JP2017519023A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017519023A5 JP2017519023A5 JP2016574907A JP2016574907A JP2017519023A5 JP 2017519023 A5 JP2017519023 A5 JP 2017519023A5 JP 2016574907 A JP2016574907 A JP 2016574907A JP 2016574907 A JP2016574907 A JP 2016574907A JP 2017519023 A5 JP2017519023 A5 JP 2017519023A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- amine
- pyrimidin
- benzenesulfonyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 29
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 10
- 150000001412 amines Chemical class 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- PPUDTILCWKIDEQ-GFCCVEGCSA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-[(2R)-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C(F)(F)F)C)N PPUDTILCWKIDEQ-GFCCVEGCSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 2
- QMOFNYJKQAKABC-UHFFFAOYSA-N 4-N-(4-chlorophenyl)-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound ClC1=CC=C(C=C1)NC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F QMOFNYJKQAKABC-UHFFFAOYSA-N 0.000 claims 2
- RRYDRDMCHZVWAA-NSHDSACASA-N 4-[(2R)-2-(fluoromethyl)morpholin-4-yl]-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)CF)C)N RRYDRDMCHZVWAA-NSHDSACASA-N 0.000 claims 2
- GUFZZHYDDQQBDT-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-N-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-2,6-diamine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)NC)N GUFZZHYDDQQBDT-UHFFFAOYSA-N 0.000 claims 2
- QPFDRGFJDHYCON-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-[2-methyl-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)(C(F)(F)F)C)C)N QPFDRGFJDHYCON-UHFFFAOYSA-N 0.000 claims 2
- INNFWAIBUHUWLL-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-methylsulfanyl-4-[2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C(F)(F)F)SC)N INNFWAIBUHUWLL-UHFFFAOYSA-N 0.000 claims 2
- KMXAPVDWEKYSHR-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-4-[2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C(F)(F)F)N KMXAPVDWEKYSHR-UHFFFAOYSA-N 0.000 claims 2
- 102100040133 Free fatty acid receptor 2 Human genes 0.000 claims 2
- 101000890668 Homo sapiens Free fatty acid receptor 2 Proteins 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 239000001301 oxygen Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- HLZDHCWNADLKPD-UHFFFAOYSA-N 4-(2,2-dimethylmorpholin-4-yl)-7-(2-fluoro-4-methoxyphenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1(CN(CCO1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=C(C=C1)OC)F)C HLZDHCWNADLKPD-UHFFFAOYSA-N 0.000 claims 1
- CGBCHKGNHBDVAP-UHFFFAOYSA-N 4-(2,2-dimethylmorpholin-4-yl)-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1(CN(CCO1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F)C CGBCHKGNHBDVAP-UHFFFAOYSA-N 0.000 claims 1
- OOTAUZPKGYREFF-UHFFFAOYSA-N 4-(2,2-dimethylmorpholin-4-yl)-7-(3-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1(CN(CCO1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC(=CC=C1)F)C OOTAUZPKGYREFF-UHFFFAOYSA-N 0.000 claims 1
- RIHBQVDMEHAPOT-UHFFFAOYSA-N 4-(2,2-dimethylmorpholin-4-yl)-7-(4-methoxyphenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1(CN(CCO1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC)C RIHBQVDMEHAPOT-UHFFFAOYSA-N 0.000 claims 1
- OZGCHBYIXSVLPI-UHFFFAOYSA-N 4-(2,2-dimethylmorpholin-4-yl)-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1(CN(CCO1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC)C OZGCHBYIXSVLPI-UHFFFAOYSA-N 0.000 claims 1
- IOQLBIPOPVJUSF-UHFFFAOYSA-N 4-(2,2-dimethyloxan-3-yl)oxy-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1(OCCCC1OC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F)C IOQLBIPOPVJUSF-UHFFFAOYSA-N 0.000 claims 1
- LRYKABOCLKXRLS-UHFFFAOYSA-N 4-(2,2-dimethyloxan-4-yl)oxy-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1(OCCC(C1)OC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F)C LRYKABOCLKXRLS-UHFFFAOYSA-N 0.000 claims 1
- IZRWCICXLFTWQS-UHFFFAOYSA-N 4-(2-ethylmorpholin-4-yl)-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C(C)C1CN(CCO1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC IZRWCICXLFTWQS-UHFFFAOYSA-N 0.000 claims 1
- VSRTWNMYWJGSGP-UHFFFAOYSA-N 4-(2-methylmorpholin-4-yl)-7-(2-methylphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N VSRTWNMYWJGSGP-UHFFFAOYSA-N 0.000 claims 1
- NYFYFXXNOFEEHK-UHFFFAOYSA-N 4-(2-methylmorpholin-4-yl)-7-(2-phenylethylsulfonyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1CN(CCO1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)CCC1=CC=CC=C1 NYFYFXXNOFEEHK-UHFFFAOYSA-N 0.000 claims 1
- LXSALCJOAYPZHJ-UHFFFAOYSA-N 4-(2-methylmorpholin-4-yl)-7-(3-methylphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC=1C=C(C=CC=1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N LXSALCJOAYPZHJ-UHFFFAOYSA-N 0.000 claims 1
- QCAPYNXALFVOBO-UHFFFAOYSA-N 4-(2-methylmorpholin-4-yl)-7-(4-propan-2-yloxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1CN(CCO1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC(C)C QCAPYNXALFVOBO-UHFFFAOYSA-N 0.000 claims 1
- MFBHEQCDBHMGQG-UHFFFAOYSA-N 4-(2-methylmorpholin-4-yl)-7-[4-(trifluoromethyl)phenyl]sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1CN(CCO1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F MFBHEQCDBHMGQG-UHFFFAOYSA-N 0.000 claims 1
- QHBLTWKEMHEMGT-UHFFFAOYSA-N 4-(2-methylmorpholin-4-yl)-7-phenylsulfanyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1CN(CCO1)C=1C2=C(N=CN=1)C(=C(N2)N)SC1=CC=CC=C1 QHBLTWKEMHEMGT-UHFFFAOYSA-N 0.000 claims 1
- KPBOIZXPQMOAPC-UHFFFAOYSA-N 4-(2-methylmorpholin-4-yl)-7-pyridin-3-ylsulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1CN(CCO1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C=1C=NC=CC=1 KPBOIZXPQMOAPC-UHFFFAOYSA-N 0.000 claims 1
- VFZDXBDENMGVLT-UHFFFAOYSA-N 4-(3,4a,5,6,7,7a-hexahydro-2H-cyclopenta[b][1,4]oxazin-4-yl)-7-(benzenesulfonyl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1=NC(N2CCOC3CCCC23)=C2NC(N)=C(C2=N1)S(=O)(=O)C1=CC=CC=C1 VFZDXBDENMGVLT-UHFFFAOYSA-N 0.000 claims 1
- NKZSZNDESSWPJR-UHFFFAOYSA-N 4-(4,4-difluoropiperidin-1-yl)-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1(CCN(CC1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F)F NKZSZNDESSWPJR-UHFFFAOYSA-N 0.000 claims 1
- ZEJADUACMQXHST-UHFFFAOYSA-N 4-(4,4-difluoropiperidin-1-yl)-7-(2-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1(CCN(CC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F)F ZEJADUACMQXHST-UHFFFAOYSA-N 0.000 claims 1
- UZHQFNDDNPJBBX-UHFFFAOYSA-N 4-(4,4-difluoropiperidin-1-yl)-7-(3-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1(CCN(CC1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC(=CC=C1)F)F UZHQFNDDNPJBBX-UHFFFAOYSA-N 0.000 claims 1
- DVUWNUQSMZIPFS-UHFFFAOYSA-N 4-(4,4-difluoropiperidin-1-yl)-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1(CCN(CC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC)F DVUWNUQSMZIPFS-UHFFFAOYSA-N 0.000 claims 1
- YWXZEVLCQYDBMX-UHFFFAOYSA-N 4-(6-azaspiro[2.5]octan-6-yl)-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1=NC(N2CCC3(CC3)CC2)=C2NC(N)=C(C2=N1)S(=O)(=O)C1=C(F)C=CC=C1 YWXZEVLCQYDBMX-UHFFFAOYSA-N 0.000 claims 1
- YCXWAJUFUOIPCK-UHFFFAOYSA-N 4-(6-azaspiro[2.5]octan-6-yl)-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1CC11CCN(CC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC YCXWAJUFUOIPCK-UHFFFAOYSA-N 0.000 claims 1
- ZCMMZGDHUDHFMH-UHFFFAOYSA-N 4-(6-azaspiro[2.5]octan-6-yl)-7-(benzenesulfonyl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1CC11CCN(CC1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC=CC=C1 ZCMMZGDHUDHFMH-UHFFFAOYSA-N 0.000 claims 1
- IYFCPFLUMCGQRH-UHFFFAOYSA-N 4-(azepan-1-yl)-7-(benzenesulfonyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound N1(CCCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=CC=C1 IYFCPFLUMCGQRH-UHFFFAOYSA-N 0.000 claims 1
