JP2013530957A5 - - Google Patents
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- Publication number
- JP2013530957A5 JP2013530957A5 JP2013513348A JP2013513348A JP2013530957A5 JP 2013530957 A5 JP2013530957 A5 JP 2013530957A5 JP 2013513348 A JP2013513348 A JP 2013513348A JP 2013513348 A JP2013513348 A JP 2013513348A JP 2013530957 A5 JP2013530957 A5 JP 2013530957A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- piperazin
- benzamide
- cyclohexyl
- difluoro
- 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.)
- Granted
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 626
- -1 2-cyanophenyl Chemical group 0.000 claims description 133
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- TURTXUSSYAAWDU-UHFFFAOYSA-N 2-chloro-n-[1-[3,3-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclopentyl]ethyl]-4-fluorobenzamide Chemical compound C1CC(F)(F)CC1(N1CCN(CC1)S(=O)(=O)C=1N=NN(C)C=1)C(C)NC(=O)C1=CC=C(F)C=C1Cl TURTXUSSYAAWDU-UHFFFAOYSA-N 0.000 claims description 8
- KZMAEPZALJYLFZ-UHFFFAOYSA-N 2-chloro-n-[1-[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]ethyl]-4-fluorobenzamide Chemical compound C1CC(F)(F)CCC1(N1CCN(CC1)S(=O)(=O)C=1N=NN(C)C=1)C(C)NC(=O)C1=CC=C(F)C=C1Cl KZMAEPZALJYLFZ-UHFFFAOYSA-N 0.000 claims description 8
- AUGUDOWJZSIKTA-UHFFFAOYSA-N 2-chloro-n-[1-[4,4-difluoro-1-[4-(2-hydroxypropylsulfonyl)piperazin-1-yl]cyclohexyl]ethyl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(S(=O)(=O)CC(O)C)CCN1C1(C(C)NC(=O)C=2C(=CC(=CC=2)C(F)(F)F)Cl)CCC(F)(F)CC1 AUGUDOWJZSIKTA-UHFFFAOYSA-N 0.000 claims description 8
- ZVZJHYTZKLHFBN-UHFFFAOYSA-N 2-chloro-n-[1-[4,4-difluoro-1-[4-(2-hydroxypropylsulfonyl)piperazin-1-yl]cyclohexyl]ethyl]-4-fluorobenzamide Chemical compound C1CN(S(=O)(=O)CC(O)C)CCN1C1(C(C)NC(=O)C=2C(=CC(F)=CC=2)Cl)CCC(F)(F)CC1 ZVZJHYTZKLHFBN-UHFFFAOYSA-N 0.000 claims description 8
- HFXBCPUSRICANI-UHFFFAOYSA-N 2-chloro-n-[[3,3-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclopentyl]methyl]-4-fluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCN(C2(CNC(=O)C=3C(=CC(F)=CC=3)Cl)CC(F)(F)CC2)CC1 HFXBCPUSRICANI-UHFFFAOYSA-N 0.000 claims description 8
- DCWUQWDXVQPWFD-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[1-(1-methyltriazol-4-yl)sulfonylpiperidin-4-yl]cyclohexyl]methyl]-4-fluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCC(C2(CNC(=O)C=3C(=CC(F)=CC=3)Cl)CCC(F)(F)CC2)CC1 DCWUQWDXVQPWFD-UHFFFAOYSA-N 0.000 claims description 8
- WVFMVRCDAYHCFP-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-4-fluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCN(C2(CNC(=O)C=3C(=CC(F)=CC=3)Cl)CCC(F)(F)CC2)CC1 WVFMVRCDAYHCFP-UHFFFAOYSA-N 0.000 claims description 8
- SAJCDXSXUPJGDH-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(2-hydroxypropylsulfonyl)piperazin-1-yl]cyclohexyl]methyl]-4-fluorobenzamide Chemical compound C1CN(S(=O)(=O)CC(O)C)CCN1C1(CNC(=O)C=2C(=CC(F)=CC=2)Cl)CCC(F)(F)CC1 SAJCDXSXUPJGDH-UHFFFAOYSA-N 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
