JP3662566B2 - エステル化合物及びその医薬用途 - Google Patents
エステル化合物及びその医薬用途 Download PDFInfo
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- JP3662566B2 JP3662566B2 JP2003053869A JP2003053869A JP3662566B2 JP 3662566 B2 JP3662566 B2 JP 3662566B2 JP 2003053869 A JP2003053869 A JP 2003053869A JP 2003053869 A JP2003053869 A JP 2003053869A JP 3662566 B2 JP3662566 B2 JP 3662566B2
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- JP
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- Prior art keywords
- phenyl
- biphenyl
- carbonyl
- trifluoromethyl
- amino
- Prior art date
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- -1 Ester compound Chemical class 0.000 title claims description 384
- 150000001875 compounds Chemical class 0.000 claims description 228
- 239000003795 chemical substances by application Substances 0.000 claims description 126
- 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 claims description 91
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 89
- 150000003839 salts Chemical class 0.000 claims description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
- 108010038232 microsomal triglyceride transfer protein Proteins 0.000 claims description 78
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 74
- 230000001225 therapeutic effect Effects 0.000 claims description 69
- 239000003814 drug Substances 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 230000000069 prophylactic effect Effects 0.000 claims description 66
- 210000004185 liver Anatomy 0.000 claims description 55
- 229940079593 drug Drugs 0.000 claims description 51
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 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
- 238000013268 sustained release Methods 0.000 claims description 44
- 239000012730 sustained-release form Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 36
- 210000000813 small intestine Anatomy 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 29
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 206010012601 diabetes mellitus Diseases 0.000 claims description 22
- 230000002401 inhibitory effect Effects 0.000 claims description 22
- 239000003112 inhibitor Substances 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 208000008589 Obesity Diseases 0.000 claims description 19
- YCTONGBVYOQJMT-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(pyrrolidine-1-carbonyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N2CCCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 YCTONGBVYOQJMT-UHFFFAOYSA-N 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 235000020824 obesity Nutrition 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 210000004369 blood Anatomy 0.000 claims description 17
- 239000008280 blood Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
- 206010020772 Hypertension Diseases 0.000 claims description 16
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 229940124597 therapeutic agent Drugs 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 15
- ZGJRLDZYCWSCCV-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[2-(trifluoromethyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZGJRLDZYCWSCCV-UHFFFAOYSA-N 0.000 claims description 15
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- CIQDMHUPCXRGEX-UHFFFAOYSA-N diethyl 2-[[2-[3-(diethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(CC)CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 CIQDMHUPCXRGEX-UHFFFAOYSA-N 0.000 claims description 13
- 239000002775 capsule Substances 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 208000029078 coronary artery disease Diseases 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- PTMSZUJDCWDNIM-UHFFFAOYSA-N 5-[2-(3-ethoxy-2-ethoxycarbonyl-3-oxo-2-phenylpropoxy)-2-oxoethyl]-2-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoic acid Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(O)=O)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 PTMSZUJDCWDNIM-UHFFFAOYSA-N 0.000 claims description 11
- CFBFLFVYKYEEJV-UHFFFAOYSA-N [3-(2-methoxyethylamino)-2-(2-methoxyethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCOC)(C(=O)NCCOC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 CFBFLFVYKYEEJV-UHFFFAOYSA-N 0.000 claims description 11
- DFGHXIXUBYPJQB-UHFFFAOYSA-N [3-(2-methylpropylamino)-2-(2-methylpropylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC(C)C)(C(=O)NCC(C)C)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DFGHXIXUBYPJQB-UHFFFAOYSA-N 0.000 claims description 11
- HIHYOELGVOQNGO-UHFFFAOYSA-N [3-(3-methylbutylamino)-2-(3-methylbutylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC(C)C)(C(=O)NCCC(C)C)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 HIHYOELGVOQNGO-UHFFFAOYSA-N 0.000 claims description 11
- XCSGKZORHSMPQF-UHFFFAOYSA-N [3-(butylamino)-2-(butylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCCC)(C(=O)NCCCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XCSGKZORHSMPQF-UHFFFAOYSA-N 0.000 claims description 11
- JQNSLKHURUPEQI-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(diethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N(CC)CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 JQNSLKHURUPEQI-UHFFFAOYSA-N 0.000 claims description 11
- DXXPLWNAZWAMJS-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(methylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)NC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DXXPLWNAZWAMJS-UHFFFAOYSA-N 0.000 claims description 11
- NHFQUJXTBLFPRU-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-[di(propan-2-yl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N(C(C)C)C(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 NHFQUJXTBLFPRU-UHFFFAOYSA-N 0.000 claims description 11
