JP2005532371A5 - - Google Patents
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- JP2005532371A5 JP2005532371A5 JP2004516551A JP2004516551A JP2005532371A5 JP 2005532371 A5 JP2005532371 A5 JP 2005532371A5 JP 2004516551 A JP2004516551 A JP 2004516551A JP 2004516551 A JP2004516551 A JP 2004516551A JP 2005532371 A5 JP2005532371 A5 JP 2005532371A5
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- JP
- Japan
- Prior art keywords
- phenyl
- tetrahydropyridine
- carboxylic acid
- ethoxy
- amide
- 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.)
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- -1 4- {4- [3- (2,3,6-trifluorophenoxy) propyl] phenyl} -1,2,5,6-tetrahydropyridine-3-carboxylic acid (2-chlorobenzyl) cyclopropylamide Chemical compound 0.000 claims 22
- 239000000203 mixture Substances 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- JHBVZGONNIVXFJ-UHFFFAOYSA-N (2,3-dichlorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1Cl JHBVZGONNIVXFJ-UHFFFAOYSA-N 0.000 claims 6
- UKLRWOHZBISUMI-UHFFFAOYSA-N (2,3-dimethylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1C UKLRWOHZBISUMI-UHFFFAOYSA-N 0.000 claims 6
- HEQDIKZGBQQWFK-UHFFFAOYSA-N 4-[4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound ClC1=CC(C)=CC(Cl)=C1OCCOC1=CC=C(C=2CCNCC=2C(O)=O)C=C1 HEQDIKZGBQQWFK-UHFFFAOYSA-N 0.000 claims 5
- 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 5
- 230000000877 morphologic effect Effects 0.000 claims 5
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000002904 solvent Chemical class 0.000 claims 5
- RWENEHDSAPYDKP-UHFFFAOYSA-N 4-[4-[2-(2,6-dichloro-4-fluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=C(Cl)C=C(F)C=C1Cl RWENEHDSAPYDKP-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- FZHYIKABBMEJMA-UHFFFAOYSA-N 4-[4-[2-(2,6-difluoro-3-methylphenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound CC1=CC=C(F)C(OCCOC=2C=CC(=CC=2)C=2CCNCC=2C(O)=O)=C1F FZHYIKABBMEJMA-UHFFFAOYSA-N 0.000 claims 2
- LXYQIBRUJZBFFC-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1=C(C)C(C)=CC(Cl)=C1OCCOC1=CC=C(C=2CCNCC=2C(O)=O)C=C1 LXYQIBRUJZBFFC-UHFFFAOYSA-N 0.000 claims 2
- OUZFDZJXZYVMMY-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=CC=C(C(F)(F)F)C=C1Cl OUZFDZJXZYVMMY-UHFFFAOYSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- TUPUHSXMDIWJQT-UHFFFAOYSA-N [3-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=CC(OC(F)(F)F)=C1 TUPUHSXMDIWJQT-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 201000006370 kidney failure Diseases 0.000 claims 2
- VDYXNMDTCPOGGV-UHFFFAOYSA-N n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-4-[4-[2-(2,4,6-trifluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(F)=CC=3F)F)=CC=2)=C1 VDYXNMDTCPOGGV-UHFFFAOYSA-N 0.000 claims 2
- 230000036454 renin-angiotensin system Effects 0.000 claims 2
- BAFHKFIYBFCXAU-UHFFFAOYSA-N (2-fluoro-5-methoxyphenyl)methanamine Chemical compound COC1=CC=C(F)C(CN)=C1 BAFHKFIYBFCXAU-UHFFFAOYSA-N 0.000 claims 1
- VJNGGOMRUHYAMC-UHFFFAOYSA-N (3,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC(F)=C1 VJNGGOMRUHYAMC-UHFFFAOYSA-N 0.000 claims 1