- DZZKZKMVWFISEJ-UHFFFAOYSA-N n-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)ONC(=O)C1=CC=CC=C1 DZZKZKMVWFISEJ-UHFFFAOYSA-N 0.000 claims description 8
- QXQAHHNEFOJTND-UHFFFAOYSA-N n-[1-[4,4-difluoro-1-[4-(2-hydroxypropylsulfonyl)piperazin-1-yl]cyclohexyl]ethyl]-2,4-bis(trifluoromethyl)benzamide Chemical compound C1CN(S(=O)(=O)CC(O)C)CCN1C1(C(C)NC(=O)C=2C(=CC(=CC=2)C(F)(F)F)C(F)(F)F)CCC(F)(F)CC1 QXQAHHNEFOJTND-UHFFFAOYSA-N 0.000 claims description 8
- WXQQATYKMOKZNA-UHFFFAOYSA-N n-[[4,4-difluoro-1-[4-(2-hydroxypropylsulfonyl)piperazin-1-yl]cyclohexyl]methyl]-2,4-bis(trifluoromethyl)benzamide Chemical compound C1CN(S(=O)(=O)CC(O)C)CCN1C1(CNC(=O)C=2C(=CC(=CC=2)C(F)(F)F)C(F)(F)F)CCC(F)(F)CC1 WXQQATYKMOKZNA-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- SVSYRJUZUMWRMS-UHFFFAOYSA-N 2,4-dichloro-n-[1-[4,4-difluoro-1-[4-(2-hydroxypropylsulfonyl)piperazin-1-yl]cyclohexyl]ethyl]benzamide Chemical compound C1CN(S(=O)(=O)CC(O)C)CCN1C1(C(C)NC(=O)C=2C(=CC(Cl)=CC=2)Cl)CCC(F)(F)CC1 SVSYRJUZUMWRMS-UHFFFAOYSA-N 0.000 claims description 7
- CMCKVSNJYGAWMX-UHFFFAOYSA-N 2,4-dichloro-n-[[4,4-difluoro-1-[4-(2-hydroxypropylsulfonyl)piperazin-1-yl]cyclohexyl]methyl]benzamide Chemical compound C1CN(S(=O)(=O)CC(O)C)CCN1C1(CNC(=O)C=2C(=CC(Cl)=CC=2)Cl)CCC(F)(F)CC1 CMCKVSNJYGAWMX-UHFFFAOYSA-N 0.000 claims description 7
- NNSLNEKLYAQUJI-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(2-hydroxypropylsulfonyl)piperazin-1-yl]cyclohexyl]methyl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(S(=O)(=O)CC(O)C)CCN1C1(CNC(=O)C=2C(=CC(=CC=2)C(F)(F)F)Cl)CCC(F)(F)CC1 NNSLNEKLYAQUJI-UHFFFAOYSA-N 0.000 claims description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims description 6
- QCIDEYLDAGNHRM-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(1-methylimidazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-4-fluorobenzamide Chemical compound CN1C=NC(S(=O)(=O)N2CCN(CC2)C2(CNC(=O)C=3C(=CC(F)=CC=3)Cl)CCC(F)(F)CC2)=C1 QCIDEYLDAGNHRM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- FGMUHFCARDYHEJ-UHFFFAOYSA-N n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-2,6-difluorobenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC=CC=2F)F)CCC(F)(F)CC1 FGMUHFCARDYHEJ-UHFFFAOYSA-N 0.000 claims description 6
- GKWBCTOARGYUIM-UHFFFAOYSA-N n-[[4,4-difluoro-1-[4-(1-methylimidazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-2,4-difluorobenzamide Chemical compound CN1C=NC(S(=O)(=O)N2CCN(CC2)C2(CNC(=O)C=3C(=CC(F)=CC=3)F)CCC(F)(F)CC2)=C1 GKWBCTOARGYUIM-UHFFFAOYSA-N 0.000 claims description 6
- AUEBMLQTZVKCHZ-UHFFFAOYSA-N n-[[4,4-difluoro-1-[4-(1-methylimidazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-2,6-difluorobenzamide Chemical compound CN1C=NC(S(=O)(=O)N2CCN(CC2)C2(CNC(=O)C=3C(=CC=CC=3F)F)CCC(F)(F)CC2)=C1 AUEBMLQTZVKCHZ-UHFFFAOYSA-N 0.000 claims description 6
