CA2593427C - Combination therapy for the treatment of diabetes and conditions related thereto and for the treatment of conditions ameliorated by increasing a blood glp-1 level - Google Patents

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Publication number

CA2593427C

CA2593427C CA2593427A CA2593427A CA2593427C CA 2593427 C CA2593427 C CA 2593427C CA 2593427 A CA2593427 A CA 2593427A CA 2593427 A CA2593427 A CA 2593427A CA 2593427 C CA2593427 C CA 2593427C

Authority

CA

Canada

Prior art keywords

pyrimidin

yloxy

dpp

phenyl

methanesulfonyl

Prior art date

2005-01-10

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.)

Expired - Fee Related

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• SQSSGVAAQHUQQD-UHFFFAOYSA-N cyclopentylmethyl 4-[1-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C2=NC=NC(OC3CCN(CC3)C(=O)OCC3CCCC3)=C2C=N1 SQSSGVAAQHUQQD-UHFFFAOYSA-N 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• KCNLVJLJDUJVMD-UHFFFAOYSA-N cyclopropylmethyl 4-[1-(2-fluoro-4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]sulfanylpiperidine-1-carboxylate Chemical compound FC1=CC(S(=O)(=O)C)=CC=C1N1C2=NC=NC(SC3CCN(CC3)C(=O)OCC3CC3)=C2C=N1 KCNLVJLJDUJVMD-UHFFFAOYSA-N 0.000 description 1
• ORTKDKSWQJZIBY-UHFFFAOYSA-N cyclopropylmethyl 4-[[[6-(4-cyano-2-fluoroanilino)pyrimidin-4-yl]-methylamino]methyl]piperidine-1-carboxylate Chemical compound C=1C(NC=2C(=CC(=CC=2)C#N)F)=NC=NC=1N(C)CC(CC1)CCN1C(=O)OCC1CC1 ORTKDKSWQJZIBY-UHFFFAOYSA-N 0.000 description 1
• 230000008021 deposition Effects 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 229960000633 dextran sulfate Drugs 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 238000003745 diagnosis Methods 0.000 description 1
• 125000005265 dialkylamine group Chemical group 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 230000006806 disease prevention Effects 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 239000006274 endogenous ligand Substances 0.000 description 1
• CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 1
• 229950010170 epalrestat Drugs 0.000 description 1
• CHNUOJQWGUIOLD-UHFFFAOYSA-N epalrestate Natural products C=1C=CC=CC=1C=C(C)C=C1SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-UHFFFAOYSA-N 0.000 description 1
• 235000019441 ethanol Nutrition 0.000 description 1
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
• USVYYPQABMCXKL-UHFFFAOYSA-N ethyl 1-[2-nitro-3-[4-(3-oxobutyl)phenoxy]phenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=CC(OC=2C=CC(CCC(C)=O)=CC=2)=C1[N+]([O-])=O USVYYPQABMCXKL-UHFFFAOYSA-N 0.000 description 1
• JFDVGACPVMKGDT-UHFFFAOYSA-N ethyl 1-[2-nitro-5-[4-(3-oxobutyl)phenoxy]phenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(OC=2C=CC(CCC(C)=O)=CC=2)=CC=C1[N+]([O-])=O JFDVGACPVMKGDT-UHFFFAOYSA-N 0.000 description 1
• PUJRIHHEFRZEKV-UHFFFAOYSA-N ethyl 1-[3-(4-benzoylphenoxy)-4-nitrophenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=C([N+]([O-])=O)C(OC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=C1 PUJRIHHEFRZEKV-UHFFFAOYSA-N 0.000 description 1