- DIWGZVQKFSFNLH-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-methylmethanamine Chemical compound CNCC1=CC=CC=C1Cl DIWGZVQKFSFNLH-UHFFFAOYSA-N 0.000 claims 1
- OWOUKRYOZIZVFK-UHFFFAOYSA-N 2-methylphenethylamine Chemical compound CC1=CC=CC=C1CCN OWOUKRYOZIZVFK-UHFFFAOYSA-N 0.000 claims 1
- JOYRYOBNNYDUMR-UHFFFAOYSA-N 4-[4-[2-(2,4,6-trifluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=C(F)C=C(F)C=C1F JOYRYOBNNYDUMR-UHFFFAOYSA-N 0.000 claims 1
- JBIOASAGZWOVGH-UHFFFAOYSA-N 4-[4-[2-(2-bromo-5-fluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=CC(F)=CC=C1Br JBIOASAGZWOVGH-UHFFFAOYSA-N 0.000 claims 1
- OLHHRXWVIGFHIL-UHFFFAOYSA-N 4-[4-[2-(2-bromo-5-fluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid N-[[2-chloro-3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound OC(C(CNCC1)=C1C(C=C1)=CC=C1OCCOC(C=C(C=C1)F)=C1Br)=O.FC(C1=CC=CC(CNC2CC2)=C1Cl)(F)F OLHHRXWVIGFHIL-UHFFFAOYSA-N 0.000 claims 1
- FIKPVBOZTALOIJ-UHFFFAOYSA-N 4-[4-[2-(2-bromo-5-fluorophenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC=C(F)C=3)Br)=CC=2)=C1C FIKPVBOZTALOIJ-UHFFFAOYSA-N 0.000 claims 1
- CZUCEGQMRLRKTB-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid N-[[2-chloro-3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound CC(C(C)=C1)=CC(OCCOC(C=C2)=CC=C2C(CCNC2)=C2C(O)=O)=C1Cl.FC(C1=CC=CC(CNC2CC2)=C1Cl)(F)F CZUCEGQMRLRKTB-UHFFFAOYSA-N 0.000 claims 1
- WHTCWJJUDHYVSP-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=C(C)C=3)Cl)=CC=2)=C1 WHTCWJJUDHYVSP-UHFFFAOYSA-N 0.000 claims 1
- HVEMAYQYZSYOGZ-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(3,5-dimethoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=C(C)C=3)Cl)=CC=2)=C1 HVEMAYQYZSYOGZ-UHFFFAOYSA-N 0.000 claims 1
- JMUJGIPCNDMYNG-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=C(C)C=3)Cl)=CC=2)=C1 JMUJGIPCNDMYNG-UHFFFAOYSA-N 0.000 claims 1
- IEBLAFHYIWKOCK-UHFFFAOYSA-N 4-[4-[2-(3-chloro-2,6-difluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=C(F)C=CC(Cl)=C1F IEBLAFHYIWKOCK-UHFFFAOYSA-N 0.000 claims 1
- WZOOWBZCJFOLAU-UHFFFAOYSA-N 4-[4-[2-(3-chloro-2,6-difluorophenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=C(Cl)C=CC=3F)F)=CC=2)=C1 WZOOWBZCJFOLAU-UHFFFAOYSA-N 0.000 claims 1
- DGIHJKQEJKQGFD-UHFFFAOYSA-N 4-[4-[2-(3-chloro-2,6-difluorophenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=C(Cl)C=CC=3F)F)=CC=2)=C1 DGIHJKQEJKQGFD-UHFFFAOYSA-N 0.000 claims 1
- MPZVIMKAJUUMSX-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methoxyphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(Cl)=CC=C1OCCOC1=CC=C(C=2CCNCC=2C(=O)N(CC=2C(=C(Cl)C=CC=2)Cl)C2CC2)C=C1 MPZVIMKAJUUMSX-UHFFFAOYSA-N 0.000 claims 1
- OZEMDWYPAFICGO-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methoxyphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(Cl)=CC=C1OCCOC1=CC=C(C=2CCNCC=2C(=O)N(CC=2C(=C(C)C=CC=2)C)C2CC2)C=C1 OZEMDWYPAFICGO-UHFFFAOYSA-N 0.000 claims 1
- CTAYAKNXEZEAIV-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methoxyphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(Cl)=CC=3)OC)=CC=2)=C1 CTAYAKNXEZEAIV-UHFFFAOYSA-N 0.000 claims 1
