JP5599788B2 - トリアジンおよびウラシルの誘導体、それらの調製、およびヒト治療薬におけるそれらの応用 - Google Patents
トリアジンおよびウラシルの誘導体、それらの調製、およびヒト治療薬におけるそれらの応用 Download PDFInfo
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- JP5599788B2 JP5599788B2 JP2011517863A JP2011517863A JP5599788B2 JP 5599788 B2 JP5599788 B2 JP 5599788B2 JP 2011517863 A JP2011517863 A JP 2011517863A JP 2011517863 A JP2011517863 A JP 2011517863A JP 5599788 B2 JP5599788 B2 JP 5599788B2
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- Prior art keywords
- triazine
- dione
- trifluoromethyl
- methyl
- group
- Prior art date
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- 239000003814 drug Substances 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title description 5
- 229940035893 uracil Drugs 0.000 title description 2
- 150000003918 triazines Chemical class 0.000 title 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 150000002825 nitriles Chemical class 0.000 claims description 24
- SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical class O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- -1 2-phenylacetyl group Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000001544 thienyl group Chemical group 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 102000004190 Enzymes Human genes 0.000 claims description 11
- 108090000790 Enzymes Proteins 0.000 claims description 11
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 235000020824 obesity Nutrition 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- YVPIZNPUQZWMID-UHFFFAOYSA-N 2,4-dimethyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(C)N=C1N1CCC(OC=2C(=CC=CC=2)C(F)(F)F)CC1 YVPIZNPUQZWMID-UHFFFAOYSA-N 0.000 claims description 7
- WDSUALVWYBTTSL-UHFFFAOYSA-N 3-[6-[4-(2-chlorophenoxy)piperidin-1-yl]-4-methyl-3,5-dioxo-1,2,4-triazin-2-yl]propanenitrile Chemical compound N#CCCN1C(=O)N(C)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)Cl)=N1 WDSUALVWYBTTSL-UHFFFAOYSA-N 0.000 claims description 7
- BBDITBPIJLQIHA-UHFFFAOYSA-N 4-methyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-2h-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)NN=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 BBDITBPIJLQIHA-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- OEMGJLHSZNUBTL-UHFFFAOYSA-N 2,4-dimethyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(C)N=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 OEMGJLHSZNUBTL-UHFFFAOYSA-N 0.000 claims description 6
- MRBFQOMANVUMGR-UHFFFAOYSA-N 2-(2-ethoxyethyl)-4-methyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(CCOCC)N=C1N1CCC(OC=2C(=CC=CC=2)C(F)(F)F)CC1 MRBFQOMANVUMGR-UHFFFAOYSA-N 0.000 claims description 6
- VOKZFQMBYKWMCU-UHFFFAOYSA-N 2-(2-hydroxyethyl)-4-methyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound OCCN1C(=O)N(C)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=N1 VOKZFQMBYKWMCU-UHFFFAOYSA-N 0.000 claims description 6
- VCBUQHDJJHMQMS-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-methyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=NN1C1=CC=C(F)C=C1 VCBUQHDJJHMQMS-UHFFFAOYSA-N 0.000 claims description 6
- YJSJYYCOMMPDMD-UHFFFAOYSA-N 2-[2-(1h-indol-3-yl)ethyl]-4-methyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound N=1N(CCC=2C3=CC=CC=C3NC=2)C(=O)N(C)C(=O)C=1N(CC1)CCC1OC1=CC=CC=C1C(F)(F)F YJSJYYCOMMPDMD-UHFFFAOYSA-N 0.000 claims description 6
- CSMKNWBDGZGADP-UHFFFAOYSA-N 2-methyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1NC(=O)N(C)N=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 CSMKNWBDGZGADP-UHFFFAOYSA-N 0.000 claims description 6
- VLTXFCIDXTVMAW-UHFFFAOYSA-N 3-[4-heptyl-3,5-dioxo-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazin-2-yl]propanenitrile Chemical compound N#CCCN1C(=O)N(CCCCCCC)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=N1 VLTXFCIDXTVMAW-UHFFFAOYSA-N 0.000 claims description 6
