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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- LYNAFYOHYQXREF-HNNXBMFYSA-N [(3S)-4-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylmorpholin-3-yl]methanol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1[C@H](COCC1)CO LYNAFYOHYQXREF-HNNXBMFYSA-N 0.000 claims 1
- KUXMPXRXMRCHGD-UHFFFAOYSA-N [1-[4-(6-fluoro-1H-indol-3-yl)phenyl]sulfonylazetidin-3-yl]methanol Chemical compound FC1=CC=C2C(=CNC2=C1)C1=CC=C(C=C1)S(=O)(=O)N1CC(C1)CO KUXMPXRXMRCHGD-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2017011951A (es) * | 2015-03-17 | 2018-06-15 | Pfizer | Derivados sustituidos de indol 3 novedosos, composiciones farmaceuticas y metodos para uso. |
| US9708412B2 (en) | 2015-05-21 | 2017-07-18 | Harpoon Therapeutics, Inc. | Trispecific binding proteins and methods of use |
| ES2910787T3 (es) * | 2016-05-12 | 2022-05-13 | Univ Michigan Regents | Inhibidores de ASH1L y métodos de tratamiento con los mismos |
| US11623958B2 (en) | 2016-05-20 | 2023-04-11 | Harpoon Therapeutics, Inc. | Single chain variable fragment CD3 binding proteins |
| EP3269714A1 (en) * | 2016-07-13 | 2018-01-17 | Netherlands Translational Research Center B.V. | Inhibitors of tryptophan 2,3-dioxygenase |
| GB201705263D0 (en) * | 2017-03-31 | 2017-05-17 | Probiodrug Ag | Novel inhibitors |
| EP3621994A4 (en) | 2017-05-12 | 2020-12-30 | Harpoon Therapeutics, Inc. | MESOTHELIN BINDING PROTEINS |
| 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 |
| MX2020003915A (es) | 2017-10-13 | 2020-10-08 | Harpoon Therapeutics Inc | Proteinas trispecificas y metodos de uso. |
| IL315737A (en) | 2017-10-13 | 2024-11-01 | Harpoon Therapeutics Inc | B-cell maturation antigen-binding proteins |
| WO2019094773A1 (en) * | 2017-11-10 | 2019-05-16 | 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 |
| US12195544B2 (en) | 2018-09-21 | 2025-01-14 | Harpoon Therapeutics, Inc. | EGFR binding proteins and methods of use |
| US10815311B2 (en) | 2018-09-25 | 2020-10-27 | Harpoon Therapeutics, Inc. | DLL3 binding proteins and methods of use |
| WO2021024020A1 (en) | 2019-08-06 | 2021-02-11 | Astellas Pharma Inc. | Combination therapy involving antibodies against claudin 18.2 and immune checkpoint inhibitors for treatment of cancer |
| WO2021174058A1 (en) * | 2020-02-27 | 2021-09-02 | Board Of Regents, The University Of Texas System | Methods and compositions for treatment of apc-deficient cancer |
| CN111825678A (zh) * | 2020-06-05 | 2020-10-27 | 连庆泉 | 一种卡马替尼的制备方法 |
| KR20230035576A (ko) | 2020-07-07 | 2023-03-14 | 비온테크 에스이 | Hpv 양성 암 치료용 rna |
| WO2022135667A1 (en) | 2020-12-21 | 2022-06-30 | BioNTech SE | Therapeutic rna for treating cancer |
| TW202245808A (zh) | 2020-12-21 | 2022-12-01 | 德商拜恩迪克公司 | 用於治療癌症之治療性ｒｎａ |
| WO2022135666A1 (en) | 2020-12-21 | 2022-06-30 | BioNTech SE | Treatment schedule for cytokine proteins |
| CA3225254A1 (en) | 2021-07-13 | 2023-01-19 | BioNTech SE | Multispecific binding agents against cd40 and cd137 in combination therapy for cancer |
| TW202333802A (zh) | 2021-10-11 | 2023-09-01 | 德商拜恩迪克公司 | 用於肺癌之治療性rna(二) |
| JP2025508076A (ja) | 2022-03-08 | 2025-03-21 | アレンティス・セラピューティクス・アクチェンゲゼルシャフト | Ｔ細胞の利用能を向上させるための抗クローディン－１抗体の使用 |
| 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 |
| TW202541837A (zh) | 2023-12-08 | 2025-11-01 | 日商安斯泰來製藥公司 | 含有結合至cldn18.2和cd3之雙特異性結合劑和穩定或增加cldn18.2表現之藥劑之組合療法 |
