JP2008504277A5 - - Google Patents
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- Publication number
- JP2008504277A5 JP2008504277A5 JP2007518296A JP2007518296A JP2008504277A5 JP 2008504277 A5 JP2008504277 A5 JP 2008504277A5 JP 2007518296 A JP2007518296 A JP 2007518296A JP 2007518296 A JP2007518296 A JP 2007518296A JP 2008504277 A5 JP2008504277 A5 JP 2008504277A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- trifluoromethyl
- benzyl
- tetrazol
- bis
- 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.)
- Granted
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- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 24
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 108010023302 HDL Cholesterol Proteins 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- HLTWGFKVNPAPIK-UHFFFAOYSA-N propan-2-yl 1h-indene-5-carboxylate Chemical compound CC(C)OC(=O)C1=CC=C2CC=CC2=C1 HLTWGFKVNPAPIK-UHFFFAOYSA-N 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- WGJBMEKISIWTOU-ZDGMYTEDSA-N (2s)-3-[5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]-2-methylpropanoic acid Chemical compound C12=CC(C)=C(C(F)(F)F)C=C2N(C[C@H](C)C(O)=O)CCCC1N(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WGJBMEKISIWTOU-ZDGMYTEDSA-N 0.000 claims 1
- XPHIEEJLRHUBSX-IBGZPJMESA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1,7-dimethyl-n-(2-methyltetrazol-5-yl)-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-5-amine Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC(=C(C)C=C21)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XPHIEEJLRHUBSX-IBGZPJMESA-N 0.000 claims 1
- FIMOBMQLBHUGEN-VWLOTQADSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(cyclopentylmethyl)-n-(2-methyltetrazol-5-yl)-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepin-5-amine Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2C3=CC=4COCC=4C=C3N(CC3CCCC3)CCC2)=N1 FIMOBMQLBHUGEN-VWLOTQADSA-N 0.000 claims 1
- LUEDXMVWKYTHAI-SANMLTNESA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(cyclopentylmethyl)-n-(2-methyltetrazol-5-yl)-3,4,5,7,8,9-hexahydro-2h-cyclopenta[h][1]benzazepin-5-amine Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2C3=CC=4CCCC=4C=C3N(CC3CCCC3)CCC2)=N1 LUEDXMVWKYTHAI-SANMLTNESA-N 0.000 claims 1
- XJVKFWFJXZOJRC-FQEVSTJZSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-ethyl-7-methyl-n-(2-methyltetrazol-5-yl)-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-5-amine Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC(=C(C)C=C21)C(F)(F)F)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XJVKFWFJXZOJRC-FQEVSTJZSA-N 0.000 claims 1
- NNGQXKJWPHTALS-IBGZPJMESA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-1-(2h-tetrazol-5-ylmethyl)-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-5-amine Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC=1N=NNN=1 NNGQXKJWPHTALS-IBGZPJMESA-N 0.000 claims 1
- PFVYSWIWCUSXDJ-DEOSSOPVSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-1-(piperidin-4-ylmethyl)-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-5-amine Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC1CCNCC1 PFVYSWIWCUSXDJ-DEOSSOPVSA-N 0.000 claims 1
- WJZVHBFKTYFQLJ-DEOSSOPVSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-1-(pyridin-4-ylmethyl)-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-5-amine Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC1=CC=NC=C1 WJZVHBFKTYFQLJ-DEOSSOPVSA-N 0.000 claims 1
