ES2569528T3 - 4-pirazolil-N-arilpirimidin-2-aminas y 4-pirazolil-N-heteroarilpirimidin-2-aminas como inhibidores de quinasas Janus - Google Patents
4-pirazolil-N-arilpirimidin-2-aminas y 4-pirazolil-N-heteroarilpirimidin-2-aminas como inhibidores de quinasas Janus Download PDFInfo
- Publication number
- ES2569528T3 ES2569528T3 ES08848610.5T ES08848610T ES2569528T3 ES 2569528 T3 ES2569528 T3 ES 2569528T3 ES 08848610 T ES08848610 T ES 08848610T ES 2569528 T3 ES2569528 T3 ES 2569528T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrazol
- pyrimidin
- phenylamino
- carbonyl
- ylamino
- 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.)
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- 229940122245 Janus kinase inhibitor Drugs 0.000 title 1
- -1 haloC1-6alkyl Chemical group 0.000 claims abstract 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 24
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 5
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- JCWBDPZBFFJJLV-NVHKAFQKSA-N (3r)-1-[4-[[4-[1-(2-cyano-1-cyclopropylethyl)pyrazol-4-yl]pyrimidin-2-yl]amino]benzoyl]pyrrolidine-3-carbonitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CC2)C=CC=1C(=O)N1CC[C@@H](C#N)C1 JCWBDPZBFFJJLV-NVHKAFQKSA-N 0.000 claims 1
- LJEBDNPJFQCMMC-OEPVSBQMSA-N (3s)-1-[4-[[4-[1-(2-cyano-1-cyclopentylethyl)pyrazol-4-yl]pyrimidin-2-yl]amino]benzoyl]pyrrolidine-3-carbonitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CCCC2)C=CC=1C(=O)N1CC[C@H](C#N)C1 LJEBDNPJFQCMMC-OEPVSBQMSA-N 0.000 claims 1
- CWCFUURQCJAWTH-UHFFFAOYSA-N 1-[4-[[4-[1-[3-cyano-1-(cyanomethyl)cyclobutyl]pyrazol-4-yl]pyrimidin-2-yl]amino]benzoyl]pyrrolidine-3-carbonitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C2(CC#N)CC(C2)C#N)C=CC=1C(=O)N1CCC(C#N)C1 CWCFUURQCJAWTH-UHFFFAOYSA-N 0.000 claims 1
- DAKLTKIALMRNMH-UHFFFAOYSA-N 2-(azetidin-3-yl)acetonitrile Chemical compound N#CCC1CNC1 DAKLTKIALMRNMH-UHFFFAOYSA-N 0.000 claims 1
- JWTGMDPCSARKPF-UHFFFAOYSA-N 2-[1-ethylsulfonyl-3-[4-[2-[4-(3-methoxypyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2N=C(NC=3C=CC(=CC=3)C(=O)N3CC(CC3)OC)N=CC=2)=C1 JWTGMDPCSARKPF-UHFFFAOYSA-N 0.000 claims 1
- QZTTVFJXTAGTRG-UHFFFAOYSA-N 2-[1-ethylsulfonyl-3-[4-[2-[4-(morpholine-4-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2N=C(NC=3C=CC(=CC=3)C(=O)N3CCOCC3)N=CC=2)=C1 QZTTVFJXTAGTRG-UHFFFAOYSA-N 0.000 claims 1
- NBPQKEMQAHIRBO-UHFFFAOYSA-N 2-[3-[4-[2-[4-(azetidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]-1-ethylsulfonylazetidin-3-yl]acetonitrile Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2N=C(NC=3C=CC(=CC=3)C(=O)N3CCC3)N=CC=2)=C1 NBPQKEMQAHIRBO-UHFFFAOYSA-N 0.000 claims 1
- KQHKNYWIKYAGIT-UHFFFAOYSA-N 2-[3-[4-[2-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]anilino]pyrimidin-4-yl]pyrazol-1-yl]-1-ethylsulfonylazetidin-3-yl]acetonitrile Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2N=C(NC=3C=CC(=CC=3)C(=O)N3CC(CC3)N(C)C)N=CC=2)=C1 KQHKNYWIKYAGIT-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- WTFUAZUTVJVMBL-UHFFFAOYSA-N 3-(cyanomethyl)-3-[4-[2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C1=C(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)N=CC=2)C=NN1C1(CC#N)CC(C#N)C1 WTFUAZUTVJVMBL-UHFFFAOYSA-N 0.000 claims 1
- CPSVQQLTLPGEEC-UHFFFAOYSA-N 3-(cyanomethyl)-3-[4-[2-[4-(3-fluoropyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C1C(F)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C2(CC#N)CC(C2)C#N)=N1 CPSVQQLTLPGEEC-UHFFFAOYSA-N 0.000 claims 1
- UZOICBWRKGPGGI-UHFFFAOYSA-N 3-(cyanomethyl)-3-[4-[2-[4-(3-hydroxypyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C1C(O)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C2(CC#N)CC(C2)C#N)=N1 UZOICBWRKGPGGI-UHFFFAOYSA-N 0.000 claims 1