- UMGAYSFKSDRYGF-UHFFFAOYSA-N 4-methyl-2-(4,4,4-trifluorobutyl)-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound FC(F)(F)CCCN1C(=O)N(C)C(=O)C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 UMGAYSFKSDRYGF-UHFFFAOYSA-N 0.000 claims description 6
- ARRUOYFMRZKRIG-UHFFFAOYSA-N 4-methyl-2-pyridin-3-yl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=NN1C1=CC=CN=C1 ARRUOYFMRZKRIG-UHFFFAOYSA-N 0.000 claims description 6
- NIUVUIDDICJVFR-UHFFFAOYSA-N 4-methyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-2h-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)NN=C1N1CCC(OC=2C(=CC=CC=2)C(F)(F)F)CC1 NIUVUIDDICJVFR-UHFFFAOYSA-N 0.000 claims description 6
- VWEYWXUTLVBUJI-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-4-methyl-2-(3-methylbutyl)-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(CCC(C)C)N=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 VWEYWXUTLVBUJI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ACKMUUCTQAVPMJ-UHFFFAOYSA-N 2,4-dimethyl-6-[4-(2-methylphenoxy)piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound CC1=CC=CC=C1OC1CCN(C=2C(N(C)C(=O)N(C)N=2)=O)CC1 ACKMUUCTQAVPMJ-UHFFFAOYSA-N 0.000 claims description 5
- DYAUXEQIHWOYIT-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4-methyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound COC1=CC=CC=C1N1C(=O)N(C)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=N1 DYAUXEQIHWOYIT-UHFFFAOYSA-N 0.000 claims description 5
- AGVALPANBTYLNK-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethyl]-4-methyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(CCOCCOCC)N=C1N1CCC(OC=2C(=CC=CC=2)C(F)(F)F)CC1 AGVALPANBTYLNK-UHFFFAOYSA-N 0.000 claims description 5
- RPUNSCZLLKIOGS-UHFFFAOYSA-N 4-[4-methyl-3,5-dioxo-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazin-2-yl]benzonitrile Chemical compound O=C1N(C)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=NN1C1=CC=C(C#N)C=C1 RPUNSCZLLKIOGS-UHFFFAOYSA-N 0.000 claims description 5
- HTYWAZMBAJNJPB-UHFFFAOYSA-N 4-methyl-2-(2-oxocyclohexyl)-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=NN1C1CCCCC1=O HTYWAZMBAJNJPB-UHFFFAOYSA-N 0.000 claims description 5
- QXMCMMCLJDGLEX-UHFFFAOYSA-N 4-methyl-2-(4,4,4-trifluorobutyl)-6-[4-[[2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound FC(F)(F)CCCN1C(=O)N(C)C(=O)C(N2CCN(CC=3C(=CC=CC=3)C(F)(F)F)CC2)=N1 QXMCMMCLJDGLEX-UHFFFAOYSA-N 0.000 claims description 5
- LKRHPAAWNAAHRN-UHFFFAOYSA-N 4-methyl-2-(4-oxo-4-thiophen-2-ylbutyl)-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)C(N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=NN1CCCC(=O)C1=CC=CS1 LKRHPAAWNAAHRN-UHFFFAOYSA-N 0.000 claims description 5
- URZFRIGBKDFGFS-UHFFFAOYSA-N 4-methyl-6-[4-[[2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-2h-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)NN=C1N1CCN(CC=2C(=CC=CC=2)C(F)(F)F)CC1 URZFRIGBKDFGFS-UHFFFAOYSA-N 0.000 claims description 5
- NQZCOQZMHJINMI-UHFFFAOYSA-N 6-[4-(2-chlorophenoxy)piperidin-1-yl]-2,4-dimethyl-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(C)N=C1N1CCC(OC=2C(=CC=CC=2)Cl)CC1 NQZCOQZMHJINMI-UHFFFAOYSA-N 0.000 claims description 5
- FYXBLLVYQZUGQS-UHFFFAOYSA-N 6-[4-(2-chlorophenoxy)piperidin-1-yl]-4-heptyl-2h-1,2,4-triazine-3,5-dione Chemical compound O=C1N(CCCCCCC)C(=O)NN=C1N1CCC(OC=2C(=CC=CC=2)Cl)CC1 FYXBLLVYQZUGQS-UHFFFAOYSA-N 0.000 claims description 5
- DQSWZGMNHNDQRL-UHFFFAOYSA-N 6-[4-(4-fluorophenoxy)piperidin-1-yl]-2,4-dimethyl-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(C)N=C1N1CCC(OC=2C=CC(F)=CC=2)CC1 DQSWZGMNHNDQRL-UHFFFAOYSA-N 0.000 claims description 5