- AUZDLAWXAUEWHC-JIDHJSLPSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-1-(pyridin-4-ylmethyl)-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-5-amine;hydrochloride Chemical compound Cl.C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC1=CC=NC=C1 AUZDLAWXAUEWHC-JIDHJSLPSA-N 0.000 claims 1
- CRGOATIHHLWYTC-VWLOTQADSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-(2-methyltetrazol-5-yl)-1-(pyridin-4-ylmethyl)-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepin-5-amine Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2C3=CC=4COCC=4C=C3N(CC=3C=CN=CC=3)CCC2)=N1 CRGOATIHHLWYTC-VWLOTQADSA-N 0.000 claims 1
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- BEIJZIGQSAGXEC-NRFANRHFSA-N 2-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepin-1-yl]ethanol Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2C3=CC=4COCC=4C=C3N(CCO)CCC2)=N1 BEIJZIGQSAGXEC-NRFANRHFSA-N 0.000 claims 1
- SFSZUUNKFVUKGS-FQEVSTJZSA-N 2-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]ethanol Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(CCO)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SFSZUUNKFVUKGS-FQEVSTJZSA-N 0.000 claims 1
- YVQWCGPHXMRYPF-QFIPXVFZSA-N 2-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]ethyl acetate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC(=C(C)C=C21)C(F)(F)F)CCOC(=O)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YVQWCGPHXMRYPF-QFIPXVFZSA-N 0.000 claims 1
- NQUZWBZHYJTRFZ-NRFANRHFSA-N 2-[2-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]ethoxy]acetic acid Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(CCOCC(O)=O)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NQUZWBZHYJTRFZ-NRFANRHFSA-N 0.000 claims 1
- DJNZBQFUPNFHIY-IRQSHYTFSA-N 2-[4-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepin-1-yl]methyl]cyclohexyl]acetic acid Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2C3=CC=4COCC=4C=C3N(CC3CCC(CC(O)=O)CC3)CCC2)=N1 DJNZBQFUPNFHIY-IRQSHYTFSA-N 0.000 claims 1
- WFDUVYKBQNFEHP-SANMLTNESA-N 2-[4-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]phenyl]acetic acid Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC1=CC=C(CC(O)=O)C=C1 WFDUVYKBQNFEHP-SANMLTNESA-N 0.000 claims 1
- FKFCLPIIFIDPKI-VWLOTQADSA-N 2-[4-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]piperidin-1-yl]acetic acid Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC1CCN(CC(O)=O)CC1 FKFCLPIIFIDPKI-VWLOTQADSA-N 0.000 claims 1
- WQZRSLLOECZVHP-UHFFFAOYSA-N 2-[4-[[5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]cyclohexyl]acetic acid Chemical compound C1=2C=C(C(F)(F)F)C(C)=CC=2C(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCCN1CC1CCC(CC(O)=O)CC1 WQZRSLLOECZVHP-UHFFFAOYSA-N 0.000 claims 1
- BRPWZGZBDZUXCA-UHFFFAOYSA-N 2-[4-[[5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(3-methyl-1,2-oxazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]cyclohexyl]acetic acid Chemical compound O1N=C(C)C=C1N(C1C2=CC(C)=C(C=C2N(CC2CCC(CC(O)=O)CC2)CCC1)C(F)(F)F)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BRPWZGZBDZUXCA-UHFFFAOYSA-N 0.000 claims 1
- IFWLEWADLFGEGJ-VWLOTQADSA-N 2-[5-[[3,5-bis(trifluoromethyl)phenyl]methyl-[(5s)-1-(cyclopentylmethyl)-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-5-yl]amino]tetrazol-2-yl]ethanol Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(CCO)N=N2)CCN1CC1CCCC1 IFWLEWADLFGEGJ-VWLOTQADSA-N 0.000 claims 1
- MULHIOPENWZDGA-FQEVSTJZSA-N 2-aminoethyl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(C(=O)OCCN)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MULHIOPENWZDGA-FQEVSTJZSA-N 0.000 claims 1
