JP2012508776A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012508776A5 JP2012508776A5 JP2011536567A JP2011536567A JP2012508776A5 JP 2012508776 A5 JP2012508776 A5 JP 2012508776A5 JP 2011536567 A JP2011536567 A JP 2011536567A JP 2011536567 A JP2011536567 A JP 2011536567A JP 2012508776 A5 JP2012508776 A5 JP 2012508776A5
- Authority
- JP
- Japan
- Prior art keywords
- benzo
- pyrazin
- alkyl
- phenyl
- yloxy
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 350
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 61
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- 229910052731 fluorine Inorganic materials 0.000 claims description 55
- 229910052801 chlorine Inorganic materials 0.000 claims description 54
- 229920006395 saturated elastomer Polymers 0.000 claims description 52
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000002619 bicyclic group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 229910005965 SO 2 Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 24
- -1 oxaspiro [3,5] nonyl Chemical group 0.000 claims 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- LIUKTCWPZUWMKH-WBVHZDCISA-N (1s,3r)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-WBVHZDCISA-N 0.000 claims 2
- LIUKTCWPZUWMKH-RDJZCZTQSA-N (1s,3s)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@@H](O)CCC[C@@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-RDJZCZTQSA-N 0.000 claims 2
- NWONINZVPVTBGN-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)C(F)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NWONINZVPVTBGN-UHFFFAOYSA-N 0.000 claims 2
- BHGBMGVTLFZRCP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methoxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(OC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 BHGBMGVTLFZRCP-UHFFFAOYSA-N 0.000 claims 2
- VIZVTXGNPQLHRZ-DLBZAZTESA-N 1h-benzimidazol-2-yl-[4-[3-[(1s,3r)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@H](O)CCC[C@@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-DLBZAZTESA-N 0.000 claims 2
- VIZVTXGNPQLHRZ-IRXDYDNUSA-N 1h-benzimidazol-2-yl-[4-[3-[(1s,3s)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@@H](O)CCC[C@@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-IRXDYDNUSA-N 0.000 claims 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- DOERLFMEMVFBQS-UHFFFAOYSA-N n-[4-(3-chloropyrazin-2-yl)oxyphenyl]-6-fluoro-1,3-benzothiazol-2-amine Chemical compound S1C2=CC(F)=CC=C2N=C1NC(C=C1)=CC=C1OC1=NC=CN=C1Cl DOERLFMEMVFBQS-UHFFFAOYSA-N 0.000 claims 2
- 210000002637 putamen Anatomy 0.000 claims 2
- YNCIDBYSTGADKV-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 YNCIDBYSTGADKV-UHFFFAOYSA-N 0.000 claims 1
- GCQAVHNIIDWDIK-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)-[4-[3-(2-methylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound CC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)C)C=C1 GCQAVHNIIDWDIK-UHFFFAOYSA-N 0.000 claims 1
- JZSMZKJZDCZCGJ-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 JZSMZKJZDCZCGJ-UHFFFAOYSA-N 0.000 claims 1
- LIUKTCWPZUWMKH-NVXWUHKLSA-N (1r,3r)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-NVXWUHKLSA-N 0.000 claims 1
- LIUKTCWPZUWMKH-DOTOQJQBSA-N (1r,3s)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LIUKTCWPZUWMKH-DOTOQJQBSA-N 0.000 claims 1
- NFJWUVZWQQNUEZ-MRXNPFEDSA-N (2r)-1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@H](F)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NFJWUVZWQQNUEZ-MRXNPFEDSA-N 0.000 claims 1
- NWONINZVPVTBGN-MRXNPFEDSA-N (2r)-1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@H](F)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NWONINZVPVTBGN-MRXNPFEDSA-N 0.000 claims 1
- NFJWUVZWQQNUEZ-INIZCTEOSA-N (2s)-1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)[C@@H](F)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NFJWUVZWQQNUEZ-INIZCTEOSA-N 0.000 claims 1
- UHRZMABESCXDJW-HNNXBMFYSA-N (3r)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CC[C@@H](C#N)C1 UHRZMABESCXDJW-HNNXBMFYSA-N 0.000 claims 1
- BLLKHCJAOCXHCW-OAHLLOKOSA-N (3r)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCC[C@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-OAHLLOKOSA-N 0.000 claims 1
- UHRZMABESCXDJW-OAHLLOKOSA-N (3s)-1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CC[C@H](C#N)C1 UHRZMABESCXDJW-OAHLLOKOSA-N 0.000 claims 1
- BLLKHCJAOCXHCW-HNNXBMFYSA-N (3s)-3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCC[C@@H]1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-HNNXBMFYSA-N 0.000 claims 1
- AFWSQFMTRFITGY-UHFFFAOYSA-N (5-fluoro-1-methylbenzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC(F)=CC=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 AFWSQFMTRFITGY-UHFFFAOYSA-N 0.000 claims 1
- CYYBRDFIVOTWLR-UHFFFAOYSA-N (6-fluoro-1-methylbenzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=C(F)C=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 CYYBRDFIVOTWLR-UHFFFAOYSA-N 0.000 claims 1
- WOMJZGSOHCMFTN-UHFFFAOYSA-N (6-fluoro-1h-benzimidazol-2-yl)-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=C(F)C=C3N=2)C=C1 WOMJZGSOHCMFTN-UHFFFAOYSA-N 0.000 claims 1
- JRIRUWHLHRZROS-UHFFFAOYSA-N (6-fluoro-1h-benzimidazol-2-yl)-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N1C2=CC(F)=CC=C2N=C1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 JRIRUWHLHRZROS-UHFFFAOYSA-N 0.000 claims 1
- AFVMYKZMYQFDLR-CQSZACIVSA-N (6r)-4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)N[C@H](C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AFVMYKZMYQFDLR-CQSZACIVSA-N 0.000 claims 1
- AFVMYKZMYQFDLR-AWEZNQCLSA-N (6s)-4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)N[C@@H](C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AFVMYKZMYQFDLR-AWEZNQCLSA-N 0.000 claims 1
- DVBCTQVDMKFPPK-UHFFFAOYSA-N 1,3-benzothiazol-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2SC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 DVBCTQVDMKFPPK-UHFFFAOYSA-N 0.000 claims 1
- GNWKATFENPQMIQ-UHFFFAOYSA-N 1-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]ethanol Chemical compound C1CC(C(O)C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 GNWKATFENPQMIQ-UHFFFAOYSA-N 0.000 claims 1
- XCPAHAVUYOTWLH-UHFFFAOYSA-N 1-[3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 XCPAHAVUYOTWLH-UHFFFAOYSA-N 0.000 claims 1
- GRZACTBGKFAAHZ-UHFFFAOYSA-N 1-[3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]azetidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 GRZACTBGKFAAHZ-UHFFFAOYSA-N 0.000 claims 1
- GZSNDCOIZXWXRF-UHFFFAOYSA-N 1-[3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 GZSNDCOIZXWXRF-UHFFFAOYSA-N 0.000 claims 1
- JCZBUCAABGISNU-UHFFFAOYSA-N 1-[3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 JCZBUCAABGISNU-UHFFFAOYSA-N 0.000 claims 1
- PODKIINFHOBJKF-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-4-methylpiperidin-4-ol Chemical compound C1CC(C)(O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 PODKIINFHOBJKF-UHFFFAOYSA-N 0.000 claims 1
- KFCTWWLEMAKQQT-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]azetidine-3-carbonitrile Chemical compound C1C(C#N)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KFCTWWLEMAKQQT-UHFFFAOYSA-N 0.000 claims 1
- OMJGZDVNBSTDBW-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 OMJGZDVNBSTDBW-UHFFFAOYSA-N 0.000 claims 1
- UPHRCPFKIVBQFD-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-3-ol Chemical compound C1C(O)CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UPHRCPFKIVBQFD-UHFFFAOYSA-N 0.000 claims 1
- UHSVYLFWFQNXRY-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UHSVYLFWFQNXRY-UHFFFAOYSA-N 0.000 claims 1
- YVTPALHJEBAVFC-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound C1CC(C#N)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YVTPALHJEBAVFC-UHFFFAOYSA-N 0.000 claims 1
