HRP20110761T1 - Spojevi za liječenje dislipidemije i njihova upotreba - Google Patents
Spojevi za liječenje dislipidemije i njihova upotreba Download PDFInfo
- Publication number
- HRP20110761T1 HRP20110761T1 HR20110761T HRP20110761T HRP20110761T1 HR P20110761 T1 HRP20110761 T1 HR P20110761T1 HR 20110761 T HR20110761 T HR 20110761T HR P20110761 T HRP20110761 T HR P20110761T HR P20110761 T1 HRP20110761 T1 HR P20110761T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- bistrifluoromethylbenzyl
- tetrazol
- amino
- trifluoromethyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 16
- 208000032928 Dyslipidaemia Diseases 0.000 title claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 title claims 2
- -1 -NR11R12 Chemical group 0.000 claims 33
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims 15
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 15
- 239000000203 mixture Substances 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- 125000004191 (C1-C6) alkoxy group Chemical group 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- ZERZIYSMNUFKBJ-SFHVURJKSA-N (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-carboxylic acid Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(C(O)=O)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZERZIYSMNUFKBJ-SFHVURJKSA-N 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- KGCXLSZXKWPIOH-FQEVSTJZSA-N (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-carboxylic acid Chemical class 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)=O)CCC2)=N1 KGCXLSZXKWPIOH-FQEVSTJZSA-N 0.000 claims 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims 2
- 108010023302 HDL Cholesterol Proteins 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000001301 oxygen Substances 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
- WLIXIBUJEFQJQM-VWLOTQADSA-N (5s)-1-benzyl-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-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=CC=C1 WLIXIBUJEFQJQM-VWLOTQADSA-N 0.000 claims 1
- WXRLRJMMKLNZCX-MHZLTWQESA-N (5s)-n-[2-(2-aminoethyl)tetrazol-5-yl]-1-benzyl-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepin-5-amine Chemical compound NCCN1N=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=CC=CC=3)CCC2)=N1 WXRLRJMMKLNZCX-MHZLTWQESA-N 0.000 claims 1
- JWRYZTSUCVVUOS-QFIPXVFZSA-N (5s)-n-[2-(2-aminoethyl)tetrazol-5-yl]-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(3,3,3-trifluoropropyl)-2,3,4,5,7,9-hexahydrofuro[3,4-h][1]benzazepin-5-amine Chemical compound NCCN1N=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(F)(F)F)CCC2)=N1 JWRYZTSUCVVUOS-QFIPXVFZSA-N 0.000 claims 1
- JVHSSSVASVBZGF-QHCPKHFHSA-N (5s)-n-[2-(2-aminoethyl)tetrazol-5-yl]-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(cyclopropylmethyl)-7-methyl-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(CCN)N=N2)CCN1CC1CC1 JVHSSSVASVBZGF-QHCPKHFHSA-N 0.000 claims 1
- DDXDRIKSOIXVTQ-BQAIUKQQSA-N (5s)-n-[2-(2-aminoethyl)tetrazol-5-yl]-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(cyclopropylmethyl)-7-methyl-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(CCN)N=N2)CCN1CC1CC1 DDXDRIKSOIXVTQ-BQAIUKQQSA-N 0.000 claims 1
- GIZOHUJIEKLOJB-QFIPXVFZSA-N (5s)-n-[2-(2-aminoethyl)tetrazol-5-yl]-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-1-(1,3-thiazol-2-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(CCN)N=N2)CCN1CC1=NC=CS1 GIZOHUJIEKLOJB-QFIPXVFZSA-N 0.000 claims 1
- YMLCJYKZIZJXSA-NDEPHWFRSA-N (5s)-n-[2-(2-aminoethyl)tetrazol-5-yl]-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-1-(2-phenylmethoxyethyl)-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(CCN)N=N2)CCN1CCOCC1=CC=CC=C1 YMLCJYKZIZJXSA-NDEPHWFRSA-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
