JP2019505500A5 - - Google Patents
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- Publication number
- JP2019505500A5 JP2019505500A5 JP2018532429A JP2018532429A JP2019505500A5 JP 2019505500 A5 JP2019505500 A5 JP 2019505500A5 JP 2018532429 A JP2018532429 A JP 2018532429A JP 2018532429 A JP2018532429 A JP 2018532429A JP 2019505500 A5 JP2019505500 A5 JP 2019505500A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- carboxamide
- benzoxazole
- phenyl
- amino
- 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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- 150000001875 compounds Chemical class 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000003814 drug Substances 0.000 claims description 12
- 229940124597 therapeutic agent Drugs 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 239000013066 combination product Substances 0.000 claims description 6
- 229940127555 combination product Drugs 0.000 claims description 6
- 230000003463 hyperproliferative effect Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 208000020016 psychiatric disease Diseases 0.000 claims description 6
- -1 5-fluoro-2-hydroxyphenyl Chemical group 0.000 claims description 4
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 4
- 229960003957 dexamethasone Drugs 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- JPMQNQZNHYYGCR-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC=C2N=C(SC2=C1)C1=CC2=C(OCO2)C=C1 JPMQNQZNHYYGCR-UHFFFAOYSA-N 0.000 claims description 2
- OZOAYCMFLIUDFO-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC3=C(OCO3)C=C2)C=C1 OZOAYCMFLIUDFO-UHFFFAOYSA-N 0.000 claims description 2
- AHIAISUUYNGXCC-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC=C2N=C(SC2=C1)C1=CC2=CC=CC=C2O1 AHIAISUUYNGXCC-UHFFFAOYSA-N 0.000 claims description 2
- IOCMEQGKYOKPTE-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound O1CCOC2=C1C=CC(=C2)C=1SC2=C(N=1)C=CC(=C2)C(=O)NO IOCMEQGKYOKPTE-UHFFFAOYSA-N 0.000 claims description 2
- PCXGGZHGEOUESG-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound O1CCOC2=C1C=CC(=C2)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO PCXGGZHGEOUESG-UHFFFAOYSA-N 0.000 claims description 2
- YBLBCJOREMKPOO-UHFFFAOYSA-N 2-(2,3-dihydro-1-benzofuran-5-yl)-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound O1CCC2=C1C=CC(=C2)C=1SC2=C(N=1)C=CC(=C2)C(=O)NO YBLBCJOREMKPOO-UHFFFAOYSA-N 0.000 claims description 2
- CDLFENIFEGWZQA-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=C(Cl)C=CC(Cl)=C2)C=C1 CDLFENIFEGWZQA-UHFFFAOYSA-N 0.000 claims description 2
- LNMKKOTVSFIBEE-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COc1ccc(OC)c(c1)-c1nc2cc(ccc2o1)C(=O)NO LNMKKOTVSFIBEE-UHFFFAOYSA-N 0.000 claims description 2
- LSAYKHJUMFGPSF-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=C(Cl)C=CC=C2Cl)C=C1 LSAYKHJUMFGPSF-UHFFFAOYSA-N 0.000 claims description 2
- QPFWEHZIGGRQHX-UHFFFAOYSA-N 2-(2,6-difluorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound FC1=C(C(=CC=C1)F)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO QPFWEHZIGGRQHX-UHFFFAOYSA-N 0.000 claims description 2