- HZYJQIWTYIOFAJ-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OCCOC1=CC=C(C=2CCNCC=2C(=O)N(CC=2C(=C(Cl)C=CC=2)Cl)C2CC2)C=C1 HZYJQIWTYIOFAJ-UHFFFAOYSA-N 0.000 claims 1
- QXPZBKGYFZEZEL-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(Cl)=CC=3)C)=CC=2)=C1C QXPZBKGYFZEZEL-UHFFFAOYSA-N 0.000 claims 1
- BJHAITPBNSBYQP-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid N-[[2-chloro-3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound OC(C(CNCC1)=C1C(C=C1)=CC=C1OCCOC(C=CC(C(F)(F)F)=C1)=C1Cl)=O.FC(C1=CC=CC(CNC2CC2)=C1Cl)(F)F BJHAITPBNSBYQP-UHFFFAOYSA-N 0.000 claims 1
- OFJPCRUQKSZFFI-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(=CC=3)C(F)(F)F)Cl)=CC=2)=C1 OFJPCRUQKSZFFI-UHFFFAOYSA-N 0.000 claims 1
- FRVXKYFYNIRBTK-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-n-cyclopropyl-n-[(3,5-dimethoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(=CC=3)C(F)(F)F)Cl)=CC=2)=C1 FRVXKYFYNIRBTK-UHFFFAOYSA-N 0.000 claims 1
- POUMYTOBNJHZMG-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(=CC=3)C(F)(F)F)Cl)=CC=2)=C1 POUMYTOBNJHZMG-UHFFFAOYSA-N 0.000 claims 1
- ZKFMOUQSZRSTGS-UHFFFAOYSA-N 4-[4-[3-(2,5-difluorophenoxy)propyl]phenyl]-N-methyl-N-(2-phenylethyl)-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C=1C=C(CCCOC=2C(=CC=C(F)C=2)F)C=CC=1C=1CCNCC=1C(=O)N(C)CCC1=CC=CC=C1 ZKFMOUQSZRSTGS-UHFFFAOYSA-N 0.000 claims 1
- CKJMNMSAMKXMGW-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1CCCOC1=CC(F)=CC=C1Br CKJMNMSAMKXMGW-UHFFFAOYSA-N 0.000 claims 1
- ZUESJUDDPXQLMZ-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-(2-phenylethyl)-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound FC1=CC=C(Br)C(OCCCC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CCC=2C=CC=CC=2)C2CC2)=C1 ZUESJUDDPXQLMZ-UHFFFAOYSA-N 0.000 claims 1
- IHMWNGLGFOAQIL-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[(2-methylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC=C1CN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=CC=C(F)C=2)Br)=CC=1)C1CC1 IHMWNGLGFOAQIL-UHFFFAOYSA-N 0.000 claims 1
- NJOFHEKRDZOEQT-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[(3,5-dimethoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(CCCOC=3C(=CC=C(F)C=3)Br)=CC=2)=C1 NJOFHEKRDZOEQT-UHFFFAOYSA-N 0.000 claims 1
- XQYYULLHWJYZAL-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[2-(2-methylphenyl)ethyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC=C1CCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=CC=C(F)C=2)Br)=CC=1)C1CC1 XQYYULLHWJYZAL-UHFFFAOYSA-N 0.000 claims 1
- WFVATWGXIDKWIS-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[2-(4-methoxyphenoxy)ethyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C1=CC(OC)=CC=C1OCCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=CC=C(F)C=2)Br)=CC=1)C1CC1 WFVATWGXIDKWIS-UHFFFAOYSA-N 0.000 claims 1