| WO2026033885A1 (en) | 2024-08-08 | 2026-02-12 | Astellas Pharma Inc. | Combination therapy involving bispecific binding agents binding to cldn18.2 and cd3 and agents stabilizing or increasing expression of cldn18.2 |
| WO2025120866A1 (en) | 2023-12-08 | 2025-06-12 | Astellas Pharma Inc. | Combination therapy involving bispecific binding agents binding to cldn18.2 and cd3 and agents stabilizing or increasing expression of cldn18.2 |
| WO2025120867A1 (en) | 2023-12-08 | 2025-06-12 | Astellas Pharma Inc. | Combination therapy involving bispecific binding agents binding to cldn18.2 and cd3 and anti-vegfr2 antibodies |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE509731C2 (sv) | 1996-05-14 | 1999-03-01 | Labwell Ab | Metod för palladium-katalyserade organiska reaktioner innefattande ett uppvärmningssteg utfört med mikrovågsenergi |
| JP2000095759A (ja) | 1998-07-21 | 2000-04-04 | Takeda Chem Ind Ltd | 三環性化合物、その製造法および剤 |
| US6265403B1 (en) | 1999-01-20 | 2001-07-24 | Merck & Co., Inc. | Angiogenesis inhibitors |
| BR0212613A (pt) | 2001-09-19 | 2004-08-31 | Pharmacia Corp | Compostos de indazol substituìdos para o tratamento de inflamação |
| WO2003082869A1 (en) | 2002-03-28 | 2003-10-09 | Eisai Co., Ltd. | Azaindoles as inhibitors of c-jun n-terminal kinases |
| TW200307542A (en) | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| FR2845996A1 (fr) | 2002-10-16 | 2004-04-23 | Servier Lab | Nouveaux derives de[3,4-a:3,4-c]carbazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN101265254A (zh) | 2003-03-27 | 2008-09-17 | 兰肯瑙医学研究所 | 新型ido抑制剂及其使用方法 |
| FR2862647B1 (fr) | 2003-11-25 | 2008-07-04 | Aventis Pharma Sa | Derives de pyrazolyle, procede de preparation et intermediaires de ce procede a titre de medicaments et de compositions pharmaceutiques les renfermant |
| GB0328909D0 (en) | 2003-12-12 | 2004-01-14 | Syngenta Participations Ag | Chemical compounds |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| KR100941205B1 (ko) | 2005-02-09 | 2010-02-10 | 아르퀼 인코포레이티드 | 말레이미드 유도체, 약제학적 조성물 및 암을 치료하는방법 |
| WO2007039580A1 (en) | 2005-10-05 | 2007-04-12 | Nycomed Gmbh | Imidazolyl-substituted benzophenone compounds |
| WO2007045622A1 (en) | 2005-10-18 | 2007-04-26 | Nycomed Gmbh | Oxazolo [4 , 5-b] pyridine compounds as nitric oxide synthase inhibitors |
| WO2007050963A1 (en) | 2005-10-27 | 2007-05-03 | Lankenau Institute For Medical Research | Novel ido inhibitors and methods of use thereof |
| CA2637933C (en) | 2006-01-24 | 2013-03-12 | Eli Lilly And Company | Indole sulfonamide modulators of progesterone receptors |
| CA2644910C (en) | 2006-03-31 | 2014-01-28 | Abbott Laboratories | Indazole compounds |
| US20090098137A1 (en) | 2006-04-05 | 2009-04-16 | Novartis Ag | Combinations of therapeutic agents for treating cancer |
| GB0624308D0 (en) | 2006-12-05 | 2007-01-17 | Molmed Spa | Combination product |
| BRPI0720049A2 (pt) | 2006-12-07 | 2014-01-07 | Novartis Ag | Derivados de piridina utilizados como inibidores de xiap |
| AU2008210455A1 (en) | 2007-01-31 | 2008-08-07 | Vertex Pharmaceuticals Incorporated | 2-aminopyridine derivatives useful as kinase inhibitors |
| US8389568B2 (en) | 2007-03-16 | 2013-03-05 | Lankenau Institute For Medical Research | IDO inhibitors and methods of use thereof |
| WO2009015067A2 (en) | 2007-07-25 | 2009-01-29 | Boehringer Ingelheim International Gmbh | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| US7868001B2 (en) | 2007-11-02 | 2011-01-11 | Hutchison Medipharma Enterprises Limited | Cytokine inhibitors |