- SIBTYGKBRHWZOC-UHFFFAOYSA-N 4-(azetidin-1-yl)-7-(benzenesulfonyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound N1(CCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=CC=C1 SIBTYGKBRHWZOC-UHFFFAOYSA-N 0.000 claims 1
- QBNSEXGNWYXCRS-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(3,4-difluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound NC1=C(C2=NC=NC(=C2N1)C1=CCCCC1)S(=O)(=O)C1=CC(F)=C(F)C=C1 QBNSEXGNWYXCRS-UHFFFAOYSA-N 0.000 claims 1
- JSMIPRJWANMCGD-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(3-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound NC1=C(C2=NC=NC(=C2N1)C1=CCCCC1)S(=O)(=O)C1=CC(F)=CC=C1 JSMIPRJWANMCGD-UHFFFAOYSA-N 0.000 claims 1
- MUNWUSBVQCHDLH-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(4-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound NC1=C(C2=NC=NC(=C2N1)C1=CCCCC1)S(=O)(=O)C1=CC=C(F)C=C1 MUNWUSBVQCHDLH-UHFFFAOYSA-N 0.000 claims 1
- SLJLDUBWZPCCEN-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C1=C(N)NC2=C(N=CN=C12)C1=CCCCC1 SLJLDUBWZPCCEN-UHFFFAOYSA-N 0.000 claims 1
- NJEDVWCVFKBJMR-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(4-methylphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1=CC=C(C=C1)S(=O)(=O)C1=C(N)NC2=C(N=CN=C12)C1=CCCCC1 NJEDVWCVFKBJMR-UHFFFAOYSA-N 0.000 claims 1
- LAMSUKGCNYWQNB-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(6-methoxypyridin-3-yl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C=1C=NC(=CC=1)OC LAMSUKGCNYWQNB-UHFFFAOYSA-N 0.000 claims 1
- NHHDJQNPZOUYAM-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(oxan-4-ylmethylsulfonyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)CC1CCOCC1 NHHDJQNPZOUYAM-UHFFFAOYSA-N 0.000 claims 1
- URWAADUWDYNLRF-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(oxan-4-ylsulfonyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1CCOCC1 URWAADUWDYNLRF-UHFFFAOYSA-N 0.000 claims 1
- RRDFIHMRUUGAOS-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-(oxolan-3-ylsulfonyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1COCC1 RRDFIHMRUUGAOS-UHFFFAOYSA-N 0.000 claims 1
- RTSYYRZCSAXPGU-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-[4-(difluoromethoxy)phenyl]sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound NC1=C(C2=C(N1)C(=NC=N2)C1=CCCCC1)S(=O)(=O)C1=CC=C(OC(F)F)C=C1 RTSYYRZCSAXPGU-UHFFFAOYSA-N 0.000 claims 1
- YRDPRMGFFAUJCV-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-cyclohexylsulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1CCCCC1 YRDPRMGFFAUJCV-UHFFFAOYSA-N 0.000 claims 1
- VERJSMGAYFOTQV-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-phenylsulfanyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)SC1=CC=CC=C1 VERJSMGAYFOTQV-UHFFFAOYSA-N 0.000 claims 1
- HELGBUUGRXIODK-UHFFFAOYSA-N 4-(cyclohexen-1-yl)-7-pyridin-2-ylsulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=NC=CC=C1 HELGBUUGRXIODK-UHFFFAOYSA-N 0.000 claims 1
- IZPISXUEIMNBJT-UHFFFAOYSA-N 4-(cyclopenten-1-yl)-7-(2-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F IZPISXUEIMNBJT-UHFFFAOYSA-N 0.000 claims 1
- HXDIHAAILKXXBJ-UHFFFAOYSA-N 4-(cyclopenten-1-yl)-7-(3-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCC1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC(=CC=C1)F HXDIHAAILKXXBJ-UHFFFAOYSA-N 0.000 claims 1
- JTYLEKYWCXDSHZ-UHFFFAOYSA-N 4-(cyclopenten-1-yl)-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC JTYLEKYWCXDSHZ-UHFFFAOYSA-N 0.000 claims 1
- XYMQNAMXAZNVCS-UHFFFAOYSA-N 4-(cyclopropylmethoxy)-7-(3-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(CC1)COC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC(=CC=C1)F XYMQNAMXAZNVCS-UHFFFAOYSA-N 0.000 claims 1
- AZEKYSPKUXGNPX-GHMZBOCLSA-N 4-[(2R,3R)-2,3-dimethylmorpholin-4-yl]-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@H]1OCCN([C@@H]1C)c1nc(C)nc2c(c(N)[nH]c12)S(=O)(=O)c1ccccc1F AZEKYSPKUXGNPX-GHMZBOCLSA-N 0.000 claims 1
- AZEKYSPKUXGNPX-WDEREUQCSA-N 4-[(2R,3S)-2,3-dimethylmorpholin-4-yl]-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@H]1OCCN([C@H]1C)c1nc(C)nc2c(c(N)[nH]c12)S(=O)(=O)c1ccccc1F AZEKYSPKUXGNPX-WDEREUQCSA-N 0.000 claims 1
- GBGBTXXOCXPTRB-GHMZBOCLSA-N 4-[(2R,5R)-2,5-dimethylmorpholin-4-yl]-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@@H]1CN([C@H](C)CO1)C1=C2NC(N)=C(C2=NC(C)=N1)S(=O)(=O)C1=C(F)C=CC=C1 GBGBTXXOCXPTRB-GHMZBOCLSA-N 0.000 claims 1
- FFKYPPBXLPNOOV-GHMZBOCLSA-N 4-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@@H]1CN(C[C@H](O1)C)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F FFKYPPBXLPNOOV-GHMZBOCLSA-N 0.000 claims 1
- ZVGIMOWURAJEGQ-GHMZBOCLSA-N 4-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-7-(3-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@@H]1CN(C[C@H](O1)C)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC(=CC=C1)F ZVGIMOWURAJEGQ-GHMZBOCLSA-N 0.000 claims 1
- GBGBTXXOCXPTRB-QWRGUYRKSA-N 4-[(2S,5S)-2,5-dimethylmorpholin-4-yl]-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@H]1CN([C@@H](C)CO1)C1=C2NC(N)=C(C2=NC(C)=N1)S(=O)(=O)C1=C(F)C=CC=C1 GBGBTXXOCXPTRB-QWRGUYRKSA-N 0.000 claims 1
- FFKYPPBXLPNOOV-PHIMTYICSA-N 4-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@@H]1CN(C[C@@H](O1)C)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F FFKYPPBXLPNOOV-PHIMTYICSA-N 0.000 claims 1
- ZVGIMOWURAJEGQ-PHIMTYICSA-N 4-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-7-(3-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@@H]1CN(C[C@@H](O1)C)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC(=CC=C1)F ZVGIMOWURAJEGQ-PHIMTYICSA-N 0.000 claims 1
- TUKJVXRYLOSHEO-TXEJJXNPSA-N 4-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C[C@@H]1CN(C[C@@H](O1)C)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC TUKJVXRYLOSHEO-TXEJJXNPSA-N 0.000 claims 1
- RRYDRDMCHZVWAA-UHFFFAOYSA-N 4-[2-(fluoromethyl)morpholin-4-yl]-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1=NC(N2CCOC(CF)C2)=C2NC(N)=C(C2=N1)S(=O)(=O)C1=C(F)C=CC=C1 RRYDRDMCHZVWAA-UHFFFAOYSA-N 0.000 claims 1
- SYQFFZIBGPIIBJ-UHFFFAOYSA-N 4-[6-amino-7-(benzenesulfonyl)-5H-pyrrolo[3,2-d]pyrimidin-4-yl]morpholine-2-carbonitrile Chemical compound NC1=C(C=2N=CN=C(C=2N1)N1CC(OCC1)C#N)S(=O)(=O)C1=CC=CC=C1 SYQFFZIBGPIIBJ-UHFFFAOYSA-N 0.000 claims 1
- UEEIBAYRNQCKCP-UHFFFAOYSA-N 4-chloro-7-(2-fluoro-4-methoxyphenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=C(C=C1)OC)F UEEIBAYRNQCKCP-UHFFFAOYSA-N 0.000 claims 1
- AVYHHLNMVRANDF-UHFFFAOYSA-N 4-chloro-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F AVYHHLNMVRANDF-UHFFFAOYSA-N 0.000 claims 1
- JNHOCUXHMTWQID-UHFFFAOYSA-N 4-chloro-7-(2-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F JNHOCUXHMTWQID-UHFFFAOYSA-N 0.000 claims 1
- KAHSMEQANKHPOZ-UHFFFAOYSA-N 4-chloro-7-(3-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC(=CC=C1)F KAHSMEQANKHPOZ-UHFFFAOYSA-N 0.000 claims 1
- SZOVDMODWDUSBX-UHFFFAOYSA-N 4-chloro-7-(4-methoxyphenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC SZOVDMODWDUSBX-UHFFFAOYSA-N 0.000 claims 1
- XNPDYDSWFSQURL-UHFFFAOYSA-N 4-chloro-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC=C(C=C1)OC XNPDYDSWFSQURL-UHFFFAOYSA-N 0.000 claims 1
- BOBYDRLWXIQMOT-UHFFFAOYSA-N 4-cyclobutyloxy-7-(2-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(CCC1)OC=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F BOBYDRLWXIQMOT-UHFFFAOYSA-N 0.000 claims 1
- BJCCBUYXXCLGIO-UHFFFAOYSA-N 4-cyclohexyl-7-(2-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F BJCCBUYXXCLGIO-UHFFFAOYSA-N 0.000 claims 1
- ALXOWYNWICJRRO-UHFFFAOYSA-N 4-cyclohexyl-7-(3,4-difluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(CCCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=CC(=C(C=C1)F)F ALXOWYNWICJRRO-UHFFFAOYSA-N 0.000 claims 1
- QOXSXOGSWOADFL-UHFFFAOYSA-N 4-cyclohexyl-7-(3-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound NC1=C(C2=C(N1)C(=NC=N2)C1CCCCC1)S(=O)(=O)C1=CC(F)=CC=C1 QOXSXOGSWOADFL-UHFFFAOYSA-N 0.000 claims 1
- DGLVXKASQUZVAJ-UHFFFAOYSA-N 4-cyclohexyl-7-(4-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound NC1=C(C2=C(N1)C(=NC=N2)C1CCCCC1)S(=O)(=O)C1=CC=C(F)C=C1 DGLVXKASQUZVAJ-UHFFFAOYSA-N 0.000 claims 1
