TW202208355A - 作為骨髓細胞觸發受體2促效劑之雜環化合物及使用方法 - Google Patents
作為骨髓細胞觸發受體2促效劑之雜環化合物及使用方法 Download PDFInfo
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- TW202208355A TW202208355A TW110115924A TW110115924A TW202208355A TW 202208355 A TW202208355 A TW 202208355A TW 110115924 A TW110115924 A TW 110115924A TW 110115924 A TW110115924 A TW 110115924A TW 202208355 A TW202208355 A TW 202208355A
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- methyl
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- pyrazol
- tautomer
- dimethyl
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- 238000000034 method Methods 0.000 title claims description 184
- 102100029678 Triggering receptor expressed on myeloid cells 2 Human genes 0.000 title abstract description 61
- 101710174937 Triggering receptor expressed on myeloid cells 2 Proteins 0.000 title abstract 2
- 239000000556 agonist Substances 0.000 title 1
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 842
- 101000795117 Homo sapiens Triggering receptor expressed on myeloid cells 2 Proteins 0.000 claims abstract description 74
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 47
- 238000011282 treatment Methods 0.000 claims abstract description 31
- -1 cyclopent-1-en-1-yl Chemical group 0.000 claims description 346
- 150000003839 salts Chemical class 0.000 claims description 300
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 claims description 253
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 172
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 164
- 125000000217 alkyl group Chemical group 0.000 claims description 130
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims description 115
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 79
- 125000001072 heteroaryl group Chemical group 0.000 claims description 79
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 72
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 57
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 52
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 52
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 37
- 239000003814 drug Substances 0.000 claims description 34
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 24
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 23
- 239000005977 Ethylene Substances 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 208000021320 Nasu-Hakola disease Diseases 0.000 claims description 20
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 208000031334 polycystic lipomembranous osteodysplasia with sclerosing leukoencephaly Diseases 0.000 claims description 20
- 208000024827 Alzheimer disease Diseases 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 17
- 230000002265 prevention Effects 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 102000048432 human TREM2 Human genes 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 13
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 12
- 208000018737 Parkinson disease Diseases 0.000 claims description 12
- 208000024777 Prion disease Diseases 0.000 claims description 11
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 11
