JP2015528018A5 - - Google Patents
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- Publication number
- JP2015528018A5 JP2015528018A5 JP2015525460A JP2015525460A JP2015528018A5 JP 2015528018 A5 JP2015528018 A5 JP 2015528018A5 JP 2015525460 A JP2015525460 A JP 2015525460A JP 2015525460 A JP2015525460 A JP 2015525460A JP 2015528018 A5 JP2015528018 A5 JP 2015528018A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- naphthyridin
- oxy
- alkyl
- methylpentyl
- 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.)
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- 125000005843 halogen group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- -1 C 1 -C 3 haloalkyl Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 4
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- LQOKRXHYUBRKJK-UHFFFAOYSA-N 3h-2,7-naphthyridin-4-one Chemical compound N1=CC=C2C(=O)CN=CC2=C1 LQOKRXHYUBRKJK-UHFFFAOYSA-N 0.000 claims 2
- XCKUSTFLSTVTCR-AWEZNQCLSA-N 8-[(2s)-2-amino-4-methylpentoxy]-2,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=C(C)C=C2C3=CC=C(OC[C@@H](N)CC(C)C)C=C3N(C)C(=O)C2=C1 XCKUSTFLSTVTCR-AWEZNQCLSA-N 0.000 claims 2
- HSHQEKUILXZVHT-ZDUSSCGKSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6-dimethyl-9-(trifluoromethyl)benzo[c][2,7]naphthyridin-5-one Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OC[C@@H](N)CC(C)C)C(C(F)(F)F)=C2 HSHQEKUILXZVHT-ZDUSSCGKSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- LOZLKDVGPQCIRZ-INIZCTEOSA-N 4,6-dimethyl-8-[(2s)-4-methyl-2-(methylamino)pentoxy]-5-oxobenzo[c][2,7]naphthyridine-9-carbonitrile Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OC[C@@H](NC)CC(C)C)C(C#N)=C2 LOZLKDVGPQCIRZ-INIZCTEOSA-N 0.000 claims 1
- WWWKOVDRVDVLRG-HNNXBMFYSA-N 4,6-dimethyl-8-[(2s)-4-methyl-2-(methylamino)pentoxy]benzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@@H](NC)CC(C)C)C=C3N(C)C(=O)C2=C1C WWWKOVDRVDVLRG-HNNXBMFYSA-N 0.000 claims 1
- GIJACGNPPUYZEJ-LBPRGKRZSA-N 4-amino-8-[(2s)-2-amino-4-methylpentoxy]-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@@H](N)CC(C)C)C=C3N(C)C(=O)C2=C1N GIJACGNPPUYZEJ-LBPRGKRZSA-N 0.000 claims 1
- FCBKDNGEEHZOJJ-NSHDSACASA-N 4-amino-8-[(2s)-2-amino-4-methylpentoxy]-9-fluoro-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound CN1C(=O)C2=C(N)N=CC=C2C2=C1C=C(OC[C@@H](N)CC(C)C)C(F)=C2 FCBKDNGEEHZOJJ-NSHDSACASA-N 0.000 claims 1
- MCBJOMAHTKEJOM-UHFFFAOYSA-N 6-methyl-8-(piperidin-2-ylmethoxy)benzo[c][2,7]naphthyridin-5-one Chemical compound C=1C=C2C3=CC=NC=C3C(=O)N(C)C2=CC=1OCC1CCCCN1 MCBJOMAHTKEJOM-UHFFFAOYSA-N 0.000 claims 1
- OAGROMXPCACYDF-AWEZNQCLSA-N 6-methyl-8-[(2s)-4-methyl-2-(methylamino)pentoxy]benzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@@H](NC)CC(C)C)C=C3N(C)C(=O)C2=C1 OAGROMXPCACYDF-AWEZNQCLSA-N 0.000 claims 1