- IAQOKMSZVOIBFV-UHFFFAOYSA-N 4-cyclohexyl-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C1=C(N)NC2=C(N=CN=C12)C1CCCCC1 IAQOKMSZVOIBFV-UHFFFAOYSA-N 0.000 claims 1
- GCXZQBUDARNJHQ-UHFFFAOYSA-N 4-cyclohexyl-7-(4-methylphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1=CC=C(C=C1)S(=O)(=O)C1=C(N)NC2=C1N=CN=C2C1CCCCC1 GCXZQBUDARNJHQ-UHFFFAOYSA-N 0.000 claims 1
- ZWOOWQAMLSSBIO-UHFFFAOYSA-N 4-cyclohexyl-7-[4-(difluoromethoxy)phenyl]sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound NC1=C(C2=C(N1)C(=NC=N2)C1CCCCC1)S(=O)(=O)C1=CC=C(OC(F)F)C=C1 ZWOOWQAMLSSBIO-UHFFFAOYSA-N 0.000 claims 1
- NQHVBEJQNXTUCJ-UHFFFAOYSA-N 4-cyclohexyl-7-cyclohexylsulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(CCCCC1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1CCCCC1)N NQHVBEJQNXTUCJ-UHFFFAOYSA-N 0.000 claims 1
- PRTJQIBGLNSHOB-UHFFFAOYSA-N 4-cyclopentyl-7-(2-fluorophenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(CCCC1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)C1=C(C=CC=C1)F PRTJQIBGLNSHOB-UHFFFAOYSA-N 0.000 claims 1
- QHXYBIJCCWSRRA-UHFFFAOYSA-N 4-cyclopentyl-7-(3-fluorophenyl)sulfonyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(CCCC1)C=1C2=C(N=C(N=1)C)C(=C(N2)N)S(=O)(=O)C1=CC(=CC=C1)F QHXYBIJCCWSRRA-UHFFFAOYSA-N 0.000 claims 1
- SJUYXUIQTSTVLZ-UHFFFAOYSA-N 4-cyclopentyl-7-(4-methoxyphenyl)sulfonyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C1=C(N)NC2=C(N=CN=C12)C1CCCC1 SJUYXUIQTSTVLZ-UHFFFAOYSA-N 0.000 claims 1
- ATQGBTGRQWFIPY-UHFFFAOYSA-N 6-amino-4-(cyclohexen-1-yl)-N-(4-methoxyphenyl)-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-7-sulfonamide Chemical compound NC1=C(C=2N=CN=C(C=2N1)C1=CCCCC1)S(=O)(=O)N(C)C1=CC=C(C=C1)OC ATQGBTGRQWFIPY-UHFFFAOYSA-N 0.000 claims 1
- DRESIGMYYZZIMO-UHFFFAOYSA-N 7-(2,3-difluorophenyl)sulfonyl-2-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C)N DRESIGMYYZZIMO-UHFFFAOYSA-N 0.000 claims 1
- MBHKLSUANWTFOS-UHFFFAOYSA-N 7-(2,4-difluorophenyl)sulfonyl-2-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC(=C1)F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C)N MBHKLSUANWTFOS-UHFFFAOYSA-N 0.000 claims 1
- IXXZSRAIVCLCIK-LBPRGKRZSA-N 7-(2,4-difluorophenyl)sulfonyl-2-methyl-4-[(2S)-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical class FC1=C(C=CC(=C1)F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@H](OCC1)C(F)(F)F)C)N IXXZSRAIVCLCIK-LBPRGKRZSA-N 0.000 claims 1
- RCEIBJIEXQXTDN-UHFFFAOYSA-N 7-(2,4-difluorophenyl)sulfonyl-4-(2,2-dimethylmorpholin-4-yl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC(=C1)F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)(C)C)C)N RCEIBJIEXQXTDN-UHFFFAOYSA-N 0.000 claims 1
- DBOFFBLMKYKHOJ-UHFFFAOYSA-N 7-(2,5-difluorophenyl)sulfonyl-2-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=C(C=C1)F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C)N DBOFFBLMKYKHOJ-UHFFFAOYSA-N 0.000 claims 1
- JLXMNAHHADOMNV-UHFFFAOYSA-N 7-(2,5-difluorophenyl)sulfonyl-4-(2,2-dimethylmorpholin-4-yl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=C(C=C1)F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)(C)C)C)N JLXMNAHHADOMNV-UHFFFAOYSA-N 0.000 claims 1
- NSQNVRCLMOBDLR-UHFFFAOYSA-N 7-(2,6-difluorophenyl)sulfonyl-2-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C(=CC=C1)F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C)N NSQNVRCLMOBDLR-UHFFFAOYSA-N 0.000 claims 1
- MCJQIGLKKYWJSZ-LLVKDONJSA-N 7-(2,6-difluorophenyl)sulfonyl-2-methyl-4-[(2R)-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical class FC1=C(C(=CC=C1)F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C(F)(F)F)C)N MCJQIGLKKYWJSZ-LLVKDONJSA-N 0.000 claims 1
- XUQPAUMXJVEHEV-UHFFFAOYSA-N 7-(2,6-difluorophenyl)sulfonyl-4-(2,2-dimethylmorpholin-4-yl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C(=CC=C1)F)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)(C)C)C)N XUQPAUMXJVEHEV-UHFFFAOYSA-N 0.000 claims 1
- AFTBSJVLSKNSMH-JTQLQIEISA-N 7-(2-chlorophenyl)sulfonyl-2-methyl-4-[(2S)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C)C)N AFTBSJVLSKNSMH-JTQLQIEISA-N 0.000 claims 1
- HCVZDBSNADMNCS-CYBMUJFWSA-N 7-(2-fluoro-4-methoxyphenyl)sulfonyl-2-methyl-4-[(2R)-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC(=C1)OC)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C(F)(F)F)C)N HCVZDBSNADMNCS-CYBMUJFWSA-N 0.000 claims 1
- HCVZDBSNADMNCS-ZDUSSCGKSA-N 7-(2-fluoro-4-methoxyphenyl)sulfonyl-2-methyl-4-[(2S)-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC(=C1)OC)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@H](OCC1)C(F)(F)F)C)N HCVZDBSNADMNCS-ZDUSSCGKSA-N 0.000 claims 1
- OXTIOUBRXQCEJM-JTQLQIEISA-N 7-(2-fluoro-4-methoxyphenyl)sulfonyl-2-methyl-4-[(2S)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC(=C1)OC)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C)C)N OXTIOUBRXQCEJM-JTQLQIEISA-N 0.000 claims 1
- QYEJSGZKDNHVQX-UHFFFAOYSA-N 7-(2-fluoro-4-methylphenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC(=C1)C)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N QYEJSGZKDNHVQX-UHFFFAOYSA-N 0.000 claims 1
- QWLHINHQBWQCCE-UHFFFAOYSA-N 7-(2-fluoro-5-methoxyphenyl)sulfonyl-2-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=C(C=C1)OC)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C)N QWLHINHQBWQCCE-UHFFFAOYSA-N 0.000 claims 1
- WELALUPYWGSYLR-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-N,2-N-dimethyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-2,6-diamine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)N(C)C)N WELALUPYWGSYLR-UHFFFAOYSA-N 0.000 claims 1
- DVCYPACFAIPPPI-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-methoxy-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)OC)N DVCYPACFAIPPPI-UHFFFAOYSA-N 0.000 claims 1
- XHJNSLWNCNFDRK-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-(1,1,1-trifluoropropan-2-yloxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC(C(F)(F)F)C)C)N XHJNSLWNCNFDRK-UHFFFAOYSA-N 0.000 claims 1
- WDWMPFKLAAZMEM-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-(2,2,3-trimethylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C(C(OCC1)(C)C)C)C)N WDWMPFKLAAZMEM-UHFFFAOYSA-N 0.000 claims 1
- JWBHQXZBMJVNDY-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C)N JWBHQXZBMJVNDY-UHFFFAOYSA-N 0.000 claims 1
- PPUDTILCWKIDEQ-LBPRGKRZSA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-[(2S)-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1=NC(N2CCO[C@@H](C2)C(F)(F)F)=C2NC(N)=C(C2=N1)S(=O)(=O)C1=C(F)C=CC=C1 PPUDTILCWKIDEQ-LBPRGKRZSA-N 0.000 claims 1
- JWBHQXZBMJVNDY-JTQLQIEISA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-[(2S)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C)C)N JWBHQXZBMJVNDY-JTQLQIEISA-N 0.000 claims 1
- PPUDTILCWKIDEQ-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-[2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C(F)(F)F)C)N PPUDTILCWKIDEQ-UHFFFAOYSA-N 0.000 claims 1
- ZXVRJMPGGMIFMG-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-2-methyl-4-propan-2-yloxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC(C)C)C)N ZXVRJMPGGMIFMG-UHFFFAOYSA-N 0.000 claims 1
- QSUZYKVTZNBJOS-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-2-(trifluoromethyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C(F)(F)F)N QSUZYKVTZNBJOS-UHFFFAOYSA-N 0.000 claims 1
- QDDAXTUUYGSAQW-UHFFFAOYSA-N 7-(2-fluorophenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-2-methylsulfanyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CSC1=NC(N2CCOC(C)C2)=C2NC(N)=C(C2=N1)S(=O)(=O)C1=C(F)C=CC=C1 QDDAXTUUYGSAQW-UHFFFAOYSA-N 0.000 claims 1
- ICMFJQZJAQIECB-UHFFFAOYSA-N 7-(2-methoxyphenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC1=C(C=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N ICMFJQZJAQIECB-UHFFFAOYSA-N 0.000 claims 1
- RNRHVGUAFZUDAZ-UHFFFAOYSA-N 7-(3,5-difluorophenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC=1C=C(C=C(C=1)F)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N RNRHVGUAFZUDAZ-UHFFFAOYSA-N 0.000 claims 1
