JP2008520645A5 - - Google Patents
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- Publication number
- JP2008520645A5 JP2008520645A5 JP2007542159A JP2007542159A JP2008520645A5 JP 2008520645 A5 JP2008520645 A5 JP 2008520645A5 JP 2007542159 A JP2007542159 A JP 2007542159A JP 2007542159 A JP2007542159 A JP 2007542159A JP 2008520645 A5 JP2008520645 A5 JP 2008520645A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- trifluoromethyl
- alkoxy
- halo
- 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.)
- Withdrawn
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- 125000000217 alkyl group Chemical group 0.000 claims 48
- 125000005843 halogen group Chemical group 0.000 claims 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 17
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 229920001577 copolymer Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- -1 Of B Chemical group 0.000 claims 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 235000019000 fluorine Nutrition 0.000 claims 5
- 229960003512 nicotinic acid Drugs 0.000 claims 5
- 239000011664 nicotinic acid Substances 0.000 claims 5
- 235000001968 nicotinic acid Nutrition 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 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 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 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 3
- 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 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 229960005370 atorvastatin Drugs 0.000 claims 3
- 208000029078 coronary artery disease Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 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 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 2
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 2
- 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 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 239000003613 bile acid Substances 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 229960002855 simvastatin Drugs 0.000 claims 2
- 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 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 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 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 102000018616 Apolipoproteins B Human genes 0.000 claims 1
- 108010027006 Apolipoproteins B Proteins 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims 1
- 229940123239 Cholesterol synthesis inhibitor Drugs 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 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 1
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 1
- 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 1
- 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 1
- 229960000528 amlodipine Drugs 0.000 claims 1
- 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 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 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 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 229960002297 fenofibrate Drugs 0.000 claims 1
- 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 1
- 229940125753 fibrate Drugs 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229960003765 fluvastatin Drugs 0.000 claims 1
- 229960003627 gemfibrozil Drugs 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 229960004844 lovastatin Drugs 0.000 claims 1
- 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 1
- 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 1
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229960002797 pitavastatin Drugs 0.000 claims 1
- 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 1
- 229960002965 pravastatin Drugs 0.000 claims 1
- 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 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229960000672 rosuvastatin Drugs 0.000 claims 1
- 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 1
- 230000028327 secretion Effects 0.000 claims 1