• ZMPAGHJNZLNDFW-UHFFFAOYSA-N ethyl 1-[3-nitro-2-[4-(3-oxobutyl)phenoxy]pyridin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=NC(OC=2C=CC(CCC(C)=O)=CC=2)=C1[N+]([O-])=O ZMPAGHJNZLNDFW-UHFFFAOYSA-N 0.000 description 1
• MZDUGMYFOHKNCK-UHFFFAOYSA-N ethyl 1-[3-nitro-4-[4-(3-oxobutyl)phenoxy]pyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=CC(OC=2C=CC(CCC(C)=O)=CC=2)=C1[N+]([O-])=O MZDUGMYFOHKNCK-UHFFFAOYSA-N 0.000 description 1
• NZPFCYHZFHSYKF-UHFFFAOYSA-N ethyl 1-[3-nitro-6-(4-pyrrol-1-ylphenoxy)pyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)N2C=CC=C2)=CC=C1[N+]([O-])=O NZPFCYHZFHSYKF-UHFFFAOYSA-N 0.000 description 1
• VTFDCIKYWYPIJN-UHFFFAOYSA-N ethyl 1-[3-nitro-6-[4-(1,2,4-triazol-1-yl)phenoxy]pyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)N2N=CN=C2)=CC=C1[N+]([O-])=O VTFDCIKYWYPIJN-UHFFFAOYSA-N 0.000 description 1
• GNTKDQJZFGDSPG-UHFFFAOYSA-N ethyl 1-[3-nitro-6-[4-(3-oxobutyl)phenoxy]pyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(CCC(C)=O)=CC=2)=CC=C1[N+]([O-])=O GNTKDQJZFGDSPG-UHFFFAOYSA-N 0.000 description 1
• QGZHQKLJPBKORX-UHFFFAOYSA-N ethyl 1-[3-nitro-6-[4-(4-oxocyclohexyl)phenoxy]pyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)C2CCC(=O)CC2)=CC=C1[N+]([O-])=O QGZHQKLJPBKORX-UHFFFAOYSA-N 0.000 description 1
• ONQUDLDCQDXIGI-UHFFFAOYSA-N ethyl 1-[4-(2-amino-4-ethylsulfonylphenoxy)-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=CC(OC=2C(=CC(=CC=2)S(=O)(=O)CC)N)=C1[N+]([O-])=O ONQUDLDCQDXIGI-UHFFFAOYSA-N 0.000 description 1
• PEIHBEGXCAZAGM-UHFFFAOYSA-N ethyl 1-[4-(4-imidazol-1-ylphenoxy)-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=CC(OC=2C=CC(=CC=2)N2C=NC=C2)=C1[N+]([O-])=O PEIHBEGXCAZAGM-UHFFFAOYSA-N 0.000 description 1
• ILZBJOYICHYCFL-UHFFFAOYSA-N ethyl 1-[4-[4-(3-methoxy-3-oxopropanoyl)phenoxy]-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=CC(OC=2C=CC(=CC=2)C(=O)CC(=O)OC)=C1[N+]([O-])=O ILZBJOYICHYCFL-UHFFFAOYSA-N 0.000 description 1
• PKPCJQOGBQPTFY-UHFFFAOYSA-N ethyl 1-[4-nitro-3-[4-(3-oxobutyl)phenoxy]phenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC=C([N+]([O-])=O)C(OC=2C=CC(CCC(C)=O)=CC=2)=C1 PKPCJQOGBQPTFY-UHFFFAOYSA-N 0.000 description 1
• QYMKMUMGXJOTQI-UHFFFAOYSA-N ethyl 1-[5-(2-amino-4-ethylsulfonylphenoxy)-2-nitrophenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(OC=2C(=CC(=CC=2)S(=O)(=O)CC)N)=CC=C1[N+]([O-])=O QYMKMUMGXJOTQI-UHFFFAOYSA-N 0.000 description 1
• KZUORSGWSYEDSJ-UHFFFAOYSA-N ethyl 1-[5-(4-benzoylanilino)-2-nitrophenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(NC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=CC=C1[N+]([O-])=O KZUORSGWSYEDSJ-UHFFFAOYSA-N 0.000 description 1
• VQDBDBXTCUKZLR-UHFFFAOYSA-N ethyl 1-[5-(4-benzoylphenoxy)-2-nitrophenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=CC=C1[N+]([O-])=O VQDBDBXTCUKZLR-UHFFFAOYSA-N 0.000 description 1
