ZA200509290B - Isoquinoline derivatives and their use as GFAT inhibitors - Google Patents
Isoquinoline derivatives and their use as GFAT inhibitors Download PDFInfo
- Publication number
- ZA200509290B ZA200509290B ZA200509290A ZA200509290A ZA200509290B ZA 200509290 B ZA200509290 B ZA 200509290B ZA 200509290 A ZA200509290 A ZA 200509290A ZA 200509290 A ZA200509290 A ZA 200509290A ZA 200509290 B ZA200509290 B ZA 200509290B
- Authority
- ZA
- South Africa
- Prior art keywords
- dimethoxy
- benzoyl
- isoquinoline
- carboxylic acid
- methoxy
- Prior art date
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- 101710185468 Glutamine-fructose-6-phosphate aminotransferase [isomerizing] Proteins 0.000 title claims 6
- 102100033429 Glutamine-fructose-6-phosphate aminotransferase [isomerizing] 1 Human genes 0.000 title claims 6
- 101710176049 Probable glutamine-fructose-6-phosphate aminotransferase [isomerizing] Proteins 0.000 title claims 6
- 101710198235 Putative glutamine-fructose-6-phosphate aminotransferase [isomerizing] Proteins 0.000 title claims 6
- 239000003112 inhibitor Substances 0.000 title description 5
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000005842 heteroatom Chemical group 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- -1 -O-CR'R}C(=O)R" Chemical group 0.000 claims description 18
- 238000011321 prophylaxis Methods 0.000 claims description 17
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 230000001225 therapeutic effect Effects 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- OQMKQUCTGTUFHP-UHFFFAOYSA-N 1-(3-butoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound CCCCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 OQMKQUCTGTUFHP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- NMJRFKJTCHZCLZ-UHFFFAOYSA-N 6,7-dimethoxy-1-(3-methoxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 NMJRFKJTCHZCLZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- HNSQVHYWYFEEAD-UHFFFAOYSA-N 1-(3-ethoxybenzoyl)-6,7-dimethoxy-n,n-dimethylisoquinoline-4-carboximidamide Chemical compound CCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(=N)N(C)C)=CN=2)=C1 HNSQVHYWYFEEAD-UHFFFAOYSA-N 0.000 claims description 6
- NMYOQKDOSNPEIR-UHFFFAOYSA-N 6,7-dimethoxy-1-(3-propan-2-yloxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=CC=CC(OC(C)C)=C1 NMYOQKDOSNPEIR-UHFFFAOYSA-N 0.000 claims description 6
- WRWWDHLZZIYYNN-UHFFFAOYSA-N 6-(3-acetyloxypropoxy)-1-(3-ethoxybenzoyl)-7-methoxyisoquinoline-4-carboxylic acid Chemical compound CCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OCCCOC(C)=O)C=C3C(C(O)=O)=CN=2)=C1 WRWWDHLZZIYYNN-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- ZJHRUJOXJRJDAI-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-(3-methoxybenzoyl)isoquinolin-4-yl]acetic acid Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(CC(O)=O)=CN=2)=C1 ZJHRUJOXJRJDAI-UHFFFAOYSA-N 0.000 claims description 5