- VMWMJWCJPOZXLU-UHFFFAOYSA-N 7-(3-chloro-4-methoxyphenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC=1C=C(C=CC=1OC)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N VMWMJWCJPOZXLU-UHFFFAOYSA-N 0.000 claims 1
- RWUXMJDOILOVDX-UHFFFAOYSA-N 7-(3-fluoro-4-methoxyphenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC=1C=C(C=CC=1OC)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N RWUXMJDOILOVDX-UHFFFAOYSA-N 0.000 claims 1
- MNGQJTBLPBKGBL-UHFFFAOYSA-N 7-(3-fluorophenyl)sulfonyl-2-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC=1C=C(C=CC=1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C)N MNGQJTBLPBKGBL-UHFFFAOYSA-N 0.000 claims 1
- IWLGLLLGRWNZKX-UHFFFAOYSA-N 7-(3-fluorophenyl)sulfonyl-2-methyl-4-(3-methylpiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC=1C=C(C=CC=1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(CCC1)C)C)N IWLGLLLGRWNZKX-UHFFFAOYSA-N 0.000 claims 1
- ZCLXTKTUOWMZDZ-UHFFFAOYSA-N 7-(3-fluorophenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-2-(trifluoromethyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC=1C=C(C=CC=1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C(F)(F)F)N ZCLXTKTUOWMZDZ-UHFFFAOYSA-N 0.000 claims 1
- PTPRBLQWOVJDRB-UHFFFAOYSA-N 7-(3-fluorophenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-2-methylsulfanyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC=1C=C(C=CC=1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)SC)N PTPRBLQWOVJDRB-UHFFFAOYSA-N 0.000 claims 1
- CICCQHAROYVQAM-UHFFFAOYSA-N 7-(3-fluorophenyl)sulfonyl-4-N,2-dimethyl-4-N-propan-2-yl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound FC=1C=C(C=CC=1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N(C(C)C)C)C)N CICCQHAROYVQAM-UHFFFAOYSA-N 0.000 claims 1
- UTWLDSSDGRHONJ-UHFFFAOYSA-N 7-(3-methoxyphenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC=1C=C(C=CC=1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N UTWLDSSDGRHONJ-UHFFFAOYSA-N 0.000 claims 1
- MIFHMXHECLXSRQ-VIFPVBQESA-N 7-(4-bromo-2-fluorophenyl)sulfonyl-2-methyl-4-[(2S)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound BrC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C)C)N)F MIFHMXHECLXSRQ-VIFPVBQESA-N 0.000 claims 1
- CZEOBUCMCFXYRK-UHFFFAOYSA-N 7-(4-bromo-2-fluorophenyl)sulfonyl-4-chloro-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound BrC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2Cl)C)N)F CZEOBUCMCFXYRK-UHFFFAOYSA-N 0.000 claims 1
- PYTJUWVZOWTLEX-GFCCVEGCSA-N 7-(4-chloro-2-fluorophenyl)sulfonyl-2-methyl-4-[(2R)-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C(F)(F)F)C)N)F PYTJUWVZOWTLEX-GFCCVEGCSA-N 0.000 claims 1
- PYTJUWVZOWTLEX-LBPRGKRZSA-N 7-(4-chloro-2-fluorophenyl)sulfonyl-2-methyl-4-[(2S)-2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@H](OCC1)C(F)(F)F)C)N)F PYTJUWVZOWTLEX-LBPRGKRZSA-N 0.000 claims 1
- VCOGGEJQZQKYSL-VIFPVBQESA-N 7-(4-chloro-2-fluorophenyl)sulfonyl-2-methyl-4-[(2S)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C)C)N)F VCOGGEJQZQKYSL-VIFPVBQESA-N 0.000 claims 1
- AXGYVGVOMLEPDU-UHFFFAOYSA-N 7-(4-chloro-2-fluorophenyl)sulfonyl-4-(2,2-dimethylmorpholin-4-yl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)(C)C)C)N)F AXGYVGVOMLEPDU-UHFFFAOYSA-N 0.000 claims 1
- AMXBLCZKVVFNJJ-UHFFFAOYSA-N 7-(4-chloro-3-fluorophenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound ClC1=C(C=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N)F AMXBLCZKVVFNJJ-UHFFFAOYSA-N 0.000 claims 1
- NFXSAGQCXSMZJB-UHFFFAOYSA-N 7-(4-chlorophenyl)sulfonyl-4-(cyclohexen-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound NC1=C(C2=NC=NC(=C2N1)C1=CCCCC1)S(=O)(=O)C1=CC=C(Cl)C=C1 NFXSAGQCXSMZJB-UHFFFAOYSA-N 0.000 claims 1
- UPKAFIVHFFETDO-UHFFFAOYSA-N 7-(4-fluoro-2-methoxyphenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N)OC UPKAFIVHFFETDO-UHFFFAOYSA-N 0.000 claims 1
- YSZAFGGKSLGCJZ-UHFFFAOYSA-N 7-(4-fluoro-2-methylphenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound FC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N)C YSZAFGGKSLGCJZ-UHFFFAOYSA-N 0.000 claims 1
- CMAUGOHLQGOYSC-UHFFFAOYSA-N 7-(4-methoxyphenyl)sulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N CMAUGOHLQGOYSC-UHFFFAOYSA-N 0.000 claims 1
- SXOUEPNKLIRGSP-UHFFFAOYSA-N 7-(4-methoxyphenyl)sulfonyl-4-(3-methylpiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CCC1)C)N SXOUEPNKLIRGSP-UHFFFAOYSA-N 0.000 claims 1
- HDLWDEWSZWMGLY-UHFFFAOYSA-N 7-(4-methoxyphenyl)sulfonyl-4-phenyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=CC=CC=C1)N HDLWDEWSZWMGLY-UHFFFAOYSA-N 0.000 claims 1
- LIIVSNVVGCGAEU-UHFFFAOYSA-N 7-(4-methoxyphenyl)sulfonyl-4-prop-1-en-2-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound COC1=CC=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C(=C)C)N LIIVSNVVGCGAEU-UHFFFAOYSA-N 0.000 claims 1
- SDVFHWXQZUFGMY-UHFFFAOYSA-N 7-(benzenesulfonyl)-2-methyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)C)N SDVFHWXQZUFGMY-UHFFFAOYSA-N 0.000 claims 1
- XXEHRLZRINTZHS-UHFFFAOYSA-N 7-(benzenesulfonyl)-2-methyl-4-(2-methylpropoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OCC(C)C)C)N XXEHRLZRINTZHS-UHFFFAOYSA-N 0.000 claims 1
- DUWLCMBELFLASB-UHFFFAOYSA-N 7-(benzenesulfonyl)-2-methyl-4-(3-methylphenyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C1=CC(=CC=C1)C)C)N DUWLCMBELFLASB-UHFFFAOYSA-N 0.000 claims 1
- RZOJBNHQSVMXPS-UHFFFAOYSA-N 7-(benzenesulfonyl)-2-methyl-4-(3-methylpiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(CCC1)C)C)N RZOJBNHQSVMXPS-UHFFFAOYSA-N 0.000 claims 1
- QFZFIYJBEDILMP-UHFFFAOYSA-N 7-(benzenesulfonyl)-2-methyl-4-(4-oxa-7-azaspiro[2.5]octan-7-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CCOC2(CC2)C1)C)N QFZFIYJBEDILMP-UHFFFAOYSA-N 0.000 claims 1
- SDVFHWXQZUFGMY-NSHDSACASA-N 7-(benzenesulfonyl)-2-methyl-4-[(2S)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C)C)N SDVFHWXQZUFGMY-NSHDSACASA-N 0.000 claims 1
- YEXBFHKMQZZHOI-UHFFFAOYSA-N 7-(benzenesulfonyl)-2-methyl-4-pentan-3-yloxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC(CC)CC)C)N YEXBFHKMQZZHOI-UHFFFAOYSA-N 0.000 claims 1
- LMTGUYVTRKRGLG-UHFFFAOYSA-N 7-(benzenesulfonyl)-2-methyl-4-prop-1-en-2-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C(=C)C)C)N LMTGUYVTRKRGLG-UHFFFAOYSA-N 0.000 claims 1
- HIENHCNRRPMKDA-UHFFFAOYSA-N 7-(benzenesulfonyl)-2-methyl-4-propan-2-yloxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC(C)C)C)N HIENHCNRRPMKDA-UHFFFAOYSA-N 0.000 claims 1
- GRIQAULUBDGGMM-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1,4-oxazepan-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCOCCC1)N GRIQAULUBDGGMM-UHFFFAOYSA-N 0.000 claims 1
- HHNCVTRHWKSBPH-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1-cyclobutylethoxy)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC(C)C1CCC1)C)N HHNCVTRHWKSBPH-UHFFFAOYSA-N 0.000 claims 1
- JDMFYJPDVDDYKK-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1-cyclohexylethoxy)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC(C)C1CCCCC1)C)N JDMFYJPDVDDYKK-UHFFFAOYSA-N 0.000 claims 1
- NPIKNBYWPYMKBR-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1-cyclopentylethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC(C)C1CCCC1)N NPIKNBYWPYMKBR-UHFFFAOYSA-N 0.000 claims 1
- RVBNNQWBJHKAPQ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1-cyclopropylethoxy)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC(C)C1CC1)C)N RVBNNQWBJHKAPQ-UHFFFAOYSA-N 0.000 claims 1
- RMSIJTKZFHESGP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1-cyclopropylethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC(C)C1CC1)N RMSIJTKZFHESGP-UHFFFAOYSA-N 0.000 claims 1
- OITKSARPRYFBDH-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1-cyclopropylpropoxy)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC(CC)C1CC1)C)N OITKSARPRYFBDH-UHFFFAOYSA-N 0.000 claims 1
- QECHMVNWCCAKFL-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1-phenylethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC(C)C1=CC=CC=C1)N QECHMVNWCCAKFL-UHFFFAOYSA-N 0.000 claims 1