- 208000006011 Stroke Diseases 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 201000006417 multiple sclerosis Diseases 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- LMUMMJCCZMWLEN-UHFFFAOYSA-N spiro[3.3]heptyl Chemical group [CH]1CCC11CCC1 LMUMMJCCZMWLEN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
- VYOKSNAATNTONM-KUHUBIRLSA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2S,4R)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pteridine Chemical compound CC1=C(C)N=C2N=C([C@H]3C[C@@H](C4=CN(C)N=C4)OCC3)N=C(C(C=CC(Cl)=C3)=C3F)C2=N1 VYOKSNAATNTONM-KUHUBIRLSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- ZLOUUGVAJKYCGE-UTKZUKDTSA-N 4-(2,4-difluorophenyl)-6,7-dimethyl-2-[(2S,4R)-2-(2-methylpyridin-4-yl)oxan-4-yl]pteridine Chemical compound CC1=CC([C@H](C2)OCC[C@H]2C(N=C2C(C=CC(F)=C3)=C3F)=NC3=C2N=C(C)C(C)=N3)=CC=N1 ZLOUUGVAJKYCGE-UTKZUKDTSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- ZLOUUGVAJKYCGE-DYESRHJHSA-N 4-(2,4-difluorophenyl)-6,7-dimethyl-2-[(2R,4R)-2-(2-methylpyridin-4-yl)oxan-4-yl]pteridine Chemical compound CC1=NC=CC([C@@H](C2)OCC[C@H]2C2=NC3=NC(C)=C(C)N=C3C(C(C=CC(F)=C3)=C3F)=N2)=C1 ZLOUUGVAJKYCGE-DYESRHJHSA-N 0.000 claims description 3
- UNLQLAOLYBVGSO-IFXJQAMLSA-N 4-(2,4-difluorophenyl)-6,7-dimethyl-2-[(2R,4S)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pteridine Chemical compound CC1=C(C)N=C2N=C([C@@H]3C[C@H](C4=CN(C)N=C4)OCC3)N=C(C(C=CC(F)=C3)=C3F)C2=N1 UNLQLAOLYBVGSO-IFXJQAMLSA-N 0.000 claims description 3
- ZLOUUGVAJKYCGE-LAUBAEHRSA-N 4-(2,4-difluorophenyl)-6,7-dimethyl-2-[(2R,4S)-2-(2-methylpyridin-4-yl)oxan-4-yl]pteridine Chemical compound CC1=CC([C@@H](C2)OCC[C@@H]2C2=NC3=NC(C)=C(C)N=C3C(C(C=CC(F)=C3)=C3F)=N2)=CC=N1 ZLOUUGVAJKYCGE-LAUBAEHRSA-N 0.000 claims description 3
- OHYOFVQXOORBMP-VFNWGFHPSA-N 4-(2,4-difluorophenyl)-6,7-dimethyl-2-[(2S,4R)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C(C)=N1)=CC2=C1N=C([C@H]1C[C@@H](C3=CN(C)N=C3)OCC1)N=C2C(C=CC(F)=C1)=C1F OHYOFVQXOORBMP-VFNWGFHPSA-N 0.000 claims description 3
- CHYLVMFGGVXHOJ-MBSDFSHPSA-N 4-(2,4-difluorophenyl)-6,7-dimethyl-2-[(2S,4S)-2-(2-methylpyridin-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC1=C(C)N=C2N=C([C@@H]3C[C@@H](C4=CC=NC(C)=C4)OCC3)N=C(C(C=CC(F)=C3)=C3F)C2=C1 CHYLVMFGGVXHOJ-MBSDFSHPSA-N 0.000 claims description 3
- FFFALYHCGHXZDG-JTSKRJEESA-N 4-(2,4-difluorophenyl)-7-methyl-2-[(2S,4S)-2-(2-methylpyridin-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C=C1)=NC2=C1C(C(C=CC(F)=C1)=C1F)=NC([C@@H]1C[C@@H](C3=CC(C)=NC=C3)OCC1)=N2 FFFALYHCGHXZDG-JTSKRJEESA-N 0.000 claims description 3
- FOZVIOCKPRGETP-GBXCKJPGSA-N 4-(2-fluoro-4-methylphenyl)-6,7-dimethyl-2-[(2R,4S)-2-(2-methylpyridin-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C=C1)=CC(F)=C1C1=NC([C@@H]2C[C@H](C3=CC(C)=NC=C3)OCC2)=NC2=C1C=C(C)C(C)=N2 FOZVIOCKPRGETP-GBXCKJPGSA-N 0.000 claims description 3
- FOZVIOCKPRGETP-YKSBVNFPSA-N 4-(2-fluoro-4-methylphenyl)-6,7-dimethyl-2-[(2S,4R)-2-(2-methylpyridin-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C=C1)=CC(F)=C1C1=NC([C@H]2C[C@@H](C3=CC(C)=NC=C3)OCC2)=NC2=C1C=C(C)C(C)=N2 FOZVIOCKPRGETP-YKSBVNFPSA-N 0.000 claims description 3
