JPWO2020070088A5 - - Google Patents
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- Publication number
- JPWO2020070088A5 JPWO2020070088A5 JP2021518664A JP2021518664A JPWO2020070088A5 JP WO2020070088 A5 JPWO2020070088 A5 JP WO2020070088A5 JP 2021518664 A JP2021518664 A JP 2021518664A JP 2021518664 A JP2021518664 A JP 2021518664A JP WO2020070088 A5 JPWO2020070088 A5 JP WO2020070088A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- chloro
- chromen
- phenoxy
- ethoxy
- Prior art date
- 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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- -1 hydroxy, amino Chemical group 0.000 claims description 150
- 125000000217 alkyl group Chemical group 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 102
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 50
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 41
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 14
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
- 239000002841 Lewis acid Substances 0.000 claims description 9
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 9
- 150000007517 lewis acids Chemical class 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 230000003301 hydrolyzing effect Effects 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims 87
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 67
- 150000003839 salts Chemical class 0.000 claims 60
- 125000003545 alkoxy group Chemical group 0.000 claims 48
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 30
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 28
- 229910052794 bromium Inorganic materials 0.000 claims 26
- 229910052801 chlorine Inorganic materials 0.000 claims 26
- 229910052731 fluorine Inorganic materials 0.000 claims 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 3
- 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 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims 3
- 125000005825 oxyethoxy group Chemical group [H]C([H])(O[*:1])C([H])([H])O[*:2] 0.000 claims 3
- KAGAMDHXJJBIKC-HRAATJIYSA-N (2R,4S)-1-(benzenesulfonyl)-4-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]pyrrolidine-2-carboxylic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)N1[C@H](C[C@@H](C1)OC1=C(C=CC(=C1)C(F)(F)F)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C(=O)O KAGAMDHXJJBIKC-HRAATJIYSA-N 0.000 claims 2
- GTISIINSWRVIRS-INIZCTEOSA-N (2S)-3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]-2-(cyclopropylsulfonylamino)propanoic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OC[C@@H](C(=O)O)NS(=O)(=O)C2CC2)C=C(C=C1)C(F)(F)F)=O GTISIINSWRVIRS-INIZCTEOSA-N 0.000 claims 2
- JGTASXBYOUIIGD-HNNXBMFYSA-N (2S)-3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]-2-(ethylsulfamoylamino)propanoic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OC[C@@H](C(=O)O)NS(NCC)(=O)=O)C=C(C=C1)C(F)(F)F)=O JGTASXBYOUIIGD-HNNXBMFYSA-N 0.000 claims 2
