JP2019504102A5 - - Google Patents

Info

Publication number

JP2019504102A5

JP2019504102A5 JP2018540796A JP2018540796A JP2019504102A5 JP 2019504102 A5 JP2019504102 A5 JP 2019504102A5 JP 2018540796 A JP2018540796 A JP 2018540796A JP 2018540796 A JP2018540796 A JP 2018540796A JP 2019504102 A5 JP2019504102 A5 JP 2019504102A5

Authority

JP

Japan

Prior art keywords

compound

methyl

imidazo

pharmaceutical composition

propyl

Prior art date

2017-02-02

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
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims description 36
• 229940126062 Compound A Drugs 0.000 claims description 16
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 16
• -1 N- (2-fluoro-6-methylphenyl) -6- ( -(5-Methyl-2- (7-oxa-2-azaspiro [3.5] nonan-2-yl) nicotinamido) benzoyl) -5,6-dihydro-4H-benzo [b] thieno [2,3 -D] azepine-2-carboxamide Chemical compound 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 206010061603 Respiratory syncytial virus infection Diseases 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 9
• MTPVBMVUENFFLL-HXUWFJFHSA-N 1-(2-fluorophenyl)-3-[(3s)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]urea Chemical compound FC1=CC=CC=C1NC(=O)N[C@@H]1C(=O)NC2=CC=CC=C2C(C=2C=CC=CC=2)=N1 MTPVBMVUENFFLL-HXUWFJFHSA-N 0.000 claims description 8
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 8
• GOFXWTVKPWJNGD-UWJYYQICSA-N n-[2-[(2s)-2-[5-[(3s)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4-chlorophenyl]methanesulfonamide Chemical compound CC1=CN2N=C([C@H]3N(CCCC3)C(=O)C=3C(=CC=C(Cl)C=3)NS(C)(=O)=O)C=C2N=C1N1CC[C@H](N)C1 GOFXWTVKPWJNGD-UWJYYQICSA-N 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 229960000329 ribavirin Drugs 0.000 claims description 8
• HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 8
• BLUJRJMLDHEMRX-UHFFFAOYSA-N 2-[[2-hydroxy-5-[(5-methyltetrazol-1-yl)iminomethyl]phenyl]-(4-hydroxyphenyl)methyl]-4-[(5-methyltetrazol-1-yl)iminomethyl]phenol Chemical compound Cc1nnnn1N=Cc1ccc(O)c(c1)C(c1ccc(O)cc1)c1cc(C=Nn2nnnc2C)ccc1O BLUJRJMLDHEMRX-UHFFFAOYSA-N 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• 229960000402 palivizumab Drugs 0.000 claims description 7
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 5
• QZSZPSDRJPPZDZ-OAQYLSRUSA-N (9bs)-9b-(4-chlorophenyl)-1-(pyridine-3-carbonyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1[C@]1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CC=CN=C1 QZSZPSDRJPPZDZ-OAQYLSRUSA-N 0.000 claims description 4
• DKORMNNYNRPTBJ-UHFFFAOYSA-N 2-[[6-[[2-(3-hydroxypropyl)-5-methylanilino]methyl]-2-(3-morpholin-4-ylpropylamino)benzimidazol-1-yl]methyl]-6-methylpyridin-3-ol Chemical compound CC1=CC=C(CCCO)C(NCC=2C=C3N(CC=4C(=CC=C(C)N=4)O)C(NCCCN4CCOCC4)=NC3=CC=2)=C1 DKORMNNYNRPTBJ-UHFFFAOYSA-N 0.000 claims description 4