- RDEMHYQMQSBPEG-UHFFFAOYSA-N 3-(cyanomethyl)-3-[4-[2-[4-(3-methoxypyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C1C(OC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C2(CC#N)CC(C2)C#N)=N1 RDEMHYQMQSBPEG-UHFFFAOYSA-N 0.000 claims 1
- LHWNPIDCQHJDKN-UHFFFAOYSA-N 3-(cyanomethyl)-3-[4-[2-[4-(4-methoxypiperidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C1CC(OC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C2(CC#N)CC(C2)C#N)=N1 LHWNPIDCQHJDKN-UHFFFAOYSA-N 0.000 claims 1
- ACWRXNXRRLEPAE-UHFFFAOYSA-N 3-(cyanomethyl)-3-[4-[2-[4-(4-methylpiperazine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C2(CC#N)CC(C2)C#N)=N1 ACWRXNXRRLEPAE-UHFFFAOYSA-N 0.000 claims 1
- NFNUNUMBHNANCV-UHFFFAOYSA-N 3-(cyanomethyl)-3-[4-[2-[4-(morpholine-4-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C2(CC#N)CC(C2)C#N)C=CC=1C(=O)N1CCOCC1 NFNUNUMBHNANCV-UHFFFAOYSA-N 0.000 claims 1
- ANXNYBPJAXAZPZ-UHFFFAOYSA-N 3-(cyanomethyl)-3-[4-[2-[4-(pyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]cyclobutane-1-carbonitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C2(CC#N)CC(C2)C#N)C=CC=1C(=O)N1CCCC1 ANXNYBPJAXAZPZ-UHFFFAOYSA-N 0.000 claims 1
- LXDOJUVLROBRRO-UHFFFAOYSA-N 3-[4-[2-[4-(4-acetylpiperazine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]-3-(cyanomethyl)cyclobutane-1-carbonitrile Chemical compound C1CN(C(=O)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C2(CC#N)CC(C2)C#N)=N1 LXDOJUVLROBRRO-UHFFFAOYSA-N 0.000 claims 1
- JJXMYGFSVKQKED-UHFFFAOYSA-N 3-[4-[2-[4-(4-acetylpiperazine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]-3-cyclopentylpropanenitrile Chemical compound C1CN(C(=O)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 JJXMYGFSVKQKED-UHFFFAOYSA-N 0.000 claims 1
- NIYQOFMBILWWRH-UHFFFAOYSA-N 3-[4-[2-[4-(4-acetylpiperazine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]-3-cyclopropylpropanenitrile Chemical compound C1CN(C(=O)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 NIYQOFMBILWWRH-UHFFFAOYSA-N 0.000 claims 1
- OFNKJXLBSOWCQO-UHFFFAOYSA-N 3-[4-[2-[4-(azetidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]-3-(cyanomethyl)cyclobutane-1-carbonitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C2(CC#N)CC(C2)C#N)C=CC=1C(=O)N1CCC1 OFNKJXLBSOWCQO-UHFFFAOYSA-N 0.000 claims 1
- VUPTUFXNTWGUGM-UHFFFAOYSA-N 3-[4-[2-[4-(azetidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]-3-cyclopropylpropanenitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CC2)C=CC=1C(=O)N1CCC1 VUPTUFXNTWGUGM-UHFFFAOYSA-N 0.000 claims 1
- OOFCWWDIXDSJNO-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[2-[4-(3-fluoropyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1C(F)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 OOFCWWDIXDSJNO-UHFFFAOYSA-N 0.000 claims 1
- NUHNUVYBUGKNNH-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[2-[4-(3-methoxypyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1C(OC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 NUHNUVYBUGKNNH-UHFFFAOYSA-N 0.000 claims 1
- MXXPKDDYDFGPPV-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[2-[4-(3-oxo-2,8-diazaspiro[4.5]decane-8-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CCCC2)C=CC=1C(=O)N(CC1)CCC21CNC(=O)C2 MXXPKDDYDFGPPV-UHFFFAOYSA-N 0.000 claims 1
- LPVPQBQOFRHSNG-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[2-[4-(3-pyridin-2-yloxypyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CCCC2)C=CC=1C(=O)N(C1)CCC1OC1=CC=CC=N1 LPVPQBQOFRHSNG-UHFFFAOYSA-N 0.000 claims 1