- DQUSXMBTTSCQQO-LFQPHHBNSA-N 2-methylpentan-3-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC(=C(C)C=C21)C(F)(F)F)C(=O)OC(CC)C(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DQUSXMBTTSCQQO-LFQPHHBNSA-N 0.000 claims 1
- CGMBVYQVWCBALY-QHCPKHFHSA-N 3-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-3,4,5,7,8,9-hexahydro-2h-cyclopenta[h][1]benzazepine-1-carbonyl]oxy-2,2-dimethylpropanoic acid Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2C3=CC=4CCCC=4C=C3N(C(=O)OCC(C)(C)C(O)=O)CCC2)=N1 CGMBVYQVWCBALY-QHCPKHFHSA-N 0.000 claims 1
- GOIUOUZURFSWCG-NRFANRHFSA-N 3-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl]oxy-2,2-dimethylpropanoic acid Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(C(=O)OCC(C)(C)C(O)=O)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GOIUOUZURFSWCG-NRFANRHFSA-N 0.000 claims 1
- TZVBICPTKXRYME-VWLOTQADSA-N 3-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]benzoic acid Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC1=CC=CC(C(O)=O)=C1 TZVBICPTKXRYME-VWLOTQADSA-N 0.000 claims 1
- XIXGBCXDMXBYBU-DEOSSOPVSA-N 4-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]benzoic acid Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1C1=CC=C(C(O)=O)C=C1 XIXGBCXDMXBYBU-DEOSSOPVSA-N 0.000 claims 1
- UFXCYRLCVZFMNQ-VWLOTQADSA-N 4-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]benzoic acid Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC1=CC=C(C(O)=O)C=C1 UFXCYRLCVZFMNQ-VWLOTQADSA-N 0.000 claims 1
- BIYYZNPVJCJREK-DEOSSOPVSA-N 5-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepin-1-yl]-3,3-dimethylpentanoic acid Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2C3=CC=4COCC=4C=C3N(CCC(C)(C)CC(O)=O)CCC2)=N1 BIYYZNPVJCJREK-DEOSSOPVSA-N 0.000 claims 1
- QFNSBPIESHLPIE-VWLOTQADSA-N 5-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-[2-(2-hydroxyethyl)tetrazol-5-yl]amino]-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepin-1-yl]-3,3-dimethylpentanoic acid Chemical compound N1=NN(CCO)N=C1N([C@H]1CCCN(C2=CC=3COCC=3C=C21)CCC(C)(C)CC(O)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QFNSBPIESHLPIE-VWLOTQADSA-N 0.000 claims 1
- NOFMZHKFQDYPSS-QFIPXVFZSA-N 5-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]thiophene-2-carboxylic acid Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1CC1=CC=C(C(O)=O)S1 NOFMZHKFQDYPSS-QFIPXVFZSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- HZBFXKPTLLFTJD-UHFFFAOYSA-N CC(C)(COC(=O)N1CC=CC=C2C1CC3CCCC3=C2)C(=O)OC Chemical compound CC(C)(COC(=O)N1CC=CC=C2C1CC3CCCC3=C2)C(=O)OC HZBFXKPTLLFTJD-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- XITPLNUGVMFLRK-QHCPKHFHSA-N cyclopentyl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1C(=O)OC1CCCC1 XITPLNUGVMFLRK-QHCPKHFHSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- GBFATWBODAFVEU-FQEVSTJZSA-N ethyl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC(=C(C)C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GBFATWBODAFVEU-FQEVSTJZSA-N 0.000 claims 1
- GYEKKNSJCCQNQX-MHZLTWQESA-N ethyl 2-[4-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1CN1C2=CC(C(F)(F)F)=C(C)C=C2[C@@H](N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCC1 GYEKKNSJCCQNQX-MHZLTWQESA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- SZESGYMIZWMYDX-UHFFFAOYSA-N methyl 2-[4-[[5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(3-methyl-1,2-oxazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]cyclohexyl]acetate Chemical compound C1CC(CC(=O)OC)CCC1CN1C2=CC(C(F)(F)F)=C(C)C=C2C(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2ON=C(C)C=2)CCC1 SZESGYMIZWMYDX-UHFFFAOYSA-N 0.000 claims 1