- ZBNUMMNPAKPRKH-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-[ethyl(methyl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N(C)CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZBNUMMNPAKPRKH-UHFFFAOYSA-N 0.000 claims description 11
- OWQAZUOJCGCXDC-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-[methyl(propan-2-yl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N(C)C(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 OWQAZUOJCGCXDC-UHFFFAOYSA-N 0.000 claims description 11
- AYWLLVATNLDIBK-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-[methyl(propyl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)N(C)CCC)=CC=1CC(=O)OCC(C(=O)NCC)(C(=O)NCC)C1=CC=CC=C1 AYWLLVATNLDIBK-UHFFFAOYSA-N 0.000 claims description 11
- VHCRJSOJSAMPCR-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-ethoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1OCC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VHCRJSOJSAMPCR-UHFFFAOYSA-N 0.000 claims description 11
- VDHCJCXXYLHWAB-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-ethyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VDHCJCXXYLHWAB-UHFFFAOYSA-N 0.000 claims description 11
- FCRDUDHCGYHDDW-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-methoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1OC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FCRDUDHCGYHDDW-UHFFFAOYSA-N 0.000 claims description 11
- IRROEFVBBOXXFG-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-phenylmethoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1OCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 IRROEFVBBOXXFG-UHFFFAOYSA-N 0.000 claims description 11
- DZVCVGDQRQMIGL-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-piperidin-1-yl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1N2CCCCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DZVCVGDQRQMIGL-UHFFFAOYSA-N 0.000 claims description 11
- SOMZASTXYLSNTM-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-propan-2-yl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 SOMZASTXYLSNTM-UHFFFAOYSA-N 0.000 claims description 11
- KCMCSGBVERRGNI-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-propan-2-yloxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1OC(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 KCMCSGBVERRGNI-UHFFFAOYSA-N 0.000 claims description 11
- GOMHCLVRTCQSTR-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-propoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(OCCC)=CC=1CC(=O)OCC(C(=O)NCC)(C(=O)NCC)C1=CC=CC=C1 GOMHCLVRTCQSTR-UHFFFAOYSA-N 0.000 claims description 11
- QEZKAQXBQPBBBT-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-pyrrolidin-1-yl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1N2CCCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QEZKAQXBQPBBBT-UHFFFAOYSA-N 0.000 claims description 11
- ZYHNGVIIMSMQEY-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[(2-phenylbenzoyl)amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=CC=C1 ZYHNGVIIMSMQEY-UHFFFAOYSA-N 0.000 claims description 11
- HOSCJSLPFBRCOK-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-(3,4-dichlorophenyl)benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(Cl)C(Cl)=C1 HOSCJSLPFBRCOK-UHFFFAOYSA-N 0.000 claims description 11
- UKWCRRMWWDPWIC-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-(4-chlorophenyl)benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(Cl)C=C1 UKWCRRMWWDPWIC-UHFFFAOYSA-N 0.000 claims description 11
- YXSJUDDDSJWUQS-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 YXSJUDDDSJWUQS-UHFFFAOYSA-N 0.000 claims description 11
- WVWLTHWFFAXMBN-UHFFFAOYSA-N [3-(methylamino)-2-(methylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NC)(C(=O)NC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WVWLTHWFFAXMBN-UHFFFAOYSA-N 0.000 claims description 11
- GYBGTVFSTMDCJK-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(2,2,2-trifluoroethylamino)-2-(2,2,2-trifluoroethylcarbamoyl)propyl] 2-[4-[(2-phenylbenzoyl)amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC(F)(F)F)(C(=O)NCC(F)(F)F)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GYBGTVFSTMDCJK-UHFFFAOYSA-N 0.000 claims description 11
- ZWQZMSAKNTZADX-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(2,2,2-trifluoroethylamino)-2-(2,2,2-trifluoroethylcarbamoyl)propyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC(F)(F)F)(C(=O)NCC(F)(F)F)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZWQZMSAKNTZADX-UHFFFAOYSA-N 0.000 claims description 11
- DEEWGADMSNAMJZ-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(propylamino)-2-(propylcarbamoyl)propyl] 2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)(C(=O)NCCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DEEWGADMSNAMJZ-UHFFFAOYSA-N 0.000 claims description 11
- DONVKTBFBUILDH-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(propylamino)-2-(propylcarbamoyl)propyl] 2-[3-methoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)(C(=O)NCCC)COC(=O)CC(C=C1OC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DONVKTBFBUILDH-UHFFFAOYSA-N 0.000 claims description 11
- HBQNCNWIWAUDEO-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(propylamino)-2-(propylcarbamoyl)propyl] 2-[3-methyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)(C(=O)NCCC)COC(=O)CC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 HBQNCNWIWAUDEO-UHFFFAOYSA-N 0.000 claims description 11
- HIBYADHVPNNANO-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[3-[ethyl(methyl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=C1C(=O)N(C)CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 HIBYADHVPNNANO-UHFFFAOYSA-N 0.000 claims description 11
