JP2018109038A5 - - Google Patents

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Publication number

JP2018109038A5

JP2018109038A5 JP2018029462A JP2018029462A JP2018109038A5 JP 2018109038 A5 JP2018109038 A5 JP 2018109038A5 JP 2018029462 A JP2018029462 A JP 2018029462A JP 2018029462 A JP2018029462 A JP 2018029462A JP 2018109038 A5 JP2018109038 A5 JP 2018109038A5

Authority

JP

Japan

Prior art keywords

methyl

pyrazol

trifluoromethyl

pyrimidine

diamine

Prior art date

2018-02-22

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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• Espacenet
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• -1 cyclopropylsulfonyl Chemical group 0.000 claims description 92
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 150000001875 compounds Chemical class 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 150000004985 diamines Chemical class 0.000 claims description 6
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 5
• 150000003839 salts Chemical class 0.000 claims description 5
• VCISAWBZRDSYAE-UHFFFAOYSA-N 1-[4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-5-methylpyrazol-1-yl]piperidin-1-yl]-2-methylpropan-1-one Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3CCN(CC3)C(=O)C(C)C)N=C2)C)=N1 VCISAWBZRDSYAE-UHFFFAOYSA-N 0.000 claims description 4
• XBQUAYXWKXQAQK-UHFFFAOYSA-N 2-methyl-1-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propan-2-ol Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(CC(C)(C)O)C=2)C)=N1 XBQUAYXWKXQAQK-UHFFFAOYSA-N 0.000 claims description 4
• UYRIPPKFZHHKOO-UHFFFAOYSA-N 2-n-[1-(2-methoxyethyl)-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(CCOC)C=2)C)=N1 UYRIPPKFZHHKOO-UHFFFAOYSA-N 0.000 claims description 4
• NUWDQLQAMMOSMC-UHFFFAOYSA-N 2-n-[1-(2-methoxyethyl)-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(CCOC)N=C2)C)=N1 NUWDQLQAMMOSMC-UHFFFAOYSA-N 0.000 claims description 4
• NBHWVIRAPWUZAU-MRVPVSSYSA-N 2-n-[1-[(2r)-1-methoxypropan-2-yl]-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N([C@H](C)COC)N=C2)C)=N1 NBHWVIRAPWUZAU-MRVPVSSYSA-N 0.000 claims description 4
• VTKNOHUCAVQNQC-UHFFFAOYSA-N 2-n-[5-chloro-1-(3-fluoro-1-methylpiperidin-4-yl)pyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C3C(CN(C)CC3)F)N=C2)Cl)=N1 VTKNOHUCAVQNQC-UHFFFAOYSA-N 0.000 claims description 4
• CYCBICICEPWXQS-UHFFFAOYSA-N 4-methyl-5-(trifluoromethyl)-1H-pyrimidine-2,4-diamine Chemical compound CC1(NC(=NC=C1C(F)(F)F)N)N CYCBICICEPWXQS-UHFFFAOYSA-N 0.000 claims description 4
• LVRGRHRVURAMCV-UHFFFAOYSA-N 4-n-methyl-2-n-[3-methyl-1-[2-(1h-1,2,4-triazol-5-yl)propan-2-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C(C)(C)C=2NC=NN=2)C)=N1 LVRGRHRVURAMCV-UHFFFAOYSA-N 0.000 claims description 4
• MOYZEDPGMAHGRR-UHFFFAOYSA-N 5-chloro-4-methoxy-n-(3-methyl-1-methylsulfonylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)S(C)(=O)=O)C)=N1 MOYZEDPGMAHGRR-UHFFFAOYSA-N 0.000 claims description 4
• QVMQIGDQNDCVJU-UHFFFAOYSA-N 1-[5-chloro-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]cyclopropane-1-carbonitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(N=C2)C2(CC2)C#N)Cl)=N1 QVMQIGDQNDCVJU-UHFFFAOYSA-N 0.000 claims description 3
• JJLXBPFAWIFXLU-UHFFFAOYSA-N 2-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]-n,2-dimethylpropanamide Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)C(=O)NC)C)=N1 JJLXBPFAWIFXLU-UHFFFAOYSA-N 0.000 claims description 3
• KXCWSMLDPVSABQ-LLVKDONJSA-N (2r)-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)[C@H](C)C(=O)N2CCCC2)C)=N1 KXCWSMLDPVSABQ-LLVKDONJSA-N 0.000 claims description 2
• VDMCENGCDUPAOP-SSDOTTSWSA-N (2r)-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)[C@H](C)C#N)C)=N1 VDMCENGCDUPAOP-SSDOTTSWSA-N 0.000 claims description 2
• URUOOTDTWWRVCU-LLVKDONJSA-N (2r)-2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N([C@H](C)C(=O)N3CCCC3)N=C2)C)=N1 URUOOTDTWWRVCU-LLVKDONJSA-N 0.000 claims description 2
• KXCWSMLDPVSABQ-NSHDSACASA-N (2s)-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)[C@@H](C)C(=O)N2CCCC2)C)=N1 KXCWSMLDPVSABQ-NSHDSACASA-N 0.000 claims description 2
• VDMCENGCDUPAOP-ZETCQYMHSA-N (2s)-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)[C@@H](C)C#N)C)=N1 VDMCENGCDUPAOP-ZETCQYMHSA-N 0.000 claims description 2
• URUOOTDTWWRVCU-NSHDSACASA-N (2s)-2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N([C@@H](C)C(=O)N3CCCC3)N=C2)C)=N1 URUOOTDTWWRVCU-NSHDSACASA-N 0.000 claims description 2
• DROSCFWTQSHEAY-ZETCQYMHSA-N (2s)-2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N([C@@H](C)C#N)N=C2)C)=N1 DROSCFWTQSHEAY-ZETCQYMHSA-N 0.000 claims description 2
• BSAIBMQUELDSOM-VIFPVBQESA-N (2s)-n,n-dimethyl-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanamide Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)[C@@H](C)C(=O)N(C)C)C)=N1 BSAIBMQUELDSOM-VIFPVBQESA-N 0.000 claims description 2
• WSKNTCKMSASUDS-UHFFFAOYSA-N 1-[3-chloro-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(CC(C)(C)O)C=2)Cl)=N1 WSKNTCKMSASUDS-UHFFFAOYSA-N 0.000 claims description 2
• GPYHHGOVZOCNTR-UHFFFAOYSA-N 1-[3-cyclopropyl-4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(CC(C)(C)O)C=2)C2CC2)=N1 GPYHHGOVZOCNTR-UHFFFAOYSA-N 0.000 claims description 2
• ABZMZCOIHUNVOW-UHFFFAOYSA-N 1-[3-cyclopropyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(CC(C)(C)O)C=2)C2CC2)=N1 ABZMZCOIHUNVOW-UHFFFAOYSA-N 0.000 claims description 2
• FXKQDSOJJGWXTI-UHFFFAOYSA-N 1-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2(CCC2)C#N)C)=N1 FXKQDSOJJGWXTI-UHFFFAOYSA-N 0.000 claims description 2
• MYGTVURNPPBOCT-UHFFFAOYSA-N 1-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]cyclopropane-1-carbonitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2(CC2)C#N)C)=N1 MYGTVURNPPBOCT-UHFFFAOYSA-N 0.000 claims description 2
• PMJBUSJOYPSBOJ-UHFFFAOYSA-N 1-[3-tert-butyl-4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(CC(C)(C)O)C=2)C(C)(C)C)=N1 PMJBUSJOYPSBOJ-UHFFFAOYSA-N 0.000 claims description 2
• ANHXDNQMHUSVLL-UHFFFAOYSA-N 1-[4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]piperidin-1-yl]-2-methylpropan-1-one Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CCN(CC2)C(=O)C(C)C)C)=N1 ANHXDNQMHUSVLL-UHFFFAOYSA-N 0.000 claims description 2
• TUZWQAYKYDMIEH-UHFFFAOYSA-N 1-[4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CCN(CC2)C(C)=O)C)=N1 TUZWQAYKYDMIEH-UHFFFAOYSA-N 0.000 claims description 2
• UNRCHRZMPHRCNO-UHFFFAOYSA-N 1-[4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-5-methylpyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3CCN(CC3)C(C)=O)N=C2)C)=N1 UNRCHRZMPHRCNO-UHFFFAOYSA-N 0.000 claims description 2