• GAAUTBFEIAPXEA-UHFFFAOYSA-N ethyl 1-[5-(4-ethenylphenoxy)-2-nitrophenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(OC=2C=CC(C=C)=CC=2)=CC=C1[N+]([O-])=O GAAUTBFEIAPXEA-UHFFFAOYSA-N 0.000 description 1
• ZUHWCQOSEKJJSX-UHFFFAOYSA-N ethyl 1-[5-[4-(3-methoxy-3-oxopropanoyl)phenoxy]-2-nitrophenyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=CC(OC=2C=CC(=CC=2)C(=O)CC(=O)OC)=CC=C1[N+]([O-])=O ZUHWCQOSEKJJSX-UHFFFAOYSA-N 0.000 description 1
• QTRCOWZRXOCIHP-UHFFFAOYSA-N ethyl 1-[5-nitro-6-(4-propanoylphenoxy)pyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C=CC(=CC=2)C(=O)CC)=C1[N+]([O-])=O QTRCOWZRXOCIHP-UHFFFAOYSA-N 0.000 description 1
• DZBNWHGYBOGICD-UHFFFAOYSA-N ethyl 1-[5-nitro-6-[4-(1,2,4-triazol-1-yl)anilino]pyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=CC(=CC=2)N2N=CN=C2)=C1[N+]([O-])=O DZBNWHGYBOGICD-UHFFFAOYSA-N 0.000 description 1
• TWNLUCSCGWJPQM-UHFFFAOYSA-N ethyl 1-[5-nitro-6-[4-(3-oxobutyl)phenoxy]pyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C=CC(CCC(C)=O)=CC=2)=C1[N+]([O-])=O TWNLUCSCGWJPQM-UHFFFAOYSA-N 0.000 description 1
• UNIAYOUJRVTMRW-UHFFFAOYSA-N ethyl 1-[5-nitro-6-[4-(thiadiazol-4-yl)phenoxy]pyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C=CC(=CC=2)C=2N=NSC=2)=C1[N+]([O-])=O UNIAYOUJRVTMRW-UHFFFAOYSA-N 0.000 description 1
• JCOFDFRBRSODDQ-UHFFFAOYSA-N ethyl 1-[5-nitro-6-[4-(trifluoromethylsulfonyl)anilino]pyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=CC(=CC=2)S(=O)(=O)C(F)(F)F)=C1[N+]([O-])=O JCOFDFRBRSODDQ-UHFFFAOYSA-N 0.000 description 1
• MRDUOEHISUEQKO-UHFFFAOYSA-N ethyl 1-[6-(2,5-dimethoxyanilino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C(=CC=C(OC)C=2)OC)=C1[N+]([O-])=O MRDUOEHISUEQKO-UHFFFAOYSA-N 0.000 description 1
• LEWGWIWBWMUNHV-UHFFFAOYSA-N ethyl 1-[6-(2-amino-4-ethylsulfonylphenoxy)-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C(=CC(=CC=2)S(=O)(=O)CC)N)=CC=C1[N+]([O-])=O LEWGWIWBWMUNHV-UHFFFAOYSA-N 0.000 description 1
• OENAFZWTMADYCH-UHFFFAOYSA-N ethyl 1-[6-(2-amino-4-ethylsulfonylphenoxy)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C(=CC(=CC=2)S(=O)(=O)CC)N)=C1[N+]([O-])=O OENAFZWTMADYCH-UHFFFAOYSA-N 0.000 description 1
• MAISMEIJSAHGQK-UHFFFAOYSA-N ethyl 1-[6-(2-benzoyl-5-methoxyphenoxy)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C(=CC=C(OC)C=2)C(=O)C=2C=CC=CC=2)=C1[N+]([O-])=O MAISMEIJSAHGQK-UHFFFAOYSA-N 0.000 description 1
• GEZNIHVTVCTWLO-UHFFFAOYSA-N ethyl 1-[6-(2-fluoroanilino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C(=CC=CC=2)F)=C1[N+]([O-])=O GEZNIHVTVCTWLO-UHFFFAOYSA-N 0.000 description 1
• HMWRBNFHOJXPAJ-UHFFFAOYSA-N ethyl 1-[6-(2-methoxyanilino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C(=CC=CC=2)OC)=C1[N+]([O-])=O HMWRBNFHOJXPAJ-UHFFFAOYSA-N 0.000 description 1
• YCAIDNAZBUSZQV-UHFFFAOYSA-N ethyl 1-[6-(3,4-dihydro-2h-1,5-benzodioxepin-7-ylamino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=C3OCCCOC3=CC=2)=C1[N+]([O-])=O YCAIDNAZBUSZQV-UHFFFAOYSA-N 0.000 description 1