- YHTAGANRCKMFTF-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(1-pyridin-2-ylethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC(C)C1=NC=CC=C1)N YHTAGANRCKMFTF-UHFFFAOYSA-N 0.000 claims 1
- FLKOVYLEBVJFJE-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,2-diethylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)(CC)CC)N FLKOVYLEBVJFJE-UHFFFAOYSA-N 0.000 claims 1
- SSCPEOHDDDQGLK-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,2-dimethylmorpholin-4-yl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)(C)C)C)N SSCPEOHDDDQGLK-UHFFFAOYSA-N 0.000 claims 1
- XJPZXMLUWMJDMI-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,2-dimethylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)(C)C)N XJPZXMLUWMJDMI-UHFFFAOYSA-N 0.000 claims 1
- ADNLDZWMGLPWMP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,2-dimethyloxan-4-yl)oxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC1CC(OCC1)(C)C)C)N ADNLDZWMGLPWMP-UHFFFAOYSA-N 0.000 claims 1
- MMSYWFAIWNIZFL-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,2-dimethyloxolan-3-yl)oxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC1C(OCC1)(C)C)C)N MMSYWFAIWNIZFL-UHFFFAOYSA-N 0.000 claims 1
- OAMORNNDZJYPSE-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,2-dimethylpropoxy)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OCC(C)(C)C)C)N OAMORNNDZJYPSE-UHFFFAOYSA-N 0.000 claims 1
- XLWSPJILJGGFRS-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,2-dimethylpyrrolidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C(CCC1)(C)C)N XLWSPJILJGGFRS-UHFFFAOYSA-N 0.000 claims 1
- RHAWBEMZGCBKJS-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,5-dimethylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1C)C)N RHAWBEMZGCBKJS-UHFFFAOYSA-N 0.000 claims 1
- DDSUNKQVBHQSER-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,6-dimethyloxan-4-yl)oxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC1CC(OC(C1)C)C)N DDSUNKQVBHQSER-UHFFFAOYSA-N 0.000 claims 1
- WZUYXAVQLYOTMB-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2,6-dimethylthiomorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(SC(C1)C)C)N WZUYXAVQLYOTMB-UHFFFAOYSA-N 0.000 claims 1
- RYANXWSHAZKMIE-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-cyclopropylethyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2CCC1CC1)N RYANXWSHAZKMIE-UHFFFAOYSA-N 0.000 claims 1
- IOXXOCGVKLEZAU-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-cyclopropylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C1CC1)N IOXXOCGVKLEZAU-UHFFFAOYSA-N 0.000 claims 1
- ISMYBXNHXNWKIZ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-ethyl-2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)(C)CC)N ISMYBXNHXNWKIZ-UHFFFAOYSA-N 0.000 claims 1
- DKGFLYWMUZMRLU-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-ethylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)CC)N DKGFLYWMUZMRLU-UHFFFAOYSA-N 0.000 claims 1
- ZNVBMENSFUNTSV-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-ethylthiomorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(SCC1)CC)N ZNVBMENSFUNTSV-UHFFFAOYSA-N 0.000 claims 1
- LTMRUBZRPJNGQD-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-methoxyethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCCOC)N LTMRUBZRPJNGQD-UHFFFAOYSA-N 0.000 claims 1
- GOJHDJHDEKPAQT-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-methylmorpholin-4-yl)-2-methylsulfanyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CC(OCC1)C)SC)N GOJHDJHDEKPAQT-UHFFFAOYSA-N 0.000 claims 1
- ADHJMTZWTHEQDG-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C)N ADHJMTZWTHEQDG-UHFFFAOYSA-N 0.000 claims 1
- ACDGHWXQQQATCV-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-methylphenyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=C(C=CC=C1)C)N ACDGHWXQQQATCV-UHFFFAOYSA-N 0.000 claims 1
- YSYXPFFMJWEYDD-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-methylpiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C(CCCC1)C)N YSYXPFFMJWEYDD-UHFFFAOYSA-N 0.000 claims 1
- YCRDDSHUGCTSEV-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-methylthiomorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(SCC1)C)N YCRDDSHUGCTSEV-UHFFFAOYSA-N 0.000 claims 1
- QXWXNBVATPZVQO-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-oxa-8-azaspiro[3.5]nonan-8-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC2(COC2)CCC1)N QXWXNBVATPZVQO-UHFFFAOYSA-N 0.000 claims 1
- IUWKISLQCWVWAB-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(2-propan-2-ylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C(C)C)N IUWKISLQCWVWAB-UHFFFAOYSA-N 0.000 claims 1
- SRDHZULQFXFMGD-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3,3-difluorocyclobutyl)oxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC1CC(C1)(F)F)C)N SRDHZULQFXFMGD-UHFFFAOYSA-N 0.000 claims 1
- WWKBFNYOVICLJH-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3,3-difluoropiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CCC1)(F)F)N WWKBFNYOVICLJH-UHFFFAOYSA-N 0.000 claims 1
- YIXXYLRHWQENOF-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3,3-difluoropyrrolidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CC1)(F)F)N YIXXYLRHWQENOF-UHFFFAOYSA-N 0.000 claims 1
- YNOJSBJHJVCISC-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3,3-dimethylpyrrolidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CC1)(C)C)N YNOJSBJHJVCISC-UHFFFAOYSA-N 0.000 claims 1
- CCEJPLMZBFVVEF-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3,5-dimethylpyrazol-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1N=C(C=C1C)C)N CCEJPLMZBFVVEF-UHFFFAOYSA-N 0.000 claims 1
- UIAZZNINVCQKOI-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3-ethoxypiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CCC1)OCC)N UIAZZNINVCQKOI-UHFFFAOYSA-N 0.000 claims 1
- HRXFNMDDJCRCAO-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3-methoxypiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CCC1)OC)N HRXFNMDDJCRCAO-UHFFFAOYSA-N 0.000 claims 1
- RIMLVPHMIIFDJP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3-methoxypyrrolidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CC1)OC)N RIMLVPHMIIFDJP-UHFFFAOYSA-N 0.000 claims 1
- MMADLXJSAWEWGK-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C(COCC1)C)N MMADLXJSAWEWGK-UHFFFAOYSA-N 0.000 claims 1
- ZCHHGAHPZZJJFA-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3-methylphenyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=CC(=CC=C1)C)N ZCHHGAHPZZJJFA-UHFFFAOYSA-N 0.000 claims 1
- UYWOZGHNXQOJGH-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3-methylpiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CCC1)C)N UYWOZGHNXQOJGH-UHFFFAOYSA-N 0.000 claims 1
- LBUUCZSQIKJONM-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(3-pyrazol-1-ylpiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(CCC1)N1N=CC=C1)N LBUUCZSQIKJONM-UHFFFAOYSA-N 0.000 claims 1
- UYFISPDRIDFBJU-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4,4-difluorocyclohexen-1-yl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C1=CCC(CC1)(F)F)C)N UYFISPDRIDFBJU-UHFFFAOYSA-N 0.000 claims 1
- UCIYEVNWTVRBJI-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4,4-difluorocyclohexen-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=CCC(CC1)(F)F)N UCIYEVNWTVRBJI-UHFFFAOYSA-N 0.000 claims 1
- FNBOUNPIRRIGEE-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4,4-difluorocyclohexyl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C1CCC(CC1)(F)F)C)N FNBOUNPIRRIGEE-UHFFFAOYSA-N 0.000 claims 1
- YJPUSWBKVNNQNA-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4,4-difluorocyclohexyl)oxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC1CCC(CC1)(F)F)C)N YJPUSWBKVNNQNA-UHFFFAOYSA-N 0.000 claims 1
- MLBXXXCUJHZEBT-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4,4-difluorocyclohexyl)oxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC1CCC(CC1)(F)F)N MLBXXXCUJHZEBT-UHFFFAOYSA-N 0.000 claims 1