- KAGAMDHXJJBIKC-IERDGZPVSA-N (2S,4R)-1-(benzenesulfonyl)-4-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]pyrrolidine-2-carboxylic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)N1[C@@H](C[C@H](C1)OC1=C(C=CC(=C1)C(F)(F)F)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C(=O)O KAGAMDHXJJBIKC-IERDGZPVSA-N 0.000 claims 2
- MJECMANRTPQMLL-UHFFFAOYSA-N 2-[3-[2-(8-bromo-4-oxochromen-2-yl)-5-methylphenoxy]propoxy]acetic acid Chemical compound BrC=1C=CC=C2C(C=C(OC=12)C1=C(OCCCOCC(=O)O)C=C(C=C1)C)=O MJECMANRTPQMLL-UHFFFAOYSA-N 0.000 claims 2
- GKPDFSCXWUESMJ-UHFFFAOYSA-N 2-[3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]propoxy]acetic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCCOCC(=O)O)C=C(C=C1)C(F)(F)F)=O GKPDFSCXWUESMJ-UHFFFAOYSA-N 0.000 claims 2
- CTJGNLAYZBQBAD-UHFFFAOYSA-N 2-[3-[2-(8-chloro-4-oxochromen-2-yl)-5-methylphenoxy]propoxy]acetic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCCOCC(=O)O)C=C(C=C1)C)=O CTJGNLAYZBQBAD-UHFFFAOYSA-N 0.000 claims 2
- RLVAFWJIOWOAPJ-UHFFFAOYSA-N 2-[3-[5-chloro-2-(8-chloro-4-oxochromen-2-yl)-4-methylphenoxy]propoxy]acetic acid Chemical compound ClC=1C(=CC(=C(OCCCOCC(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C RLVAFWJIOWOAPJ-UHFFFAOYSA-N 0.000 claims 2
- ZFCVKSCWTKIWGL-UHFFFAOYSA-N 2-[3-[5-chloro-2-(8-chloro-4-oxochromen-2-yl)phenoxy]propoxy]acetic acid Chemical compound ClC=1C=CC(=C(OCCCOCC(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl ZFCVKSCWTKIWGL-UHFFFAOYSA-N 0.000 claims 2
- IKBFZBDQNBRXFY-UHFFFAOYSA-N 3-[2-(8-bromo-4-oxochromen-2-yl)-5-chloro-4-methylphenoxy]propanoic acid Chemical compound BrC=1C=CC=C2C(C=C(OC=12)C1=C(OCCC(=O)O)C=C(C(=C1)C)Cl)=O IKBFZBDQNBRXFY-UHFFFAOYSA-N 0.000 claims 2
- UKMOBIMZKRFSBF-UHFFFAOYSA-N 3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethoxy)phenoxy]propanoic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCC(=O)O)C=C(C=C1)OC(F)(F)F)=O UKMOBIMZKRFSBF-UHFFFAOYSA-N 0.000 claims 2
- FOKVNPGPHSDVJA-UHFFFAOYSA-N 3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]cyclobutane-1-carboxylic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OC2CC(C2)C(=O)O)C=C(C=C1)C(F)(F)F)=O FOKVNPGPHSDVJA-UHFFFAOYSA-N 0.000 claims 2
- CFOLGLUPCCYCKY-UHFFFAOYSA-N 3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]propanoic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCC(=O)O)C=C(C=C1)C(F)(F)F)=O CFOLGLUPCCYCKY-UHFFFAOYSA-N 0.000 claims 2
- VUBABKJBLZHQAX-UHFFFAOYSA-N 3-[2-(8-chloro-4-oxochromen-2-yl)-5-methoxy-4-methylphenoxy]propanoic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCC(=O)O)C=C(C(=C1)C)OC)=O VUBABKJBLZHQAX-UHFFFAOYSA-N 0.000 claims 2
- HMAPIXHSDCETAW-UHFFFAOYSA-N 3-[5-bromo-2-(8-chloro-4-oxochromen-2-yl)-4-methylphenoxy]propanoic acid Chemical compound BrC=1C(=CC(=C(OCCC(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C HMAPIXHSDCETAW-UHFFFAOYSA-N 0.000 claims 2