- VIGSQDXGNZMWCB-NDEPHWFRSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(cyclopentylmethyl)-11-methyl-n-(2-methyltetrazol-5-yl)-2,3,4,5,7,8,9,10-octahydrobenzo[h][1]benzazepin-5-amine Chemical compound C([C@@H](C=1C=C2CCCCC2=C(C2=1)C)N(CC=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C1=NN(C)N=N1)CCN2CC1CCCC1 VIGSQDXGNZMWCB-NDEPHWFRSA-N 0.000 claims 1
- WYAPCMZWOKMLHV-DEOSSOPVSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(cyclopentylmethyl)-7-methyl-n-(2-methyltetrazol-5-yl)-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)CCN1CC1CCCC1 WYAPCMZWOKMLHV-DEOSSOPVSA-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
- GFQMOOFXDAULBL-QFIPXVFZSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-1-(cyclopropylmethyl)-7-methyl-n-(2-methyltetrazol-5-yl)-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)CCN1CC1CC1 GFQMOOFXDAULBL-QFIPXVFZSA-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
- WZOIUSUTQFCHGW-VWLOTQADSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7,9-dimethyl-n-(2-methyltetrazol-5-yl)-1-[[4-(2h-tetrazol-5-yl)phenyl]methyl]-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepin-5-amine Chemical compound C([C@@H](C=1C=C(C(=C(C)C=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(C=C1)=CC=C1C1=NN=NN1 WZOIUSUTQFCHGW-VWLOTQADSA-N 0.000 claims 1
- IYKHUEFRFDFUTI-QFIPXVFZSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-1-[(1-methylimidazol-2-yl)methyl]-n-(2-methyltetrazol-5-yl)-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=NC=CN1C IYKHUEFRFDFUTI-QFIPXVFZSA-N 0.000 claims 1
- LAUOYVFATJLYDU-NRFANRHFSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-1-(1,3-thiazol-2-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=NC=CS1 LAUOYVFATJLYDU-NRFANRHFSA-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
- HAZOBLNDKHJLFM-DEOSSOPVSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-1-(pyridin-3-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=CN=C1 HAZOBLNDKHJLFM-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
- VYJWGFAYXAFWTL-AKRCKQFNSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-1-(pyrrolidin-2-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)CCN1CC1CCCN1 VYJWGFAYXAFWTL-AKRCKQFNSA-N 0.000 claims 1
- SRHWQOQEIYHHDU-VWLOTQADSA-N (5s)-n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-7-methyl-n-(2-methyltetrazol-5-yl)-1-[[4-(2h-tetrazol-5-yl)phenyl]methyl]-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(C=C1)=CC=C1C1=NN=NN1 SRHWQOQEIYHHDU-VWLOTQADSA-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
- YPCQNWDNTQVBNF-NRFANRHFSA-N 2-[(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-benzazepin-1-yl]ethanol Chemical compound N1=NN(CCN)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 YPCQNWDNTQVBNF-NRFANRHFSA-N 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
- UZVFPEBKIURQPH-NRFANRHFSA-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]ethanol Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(CCO)CCC1)C(F)(F)F)CC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UZVFPEBKIURQPH-NRFANRHFSA-N 0.000 claims 1
- OJHQTXXFFZAHEI-IBGZPJMESA-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]acetic acid Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(CC(O)=O)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OJHQTXXFFZAHEI-IBGZPJMESA-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
- 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
- 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
- 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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 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
- WIJMQWOWSQFTBB-NRFANRHFSA-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]butanoic acid Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(CCCC(O)=O)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WIJMQWOWSQFTBB-NRFANRHFSA-N 0.000 claims 1
- YEENIBAWVGXMGC-SANMLTNESA-N 4-[[(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]methyl]benzoic acid Chemical compound C([C@@H](C=1C=C(C(=CC=11)C(F)(F)F)CC)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 YEENIBAWVGXMGC-SANMLTNESA-N 0.000 claims 1