- OOUSUYBNSIFBRY-SANMLTNESA-N methyl 3-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C3=CC(=C(C)C=C3[C@@H](N(CC=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)C3=NN(C)N=N3)CCC2)C(F)(F)F)=C1 OOUSUYBNSIFBRY-SANMLTNESA-N 0.000 claims 1
- CNCAXBRVYBNCPG-SANMLTNESA-N methyl 4-[[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C2=CC(C(F)(F)F)=C(C)C=C2[C@@H](N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCC1 CNCAXBRVYBNCPG-SANMLTNESA-N 0.000 claims 1
- LPKMGYHNCFNWCR-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(cyclopentylmethyl)-n-(2-methyltetrazol-5-yl)-2,3,4,5,7,8,9,10-octahydrobenzo[h][1]benzazepin-5-amine Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2C3=CC=4CCCCC=4C=C3N(CC3CCCC3)CCC2)=N1 LPKMGYHNCFNWCR-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- DSQNFULSOJERBB-QHCPKHFHSA-N oxan-4-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)C)N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)CCN1C(=O)OC1CCOCC1 DSQNFULSOJERBB-QHCPKHFHSA-N 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- XNVIGELDDWQMPP-QHCPKHFHSA-N pentan-3-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC(=C(C)C=C21)C(F)(F)F)C(=O)OC(CC)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XNVIGELDDWQMPP-QHCPKHFHSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000036470 plasma concentration Effects 0.000 claims 1
- DVPOEQYHIZNFLH-HSZRJFAPSA-N propan-2-yl (5r)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-3,4,5,7,8,9-hexahydro-2h-cyclopenta[h][1]benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@@H]1CCCN(C2=CC=3CCCC=3C=C21)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DVPOEQYHIZNFLH-HSZRJFAPSA-N 0.000 claims 1
- DAFQXBZNJZQTKI-QFIPXVFZSA-N propan-2-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC=3COCC=3C=C21)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DAFQXBZNJZQTKI-QFIPXVFZSA-N 0.000 claims 1
- DVPOEQYHIZNFLH-QHCPKHFHSA-N propan-2-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-3,4,5,7,8,9-hexahydro-2h-cyclopenta[h][1]benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC=3CCCC=3C=C21)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DVPOEQYHIZNFLH-QHCPKHFHSA-N 0.000 claims 1
- XXBYALLEYGCVLW-DEOSSOPVSA-N propan-2-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-3,4,5,8,9,10-hexahydro-2h-cyclopenta[i][1]benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=C3CCCC3=C(C)C=C21)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XXBYALLEYGCVLW-DEOSSOPVSA-N 0.000 claims 1
- NJOMLQFRPPNZOD-NRFANRHFSA-N propan-2-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=CC(=C(C)C=C21)C(F)(F)F)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NJOMLQFRPPNZOD-NRFANRHFSA-N 0.000 claims 1
- JGYFOQYFSSXJHV-QFIPXVFZSA-N propan-2-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-8,9-dimethyl-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@H]1CCCN(C2=C(C)C(C)=CC=C21)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JGYFOQYFSSXJHV-QFIPXVFZSA-N 0.000 claims 1
- VRJSPBBAONBYEC-VWLOTQADSA-N propan-2-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-[2-(2-hydroxyethyl)tetrazol-5-yl]amino]-7-methyl-3,4,5,8,9,10-hexahydro-2h-cyclopenta[i][1]benzazepine-1-carboxylate Chemical compound N1=NN(CCO)N=C1N([C@H]1CCCN(C2=C3CCCC3=C(C)C=C21)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VRJSPBBAONBYEC-VWLOTQADSA-N 0.000 claims 1