- UQAAVQMLMPWQQK-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[2-[4-(4-methoxypiperidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1CC(OC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 UQAAVQMLMPWQQK-UHFFFAOYSA-N 0.000 claims 1
- HBTHWGNTZZEKTD-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[2-[4-(morpholine-4-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CCCC2)C=CC=1C(=O)N1CCOCC1 HBTHWGNTZZEKTD-UHFFFAOYSA-N 0.000 claims 1
- ILQCGNDTPJZGFE-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[2-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 ILQCGNDTPJZGFE-UHFFFAOYSA-N 0.000 claims 1
- VLAMQWPDPICALA-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[2-[4-(3-fluoropyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1C(F)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 VLAMQWPDPICALA-UHFFFAOYSA-N 0.000 claims 1
- WZUWCGJTZXLPKD-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[2-[4-(3-methoxypyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1C(OC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 WZUWCGJTZXLPKD-UHFFFAOYSA-N 0.000 claims 1
- OYSPEILBMGTDEP-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[2-[4-(4-hydroxypiperidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1CC(O)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 OYSPEILBMGTDEP-UHFFFAOYSA-N 0.000 claims 1
- BVIFQNOFYQWFJS-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[2-[4-(4-methoxypiperidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1CC(OC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 BVIFQNOFYQWFJS-UHFFFAOYSA-N 0.000 claims 1
- WSXAZBCOKNZEQJ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[2-[4-(4-methylpiperazine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 WSXAZBCOKNZEQJ-UHFFFAOYSA-N 0.000 claims 1
- SMQORXYBUBYFBG-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[2-[4-(morpholine-4-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CC2)C=CC=1C(=O)N1CCOCC1 SMQORXYBUBYFBG-UHFFFAOYSA-N 0.000 claims 1
- DBTOQSSCDXHDJV-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[2-[4-(pyrrolidine-1-carbonyl)anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CC2)C=CC=1C(=O)N1CCCC1 DBTOQSSCDXHDJV-UHFFFAOYSA-N 0.000 claims 1
- IMZDJMNJEZSMNB-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[2-[4-[3-(dimethylamino)pyrrolidine-1-carbonyl]anilino]pyrimidin-4-yl]pyrazol-1-yl]propanenitrile Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 IMZDJMNJEZSMNB-UHFFFAOYSA-N 0.000 claims 1
- DXGSKKPAAZHYQN-UHFFFAOYSA-N 4-[[4-[1-(2-cyano-1-cyclopentylethyl)pyrazol-4-yl]-5-methoxypyrimidin-2-yl]amino]benzoic acid Chemical compound N1=C(C2=CN(N=C2)C(CC#N)C2CCCC2)C(OC)=CN=C1NC1=CC=C(C(O)=O)C=C1 DXGSKKPAAZHYQN-UHFFFAOYSA-N 0.000 claims 1
- VFBRLYVOCBPPCB-UHFFFAOYSA-N 4-[[4-[1-(2-cyano-1-cyclopentylethyl)pyrazol-4-yl]pyrimidin-2-yl]amino]-n-(1-pyridin-2-ylpyrrolidin-3-yl)benzamide Chemical compound C=1C=C(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CCCC2)C=CC=1C(=O)NC(C1)CCN1C1=CC=CC=N1 VFBRLYVOCBPPCB-UHFFFAOYSA-N 0.000 claims 1
- BJQCBZDEGUCZOI-UHFFFAOYSA-N 4-[[4-[1-(2-cyano-1-cyclopropylethyl)pyrazol-4-yl]pyrimidin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 BJQCBZDEGUCZOI-UHFFFAOYSA-N 0.000 claims 1
- NSDQJFQLPRUICH-UHFFFAOYSA-N 4-[[4-[1-[3-(cyanomethyl)-1-ethylsulfonylazetidin-3-yl]pyrazol-4-yl]pyrimidin-2-yl]amino]benzoic acid Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2N=C(NC=3C=CC(=CC=3)C(O)=O)N=CC=2)=C1 NSDQJFQLPRUICH-UHFFFAOYSA-N 0.000 claims 1
- QZOSARGQGHPUQQ-UHFFFAOYSA-N 4-[[4-[1-[3-cyano-1-(cyanomethyl)cyclobutyl]pyrazol-4-yl]pyrimidin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=CC(C2=CN(N=C2)C2(CC#N)CC(C2)C#N)=N1 QZOSARGQGHPUQQ-UHFFFAOYSA-N 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- YKOUDTFFCQQDLK-UHFFFAOYSA-N n'-(cyclopropylmethyl)acetohydrazide Chemical compound CC(=O)NNCC1CC1 YKOUDTFFCQQDLK-UHFFFAOYSA-N 0.000 claims 1
