RU2294937C9 - Тиенопиримидиндионы, способ их получения (варианты) и фармацевтическая композиция - Google Patents

Info

Publication number

RU2294937C9

RU2294937C9 RU2004102392/04A RU2004102392A RU2294937C9 RU 2294937 C9 RU2294937 C9 RU 2294937C9 RU 2004102392/04 A RU2004102392/04 A RU 2004102392/04A RU 2004102392 A RU2004102392 A RU 2004102392A RU 2294937 C9 RU2294937 C9 RU 2294937C9

Authority

RU

Russia

Prior art keywords

methyl

dione

thieno

ylcarbonyl

hydroxyisoxazolidin

Prior art date

2001-07-28

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• 238000000034 method Methods 0.000 title claims abstract description 211
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 411
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 81
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 63
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 55
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 38
• 125000003118 aryl group Chemical group 0.000 claims abstract description 29
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 26
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 24
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
• 239000001301 oxygen Substances 0.000 claims abstract description 24
• 125000004122 cyclic group Chemical class 0.000 claims abstract description 17
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
• 125000006413 ring segment Chemical group 0.000 claims abstract description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 8
• 238000003786 synthesis reaction Methods 0.000 claims abstract description 8
• 125000005843 halogen group Chemical group 0.000 claims abstract description 6
• -1 isoxazolidin-2-ylcarbonyl Chemical group 0.000 claims description 265
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 87
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 49
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• JGOOQALRLGHKIY-UHFFFAOYSA-N 1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)NC2=C1C=CS2 JGOOQALRLGHKIY-UHFFFAOYSA-N 0.000 claims description 37
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 34
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000004043 oxo group Chemical group O=* 0.000 claims description 26
• 229910052717 sulfur Chemical group 0.000 claims description 25
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
• 239000011593 sulfur Chemical group 0.000 claims description 24
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000004385 trihaloalkyl group Chemical group 0.000 claims description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• 125000004982 dihaloalkyl group Chemical group 0.000 claims description 13
• 125000001188 haloalkyl group Chemical group 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 11
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 125000002883 imidazolyl group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 claims description 9
• 125000005493 quinolyl group Chemical group 0.000 claims description 9
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 230000035755 proliferation Effects 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
• 125000000524 functional group Chemical group 0.000 claims description 6
• 230000003993 interaction Effects 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• ZIQASVKKDANPDO-ABLWVSNPSA-N 5-(4-hydroxy-1,2-oxazolidine-2-carbonyl)-3-methyl-6-[[(2s)-6-methyl-3-oxo-2h-pyrazin-2-yl]methyl]-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1C(O)CON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1C[C@@H]1N=C(C)C=NC1=O ZIQASVKKDANPDO-ABLWVSNPSA-N 0.000 claims description 5