- LLXSNPMNFABCNW-UHFFFAOYSA-N [4-(aminomethyl)-6,7-dimethoxyisoquinolin-1-yl]-(3-propan-2-yloxyphenyl)methanone Chemical compound C=12C=C(OC)C(OC)=CC2=C(CN)C=NC=1C(=O)C1=CC=CC(OC(C)C)=C1 LLXSNPMNFABCNW-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- QZLGWUVXUHSDDH-UHFFFAOYSA-N 1-(2-fluoro-5-methoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound COC1=CC=C(F)C(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 QZLGWUVXUHSDDH-UHFFFAOYSA-N 0.000 claims description 4
- PZJIETQEHNYXCX-UHFFFAOYSA-N 1-(2-fluoro-5-propan-2-yloxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=CC(OC(C)C)=CC=C1F PZJIETQEHNYXCX-UHFFFAOYSA-N 0.000 claims description 4
- QGCVZSQOARNTOU-UHFFFAOYSA-N 1-(3-ethoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound CCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 QGCVZSQOARNTOU-UHFFFAOYSA-N 0.000 claims description 4
- RVOKMSGITHBDRW-UHFFFAOYSA-N 1-(3-ethoxybenzoyl)-6-(2-ethoxyethoxy)-7-methoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OCCOCC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=CC=CC(OCC)=C1 RVOKMSGITHBDRW-UHFFFAOYSA-N 0.000 claims description 4
- WBXKXJKXCXSWRY-UHFFFAOYSA-N 1-(3-ethoxybenzoyl)-6-(2-hydroxyethoxy)-7-methoxyisoquinoline-4-carboxylic acid Chemical compound CCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OCCO)C=C3C(C(O)=O)=CN=2)=C1 WBXKXJKXCXSWRY-UHFFFAOYSA-N 0.000 claims description 4
- HCILHNAOHZZEQJ-UHFFFAOYSA-N 1-(3-ethoxybenzoyl)-7-methoxy-6-(2-morpholin-4-ylethoxy)isoquinoline-4-carboxylic acid Chemical compound CCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OCCN4CCOCC4)C=C3C(C(O)=O)=CN=2)=C1 HCILHNAOHZZEQJ-UHFFFAOYSA-N 0.000 claims description 4
- AGSSTUSBHYXURX-UHFFFAOYSA-N 1-(3-ethoxybenzoyl)-7-methoxy-6-propan-2-yloxyisoquinoline-4-carboxylic acid Chemical compound CCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC(C)C)C=C3C(C(O)=O)=CN=2)=C1 AGSSTUSBHYXURX-UHFFFAOYSA-N 0.000 claims description 4
- BDMCUZOEFZNVCE-UHFFFAOYSA-N 1-[3-(carboxymethoxy)benzoyl]-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=CC=CC(OCC(O)=O)=C1 BDMCUZOEFZNVCE-UHFFFAOYSA-N 0.000 claims description 4
- WIFVFFIPPWYTQQ-UHFFFAOYSA-N 1-[3-[2-[benzyl(methyl)amino]-2-oxoethoxy]benzoyl]-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C(C=1)=CC=CC=1OCC(=O)N(C)CC1=CC=CC=C1 WIFVFFIPPWYTQQ-UHFFFAOYSA-N 0.000 claims description 4
- CIWZIFBKVZBTFZ-UHFFFAOYSA-N 2-[1-(2-fluoro-5-propan-2-yloxybenzoyl)-6,7-dimethoxyisoquinolin-4-yl]-4-methylpentanoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(CC(C)C)C(O)=O)C=NC=1C(=O)C1=CC(OC(C)C)=CC=C1F CIWZIFBKVZBTFZ-UHFFFAOYSA-N 0.000 claims description 4
- RDENMHTWPVIFSO-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-(3-methoxybenzoyl)isoquinolin-4-yl]acetamide Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(CC(N)=O)=CN=2)=C1 RDENMHTWPVIFSO-UHFFFAOYSA-N 0.000 claims description 4