- QRDINOXMOOVSQB-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[3-[methyl(propyl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)N(C)CCC)=CC=1CC(=O)OCCC(C(=O)NCC)(C(=O)NCC)C1=CC=CC=C1 QRDINOXMOOVSQB-UHFFFAOYSA-N 0.000 claims description 11
- FURGMBSIHLXZPV-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[3-ethoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=C1OCC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FURGMBSIHLXZPV-UHFFFAOYSA-N 0.000 claims description 11
- VKQWBAHJJDDKIS-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[3-ethyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=C1CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VKQWBAHJJDDKIS-UHFFFAOYSA-N 0.000 claims description 11
- XWFCGZFKTKCKQH-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[3-methoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=C1OC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XWFCGZFKTKCKQH-UHFFFAOYSA-N 0.000 claims description 11
- NJEHRVLBDMDIMY-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[3-propan-2-yloxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=C1OC(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 NJEHRVLBDMDIMY-UHFFFAOYSA-N 0.000 claims description 11
- NIIOQUAZHXNTQW-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 NIIOQUAZHXNTQW-UHFFFAOYSA-N 0.000 claims description 11
- PFXWMKPZCNOEGO-UHFFFAOYSA-N [4-[2-oxo-2-[3-oxo-2-phenyl-3-(2,2,2-trifluoroethylamino)-2-(2,2,2-trifluoroethylcarbamoyl)propoxy]ethyl]phenyl] 2-[4-(trifluoromethyl)phenyl]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC(F)(F)F)(C(=O)NCC(F)(F)F)COC(=O)CC(C=C1)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 PFXWMKPZCNOEGO-UHFFFAOYSA-N 0.000 claims description 11
- DMFXDHPZDPSKKE-UHFFFAOYSA-N [4-[2-oxo-2-[3-oxo-2-phenyl-3-(2,2,2-trifluoroethylamino)-2-(2,2,2-trifluoroethylcarbamoyl)propoxy]ethyl]phenyl] 2-phenylbenzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC(F)(F)F)(C(=O)NCC(F)(F)F)COC(=O)CC(C=C1)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=CC=C1 DMFXDHPZDPSKKE-UHFFFAOYSA-N 0.000 claims description 11
- BGFXOQFHFAXQIL-UHFFFAOYSA-N [4-[4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutoxy]carbonylphenyl] 2-[4-(trifluoromethyl)phenyl]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)C(C=C1)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 BGFXOQFHFAXQIL-UHFFFAOYSA-N 0.000 claims description 11
- SEQUXWDZPPNBFG-UHFFFAOYSA-N [4-oxo-3-phenyl-4-(propylamino)-3-(propylcarbamoyl)butyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)(C(=O)NCCC)CCOC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 SEQUXWDZPPNBFG-UHFFFAOYSA-N 0.000 claims description 11
- KMOJSUYDGMMPKZ-UHFFFAOYSA-N [5-(ethylamino)-4-(ethylcarbamoyl)-5-oxo-4-phenylpentyl] 2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCCOC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 KMOJSUYDGMMPKZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- LUYWZYCPFLPYCW-UHFFFAOYSA-N benzyl 5-[2-[3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropoxy]-2-oxoethyl]-2-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)OCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 LUYWZYCPFLPYCW-UHFFFAOYSA-N 0.000 claims description 11
- NMGIQDDNASBFBY-UHFFFAOYSA-N dicyclohexyl 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CC(=O)OCC(C=1C=CC=CC=1)(C(=O)OC1CCCCC1)C(=O)OC1CCCCC1 NMGIQDDNASBFBY-UHFFFAOYSA-N 0.000 claims description 11
- DGZFWSSCJDGXTC-UHFFFAOYSA-N diethyl 2-[2-[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DGZFWSSCJDGXTC-UHFFFAOYSA-N 0.000 claims description 11
- WDDZGKRLQQENAE-UHFFFAOYSA-N diethyl 2-[2-[2-[3-(dimethylcarbamoyl)-4-[[4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(F)(F)F)C=C1 WDDZGKRLQQENAE-UHFFFAOYSA-N 0.000 claims description 11
- ZOLGRHUWNCZOFY-UHFFFAOYSA-N diethyl 2-[2-[2-[3-(dimethylcarbamoyl)-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(C)C=C1C1=CC=C(C(F)(F)F)C=C1 ZOLGRHUWNCZOFY-UHFFFAOYSA-N 0.000 claims description 11
- KZKOOWGZUAINSN-UHFFFAOYSA-N diethyl 2-[2-[2-chloro-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)C(C(=C1)Cl)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 KZKOOWGZUAINSN-UHFFFAOYSA-N 0.000 claims description 11
- RXQBXNWFJRSNLR-UHFFFAOYSA-N diethyl 2-[3-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]propanoyloxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CCC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 RXQBXNWFJRSNLR-UHFFFAOYSA-N 0.000 claims description 11
- ZCFVKPQPKGPBJV-UHFFFAOYSA-N diethyl 2-[[2-[3-(2-methylpropanoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)C(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZCFVKPQPKGPBJV-UHFFFAOYSA-N 0.000 claims description 11
- VJHDWFVDJGEATB-UHFFFAOYSA-N diethyl 2-[[2-[3-(2-methylpropyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1CC(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VJHDWFVDJGEATB-UHFFFAOYSA-N 0.000 claims description 11
- KGENKWUIWLJMTO-UHFFFAOYSA-N diethyl 2-[[2-[3-(4-methyl-1,3-thiazol-2-yl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C=2SC=C(C)N=2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 KGENKWUIWLJMTO-UHFFFAOYSA-N 0.000 claims description 11
- XIRSBALRSUGZJS-UHFFFAOYSA-N diethyl 2-[[2-[3-(diethylamino)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1N(CC)CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XIRSBALRSUGZJS-UHFFFAOYSA-N 0.000 claims description 11
- DNIUSHRQIMHNGP-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylamino)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DNIUSHRQIMHNGP-UHFFFAOYSA-N 0.000 claims description 11
- YADROHWZRUUBQB-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[2-[4-(trifluoromethyl)phenyl]benzoyl]oxyphenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 YADROHWZRUUBQB-UHFFFAOYSA-N 0.000 claims description 11
