CA2589322A1 - Dibenzyl amine compounds and derivatives - Google Patents
Dibenzyl amine compounds and derivatives Download PDFInfo
- Publication number
- CA2589322A1 CA2589322A1 CA002589322A CA2589322A CA2589322A1 CA 2589322 A1 CA2589322 A1 CA 2589322A1 CA 002589322 A CA002589322 A CA 002589322A CA 2589322 A CA2589322 A CA 2589322A CA 2589322 A1 CA2589322 A1 CA 2589322A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- methyl
- trifluoromethyl
- benzyl
- 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.)
- Abandoned
Links
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical class C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 441
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 20
- 241000124008 Mammalia Species 0.000 claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 196
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 106
- -1 cyano, hydroxy Chemical group 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 103
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 76
- 239000003112 inhibitor Substances 0.000 claims description 74
- 125000005843 halogen group Chemical group 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 229940002612 prodrug Drugs 0.000 claims description 32
- 239000000651 prodrug Substances 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 20
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 18
- 208000029078 coronary artery disease Diseases 0.000 claims description 18
- 235000001968 nicotinic acid Nutrition 0.000 claims description 18
- 239000011664 nicotinic acid Substances 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
- 125000004043 oxo group Chemical group O=* 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 229960003512 nicotinic acid Drugs 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 239000003981 vehicle Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 235000019000 fluorine Nutrition 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 230000028327 secretion Effects 0.000 claims description 11
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 10
- 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 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 9
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 201000001386 familial hypercholesterolemia Diseases 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 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
- 229960000528 amlodipine Drugs 0.000 claims description 7
- 239000003085 diluting agent Substances 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
- 206010021024 Hypolipidaemia Diseases 0.000 claims description 6
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 6
- 229960005370 atorvastatin Drugs 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 208000029498 hypoalphalipoproteinemia Diseases 0.000 claims description 6
- 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 6
- 208000035150 Hypercholesterolemia Diseases 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
- 125000003368 amide group Chemical group 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 229920000080 bile acid sequestrant Polymers 0.000 claims description 5
- 229940125753 fibrate Drugs 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 229960000672 rosuvastatin Drugs 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
- 229960002855 simvastatin Drugs 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
- 208000019553 vascular disease Diseases 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 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 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 229940123239 Cholesterol synthesis inhibitor Drugs 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
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 230000003078 antioxidant effect Effects 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
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 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 3
- 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 3
- 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 3
- 239000003613 bile acid Substances 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
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 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 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229960003627 gemfibrozil Drugs 0.000 claims description 2
- JUJVGWUAVZOEFT-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-methyl-n-[[2-(3-propan-2-ylphenyl)-5-(trifluoromethyl)phenyl]methyl]tetrazol-5-amine Chemical compound CC(C)C1=CC=CC(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 JUJVGWUAVZOEFT-UHFFFAOYSA-N 0.000 claims description 2
- MUCHOHIGNBIVJF-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(2-ethoxyphenyl)-5-(trifluoromethyl)phenyl]methyl]-2-methyltetrazol-5-amine Chemical compound CCOC1=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 MUCHOHIGNBIVJF-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