• DQSKWTJRYAQOEN-UHFFFAOYSA-N 1-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(CC(C)(C)O)C=2)C)=N1 DQSKWTJRYAQOEN-UHFFFAOYSA-N 0.000 claims description 2
• MAIPJZAUYBSGNY-UHFFFAOYSA-N 1-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-propan-2-ylpyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(CC(C)(C)O)C=2)C(C)C)=N1 MAIPJZAUYBSGNY-UHFFFAOYSA-N 0.000 claims description 2
• DBOKVPCOQFCTCI-UHFFFAOYSA-N 1-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-5-methylpyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(CC(C)(C)O)N=C2)C)=N1 DBOKVPCOQFCTCI-UHFFFAOYSA-N 0.000 claims description 2
• CIZNGWPPRKQMSM-UHFFFAOYSA-N 1-[4-[[5-chloro-4-(methylamino)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(Cl)C(NC)=NC(NC=2C(=NN(CC(C)(C)O)C=2)C)=N1 CIZNGWPPRKQMSM-UHFFFAOYSA-N 0.000 claims description 2
• KJZCKIGWOBSZIZ-UHFFFAOYSA-N 1-[5-chloro-4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(CC(C)(C)O)N=C2)Cl)=N1 KJZCKIGWOBSZIZ-UHFFFAOYSA-N 0.000 claims description 2
• IKBCWJODRQLGHR-UHFFFAOYSA-N 1-[5-chloro-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropan-2-ol Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(CC(C)(C)O)N=C2)Cl)=N1 IKBCWJODRQLGHR-UHFFFAOYSA-N 0.000 claims description 2
• JYKOFBJKGMDNNI-UHFFFAOYSA-N 1-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(N=C2)C2(CCC2)C#N)C)=N1 JYKOFBJKGMDNNI-UHFFFAOYSA-N 0.000 claims description 2
• QBIIPMKUEZQNFW-UHFFFAOYSA-N 2,2-dimethyl-3-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(CC(C)(C)C#N)C=2)C)=N1 QBIIPMKUEZQNFW-UHFFFAOYSA-N 0.000 claims description 2
• PDISIGKAKURBGN-UHFFFAOYSA-N 2,2-dimethyl-3-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(CC(C)(C)C#N)N=C2)C)=N1 PDISIGKAKURBGN-UHFFFAOYSA-N 0.000 claims description 2
• JMPAUGJZZZVNSP-UHFFFAOYSA-N 2-[(1,3-dimethylpyrazol-4-yl)amino]-4-(methylamino)pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC=2C(=NN(C)C=2)C)=N1 JMPAUGJZZZVNSP-UHFFFAOYSA-N 0.000 claims description 2
• TYQQFDCVHCYAAQ-UHFFFAOYSA-N 2-[(1,5-dimethylpyrazol-4-yl)amino]-4-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonitrile Chemical compound C1=NN(C)C(C)=C1NC1=NC=C(C#N)C(OCC(F)(F)F)=N1 TYQQFDCVHCYAAQ-UHFFFAOYSA-N 0.000 claims description 2
• FBJLNXDBSYRGOX-UHFFFAOYSA-N 2-[(1,5-dimethylpyrazol-4-yl)amino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carbonitrile Chemical compound C1=NN(C)C(C)=C1NC1=NC=C(C#N)C(NCC(F)(F)F)=N1 FBJLNXDBSYRGOX-UHFFFAOYSA-N 0.000 claims description 2
• AJVGIWGWKVAECK-UHFFFAOYSA-N 2-[(1,5-dimethylpyrazol-4-yl)amino]-4-(ethylamino)pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NCC)=NC(NC2=C(N(C)N=C2)C)=N1 AJVGIWGWKVAECK-UHFFFAOYSA-N 0.000 claims description 2
• DHBYPNGGSQZPSR-UHFFFAOYSA-N 2-[(1,5-dimethylpyrazol-4-yl)amino]-4-(methylamino)pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC2=C(N(C)N=C2)C)=N1 DHBYPNGGSQZPSR-UHFFFAOYSA-N 0.000 claims description 2
• KMDGFQKNLCAUSR-UHFFFAOYSA-N 2-[(1,5-dimethylpyrazol-4-yl)amino]-4-methoxypyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(OC)=NC(NC2=C(N(C)N=C2)C)=N1 KMDGFQKNLCAUSR-UHFFFAOYSA-N 0.000 claims description 2
• SHGBCEKYABDSAI-UHFFFAOYSA-N 2-[(1-ethyl-3-methylpyrazol-4-yl)amino]-4-(methylamino)pyrimidine-5-carbonitrile Chemical compound CC1=NN(CC)C=C1NC1=NC=C(C#N)C(NC)=N1 SHGBCEKYABDSAI-UHFFFAOYSA-N 0.000 claims description 2
• ZPJYLUOMTWDLAI-UHFFFAOYSA-N 2-[(1-ethyl-5-methylpyrazol-4-yl)amino]-4-(methylamino)pyrimidine-5-carbonitrile Chemical compound CCN1N=CC(NC=2N=C(NC)C(C#N)=CN=2)=C1C ZPJYLUOMTWDLAI-UHFFFAOYSA-N 0.000 claims description 2
• OJEWMLUIKQSZPR-UHFFFAOYSA-N 2-[(1-ethyl-5-methylpyrazol-4-yl)amino]-4-methoxypyrimidine-5-carbonitrile Chemical compound CCN1N=CC(NC=2N=C(OC)C(C#N)=CN=2)=C1C OJEWMLUIKQSZPR-UHFFFAOYSA-N 0.000 claims description 2
• RJYKAQHJDHRVCS-UHFFFAOYSA-N 2-[3-chloro-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C(C)(C)C#N)Cl)=N1 RJYKAQHJDHRVCS-UHFFFAOYSA-N 0.000 claims description 2
• FZYTYNCBJMMBBJ-UHFFFAOYSA-N 2-[3-cyclopropyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C(C)(C)C#N)C2CC2)=N1 FZYTYNCBJMMBBJ-UHFFFAOYSA-N 0.000 claims description 2
• ZRWMINOKUFLOOK-UHFFFAOYSA-N 2-[3-ethyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-2-methylpropanenitrile Chemical compound CCC1=NN(C(C)(C)C#N)C=C1NC1=NC=C(C(F)(F)F)C(NC)=N1 ZRWMINOKUFLOOK-UHFFFAOYSA-N 0.000 claims description 2
• XTXIOXRTGSWVQZ-UHFFFAOYSA-N 2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]cyclopentan-1-ol Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2C(CCC2)O)C)=N1 XTXIOXRTGSWVQZ-UHFFFAOYSA-N 0.000 claims description 2
• BQPOLMVAASMQGL-UHFFFAOYSA-N 2-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-3-cyclopropylpyrazol-1-yl]-2-methylpropanenitrile Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C(C)(C)C#N)C2CC2)=N1 BQPOLMVAASMQGL-UHFFFAOYSA-N 0.000 claims description 2
• GPGVVCGTAPAQOE-UHFFFAOYSA-N 2-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-3-methylpyrazol-1-yl]-2-methylpropanenitrile Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C(C)(C)C#N)C)=N1 GPGVVCGTAPAQOE-UHFFFAOYSA-N 0.000 claims description 2
• ZBHGYOPZGYZBQP-UHFFFAOYSA-N 2-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-5-methylpyrazol-1-yl]-2-methylpropanenitrile Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(N=C2)C(C)(C)C#N)C)=N1 ZBHGYOPZGYZBQP-UHFFFAOYSA-N 0.000 claims description 2
• SIWVTKBPTPATQW-UHFFFAOYSA-N 2-[4-[[4-(cyclopropylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]-2-methylpropanenitrile Chemical compound CC1=NN(C(C)(C)C#N)C=C1NC1=NC=C(C(F)(F)F)C(NC2CC2)=N1 SIWVTKBPTPATQW-UHFFFAOYSA-N 0.000 claims description 2
• OEZVRXBTAQZHBE-UHFFFAOYSA-N 2-[4-[[4-(cyclopropylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]-n,2-dimethylpropanamide Chemical compound CC1=NN(C(C)(C)C(=O)NC)C=C1NC1=NC=C(C(F)(F)F)C(NC2CC2)=N1 OEZVRXBTAQZHBE-UHFFFAOYSA-N 0.000 claims description 2
• AITFWELTOGQGJL-UHFFFAOYSA-N 2-[4-[[4-(cyclopropylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-5-methylpyrazol-1-yl]-n,2-dimethylpropanamide Chemical compound CNC(=O)C(C)(C)N1N=CC(NC=2N=C(NC3CC3)C(=CN=2)C(F)(F)F)=C1C AITFWELTOGQGJL-UHFFFAOYSA-N 0.000 claims description 2
• JOGFTGFXYFZCEZ-UHFFFAOYSA-N 2-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-5-methylpyrazol-1-yl]-n,2-dimethylpropanamide Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(N=C2)C(C)(C)C(=O)NC)C)=N1 JOGFTGFXYFZCEZ-UHFFFAOYSA-N 0.000 claims description 2
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• OFEKPYXOGYKSGL-UHFFFAOYSA-N 2-[5-chloro-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-n,2-dimethylpropanamide Chemical compound CNC(=O)C(C)(C)N1N=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C1Cl OFEKPYXOGYKSGL-UHFFFAOYSA-N 0.000 claims description 2