- UQQAALQDDBGGJU-UHFFFAOYSA-N 1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidine-3-carbonitrile Chemical compound C1C(C#N)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UQQAALQDDBGGJU-UHFFFAOYSA-N 0.000 claims 1
- ZTGZWFZNVOVCSI-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-4-one Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCC(=O)CC1 ZTGZWFZNVOVCSI-UHFFFAOYSA-N 0.000 claims 1
- CRADTAWBRCPFQI-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCCC(C#N)C1 CRADTAWBRCPFQI-UHFFFAOYSA-N 0.000 claims 1
- YSQISUXUOMBANZ-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-4-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCC(C#N)CC1 YSQISUXUOMBANZ-UHFFFAOYSA-N 0.000 claims 1
- OLXGCABQYDQRKC-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OLXGCABQYDQRKC-UHFFFAOYSA-N 0.000 claims 1
- UHRZMABESCXDJW-UHFFFAOYSA-N 1-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]pyrrolidine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCC(C#N)C1 UHRZMABESCXDJW-UHFFFAOYSA-N 0.000 claims 1
- BFSXGZFTNAZQQI-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)-2-fluorophenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C(=C1)F)=CC=C1NC1=NC2=CC=CC=C2S1 BFSXGZFTNAZQQI-UHFFFAOYSA-N 0.000 claims 1
- CHAZKGHHVDIGDH-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 CHAZKGHHVDIGDH-UHFFFAOYSA-N 0.000 claims 1
- JVXPQSSXFIEQET-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 JVXPQSSXFIEQET-UHFFFAOYSA-N 0.000 claims 1
- NFJWUVZWQQNUEZ-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-fluoropropan-1-one Chemical compound C1CN(C(=O)C(F)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 NFJWUVZWQQNUEZ-UHFFFAOYSA-N 0.000 claims 1
- YYQXJEOOPHCARO-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)C(O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YYQXJEOOPHCARO-UHFFFAOYSA-N 0.000 claims 1
- AJWGKNQBAKXMGL-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AJWGKNQBAKXMGL-UHFFFAOYSA-N 0.000 claims 1
- LYBQDBKBWCXHLB-UHFFFAOYSA-N 1-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LYBQDBKBWCXHLB-UHFFFAOYSA-N 0.000 claims 1
- FGCGQRSGPBXQSO-UHFFFAOYSA-N 1-[4-[3-[4-(1-methylbenzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)C)C=C1 FGCGQRSGPBXQSO-UHFFFAOYSA-N 0.000 claims 1
- CDKHCVAKJVNZMB-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 CDKHCVAKJVNZMB-UHFFFAOYSA-N 0.000 claims 1
- MRTTVYSHGAWTBQ-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 MRTTVYSHGAWTBQ-UHFFFAOYSA-N 0.000 claims 1
- LIPDYWGPFVKQEM-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 LIPDYWGPFVKQEM-UHFFFAOYSA-N 0.000 claims 1
- LXMWZAOZSLGOQC-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 LXMWZAOZSLGOQC-UHFFFAOYSA-N 0.000 claims 1
- ZNPDAYJZIRPRFQ-UHFFFAOYSA-N 1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ZNPDAYJZIRPRFQ-UHFFFAOYSA-N 0.000 claims 1
- GGDCZBXCIWBJKS-UHFFFAOYSA-N 1-[4-[3-[4-[1h-benzimidazol-2-yl(hydroxy)methyl]phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(O)C=2NC3=CC=CC=C3N=2)C=C1 GGDCZBXCIWBJKS-UHFFFAOYSA-N 0.000 claims 1
- CKKWDWPXKBMQAE-UHFFFAOYSA-N 1-[4-[3-[6-(1,3-benzothiazol-2-ylamino)pyridin-3-yl]oxypyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC=CN=C1OC(C=N1)=CC=C1NC1=NC2=CC=CC=C2S1 CKKWDWPXKBMQAE-UHFFFAOYSA-N 0.000 claims 1
- IAHTUGZTRUZUTH-UHFFFAOYSA-N 1-o-tert-butyl 4-o-methyl 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidine-1,4-dicarboxylate Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(C(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 IAHTUGZTRUZUTH-UHFFFAOYSA-N 0.000 claims 1
- TXAUAAZUMGMJJK-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-but-2-ynoxypyrazin-2-yl)oxyphenyl]methanone Chemical compound CC#CCOC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 TXAUAAZUMGMJJK-UHFFFAOYSA-N 0.000 claims 1
- JNPBJEDWNUKIQL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-chloropyrazin-2-yl)oxyphenyl]methanone Chemical compound ClC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 JNPBJEDWNUKIQL-UHFFFAOYSA-N 0.000 claims 1
- XDJJEQSKDPNXSQ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-cyclopentylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCC1 XDJJEQSKDPNXSQ-UHFFFAOYSA-N 0.000 claims 1
- XGMFORCAQZEHMJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-methoxypyrazin-2-yl)oxyphenyl]methanone Chemical compound COC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 XGMFORCAQZEHMJ-UHFFFAOYSA-N 0.000 claims 1
- YWFDAAMTUBHJGI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 YWFDAAMTUBHJGI-UHFFFAOYSA-N 0.000 claims 1
- IRKXWIGDPRTXGR-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-phenoxypyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OC1=CC=CC=C1 IRKXWIGDPRTXGR-UHFFFAOYSA-N 0.000 claims 1
- YZVPBDASJFHUAL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-piperidin-1-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCCCC1 YZVPBDASJFHUAL-UHFFFAOYSA-N 0.000 claims 1
- RETLSFLATJJXAP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-piperidin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCNCC1 RETLSFLATJJXAP-UHFFFAOYSA-N 0.000 claims 1
- TYXPCBWLQQKCMR-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-propan-2-yloxypyrazin-2-yl)oxyphenyl]methanone Chemical compound CC(C)OC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 TYXPCBWLQQKCMR-UHFFFAOYSA-N 0.000 claims 1
- HEVAGNFHYYJCDW-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-propoxypyrazin-2-yl)oxyphenyl]methanone Chemical compound CCCOC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 HEVAGNFHYYJCDW-UHFFFAOYSA-N 0.000 claims 1
- ZCFIQKOLFBWTNU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-3-yloxypyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OC1=CC=CN=C1 ZCFIQKOLFBWTNU-UHFFFAOYSA-N 0.000 claims 1
- SKXVGFCQSAGRMV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-3-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CN=C1 SKXVGFCQSAGRMV-UHFFFAOYSA-N 0.000 claims 1
- BXZUDQZZCUTONO-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyridin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=NC=C1 BXZUDQZZCUTONO-UHFFFAOYSA-N 0.000 claims 1
- ARDZLOLLOQEMHJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-pyrrolidin-1-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCCC1 ARDZLOLLOQEMHJ-UHFFFAOYSA-N 0.000 claims 1
- ARGSJRSVVCPPON-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-quinolin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound C1=CC=C2C(C3=NC=CN=C3OC3=CC=C(C=C3)C(C=3NC4=CC=CC=C4N=3)=O)=CC=NC2=C1 ARGSJRSVVCPPON-UHFFFAOYSA-N 0.000 claims 1
- HTWNAFJOAGRRBM-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-(3-quinolin-5-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound C1=CC=C2C(C3=NC=CN=C3OC3=CC=C(C=C3)C(C=3NC4=CC=CC=C4N=3)=O)=CC=CC2=N1 HTWNAFJOAGRRBM-UHFFFAOYSA-N 0.000 claims 1
- FSOBJGLZSZGYOL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(1,4-oxazepan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCCOCC1 FSOBJGLZSZGYOL-UHFFFAOYSA-N 0.000 claims 1
- SZFIMBCKCJWNGK-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2,2,2-trifluoroethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound FC(F)(F)COC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 SZFIMBCKCJWNGK-UHFFFAOYSA-N 0.000 claims 1
- RPOWDMWZGNQSBU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2,6-dimethoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC(OC)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 RPOWDMWZGNQSBU-UHFFFAOYSA-N 0.000 claims 1
- WZICCIUGDUKRRN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2,6-dimethylmorpholin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(C)OC(C)CN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WZICCIUGDUKRRN-UHFFFAOYSA-N 0.000 claims 1
- CSLGREMHQJJFEP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxyethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COCCOC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 CSLGREMHQJJFEP-UHFFFAOYSA-N 0.000 claims 1
