HRP20241444T1 - Derivati alkohola kao otvarači kv7 kalijevih kanala - Google Patents
Derivati alkohola kao otvarači kv7 kalijevih kanala Download PDFInfo
- Publication number
- HRP20241444T1 HRP20241444T1 HRP20241444TT HRP20241444T HRP20241444T1 HR P20241444 T1 HRP20241444 T1 HR P20241444T1 HR P20241444T T HRP20241444T T HR P20241444TT HR P20241444 T HRP20241444 T HR P20241444T HR P20241444 T1 HRP20241444 T1 HR P20241444T1
- Authority
- HR
- Croatia
- Prior art keywords
- difluoromethoxy
- phenyl
- ethyl
- hydroxy
- trifluoromethoxy
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title 1
- 229940127315 Potassium Channel Openers Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 3
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 3
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- BVCFMTPSASIOGN-DZGCQCFKSA-N (3R)-3-(1-fluorocyclopropyl)-3-hydroxy-N-[(1R)-2-methoxy-1-[3-(trifluoromethoxy)phenyl]ethyl]butanamide Chemical compound FC1(CC1)[C@](CC(=O)N[C@@H](COC)C1=CC(=CC=C1)OC(F)(F)F)(C)O BVCFMTPSASIOGN-DZGCQCFKSA-N 0.000 claims 1
- JXROOIQJGMWIPA-QWHCGFSZSA-N (3R)-3-(3,3-difluorocyclobutyl)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxypropanamide Chemical compound FC1(CC(C1)[C@@H](CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)F)O)F JXROOIQJGMWIPA-QWHCGFSZSA-N 0.000 claims 1
- NXCGVJRTEVJPJV-QWHCGFSZSA-N (3R)-3-(3,3-difluorocyclobutyl)-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxypropanamide Chemical compound FC1(CC(C1)[C@@H](CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)(F)F)O)F NXCGVJRTEVJPJV-QWHCGFSZSA-N 0.000 claims 1
- PWNSUVWRMNJZBR-LSDHHAIUSA-N (3R)-3-(3,3-difluorocyclobutyl)-N-[(1S)-1-[3-(difluoromethoxy)phenyl]butyl]-3-hydroxypropanamide Chemical compound FC1(CC(C1)[C@@H](CC(=O)N[C@@H](CCC)C1=CC(=CC=C1)OC(F)F)O)F PWNSUVWRMNJZBR-LSDHHAIUSA-N 0.000 claims 1
- SJXBACWMIQQWOB-LSDHHAIUSA-N (3R)-3-cyclopentyl-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxypropanamide Chemical compound C1(CCCC1)[C@@H](CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)F)O SJXBACWMIQQWOB-LSDHHAIUSA-N 0.000 claims 1
- CNUMXNCWPQLNDB-XJKSGUPXSA-N (3R)-3-cyclopropyl-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxybutanamide Chemical compound C1(CC1)[C@](CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)(F)F)(C)O CNUMXNCWPQLNDB-XJKSGUPXSA-N 0.000 claims 1
- YFEXROIPFBZMJX-UONOGXRCSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-(1-ethylcyclopropyl)-3-hydroxypropanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@H](O)C1(CC1)CC)=O)F YFEXROIPFBZMJX-UONOGXRCSA-N 0.000 claims 1
- JKKHWVGGTHKOOY-BLLLJJGKSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-(1-fluorocyclopropyl)-3-hydroxybutanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@](C)(O)C1(CC1)F)=O)F JKKHWVGGTHKOOY-BLLLJJGKSA-N 0.000 claims 1
- RITNVXLACQQIDC-LSDHHAIUSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-(3,3-dimethylcyclobutyl)-3-hydroxypropanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@H](O)C1CC(C1)(C)C)=O)F RITNVXLACQQIDC-LSDHHAIUSA-N 0.000 claims 1