• HKURXGMWTBDIRM-UHFFFAOYSA-N 2-[5-chloro-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-n-ethyl-2-methylpropanamide Chemical compound CCNC(=O)C(C)(C)N1N=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C1Cl HKURXGMWTBDIRM-UHFFFAOYSA-N 0.000 claims description 2
• GTCMDRGDGIXHNJ-UHFFFAOYSA-N 2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]cyclopentan-1-ol Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C3C(CCC3)O)N=C2)C)=N1 GTCMDRGDGIXHNJ-UHFFFAOYSA-N 0.000 claims description 2
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• FJCJNABMUKFNKF-UHFFFAOYSA-N 2-[[3-methyl-1-(oxetan-3-yl)pyrazol-4-yl]amino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carbonitrile Chemical compound CC1=NN(C2COC2)C=C1NC1=NC=C(C#N)C(NCC(F)(F)F)=N1 FJCJNABMUKFNKF-UHFFFAOYSA-N 0.000 claims description 2
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• ZPPUMAMZIMPJGP-UHFFFAOYSA-N 2-methyl-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C(C)(C)C#N)C)=N1 ZPPUMAMZIMPJGP-UHFFFAOYSA-N 0.000 claims description 2
• PIXIVQOHSXFPNB-UHFFFAOYSA-N 2-methyl-2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(N=C2)C(C)(C)C(=O)N2CCCC2)C)=N1 PIXIVQOHSXFPNB-UHFFFAOYSA-N 0.000 claims description 2
• MCSOTLQDXSOUIK-UHFFFAOYSA-N 2-methyl-2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]-n-(2,2,2-trifluoroethyl)propanamide Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(N=C2)C(C)(C)C(=O)NCC(F)(F)F)C)=N1 MCSOTLQDXSOUIK-UHFFFAOYSA-N 0.000 claims description 2
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• PNVGBJCKBAVGIZ-UHFFFAOYSA-N 2-n-(1-butan-2-ylsulfonyl-5-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound CCC(C)S(=O)(=O)N1N=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C1C PNVGBJCKBAVGIZ-UHFFFAOYSA-N 0.000 claims description 2
• FWNMRJUFVPADOZ-UHFFFAOYSA-N 2-n-(1-butyl-5-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound CCCCN1N=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C1C FWNMRJUFVPADOZ-UHFFFAOYSA-N 0.000 claims description 2
• KBLIASYDZLOKGS-UHFFFAOYSA-N 2-n-(1-cyclopropylsulfonyl-3-methylpyrazol-4-yl)-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)S(=O)(=O)C2CC2)C)=N1 KBLIASYDZLOKGS-UHFFFAOYSA-N 0.000 claims description 2
• PXPZQOZZYAJGQB-UHFFFAOYSA-N 2-n-(1-cyclopropylsulfonyl-3-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)S(=O)(=O)C2CC2)C)=N1 PXPZQOZZYAJGQB-UHFFFAOYSA-N 0.000 claims description 2
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• CWXRZAQVLAXZEA-UHFFFAOYSA-N 2-n-(1-ethylpyrazol-3-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound CCN1C=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=N1 CWXRZAQVLAXZEA-UHFFFAOYSA-N 0.000 claims description 2
• PAZJJZMRMPCJKO-UHFFFAOYSA-N 2-n-(1-ethylsulfonyl-3-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound CC1=NN(S(=O)(=O)CC)C=C1NC1=NC=C(C(F)(F)F)C(NC)=N1 PAZJJZMRMPCJKO-UHFFFAOYSA-N 0.000 claims description 2
• MWKAXAWQIIXQKL-UHFFFAOYSA-N 2-n-(1-ethylsulfonyl-5-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound CCS(=O)(=O)N1N=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C1C MWKAXAWQIIXQKL-UHFFFAOYSA-N 0.000 claims description 2
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• VCUZXNAXBCTLQJ-UHFFFAOYSA-N 2-n-(3-cyclobutyl-1-methylpyrazol-4-yl)-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C)C=2)C2CCC2)=N1 VCUZXNAXBCTLQJ-UHFFFAOYSA-N 0.000 claims description 2
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• QSRNIRWKKRHBNL-UHFFFAOYSA-N 2-n-(5-chloro-1-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C)N=C2)Cl)=N1 QSRNIRWKKRHBNL-UHFFFAOYSA-N 0.000 claims description 2
• DHOQVBNMFBZGTO-UHFFFAOYSA-N 2-n-(5-chloro-1-propan-2-ylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C(C)C)N=C2)Cl)=N1 DHOQVBNMFBZGTO-UHFFFAOYSA-N 0.000 claims description 2
• NZDQZCWCFVSEFG-UHFFFAOYSA-N 2-n-(5-cyclobutyl-1-methylpyrazol-4-yl)-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C)N=C2)C2CCC2)=N1 NZDQZCWCFVSEFG-UHFFFAOYSA-N 0.000 claims description 2
• CJCQHXHUDFJHSV-UHFFFAOYSA-N 2-n-(5-cyclobutyl-1-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C)N=C2)C2CCC2)=N1 CJCQHXHUDFJHSV-UHFFFAOYSA-N 0.000 claims description 2
• WWTGILZJUOKRHR-UHFFFAOYSA-N 2-n-(5-cyclopropyl-1-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C)N=C2)C2CC2)=N1 WWTGILZJUOKRHR-UHFFFAOYSA-N 0.000 claims description 2
• CTDFPOAQLDAERJ-UHFFFAOYSA-N 2-n-(5-cyclopropyl-2-methylpyrazol-3-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2N(N=C(C=2)C2CC2)C)=N1 CTDFPOAQLDAERJ-UHFFFAOYSA-N 0.000 claims description 2
• XTZNRGPELVIIPV-UHFFFAOYSA-N 2-n-(5-methoxy-1-methylpyrazol-4-yl)-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C)N=C2)OC)=N1 XTZNRGPELVIIPV-UHFFFAOYSA-N 0.000 claims description 2
• BINSQRWUKUWERN-UHFFFAOYSA-N 2-n-[1-(1-ethyl-3-fluoropiperidin-4-yl)-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound FC1CN(CC)CCC1N1N=C(C)C(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C1 BINSQRWUKUWERN-UHFFFAOYSA-N 0.000 claims description 2
• QBRPYAXUPKIKML-UHFFFAOYSA-N 2-n-[1-(1-methoxy-2-methylpropan-2-yl)-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C(C)(C)COC)C)=N1 QBRPYAXUPKIKML-UHFFFAOYSA-N 0.000 claims description 2
• IMCOYUGEGVGEJN-UHFFFAOYSA-N 2-n-[1-(1-methoxy-2-methylpropan-2-yl)-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(N=C2)C(C)(C)COC)C)=N1 IMCOYUGEGVGEJN-UHFFFAOYSA-N 0.000 claims description 2
• QPEVTQXLTTXBIX-UHFFFAOYSA-N 2-n-[1-(2,2-dimethyl-1,3-dioxan-5-yl)-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2COC(C)(C)OC2)C)=N1 QPEVTQXLTTXBIX-UHFFFAOYSA-N 0.000 claims description 2
• LWCCBIBAYGOWTG-UHFFFAOYSA-N 2-n-[1-(2,6-dimethyloxan-4-yl)-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2CC(C)OC(C)C2)C)=N1 LWCCBIBAYGOWTG-UHFFFAOYSA-N 0.000 claims description 2
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• RNCMKOWVACJZQS-UHFFFAOYSA-N 2-n-[1-(2-methoxycyclopentyl)-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2C(CCC2)OC)C)=N1 RNCMKOWVACJZQS-UHFFFAOYSA-N 0.000 claims description 2
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• CJYZGTCNHHTRNA-UHFFFAOYSA-N 2-n-[1-(4-chlorophenyl)-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C=2C=CC(Cl)=CC=2)C)=N1 CJYZGTCNHHTRNA-UHFFFAOYSA-N 0.000 claims description 2
• YIRPGGXCZZSLPJ-UHFFFAOYSA-N 2-n-[1-(4-chlorophenyl)-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(N=C2)C=2C=CC(Cl)=CC=2)C)=N1 YIRPGGXCZZSLPJ-UHFFFAOYSA-N 0.000 claims description 2