- SUZSGSKEACPBFF-UHFFFAOYSA-N 3-[5-chloro-2-(8-chloro-4-oxochromen-2-yl)-4-methoxyphenoxy]propanoic acid Chemical compound ClC=1C(=CC(=C(OCCC(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)OC SUZSGSKEACPBFF-UHFFFAOYSA-N 0.000 claims 2
- FWKYXYNGVIBNKJ-UHFFFAOYSA-N 3-[5-chloro-2-(8-chloro-4-oxochromen-2-yl)-4-methylphenoxy]propanoic acid Chemical compound ClC=1C(=CC(=C(OCCC(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C FWKYXYNGVIBNKJ-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- LMPXZBUDWWXTCV-HAQNSBGRSA-N CC(C(Cl)=C1)=CC(C(OC(C2=CC=C3)=C3Cl)=CC2=O)=C1O[C@H](C1)C[C@@H]1C(O)=O Chemical compound CC(C(Cl)=C1)=CC(C(OC(C2=CC=C3)=C3Cl)=CC2=O)=C1O[C@H](C1)C[C@@H]1C(O)=O LMPXZBUDWWXTCV-HAQNSBGRSA-N 0.000 claims 2
- QHJVMHZOKDNTKF-MQMHXKEQSA-N ClC=1C=CC=C2C(C=C(OC=12)C1=C(O[C@@H]2C[C@H](C2)C(=O)NS(=O)(=O)C2CC2)C=C(C=C1)C(F)(F)F)=O Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(O[C@@H]2C[C@H](C2)C(=O)NS(=O)(=O)C2CC2)C=C(C=C1)C(F)(F)F)=O QHJVMHZOKDNTKF-MQMHXKEQSA-N 0.000 claims 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- MDYWBYUFQZIRRV-UHFFFAOYSA-N methyl 3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]propanoate Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCC(=O)OC)C=C(C=C1)C(F)(F)F)=O MDYWBYUFQZIRRV-UHFFFAOYSA-N 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- IFKJBBQWLDDQTL-MRXNPFEDSA-N (2R)-1-[2-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]acetyl]pyrrolidine-2-carboxylic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCC(=O)N2[C@H](CCC2)C(=O)O)C=C(C=C1)C(F)(F)F)=O IFKJBBQWLDDQTL-MRXNPFEDSA-N 0.000 claims 1
- XXIDQGOBAVCHRJ-GOSISDBHSA-N (2R)-1-[2-[2-(8-chloro-4-oxochromen-2-yl)-5-methylphenoxy]acetyl]-N-methylsulfonylpyrrolidine-2-carboxamide Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCC(=O)N2[C@H](CCC2)C(=O)NS(=O)(=O)C)C=C(C=C1)C)=O XXIDQGOBAVCHRJ-GOSISDBHSA-N 0.000 claims 1
- KNUADDIJMDXGKT-QGZVFWFLSA-N (2R)-1-[2-[2-(8-chloro-4-oxochromen-2-yl)-5-methylphenoxy]acetyl]pyrrolidine-2-carboxylic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCC(=O)N2[C@H](CCC2)C(=O)O)C=C(C=C1)C)=O KNUADDIJMDXGKT-QGZVFWFLSA-N 0.000 claims 1
- CSNBWUDILIPWAK-QGZVFWFLSA-N (2R)-1-[2-[5-bromo-2-(8-chloro-4-oxochromen-2-yl)-4-methylphenoxy]acetyl]pyrrolidine-2-carboxylic acid Chemical compound BrC=1C(=CC(=C(OCC(=O)N2[C@H](CCC2)C(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C CSNBWUDILIPWAK-QGZVFWFLSA-N 0.000 claims 1
- VSYRETFQCKQICD-QGZVFWFLSA-N (2R)-1-[3-[5-bromo-2-(8-chloro-4-oxochromen-2-yl)phenoxy]propanoyl]pyrrolidine-2-carboxylic acid Chemical compound BrC=1C=CC(=C(OCCC(=O)N2[C@H](CCC2)C(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl VSYRETFQCKQICD-QGZVFWFLSA-N 0.000 claims 1
- KAGAMDHXJJBIKC-IIBYNOLFSA-N (2R,4R)-1-(benzenesulfonyl)-4-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]pyrrolidine-2-carboxylic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)N1[C@H](C[C@H](C1)OC1=C(C=CC(=C1)C(F)(F)F)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C(=O)O KAGAMDHXJJBIKC-IIBYNOLFSA-N 0.000 claims 1