- VLYJRGUWIXOODC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxyphenyl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VLYJRGUWIXOODC-UHFFFAOYSA-N 0.000 claims 1
- FQSMBMOXHXXZFB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanol Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(O)C=2NC3=CC=CC=C3N=2)C=C1 FQSMBMOXHXXZFB-UHFFFAOYSA-N 0.000 claims 1
- VLBHJGKQIHPSBA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VLBHJGKQIHPSBA-UHFFFAOYSA-N 0.000 claims 1
- YLASKEPHIYXYHN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(OC)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 YLASKEPHIYXYHN-UHFFFAOYSA-N 0.000 claims 1
- NASLEEKYYZHLMU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methoxyquinolin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=CC=C2NC(C(=O)C3=CC=C(C=C3)OC3=NC=CN=C3C3=CC4=CC=CC=C4N=C3OC)=NC2=C1 NASLEEKYYZHLMU-UHFFFAOYSA-N 0.000 claims 1
- WKXMBUVKQCWZQC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methylpropoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound CC(C)COC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WKXMBUVKQCWZQC-UHFFFAOYSA-N 0.000 claims 1
- WINCBLQQJITJLB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound CC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WINCBLQQJITJLB-UHFFFAOYSA-N 0.000 claims 1
- MOMKNNQNCSGNRV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 MOMKNNQNCSGNRV-UHFFFAOYSA-N 0.000 claims 1
- OYMQPGWLPLRUOX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-morpholin-4-ylethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCN1CCOCC1 OYMQPGWLPLRUOX-UHFFFAOYSA-N 0.000 claims 1
- OBRWVGKIAUHLFT-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-pyridin-2-ylethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCC1=CC=CC=N1 OBRWVGKIAUHLFT-UHFFFAOYSA-N 0.000 claims 1
- OGHGNHXUOKXZCX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(2-pyrrolidin-1-ylethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCN1CCCC1 OGHGNHXUOKXZCX-UHFFFAOYSA-N 0.000 claims 1
- JGLJRVWZCSNEDY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N(C1)CCC2=C1N=CN2 JGLJRVWZCSNEDY-UHFFFAOYSA-N 0.000 claims 1
- TZBWLCHZJRCGOQ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-hydroxyazetidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(O)CN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 TZBWLCHZJRCGOQ-UHFFFAOYSA-N 0.000 claims 1
- NOXUPUUDBQZEQB-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-hydroxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(O)CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NOXUPUUDBQZEQB-UHFFFAOYSA-N 0.000 claims 1
- QRHDFAZLVIKPOI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-hydroxypyrrolidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(O)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QRHDFAZLVIKPOI-UHFFFAOYSA-N 0.000 claims 1
- GYAHJLWOOSIHGS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methoxyphenyl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 GYAHJLWOOSIHGS-UHFFFAOYSA-N 0.000 claims 1
- AXMKWTHOPXEJGI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CN=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 AXMKWTHOPXEJGI-UHFFFAOYSA-N 0.000 claims 1
- XDFYJILYPSGECF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-methyl-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=CC=C2NC(C(=O)C3=CC=C(C=C3)OC3=NC=CN=C3N3CC4=NN=C(N4CC3)C)=NC2=C1 XDFYJILYPSGECF-UHFFFAOYSA-N 0.000 claims 1
- PIBYUXDUMHDTHI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(3-pyridin-3-ylpropoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCCCC1=CC=CN=C1 PIBYUXDUMHDTHI-UHFFFAOYSA-N 0.000 claims 1
- QHDKAYNNBNHBEI-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4,4-difluorocyclohexen-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(F)(F)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 QHDKAYNNBNHBEI-UHFFFAOYSA-N 0.000 claims 1
- VQQUKLCJIHBWMK-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-fluorooxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C=CN=C(OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)C=1C1(F)CCOCC1 VQQUKLCJIHBWMK-UHFFFAOYSA-N 0.000 claims 1
- OXOUFDALYKGXIH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-hydroxycyclohexyl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(O)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OXOUFDALYKGXIH-UHFFFAOYSA-N 0.000 claims 1
- IZNYREVXKAXHFT-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-hydroxyoxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C=CN=C(OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)C=1C1(O)CCOCC1 IZNYREVXKAXHFT-UHFFFAOYSA-N 0.000 claims 1
- MSLMVJKRPSMSRP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-hydroxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(O)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 MSLMVJKRPSMSRP-UHFFFAOYSA-N 0.000 claims 1
- LXMLTIANVJGYBZ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methoxycyclohexen-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(OC)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 LXMLTIANVJGYBZ-UHFFFAOYSA-N 0.000 claims 1
- DLHLXYVYQGDEPM-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CC=NC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 DLHLXYVYQGDEPM-UHFFFAOYSA-N 0.000 claims 1
- DEPGKFSRVIIJKU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-methylpiperazin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CN(C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 DEPGKFSRVIIJKU-UHFFFAOYSA-N 0.000 claims 1
- RSFBEXTXIDVAHU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(4-morpholin-4-ylpiperidin-1-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N(CC1)CCC1N1CCOCC1 RSFBEXTXIDVAHU-UHFFFAOYSA-N 0.000 claims 1
- BXRWUPRQTKCGON-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(5-fluoro-2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=C(F)C=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 BXRWUPRQTKCGON-UHFFFAOYSA-N 0.000 claims 1
- QBFPMCPDBZLNIY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(5-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=CN=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 QBFPMCPDBZLNIY-UHFFFAOYSA-N 0.000 claims 1
- UYKPWRCLQFWBMS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(6-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(OC)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 UYKPWRCLQFWBMS-UHFFFAOYSA-N 0.000 claims 1
- MEDCWBFNYPAKKN-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(cyclopropylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1CC1 MEDCWBFNYPAKKN-UHFFFAOYSA-N 0.000 claims 1
- BKTPDUKLTUVKDY-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCOC1 BKTPDUKLTUVKDY-UHFFFAOYSA-N 0.000 claims 1
- VJEDECJAJOUHQS-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-3-ylamino)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1NC1CCCOC1 VJEDECJAJOUHQS-UHFFFAOYSA-N 0.000 claims 1
- MRMLYEPTQBRISE-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 MRMLYEPTQBRISE-UHFFFAOYSA-N 0.000 claims 1
- YAQXVILTNUOAIK-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxan-4-ylamino)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1NC1CCOCC1 YAQXVILTNUOAIK-UHFFFAOYSA-N 0.000 claims 1
- NVZBDCOGNZHANV-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxepan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCCOCC1 NVZBDCOGNZHANV-UHFFFAOYSA-N 0.000 claims 1
- FLFJGUVHSXRKII-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(oxolan-3-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1CCOC1 FLFJGUVHSXRKII-UHFFFAOYSA-N 0.000 claims 1
- KUWDSKWHERONCX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(pyridin-2-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1=CC=CC=N1 KUWDSKWHERONCX-UHFFFAOYSA-N 0.000 claims 1
- JEUOFPDZFFENPA-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(pyridin-3-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1=CC=CN=C1 JEUOFPDZFFENPA-UHFFFAOYSA-N 0.000 claims 1