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• SHZYCRUAOFEGJN-UHFFFAOYSA-N 2-n-[1-(4-cyclopropylsulfonylphenyl)-5-methylpyrazol-4-yl]-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(N=C2)C=2C=CC(=CC=2)S(=O)(=O)C2CC2)C)=N1 SHZYCRUAOFEGJN-UHFFFAOYSA-N 0.000 claims description 2
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• YKJFUBQPXZWRQL-UHFFFAOYSA-N 2-n-[1-(cyclopropylmethyl)-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(CC3CC3)N=C2)C)=N1 YKJFUBQPXZWRQL-UHFFFAOYSA-N 0.000 claims description 2
• CPJYLVFAIWDLTI-UHFFFAOYSA-N 2-n-[1-(difluoromethyl)-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C(F)F)C)=N1 CPJYLVFAIWDLTI-UHFFFAOYSA-N 0.000 claims description 2
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• QKMHJNMVLOYTSC-MRVPVSSYSA-N 2-n-[1-[(2r)-2-methoxypropyl]-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C[C@@H](C)OC)C=2)C)=N1 QKMHJNMVLOYTSC-MRVPVSSYSA-N 0.000 claims description 2
• MZGFHCBTAJGNMO-MRVPVSSYSA-N 2-n-[1-[(2r)-2-methoxypropyl]-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C[C@@H](C)OC)N=C2)C)=N1 MZGFHCBTAJGNMO-MRVPVSSYSA-N 0.000 claims description 2
• MHOPIRARAOAFTG-QMMMGPOBSA-N 2-n-[1-[(2s)-1-methoxypropan-2-yl]-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)[C@@H](C)COC)C)=N1 MHOPIRARAOAFTG-QMMMGPOBSA-N 0.000 claims description 2
• QKMHJNMVLOYTSC-QMMMGPOBSA-N 2-n-[1-[(2s)-2-methoxypropyl]-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C[C@H](C)OC)C=2)C)=N1 QKMHJNMVLOYTSC-QMMMGPOBSA-N 0.000 claims description 2
• MZGFHCBTAJGNMO-QMMMGPOBSA-N 2-n-[1-[(2s)-2-methoxypropyl]-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C[C@H](C)OC)N=C2)C)=N1 MZGFHCBTAJGNMO-QMMMGPOBSA-N 0.000 claims description 2
• HJAUQNCGNYFLKU-UHFFFAOYSA-N 2-n-[1-[1-(1,3-dioxolan-2-ylmethyl)piperidin-4-yl]-3-methylpyrazol-4-yl]-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CCN(CC3OCCO3)CC2)C)=N1 HJAUQNCGNYFLKU-UHFFFAOYSA-N 0.000 claims description 2
• DEKQSPVBLYHDOA-UHFFFAOYSA-N 2-n-[1-[1-(1,3-dioxolan-2-ylmethyl)piperidin-4-yl]-5-methylpyrazol-4-yl]-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3CCN(CC4OCCO4)CC3)N=C2)C)=N1 DEKQSPVBLYHDOA-UHFFFAOYSA-N 0.000 claims description 2
• CZMUHYCRECWZCX-UHFFFAOYSA-N 2-n-[1-[1-(1,3-dioxolan-2-ylmethyl)pyrrolidin-3-yl]-3-methylpyrazol-4-yl]-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CN(CC3OCCO3)CC2)C)=N1 CZMUHYCRECWZCX-UHFFFAOYSA-N 0.000 claims description 2
• UVAFUEAVNVTIMW-UHFFFAOYSA-N 2-n-[1-[1-(1,3-dioxolan-2-ylmethyl)pyrrolidin-3-yl]-5-methylpyrazol-4-yl]-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3CN(CC4OCCO4)CC3)N=C2)C)=N1 UVAFUEAVNVTIMW-UHFFFAOYSA-N 0.000 claims description 2
• LCKMLIPPUMPDCV-UHFFFAOYSA-N 2-n-[1-[1-(2-fluoroethyl)piperidin-4-yl]-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2CCN(CCF)CC2)C)=N1 LCKMLIPPUMPDCV-UHFFFAOYSA-N 0.000 claims description 2
• YJUWLJLTEPZWBY-UHFFFAOYSA-N 2-n-[1-[1-(2-fluoroethyl)piperidin-4-yl]-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C3CCN(CCF)CC3)N=C2)C)=N1 YJUWLJLTEPZWBY-UHFFFAOYSA-N 0.000 claims description 2
• KQZXYJBWIDZBDR-UHFFFAOYSA-N 2-n-[1-[1-(2-methoxyethyl)piperidin-4-yl]-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2CCN(CCOC)CC2)C)=N1 KQZXYJBWIDZBDR-UHFFFAOYSA-N 0.000 claims description 2
• RQLBMEWUVWNMGM-UHFFFAOYSA-N 2-n-[1-[1-(2-methoxyethyl)piperidin-4-yl]-5-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C3CCN(CCOC)CC3)N=C2)C)=N1 RQLBMEWUVWNMGM-UHFFFAOYSA-N 0.000 claims description 2
• WQELVDRHGRUOCD-UHFFFAOYSA-N 2-n-[1-[3-fluoro-1-(oxetan-3-yl)piperidin-4-yl]-3-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2C(CN(CC2)C2COC2)F)C)=N1 WQELVDRHGRUOCD-UHFFFAOYSA-N 0.000 claims description 2
• WBVTVUDAJGWWNN-UHFFFAOYSA-N 2-n-[5-(dimethylamino)-1-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C)N=C2)N(C)C)=N1 WBVTVUDAJGWWNN-UHFFFAOYSA-N 0.000 claims description 2
• WKMNBGTUXNDAQB-UHFFFAOYSA-N 2-n-[5-(fluoromethyl)-1-methylpyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C)N=C2)CF)=N1 WKMNBGTUXNDAQB-UHFFFAOYSA-N 0.000 claims description 2
• AJOLUFNTIPATNW-UHFFFAOYSA-N 2-n-[5-chloro-1-(1-ethyl-3-fluoropiperidin-4-yl)pyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound FC1CN(CC)CCC1N1C(Cl)=C(NC=2N=C(NC)C(=CN=2)C(F)(F)F)C=N1 AJOLUFNTIPATNW-UHFFFAOYSA-N 0.000 claims description 2
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• UKONAAOPUWORRD-UHFFFAOYSA-N 2-n-[5-chloro-1-(oxetan-3-yl)pyrazol-4-yl]-4-n-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C3COC3)N=C2)Cl)=N1 UKONAAOPUWORRD-UHFFFAOYSA-N 0.000 claims description 2
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• QMBBRYHGFXKLAF-UHFFFAOYSA-N 2-n-[5-chloro-1-[3-fluoro-1-(oxetan-3-yl)piperidin-4-yl]pyrazol-4-yl]-4-n-ethyl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3C(CN(CC3)C3COC3)F)N=C2)Cl)=N1 QMBBRYHGFXKLAF-UHFFFAOYSA-N 0.000 claims description 2
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• YCILXEGUNDPVFC-UHFFFAOYSA-N 3-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(CCC#N)C=2)C)=N1 YCILXEGUNDPVFC-UHFFFAOYSA-N 0.000 claims description 2
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• KULFBTUVKAKKJL-UHFFFAOYSA-N 3-methyl-1-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]butan-2-ol Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(CC(O)C(C)C)C=2)C)=N1 KULFBTUVKAKKJL-UHFFFAOYSA-N 0.000 claims description 2
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• ABNVVPZQDZUQDH-UHFFFAOYSA-N 4-(methylamino)-2-[(5-methyl-1-propan-2-ylpyrazol-4-yl)amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC2=C(N(C(C)C)N=C2)C)=N1 ABNVVPZQDZUQDH-UHFFFAOYSA-N 0.000 claims description 2
• JTUHMKIXBOISSW-UHFFFAOYSA-N 4-(methylamino)-2-[(5-methyl-1-propylpyrazol-4-yl)amino]pyrimidine-5-carbonitrile Chemical compound CCCN1N=CC(NC=2N=C(NC)C(C#N)=CN=2)=C1C JTUHMKIXBOISSW-UHFFFAOYSA-N 0.000 claims description 2
• PELWZUJUSISLDT-UHFFFAOYSA-N 4-(methylamino)-2-[[3-methyl-1-(2,2,2-trifluoroethyl)pyrazol-4-yl]amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC=2C(=NN(CC(F)(F)F)C=2)C)=N1 PELWZUJUSISLDT-UHFFFAOYSA-N 0.000 claims description 2
• GJBZNFWVWJFMBF-UHFFFAOYSA-N 4-(methylamino)-2-[[3-methyl-1-(oxan-4-yl)pyrazol-4-yl]amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC=2C(=NN(C=2)C2CCOCC2)C)=N1 GJBZNFWVWJFMBF-UHFFFAOYSA-N 0.000 claims description 2
• MZAIPMWQLSUUDP-UHFFFAOYSA-N 4-(methylamino)-2-[[3-methyl-1-(oxetan-3-yl)pyrazol-4-yl]amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC=2C(=NN(C=2)C2COC2)C)=N1 MZAIPMWQLSUUDP-UHFFFAOYSA-N 0.000 claims description 2
• RQAZXNDENUGYJO-UHFFFAOYSA-N 4-(methylamino)-2-[[3-methyl-1-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyrazol-4-yl]amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC=2C(=NN(C=2)C2CCN(CC(F)(F)F)CC2)C)=N1 RQAZXNDENUGYJO-UHFFFAOYSA-N 0.000 claims description 2
