JP4471842B2 - アミド化合物および該化合物を用いる方法 - Google Patents
アミド化合物および該化合物を用いる方法 Download PDFInfo
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- JP4471842B2 JP4471842B2 JP2004551393A JP2004551393A JP4471842B2 JP 4471842 B2 JP4471842 B2 JP 4471842B2 JP 2004551393 A JP2004551393 A JP 2004551393A JP 2004551393 A JP2004551393 A JP 2004551393A JP 4471842 B2 JP4471842 B2 JP 4471842B2
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- Prior art keywords
- alkyl
- phenyl
- amino
- chloro
- benzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims description 190
- -1 Amide compound Chemical class 0.000 title claims description 114
- 238000000034 method Methods 0.000 title description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 145
- 239000000203 mixture Substances 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 39
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 35
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000012453 solvate Substances 0.000 claims description 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- JGDAUYINPFOWKO-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n,n-bis(2-methoxyethyl)acetamide Chemical compound COCCN(CCOC)C(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 JGDAUYINPFOWKO-UHFFFAOYSA-N 0.000 claims description 4
- VQSVIGRDQHFJRV-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 VQSVIGRDQHFJRV-UHFFFAOYSA-N 0.000 claims description 4
- PUBWYHPDDAABEY-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(thiophen-3-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCC3=CSC=C3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl PUBWYHPDDAABEY-UHFFFAOYSA-N 0.000 claims description 4
- NZBJBYFAEOMOLK-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-ethylacetamide Chemical compound CCNC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 NZBJBYFAEOMOLK-UHFFFAOYSA-N 0.000 claims description 4
- ROOSXCIEEMPICJ-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-methylacetamide Chemical compound CNC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 ROOSXCIEEMPICJ-UHFFFAOYSA-N 0.000 claims description 4
- FBAWYDRIEYMSRF-NRFANRHFSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-[(2r)-2-phenylpropyl]amino]propoxy]phenyl]-n-methylacetamide Chemical compound CNC(=O)CC1=CC=CC(OCCCN(C[C@H](C)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 FBAWYDRIEYMSRF-NRFANRHFSA-N 0.000 claims description 4
- VPKIEXZUKCEULY-HXUWFJFHSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-[(2s)-2-phenylpropyl]amino]propoxy]phenyl]acetamide Chemical compound C([C@@H](C)C=1C=CC=CC=1)N(CC=1C(=C(C=CC=1)C(F)(F)F)Cl)CCCOC1=CC=CC(CC(N)=O)=C1 VPKIEXZUKCEULY-HXUWFJFHSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- RHAZNLRGJLWIEP-UHFFFAOYSA-N [4-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-morpholin-4-ylmethanone Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=CC(=CC=2)C(=O)N2CCOCC2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl RHAZNLRGJLWIEP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- JIJRRSWBUNLYLJ-UHFFFAOYSA-N 2-[3-[3-[(1-chloro-2,2,2-trifluoro-1-phenylethyl)-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-methyl-n-methylsulfonylacetamide Chemical compound CS(=O)(=O)N(C)C(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)C(Cl)(C=2C=CC=CC=2)C(F)(F)F)=C1 JIJRRSWBUNLYLJ-UHFFFAOYSA-N 0.000 claims description 3
- JPDITNPFVNARTM-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-1-morpholin-4-ylethanone Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)N3CCOCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl JPDITNPFVNARTM-UHFFFAOYSA-N 0.000 claims description 3
