JP2018527336A5 - - Google Patents
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- JP2018527336A5 JP2018527336A5 JP2018506432A JP2018506432A JP2018527336A5 JP 2018527336 A5 JP2018527336 A5 JP 2018527336A5 JP 2018506432 A JP2018506432 A JP 2018506432A JP 2018506432 A JP2018506432 A JP 2018506432A JP 2018527336 A5 JP2018527336 A5 JP 2018527336A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- indol
- phenyl
- sulfonyl
- benzenesulfonamide
- 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.)
- Ceased
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- -1 6-fluoro-1H-indol-3-yl Chemical group 0.000 claims 29
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 9
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 3
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- LXHXFLKPMOIAAG-DLBZAZTESA-N (3R,4S)-4-fluoro-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidin-3-amine Chemical compound F[C@@H]1[C@@H](CN(C1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(=CC=C12)F)N LXHXFLKPMOIAAG-DLBZAZTESA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- USVDVLNQDDGINX-UHFFFAOYSA-N [1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperazin-2-yl]methanol Chemical compound OCC1CNCCN1S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(F)=CC=C12 USVDVLNQDDGINX-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- BEFLCWOSSCEMOC-MTFMMBMASA-N (2R,3R,4S,5S)-5-fluoro-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-2-(hydroxymethyl)piperidine-3,4-diol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](F)CN1S(=O)(=O)c1ccc(cc1)-c1c[nH]c2cc(F)ccc12 BEFLCWOSSCEMOC-MTFMMBMASA-N 0.000 claims 1
- DCHHDRUOBFRHMA-FHWLQOOXSA-N (2S,3S,4S)-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OC[C@H]1[C@H](O)[C@@H](O)CN1S(=O)(=O)c1ccc(cc1)-c1c[nH]c2cc(F)ccc12 DCHHDRUOBFRHMA-FHWLQOOXSA-N 0.000 claims 1
- ZVXBJCWWVUKJDZ-CQSZACIVSA-N (3R)-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidin-3-ol Chemical compound O[C@@H]1CCN(C1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(F)=CC=C12 ZVXBJCWWVUKJDZ-CQSZACIVSA-N 0.000 claims 1
- WLLIXOIHPQOJOZ-RTBURBONSA-N (3R,4R)-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperidine-3,4-diol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1C[C@H]([C@@H](CC1)O)O WLLIXOIHPQOJOZ-RTBURBONSA-N 0.000 claims 1
- DRDFZHHEBIDCJX-QZTJIDSGSA-N (3R,4R)-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidine-3,4-diol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1C[C@H]([C@@H](C1)O)O DRDFZHHEBIDCJX-QZTJIDSGSA-N 0.000 claims 1
- LXHXFLKPMOIAAG-IAGOWNOFSA-N (3R,4R)-4-fluoro-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidin-3-amine Chemical compound F[C@H]1[C@@H](CN(C1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(=CC=C12)F)N LXHXFLKPMOIAAG-IAGOWNOFSA-N 0.000 claims 1
- DRDFZHHEBIDCJX-HDICACEKSA-N (3R,4S)-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidine-3,4-diol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1C[C@H]([C@H](C1)O)O DRDFZHHEBIDCJX-HDICACEKSA-N 0.000 claims 1
- ZVXBJCWWVUKJDZ-AWEZNQCLSA-N (3S)-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidin-3-ol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1C[C@H](CC1)O ZVXBJCWWVUKJDZ-AWEZNQCLSA-N 0.000 claims 1
- WLLIXOIHPQOJOZ-MOPGFXCFSA-N (3S,4R)-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperidine-3,4-diol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1C[C@@H]([C@@H](CC1)O)O WLLIXOIHPQOJOZ-MOPGFXCFSA-N 0.000 claims 1