- IFKJBBQWLDDQTL-INIZCTEOSA-N (2S)-1-[2-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]acetyl]pyrrolidine-2-carboxylic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCC(=O)N2[C@@H](CCC2)C(=O)O)C=C(C=C1)C(F)(F)F)=O IFKJBBQWLDDQTL-INIZCTEOSA-N 0.000 claims 1
- XXIDQGOBAVCHRJ-SFHVURJKSA-N (2S)-1-[2-[2-(8-chloro-4-oxochromen-2-yl)-5-methylphenoxy]acetyl]-N-methylsulfonylpyrrolidine-2-carboxamide Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCC(=O)N2[C@@H](CCC2)C(=O)NS(=O)(=O)C)C=C(C=C1)C)=O XXIDQGOBAVCHRJ-SFHVURJKSA-N 0.000 claims 1
- KNUADDIJMDXGKT-KRWDZBQOSA-N (2S)-1-[2-[2-(8-chloro-4-oxochromen-2-yl)-5-methylphenoxy]acetyl]pyrrolidine-2-carboxylic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCC(=O)N2[C@@H](CCC2)C(=O)O)C=C(C=C1)C)=O KNUADDIJMDXGKT-KRWDZBQOSA-N 0.000 claims 1
- CSNBWUDILIPWAK-KRWDZBQOSA-N (2S)-1-[2-[5-bromo-2-(8-chloro-4-oxochromen-2-yl)-4-methylphenoxy]acetyl]pyrrolidine-2-carboxylic acid Chemical compound BrC=1C(=CC(=C(OCC(=O)N2[C@@H](CCC2)C(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C CSNBWUDILIPWAK-KRWDZBQOSA-N 0.000 claims 1
- VSYRETFQCKQICD-KRWDZBQOSA-N (2S)-1-[3-[5-bromo-2-(8-chloro-4-oxochromen-2-yl)phenoxy]propanoyl]pyrrolidine-2-carboxylic acid Chemical compound BrC=1C=CC(=C(OCCC(=O)N2[C@@H](CCC2)C(=O)O)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl VSYRETFQCKQICD-KRWDZBQOSA-N 0.000 claims 1
- SGUDSIBVUPDMDH-ZDUSSCGKSA-N (2S)-2-amino-3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]propanoic acid Chemical compound N[C@H](C(=O)O)COC1=C(C=CC(=C1)C(F)(F)F)C=1OC2=C(C=CC=C2C(C=1)=O)Cl SGUDSIBVUPDMDH-ZDUSSCGKSA-N 0.000 claims 1
- DUEXLXTZNSNUKY-FQEVSTJZSA-N (2S)-3-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]-2-[(4-methylphenyl)sulfonylamino]propanoic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OC[C@@H](C(=O)O)NS(=O)(=O)C2=CC=C(C=C2)C)C=C(C=C1)C(F)(F)F)=O DUEXLXTZNSNUKY-FQEVSTJZSA-N 0.000 claims 1
- SNLNOUWXZCCLAC-ACJLOTCBSA-N (2S,4R)-4-[2-(8-chloro-4-oxochromen-2-yl)-5-(trifluoromethyl)phenoxy]-1-cyclopropylsulfonylpyrrolidine-2-carboxylic acid Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(O[C@@H]2C[C@H](N(C2)S(=O)(=O)C2CC2)C(=O)O)C=C(C=C1)C(F)(F)F)=O SNLNOUWXZCCLAC-ACJLOTCBSA-N 0.000 claims 1
- SSAIWAQGABURSN-UWJYYQICSA-N (2S,4S)-1-benzoyl-4-[5-bromo-2-(8-chloro-4-oxochromen-2-yl)phenoxy]pyrrolidine-2-carboxylic acid Chemical compound C(C1=CC=CC=C1)(=O)N1[C@@H](C[C@@H](C1)OC1=C(C=CC(=C1)Br)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C(=O)O SSAIWAQGABURSN-UWJYYQICSA-N 0.000 claims 1
- KKRFLXBDWVPTRO-NHYWBVRUSA-N (2S,4S)-4-[5-bromo-2-(8-chloro-4-oxochromen-2-yl)phenoxy]pyrrolidine-2-carboxylic acid Chemical compound C1(=CC=C(C=C1O[C@H]1C[C@@H](C(=O)O)NC1)Br)C=1OC2=C(C(=O)C=1)C=CC=C2Cl KKRFLXBDWVPTRO-NHYWBVRUSA-N 0.000 claims 1
