ES2324477T3 - Deteccion de no mediante el uso de la produccion de guanilil ciclasa y de cgmp como sistema de lectura. - Google Patents
Deteccion de no mediante el uso de la produccion de guanilil ciclasa y de cgmp como sistema de lectura. Download PDFInfo
- Publication number
- ES2324477T3 ES2324477T3 ES04819231T ES04819231T ES2324477T3 ES 2324477 T3 ES2324477 T3 ES 2324477T3 ES 04819231 T ES04819231 T ES 04819231T ES 04819231 T ES04819231 T ES 04819231T ES 2324477 T3 ES2324477 T3 ES 2324477T3
- Authority
- ES
- Spain
- Prior art keywords
- cgmp
- nitric oxide
- nos
- oxide synthase
- cyclase
- 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 - Lifetime
Links
- 238000001514 detection method Methods 0.000 title description 19
- 238000004519 manufacturing process Methods 0.000 title description 7
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 95
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims abstract description 65
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 42
- 230000000694 effects Effects 0.000 claims abstract description 39
- 101710095468 Cyclase Proteins 0.000 claims abstract description 36
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 14
- 238000012216 screening Methods 0.000 claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract description 12
- 238000012360 testing method Methods 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 22
- 102000019197 Superoxide Dismutase Human genes 0.000 claims description 19
- 108010012715 Superoxide dismutase Proteins 0.000 claims description 19
- XKMLYUALXHKNFT-UUOKFMHZSA-N Guanosine-5'-triphosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XKMLYUALXHKNFT-UUOKFMHZSA-N 0.000 claims description 13
- 239000004475 Arginine Substances 0.000 claims description 10
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 239000012190 activator Substances 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 2
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 claims 17
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 abstract description 58
- 238000002820 assay format Methods 0.000 abstract description 2
- 102000004190 Enzymes Human genes 0.000 description 16
- 108090000790 Enzymes Proteins 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 235000009697 arginine Nutrition 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 229960003753 nitric oxide Drugs 0.000 description 8
- 238000003359 percent control normalization Methods 0.000 description 8
- 238000003016 alphascreen Methods 0.000 description 7
- 239000002077 nanosphere Substances 0.000 description 7
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 6
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 239000012131 assay buffer Substances 0.000 description 6
- 235000013477 citrulline Nutrition 0.000 description 6
- 229960002173 citrulline Drugs 0.000 description 6
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VWWQXMAJTJZDQX-UHFFFAOYSA-N Flavine adenine dinucleotide Natural products C1=NC2=C(N)N=CN=C2N1C(C(O)C1O)OC1COP(O)(=O)OP(O)(=O)OCC(O)C(O)C(O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UHFFFAOYSA-N 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 3
- FVTCRASFADXXNN-UHFFFAOYSA-N flavin mononucleotide Natural products OP(=O)(O)OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003259 recombinant expression Methods 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- BCWUDVHLRZWMBE-YJOCEBFMSA-N (Z)-diethylamino-hydroxyimino-oxidoazanium N-ethylethanamine Chemical compound CC[NH2+]CC.CCN(CC)[N+](\[O-])=N\[O-] BCWUDVHLRZWMBE-YJOCEBFMSA-N 0.000 description 2
- 102000000584 Calmodulin Human genes 0.000 description 2
- 108010041952 Calmodulin Proteins 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- GZQGUYVURISNFJ-UHFFFAOYSA-N N-(1,3-benzodioxol-5-ylmethyl)-6-methoxy-4-quinazolinamine Chemical compound C1=C2OCOC2=CC(CNC2=NC=NC3=CC=C(C=C32)OC)=C1 GZQGUYVURISNFJ-UHFFFAOYSA-N 0.000 description 2
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 2
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 238000007405 data analysis Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000007877 drug screening Methods 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 1