- KLLKJQSKBGRMFP-UHFFFAOYSA-N 8-(2-amino-2,4-dimethylpentoxy)-1-fluoro-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC(F)=C2C3=CC=C(OCC(C)(N)CC(C)C)C=C3N(C)C(=O)C2=C1 KLLKJQSKBGRMFP-UHFFFAOYSA-N 0.000 claims 1
- KAXLZTZBXHYOSC-UHFFFAOYSA-N 8-(2-amino-2,4-dimethylpentoxy)-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OCC(C)(N)CC(C)C)C=C3N(C)C(=O)C2=C1C KAXLZTZBXHYOSC-UHFFFAOYSA-N 0.000 claims 1
- NBHCBBXZBQCGBZ-UHFFFAOYSA-N 8-(2-amino-2,4-dimethylpentoxy)-7-fluoro-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C1=NC(C)=C2C(=O)N(C)C3=C(F)C(OCC(C)(N)CC(C)C)=CC=C3C2=C1 NBHCBBXZBQCGBZ-UHFFFAOYSA-N 0.000 claims 1
- KMUIQNNSUSDHKH-UHFFFAOYSA-N 8-(2-amino-2,4-dimethylpentoxy)-7-fluoro-4-methyl-6h-benzo[c][2,7]naphthyridin-5-one Chemical compound C1=NC(C)=C2C(=O)NC3=C(F)C(OCC(C)(N)CC(C)C)=CC=C3C2=C1 KMUIQNNSUSDHKH-UHFFFAOYSA-N 0.000 claims 1
- CMHHZVVLJLNEHM-UHFFFAOYSA-N 8-(2-amino-2,4-dimethylpentoxy)-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OCC(C)(N)CC(C)C)C(Cl)=C2 CMHHZVVLJLNEHM-UHFFFAOYSA-N 0.000 claims 1
- XKLGKAZUFOBXOV-UHFFFAOYSA-N 8-(2-amino-2,4-dimethylpentoxy)-9-fluoro-4-methyl-6h-benzo[c][2,7]naphthyridin-5-one Chemical compound N1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OCC(C)(N)CC(C)C)C(F)=C2 XKLGKAZUFOBXOV-UHFFFAOYSA-N 0.000 claims 1
- STLIWKILGDSCFT-UHFFFAOYSA-N 8-(2-amino-2,4-dimethylpentoxy)-9-methoxy-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OCC(C)(N)CC(C)C)C(OC)=C2 STLIWKILGDSCFT-UHFFFAOYSA-N 0.000 claims 1
- HZWYAONXPMPCBU-UHFFFAOYSA-N 8-(2-amino-4,4,4-trifluorobutoxy)-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound C1=NC=C2C(=O)N(C)C3=CC(OCC(N)CC(F)(F)F)=CC=C3C2=C1 HZWYAONXPMPCBU-UHFFFAOYSA-N 0.000 claims 1
- FXZTVDZYBASRIS-UHFFFAOYSA-N 8-(2-amino-5,5,5-trifluoropentoxy)-4,6-dimethyl-5-oxobenzo[c][2,7]naphthyridine-9-carbonitrile Chemical compound C12=CC(C#N)=C(OCC(N)CCC(F)(F)F)C=C2N(C)C(=O)C2=C1C=CN=C2C FXZTVDZYBASRIS-UHFFFAOYSA-N 0.000 claims 1
- ZSCOHFKAMHDAOA-UHFFFAOYSA-N 8-(2-amino-5,5,5-trifluoropentoxy)-6-methyl-5-oxobenzo[c][2,7]naphthyridine-9-carbonitrile Chemical compound C1=NC=C2C(=O)N(C)C3=CC(OCC(N)CCC(F)(F)F)=C(C#N)C=C3C2=C1 ZSCOHFKAMHDAOA-UHFFFAOYSA-N 0.000 claims 1
- XWZXCIPLOWRHAC-UHFFFAOYSA-N 8-(2-amino-5,5,5-trifluoropentoxy)-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound C1=NC=C2C(=O)N(C)C3=CC(OCC(N)CCC(F)(F)F)=CC=C3C2=C1 XWZXCIPLOWRHAC-UHFFFAOYSA-N 0.000 claims 1
- KAXLZTZBXHYOSC-OAQYLSRUSA-N 8-[(2r)-2-amino-2,4-dimethylpentoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@](C)(N)CC(C)C)C=C3N(C)C(=O)C2=C1C KAXLZTZBXHYOSC-OAQYLSRUSA-N 0.000 claims 1
- YRGHZZQVZHUGHW-LLVKDONJSA-N 8-[(2r)-2-amino-4,4,4-trifluorobutoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C12=CC=C(OC[C@H](N)CC(F)(F)F)C=C2N(C)C(=O)C2=C1C=CN=C2C YRGHZZQVZHUGHW-LLVKDONJSA-N 0.000 claims 1
- NQXBZPJVVGIFBJ-OAHLLOKOSA-N 8-[(2r)-2-amino-4-methylpentoxy]-4,6-dimethyl-5-oxobenzo[c][2,7]naphthyridine-9-carbonitrile Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OC[C@H](N)CC(C)C)C(C#N)=C2 NQXBZPJVVGIFBJ-OAHLLOKOSA-N 0.000 claims 1