- VIODYOKNCDHZFQ-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[2-(4-methylphenyl)ethyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C1=CC(C)=CC=C1CCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=CC=C(F)C=2)Br)=CC=1)C1CC1 VIODYOKNCDHZFQ-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- UZWCDNSYWBBQFF-UHFFFAOYSA-N CC(C(C)=C1)=CC(OCCOC(C=C2)=CC=C2C(CCNC2)=C2C(O)=O)=C1Cl.BrC1=C(CNC2CC2)C=CC=C1 Chemical compound CC(C(C)=C1)=CC(OCCOC(C=C2)=CC=C2C(CCNC2)=C2C(O)=O)=C1Cl.BrC1=C(CNC2CC2)C=CC=C1 UZWCDNSYWBBQFF-UHFFFAOYSA-N 0.000 claims 1
- INCNPQBMBHXFKB-UHFFFAOYSA-N CC(C(F)=C1OCCOC(C=C2)=CC=C2C(CCNC2)=C2C(O)=O)=CC=C1F.BrC1=C(CNC2CC2)C=CC=C1 Chemical compound CC(C(F)=C1OCCOC(C=C2)=CC=C2C(CCNC2)=C2C(O)=O)=CC=C1F.BrC1=C(CNC2CC2)C=CC=C1 INCNPQBMBHXFKB-UHFFFAOYSA-N 0.000 claims 1
- ONZHLAVSPLFYDK-UHFFFAOYSA-N CC(C=C1Cl)=CC(Cl)=C1OCCOC(C=C1)=CC=C1C(CCNC1)=C1C(O)=O.BrC1=C(CNC2CC2)C=CC=C1 Chemical compound CC(C=C1Cl)=CC(Cl)=C1OCCOC(C=C1)=CC=C1C(CCNC1)=C1C(O)=O.BrC1=C(CNC2CC2)C=CC=C1 ONZHLAVSPLFYDK-UHFFFAOYSA-N 0.000 claims 1
- BZGDDLVKNMVGEY-UHFFFAOYSA-N CC(C=C1Cl)=CC(Cl)=C1OCCOC(C=C1)=CC=C1C(CCNC1)=C1C(O)=O.ClC1=CC=CC(CNC2CC2)=C1 Chemical compound CC(C=C1Cl)=CC(Cl)=C1OCCOC(C=C1)=CC=C1C(CCNC1)=C1C(O)=O.ClC1=CC=CC(CNC2CC2)=C1 BZGDDLVKNMVGEY-UHFFFAOYSA-N 0.000 claims 1
- WCFHYCYQPQZUPW-UHFFFAOYSA-N CC1=CC=CC(Cl)=C1OCCOC(C=C1)=CC=C1C(CCNC1)=C1C(O)=O.ClC1=C(CNC2CC2)C=CC=C1 Chemical compound CC1=CC=CC(Cl)=C1OCCOC(C=C1)=CC=C1C(CCNC1)=C1C(O)=O.ClC1=C(CNC2CC2)C=CC=C1 WCFHYCYQPQZUPW-UHFFFAOYSA-N 0.000 claims 1
- KYGRGPSFZXXEOQ-UHFFFAOYSA-N CCNCC(C=CC=C1)=C1Cl.CC(C=C1Cl)=CC(Cl)=C1OCCOC(C=C1)=CC=C1C(CCNC1)=C1C(O)=O Chemical compound CCNCC(C=CC=C1)=C1Cl.CC(C=C1Cl)=CC(Cl)=C1OCCOC(C=C1)=CC=C1C(CCNC1)=C1C(O)=O KYGRGPSFZXXEOQ-UHFFFAOYSA-N 0.000 claims 1
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- VWTMZTDMQGUISR-UHFFFAOYSA-N n-cyclopropyl-4-[4-[2-(2,5-dichlorophenoxy)ethoxy]phenyl]-n-[(2,3-dichlorophenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound ClC1=CC=C(Cl)C(OCCOC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CC=2C(=C(Cl)C=CC=2)Cl)C2CC2)=C1 VWTMZTDMQGUISR-UHFFFAOYSA-N 0.000 claims 1
- ADXFRUBZWDKAKF-UHFFFAOYSA-N n-cyclopropyl-4-[4-[2-(2,5-dichlorophenoxy)ethoxy]phenyl]-n-[(2,3-dimethylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC=C(Cl)C=3)Cl)=CC=2)=C1C ADXFRUBZWDKAKF-UHFFFAOYSA-N 0.000 claims 1
- UGRNCMOBEXTPMA-UHFFFAOYSA-N n-cyclopropyl-4-[4-[2-(2,5-dichlorophenoxy)ethoxy]phenyl]-n-[(3,5-dimethoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC=C(Cl)C=3)Cl)=CC=2)=C1 UGRNCMOBEXTPMA-UHFFFAOYSA-N 0.000 claims 1
- WHYZTWUXNYYKEF-UHFFFAOYSA-N n-cyclopropyl-4-[4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl]-n-[(2-fluoro-5-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=CC=3Cl)Cl)=CC=2)=C1 WHYZTWUXNYYKEF-UHFFFAOYSA-N 0.000 claims 1
- VRPGPAGCRYVLMT-UHFFFAOYSA-N n-cyclopropyl-4-[4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl]-n-[(3,4-dimethoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1CN(C(=O)C=1CNCCC=1C=1C=CC(OCCOC=2C(=CC(C)=CC=2Cl)Cl)=CC=1)C1CC1 VRPGPAGCRYVLMT-UHFFFAOYSA-N 0.000 claims 1