- OFVKXXQFIREQHU-UHFFFAOYSA-N 2-(2,6-dimethoxypyridin-3-yl)-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound COC1=CC=C(C2=NC3=CC=C(C=C3S2)C(=O)NO)C(OC)=N1 OFVKXXQFIREQHU-UHFFFAOYSA-N 0.000 claims description 2
- BZFMZFTZWKLIGM-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ClC1=C(C(=CC=C1)F)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO BZFMZFTZWKLIGM-UHFFFAOYSA-N 0.000 claims description 2
- SOQHGPLOGBSSPZ-UHFFFAOYSA-N 2-(2-chlorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ClC1=C(C=CC=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO SOQHGPLOGBSSPZ-UHFFFAOYSA-N 0.000 claims description 2
- PKTZAUDORDMJDX-UHFFFAOYSA-N 2-(2-fluoro-3-methoxyphenyl)-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound COC1=CC=CC(C2=NC3=CC=C(C=C3S2)C(=O)NO)=C1F PKTZAUDORDMJDX-UHFFFAOYSA-N 0.000 claims description 2
- NIFTXKKOEPFJNJ-UHFFFAOYSA-N 2-(2-fluoro-4-phenylphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound FC=1C=C(C=CC=1C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)C1=CC=CC=C1 NIFTXKKOEPFJNJ-UHFFFAOYSA-N 0.000 claims description 2
- GDLXCAFFMCMTKY-UHFFFAOYSA-N 2-(2-fluoro-4-propan-2-ylphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)c1ccc(-c2nc3cc(ccc3o2)C(=O)NO)c(F)c1 GDLXCAFFMCMTKY-UHFFFAOYSA-N 0.000 claims description 2
- ATUUDUZQUVUJNK-UHFFFAOYSA-N 2-(2-fluoro-4-pyridin-3-ylphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)c1ccc2oc(nc2c1)-c1ccc(cc1F)-c1cccnc1 ATUUDUZQUVUJNK-UHFFFAOYSA-N 0.000 claims description 2
- WNUHXKJWXPJEJT-UHFFFAOYSA-N 2-(2H-benzotriazol-5-yl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC=C3NN=NC3=C2)C=C1 WNUHXKJWXPJEJT-UHFFFAOYSA-N 0.000 claims description 2
- PEJMEJGSUMWYKV-UHFFFAOYSA-N 2-(2H-benzotriazol-5-yl)-N-hydroxy-1,3-benzoxazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C1)N=C(O2)C1=CC=C2NN=NC2=C1 PEJMEJGSUMWYKV-UHFFFAOYSA-N 0.000 claims description 2
- MYIIQQPLIYCSBK-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC(F)=C(F)C=C2)C=C1 MYIIQQPLIYCSBK-UHFFFAOYSA-N 0.000 claims description 2
- OQWFPBVWHUAJOL-UHFFFAOYSA-N 2-(3,4-dihydro-1H-isoquinolin-2-yl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)N2CCC3=C(C2)C=CC=C3)C=C1 OQWFPBVWHUAJOL-UHFFFAOYSA-N 0.000 claims description 2
- DJGRPHRQJJDDGG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COc1ccc(cc1OC)-c1nc2cc(ccc2o1)C(=O)NO DJGRPHRQJJDDGG-UHFFFAOYSA-N 0.000 claims description 2
- FLGVJMXYBGFSED-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-N-hydroxy-1-benzothiophene-6-carboxamide Chemical compound COC=1C=C(C=CC=1OC)C=1SC2=C(C=1)C=CC(=C2)C(=O)NO FLGVJMXYBGFSED-UHFFFAOYSA-N 0.000 claims description 2
- ADQKQAPJWOVGJB-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CC1=C(C)C=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO ADQKQAPJWOVGJB-UHFFFAOYSA-N 0.000 claims description 2
- ACZCHLZGYLVSCS-UHFFFAOYSA-N 2-(3,5-dimethyl-1,2-oxazol-4-yl)-N-hydroxy-1-benzothiophene-5-carboxamide Chemical compound CC1=NOC(=C1C=1SC2=C(C=1)C=C(C=C2)C(=O)NO)C ACZCHLZGYLVSCS-UHFFFAOYSA-N 0.000 claims description 2