- ACJGLVNGBARSHS-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-methylsulfonylacetamide Chemical compound CS(=O)(=O)NC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 ACJGLVNGBARSHS-UHFFFAOYSA-N 0.000 claims description 3
- BDJPUZLCFVSBKJ-UHFFFAOYSA-N 3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]-n-methylsulfonylbenzamide Chemical compound CS(=O)(=O)NC(=O)C1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 BDJPUZLCFVSBKJ-UHFFFAOYSA-N 0.000 claims description 3
- KHAKOMLENQVTIM-UHFFFAOYSA-N 3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]-n-phenylbenzamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(C=CC=2)C(=O)NC=2C=CC=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl KHAKOMLENQVTIM-UHFFFAOYSA-N 0.000 claims description 3
- ROGYVMRWKMIZHL-UHFFFAOYSA-N [3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-morpholin-4-ylmethanone Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(C=CC=2)C(=O)N2CCOCC2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl ROGYVMRWKMIZHL-UHFFFAOYSA-N 0.000 claims description 3
- KRAYPQRGXBDPLU-UHFFFAOYSA-N n-(benzenesulfonyl)-2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NS(=O)(=O)C=3C=CC=CC=3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl KRAYPQRGXBDPLU-UHFFFAOYSA-N 0.000 claims description 3
- VUTFHZRXXLFPJG-UHFFFAOYSA-N n-(benzenesulfonyl)-3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]benzamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(C=CC=2)C(=O)NS(=O)(=O)C=2C=CC=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl VUTFHZRXXLFPJG-UHFFFAOYSA-N 0.000 claims description 3
- UNCCRIIQFWXPTD-UHFFFAOYSA-N 1-(azepan-1-yl)-2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)N3CCCCCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl UNCCRIIQFWXPTD-UHFFFAOYSA-N 0.000 claims description 2
- RBCAQTJXLDEOGI-UHFFFAOYSA-N 1-(azetidin-1-yl)-2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)N3CCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl RBCAQTJXLDEOGI-UHFFFAOYSA-N 0.000 claims description 2
- WUZMUUCMIBORGO-MUUNZHRXSA-N 2-[3-[(2r)-3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]-2-methylpropoxy]phenyl]-1-morpholin-4-ylethanone Chemical compound C([C@H](C)CN(CC(C=1C=CC=CC=1)C=1C=CC=CC=1)CC=1C(=C(C=CC=1)C(F)(F)F)Cl)OC(C=1)=CC=CC=1CC(=O)N1CCOCC1 WUZMUUCMIBORGO-MUUNZHRXSA-N 0.000 claims description 2
- ZMMUPZWDFRESBH-MUUNZHRXSA-N 2-[3-[(3r)-3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]butoxy]phenyl]-1-morpholin-4-ylethanone Chemical compound C([C@@H](C)N(CC(C=1C=CC=CC=1)C=1C=CC=CC=1)CC=1C(=C(C=CC=1)C(F)(F)F)Cl)COC(C=1)=CC=CC=1CC(=O)N1CCOCC1 ZMMUPZWDFRESBH-MUUNZHRXSA-N 0.000 claims description 2
- UWOKZLHWMCAKNL-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 UWOKZLHWMCAKNL-UHFFFAOYSA-N 0.000 claims description 2
- UVPIUWZHXDPFLT-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-1-piperidin-1-ylethanone Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)N3CCCCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl UVPIUWZHXDPFLT-UHFFFAOYSA-N 0.000 claims description 2
- LXCKRLSGYBLLQC-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-1-pyrrolidin-1-ylethanone Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)N3CCCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl LXCKRLSGYBLLQC-UHFFFAOYSA-N 0.000 claims description 2
- QAERNMYXUAECKG-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)NC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 QAERNMYXUAECKG-UHFFFAOYSA-N 0.000 claims description 2
- IYOOJNDWYAWJAJ-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(1-thiophen-2-ylethyl)acetamide Chemical compound C=1C=CSC=1C(C)NC(=O)CC(C=1)=CC=CC=1OCCCN(CC=1C(=C(C=CC=1)C(F)(F)F)Cl)CC(C=1C=CC=CC=1)C1=CC=CC=C1 IYOOJNDWYAWJAJ-UHFFFAOYSA-N 0.000 claims description 2