- DHGVRVNVNPHFIK-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-(4-ethylphenyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(CC)C=C1 DHGVRVNVNPHFIK-UHFFFAOYSA-N 0.000 claims description 11
- ITUZZAFKZDHVQE-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-(4-fluorophenyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(F)C=C1 ITUZZAFKZDHVQE-UHFFFAOYSA-N 0.000 claims description 11
- ZBSOGIQKERKSCH-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-(4-methylphenyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C)C=C1 ZBSOGIQKERKSCH-UHFFFAOYSA-N 0.000 claims description 11
- CQQKNFFDPBRYCS-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-(4-prop-1-en-2-ylphenyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(C)=C)C=C1 CQQKNFFDPBRYCS-UHFFFAOYSA-N 0.000 claims description 11
- TVZOEIGIFBAXHY-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-(4-propan-2-ylphenyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(C)C)C=C1 TVZOEIGIFBAXHY-UHFFFAOYSA-N 0.000 claims description 11
- YHNSSFYTXVDPMR-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[2-fluoro-4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1F YHNSSFYTXVDPMR-UHFFFAOYSA-N 0.000 claims description 11
- LHQHRAXQAXGXQN-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[3-fluoro-4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C(F)=C1 LHQHRAXQAXGXQN-UHFFFAOYSA-N 0.000 claims description 11
- OFPAVWJFHPRWJZ-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-(1,3-thiazol-2-yl)propanedioate Chemical compound N=1C=CSC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 OFPAVWJFHPRWJZ-UHFFFAOYSA-N 0.000 claims description 11
- UQNZJMYBNXNYTD-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-(2-methylphenyl)propanedioate Chemical compound C=1C=CC=C(C)C=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UQNZJMYBNXNYTD-UHFFFAOYSA-N 0.000 claims description 11
- RHQFACXKVAZQEQ-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-(3-methylphenyl)propanedioate Chemical compound C=1C=CC(C)=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 RHQFACXKVAZQEQ-UHFFFAOYSA-N 0.000 claims description 11
- PKPOUGBPUSRAEB-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-(3-methylthiophen-2-yl)propanedioate Chemical compound S1C=CC(C)=C1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 PKPOUGBPUSRAEB-UHFFFAOYSA-N 0.000 claims description 11
- FPUQGCOBYOXAED-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FPUQGCOBYOXAED-UHFFFAOYSA-N 0.000 claims description 11
- ZBORAOCCJCJTHA-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-pyridin-2-ylpropanedioate Chemical compound C=1C=CC=NC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZBORAOCCJCJTHA-UHFFFAOYSA-N 0.000 claims description 11
- NEBLXFSOGXOHGE-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-thiophen-3-ylpropanedioate Chemical compound C1=CSC=C1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 NEBLXFSOGXOHGE-UHFFFAOYSA-N 0.000 claims description 11
- RQAZMVFZXSXJJY-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-methyl-6-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=C(C)C=CC=C1C1=CC=C(C(F)(F)F)C=C1 RQAZMVFZXSXJJY-UHFFFAOYSA-N 0.000 claims description 11
- UQVFFSRYZKEVAA-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[3-fluoro-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC(F)=C1C1=CC=C(C(F)(F)F)C=C1 UQVFFSRYZKEVAA-UHFFFAOYSA-N 0.000 claims description 11
- TXZREXQQNQNFOJ-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[3-methyl-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC(C)=C1C1=CC=C(C(F)(F)F)C=C1 TXZREXQQNQNFOJ-UHFFFAOYSA-N 0.000 claims description 11
- NKGWHTODKOYZMP-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1C1=CC=C(C(F)(F)F)C=C1 NKGWHTODKOYZMP-UHFFFAOYSA-N 0.000 claims description 11
- YMWUDKGZMSDSCV-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[4-ethoxy-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(OCC)C=C1C1=CC=C(C(F)(F)F)C=C1 YMWUDKGZMSDSCV-UHFFFAOYSA-N 0.000 claims description 11
- OZOLXOKXJZKKAP-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[4-methoxy-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(OC)C=C1C1=CC=C(C(F)(F)F)C=C1 OZOLXOKXJZKKAP-UHFFFAOYSA-N 0.000 claims description 11
- AQAQSTFAUQIWBD-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(C)C=C1C1=CC=C(C(F)(F)F)C=C1 AQAQSTFAUQIWBD-UHFFFAOYSA-N 0.000 claims description 11
- QKDJFYOBSFGMFD-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[4-propan-2-yloxy-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(OC(C)C)C=C1C1=CC=C(C(F)(F)F)C=C1 QKDJFYOBSFGMFD-UHFFFAOYSA-N 0.000 claims description 11
- FMXXDZOSHNWORQ-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[5-methyl-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC(C)=CC=C1C1=CC=C(C(F)(F)F)C=C1 FMXXDZOSHNWORQ-UHFFFAOYSA-N 0.000 claims description 11
- JPLWDRVFJCTLTM-UHFFFAOYSA-N diethyl 2-[[2-[3-[(dimethylamino)methyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1CN(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 JPLWDRVFJCTLTM-UHFFFAOYSA-N 0.000 claims description 11
- XFWHHJAJDSGMDJ-UHFFFAOYSA-N diethyl 2-[[2-[3-[di(propan-2-yl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C(C)C)C(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XFWHHJAJDSGMDJ-UHFFFAOYSA-N 0.000 claims description 11
- AONKRNBFMYDDNY-UHFFFAOYSA-N diethyl 2-[[2-[3-[methoxy(methyl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)OC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 AONKRNBFMYDDNY-UHFFFAOYSA-N 0.000 claims description 11
- BFLQTUDYSYNTFK-UHFFFAOYSA-N diethyl 2-[[2-[3-acetamido-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1NC(C)=O)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 BFLQTUDYSYNTFK-UHFFFAOYSA-N 0.000 claims description 11