- NRJMLYWCUZPYAR-UHFFFAOYSA-N 2-(3-bromophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound BrC=1C=C(C=CC=1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO NRJMLYWCUZPYAR-UHFFFAOYSA-N 0.000 claims description 2
- STPLZSZCVRLQKM-UHFFFAOYSA-N 2-(3-chloro-4-propan-2-yloxyphenyl)-N-hydroxy-1-benzothiophene-5-carboxamide Chemical compound ClC=1C=C(C=CC=1OC(C)C)C=1SC2=C(C=1)C=C(C=C2)C(=O)NO STPLZSZCVRLQKM-UHFFFAOYSA-N 0.000 claims description 2
- ZJRDTFSNJGFZDT-UHFFFAOYSA-N 2-(3-fluoro-4-propan-2-ylphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)c1ccc(cc1F)-c1nc2cc(ccc2o1)C(=O)NO ZJRDTFSNJGFZDT-UHFFFAOYSA-N 0.000 claims description 2
- MDCAIJSNNJFFAM-UHFFFAOYSA-N 2-(3-fluoroanilino)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound FC=1C=C(C=CC=1)NC=1OC2=C(N=1)C=C(C=C2)C(=O)NO MDCAIJSNNJFFAM-UHFFFAOYSA-N 0.000 claims description 2
- VILKFPSNSYKDSR-UHFFFAOYSA-N 2-(3-fluorophenyl)-N-hydroxy-1-benzofuran-5-carboxamide Chemical compound FC=1C=C(C=CC=1)C=1OC2=C(C=1)C=C(C=C2)C(=O)NO VILKFPSNSYKDSR-UHFFFAOYSA-N 0.000 claims description 2
- DVWGOHLCUXYJGR-UHFFFAOYSA-N 2-(4-aminophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound NC1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO DVWGOHLCUXYJGR-UHFFFAOYSA-N 0.000 claims description 2
- MNBCFZJDNJDPQU-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)C1CCN(CC1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO MNBCFZJDNJDPQU-UHFFFAOYSA-N 0.000 claims description 2
- YNEJXMDSQPLEJA-UHFFFAOYSA-N 2-(4-bromo-2-chlorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=C(Cl)C=C(Br)C=C2)C=C1 YNEJXMDSQPLEJA-UHFFFAOYSA-N 0.000 claims description 2
- SKPKSASKGQEEGX-UHFFFAOYSA-N 2-(4-bromo-2-ethoxyphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CCOC1=C(C=CC(Br)=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO SKPKSASKGQEEGX-UHFFFAOYSA-N 0.000 claims description 2
- UECIFWMYJIROCT-UHFFFAOYSA-N 2-(4-bromo-2-fluorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=C(F)C=C(Br)C=C2)C=C1 UECIFWMYJIROCT-UHFFFAOYSA-N 0.000 claims description 2
- PITRKDLJSFRERV-UHFFFAOYSA-N 2-(4-bromo-2-methoxyphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COC1=C(C=CC(Br)=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO PITRKDLJSFRERV-UHFFFAOYSA-N 0.000 claims description 2
- ZHDIHHKZOKUPNO-UHFFFAOYSA-N 2-(4-bromo-2-morpholin-4-ylphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound BrC1=CC(=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)N1CCOCC1 ZHDIHHKZOKUPNO-UHFFFAOYSA-N 0.000 claims description 2
- JHBAPBAEQCVMNV-UHFFFAOYSA-N 2-(4-bromo-3-fluorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound BrC1=C(C=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)F JHBAPBAEQCVMNV-UHFFFAOYSA-N 0.000 claims description 2
- IANPJQMNEHMBBE-UHFFFAOYSA-N 2-(4-bromophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound BrC1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO IANPJQMNEHMBBE-UHFFFAOYSA-N 0.000 claims description 2
- QLDQWNFUYWMVTO-UHFFFAOYSA-N 2-(4-butylphenyl)-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound C(CCC)C1=CC=C(C=C1)C=1SC2=C(N=1)C=CC(=C2)C(=O)NO QLDQWNFUYWMVTO-UHFFFAOYSA-N 0.000 claims description 2
