003-11-04 EP EP03767889A patent/EP1558612B1/fr not_active Expired - Lifetime
- 2003-11-04 EA EA200500717A patent/EA008446B1/ru not_active IP Right Cessation
- 2003-11-04 WO PCT/FR2003/003277 patent/WO2004043957A1/fr active IP Right Grant
- 2003-11-04 DE DE60307875T patent/DE60307875T2/de not_active Expired - Fee Related
- 2003-11-04 PT PT03767889T patent/PT1558612E/pt unknown
- 2003-11-04 US US10/533,699 patent/US7098220B2/en not_active Expired - Fee Related
- 2003-11-04 KR KR1020057007914A patent/KR100717488B1/ko not_active IP Right Cessation
- 2003-11-04 BR BR0315800-4A patent/BR0315800A/pt not_active IP Right Cessation
- 2003-11-04 AT AT03767889T patent/ATE337317T1/de not_active IP Right Cessation
- 2003-11-04 CN CNB2003801027143A patent/CN100335480C/zh not_active Expired - Fee Related
- 2003-11-04 ES ES03767889T patent/ES2271653T3/es not_active Expired - Lifetime
- 2003-11-04 PL PL03375373A patent/PL375373A1/xx not_active Application Discontinuation
- 2003-11-04 JP JP2004550729A patent/JP2006508111A/ja active Pending
- 2003-11-04 CA CA002504008A patent/CA2504008A1/fr not_active Abandoned
- 2003-11-04 DK DK03767889T patent/DK1558612T3/da active
- 2003-11-04 AU AU2003292323A patent/AU2003292323A1/en not_active Abandoned
- 2003-11-04 AR ARP030104024A patent/AR041882A1/es not_active Application Discontinuation
- 2003-11-04 MX MXPA05004791A patent/MXPA05004791A/es active IP Right Grant
- 2003-11-04 NZ NZ539599A patent/NZ539599A/en unknown
-
2005
- 2005-04-19 MA MA28233A patent/MA27411A1/fr unknown
- 2005-04-21 ZA ZA200503234A patent/ZA200503234B/en unknown
- 2005-06-06 NO NO20052710A patent/NO20052710L/no not_active Application Discontinuation
-
2006
- 2006-02-22 HK HK06102330A patent/HK1081964A1/xx not_active IP Right Cessation
- 2006-11-02 CY CY20061101581T patent/CY1105752T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20052710L (no) | 2005-06-06 |
| AR041882A1 (es) | 2005-06-01 |
| ATE337317T1 (de) | 2006-09-15 |
| KR20050084663A (ko) | 2005-08-26 |
| DE60307875D1 (de) | 2006-10-05 |
| CN1711261A (zh) | 2005-12-21 |
| US7098220B2 (en) | 2006-08-29 |
| NZ539599A (en) | 2007-06-29 |
| MY135191A (en) | 2008-02-29 |
| US20060069117A1 (en) | 2006-03-30 |
| ES2271653T3 (es) | 2007-04-16 |
| HK1081964A1 (en) | 2006-05-26 |
| ZA200503234B (en) | 2006-06-28 |
| PT1558612E (pt) | 2006-12-29 |
| DE60307875T2 (de) | 2007-04-12 |
| AU2003292323A1 (en) | 2004-06-03 |
| EA200500717A1 (ru) | 2005-10-27 |
| CN100335480C (zh) | 2007-09-05 |
| BR0315800A (pt) | 2005-09-20 |
| PL375373A1 (en) | 2005-11-28 |
| WO2004043957A1 (fr) | 2004-05-27 |
| JP2006508111A (ja) | 2006-03-09 |
| EP1558612A1 (fr) | 2005-08-03 |
| MA27411A1 (fr) | 2005-06-01 |
| CA2504008A1 (fr) | 2004-05-27 |
| KR100717488B1 (ko) | 2007-05-14 |
| DK1558612T3 (da) | 2006-12-27 |
| MXPA05004791A (es) | 2005-07-22 |
| EP1558612B1 (fr) | 2006-08-23 |
| FR2846656A1 (fr) | 2004-05-07 |
| FR2846656B1 (fr) | 2004-12-24 |
| EA008446B1 (ru) | 2007-06-29 |
| CY1105752T1 (el) | 2010-12-22 |
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