- YFUPRQYCJVAJKB-SANMLTNESA-N 5-[(5s)-5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-2,3,4,5,7,8,9,10-octahydrobenzo[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=4CCCCC=4C=C3N(CCC(C)(C)CC(O)=O)CCC2)=N1 YFUPRQYCJVAJKB-SANMLTNESA-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
- FSFOGTPFHDZVDY-QHCPKHFHSA-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]-3,3-dimethylpentanoic acid Chemical compound N1=NN(C)N=C1N([C@@H]1C=2C=C(C(=CC=2N(CCC(C)(C)CC(O)=O)CCC1)C(F)(F)F)C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FSFOGTPFHDZVDY-QHCPKHFHSA-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
- ZDKDDGYIIGDYRT-QHCPKHFHSA-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]methyl]thiophene-2-carboxylic 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(CC=3SC(=CC=3)C(O)=O)CCC2)=N1 ZDKDDGYIIGDYRT-QHCPKHFHSA-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
- BWDIHHDYBZAECJ-UHFFFAOYSA-N 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-carboxylic acid Chemical compound FC(C=1C=C(CN(C2C3=C(N(CCC2)C(=O)O)C=C2CCCCC2=C3)C=2N=NN(N=2)C)C=C(C=1)C(F)(F)F)(F)F BWDIHHDYBZAECJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 235000019439 ethyl acetate Nutrition 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 230000001575 pathological effect Effects 0.000 claims 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 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
- 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
- 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
- XTMYYLBYBDPRGG-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]-9-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(C(F)(F)F)C(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 XTMYYLBYBDPRGG-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
- 239000000126 substance Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
-
- 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
- C07D401/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- 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
- C07D405/14—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 three or more hetero rings
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- 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
- C07D413/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58270804P | 2004-06-24 | 2004-06-24 | |
| US62724104P | 2004-11-12 | 2004-11-12 | |
| US66486205P | 2005-03-24 | 2005-03-24 | |
| PCT/US2005/022389 WO2006002342A1 (en) | 2004-06-24 | 2005-06-23 | Compounds and methods for treating dyslipidemia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110761T1 true HRP20110761T1 (hr) | 2011-11-30 |
Family
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| HR20110761T HRP20110761T1 (hr) | 2004-06-24 | 2011-10-19 | Spojevi za liječenje dislipidemije i njihova upotreba |
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| EP (3) | EP1761521A1 (es) |
| JP (2) | JP2008504266A (es) |
| KR (1) | KR20070041452A (es) |
| CN (1) | CN1972932B (es) |
| AT (1) | ATE528304T1 (es) |
| AU (2) | AU2005267436A1 (es) |
| BR (2) | BRPI0512523A (es) |
| CA (2) | CA2570688A1 (es) |
| CR (1) | CR8831A (es) |
| CY (1) | CY1112124T1 (es) |
| DK (1) | DK1761522T3 (es) |
| EA (2) | EA200700119A1 (es) |
| EC (2) | ECSP067098A (es) |
| ES (1) | ES2372291T3 (es) |
| HK (1) | HK1104528A1 (es) |
| HR (1) | HRP20110761T1 (es) |
| IL (2) | IL180276A0 (es) |
| MA (2) | MA28729B1 (es) |
| MX (2) | MXPA06014716A (es) |
| NO (2) | NO20070470L (es) |
| NZ (1) | NZ550978A (es) |
| PL (1) | PL1761522T3 (es) |
| PT (1) | PT1761522E (es) |
| RS (1) | RS52064B (es) |
| SI (1) | SI1761522T1 (es) |
| WO (2) | WO2006012093A1 (es) |
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| MXPA06003927A (es) * | 2003-10-08 | 2008-02-07 | Lilly Co Eli | Compuestos y metodos para tratar dislipidemia. |