- PYLGJGUNBJTIJE-UHFFFAOYSA-N n-cyclopropyl-4-[4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl]-n-[(3,5-dimethoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=CC=3Cl)Cl)=CC=2)=C1 PYLGJGUNBJTIJE-UHFFFAOYSA-N 0.000 claims 1
- BXVDHBNLVXCTPN-UHFFFAOYSA-N n-cyclopropyl-4-[4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl]-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=CC=3Cl)Cl)=CC=2)=C1 BXVDHBNLVXCTPN-UHFFFAOYSA-N 0.000 claims 1
- JXLFQDMWYFNGSU-UHFFFAOYSA-N n-cyclopropyl-4-[4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl]-n-[(3-methylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=CC=3Cl)Cl)=CC=2)=C1 JXLFQDMWYFNGSU-UHFFFAOYSA-N 0.000 claims 1
- ABRBXBOXWBLKLD-UHFFFAOYSA-N n-cyclopropyl-n-(2-phenylethyl)-4-[4-[2-(2,3,5-trimethylphenoxy)ethyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC(C)=C(C)C(OCCC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CCC=2C=CC=CC=2)C2CC2)=C1 ABRBXBOXWBLKLD-UHFFFAOYSA-N 0.000 claims 1
- ZNNLEYGKPJUHNQ-UHFFFAOYSA-N n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-4-[4-[2-(2,3,6-trifluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound FC1=CC=C(F)C(OCCOC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CC=2C(=C(Cl)C=CC=2)Cl)C2CC2)=C1F ZNNLEYGKPJUHNQ-UHFFFAOYSA-N 0.000 claims 1
- HDQPTIPOGOEXBF-UHFFFAOYSA-N n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-4-[4-[2-(2,4,6-trifluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound FC1=CC(F)=CC(F)=C1OCCOC1=CC=C(C=2CCNCC=2C(=O)N(CC=2C(=C(Cl)C=CC=2)Cl)C2CC2)C=C1 HDQPTIPOGOEXBF-UHFFFAOYSA-N 0.000 claims 1
- AACNNDPTVFTJPH-UHFFFAOYSA-N n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound FC1=CC=C(F)C(OCCCC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CC=2C(=C(Cl)C=CC=2)Cl)C2CC2)=C1F AACNNDPTVFTJPH-UHFFFAOYSA-N 0.000 claims 1
- XBZBUNYFHDRCSR-UHFFFAOYSA-N n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-4-[4-[2-(2,3,6-trifluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=C(F)C=CC=3F)F)=CC=2)=C1C XBZBUNYFHDRCSR-UHFFFAOYSA-N 0.000 claims 1
- WXKNSKDTTOYEPS-UHFFFAOYSA-N n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-4-[4-[2-(2,4,5-trichlorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(Cl)=C(Cl)C=3)Cl)=CC=2)=C1C WXKNSKDTTOYEPS-UHFFFAOYSA-N 0.000 claims 1
- VYUXXHVGFQGRLI-UHFFFAOYSA-N n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-4-[4-[2-(2,4,6-trifluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(F)=CC=3F)F)=CC=2)=C1C VYUXXHVGFQGRLI-UHFFFAOYSA-N 0.000 claims 1
- IAHJGXLQQDMRIQ-UHFFFAOYSA-N n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(CCCOC=3C(=C(F)C=CC=3F)F)=CC=2)=C1C IAHJGXLQQDMRIQ-UHFFFAOYSA-N 0.000 claims 1
- QAGNFLCUCZFIDL-UHFFFAOYSA-N n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(CCCOC=3C(=C(F)C=CC=3F)F)=CC=2)=C1 QAGNFLCUCZFIDL-UHFFFAOYSA-N 0.000 claims 1
- BGTOFZQHCGWVAP-UHFFFAOYSA-N n-cyclopropyl-n-[(2-fluorophenyl)methyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound FC1=CC=CC=C1CN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=C(F)C=CC=2F)F)=CC=1)C1CC1 BGTOFZQHCGWVAP-UHFFFAOYSA-N 0.000 claims 1
