JP2019505500A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- DUAGNVODMZXKIG-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-N-hydroxy-1,3-benzothiazole-5-carboxamide Chemical compound ONC(=O)C1=CC=C2SC(CC3=CC=C(F)C=C3)=NC2=C1 DUAGNVODMZXKIG-UHFFFAOYSA-N 0.000 claims description 2
- CCWOZBMCGDMOEG-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]-N-hydroxy-1-benzofuran-5-carboxamide Chemical compound C(C)(C)(C)C1=CC=C(OCC=2OC3=C(C=2)C=C(C=C3)C(=O)NO)C=C1 CCWOZBMCGDMOEG-UHFFFAOYSA-N 0.000 claims description 2
- FPJSESLHNWQRAY-XVNBXDOJSA-N 2-[(E)-2-(4-fluorophenyl)ethenyl]-N-hydroxy-1-benzothiophene-5-carboxamide Chemical compound FC1=CC=C(C=C1)/C=C/C=1SC2=C(C=1)C=C(C=C2)C(=O)NO FPJSESLHNWQRAY-XVNBXDOJSA-N 0.000 claims description 2
- BJLFHGLBOQENLI-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CCN(CC)CCC1=NC2=C(O1)C=CC(=C2)C(=O)NO BJLFHGLBOQENLI-UHFFFAOYSA-N 0.000 claims description 2
- CSFDSVYIYAMAII-UHFFFAOYSA-N 2-[2-fluoro-4-(2-fluorophenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=C(F)C=C(C=C2)C2=C(F)C=CC=C2)C=C1 CSFDSVYIYAMAII-UHFFFAOYSA-N 0.000 claims description 2
- LMNFLUFJXVYQLI-UHFFFAOYSA-N 2-[2-fluoro-4-(3-fluoro-2-hydroxyphenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=C(F)C=C(C=C2)C2=C(O)C(F)=CC=C2)C=C1 LMNFLUFJXVYQLI-UHFFFAOYSA-N 0.000 claims description 2
- COKGQMRSHHGYFA-UHFFFAOYSA-N 2-[2-fluoro-4-(4-hydroxyphenyl)phenyl]-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=C(C=C1)O COKGQMRSHHGYFA-UHFFFAOYSA-N 0.000 claims description 2
- KMOCFWFAWNCXCR-UHFFFAOYSA-N 2-[2-fluoro-4-(5-fluoro-2-methoxyphenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COC1=C(C=C(F)C=C1)C1=CC(F)=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO KMOCFWFAWNCXCR-UHFFFAOYSA-N 0.000 claims description 2
- PGXHUMLRLVHWIX-UHFFFAOYSA-N 2-[2-fluoro-4-[2-(hydroxymethyl)phenyl]phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound OCc1ccccc1-c1ccc(-c2nc3cc(ccc3o2)C(=O)NO)c(F)c1 PGXHUMLRLVHWIX-UHFFFAOYSA-N 0.000 claims description 2
- YZYOSOHSYDDZSJ-UHFFFAOYSA-N 2-[2-fluoro-4-[4-(hydroxymethyl)phenyl]phenyl]-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=C(C=C1)CO YZYOSOHSYDDZSJ-UHFFFAOYSA-N 0.000 claims description 2
- HLMFSBOYGDGOPD-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)c1ccc2oc(nc2c1)-c1cc(cc(c1)C(F)(F)F)C(F)(F)F HLMFSBOYGDGOPD-UHFFFAOYSA-N 0.000 claims description 2
- LOMFRTGVNVYCIB-UHFFFAOYSA-N 2-[3-(2-ethoxyethoxy)anilino]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C(C)OCCOC=1C=C(C=CC=1)NC=1OC2=C(N=1)C=C(C=C2)C(=O)NO LOMFRTGVNVYCIB-UHFFFAOYSA-N 0.000 claims description 2
- LJFGGVSSFQUFMO-UHFFFAOYSA-N 2-[3-(diethylamino)propyl]-N-hydroxy-1-benzofuran-6-carboxamide Chemical compound CCN(CC)CCCC1=CC2=C(O1)C=C(C=C2)C(=O)NO LJFGGVSSFQUFMO-UHFFFAOYSA-N 0.000 claims description 2
- GCTYHYUZQXWFEE-OKILXGFUSA-N 2-[3-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C[C@H]1CN(Cc2cccc(c2)-c2nc3cc(ccc3o2)C(=O)NO)C[C@@H](C)O1 GCTYHYUZQXWFEE-OKILXGFUSA-N 0.000 claims description 2
- KAACMPOMWXFWAS-UHFFFAOYSA-N 2-[3-[[bis(2-methylpropyl)amino]methyl]phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)CN(CC(C)C)CC1=CC=CC(=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO KAACMPOMWXFWAS-UHFFFAOYSA-N 0.000 claims description 2
- SRJWVVDDLMEMFH-UHFFFAOYSA-N 2-[3-[[cyclohexyl(methyl)amino]methyl]phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CN(Cc1cccc(c1)-c1nc2cc(ccc2o1)C(=O)NO)C1CCCCC1 SRJWVVDDLMEMFH-UHFFFAOYSA-N 0.000 claims description 2
- NTJMMXWCIJVTGK-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-fluorophenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound O1CCOC2=C1C=CC(=C2)C1=CC(=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)F NTJMMXWCIJVTGK-UHFFFAOYSA-N 0.000 claims description 2
- QAURFBZIWGTLMX-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1-benzofuran-5-yl)-2-fluorophenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound O1CCC2=C1C=CC(=C2)C1=CC(=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)F QAURFBZIWGTLMX-UHFFFAOYSA-N 0.000 claims description 2
- GUQZJQWUYMEFKS-UHFFFAOYSA-N 2-[4-(2,5-difluorophenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC=C(C=C2)C2=C(F)C=CC(F)=C2)C=C1 GUQZJQWUYMEFKS-UHFFFAOYSA-N 0.000 claims description 2
- ALXQIEFTPURNGM-UHFFFAOYSA-N 2-[4-(2-ethoxyethoxy)anilino]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CCOCCOC1=CC=C(NC2=NC3=C(O2)C=CC(=C3)C(=O)NO)C=C1 ALXQIEFTPURNGM-UHFFFAOYSA-N 0.000 claims description 2
- DRTYPYHUAWTDRY-UHFFFAOYSA-N 2-[4-(2-fluoro-3-methoxyphenyl)-2-methoxyphenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COC1=CC=CC(=C1F)C1=CC(OC)=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO DRTYPYHUAWTDRY-UHFFFAOYSA-N 0.000 claims description 2
- WRNYSVXHJONWMJ-UHFFFAOYSA-N 2-[4-(2-fluoro-3-methoxyphenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COc1cccc(-c2ccc(cc2)-c2nc3cc(ccc3o2)C(=O)NO)c1F WRNYSVXHJONWMJ-UHFFFAOYSA-N 0.000 claims description 2
- OIGQMNXCYJPOOY-UHFFFAOYSA-N 2-[4-(2-fluorophenyl)-2-methoxyphenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COC1=C(C=CC(=C1)C1=C(F)C=CC=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO OIGQMNXCYJPOOY-UHFFFAOYSA-N 0.000 claims description 2
- RTHOMIJNOJGNEL-UHFFFAOYSA-N 2-[4-(2-fluorophenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound FC1=C(C=CC=C1)C1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO RTHOMIJNOJGNEL-UHFFFAOYSA-N 0.000 claims description 2
- UBGNMQPIEKCAAV-UHFFFAOYSA-N 2-[4-(3,4-dimethoxyphenyl)-2-fluorophenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COC1=C(OC)C=C(C=C1)C1=CC(F)=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO UBGNMQPIEKCAAV-UHFFFAOYSA-N 0.000 claims description 2
- WHOUVABJLQYHKG-UHFFFAOYSA-N 2-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CC1=C(C(C)=NO1)C1=CC=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO WHOUVABJLQYHKG-UHFFFAOYSA-N 0.000 claims description 2
- AEMJKKYVAIBCKD-UHFFFAOYSA-N 2-[4-(3-fluoro-4-hydroxyphenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC=C(C=C2)C2=CC(F)=C(O)C=C2)C=C1 AEMJKKYVAIBCKD-UHFFFAOYSA-N 0.000 claims description 2
- ZKKZXUFXSAHNGM-UHFFFAOYSA-N 2-[4-(4-amino-3-methoxyphenyl)-2-methoxyphenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COC1=C(N)C=CC(=C1)C1=CC(OC)=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO ZKKZXUFXSAHNGM-UHFFFAOYSA-N 0.000 claims description 2
- BMWXHEGUDNBOHZ-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-2-methoxyphenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COC1=C(C=CC(=C1)C1=CC=C(F)C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO BMWXHEGUDNBOHZ-UHFFFAOYSA-N 0.000 claims description 2