| DK1732933T3 (da) | 2004-03-26 | 2008-10-27 | Lilly Co Eli | Forobindelser til behandling af dyslipidæmi |
| UA90269C2 (ru) | 2004-04-02 | 2010-04-26 | Мицубиси Танабе Фарма Корпорейшн | Тетрагидрохинолиновые производные и способ их получения |
| JP2008504266A (ja) | 2004-06-24 | 2008-02-14 | イーライ リリー アンド カンパニー | 異脂肪血症を治療するための化合物及び方法 |
| WO2007107843A1 (en) * | 2006-03-22 | 2007-09-27 | Pfizer Products Inc. | Methods of treatment with cetp inhibitors |
| UY30244A1 (es) | 2006-03-30 | 2007-11-30 | Tanabe Seiyaku Co | Un proceso para preparar derivados de tetrahidroquinolina |
| WO2008017381A1 (de) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituierte imidazolidin-2,4-dione, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
| DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP2157190B1 (en) | 2007-05-17 | 2017-05-03 | EA Pharma Co., Ltd. | Method of measuring the activity of lipid-modified enzyme |
| 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 |
| EP2310372B1 (en) | 2008-07-09 | 2012-05-23 | Sanofi | 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 |
| AR077208A1 (es) * | 2009-06-30 | 2011-08-10 | Lilly Co Eli | Derivados del acido trans-4-[[(5s)-5-[[[3,5-bis(trifluorometil) fenil] metil] (2-metil-2h-tetrazol-5-il) amino) -2,3,4,5-tetrahidro-7,9-dimetil-1h-1-benzazepin-1-il) metil)-ciclohexancarboxilico y sus formas cristalinas, composiciones farmaceuticas que los comprenden, su uso para preparar un medicam |
| EP2470552B1 (en) | 2009-08-26 | 2013-11-13 | Sanofi | Novel crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2012120057A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives 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 |
| US8846666B2 (en) | 2011-03-08 | 2014-09-30 | Sanofi | Oxathiazine derivatives which are substituted with benzyl or heteromethylene groups, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| AU2012282109B2 (en) * | 2011-07-08 | 2016-06-23 | Novartis Ag | Method of treating atherosclerosis in high triglyceride subjects |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| DK2860175T3 (da) | 2012-06-11 | 2018-01-29 | Tacurion | Fremgangsmåde til fremstilling af 4,4,7-trifluor-1,2,3,4-tetrahydro-5h-1-benzazepin-forbindelse og intermediat til syntese deraf |
| CN103958501B (zh) * | 2012-07-16 | 2016-08-17 | 上海恒瑞医药有限公司 | 苯并七元杂环类衍生物、其制备方法及其在医药上的应用 |
| WO2015119495A1 (en) * | 2014-02-05 | 2015-08-13 | Dezima Pharma B.V. | Cholesteryl ester transfer protein (cetp) inhibitor and pharmaceutical compositions comprising said inhibitor for use in the treatment or prevention of cardiovascular diseases |
| CN103833637B (zh) * | 2014-03-31 | 2016-01-06 | 武汉武药制药有限公司 | 一种制备依塞曲匹（Evacetrapib）中间体的方法 |
| TWI726888B (zh) | 2015-06-09 | 2021-05-11 | 美商艾伯維有限公司 | 核受體調節劑 |
| WO2016198908A1 (en) | 2015-06-09 | 2016-12-15 | Abbvie Inc. | Ror nuclear receptor modulators |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2402506A1 (fr) * | 1977-09-09 | 1979-04-06 | Guelennec Emile Le | Cisaille pour la decoupe de ferrailles de grandes dimensions |
| US6147089A (en) * | 1998-09-17 | 2000-11-14 | Pfizer Inc. | Annulated 4-carboxyamino-2-methyl-1,2,3,4,-tetrahydroquinolines |
| US6197786B1 (en) * | 1998-09-17 | 2001-03-06 | Pfizer Inc | 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines |
| GT199900147A (es) * | 1998-09-17 | 1999-09-06 | 1, 2, 3, 4- tetrahidroquinolinas 2-sustituidas 4-amino sustituidas. | |
| CO5271716A1 (es) * | 1999-11-30 | 2003-04-30 | Pfizer Prod Inc | Cristales de 4- carboxamino 1,2,3,4-tetrahidroquinolina 2- sustituida |
| HN2000000203A (es) * | 1999-11-30 | 2001-06-13 | Pfizer Prod Inc | Procedimiento para la obtencion de 1,2,3,4-tetrahidroquinolinas 4-carboxiamino-2- sustituidas. |
| HU225777B1 (en) * | 2001-04-30 | 2007-08-28 | Pfizer Prod Inc | Compounds useful as intermediates for 4-aminoquinoline derivatwes and process for producing them |