• QJZSZLBKUDJMSE-UHFFFAOYSA-N ethyl 1-[6-(3-fluoroanilino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=C(F)C=CC=2)=C1[N+]([O-])=O QJZSZLBKUDJMSE-UHFFFAOYSA-N 0.000 description 1
• BZOZLFDYKVNABV-UHFFFAOYSA-N ethyl 1-[6-(3-methoxyanilino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=C(OC)C=CC=2)=C1[N+]([O-])=O BZOZLFDYKVNABV-UHFFFAOYSA-N 0.000 description 1
• QIXRWHNWCLYVCF-UHFFFAOYSA-N ethyl 1-[6-(4-acetylphenoxy)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C=CC(=CC=2)C(C)=O)=C1[N+]([O-])=O QIXRWHNWCLYVCF-UHFFFAOYSA-N 0.000 description 1
• DWAPBILGBZARMB-UHFFFAOYSA-N ethyl 1-[6-(4-carbamoylphenoxy)-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)C(N)=O)=CC=C1[N+]([O-])=O DWAPBILGBZARMB-UHFFFAOYSA-N 0.000 description 1
• PBDKASMGVNGAJF-UHFFFAOYSA-N ethyl 1-[6-(4-cyclohexylanilino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=CC(=CC=2)C2CCCCC2)=C1[N+]([O-])=O PBDKASMGVNGAJF-UHFFFAOYSA-N 0.000 description 1
• DGWANMFVICABIN-UHFFFAOYSA-N ethyl 1-[6-(4-cyclopentylphenoxy)-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)C2CCCC2)=CC=C1[N+]([O-])=O DGWANMFVICABIN-UHFFFAOYSA-N 0.000 description 1
• AOGLXQMWGPBJRJ-UHFFFAOYSA-N ethyl 1-[6-(4-imidazol-1-ylphenoxy)-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)N2C=NC=C2)=CC=C1[N+]([O-])=O AOGLXQMWGPBJRJ-UHFFFAOYSA-N 0.000 description 1
• NMFLPNKHJXTHLM-UHFFFAOYSA-N ethyl 1-[6-(4-methylsulfonylanilino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=C1[N+]([O-])=O NMFLPNKHJXTHLM-UHFFFAOYSA-N 0.000 description 1
• GXDYPCVLMNSCLA-UHFFFAOYSA-N ethyl 1-[6-(4-methylsulfonylphenoxy)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C=CC(=CC=2)S(C)(=O)=O)=C1[N+]([O-])=O GXDYPCVLMNSCLA-UHFFFAOYSA-N 0.000 description 1
• RYIPABQIIBFYJC-UHFFFAOYSA-N ethyl 1-[6-(4-morpholin-4-ylsulfonylanilino)-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=CC(=CC=2)S(=O)(=O)N2CCOCC2)=C1[N+]([O-])=O RYIPABQIIBFYJC-UHFFFAOYSA-N 0.000 description 1
• LKZNHRRRGKKHCH-UHFFFAOYSA-N ethyl 1-[6-(5-ethylsulfonyl-2-hydroxyanilino)-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(NC=2C(=CC=C(C=2)S(=O)(=O)CC)O)=CC=C1[N+]([O-])=O LKZNHRRRGKKHCH-UHFFFAOYSA-N 0.000 description 1
• MHFAJMGQIFZAOA-UHFFFAOYSA-N ethyl 1-[6-(benzenesulfonamido)-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(NS(=O)(=O)C=2C=CC=CC=2)=CC=C1[N+]([O-])=O MHFAJMGQIFZAOA-UHFFFAOYSA-N 0.000 description 1
• LZZYZGYUVKYCNG-UHFFFAOYSA-N ethyl 1-[6-[4-(1,3-dioxoisoindol-2-yl)phenoxy]-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)N2C(C3=CC=CC=C3C2=O)=O)=CC=C1[N+]([O-])=O LZZYZGYUVKYCNG-UHFFFAOYSA-N 0.000 description 1
• XNBABNCOAPFYAA-UHFFFAOYSA-N ethyl 1-[6-[4-(1,3-dioxoisoindol-2-yl)phenoxy]-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C=CC(=CC=2)N2C(C3=CC=CC=C3C2=O)=O)=C1[N+]([O-])=O XNBABNCOAPFYAA-UHFFFAOYSA-N 0.000 description 1
• USWBOYMNSYZWNF-UHFFFAOYSA-N ethyl 1-[6-[4-(2,5-dioxoimidazolidin-4-yl)phenoxy]-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C=CC(=CC=2)C2C(NC(=O)N2)=O)=C1[N+]([O-])=O USWBOYMNSYZWNF-UHFFFAOYSA-N 0.000 description 1