- QSALIZYUAMVOJD-UHFFFAOYSA-N diethyl 2-[[2-[3-bromo-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1Br)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QSALIZYUAMVOJD-UHFFFAOYSA-N 0.000 claims description 11
- DITBXJLZCBMEJK-UHFFFAOYSA-N diethyl 2-[[2-[3-bromo-5-(dimethylcarbamoyl)-2-fluoro-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C(=C1Br)F)=CC(C(=O)N(C)C)=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DITBXJLZCBMEJK-UHFFFAOYSA-N 0.000 claims description 11
- VLJMVLJVRQYUNA-UHFFFAOYSA-N diethyl 2-[[2-[3-bromo-5-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC(Br)=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VLJMVLJVRQYUNA-UHFFFAOYSA-N 0.000 claims description 11
- BJYOVAQOPCNJJZ-UHFFFAOYSA-N diethyl 2-[[2-[3-chloro-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1Cl)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 BJYOVAQOPCNJJZ-UHFFFAOYSA-N 0.000 claims description 11
- JQVSERUQWKUTNM-UHFFFAOYSA-N diethyl 2-[[2-[3-chloro-5-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC(Cl)=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 JQVSERUQWKUTNM-UHFFFAOYSA-N 0.000 claims description 11
- ZPQCSGMTOBGHEX-UHFFFAOYSA-N diethyl 2-[[2-[3-ethoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1OCC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZPQCSGMTOBGHEX-UHFFFAOYSA-N 0.000 claims description 11
- JNNUTCZXEWHFAE-UHFFFAOYSA-N diethyl 2-[[2-[3-ethoxycarbonyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)OCC)=CC=1CC(=O)OCC(C(=O)OCC)(C(=O)OCC)C1=CC=CC=C1 JNNUTCZXEWHFAE-UHFFFAOYSA-N 0.000 claims description 11
- JJNIUYYXGTZUAE-UHFFFAOYSA-N diethyl 2-[[2-[3-ethyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 JJNIUYYXGTZUAE-UHFFFAOYSA-N 0.000 claims description 11
- QYBKHGFPCWVXGA-UHFFFAOYSA-N diethyl 2-[[2-[3-formyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C=O)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QYBKHGFPCWVXGA-UHFFFAOYSA-N 0.000 claims description 11
- UQMLHUONUHEPTG-UHFFFAOYSA-N diethyl 2-[[2-[3-hydroxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1O)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UQMLHUONUHEPTG-UHFFFAOYSA-N 0.000 claims description 11
- WCSFLQQQRIFLOM-UHFFFAOYSA-N diethyl 2-[[2-[3-methoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1OC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WCSFLQQQRIFLOM-UHFFFAOYSA-N 0.000 claims description 11
- JTSALHZINIJVKA-UHFFFAOYSA-N diethyl 2-[[2-[3-methoxycarbonyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)OC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 JTSALHZINIJVKA-UHFFFAOYSA-N 0.000 claims description 11
- HNUHDUOAQMEOMU-UHFFFAOYSA-N diethyl 2-[[2-[3-methyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 HNUHDUOAQMEOMU-UHFFFAOYSA-N 0.000 claims description 11
- PWHCSPVQLQMAKI-UHFFFAOYSA-N diethyl 2-[[2-[3-morpholin-4-yl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1N2CCOCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 PWHCSPVQLQMAKI-UHFFFAOYSA-N 0.000 claims description 11
- QPWRSIOICZIZFE-UHFFFAOYSA-N diethyl 2-[[2-[4-(dimethylcarbamoyl)-5-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]pyridin-2-yl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(N=C1)=CC(C(=O)N(C)C)=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QPWRSIOICZIZFE-UHFFFAOYSA-N 0.000 claims description 11
- XFTJHJQRJIJEJH-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-(4-acetylphenyl)benzoyl]amino]-3-(dimethylcarbamoyl)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(C)=O)C=C1 XFTJHJQRJIJEJH-UHFFFAOYSA-N 0.000 claims description 11
- JRWZHGOZIIGYDU-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-(4-bromophenyl)benzoyl]amino]-3-(dimethylcarbamoyl)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(Br)C=C1 JRWZHGOZIIGYDU-UHFFFAOYSA-N 0.000 claims description 11
- JNZGMEMZRZAERN-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-(4-chlorophenyl)benzoyl]amino]-3-(dimethylcarbamoyl)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(Cl)C=C1 JNZGMEMZRZAERN-UHFFFAOYSA-N 0.000 claims description 11
- KGCDKDLWNXXRFV-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-(4-cyanophenyl)benzoyl]amino]-3-(dimethylcarbamoyl)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C#N)C=C1 KGCDKDLWNXXRFV-UHFFFAOYSA-N 0.000 claims description 11
- LZCHVDSKNDHAOJ-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-(4-methoxyphenyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(OC)C=C1 LZCHVDSKNDHAOJ-UHFFFAOYSA-N 0.000 claims description 11
- BGLKZLSYHVCCKG-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-(4-methylphenyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C)C=C1 BGLKZLSYHVCCKG-UHFFFAOYSA-N 0.000 claims description 11
- BHNMYNFFQOTSHQ-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-[3-chloro-4-(trifluoromethyl)phenyl]benzoyl]amino]-3-(dimethylcarbamoyl)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C(Cl)=C1 BHNMYNFFQOTSHQ-UHFFFAOYSA-N 0.000 claims description 11
- ULLUGLVTASFFSI-UHFFFAOYSA-N diethyl 2-[[2-[4-[[3-chloro-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]-3-(dimethylcarbamoyl)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC(Cl)=C1C1=CC=C(C(F)(F)F)C=C1 ULLUGLVTASFFSI-UHFFFAOYSA-N 0.000 claims description 11
- KNZWSIOXCHPTIY-UHFFFAOYSA-N diethyl 2-[[2-[4-[[4-chloro-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]-3-(dimethylcarbamoyl)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(Cl)C=C1C1=CC=C(C(F)(F)F)C=C1 KNZWSIOXCHPTIY-UHFFFAOYSA-N 0.000 claims description 11
- RHQODGJKTHSOSK-UHFFFAOYSA-N diethyl 2-[[2-[4-[cyclohexyl-[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1N(C(=O)C=1C(=CC=CC=1)C=1C=CC(=CC=1)C(F)(F)F)C1CCCCC1 RHQODGJKTHSOSK-UHFFFAOYSA-N 0.000 claims description 11