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- CUIVJHGAINGCGA-XYPYZODXSA-N COC(C(Br)=C1)=CC(O[C@H](C2)C[C@@H]2C(O)=O)=C1C(OC(C1=CC=C2)=C2Cl)=CC1=O Chemical compound COC(C(Br)=C1)=CC(O[C@H](C2)C[C@@H]2C(O)=O)=C1C(OC(C1=CC=C2)=C2Cl)=CC1=O CUIVJHGAINGCGA-XYPYZODXSA-N 0.000 claims 1
- FJWIQUFMYHOMLT-UHFFFAOYSA-N COC(C(OC)=C1)=CC(C(OC(C2=CC=C3)=C3Cl)=CC2=O)=C1OCC1(CC(O)=O)CC1 Chemical compound COC(C(OC)=C1)=CC(C(OC(C2=CC=C3)=C3Cl)=CC2=O)=C1OCC1(CC(O)=O)CC1 FJWIQUFMYHOMLT-UHFFFAOYSA-N 0.000 claims 1
- UVZUWTRIRMGJOG-JOCQHMNTSA-N COC(C=C1)=CC(C(OC(C2=CC=C3)=C3Cl)=CC2=O)=C1OC[C@H](C1)C[C@@H]1C(O)=O Chemical compound COC(C=C1)=CC(C(OC(C2=CC=C3)=C3Cl)=CC2=O)=C1OC[C@H](C1)C[C@@H]1C(O)=O UVZUWTRIRMGJOG-JOCQHMNTSA-N 0.000 claims 1
- VOWHGRWMVZESFU-UHFFFAOYSA-N CS(NC(COCCOC(C=C(C(F)(F)F)C=C1)=C1C(OC(C1=CC=C2)=C2Cl)=CC1=O)=O)(=O)=O Chemical compound CS(NC(COCCOC(C=C(C(F)(F)F)C=C1)=C1C(OC(C1=CC=C2)=C2Cl)=CC1=O)=O)(=O)=O VOWHGRWMVZESFU-UHFFFAOYSA-N 0.000 claims 1
- 108091036055 CccDNA Proteins 0.000 claims 1
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- YVMLXCUCDOPWKX-SHTZXODSSA-N ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCO[C@@H]2C[C@H](C2)C(=O)OC)C=C(C=C1)S(=O)(=O)C)=O Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCO[C@@H]2C[C@H](C2)C(=O)OC)C=C(C=C1)S(=O)(=O)C)=O YVMLXCUCDOPWKX-SHTZXODSSA-N 0.000 claims 1
- UIFLNCAXOSAOND-SHTZXODSSA-N ClC=1C=CC=C2C(C=C(OC=12)C1=C(O[C@@H]2C[C@H](C2)C(=O)O)C=C(C=C1)C1CC1)=O Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(O[C@@H]2C[C@H](C2)C(=O)O)C=C(C=C1)C1CC1)=O UIFLNCAXOSAOND-SHTZXODSSA-N 0.000 claims 1
- QSBDMOYVKWVIDO-HAQNSBGRSA-N ClC=1C=CC=C2C(C=C(OC=12)C1=C(O[C@@H]2C[C@H](C2)C(=O)O)C=CC=C1)=O Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(O[C@@H]2C[C@H](C2)C(=O)O)C=CC=C1)=O QSBDMOYVKWVIDO-HAQNSBGRSA-N 0.000 claims 1
- 108020004414 DNA Proteins 0.000 claims 1
- 101710142246 External core antigen Proteins 0.000 claims 1
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- MSAPNZITTQMAIY-HOMQSWHASA-N OC([C@H](C1)C[C@@H]1OC1=CC(Br)=CN=C1C(OC(C1=CC=C2)=C2Cl)=CC1=O)=O Chemical compound OC([C@H](C1)C[C@@H]1OC1=CC(Br)=CN=C1C(OC(C1=CC=C2)=C2Cl)=CC1=O)=O MSAPNZITTQMAIY-HOMQSWHASA-N 0.000 claims 1
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- 239000003814 drug Substances 0.000 claims 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims 1
- UZLWJEORFOSJQL-UHFFFAOYSA-N methyl 3-[2-[2-(8-chloro-4-oxochromen-2-yl)-5-(2-oxo-1,3-oxazolidin-3-yl)phenoxy]ethoxy]cyclobutane-1-carboxylate Chemical compound ClC=1C=CC=C2C(C=C(OC=12)C1=C(OCCOC2CC(C2)C(=O)OC)C=C(C=C1)N1C(OCC1)=O)=O UZLWJEORFOSJQL-UHFFFAOYSA-N 0.000 claims 1
- XTKUKYHZWYSTDE-UHFFFAOYSA-N methyl 3-[2-[5-bromo-2-(8-chloro-4-oxochromen-2-yl)phenoxy]ethoxy]cyclobutane-1-carboxylate Chemical compound BrC=1C=CC(=C(OCCOC2CC(C2)C(=O)OC)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl XTKUKYHZWYSTDE-UHFFFAOYSA-N 0.000 claims 1