- UZKSBOFNIMRSDU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(pyridin-4-ylmethoxy)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1OCC1=CC=NC=C1 UZKSBOFNIMRSDU-UHFFFAOYSA-N 0.000 claims 1
- VOFJMVKNCQVTIF-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-(thian-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCSCC1 VOFJMVKNCQVTIF-UHFFFAOYSA-N 0.000 claims 1
- VIZVTXGNPQLHRZ-IAGOWNOFSA-N 1h-benzimidazol-2-yl-[4-[3-[(1r,3r)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@H](O)CCC[C@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-IAGOWNOFSA-N 0.000 claims 1
- VIZVTXGNPQLHRZ-SJORKVTESA-N 1h-benzimidazol-2-yl-[4-[3-[(1r,3s)-3-hydroxycyclohexyl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@@H](O)CCC[C@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VIZVTXGNPQLHRZ-SJORKVTESA-N 0.000 claims 1
- PIZNUGDDGNOQHG-QGZVFWFLSA-N 1h-benzimidazol-2-yl-[4-[3-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC[C@H]1CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PIZNUGDDGNOQHG-QGZVFWFLSA-N 0.000 claims 1
- PCUFMTNTOOPRHU-INIZCTEOSA-N 1h-benzimidazol-2-yl-[4-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound OC[C@@H]1CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PCUFMTNTOOPRHU-INIZCTEOSA-N 0.000 claims 1
- PIZNUGDDGNOQHG-KRWDZBQOSA-N 1h-benzimidazol-2-yl-[4-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC[C@@H]1CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PIZNUGDDGNOQHG-KRWDZBQOSA-N 0.000 claims 1
- WIJUCVHWNZQALU-OAHLLOKOSA-N 1h-benzimidazol-2-yl-[4-[3-[(3r)-3-(hydroxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@H](CO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 WIJUCVHWNZQALU-OAHLLOKOSA-N 0.000 claims 1
- QRHDFAZLVIKPOI-HNNXBMFYSA-N 1h-benzimidazol-2-yl-[4-[3-[(3s)-3-hydroxypyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1[C@@H](O)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QRHDFAZLVIKPOI-HNNXBMFYSA-N 0.000 claims 1
- CBTCHLZKZTYQSJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[1-(2-fluoroethyl)piperidin-4-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CN(CCF)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 CBTCHLZKZTYQSJ-UHFFFAOYSA-N 0.000 claims 1
- PLJXWUBEQUVCBH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(1-methylpyrrolidin-2-yl)ethoxy]pyrazin-2-yl]oxyphenyl]methanone Chemical compound CN1CCCC1CCOC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PLJXWUBEQUVCBH-UHFFFAOYSA-N 0.000 claims 1
- XQFKWIKPJOIRMC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]pyrazin-2-yl]oxyphenyl]methanone Chemical compound N1=CSC(CCOC=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1C XQFKWIKPJOIRMC-UHFFFAOYSA-N 0.000 claims 1
- PMVQZUKKBJQXCZ-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(dimethylamino)ethoxy]pyrazin-2-yl]oxyphenyl]methanone Chemical compound CN(C)CCOC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 PMVQZUKKBJQXCZ-UHFFFAOYSA-N 0.000 claims 1
- BKUZKFYKHUKHQD-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[2-(trifluoromethyl)pyridin-4-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1=NC(C(F)(F)F)=CC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 BKUZKFYKHUKHQD-UHFFFAOYSA-N 0.000 claims 1
- ODFQXHMEQZGZRL-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[3-(2-hydroxyethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(CCO)CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ODFQXHMEQZGZRL-UHFFFAOYSA-N 0.000 claims 1
- XEMQHVLBGHISBX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[3-(2-hydroxypropan-2-yl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1C(C(C)(O)C)CCCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 XEMQHVLBGHISBX-UHFFFAOYSA-N 0.000 claims 1
- GUOBQKGNQBIELU-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(1-hydroxyethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(C(O)C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 GUOBQKGNQBIELU-UHFFFAOYSA-N 0.000 claims 1
- QJEPBHICDVQIMD-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(2-hydroxyethyl)piperazin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CN(CCO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 QJEPBHICDVQIMD-UHFFFAOYSA-N 0.000 claims 1
- KANNKAQVIUSRKP-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(2-hydroxyethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(CCO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 KANNKAQVIUSRKP-UHFFFAOYSA-N 0.000 claims 1
- MHWRPPDPBNSAHO-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(C(C)(O)C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 MHWRPPDPBNSAHO-UHFFFAOYSA-N 0.000 claims 1
- OVOUUAFYHZWGSH-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(hydroxymethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(CO)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OVOUUAFYHZWGSH-UHFFFAOYSA-N 0.000 claims 1
- OZUQEIMBSCUUPC-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(methoxymethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(COC)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OZUQEIMBSCUUPC-UHFFFAOYSA-N 0.000 claims 1
- ILOXGTYENJEMOX-UHFFFAOYSA-N 1h-benzimidazol-2-yl-[4-[3-[4-(trifluoromethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]methanone Chemical compound C1CC(C(F)(F)F)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ILOXGTYENJEMOX-UHFFFAOYSA-N 0.000 claims 1
- SGVADHZEXLKTJV-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridin-2-yl-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 SGVADHZEXLKTJV-UHFFFAOYSA-N 0.000 claims 1
- QAKJQHVIJCQZKR-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridin-2-yl-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 QAKJQHVIJCQZKR-UHFFFAOYSA-N 0.000 claims 1
- MEAZAXUDNCFOIG-FQEVSTJZSA-N 2-[(2s)-1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-2-yl]propan-2-ol Chemical compound CC(C)(O)[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 MEAZAXUDNCFOIG-FQEVSTJZSA-N 0.000 claims 1
- DXWVYUAWMGHOEQ-UHFFFAOYSA-N 2-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]-1,1,1-trifluoropropan-2-ol Chemical compound C1CC(C(O)(C)C(F)(F)F)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 DXWVYUAWMGHOEQ-UHFFFAOYSA-N 0.000 claims 1
- LSXLNZAVKKFYLI-UHFFFAOYSA-N 2-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LSXLNZAVKKFYLI-UHFFFAOYSA-N 0.000 claims 1
- ARBDZNDJQUKKDD-UHFFFAOYSA-N 2-[1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]propan-2-ol Chemical compound C1CC(C(C)(O)C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 ARBDZNDJQUKKDD-UHFFFAOYSA-N 0.000 claims 1
- HTFXSBUOJAQECG-UHFFFAOYSA-N 2-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-4,4-dimethylcyclohex-2-en-1-one Chemical compound CC1(C)CCC(=O)C(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 HTFXSBUOJAQECG-UHFFFAOYSA-N 0.000 claims 1
- VQBSHRMJYCLXMB-UHFFFAOYSA-N 2-[4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 VQBSHRMJYCLXMB-UHFFFAOYSA-N 0.000 claims 1
- GXNWIQSFJQCNPM-UHFFFAOYSA-N 2-methoxy-1-[4-[3-[4-(1-methylbenzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)C)C=C1 GXNWIQSFJQCNPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- PYCDSETUWLDZCK-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenoxy]pyrazin-2-yl]cyclohex-2-en-1-ol Chemical compound OC1CCCC(C=2C(=NC=CN=2)OC=2C=C(F)C(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 PYCDSETUWLDZCK-UHFFFAOYSA-N 0.000 claims 1
- KLDFOQPHBRUMBD-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenoxy]pyrazin-2-yl]cyclohex-2-en-1-one Chemical compound C=1C=C(NC=2SC3=CC=CC=C3N=2)C(F)=CC=1OC1=NC=CN=C1C1=CC(=O)CCC1 KLDFOQPHBRUMBD-UHFFFAOYSA-N 0.000 claims 1
- BLLKHCJAOCXHCW-UHFFFAOYSA-N 3-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]cyclohexan-1-one Chemical compound C1C(=O)CCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BLLKHCJAOCXHCW-UHFFFAOYSA-N 0.000 claims 1