• OMGZVVXSKYHGQV-UHFFFAOYSA-N ethyl 1-[6-[4-(3-methoxy-3-oxopropanoyl)phenoxy]-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)C(=O)CC(=O)OC)=CC=C1[N+]([O-])=O OMGZVVXSKYHGQV-UHFFFAOYSA-N 0.000 description 1
• WVXNTMHIBPWSRW-UHFFFAOYSA-N ethyl 1-[6-[4-(3-methoxy-3-oxopropanoyl)phenoxy]-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(OC=2C=CC(=CC=2)C(=O)CC(=O)OC)=C1[N+]([O-])=O WVXNTMHIBPWSRW-UHFFFAOYSA-N 0.000 description 1
• WZRQWJLHODGALH-UHFFFAOYSA-N ethyl 1-[6-[4-(4,5-dichloroimidazol-1-yl)anilino]-5-nitropyrimidin-4-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC=NC(NC=2C=CC(=CC=2)N2C(=C(Cl)N=C2)Cl)=C1[N+]([O-])=O WZRQWJLHODGALH-UHFFFAOYSA-N 0.000 description 1
• BWFUPKDMUFTLHL-UHFFFAOYSA-N ethyl 1-[6-[4-(4-hydroxyphenyl)sulfonylphenoxy]-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(O)=CC=2)=CC=C1[N+]([O-])=O BWFUPKDMUFTLHL-UHFFFAOYSA-N 0.000 description 1
• FDIBPXXJKKCOTM-UHFFFAOYSA-N ethyl 1-[6-[4-(4-methoxyphenyl)phenoxy]-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(OC=2C=CC(=CC=2)C=2C=CC(OC)=CC=2)=CC=C1[N+]([O-])=O FDIBPXXJKKCOTM-UHFFFAOYSA-N 0.000 description 1
• KLZFDZVHELHGKK-UHFFFAOYSA-N ethyl 1-[6-[[2-bromo-4-(trifluoromethyl)phenyl]sulfonylamino]-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C1=NC(NS(=O)(=O)C=2C(=CC(=CC=2)C(F)(F)F)Br)=CC=C1[N+]([O-])=O KLZFDZVHELHGKK-UHFFFAOYSA-N 0.000 description 1
• MXKSRGCQGNJXTN-UHFFFAOYSA-N ethyl 1-[6-[benzenesulfonyl(butyl)amino]-3-nitropyridin-2-yl]piperidine-4-carboxylate Chemical compound C=1C=CC=CC=1S(=O)(=O)N(CCCC)C(N=1)=CC=C([N+]([O-])=O)C=1N1CCC(C(=O)OCC)CC1 MXKSRGCQGNJXTN-UHFFFAOYSA-N 0.000 description 1
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• NQAAIDPRSHSKTI-UHFFFAOYSA-N tert-butyl 4-[5-amino-6-(2-fluoro-4-methylsulfonylanilino)pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC(NC=2C(=CC(=CC=2)S(C)(=O)=O)F)=C1N NQAAIDPRSHSKTI-UHFFFAOYSA-N 0.000 description 1
• QVKBITMZDPTZKG-UHFFFAOYSA-N tert-butyl 4-[5-cyano-6-(4-methylsulfonylanilino)pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=C1C#N QVKBITMZDPTZKG-UHFFFAOYSA-N 0.000 description 1
• NPLFMYQACYYFBY-UHFFFAOYSA-N tert-butyl 4-[5-cyano-6-[(6-methylsulfonylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC(NC=2C=NC(=CC=2)S(C)(=O)=O)=C1C#N NPLFMYQACYYFBY-UHFFFAOYSA-N 0.000 description 1
• SOPMLHHWPHCHTJ-UHFFFAOYSA-N tert-butyl 4-[6-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(NC=2C=C3OCCOC3=CC=2)=NC=N1 SOPMLHHWPHCHTJ-UHFFFAOYSA-N 0.000 description 1
• DXMWOHKWJKAKKF-UHFFFAOYSA-N tert-butyl 4-[6-(2,4,5-trifluoroanilino)pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(NC=2C(=CC(F)=C(F)C=2)F)=NC=N1 DXMWOHKWJKAKKF-UHFFFAOYSA-N 0.000 description 1
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• NKIHODQBENXCGU-UHFFFAOYSA-N tert-butyl 4-[6-(2-fluoro-4-methylsulfonylanilino)-5-nitropyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC(NC=2C(=CC(=CC=2)S(C)(=O)=O)F)=C1[N+]([O-])=O NKIHODQBENXCGU-UHFFFAOYSA-N 0.000 description 1