- AZPMACHLOBTJJB-UHFFFAOYSA-N 2-[4-(5-chloro-2-methoxyphenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COC1=C(C=C(Cl)C=C1)C1=CC=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO AZPMACHLOBTJJB-UHFFFAOYSA-N 0.000 claims description 2
- DMNPPJXGHAYKEH-UHFFFAOYSA-N 2-[4-(5-fluoro-2-hydroxyphenyl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC=C(C=C2)C2=C(O)C=CC(F)=C2)C=C1 DMNPPJXGHAYKEH-UHFFFAOYSA-N 0.000 claims description 2
- CHYHVAVXYVIMTQ-UHFFFAOYSA-N 2-[4-(benzenesulfonamido)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)NS(=O)(=O)C2=CC=CC=C2)C=1 CHYHVAVXYVIMTQ-UHFFFAOYSA-N 0.000 claims description 2
- RRSVPHSVFCCKOW-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound FC(OC1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)F RRSVPHSVFCCKOW-UHFFFAOYSA-N 0.000 claims description 2
- LJDJIOWRTHTPJH-UHFFFAOYSA-N 2-[4-(dimethylcarbamoyl)phenyl]-N-hydroxy-1-benzothiophene-5-carboxamide Chemical compound CN(C(=O)C1=CC=C(C=C1)C=1SC2=C(C=1)C=C(C=C2)C(=O)NO)C LJDJIOWRTHTPJH-UHFFFAOYSA-N 0.000 claims description 2
- IPGPGTXJVDINDE-UHFFFAOYSA-N 2-[4-[(benzylamino)methyl]piperidin-1-yl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)NCC1CCN(CC1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO IPGPGTXJVDINDE-UHFFFAOYSA-N 0.000 claims description 2
- XIKANKDKIIFYSU-UHFFFAOYSA-N 2-[4-[(dimethylamino)methyl]phenyl]-N-hydroxy-1,3-benzothiazole-6-carboxamide Chemical compound CN(C)CC1=CC=C(C=C1)C=1SC2=C(N=1)C=CC(=C2)C(=O)NO XIKANKDKIIFYSU-UHFFFAOYSA-N 0.000 claims description 2
- SNMGEAAXUNEHMR-UHFFFAOYSA-N 2-[4-[(dimethylamino)methyl]phenyl]-N-hydroxy-1-benzofuran-6-carboxamide Chemical compound CN(C)CC1=CC=C(C=C1)C=1OC2=C(C=1)C=CC(=C2)C(=O)NO SNMGEAAXUNEHMR-UHFFFAOYSA-N 0.000 claims description 2
- GANOCNVSSQIISP-UHFFFAOYSA-N 2-[4-[(tert-butylamino)methyl]phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C(C)(C)(C)NCC1=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO GANOCNVSSQIISP-UHFFFAOYSA-N 0.000 claims description 2
- ZGDROGDZZCBQRI-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethyl]phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CCN(CC)CCC1=CC=C(C=C1)C2=NC3=C(O2)C=CC(=C3)C(=O)NO ZGDROGDZZCBQRI-UHFFFAOYSA-N 0.000 claims description 2
- FXCPEOVPZGWFQB-OKILXGFUSA-N 2-[4-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C[C@H]1CN(CC2=CC=C(C=C2)C2=NC3=C(O2)C=CC(=C3)C(=O)NO)C[C@@H](C)O1 FXCPEOVPZGWFQB-OKILXGFUSA-N 0.000 claims description 2
- GPGLAWZPSUEMKD-UHFFFAOYSA-N 2-[4-[[bis(2-methylpropyl)amino]methyl]phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)CN(CC(C)C)CC1=CC=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO GPGLAWZPSUEMKD-UHFFFAOYSA-N 0.000 claims description 2
- HWNAEWSZZBSTMT-UHFFFAOYSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-N-hydroxy-1-benzothiophene-5-carboxamide Chemical compound FC1=C(C=C(C=C1)C=1SC2=C(C=1)C=C(C=C2)C(=O)NO)C(F)(F)F HWNAEWSZZBSTMT-UHFFFAOYSA-N 0.000 claims description 2
- MODDSNXIPUDZFG-UHFFFAOYSA-N 2-[6-(cycloheptylamino)pyridin-3-yl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)c1ccc2oc(nc2c1)-c1ccc(NC2CCCCCC2)nc1 MODDSNXIPUDZFG-UHFFFAOYSA-N 0.000 claims description 2
- JQKGVLVRYWMBHT-TXEJJXNPSA-N 2-[6-[(2S,6R)-2,6-dimethylmorpholin-4-yl]pyridin-3-yl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound C[C@@H]1CN(C[C@@H](O1)C)C1=CC=C(C=N1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO JQKGVLVRYWMBHT-TXEJJXNPSA-N 0.000 claims description 2
- KOEIILZCXBNLBI-UHFFFAOYSA-N 2-[6-[bis(2-methoxyethyl)amino]pyridin-3-yl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COCCN(C1=CC=C(C=N1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)CCOC KOEIILZCXBNLBI-UHFFFAOYSA-N 0.000 claims description 2
- MRRTWODSDBERAQ-UHFFFAOYSA-N 2-[[1-(3-fluorophenyl)cyclohexyl]amino]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound FC=1C=C(C=CC=1)C1(CCCCC1)NC=1OC2=C(N=1)C=C(C=C2)C(=O)NO MRRTWODSDBERAQ-UHFFFAOYSA-N 0.000 claims description 2
- CWAILNPRJARNII-UHFFFAOYSA-N 2-[benzyl(methyl)amino]-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)C CWAILNPRJARNII-UHFFFAOYSA-N 0.000 claims description 2
- WJXINWQHSJTFFR-UHFFFAOYSA-N 2-anilino-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)NC2=CC=CC=C2)C=1 WJXINWQHSJTFFR-UHFFFAOYSA-N 0.000 claims description 2
- RVERRVNAICJDCL-UHFFFAOYSA-N 2-dibenzofuran-4-yl-N-hydroxy-1-benzothiophene-6-carboxamide Chemical compound C1=CC=C(C=2OC3=C(C=21)C=CC=C3)C=1SC2=C(C=1)C=CC(=C2)C(=O)NO RVERRVNAICJDCL-UHFFFAOYSA-N 0.000 claims description 2
- SIGVPSDCBNOGEB-UHFFFAOYSA-N N-hydroxy-2-(1-methylpyrazol-4-yl)-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C=2C=NN(C=2)C)C=1 SIGVPSDCBNOGEB-UHFFFAOYSA-N 0.000 claims description 2
- OURIXHGRFIUGQY-UHFFFAOYSA-N N-hydroxy-2-(1H-indol-5-yl)-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)c1ccc2sc(cc2c1)-c1ccc2[nH]ccc2c1 OURIXHGRFIUGQY-UHFFFAOYSA-N 0.000 claims description 2
- CADRTLGROCEXPO-UHFFFAOYSA-N N-hydroxy-2-(1H-pyrazol-4-yl)-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C=2C=NNC=2)C=1 CADRTLGROCEXPO-UHFFFAOYSA-N 0.000 claims description 2
- YVYYJMSPZWRCHG-UHFFFAOYSA-N N-hydroxy-2-(2-hydroxynaphthalen-1-yl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=C(C=CC3=CC=CC=C23)O)C=1 YVYYJMSPZWRCHG-UHFFFAOYSA-N 0.000 claims description 2
- ICEMYPPWRPXCEL-UHFFFAOYSA-N N-hydroxy-2-(2-hydroxyphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=C(C=CC=C2)O)C=1 ICEMYPPWRPXCEL-UHFFFAOYSA-N 0.000 claims description 2
- YEYVLINFRJUZHY-UHFFFAOYSA-N N-hydroxy-2-(2-hydroxypropan-2-yl)-1-benzofuran-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C(O2)C(C)(C)O)C=C1 YEYVLINFRJUZHY-UHFFFAOYSA-N 0.000 claims description 2
- CBQZVWQTASQSEF-UHFFFAOYSA-N N-hydroxy-2-(2-methoxy-4-phenylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=C(C=C(C=C2)C2=CC=CC=C2)OC)C=1 CBQZVWQTASQSEF-UHFFFAOYSA-N 0.000 claims description 2
- OUDCUBUZXKHHPM-UHFFFAOYSA-N N-hydroxy-2-(2-methoxyanilino)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)NC2=C(C=CC=C2)OC)C=1 OUDCUBUZXKHHPM-UHFFFAOYSA-N 0.000 claims description 2
- WYDMVJRPZOTDDW-UHFFFAOYSA-N N-hydroxy-2-(2-methoxyphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=C(C=CC=C2)OC)C=1 WYDMVJRPZOTDDW-UHFFFAOYSA-N 0.000 claims description 2
- MRAJNHXZHWMGEZ-UHFFFAOYSA-N N-hydroxy-2-(2-methoxypyridin-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound COC1=NC=CC=C1C1=NC2=C(O1)C=CC(=C2)C(=O)NO MRAJNHXZHWMGEZ-UHFFFAOYSA-N 0.000 claims description 2
- SOJLYPIYVCFZTG-UHFFFAOYSA-N N-hydroxy-2-(2-methoxypyridin-4-yl)-1,3-benzothiazole-6-carboxamide Chemical compound COC1=NC=CC(=C1)C1=NC2=CC=C(C=C2S1)C(=O)NO SOJLYPIYVCFZTG-UHFFFAOYSA-N 0.000 claims description 2