- XAAMFKCXLAEEKG-UHFFFAOYSA-N 2-(4-cyanophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C(#N)C1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO XAAMFKCXLAEEKG-UHFFFAOYSA-N 0.000 claims description 2
- CNOMJOIZUONELB-UHFFFAOYSA-N 2-(4-cyclopropylphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C1(CC1)C1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO CNOMJOIZUONELB-UHFFFAOYSA-N 0.000 claims description 2
- CPJSFVGLZPEXLC-UHFFFAOYSA-N 2-(4-ethylphenyl)-N-hydroxy-1,3-benzothiazole-5-carboxamide Chemical compound C(C)C1=CC=C(C=C1)C=1SC2=C(N=1)C=C(C=C2)C(=O)NO CPJSFVGLZPEXLC-UHFFFAOYSA-N 0.000 claims description 2
- NBYWMEZLKSLXCD-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-hydroxy-1,3-benzothiazole-5-carboxamide Chemical compound FC1=CC=C(C=C1)C=1SC2=C(N=1)C=C(C=C2)C(=O)NO NBYWMEZLKSLXCD-UHFFFAOYSA-N 0.000 claims description 2
- WQXXOANAQOBBPO-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound FC1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO WQXXOANAQOBBPO-UHFFFAOYSA-N 0.000 claims description 2
- DDKPLLRARCBBLA-UHFFFAOYSA-N 2-(4-fluorophenyl)-N-hydroxy-1,3-benzoxazole-6-carboxamide Chemical compound FC1=CC=C(C=C1)C=1OC2=C(N=1)C=CC(=C2)C(=O)NO DDKPLLRARCBBLA-UHFFFAOYSA-N 0.000 claims description 2
- YMNNNLPWLQITCS-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-N-hydroxy-1,3-benzothiazole-5-carboxamide Chemical compound CC(C)(C)C1=CC=C(C=C1)C1=NC2=CC(=CC=C2S1)C(=O)NO YMNNNLPWLQITCS-UHFFFAOYSA-N 0.000 claims description 2
- ZOMWRWDAADUBSA-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO ZOMWRWDAADUBSA-UHFFFAOYSA-N 0.000 claims description 2
- YOERBUNMASZKJF-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-N-hydroxy-1,3-benzoxazole-6-carboxamide Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1OC2=C(N=1)C=CC(=C2)C(=O)NO YOERBUNMASZKJF-UHFFFAOYSA-N 0.000 claims description 2
- FSXJBJGPJFBPQW-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-N-hydroxy-1-benzothiophene-5-carboxamide Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C=1SC2=C(C=1)C=C(C=C2)C(=O)NO FSXJBJGPJFBPQW-UHFFFAOYSA-N 0.000 claims description 2
- KQIZOYLTKIEETE-UHFFFAOYSA-N 2-(5-bromopyridin-3-yl)-N-hydroxy-1,3-benzothiazole-5-carboxamide Chemical compound ONC(=O)c1ccc2sc(nc2c1)-c1cncc(Br)c1 KQIZOYLTKIEETE-UHFFFAOYSA-N 0.000 claims description 2
- GBUHQUZLFIOQPB-UHFFFAOYSA-N 2-(5-chloro-2-hydroxyphenyl)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=C(O)C=CC(Cl)=C2)C=C1 GBUHQUZLFIOQPB-UHFFFAOYSA-N 0.000 claims description 2
- PPAXXIIHBPIMNJ-UHFFFAOYSA-N 2-(5-chloro-2-methoxyphenyl)-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound COC1=C(C=C(Cl)C=C1)C1=NC2=CC=C(C=C2S1)C(=O)NO PPAXXIIHBPIMNJ-UHFFFAOYSA-N 0.000 claims description 2
- FRSHCEDPAMQAHV-UHFFFAOYSA-N 2-(5-fluoro-2-methoxyphenyl)-N-hydroxy-1-benzothiophene-5-carboxamide Chemical compound FC=1C=CC(=C(C=1)C=1SC2=C(C=1)C=C(C=C2)C(=O)NO)OC FRSHCEDPAMQAHV-UHFFFAOYSA-N 0.000 claims description 2