- DRDFZHHEBIDCJX-ROUUACIJSA-N (3S,4S)-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidine-3,4-diol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1C[C@@H]([C@H](C1)O)O DRDFZHHEBIDCJX-ROUUACIJSA-N 0.000 claims 1
- LXHXFLKPMOIAAG-IRXDYDNUSA-N (3S,4S)-4-fluoro-1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidin-3-amine Chemical compound F[C@@H]1[C@H](CN(C1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(=CC=C12)F)N LXHXFLKPMOIAAG-IRXDYDNUSA-N 0.000 claims 1
- MCUULSPCLNTZND-UHFFFAOYSA-N 1-(2-aminoethyl)-4-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperazin-2-one Chemical compound NCCN1CCN(CC1=O)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(F)=CC=C12 MCUULSPCLNTZND-UHFFFAOYSA-N 0.000 claims 1
- KZRZHZSIHHHXOU-UHFFFAOYSA-N 1-(3-aminopropyl)-4-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperazin-2-one Chemical compound NCCCN1C(CN(CC1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(=CC=C12)F)=O KZRZHZSIHHHXOU-UHFFFAOYSA-N 0.000 claims 1
- KPSFBAPMIVIYKY-MRXNPFEDSA-N 1-[(2R)-2,3-dihydroxypropyl]-4-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperazin-2-one Chemical compound O[C@H](CN1C(CN(CC1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(=CC=C12)F)=O)CO KPSFBAPMIVIYKY-MRXNPFEDSA-N 0.000 claims 1
- KPSFBAPMIVIYKY-INIZCTEOSA-N 1-[(2S)-2,3-dihydroxypropyl]-4-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperazin-2-one Chemical compound O[C@@H](CN1C(CN(CC1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(=CC=C12)F)=O)CO KPSFBAPMIVIYKY-INIZCTEOSA-N 0.000 claims 1
- XTEXWRBMDKDLBA-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-4-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperazin-2-one Chemical compound CN(CCN1C(CN(CC1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(=CC=C12)F)=O)C XTEXWRBMDKDLBA-UHFFFAOYSA-N 0.000 claims 1
- YDKROAUMUPAUDN-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-4-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperazin-2-one Chemical compound CN(C)CCCN1CCN(CC1=O)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(F)=CC=C12 YDKROAUMUPAUDN-UHFFFAOYSA-N 0.000 claims 1
- VXEAJCMTXUMDSS-UHFFFAOYSA-N 1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-1,4-diazepan-5-one Chemical compound FC1=CC=C2C(NC=C2C2=CC=C(C=C2)S(=O)(=O)N2CCNC(=O)CC2)=C1 VXEAJCMTXUMDSS-UHFFFAOYSA-N 0.000 claims 1
- OYWBDXZZBKJGOD-UHFFFAOYSA-N 1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-3-(2-methylpyrazol-3-yl)pyrrolidin-3-ol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1CC(CC1)(O)C1=CC=NN1C OYWBDXZZBKJGOD-UHFFFAOYSA-N 0.000 claims 1
- NRWZKXXYLJNRQD-UHFFFAOYSA-N 1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-3-[(2-methylimidazol-1-yl)methyl]piperidin-3-ol Chemical compound Cc1nccn1CC1(O)CCCN(C1)S(=O)(=O)c1ccc(cc1)-c1c[nH]c2cc(F)ccc12 NRWZKXXYLJNRQD-UHFFFAOYSA-N 0.000 claims 1
- UAAIQIGBIXIRBU-UHFFFAOYSA-N 1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-3-[(2-methylimidazol-1-yl)methyl]pyrrolidin-3-ol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1CC(CC1)(O)CN1C(=NC=C1)C UAAIQIGBIXIRBU-UHFFFAOYSA-N 0.000 claims 1
- OCGIPRBQXPZIFF-UHFFFAOYSA-N 1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-3-pyrimidin-4-ylpyrrolidin-3-ol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1CC(CC1)(O)C1=NC=NC=C1 OCGIPRBQXPZIFF-UHFFFAOYSA-N 0.000 claims 1