- GUJJUCVFRWSOPX-UHFFFAOYSA-N N-hydroxy-2-(2-methylanilino)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)NC2=C(C=CC=C2)C)C=1 GUJJUCVFRWSOPX-UHFFFAOYSA-N 0.000 claims description 2
- ZGMGQEOFFVNHBS-UHFFFAOYSA-N N-hydroxy-2-(2-methylpyridin-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound CC1=NC=CC=C1C1=NC2=C(O1)C=CC(=C2)C(=O)NO ZGMGQEOFFVNHBS-UHFFFAOYSA-N 0.000 claims description 2
- ZPMUTFQKNARTJQ-UHFFFAOYSA-N N-hydroxy-2-(2-methylsulfonylphenyl)-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(N=C(S2)C2=C(C=CC=C2)S(=O)(=O)C)C=C1 ZPMUTFQKNARTJQ-UHFFFAOYSA-N 0.000 claims description 2
- ONDNPYVUUHZXMB-UHFFFAOYSA-N N-hydroxy-2-(2-phenyl-1H-imidazol-5-yl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CN=C(N2)C2=CC=CC=C2)C=C1 ONDNPYVUUHZXMB-UHFFFAOYSA-N 0.000 claims description 2
- CNYVEXDMLLJLKS-UHFFFAOYSA-N N-hydroxy-2-(2-phenylethylamino)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(NCCC3=CC=CC=C3)=N2)C=C1 CNYVEXDMLLJLKS-UHFFFAOYSA-N 0.000 claims description 2
- OLQHVVRQPKVCNI-UHFFFAOYSA-N N-hydroxy-2-(2-propan-2-ylanilino)-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)c1ccccc1Nc1nc2cc(ccc2o1)C(=O)NO OLQHVVRQPKVCNI-UHFFFAOYSA-N 0.000 claims description 2
- KHXLRABDBUMMLL-UHFFFAOYSA-N N-hydroxy-2-(3-hydroxyphenyl)-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(N=C(S2)C2=CC(=CC=C2)O)C=C1 KHXLRABDBUMMLL-UHFFFAOYSA-N 0.000 claims description 2
- VSWDZCHGKXFLKN-UHFFFAOYSA-N N-hydroxy-2-(3-hydroxyphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC(=CC=C2)O)C=1 VSWDZCHGKXFLKN-UHFFFAOYSA-N 0.000 claims description 2
- BLCXEQCVKXNNQH-UHFFFAOYSA-N N-hydroxy-2-(3-hydroxyphenyl)-1-benzofuran-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C(O2)C2=CC(=CC=C2)O)C=C1 BLCXEQCVKXNNQH-UHFFFAOYSA-N 0.000 claims description 2
- SNALKNOKEFBQTR-UHFFFAOYSA-N N-hydroxy-2-(3-methoxyanilino)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)NC2=CC(=CC=C2)OC)C=1 SNALKNOKEFBQTR-UHFFFAOYSA-N 0.000 claims description 2
- FDUWAKJKLASRSS-UHFFFAOYSA-N N-hydroxy-2-(3-methoxyphenyl)-1-benzofuran-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C(O2)C2=CC(=CC=C2)OC)C=C1 FDUWAKJKLASRSS-UHFFFAOYSA-N 0.000 claims description 2
- IPAPKWURZXGSMP-UHFFFAOYSA-N N-hydroxy-2-(3-methoxyphenyl)-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C2=CC(=CC=C2)OC)C=1 IPAPKWURZXGSMP-UHFFFAOYSA-N 0.000 claims description 2
- APJKUPVVGRXFDX-UHFFFAOYSA-N N-hydroxy-2-(3-phenylanilino)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(NC3=CC=CC(=C3)C3=CC=CC=C3)=N2)C=C1 APJKUPVVGRXFDX-UHFFFAOYSA-N 0.000 claims description 2
- VXYPCRJQOSUZMF-UHFFFAOYSA-N N-hydroxy-2-(3-phenylmethoxyanilino)-1,3-benzoxazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=CC=1)NC=1OC2=C(N=1)C=C(C=C2)C(=O)NO VXYPCRJQOSUZMF-UHFFFAOYSA-N 0.000 claims description 2
- UYRFCSPAWPLMHW-UHFFFAOYSA-N N-hydroxy-2-(3-phenylmethoxyphenyl)-1,3-benzothiazole-6-carboxamide Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=CC=1)C=1SC2=C(N=1)C=CC(=C2)C(=O)NO UYRFCSPAWPLMHW-UHFFFAOYSA-N 0.000 claims description 2
- CFNRLZCKBPTNCB-UHFFFAOYSA-N N-hydroxy-2-(3-propan-2-ylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)c1cccc(c1)-c1nc2cc(ccc2o1)C(=O)NO CFNRLZCKBPTNCB-UHFFFAOYSA-N 0.000 claims description 2
- PHKBUERRKRYELH-UHFFFAOYSA-N N-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=C(C=C(C=C2)O)OC)C=1 PHKBUERRKRYELH-UHFFFAOYSA-N 0.000 claims description 2
- NHLRGYSMYXQUER-UHFFFAOYSA-N N-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzothiophene-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C(S2)C2=CC(=C(C=C2)O)OC)C=C1 NHLRGYSMYXQUER-UHFFFAOYSA-N 0.000 claims description 2
- OFYWDDGDKBXSCY-UHFFFAOYSA-N N-hydroxy-2-(4-hydroxyphenyl)-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(N=C(S2)C2=CC=C(C=C2)O)C=C1 OFYWDDGDKBXSCY-UHFFFAOYSA-N 0.000 claims description 2
- CODFYVNOADIAMB-UHFFFAOYSA-N N-hydroxy-2-(4-hydroxyphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)O)C=1 CODFYVNOADIAMB-UHFFFAOYSA-N 0.000 claims description 2
- ITGOKTYUTLMRDA-UHFFFAOYSA-N N-hydroxy-2-(4-methoxy-N-methylanilino)-1,3-benzoxazole-5-carboxamide Chemical compound COc1ccc(cc1)N(C)c1nc2cc(ccc2o1)C(=O)NO ITGOKTYUTLMRDA-UHFFFAOYSA-N 0.000 claims description 2
- IOLHLQQLEIJQSR-UHFFFAOYSA-N N-hydroxy-2-(4-methoxyanilino)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)OC)C=1 IOLHLQQLEIJQSR-UHFFFAOYSA-N 0.000 claims description 2
- YSLCRWROSQIAEX-UHFFFAOYSA-N N-hydroxy-2-(4-methoxyphenyl)-1,3-benzothiazole-5-carboxamide Chemical compound COc1ccc(cc1)-c1nc2cc(ccc2s1)C(=O)NO YSLCRWROSQIAEX-UHFFFAOYSA-N 0.000 claims description 2
- SFAFNFBAORPLMN-UHFFFAOYSA-N N-hydroxy-2-(4-methoxyphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)OC)C=1 SFAFNFBAORPLMN-UHFFFAOYSA-N 0.000 claims description 2
- UZOPAAOBLZZNTA-UHFFFAOYSA-N N-hydroxy-2-(4-methoxyphenyl)-1,3-benzoxazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(N=C(O2)C2=CC=C(C=C2)OC)C=C1 UZOPAAOBLZZNTA-UHFFFAOYSA-N 0.000 claims description 2
- IRRANJDNTWUUMB-UHFFFAOYSA-N N-hydroxy-2-(4-methoxyphenyl)-1-benzofuran-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(O2)C2=CC=C(C=C2)OC)C=1 IRRANJDNTWUUMB-UHFFFAOYSA-N 0.000 claims description 2
- FRWQPOCGDYGKBY-UHFFFAOYSA-N N-hydroxy-2-(4-methoxyphenyl)-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C2=CC=C(C=C2)OC)C=1 FRWQPOCGDYGKBY-UHFFFAOYSA-N 0.000 claims description 2
- PFWVFIXKPQEYBO-UHFFFAOYSA-N N-hydroxy-2-(4-methylanilino)-1,3-benzoxazole-5-carboxamide Chemical compound Cc1ccc(Nc2nc3cc(ccc3o2)C(=O)NO)cc1 PFWVFIXKPQEYBO-UHFFFAOYSA-N 0.000 claims description 2
- PNVDYZFHFVVQNT-UHFFFAOYSA-N N-hydroxy-2-(4-methylsulfonylphenyl)-1,3-benzothiazole-6-carboxamide Chemical compound CS(=O)(=O)c1ccc(cc1)-c1nc2ccc(cc2s1)C(=O)NO PNVDYZFHFVVQNT-UHFFFAOYSA-N 0.000 claims description 2
- YZVIESOYMFUBPW-UHFFFAOYSA-N N-hydroxy-2-(4-phenylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound C1(=CC=C(C=C1)C=1OC2=C(N=1)C=C(C=C2)C(=O)NO)C1=CC=CC=C1 YZVIESOYMFUBPW-UHFFFAOYSA-N 0.000 claims description 2
- CGJYNSJSIUMDOC-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-yl-2-pyrrolidin-1-ylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)c1ccc(-c2nc3cc(ccc3o2)C(=O)NO)c(c1)N1CCCC1 CGJYNSJSIUMDOC-UHFFFAOYSA-N 0.000 claims description 2
- JUGAAXDFRYLQLC-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylanilino)-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)c1ccc(Nc2nc3cc(ccc3o2)C(=O)NO)cc1 JUGAAXDFRYLQLC-UHFFFAOYSA-N 0.000 claims description 2
- YIQVYQNMHZMEBO-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1,3-benzothiazole-5-carboxamide Chemical compound CC(C)c1ccc(cc1)-c1nc2cc(ccc2s1)C(=O)NO YIQVYQNMHZMEBO-UHFFFAOYSA-N 0.000 claims description 2