- UEOVIJRSLCPDLW-UHFFFAOYSA-N diethyl 2-[[2-[4-[methyl-[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1N(C)C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UEOVIJRSLCPDLW-UHFFFAOYSA-N 0.000 claims description 11
- XKIOHZHJOXNEDD-UHFFFAOYSA-N diethyl 2-[[2-[5-(dimethylcarbamoyl)-2-fluoro-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C(=C1)F)=CC(C(=O)N(C)C)=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XKIOHZHJOXNEDD-UHFFFAOYSA-N 0.000 claims description 11
- CAUSRFIXGJUMIM-UHFFFAOYSA-N diethyl 2-cyclohexyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C1CCCCC1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 CAUSRFIXGJUMIM-UHFFFAOYSA-N 0.000 claims description 11
- XSURSZJBHYZJJO-UHFFFAOYSA-N diethyl 2-cyclopentyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C1CCCC1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XSURSZJBHYZJJO-UHFFFAOYSA-N 0.000 claims description 11
- OHSMIXHPCYFYCG-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-(piperidine-1-carbonyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N2CCCCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 OHSMIXHPCYFYCG-UHFFFAOYSA-N 0.000 claims description 11
- ZEHFIMSMADZESI-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-(pyrrolidine-1-carbonyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N2CCCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZEHFIMSMADZESI-UHFFFAOYSA-N 0.000 claims description 11
- LZKKTMHAHINRDI-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-(trifluoromethyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 LZKKTMHAHINRDI-UHFFFAOYSA-N 0.000 claims description 11
- BZBRIHBDVDUCFO-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-phenyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 BZBRIHBDVDUCFO-UHFFFAOYSA-N 0.000 claims description 11
- QJZMAIDVXSIIFK-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-phenylmethoxycarbonyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)OCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QJZMAIDVXSIIFK-UHFFFAOYSA-N 0.000 claims description 11
- UFYDSTAIJUDNHE-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-piperidin-1-yl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1N2CCCCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UFYDSTAIJUDNHE-UHFFFAOYSA-N 0.000 claims description 11
- FEWGQHYTEGBJFY-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-propan-2-yl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FEWGQHYTEGBJFY-UHFFFAOYSA-N 0.000 claims description 11
- FPDIEXMCHOROPA-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-propan-2-yloxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1OC(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FPDIEXMCHOROPA-UHFFFAOYSA-N 0.000 claims description 11
- WEHSHKXBBBYNFJ-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-propan-2-yloxycarbonyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)OC(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WEHSHKXBBBYNFJ-UHFFFAOYSA-N 0.000 claims description 11
- FLFIHJWMQVMSMT-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-pyrrolidin-1-yl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1N2CCCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FLFIHJWMQVMSMT-UHFFFAOYSA-N 0.000 claims description 11
- YUNQRDJOOWZLOS-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[2-[4-(trifluoromethyl)phenyl]benzoyl]oxyphenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 YUNQRDJOOWZLOS-UHFFFAOYSA-N 0.000 claims description 11
- VHDOPMHJSBYYHC-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[[2-[3-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=CC(C(F)(F)F)=C1 VHDOPMHJSBYYHC-UHFFFAOYSA-N 0.000 claims description 11
- MPAQJJHEYFQVKF-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 MPAQJJHEYFQVKF-UHFFFAOYSA-N 0.000 claims description 11
- FJYWNJJUAJOEJL-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[propan-2-yl-[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1N(C(C)C)C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FJYWNJJUAJOEJL-UHFFFAOYSA-N 0.000 claims description 11
- VILOIKMDJRUCLA-UHFFFAOYSA-N diethyl 2-pyridin-2-yl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=NC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VILOIKMDJRUCLA-UHFFFAOYSA-N 0.000 claims description 11
- UMLUDJUUFTZTNT-UHFFFAOYSA-N diethyl 2-pyridin-3-yl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CN=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UMLUDJUUFTZTNT-UHFFFAOYSA-N 0.000 claims description 11
- XCLRUDOZRXMGPG-UHFFFAOYSA-N dimethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OC)(C(=O)OC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XCLRUDOZRXMGPG-UHFFFAOYSA-N 0.000 claims description 11
- MKCRYYQSLDSGEA-UHFFFAOYSA-N dimethyl 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OC)(C(=O)OC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 MKCRYYQSLDSGEA-UHFFFAOYSA-N 0.000 claims description 11
- GAESNEVCLFYTIY-UHFFFAOYSA-N dipropan-2-yl 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OC(C)C)(C(=O)OC(C)C)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 GAESNEVCLFYTIY-UHFFFAOYSA-N 0.000 claims description 11
- CFVBWOFPRDHFBM-UHFFFAOYSA-N dipropyl 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCCC)(C(=O)OCCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 CFVBWOFPRDHFBM-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical group 0.000 claims description 11
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol hydrochloride Natural products C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 11