- HSPOBKWYNBSHJL-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(1h-imidazol-2-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCC=3NC=CN=3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl HSPOBKWYNBSHJL-UHFFFAOYSA-N 0.000 claims description 2
- MBSMRYBWOFLRRS-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(2-methoxyethyl)-n-methylacetamide Chemical compound COCCN(C)C(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 MBSMRYBWOFLRRS-UHFFFAOYSA-N 0.000 claims description 2
- VRKGFNPCMGDSDP-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(2-methoxyethyl)acetamide Chemical compound COCCNC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 VRKGFNPCMGDSDP-UHFFFAOYSA-N 0.000 claims description 2
- UGJJIIIGYODIIQ-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(2-morpholin-4-ylethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCCN3CCOCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl UGJJIIIGYODIIQ-UHFFFAOYSA-N 0.000 claims description 2
- YBSOHRFWROHJGO-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(2-pyridin-2-ylethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCCC=3N=CC=CC=3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl YBSOHRFWROHJGO-UHFFFAOYSA-N 0.000 claims description 2
- YKZZSMXWFDRQLL-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(2-pyrrolidin-1-ylethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCCN3CCCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl YKZZSMXWFDRQLL-UHFFFAOYSA-N 0.000 claims description 2
- PAXDFWWAIAUTPS-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(2-thiomorpholin-4-ylethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCCN3CCSCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl PAXDFWWAIAUTPS-UHFFFAOYSA-N 0.000 claims description 2
- VLPAWSOBMDEXDU-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(3-methoxypropyl)acetamide Chemical compound COCCCNC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 VLPAWSOBMDEXDU-UHFFFAOYSA-N 0.000 claims description 2
- WBQXQCKPFPSGEA-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(3-propan-2-yloxypropyl)acetamide Chemical compound CC(C)OCCCNC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 WBQXQCKPFPSGEA-UHFFFAOYSA-N 0.000 claims description 2
- RBFMRFYPOLGLOE-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(furan-2-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCC=3OC=CC=3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl RBFMRFYPOLGLOE-UHFFFAOYSA-N 0.000 claims description 2
- FUSUQAJTALNVLX-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(oxolan-2-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCC3OCCC3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl FUSUQAJTALNVLX-UHFFFAOYSA-N 0.000 claims description 2
- NRXITTYWWDPXFP-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCC=3N=CC=CC=3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl NRXITTYWWDPXFP-UHFFFAOYSA-N 0.000 claims description 2
- QERBGEQZQLBSQZ-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(pyridin-3-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCC=3C=NC=CC=3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl QERBGEQZQLBSQZ-UHFFFAOYSA-N 0.000 claims description 2
- QWGCDALYJUVOAK-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-(thiophen-2-ylmethyl)acetamide Chemical compound FC(F)(F)C1=CC=CC(CN(CCCOC=2C=C(CC(=O)NCC=3SC=CC=3)C=CC=2)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1Cl QWGCDALYJUVOAK-UHFFFAOYSA-N 0.000 claims description 2
- SFLJYYWLTXMLMW-UHFFFAOYSA-N 2-[3-[3-[[2-chloro-3-(trifluoromethyl)phenyl]methyl-(2,2-diphenylethyl)amino]propoxy]phenyl]-n-[(1-ethylpyrrolidin-2-yl)methyl]acetamide Chemical compound CCN1CCCC1CNC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C(=C(C=CC=2)C(F)(F)F)Cl)=C1 SFLJYYWLTXMLMW-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- 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