- MFSKCGMUXCCXFA-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1,3-benzothiazole-6-carboxamide Chemical compound CC(C)c1ccc(cc1)-c1nc2ccc(cc2s1)C(=O)NO MFSKCGMUXCCXFA-UHFFFAOYSA-N 0.000 claims description 2
- BIFARDGGEYHWIF-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)c1ccc(cc1)-c1nc2cc(ccc2o1)C(=O)NO BIFARDGGEYHWIF-UHFFFAOYSA-N 0.000 claims description 2
- HYXBUQVNHGSUGX-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1-benzofuran-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(O2)C2=CC=C(C=C2)C(C)C)C=1 HYXBUQVNHGSUGX-UHFFFAOYSA-N 0.000 claims description 2
- IJJQANUHOQGNJT-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1-benzofuran-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C(O2)C2=CC=C(C=C2)C(C)C)C=C1 IJJQANUHOQGNJT-UHFFFAOYSA-N 0.000 claims description 2
- YIHDPUFALLFOEE-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C2=CC=C(C=C2)C(C)C)C=1 YIHDPUFALLFOEE-UHFFFAOYSA-N 0.000 claims description 2
- MAIAQNBLEGJEJE-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1-benzothiophene-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C(S2)C2=CC=C(C=C2)C(C)C)C=C1 MAIAQNBLEGJEJE-UHFFFAOYSA-N 0.000 claims description 2
- BFFLLQYEXGNTDM-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)furo[2,3-b]pyridine-5-carboxamide Chemical compound ONC(=O)C=1C=C2C(=NC=1)OC(=C2)C1=CC=C(C=C1)C(C)C BFFLLQYEXGNTDM-UHFFFAOYSA-N 0.000 claims description 2
- MHKYIRMQWKSSJH-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)furo[3,2-b]pyridine-6-carboxamide Chemical compound CC(C)C1=CC=C(C=C1)C1=CC2=NC=C(C=C2O1)C(=O)NO MHKYIRMQWKSSJH-UHFFFAOYSA-N 0.000 claims description 2
- GFYQIAIMLPJEAP-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)thieno[3,2-b]pyridine-6-carboxamide Chemical compound ONC(=O)C=1C=C2C(=NC=1)C=C(S2)C1=CC=C(C=C1)C(C)C GFYQIAIMLPJEAP-UHFFFAOYSA-N 0.000 claims description 2
- XKVZVVDXUHSRPY-UHFFFAOYSA-N N-hydroxy-2-(4-propylanilino)-1,3-benzoxazole-5-carboxamide Chemical compound CCCC1=CC=C(NC2=NC3=C(O2)C=CC(=C3)C(=O)NO)C=C1 XKVZVVDXUHSRPY-UHFFFAOYSA-N 0.000 claims description 2
- HQGQRFVCJNKHCX-UHFFFAOYSA-N N-hydroxy-2-(4-propylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)CCC)C=1 HQGQRFVCJNKHCX-UHFFFAOYSA-N 0.000 claims description 2
- LILXXFHWGZEZCS-UHFFFAOYSA-N N-hydroxy-2-(4-pyridin-3-ylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC=C(C=C2)C2=CC=CN=C2)C=C1 LILXXFHWGZEZCS-UHFFFAOYSA-N 0.000 claims description 2
- KCTZDQYHRDERPO-UHFFFAOYSA-N N-hydroxy-2-(4-pyridin-4-ylphenyl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)C2=CC=NC=C2)C=1 KCTZDQYHRDERPO-UHFFFAOYSA-N 0.000 claims description 2
- OVCODCDMWLWKOU-UHFFFAOYSA-N N-hydroxy-2-(5-methoxypyridin-3-yl)-1,3-benzothiazole-6-carboxamide Chemical compound COc1cncc(c1)-c1nc2ccc(cc2s1)C(=O)NO OVCODCDMWLWKOU-UHFFFAOYSA-N 0.000 claims description 2
- IRRUSUSXUVCITQ-UHFFFAOYSA-N N-hydroxy-2-(6-methoxypyridin-3-yl)-1,3-benzothiazole-6-carboxamide Chemical compound COC1=CC=C(C=N1)C1=NC2=CC=C(C=C2S1)C(=O)NO IRRUSUSXUVCITQ-UHFFFAOYSA-N 0.000 claims description 2
- RVMUUCQXXKQQQV-UHFFFAOYSA-N N-hydroxy-2-(6-methoxypyridin-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound COC1=CC=C(C=N1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO RVMUUCQXXKQQQV-UHFFFAOYSA-N 0.000 claims description 2
- NLEZIYCWQRHNON-UHFFFAOYSA-N N-hydroxy-2-(6-methoxypyridin-3-yl)-1-benzofuran-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(O2)C=2C=NC(=CC=2)OC)C=1 NLEZIYCWQRHNON-UHFFFAOYSA-N 0.000 claims description 2
- AWOCKKLSTRUNPG-UHFFFAOYSA-N N-hydroxy-2-(6-methoxypyridin-3-yl)-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C=2C=NC(=CC=2)OC)C=1 AWOCKKLSTRUNPG-UHFFFAOYSA-N 0.000 claims description 2
- JLMMNKYRUZZAIY-UHFFFAOYSA-N N-hydroxy-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC=C(N=C2)N2CCOCC2)C=C1 JLMMNKYRUZZAIY-UHFFFAOYSA-N 0.000 claims description 2
- YLKMMDVEGDQABC-UHFFFAOYSA-N N-hydroxy-2-(6-phenylpyridin-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC=C(N=C2)C2=CC=CC=C2)C=C1 YLKMMDVEGDQABC-UHFFFAOYSA-N 0.000 claims description 2
- PVHDXEDJKKAKFI-UHFFFAOYSA-N N-hydroxy-2-(6-propan-2-yloxypyridin-3-yl)-1,3-benzothiazole-6-carboxamide Chemical compound CC(C)Oc1ccc(cn1)-c1nc2ccc(cc2s1)C(=O)NO PVHDXEDJKKAKFI-UHFFFAOYSA-N 0.000 claims description 2
- UIRCTMJWGCXSIW-UHFFFAOYSA-N N-hydroxy-2-(6-propan-2-ylpyridin-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound CC(C)c1ccc(cn1)-c1nc2cc(ccc2o1)C(=O)NO UIRCTMJWGCXSIW-UHFFFAOYSA-N 0.000 claims description 2
- CWKUKDMTXXCLDS-UHFFFAOYSA-N N-hydroxy-2-(6-propan-2-ylsulfanylpyridin-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)SC(C)C)C=1 CWKUKDMTXXCLDS-UHFFFAOYSA-N 0.000 claims description 2
- DIBJDJFVAPFZLX-UHFFFAOYSA-N N-hydroxy-2-(6-pyridin-3-ylpyridin-3-yl)-1,3-benzoxazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C1)N=C(O2)C1=CN=C(C=C1)C1=CC=CN=C1 DIBJDJFVAPFZLX-UHFFFAOYSA-N 0.000 claims description 2
- AZEPNDSLQBDQSA-UHFFFAOYSA-N N-hydroxy-2-(6-pyrrolidin-1-ylpyridin-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)N2CCCC2)C=1 AZEPNDSLQBDQSA-UHFFFAOYSA-N 0.000 claims description 2
- JAALYXHFRPXEPF-UHFFFAOYSA-N N-hydroxy-2-(7-methoxy-1-benzofuran-2-yl)-1,3-benzothiazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(S2)C=2OC3=C(C=2)C=CC=C3OC)C=1 JAALYXHFRPXEPF-UHFFFAOYSA-N 0.000 claims description 2
- OKPVMXPCTHGYGG-UHFFFAOYSA-N N-hydroxy-2-(hydroxymethyl)-1,3-benzothiazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(S2)CO)C=1 OKPVMXPCTHGYGG-UHFFFAOYSA-N 0.000 claims description 2
- GPXRWKYSWGOWSO-UHFFFAOYSA-N N-hydroxy-2-(hydroxymethyl)-1-benzofuran-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(O2)CO)C=1 GPXRWKYSWGOWSO-UHFFFAOYSA-N 0.000 claims description 2
- XTIJGZAOXHHBCT-UHFFFAOYSA-N N-hydroxy-2-(hydroxymethyl)-1-benzofuran-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C(O2)CO)C=C1 XTIJGZAOXHHBCT-UHFFFAOYSA-N 0.000 claims description 2
- YQXPZEOEHDZXKI-UHFFFAOYSA-N N-hydroxy-2-(naphthalen-1-ylmethylamino)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)NCC2=CC=CC3=CC=CC=C23)C=1 YQXPZEOEHDZXKI-UHFFFAOYSA-N 0.000 claims description 2
- TWWLEKVJHSMORL-UHFFFAOYSA-N N-hydroxy-2-(phenylmethoxymethyl)-1,3-benzothiazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)OCC=1SC2=C(N=1)C=C(C=C2)C(=O)NO TWWLEKVJHSMORL-UHFFFAOYSA-N 0.000 claims description 2
- AELIOMOOVZVZDJ-UHFFFAOYSA-N N-hydroxy-2-(piperidin-1-ylmethyl)-1,3-benzothiazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(S2)CN2CCCCC2)C=1 AELIOMOOVZVZDJ-UHFFFAOYSA-N 0.000 claims description 2