- NQJUOWYPUVKYTM-QHCPKHFHSA-N propan-2-yl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-[2-(2-hydroxyethyl)tetrazol-5-yl]amino]-8,9-dimethyl-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(CCO)N=C1N([C@H]1CCCN(C2=C(C)C(C)=CC=C21)C(=O)OC(C)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NQJUOWYPUVKYTM-QHCPKHFHSA-N 0.000 claims 1
- PAAMHDIEMJHSPM-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-2,3,4,5,7,8,9,10-octahydrobenzo[h][1]benzazepine-1-carboxylate Chemical compound C12=CC=3CCCCC=3C=C2N(C(=O)OC(C)C)CCCC1N(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PAAMHDIEMJHSPM-UHFFFAOYSA-N 0.000 claims 1
- DVPOEQYHIZNFLH-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-3,4,5,7,8,9-hexahydro-2h-cyclopenta[h][1]benzazepine-1-carboxylate Chemical compound C12=CC=3CCCC=3C=C2N(C(=O)OC(C)C)CCCC1N(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DVPOEQYHIZNFLH-UHFFFAOYSA-N 0.000 claims 1
- UWWFUIBLXISBCB-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(Cl)C=C2N(C(=O)OC(C)C)CCCC1N(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UWWFUIBLXISBCB-UHFFFAOYSA-N 0.000 claims 1
- XSRGXANGXYYSLC-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2h-tetrazol-5-yl)amino]-3,4,5,7,8,9-hexahydro-2h-cyclopenta[h][1]benzazepine-1-carboxylate Chemical compound C12=CC=3CCCC=3C=C2N(C(=O)OC(C)C)CCCC1N(C1=NNN=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XSRGXANGXYYSLC-UHFFFAOYSA-N 0.000 claims 1
- OHBFCIQJIARLEG-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2h-tetrazol-5-yl)amino]-3,4,5,8,9,10-hexahydro-2h-cyclopenta[i][1]benzazepine-1-carboxylate Chemical compound C12=CC=C3CCCC3=C2N(C(=O)OC(C)C)CCCC1N(C1=NNN=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OHBFCIQJIARLEG-UHFFFAOYSA-N 0.000 claims 1
- RXZOHYMVEIIJBK-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2h-tetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C)=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)CCCC1N(C=1NN=NN=1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RXZOHYMVEIIJBK-UHFFFAOYSA-N 0.000 claims 1
- OKOIBAJDFPVHSX-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2h-tetrazol-5-yl)amino]-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(Cl)C=C2N(C(=O)OC(C)C)CCCC1N(C=1NN=NN=1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OKOIBAJDFPVHSX-UHFFFAOYSA-N 0.000 claims 1
- JNYUKXLOCJSLJF-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-methyl-1h-pyrazol-3-yl)amino]-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(Cl)C=C2N(C(=O)OC(C)C)CCCC1N(C1=NNC(C)=C1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JNYUKXLOCJSLJF-UHFFFAOYSA-N 0.000 claims 1
- WQJOJBGYFCMEHK-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-methyl-2h-1,2-oxazol-5-yl)amino]-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(Cl)C=C2N(C(=O)OC(C)C)CCCC1N(C1(C)C=CNO1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WQJOJBGYFCMEHK-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- GTMFLRLAOYVQAO-QFIPXVFZSA-N tert-butyl (5s)-5-[[2-(2-aminoethyl)tetrazol-5-yl]-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(CCN)N=C1N([C@@H]1C=2C=C(C(=CC=2N(C(=O)OC(C)(C)C)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GTMFLRLAOYVQAO-QFIPXVFZSA-N 0.000 claims 1
- UIADFZNXRVKQNY-QHCPKHFHSA-N tert-butyl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-3,4,5,7,8,9-hexahydro-2h-cyclopenta[h][1]benzazepine-1-carboxylate Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)[C@@H]2C3=CC=4CCCC=4C=C3N(C(=O)OC(C)(C)C)CCC2)=N1 UIADFZNXRVKQNY-QHCPKHFHSA-N 0.000 claims 1