- KUYSFGBZQSUGID-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4,4-difluoropiperidin-1-yl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1CCC(CC1)(F)F)C)N KUYSFGBZQSUGID-UHFFFAOYSA-N 0.000 claims 1
- JVOOJVWAWXSPFI-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4,4-difluoropiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCC(CC1)(F)F)N JVOOJVWAWXSPFI-UHFFFAOYSA-N 0.000 claims 1
- VOTYXMMQYXDZTR-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4-fluoropiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCC(CC1)F)N VOTYXMMQYXDZTR-UHFFFAOYSA-N 0.000 claims 1
- QZQXROUEYFPYDJ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4-methoxypiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCC(CC1)OC)N QZQXROUEYFPYDJ-UHFFFAOYSA-N 0.000 claims 1
- BIVSMSQZSIMLSD-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4-methylphenyl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=CC=C(C=C1)C)N BIVSMSQZSIMLSD-UHFFFAOYSA-N 0.000 claims 1
- MJXOTTIANSHING-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4-methylpiperidin-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCC(CC1)C)N MJXOTTIANSHING-UHFFFAOYSA-N 0.000 claims 1
- DAKRENKOZQEUEV-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(4-oxa-7-azaspiro[2.5]octan-7-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCOC2(CC2)C1)N DAKRENKOZQEUEV-UHFFFAOYSA-N 0.000 claims 1
- WAGPENIWGUQZBL-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(6-oxa-9-azaspiro[4.5]decan-9-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCOC2(CCCC2)C1)N WAGPENIWGUQZBL-UHFFFAOYSA-N 0.000 claims 1
- XVIKLXXEJNNYMH-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC2CCC(C1)O2)N XVIKLXXEJNNYMH-UHFFFAOYSA-N 0.000 claims 1
- MDTFJAYDLVZSBA-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(cyclobutylmethoxy)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OCC1CCC1)C)N MDTFJAYDLVZSBA-UHFFFAOYSA-N 0.000 claims 1
- FYVHJOGNKAMKAM-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(cyclohexen-1-yl)-2-ethyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C1=CCCCC1)CC)N FYVHJOGNKAMKAM-UHFFFAOYSA-N 0.000 claims 1
- DFJJQQZBDDEONY-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(cyclohexen-1-yl)-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C1=CCCCC1)C)N DFJJQQZBDDEONY-UHFFFAOYSA-N 0.000 claims 1
- PYSSDFKTCRXSGC-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(cyclohexen-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=CCCCC1)N PYSSDFKTCRXSGC-UHFFFAOYSA-N 0.000 claims 1
- CMWXNEJFGFQTOV-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(cyclohexylmethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1CCCCC1)N CMWXNEJFGFQTOV-UHFFFAOYSA-N 0.000 claims 1
- HCCBONGDMGKUGI-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(cyclopenten-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=CCCC1)N HCCBONGDMGKUGI-UHFFFAOYSA-N 0.000 claims 1
- ZZMOVIVPHQVKDR-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(cyclopentylmethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1CCCC1)N ZZMOVIVPHQVKDR-UHFFFAOYSA-N 0.000 claims 1
- JVHFYHVACPHNMJ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(cyclopropylmethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1CC1)N JVHFYHVACPHNMJ-UHFFFAOYSA-N 0.000 claims 1
- VGMYPGRYVYEWEN-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(oxan-2-ylmethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1OCCCC1)N VGMYPGRYVYEWEN-UHFFFAOYSA-N 0.000 claims 1
- HRHVBFUFAWGFHW-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(oxan-3-ylmethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1COCCC1)N HRHVBFUFAWGFHW-UHFFFAOYSA-N 0.000 claims 1
- AOXHNKWIHOGZLY-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(oxan-4-ylmethoxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1CCOCC1)N AOXHNKWIHOGZLY-UHFFFAOYSA-N 0.000 claims 1
- TVMMWMJTYOLHRC-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-(oxan-4-yloxy)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC1CCOCC1)N TVMMWMJTYOLHRC-UHFFFAOYSA-N 0.000 claims 1
- OTRJKPMQFDVVGF-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N,4-N-diethyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(CC)CC)N OTRJKPMQFDVVGF-UHFFFAOYSA-N 0.000 claims 1
- WOMWSPLLLOWLER-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-(1,3-dioxolan-2-ylmethyl)-4-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(C)CC1OCCO1)N WOMWSPLLLOWLER-UHFFFAOYSA-N 0.000 claims 1
- HLTKNKAIVNHEGZ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-(2,2-difluoroethyl)-4-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(C)CC(F)F)N HLTKNKAIVNHEGZ-UHFFFAOYSA-N 0.000 claims 1
- BOMOQBKEDKRAPQ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-(2,2-dimethyloxan-4-yl)-4-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(C)C1CC(OCC1)(C)C)N BOMOQBKEDKRAPQ-UHFFFAOYSA-N 0.000 claims 1
- VTQVIPNXLCHNER-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-(cyclopropylmethyl)-4-N-(oxolan-2-ylmethyl)-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(CC1OCCC1)CC1CC1)N VTQVIPNXLCHNER-UHFFFAOYSA-N 0.000 claims 1
- UFWCOWDWVOJJJY-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-(cyclopropylmethyl)-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2NCC1CC1)N UFWCOWDWVOJJJY-UHFFFAOYSA-N 0.000 claims 1
- ALZQLRNHFQNXQP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-[(2-methoxyphenyl)methyl]-4-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(C)CC1=C(C=CC=C1)OC)N ALZQLRNHFQNXQP-UHFFFAOYSA-N 0.000 claims 1
- UNSMQUQMDRDQCP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-[(3-chlorophenyl)methyl]-4-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(C)CC1=CC(=CC=C1)Cl)N UNSMQUQMDRDQCP-UHFFFAOYSA-N 0.000 claims 1
- ULAJZNOCNLQSCW-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-cyclopropyl-4-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(C)C1CC1)N ULAJZNOCNLQSCW-UHFFFAOYSA-N 0.000 claims 1
- KWOZONIVKFXRGR-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-ethyl-4-N-(furan-2-ylmethyl)-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(CC=1OC=CC=1)CC)N KWOZONIVKFXRGR-UHFFFAOYSA-N 0.000 claims 1
- KAJCBUPZXRONTO-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-ethyl-4-N-(oxan-4-ylmethyl)-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(CC1CCOCC1)CC)N KAJCBUPZXRONTO-UHFFFAOYSA-N 0.000 claims 1
- PCYFXQVMGNTPDP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-ethyl-4-N-[(1-methylpyrazol-4-yl)methyl]-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical class C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(CC=1C=NN(C=1)C)CC)N PCYFXQVMGNTPDP-UHFFFAOYSA-N 0.000 claims 1
- PBJMKNCCYFNSLX-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-ethyl-4-N-methyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(C)CC)N PBJMKNCCYFNSLX-UHFFFAOYSA-N 0.000 claims 1
- JBSDGDDPLLFIDC-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-ethyl-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2NCC)N JBSDGDDPLLFIDC-UHFFFAOYSA-N 0.000 claims 1
- HNRRPEJWZCQOTP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-methyl-4-N-(oxan-2-ylmethyl)-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(CC1OCCCC1)C)N HNRRPEJWZCQOTP-UHFFFAOYSA-N 0.000 claims 1
- FXOUMGZYOLJUAY-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-methyl-4-N-(oxan-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(C1CCOCC1)C)N FXOUMGZYOLJUAY-UHFFFAOYSA-N 0.000 claims 1
- OUFOWDUIRPIIBL-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-methyl-4-N-(pyridin-2-ylmethyl)-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(CC1=NC=CC=C1)C)N OUFOWDUIRPIIBL-UHFFFAOYSA-N 0.000 claims 1
- PXARLDFRLLJCIY-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-N-methyl-4-N-[(5-methyl-1,2-oxazol-3-yl)methyl]-5H-pyrrolo[3,2-d]pyrimidine-4,6-diamine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N(CC1=NOC(=C1)C)C)N PXARLDFRLLJCIY-UHFFFAOYSA-N 0.000 claims 1
- QYTSGLRBQNDQFX-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[(1-methylcyclopropyl)methoxy]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1(CC1)C)N QYTSGLRBQNDQFX-UHFFFAOYSA-N 0.000 claims 1