- NCOLOMCPTZJRSC-SUMWQHHRSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-3,4-dimethylpentanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@](C(C)C)(C)O)=O)F NCOLOMCPTZJRSC-SUMWQHHRSA-N 0.000 claims 1
- HASQLFGGRHZQOE-KBXCAEBGSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-3,5-dimethylhexanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@](CC(C)C)(C)O)=O)F HASQLFGGRHZQOE-KBXCAEBGSA-N 0.000 claims 1
- VSBSHZWNFVHXRL-NWDGAFQWSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-3-[1-(trifluoromethyl)cyclopropyl]propanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@H](C1(CC1)C(F)(F)F)O)=O)F VSBSHZWNFVHXRL-NWDGAFQWSA-N 0.000 claims 1
- UYQMYWWYVZCQIW-QWHCGFSZSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@H](C(C)(C)C)O)=O)F UYQMYWWYVZCQIW-QWHCGFSZSA-N 0.000 claims 1
- RQEXYYDMJVKYGK-XHDPSFHLSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-5,5,5-trifluoro-3-hydroxy-3-methylpentanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@](CC(F)(F)F)(C)O)=O)F RQEXYYDMJVKYGK-XHDPSFHLSA-N 0.000 claims 1
- FQPRANNXIAWLCE-SWLSCSKDSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-(1-fluorocyclopropyl)-3-hydroxybutanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)(F)F)NC(C[C@@](C)(O)C1(CC1)F)=O)F FQPRANNXIAWLCE-SWLSCSKDSA-N 0.000 claims 1
- JSFJBYFZDTYEHX-NWDGAFQWSA-N (3R)-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxy-3-[1-(trifluoromethyl)cyclopropyl]propanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)(F)F)NC(C[C@H](C1(CC1)C(F)(F)F)O)=O)F JSFJBYFZDTYEHX-NWDGAFQWSA-N 0.000 claims 1
- YARFWJMTHTWPBY-LSDHHAIUSA-N (3R)-N-[(1R)-2-ethoxy-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound CCOC[C@H](NC(=O)C[C@@H](O)C(C)(C)C)C1=CC=CC(OC(F)(F)F)=C1 YARFWJMTHTWPBY-LSDHHAIUSA-N 0.000 claims 1
- BVCFMTPSASIOGN-ZFWWWQNUSA-N (3S)-3-(1-fluorocyclopropyl)-3-hydroxy-N-[(1R)-2-methoxy-1-[3-(trifluoromethoxy)phenyl]ethyl]butanamide Chemical compound FC1(CC1)[C@@](CC(=O)N[C@@H](COC)C1=CC(=CC=C1)OC(F)(F)F)(C)O BVCFMTPSASIOGN-ZFWWWQNUSA-N 0.000 claims 1
- JXROOIQJGMWIPA-STQMWFEESA-N (3S)-3-(3,3-difluorocyclobutyl)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxypropanamide Chemical compound FC1(CC(C1)[C@H](CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)F)O)F JXROOIQJGMWIPA-STQMWFEESA-N 0.000 claims 1
- NXCGVJRTEVJPJV-STQMWFEESA-N (3S)-3-(3,3-difluorocyclobutyl)-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxypropanamide Chemical compound FC1(CC(C1)[C@H](CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)(F)F)O)F NXCGVJRTEVJPJV-STQMWFEESA-N 0.000 claims 1
- PWNSUVWRMNJZBR-GJZGRUSLSA-N (3S)-3-(3,3-difluorocyclobutyl)-N-[(1S)-1-[3-(difluoromethoxy)phenyl]butyl]-3-hydroxypropanamide Chemical compound FC1(CC(C1)[C@H](CC(=O)N[C@@H](CCC)C1=CC(=CC=C1)OC(F)F)O)F PWNSUVWRMNJZBR-GJZGRUSLSA-N 0.000 claims 1
- SJXBACWMIQQWOB-GJZGRUSLSA-N (3S)-3-cyclopentyl-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxypropanamide Chemical compound C1(CCCC1)[C@H](CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)F)O SJXBACWMIQQWOB-GJZGRUSLSA-N 0.000 claims 1