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- QGGJOTOQZNLIGD-UHFFFAOYSA-N n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(CCCOC=3C(=C(F)C=CC=3F)F)=CC=2)=C1 QGGJOTOQZNLIGD-UHFFFAOYSA-N 0.000 claims 1
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- IYEVDYHMIMZNNG-UHFFFAOYSA-N n-cyclopropyl-n-[2-(3-methoxyphenoxy)ethyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(OCCN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(CCCOC=3C(=C(F)C=CC=3F)F)=CC=2)=C1 IYEVDYHMIMZNNG-UHFFFAOYSA-N 0.000 claims 1
- XBVPVGJVPQEDQE-UHFFFAOYSA-N n-cyclopropyl-n-[2-(3-methylphenoxy)ethyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(OCCN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(CCCOC=3C(=C(F)C=CC=3F)F)=CC=2)=C1 XBVPVGJVPQEDQE-UHFFFAOYSA-N 0.000 claims 1
- NFRPVBVBVJEDEB-UHFFFAOYSA-N n-cyclopropyl-n-[2-(4-fluorophenyl)ethyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C1=CC(F)=CC=C1CCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=C(F)C=CC=2F)F)=CC=1)C1CC1 NFRPVBVBVJEDEB-UHFFFAOYSA-N 0.000 claims 1
- VXZZJQBCCVUFEI-UHFFFAOYSA-N n-cyclopropyl-n-[2-(4-methoxyphenoxy)ethyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C1=CC(OC)=CC=C1OCCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=C(F)C=CC=2F)F)=CC=1)C1CC1 VXZZJQBCCVUFEI-UHFFFAOYSA-N 0.000 claims 1
- KIZRFMZYNFOFNA-UHFFFAOYSA-N n-cyclopropyl-n-[2-(4-methylphenyl)ethyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C1=CC(C)=CC=C1CCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=C(F)C=CC=2F)F)=CC=1)C1CC1 KIZRFMZYNFOFNA-UHFFFAOYSA-N 0.000 claims 1
- ATWFXAVUNFGOGR-UHFFFAOYSA-N n-cyclopropyl-n-[[3-(trifluoromethyl)phenyl]methyl]-4-[4-[2-(2,3,5-trimethylphenoxy)ethyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC(C)=C(C)C(OCCC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CC=2C=C(C=CC=2)C(F)(F)F)C2CC2)=C1 ATWFXAVUNFGOGR-UHFFFAOYSA-N 0.000 claims 1
- FBUDTQSNZRKBAS-UHFFFAOYSA-N n-cyclopropyl-n-[[3-(trifluoromethyl)phenyl]methyl]-4-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound FC1=CC=C(F)C(OCCCC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CC=2C=C(C=CC=2)C(F)(F)F)C2CC2)=C1F FBUDTQSNZRKBAS-UHFFFAOYSA-N 0.000 claims 1
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| KR20060007041A (ko) * | 2003-04-29 | 2006-01-23 | 액테리온 파마슈티칼 리미티드 | 신규의 3,4-이치환된 1,2,3,6-테트라하이드로피리딘 유도체 |
| CA2521938A1 (en) * | 2003-04-30 | 2004-11-11 | Actelion Pharmaceuticals Ltd | 9-azabicyclo[3.3.1]non-6-ene derivatives with a heteroatom at the 3-position as renin inhibitors |
| KR20060015573A (ko) * | 2003-05-02 | 2006-02-17 | 액테리온 파마슈티칼 리미티드 | 신규한 디아자비시클로노넨 유도체 |
| WO2004105738A2 (en) * | 2003-05-30 | 2004-12-09 | Actelion Pharmaceuticals Ltd | Use of tetrahydropyridine derivatives |
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| WO2005054243A1 (en) * | 2003-12-05 | 2005-06-16 | Actelion Pharmaceuticals Ltd | Diazabicyclononene derivatives and their use as renin inhibitors |
| JPWO2005068427A1 (ja) * | 2004-01-14 | 2007-09-06 | 武田薬品工業株式会社 | カルボキサミド誘導体およびその用途 |
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| JP2008510755A (ja) | 2004-08-25 | 2008-04-10 | アクテリオン ファーマシューティカルズ リミテッド | ビシクロノネン誘導体 |