- QXWWMLWCEYKQNC-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-4-methyl-2-(4,4,4-trifluorobutyl)-1,2,4-triazine-3,5-dione Chemical compound FC(F)(F)CCCN1C(=O)N(C)C(=O)C(N2CCN(CC2)C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)=N1 QXWWMLWCEYKQNC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- SJLYCKNRYFZTLY-UHFFFAOYSA-N n-methyl-2-[4-methyl-3,5-dioxo-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazin-2-yl]acetamide Chemical compound O=C1N(C)C(=O)N(CC(=O)NC)N=C1N1CCC(OC=2C(=CC=CC=2)C(F)(F)F)CC1 SJLYCKNRYFZTLY-UHFFFAOYSA-N 0.000 claims description 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 101150065749 Churc1 gene Proteins 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- LHCFGTZZVBYISM-UHFFFAOYSA-N 2,4-dimethyl-6-[4-[[2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(C)N=C1N1CCN(CC=2C(=CC=CC=2)C(F)(F)F)CC1 LHCFGTZZVBYISM-UHFFFAOYSA-N 0.000 claims description 3
- AROJJNWSBAEDAI-UHFFFAOYSA-N 2-butyl-4-methyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(CCCC)N=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 AROJJNWSBAEDAI-UHFFFAOYSA-N 0.000 claims description 3
- YRQZSAGPFZSEMC-UHFFFAOYSA-N 2-butyl-4-methyl-6-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(CCCC)N=C1N1CCC(OC=2C(=CC=CC=2)C(F)(F)F)CC1 YRQZSAGPFZSEMC-UHFFFAOYSA-N 0.000 claims description 3
- RQTRGKKQVBSRIX-UHFFFAOYSA-N 4-heptyl-2-methyl-6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]-1,2,4-triazine-3,5-dione Chemical compound CN1C(=O)N(CCCCCCC)C(=O)C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 RQTRGKKQVBSRIX-UHFFFAOYSA-N 0.000 claims description 3
- XXJYPVKFYYQUKP-UHFFFAOYSA-N 6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-2,4-dimethyl-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(C)N=C1N1CCC(OC=2C(=CC=C(F)C=2)Cl)CC1 XXJYPVKFYYQUKP-UHFFFAOYSA-N 0.000 claims description 3
- WMCGNJFBYSTLNU-UHFFFAOYSA-N 6-[4-[2-chloro-5-(trifluoromethyl)phenoxy]piperidin-1-yl]-2,4-dimethyl-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)N(C)N=C1N1CCC(OC=2C(=CC=C(C=2)C(F)(F)F)Cl)CC1 WMCGNJFBYSTLNU-UHFFFAOYSA-N 0.000 claims description 3
- WNUCYSMCOZYPAF-UHFFFAOYSA-N 6-[4-[4-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-4-methyl-2h-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)NN=C1N1CCN(C(=O)C=2C(=CC(F)=CC=2)C(F)(F)F)CC1 WNUCYSMCOZYPAF-UHFFFAOYSA-N 0.000 claims description 3
- AUKKFPBHMYULGQ-UHFFFAOYSA-N 6-[4-[5-fluoro-2-(trifluoromethyl)benzoyl]piperazin-1-yl]-4-methyl-2h-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)NN=C1N1CCN(C(=O)C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 AUKKFPBHMYULGQ-UHFFFAOYSA-N 0.000 claims description 3
- IOSUVXBLSSRABZ-UHFFFAOYSA-N 6-[4-[[4-fluoro-2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-4-methyl-2h-1,2,4-triazine-3,5-dione Chemical compound O=C1N(C)C(=O)NN=C1N1CCN(CC=2C(=CC(F)=CC=2)C(F)(F)F)CC1 IOSUVXBLSSRABZ-UHFFFAOYSA-N 0.000 claims description 3
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 2
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
- 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
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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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0854794 | 2008-07-15 | ||
| FR0854794A FR2933979B1 (fr) | 2008-07-15 | 2008-07-15 | Derives de triazines et uraciles, leur preparation et leur application en therapeutique humaine |
| PCT/EP2009/058609 WO2010006962A1 (en) | 2008-07-15 | 2009-07-07 | Derivatives of triazines and uracils, their preparation and their application in human therapeutics |
Publications (3)
| Publication Number | Publication Date |
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| JP2011528007A JP2011528007A (ja) | 2011-11-10 |
| JP2011528007A5 JP2011528007A5 (enExample) | 2012-08-30 |
| JP5599788B2 true JP5599788B2 (ja) | 2014-10-01 |
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Family Applications (1)