- OHFQGIGQVDLYLJ-NRFANRHFSA-N tert-butyl (5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(C(=O)OC(C)(C)C)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OHFQGIGQVDLYLJ-NRFANRHFSA-N 0.000 claims 1
- JUKWZDOXLZRSRS-UHFFFAOYSA-N tert-butyl 1h-indene-5-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=C2CC=CC2=C1 JUKWZDOXLZRSRS-UHFFFAOYSA-N 0.000 claims 1
- RSWQLSGHWCNKOC-DEOSSOPVSA-N tert-butyl n-[2-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-7-ethyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-1-yl]ethyl]carbamate Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(CCNC(=O)OC(C)(C)C)CCC1)C(F)(F)F)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RSWQLSGHWCNKOC-DEOSSOPVSA-N 0.000 claims 1
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| 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 |
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| JP5644106B2 (ja) | 2007-05-17 | 2014-12-24 | 味の素株式会社 | 脂質修飾酵素の活性測定法 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
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2005
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- 2005-06-22 EA EA200700119A patent/EA200700119A1/ru unknown
- 2005-06-22 WO PCT/US2005/021789 patent/WO2006012093A1/en not_active Ceased
- 2005-06-22 AU AU2005267436A patent/AU2005267436A1/en not_active Abandoned
- 2005-06-22 MX MXPA06014716A patent/MXPA06014716A/es not_active Application Discontinuation
- 2005-06-22 US US11/570,540 patent/US20080269284A1/en not_active Abandoned
- 2005-06-22 CA CA002570688A patent/CA2570688A1/en not_active Abandoned
- 2005-06-22 KR KR1020067027038A patent/KR20070041452A/ko not_active Ceased
- 2005-06-22 BR BRPI0512523-5A patent/BRPI0512523A/pt not_active Application Discontinuation
- 2005-06-22 EP EP05768995A patent/EP1761521A1/en not_active Withdrawn
- 2005-06-23 EP EP11184746A patent/EP2479175A1/en not_active Withdrawn
- 2005-06-23 WO PCT/US2005/022389 patent/WO2006002342A1/en not_active Ceased
- 2005-06-23 MX MXPA06014706A patent/MXPA06014706A/es active IP Right Grant
- 2005-06-23 ES ES05763328T patent/ES2372291T3/es not_active Expired - Lifetime
- 2005-06-23 DK DK05763328.1T patent/DK1761522T3/da active
- 2005-06-23 PT PT05763328T patent/PT1761522E/pt unknown
- 2005-06-23 EA EA200700120A patent/EA012585B1/ru not_active IP Right Cessation
- 2005-06-23 PL PL05763328T patent/PL1761522T3/pl unknown
- 2005-06-23 AT AT05763328T patent/ATE528304T1/de active
- 2005-06-23 RS RS20110559A patent/RS52064B/sr unknown
- 2005-06-23 AU AU2005258241A patent/AU2005258241B2/en not_active Ceased
- 2005-06-23 EP EP05763328A patent/EP1761522B1/en not_active Expired - Lifetime
- 2005-06-23 SI SI200531438T patent/SI1761522T1/sl unknown
- 2005-06-23 US US11/570,542 patent/US7786108B2/en not_active Expired - Fee Related
- 2005-06-23 JP JP2007518296A patent/JP4836945B2/ja not_active Expired - Fee Related
- 2005-06-23 CN CN2005800206855A patent/CN1972932B/zh not_active Expired - Fee Related
- 2005-06-23 CA CA2570673A patent/CA2570673C/en not_active Expired - Fee Related
- 2005-06-23 NZ NZ550978A patent/NZ550978A/en not_active IP Right Cessation
- 2005-06-23 BR BRPI0512516-2A patent/BRPI0512516A/pt active Search and Examination
- 2005-06-23 HR HR20110761T patent/HRP20110761T1/hr unknown
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- 2006-12-19 EC EC2006007098A patent/ECSP067098A/es unknown
- 2006-12-19 EC EC2006007095A patent/ECSP067095A/es unknown
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- 2007-01-24 NO NO20070468A patent/NO20070468L/no not_active Application Discontinuation
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