- UWXGULKLJNSGCD-UHFFFAOYSA-N 3-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]benzonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CC(C#N)=C1 UWXGULKLJNSGCD-UHFFFAOYSA-N 0.000 claims 1
- MYZVLLYBDAJDOF-UHFFFAOYSA-N 3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]-n-(2-phenylethyl)pyrazine-2-carboxamide Chemical compound N=1C=CN=C(OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)C=1C(=O)NCCC1=CC=CC=C1 MYZVLLYBDAJDOF-UHFFFAOYSA-N 0.000 claims 1
- VLXIWTVVCJCPGQ-UHFFFAOYSA-N 3-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-3-oxopropanenitrile Chemical compound C1CN(C(CC#N)=O)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 VLXIWTVVCJCPGQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GVPAVKDFZQLKML-UHFFFAOYSA-N 4-[2-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyridin-3-yl]cyclohexan-1-one Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CC=C1C1CCC(=O)CC1 GVPAVKDFZQLKML-UHFFFAOYSA-N 0.000 claims 1
- AFVMYKZMYQFDLR-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)NC(C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 AFVMYKZMYQFDLR-UHFFFAOYSA-N 0.000 claims 1
- GFIJTCIBSLRCRB-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]oxan-4-ol Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(O)CCOCC1 GFIJTCIBSLRCRB-UHFFFAOYSA-N 0.000 claims 1
- WCMGHWBMVDXNQE-UHFFFAOYSA-N 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]oxane-4-carbonitrile Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(C#N)CCOCC1 WCMGHWBMVDXNQE-UHFFFAOYSA-N 0.000 claims 1
- MNBKHXOOKZPRRO-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-1-methyl-2,3-dihydropyridin-6-one Chemical compound O=C1N(C)CCC(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)=C1 MNBKHXOOKZPRRO-UHFFFAOYSA-N 0.000 claims 1
- OUGAZDLWIKVYON-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OUGAZDLWIKVYON-UHFFFAOYSA-N 0.000 claims 1
- AYGYYFLHDJHALN-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-1-methylpiperidin-2-one Chemical compound C1C(=O)N(C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 AYGYYFLHDJHALN-UHFFFAOYSA-N 0.000 claims 1
- IBBNCEJNFIIDIK-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-6-methylpiperazin-2-one Chemical compound C1C(=O)NC(C)CN1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 IBBNCEJNFIIDIK-UHFFFAOYSA-N 0.000 claims 1
- ZXQSIZFCBGTLEV-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 ZXQSIZFCBGTLEV-UHFFFAOYSA-N 0.000 claims 1
- UHCCFVNTZKQAGF-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]benzonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=C(C#N)C=C1 UHCCFVNTZKQAGF-UHFFFAOYSA-N 0.000 claims 1
- QDGUFUYNPQKEQO-UHFFFAOYSA-N 4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]oxane-4-carbonitrile Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1(C#N)CCOCC1 QDGUFUYNPQKEQO-UHFFFAOYSA-N 0.000 claims 1
- RHFMRDMSSVUEDF-UHFFFAOYSA-N 4-[3-[4-[1h-benzimidazol-2-yl(difluoro)methyl]phenoxy]pyrazin-2-yl]morpholine Chemical compound N=1C2=CC=CC=C2NC=1C(F)(F)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 RHFMRDMSSVUEDF-UHFFFAOYSA-N 0.000 claims 1
- PSLBMKSKQBUSDG-UHFFFAOYSA-N 4-methoxy-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1h-benzimidazol-2-amine Chemical compound N1C=2C(OC)=CC=CC=2N=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 PSLBMKSKQBUSDG-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- QSDGSLXMILIOLA-UHFFFAOYSA-N 5-fluoro-n-(4-pyrazin-2-yloxyphenyl)-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC(F)=CC=C2SC=1NC(C=C1)=CC=C1OC1=CN=CC=N1 QSDGSLXMILIOLA-UHFFFAOYSA-N 0.000 claims 1
- FQOWBVCZKJZQOG-UHFFFAOYSA-N 5-fluoro-n-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC(F)=CC=C2S1 FQOWBVCZKJZQOG-UHFFFAOYSA-N 0.000 claims 1
- SMYDNCOXQKJCTH-UHFFFAOYSA-N 5-fluoro-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC(F)=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 SMYDNCOXQKJCTH-UHFFFAOYSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- HRQSHDCWHGQGAC-UHFFFAOYSA-N 6-fluoro-n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-1h-benzimidazol-2-amine Chemical compound N=1C2=CC(F)=CC=C2NC=1NC(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 HRQSHDCWHGQGAC-UHFFFAOYSA-N 0.000 claims 1
- KERONYYLEGQYEG-UHFFFAOYSA-N 6-fluoro-n-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=C(F)C=C2S1 KERONYYLEGQYEG-UHFFFAOYSA-N 0.000 claims 1
- BSGFESLJQKRQEU-UHFFFAOYSA-N 6-fluoro-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound S1C2=CC(F)=CC=C2N=C1NC(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 BSGFESLJQKRQEU-UHFFFAOYSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- KGMCMFUARAQLBO-UHFFFAOYSA-N 7-fluoro-n-(4-pyrazin-2-yloxyphenyl)-1,3-benzothiazol-2-amine Chemical compound S1C=2C(F)=CC=CC=2N=C1NC(C=C1)=CC=C1OC1=CN=CC=N1 KGMCMFUARAQLBO-UHFFFAOYSA-N 0.000 claims 1
- MVFREHJVIKPVSY-UHFFFAOYSA-N 7-fluoro-n-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC(F)=C2S1 MVFREHJVIKPVSY-UHFFFAOYSA-N 0.000 claims 1
- FPXFNDLAKFLGMO-UHFFFAOYSA-N 8-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]-2-methyl-2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1N(C)CCC11CCN(C=2C(=NC=CN=2)OC=2C=CC(=CC=2)C(=O)C=2NC3=CC=CC=C3N=2)CC1 FPXFNDLAKFLGMO-UHFFFAOYSA-N 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- OXOUFDALYKGXIH-JCNLHEQBSA-N C1C[C@@H](O)CC[C@@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 Chemical compound C1C[C@@H](O)CC[C@@H]1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 OXOUFDALYKGXIH-JCNLHEQBSA-N 0.000 claims 1
- QRMZFQXVLGUEPK-UHFFFAOYSA-N COCC1CN(CC1)C=1C(=NC=CN1)OC=1C=C(C=CC1)C1=CC=CC2=C1N=C(S2)N Chemical compound COCC1CN(CC1)C=1C(=NC=CN1)OC=1C=C(C=CC1)C1=CC=CC2=C1N=C(S2)N QRMZFQXVLGUEPK-UHFFFAOYSA-N 0.000 claims 1
- UGNGHQXFNVAKGN-UHFFFAOYSA-N COCC1CN(CCC1)C=1C(=NC=CN1)OC=1C=C(C=CC1)C1=CC=CC2=C1N=C(S2)N Chemical compound COCC1CN(CCC1)C=1C(=NC=CN1)OC=1C=C(C=CC1)C1=CC=CC2=C1N=C(S2)N UGNGHQXFNVAKGN-UHFFFAOYSA-N 0.000 claims 1
- 206010008748 Chorea Diseases 0.000 claims 1
- 206010010219 Compulsions Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- WXFJXGLHWRJLAP-UHFFFAOYSA-N N1=CN=CC(=C1)C=1C(=NC=CN1)OC1=CC=C(C=C1)NC=1SC2=C(N1)C=CC=C2.N2=C(C=CC=C2)C#N Chemical compound N1=CN=CC(=C1)C=1C(=NC=CN1)OC1=CC=C(C=C1)NC=1SC2=C(N1)C=CC=C2.N2=C(C=CC=C2)C#N WXFJXGLHWRJLAP-UHFFFAOYSA-N 0.000 claims 1
- ZGGBZQTVJPDFMC-UHFFFAOYSA-N NC1=NC(C(C(C=C2)=CC=C2OC2=NC=CN=C2C2=CN=C3NC=CC3=C2)=CC=C2)=C2S1 Chemical compound NC1=NC(C(C(C=C2)=CC=C2OC2=NC=CN=C2C2=CN=C3NC=CC3=C2)=CC=C2)=C2S1 ZGGBZQTVJPDFMC-UHFFFAOYSA-N 0.000 claims 1
- ARDMDTLQZVFVAY-UHFFFAOYSA-N O=C(C1=NC(C=CC=C2)=C2N1)C(C=C1)=CC=C1OC1=NC=CN=C1C(CCCC1)C1=O Chemical compound O=C(C1=NC(C=CC=C2)=C2N1)C(C=C1)=CC=C1OC1=NC=CN=C1C(CCCC1)C1=O ARDMDTLQZVFVAY-UHFFFAOYSA-N 0.000 claims 1
- ZNEMNHKOCNTEPX-UHFFFAOYSA-N OCC1CN(CC1)C=1C(=NC=CN1)OC1=CC=C(C=C1)C=O Chemical compound OCC1CN(CC1)C=1C(=NC=CN1)OC1=CC=C(C=C1)C=O ZNEMNHKOCNTEPX-UHFFFAOYSA-N 0.000 claims 1
- 206010034719 Personality change Diseases 0.000 claims 1
- 206010037211 Psychomotor hyperactivity Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- SZGBCWRPVTXMHW-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)NC2=CC=C(OC=1C(=NC=CN1)C1CC(N(CC1)C(C)C)=O)C=C2 Chemical compound S1C(=NC2=C1C=CC=C2)NC2=CC=C(OC=1C(=NC=CN1)C1CC(N(CC1)C(C)C)=O)C=C2 SZGBCWRPVTXMHW-UHFFFAOYSA-N 0.000 claims 1
- FAXFNYUZSSDJMR-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)NC2=CC=C(OC=1C(=NC=CN1)C1CC(NCC1)=O)C=C2 Chemical compound S1C(=NC2=C1C=CC=C2)NC2=CC=C(OC=1C(=NC=CN1)C1CC(NCC1)=O)C=C2 FAXFNYUZSSDJMR-UHFFFAOYSA-N 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- JIPQSVBYFDEBMH-INIZCTEOSA-N [(2s)-1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 JIPQSVBYFDEBMH-INIZCTEOSA-N 0.000 claims 1