- GVSIOLJABVAKDN-FUHWJXTLSA-N 4-(4,4-difluorocyclohexyl)-6,7-dimethyl-2-[(2R,4S)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pteridine Chemical compound CC1=C(C)N=C2N=C([C@@H]3C[C@H](C4=CN(C)N=C4)OCC3)N=C(C(CC3)CCC3(F)F)C2=N1 GVSIOLJABVAKDN-FUHWJXTLSA-N 0.000 claims description 3
- GVSIOLJABVAKDN-AEFFLSMTSA-N 4-(4,4-difluorocyclohexyl)-6,7-dimethyl-2-[(2S,4R)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pteridine Chemical compound CC1=C(C)N=C2N=C([C@H]3C[C@@H](C4=CN(C)N=C4)OCC3)N=C(C(CC3)CCC3(F)F)C2=N1 GVSIOLJABVAKDN-AEFFLSMTSA-N 0.000 claims description 3
- SBACYKYUXDVWEI-YCRPNKLZSA-N 4-(4-chloro-2-fluorophenyl)-2-[(2R,4S)-2-(1-cyclopropylpyrazol-4-yl)oxan-4-yl]-6,7-dimethylpteridine Chemical compound CC1=C(C)N=C2N=C([C@@H]3C[C@H](C4=CN(C5CC5)N=C4)OCC3)N=C(C(C=CC(Cl)=C3)=C3F)C2=N1 SBACYKYUXDVWEI-YCRPNKLZSA-N 0.000 claims description 3
- WXESIJLUFGHNIJ-QMHKHESXSA-N 4-(4-chloro-2-fluorophenyl)-2-[(2R,4S)-2-(1-cyclopropylpyrazol-4-yl)oxan-4-yl]-6,7-dimethylpyrido[2,3-d]pyrimidine Chemical compound CC(C(C)=N1)=CC2=C1N=C([C@@H]1C[C@H](C3=CN(C4CC4)N=C3)OCC1)N=C2C(C=CC(Cl)=C1)=C1F WXESIJLUFGHNIJ-QMHKHESXSA-N 0.000 claims description 3
- KKKWHFATPFAIJN-OYHNWAKOSA-N 4-(4-chloro-2-fluorophenyl)-2-[(2R,4S)-2-(1-cyclopropylpyrazol-4-yl)oxan-4-yl]-7-methylpyrido[2,3-d]pyrimidine Chemical compound CC(C=C1)=NC2=C1C(C(C=CC(Cl)=C1)=C1F)=NC([C@@H]1C[C@H](C3=CN(C4CC4)N=C3)OCC1)=N2 KKKWHFATPFAIJN-OYHNWAKOSA-N 0.000 claims description 3
- NOLQHMIRMFVQEM-OXJNMPFZSA-N 4-(4-chloro-2-fluorophenyl)-2-[(2R,4S)-2-(2-methoxypyridin-4-yl)oxan-4-yl]-6,7-dimethylpteridine Chemical compound CC1=C(C)N=C2N=C([C@@H]3C[C@H](C4=CC(OC)=NC=C4)OCC3)N=C(C(C=CC(Cl)=C3)=C3F)C2=N1 NOLQHMIRMFVQEM-OXJNMPFZSA-N 0.000 claims description 3
- VYOKSNAATNTONM-AUUYWEPGSA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2R,4R)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pteridine Chemical compound CC1=C(C)N=C2N=C([C@H]3C[C@H](C4=CN(C)N=C4)OCC3)N=C(C(C=CC(Cl)=C3)=C3F)C2=N1 VYOKSNAATNTONM-AUUYWEPGSA-N 0.000 claims description 3
- DEYIDPGOSWKBRS-QVKFZJNVSA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2R,4R)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C(C)=N1)=CC2=C1N=C([C@H]1C[C@H](C3=CN(C)N=C3)OCC1)N=C2C(C=CC(Cl)=C1)=C1F DEYIDPGOSWKBRS-QVKFZJNVSA-N 0.000 claims description 3
- VYOKSNAATNTONM-IFXJQAMLSA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2R,4S)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pteridine Chemical compound CC1=C(C)N=C2N=C([C@@H]3C[C@H](C4=CN(C)N=C4)OCC3)N=C(C(C=CC(Cl)=C3)=C3F)C2=N1 VYOKSNAATNTONM-IFXJQAMLSA-N 0.000 claims description 3
- MBVNCLKGZIZRLQ-UFAGZECESA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2R,4S,6R)-2-methyl-6-(1-methylpyrazol-4-yl)oxan-4-yl]pteridine Chemical compound C[C@H](C[C@@H](C1)C2=NC3=NC(C)=C(C)N=C3C(C(C=CC(Cl)=C3)=C3F)=N2)O[C@H]1C1=CN(C)N=C1 MBVNCLKGZIZRLQ-UFAGZECESA-N 0.000 claims description 3
- NRNSYHPYZQHQKD-WEBUEUPWSA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2R,4S,6R)-2-methyl-6-(1-methylpyrazol-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound C[C@H](C[C@@H](C1)C2=NC(N=C(C)C(C)=C3)=C3C(C(C=CC(Cl)=C3)=C3F)=N2)O[C@H]1C1=CN(C)N=C1 NRNSYHPYZQHQKD-WEBUEUPWSA-N 0.000 claims description 3