- DTTKFKHSALHCPK-UHFFFAOYSA-N N-hydroxy-2-[(4-methoxyphenyl)methyl-methylamino]-1,3-benzoxazole-5-carboxamide Chemical compound COc1ccc(CN(C)c2nc3cc(ccc3o2)C(=O)NO)cc1 DTTKFKHSALHCPK-UHFFFAOYSA-N 0.000 claims description 2
- XQQFQLILSJPDKY-UHFFFAOYSA-N N-hydroxy-2-[(4-methoxyphenyl)methylamino]-1,3-benzoxazole-5-carboxamide Chemical compound COC1=CC=C(CNC2=NC3=C(O2)C=CC(=C3)C(=O)NO)C=C1 XQQFQLILSJPDKY-UHFFFAOYSA-N 0.000 claims description 2
- DCWBAQUXOGGDPJ-UHFFFAOYSA-N N-hydroxy-2-[(4-phenylphenyl)methylamino]-1,3-benzoxazole-5-carboxamide Chemical compound C1(=CC=C(C=C1)CNC=1OC2=C(N=1)C=C(C=C2)C(=O)NO)C1=CC=CC=C1 DCWBAQUXOGGDPJ-UHFFFAOYSA-N 0.000 claims description 2
- PQQKNJMXCUZIKX-UHFFFAOYSA-N N-hydroxy-2-[(4-propan-2-ylanilino)methyl]-1,3-benzothiazole-5-carboxamide Chemical compound CC(C)C1=CC=C(NCC2=NC3=CC(=CC=C3S2)C(=O)NO)C=C1 PQQKNJMXCUZIKX-UHFFFAOYSA-N 0.000 claims description 2
- VQEUGYKZCYXMPQ-UHFFFAOYSA-N N-hydroxy-2-[(4-pyridin-4-ylphenyl)methyl]-1,3-benzothiazole-5-carboxamide Chemical compound ONC(=O)C1=CC=C2SC(CC3=CC=C(C=C3)C3=CC=NC=C3)=NC2=C1 VQEUGYKZCYXMPQ-UHFFFAOYSA-N 0.000 claims description 2
- KIWNVBRNYIOXRR-UHFFFAOYSA-N N-hydroxy-2-[2-(4-methoxyphenyl)ethylamino]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)NCCC2=CC=C(C=C2)OC)C=1 KIWNVBRNYIOXRR-UHFFFAOYSA-N 0.000 claims description 2
- ORFMTGSQGREDEW-UHFFFAOYSA-N N-hydroxy-2-[2-(hydroxymethyl)phenyl]-1-benzofuran-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(O2)C2=C(C=CC=C2)CO)C=1 ORFMTGSQGREDEW-UHFFFAOYSA-N 0.000 claims description 2
- QVYCRWCTBXIDPH-UHFFFAOYSA-N N-hydroxy-2-[2-methoxy-4-(4-propan-2-ylphenyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound COc1cc(ccc1-c1nc2cc(ccc2o1)C(=O)NO)-c1ccc(cc1)C(C)C QVYCRWCTBXIDPH-UHFFFAOYSA-N 0.000 claims description 2
- VCCQPYCFMZXUNS-UHFFFAOYSA-N N-hydroxy-2-[3-(2-morpholin-4-ylethoxy)anilino]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)c1ccc2oc(Nc3cccc(OCCN4CCOCC4)c3)nc2c1 VCCQPYCFMZXUNS-UHFFFAOYSA-N 0.000 claims description 2
- NKAGCJQGHRYBMQ-UHFFFAOYSA-N N-hydroxy-2-[3-(hydroxymethyl)phenyl]-1,3-benzothiazole-6-carboxamide Chemical compound OCc1cccc(c1)-c1nc2ccc(cc2s1)C(=O)NO NKAGCJQGHRYBMQ-UHFFFAOYSA-N 0.000 claims description 2
- POJHJPYPQFMQRK-UHFFFAOYSA-N N-hydroxy-2-[3-(piperidin-1-ylmethyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)c1ccc2oc(nc2c1)-c1cccc(CN2CCCCC2)c1 POJHJPYPQFMQRK-UHFFFAOYSA-N 0.000 claims description 2
- VDHSTDQQCICFGQ-UHFFFAOYSA-N N-hydroxy-2-[3-(piperidin-1-ylmethyl)phenyl]-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C2=CC(=CC=C2)CN2CCCCC2)C=1 VDHSTDQQCICFGQ-UHFFFAOYSA-N 0.000 claims description 2
- TYCGHEJXKLGQRS-UHFFFAOYSA-N N-hydroxy-2-[3-(trifluoromethyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)c1ccc2oc(nc2c1)-c1cccc(c1)C(F)(F)F TYCGHEJXKLGQRS-UHFFFAOYSA-N 0.000 claims description 2
- MNNONRQHUOGXID-UHFFFAOYSA-N N-hydroxy-2-[3-(trifluoromethyl)phenyl]-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C2=CC(=CC=C2)C(F)(F)F)C=1 MNNONRQHUOGXID-UHFFFAOYSA-N 0.000 claims description 2
- WZFDEYMWGCSUOK-UHFFFAOYSA-N N-hydroxy-2-[3-[[2-methoxyethyl(methyl)amino]methyl]phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound COCCN(C)Cc1cccc(c1)-c1nc2cc(ccc2o1)C(=O)NO WZFDEYMWGCSUOK-UHFFFAOYSA-N 0.000 claims description 2
- RKXLNXBWUFSQIR-UHFFFAOYSA-N N-hydroxy-2-[4-(2-hydroxyphenyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)C2=C(C=CC=C2)O)C=1 RKXLNXBWUFSQIR-UHFFFAOYSA-N 0.000 claims description 2
- XQWPVWMTMYJQBE-UHFFFAOYSA-N N-hydroxy-2-[4-(2-methoxyphenyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound COC1=C(C=CC=C1)C1=CC=C(C=C1)C1=NC2=C(O1)C=CC(=C2)C(=O)NO XQWPVWMTMYJQBE-UHFFFAOYSA-N 0.000 claims description 2
- RXFAEAGZQHBTJE-UHFFFAOYSA-N N-hydroxy-2-[4-(2-methoxypyridin-3-yl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound COc1ncccc1-c1ccc(cc1)-c1nc2cc(ccc2o1)C(=O)NO RXFAEAGZQHBTJE-UHFFFAOYSA-N 0.000 claims description 2
- KSANADGXUNXXGO-UHFFFAOYSA-N N-hydroxy-2-[4-(2-morpholin-4-ylethoxy)anilino]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)NC2=CC=C(C=C2)OCCN2CCOCC2)C=1 KSANADGXUNXXGO-UHFFFAOYSA-N 0.000 claims description 2
- NSKVDURPZQGXBW-UHFFFAOYSA-N N-hydroxy-2-[4-(4-methoxypyridin-3-yl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound COc1ccncc1-c1ccc(cc1)-c1nc2cc(ccc2o1)C(=O)NO NSKVDURPZQGXBW-UHFFFAOYSA-N 0.000 claims description 2
- RBOXENCKUPVFMS-UHFFFAOYSA-N N-hydroxy-2-[4-(4-methylsulfonylphenyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound CS(=O)(=O)c1ccc(cc1)-c1ccc(cc1)-c1nc2cc(ccc2o1)C(=O)NO RBOXENCKUPVFMS-UHFFFAOYSA-N 0.000 claims description 2
- SJVMHCKWSVQJIO-UHFFFAOYSA-N N-hydroxy-2-[4-(6-methoxypyridin-3-yl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)C=2C=NC(=CC=2)OC)C=1 SJVMHCKWSVQJIO-UHFFFAOYSA-N 0.000 claims description 2
- UEOSYZMZNHHYIL-UHFFFAOYSA-N N-hydroxy-2-[4-(hydroxymethyl)phenyl]-1,3-benzothiazole-6-carboxamide Chemical compound OCc1ccc(cc1)-c1nc2ccc(cc2s1)C(=O)NO UEOSYZMZNHHYIL-UHFFFAOYSA-N 0.000 claims description 2
- FWQFLICSJPZRJQ-UHFFFAOYSA-N N-hydroxy-2-[4-(methanesulfonamido)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)NS(=O)(=O)C)C=1 FWQFLICSJPZRJQ-UHFFFAOYSA-N 0.000 claims description 2
- DARUGKLUYXMHPR-UHFFFAOYSA-N N-hydroxy-2-[4-(methanesulfonamido)phenyl]-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C2=CC=C(C=C2)NS(=O)(=O)C)C=1 DARUGKLUYXMHPR-UHFFFAOYSA-N 0.000 claims description 2
- RWOOVHUABHYSIR-UHFFFAOYSA-N N-hydroxy-2-[4-(piperidin-1-ylmethyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C1=CC2=C(OC(=N2)C2=CC=C(CN3CCCCC3)C=C2)C=C1 RWOOVHUABHYSIR-UHFFFAOYSA-N 0.000 claims description 2
- OMXHGQOOQBESNZ-UHFFFAOYSA-N N-hydroxy-2-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)OC(F)(F)F)C=1 OMXHGQOOQBESNZ-UHFFFAOYSA-N 0.000 claims description 2
- QSSGKCWXYUURJE-UHFFFAOYSA-N N-hydroxy-2-[4-(trifluoromethoxy)phenyl]-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C2=CC=C(C=C2)OC(F)(F)F)C=1 QSSGKCWXYUURJE-UHFFFAOYSA-N 0.000 claims description 2
- DEECLJKYPGDMNV-UHFFFAOYSA-N N-hydroxy-2-[4-(trifluoromethyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)c1ccc2oc(nc2c1)-c1ccc(cc1)C(F)(F)F DEECLJKYPGDMNV-UHFFFAOYSA-N 0.000 claims description 2
- GABYMYXBFYXQHS-UHFFFAOYSA-N N-hydroxy-2-[4-(trifluoromethyl)phenyl]-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C2=CC=C(C=C2)C(F)(F)F)C=1 GABYMYXBFYXQHS-UHFFFAOYSA-N 0.000 claims description 2
- XMLROSZLPDZOET-UHFFFAOYSA-N N-hydroxy-2-[4-[(4-pyridin-4-ylpiperazin-1-yl)methyl]phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)CN2CCN(CC2)C2=CC=NC=C2)C=1 XMLROSZLPDZOET-UHFFFAOYSA-N 0.000 claims description 2