- HNMSMTGDTYALID-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[(2,2-difluorocyclopropyl)methoxy]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1C(C1)(F)F)N HNMSMTGDTYALID-UHFFFAOYSA-N 0.000 claims 1
- HLMKILGNYCHACU-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[(2,2-dimethylcyclopropyl)methoxy]-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OCC1C(C1)(C)C)C)N HLMKILGNYCHACU-UHFFFAOYSA-N 0.000 claims 1
- WTXRVZGPTCZOEO-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[(2,5-dimethyl-1,3-oxazol-4-yl)methoxy]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC=1N=C(OC=1C)C)N WTXRVZGPTCZOEO-UHFFFAOYSA-N 0.000 claims 1
- ZMTMFCFWCNTGIY-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[(2-methylcyclopropyl)methoxy]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1CC1COC1=C2NC(N)=C(C2=NC=N1)S(=O)(=O)C1=CC=CC=C1 ZMTMFCFWCNTGIY-UHFFFAOYSA-N 0.000 claims 1
- LINHFPLCYJVSFD-GFCCVEGCSA-N 7-(benzenesulfonyl)-4-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1[C@H](CCC1)COC)N LINHFPLCYJVSFD-GFCCVEGCSA-N 0.000 claims 1
- ADHJMTZWTHEQDG-LLVKDONJSA-N 7-(benzenesulfonyl)-4-[(2R)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C[C@H](OCC1)C)N ADHJMTZWTHEQDG-LLVKDONJSA-N 0.000 claims 1
- KALZHOWTOQPNDR-KRWDZBQOSA-N 7-(benzenesulfonyl)-4-[(2R)-2-phenylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C[C@H](OCC1)C1=CC=CC=C1)N KALZHOWTOQPNDR-KRWDZBQOSA-N 0.000 claims 1
- UVGGZCKTGOSNJJ-SNVBAGLBSA-N 7-(benzenesulfonyl)-4-[(2R)-butan-2-yl]oxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2O[C@H](C)CC)C)N UVGGZCKTGOSNJJ-SNVBAGLBSA-N 0.000 claims 1
- PDTVIYFUEMCZIY-VXGBXAGGSA-N 7-(benzenesulfonyl)-4-[(2R,5R)-2,5-dimethylmorpholin-4-yl]-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@H](OC[C@H]1C)C)C)N PDTVIYFUEMCZIY-VXGBXAGGSA-N 0.000 claims 1
- FXSLJKLOYQUMHL-VXGBXAGGSA-N 7-(benzenesulfonyl)-4-[(2R,6R)-2,6-dimethylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C[C@H](O[C@@H](C1)C)C)N FXSLJKLOYQUMHL-VXGBXAGGSA-N 0.000 claims 1
- FXSLJKLOYQUMHL-TXEJJXNPSA-N 7-(benzenesulfonyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C[C@H](O[C@H](C1)C)C)N FXSLJKLOYQUMHL-TXEJJXNPSA-N 0.000 claims 1
- ADHJMTZWTHEQDG-NSHDSACASA-N 7-(benzenesulfonyl)-4-[(2S)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C[C@@H](OCC1)C)N ADHJMTZWTHEQDG-NSHDSACASA-N 0.000 claims 1
- KALZHOWTOQPNDR-QGZVFWFLSA-N 7-(benzenesulfonyl)-4-[(2S)-2-phenylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1C[C@@H](OCC1)C1=CC=CC=C1)N KALZHOWTOQPNDR-QGZVFWFLSA-N 0.000 claims 1
- UVGGZCKTGOSNJJ-JTQLQIEISA-N 7-(benzenesulfonyl)-4-[(2S)-butan-2-yl]oxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2O[C@@H](C)CC)C)N UVGGZCKTGOSNJJ-JTQLQIEISA-N 0.000 claims 1
- PDTVIYFUEMCZIY-RYUDHWBXSA-N 7-(benzenesulfonyl)-4-[(2S,5S)-2,5-dimethylmorpholin-4-yl]-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OC[C@@H]1C)C)C)N PDTVIYFUEMCZIY-RYUDHWBXSA-N 0.000 claims 1
- XMYWVTITRZCPIM-TXEJJXNPSA-N 7-(benzenesulfonyl)-4-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@H](O[C@H](C1)C)C)C)N XMYWVTITRZCPIM-TXEJJXNPSA-N 0.000 claims 1
- VUAHMOBPTDMZBI-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[(3,3-difluorocyclobutyl)methoxy]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1CC(C1)(F)F)N VUAHMOBPTDMZBI-UHFFFAOYSA-N 0.000 claims 1
- SROSXNOUBXSTIX-SNVBAGLBSA-N 7-(benzenesulfonyl)-4-[(3R)-oxolan-3-yl]oxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2O[C@H]1COCC1)N SROSXNOUBXSTIX-SNVBAGLBSA-N 0.000 claims 1
- SROSXNOUBXSTIX-JTQLQIEISA-N 7-(benzenesulfonyl)-4-[(3S)-oxolan-3-yl]oxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2O[C@@H]1COCC1)N SROSXNOUBXSTIX-JTQLQIEISA-N 0.000 claims 1
- NJXVYLGMLRFHQJ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[(4-methyl-1,3-thiazol-2-yl)methoxy]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC=1SC=C(N=1)C)N NJXVYLGMLRFHQJ-UHFFFAOYSA-N 0.000 claims 1
- QAPBEAGSBUREKH-CMDGGOBGSA-N 7-(benzenesulfonyl)-4-[(E)-2-cyclopropylethenyl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2\C=C\C1CC1)N QAPBEAGSBUREKH-CMDGGOBGSA-N 0.000 claims 1
- KSUYFJSRZSRLAP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[2-(2-methylpropyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)CC(C)C)N KSUYFJSRZSRLAP-UHFFFAOYSA-N 0.000 claims 1
- PPJOKKBMDGZSBB-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[2-(methoxymethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)COC)N PPJOKKBMDGZSBB-UHFFFAOYSA-N 0.000 claims 1
- SNUSHWWWEWJAEK-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[2-(trifluoromethyl)morpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CC(OCC1)C(F)(F)F)N SNUSHWWWEWJAEK-UHFFFAOYSA-N 0.000 claims 1
- BGWSGJQEUIZGKR-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[4-(cyclopropylmethoxy)piperidin-1-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCC(CC1)OCC1CC1)N BGWSGJQEUIZGKR-UHFFFAOYSA-N 0.000 claims 1
- NNTOFULFRSISAG-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-[4-(methoxymethyl)piperidin-1-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCC(CC1)COC)N NNTOFULFRSISAG-UHFFFAOYSA-N 0.000 claims 1
- IFSBHEUWQGWXLZ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-chloro-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2Cl)C)N IFSBHEUWQGWXLZ-UHFFFAOYSA-N 0.000 claims 1
- BJPXMJZZCNWSIG-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-chloro-2-methylsulfanyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2Cl)SC)N BJPXMJZZCNWSIG-UHFFFAOYSA-N 0.000 claims 1
- RXXYWOWOXNGCBG-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2Cl)N RXXYWOWOXNGCBG-UHFFFAOYSA-N 0.000 claims 1
- QKHHUOYVRLLXMJ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclobutyloxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC1CCC1)C)N QKHHUOYVRLLXMJ-UHFFFAOYSA-N 0.000 claims 1
- XOEYKBJKXAWJOL-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclobutyloxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC1CCC1)N XOEYKBJKXAWJOL-UHFFFAOYSA-N 0.000 claims 1
- NIIRHVSUEBTMCE-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclohexyl-2-cyclopropyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C1CCCCC1)C1CC1)N NIIRHVSUEBTMCE-UHFFFAOYSA-N 0.000 claims 1
- DEXHQVBBDQVQIH-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclohexyl-2-ethyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C1CCCCC1)CC)N DEXHQVBBDQVQIH-UHFFFAOYSA-N 0.000 claims 1
- FTSXZSDAYGPPCY-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclohexyl-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2C1CCCCC1)C)N FTSXZSDAYGPPCY-UHFFFAOYSA-N 0.000 claims 1
- PWQLLKSZCAOCHC-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclohexyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1CCCCC1)N PWQLLKSZCAOCHC-UHFFFAOYSA-N 0.000 claims 1
- UPBBEBMYELQXPF-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclohexyl-N-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1CCCCC1)NC UPBBEBMYELQXPF-UHFFFAOYSA-N 0.000 claims 1
- RYIVFSQKUDSQIB-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclohexyloxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC1CCCCC1)N RYIVFSQKUDSQIB-UHFFFAOYSA-N 0.000 claims 1
- CTFOIDPGUZIXLC-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclopentyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1CCCC1)N CTFOIDPGUZIXLC-UHFFFAOYSA-N 0.000 claims 1
- BZKZAMKTXFYNNU-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclopentyloxy-2-methyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2OC1CCCC1)C)N BZKZAMKTXFYNNU-UHFFFAOYSA-N 0.000 claims 1
- CJMRZUPDWUHWAE-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-cyclopentyloxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC1CCCC1)N CJMRZUPDWUHWAE-UHFFFAOYSA-N 0.000 claims 1
- YTDBHTZELLWIGP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-morpholin-4-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCOCC1)N YTDBHTZELLWIGP-UHFFFAOYSA-N 0.000 claims 1