- 239000003352 sequestering agent Substances 0.000 claims 1
- 238000013268 sustained release Methods 0.000 claims 1
- 239000012730 sustained-release form Substances 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63043404P | 2004-11-23 | 2004-11-23 | |
| US71561705P | 2005-09-12 | 2005-09-12 | |
| PCT/IB2005/003500 WO2006056854A1 (en) | 2004-11-23 | 2005-11-21 | Dibenzyl amine compounds and derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008520645A JP2008520645A (ja) | 2008-06-19 |
| JP2008520645A5 true JP2008520645A5 (enExample) | 2009-01-15 |
Family
ID=35828305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007542159A Withdrawn JP2008520645A (ja) | 2004-11-23 | 2005-11-21 | ジベンジルアミン化合物および誘導体 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US20090239865A1 (enExample) |
| EP (1) | EP1817297A1 (enExample) |
| JP (1) | JP2008520645A (enExample) |
| KR (1) | KR20070069213A (enExample) |
| AP (1) | AP2007003980A0 (enExample) |
| AR (1) | AR053784A1 (enExample) |
| AU (1) | AU2005308584A1 (enExample) |
| BR (1) | BRPI0518476A2 (enExample) |
| CA (1) | CA2589322A1 (enExample) |
| CR (1) | CR9089A (enExample) |
| EA (1) | EA200700924A1 (enExample) |
| GT (1) | GT200500339A (enExample) |
| IL (1) | IL183133A0 (enExample) |
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| US8604055B2 (en) | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| WO2007075194A1 (en) * | 2005-12-28 | 2007-07-05 | Reddy Us Therapeutics, Inc. | Selective benzylamine derivatives and their utility as cholesterol ester-transfer protein inhibitors |
| US9040558B2 (en) | 2004-12-31 | 2015-05-26 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| WO2007041494A2 (en) * | 2005-09-30 | 2007-04-12 | Merck & Co., Inc. | Cholesteryl ester transfer protein inhibitors |
| CA2634833A1 (en) * | 2005-12-29 | 2007-07-05 | Novartis Ag | Pyridinyl amine derivatives as inhibitors of cholesteryl ester transfer protein (cetp) |
| UY30117A1 (es) * | 2006-01-31 | 2007-06-29 | Tanabe Seiyaku Co | Compuesto amina trisustituido |
| PE20071025A1 (es) * | 2006-01-31 | 2007-10-17 | Mitsubishi Tanabe Pharma Corp | Compuesto amina trisustituido |
| US7919506B2 (en) | 2006-03-10 | 2011-04-05 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| US8383660B2 (en) * | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| AR060873A1 (es) | 2006-05-10 | 2008-07-16 | Novartis Ag | Derivados biciclicos como inhibidores de cetp |
| CA2650515A1 (en) * | 2006-05-11 | 2007-11-22 | Novartis Ag | Benzylamine derivatives as cetp inhibitors |
| US7750019B2 (en) | 2006-08-11 | 2010-07-06 | Kowa Company, Ltd. | Pyrimidine compound having benzyl(pyridylmethyl)amine structure and medicament comprising the same |
| US7790737B2 (en) | 2007-03-13 | 2010-09-07 | Kowa Company, Ltd. | Substituted pyrimidine compounds and their utility as CETP inhibitors |
| CN101679309B (zh) * | 2007-04-13 | 2012-02-29 | 兴和株式会社 | 具有二苄胺结构的新型嘧啶化合物和含有该化合物的药物 |
| JP4834699B2 (ja) * | 2007-07-30 | 2011-12-14 | 田辺三菱製薬株式会社 | 医薬組成物 |
| JP4846769B2 (ja) * | 2007-07-30 | 2011-12-28 | 田辺三菱製薬株式会社 | 医薬組成物 |
| EP2222638A2 (en) * | 2007-11-21 | 2010-09-01 | Decode Genetics EHF | Biaryl pde4 inhibitors for treating inflammation |
| EP2222639A1 (en) * | 2007-11-21 | 2010-09-01 | Decode Genetics EHF | Biaryl pde4 inhibitors for treating pulmonary and cardiovascular disorders |
| ES2566739T3 (es) * | 2008-02-01 | 2016-04-15 | Brickell Biotech, Inc. | Aminoalquilbifenilo N,N-disustituidos antagonistas de receptores de prostaglandina D2 |
| EP2245002A4 (en) * | 2008-02-01 | 2011-08-17 | Amira Pharmaceuticals Inc | AMINOALKYLBIPHENYL ANTAGONISTS N, N 'DISUBSTITUTED FROM D2 RECEPTORS OF PROSTAGLANDIN |
| JP2011512359A (ja) | 2008-02-14 | 2011-04-21 | アミラ ファーマシューティカルズ，インク． | プロスタグランジンｄ２受容体のアンタゴニストとしての環式ジアリールエーテル化合物 |
| WO2009108720A2 (en) | 2008-02-25 | 2009-09-03 | Amira Pharmaceuticals, Inc. | Antagonists of prostaglandin d2 receptors |