- VJSYMNWZRKGSPF-UHFFFAOYSA-N N-hydroxy-2-[4-[4-(piperidin-1-ylmethyl)phenyl]phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=C(C=C2)C2=CC=C(C=C2)CN2CCCCC2)C=1 VJSYMNWZRKGSPF-UHFFFAOYSA-N 0.000 claims description 2
- UMUBIUVIMALCCX-UHFFFAOYSA-N N-hydroxy-2-[4-[[(1-methylindol-3-yl)methylamino]methyl]piperidin-1-yl]-1,3-benzoxazole-5-carboxamide Chemical compound Cn1cc(CNCC2CCN(CC2)c2nc3cc(ccc3o2)C(=O)NO)c2ccccc12 UMUBIUVIMALCCX-UHFFFAOYSA-N 0.000 claims description 2
- RZXKDRZYRIXQFO-UHFFFAOYSA-N N-hydroxy-2-[6-(1-phenylethylamino)pyridin-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)NC(C)C2=CC=CC=C2)C=1 RZXKDRZYRIXQFO-UHFFFAOYSA-N 0.000 claims description 2
- IJNSXQNOHBEEPB-UHFFFAOYSA-N N-hydroxy-2-[6-(2-methylpropylamino)pyridin-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)NCC(C)C)C=1 IJNSXQNOHBEEPB-UHFFFAOYSA-N 0.000 claims description 2
- FOXZDNVOMAWWHO-UHFFFAOYSA-N N-hydroxy-2-[6-(4-methylpiperidin-1-yl)pyridin-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound CC1CCN(CC1)c1ccc(cn1)-c1nc2cc(ccc2o1)C(=O)NO FOXZDNVOMAWWHO-UHFFFAOYSA-N 0.000 claims description 2
- VXBYJHUVPLRYOB-UHFFFAOYSA-N N-hydroxy-2-[6-(pyridin-2-ylmethylamino)pyridin-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)NCC2=NC=CC=C2)C=1 VXBYJHUVPLRYOB-UHFFFAOYSA-N 0.000 claims description 2
- NWQLMGLPBUEAOJ-CQSZACIVSA-N N-hydroxy-2-[6-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]pyridin-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)N2[C@H](CCC2)COC)C=1 NWQLMGLPBUEAOJ-CQSZACIVSA-N 0.000 claims description 2
- JSJJAKICSQVJNE-UHFFFAOYSA-N N-hydroxy-2-[6-[4-(2-methoxyphenyl)piperazin-1-yl]pyridin-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC(=CC=2)N2CCN(CC2)C2=C(C=CC=C2)OC)C=1 JSJJAKICSQVJNE-UHFFFAOYSA-N 0.000 claims description 2
- GPOXGFIWWSMWLJ-UHFFFAOYSA-N N-hydroxy-2-naphthalen-2-yl-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(N=C(S2)C2=CC3=CC=CC=C3C=C2)C=C1 GPOXGFIWWSMWLJ-UHFFFAOYSA-N 0.000 claims description 2
- ZDTVSGOQESDESQ-UHFFFAOYSA-N N-hydroxy-2-pyridin-2-yl-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=NC=CC=C2)C=1 ZDTVSGOQESDESQ-UHFFFAOYSA-N 0.000 claims description 2
- RPQQRQLPQSCBFG-UHFFFAOYSA-N N-hydroxy-2-pyridin-3-yl-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C=2C=NC=CC=2)C=1 RPQQRQLPQSCBFG-UHFFFAOYSA-N 0.000 claims description 2
- QXYZANPMQXKHKD-UHFFFAOYSA-N N-hydroxy-2-pyridin-3-yl-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C=2C=NC=CC=2)C=1 QXYZANPMQXKHKD-UHFFFAOYSA-N 0.000 claims description 2
- ZOKVZDIJCXXSPA-UHFFFAOYSA-N N-hydroxy-2-pyridin-4-yl-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(N=C(S2)C2=CC=NC=C2)C=C1 ZOKVZDIJCXXSPA-UHFFFAOYSA-N 0.000 claims description 2
- WQJGTHMVLGQBBU-UHFFFAOYSA-N N-hydroxy-2-pyrimidin-5-yl-1-benzofuran-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(O2)C=2C=NC=NC=2)C=1 WQJGTHMVLGQBBU-UHFFFAOYSA-N 0.000 claims description 2
- VTDJWTMUBIREHK-UHFFFAOYSA-N N-hydroxy-2-quinolin-8-yl-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(N=C(S2)C=2C=CC=C3C=CC=NC=23)C=C1 VTDJWTMUBIREHK-UHFFFAOYSA-N 0.000 claims description 2
- OOTAUALCODVCOP-UHFFFAOYSA-N N-hydroxy-2-thiophen-3-yl-1,3-benzothiazole-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(N=C(S2)C2=CSC=C2)C=C1 OOTAUALCODVCOP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- SLKMTZKOMSIJGI-UHFFFAOYSA-N 2-[[bis(2-methylpropyl)amino]methyl]-N-hydroxy-1,3-benzothiazole-5-carboxamide Chemical compound CC(C)CN(CC(C)C)CC1=NC2=CC(=CC=C2S1)C(=O)NO SLKMTZKOMSIJGI-UHFFFAOYSA-N 0.000 claims 1
- DCUNRFZLKCDAKX-UHFFFAOYSA-N 2-amino-N-hydroxy-1,3-benzothiazole-5-carboxamide Chemical compound NC=1SC2=C(N=1)C=C(C=C2)C(=O)NO DCUNRFZLKCDAKX-UHFFFAOYSA-N 0.000 claims 1
- WZANXMBVMOCCKP-UHFFFAOYSA-N N-hydroxy-2-(2-methoxypyridin-3-yl)-1-benzothiophene-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(S2)C=2C(=NC=CC=2)OC)C=1 WZANXMBVMOCCKP-UHFFFAOYSA-N 0.000 claims 1
- IQAJIZXYXADIAL-UHFFFAOYSA-N N-hydroxy-2-(2-methyl-1H-indol-3-yl)-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=C(NC3=CC=CC=C23)C)C=1 IQAJIZXYXADIAL-UHFFFAOYSA-N 0.000 claims 1
- KYRHMBQWDIUOFE-UHFFFAOYSA-N N-hydroxy-2-[4-(3-methylsulfonylphenyl)phenyl]-1,3-benzoxazole-5-carboxamide Chemical compound CS(=O)(=O)c1cccc(c1)-c1ccc(cc1)-c1nc2cc(ccc2o1)C(=O)NO KYRHMBQWDIUOFE-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 102100038715 Histone deacetylase 8 Human genes 0.000 description 2
- 101710177327 Histone deacetylase 8 Proteins 0.000 description 2
- XSCMPUMSWGUHBS-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-3H-imidazo[4,5-c]pyridine-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=N1)N=C(N2)C1=CC=C(C=C1)C(C)C XSCMPUMSWGUHBS-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 description 1
- PFRXPDLRVXWJSK-UHFFFAOYSA-N 2-(3,4-dihydro-1H-isoquinolin-2-yl)-N-hydroxy-1-methylbenzimidazole-5-carboxamide Chemical compound C1N(CCC2=CC=CC=C12)C1=NC2=C(N1C)C=CC(=C2)C(=O)NO PFRXPDLRVXWJSK-UHFFFAOYSA-N 0.000 description 1
- AXEYNESRQWHZSR-UHFFFAOYSA-N 2-(3-bromoanilino)-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound ONC(=O)C1=CC=C2N=C(NC3=CC(Br)=CC=C3)NC2=C1 AXEYNESRQWHZSR-UHFFFAOYSA-N 0.000 description 1
- VUTUNJXKIRBTNW-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-N-hydroxy-1-methylbenzimidazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)C1CCN(CC1)C1=NC2=C(N1C)C=CC(=C2)C(=O)NO VUTUNJXKIRBTNW-UHFFFAOYSA-N 0.000 description 1
- QVSFVJRDNXKHMC-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound ONC(=O)C1=CC=C2N=C(NC2=C1)N1CCC(CC2=CC=CC=C2)CC1 QVSFVJRDNXKHMC-UHFFFAOYSA-N 0.000 description 1
- NRFKOLDAPNTDEL-UHFFFAOYSA-N 2-(4-bromoanilino)-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound ONC(=O)C1=CC=C2N=C(NC3=CC=C(Br)C=C3)NC2=C1 NRFKOLDAPNTDEL-UHFFFAOYSA-N 0.000 description 1
- REOPVWFCIDGOKR-UHFFFAOYSA-N 2-(4-chloro-N-methylanilino)-N-hydroxy-1-methylbenzimidazole-5-carboxamide Chemical compound ClC1=CC=C(C=C1)N(C1=NC2=C(N1C)C=CC(=C2)C(=O)NO)C REOPVWFCIDGOKR-UHFFFAOYSA-N 0.000 description 1
- KQXOCTMPXLXXKO-UHFFFAOYSA-N 2-(4-chloro-N-methylanilino)-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound ClC1=CC=C(C=C1)N(C1=NC2=C(N1)C=C(C=C2)C(=O)NO)C KQXOCTMPXLXXKO-UHFFFAOYSA-N 0.000 description 1
- VXWMWMQKRGVGHN-UHFFFAOYSA-N 2-(5-fluoro-2-hydroxyphenyl)-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)O VXWMWMQKRGVGHN-UHFFFAOYSA-N 0.000 description 1
- IISSMHBVOWYKBT-UHFFFAOYSA-N 2-(N-benzylanilino)-N-hydroxy-1-methylbenzimidazole-5-carboxamide Chemical compound Cn1c(nc2cc(ccc12)C(=O)NO)N(Cc1ccccc1)c1ccccc1 IISSMHBVOWYKBT-UHFFFAOYSA-N 0.000 description 1
