JP2017519023A5 - - Google Patents
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- 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
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- 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
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- 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)
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|---|---|---|---|
| GBGB1411236.1A GB201411236D0 (en) | 2014-06-25 | 2014-06-25 | Novel compounds |
| GB1411236.1 | 2014-06-25 | ||
| 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 (https=) | 2018-08-02 |
| JP6574450B2 JP6574450B2 (ja) | 2019-09-11 |
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| 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 |
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| US (1) | US10059713B2 (https=) |
| EP (1) | EP3160965A1 (https=) |
| JP (1) | JP6574450B2 (https=) |
| CN (1) | CN106488919B (https=) |
| CA (1) | CA2952339A1 (https=) |
| GB (1) | GB201411236D0 (https=) |
| WO (1) | WO2015198045A1 (https=) |
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| CA3005766A1 (en) | 2015-12-17 | 2017-06-22 | Merck Patent Gmbh | Polycyclic tlr7/8 antagonists and use thereof in the treatment of immune disorders |
| JP7125385B2 (ja) | 2016-08-08 | 2022-08-24 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｔｌｒ７／８アンタゴニストおよびそれらの使用 |
| BR102018007822A2 (pt) | 2017-04-20 | 2018-11-06 | Gilead Sciences, Inc. | composto, métodos para inibir pd-1, pd-l1 e/ou interação de pd-1/pd-l1 e para tratamento de câncer, composição farmacêutica, e, kit para tratamento de ou prevenção de câncer ou uma doença ou condição |
| TWI707849B (zh) | 2018-02-13 | 2020-10-21 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| 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 |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| KR102591947B1 (ko) | 2018-04-19 | 2023-10-25 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| EP3820572B1 (en) | 2018-07-13 | 2023-08-16 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| US11236085B2 (en) | 2018-10-24 | 2022-02-01 | Gilead Sciences, Inc. | PD-1/PD-L1 inhibitors |
| CN114829362A (zh) * | 2019-12-10 | 2022-07-29 | 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 |
| EP1670804A2 (en) | 2003-09-10 | 2006-06-21 | GPC Biotech AG | 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 WO PCT/GB2015/051840 patent/WO2015198045A1/en not_active Ceased
- 2015-06-24 US US15/320,887 patent/US10059713B2/en not_active Expired - Fee Related
- 2015-06-24 JP JP2016574907A patent/JP6574450B2/ja not_active Expired - Fee Related
- 2015-06-24 CA CA2952339A patent/CA2952339A1/en not_active Abandoned
- 2015-06-24 CN CN201580034535.3A patent/CN106488919B/zh not_active Expired - Fee Related
- 2015-06-24 EP EP15732916.0A patent/EP3160965A1/en not_active Withdrawn
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