- HOKJHFHSIPMSIR-LETIRJCYSA-N n-[(3r)-1-[4-[[4-[1-(2-cyano-1-cyclopropylethyl)pyrazol-4-yl]pyrimidin-2-yl]amino]benzoyl]pyrrolidin-3-yl]acetamide Chemical compound C1[C@H](NC(=O)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CC2)=N1 HOKJHFHSIPMSIR-LETIRJCYSA-N 0.000 claims 1
- IEHFEXNNXJHASJ-QSAPEBAKSA-N n-[(3s)-1-[4-[[4-[1-(2-cyano-1-cyclopentylethyl)pyrazol-4-yl]pyrimidin-2-yl]amino]benzoyl]pyrrolidin-3-yl]acetamide Chemical compound C1[C@@H](NC(=O)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=CC(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 IEHFEXNNXJHASJ-QSAPEBAKSA-N 0.000 claims 1
- QMRZMCCTPQZZSR-UHFFFAOYSA-N n-[3-[[4-[1-(2-cyano-1-cyclopentylethyl)pyrazol-4-yl]pyrimidin-2-yl]amino]phenyl]-2-morpholin-4-ylacetamide Chemical compound C=1C=CC(NC=2N=C(C=CN=2)C2=CN(N=C2)C(CC#N)C2CCCC2)=CC=1NC(=O)CN1CCOCC1 QMRZMCCTPQZZSR-UHFFFAOYSA-N 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 16
- 125000005843 halogen group Chemical group 0.000 abstract 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 14
- 125000001072 heteroaryl group Chemical group 0.000 abstract 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 12
- 125000003118 aryl group Chemical group 0.000 abstract 10
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 9
- 125000001424 substituent group Chemical group 0.000 abstract 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 6
- 102100038417 Cytoplasmic FMR1-interacting protein 1 Human genes 0.000 abstract 6
- 101710181791 Cytoplasmic FMR1-interacting protein 1 Proteins 0.000 abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 6
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000005311 halosulfanyl group Chemical group 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 101100310920 Caenorhabditis elegans sra-2 gene Proteins 0.000 abstract 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
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| US988606P | 2007-11-16 | ||
| PCT/US2008/083319 WO2009064835A1 (en) | 2007-11-16 | 2008-11-13 | 4-pyrazolyl-n-arylpyrimidin-2-amines and 4-pyrazolyl-n-heteroarylpyrimidin-2-amines as janus kinase inhibitors |
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| ES2569528T3 true ES2569528T3 (es) | 2016-05-11 |
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Families Citing this family (113)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2005105814A1 (en) * | 2004-04-28 | 2005-11-10 | Incyte Corporation | Tetracyclic inhibitors of janus kinases |
| TWI630207B (zh) | 2005-12-13 | 2018-07-21 | 英塞特控股公司 | 作為傑納斯激酶(JANUS KINASE)抑制劑之經雜芳基取代之吡咯并〔2,3-b〕吡啶及吡咯并〔2,3-b〕嘧啶 |
| EP2121692B1 (en) | 2006-12-22 | 2013-04-10 | Incyte Corporation | Substituted heterocycles as janus kinase inhibitors |
| CL2008001709A1 (es) | 2007-06-13 | 2008-11-03 | Incyte Corp | Compuestos derivados de pirrolo [2,3-b]pirimidina, moduladores de quinasas jak; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como cancer, psoriasis, artritis reumatoide, entre otras. |
| EP3070090B1 (en) | 2007-06-13 | 2018-12-12 | Incyte Holdings Corporation | Use of salts of the janus kinase inhibitor (r)-3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h- pyrazol-1-yl)-3- cyclopentylpropanenitrile |
| FR2938537B1 (fr) | 2008-11-14 | 2012-10-26 | Sanofi Aventis | Derives de carbamates d'alkyl-heterocycles, leur preparation et leur application en therapeutique. |
| TWI665200B (zh) | 2009-01-15 | 2019-07-11 | 英塞特公司 | 製造jak抑制劑之方法及相關中間化合物 |