- XDTHCSCPAHXXCW-UHFFFAOYSA-N 2-(N-benzylanilino)-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound ONC(=O)C1=CC=C2N=C(NC2=C1)N(CC1=CC=CC=C1)C1=CC=CC=C1 XDTHCSCPAHXXCW-UHFFFAOYSA-N 0.000 description 1
- PMOMAAXWTOSWGN-UHFFFAOYSA-N 2-(benzylamino)-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)NC1=NC2=C(N1)C=C(C=C2)C(=O)NO PMOMAAXWTOSWGN-UHFFFAOYSA-N 0.000 description 1
- ZPXAGNZHTWVGJU-UHFFFAOYSA-N 2-[2-fluoro-4-(6-methoxypyridin-3-yl)phenyl]-N-hydroxy-1,3-benzoxazole-5-carboxamide Chemical compound COc1ccc(cn1)-c1ccc(-c2nc3cc(ccc3o2)C(=O)NO)c(F)c1 ZPXAGNZHTWVGJU-UHFFFAOYSA-N 0.000 description 1
- ZHSZBCXWPYSLHZ-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)piperazin-1-yl]-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound FC1=CC=C(C=C1)N1CCN(CC1)C1=NC2=C(N1)C=C(C=C2)C(=O)NO ZHSZBCXWPYSLHZ-UHFFFAOYSA-N 0.000 description 1
- NQUOTVISPTWHJX-UHFFFAOYSA-N 2-[benzyl(methyl)amino]-N-hydroxy-1-methylbenzimidazole-5-carboxamide Chemical compound CN(Cc1ccccc1)c1nc2cc(ccc2n1C)C(=O)NO NQUOTVISPTWHJX-UHFFFAOYSA-N 0.000 description 1
- HHMPSWYZZRJYOI-UHFFFAOYSA-N 2-[benzyl(methyl)amino]-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)N(C1=NC2=C(N1)C=C(C=C2)C(=O)NO)C HHMPSWYZZRJYOI-UHFFFAOYSA-N 0.000 description 1
- TZAJHIBAJPPOAL-UHFFFAOYSA-N 2-anilino-N-hydroxy-1-methylbenzimidazole-5-carboxamide Chemical compound Cn1c(Nc2ccccc2)nc2cc(ccc12)C(=O)NO TZAJHIBAJPPOAL-UHFFFAOYSA-N 0.000 description 1
- TYOPXOXIFCEQNQ-UHFFFAOYSA-N 2-anilino-N-hydroxy-3H-benzimidazole-5-carboxamide Chemical compound ONC(=O)C1=CC=C2N=C(NC3=CC=CC=C3)NC2=C1 TYOPXOXIFCEQNQ-UHFFFAOYSA-N 0.000 description 1
- VJZZEVABRIDARR-UHFFFAOYSA-N 2-bromo-3-chloro-N-hydroxy-1H-indole-6-carboxamide Chemical compound BrC=1NC2=CC(=CC=C2C=1Cl)C(=O)NO VJZZEVABRIDARR-UHFFFAOYSA-N 0.000 description 1
- ALPXMCXAFAUHNP-UHFFFAOYSA-N 3-chloro-N-hydroxy-2-(4-propan-2-ylphenyl)-1H-indole-6-carboxamide Chemical compound CC(C)c1ccc(cc1)-c1[nH]c2cc(ccc2c1Cl)C(=O)NO ALPXMCXAFAUHNP-UHFFFAOYSA-N 0.000 description 1
- PPAIXKOHCKKYKK-UHFFFAOYSA-N 3-chloro-N-hydroxy-2-phenyl-1H-indole-6-carboxamide Chemical compound ClC1=C(NC2=CC(=CC=C12)C(=O)NO)C1=CC=CC=C1 PPAIXKOHCKKYKK-UHFFFAOYSA-N 0.000 description 1
- NUHXTBLPVDEUKY-UHFFFAOYSA-N CC(NC1=CC=CC=C11)=C1C1=NC(C=C(C=C2)C(N)=O)=C2O1 Chemical compound CC(NC1=CC=CC=C11)=C1C1=NC(C=C(C=C2)C(N)=O)=C2O1 NUHXTBLPVDEUKY-UHFFFAOYSA-N 0.000 description 1
- 102100022537 Histone deacetylase 6 Human genes 0.000 description 1
- 101000899330 Homo sapiens Histone deacetylase 6 Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- WWGBHDIHIVGYLZ-UHFFFAOYSA-N N-[4-[3-[[[7-(hydroxyamino)-7-oxoheptyl]amino]-oxomethyl]-5-isoxazolyl]phenyl]carbamic acid tert-butyl ester Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C1=CC(C(=O)NCCCCCCC(=O)NO)=NO1 WWGBHDIHIVGYLZ-UHFFFAOYSA-N 0.000 description 1
- AJRGHIGYPXNABY-UHFFFAOYSA-N N-hydroxy-1-[(4-methoxyphenyl)methyl]-6-indolecarboxamide Chemical compound C1=CC(OC)=CC=C1CN1C2=CC(C(=O)NO)=CC=C2C=C1 AJRGHIGYPXNABY-UHFFFAOYSA-N 0.000 description 1
- HIKRFZSEUFPTJU-UHFFFAOYSA-N N-hydroxy-1-methyl-2-(2-phenylethylamino)benzimidazole-5-carboxamide Chemical compound Cn1c(NCCc2ccccc2)nc2cc(ccc12)C(=O)NO HIKRFZSEUFPTJU-UHFFFAOYSA-N 0.000 description 1
- KLNBRNPKIRVLDO-UHFFFAOYSA-N N-hydroxy-1-methyl-2-(3-phenylanilino)benzimidazole-5-carboxamide Chemical compound C1(=CC(=CC=C1)NC1=NC2=C(N1C)C=CC(=C2)C(=O)NO)C1=CC=CC=C1 KLNBRNPKIRVLDO-UHFFFAOYSA-N 0.000 description 1
- LEGVHTHDGRLPFQ-UHFFFAOYSA-N N-hydroxy-1-methyl-2-(4-propan-2-ylanilino)benzimidazole-5-carboxamide Chemical compound CC(C)c1ccc(Nc2nc3cc(ccc3n2C)C(=O)NO)cc1 LEGVHTHDGRLPFQ-UHFFFAOYSA-N 0.000 description 1
- YHNAHGDELYOYSK-UHFFFAOYSA-N N-hydroxy-2-(3-phenylmethoxyanilino)-3H-benzimidazole-5-carboxamide Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=CC=1)NC1=NC2=C(N1)C=C(C=C2)C(=O)NO YHNAHGDELYOYSK-UHFFFAOYSA-N 0.000 description 1
- OVIACGUBEMMHLD-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylanilino)-3H-benzimidazole-5-carboxamide Chemical compound CC(C)C1=CC=C(NC2=NC3=CC=C(C=C3N2)C(=O)NO)C=C1 OVIACGUBEMMHLD-UHFFFAOYSA-N 0.000 description 1
- GRHDIBKTKSJWIW-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1,3-benzoxazole-6-carboxamide Chemical compound CC(C)c1ccc(cc1)-c1nc2ccc(cc2o1)C(=O)NO GRHDIBKTKSJWIW-UHFFFAOYSA-N 0.000 description 1
- XNTORRKTCIASJL-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1H-imidazo[4,5-b]pyridine-6-carboxamide Chemical compound ONC(=O)C=1C=C2C(=NC=1)N=C(N2)C1=CC=C(C=C1)C(C)C XNTORRKTCIASJL-UHFFFAOYSA-N 0.000 description 1
- YCPWQLIHVDDGFY-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1H-indole-5-carboxamide Chemical compound CC(C)c1ccc(cc1)-c1cc2cc(ccc2[nH]1)C(=O)NO YCPWQLIHVDDGFY-UHFFFAOYSA-N 0.000 description 1
- TURVILMWLWAXJH-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1H-indole-6-carboxamide Chemical compound ONC(=O)C1=CC=C2C=C(NC2=C1)C1=CC=C(C=C1)C(C)C TURVILMWLWAXJH-UHFFFAOYSA-N 0.000 description 1
- DTLGZKVDJMIFBU-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxamide Chemical compound ONC(=O)C=1C=C2C(=NC=1)NC(=C2)C1=CC=C(C=C1)C(C)C DTLGZKVDJMIFBU-UHFFFAOYSA-N 0.000 description 1
- JNBCKCAQIWDJRZ-UHFFFAOYSA-N N-hydroxy-2-(4-propan-2-ylphenyl)-1H-pyrrolo[3,2-b]pyridine-5-carboxamide Chemical compound CC(C)C1=CC=C(C=C1)C1=CC2=C(N1)C=CC(=N2)C(=O)NO JNBCKCAQIWDJRZ-UHFFFAOYSA-N 0.000 description 1
- ZYBQPIUVDLPCKB-UHFFFAOYSA-N N-hydroxy-2-[(4-phenylphenyl)methylamino]-3H-benzimidazole-5-carboxamide Chemical compound C1(=CC=C(C=C1)CNC1=NC2=C(N1)C=C(C=C2)C(=O)NO)C1=CC=CC=C1 ZYBQPIUVDLPCKB-UHFFFAOYSA-N 0.000 description 1
- HUQCKPJZHBQXLS-UHFFFAOYSA-N N-hydroxy-2-phenyl-1,3-benzoxazole-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(N=C(O2)C2=CC=CC=C2)C=1 HUQCKPJZHBQXLS-UHFFFAOYSA-N 0.000 description 1
- DFCIVGNXIIABGD-UHFFFAOYSA-N N-hydroxy-2-phenyl-1-benzofuran-5-carboxamide Chemical compound ONC(=O)C=1C=CC2=C(C=C(O2)C2=CC=CC=C2)C=1 DFCIVGNXIIABGD-UHFFFAOYSA-N 0.000 description 1
- SVSFPYUYTVAWRG-UHFFFAOYSA-N N-hydroxy-2-phenyl-1-benzofuran-6-carboxamide Chemical compound ONC(=O)C1=CC2=C(C=C(O2)C2=CC=CC=C2)C=C1 SVSFPYUYTVAWRG-UHFFFAOYSA-N 0.000 description 1
- QBMJWULNLAEKKH-UHFFFAOYSA-N N-hydroxy-6-(4-propan-2-ylphenyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carboxamide Chemical compound ONC(=O)C=1N=CC2=C(N=1)NC(=C2)C1=CC=C(C=C1)C(C)C QBMJWULNLAEKKH-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010042971 T-cell lymphoma Diseases 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15201841 | 2015-12-22 | ||
| EP15201841.2 | 2015-12-22 | ||
| PCT/EP2016/077914 WO2017108282A1 (en) | 2015-12-22 | 2016-11-16 | Bicyclic hydroxamic acids useful as inhibitors of mammalian histone deacetylase activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019505500A JP2019505500A (ja) | 2019-02-28 |