- AMMQOFIWXLHNJW-UHFFFAOYSA-N 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioic acid Chemical compound C=1C=C(NC(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)N(C)C)=CC=1CC(=O)OCC(C(O)=O)(C(O)=O)C1=CC=CC=C1 AMMQOFIWXLHNJW-UHFFFAOYSA-N 0.000 claims description 10
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 10
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 10
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
- WYONJIPEZCTNQA-UHFFFAOYSA-N 5-[2-[3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropoxy]-2-oxoethyl]-2-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoic acid Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(O)=O)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WYONJIPEZCTNQA-UHFFFAOYSA-N 0.000 claims description 10
- MAGIMDGNASRRRZ-UHFFFAOYSA-N [3-(cyclohexylamino)-2-(cyclohexylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CC(=O)OCC(C=1C=CC=CC=1)(C(=O)NC1CCCCC1)C(=O)NC1CCCCC1 MAGIMDGNASRRRZ-UHFFFAOYSA-N 0.000 claims description 10
- WAIYBHJEIRHQGY-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(2-methylpropyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1CC(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WAIYBHJEIRHQGY-UHFFFAOYSA-N 0.000 claims description 10
- LPHFJAHVHXGCJC-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(dimethylamino)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 LPHFJAHVHXGCJC-UHFFFAOYSA-N 0.000 claims description 10
- FWKFITSVDODGAF-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(piperidine-1-carbonyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N2CCCCC2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FWKFITSVDODGAF-UHFFFAOYSA-N 0.000 claims description 10
- NZNUZVSFKVHRSA-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-hydroxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1O)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 NZNUZVSFKVHRSA-UHFFFAOYSA-N 0.000 claims description 10
- YGRZKEKEFVYSER-UHFFFAOYSA-N [3-anilino-3-oxo-2-phenyl-2-(phenylcarbamoyl)propyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CC(=O)OCC(C=1C=CC=CC=1)(C(=O)NC=1C=CC=CC=1)C(=O)NC1=CC=CC=C1 YGRZKEKEFVYSER-UHFFFAOYSA-N 0.000 claims description 10
- XGRAWMZOYKHADZ-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(propan-2-ylamino)-2-(propan-2-ylcarbamoyl)propyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NC(C)C)(C(=O)NC(C)C)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XGRAWMZOYKHADZ-UHFFFAOYSA-N 0.000 claims description 10
- LHFAGDIJHIHIFC-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 LHFAGDIJHIHIFC-UHFFFAOYSA-N 0.000 claims description 10
- QKAKMQICFFRSCS-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 3-chloro-4-[2-[4-(trifluoromethyl)phenyl]benzoyl]oxybenzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)C(C=C1Cl)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QKAKMQICFFRSCS-UHFFFAOYSA-N 0.000 claims description 10
- 239000002220 antihypertensive agent Substances 0.000 claims description 10
- WCHYAQSECVPREY-UHFFFAOYSA-N bis(2-methylpropyl) 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC(C)C)(C(=O)OCC(C)C)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WCHYAQSECVPREY-UHFFFAOYSA-N 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- KADUHNHNLIGUPU-UHFFFAOYSA-N diethyl 2-(5-aminopyridin-2-yl)-2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=C(N)C=NC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 KADUHNHNLIGUPU-UHFFFAOYSA-N 0.000 claims description 10
- YHQGUNJPAAVYRT-UHFFFAOYSA-N diethyl 2-[3-[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxypropyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCCOC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 YHQGUNJPAAVYRT-UHFFFAOYSA-N 0.000 claims description 10
- PQYQHQHKLZPUGP-UHFFFAOYSA-N diethyl 2-[[2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C(=C1)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 PQYQHQHKLZPUGP-UHFFFAOYSA-N 0.000 claims description 10
- UDLMNDUFPKUJSY-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-(4-methylphenyl)propanedioate Chemical compound C=1C=C(C)C=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UDLMNDUFPKUJSY-UHFFFAOYSA-N 0.000 claims description 10
- XPRIDZRFMYZQSM-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-(5-methylthiophen-2-yl)propanedioate Chemical compound C=1C=C(C)SC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XPRIDZRFMYZQSM-UHFFFAOYSA-N 0.000 claims description 10
- XEMLRDPGOJPHDL-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-(5-nitropyridin-2-yl)propanedioate Chemical compound C=1C=C([N+]([O-])=O)C=NC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XEMLRDPGOJPHDL-UHFFFAOYSA-N 0.000 claims description 10
- DAPBKZSHKPPWKF-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-thiophen-2-ylpropanedioate Chemical compound C=1C=CSC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DAPBKZSHKPPWKF-UHFFFAOYSA-N 0.000 claims description 10
- NSHDBBXTDASVHG-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[3-methoxy-2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC(OC)=C1C1=CC=C(C(F)(F)F)C=C1 NSHDBBXTDASVHG-UHFFFAOYSA-N 0.000 claims description 10
- VOCOBGKMMMDCLO-UHFFFAOYSA-N diethyl 2-[[2-[3-(methoxycarbonylamino)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1NC(=O)OC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VOCOBGKMMMDCLO-UHFFFAOYSA-N 0.000 claims description 10
- WDYJRWDDNFJIIF-UHFFFAOYSA-N diethyl 2-[[2-[3-[ethyl(methyl)carbamoyl]-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)CC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WDYJRWDDNFJIIF-UHFFFAOYSA-N 0.000 claims description 10