- VXGYFEOSZYEJBK-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1-oxa-2-aza-3-azonia-4-azanidacyclopent-2-en-5-imine Chemical compound C1=C(Cl)C(Cl)=CC=C1[N+]1=NOC(=N)[N-]1 VXGYFEOSZYEJBK-UHFFFAOYSA-N 0.000 description 1
- 238000003284 AlphaScreen IgG detection kit Methods 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- LHQIJBMDNUYRAM-AWFVSMACSA-N D-erythro-biopterin Chemical compound N1=C(N)NC(=O)C2=NC([C@H](O)[C@H](O)C)=CN=C21 LHQIJBMDNUYRAM-AWFVSMACSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- LHQIJBMDNUYRAM-UHFFFAOYSA-N L-erythro-Biopterin Natural products N1=C(N)NC(=O)C2=NC(C(O)C(O)C)=CN=C21 LHQIJBMDNUYRAM-UHFFFAOYSA-N 0.000 description 1
- ONYFNWIHJBLQKE-ZETCQYMHSA-N N(6)-acetimidoyl-L-lysine Chemical compound CC(=N)NCCCC[C@H](N)C(O)=O ONYFNWIHJBLQKE-ZETCQYMHSA-N 0.000 description 1
- NTNWOCRCBQPEKQ-YFKPBYRVSA-N N(omega)-methyl-L-arginine Chemical compound CN=C(N)NCCC[C@H](N)C(O)=O NTNWOCRCBQPEKQ-YFKPBYRVSA-N 0.000 description 1
- NTNWOCRCBQPEKQ-UHFFFAOYSA-N NG-mono-methyl-L-arginine Natural products CN=C(N)NCCCC(N)C(O)=O NTNWOCRCBQPEKQ-UHFFFAOYSA-N 0.000 description 1
- 102100022397 Nitric oxide synthase, brain Human genes 0.000 description 1
- 101710111444 Nitric oxide synthase, brain Proteins 0.000 description 1
- 102100028452 Nitric oxide synthase, endothelial Human genes 0.000 description 1
- 101710090055 Nitric oxide synthase, endothelial Proteins 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000002840 nitric oxide donor Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/32—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving dehydrogenase
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03027159 | 2003-11-26 | ||
| EP03027159 | 2003-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2324477T3 true ES2324477T3 (es) | 2009-08-07 |
Family
ID=34626376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04819231T Expired - Lifetime ES2324477T3 (es) | 2003-11-26 | 2004-11-25 | Deteccion de no mediante el uso de la produccion de guanilil ciclasa y de cgmp como sistema de lectura. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1689880B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5671194B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE429508T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2540822C (cg-RX-API-DMAC7.html) |
| DE (1) | DE602004020795D1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK1689880T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2324477T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2005052185A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006038942A1 (de) * | 2006-08-18 | 2008-02-21 | Bayer Healthcare Ag | Verfahren zur Identifizierung von Stickstoffmonoxid Modulatoren |
| JP5350607B2 (ja) * | 2007-06-14 | 2013-11-27 | キッコーマン株式会社 | グアニル酸シクラーゼ活性測定法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10043845A1 (de) * | 2000-09-06 | 2002-03-14 | Gruenenthal Gmbh | Verfahren zur Messung der Aktivität der NO-Synthase |
-
2004
- 2004-11-25 WO PCT/EP2004/013707 patent/WO2005052185A1/en not_active Ceased
- 2004-11-25 ES ES04819231T patent/ES2324477T3/es not_active Expired - Lifetime
- 2004-11-25 DE DE602004020795T patent/DE602004020795D1/de not_active Expired - Lifetime
- 2004-11-25 JP JP2006540410A patent/JP5671194B2/ja not_active Expired - Lifetime
- 2004-11-25 CA CA2540822A patent/CA2540822C/en not_active Expired - Lifetime
- 2004-11-25 DK DK04819231T patent/DK1689880T3/da active
- 2004-11-25 EP EP04819231A patent/EP1689880B1/en not_active Expired - Lifetime
- 2004-11-25 AT AT04819231T patent/ATE429508T1/de active
Also Published As
| Publication number | Publication date |
|---|---|
| JP5671194B2 (ja) | 2015-02-18 |
| WO2005052185A1 (en) | 2005-06-09 |
| JP2007512011A (ja) | 2007-05-17 |
| EP1689880B1 (en) | 2009-04-22 |
| ATE429508T1 (de) | 2009-05-15 |
| DE602004020795D1 (de) | 2009-06-04 |
| CA2540822C (en) | 2010-09-21 |
| CA2540822A1 (en) | 2005-06-09 |
| DK1689880T3 (da) | 2009-07-27 |
| EP1689880A1 (en) | 2006-08-16 |
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