- CNUMXNCWPQLNDB-BBRMVZONSA-N (3S)-3-cyclopropyl-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxybutanamide Chemical compound C1(CC1)[C@@](CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)(F)F)(C)O CNUMXNCWPQLNDB-BBRMVZONSA-N 0.000 claims 1
- GUBAUVBQJNTWJV-STQMWFEESA-N (3S)-3-hydroxy-4,4-dimethyl-N-[(1R)-2-(trifluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]pentanamide Chemical compound FC(OC=1C=C(C=CC=1)[C@H](COC(F)(F)F)NC(C[C@@H](C(C)(C)C)O)=O)(F)F GUBAUVBQJNTWJV-STQMWFEESA-N 0.000 claims 1
- DZHRVMQRFKIUTR-STQMWFEESA-N (3S)-N-[(1R)-1-[3-(difluoromethoxy)phenyl]-2-(trifluoromethoxy)ethyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound FC(OC=1C=C(C=CC=1)[C@H](COC(F)(F)F)NC(C[C@@H](C(C)(C)C)O)=O)F DZHRVMQRFKIUTR-STQMWFEESA-N 0.000 claims 1
- YFEXROIPFBZMJX-KBPBESRZSA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-(1-ethylcyclopropyl)-3-hydroxypropanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@H](O)C1(CC1)CC)=O)F YFEXROIPFBZMJX-KBPBESRZSA-N 0.000 claims 1
- JKKHWVGGTHKOOY-LRDDRELGSA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-(1-fluorocyclopropyl)-3-hydroxybutanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@](C)(O)C1(CC1)F)=O)F JKKHWVGGTHKOOY-LRDDRELGSA-N 0.000 claims 1
- RITNVXLACQQIDC-GJZGRUSLSA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-(3,3-dimethylcyclobutyl)-3-hydroxypropanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@H](O)C1CC(C1)(C)C)=O)F RITNVXLACQQIDC-GJZGRUSLSA-N 0.000 claims 1
- NCOLOMCPTZJRSC-GUYCJALGSA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-3,4-dimethylpentanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@](C(C)C)(C)O)=O)F NCOLOMCPTZJRSC-GUYCJALGSA-N 0.000 claims 1
- HASQLFGGRHZQOE-KSSFIOAISA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-3,5-dimethylhexanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@](CC(C)C)(C)O)=O)F HASQLFGGRHZQOE-KSSFIOAISA-N 0.000 claims 1
- VSBSHZWNFVHXRL-RYUDHWBXSA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-3-[1-(trifluoromethyl)cyclopropyl]propanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@H](C1(CC1)C(F)(F)F)O)=O)F VSBSHZWNFVHXRL-RYUDHWBXSA-N 0.000 claims 1
- UYQMYWWYVZCQIW-STQMWFEESA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@H](C(C)(C)C)O)=O)F UYQMYWWYVZCQIW-STQMWFEESA-N 0.000 claims 1
- RQEXYYDMJVKYGK-NHYWBVRUSA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]-5,5,5-trifluoro-3-hydroxy-3-methylpentanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@](CC(F)(F)F)(C)O)=O)F RQEXYYDMJVKYGK-NHYWBVRUSA-N 0.000 claims 1
- FQPRANNXIAWLCE-WFASDCNBSA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-(1-fluorocyclopropyl)-3-hydroxybutanamide Chemical compound FC(OC[C@@H](C1=CC(=CC=C1)OC(F)(F)F)NC(C[C@](C)(O)C1(CC1)F)=O)F FQPRANNXIAWLCE-WFASDCNBSA-N 0.000 claims 1
- JSFJBYFZDTYEHX-RYUDHWBXSA-N (3S)-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxy-3-[1-(trifluoromethyl)cyclopropyl]propanamide Chemical compound O[C@@H](CC(=O)N[C@@H](COC(F)F)C1=CC=CC(OC(F)(F)F)=C1)C1(CC1)C(F)(F)F JSFJBYFZDTYEHX-RYUDHWBXSA-N 0.000 claims 1