- IDGULWSAVILSTK-UHFFFAOYSA-N n-[[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-2,6-difluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCN(C2(CNC(=O)C=3C(=CC=CC=3F)F)CCC(F)(F)CC2)CC1 IDGULWSAVILSTK-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- VJLVVCSODSTMLL-UHFFFAOYSA-N 2,4-dichloro-n-[[1-[4-(cyclopropylmethylsulfonyl)piperazin-1-yl]cyclohexyl]methyl]benzamide Chemical compound ClC1=CC(Cl)=CC=C1C(=O)NCC1(N2CCN(CC2)S(=O)(=O)CC2CC2)CCCCC1 VJLVVCSODSTMLL-UHFFFAOYSA-N 0.000 claims description 4
- FWLOIOZRFHTSGQ-UHFFFAOYSA-N 2,4-dichloro-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-6-fluorobenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC(Cl)=CC=2F)Cl)CCC(F)(F)CC1 FWLOIOZRFHTSGQ-UHFFFAOYSA-N 0.000 claims description 4
- ALDDUEZQMUCKST-UHFFFAOYSA-N 2,4-dichloro-n-[[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-5-fluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCN(C2(CNC(=O)C=3C(=CC(Cl)=C(F)C=3)Cl)CCC(F)(F)CC2)CC1 ALDDUEZQMUCKST-UHFFFAOYSA-N 0.000 claims description 4
- PIEOCXSJAKIRDH-UHFFFAOYSA-N 2,4-dichloro-n-[[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-6-fluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCN(C2(CNC(=O)C=3C(=CC(Cl)=CC=3F)Cl)CCC(F)(F)CC2)CC1 PIEOCXSJAKIRDH-UHFFFAOYSA-N 0.000 claims description 4
- XASFTYNOHQXSBP-UHFFFAOYSA-N 2-(difluoromethoxy)-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-6-fluorobenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC=CC=2F)OC(F)F)CCC(F)(F)CC1 XASFTYNOHQXSBP-UHFFFAOYSA-N 0.000 claims description 4
- DESJHZMZICSFLF-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-4-fluorobenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC(F)=CC=2)Cl)CCC(F)(F)CC1 DESJHZMZICSFLF-UHFFFAOYSA-N 0.000 claims description 4
- PVRPGBYPVMWMJP-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-6-fluorobenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC=CC=2F)Cl)CCC(F)(F)CC1 PVRPGBYPVMWMJP-UHFFFAOYSA-N 0.000 claims description 4
- HYGYDYZYVIJRAT-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-6-methylbenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC=CC=2C)Cl)CCC(F)(F)CC1 HYGYDYZYVIJRAT-UHFFFAOYSA-N 0.000 claims description 4
- BGYGHCORXUALDD-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(1-fluoropropylsulfonyl)piperazin-1-yl]cyclohexyl]methyl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(S(=O)(=O)C(F)CC)CCN1C1(CNC(=O)C=2C(=CC(=CC=2)C(F)(F)F)Cl)CCC(F)(F)CC1 BGYGHCORXUALDD-UHFFFAOYSA-N 0.000 claims description 4
- IIJNRBXCHDFXSK-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(1-methylimidazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-6-fluorobenzamide Chemical compound CN1C=NC(S(=O)(=O)N2CCN(CC2)C2(CNC(=O)C=3C(=CC=CC=3F)Cl)CCC(F)(F)CC2)=C1 IIJNRBXCHDFXSK-UHFFFAOYSA-N 0.000 claims description 4