- ZGZDZHDVYRHMBM-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-pentan-3-yloxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OC(CC)CC)N ZGZDZHDVYRHMBM-UHFFFAOYSA-N 0.000 claims 1
- LRQLLYRQKMQSIG-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-phenyl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=CC=CC=C1)N LRQLLYRQKMQSIG-UHFFFAOYSA-N 0.000 claims 1
- MTTKTFHNSDKTLP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-phenylmethoxy-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2OCC1=CC=CC=C1)N MTTKTFHNSDKTLP-UHFFFAOYSA-N 0.000 claims 1
- DIUCXEDEQZEBLE-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-piperidin-1-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCCCC1)N DIUCXEDEQZEBLE-UHFFFAOYSA-N 0.000 claims 1
- DWFXJZCBWXSADJ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-prop-1-en-2-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C(=C)C)N DWFXJZCBWXSADJ-UHFFFAOYSA-N 0.000 claims 1
- GEFVLULAOLZZDF-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-propan-2-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C(C)C)N GEFVLULAOLZZDF-UHFFFAOYSA-N 0.000 claims 1
- FIHVLROLRBBANA-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-pyrazol-1-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1N=CC=C1)N FIHVLROLRBBANA-UHFFFAOYSA-N 0.000 claims 1
- XFEHMJKBPHCJFJ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-pyridin-3-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C=1C=NC=CC=1)N XFEHMJKBPHCJFJ-UHFFFAOYSA-N 0.000 claims 1
- MBKXFBURAMWWGP-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-pyridin-4-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2C1=CC=NC=C1)N MBKXFBURAMWWGP-UHFFFAOYSA-N 0.000 claims 1
- KWNIVSQOHJDERJ-UHFFFAOYSA-N 7-(benzenesulfonyl)-4-pyrrolidin-1-yl-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=C(NC2=C1N=CN=C2N1CCCC1)N KWNIVSQOHJDERJ-UHFFFAOYSA-N 0.000 claims 1
- YFGWLJVEXUVRBE-KBPBESRZSA-N 7-[4-bromo-2-[(2S)-2-methylmorpholin-4-yl]phenyl]sulfonyl-2-methyl-4-[(2S)-2-methylmorpholin-4-yl]-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound BrC1=CC(=C(C=C1)S(=O)(=O)C1=C(NC2=C1N=C(N=C2N1C[C@@H](OCC1)C)C)N)N1C[C@@H](OCC1)C YFGWLJVEXUVRBE-KBPBESRZSA-N 0.000 claims 1
- WORHWIXDGMUKFP-UHFFFAOYSA-N 7-benzylsulfonyl-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine Chemical compound CC1CN(CCO1)C=1C2=C(N=CN=1)C(=C(N2)N)S(=O)(=O)CC1=CC=CC=C1 WORHWIXDGMUKFP-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- TUGOMGSGZQSKGZ-UHFFFAOYSA-N benzyl 4-[[6-amino-4-(2-methylmorpholin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]sulfonyl]piperidine-1-carboxylate Chemical compound NC1=C(C=2N=CN=C(C=2N1)N1CC(OCC1)C)S(=O)(=O)C1CCN(CC1)C(=O)OCC1=CC=CC=C1 TUGOMGSGZQSKGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 1
- 125000005961 oxazepanyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1411236.1 | 2014-06-25 | ||
| GBGB1411236.1A GB201411236D0 (en) | 2014-06-25 | 2014-06-25 | Novel compounds |
| PCT/GB2015/051840 WO2015198045A1 (en) | 2014-06-25 | 2015-06-24 | 3-substituted 2-amino-indole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017519023A JP2017519023A (ja) | 2017-07-13 |
| JP2017519023A5 true JP2017519023A5 (enExample) | 2018-08-02 |
| JP6574450B2 JP6574450B2 (ja) | 2019-09-11 |
Family
ID=51410054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016574907A Expired - Fee Related JP6574450B2 (ja) | 2014-06-25 | 2015-06-24 | ３−置換２−アミノ−インドール誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10059713B2 (enExample) |
| EP (1) | EP3160965A1 (enExample) |
| JP (1) | JP6574450B2 (enExample) |
| CN (1) | CN106488919B (enExample) |
| CA (1) | CA2952339A1 (enExample) |
| GB (1) | GB201411236D0 (enExample) |
| WO (1) | WO2015198045A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3889145B1 (en) | 2015-12-17 | 2024-02-21 | Merck Patent GmbH | 8-cyano-5-piperidino-quinolines as tlr7/8 antagonists and their uses for treating immune disorders |
| US10947214B2 (en) | 2016-08-08 | 2021-03-16 | Merck Patent Gmbh | TLR7/8 antagonists and uses thereof |
| JP7062792B2 (ja) | 2018-02-13 | 2022-05-06 | ギリアード サイエンシーズ， インコーポレイテッド | Ｐｄ－１／ｐｄ－ｌ１阻害剤 |
| CN108440496B (zh) * | 2018-03-01 | 2019-09-10 | 苏州大学 | 一种制备2-氨基吲哚衍生物的方法 |
| PT3762368T (pt) | 2018-03-08 | 2022-05-06 | Incyte Corp | Compostos de aminopirazina diol como inibidores de pi3k-y |
| EP3781556B1 (en) | 2018-04-19 | 2025-06-18 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| CN118221646A (zh) | 2018-07-13 | 2024-06-21 | 吉利德科学公司 | Pd-1/pd-l1抑制剂 |
| KR102635333B1 (ko) | 2018-10-24 | 2024-02-15 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| WO2021115286A1 (zh) * | 2019-12-10 | 2021-06-17 | 成都倍特药业股份有限公司 | 一种可用作shp2抑制剂的含氮杂原子的六元并五元芳环衍生物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| TW200306191A (en) * | 2002-02-22 | 2003-11-16 | Teijin Ltd | Pyrrolopyrimidine derivatives |
| US20040122218A1 (en) * | 2002-12-20 | 2004-06-24 | Sean Turner | Pyrrolopyridine potassium channel openers |
| CA2572750A1 (en) * | 2003-09-10 | 2005-03-17 | Anil Koul | Heterobicyclic compounds as pharmaceutically active agents |
| AU2011248175A1 (en) * | 2010-05-06 | 2012-10-25 | Merck Sharp & Dohme Corp. | Aza-Indole derivatives useful as modulators of FAAH |
| WO2011153553A2 (en) | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| WO2012064898A1 (en) | 2010-11-09 | 2012-05-18 | Yuan Chen | Singleton inhibitors of sumoylation enzymes and methods for their use |
| US20140018361A1 (en) | 2012-07-11 | 2014-01-16 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
-
2014
- 2014-06-25 GB GBGB1411236.1A patent/GB201411236D0/en not_active Ceased
-
2015
- 2015-06-24 CN CN201580034535.3A patent/CN106488919B/zh not_active Expired - Fee Related
- 2015-06-24 WO PCT/GB2015/051840 patent/WO2015198045A1/en not_active Ceased
- 2015-06-24 JP JP2016574907A patent/JP6574450B2/ja not_active Expired - Fee Related
- 2015-06-24 EP EP15732916.0A patent/EP3160965A1/en not_active Withdrawn
- 2015-06-24 US US15/320,887 patent/US10059713B2/en not_active Expired - Fee Related
- 2015-06-24 CA CA2952339A patent/CA2952339A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017519023A5 (enExample) | ||
| JP2023071767A (ja) | Ｂｒｍ標的化化合物および関連使用方法 | |
| EP3515916B1 (en) | Shp2 phosphatase inhibitors and methods of use thereof | |
| EP3468972B1 (en) | Compounds and compositions for inhibiting the activity of shp2 | |
| CN107108637B (zh) | 三唑并嘧啶化合物及其用途 | |
| US10287266B2 (en) | Compounds and compositions for inhibiting the activity of SHP2 | |
| US10966980B2 (en) | Pyrrolo[2,3-d]pyrimidine derivatives | |
| DK3183247T3 (en) | Aminopyrimidinyl compounds as JAK inhibitors | |
| US20200181168A1 (en) | N-azaspirocycloalkane substituted n-heteroaryl compounds and compositions for inhibiting the activity of shp2 | |
| TW202517628A (zh) | Shp2之八氫環戊烷并[c]吡咯別構抑制劑 | |
| TW201819386A (zh) | Shp2磷酸酶抑制劑及其使用方法 | |
| AU2018233402A1 (en) | Pyrimidinyl-pyridyloxy-naphthyl compounds and methods of treating ire1-related diseases and disorders | |
| EP3310771A1 (en) | Compounds and compositions for inhibiting the activity of shp2 | |
| RU2019115115A (ru) | Производные пиперидина в качестве ингибиторов убиквитин-специфической протеазы 7 | |
| JP2017525757A5 (enExample) | ||
| HRP20201618T1 (hr) | N-SULFONILIRANI PIRAZOLO[3,4-b]PIRIDIN-6-KARBOKSAMIDI I POSTUPAK NJIHOVE UPOTREBE | |
| KR20240018446A (ko) | 돌연변이 braf의 분해를 위한 요법 | |
| CN105209460A (zh) | 作为突变idh抑制剂的3-嘧啶-4-基-噁唑烷-2-酮化合物 | |
| JP2014528951A (ja) | 変異体ｉｄｈの阻害剤としての３−ピリミジン−４−イル−オキサゾリジン−２−オン類 | |
| JP7763753B2 (ja) | アザキノリン化合物およびその使用 | |
| NZ728122A (en) | 6,7-dihydropyrazolo[1,5-a]pyrazin-4(5h)-one compounds and their use as negative allosteric modulators of mglur2 receptors | |
| US10577362B2 (en) | Substituted 2, 4-diamino-quinoline derivatives for use in the treatment of proliferative diseases | |
| JP2017531672A5 (enExample) | ||
| JP7768880B2 (ja) | Ｅｚｈ２を阻害するためのキノリン化合物および組成物 | |
| RU2010148534A (ru) | Производные имидазолидинона в качестве ингибиторов в 11b-hsd1 |