- CZCKKOVHOCTKFV-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-(3-propan-2-yloxybenzoyl)isoquinolin-4-yl]acetic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(CC(O)=O)C=NC=1C(=O)C1=CC=CC(OC(C)C)=C1 CZCKKOVHOCTKFV-UHFFFAOYSA-N 0.000 claims description 4
- WUHFZVIZOLHEBI-UHFFFAOYSA-N 6-(carboxymethoxy)-7-methoxy-1-(3-propan-2-yloxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound N1=CC(C(O)=O)=C2C=C(OCC(O)=O)C(OC)=CC2=C1C(=O)C1=CC=CC(OC(C)C)=C1 WUHFZVIZOLHEBI-UHFFFAOYSA-N 0.000 claims description 4
- HFQLHGBLHILBPW-UHFFFAOYSA-N 6-cyclopentyloxy-7-methoxy-1-(3-methoxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC4CCCC4)C=C3C(C(O)=O)=CN=2)=C1 HFQLHGBLHILBPW-UHFFFAOYSA-N 0.000 claims description 4
- OZJNJUBSWRYTJV-UHFFFAOYSA-N 6-methoxy-1-(3-methoxybenzoyl)-7-phenylmethoxyisoquinoline-4-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OCC=4C=CC=CC=4)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 OZJNJUBSWRYTJV-UHFFFAOYSA-N 0.000 claims description 4
- DMFCFTOSUVGCKY-UHFFFAOYSA-N 7-(2-hydroxyethoxy)-6-methoxy-1-(3-methoxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OCCO)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 DMFCFTOSUVGCKY-UHFFFAOYSA-N 0.000 claims description 4
- XAUJBVHMXOBTFW-UHFFFAOYSA-N 7-butoxy-6-methoxy-1-(3-methoxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound N1=CC(C(O)=O)=C2C=C(OC)C(OCCCC)=CC2=C1C(=O)C1=CC=CC(OC)=C1 XAUJBVHMXOBTFW-UHFFFAOYSA-N 0.000 claims description 4
- KYRFLPQBISQXTM-UHFFFAOYSA-N 7-methoxy-1-(3-methoxybenzoyl)-6-phenylmethoxyisoquinoline-4-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OCC=4C=CC=CC=4)C=C3C(C(O)=O)=CN=2)=C1 KYRFLPQBISQXTM-UHFFFAOYSA-N 0.000 claims description 4
- DLONVCVQTUECTM-UHFFFAOYSA-N 7-methoxy-1-(3-propan-2-yloxybenzoyl)-6-(2-pyrrolidin-1-ylethoxy)isoquinoline-4-carboxylic acid;hydrochloride Chemical compound Cl.COC1=CC2=C(C(=O)C=3C=C(OC(C)C)C=CC=3)N=CC(C(O)=O)=C2C=C1OCCN1CCCC1 DLONVCVQTUECTM-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 claims description 4
- OVMYWBYXZYUEKY-UHFFFAOYSA-N n-(2-cyanoethyl)-6,7-dimethoxy-1-(3-methoxybenzoyl)isoquinoline-4-carboxamide Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(=O)NCCC#N)=CN=2)=C1 OVMYWBYXZYUEKY-UHFFFAOYSA-N 0.000 claims description 4
- CSMBQEIXZHYGLW-UHFFFAOYSA-N n-[[6,7-dimethoxy-1-(3-propan-2-yloxybenzoyl)isoquinolin-4-yl]methyl]ethanesulfonamide Chemical compound C12=CC(OC)=C(OC)C=C2C(CNS(=O)(=O)CC)=CN=C1C(=O)C1=CC=CC(OC(C)C)=C1 CSMBQEIXZHYGLW-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003536 tetrazoles Chemical class 0.000 claims description 4
- JKXXETLOZUYDQA-UHFFFAOYSA-N 1-(2,6-difluoro-3-methoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound COC1=CC=C(F)C(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(O)=O)=CN=2)=C1F JKXXETLOZUYDQA-UHFFFAOYSA-N 0.000 claims description 3
- LAEOTYPYJMLYGD-UHFFFAOYSA-N 1-(2,6-difluorobenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=C(F)C=CC=C1F LAEOTYPYJMLYGD-UHFFFAOYSA-N 0.000 claims description 3