• FIWDXFIMKVZZGV-UHFFFAOYSA-N 4-(methylamino)-2-[[5-methyl-1-(2,2,2-trifluoroethyl)pyrazol-4-yl]amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC2=C(N(CC(F)(F)F)N=C2)C)=N1 FIWDXFIMKVZZGV-UHFFFAOYSA-N 0.000 claims description 2
• AUSGXPJGVCMPCN-UHFFFAOYSA-N 4-(methylamino)-2-[[5-methyl-1-(oxan-4-yl)pyrazol-4-yl]amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC2=C(N(C3CCOCC3)N=C2)C)=N1 AUSGXPJGVCMPCN-UHFFFAOYSA-N 0.000 claims description 2
• WYTFXJSJWAQPLE-UHFFFAOYSA-N 4-(methylamino)-2-[[5-methyl-1-(oxetan-3-yl)pyrazol-4-yl]amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC2=C(N(C3COC3)N=C2)C)=N1 WYTFXJSJWAQPLE-UHFFFAOYSA-N 0.000 claims description 2
• JFJYNKFUCMWUPC-UHFFFAOYSA-N 4-(methylamino)-2-[[5-methyl-1-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyrazol-4-yl]amino]pyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(NC)=NC(NC2=C(N(C3CCN(CC(F)(F)F)CC3)N=C2)C)=N1 JFJYNKFUCMWUPC-UHFFFAOYSA-N 0.000 claims description 2
• SHXOROCKOCBNPB-UHFFFAOYSA-N 4-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]benzonitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C=2C=CC(=CC=2)C#N)C)=N1 SHXOROCKOCBNPB-UHFFFAOYSA-N 0.000 claims description 2
• KVYCHJLMEFCGPP-UHFFFAOYSA-N 4-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-3-methylpyrazol-1-yl]-n,n-dimethylbenzamide Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C=2C=CC(=CC=2)C(=O)N(C)C)C)=N1 KVYCHJLMEFCGPP-UHFFFAOYSA-N 0.000 claims description 2
• GJVUSQSFOPXDPE-UHFFFAOYSA-N 4-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-3-methylpyrazol-1-yl]benzonitrile Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C=2C=CC(=CC=2)C#N)C)=N1 GJVUSQSFOPXDPE-UHFFFAOYSA-N 0.000 claims description 2
• IKKSSBRMCKIQCO-UHFFFAOYSA-N 4-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-5-methylpyrazol-1-yl]-n,n-dimethylbenzamide Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(N=C2)C=2C=CC(=CC=2)C(=O)N(C)C)C)=N1 IKKSSBRMCKIQCO-UHFFFAOYSA-N 0.000 claims description 2
• CXVKMPLJTKMTRO-UHFFFAOYSA-N 4-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-5-methylpyrazol-1-yl]benzonitrile Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(N=C2)C=2C=CC(=CC=2)C#N)C)=N1 CXVKMPLJTKMTRO-UHFFFAOYSA-N 0.000 claims description 2
• SJCPFWIHRGBONQ-UHFFFAOYSA-N 4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]-n,n-dimethylbenzamide Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C=2C=CC(=CC=2)C(=O)N(C)C)C)=N1 SJCPFWIHRGBONQ-UHFFFAOYSA-N 0.000 claims description 2
• FZRYMYKRTQRNNV-UHFFFAOYSA-N 4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]benzonitrile Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C=2C=CC(=CC=2)C#N)C)=N1 FZRYMYKRTQRNNV-UHFFFAOYSA-N 0.000 claims description 2
• IEINCFLKAKRJAW-UHFFFAOYSA-N 4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-5-methylpyrazol-1-yl]-n,n-dimethylbenzamide Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(N=C2)C=2C=CC(=CC=2)C(=O)N(C)C)C)=N1 IEINCFLKAKRJAW-UHFFFAOYSA-N 0.000 claims description 2
• CQLSMRRTGKFHDN-UHFFFAOYSA-N 4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-5-methylpyrazol-1-yl]benzonitrile Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(N=C2)C=2C=CC(=CC=2)C#N)C)=N1 CQLSMRRTGKFHDN-UHFFFAOYSA-N 0.000 claims description 2
• OVDHESHDUWENLT-UHFFFAOYSA-N 4-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]benzonitrile Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(N=C2)C=2C=CC(=CC=2)C#N)C)=N1 OVDHESHDUWENLT-UHFFFAOYSA-N 0.000 claims description 2
• XGFZUYSBUTUUCF-UHFFFAOYSA-N 4-methoxy-n-(3-methyl-1-phenylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1=C(C(F)(F)F)C(OC)=NC(NC=2C(=NN(C=2)C=2C=CC=CC=2)C)=N1 XGFZUYSBUTUUCF-UHFFFAOYSA-N 0.000 claims description 2
• FEHNRYWQSUXWMJ-UHFFFAOYSA-N 4-methoxy-n-(5-methyl-1-phenylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1=C(C(F)(F)F)C(OC)=NC(NC2=C(N(N=C2)C=2C=CC=CC=2)C)=N1 FEHNRYWQSUXWMJ-UHFFFAOYSA-N 0.000 claims description 2
• JRQSZSLKAFTNDJ-UHFFFAOYSA-N 4-n-cyclopropyl-2-n-(3-methyl-1-methylsulfonylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound CC1=NN(S(C)(=O)=O)C=C1NC1=NC=C(C(F)(F)F)C(NC2CC2)=N1 JRQSZSLKAFTNDJ-UHFFFAOYSA-N 0.000 claims description 2
• AFMIJBNISXHNLO-UHFFFAOYSA-N 4-n-cyclopropyl-2-n-(5-methyl-1-methylsulfonylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=NN(S(C)(=O)=O)C(C)=C1NC1=NC=C(C(F)(F)F)C(NC2CC2)=N1 AFMIJBNISXHNLO-UHFFFAOYSA-N 0.000 claims description 2
• AWNALKZYYCBNAV-UHFFFAOYSA-N 4-n-ethyl-2-n-(1-ethylpyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=NN(CC)C=C2)=N1 AWNALKZYYCBNAV-UHFFFAOYSA-N 0.000 claims description 2
• SRVSVJPSGYJRIA-UHFFFAOYSA-N 4-n-ethyl-2-n-(1-ethylsulfonyl-3-methylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)S(=O)(=O)CC)C)=N1 SRVSVJPSGYJRIA-UHFFFAOYSA-N 0.000 claims description 2
• PQAIJUVYESESLO-UHFFFAOYSA-N 4-n-ethyl-2-n-(1-ethylsulfonyl-5-methylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(N=C2)S(=O)(=O)CC)C)=N1 PQAIJUVYESESLO-UHFFFAOYSA-N 0.000 claims description 2
• IHBRBGFLRXIAKQ-UHFFFAOYSA-N 4-n-ethyl-2-n-(1-methylpyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=NN(C)C=C2)=N1 IHBRBGFLRXIAKQ-UHFFFAOYSA-N 0.000 claims description 2
• NQXZMUGIZUWSIA-UHFFFAOYSA-N 4-n-ethyl-2-n-(2-methylpyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2N(N=CC=2)C)=N1 NQXZMUGIZUWSIA-UHFFFAOYSA-N 0.000 claims description 2
• LLDXOXJFKMLSPW-UHFFFAOYSA-N 4-n-ethyl-2-n-(3-methyl-1-methylsulfonylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)S(C)(=O)=O)C)=N1 LLDXOXJFKMLSPW-UHFFFAOYSA-N 0.000 claims description 2
• UJNQENGUTRGGLV-UHFFFAOYSA-N 4-n-ethyl-2-n-(3-methyl-1-propan-2-ylsulfonylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)S(=O)(=O)C(C)C)C)=N1 UJNQENGUTRGGLV-UHFFFAOYSA-N 0.000 claims description 2
• GNGJXCKFLASZMM-UHFFFAOYSA-N 4-n-ethyl-2-n-(5-methyl-1-propan-2-ylsulfonylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(N=C2)S(=O)(=O)C(C)C)C)=N1 GNGJXCKFLASZMM-UHFFFAOYSA-N 0.000 claims description 2
• FCHKFBSJSPDYPE-UHFFFAOYSA-N 4-n-ethyl-2-n-[1-(2-methoxyethyl)-3-methylpyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(CCOC)C=2)C)=N1 FCHKFBSJSPDYPE-UHFFFAOYSA-N 0.000 claims description 2
• NGPQDTADJHATJB-UHFFFAOYSA-N 4-n-ethyl-2-n-[1-(2-methoxyethyl)-5-methylpyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(CCOC)N=C2)C)=N1 NGPQDTADJHATJB-UHFFFAOYSA-N 0.000 claims description 2
• DRROYQJGFAVRLD-UHFFFAOYSA-N 4-n-ethyl-2-n-[1-(3-fluoropiperidin-4-yl)-3-methylpyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2C(CNCC2)F)C)=N1 DRROYQJGFAVRLD-UHFFFAOYSA-N 0.000 claims description 2