- FKYDTEWCMGFQME-HOTGVXAUSA-N (3S)-N-[(1R)-2-cyclopropyloxy-1-[3-(difluoromethoxy)phenyl]ethyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound C1(CC1)OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(C[C@@H](C(C)(C)C)O)=O FKYDTEWCMGFQME-HOTGVXAUSA-N 0.000 claims 1
- YARFWJMTHTWPBY-GJZGRUSLSA-N (3S)-N-[(1R)-2-ethoxy-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound CCOC[C@H](NC(=O)C[C@H](O)C(C)(C)C)C1=CC=CC(OC(F)(F)F)=C1 YARFWJMTHTWPBY-GJZGRUSLSA-N 0.000 claims 1
- RCTWVMOPWPEPRZ-STQMWFEESA-N (3S)-N-[(1S)-1-[3-(difluoromethoxy)phenyl]-3,3-difluoropropyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound FC(OC=1C=C(C=CC=1)[C@H](CC(F)F)NC(C[C@@H](C(C)(C)C)O)=O)F RCTWVMOPWPEPRZ-STQMWFEESA-N 0.000 claims 1
- XRSYTQBBNZBUGO-KBPBESRZSA-N (3S)-N-[(1S)-1-[3-(difluoromethoxy)phenyl]-4,4-difluorobutyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound FC(OC=1C=C(C=CC=1)[C@H](CCC(F)F)NC(C[C@@H](C(C)(C)C)O)=O)F XRSYTQBBNZBUGO-KBPBESRZSA-N 0.000 claims 1
- PAEIGVRFOXLAPN-GJZGRUSLSA-N (3S)-N-[(1S)-1-[3-(difluoromethoxy)phenyl]butyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound FC(OC=1C=C(C=CC=1)[C@H](CCC)NC(C[C@@H](C(C)(C)C)O)=O)F PAEIGVRFOXLAPN-GJZGRUSLSA-N 0.000 claims 1
- NZULTRWXRLHUJE-KBPBESRZSA-N (3S)-N-[(1S)-2-cyano-1-[3-(trifluoromethoxy)phenyl]ethyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound C(#N)C[C@@H](C1=CC(=CC=C1)OC(F)(F)F)NC(C[C@@H](C(C)(C)C)O)=O NZULTRWXRLHUJE-KBPBESRZSA-N 0.000 claims 1
- MCPFPIFHVGHVKC-GJZGRUSLSA-N (3S)-N-[(1S)-3-cyano-1-[3-(trifluoromethoxy)phenyl]propyl]-3-hydroxy-4,4-dimethylpentanamide Chemical compound C(#N)CC[C@@H](C1=CC(=CC=C1)OC(F)(F)F)NC(C[C@@H](C(C)(C)C)O)=O MCPFPIFHVGHVKC-GJZGRUSLSA-N 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- OSYNGASVTMRBTH-NSHDSACASA-N 2-(3,3-difluoro-1-hydroxycyclobutyl)-N-[(1R)-1-[3-(difluoromethoxy)phenyl]-2-(trifluoromethoxy)ethyl]acetamide Chemical compound FC1(CC(C1)(O)CC(=O)N[C@@H](COC(F)(F)F)C1=CC(=CC=C1)OC(F)F)F OSYNGASVTMRBTH-NSHDSACASA-N 0.000 claims 1
- XKXZUZYXIMBRHM-NSHDSACASA-N 2-(3,3-difluoro-1-hydroxycyclobutyl)-N-[(1R)-2-(difluoromethoxy)-1-[3-(difluoromethoxy)phenyl]ethyl]acetamide Chemical compound FC1(CC(C1)(O)CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)F)F XKXZUZYXIMBRHM-NSHDSACASA-N 0.000 claims 1
- LGBTWNLXSWDIKU-NSHDSACASA-N 2-(3,3-difluoro-1-hydroxycyclobutyl)-N-[(1R)-2-(difluoromethoxy)-1-[3-(trifluoromethoxy)phenyl]ethyl]acetamide Chemical compound FC1(CC(C1)(O)CC(=O)N[C@@H](COC(F)F)C1=CC(=CC=C1)OC(F)(F)F)F LGBTWNLXSWDIKU-NSHDSACASA-N 0.000 claims 1
- WRRRGEGPSKEFOF-LBPRGKRZSA-N 2-(3,3-difluoro-1-hydroxycyclobutyl)-N-[(1S)-1-[3-(difluoromethoxy)phenyl]-4,4-difluorobutyl]acetamide Chemical compound FC1(CC(C1)(O)CC(=O)N[C@@H](CCC(F)F)C1=CC(=CC=C1)OC(F)F)F WRRRGEGPSKEFOF-LBPRGKRZSA-N 0.000 claims 1
- JKUCYYBPLCNZNR-ZDUSSCGKSA-N 2-(3,3-difluoro-1-hydroxycyclobutyl)-N-[(1S)-1-[3-(difluoromethoxy)phenyl]butyl]acetamide Chemical compound FC1(CC(C1)(O)CC(=O)N[C@@H](CCC)C1=CC(=CC=C1)OC(F)F)F JKUCYYBPLCNZNR-ZDUSSCGKSA-N 0.000 claims 1