• LNZKOJMCKWERFO-UHFFFAOYSA-N 2H-thieno[2,3-d]azepine-2-carboxamide Chemical compound S1C(C=C2C1=CC=NC=C2)C(=O)N LNZKOJMCKWERFO-UHFFFAOYSA-N 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• UHHHWFCTIQAQKF-UHFFFAOYSA-N n-cyclopropyl-6-[4-[[2-(2-oxa-7-azaspiro[3.5]nonan-7-yl)pyridine-3-carbonyl]amino]benzoyl]-4,5-dihydrothieno[3,2-d][1]benzazepine-2-carboxamide Chemical compound C=1C=2CCN(C(=O)C=3C=CC(NC(=O)C=4C(=NC=CC=4)N4CCC5(COC5)CC4)=CC=3)C3=CC=CC=C3C=2SC=1C(=O)NC1CC1 UHHHWFCTIQAQKF-UHFFFAOYSA-N 0.000 claims description 4
• UNNCHYARSNZOPF-UHFFFAOYSA-L way-154641 Chemical compound [Na+].[Na+].NC(=O)CN(CC(N)=O)S(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C(C(C=4C(=CC(NC=5N=C(NC=6C=C(C=CC=6)S(=O)(=O)N(CC(N)=O)CC(N)=O)N=C(NC=6C=C(C=CC=6)S(=O)(=O)N(CC(N)=O)CC(N)=O)N=5)=CC=4)S([O-])(=O)=O)=CC=3)S([O-])(=O)=O)N=C(NC=3C=C(C=CC=3)S(=O)(=O)N(CC(N)=O)CC(N)=O)N=2)=C1 UNNCHYARSNZOPF-UHFFFAOYSA-L 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 229960003966 nicotinamide Drugs 0.000 claims description 3
• 235000005152 nicotinamide Nutrition 0.000 claims description 3
• 239000011570 nicotinamide Substances 0.000 claims description 3
• 230000000840 anti-viral effect Effects 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000002195 synergetic effect Effects 0.000 claims description 2
• SWWRPROUTDGFFV-UHFFFAOYSA-N CCS(=O)(=O)CCc1c(CN2C(=O)N(C3CC3)c4ccncc24)nc5cc(Cl)ccn15 Chemical compound CCS(=O)(=O)CCc1c(CN2C(=O)N(C3CC3)c4ccncc24)nc5cc(Cl)ccn15 SWWRPROUTDGFFV-UHFFFAOYSA-N 0.000 claims 2
• ALMZSKFFZDETDT-UHFFFAOYSA-N O=S(=O)(C)CCCN1C2=C(C=C(Cl)C=C2)N=C1CN1C2=C(N(C1=O)C1CC1)C=CN=C2 Chemical compound O=S(=O)(C)CCCN1C2=C(C=C(Cl)C=C2)N=C1CN1C2=C(N(C1=O)C1CC1)C=CN=C2 ALMZSKFFZDETDT-UHFFFAOYSA-N 0.000 claims 2
• ZJSVBILSBHWRTN-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-c]pyridin-2-one Chemical compound C1=NC=C2NC(=O)NC2=C1 ZJSVBILSBHWRTN-UHFFFAOYSA-N 0.000 claims 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
• GTQTUABHRCWVLL-UHFFFAOYSA-N C(CCN1C(=CC2=CC(=CC=C12)Cl)CN1C2=C(N(C1=O)CC(F)(F)F)C=CN=C2)S(=O)(=O)C Chemical compound C(CCN1C(=CC2=CC(=CC=C12)Cl)CN1C2=C(N(C1=O)CC(F)(F)F)C=CN=C2)S(=O)(=O)C GTQTUABHRCWVLL-UHFFFAOYSA-N 0.000 claims 1
• VTCJNYICQADBJD-UHFFFAOYSA-N N-(2-fluoro-6-methylphenyl)-6-[4-[[5-methyl-2-(7-oxa-2-azaspiro[3.5]nonan-2-yl)pyridine-3-carbonyl]amino]benzoyl]-4,5-dihydrothieno[3,2-d][1]benzazepine-2-carboxamide Chemical compound FC1=C(C(=CC=C1)C)NC(=O)C1=CC2=C(C3=C(N(CC2)C(C2=CC=C(C=C2)NC(C2=C(N=CC(=C2)C)N2CC4(C2)CCOCC4)=O)=O)C=CC=C3)S1 VTCJNYICQADBJD-UHFFFAOYSA-N 0.000 claims 1
• JWTOLVMZWVMYJU-UHFFFAOYSA-N S1C(=CC2=C1C1=C(NCC2)C=CC=C1)C(=O)N Chemical compound S1C(=CC2=C1C1=C(NCC2)C=CC=C1)C(=O)N JWTOLVMZWVMYJU-UHFFFAOYSA-N 0.000 claims 1
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 101150062136 mdt-6 gene Proteins 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1