- JAWSSYYDXOMZKI-UHFFFAOYSA-N methyl 3-[5-chloro-2-(8-chloro-4-oxochromen-2-yl)-4-methylphenoxy]propanoate Chemical compound ClC=1C(=CC(=C(OCCC(=O)OC)C=1)C=1OC2=C(C=CC=C2C(C=1)=O)Cl)C JAWSSYYDXOMZKI-UHFFFAOYSA-N 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007821 HATU Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- UABRYPURASNHRO-UHFFFAOYSA-N trimethyltin;hydrate Chemical compound O.C[Sn](C)C UABRYPURASNHRO-UHFFFAOYSA-N 0.000 description 1
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| CNPCT/CN2018/109241 | 2018-10-03 | ||
| CN2018109241 | 2018-10-03 | ||
| PCT/EP2019/076502 WO2020070088A1 (en) | 2018-10-03 | 2019-10-01 | Flavone derivatives for the treatment and prophylaxis of hepatitis b virus disease |
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| JP2022504298A JP2022504298A (ja) | 2022-01-13 |
| JP2022504298A5 JP2022504298A5 (https=) | 2024-03-04 |
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| WO2020052774A1 (en) * | 2018-09-14 | 2020-03-19 | F. Hoffmann-La Roche Ag | Flavone derivatives for the treatment and prophylaxis of hepatitis b virus disease |
| WO2020120528A1 (en) * | 2018-12-14 | 2020-06-18 | F. Hoffmann-La Roche Ag | N-containing chromen-4-one derivatives for the treatment and prophylaxis of hepatitis b virus infection |
| JP2022514470A (ja) * | 2018-12-14 | 2022-02-14 | エフ．ホフマン－ラ ロシュ アーゲー | Ｂ型肝炎ウイルス感染症を治療および予防するためのクロマン－４－オン誘導体 |
| CN116947799B (zh) * | 2023-03-08 | 2024-05-03 | 上海泽德曼医药科技有限公司 | 酚类化合物、其制备方法及其在医药上的应用 |
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| EP1223928A2 (en) * | 1999-07-08 | 2002-07-24 | Patrick Thomas Prendergast | Use of flavones, coumarins and related compounds to treat infections |
| GB0216371D0 (en) | 2002-07-13 | 2002-08-21 | Rowett Res Inst The | Compounds |
| CN100415731C (zh) | 2004-12-30 | 2008-09-03 | 财团法人工业技术研究院 | 治疗b型肝炎的化合物及其医药组合物 |
| CA2652617A1 (en) | 2006-05-19 | 2007-11-29 | The Hong Kong Polytechnic University | Flavonoid dimers and methods of making and using such |
| WO2013127361A1 (en) | 2012-03-01 | 2013-09-06 | The Hong Kong Polytechnic University | Alkyne-, azide- and triazole-containing flavonoids as modulators for multidrug resistance in cancers |
| WO2014074976A1 (en) | 2012-11-09 | 2014-05-15 | Musc Foundation For Research Development | Compositions and methods for treating neurological diseases or injury |
| CN109394752A (zh) | 2013-10-21 | 2019-03-01 | 德雷克塞尔大学 | 治疗慢性乙型肝炎病毒感染的sting激动剂的用途 |
| WO2015161309A1 (en) | 2014-04-19 | 2015-10-22 | Jia Zhou | Apigenin analogs, compositions, and methods related thereto |
| US20210387996A1 (en) | 2018-10-24 | 2021-12-16 | Hoffmann-La Roche Inc. | Tricyclic compounds for the treatment and prophylaxis of hepatitis b virus disease |
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- 2019-10-01 US US17/282,369 patent/US11708344B2/en active Active
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- 2019-10-01 WO PCT/EP2019/076502 patent/WO2020070088A1/en not_active Ceased
- 2019-10-01 EP EP19784006.9A patent/EP3860984A1/en not_active Withdrawn
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