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| WO2007049224A1 (en) * | 2005-10-25 | 2007-05-03 | Actelion Pharmaceuticals Ltd | Novel hexahydro- or octahydro-cyclopenta[c]pyrrole derivatives |
| AU2007210813A1 (en) * | 2006-02-02 | 2007-08-09 | Actelion Pharmaceuticals Ltd | Secondary amines as renin inhibitors |
| EP2029542A2 (en) * | 2006-03-03 | 2009-03-04 | Actelion Pharmaceuticals Ltd. | Primary amines as renin inhibitors |
| AU2007224368A1 (en) * | 2006-03-08 | 2007-09-13 | Actelion Pharmaceuticals Ltd | New amines |
| EP1908471A1 (en) * | 2006-10-04 | 2008-04-09 | Speedel Experimenta AG | Tetrahydropyridines as renin inhibitors |
| CA2688057A1 (en) | 2007-05-24 | 2008-11-27 | Merck Frosst Canada Ltd. | Novel case of renin inhibitors |
| EP2190811B1 (en) | 2007-08-20 | 2013-08-07 | Merck Canada Inc. | Renin inhibitors |
| SG192543A1 (en) | 2008-05-05 | 2013-08-30 | Merck Canada Inc | 3, 4 - substituted piperidine derivatives as renin inhibitors |
| EP2580201B1 (en) | 2010-06-11 | 2017-08-02 | Rhodes Technologies | Transition metal-catalyzed processes for the preparation of n-allyl compounds and use thereof |
| TWI471289B (zh) | 2010-06-11 | 2015-02-01 | Rhodes Technologies | 使三級胺進行ｎ－脫烷反應之方法 |
| CN117865941B (zh) * | 2024-03-13 | 2024-06-28 | 上海方予健康医药科技有限公司 | 取代哌啶化合物及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5376666A (en) * | 1992-11-30 | 1994-12-27 | The Du Pont Merck Pharmaceutical Company | Angiotension-II receptor blocking, azacycloalkyl or azacycloalkenyl |
| TR199800409T1 (xx) * | 1995-09-07 | 1998-05-21 | F.Hoffmann-La Roche Ag | Kalp ve b�brek yetersizli�inin tedavii�in yeni 4-(oksialkoksifenil)-3-oksi-piperidinler |
| US6376672B1 (en) * | 1999-04-27 | 2002-04-23 | Hoffmann-La Roche Inc. | Naphthalenylmethoxypiperidines as renin inhibitors |
-
2003
- 2003-04-29 BR BR0312000-7A patent/BR0312000A/pt not_active IP Right Cessation
- 2003-04-29 WO PCT/EP2003/004445 patent/WO2004002957A1/en not_active Ceased
- 2003-04-29 US US10/514,164 patent/US20060009497A1/en not_active Abandoned
- 2003-04-29 CA CA002490138A patent/CA2490138A1/en not_active Abandoned
- 2003-04-29 EP EP03722566A patent/EP1519920A1/en not_active Withdrawn
- 2003-04-29 JP JP2004516551A patent/JP2005532371A/ja active Pending
- 2003-04-29 AU AU2003229746A patent/AU2003229746A1/en not_active Abandoned
- 2003-04-29 RU RU2005102002/04A patent/RU2005102002A/ru not_active Application Discontinuation
- 2003-04-29 PL PL03375214A patent/PL375214A1/xx not_active Application Discontinuation
- 2003-04-29 MX MXPA04012136A patent/MXPA04012136A/es unknown
- 2003-04-29 CN CN038138875A patent/CN1662498A/zh active Pending
- 2003-10-10 CL CL200302043A patent/CL2003002043A1/es unknown
- 2003-10-28 TW TW092129927A patent/TW200514772A/zh unknown
-
2004
- 2004-10-18 ZA ZA200408423A patent/ZA200408423B/xx unknown
- 2004-12-21 IL IL16588704A patent/IL165887A0/xx unknown
-
2005
- 2005-01-19 NO NO20050290A patent/NO20050290L/no not_active Application Discontinuation
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