• FOUGTHXAKKBTGL-MRXNPFEDSA-N 5-[(4r)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CC=C3N=CC=2)=C1C(=O)N1C[C@@H](O)CO1 FOUGTHXAKKBTGL-MRXNPFEDSA-N 0.000 claims description 5
• XEVQNMOABVOAGK-OAHLLOKOSA-N 5-[(4r)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(2-methyl-1h-indol-3-yl)methyl]-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CC=C3NC=2C)=C1C(=O)N1C[C@@H](O)CO1 XEVQNMOABVOAGK-OAHLLOKOSA-N 0.000 claims description 5
• PYLXXPJXPHUENG-LBPRGKRZSA-N 6-[(3,5-dimethyl-1h-pyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC=1C(C)=NNC=1C PYLXXPJXPHUENG-LBPRGKRZSA-N 0.000 claims description 5
• ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
• MMEGHQPYDCKIFC-LBPRGKRZSA-N 1-ethyl-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC)C=2SC(CC=2C3=CC=CN=C3NC=2)=C1C(=O)N1C[C@H](O)CO1 MMEGHQPYDCKIFC-LBPRGKRZSA-N 0.000 claims description 4
• ZHWYUYWJISNICI-LBPRGKRZSA-N 1-ethyl-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(2-methyl-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC)C=2SC(CC=2C3=CC=CN=C3NC=2C)=C1C(=O)N1C[C@H](O)CO1 ZHWYUYWJISNICI-LBPRGKRZSA-N 0.000 claims description 4
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 4
• KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 claims description 4
• HMICMRQBKBXVSC-AWEZNQCLSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CN=C3NC=2)=C1C(=O)N1C[C@H](O)CO1 HMICMRQBKBXVSC-AWEZNQCLSA-N 0.000 claims description 4
• ZNHPAUWDRKNNNX-HNNXBMFYSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(pyrrolo[2,3-b]pyridin-1-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C3=NC=CC=C3C=C2)=C1C(=O)N1C[C@H](O)CO1 ZNHPAUWDRKNNNX-HNNXBMFYSA-N 0.000 claims description 4
• FOUGTHXAKKBTGL-INIZCTEOSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CC=C3N=CC=2)=C1C(=O)N1C[C@H](O)CO1 FOUGTHXAKKBTGL-INIZCTEOSA-N 0.000 claims description 4
• OAOKFYWAUWUPNT-INIZCTEOSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(quinolin-5-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CN=C3C=CC=2)=C1C(=O)N1C[C@H](O)CO1 OAOKFYWAUWUPNT-INIZCTEOSA-N 0.000 claims description 4
• SYABSTPXYAKTOJ-AWEZNQCLSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[(1,3,5-trimethylpyrazol-4-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC=1C(C)=NN(C)C=1C SYABSTPXYAKTOJ-AWEZNQCLSA-N 0.000 claims description 4
• HPEIANKQXRRLBL-AWEZNQCLSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[(2-methylsulfanylbenzimidazol-1-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CSC1=NC2=CC=CC=C2N1CC=1SC=2N(CC(C)C)C(=O)N(C)C(=O)C=2C=1C(=O)N1C[C@H](O)CO1 HPEIANKQXRRLBL-AWEZNQCLSA-N 0.000 claims description 4
• HIQNRBQEGNXQIY-ZDUSSCGKSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[(2-methylsulfanylimidazo[4,5-b]pyridin-3-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CSC1=NC2=CC=CN=C2N1CC=1SC=2N(CC(C)C)C(=O)N(C)C(=O)C=2C=1C(=O)N1C[C@H](O)CO1 HIQNRBQEGNXQIY-ZDUSSCGKSA-N 0.000 claims description 4
• MONIFZUOJGZTAE-ZDUSSCGKSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[(2-oxo-3h-benzimidazol-1-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C(NC3=CC=CC=C32)=O)=C1C(=O)N1C[C@H](O)CO1 MONIFZUOJGZTAE-ZDUSSCGKSA-N 0.000 claims description 4
• HWCXNAYSPUDWJO-ZDUSSCGKSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[(2-sulfanylidene-1,3-benzothiazol-3-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C(SC3=CC=CC=C32)=S)=C1C(=O)N1C[C@H](O)CO1 HWCXNAYSPUDWJO-ZDUSSCGKSA-N 0.000 claims description 4
• IJOXULDVIPXPSA-NSHDSACASA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-[[5-methyl-3-(trifluoromethyl)-1h-pyrazol-4-yl]methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=C(C)NN=C1C(F)(F)F IJOXULDVIPXPSA-NSHDSACASA-N 0.000 claims description 4