- ZDOFNGNHYFRWHV-LBPRGKRZSA-N 2-(3,3-difluoro-1-hydroxycyclobutyl)-N-[(1S)-1-[3-(trifluoromethoxy)phenyl]propyl]acetamide Chemical compound FC1(CC(C1)(O)CC(=O)N[C@@H](CC)C1=CC(=CC=C1)OC(F)(F)F)F ZDOFNGNHYFRWHV-LBPRGKRZSA-N 0.000 claims 1
- OIAURZOOVQHDDC-NSHDSACASA-N 2-(3,3-difluoro-1-hydroxycyclobutyl)-N-[(1S)-3,3-difluoro-1-[3-(trifluoromethoxy)phenyl]propyl]acetamide Chemical compound FC(C[C@@H](C1=CC(=CC=C1)OC(F)(F)F)NC(CC1(CC(C1)(F)F)O)=O)F OIAURZOOVQHDDC-NSHDSACASA-N 0.000 claims 1
- -1 CF2CHF2 Chemical group 0.000 claims 1
- AZSUUBKZIUKMNP-AWEZNQCLSA-N N-[(1R)-2-cyclopropyloxy-1-[3-(difluoromethoxy)phenyl]ethyl]-2-(3,3-difluoro-1-hydroxycyclobutyl)acetamide Chemical compound C1(CC1)OC[C@@H](C1=CC(=CC=C1)OC(F)F)NC(CC1(CC(C1)(F)F)O)=O AZSUUBKZIUKMNP-AWEZNQCLSA-N 0.000 claims 1
- WRUIJTRYCPBOMY-AWEZNQCLSA-N N-[(1R)-2-cyclopropyloxy-1-[3-(trifluoromethoxy)phenyl]ethyl]-2-(3,3-difluoro-1-hydroxycyclobutyl)acetamide Chemical compound C1(CC1)OC[C@@H](C1=CC(=CC=C1)OC(F)(F)F)NC(CC1(CC(C1)(F)F)O)=O WRUIJTRYCPBOMY-AWEZNQCLSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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- C07C235/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being saturated and containing rings
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- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
- C07C255/44—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms at least one of the singly-bound nitrogen atoms being acylated
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- C07C2601/00—Systems containing only non-condensed rings
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- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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Applications Claiming Priority (5)
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| EP19189750 | 2019-08-02 | ||
| CN201910734123 | 2019-08-09 | ||
| EP19191887 | 2019-08-15 | ||
| PCT/EP2020/071520 WO2021023617A1 (en) | 2019-08-02 | 2020-07-30 | Alcohol derivatives as kv7 potassium channel openers |
| EP20749879.1A EP4007634B1 (en) | 2019-08-02 | 2020-07-30 | Alcohol derivatives as kv7 potassium channel openers |
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| WO2001096540A2 (en) | 2000-06-11 | 2001-12-20 | Dupont Pharmaceuticals Company | Hepatitis c protease exosite for inhibitor design |
| US7091202B2 (en) * | 2004-09-15 | 2006-08-15 | Bristol-Myers Squibb Company | 4-arylspirocycloalkyl-2-aminopyrimidine carboxamide KCNQ potassium channel modulators |
| US7790770B2 (en) * | 2005-11-23 | 2010-09-07 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
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| CN101790374A (zh) | 2007-08-01 | 2010-07-28 | H.隆德贝克有限公司 | Kcnq钾通道开放剂用于减轻多巴胺能系统受到干扰的障碍或病症的症状或治疗这种障碍或病症的用途 |
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| ES2749103T3 (es) * | 2014-09-12 | 2020-03-19 | Knopp Biosciences Llc | Benzoimidazol-1,2-ilamidas como activadores del canal Kv7 |
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