• BTSSYBIKLLGTAS-UHFFFAOYSA-N 4-n-ethyl-2-n-[1-[1-(2-methoxyethyl)piperidin-4-yl]-3-methylpyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CCN(CCOC)CC2)C)=N1 BTSSYBIKLLGTAS-UHFFFAOYSA-N 0.000 claims description 2
• DTPGICRTCBMOEC-UHFFFAOYSA-N 4-n-ethyl-2-n-[1-[1-(2-methoxyethyl)piperidin-4-yl]-5-methylpyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3CCN(CCOC)CC3)N=C2)C)=N1 DTPGICRTCBMOEC-UHFFFAOYSA-N 0.000 claims description 2
• WZVSBUMZSPUAQD-UHFFFAOYSA-N 4-n-ethyl-2-n-[1-[3-fluoro-1-(oxetan-3-yl)piperidin-4-yl]-3-methylpyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2C(CN(CC2)C2COC2)F)C)=N1 WZVSBUMZSPUAQD-UHFFFAOYSA-N 0.000 claims description 2
• DYQJWHDVUAGBAV-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-(1-methylpiperidin-4-yl)pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CCN(C)CC2)C)=N1 DYQJWHDVUAGBAV-UHFFFAOYSA-N 0.000 claims description 2
• HIZATHJVJUYAJX-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-(2-methyl-1-morpholin-4-ylpropan-2-yl)pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)CN2CCOCC2)C)=N1 HIZATHJVJUYAJX-UHFFFAOYSA-N 0.000 claims description 2
• OLFINRBYCWQNOD-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-(4-methylsulfonylphenyl)pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C=2C=CC(=CC=2)S(C)(=O)=O)C)=N1 OLFINRBYCWQNOD-UHFFFAOYSA-N 0.000 claims description 2
• OGSCLIHBMIEWTR-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-(oxan-4-yl)pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CCOCC2)C)=N1 OGSCLIHBMIEWTR-UHFFFAOYSA-N 0.000 claims description 2
• WJRQMFZCMMTZNA-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-(oxetan-3-yl)pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2COC2)C)=N1 WJRQMFZCMMTZNA-UHFFFAOYSA-N 0.000 claims description 2
• NZUXNOHPTZMKDU-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[(3-methyloxetan-3-yl)methyl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(CC3(C)COC3)C=2)C)=N1 NZUXNOHPTZMKDU-UHFFFAOYSA-N 0.000 claims description 2
• VACNHCXCQFUATR-ZDUSSCGKSA-N 4-n-ethyl-2-n-[3-methyl-1-[(3s)-1-(oxetan-3-yl)piperidin-3-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)[C@@H]2CN(CCC2)C2COC2)C)=N1 VACNHCXCQFUATR-ZDUSSCGKSA-N 0.000 claims description 2
• FFTYRJJAHOXRMP-LBPRGKRZSA-N 4-n-ethyl-2-n-[3-methyl-1-[(3s)-1-methylpiperidin-3-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)[C@@H]2CN(C)CCC2)C)=N1 FFTYRJJAHOXRMP-LBPRGKRZSA-N 0.000 claims description 2
• YRMDHIZGJDGDLM-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[1-(oxetan-3-yl)azetidin-3-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CN(C2)C2COC2)C)=N1 YRMDHIZGJDGDLM-UHFFFAOYSA-N 0.000 claims description 2
• FARVYMLSEJPCES-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[2-(1-methyl-1,2,4-triazol-3-yl)propan-2-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)C2=NN(C)C=N2)C)=N1 FARVYMLSEJPCES-UHFFFAOYSA-N 0.000 claims description 2
• ISZJAZJOOJYYPL-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[2-(1-methylpyrazol-3-yl)propan-2-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)C2=NN(C)C=C2)C)=N1 ISZJAZJOOJYYPL-UHFFFAOYSA-N 0.000 claims description 2
• DAEAQDNSCJOSHE-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[2-(1h-1,2,4-triazol-5-yl)propan-2-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)C=2NC=NN=2)C)=N1 DAEAQDNSCJOSHE-UHFFFAOYSA-N 0.000 claims description 2
• STYGOSMNCGOQPZ-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[2-(2-methylpyrazol-3-yl)propan-2-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)C=2N(N=CC=2)C)C)=N1 STYGOSMNCGOQPZ-UHFFFAOYSA-N 0.000 claims description 2
• KYPVWCPLQNDFGY-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[2-(4-methyl-1,2,4-triazol-3-yl)propan-2-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)C=2N(C=NN=2)C)C)=N1 KYPVWCPLQNDFGY-UHFFFAOYSA-N 0.000 claims description 2
• ADTTYQMAJZUGOY-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[2-(5-methyl-1,3,4-oxadiazol-2-yl)propan-2-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)C=2OC(C)=NN=2)C)=N1 ADTTYQMAJZUGOY-UHFFFAOYSA-N 0.000 claims description 2
• DCMZVIZIYJKCQH-UHFFFAOYSA-N 4-n-ethyl-2-n-[3-methyl-1-[2-(5-methyl-1h-1,2,4-triazol-3-yl)propan-2-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C(C)(C)C=2NC(C)=NN=2)C)=N1 DCMZVIZIYJKCQH-UHFFFAOYSA-N 0.000 claims description 2
• VNZSPNWLCKENPV-UHFFFAOYSA-N 4-n-ethyl-2-n-[5-methyl-1-(1-methylpiperidin-4-yl)pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3CCN(C)CC3)N=C2)C)=N1 VNZSPNWLCKENPV-UHFFFAOYSA-N 0.000 claims description 2
• AVIROIBUGXDXIY-UHFFFAOYSA-N 4-n-ethyl-2-n-[5-methyl-1-(4-methylsulfonylphenyl)pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(N=C2)C=2C=CC(=CC=2)S(C)(=O)=O)C)=N1 AVIROIBUGXDXIY-UHFFFAOYSA-N 0.000 claims description 2
• GFPAWYQBVAEYSD-UHFFFAOYSA-N 4-n-ethyl-2-n-[5-methyl-1-(oxan-4-yl)pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3CCOCC3)N=C2)C)=N1 GFPAWYQBVAEYSD-UHFFFAOYSA-N 0.000 claims description 2
• QVTSJOICCKGHOC-ZDUSSCGKSA-N 4-n-ethyl-2-n-[5-methyl-1-[(3s)-1-(oxetan-3-yl)piperidin-3-yl]pyrazol-4-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N([C@@H]3CN(CCC3)C3COC3)N=C2)C)=N1 QVTSJOICCKGHOC-ZDUSSCGKSA-N 0.000 claims description 2
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• PGPBOFLUUUBPSZ-UHFFFAOYSA-N 5-chloro-2-n-(1,3-dimethylpyrazol-4-yl)-4-n-methylpyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC=2C(=NN(C)C=2)C)=N1 PGPBOFLUUUBPSZ-UHFFFAOYSA-N 0.000 claims description 2
• DZUFOGTVCGMAFN-UHFFFAOYSA-N 5-chloro-2-n-(1-ethyl-3-methylpyrazol-4-yl)-4-n-methylpyrimidine-2,4-diamine Chemical compound CC1=NN(CC)C=C1NC1=NC=C(Cl)C(NC)=N1 DZUFOGTVCGMAFN-UHFFFAOYSA-N 0.000 claims description 2
• WAUXNUZZWHMFPK-UHFFFAOYSA-N 5-chloro-2-n-(1-ethyl-5-methylpyrazol-4-yl)-4-n-methylpyrimidine-2,4-diamine Chemical compound CCN1N=CC(NC=2N=C(NC)C(Cl)=CN=2)=C1C WAUXNUZZWHMFPK-UHFFFAOYSA-N 0.000 claims description 2
• QJAMIFLMEZSRFI-UHFFFAOYSA-N 5-chloro-2-n-(5-cyclopropyl-2-methylpyrazol-3-yl)-4-n-methylpyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC=2N(N=C(C=2)C2CC2)C)=N1 QJAMIFLMEZSRFI-UHFFFAOYSA-N 0.000 claims description 2
• OOYGKBKEKASCHJ-UHFFFAOYSA-N 5-chloro-4-(2,2-difluoroethoxy)-n-(1,5-dimethylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C1=NN(C)C(C)=C1NC1=NC=C(Cl)C(OCC(F)F)=N1 OOYGKBKEKASCHJ-UHFFFAOYSA-N 0.000 claims description 2
• XDHRQDCHZBZRPC-UHFFFAOYSA-N 5-chloro-4-(oxan-4-yloxy)-n-(1-propan-2-ylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C1=NN(C(C)C)C=C1NC1=NC=C(Cl)C(OC2CCOCC2)=N1 XDHRQDCHZBZRPC-UHFFFAOYSA-N 0.000 claims description 2
• VWPZHHHTCPKEQV-UHFFFAOYSA-N 5-chloro-4-methoxy-n-(1,3,5-trimethylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(C)N=C2C)C)=N1 VWPZHHHTCPKEQV-UHFFFAOYSA-N 0.000 claims description 2