• CMNXDCPCRZRYRA-ZDUSSCGKSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-yl-6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CC=2C3=CC=CN=C3NC=2)=C1C(=O)N1C[C@H](O)CO1 CMNXDCPCRZRYRA-ZDUSSCGKSA-N 0.000 claims description 4
• PDNPKVIMVPDBRT-ZDUSSCGKSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propyl-6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CCC)C=2SC(CC=2C3=CC=CN=C3NC=2)=C1C(=O)N1C[C@H](O)CO1 PDNPKVIMVPDBRT-ZDUSSCGKSA-N 0.000 claims description 4
• HXZVKQYSAPGSDO-HNNXBMFYSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propyl-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CCC)C=2SC(CC=2C3=CC=CC=C3N=CC=2)=C1C(=O)N1C[C@H](O)CO1 HXZVKQYSAPGSDO-HNNXBMFYSA-N 0.000 claims description 4
• XEVQNMOABVOAGK-HNNXBMFYSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(2-methyl-1h-indol-3-yl)methyl]-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CC=C3NC=2C)=C1C(=O)N1C[C@H](O)CO1 XEVQNMOABVOAGK-HNNXBMFYSA-N 0.000 claims description 4
• WCXCSEWUMQNJDV-ZDUSSCGKSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(2-methyl-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CC=2C3=CC=CN=C3NC=2C)=C1C(=O)N1C[C@H](O)CO1 WCXCSEWUMQNJDV-ZDUSSCGKSA-N 0.000 claims description 4
• LGTFKFFKZHGUGS-HNNXBMFYSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(2-methylbenzimidazol-1-yl)methyl]-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C3=CC=CC=C3N=C2C)=C1C(=O)N1C[C@H](O)CO1 LGTFKFFKZHGUGS-HNNXBMFYSA-N 0.000 claims description 4
• CYXVQFUBNAVJSY-KRWDZBQOSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(5-methyl-3-phenyl-1h-pyrazol-4-yl)methyl]-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=C(C)NN=C1C1=CC=CC=C1 CYXVQFUBNAVJSY-KRWDZBQOSA-N 0.000 claims description 4
• XIXMTIJQLLRJIJ-AWEZNQCLSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(5-methyl-3-propan-2-yl-1h-pyrazol-4-yl)methyl]-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC1=C(C)NN=C1C(C)C XIXMTIJQLLRJIJ-AWEZNQCLSA-N 0.000 claims description 4
• HAFALVDBJMSQDY-ZDUSSCGKSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[[2-(methylamino)benzimidazol-1-yl]methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound CNC1=NC2=CC=CC=C2N1CC=1SC=2N(C(C)C)C(=O)N(C)C(=O)C=2C=1C(=O)N1C[C@H](O)CO1 HAFALVDBJMSQDY-ZDUSSCGKSA-N 0.000 claims description 4
• PHTPNKIHLRLMJH-HNNXBMFYSA-N 5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-6-(imidazo[1,2-a]pyridin-3-ylmethyl)-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2N3C=CC=CC3=NC=2)=C1C(=O)N1C[C@H](O)CO1 PHTPNKIHLRLMJH-HNNXBMFYSA-N 0.000 claims description 4
• SALVKLFWQWNMJO-ZDUSSCGKSA-N 6-[(2-aminobenzimidazol-1-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CN2C3=CC=CC=C3N=C2N)=C1C(=O)N1C[C@H](O)CO1 SALVKLFWQWNMJO-ZDUSSCGKSA-N 0.000 claims description 4
• OFTBDTAMUXEDOO-LBPRGKRZSA-N 6-[(2-aminobenzimidazol-1-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CN2C3=CC=CC=C3N=C2N)=C1C(=O)N1C[C@H](O)CO1 OFTBDTAMUXEDOO-LBPRGKRZSA-N 0.000 claims description 4
• RECMMXWFDZIIOE-HNNXBMFYSA-N 6-[(2-ethylbenzimidazol-1-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound CCC1=NC2=CC=CC=C2N1CC=1SC=2N(CC(C)C)C(=O)N(C)C(=O)C=2C=1C(=O)N1C[C@H](O)CO1 RECMMXWFDZIIOE-HNNXBMFYSA-N 0.000 claims description 4
• ZOIKLFOXYZTZJG-ZDUSSCGKSA-N 6-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC=1C(C)=NOC=1C ZOIKLFOXYZTZJG-ZDUSSCGKSA-N 0.000 claims description 4
• NWDXTHRUMCBLPT-IBGZPJMESA-N 6-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@H](O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC(=C1C)C(C)=NN1C1=CC=CC=C1 NWDXTHRUMCBLPT-IBGZPJMESA-N 0.000 claims description 4