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• ODYICEBBILZEES-UHFFFAOYSA-N tert-butyl 4-[6-(3-chloro-4-cyanoanilino)pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(NC=2C=C(Cl)C(C#N)=CC=2)=NC=N1 ODYICEBBILZEES-UHFFFAOYSA-N 0.000 description 1
• MIIUYCQVBMKGHW-UHFFFAOYSA-N tert-butyl 4-[6-(3-fluoro-4-methylanilino)pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=C(F)C(C)=CC=C1NC1=CC(OC2CCN(CC2)C(=O)OC(C)(C)C)=NC=N1 MIIUYCQVBMKGHW-UHFFFAOYSA-N 0.000 description 1
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• AJCVEPRHZPDGKL-UHFFFAOYSA-N tert-butyl 4-[6-[(2-fluoropyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(NC=2C(=NC=CC=2)F)=NC=N1 AJCVEPRHZPDGKL-UHFFFAOYSA-N 0.000 description 1
• QQDJBTGICVXVCN-UHFFFAOYSA-N tert-butyl 4-[6-[(2-methoxypyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound COC1=NC=CC=C1NC1=CC(OC2CCN(CC2)C(=O)OC(C)(C)C)=NC=N1 QQDJBTGICVXVCN-UHFFFAOYSA-N 0.000 description 1
• UTTFZIMHPCSNCH-UHFFFAOYSA-N tert-butyl 4-[6-[(2-methylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=NC=CC=C1NC1=CC(OC2CCN(CC2)C(=O)OC(C)(C)C)=NC=N1 UTTFZIMHPCSNCH-UHFFFAOYSA-N 0.000 description 1
• SPPCJADMSJBJEM-UHFFFAOYSA-N tert-butyl 4-[6-[(2-methylpyridin-4-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=NC(C)=CC(NC=2N=CN=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C=2)=C1 SPPCJADMSJBJEM-UHFFFAOYSA-N 0.000 description 1
• MTKAAQXJBGEGCA-UHFFFAOYSA-N tert-butyl 4-[6-[(4-methylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=CC=NC=C1NC1=CC(OC2CCN(CC2)C(=O)OC(C)(C)C)=NC=N1 MTKAAQXJBGEGCA-UHFFFAOYSA-N 0.000 description 1
• MHCGMFYDBQLSBG-UHFFFAOYSA-N tert-butyl 4-[6-[(5-fluoro-4-methylpyridin-2-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=C(F)C(C)=CC(NC=2N=CN=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C=2)=N1 MHCGMFYDBQLSBG-UHFFFAOYSA-N 0.000 description 1
• LUHHZPSVZXSYEU-UHFFFAOYSA-N tert-butyl 4-[6-[(5-fluoropyridin-2-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(NC=2N=CC(F)=CC=2)=NC=N1 LUHHZPSVZXSYEU-UHFFFAOYSA-N 0.000 description 1
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• GGGPLIXPJOFOHA-UHFFFAOYSA-N tert-butyl 4-[6-[(6-chloro-5-methylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound N1=C(Cl)C(C)=CC(NC=2N=CN=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C=2)=C1 GGGPLIXPJOFOHA-UHFFFAOYSA-N 0.000 description 1
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• UTXWLRPTKGUABC-UHFFFAOYSA-N tert-butyl 4-[6-[(6-cyanopyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(NC=2C=NC(=CC=2)C#N)=NC=N1 UTXWLRPTKGUABC-UHFFFAOYSA-N 0.000 description 1
• FEYLXVDOTUMFRX-UHFFFAOYSA-N tert-butyl 4-[6-[(6-fluoropyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(NC=2C=NC(F)=CC=2)=NC=N1 FEYLXVDOTUMFRX-UHFFFAOYSA-N 0.000 description 1
• NWWQTKSOSNGVFO-UHFFFAOYSA-N tert-butyl 4-[6-[(6-methoxy-2-methylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound CC1=NC(OC)=CC=C1NC1=CC(OC2CCN(CC2)C(=O)OC(C)(C)C)=NC=N1 NWWQTKSOSNGVFO-UHFFFAOYSA-N 0.000 description 1