- HRMGBYSRWUAWIG-CQSZACIVSA-N 8-[(2r)-2-amino-4-methylpentoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@H](N)CC(C)C)C=C3N(C)C(=O)C2=C1C HRMGBYSRWUAWIG-CQSZACIVSA-N 0.000 claims 1
- URECUINDIIRBJP-CYBMUJFWSA-N 8-[(2r)-2-amino-4-methylpentoxy]-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OC[C@H](N)CC(C)C)C(Cl)=C2 URECUINDIIRBJP-CYBMUJFWSA-N 0.000 claims 1
- RXVZYVSEPCPLIQ-INIZCTEOSA-N 8-[(2s)-2-(dimethylamino)-4-methylpentoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@H](CC(C)C)N(C)C)C=C3N(C)C(=O)C2=C1C RXVZYVSEPCPLIQ-INIZCTEOSA-N 0.000 claims 1
- GSMCIADOCFDNFO-HNNXBMFYSA-N 8-[(2s)-2-(dimethylamino)-4-methylpentoxy]-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@H](CC(C)C)N(C)C)C=C3N(C)C(=O)C2=C1 GSMCIADOCFDNFO-HNNXBMFYSA-N 0.000 claims 1
- KAXLZTZBXHYOSC-NRFANRHFSA-N 8-[(2s)-2-amino-2,4-dimethylpentoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@@](C)(N)CC(C)C)C=C3N(C)C(=O)C2=C1C KAXLZTZBXHYOSC-NRFANRHFSA-N 0.000 claims 1
- OOOPDKTUMJEDEK-INIZCTEOSA-N 8-[(2s)-2-amino-3-cyclobutylpropoxy]-4,6,9-trimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C([C@H](N)COC1=CC2=C(C3=CC=NC(C)=C3C(=O)N2C)C=C1C)C1CCC1 OOOPDKTUMJEDEK-INIZCTEOSA-N 0.000 claims 1
- SPLKFCCVHVFPQH-HNNXBMFYSA-N 8-[(2s)-2-amino-3-cyclobutylpropoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C([C@H](N)COC1=CC=C2C=3C=CN=C(C=3C(=O)N(C)C2=C1)C)C1CCC1 SPLKFCCVHVFPQH-HNNXBMFYSA-N 0.000 claims 1
- SNEOIKHHDVLVOX-AWEZNQCLSA-N 8-[(2s)-2-amino-3-cyclobutylpropoxy]-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C([C@H](N)COC1=C(Cl)C=C2C=3C=CN=C(C=3C(=O)N(C)C2=C1)C)C1CCC1 SNEOIKHHDVLVOX-AWEZNQCLSA-N 0.000 claims 1
- QWYVFLDYWGJEQU-HNNXBMFYSA-N 8-[(2s)-2-amino-3-cyclopropylpropoxy]-4,6,9-trimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C([C@H](N)COC1=CC2=C(C3=CC=NC(C)=C3C(=O)N2C)C=C1C)C1CC1 QWYVFLDYWGJEQU-HNNXBMFYSA-N 0.000 claims 1
- NJUOJAQINHVMBT-AWEZNQCLSA-N 8-[(2s)-2-amino-3-cyclopropylpropoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C([C@H](N)COC1=CC=C2C=3C=CN=C(C=3C(=O)N(C)C2=C1)C)C1CC1 NJUOJAQINHVMBT-AWEZNQCLSA-N 0.000 claims 1
- UVIQIJWVZHLOOF-ZDUSSCGKSA-N 8-[(2s)-2-amino-3-cyclopropylpropoxy]-9-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C([C@H](N)COC1=C(Cl)C=C2C=3C=CN=C(C=3C(=O)N(C)C2=C1)C)C1CC1 UVIQIJWVZHLOOF-ZDUSSCGKSA-N 0.000 claims 1
- YGIQORZXXQTXBN-ZDUSSCGKSA-N 8-[(2s)-2-amino-3-propan-2-yloxypropoxy]-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@@H](N)COC(C)C)C=C3N(C)C(=O)C2=C1 YGIQORZXXQTXBN-ZDUSSCGKSA-N 0.000 claims 1
- YRGHZZQVZHUGHW-NSHDSACASA-N 8-[(2s)-2-amino-4,4,4-trifluorobutoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound C12=CC=C(OC[C@@H](N)CC(F)(F)F)C=C2N(C)C(=O)C2=C1C=CN=C2C YRGHZZQVZHUGHW-NSHDSACASA-N 0.000 claims 1
