JP2012508776A5 - - Google Patents
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- 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
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- 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
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| US8846713B2 (en) | 2010-06-24 | 2014-09-30 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds as phosphodiesterases (PDEs) inhibitors |
| US8883788B2 (en) | 2010-08-04 | 2014-11-11 | Takeda Pharmaceutical Company Limited | Fused heterocyclic ring compound |
| EP2601192B1 (en) | 2010-08-04 | 2017-03-01 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds |
| EP2604597B1 (en) | 2010-08-10 | 2017-01-04 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof inhibitor of phosphodiesterase 10a |
| KR20180099933A (ko) | 2010-11-19 | 2018-09-05 | 리간드 파마슈티칼스 인코포레이티드 | 복소환 아민 및 이의 용도 |
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| 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 |
| BR112016006319A2 (pt) | 2013-09-27 | 2017-08-01 | Nimbus Iris Inc | inibidores de irak e usos dos mesmos |
| 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 |
| SG11201801856XA (en) * | 2015-09-18 | 2018-04-27 | Kaken Pharmaceutical Co Ltd | Biaryl derivative and medicine containing same |
| WO2019141259A1 (zh) * | 2018-01-19 | 2019-07-25 | 苏州信诺维医药科技有限公司 | 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 |
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| 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 |
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| 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 |
| JP2009503073A (ja) | 2005-08-02 | 2009-01-29 | アイアールエム・リミテッド・ライアビリティ・カンパニー | タンパク質キナーゼ阻害剤としての５−置換チアゾール−２−イルアミノ化合物および組成物 |
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| US7868177B2 (en) | 2006-02-24 | 2011-01-11 | Amgen Inc. | Multi-cyclic compounds and method of use |
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| 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 |
| SI2125786T1 (sl) * | 2006-12-21 | 2011-05-31 | Pfizer Prod Inc | Sukcinat sol 2-((4-(1-metil-4-(piridin-4-il)-1H-pirazol-3-il)fenoksi)metil)kinolina |
| ATE523508T1 (de) | 2007-10-25 | 2011-09-15 | Astrazeneca Ab | Für die behandlung von zellproliferativen erkrankungen geeignete pyridin- und pyrazinderivate |
| WO2009081259A1 (en) | 2007-12-21 | 2009-07-02 | Pfizer Inc. | Phenoxy-pyridyl derivatives |
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-
2009
- 2009-11-13 TW TW098138718A patent/TWI396689B/zh not_active IP Right Cessation
- 2009-11-16 PL PL09752705T patent/PL2364308T3/pl unknown
- 2009-11-16 EP EP09752705A patent/EP2364308B1/en active Active
- 2009-11-16 PT PT97527055T patent/PT2364308E/pt unknown
- 2009-11-16 EA EA201100748A patent/EA019206B1/ru 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 CN CN200980154871.6A patent/CN102300860B/zh not_active Expired - Fee Related
- 2009-11-16 AR ARP090104436A patent/AR074358A1/es not_active Application Discontinuation
- 2009-11-16 HR HRP20130054AT patent/HRP20130054T1/hr unknown
- 2009-11-16 CA CA2742993A patent/CA2742993C/en not_active Expired - Fee Related
- 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 BR BRPI0922095A patent/BRPI0922095A2/pt not_active IP Right Cessation
- 2009-11-16 NZ NZ592508A patent/NZ592508A/xx not_active IP Right Cessation
- 2009-11-16 WO PCT/US2009/064637 patent/WO2010057121A1/en not_active Ceased
- 2009-11-16 RS RS20120569A patent/RS52598B/sr unknown
- 2009-11-16 DK DK09752705.5T patent/DK2364308T3/da active
- 2009-11-16 ES ES09752705T patent/ES2397218T3/es active Active
- 2009-11-16 AU AU2009313768A patent/AU2009313768B2/en not_active Ceased
- 2009-11-16 MX MX2011005100A patent/MX2011005100A/es active IP Right Grant
- 2009-11-16 PE PE2011001035A patent/PE20110581A1/es not_active Application Discontinuation
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2011
- 2011-03-07 US US13/042,421 patent/US8247418B2/en not_active Expired - Fee Related
- 2011-03-07 US US13/042,410 patent/US8329700B2/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
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- 2012-06-22 US US13/531,453 patent/US20120277209A1/en not_active Abandoned
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- 2012-12-21 CY CY20121101246T patent/CY1113680T1/el unknown
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