- SLRUUDUAKQXMMV-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-[[2-(2-methoxy-5-propan-2-ylphenyl)-5-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound COC1=CC=C(C(C)C)C=C1C1=CC=C(C(F)(F)F)C=C1CN(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SLRUUDUAKQXMMV-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 32
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 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
- 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
- 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
- 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
- BWLXITQJJPHUSN-UHFFFAOYSA-N 4-[1-[2-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]methyl]-4-(trifluoromethyl)phenyl]propoxy]benzamide Chemical compound C=1C=C(C(F)(F)F)C=C(CN(CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C2=NN(C)N=N2)C=1C(CC)OC1=CC=C(C(N)=O)C=C1 BWLXITQJJPHUSN-UHFFFAOYSA-N 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
- MVZPUCFZKGMLOU-UHFFFAOYSA-N methyl 2-[[3-[2-[[[3,5-bis(trifluoromethyl)phenyl]methyl-(2-methyltetrazol-5-yl)amino]methyl]-4-(trifluoromethyl)phenyl]-4-methoxyphenyl]methyl-methylamino]acetate Chemical compound COC(=O)CN(C)CC1=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 MVZPUCFZKGMLOU-UHFFFAOYSA-N 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
- 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
- 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
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- 229950004678 tripamide Drugs 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 229940054495 univasc Drugs 0.000 description 1
- 239000000777 urocortin Substances 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
- 229940099270 vasotec Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 229940055010 verelan Drugs 0.000 description 1
- 229960002726 vincamine Drugs 0.000 description 1
- 229960000744 vinpocetine Drugs 0.000 description 1
- DKRSEIPLAZTSFD-LSDHHAIUSA-N viquidil Chemical compound C12=CC(OC)=CC=C2N=CC=C1C(=O)CC[C@@H]1CCNC[C@@H]1C=C DKRSEIPLAZTSFD-LSDHHAIUSA-N 0.000 description 1
- 229960003353 viquidil Drugs 0.000 description 1
- 229960000821 visnadine Drugs 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229940111503 welchol Drugs 0.000 description 1
- 229940045854 xanthinol niacinate Drugs 0.000 description 1
- RKUQLAPSGZJLGP-UHFFFAOYSA-N xibenolol Chemical compound CC1=CC=CC(OCC(O)CNC(C)(C)C)=C1C RKUQLAPSGZJLGP-UHFFFAOYSA-N 0.000 description 1
- 229950001124 xibenolol Drugs 0.000 description 1
- 229960000537 xipamide Drugs 0.000 description 1
- MTZBBNMLMNBNJL-UHFFFAOYSA-N xipamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1O MTZBBNMLMNBNJL-UHFFFAOYSA-N 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- 229930188494 zaragozic acid Natural products 0.000 description 1
- DFKDOZMCHOGOBR-UHFFFAOYSA-N zaragozic acid A Natural products O1C(C(O)(C(O2)C(O)=O)C(O)=O)(C(O)=O)C(OC(=O)C=CC(C)CC(C)CC)C(O)C21CCC(=C)C(OC(C)=O)C(C)CC1=CC=CC=C1 DFKDOZMCHOGOBR-UHFFFAOYSA-N 0.000 description 1
- 229940051223 zetia Drugs 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- 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
-
- 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
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63043404P | 2004-11-23 | 2004-11-23 | |
| US60/630,434 | 2004-11-23 | ||
| US71561705P | 2005-09-12 | 2005-09-12 | |
| US60/715,617 | 2005-09-12 | ||
| PCT/IB2005/003500 WO2006056854A1 (en) | 2004-11-23 | 2005-11-21 | Dibenzyl amine compounds and derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2589322A1 true CA2589322A1 (en) | 2006-06-01 |
Family
ID=35828305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002589322A Abandoned CA2589322A1 (en) | 2004-11-23 | 2005-11-21 | Dibenzyl amine compounds and derivatives |
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) |
| MA (1) | MA29039B1 (enExample) |
| MX (1) | MX2007006137A (enExample) |
| NL (1) | NL1030486C2 (enExample) |
| NO (1) | NO20073025L (enExample) |
| PE (1) | PE20061124A1 (enExample) |
| TN (1) | TNSN07200A1 (enExample) |
| TW (1) | TW200630350A (enExample) |
| UY (1) | UY29222A1 (enExample) |
| WO (1) | WO2006056854A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8604055B2 (en) | 2004-12-31 | 2013-12-10 | Dr. Reddy's Laboratories Ltd. | Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors |
| JP5096927B2 (ja) | 2004-12-31 | 2012-12-12 | レディ ユーエス セラピューティックス， インコーポレイテッド | Ｃｅｔｐインヒビターとしての新規ベンジルアミン誘導体 |
| WO2007041494A2 (en) * | 2005-09-30 | 2007-04-12 | Merck & Co., Inc. | Cholesteryl ester transfer protein inhibitors |
| CN101448397B (zh) * | 2005-12-28 | 2013-04-24 | 雷迪博士实验室有限公司 | 选择性的苄胺衍生物和其作为胆固醇酯转运蛋白抑制剂的应用 |
| AU2006331032A1 (en) * | 2005-12-29 | 2007-07-05 | Novartis Ag | Pyridinyl amine derivatives as inhibitors of cholesteryl ester transfer protein (CETP) |
| UY30118A1 (es) * | 2006-01-31 | 2007-06-29 | Tanabe Seiyaku Co | Compueto amina trisustituido |