- NNXNSPNPDLOLRG-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(1-methylimidazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-6-methoxybenzamide Chemical compound COC1=CC=CC(Cl)=C1C(=O)NCC1(N2CCN(CC2)S(=O)(=O)C=2N=CN(C)C=2)CCC(F)(F)CC1 NNXNSPNPDLOLRG-UHFFFAOYSA-N 0.000 claims description 4
- YEZPFCRVALSCAQ-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(1-methylimidazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-6-methylbenzamide Chemical compound CC1=CC=CC(Cl)=C1C(=O)NCC1(N2CCN(CC2)S(=O)(=O)C=2N=CN(C)C=2)CCC(F)(F)CC1 YEZPFCRVALSCAQ-UHFFFAOYSA-N 0.000 claims description 4
- QWHQQIRSFCCJOZ-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-3-fluoro-4-methylbenzamide Chemical compound ClC1=C(F)C(C)=CC=C1C(=O)NCC1(N2CCN(CC2)S(=O)(=O)C=2N=NN(C)C=2)CCC(F)(F)CC1 QWHQQIRSFCCJOZ-UHFFFAOYSA-N 0.000 claims description 4
- AWTLKEUDKQJATH-UHFFFAOYSA-N 2-chloro-n-[[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-4,5-difluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCN(C2(CNC(=O)C=3C(=CC(F)=C(F)C=3)Cl)CCC(F)(F)CC2)CC1 AWTLKEUDKQJATH-UHFFFAOYSA-N 0.000 claims description 4
- RIXBTGOYSZHJIC-UHFFFAOYSA-N 4-chloro-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-2,6-difluorobenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC(Cl)=CC=2F)F)CCC(F)(F)CC1 RIXBTGOYSZHJIC-UHFFFAOYSA-N 0.000 claims description 4
- GFJHJGBECCURJV-UHFFFAOYSA-N 4-chloro-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-2,6-dimethylbenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC(Cl)=CC=2C)C)CCC(F)(F)CC1 GFJHJGBECCURJV-UHFFFAOYSA-N 0.000 claims description 4
- YKOUJOAFGPOWTC-UHFFFAOYSA-N 4-chloro-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-2-fluorobenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC(Cl)=CC=2)F)CCC(F)(F)CC1 YKOUJOAFGPOWTC-UHFFFAOYSA-N 0.000 claims description 4
- FKLBDZITQCWCBL-UHFFFAOYSA-N 4-chloro-n-[[4,4-difluoro-1-(4-propylsulfonylpiperazin-1-yl)cyclohexyl]methyl]-2-methylbenzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC(Cl)=CC=2)C)CCC(F)(F)CC1 FKLBDZITQCWCBL-UHFFFAOYSA-N 0.000 claims description 4
- COKPKOWZXUWPMW-UHFFFAOYSA-N 4-chloro-n-[[4,4-difluoro-1-[4-(1-methylimidazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-2-fluorobenzamide Chemical compound CN1C=NC(S(=O)(=O)N2CCN(CC2)C2(CNC(=O)C=3C(=CC(Cl)=CC=3)F)CCC(F)(F)CC2)=C1 COKPKOWZXUWPMW-UHFFFAOYSA-N 0.000 claims description 4
- UKHPDLGABCXRFF-UHFFFAOYSA-N 4-chloro-n-[[4,4-difluoro-1-[4-(1-methylimidazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-2-methylbenzamide Chemical compound CC1=CC(Cl)=CC=C1C(=O)NCC1(N2CCN(CC2)S(=O)(=O)C=2N=CN(C)C=2)CCC(F)(F)CC1 UKHPDLGABCXRFF-UHFFFAOYSA-N 0.000 claims description 4
- XDALBVGXFIUNBI-UHFFFAOYSA-N 4-chloro-n-[[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-2,5-difluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCN(C2(CNC(=O)C=3C(=CC(Cl)=C(F)C=3)F)CCC(F)(F)CC2)CC1 XDALBVGXFIUNBI-UHFFFAOYSA-N 0.000 claims description 4