- XQQVEIPSNNREQS-OAHLLOKOSA-N [(3r)-1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyrrolidin-3-yl]methanol Chemical compound C1[C@H](CO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 XQQVEIPSNNREQS-OAHLLOKOSA-N 0.000 claims 1
- CBPDLAAUWWVMKL-UHFFFAOYSA-N [1-(2-fluoroethyl)benzimidazol-2-yl]-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)CCF)C=C1 CBPDLAAUWWVMKL-UHFFFAOYSA-N 0.000 claims 1
- KSDGDEIZWGGUDZ-UHFFFAOYSA-N [1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-2-yl]methanol Chemical compound OCC1CCCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KSDGDEIZWGGUDZ-UHFFFAOYSA-N 0.000 claims 1
- WLRYRZNBAXGEKR-UHFFFAOYSA-N [1-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 WLRYRZNBAXGEKR-UHFFFAOYSA-N 0.000 claims 1
- NBNXTDSTFXNNPW-UHFFFAOYSA-N [1-[4-[3-[4-(1h-benzimidazole-2-carbonyl)phenoxy]pyrazin-2-yl]piperidin-1-yl]-1-oxopropan-2-yl] acetate Chemical compound C1CN(C(=O)C(OC(C)=O)C)CCC1C1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CC=C3N=2)C=C1 NBNXTDSTFXNNPW-UHFFFAOYSA-N 0.000 claims 1
- JRCRNXCJLKEQBP-UHFFFAOYSA-N [4-(3-chloropyrazin-2-yl)oxyphenyl]-(1-methylbenzimidazol-2-yl)methanone Chemical compound N=1C2=CC=CC=C2N(C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1Cl JRCRNXCJLKEQBP-UHFFFAOYSA-N 0.000 claims 1
- BGDGOLPKPABEDN-UHFFFAOYSA-N [4-(3-chloropyrazin-2-yl)oxyphenyl]-(1h-imidazo[4,5-b]pyridin-2-yl)methanone Chemical compound ClC1=NC=CN=C1OC1=CC=C(C(=O)C=2NC3=CC=CN=C3N=2)C=C1 BGDGOLPKPABEDN-UHFFFAOYSA-N 0.000 claims 1
- MXZCWXPWJCAQAE-UHFFFAOYSA-N [4-(3-chloropyrazin-2-yl)oxyphenyl]-(4-fluoro-1h-benzimidazol-2-yl)methanone Chemical compound N1C=2C(F)=CC=CC=2N=C1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1Cl MXZCWXPWJCAQAE-UHFFFAOYSA-N 0.000 claims 1
- JASCRWQJWADYOW-UHFFFAOYSA-N [4-(3-chloropyrazin-2-yl)oxyphenyl]-(6-fluoro-1h-benzimidazol-2-yl)methanone Chemical compound N1C2=CC(F)=CC=C2N=C1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1Cl JASCRWQJWADYOW-UHFFFAOYSA-N 0.000 claims 1
- UESDQIHAOCLDAK-UHFFFAOYSA-N [4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-(1-propan-2-ylbenzimidazol-2-yl)methanone Chemical compound N=1C2=CC=CC=C2N(C(C)C)C=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1N1CCOCC1 UESDQIHAOCLDAK-UHFFFAOYSA-N 0.000 claims 1
- RPIVFFXGWTXQJQ-UHFFFAOYSA-N [4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-(1-methylbenzimidazol-2-yl)methanone Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC1=CC=C(C(=O)C=2N(C3=CC=CC=C3N=2)C)C=C1 RPIVFFXGWTXQJQ-UHFFFAOYSA-N 0.000 claims 1
- UNKROODATZENFE-UHFFFAOYSA-N [4-[3-(3,6-dihydro-2h-pyran-4-yl)pyrazin-2-yl]oxyphenyl]-(1h-imidazo[4,5-b]pyridin-2-yl)methanone Chemical compound N=1C2=NC=CC=C2NC=1C(=O)C(C=C1)=CC=C1OC1=NC=CN=C1C1=CCOCC1 UNKROODATZENFE-UHFFFAOYSA-N 0.000 claims 1
- WYCKYHDIMMRRSA-UHFFFAOYSA-N [5-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]pyridin-2-yl]methanol Chemical compound C1=NC(CO)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 WYCKYHDIMMRRSA-UHFFFAOYSA-N 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 210000001159 caudate nucleus Anatomy 0.000 claims 1
- 208000012601 choreatic disease Diseases 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 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 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- BZRRNYAPVFYOIN-UHFFFAOYSA-N n-(2-fluoro-4-pyrazin-2-yloxyphenyl)-1,3-benzothiazol-2-amine Chemical compound C=1C=C(NC=2SC3=CC=CC=C3N=2)C(F)=CC=1OC1=CN=CC=N1 BZRRNYAPVFYOIN-UHFFFAOYSA-N 0.000 claims 1
- UYYCSYQCVZFJMO-UHFFFAOYSA-N n-[2-fluoro-4-[3-(2-fluoropyridin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(F)=CC(C=2C(=NC=CN=2)OC=2C=C(F)C(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 UYYCSYQCVZFJMO-UHFFFAOYSA-N 0.000 claims 1
- OCQDDOPNHKDUIT-UHFFFAOYSA-N n-[2-fluoro-4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1F)=CC=C1NC1=NC2=CC=CC=C2S1 OCQDDOPNHKDUIT-UHFFFAOYSA-N 0.000 claims 1
- QHVJMPHJSJZSJT-UHFFFAOYSA-N n-[2-fluoro-4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C=1C=C(NC=2SC3=CC=CC=C3N=2)C(F)=CC=1OC1=NC=CN=C1C1CCOCC1 QHVJMPHJSJZSJT-UHFFFAOYSA-N 0.000 claims 1
- GIMGXQBCZAFEOK-UHFFFAOYSA-N n-[4-(3-chloropyrazin-2-yl)oxy-2-fluorophenyl]-1,3-benzothiazol-2-amine Chemical compound C=1C=C(NC=2SC3=CC=CC=C3N=2)C(F)=CC=1OC1=NC=CN=C1Cl GIMGXQBCZAFEOK-UHFFFAOYSA-N 0.000 claims 1
- RRSIEDWCWJOWBL-UHFFFAOYSA-N n-[4-(3-chloropyrazin-2-yl)oxyphenyl]-5-fluoro-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC(F)=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CN=C1Cl RRSIEDWCWJOWBL-UHFFFAOYSA-N 0.000 claims 1
- IKDYSBHEYDDLHF-UHFFFAOYSA-N n-[4-(3-chloropyrazin-2-yl)oxyphenyl]-7-fluoro-1,3-benzothiazol-2-amine Chemical compound S1C=2C(F)=CC=CC=2N=C1NC(C=C1)=CC=C1OC1=NC=CN=C1Cl IKDYSBHEYDDLHF-UHFFFAOYSA-N 0.000 claims 1
- QHQXBNYKAMDUDS-UHFFFAOYSA-N n-[4-(3-cyclopentylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 QHQXBNYKAMDUDS-UHFFFAOYSA-N 0.000 claims 1
- MCPHJRVZGYLLFS-UHFFFAOYSA-N n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 MCPHJRVZGYLLFS-UHFFFAOYSA-N 0.000 claims 1
- AYQCPWIILRLNBK-UHFFFAOYSA-N n-[4-(3-morpholin-4-ylpyrazin-2-yl)oxyphenyl]-1h-benzimidazol-2-amine Chemical compound C1COCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2N1 AYQCPWIILRLNBK-UHFFFAOYSA-N 0.000 claims 1
- KZQUGAMNOZLLRA-UHFFFAOYSA-N n-[4-(3-pyridin-3-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC(C=C1)=CC=C1OC1=NC=CN=C1C1=CC=CN=C1 KZQUGAMNOZLLRA-UHFFFAOYSA-N 0.000 claims 1
- LHQWYDHZOBIFCY-UHFFFAOYSA-N n-[4-(3-quinolin-5-ylpyrazin-2-yl)oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2C(C3=NC=CN=C3OC3=CC=C(C=C3)NC=3SC4=CC=CC=C4N=3)=CC=CC2=N1 LHQWYDHZOBIFCY-UHFFFAOYSA-N 0.000 claims 1
- OAIAEZMDZTUQTO-UHFFFAOYSA-N n-[4-[3-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound O1CCOC11CCN(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)CC1 OAIAEZMDZTUQTO-UHFFFAOYSA-N 0.000 claims 1
- DLBUCAJUNWPCLY-UHFFFAOYSA-N n-[4-[3-(1-methylpiperidin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 DLBUCAJUNWPCLY-UHFFFAOYSA-N 0.000 claims 1
- YLSRTMOLPMOJMY-UHFFFAOYSA-N n-[4-[3-(2,6-dimethylmorpholin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1C(C)OC(C)CN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YLSRTMOLPMOJMY-UHFFFAOYSA-N 0.000 claims 1
- VYKPDJKTQCAODH-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=NC=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 VYKPDJKTQCAODH-UHFFFAOYSA-N 0.000 claims 1
- VGLPMMNLRBDBMX-UHFFFAOYSA-N n-[4-[3-(2-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(OC)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 VGLPMMNLRBDBMX-UHFFFAOYSA-N 0.000 claims 1
- PQTNAWRVUJHRJJ-UHFFFAOYSA-N n-[4-[3-(2-methoxypyrimidin-5-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(OC)=NC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 PQTNAWRVUJHRJJ-UHFFFAOYSA-N 0.000 claims 1
- ANYKNJNYLGGMOX-UHFFFAOYSA-N n-[4-[3-(2-methylpyridin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C)=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 ANYKNJNYLGGMOX-UHFFFAOYSA-N 0.000 claims 1
- CRKFRXWSFJBSLF-UHFFFAOYSA-N n-[4-[3-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical class C1=CC=C2SC(NC3=CC=C(C=C3)OC3=NC=CN=C3N3CC=4N=CNC=4CC3)=NC2=C1 CRKFRXWSFJBSLF-UHFFFAOYSA-N 0.000 claims 1
- OJPKDYDFGPBSEW-UHFFFAOYSA-N n-[4-[3-(3-methoxyphenyl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=CC=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 OJPKDYDFGPBSEW-UHFFFAOYSA-N 0.000 claims 1
- BJDKNNDIYCAXMV-UHFFFAOYSA-N n-[4-[3-(3-methoxypyridin-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=CN=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 BJDKNNDIYCAXMV-UHFFFAOYSA-N 0.000 claims 1
- SOOCRXWTSFOYSK-UHFFFAOYSA-N n-[4-[3-(4-fluorooxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C=CN=C(OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=1C1(F)CCOCC1 SOOCRXWTSFOYSK-UHFFFAOYSA-N 0.000 claims 1
