JP2019509315A5 - - Google Patents

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Publication number

JP2019509315A5

JP2019509315A5 JP2018549836A JP2018549836A JP2019509315A5 JP 2019509315 A5 JP2019509315 A5 JP 2019509315A5 JP 2018549836 A JP2018549836 A JP 2018549836A JP 2018549836 A JP2018549836 A JP 2018549836A JP 2019509315 A5 JP2019509315 A5 JP 2019509315A5

Authority

JP

Japan

Prior art keywords

mannopyranosyloxy

methyl

methylphenyl

pharmaceutical composition

mannopyranoside

Prior art date

2017-03-23

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.)

Pending

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• 239000008194 pharmaceutical composition Substances 0.000 claims 16
• -1 2-methyl-4- [4- (pyridin-3-yl) -1H-1,2,3-triazol-1-yl] phenyl Chemical group 0.000 claims 11
• 150000001875 compounds Chemical class 0.000 claims 11
• 201000010099 disease Diseases 0.000 claims 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
• 208000019206 urinary tract infection Diseases 0.000 claims 6
• 208000035143 Bacterial infection Diseases 0.000 claims 4
• 208000011231 Crohn disease Diseases 0.000 claims 4
• 125000000217 alkyl group Chemical group 0.000 claims 4
• 208000022362 bacterial infectious disease Diseases 0.000 claims 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
• 239000003814 drug Substances 0.000 claims 3
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
• 125000003118 aryl group Chemical group 0.000 claims 2
• 229910052736 halogen Inorganic materials 0.000 claims 2
• 150000002367 halogens Chemical class 0.000 claims 2
• 125000001072 heteroaryl group Chemical group 0.000 claims 2
• 230000001404 mediated effect Effects 0.000 claims 2
• ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 2
• VMUFHDKHYAGHQP-AANPDWTMSA-N (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(4-isoquinolin-5-yl-2-methylphenoxy)oxane-3,4,5-triol Chemical compound Cc1cc(ccc1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)-c1cccc2cnccc12 VMUFHDKHYAGHQP-AANPDWTMSA-N 0.000 claims 1
• HYFAFWNEPWXODM-AANPDWTMSA-N (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(4-isoquinolin-7-yloxy-2-methyl-5-nitrophenoxy)oxane-3,4,5-triol Chemical compound CC1=CC(OC2=CC=C3C=CN=CC3=C2)=C(C=C1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)[N+]([O-])=O HYFAFWNEPWXODM-AANPDWTMSA-N 0.000 claims 1
• VXDBKXRJILGITM-AANPDWTMSA-N (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[2-methyl-4-(1,2,3,4-tetrahydroisoquinolin-5-yl)phenoxy]oxane-3,4,5-triol Chemical compound Cc1cc(ccc1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)-c1cccc2CNCCc12 VXDBKXRJILGITM-AANPDWTMSA-N 0.000 claims 1
• KTMKCNBRKXDKAM-VROINQGHSA-N (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[2-methyl-4-(2-methyl-3,4-dihydro-1H-isoquinolin-5-yl)phenoxy]oxane-3,4,5-triol Chemical compound CN1CCc2c(C1)cccc2-c1ccc(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)c(C)c1 KTMKCNBRKXDKAM-VROINQGHSA-N 0.000 claims 1
• BWIGSUSEUMXPNK-MJCUULBUSA-N (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[2-methyl-4-(3-methyl-2H-indazol-5-yl)phenoxy]oxane-3,4,5-triol Chemical compound Cc1[nH]nc2ccc(cc12)-c1ccc(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)c(C)c1 BWIGSUSEUMXPNK-MJCUULBUSA-N 0.000 claims 1
• WDFFHFXEWUACJA-GFEQUFNTSA-N (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[2-methyl-5-nitro-4-(2-nitrophenoxy)phenoxy]oxane-3,4,5-triol Chemical compound CC1=CC(OC2=C(C=CC=C2)[N+]([O-])=O)=C(C=C1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)[N+]([O-])=O WDFFHFXEWUACJA-GFEQUFNTSA-N 0.000 claims 1
• IJFNSHLIJCWAJG-KOVVAJLHSA-N (2R,3S,4S,5S,6R)-2-[4-(1-aminoisoquinolin-5-yl)-2-methylphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound Cc1cc(ccc1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)-c1cccc2c(N)nccc12 IJFNSHLIJCWAJG-KOVVAJLHSA-N 0.000 claims 1
• RLXZKGQVICOTPJ-KOVVAJLHSA-N (2R,3S,4S,5S,6R)-2-[4-(1-aminoisoquinolin-7-yl)-2-methylphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound [C@H]1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=C(C=C(C=C1)C1=CC=C2C=CN=C(C2=C1)N)C RLXZKGQVICOTPJ-KOVVAJLHSA-N 0.000 claims 1
• UIOBZAJGQPFERJ-JGLNRKDHSA-N (2R,3S,4S,5S,6R)-2-[4-(3-amino-1H-indazol-5-yl)-2-methylphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound Cc1cc(ccc1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)-c1ccc2[nH]nc(N)c2c1 UIOBZAJGQPFERJ-JGLNRKDHSA-N 0.000 claims 1
• BAGVLHOGIGVWNO-SLHNCBLASA-N 2-[5-methyl-2-nitro-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]benzonitrile Chemical compound CC1=CC(OC2=C(C=CC=C2)C#N)=C(C=C1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)[N+]([O-])=O BAGVLHOGIGVWNO-SLHNCBLASA-N 0.000 claims 1
