JP2008520645A - ジベンジルアミン化合物および誘導体 - Google Patents

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Publication number

JP2008520645A

JP2008520645A JP2007542159A JP2007542159A JP2008520645A JP 2008520645 A JP2008520645 A JP 2008520645A JP 2007542159 A JP2007542159 A JP 2007542159A JP 2007542159 A JP2007542159 A JP 2007542159A JP 2008520645 A JP2008520645 A JP 2008520645A

Authority

JP

Japan

Prior art keywords

alkyl

methyl

trifluoromethyl

prepared

benzyl

Prior art date

2004-11-23

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.)

Withdrawn

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• BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical class C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 373
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 20
• 241000124008 Mammalia Species 0.000 claims abstract description 19
• 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 18
• 201000010099 disease Diseases 0.000 claims abstract description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 110
• 239000000203 mixture Substances 0.000 claims description 104
• -1 Of B Chemical group 0.000 claims description 75
• 239000003112 inhibitor Substances 0.000 claims description 75
• 238000000034 method Methods 0.000 claims description 75
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 65
• 125000005843 halogen group Chemical group 0.000 claims description 63
• 229910052739 hydrogen Inorganic materials 0.000 claims description 55
• 239000001257 hydrogen Substances 0.000 claims description 53
• 150000003839 salts Chemical class 0.000 claims description 43
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 39
• 229940002612 prodrug Drugs 0.000 claims description 32
• 239000000651 prodrug Substances 0.000 claims description 32
• 150000002431 hydrogen Chemical class 0.000 claims description 29
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 229920001577 copolymer Chemical group 0.000 claims description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 208000029078 coronary artery disease Diseases 0.000 claims description 20
• 125000004043 oxo group Chemical group O=* 0.000 claims description 20
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 19
• 239000011664 nicotinic acid Substances 0.000 claims description 19
• 235000001968 nicotinic acid Nutrition 0.000 claims description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 238000011282 treatment Methods 0.000 claims description 18
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 17
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 17
• 229960003512 nicotinic acid Drugs 0.000 claims description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 235000019000 fluorine Nutrition 0.000 claims description 13
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 102000018616 Apolipoproteins B Human genes 0.000 claims description 9
• 108010027006 Apolipoproteins B Proteins 0.000 claims description 9
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 9
• 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 230000028327 secretion Effects 0.000 claims description 9
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims description 7
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 7
• 201000001386 familial hypercholesterolemia Diseases 0.000 claims description 7
• 229960004844 lovastatin Drugs 0.000 claims description 7
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 7
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 7
• XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 6
• XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 6
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 6
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 6
• 229960000528 amlodipine Drugs 0.000 claims description 6
• 229960005370 atorvastatin Drugs 0.000 claims description 6
• 229940125753 fibrate Drugs 0.000 claims description 6
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 5
• YVPOVOVZCOOSBQ-AXHZAXLDSA-N [(1s,3r,7s,8s,8ar)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2s)-2-methylbutanoate;pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1.C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 YVPOVOVZCOOSBQ-AXHZAXLDSA-N 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 239000003963 antioxidant agent Substances 0.000 claims description 5
• 239000003613 bile acid Substances 0.000 claims description 5
• GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 208000010125 myocardial infarction Diseases 0.000 claims description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims description 5
• 229960000672 rosuvastatin Drugs 0.000 claims description 5
• 229960002855 simvastatin Drugs 0.000 claims description 5
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 5
• 239000012730 sustained-release form Substances 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
• 125000001425 triazolyl group Chemical group 0.000 claims description 5
• ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 4
• HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 claims description 4
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 4
• 206010021024 Hypolipidaemia Diseases 0.000 claims description 4
• 102100024640 Low-density lipoprotein receptor Human genes 0.000 claims description 4
• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims description 4
• 206010045261 Type IIa hyperlipidaemia Diseases 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 claims description 4
• 229960003765 fluvastatin Drugs 0.000 claims description 4
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 4
• 208000029498 hypoalphalipoproteinemia Diseases 0.000 claims description 4
• 239000003456 ion exchange resin Substances 0.000 claims description 4
• 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
• 229960002797 pitavastatin Drugs 0.000 claims description 4
• VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 claims description 4
• 229960002965 pravastatin Drugs 0.000 claims description 4
• TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims description 4
• SRDCONKRNRXDFD-UHFFFAOYSA-N 3-[2-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]methyl]-4-(trifluoromethyl)phenyl]-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1C1=CC=C(C(F)(F)F)C=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SRDCONKRNRXDFD-UHFFFAOYSA-N 0.000 claims description 3
• 229940123239 Cholesterol synthesis inhibitor Drugs 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 230000003078 antioxidant effect Effects 0.000 claims description 3
• GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 claims description 3
• 229960002297 fenofibrate Drugs 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 229960003627 gemfibrozil Drugs 0.000 claims description 3
• ATLNMVNKNWYFGL-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(2-methoxy-5-propan-2-ylphenyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound COC1=CC=C(C(C)C)C=C1C1=CC=CC=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ATLNMVNKNWYFGL-UHFFFAOYSA-N 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 239000003352 sequestering agent Substances 0.000 claims description 3
• 238000013268 sustained release Methods 0.000 claims description 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
• TXLPBBOMUYSABG-UHFFFAOYSA-N 1-[3-[2-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]methyl]-4-(trifluoromethyl)phenyl]-4-fluorophenyl]ethanone Chemical compound CC(=O)C1=CC=C(F)C(C=2C(=CC(=CC=2)C(F)(F)F)CN(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)=C1 TXLPBBOMUYSABG-UHFFFAOYSA-N 0.000 claims description 2
• OBZBVYOIXKKXKG-UHFFFAOYSA-N 2-[3-[2-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]methyl]-4-(trifluoromethyl)phenyl]-4-methoxyphenyl]acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1C1=CC=C(C(F)(F)F)C=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OBZBVYOIXKKXKG-UHFFFAOYSA-N 0.000 claims description 2
• QJKUHJVDVWDZLK-UHFFFAOYSA-N 3-[2-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]methyl]-4-(trifluoromethyl)phenyl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1C1=CC=C(C(F)(F)F)C=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QJKUHJVDVWDZLK-UHFFFAOYSA-N 0.000 claims description 2
• HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims description 2
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 2
• KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims description 2
• RXCHLDAWZXXJNK-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-methyl-n-[[2-(2-methylsulfanylphenyl)-5-(trifluoromethyl)phenyl]methyl]tetrazol-5-amine Chemical compound CSC1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RXCHLDAWZXXJNK-UHFFFAOYSA-N 0.000 claims description 2
• GFDBIYSJOFAHLA-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-methyl-n-[[2-[2-(trifluoromethoxy)phenyl]-5-(trifluoromethyl)phenyl]methyl]tetrazol-5-amine Chemical compound CN1N=NC(N(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC=2C(=CC=C(C=2)C(F)(F)F)C=2C(=CC=CC=2)OC(F)(F)F)=N1 GFDBIYSJOFAHLA-UHFFFAOYSA-N 0.000 claims description 2
• ZUVZOHUYPUWISX-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(2,5-dimethoxyphenyl)-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound COC1=CC=C(OC)C(C=2C(=CC(=CC=2)C(F)(F)F)CN(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)=C1 ZUVZOHUYPUWISX-UHFFFAOYSA-N 0.000 claims description 2
• OQQFIWZXDDWJDC-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(2-chloro-5-methylphenyl)-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound CC1=CC=C(Cl)C(C=2C(=CC(=CC=2)C(F)(F)F)CN(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)=C1 OQQFIWZXDDWJDC-UHFFFAOYSA-N 0.000 claims description 2
• SDJVFZVIUOEKTL-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(2-fluoro-5-methylphenyl)-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound CC1=CC=C(F)C(C=2C(=CC(=CC=2)C(F)(F)F)CN(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)=C1 SDJVFZVIUOEKTL-UHFFFAOYSA-N 0.000 claims description 2
• NYAKIFLJDVZGMQ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(2-methoxy-5-methylphenyl)-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound COC1=CC=C(C)C=C1C1=CC=C(C(F)(F)F)C=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NYAKIFLJDVZGMQ-UHFFFAOYSA-N 0.000 claims description 2
• QXLUAMIFPVGZSR-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(2-methoxy-5-propan-2-ylphenyl)-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound COC1=CC=C(C(C)C)C=C1C1=CC=C(C(F)(F)F)C=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QXLUAMIFPVGZSR-UHFFFAOYSA-N 0.000 claims description 2
• XHNVBOHJDKMNOH-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(5-fluoro-2-methoxyphenyl)-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound COC1=CC=C(F)C=C1C1=CC=C(C(F)(F)F)C=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XHNVBOHJDKMNOH-UHFFFAOYSA-N 0.000 claims description 2
• WIAKUCPQRWZJAB-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-[2-methoxy-5-[(4-methylpiperazin-1-yl)methyl]phenyl]-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound C1=C(C=2C(=CC(=CC=2)C(F)(F)F)CN(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)C(OC)=CC=C1CN1CCN(C)CC1 WIAKUCPQRWZJAB-UHFFFAOYSA-N 0.000 claims description 2
• VERZDMLBNATJKG-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-[5-[(dimethylamino)methyl]-2-methoxyphenyl]-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound COC1=CC=C(CN(C)C)C=C1C1=CC=C(C(F)(F)F)C=C1CN(C1=NN(C)N=N1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VERZDMLBNATJKG-UHFFFAOYSA-N 0.000 claims description 2
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 2
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 2
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