• LSHXWYPMXJXOHQ-UHFFFAOYSA-N 5-chloro-4-methoxy-n-(2-methyl-5-propan-2-ylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2N(N=C(C=2)C(C)C)C)=N1 LSHXWYPMXJXOHQ-UHFFFAOYSA-N 0.000 claims description 2
• BTWSEGCECGHDHD-UHFFFAOYSA-N 5-chloro-4-methoxy-n-(2-propan-2-ylpyrazol-3-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2N(N=CC=2)C(C)C)=N1 BTWSEGCECGHDHD-UHFFFAOYSA-N 0.000 claims description 2
• BPEZDYHAGGKIJX-UHFFFAOYSA-N 5-chloro-4-methoxy-n-(3-methyl-1-phenylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C=2C=CC=CC=2)C)=N1 BPEZDYHAGGKIJX-UHFFFAOYSA-N 0.000 claims description 2
• QCJLLUPUWCLEBC-UHFFFAOYSA-N 5-chloro-4-methoxy-n-(3-methyl-1-propan-2-ylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C(C)C)C)=N1 QCJLLUPUWCLEBC-UHFFFAOYSA-N 0.000 claims description 2
• XWPKPKSGGUAEHZ-UHFFFAOYSA-N 5-chloro-4-methoxy-n-(5-methyl-1-phenylpyrazol-4-yl)pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(N=C2)C=2C=CC=CC=2)C)=N1 XWPKPKSGGUAEHZ-UHFFFAOYSA-N 0.000 claims description 2
• MGXHPPITINYTDB-UHFFFAOYSA-N 5-chloro-4-methoxy-n-[1-(2-methoxyethyl)-3-methylpyrazol-4-yl]pyrimidin-2-amine Chemical compound CC1=NN(CCOC)C=C1NC1=NC=C(Cl)C(OC)=N1 MGXHPPITINYTDB-UHFFFAOYSA-N 0.000 claims description 2
• RELVMZVJNWYMEF-UHFFFAOYSA-N 5-chloro-4-methoxy-n-[1-(2-methoxyethyl)-5-methylpyrazol-4-yl]pyrimidin-2-amine Chemical compound COCCN1N=CC(NC=2N=C(OC)C(Cl)=CN=2)=C1C RELVMZVJNWYMEF-UHFFFAOYSA-N 0.000 claims description 2
• ZSRTVEXQYKKFOU-UHFFFAOYSA-N 5-chloro-4-methoxy-n-[3-methyl-1-(3-methylpyridin-4-yl)pyrazol-4-yl]pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C=2C(=CN=CC=2)C)C)=N1 ZSRTVEXQYKKFOU-UHFFFAOYSA-N 0.000 claims description 2
• IILDBUHBXYCREP-UHFFFAOYSA-N 5-chloro-4-methoxy-n-[3-methyl-1-(4-methylsulfonylphenyl)pyrazol-4-yl]pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C=2C=CC(=CC=2)S(C)(=O)=O)C)=N1 IILDBUHBXYCREP-UHFFFAOYSA-N 0.000 claims description 2
• KKNDTJZYELYKEQ-UHFFFAOYSA-N 5-chloro-4-methoxy-n-[3-methyl-1-(oxan-4-yl)pyrazol-4-yl]pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C2CCOCC2)C)=N1 KKNDTJZYELYKEQ-UHFFFAOYSA-N 0.000 claims description 2
• UIVGFKKCBRWSAD-UHFFFAOYSA-N 5-chloro-4-methoxy-n-[3-methyl-1-(oxetan-3-yl)pyrazol-4-yl]pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C2COC2)C)=N1 UIVGFKKCBRWSAD-UHFFFAOYSA-N 0.000 claims description 2
• AMNGGHWNIWAGNA-UHFFFAOYSA-N 5-chloro-4-methoxy-n-[5-methyl-1-(4-methylsulfonylphenyl)pyrazol-4-yl]pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(N=C2)C=2C=CC(=CC=2)S(C)(=O)=O)C)=N1 AMNGGHWNIWAGNA-UHFFFAOYSA-N 0.000 claims description 2
• SMPBEXACOUQNJF-UHFFFAOYSA-N 5-chloro-4-methoxy-n-[5-methyl-1-(oxan-4-yl)pyrazol-4-yl]pyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(C3CCOCC3)N=C2)C)=N1 SMPBEXACOUQNJF-UHFFFAOYSA-N 0.000 claims description 2
• DGJBCXRZXAZSHQ-UHFFFAOYSA-N 5-chloro-4-methyl-n-[3-methyl-1-(4-methylsulfonylphenyl)pyrazol-4-yl]pyrimidin-2-amine Chemical compound CC1=NN(C=2C=CC(=CC=2)S(C)(=O)=O)C=C1NC1=NC=C(Cl)C(C)=N1 DGJBCXRZXAZSHQ-UHFFFAOYSA-N 0.000 claims description 2
• WXKOFSMSYCZRGZ-UHFFFAOYSA-N 5-chloro-4-n-(2,2-difluoroethyl)-2-n-(1,5-dimethylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C(C)=C1NC1=NC=C(Cl)C(NCC(F)F)=N1 WXKOFSMSYCZRGZ-UHFFFAOYSA-N 0.000 claims description 2
• IFYAPSWSFXUJQL-UHFFFAOYSA-N 5-chloro-4-n-ethyl-2-n-[3-methyl-1-(oxetan-3-yl)pyrazol-4-yl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NCC)=NC(NC=2C(=NN(C=2)C2COC2)C)=N1 IFYAPSWSFXUJQL-UHFFFAOYSA-N 0.000 claims description 2
• KBJQHFKDRFUAJJ-UHFFFAOYSA-N 5-chloro-4-n-methyl-2-n-(1,3,5-trimethylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC2=C(N(C)N=C2C)C)=N1 KBJQHFKDRFUAJJ-UHFFFAOYSA-N 0.000 claims description 2
• OWPIFHMSKZNUAB-UHFFFAOYSA-N 5-chloro-4-n-methyl-2-n-(1-propan-2-ylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC2=CN(N=C2)C(C)C)=N1 OWPIFHMSKZNUAB-UHFFFAOYSA-N 0.000 claims description 2
• GYDZDFPBYDLSNB-UHFFFAOYSA-N 5-chloro-4-n-methyl-2-n-(2-methyl-5-propan-2-ylpyrazol-3-yl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC=2N(N=C(C=2)C(C)C)C)=N1 GYDZDFPBYDLSNB-UHFFFAOYSA-N 0.000 claims description 2
• CFNGJMAFDHINJE-UHFFFAOYSA-N 5-chloro-4-n-methyl-2-n-(2-propan-2-ylpyrazol-3-yl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC=2N(N=CC=2)C(C)C)=N1 CFNGJMAFDHINJE-UHFFFAOYSA-N 0.000 claims description 2
• NQANBNXOKMIMDH-UHFFFAOYSA-N 5-chloro-4-n-methyl-2-n-(3-methyl-1-methylsulfonylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC=2C(=NN(C=2)S(C)(=O)=O)C)=N1 NQANBNXOKMIMDH-UHFFFAOYSA-N 0.000 claims description 2
• VNIWAFUMIAVVTJ-UHFFFAOYSA-N 5-chloro-4-n-methyl-2-n-(3-methyl-1-propan-2-ylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC=2C(=NN(C=2)C(C)C)C)=N1 VNIWAFUMIAVVTJ-UHFFFAOYSA-N 0.000 claims description 2
• PJPZWPSWHAMCBT-UHFFFAOYSA-N 5-chloro-4-n-methyl-2-n-[3-methyl-1-(oxetan-3-yl)pyrazol-4-yl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC=2C(=NN(C=2)C2COC2)C)=N1 PJPZWPSWHAMCBT-UHFFFAOYSA-N 0.000 claims description 2
• OPRYEOKZWOHPBS-UHFFFAOYSA-N 5-chloro-4-n-methyl-2-n-[3-methyl-1-[(3-methyloxetan-3-yl)methyl]pyrazol-4-yl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(NC)=NC(NC=2C(=NN(CC3(C)COC3)C=2)C)=N1 OPRYEOKZWOHPBS-UHFFFAOYSA-N 0.000 claims description 2
• MKUUDCKLCVNMPZ-UHFFFAOYSA-N 5-chloro-n-(1,3-dimethylpyrazol-4-yl)-4-methoxypyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C)C=2)C)=N1 MKUUDCKLCVNMPZ-UHFFFAOYSA-N 0.000 claims description 2
• UQCNNXIOWIQDNU-UHFFFAOYSA-N 5-chloro-n-(1,5-dimethylpyrazol-4-yl)-4-(2,2,2-trifluoroethoxy)pyrimidin-2-amine Chemical compound C1=NN(C)C(C)=C1NC1=NC=C(Cl)C(OCC(F)(F)F)=N1 UQCNNXIOWIQDNU-UHFFFAOYSA-N 0.000 claims description 2
• PJHNMLLJMPTOCP-UHFFFAOYSA-N 5-chloro-n-(1,5-dimethylpyrazol-4-yl)-4-(oxan-4-yloxy)pyrimidin-2-amine Chemical compound C1=NN(C)C(C)=C1NC1=NC=C(Cl)C(OC2CCOCC2)=N1 PJHNMLLJMPTOCP-UHFFFAOYSA-N 0.000 claims description 2
• NAPGBRUDIGVTLH-UHFFFAOYSA-N 5-chloro-n-(1,5-dimethylpyrazol-4-yl)-4-(oxetan-3-yloxy)pyrimidin-2-amine Chemical compound C1=NN(C)C(C)=C1NC1=NC=C(Cl)C(OC2COC2)=N1 NAPGBRUDIGVTLH-UHFFFAOYSA-N 0.000 claims description 2
• RVPUYHJENAIFMX-UHFFFAOYSA-N 5-chloro-n-(1,5-dimethylpyrazol-4-yl)-4-methoxypyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(C)N=C2)C)=N1 RVPUYHJENAIFMX-UHFFFAOYSA-N 0.000 claims description 2
• FCAJZHRAOBOUND-UHFFFAOYSA-N 5-chloro-n-(1-cyclopropylsulfonyl-3-methylpyrazol-4-yl)-4-methoxypyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)S(=O)(=O)C2CC2)C)=N1 FCAJZHRAOBOUND-UHFFFAOYSA-N 0.000 claims description 2
• WTUCJCAYSDAGCQ-UHFFFAOYSA-N 5-chloro-n-(1-cyclopropylsulfonyl-5-methylpyrazol-4-yl)-4-methoxypyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(N=C2)S(=O)(=O)C2CC2)C)=N1 WTUCJCAYSDAGCQ-UHFFFAOYSA-N 0.000 claims description 2