- RGVLBUNAHFJQLG-UHFFFAOYSA-N 1-(3,5-dimethoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound COC1=CC(OC)=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 RGVLBUNAHFJQLG-UHFFFAOYSA-N 0.000 claims description 3
- MHXZHXGKTRMAOA-UHFFFAOYSA-N 1-(3-ethoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboxamide Chemical compound CCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(N)=O)=CN=2)=C1 MHXZHXGKTRMAOA-UHFFFAOYSA-N 0.000 claims description 3
- LYFGVNFVQWUQMK-UHFFFAOYSA-N 1-[3-(2-hydroxyethoxy)benzoyl]-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=CC=CC(OCCO)=C1 LYFGVNFVQWUQMK-UHFFFAOYSA-N 0.000 claims description 3
- HBCMKCCUKFLAPY-UHFFFAOYSA-N 1-[3-(furan-2-yl)benzoyl]-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C(C=1)=CC=CC=1C1=CC=CO1 HBCMKCCUKFLAPY-UHFFFAOYSA-N 0.000 claims description 3
- ZFAWIXGDMQCCNV-UHFFFAOYSA-N 1-[3-[2-(2-chloroethoxy)ethoxy]benzoyl]-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=CC=CC(OCCOCCCl)=C1 ZFAWIXGDMQCCNV-UHFFFAOYSA-N 0.000 claims description 3
- AQZSGRMIODATRA-UHFFFAOYSA-N 1-[3-[2-(4-benzylpiperazin-1-yl)-2-oxoethoxy]benzoyl]-6,7-dimethoxyisoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C(C=1)=CC=CC=1OCC(=O)N(CC1)CCN1CC1=CC=CC=C1 AQZSGRMIODATRA-UHFFFAOYSA-N 0.000 claims description 3
- IHHCEAVIVZKYAB-UHFFFAOYSA-N 2-[1-(2-fluoro-5-propan-2-yloxybenzoyl)-6,7-dimethoxyisoquinolin-4-yl]acetic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(CC(O)=O)C=NC=1C(=O)C1=CC(OC(C)C)=CC=C1F IHHCEAVIVZKYAB-UHFFFAOYSA-N 0.000 claims description 3
- DYMFUGTVUHCSFA-UHFFFAOYSA-N 2-[1-(3-butan-2-yloxybenzoyl)-6,7-dimethoxyisoquinolin-4-yl]acetic acid Chemical compound CCC(C)OC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(CC(O)=O)=CN=2)=C1 DYMFUGTVUHCSFA-UHFFFAOYSA-N 0.000 claims description 3
- FIFPISURNPHURB-UHFFFAOYSA-N 3-[6,7-dimethoxy-1-(3-propan-2-yloxybenzoyl)isoquinolin-4-yl]propanamide Chemical compound C=12C=C(OC)C(OC)=CC2=C(CCC(N)=O)C=NC=1C(=O)C1=CC=CC(OC(C)C)=C1 FIFPISURNPHURB-UHFFFAOYSA-N 0.000 claims description 3
- JUJPGFLTKNRTSR-UHFFFAOYSA-N 6,7-dimethoxy-1-(3-methylsulfanylbenzoyl)isoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=CC=CC(SC)=C1 JUJPGFLTKNRTSR-UHFFFAOYSA-N 0.000 claims description 3
- BZMWZGHERLVDIV-UHFFFAOYSA-N 6,7-dimethoxy-1-[3-[2-oxo-2-(propan-2-ylamino)ethoxy]benzoyl]isoquinoline-4-carboxylic acid Chemical compound C=12C=C(OC)C(OC)=CC2=C(C(O)=O)C=NC=1C(=O)C1=CC=CC(OCC(=O)NC(C)C)=C1 BZMWZGHERLVDIV-UHFFFAOYSA-N 0.000 claims description 3
- YNNXMBCRTVEXHY-UHFFFAOYSA-N 6-(3-acetyloxypropoxy)-7-methoxy-1-(3-methoxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OCCCOC(C)=O)C=C3C(C(O)=O)=CN=2)=C1 YNNXMBCRTVEXHY-UHFFFAOYSA-N 0.000 claims description 3
- NXNDUMUJDQMNJZ-UHFFFAOYSA-N 6-(3-hydroxypropoxy)-7-methoxy-1-(3-propan-2-yloxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound N1=CC(C(O)=O)=C2C=C(OCCCO)C(OC)=CC2=C1C(=O)C1=CC=CC(OC(C)C)=C1 NXNDUMUJDQMNJZ-UHFFFAOYSA-N 0.000 claims description 3