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• QZBMZXZAQVDMAM-UHFFFAOYSA-N methyl 3,6-dimethyl-2,4-dioxo-1-propylthieno[2,3-d]pyrimidine-5-carboxylate Chemical compound O=C1N(C)C(=O)N(CCC)C2=C1C(C(=O)OC)=C(C)S2 QZBMZXZAQVDMAM-UHFFFAOYSA-N 0.000 description 1
• JFIHRJQSMSDCOL-UHFFFAOYSA-N methyl 3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[(2-sulfanylidene-1,3-benzothiazol-3-yl)methyl]thieno[2,3-d]pyrimidine-5-carboxylate Chemical compound CC(C)CN1C(=O)N(C)C(=O)C2=C1SC(CN1C(SC3=CC=CC=C31)=S)=C2C(=O)OC JFIHRJQSMSDCOL-UHFFFAOYSA-N 0.000 description 1
• GYGCMSSNBCCUKA-UHFFFAOYSA-N methyl 3-methyl-1-(2-methylpropyl)-6-[(2-methylsulfanylbenzimidazol-1-yl)methyl]-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate Chemical compound CC(C)CN1C(=O)N(C)C(=O)C2=C1SC(CN1C3=CC=CC=C3N=C1SC)=C2C(=O)OC GYGCMSSNBCCUKA-UHFFFAOYSA-N 0.000 description 1
• QFKMGNOSMBRYFH-UHFFFAOYSA-N methyl 3-methyl-1-(2-methylpropyl)-6-[[5-methyl-3-(trifluoromethyl)-1h-pyrazol-4-yl]methyl]-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate Chemical compound S1C=2N(CC(C)C)C(=O)N(C)C(=O)C=2C(C(=O)OC)=C1CC1=C(C)NN=C1C(F)(F)F QFKMGNOSMBRYFH-UHFFFAOYSA-N 0.000 description 1
• MGOCOCSPEPHNCF-UHFFFAOYSA-N methyl 3-methyl-6-[(2-methyl-1h-indol-3-yl)methyl]-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate Chemical compound CC(C)CN1C(=O)N(C)C(=O)C2=C1SC(CC=1C3=CC=CC=C3NC=1C)=C2C(=O)OC MGOCOCSPEPHNCF-UHFFFAOYSA-N 0.000 description 1
• YLSOHOCHAICMRS-UHFFFAOYSA-N methyl 3-methyl-6-[(2-methyl-1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-2,4-dioxo-1-propan-2-ylthieno[2,3-d]pyrimidine-5-carboxylate Chemical compound CC(C)N1C(=O)N(C)C(=O)C2=C1SC(CC=1C3=CC=CN=C3NC=1C)=C2C(=O)OC YLSOHOCHAICMRS-UHFFFAOYSA-N 0.000 description 1
• HJAJQDYYYCUIGH-UHFFFAOYSA-N methyl 3-methyl-6-[(5-methyl-3-phenyl-1h-pyrazol-4-yl)methyl]-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate Chemical compound S1C=2N(CC(C)C)C(=O)N(C)C(=O)C=2C(C(=O)OC)=C1CC1=C(C)NN=C1C1=CC=CC=C1 HJAJQDYYYCUIGH-UHFFFAOYSA-N 0.000 description 1
• SNHHFXFXVMYFKN-UHFFFAOYSA-N methyl 3-methyl-6-[(6-methyl-3-oxo-2h-pyrazin-2-yl)methyl]-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate Chemical compound S1C=2N(CC(C)C)C(=O)N(C)C(=O)C=2C(C(=O)OC)=C1CC1N=C(C)C=NC1=O SNHHFXFXVMYFKN-UHFFFAOYSA-N 0.000 description 1
• ARTZNFGMGKSPCE-UHFFFAOYSA-N methyl 6-(bromomethyl)-1-ethyl-3-methyl-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate Chemical compound O=C1N(C)C(=O)N(CC)C2=C1C(C(=O)OC)=C(CBr)S2 ARTZNFGMGKSPCE-UHFFFAOYSA-N 0.000 description 1
• RLLAUUFNVFMHCQ-UHFFFAOYSA-N methyl 6-(bromomethyl)-3-ethyl-2,4-dioxo-1-propan-2-ylthieno[2,3-d]pyrimidine-5-carboxylate Chemical compound COC(=O)C1=C(SC=2N(C(N(C(C=21)=O)CC)=O)C(C)C)CBr RLLAUUFNVFMHCQ-UHFFFAOYSA-N 0.000 description 1
• RXDGBUXQXYYFJA-UHFFFAOYSA-N methyl 6-(bromomethyl)-3-methyl-2,4-dioxo-1-propylthieno[2,3-d]pyrimidine-5-carboxylate Chemical compound O=C1N(C)C(=O)N(CCC)C2=C1C(C(=O)OC)=C(CBr)S2 RXDGBUXQXYYFJA-UHFFFAOYSA-N 0.000 description 1
• KHAWVZIFPDUFGR-UHFFFAOYSA-N methyl 6-(imidazo[1,2-a]pyridin-3-ylmethyl)-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate Chemical compound CC(C)CN1C(=O)N(C)C(=O)C2=C1SC(CC=1N3C=CC=CC3=NC=1)=C2C(=O)OC KHAWVZIFPDUFGR-UHFFFAOYSA-N 0.000 description 1
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• ZCSTWQVRNBREBP-UHFFFAOYSA-N methyl 6-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methyl]-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate Chemical compound S1C=2N(CC(C)C)C(=O)N(C)C(=O)C=2C(C(=O)OC)=C1CC(=C1C)C(C)=NN1C1=CC=CC=C1 ZCSTWQVRNBREBP-UHFFFAOYSA-N 0.000 description 1
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