• YRJRKSRZKYOCIK-UHFFFAOYSA-N 5-chloro-n-(1-ethyl-3-methylpyrazol-4-yl)-4-methoxypyrimidin-2-amine Chemical compound CC1=NN(CC)C=C1NC1=NC=C(Cl)C(OC)=N1 YRJRKSRZKYOCIK-UHFFFAOYSA-N 0.000 claims description 2
• XSJSXDQNRMDJMK-UHFFFAOYSA-N 5-chloro-n-(1-ethyl-5-methylpyrazol-4-yl)-4-methoxypyrimidin-2-amine Chemical compound CCN1N=CC(NC=2N=C(OC)C(Cl)=CN=2)=C1C XSJSXDQNRMDJMK-UHFFFAOYSA-N 0.000 claims description 2
• SXKYVVQABRZHIM-UHFFFAOYSA-N 5-chloro-n-(5-chloro-1-methylpyrazol-4-yl)-4-methoxypyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(C)N=C2)Cl)=N1 SXKYVVQABRZHIM-UHFFFAOYSA-N 0.000 claims description 2
• PTVDQKZNSITFII-UHFFFAOYSA-N 5-chloro-n-(5-cyclopropyl-2-methylpyrazol-3-yl)-4-methoxypyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC=2N(N=C(C=2)C2CC2)C)=N1 PTVDQKZNSITFII-UHFFFAOYSA-N 0.000 claims description 2
• DNMBWXQLGPFZKH-UHFFFAOYSA-N 5-chloro-n-[1-[1-(2-fluoroethyl)piperidin-4-yl]-3-methylpyrazol-4-yl]-4-methoxypyrimidin-2-amine Chemical class C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C2CCN(CCF)CC2)C)=N1 DNMBWXQLGPFZKH-UHFFFAOYSA-N 0.000 claims description 2
• GOTOJCFRBSNHGY-UHFFFAOYSA-N 5-chloro-n-[1-[1-(2-fluoroethyl)piperidin-4-yl]-5-methylpyrazol-4-yl]-4-methoxypyrimidin-2-amine Chemical class C1=C(Cl)C(OC)=NC(NC2=C(N(C3CCN(CCF)CC3)N=C2)C)=N1 GOTOJCFRBSNHGY-UHFFFAOYSA-N 0.000 claims description 2
• PNEHRDPFYHTGKZ-UHFFFAOYSA-N 5-chloro-n-[5-chloro-1-(oxan-4-yl)pyrazol-4-yl]-4-methoxypyrimidin-2-amine Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(C3CCOCC3)N=C2)Cl)=N1 PNEHRDPFYHTGKZ-UHFFFAOYSA-N 0.000 claims description 2
• NQKRLTDEGNMBPL-UHFFFAOYSA-N 5-fluoro-4-n-methyl-2-n-(2-methylpyrazol-3-yl)pyrimidine-2,4-diamine Chemical compound C1=C(F)C(NC)=NC(NC=2N(N=CC=2)C)=N1 NQKRLTDEGNMBPL-UHFFFAOYSA-N 0.000 claims description 2
• PPLRHHLJSBTVNH-UHFFFAOYSA-N 5-fluoro-4-n-methyl-4-n-(2-propylpyrazol-3-yl)pyrimidine-2,4-diamine Chemical compound CCCN1N=CC=C1N(C)C1=NC(N)=NC=C1F PPLRHHLJSBTVNH-UHFFFAOYSA-N 0.000 claims description 2
• RJIYKTGSGQFBSO-UHFFFAOYSA-N [4-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-3-methylpyrazol-1-yl]piperidin-1-yl]-(1-methylcyclopropyl)methanone Chemical compound C1=C(Cl)C(OC)=NC(NC=2C(=NN(C=2)C2CCN(CC2)C(=O)C2(C)CC2)C)=N1 RJIYKTGSGQFBSO-UHFFFAOYSA-N 0.000 claims description 2
• SSTZXVPEWNNOTP-UHFFFAOYSA-N [4-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-5-methylpyrazol-1-yl]piperidin-1-yl]-(1-methylcyclopropyl)methanone Chemical compound C1=C(Cl)C(OC)=NC(NC2=C(N(C3CCN(CC3)C(=O)C3(C)CC3)N=C2)C)=N1 SSTZXVPEWNNOTP-UHFFFAOYSA-N 0.000 claims description 2
• NAASRVIDXCMKNO-UHFFFAOYSA-N [5-[[5-chloro-4-(methylamino)pyrimidin-2-yl]amino]-1-methylpyrazol-3-yl]-morpholin-4-ylmethanone Chemical compound C1=C(Cl)C(NC)=NC(NC=2N(N=C(C=2)C(=O)N2CCOCC2)C)=N1 NAASRVIDXCMKNO-UHFFFAOYSA-N 0.000 claims description 2
• VPHJCDJCSJKDGS-UHFFFAOYSA-N cyclopropyl-[4-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]piperidin-1-yl]methanone Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC=2C(=NN(C=2)C2CCN(CC2)C(=O)C2CC2)C)=N1 VPHJCDJCSJKDGS-UHFFFAOYSA-N 0.000 claims description 2
• PZEOKMGQCHATMJ-UHFFFAOYSA-N cyclopropyl-[4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-3-methylpyrazol-1-yl]piperidin-1-yl]methanone Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC=2C(=NN(C=2)C2CCN(CC2)C(=O)C2CC2)C)=N1 PZEOKMGQCHATMJ-UHFFFAOYSA-N 0.000 claims description 2
• SVJZXWPMOUUMIJ-UHFFFAOYSA-N cyclopropyl-[4-[4-[[4-(ethylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]-5-methylpyrazol-1-yl]piperidin-1-yl]methanone Chemical compound C1=C(C(F)(F)F)C(NCC)=NC(NC2=C(N(C3CCN(CC3)C(=O)C3CC3)N=C2)C)=N1 SVJZXWPMOUUMIJ-UHFFFAOYSA-N 0.000 claims description 2
• ILBYROKDMYHXJA-UHFFFAOYSA-N cyclopropyl-[4-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]piperidin-1-yl]methanone Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(C3CCN(CC3)C(=O)C3CC3)N=C2)C)=N1 ILBYROKDMYHXJA-UHFFFAOYSA-N 0.000 claims description 2
• 238000000034 method Methods 0.000 claims description 2
• PVVAZLOSHWOIHD-UHFFFAOYSA-N methyl 2-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-3-methylpyrazol-1-yl]-2-methylpropanoate Chemical compound CC1=NN(C(C)(C)C(=O)OC)C=C1NC1=NC=C(Cl)C(OC)=N1 PVVAZLOSHWOIHD-UHFFFAOYSA-N 0.000 claims description 2
• XSSWGGZWGOUOCQ-UHFFFAOYSA-N methyl 2-[4-[(5-chloro-4-methoxypyrimidin-2-yl)amino]-5-methylpyrazol-1-yl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N1N=CC(NC=2N=C(OC)C(Cl)=CN=2)=C1C XSSWGGZWGOUOCQ-UHFFFAOYSA-N 0.000 claims description 2
• PGKQHCLOOJVKTQ-UHFFFAOYSA-N n,2-dimethyl-2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanamide Chemical compound CNC(=O)C(C)(C)N1N=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C1C PGKQHCLOOJVKTQ-UHFFFAOYSA-N 0.000 claims description 2
• AURRWRJLWWRZBB-UHFFFAOYSA-N n-(1,5-dimethylpyrazol-4-yl)-4-pyrrolidin-1-yl-5-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1=NN(C)C(C)=C1NC1=NC=C(C(F)(F)F)C(N2CCCC2)=N1 AURRWRJLWWRZBB-UHFFFAOYSA-N 0.000 claims description 2
• MZTIMVYQYPAQSZ-UHFFFAOYSA-N n-ethyl-1-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]cyclobutane-1-carboxamide Chemical compound N1=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C(C)N1C1(C(=O)NCC)CCC1 MZTIMVYQYPAQSZ-UHFFFAOYSA-N 0.000 claims description 2
• RZHUFHGNDAWQOJ-UHFFFAOYSA-N n-ethyl-2-methyl-2-[3-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanamide Chemical compound CC1=NN(C(C)(C)C(=O)NCC)C=C1NC1=NC=C(C(F)(F)F)C(NC)=N1 RZHUFHGNDAWQOJ-UHFFFAOYSA-N 0.000 claims description 2
• OCPXFRLTGCHXHT-UHFFFAOYSA-N n-ethyl-2-methyl-2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanamide Chemical compound CCNC(=O)C(C)(C)N1N=CC(NC=2N=C(NC)C(=CN=2)C(F)(F)F)=C1C OCPXFRLTGCHXHT-UHFFFAOYSA-N 0.000 claims description 2
• BRDOWWROMOXEAJ-UHFFFAOYSA-N n-tert-butyl-2-methyl-2-[5-methyl-4-[[4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-yl]amino]pyrazol-1-yl]propanamide Chemical compound C1=C(C(F)(F)F)C(NC)=NC(NC2=C(N(N=C2)C(C)(C)C(=O)NC(C)(C)C)C)=N1 BRDOWWROMOXEAJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims 127
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 23
• 125000000623 heterocyclic group Chemical group 0.000 claims 23
• 125000005843 halogen group Chemical group 0.000 claims 22
• 239000008194 pharmaceutical composition Substances 0.000 claims 22
• 125000003545 alkoxy group Chemical group 0.000 claims 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims 18
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 15
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