- RARJOVGFIZHQDW-UHFFFAOYSA-N 7-(2-amino-2-oxoethoxy)-6-methoxy-1-(3-methoxybenzoyl)isoquinoline-4-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OCC(N)=O)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 RARJOVGFIZHQDW-UHFFFAOYSA-N 0.000 claims description 3
- RVNNYUUXGPALGR-UHFFFAOYSA-N [3-(3-azido-2-hydroxypropoxy)phenyl]-[6,7-dimethoxy-4-(2h-tetrazol-5-yl)isoquinolin-1-yl]methanone Chemical compound C=12C=C(OC)C(OC)=CC2=C(C=2NN=NN=2)C=NC=1C(=O)C1=CC=CC(OCC(O)CN=[N+]=[N-])=C1 RVNNYUUXGPALGR-UHFFFAOYSA-N 0.000 claims description 3
- HHWUMMLSJWGDBV-UHFFFAOYSA-N [4-(4-hydroxypiperidine-1-carbonyl)-6,7-dimethoxyisoquinolin-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(=O)N3CCC(O)CC3)=CN=2)=C1 HHWUMMLSJWGDBV-UHFFFAOYSA-N 0.000 claims description 3
- MGPNYSDYCUAFNW-UHFFFAOYSA-N [6,7-dimethoxy-4-(2h-tetrazol-5-yl)isoquinolin-1-yl]-(3-ethoxyphenyl)methanone Chemical compound CCOC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C=3NN=NN=3)=CN=2)=C1 MGPNYSDYCUAFNW-UHFFFAOYSA-N 0.000 claims description 3
- OMQCONDMBJMUDU-UHFFFAOYSA-N ethyl 1-(3-ethoxybenzoyl)-6,7-dimethoxyisoquinoline-4-carboximidate Chemical compound C12=CC(OC)=C(OC)C=C2C(C(=N)OCC)=CN=C1C(=O)C1=CC=CC(OCC)=C1 OMQCONDMBJMUDU-UHFFFAOYSA-N 0.000 claims description 3
- RNUJJMNSFQUYOH-UHFFFAOYSA-N n-[6,7-dimethoxy-1-(3-methoxybenzoyl)isoquinolin-4-yl]acetamide Chemical compound COC1=CC=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(NC(C)=O)=CN=2)=C1 RNUJJMNSFQUYOH-UHFFFAOYSA-N 0.000 claims description 3
- MHLCDPDJXUKYTR-UHFFFAOYSA-N 1,1,1-trifluoro-n-[[1-(2-fluoro-5-methoxybenzoyl)-6,7-dimethoxyisoquinolin-4-yl]methyl]methanesulfonamide Chemical compound COC1=CC=C(F)C(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(CNS(=O)(=O)C(F)(F)F)=CN=2)=C1 MHLCDPDJXUKYTR-UHFFFAOYSA-N 0.000 claims description 2
- KSULCBJYMQZVSW-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-(3-propan-2-yloxybenzoyl)isoquinolin-4-yl]acetamide Chemical compound C=12C=C(OC)C(OC)=CC2=C(CC(N)=O)C=NC=1C(=O)C1=CC=CC(OC(C)C)=C1 KSULCBJYMQZVSW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- QUNJMSZHTIOVEZ-UHFFFAOYSA-N 6,7-dimethoxy-1-(3-methoxy-5-methylbenzoyl)isoquinoline-4-carboxylic acid Chemical compound COC1=CC(C)=CC(C(=O)C=2C3=CC(OC)=C(OC)C=C3C(C(O)=O)=CN=2)=C1 QUNJMSZHTIOVEZ-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Application Number | Priority Date | Filing Date | Title |
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US47169003P | 2003-05-19 | 2003-05-19 |
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ZA200509290B true ZA200509290B (en) | 2007-04-25 |
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ZA200509290A ZA200509290B (en) | 2003-05-19 | 2005-11-16 | Isoquinoline derivatives and their use as GFAT inhibitors |
Country Status (20)
Country | Link |
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US (1) | US7067529B2 (fr) |
EP (1) | EP1631551A2 (fr) |