• UMCCJEZRYHJXRD-UHFFFAOYSA-N tert-butyl 4-[6-[(6-methoxy-5-methylpyridin-3-yl)amino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=C(C)C(OC)=NC=C1NC1=CC(OC2CCN(CC2)C(=O)OC(C)(C)C)=NC=N1 UMCCJEZRYHJXRD-UHFFFAOYSA-N 0.000 description 1
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• MRONFGQLGIAZRT-UHFFFAOYSA-N tert-butyl 4-[6-[(6-methylsulfonylpyridin-3-yl)amino]-5-nitropyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC(NC=2C=NC(=CC=2)S(C)(=O)=O)=C1[N+]([O-])=O MRONFGQLGIAZRT-UHFFFAOYSA-N 0.000 description 1
• DUUPUBWFRFCDSF-UHFFFAOYSA-N tert-butyl 4-[6-[4-cyano-5-(ethylamino)-2-fluoroanilino]pyrimidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1=C(C#N)C(NCC)=CC(NC=2N=CN=C(OC3CCN(CC3)C(=O)OC(C)(C)C)C=2)=C1F DUUPUBWFRFCDSF-UHFFFAOYSA-N 0.000 description 1
• OCYNFFJJVQTMHY-UHFFFAOYSA-N tert-butyl 4-[9-(2-fluoro-4-methylsulfonylphenyl)purin-6-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC2=C1N=CN2C1=CC=C(S(C)(=O)=O)C=C1F OCYNFFJJVQTMHY-UHFFFAOYSA-N 0.000 description 1
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• OBHZOKPGFQXCPV-UHFFFAOYSA-N tert-butyl 4-[[1-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=NC=NC2=C1C=NN2C1=CC=C(S(C)(=O)=O)C=C1 OBHZOKPGFQXCPV-UHFFFAOYSA-N 0.000 description 1
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• JYRWUSXRTGACLY-UHFFFAOYSA-N tert-butyl 4-[[3-(4-methylsulfonylphenyl)-[1,2]oxazolo[4,5-d]pyrimidin-7-yl]oxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=NC=NC2=C1ON=C2C1=CC=C(S(C)(=O)=O)C=C1 JYRWUSXRTGACLY-UHFFFAOYSA-N 0.000 description 1
• AWEXVOQVKODMQO-UHFFFAOYSA-N tert-butyl 4-[[3-(4-methylsulfonylphenyl)-[1,2]oxazolo[4,5-d]pyrimidin-7-yl]sulfanyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1SC1=NC=NC2=C1ON=C2C1=CC=C(S(C)(=O)=O)C=C1 AWEXVOQVKODMQO-UHFFFAOYSA-N 0.000 description 1
• HIKDUJLDWLIQCD-UHFFFAOYSA-N tert-butyl 4-[[5-(2-cyanopyridin-4-yl)-1,2,4-oxadiazol-3-yl]methoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OCC1=NOC(C=2C=C(N=CC=2)C#N)=N1 HIKDUJLDWLIQCD-UHFFFAOYSA-N 0.000 description 1
• NVZBQORIAUOFIZ-UHFFFAOYSA-N tert-butyl 4-[[5-[2-(2-cyanopyridin-4-yl)ethyl]-1,2,4-oxadiazol-3-yl]methoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OCC1=NOC(CCC=2C=C(N=CC=2)C#N)=N1 NVZBQORIAUOFIZ-UHFFFAOYSA-N 0.000 description 1
• CYXRQUWMIRUEEF-UHFFFAOYSA-N tert-butyl 4-[[5-[2-(2-cyanopyridin-4-yl)ethyl]-1,2,4-oxadiazol-3-yl]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CC1=NOC(CCC=2C=C(N=CC=2)C#N)=N1 CYXRQUWMIRUEEF-UHFFFAOYSA-N 0.000 description 1
• DKWHSYDHMNJQSL-UHFFFAOYSA-N tert-butyl 4-[[5-[2-(2h-tetrazol-5-yl)pyridin-4-yl]-1,2,4-oxadiazol-3-yl]methoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OCC1=NOC(C=2C=C(N=CC=2)C2=NNN=N2)=N1 DKWHSYDHMNJQSL-UHFFFAOYSA-N 0.000 description 1
• BEHIWMRJLUNCOY-UHFFFAOYSA-N tert-butyl 4-[[6-(2-fluoro-4-methylsulfonylanilino)pyrimidin-4-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC(NC=2C(=CC(=CC=2)S(C)(=O)=O)F)=NC=N1 BEHIWMRJLUNCOY-UHFFFAOYSA-N 0.000 description 1