- FBDXNCXBTOVFNJ-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-N-hydroxy-1,3-benzoxazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C1)N=C(O2)C1=CC=C(Cl)N=C1 FBDXNCXBTOVFNJ-UHFFFAOYSA-N 0.000 claims description 2
- BQALFDLVSCOCOH-UHFFFAOYSA-N 2-(N,4-dimethylanilino)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CN(c1nc2cc(ccc2o1)C(=O)NO)c1ccc(C)cc1 BQALFDLVSCOCOH-UHFFFAOYSA-N 0.000 claims description 2
- CMLPQBSORGPKKM-UHFFFAOYSA-N 2-(N-benzylanilino)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)N(C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)C1=CC=CC=C1 CMLPQBSORGPKKM-UHFFFAOYSA-N 0.000 claims description 2
- HMCJRIPVVMJBHS-UHFFFAOYSA-N 2-(benzylamino)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)NC=1OC2=C(N=1)C=C(C=C2)C(=O)NO HMCJRIPVVMJBHS-UHFFFAOYSA-N 0.000 claims description 2
- WXBVHSIJDKHARY-UHFFFAOYSA-N 2-(cyclohexylamino)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C1(CCCCC1)NC=1OC2=C(N=1)C=C(C=C2)C(=O)NO WXBVHSIJDKHARY-UHFFFAOYSA-N 0.000 claims description 2
- JQFAYUIHMVKXCJ-UHFFFAOYSA-N 2-(cyclooctylamino)-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C1(CCCCCCC1)NC=1OC2=C(N=1)C=C(C=C2)C(=O)NO JQFAYUIHMVKXCJ-UHFFFAOYSA-N 0.000 claims description 2
- BELBLJBHEPHLAN-UHFFFAOYSA-N 2-(furan-3-yl)-N-hydroxy-1-benzothiophene-6-carboxamide Chemical compound O1C=C(C=C1)C=1SC2=C(C=1)C=CC(=C2)C(=O)NO BELBLJBHEPHLAN-UHFFFAOYSA-N 0.000 claims description 2
- MEEXRZGBOFXWBZ-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methyl-[2-(dimethylamino)ethyl]amino]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COc1ccc(CN(CCN(C)C)c2nc3cc(ccc3o2)C(=O)NO)cc1OC MEEXRZGBOFXWBZ-UHFFFAOYSA-N 0.000 claims description 2
- RFGRVPIGCXCSIK-UHFFFAOYSA-N 2-[(3-fluorophenoxy)methyl]-N-hydroxy-1-benzofuran-5-carboxamide Chemical compound FC=1C=C(OCC=2OC3=C(C=2)C=C(C=C3)C(=O)NO)C=CC=1 RFGRVPIGCXCSIK-UHFFFAOYSA-N 0.000 claims description 2
- WKQSVJNBERWAKC-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-N-hydroxy-1,3-benzothiazole-5-carboxamide Chemical compound ClC1=CC=C(CC=2SC3=C(N=2)C=C(C=C3)C(=O)NO)C=C1 WKQSVJNBERWAKC-UHFFFAOYSA-N 0.000 claims description 2
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| KR20210068399A (ko) * | 2018-08-06 | 2021-06-09 | 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 주니어 유니버시티 | 신경퇴행성 질병의 치료를 위한 피피에이알지씨1알파 활성제로서 2-아릴벤즈이미다졸 |
| US11524959B1 (en) | 2018-08-08 | 2022-12-13 | Bristol-Myers Squibb Company | Indole and azaindole inhibitors of pad enzymes |
| ES2929200T3 (es) | 2018-08-08 | 2022-11-25 | Bristol Myers Squibb Co | Tienopirroles sustituidos como inhibidores de PAD4 |
| KR102146741B1 (ko) * | 2018-10-31 | 2020-08-21 | 계명대학교 산학협력단 | 항바이러스 조성물 |
| KR20200061310A (ko) * | 2018-11-23 | 2020-06-02 | 주식회사 종근당 | 히스톤 탈아세틸화효소 6 억제제를 포함하는 약학적 조성물 |
| AU2020407664A1 (en) | 2019-12-20 | 2022-08-18 | Tenaya Therapeutics, Inc. | Fluoroalkyl-oxadiazoles and uses thereof |
| TW202140477A (zh) * | 2020-02-12 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 雜環ｐａｄ４抑制劑 |
| EP4161908A1 (en) * | 2020-06-08 | 2023-04-12 | Annji Pharmaceutical Co., Ltd. | Quinazoline derivatives useful as selective hdac6 inhibitors |