- DSXIECZMNKXIAD-UHFFFAOYSA-N 1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-3-pyrimidin-5-ylpyrrolidin-3-ol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1CC(CC1)(O)C=1C=NC=NC=1 DSXIECZMNKXIAD-UHFFFAOYSA-N 0.000 claims 1
- IVBSJRPDKKLIIN-UHFFFAOYSA-N 1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylazetidin-3-ol Chemical compound OC1CN(C1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(F)=CC=C12 IVBSJRPDKKLIIN-UHFFFAOYSA-N 0.000 claims 1
- ZVXBJCWWVUKJDZ-UHFFFAOYSA-N 1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpyrrolidin-3-ol Chemical compound OC1CCN(C1)S(=O)(=O)c1ccc(cc1)-c1c[nH]c2cc(F)ccc12 ZVXBJCWWVUKJDZ-UHFFFAOYSA-N 0.000 claims 1
- VHMKUTVZSIHDFK-UHFFFAOYSA-N 1-[6-fluoro-3-(4-piperazin-1-ylsulfonylphenyl)indol-1-yl]-3-methylbutan-1-one Chemical compound FC1=CC=C2C(=CN(C2=C1)C(CC(C)C)=O)C1=CC=C(C=C1)S(=O)(=O)N1CCNCC1 VHMKUTVZSIHDFK-UHFFFAOYSA-N 0.000 claims 1
- BENJUIUUDPZNBB-UHFFFAOYSA-N 1-[6-fluoro-3-(4-piperazin-1-ylsulfonylphenyl)indol-1-yl]ethanone Chemical compound FC1=CC=C2C(=CN(C2=C1)C(C)=O)C1=CC=C(C=C1)S(=O)(=O)N1CCNCC1 BENJUIUUDPZNBB-UHFFFAOYSA-N 0.000 claims 1
- JYSQGHFUNZQSDO-UHFFFAOYSA-N 1-[6-fluoro-3-(4-piperazin-1-ylsulfonylphenyl)indol-1-yl]propan-1-one Chemical compound FC1=CC=C2C(=CN(C2=C1)C(CC)=O)C1=CC=C(C=C1)S(=O)(=O)N1CCNCC1 JYSQGHFUNZQSDO-UHFFFAOYSA-N 0.000 claims 1
- AJXIWJLNLFGCBK-UHFFFAOYSA-N 1-[[1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-3-hydroxypiperidin-3-yl]methyl]pyrrolidin-2-one Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1CC(CCC1)(O)CN1C(CCC1)=O AJXIWJLNLFGCBK-UHFFFAOYSA-N 0.000 claims 1
- FRXFHAZKMMZLPL-UHFFFAOYSA-N 1-[[1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-3-hydroxypyrrolidin-3-yl]methyl]pyrrolidin-2-one Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1CC(CC1)(O)CN1C(CCC1)=O FRXFHAZKMMZLPL-UHFFFAOYSA-N 0.000 claims 1
- SZFVPNNRLKXAGR-UHFFFAOYSA-N 2-(6-fluoro-1H-indol-3-yl)-5-piperazin-1-ylsulfonylbenzonitrile Chemical compound FC1=CC=C2C(=CNC2=C1)C1=C(C#N)C=C(C=C1)S(=O)(=O)N1CCNCC1 SZFVPNNRLKXAGR-UHFFFAOYSA-N 0.000 claims 1
- HMSVNIFIIXMIRW-NSHDSACASA-N 2-(6-fluoro-1H-indol-3-yl)-N-[(2S)-1-hydroxypropan-2-yl]benzenesulfonamide Chemical compound FC1=CC=C2C(=CNC2=C1)C1=C(C=CC=C1)S(=O)(=O)N[C@H](CO)C HMSVNIFIIXMIRW-NSHDSACASA-N 0.000 claims 1
- RQASTTLPQZDDGH-UHFFFAOYSA-N 2-(aminomethyl)-4-(6-fluoro-1H-indol-3-yl)benzenesulfonamide Chemical compound NCC1=C(C=CC(=C1)C1=CNC2=CC(=CC=C12)F)S(=O)(=O)N RQASTTLPQZDDGH-UHFFFAOYSA-N 0.000 claims 1
- MXOYHZOAMCWGEC-UHFFFAOYSA-N 2-[1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylpiperidin-4-yl]oxyacetamide Chemical compound NC(=O)COC1CCN(CC1)S(=O)(=O)C1=CC=C(C=C1)C1=CNC2=CC(F)=CC=C12 MXOYHZOAMCWGEC-UHFFFAOYSA-N 0.000 claims 1
- OROZMZALIFOPCY-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-4-(6-fluoro-1H-indol-3-yl)benzenesulfonamide Chemical compound CN(C)CCC1=C(C=CC(=C1)C1=CNC2=CC(F)=CC=C12)S(N)(=O)=O OROZMZALIFOPCY-UHFFFAOYSA-N 0.000 claims 1
- AVFXXPZJUCNLPZ-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-2-methylsulfonylphenyl]ethanol Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC(=C(C=1)CCO)S(=O)(=O)C AVFXXPZJUCNLPZ-UHFFFAOYSA-N 0.000 claims 1
- SXKGXICGVUDAGZ-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-2-sulfamoylphenyl]-N,N-dimethylacetamide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC(=C(C=1)CC(=O)N(C)C)S(N)(=O)=O SXKGXICGVUDAGZ-UHFFFAOYSA-N 0.000 claims 1