- C07C235/32—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 containing six-membered aromatic rings
- C07C235/34—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 containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C—CHEMISTRY; METALLURGY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
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- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
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- Chemical & Material Sciences (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
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| US7365085B2 (en) * | 2002-03-27 | 2008-04-29 | Smithkline Beecham Corporation | Compounds and methods |
| JP2005521721A (ja) * | 2002-03-27 | 2005-07-21 | スミスクライン・ビーチャム・コーポレイション | 酸およびエステル化合物ならびにその使用方法 |
| AU2003223340A1 (en) | 2002-03-27 | 2003-10-13 | Smithkline Beecham Corporation | Certain pharmaceutically useful substituted aminoalkyl heterocycles |
| AU2003220558A1 (en) | 2002-03-27 | 2004-06-03 | Smithkline Beecham Corporation | Amide compounds and methods of using the same |
| WO2007002654A2 (en) * | 2005-06-28 | 2007-01-04 | Daiichi Sankyo Company, Limited. | Lxr ligand testing method |
| AU2007260356B2 (en) * | 2006-06-16 | 2013-01-24 | H. Lundbeck A/S | Crystalline forms of 4- [2- (4-methylphenylsulfanyl) -phenyl] piperidine with combined serotonin and norepinephrine reuptake inhibition for the treatment of neuropathic pain |
| AR076753A1 (es) | 2009-05-07 | 2011-07-06 | Gruenenthal Chemie | Derivados de carboxamida y urea aromaticas sustituidas como ligandos del receptor de vanilloides. |
| CA3211094A1 (en) | 2012-08-13 | 2014-02-20 | The Rockefeller University | Treatment and diagnosis of melanoma |
| US10669296B2 (en) | 2014-01-10 | 2020-06-02 | Rgenix, Inc. | LXR agonists and uses thereof |
| IL313498A (en) | 2014-10-06 | 2024-08-01 | Vertex Pharma | Modulators of the cystic fibrosis transmembrane conductance regulator |
| CN109069461A (zh) | 2016-01-11 | 2018-12-21 | 洛克菲勒大学 | 与髓源性抑制细胞相关的病症的治疗方法 |
| EP3436446B1 (en) | 2016-03-31 | 2023-06-07 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| HRP20211683T1 (hr) | 2016-09-30 | 2022-03-04 | Vertex Pharmaceuticals Incorporated | Modulator transmembranskog regulatora provodljivosti cistične fibroze, farmaceutski pripravci, postupci liječenja, i postupak za pripravu modulatora |
| MX2021013639A (es) | 2016-12-09 | 2022-09-30 | Vertex Pharma | Forma cristalina del compuesto 1, un modulador del regulador de conductancia transmembrana de fibrosis quística, procesos para su preparación, composiciones farmacéuticas del compuesto 1, y su uso en el tratamiento de fibrosis quística. |
| AU2018226879B2 (en) | 2017-03-03 | 2023-09-14 | Inspirna, Inc. | Formulations with improved stability |
| AU2018279646B2 (en) | 2017-06-08 | 2023-04-06 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| AU2018304168B2 (en) | 2017-07-17 | 2023-05-04 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| TWI799435B (zh) | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | 製備化合物之製程 |
| WO2019079760A1 (en) | 2017-10-19 | 2019-04-25 | Vertex Pharmaceuticals Incorporated | CRYSTALLINE FORMS AND COMPOSITIONS OF CFTR MODULATORS |
| EP3713575A4 (en) | 2017-11-21 | 2021-08-25 | Rgenix, Inc. | POLYMORPHS AND THEIR USES |
| US11465985B2 (en) | 2017-12-08 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| CN114195672A (zh) * | 2018-03-02 | 2022-03-18 | 俄勒冈健康科学大学 | 小分子核受体调节剂的酰胺前药 |