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| JP2011517863A Expired - Fee Related JP5599788B2 (ja) | 2008-07-15 | 2009-07-07 | トリアジンおよびウラシルの誘導体、それらの調製、およびヒト治療薬におけるそれらの応用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8618287B2 (enExample) |
| EP (1) | EP2328886B1 (enExample) |
| JP (1) | JP5599788B2 (enExample) |
| AR (1) | AR072510A1 (enExample) |
| FR (1) | FR2933979B1 (enExample) |
| TW (1) | TW201006815A (enExample) |
| WO (1) | WO2010006962A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103664873B (zh) | 2009-12-30 | 2016-06-15 | 深圳信立泰药业股份有限公司 | 作为二肽基肽酶iv(dpp-iv)抑制剂的3-(3-氨基哌啶-1-基)-5-氧代-1,2,4-三嗪衍生物 |
| FR2958935B1 (fr) | 2010-04-19 | 2012-06-22 | Pf Medicament | Derives d'heterocycles azotes, leur preparation et leur application en therapeutique humaine |
| CN104803971B (zh) * | 2014-01-24 | 2021-11-30 | 深圳信立泰药业股份有限公司 | 化合物A单苯甲酸盐的晶型α及其制备方法和含有该晶型的药物组合物 |
| CN105017213B (zh) * | 2014-04-30 | 2017-11-14 | 成都苑东生物制药股份有限公司 | 尿嘧啶衍生物 |
| CN107074823B (zh) * | 2014-09-05 | 2021-05-04 | 基因泰克公司 | 治疗性化合物及其用途 |
| CN110099898B (zh) | 2016-10-24 | 2023-07-25 | 优曼尼蒂治疗公司 | 化合物及其用途 |
| KR20190108118A (ko) | 2017-01-06 | 2019-09-23 | 유마니티 테라퓨틱스, 인크. | 신경계 장애의 치료를 위한 방법 |
| EP3700934A4 (en) | 2017-10-24 | 2021-10-27 | Yumanity Therapeutics, Inc. | COMPOUNDS AND USES OF THESE COMPOUNDS |
| BR112020019191A2 (pt) | 2018-03-23 | 2021-01-05 | Yumanity Therapeutics, Inc. | Compostos e seus usos |
| TWI884745B (zh) * | 2018-10-12 | 2025-05-21 | 美商拓臻股份有限公司 | 甲狀腺素受體β促效劑化合物 |
| CN121081472A (zh) | 2018-12-13 | 2025-12-09 | 拓臻股份有限公司 | 一种THRβ受体激动剂化合物及其制备方法和用途 |
| EP3914593A4 (en) | 2019-01-24 | 2022-11-02 | Yumanity Therapeutics, Inc. | CONNECTIONS AND USES THEREOF |
| EP4028008A4 (en) | 2019-09-12 | 2023-09-13 | Terns Pharmaceuticals, Inc. | Thyroid hormone receptor beta agonist compounds |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
| TWI763147B (zh) | 2019-11-26 | 2022-05-01 | 大陸商昆藥集團股份有限公司 | 1,2,4-三嗪-3,5-二酮類化合物及其製備方法和應用 |
| WO2024102455A1 (en) * | 2022-11-09 | 2024-05-16 | Emory University | Non-covalent inhibitors of coronavirus main protease |
| KR20250166323A (ko) | 2023-04-07 | 2025-11-27 | 테른스 파마슈티칼스, 인크. | 간 장애 또는 심장대사 질환의 치료에 사용하기 위한 thr베타 효현제 및 glp-1r 효현제를 포함하는 조합 |
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| JPS5973573A (ja) * | 1982-09-09 | 1984-04-25 | ワ−ナ−−ランバ−ト・コンパニ− | ジアミノピリミジン化合物 |
| US20050256159A1 (en) * | 2002-10-11 | 2005-11-17 | Astrazeneca Ab | 1,4-disubstituted piperidine derivatives and their use as 11,betahsd1 inhibitors |
| FR2866339B1 (fr) * | 2004-02-18 | 2006-05-05 | Pf Medicament | Derives de 1,2,4-triazines, leur preparation et leur application en therapeutique humaine |
| TW200609219A (en) * | 2004-06-17 | 2006-03-16 | Neurogen Corp | Aryl-substituted piperazine derivatives |
| AU2006326815A1 (en) * | 2005-12-20 | 2007-06-28 | Merck Frosst Canada Ltd. | Heteroaromatic compounds as inhibitors of stearoyl-coenzyme A delta-9 desaturase |
-
2008
- 2008-07-15 FR FR0854794A patent/FR2933979B1/fr not_active Expired - Fee Related
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2009
- 2009-07-07 JP JP2011517863A patent/JP5599788B2/ja not_active Expired - Fee Related
- 2009-07-07 WO PCT/EP2009/058609 patent/WO2010006962A1/en not_active Ceased
- 2009-07-07 US US13/054,293 patent/US8618287B2/en not_active Expired - Fee Related
- 2009-07-07 EP EP09797466.1A patent/EP2328886B1/en not_active Not-in-force
- 2009-07-10 TW TW098123438A patent/TW201006815A/zh unknown
- 2009-07-15 AR ARP090102680A patent/AR072510A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010006962A1 (en) | 2010-01-21 |
| EP2328886B1 (en) | 2016-12-28 |
| FR2933979B1 (fr) | 2012-08-24 |
| US20110118266A1 (en) | 2011-05-19 |
| FR2933979A1 (fr) | 2010-01-22 |
| US8618287B2 (en) | 2013-12-31 |
| JP2011528007A (ja) | 2011-11-10 |
| AR072510A1 (es) | 2010-09-01 |
| TW201006815A (en) | 2010-02-16 |
| EP2328886A1 (en) | 2011-06-08 |
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