| CN112516142B (zh) * | 2020-12-11 | 2021-10-15 | 北京华氏精恒医药科技有限公司 | 一种具有hdac抑制活性的药物组合物、制备方法及其用途 |
| IL307883A (en) | 2021-04-23 | 2023-12-01 | Tenaya Therapeutics Inc | HDAC6 inhibitors for use in the treatment of dilated myocardial disease |
| EP4333841A1 (en) | 2021-05-04 | 2024-03-13 | Tenaya Therapeutics, Inc. | 2-fluoroalkyl-1,3,4-oxadiazol-5-yl-thiazol, hdac6 inhibitors for use in the treatment of metabolic disease and hfpef |
| CN114409638B (zh) * | 2022-02-09 | 2023-02-14 | 深圳大学 | 组蛋白去乙酰化酶8选择性降解剂、制备方法及其在抗肿瘤活性中的应用 |
| CN119212701A (zh) * | 2022-03-17 | 2024-12-27 | 淑明女子大学校 产学协力团 | 新型组蛋白脱乙酰酶杂环抑制剂及包含该抑制剂的药物组合物 |
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| CN118459418B (zh) * | 2024-04-26 | 2025-04-08 | 河北中医药大学 | 一种异羟肟酸类hdac抑制剂及其在制备抗肿瘤药物中的应用 |
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| TWI349664B (en) * | 2003-09-22 | 2011-10-01 | S Bio Pte Ltd | Benzimidazole derivatives: preparation and pharmaceutical applications |
| CN100546980C (zh) * | 2003-09-22 | 2009-10-07 | S*Bio私人有限公司 | 苯并咪唑衍生物:制备方法及医药应用 |
| US20050137234A1 (en) * | 2003-12-19 | 2005-06-23 | Syrrx, Inc. | Histone deacetylase inhibitors |
| ITFI20050041A1 (it) * | 2005-03-15 | 2006-09-16 | Menarini Internat Operations Luxembourg Sa | Idrossammati come inibitori dell'istone deacelitasi, loro preparazione e formulazioni farmaceutiche che li contengono |
| KR101524817B1 (ko) | 2007-04-18 | 2015-06-01 | 깃세이 야쿠힌 고교 가부시키가이샤 | 질소 함유 축합환 유도체, 그것을 함유하는 의약 조성물 및 그 의약 용도 |
| WO2008129276A1 (en) | 2007-04-19 | 2008-10-30 | Boehringer Ingelheim International Gmbh | Disulfonamides useful in the treatment of inflammation |
| EP2217588A4 (en) * | 2007-11-02 | 2013-12-04 | Methylgene Inc | INHIBITORS OF HISTONE DEACETYLASE |
| UA103013C2 (uk) | 2007-12-06 | 2013-09-10 | Тиботек Фармасьютикелз | Амідні сполуки як активатори противірусних препаратів |
| WO2009129335A2 (en) * | 2008-04-15 | 2009-10-22 | Pharmacyclics, Inc. | Selective inhibitors of histone deacetylase |
| TW201028399A (en) * | 2008-11-27 | 2010-08-01 | Shionogi & Co | Pyrimidine derivative and pyridine derivative both having pi3k inhibitory activity |
| US20120015943A1 (en) * | 2010-07-19 | 2012-01-19 | Millennium Pharmacuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| US8987314B2 (en) | 2012-07-19 | 2015-03-24 | Bristol-Myers Squibb Company | Amide, urea or sulfone amide linked benzothiazole inhibitors of endothelial lipase |
| RU2016111675A (ru) | 2013-08-30 | 2017-10-04 | Эмбит Байосайенсиз Корпорейшн | Соединения биарилацетамида и способы их применения |
| ES2694053T3 (es) | 2014-03-12 | 2018-12-17 | Chong Kun Dang Pharmaceutical Corp. | Compuestos novedosos como inhibidores de histona desacetilasa 6 y composiciones farmacéuticas que comprenden los mismos |
| EP3152190B1 (en) * | 2014-06-04 | 2024-07-31 | Haro Pharmaceutical Inc. | 18-20 member bi-polycyclic compounds |
| WO2016180472A1 (en) | 2015-05-11 | 2016-11-17 | Kancera Ab | Benzimidazole derivates useful as inhibitors of mammalian histone deacetylase activity |
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