• DBMOHJYMORNGSY-FNIAAEIWSA-N 3-(methylcarbamoyl)-5-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]benzoic acid Chemical compound CNC(=O)C1=CC(=CC(=C1)C(O)=O)C1=CC(C)=C(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)C=C1 DBMOHJYMORNGSY-FNIAAEIWSA-N 0.000 claims 1
• IYZIARNSXPGYSC-UHFFFAOYSA-N 3-phenylbenzamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 IYZIARNSXPGYSC-UHFFFAOYSA-N 0.000 claims 1
• LRTFJRXRGJISBO-SLHNCBLASA-N 4-[5-methyl-2-nitro-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]benzonitrile Chemical compound CC1=CC(OC2=CC=C(C=C2)C#N)=C(C=C1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)[N+]([O-])=O LRTFJRXRGJISBO-SLHNCBLASA-N 0.000 claims 1
• QNQFUHVFWRHJRE-KOVVAJLHSA-N 5-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2H-isoquinolin-1-one Chemical compound Cc1cc(ccc1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)-c1cccc2c1cc[nH]c2=O QNQFUHVFWRHJRE-KOVVAJLHSA-N 0.000 claims 1
• NHKSUDAJGASANW-KOVVAJLHSA-N 5-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-N-propan-2-ylpyridine-3-carboxamide Chemical compound CC(C)NC(=O)C1=CC(=CN=C1)C1=CC(C)=C(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)C=C1 NHKSUDAJGASANW-KOVVAJLHSA-N 0.000 claims 1
• XBHYZDSPLLPGBC-GJGATLCTSA-N 5-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]pyridine-3-carboxylic acid Chemical compound CC1=C(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)C=CC(=C1)C1=CN=CC(=C1)C(O)=O XBHYZDSPLLPGBC-GJGATLCTSA-N 0.000 claims 1
• KZOQVRGVRZMRCJ-FJBDOQBJSA-N 6-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1H-thieno[3,2-d]pyrimidine-2,4-dione Chemical compound Cc1cc(ccc1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)-c1cc2[nH]c(=O)[nH]c(=O)c2s1 KZOQVRGVRZMRCJ-FJBDOQBJSA-N 0.000 claims 1
• ZCVUFIIEULABCG-BZDYCCQFSA-N 7-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2-propan-2-yl-3,4-dihydroisoquinolin-1-one Chemical compound CC(C)N1CCC2=C(C=C(C=C2)C2=CC(C)=C(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)C=C2)C1=O ZCVUFIIEULABCG-BZDYCCQFSA-N 0.000 claims 1
• PTHYFAHVFNGFOH-BZDYCCQFSA-N 7-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-2-propan-2-ylisoquinolin-1-one Chemical compound CC(C)N1C=CC2=C(C=C(C=C2)C2=CC(C)=C(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)C=C2)C1=O PTHYFAHVFNGFOH-BZDYCCQFSA-N 0.000 claims 1
• WIVGXNONBDCUDO-UHFFFAOYSA-N CC1=CC(=CC=C1)C2=CC(CC(=C2)C(=O)O)(C)C(=O)O Chemical compound CC1=CC(=CC=C1)C2=CC(CC(=C2)C(=O)O)(C)C(=O)O WIVGXNONBDCUDO-UHFFFAOYSA-N 0.000 claims 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
• GTXGXWLIQNJDAP-MJCUULBUSA-N N-[2-[5-methyl-2-nitro-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]phenyl]acetamide Chemical compound CC(=O)NC1=C(OC2=C(C=C(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)C(C)=C2)[N+]([O-])=O)C=CC=C1 GTXGXWLIQNJDAP-MJCUULBUSA-N 0.000 claims 1
• XOPAVIQSCDWFEN-MJCUULBUSA-N N-[3-[5-methyl-2-nitro-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC(OC2=C(C=C(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)C(C)=C2)[N+]([O-])=O)=CC=C1 XOPAVIQSCDWFEN-MJCUULBUSA-N 0.000 claims 1
• PBBCIAAVPBHHHB-MJCUULBUSA-N N-[4-[5-methyl-2-nitro-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OC2=C(C=C(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)C(C)=C2)[N+]([O-])=O)C=C1 PBBCIAAVPBHHHB-MJCUULBUSA-N 0.000 claims 1
• 230000001668 ameliorated effect Effects 0.000 claims 1
• 239000003242 anti bacterial agent Substances 0.000 claims 1
• 230000003115 biocidal effect Effects 0.000 claims 1
• 239000002775 capsule Substances 0.000 claims 1
• 230000001684 chronic effect Effects 0.000 claims 1
• 125000000753 cycloalkyl group Chemical group 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 230000000694 effects Effects 0.000 claims 1
• 150000002148 esters Chemical class 0.000 claims 1
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 claims 1
• 230000005764 inhibitory process Effects 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 238000000034 method Methods 0.000 claims 1
• WWZAJMUDBKQTLG-JGLNRKDHSA-N methyl 5-[3-methyl-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]pyridine-3-carboxylate Chemical compound COC(=O)C1=CC(=CN=C1)C1=CC(C)=C(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)C=C1 WWZAJMUDBKQTLG-JGLNRKDHSA-N 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 230000000306 recurrent effect Effects 0.000 claims 1
• 150000003839 salts Chemical class 0.000 claims 1
• 229940124597 therapeutic agent Drugs 0.000 claims 1
• 238000011200 topical administration Methods 0.000 claims 1