JP2018524333A5 - - Google Patents

Info

Publication number

JP2018524333A5

JP2018524333A5 JP2017567064A JP2017567064A JP2018524333A5 JP 2018524333 A5 JP2018524333 A5 JP 2018524333A5 JP 2017567064 A JP2017567064 A JP 2017567064A JP 2017567064 A JP2017567064 A JP 2017567064A JP 2018524333 A5 JP2018524333 A5 JP 2018524333A5

Authority

JP

Japan

Prior art keywords

alkyl

optionally

group

fluoro

hydrogen

Prior art date

2016-07-01

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

• Espacenet
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• 229910052739 hydrogen Inorganic materials 0.000 claims description 162
• 239000001257 hydrogen Substances 0.000 claims description 162
• 125000001153 fluoro group Chemical group F* 0.000 claims description 124
• 125000005842 heteroatom Chemical group 0.000 claims description 118
• 125000000217 alkyl group Chemical group 0.000 claims description 105
• 125000001424 substituent group Chemical group 0.000 claims description 105
• 150000001875 compounds Chemical class 0.000 claims description 92
• 150000002431 hydrogen Chemical class 0.000 claims description 82
• 229910052736 halogen Inorganic materials 0.000 claims description 80
• 150000002367 halogens Chemical class 0.000 claims description 80
• 229920006395 saturated elastomer Polymers 0.000 claims description 79
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 74
• 229910052760 oxygen Inorganic materials 0.000 claims description 67
• 229910052757 nitrogen Inorganic materials 0.000 claims description 61
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 229910052717 sulfur Inorganic materials 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 48
• 239000012453 solvate Substances 0.000 claims description 47
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
• 229910052799 carbon Inorganic materials 0.000 claims description 29
• 125000004043 oxo group Chemical group O=* 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• -1 3-cyano-4-fluoro-phenyl Chemical group 0.000 claims description 16
• 150000001412 amines Chemical class 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 8
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 208000015181 infectious disease Diseases 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 239000002904 solvent Substances 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 238000007341 Heck reaction Methods 0.000 claims description 2
• 241001465754 Metazoa Species 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 239000003112 inhibitor Substances 0.000 claims description 2
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
• 229940127557 pharmaceutical product Drugs 0.000 claims description 2
• CUQMVKFZIUMOFU-UHFFFAOYSA-N 3H-oxathiazepine-6-carboxamide Chemical compound O1SNC=CC(=C1)C(=O)N CUQMVKFZIUMOFU-UHFFFAOYSA-N 0.000 claims 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 6
• UESJZZNESAYQNC-ISVAXAHUSA-N (3R)-3-[(1S)-1-hydroxyethyl]-7-methyl-1,1-dioxo-N-(3,4,5-trifluorophenyl)-2,3-dihydropyrrolo[3,4-f]thiazepine-6-carboxamide Chemical compound O[C@@H](C)[C@@H]1NS(C=2C(C=C1)=C(N(C=2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F)(=O)=O UESJZZNESAYQNC-ISVAXAHUSA-N 0.000 claims 4
• WNLANMOBNSBQNN-UHFFFAOYSA-N thiazepine-6-carboxamide Chemical compound S1N=CC=CC(=C1)C(=O)N WNLANMOBNSBQNN-UHFFFAOYSA-N 0.000 claims 3
• GYQOFSAOVXQOKF-UHFFFAOYSA-N N-[3-(difluoromethyl)-4-fluorophenyl]-3,7-dimethyl-3-[(1-methylimidazol-2-yl)methyl]-1,1-dioxo-2,4-dihydropyrrolo[3,4-b][1,4,5]oxathiazepine-6-carboxamide Chemical class FC(C=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1OCC(NS2(=O)=O)(CC=1N(C=CN=1)C)C)C)F GYQOFSAOVXQOKF-UHFFFAOYSA-N 0.000 claims 2
• IQITWXNBCPTDCI-JTQLQIEISA-N (3S)-N-(3-cyano-4-fluorophenyl)-3,7-dimethyl-1,1-dioxo-2,3,4,5-tetrahydropyrrolo[3,4-f]thiazepine-6-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1F)NC(=O)C=1N(C=C2C=1CC[C@@H](NS2(=O)=O)C)C IQITWXNBCPTDCI-JTQLQIEISA-N 0.000 claims 1
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 1
• YGNQRHNWUQGENW-UHFFFAOYSA-N S1NC=CC=C2C1=CN=C2C(=O)N Chemical compound S1NC=CC=C2C1=CN=C2C(=O)N YGNQRHNWUQGENW-UHFFFAOYSA-N 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 239000000203 mixture Substances 0.000 claims 1
• 125000002950 monocyclic group Chemical group 0.000 description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 description 11
• 125000000753 cycloalkyl group Chemical group 0.000 description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
• 125000002971 oxazolyl group Chemical group 0.000 description 7
• 125000003226 pyrazolyl group Chemical group 0.000 description 7
• 125000004429 atom Chemical group 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 125000003566 oxetanyl group Chemical group 0.000 description 5
• 125000003386 piperidinyl group Chemical group 0.000 description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
• 125000001072 heteroaryl group Chemical group 0.000 description 3
• 125000003373 pyrazinyl group Chemical group 0.000 description 3
• 125000000168 pyrrolyl group Chemical group 0.000 description 3
• 125000001544 thienyl group Chemical group 0.000 description 3
• DEFLNOSTNCSZRB-IDTAVKCVSA-N 9-[(2r,3r,4r,5r)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]-n-methoxypurin-6-amine Chemical compound CO[C@@H]1[C@H](OC)[C@@H](COC)O[C@H]1N1C2=NC=NC(NOC)=C2N=C1 DEFLNOSTNCSZRB-IDTAVKCVSA-N 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• 125000003545 alkoxy group Chemical group 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 1
• 150000001335 aliphatic alkanes Chemical class 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• 125000000623 heterocyclic group Chemical group 0.000 description 1