| JP2019505500A5 true JP2019505500A5 (https=) | 2019-12-19 |
| JP6927589B2 JP6927589B2 (ja) | 2021-09-01 |
Family
ID=55068815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018532429A Expired - Fee Related JP6927589B2 (ja) | 2015-12-22 | 2016-11-16 | 哺乳類ヒストンデアセチラーゼ活性の阻害剤として有用な二環式ヒドロキサム酸 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10654814B2 (https=) |
| EP (1) | EP3394052B1 (https=) |
| JP (1) | JP6927589B2 (https=) |
| KR (1) | KR20180098593A (https=) |
| CN (1) | CN108602812B (https=) |
| AU (1) | AU2016375634B2 (https=) |
| CA (1) | CA3007025A1 (https=) |
| ES (1) | ES2893099T3 (https=) |
| RU (1) | RU2747431C2 (https=) |
| WO (1) | WO2017108282A1 (https=) |
| ZA (1) | ZA201804568B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7293343B2 (ja) * | 2018-05-09 | 2023-06-19 | アプリノイア セラピューティクス リミテッド | ヘテロアリール化合物及びその使用 |
| US12195432B2 (en) * | 2018-08-06 | 2025-01-14 | The Board Of Trustees Of The Leland Stanford Junior University | 2-arylbenzimidazoles as Ppargc1a activators for treating neurodegenerative diseases |
| EP3833671B1 (en) | 2018-08-08 | 2022-08-24 | Bristol-Myers Squibb Company | Substituted thienopyrroles as pad4 inhibitors |
| AU2019319835A1 (en) | 2018-08-08 | 2021-03-25 | Bristol-Myers Squibb Company | Indole and azaindole inhibitors of PAD enzymes |
| KR102146741B1 (ko) * | 2018-10-31 | 2020-08-21 | 계명대학교 산학협력단 | 항바이러스 조성물 |
| US20220008414A1 (en) * | 2018-11-23 | 2022-01-13 | Chong Kun Dang Pharmaceutical Corp. | Pharmaceutical composition comprising histone deacetylase 6 inhibitors |
| 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 |
| JP2023530788A (ja) * | 2020-06-08 | 2023-07-19 | アンジー ファーマシューティカル カンパニー リミテッド | 選択的ｈｄａｃ６阻害剤として有用なキナゾリン誘導体 |
| 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 |
| EP4326263A1 (en) | 2021-04-23 | 2024-02-28 | Tenaya Therapeutics, Inc. | Hdac6 inhibitors for use in the treatment of dilated cardiomyopathy |
| AU2022270657A1 (en) | 2021-05-04 | 2023-11-16 | 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 |
| CA3254742A1 (en) * | 2022-03-17 | 2025-03-04 | Sookmyung Women's University Industry-Academic Cooperation Foundation | NEW HETEROCYCLIC HISTONE DEACETYLASE INHIBITOR, AND PHARMACEUTICAL COMPOSITION INCLUDING IT |
| WO2025160629A1 (en) * | 2024-01-31 | 2025-08-07 | Certa Therapeutics Pty Ltd | Proton sensing gpcr modulators |
| WO2025215092A1 (en) | 2024-04-10 | 2025-10-16 | Institut National de la Santé et de la Recherche Médicale | Selective hdac6 inhibitors for use in the treatment of myotonic dystrophy type 1 |
| 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 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6861533B2 (en) | 2001-11-23 | 2005-03-01 | Irm Llc | Solution phase sythesis of arylbenzoxazoles |
| 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 |
| PT1673349E (pt) * | 2003-09-22 | 2010-09-28 | S Bio Pte Ltd | Derivados benzimidazole: preparação e aplicações farmacêuticas |
| 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 |
| ES2441196T3 (es) | 2007-04-18 | 2014-02-03 | Kissei Pharmaceutical Co., Ltd. | Derivado de anillo condensado nitrogenado, composiciones farmacéuticas que lo contienen, y su uso con fines médicos |
| WO2008129276A1 (en) | 2007-04-19 | 2008-10-30 | Boehringer Ingelheim International Gmbh | Disulfonamides useful in the treatment of inflammation |
| BRPI0817897A2 (pt) | 2007-11-02 | 2019-09-24 | Methylgene Inc | composto, composição, e, métodos de inibição da atividade hdac, e de tratamento de uma doença responsiva a um inibidor de atividade hdac |
| UA103013C2 (uk) | 2007-12-06 | 2013-09-10 | Тиботек Фармасьютикелз | Амідні сполуки як активатори противірусних препаратів |
| MX2010011168A (es) | 2008-04-15 | 2010-12-21 | Pharmacyclics Inc | Inhibidores selectivos de histona-desacetilasa. |
| WO2010061903A1 (ja) * | 2008-11-27 | 2010-06-03 | 塩野義製薬株式会社 | Pi3k阻害活性を有するピリミジン誘導体およびピリジン誘導体 |
| WO2012012322A1 (en) | 2010-07-19 | 2012-01-26 | Millennium Pharmaceuticals, Inc. | Substituted hydroxamic acids and uses thereof |
| WO2014015088A1 (en) | 2012-07-19 | 2014-01-23 | Bristol-Myers Squibb Company | Amide, urea or sulfone amide linked benzothiazole inhibitors of endothelial lipase |
| KR20160055170A (ko) | 2013-08-30 | 2016-05-17 | 암비트 바이오사이언시즈 코포레이션 | 바이아릴 아세트아미드 화합물 및 이의 사용 방법 |
| CA2941581C (en) * | 2014-03-12 | 2018-07-24 | Chong Kun Dang Pharmaceutical Corp. | Novel compounds as histone deacetylase 6 inhibitors and pharmaceutical compositions comprising the same |
| US20170114019A1 (en) * | 2014-06-04 | 2017-04-27 | Haro Pharmaceutical Inc. | 18-20 member bi-polycyclic compounds |
| CA2984971A1 (en) | 2015-05-11 | 2016-11-17 | Kancera Ab | Benzimidazole derivates useful as inhibitors of mammalian histone deacetylase activity |
-
2016
- 2016-11-16 RU RU2018126815A patent/RU2747431C2/ru active
- 2016-11-16 CA CA3007025A patent/CA3007025A1/en not_active Abandoned
- 2016-11-16 EP EP16797555.6A patent/EP3394052B1/en active Active
- 2016-11-16 US US16/063,682 patent/US10654814B2/en not_active Expired - Fee Related
- 2016-11-16 WO PCT/EP2016/077914 patent/WO2017108282A1/en not_active Ceased
- 2016-11-16 ES ES16797555T patent/ES2893099T3/es active Active
- 2016-11-16 JP JP2018532429A patent/JP6927589B2/ja not_active Expired - Fee Related
- 2016-11-16 KR KR1020187021065A patent/KR20180098593A/ko not_active Withdrawn
- 2016-11-16 CN CN201680072487.1A patent/CN108602812B/zh not_active Expired - Fee Related
- 2016-11-16 AU AU2016375634A patent/AU2016375634B2/en not_active Ceased
-
2018
- 2018-07-09 ZA ZA2018/04568A patent/ZA201804568B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019505500A5 (https=) | ||
| RU2747431C2 (ru) | Бициклические гидроксамовые кислоты, полезные в качестве ингибиторов активности деацетилазы гистонов млекопитающих | |
| JP7264060B2 (ja) | 二環式化合物および癌の処置におけるそれらの使用 | |
| JP6412148B2 (ja) | 自己免疫疾患治療のためのピラゾール | |
| KR102781404B1 (ko) | 통합 스트레스 경로의 조정제 | |
| US10864196B2 (en) | Modulators of the integrated stress pathway | |
| JP7307057B2 (ja) | 統合的ストレス経路の調節剤 | |
| US10357484B2 (en) | Heterocyclic compound | |
| BR112020008827A2 (pt) | moduladores da via de estresse integrada | |
| WO2016031815A1 (ja) | 複素環化合物 | |
| WO2017033946A1 (ja) | 複素環化合物 | |
| JPWO2015002230A1 (ja) | アミド化合物 | |
| JP2024096821A (ja) | 癌または炎症性疾患の治療のためのヘテロ二環式カルボキシ酸 | |
| HK40029801A (en) | Heterobicyclic carboxylic acids for treating cancer or inflammatory diseases | |
| US20200181128A1 (en) | 3-hydroxy-imidazolidin-4-one compounds as inhibitors of indoleamine 2,3-dioxygenase |