| WO2019200246A1 (en) | 2018-04-13 | 2019-10-17 | Alexander Russell Abela | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| EP3870292A4 (en) | 2018-10-26 | 2022-11-09 | The Research Foundation for The State University of New York | COMBINATION OF SEROTONIN-SPECIFIC RESUPPUT INHIBITOR AND SEROTONIN 1A RECEPTOR PARTIAL AGONIST TO REDUCE L-DOPA-INDUCED DYSKINESIA |
| US11827596B2 (en) | 2018-12-12 | 2023-11-28 | Autobahn Therapeutics, Inc. | Thyromimetics |
| AU2020232205A1 (en) | 2019-03-01 | 2021-10-21 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| WO2021050648A1 (en) * | 2019-09-11 | 2021-03-18 | Rgenix, Inc. | Methods of treating cancer |
| CA3163089A1 (en) | 2019-11-29 | 2021-06-03 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| HUE067466T2 (hu) | 2019-12-13 | 2024-10-28 | Inspirna Inc | Fémsók és alkalmazásuk |
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| US4139623A (en) * | 1974-05-14 | 1979-02-13 | C-G Corp. | Cyclic-substituted derivatives of 1-amino-2-propanol |
| EP0394440B1 (en) | 1987-10-20 | 1994-05-11 | Otsuka Pharmaceutical Co., Ltd. | Phenylcarboxylic acid derivatives |
| US20030153541A1 (en) * | 1997-10-31 | 2003-08-14 | Robert Dudley | Novel anticholesterol compositions and method for using same |
| US6316503B1 (en) | 1999-03-15 | 2001-11-13 | Tularik Inc. | LXR modulators |
| WO2001060818A1 (en) * | 2000-02-14 | 2001-08-23 | Tularik Inc. | Lxr modulators |
| WO2002024632A2 (en) * | 2000-09-18 | 2002-03-28 | Glaxo Group Limited | Substituted aminopropoxyaryl derivatives useful as agonists for lxr |
| US20030229062A1 (en) * | 2001-12-07 | 2003-12-11 | The Regents Of The University Of California | Treatments for age-related macular degeneration (AMD) |
| EP1461028A4 (en) * | 2001-12-07 | 2007-07-25 | Univ California | TREATMENT FOR AGE-RELATED MACULAR AGENCY |
| US7470659B2 (en) * | 2001-12-07 | 2008-12-30 | The Regents Of The University Of California | Methods to increase reverse cholesterol transport in the retinal pigment epithelium (RPE) and Bruch's membrane (BM) |
| AU2003220521A1 (en) * | 2002-03-27 | 2003-10-13 | Smithkline Beecham Corporation | Methods of treatment with lxr modulators |
| US7365085B2 (en) * | 2002-03-27 | 2008-04-29 | Smithkline Beecham Corporation | Compounds and methods |
| AU2003223340A1 (en) | 2002-03-27 | 2003-10-13 | Smithkline Beecham Corporation | Certain pharmaceutically useful substituted aminoalkyl heterocycles |
| JP2005521721A (ja) | 2002-03-27 | 2005-07-21 | スミスクライン・ビーチャム・コーポレイション | 酸およびエステル化合物ならびにその使用方法 |
| AU2003220558A1 (en) | 2002-03-27 | 2004-06-03 | Smithkline Beecham Corporation | Amide compounds and methods of using the same |
| US20050036992A1 (en) * | 2002-12-23 | 2005-02-17 | Irm Llc | Novel use of liver X receptor agonists |
| GB0230177D0 (en) | 2002-12-24 | 2003-02-05 | Karobio Ab | LXR beta crystal |
| US20060160834A1 (en) | 2003-06-06 | 2006-07-20 | Fong Tung M | Combination therapy for the treatment of hypertension |
| US20070099884A1 (en) | 2003-06-06 | 2007-05-03 | Erondu Ngozi E | Combination therapy for the treatment of diabetes |
| US20060189693A1 (en) | 2003-07-22 | 2006-08-24 | Barone Frank C | Methods of treatment with lxr agonists |
| JP2007500158A (ja) | 2003-07-28 | 2007-01-11 | グラクソ グループ リミテッド | Lxrアゴニストを用いる炎症性腸疾患の治療方法 |
| WO2005055998A1 (en) | 2003-12-04 | 2005-06-23 | Smithkline Beecham Corporation | Methods of treatment with lxr agonists |
| JP2007516258A (ja) * | 2003-12-12 | 2007-06-21 | ワイス | 心臓血管の疾患治療に有用なキノリン誘導体 |
| US20060014231A1 (en) | 2004-06-24 | 2006-01-19 | Luc Van Rompaey | Methods and compositions to promote bone homeostasis |
| KR101266587B1 (ko) | 2004-07-02 | 2013-05-22 | 상꾜 가부시키가이샤 | 조직 인자 생성 억제제 |
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| EP1497270A1 (en) | 2005-01-19 |
| WO2004043939A1 (en) | 2004-05-27 |
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