- DXUNCNNNBZUHMT-UHFFFAOYSA-N 4-chloro-n-[[4,4-difluoro-1-[4-(1-methyltriazol-4-yl)sulfonylpiperazin-1-yl]cyclohexyl]methyl]-2,6-difluorobenzamide Chemical compound N1=NN(C)C=C1S(=O)(=O)N1CCN(C2(CNC(=O)C=3C(=CC(Cl)=CC=3F)F)CCC(F)(F)CC2)CC1 DXUNCNNNBZUHMT-UHFFFAOYSA-N 0.000 claims description 4
- YVXNOVMSRCGLIH-UHFFFAOYSA-N C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC(F)=C(F)C=2)Cl)CCC(F)(F)CC1 Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1(CNC(=O)C=2C(=CC(F)=C(F)C=2)Cl)CCC(F)(F)CC1 YVXNOVMSRCGLIH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
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| CN102448951B (zh) | 2009-04-06 | 2017-05-10 | 安吉奥斯医药品有限公司 | 丙酮酸激酶m2调节剂、治疗组合物和相关使用方法 |
| PL2427441T3 (pl) | 2009-05-04 | 2017-06-30 | Agios Pharmaceuticals, Inc. | Aktywatory PKM2 do stosowania w leczeniu raka |
| EP2448581B1 (en) | 2009-06-29 | 2016-12-07 | Agios Pharmaceuticals, Inc. | Therapeutic compositions and related methods of use |
| PT2448582T (pt) * | 2009-06-29 | 2017-07-10 | Agios Pharmaceuticals Inc | Compostos e composições terapêuticas |
| US20130109672A1 (en) | 2010-04-29 | 2013-05-02 | The United States Of America,As Represented By The Secretary, Department Of Health And Human Service | Activators of human pyruvate kinase |
| SG186885A1 (en) | 2010-06-04 | 2013-02-28 | Albany Molecular Res Inc | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| JP5837091B2 (ja) | 2010-12-17 | 2015-12-24 | アジオス ファーマシューティカルズ， インコーポレイテッド | ピルビン酸キナーゼｍ２（ｐｋｍ２）調節剤としての新規ｎ−（４−（アゼチジン−１−カルボニル）フェニル）−（ヘテロ−）アリールスルホンアミド誘導体 |
| US9328077B2 (en) | 2010-12-21 | 2016-05-03 | Agios Pharmaceuticals, Inc | Bicyclic PKM2 activators |
| TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
| CN108451955B (zh) | 2011-05-03 | 2022-02-01 | 安吉奥斯医药品有限公司 | 用于治疗的丙酮酸激酶活化剂 |
| CN103254127B (zh) * | 2013-05-28 | 2015-08-19 | 北京哈三联科技有限责任公司 | 甘氨酸重摄取抑制剂及其应用 |
| SMT202300344T1 (it) | 2015-06-11 | 2023-11-13 | Agios Pharmaceuticals Inc | Metodi di utilizzo degli attivatori della piruvato chinasi |
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-
2011
- 2011-06-02 SG SG2013000047A patent/SG186885A1/en unknown
- 2011-06-02 NZ NZ604035A patent/NZ604035A/en not_active IP Right Cessation
- 2011-06-02 AU AU2011261375A patent/AU2011261375B2/en not_active Expired - Fee Related
- 2011-06-02 US US13/151,992 patent/US9045445B2/en active Active
- 2011-06-02 KR KR1020137000117A patent/KR20130087002A/ko not_active Abandoned
- 2011-06-02 CN CN201180038081.9A patent/CN103096893B/zh active Active
- 2011-06-02 EP EP11790414.4A patent/EP2575815A4/en not_active Withdrawn
- 2011-06-02 WO PCT/US2011/038939 patent/WO2011153359A1/en not_active Ceased
- 2011-06-02 CA CA2801074A patent/CA2801074A1/en not_active Abandoned
- 2011-06-02 JP JP2013513348A patent/JP5813101B2/ja not_active Expired - Fee Related
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