| UY30117A1 (es) * | 2006-01-31 | 2007-06-29 | Tanabe Seiyaku Co | Compuesto amina trisustituido |
| US8383660B2 (en) * | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| US7919506B2 (en) * | 2006-03-10 | 2011-04-05 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| EP2024356A1 (en) | 2006-05-10 | 2009-02-18 | Novartis AG | Bicyclic derivatives as cetp inhibitors |
| WO2007132906A1 (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 |
| DK2149563T3 (en) | 2007-04-13 | 2015-02-02 | Kowa Co | Novel pyrimidine compound with dibenzylaminstruktur, and medicine comprising the compound |
| 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 |
| CA2722582A1 (en) * | 2007-11-21 | 2009-05-28 | Decode Genetics Ehf. | Biaryl pde4 inhibitors for treating inflammation |
| US20090136473A1 (en) | 2007-11-21 | 2009-05-28 | Decode Genetics Ehf | Biaryl pde4 inhibitors for treating pulmonary and cardiovascular disorders |
| US8168678B2 (en) | 2008-02-01 | 2012-05-01 | Panmira Pharmaceuticals, Inc. | N,N-disubstituted aminoalkylbiphenyl antagonists of prostaglandin D2 receptors |
| EP2245002A4 (en) * | 2008-02-01 | 2011-08-17 | Amira Pharmaceuticals Inc | AMINOALKYLBIPHENYL ANTAGONISTS N, N 'DISUBSTITUTED FROM D2 RECEPTORS OF PROSTAGLANDIN |
| EP2257536A4 (en) | 2008-02-14 | 2011-03-23 | Amira Pharmaceuticals Inc | CYCLIC DIARYL ETHERS AS ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS |
| WO2009108720A2 (en) | 2008-02-25 | 2009-09-03 | Amira Pharmaceuticals, Inc. | Antagonists of prostaglandin d2 receptors |
| EP2268611A2 (en) | 2008-04-02 | 2011-01-05 | Amira Pharmaceuticals, Inc. | Aminoalkylphenyl antagonists of prostaglandin d2 receptors |
| 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 |
| WO2010057118A2 (en) | 2008-11-17 | 2010-05-20 | Amira Pharmaceuticals, Inc. | 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 |
| CN102596902A (zh) | 2009-08-05 | 2012-07-18 | 潘米拉制药公司 | Dp2拮抗剂及其用途 |
| CA2782085A1 (en) | 2010-01-06 | 2011-07-14 | Panmira Pharmaceuticals, Llc | Dp2 antagonist and uses thereof |
| KR101898610B1 (ko) | 2010-08-31 | 2018-09-14 | 서울대학교산학협력단 | ＰＰＡＲδ 활성물질의 태자 재프로그래밍 용도 |
| ES2683350T3 (es) * | 2011-07-08 | 2018-09-26 | Novartis Ag | Método para tratar la aterosclerosis en sujetos con alto nivel de triglicéridos |
| JP5964965B2 (ja) * | 2011-08-18 | 2016-08-03 | ドクター レディズ ラボラトリーズ リミテッド | コレステリルエステル転送タンパク質（ｃｅｔｐ）インヒビターとしての置換複素環式アミン化合物 |
| HK1197238A1 (en) | 2011-09-27 | 2015-01-09 | 雷迪博士实验室有限公司 | 5 - benzylaminomethyl - 6 - aminopyrazolo [3, 4 -b] pyridine derivatives as cholesteryl ester -transfer protein (cetp) inhibitors useful for the treatment of atherosclerosis |
| EP2934518B1 (en) | 2012-12-19 | 2020-02-19 | Merck Sharp & Dohme Corp. | Spirocyclic cetp inhibitors |
| RS63124B1 (sr) | 2018-03-08 | 2022-05-31 | Incyte Corp | Aminopirazin diol jedinjenja kao pi3k-y inhibitori |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1360172A1 (en) * | 2001-02-15 | 2003-11-12 | 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 |
| JP4922924B2 (ja) * | 2004-04-13 | 2012-04-25 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｃｅｔｐ阻害薬 |
-
2005
- 2005-11-21 CA CA002589322A patent/CA2589322A1/en not_active Abandoned
- 2005-11-21 BR BRPI0518476-2A patent/BRPI0518476A2/pt 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 AU AU2005308584A patent/AU2005308584A1/en not_active Abandoned
- 2005-11-21 AP AP2007003980A patent/AP2007003980A0/xx unknown
- 2005-11-21 US US11/719,885 patent/US20090239865A1/en not_active Abandoned
- 2005-11-21 EA EA200700924A patent/EA200700924A1/ru unknown
- 2005-11-21 JP JP2007542159A patent/JP2008520645A/ja not_active Withdrawn
- 2005-11-21 AR ARP050104864A patent/AR053784A1/es unknown
- 2005-11-21 PE PE2005001363A patent/PE20061124A1/es not_active Application Discontinuation
- 2005-11-21 TW TW094140833A patent/TW200630350A/zh unknown
- 2005-11-21 EP EP05805656A patent/EP1817297A1/en not_active Withdrawn
- 2005-11-21 WO PCT/IB2005/003500 patent/WO2006056854A1/en not_active Ceased
- 2005-11-22 NL NL1030486A patent/NL1030486C2/nl not_active IP Right Cessation
- 2005-11-22 UY UY29222A patent/UY29222A1/es not_active Application Discontinuation
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008520645A (ja) | 2008-06-19 |
| TW200630350A (en) | 2006-09-01 |
| EP1817297A1 (en) | 2007-08-15 |
| BRPI0518476A2 (pt) | 2008-11-18 |
| NL1030486C2 (nl) | 2006-10-24 |
| WO2006056854A1 (en) | 2006-06-01 |
| UY29222A1 (es) | 2006-06-30 |
| EA200700924A1 (ru) | 2007-10-26 |
| AP2007003980A0 (en) | 2007-06-30 |
| MA29039B1 (fr) | 2007-11-01 |
| KR20070069213A (ko) | 2007-07-02 |
| IL183133A0 (en) | 2007-09-20 |
| NO20073025L (no) | 2007-08-20 |
| TNSN07200A1 (fr) | 2008-11-21 |
| AR053784A1 (es) | 2007-05-23 |
| US20090239865A1 (en) | 2009-09-24 |
| MX2007006137A (es) | 2007-07-19 |
| AU2005308584A1 (en) | 2006-06-01 |
| PE20061124A1 (es) | 2006-10-13 |
| NL1030486A1 (nl) | 2006-05-24 |
| GT200500339A (es) | 2006-06-22 |
| CR9089A (es) | 2007-05-30 |
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