- UKLGJMYHGVHXBA-UHFFFAOYSA-N n-[4-[3-(4-methoxypiperidin-1-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CC(OC)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UKLGJMYHGVHXBA-UHFFFAOYSA-N 0.000 claims 1
- QHUHGALOARSWFD-UHFFFAOYSA-N n-[4-[3-(4-methylpiperazin-1-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CN(C)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 QHUHGALOARSWFD-UHFFFAOYSA-N 0.000 claims 1
- WHOJKFJRZQKXOH-UHFFFAOYSA-N n-[4-[3-(4-morpholin-4-ylphenyl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCN1C1=CC=C(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=C1 WHOJKFJRZQKXOH-UHFFFAOYSA-N 0.000 claims 1
- WNQBRQMCAFCYDT-UHFFFAOYSA-N n-[4-[3-(5-methoxypyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC1=CN=CC(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 WNQBRQMCAFCYDT-UHFFFAOYSA-N 0.000 claims 1
- WKUQNNALEOPDOR-UHFFFAOYSA-N n-[4-[3-(6-chloropyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(Cl)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 WKUQNNALEOPDOR-UHFFFAOYSA-N 0.000 claims 1
- KMGSAXQZYDPDMN-UHFFFAOYSA-N n-[4-[3-(6-methylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC(C)=CC=C1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KMGSAXQZYDPDMN-UHFFFAOYSA-N 0.000 claims 1
- AOBDSAPMYHFWOL-UHFFFAOYSA-N n-[4-[3-(6-morpholin-4-ylpyridin-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCN1C1=CC=C(C=2C(=NC=CN=2)OC=2C=CC(NC=3SC4=CC=CC=C4N=3)=CC=2)C=N1 AOBDSAPMYHFWOL-UHFFFAOYSA-N 0.000 claims 1
- PAUMHWVEIXSVLQ-UHFFFAOYSA-N n-[4-[3-(azetidin-1-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 PAUMHWVEIXSVLQ-UHFFFAOYSA-N 0.000 claims 1
- QNHDLOODKNRIRQ-UHFFFAOYSA-N n-[4-[3-(oxan-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCOCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 QNHDLOODKNRIRQ-UHFFFAOYSA-N 0.000 claims 1
- YWNIKPNVTJLBHN-UHFFFAOYSA-N n-[4-[3-(oxan-3-ylamino)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CCOCC1NC1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 YWNIKPNVTJLBHN-UHFFFAOYSA-N 0.000 claims 1
- CSQHJQJUFABKBU-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1COCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 CSQHJQJUFABKBU-UHFFFAOYSA-N 0.000 claims 1
- QNKGFWCQMGOKAR-UHFFFAOYSA-N n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1h-benzimidazol-2-amine Chemical compound C1COCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2N1 QNKGFWCQMGOKAR-UHFFFAOYSA-N 0.000 claims 1
- UJVGWVCHGJXURF-UHFFFAOYSA-N n-[4-[3-(oxolan-3-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1OCCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UJVGWVCHGJXURF-UHFFFAOYSA-N 0.000 claims 1
- KRRMOUBLHUGKFX-KRWDZBQOSA-N n-[4-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound COC[C@@H]1CCCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 KRRMOUBLHUGKFX-KRWDZBQOSA-N 0.000 claims 1
- SCFZQVUXBBPHTC-UHFFFAOYSA-N n-[4-[3-[1-(2-fluoroethyl)piperidin-4-yl]pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CN(CCF)CCC1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 SCFZQVUXBBPHTC-UHFFFAOYSA-N 0.000 claims 1
- UQNGKGCQRCJBTD-UHFFFAOYSA-N n-[4-[3-[4-(methoxymethyl)piperidin-1-yl]pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound C1CC(COC)CCN1C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 UQNGKGCQRCJBTD-UHFFFAOYSA-N 0.000 claims 1
- ROZAUDGDBWPBMH-UHFFFAOYSA-N n-methyl-n-[4-[3-(oxan-4-yl)pyrazin-2-yl]oxyphenyl]-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1N(C)C(C=C1)=CC=C1OC1=NC=CN=C1C1CCOCC1 ROZAUDGDBWPBMH-UHFFFAOYSA-N 0.000 claims 1
- 125000003551 oxepanyl group Chemical group 0.000 claims 1
- 230000001898 pallidal effect Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- RYHUNAYGLCGAKL-UHFFFAOYSA-N tert-butyl 4-[3-[4-(1,3-benzothiazol-2-ylamino)-3-fluorophenoxy]pyrazin-2-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C(=NC=CN=2)OC=2C=C(F)C(NC=3SC4=CC=CC=C4N=3)=CC=2)=C1 RYHUNAYGLCGAKL-UHFFFAOYSA-N 0.000 claims 1
- LKOZXUZYHCPBES-UHFFFAOYSA-N tert-butyl 4-[3-[4-(1,3-benzothiazol-2-ylamino)phenoxy]pyrazin-2-yl]-4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1(CO)C1=NC=CN=C1OC(C=C1)=CC=C1NC1=NC2=CC=CC=C2S1 LKOZXUZYHCPBES-UHFFFAOYSA-N 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11456708P | 2008-11-14 | 2008-11-14 | |
| US61/114,567 | 2008-11-14 | ||
| US16621209P | 2009-04-02 | 2009-04-02 | |
| US61/166,212 | 2009-04-02 | ||
| PCT/US2009/064637 WO2010057121A1 (en) | 2008-11-14 | 2009-11-16 | Pyrazine compounds as phosphodiesterase 10 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012508776A JP2012508776A (ja) | 2012-04-12 |
| JP2012508776A5 true JP2012508776A5 (enExample) | 2014-12-04 |
| JP5746972B2 JP5746972B2 (ja) | 2015-07-08 |
Family
ID=41478512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011536567A Expired - Fee Related JP5746972B2 (ja) | 2008-11-14 | 2009-11-16 | ホスホジエステラーゼ１０阻害剤としてのピラジン化合物 |
Country Status (30)
| Country | Link |
|---|---|
| US (4) | US8053438B2 (enExample) |
| EP (1) | EP2364308B1 (enExample) |
| JP (1) | JP5746972B2 (enExample) |
| KR (1) | KR20110083746A (enExample) |
| CN (1) | CN102300860B (enExample) |
| AR (1) | AR074358A1 (enExample) |
| AU (1) | AU2009313768B2 (enExample) |
| BR (1) | BRPI0922095A2 (enExample) |
| CA (1) | CA2742993C (enExample) |
| CL (1) | CL2011001094A1 (enExample) |
| CO (1) | CO6382157A2 (enExample) |
| CR (1) | CR20110326A (enExample) |
| CY (1) | CY1113680T1 (enExample) |
| DK (1) | DK2364308T3 (enExample) |
| EA (1) | EA019206B1 (enExample) |
| ES (1) | ES2397218T3 (enExample) |
| HR (1) | HRP20130054T1 (enExample) |
| IL (1) | IL212687A0 (enExample) |
| MA (1) | MA32889B1 (enExample) |
| MX (1) | MX2011005100A (enExample) |
| NZ (1) | NZ592508A (enExample) |
| PE (1) | PE20110581A1 (enExample) |
| PL (1) | PL2364308T3 (enExample) |
| PT (1) | PT2364308E (enExample) |
| RS (1) | RS52598B (enExample) |
| SI (1) | SI2364308T1 (enExample) |
| SM (1) | SMT201200061B (enExample) |
| TN (1) | TN2011000221A1 (enExample) |
| TW (1) | TWI396689B (enExample) |
| WO (1) | WO2010057121A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| MX2011006575A (es) * | 2008-12-17 | 2011-10-06 | Amgen Inc | Compuestos de aminopiridina y carboxipiridina como inhibidores de la fosfodiesterasa 10. |
| EP2393360B1 (en) | 2009-02-05 | 2015-11-04 | Takeda Pharmaceutical Company Limited | Pyridazinone compounds |
| CN102638982B (zh) | 2009-05-12 | 2015-07-08 | 百时美施贵宝公司 | (S)-7-([1,2,4]三唑并[1,5-a]吡啶-6-基)-4-(3,4-二氯苯基)-1,2,3,4-四氢异喹啉的晶型及其用途 |
| KR101830447B1 (ko) * | 2009-05-12 | 2018-02-20 | 알바니 몰레큘라 리써치, 인크. | 7-(［1,2,4］트리아졸로［1,5-α］피리딘-6-일)-4-(3,4-디클로로페닐)-1,2,3,4-테트라하이드로이소퀴놀린 및 이의 용도 |
| PE20121743A1 (es) | 2010-02-19 | 2012-12-22 | Boehringer Ingelheim Int | Derivados de piridina triciclicos, medicamentos que contienen tales compuestos, su uso y proceso para su preparacion |
| TWI546302B (zh) | 2010-06-24 | 2016-08-21 | 武田藥品工業股份有限公司 | 稠合雜環化合物 |
| WO2012018909A1 (en) | 2010-08-04 | 2012-02-09 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds |
| EP2602255B1 (en) | 2010-08-04 | 2017-04-26 | Takeda Pharmaceutical Company Limited | Fused heterocyclic ring compound |
| WO2012020780A1 (ja) | 2010-08-10 | 2012-02-16 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| MX344521B (es) | 2010-11-19 | 2016-12-19 | Ligand Pharm Inc | Aminas heterociclicas y sus usos. |
| WO2012096929A2 (en) | 2011-01-11 | 2012-07-19 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| EP2687529B1 (en) | 2011-03-16 | 2016-07-13 | Takeda Pharmaceutical Company Limited | Condensed heterocyclic compound |
| TWI570122B (zh) | 2011-06-22 | 2017-02-11 | 武田藥品工業股份有限公司 | 稠合雜環化合物之結晶 |
| CA2922849A1 (en) * | 2012-08-31 | 2014-03-06 | Ixchel Pharma, Llc | Agents useful for treating obesity, diabetes and related disorders |
| CN102911135B (zh) * | 2012-10-18 | 2016-01-13 | 内蒙古工业大学 | 2-巯基苯并噻唑类衍生物的合成方法 |
| AP2015008579A0 (en) | 2013-02-05 | 2015-07-31 | Purdue Pharma Lp | Tamper resistant pharmaceutical formulations |