| JP2011518130A (ja) | 2008-04-02 | 2011-06-23 | アミラ ファーマシューティカルズ，インク． | プロスタグランジンｄ２受容体のアミノアルキルフェニルアンタゴニスト |
| GB2463788B (en) | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
| WO2010039977A2 (en) * | 2008-10-01 | 2010-04-08 | Amira Pharmaceuticals, Inc. | Heteroaryl antagonists of prostaglandin d2 receptors |
| US8524748B2 (en) | 2008-10-08 | 2013-09-03 | Panmira Pharmaceuticals, Llc | Heteroalkyl biphenyl antagonists of prostaglandin D2 receptors |
| US8383654B2 (en) | 2008-11-17 | 2013-02-26 | Panmira Pharmaceuticals, Llc | Heterocyclic antagonists of prostaglandin D2 receptors |
| WO2010059838A2 (en) * | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Pde4 inhibitors selective for the long form of pde4 for treating inflammation and avoiding side effects |
| CA2768587A1 (en) | 2009-08-05 | 2011-02-10 | Panmira Pharmaceuticals, Llc | Dp2 antagonist and uses thereof |
| PH12012501349A1 (en) | 2010-01-06 | 2013-01-14 | Panmira Pharmaceuticals Llc | Dp2 antagonist and uses thereof |
| JP2013538215A (ja) | 2010-08-31 | 2013-10-10 | エスエヌユー アールアンドディービー ファウンデーション | ＰＰＡＲδアゴニストの胎児再プログラミング用途 |
| US9867811B2 (en) * | 2011-07-08 | 2018-01-16 | Novartis Ag | Method of treating atherosclerosis in high triglyceride subjects |
| US9199967B2 (en) | 2011-08-18 | 2015-12-01 | Dr. Reddy's Laboratories Ltd. | Substituted heterocyclic amine compounds as cholestryl ester-transfer protein (CETP) inhibitors |
| IN2014CN02290A (enExample) | 2011-09-27 | 2015-06-19 | Reddys Lab Ltd Dr | |
| US9717714B2 (en) | 2012-12-19 | 2017-08-01 | Merck Sharp & Dohme Corp. | Spirocyclic CETP inhibitors |
| PT3762368T (pt) | 2018-03-08 | 2022-05-06 | Incyte Corp | Compostos de aminopirazina diol como inibidores de pi3k-y |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| CN115677572B (zh) * | 2021-07-29 | 2024-05-28 | 武汉思瓴生物科技有限公司 | 氟代酰胺类衍生物、药物组合物及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2438551A1 (en) * | 2001-02-15 | 2002-08-22 | Pfizer Products Inc. | Ppar agonists |
| JP2003221376A (ja) * | 2001-11-21 | 2003-08-05 | Japan Tobacco Inc | Ｃｅｔｐ活性阻害剤 |
| US6653334B1 (en) * | 2002-12-27 | 2003-11-25 | Kowa Co., Ltd. | Benzoxazole compound and pharmaceutical composition containing the same |
| CA2562082C (en) * | 2004-04-13 | 2013-06-25 | Merck & Co., Inc. | Cetp inhibitors for the treatment and prevention of atherosclerosis |
-
2005
- 2005-11-21 AP AP2007003980A patent/AP2007003980A0/xx unknown
- 2005-11-21 WO PCT/IB2005/003500 patent/WO2006056854A1/en not_active Ceased
- 2005-11-21 AU AU2005308584A patent/AU2005308584A1/en not_active Abandoned
- 2005-11-21 CA CA002589322A patent/CA2589322A1/en not_active Abandoned
- 2005-11-21 PE PE2005001363A patent/PE20061124A1/es not_active Application Discontinuation
- 2005-11-21 MX MX2007006137A patent/MX2007006137A/es unknown
- 2005-11-21 KR KR1020077011611A patent/KR20070069213A/ko not_active Ceased
- 2005-11-21 AR ARP050104864A patent/AR053784A1/es unknown
- 2005-11-21 JP JP2007542159A patent/JP2008520645A/ja not_active Withdrawn
- 2005-11-21 EA EA200700924A patent/EA200700924A1/ru unknown
- 2005-11-21 BR BRPI0518476-2A patent/BRPI0518476A2/pt not_active Application Discontinuation
- 2005-11-21 US US11/719,885 patent/US20090239865A1/en not_active Abandoned
- 2005-11-21 EP EP05805656A patent/EP1817297A1/en not_active Withdrawn
- 2005-11-21 TW TW094140833A patent/TW200630350A/zh unknown
- 2005-11-22 UY UY29222A patent/UY29222A1/es not_active Application Discontinuation
- 2005-11-22 NL NL1030486A patent/NL1030486C2/nl not_active IP Right Cessation
- 2005-11-23 GT GT200500339A patent/GT200500339A/es unknown
-
2007
- 2007-04-30 CR CR9089A patent/CR9089A/es not_active Application Discontinuation
- 2007-05-10 IL IL183133A patent/IL183133A0/en unknown
- 2007-05-22 TN TNP2007000200A patent/TNSN07200A1/fr unknown
- 2007-05-23 MA MA29936A patent/MA29039B1/fr unknown
- 2007-06-13 NO NO20073025A patent/NO20073025L/no not_active Application Discontinuation
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