| BR0306208A (pt) | 2002-08-30 | 2004-10-13 | Japan Tobacco Inc | Compostos de dibenzilamina e seu uso farmacêutico |
| JP2006508077A (ja) | 2002-10-04 | 2006-03-09 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 炎症疾患を治療するためのｐｇｄ２レセプタアンタゴニスト |
| EP1601655A2 (en) | 2003-03-04 | 2005-12-07 | Takasago International Corporation | Method for producing optically active amines |
| US20040204450A1 (en) * | 2003-03-28 | 2004-10-14 | Pfizer Inc | Quinoline and quinoxaline compounds |
| MXPA06003927A (es) | 2003-10-08 | 2008-02-07 | Lilly Co Eli | Compuestos y metodos para tratar dislipidemia. |
| DK1732933T3 (da) | 2004-03-26 | 2008-10-27 | Lilly Co Eli | Forobindelser til behandling af dyslipidæmi |
| UA90269C2 (ru) * | 2004-04-02 | 2010-04-26 | Мицубиси Танабе Фарма Корпорейшн | Тетрагидрохинолиновые производные и способ их получения |
| JP2008504266A (ja) | 2004-06-24 | 2008-02-14 | イーライ リリー アンド カンパニー | 異脂肪血症を治療するための化合物及び方法 |
| US7700774B2 (en) | 2004-12-20 | 2010-04-20 | Dr. Reddy's Laboratories Ltd. | Heterocyclic compounds and their pharmaceutical compositions |
| AR077208A1 (es) * | 2009-06-30 | 2011-08-10 | Lilly Co Eli | Derivados del acido trans-4-[[(5s)-5-[[[3,5-bis(trifluorometil) fenil] metil] (2-metil-2h-tetrazol-5-il) amino) -2,3,4,5-tetrahidro-7,9-dimetil-1h-1-benzazepin-1-il) metil)-ciclohexancarboxilico y sus formas cristalinas, composiciones farmaceuticas que los comprenden, su uso para preparar un medicam |
-
2005
- 2005-06-22 JP JP2007518182A patent/JP2008504266A/ja active Pending
- 2005-06-22 AU AU2005267436A patent/AU2005267436A1/en not_active Abandoned
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- 2005-06-22 MX MXPA06014716A patent/MXPA06014716A/es not_active Application Discontinuation
- 2005-06-22 EP EP05768995A patent/EP1761521A1/en not_active Withdrawn
- 2005-06-22 CA CA002570688A patent/CA2570688A1/en not_active Abandoned
- 2005-06-22 US US11/570,540 patent/US20080269284A1/en not_active Abandoned
- 2005-06-22 WO PCT/US2005/021789 patent/WO2006012093A1/en active Application Filing
- 2005-06-22 KR KR1020067027038A patent/KR20070041452A/ko not_active Application Discontinuation
- 2005-06-22 EA EA200700119A patent/EA200700119A1/ru unknown
- 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
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- 2005-06-23 CA CA2570673A patent/CA2570673C/en not_active Expired - Fee Related
- 2005-06-23 AU AU2005258241A patent/AU2005258241B2/en not_active Ceased
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- 2005-06-23 CN CN2005800206855A patent/CN1972932B/zh not_active Expired - Fee Related
- 2005-06-23 BR BRPI0512516-2A patent/BRPI0512516A/pt active Search and Examination
- 2005-06-23 PL PL05763328T patent/PL1761522T3/pl unknown
- 2005-06-23 EP EP05763328A patent/EP1761522B1/en active Active
- 2005-06-23 PT PT05763328T patent/PT1761522E/pt unknown
- 2005-06-23 AT AT05763328T patent/ATE528304T1/de active
- 2005-06-23 EA EA200700120A patent/EA012585B1/ru not_active IP Right Cessation
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- 2005-06-23 EP EP11184746A patent/EP2479175A1/en not_active Withdrawn
- 2005-06-23 RS RS20110559A patent/RS52064B/en unknown
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2006
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- 2006-12-19 EC EC2006007095A patent/ECSP067095A/es unknown
- 2006-12-22 CR CR8831A patent/CR8831A/es unknown
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- 2006-12-29 MA MA29595A patent/MA28729B1/fr unknown
- 2006-12-29 MA MA29596A patent/MA28730B1/fr unknown
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2007
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2010
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2011
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- 2011-11-25 CY CY20111101160T patent/CY1112124T1/el unknown
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