- SCANDCLWBAULPS-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-2-sulfamoylphenyl]-N-methylacetamide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC(=C(C=1)CC(=O)NC)S(N)(=O)=O SCANDCLWBAULPS-UHFFFAOYSA-N 0.000 claims 1
- RQODVMGMCIMDRP-UHFFFAOYSA-N 2-[5-(6-fluoro-1H-indol-3-yl)-2-sulfamoylphenyl]acetamide Chemical compound FC1=CC=C2C(=CNC2=C1)C=1C=CC(=C(C=1)CC(=O)N)S(N)(=O)=O RQODVMGMCIMDRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- HPMSAGLCIMNKPM-UHFFFAOYSA-N 3,5-dichloro-4-(6-fluoro-1H-indol-3-yl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(Cl)=C(C2=CNC3=CC(F)=CC=C23)C(Cl)=C1 HPMSAGLCIMNKPM-UHFFFAOYSA-N 0.000 claims 1
- VPKXRSVFZMPLOX-UHFFFAOYSA-N 3-(3,5-dichloro-4-piperazin-1-ylsulfonylphenyl)-6-fluoro-1H-indole Chemical compound ClC=1C=C(C=C(C=1S(=O)(=O)N1CCNCC1)Cl)C1=CNC2=CC(=CC=C12)F VPKXRSVFZMPLOX-UHFFFAOYSA-N 0.000 claims 1
- QBFIFTWGUYTCTG-UHFFFAOYSA-N 3-(3,5-difluoro-4-piperazin-1-ylsulfonylphenyl)-6-fluoro-1H-indole Chemical compound FC=1C=C(C=C(C=1S(=O)(=O)N1CCNCC1)F)C1=CNC2=CC(=CC=C12)F QBFIFTWGUYTCTG-UHFFFAOYSA-N 0.000 claims 1
- BAOKAVUKWSTFEY-UHFFFAOYSA-N 3-(3,5-dimethyl-4-piperazin-1-ylsulfonylphenyl)-6-fluoro-1H-indole Chemical compound CC=1C=C(C=C(C=1S(=O)(=O)N1CCNCC1)C)C1=CNC2=CC(=CC=C12)F BAOKAVUKWSTFEY-UHFFFAOYSA-N 0.000 claims 1
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- VDXFXOOVWIKTGE-OKILXGFUSA-N 3-[4-[(3R,5S)-3,5-dimethylpiperazin-1-yl]sulfonylphenyl]-6-fluoro-1H-indole Chemical compound C[C@H]1CN(C[C@@H](C)N1)S(=O)(=O)c1ccc(cc1)-c1c[nH]c2cc(F)ccc12 VDXFXOOVWIKTGE-OKILXGFUSA-N 0.000 claims 1
- VDXFXOOVWIKTGE-KBPBESRZSA-N 3-[4-[(3S,5S)-3,5-dimethylpiperazin-1-yl]sulfonylphenyl]-6-fluoro-1H-indole Chemical compound C[C@H]1CN(C[C@H](C)N1)S(=O)(=O)c1ccc(cc1)-c1c[nH]c2cc(F)ccc12 VDXFXOOVWIKTGE-KBPBESRZSA-N 0.000 claims 1
- JYIAWOUNEVBZIX-UHFFFAOYSA-N 3-[[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonyl-methylamino]propanamide Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N(C)CCC(=O)N JYIAWOUNEVBZIX-UHFFFAOYSA-N 0.000 claims 1
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| CN108948002A (zh) * | 2017-05-19 | 2018-12-07 | 厦门大学 | 五元并六元氮杂芳环类化合物、其制备方法、药用组合物及其应用 |
| JP2020522495A (ja) | 2017-05-30 | 2020-07-30 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 抗ｌａｇ−３抗体、ｐｄ−１経路阻害剤および免疫療法剤の組み合わせを含む組成物 |
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| CA3078969A1 (en) | 2017-10-13 | 2019-04-18 | Harpoon Therapeutics, Inc. | Trispecific proteins and methods of use |
| US10632209B2 (en) | 2017-11-10 | 2020-04-28 | The Regents Of The University Of Michigan | ASH1L inhibitors and methods of treatment therewith |
| CN108794376B (zh) * | 2018-04-28 | 2021-01-05 | 北京施安泰医药技术开发有限公司 | 甲酰胺类衍生物、其药物组合物、制备方法与用途 |
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| JP2026501506A (ja) | 2022-12-14 | 2026-01-16 | アステラス・ファーマ・ヨーロッパ・ベスローデン・フェンノートシャップ | Ｃｌｄｎ１８．２及びｃｄ３に結合する二重特異性結合剤並びに免疫チェックポイント阻害剤を含む併用療法 |
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- 2016-08-04 JP JP2018506432A patent/JP2018527336A/ja not_active Ceased
- 2016-08-04 EP EP16757354.2A patent/EP3334733A1/en not_active Withdrawn
- 2016-08-04 CA CA2994917A patent/CA2994917A1/en not_active Abandoned
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