JP (1) | JP2006528218A (fr) |
KR (1) | KR100785571B1 (fr) |
CN (1) | CN100540537C (fr) |
AR (1) | AR044371A1 (fr) |
AU (1) | AU2004238521B2 (fr) |
BR (1) | BRPI0410760A (fr) |
CA (1) | CA2524958A1 (fr) |
CL (1) | CL2004001069A1 (fr) |
CO (1) | CO5630035A2 (fr) |
HK (1) | HK1091838A1 (fr) |
MX (1) | MXPA05012415A (fr) |
MY (1) | MY142768A (fr) |
NO (1) | NO20054852L (fr) |
NZ (1) | NZ543065A (fr) |
RU (1) | RU2320648C2 (fr) |
TW (1) | TW200426144A (fr) |
WO (1) | WO2004101528A2 (fr) |
ZA (1) | ZA200509290B (fr) |
Families Citing this family (37)
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US20090325944A1 (en) * | 2006-04-12 | 2009-12-31 | Suzanne Walker Kahne | Methods and Compositions for Modulating Glycosylation |
BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
US8524444B2 (en) * | 2007-06-15 | 2013-09-03 | President And Fellows Of Harvard College | Methods and compositions for detections and modulating O-glycosylation |
EP2025674A1 (fr) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Tetrahydronaphthaline substituée, son procédé de fabrication et son utilisation en tant que médicament |
EP2085397A1 (fr) * | 2008-01-21 | 2009-08-05 | Esteve Quimica, S.A. | Forme cristalline d'abacavir |
ES2646787T3 (es) * | 2008-02-29 | 2017-12-18 | The Procter & Gamble Company | Composiciones para el cuidado del cabello y métodos para aumentar el diámetro del cabello |
WO2010003624A2 (fr) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Composés hétérocycliques, leurs procédés de préparation, médicaments comprenant lesdits composés et leur utilisation |
WO2010068601A1 (fr) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | Hydrate de fluoroglycoside hétéroaromatique cristallin, ses procédés de fabrication, ses procédés d'utilisation et compositions pharmaceutiques le contenant |
BRPI0923592A2 (pt) * | 2008-12-25 | 2016-01-26 | Taisho Pharmaceutical Co Ltd | composto |
JP2012528858A (ja) | 2009-06-01 | 2012-11-15 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | O−GlcNAc転移酵素阻害剤およびその使用 |
RU2012111354A (ru) | 2009-08-26 | 2013-10-10 | Санофи | Новые кристаллические гидраты фторгликозидов, содержащие их фармацевтические препараты и их использование |
WO2011107494A1 (fr) | 2010-03-03 | 2011-09-09 | Sanofi | Nouveaux dérivés aromatiques de glycoside, médicaments contenants ces composés, et leur utilisation |
EP2582709B1 (fr) | 2010-06-18 | 2018-01-24 | Sanofi | Dérivés d'azolopyridin-3-one en tant qu'inhibiteurs de lipases et de phospholipases |
US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
US20130096310A1 (en) * | 2010-06-23 | 2013-04-18 | Taisho Pharmaceutical Co., Ltd. | Isoquinoline derivative |
TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
EP2683705B1 (fr) | 2011-03-08 | 2015-04-22 | Sanofi | Dérivés oxathiazine di- et tri-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation |
WO2012120056A1 (fr) | 2011-03-08 | 2012-09-13 | Sanofi | Dérivés oxathiazine tétra-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation |
WO2012120053A1 (fr) | 2011-03-08 | 2012-09-13 | Sanofi | Dérivés oxathiazine ramifiés, procédé pour leur préparation, utilisation en tant que médicament, agents pharmaceutiques contenant ces dérivés et leur utilisation |
WO2012120055A1 (fr) | 2011-03-08 | 2012-09-13 | Sanofi | Dérivés oxathiazine di- et tri-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation |
EP2683702B1 (fr) | 2011-03-08 | 2014-12-24 | Sanofi | Nouveaux dérivés de phényle-oxathiazine substitués, leur procédé de fabrication, médicament contenant ces liaisons et son utilisation |
EP2683701B1 (fr) | 2011-03-08 | 2014-12-24 | Sanofi | Dérivés d'oxathiazine substitués par des groupes de benzyle-méthyles ou d'hétéro-méthyles, leur procédé de fabrication, leur utilisation comme médicament ainsi que médicaments en étant pourvu et leur utilisation |
US8901114B2 (en) | 2011-03-08 | 2014-12-02 | Sanofi | Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof |
US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
WO2012120057A1 (fr) | 2011-03-08 | 2012-09-13 | Sanofi | Nouveaux dérivés phényl-oxathiazine substitués, procédé pour leur préparation, agent pharmaceutique contenant ces composés et leur utilisation |
US9573911B2 (en) | 2011-07-06 | 2017-02-21 | President And Fellows Of Harvard College | Diphosphate mimetics and uses thereof |
EP2567959B1 (fr) | 2011-09-12 | 2014-04-16 | Sanofi | Dérivés d'amide d'acide 6-(4-hydroxy-phényl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs de kinase |
WO2013037390A1 (fr) | 2011-09-12 | 2013-03-21 | Sanofi | Dérivés amides d'acide 6-(4-hydroxyphényl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs de kinase |
WO2013045413A1 (fr) | 2011-09-27 | 2013-04-04 | Sanofi | Dérivés d'amide d'acide 6-(4-hydroxyphényl)-3-alkyl-1h-pyrazolo[3,4-b] pyridine-4-carboxylique utilisés comme inhibiteurs de kinase |
US10123966B2 (en) | 2013-05-16 | 2018-11-13 | The Procter And Gamble Company | Hair thickening compositions and methods of use |
CN109456268A (zh) * | 2018-11-08 | 2019-03-12 | 中国药科大学 | C1位取代的3,4-二氢异喹啉类生物碱的制备及其医药用途 |
CN110642854A (zh) * | 2019-11-20 | 2020-01-03 | 成都克莱蒙医药科技有限公司 | 一种稠环化合物的多晶型、其组合物、制备方法及其应用 |
TW202214585A (zh) * | 2020-06-08 | 2022-04-16 | 加拿大商愛彼特生物製藥公司 | 經取代之異喹啉基甲基醯胺類、其類似物及使用其之方法 |
WO2022150962A1 (fr) * | 2021-01-12 | 2022-07-21 | Westlake Pharmaceutical (Hangzhou) Co., Ltd. | Inhibiteurs de protéase, leur préparation et leurs utilisations |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2199462A1 (en) | 1972-09-21 | 1974-04-12 | Bruneau & Cie Lab | Papaveraldime oxime ethers and esters - analgesics and antiinflammatories prepd by treatment of papaveraldime oxime with an alkyl or acyl halide |
GB1407685A (en) * | 1972-10-19 | 1975-09-24 | Allen & Hanburys Ltd | Isoquinolinium compounds |
US4042697A (en) * | 1972-10-19 | 1977-08-16 | Allen & Hanburys Limited | Isoquinolium compounds for treating diabetes |