| EP3643312A1 (en) | 2009-05-22 | 2020-04-29 | Incyte Holdings Corporation | 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]octane- or heptane-nitrile as jak inhibitors |
| AR076794A1 (es) | 2009-05-22 | 2011-07-06 | Incyte Corp | Derivados de n-(hetero)aril-pirrolidina de pirazol-4-il-pirrolo [2,3-d]pirimidinas y pirrol-3-il-pirrolo [2,3-d ]pirimidinas como inhibidores de la quinasa janus y composiciones farmaceuticas que los contienen |
| AR078012A1 (es) | 2009-09-01 | 2011-10-05 | Incyte Corp | Derivados heterociclicos de las pirazol-4-il- pirrolo (2,3-d) pirimidinas como inhibidores de la quinasa janus |
| WO2011079231A1 (en) * | 2009-12-23 | 2011-06-30 | Gatekeeper Pharmaceutical, Inc. | Compounds that modulate egfr activity and methods for treating or preventing conditions therewith |
| US8841078B2 (en) * | 2010-02-10 | 2014-09-23 | Genon Biotechnologies Oy | Dual activity kinase domains and uses thereof |
| CN102844317B (zh) * | 2010-02-18 | 2015-06-03 | 因西特公司 | 作为Janus激酶抑制剂的环丁烷和甲基环丁烷衍生物 |
| EP3050882B1 (en) | 2010-03-10 | 2018-01-31 | Incyte Holdings Corporation | Piperidin-4-yl azetidine derivatives as jak1 inhibitors |
| GB201007286D0 (en) | 2010-04-30 | 2010-06-16 | Astex Therapeutics Ltd | New compounds |
| SG10201503983QA (en) | 2010-05-21 | 2015-06-29 | Incyte Corp | Topical Formulation for a JAK Inhibitor |
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- 2008-11-13 CA CA2704599A patent/CA2704599C/en active Active
- 2008-11-13 WO PCT/US2008/083319 patent/WO2009064835A1/en not_active Ceased
- 2008-11-13 KR KR1020107012777A patent/KR101580482B1/ko not_active Expired - Fee Related
- 2008-11-13 MX MX2010005300A patent/MX2010005300A/es active IP Right Grant
- 2008-11-13 JP JP2010534154A patent/JP5480813B2/ja not_active Expired - Fee Related
- 2008-11-13 EP EP08848610.5A patent/EP2220068B1/en active Active
- 2008-11-13 BR BRPI0820544-2A patent/BRPI0820544A2/pt not_active Application Discontinuation
- 2008-11-13 UA UAA201007505A patent/UA104849C2/uk unknown
- 2008-11-13 MY MYPI20102079 patent/MY152948A/en unknown
- 2008-11-13 EA EA201070618A patent/EA020777B1/ru unknown
- 2008-11-13 CN CN200880123789.2A patent/CN101910152B/zh active Active
-
2010
- 2010-05-06 IL IL205571A patent/IL205571A/en active IP Right Grant
- 2010-05-14 CR CR11430A patent/CR11430A/es unknown
- 2010-05-26 CO CO10063312A patent/CO6280420A2/es active IP Right Grant
- 2010-06-07 ZA ZA2010/04055A patent/ZA201004055B/en unknown
- 2010-06-16 EC EC2010010263A patent/ECSP10010263A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CR11430A (es) | 2010-07-01 |
| AU2008321046B2 (en) | 2013-10-24 |
| JP2011503194A (ja) | 2011-01-27 |
| KR101580482B1 (ko) | 2015-12-28 |
| UA104849C2 (uk) | 2014-03-25 |
| IL205571A (en) | 2015-09-24 |
| CA2704599C (en) | 2015-05-12 |
| JP5480813B2 (ja) | 2014-04-23 |
| CA2704599A1 (en) | 2009-05-22 |
| ZA201004055B (en) | 2012-09-26 |
| EP2220068A1 (en) | 2010-08-25 |
| EP2220068B1 (en) | 2016-01-27 |
| MX2010005300A (es) | 2010-06-25 |
| WO2009064835A1 (en) | 2009-05-22 |
| EA201070618A1 (ru) | 2010-12-30 |
| ECSP10010263A (es) | 2010-07-30 |
| NZ585139A (en) | 2012-05-25 |
| IL205571A0 (en) | 2010-12-30 |
| HK1147476A1 (zh) | 2011-08-12 |
| US20090318405A1 (en) | 2009-12-24 |
| CN101910152A (zh) | 2010-12-08 |
| CN101910152B (zh) | 2014-08-06 |
| US8309718B2 (en) | 2012-11-13 |
| AU2008321046A1 (en) | 2009-05-22 |
| BRPI0820544A2 (pt) | 2015-06-16 |
| CO6280420A2 (es) | 2011-05-20 |
| EA020777B1 (ru) | 2015-01-30 |
| KR20100095582A (ko) | 2010-08-31 |
| MY152948A (en) | 2014-12-15 |
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