• HDNLCVYUCUEBDC-UHFFFAOYSA-N tert-butyl 4-[[6-(4-methylsulfonylanilino)-5-nitropyrimidin-4-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=NC=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=C1[N+]([O-])=O HDNLCVYUCUEBDC-UHFFFAOYSA-N 0.000 description 1
• NRKBXROHFGYKMJ-UHFFFAOYSA-N tert-butyl 4-[[6-(4-methylsulfonylanilino)-5-nitropyrimidin-4-yl]oxymethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1COC1=NC=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=C1[N+]([O-])=O NRKBXROHFGYKMJ-UHFFFAOYSA-N 0.000 description 1
• FLYBMKKZGKKMNS-UHFFFAOYSA-N tert-butyl 4-[[[1-(2,5-difluorophenyl)pyrazolo[3,4-d]pyrimidin-4-yl]-methylamino]methyl]piperidine-1-carboxylate Chemical compound N=1C=NC=2N(C=3C(=CC=C(F)C=3)F)N=CC=2C=1N(C)CC1CCN(C(=O)OC(C)(C)C)CC1 FLYBMKKZGKKMNS-UHFFFAOYSA-N 0.000 description 1
• BKINGJBZLOUMCM-UHFFFAOYSA-N tert-butyl 4-[[[1-(2-fluoro-4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]-propan-2-ylamino]methyl]piperidine-1-carboxylate Chemical compound N=1C=NC=2N(C=3C(=CC(=CC=3)S(C)(=O)=O)F)N=CC=2C=1N(C(C)C)CC1CCN(C(=O)OC(C)(C)C)CC1 BKINGJBZLOUMCM-UHFFFAOYSA-N 0.000 description 1
• ZLEVVZJCRQACCT-UHFFFAOYSA-N tert-butyl 4-[[[1-(4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CNC1=NC=NC2=C1C=NN2C1=CC=C(S(C)(=O)=O)C=C1 ZLEVVZJCRQACCT-UHFFFAOYSA-N 0.000 description 1
• JCLVXUYUUWAWLM-UHFFFAOYSA-N tert-butyl 4-[[[6-(1,3-benzodioxol-5-ylamino)pyrimidin-4-yl]-methylamino]methyl]piperidine-1-carboxylate Chemical compound C=1C(NC=2C=C3OCOC3=CC=2)=NC=NC=1N(C)CC1CCN(C(=O)OC(C)(C)C)CC1 JCLVXUYUUWAWLM-UHFFFAOYSA-N 0.000 description 1
• FBGQLNUXCINDQY-UHFFFAOYSA-N tert-butyl 4-[[[6-(2,3-difluoroanilino)pyrimidin-4-yl]-methylamino]methyl]piperidine-1-carboxylate Chemical compound C=1C(NC=2C(=C(F)C=CC=2)F)=NC=NC=1N(C)CC1CCN(C(=O)OC(C)(C)C)CC1 FBGQLNUXCINDQY-UHFFFAOYSA-N 0.000 description 1
• DSYMWFLIFGGMHR-UHFFFAOYSA-N tert-butyl 4-[[[6-(2,4-difluoroanilino)pyrimidin-4-yl]-methylamino]methyl]piperidine-1-carboxylate Chemical compound C=1C(NC=2C(=CC(F)=CC=2)F)=NC=NC=1N(C)CC1CCN(C(=O)OC(C)(C)C)CC1 DSYMWFLIFGGMHR-UHFFFAOYSA-N 0.000 description 1
• XILPAWRVKHJCSW-UHFFFAOYSA-N tert-butyl 4-[[[6-(2,5-difluoro-4-methoxyanilino)pyrimidin-4-yl]-ethylamino]methyl]piperidine-1-carboxylate Chemical compound C=1C(NC=2C(=CC(OC)=C(F)C=2)F)=NC=NC=1N(CC)CC1CCN(C(=O)OC(C)(C)C)CC1 XILPAWRVKHJCSW-UHFFFAOYSA-N 0.000 description 1
• FMGNLQXFTXYFRO-UHFFFAOYSA-N tert-butyl 4-[[[6-(2,5-difluoro-4-methylsulfonylanilino)pyrimidin-4-yl]-ethylamino]methyl]piperidine-1-carboxylate Chemical compound C=1C(NC=2C(=CC(=C(F)C=2)S(C)(=O)=O)F)=NC=NC=1N(CC)CC1CCN(C(=O)OC(C)(C)C)CC1 FMGNLQXFTXYFRO-UHFFFAOYSA-N 0.000 description 1
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• SBLGYKMIWXUSJX-UHFFFAOYSA-N tert-butyl 4-[[methyl-[6-[[5-(trifluoromethyl)pyridin-2-yl]amino]pyrimidin-4-yl]amino]methyl]piperidine-1-carboxylate Chemical compound C=1C(NC=2N=CC(=CC=2)C(F)(F)F)=NC=NC=1N(C)CC1CCN(C(=O)OC(C)(C)C)CC1 SBLGYKMIWXUSJX-UHFFFAOYSA-N 0.000 description 1
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