- WHQDGHKLJVQMRP-NSHDSACASA-N 8-[(2s)-2-amino-4,4-difluoropentoxy]-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound C1=NC=C2C(=O)N(C)C3=CC(OC[C@@H](N)CC(C)(F)F)=CC=C3C2=C1 WHQDGHKLJVQMRP-NSHDSACASA-N 0.000 claims 1
- NLRSBHGTESEGQM-LBPRGKRZSA-N 8-[(2s)-2-amino-4-methylpentoxy]-1-fluoro-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC(F)=C2C3=CC=C(OC[C@@H](N)CC(C)C)C=C3N(C)C(=O)C2=C1 NLRSBHGTESEGQM-LBPRGKRZSA-N 0.000 claims 1
- XVIGNJJPLOWARI-ZDUSSCGKSA-N 8-[(2s)-2-amino-4-methylpentoxy]-1-methoxy-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound C12=CC=C(OC[C@@H](N)CC(C)C)C=C2N(C)C(=O)C2=C1C(OC)=CN=C2 XVIGNJJPLOWARI-ZDUSSCGKSA-N 0.000 claims 1
- VKDHJNPPKCHVLP-HNNXBMFYSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6,9-trimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OC[C@@H](N)CC(C)C)C(C)=C2 VKDHJNPPKCHVLP-HNNXBMFYSA-N 0.000 claims 1
- NQXBZPJVVGIFBJ-HNNXBMFYSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6-dimethyl-5-oxobenzo[c][2,7]naphthyridine-9-carbonitrile Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OC[C@@H](N)CC(C)C)C(C#N)=C2 NQXBZPJVVGIFBJ-HNNXBMFYSA-N 0.000 claims 1
- BLTIFWQUIKJLLO-ZDUSSCGKSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6-dimethyl-5-oxobenzo[c][2,7]naphthyridine-9-carboxamide Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OC[C@@H](N)CC(C)C)C(C(N)=O)=C2 BLTIFWQUIKJLLO-ZDUSSCGKSA-N 0.000 claims 1
- PBOYTVVOMMRCKA-HNNXBMFYSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6-dimethyl-9-(1,3-oxazol-5-yl)benzo[c][2,7]naphthyridin-5-one Chemical compound CC(C)C[C@H](N)COC1=CC=2N(C)C(=O)C3=C(C)N=CC=C3C=2C=C1C1=CN=CO1 PBOYTVVOMMRCKA-HNNXBMFYSA-N 0.000 claims 1
- WVWZWEDZULHZHM-HNNXBMFYSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6-dimethyl-9-(1,3-thiazol-5-yl)benzo[c][2,7]naphthyridin-5-one Chemical compound CC(C)C[C@H](N)COC1=CC=2N(C)C(=O)C3=C(C)N=CC=C3C=2C=C1C1=CN=CS1 WVWZWEDZULHZHM-HNNXBMFYSA-N 0.000 claims 1
- VNYWTAUYKHVQTO-AWEZNQCLSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6-dimethyl-9-methylsulfonylbenzo[c][2,7]naphthyridin-5-one Chemical compound CN1C(=O)C2=C(C)N=CC=C2C2=C1C=C(OC[C@@H](N)CC(C)C)C(S(C)(=O)=O)=C2 VNYWTAUYKHVQTO-AWEZNQCLSA-N 0.000 claims 1
- CJYBTGCGPOINHK-KRWDZBQOSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6-dimethyl-9-pyridin-2-ylbenzo[c][2,7]naphthyridin-5-one Chemical compound CC(C)C[C@H](N)COC1=CC=2N(C)C(=O)C3=C(C)N=CC=C3C=2C=C1C1=CC=CC=N1 CJYBTGCGPOINHK-KRWDZBQOSA-N 0.000 claims 1
- HRMGBYSRWUAWIG-AWEZNQCLSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4,6-dimethylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@@H](N)CC(C)C)C=C3N(C)C(=O)C2=C1C HRMGBYSRWUAWIG-AWEZNQCLSA-N 0.000 claims 1
- BGLUCWKQMAHNGQ-LBPRGKRZSA-N 8-[(2s)-2-amino-4-methylpentoxy]-4-(difluoromethyl)-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound N1=CC=C2C3=CC=C(OC[C@@H](N)CC(C)C)C=C3N(C)C(=O)C2=C1C(F)F BGLUCWKQMAHNGQ-LBPRGKRZSA-N 0.000 claims 1