JPS63310813A (ja) | 1987-06-12 | 1988-12-19 | Keikichi Sugiyama | 毛髪用組成物 |
US6400710B1 (en) * | 1999-07-09 | 2002-06-04 | Enron Warspeed Services, Inc. | Network with hot button for providing switched broadband multipoint/multimedia intercommunication |
ES2172376B1 (es) | 2000-01-28 | 2003-11-16 | Servier Lab | Nuevos derivados de isoquinoleinas, su procedimiento de preparacion y las composiciones farmaceuticas que los contienen. |
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2004
- 2004-04-19 US US10/827,514 patent/US7067529B2/en not_active Expired - Fee Related
- 2004-05-11 KR KR1020057021998A patent/KR100785571B1/ko not_active IP Right Cessation
- 2004-05-11 WO PCT/EP2004/005025 patent/WO2004101528A2/fr active IP Right Grant
- 2004-05-11 AU AU2004238521A patent/AU2004238521B2/en not_active Ceased
- 2004-05-11 EP EP04732111A patent/EP1631551A2/fr not_active Withdrawn
- 2004-05-11 NZ NZ543065A patent/NZ543065A/en unknown
- 2004-05-11 JP JP2006529779A patent/JP2006528218A/ja active Pending
- 2004-05-11 MX MXPA05012415A patent/MXPA05012415A/es active IP Right Grant
- 2004-05-11 BR BRPI0410760-8A patent/BRPI0410760A/pt not_active IP Right Cessation
- 2004-05-11 CA CA002524958A patent/CA2524958A1/fr not_active Abandoned
- 2004-05-11 RU RU2005139524/04A patent/RU2320648C2/ru not_active IP Right Cessation
- 2004-05-11 CN CNB2004800136909A patent/CN100540537C/zh not_active Expired - Fee Related
- 2004-05-14 TW TW093113583A patent/TW200426144A/zh unknown
- 2004-05-17 MY MYPI20041856A patent/MY142768A/en unknown
- 2004-05-17 AR ARP040101698A patent/AR044371A1/es unknown
- 2004-05-17 CL CL200401069A patent/CL2004001069A1/es unknown
-
2005
- 2005-10-20 NO NO20054852A patent/NO20054852L/no unknown
- 2005-11-16 CO CO05116287A patent/CO5630035A2/es not_active Application Discontinuation
- 2005-11-16 ZA ZA200509290A patent/ZA200509290B/en unknown
-
2006
- 2006-12-12 HK HK06113605.4A patent/HK1091838A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NZ543065A (en) | 2009-07-31 |
CA2524958A1 (fr) | 2004-11-25 |
MY142768A (en) | 2010-12-31 |
HK1091838A1 (en) | 2007-01-26 |
MXPA05012415A (es) | 2006-02-13 |
RU2320648C2 (ru) | 2008-03-27 |
US20040259910A1 (en) | 2004-12-23 |
AU2004238521B2 (en) | 2007-07-26 |
CL2004001069A1 (es) | 2005-04-01 |
US7067529B2 (en) | 2006-06-27 |
JP2006528218A (ja) | 2006-12-14 |
RU2005139524A (ru) | 2007-06-27 |
NO20054852L (no) | 2005-12-13 |
NO20054852D0 (no) | 2005-10-20 |
KR100785571B1 (ko) | 2007-12-13 |
AR044371A1 (es) | 2005-09-07 |
CN1791581A (zh) | 2006-06-21 |
WO2004101528A2 (fr) | 2004-11-25 |
EP1631551A2 (fr) | 2006-03-08 |
CN100540537C (zh) | 2009-09-16 |
TW200426144A (en) | 2004-12-01 |
WO2004101528A3 (fr) | 2005-01-06 |
AU2004238521A1 (en) | 2004-11-25 |
KR20060015267A (ko) | 2006-02-16 |
CO5630035A2 (es) | 2006-04-28 |
BRPI0410760A (pt) | 2006-06-27 |
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