- DEYIDPGOSWKBRS-VFNWGFHPSA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2S,4R)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C(C)=N1)=CC2=C1N=C([C@H]1C[C@@H](C3=CN(C)N=C3)OCC1)N=C2C(C=CC(Cl)=C1)=C1F DEYIDPGOSWKBRS-VFNWGFHPSA-N 0.000 claims description 3
- OHYOFVQXOORBMP-YCRPNKLZSA-N CC(C(C)=N1)=CC2=C1N=C([C@@H]1C[C@H](C3=CN(C)N=C3)OCC1)N=C2C(C=CC(F)=C1)=C1F Chemical compound CC(C(C)=N1)=CC2=C1N=C([C@@H]1C[C@H](C3=CN(C)N=C3)OCC1)N=C2C(C=CC(F)=C1)=C1F OHYOFVQXOORBMP-YCRPNKLZSA-N 0.000 claims description 3
- CCKBMAATPFMHFW-CADBVGFASA-N CC1=CC([C@@H](C2)OCC[C@@H]2C2=NC3=NC(C)=C(C)N=C3C([C@H](C3)C[C@@H]3C(F)(F)F)=N2)=CC=N1 Chemical compound CC1=CC([C@@H](C2)OCC[C@@H]2C2=NC3=NC(C)=C(C)N=C3C([C@H](C3)C[C@@H]3C(F)(F)F)=N2)=CC=N1 CCKBMAATPFMHFW-CADBVGFASA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- CHYLVMFGGVXHOJ-WZONZLPQSA-N 4-(2,4-difluorophenyl)-6,7-dimethyl-2-[(2R,4R)-2-(2-methylpyridin-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C(C)=N1)=CC2=C1N=C([C@H]1C[C@H](C3=CC(C)=NC=C3)OCC1)N=C2C(C=CC(F)=C1)=C1F CHYLVMFGGVXHOJ-WZONZLPQSA-N 0.000 claims description 2
- KLQIEPGDFZCIEM-HTAPYJJXSA-N 4-(2-fluoro-4-methylphenyl)-6,7-dimethyl-2-[(2R,4S)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C=C1)=CC(F)=C1C1=NC([C@@H]2C[C@H](C3=CN(C)N=C3)OCC2)=NC2=C1C=C(C)C(C)=N2 KLQIEPGDFZCIEM-HTAPYJJXSA-N 0.000 claims description 2
- UIWAILCISYHSMT-UZLBHIALSA-N 4-(2-fluoro-4-methylphenyl)-6,7-dimethyl-2-[(2S,4R)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pteridine Chemical compound CC(C=C1)=CC(F)=C1C1=NC([C@H]2C[C@@H](C3=CN(C)N=C3)OCC2)=NC2=NC(C)=C(C)N=C12 UIWAILCISYHSMT-UZLBHIALSA-N 0.000 claims description 2
- KLQIEPGDFZCIEM-VGSWGCGISA-N 4-(2-fluoro-4-methylphenyl)-6,7-dimethyl-2-[(2S,4R)-2-(1-methylpyrazol-4-yl)oxan-4-yl]pyrido[2,3-d]pyrimidine Chemical compound CC(C=C1)=CC(F)=C1C1=NC([C@H]2C[C@@H](C3=CN(C)N=C3)OCC2)=NC2=C1C=C(C)C(C)=N2 KLQIEPGDFZCIEM-VGSWGCGISA-N 0.000 claims description 2
- WXESIJLUFGHNIJ-MWTRTKDXSA-N 4-(4-chloro-2-fluorophenyl)-2-[(2S,4R)-2-(1-cyclopropylpyrazol-4-yl)oxan-4-yl]-6,7-dimethylpyrido[2,3-d]pyrimidine Chemical compound CC(C(C)=N1)=CC2=C1N=C([C@H]1C[C@@H](C3=CN(C4CC4)N=C3)OCC1)N=C2C(C=CC(Cl)=C1)=C1F WXESIJLUFGHNIJ-MWTRTKDXSA-N 0.000 claims description 2
- AHLNBERAINLMRO-KRWDZBQOSA-N 4-(4-chloro-2-fluorophenyl)-2-[(3R)-4,4-difluoro-3-(1-methylpyrazol-4-yl)piperidin-1-yl]-6,7-dimethylpteridine Chemical compound CC1=C(C)N=C2N=C(N(CCC3(F)F)C[C@H]3C3=CN(C)N=C3)N=C(C(C=CC(Cl)=C3)=C3F)C2=N1 AHLNBERAINLMRO-KRWDZBQOSA-N 0.000 claims description 2
- XASHGAXCRHFOLT-LAUBAEHRSA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2R,4S)-2-(2-methylpyridin-4-yl)oxan-4-yl]pteridine Chemical compound CC1=NC=CC([C@@H](C2)OCC[C@@H]2C2=NC3=NC(C)=C(C)N=C3C(C(C=CC(Cl)=C3)=C3F)=N2)=C1 XASHGAXCRHFOLT-LAUBAEHRSA-N 0.000 claims description 2
- OSODVIINYNBVOM-MGPUTAFESA-N 4-(4-chloro-2-fluorophenyl)-6,7-dimethyl-2-[(2R,4S)-2-(2-methylpyrimidin-5-yl)oxan-4-yl]pteridine Chemical compound CC1=C(C)N=C2N=C([C@@H]3C[C@H](C4=CN=C(C)N=C4)OCC3)N=C(C(C=CC(Cl)=C3)=C3F)C2=N1 OSODVIINYNBVOM-MGPUTAFESA-N 0.000 claims description 2
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