- SVROKGXYLBYIMC-IBGZPJMESA-N 8-[(2s)-2-amino-4-methylpentoxy]-4-[(4-methoxyphenyl)methylamino]-6-methylbenzo[c][2,7]naphthyridin-5-one Chemical compound C1=CC(OC)=CC=C1CNC1=NC=CC2=C1C(=O)N(C)C1=CC(OC[C@@H](N)CC(C)C)=CC=C12 SVROKGXYLBYIMC-IBGZPJMESA-N 0.000 claims 1
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| CA2944466C (en) | 2014-04-02 | 2020-06-09 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| EP3292124B1 (en) * | 2015-04-10 | 2019-05-22 | Bristol-Myers Squibb Company | 6h-isochromeno[3,4-c]pyridines and benzo[c][1,7]naphthyridin-6-(5h)-ones as adaptor associated kinase 1 (aak1) inhibitors |
| EP3356330B1 (en) * | 2015-10-01 | 2019-11-20 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| CN108368084B (zh) * | 2015-10-01 | 2020-10-16 | 百时美施贵宝公司 | 联芳基激酶抑制剂 |
| WO2021026349A1 (en) * | 2019-08-08 | 2021-02-11 | Institute For Cancer Research D/B/A The Research Institute Of Fox Chase Cancer Center | Combination therapy for treatment of cancer |
| CN114853664B (zh) * | 2022-06-02 | 2023-09-29 | 河南大学 | 一种钯催化条件下合成α,β-不饱和杂环己基酮类化合物的方法 |
| CN116102542A (zh) * | 2023-02-15 | 2023-05-12 | 如东众意化工有限公司 | 环丙唑醇精制母液中环丙唑醇的回收方法 |
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| FR2955109B1 (fr) * | 2010-01-08 | 2012-09-07 | Sanofi Aventis | Derives de 5-oxo-5,8-dihydro-pyrido[2, 3-d]pyrimidine, leur preparation et leur application en therapeutique |
| JP5752232B2 (ja) * | 2010-03-31 | 2015-07-22 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | プロテインキナーゼ阻害剤としての置換ピロロトリアジン化合物 |
| DK2822555T3 (en) | 2012-03-09 | 2018-02-05 | Lexicon Pharmaceuticals Inc | Inhibition of adapter-associated kinase 1 for the treatment of pain |
| NZ630719A (en) | 2012-03-09 | 2017-01-27 | Lexicon Pharmaceuticals Inc | Imidazo [1, 2 - b] pyridazine - based compounds, compositions comprising them, and uses thereof |
| US8703953B2 (en) | 2012-03-09 | 2014-04-22 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| IN2014DN07384A (enExample) | 2012-03-09 | 2015-04-24 | Lexicon Pharmaceuticals Inc |
-
2013
- 2013-07-19 US US13/946,344 patent/US8901305B2/en active Active
- 2013-07-24 CN CN201380041073.9A patent/CN104507941A/zh active Pending
- 2013-07-24 BR BR112015001890A patent/BR112015001890A2/pt not_active Application Discontinuation
- 2013-07-24 EP EP13744927.8A patent/EP2880032B1/en active Active
- 2013-07-24 EA EA201590268A patent/EA201590268A1/ru unknown
- 2013-07-24 CA CA2880523A patent/CA2880523A1/en not_active Abandoned
- 2013-07-24 MX MX2015000980A patent/MX2015000980A/es unknown
- 2013-07-24 WO PCT/US2013/051831 patent/WO2014022167A1/en not_active Ceased
- 2013-07-24 JP JP2015525460A patent/JP2015528018A/ja not_active Withdrawn
- 2013-07-24 ES ES13744927.8T patent/ES2602965T3/es active Active
- 2013-07-30 TW TW102127296A patent/TW201410676A/zh unknown
- 2013-07-31 AR ARP130102716A patent/AR093758A1/es unknown
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