| US9464076B2 (en) | 2013-03-15 | 2016-10-11 | Daiichi Sankyo Company, Limited | Benzothiophene derivative |
| WO2015006689A1 (en) | 2013-07-12 | 2015-01-15 | University Of South Alabama | Treatment and diagnosis of cancer and precancerous conditions using pde10a inhibitors and methods to measure pde10a expression |
| KR20160092991A (ko) | 2013-09-27 | 2016-08-05 | 님버스 아이리스 인코포레이티드 | Irak 억제제 및 이의 용도 |
| US9657015B2 (en) | 2014-07-31 | 2017-05-23 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| CN104649882A (zh) * | 2015-02-11 | 2015-05-27 | 南通恒盛精细化工有限公司 | 一种磷酸二酯酶抑制剂的中间体制备工艺 |
| US10807983B2 (en) | 2015-03-16 | 2020-10-20 | Ligand Pharmaceuticals, Inc. | Imidazo-fused heterocycles and uses thereof |
| TWI730002B (zh) * | 2015-09-18 | 2021-06-11 | 日商科研製藥股份有限公司 | 聯芳系化合物及含有此化合物之醫藥 |
| CN111615515B (zh) * | 2018-01-19 | 2023-11-24 | 苏州信诺维医药科技股份有限公司 | 杂环化合物、制备方法及其在医药上的应用 |
| CN109020977B (zh) * | 2018-10-26 | 2020-11-13 | 安庆奇创药业有限公司 | 一种Acalabrutinib的制备方法 |
| EP4263751B1 (en) | 2020-12-17 | 2025-08-13 | Merck Patent GmbH | Heteroaromatic isothiocyanates |
| CN113929598A (zh) * | 2021-11-24 | 2022-01-14 | 上海吉奉生物科技有限公司 | 一种（s）-2-叔丁氧羰基氨基-3-（4,4-二氟环己基）丙酸的合成方法 |
| EP4524134A1 (en) * | 2022-05-09 | 2025-03-19 | TYK Medicines Inc. | Polycyclic compound and use thereof |
| CN115894181A (zh) * | 2022-09-30 | 2023-04-04 | 渭南高新区海泰新型电子材料有限责任公司 | 一种环己烯基环己基二氟苯类液晶化合物的合成方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4198417A (en) * | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Phenoxyphenylpiperidines |
| PT1635828E (pt) | 2003-04-04 | 2008-07-01 | Lundbeck & Co As H | Derivados de 4-(2-feniloxifenil) piperidina ou de 1,2,3,6-tetrahidropiridina como inibidores da recaptação da serotonina |
| DE10337942A1 (de) | 2003-08-18 | 2005-03-17 | Merck Patent Gmbh | Aminobenzimidazolderivate |
| DE10344223A1 (de) * | 2003-09-24 | 2005-04-21 | Merck Patent Gmbh | 1,3-Benzoxazolylderivate als Kinase-Inhibitoren |
| DE10349587A1 (de) | 2003-10-24 | 2005-05-25 | Merck Patent Gmbh | Benzimidazolylderivate |
| US7470712B2 (en) | 2004-01-21 | 2008-12-30 | Bristol-Myers Squibb Company | Amino-benzazoles as P2Y1 receptor inhibitors |
| BRPI0511295A (pt) * | 2004-05-18 | 2007-12-04 | Schering Corp | 2-quinolil-oxazóis substituìdos úteis como inibidores de pde4 |
| EP1755611A1 (en) * | 2004-06-07 | 2007-02-28 | Pfizer Products Inc. | Phosphodiesterase 10 inhibition as treatment for obesity-related and metabolic syndrome-related conditions |
| US20060183763A1 (en) * | 2004-12-31 | 2006-08-17 | Pfizer Inc | Novel pyrrolidyl derivatives of heteroaromatic compounds |
| DE102005016634A1 (de) * | 2005-04-12 | 2006-10-19 | Merck Patent Gmbh | Neuartige Aza-Hetercyclen als Kinase-Inhibitoren |
| CA2615890A1 (en) | 2005-08-02 | 2007-02-08 | Irm Llc | 5-substituted thiazol-2-yl amino compounds and compositions as protein kinase inhibitors |
| AU2007217750A1 (en) * | 2006-02-21 | 2007-08-30 | Amgen Inc. | Cinnoline derivatives as phosphodiesterase 10 inhibitors |
| US7868177B2 (en) | 2006-02-24 | 2011-01-11 | Amgen Inc. | Multi-cyclic compounds and method of use |
| CA2650976A1 (en) * | 2006-05-02 | 2007-11-15 | Pfizer Products Inc. | Bicyclic heteroaryl compounds as pde10 inhibitors |
| US20080090834A1 (en) * | 2006-07-06 | 2008-04-17 | Pfizer Inc | Selective azole pde10a inhibitor compounds |
| WO2008057280A1 (en) | 2006-10-27 | 2008-05-15 | Amgen Inc. | Multi-cyclic compounds and methods of use |
| PT2125786E (pt) | 2006-12-21 | 2011-04-21 | Pfizer Prod Inc | Sal succinato de 2-((4-(1-metil-4-(piridin-4-il)-1hpirazol- 3-il)fenoxi)metil)quinolina |
| AU2008315746A1 (en) | 2007-10-25 | 2009-04-30 | Astrazeneca Ab | Pyridine and pyrazine derivatives useful in the treatment of cell proliferative disorders |
| WO2009081259A1 (en) | 2007-12-21 | 2009-07-02 | Pfizer Inc. | Phenoxy-pyridyl derivatives |
| CN102203074A (zh) | 2008-06-20 | 2011-09-28 | 麦它波莱克斯股份有限公司 | 芳基gpr119激动剂及其用途 |
-
2009
- 2009-11-13 TW TW098138718A patent/TWI396689B/zh not_active IP Right Cessation
- 2009-11-16 EP EP09752705A patent/EP2364308B1/en active Active
- 2009-11-16 EA EA201100748A patent/EA019206B1/ru not_active IP Right Cessation
- 2009-11-16 PE PE2011001035A patent/PE20110581A1/es not_active Application Discontinuation
- 2009-11-16 BR BRPI0922095A patent/BRPI0922095A2/pt not_active IP Right Cessation
- 2009-11-16 SI SI200930429T patent/SI2364308T1/sl unknown
- 2009-11-16 JP JP2011536567A patent/JP5746972B2/ja not_active Expired - Fee Related
- 2009-11-16 MX MX2011005100A patent/MX2011005100A/es active IP Right Grant
- 2009-11-16 NZ NZ592508A patent/NZ592508A/xx not_active IP Right Cessation
- 2009-11-16 PT PT97527055T patent/PT2364308E/pt unknown
- 2009-11-16 CA CA2742993A patent/CA2742993C/en not_active Expired - Fee Related
- 2009-11-16 WO PCT/US2009/064637 patent/WO2010057121A1/en not_active Ceased
- 2009-11-16 HR HRP20130054AT patent/HRP20130054T1/hr unknown
- 2009-11-16 RS RS20120569A patent/RS52598B/sr unknown
- 2009-11-16 KR KR1020117013506A patent/KR20110083746A/ko not_active Withdrawn
- 2009-11-16 US US12/619,574 patent/US8053438B2/en not_active Expired - Fee Related
- 2009-11-16 CN CN200980154871.6A patent/CN102300860B/zh not_active Expired - Fee Related
- 2009-11-16 PL PL09752705T patent/PL2364308T3/pl unknown
- 2009-11-16 DK DK09752705.5T patent/DK2364308T3/da active
- 2009-11-16 AU AU2009313768A patent/AU2009313768B2/en not_active Ceased
- 2009-11-16 ES ES09752705T patent/ES2397218T3/es active Active
- 2009-11-16 AR ARP090104436A patent/AR074358A1/es not_active Application Discontinuation
-
2011
- 2011-03-07 US US13/042,410 patent/US8329700B2/en not_active Expired - Fee Related
- 2011-03-07 US US13/042,421 patent/US8247418B2/en not_active Expired - Fee Related
- 2011-05-04 IL IL212687A patent/IL212687A0/en unknown
- 2011-05-05 TN TN2011000221A patent/TN2011000221A1/fr unknown
- 2011-05-13 CL CL2011001094A patent/CL2011001094A1/es unknown
- 2011-06-10 MA MA33928A patent/MA32889B1/fr unknown
- 2011-06-14 CR CR20110326A patent/CR20110326A/es not_active Application Discontinuation
- 2011-06-14 CO CO11073978A patent/CO6382157A2/es not_active Application Discontinuation
-
2012
- 2012-06-22 US US13/531,453 patent/US20120277209A1/en not_active Abandoned
- 2012-12-19 SM SM201200061T patent/SMT201200061B/it unknown
- 2012-12-21 CY CY20121101246T patent/CY1113680T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012508776A5 (enExample) | ||
| HRP20130054T1 (hr) | Spojevi pirazina kao inhibitori fosfodiesteraze 10 | |
| JP7028861B2 (ja) | ピリジル置換のインドール化合物 | |
| JP6348891B2 (ja) | Ｃｘｃｒ４受容体アンタゴニスト | |
| JP5714573B2 (ja) | キヌレニン産生抑制作用を有する含窒素複素環化合物 | |
| CA2798325A1 (en) | Heteroaryloxyheterocyclyl compounds as pde10 inhibitors | |
| JP2013539777A5 (enExample) | ||
| JP2013526536A5 (enExample) | ||
| JP6067181B2 (ja) | アルドステロンシンターゼ阻害薬 | |
| SI3177619T1 (en) | 2- (morpholin-4-yl) -1,7-naphthyridines | |
| JP2018524343A5 (enExample) | ||
| AU2015320675A1 (en) | Aminotriazine derivatives useful as tank-binding kinase inhibitor compounds | |
| SI3083586T1 (en) | The new carboxamides, the process of their manufacture, the pharmaceutical preparations they contain and their use for the manufacture of medicinal products | |
| JPWO2005063743A1 (ja) | チアゾール誘導体 | |
| JP2014501269A5 (enExample) | ||
| JP2019514878A5 (enExample) | ||
| AU2015249753A1 (en) | Substituted [1,2,4] triazolo [1,5-a] pyrimidin-7-yl compounds as PDE2 inhibitors | |
| JP2015500332A5 (enExample) | ||
| JP2020510621A (ja) | Ｇａｂａ ａ ａｌｐｈａ５ ｐａｍとしての新規イソキサゾリルエーテル誘導体 | |
| RU2015107979A (ru) | Новые бициклические производные пиридина | |
| JP2015526452A5 (enExample) | ||
| JPWO2020201773A5 (enExample) | ||
| US11840528B2 (en) | Isoxazolyl ether derivatives as GABAA α5 PAM | |
| JPWO2020203609A5 (enExample) | ||
| WO2025255288A1 (en) | Pkc-theta inhibitors, compositions, and methods of use |