| EA201000915A1 (ru) | 2007-11-30 | 2011-02-28 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | Ингибиторы пролилгидроксилазы |
| AU2009228765B2 (en) * | 2008-03-24 | 2012-05-31 | Novartis Ag | Arylsulfonamide-based matrix metalloprotease inhibitors |
| WO2010008427A1 (en) | 2008-04-11 | 2010-01-21 | Ludwig Institute For Cancer Research Ltd. | Tryptophan catabolism in cancer treatment and diagnosis |
| DE102008052943A1 (de) | 2008-10-23 | 2010-04-29 | Merck Patent Gmbh | Azaindolderivate |
| MX2011008645A (es) | 2009-02-17 | 2011-09-30 | Vertex Pharma | Inhibidores de tetrahidrotiazolopiridina de fosfatidilinositol 3 cinasa. |
| US8158625B2 (en) | 2009-05-27 | 2012-04-17 | Genentech, Inc. | Bicyclic indole-pyrimidine PI3K inhibitor compounds selective for P110 delta, and methods of use |
| CA2668905A1 (en) * | 2009-06-15 | 2010-12-15 | University Of Saskatchewan | Method for inhibiting brassinin oxidase |
| KR101256018B1 (ko) | 2009-08-20 | 2013-04-18 | 한국과학기술연구원 | 단백질 키나아제 저해활성을 갖는 1,3,6-치환된 인돌 화합물 |
| US9079904B2 (en) | 2009-09-23 | 2015-07-14 | Medivation Technologies, Inc. | Pyrido[3,4-B]indoles and methods of use |
| BR112012006956A2 (pt) | 2009-10-12 | 2015-09-15 | Bayer Cropscience Ag | 1- (pirida-3-il) -pirazóisol e 1- (pirimida-5-il) - pirazóisol como pesticidas |
| WO2011046954A1 (en) | 2009-10-13 | 2011-04-21 | Ligand Pharmaceuticals Inc. | Hematopoietic growth factor mimetic small molecule compounds and their uses |
| CN103282034A (zh) | 2010-11-18 | 2013-09-04 | 利亘制药公司 | 造血生长因子模拟物的用途 |
| JP2014510105A (ja) | 2011-03-22 | 2014-04-24 | アムジエン・インコーポレーテツド | Ｐｉｍ阻害剤としてのアゾール化合物 |
| LT2714677T (lt) | 2011-05-23 | 2018-12-10 | Merck Patent Gmbh | Piridino ir pirazino dariniai |
| MX2014001851A (es) | 2011-08-17 | 2014-10-24 | Amgen Inc | Inhibidores del canal de heteroarilo sodio. |
| US9126984B2 (en) | 2013-11-08 | 2015-09-08 | Iteos Therapeutics | 4-(indol-3-yl)-pyrazole derivatives, pharmaceutical compositions and methods for use |
| US20160263087A1 (en) | 2013-11-08 | 2016-09-15 | Iteos Therapeutics | Novel 4-(indol-3-yl)-pyrazole derivatives, pharmaceutical compositions and methods for use |
| US9931347B2 (en) * | 2013-12-03 | 2018-04-03 | Iomet Pharma Ltd. | Pharmaceutical compound |
| US9758505B2 (en) | 2014-02-12 | 2017-09-12 | Iteos Therapeutics | 3-(indol-3-yl)-pyridine derivatives, pharmaceutical compositions and methods for use |
| US20150266857A1 (en) | 2014-03-18 | 2015-09-24 | Iteos Therapeutics | Novel 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| EP3119763A1 (en) | 2014-03-18 | 2017-01-25 | Iteos Therapeutics | Novel 3-indol substituted derivatives, pharmaceutical compositions and methods for use |
| EA201650031A1 (ru) | 2014-05-15 | 2017-06-30 | Итеос Терапьютик | Производные пирролидин-2,5-диона, фармацевтические композиции и способы применения в качестве ингибиторов ido1 |
| EP3269714A1 (en) * | 2016-07-13 | 2018-01-17 | Netherlands Translational Research Center B.V. | Inhibitors of tryptophan 2,3-dioxygenase |
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- 2016-08-04 WO PCT/IB2016/054701 patent/WO2017025868A1/en not_active Ceased
- 2016-08-04 CA CA2994917A patent/CA2994917A1/en not_active Abandoned
- 2016-08-04 US US15/749,963 patent/US10544095B2/en active Active
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