- JIGCNLSLFSZUBN-UHFFFAOYSA-N diethyl 2-[[2-[3-chloro-5-(dimethylcarbamoyl)-2-fluoro-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C(=C1Cl)F)=CC(C(=O)N(C)C)=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 JIGCNLSLFSZUBN-UHFFFAOYSA-N 0.000 claims description 10
- ZSFJTLSWCMMWQS-UHFFFAOYSA-N diethyl 2-[[2-[3-methoxy-4-[2-[4-(trifluoromethyl)phenyl]benzoyl]oxyphenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1OC)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZSFJTLSWCMMWQS-UHFFFAOYSA-N 0.000 claims description 10
- BYZSMHCEVWSYNZ-UHFFFAOYSA-N diethyl 2-[[2-[4-[ethyl-[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1N(CC)C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 BYZSMHCEVWSYNZ-UHFFFAOYSA-N 0.000 claims description 10
- AUZVZFRTWPBNSU-UHFFFAOYSA-N diethyl 2-cyclohexyl-2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C1CCCCC1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 AUZVZFRTWPBNSU-UHFFFAOYSA-N 0.000 claims description 10
- WNAGUAJYPFLTNP-UHFFFAOYSA-N diethyl 2-cyclopentyl-2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C1CCCC1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WNAGUAJYPFLTNP-UHFFFAOYSA-N 0.000 claims description 10
- LGYSSKPTXWNPKH-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-phenylmethoxy-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1OCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 LGYSSKPTXWNPKH-UHFFFAOYSA-N 0.000 claims description 10
- HSXVEGHKRDFWIU-UHFFFAOYSA-N ethyl 5-[2-[3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropoxy]-2-oxoethyl]-2-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)OCC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 HSXVEGHKRDFWIU-UHFFFAOYSA-N 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 claims description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 9
- YDYOHTBZCQGLMH-UHFFFAOYSA-N [2-chloro-4-[2-[3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropoxy]-2-oxoethyl]phenyl] 2-[4-(trifluoromethyl)phenyl]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1Cl)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 YDYOHTBZCQGLMH-UHFFFAOYSA-N 0.000 claims description 9
- HKQLLOCMUWZCAB-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(benzylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)NCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 HKQLLOCMUWZCAB-UHFFFAOYSA-N 0.000 claims description 9
- UCMNZVKXQRAGGY-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-methyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UCMNZVKXQRAGGY-UHFFFAOYSA-N 0.000 claims description 9
- HMDOGEKFEHPEOR-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[2-ethoxy-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=1OCC)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 HMDOGEKFEHPEOR-UHFFFAOYSA-N 0.000 claims description 9
- TZJVBXLUNRXPSD-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[2-methoxy-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=1OC)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 TZJVBXLUNRXPSD-UHFFFAOYSA-N 0.000 claims description 9
- MPGUAMBHIDDTBK-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 MPGUAMBHIDDTBK-UHFFFAOYSA-N 0.000 claims description 9
- AASLRCUIMHVVAU-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 AASLRCUIMHVVAU-UHFFFAOYSA-N 0.000 claims description 9
- NIIUYOQBXOYVNI-UHFFFAOYSA-N [4-[2-[3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropoxy]-2-oxoethyl]phenyl] 2-[4-(trifluoromethyl)phenyl]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 NIIUYOQBXOYVNI-UHFFFAOYSA-N 0.000 claims description 9
- WTVHRXVSMGLFJD-UHFFFAOYSA-N [4-oxo-3-phenyl-4-(propan-2-ylamino)-3-(propan-2-ylcarbamoyl)butyl] 2-[3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NC(C)C)(C(=O)NC(C)C)CCOC(=O)CC(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WTVHRXVSMGLFJD-UHFFFAOYSA-N 0.000 claims description 9
- ADAGVMBJRMVJDJ-UHFFFAOYSA-N [4-oxo-3-phenyl-4-(propylamino)-3-(propylcarbamoyl)butyl] 2-[2-methyl-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)(C(=O)NCCC)CCOC(=O)CC(C=1C)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ADAGVMBJRMVJDJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- SQZJVABVAIDAOE-UHFFFAOYSA-N diethyl 2-[2-[2-[2-ethoxy-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=1OCC)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 SQZJVABVAIDAOE-UHFFFAOYSA-N 0.000 claims description 9
- CHIDDXJLXFNGCE-UHFFFAOYSA-N diethyl 2-[2-[2-[2-ethoxy-5-methyl-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=1OCC)=CC(C)=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 CHIDDXJLXFNGCE-UHFFFAOYSA-N 0.000 claims description 9
- DDHVJBQPFURWLA-UHFFFAOYSA-N diethyl 2-[2-[2-[2-methoxy-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=1OC)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DDHVJBQPFURWLA-UHFFFAOYSA-N 0.000 claims description 9
- QYPDKASDOYGDDD-UHFFFAOYSA-N diethyl 2-[2-[2-[2-methoxycarbonyl-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=1C(=O)OC)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 QYPDKASDOYGDDD-UHFFFAOYSA-N 0.000 claims description 9
- VWQDSJYQZGFUSZ-UHFFFAOYSA-N diethyl 2-[2-[2-[2-methyl-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=1C)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VWQDSJYQZGFUSZ-UHFFFAOYSA-N 0.000 claims description 9
- MVLYOUJBOXHPKU-UHFFFAOYSA-N diethyl 2-[2-[2-[2-methyl-5-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C(=CC=1)C)=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 MVLYOUJBOXHPKU-UHFFFAOYSA-N 0.000 claims description 9
- CYHJKLKOINRIOD-UHFFFAOYSA-N diethyl 2-[2-[2-[4-methyl-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=1)=CC=C(C)C=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 CYHJKLKOINRIOD-UHFFFAOYSA-N 0.000 claims description 9
- RQTRHOJDEWHFRL-UHFFFAOYSA-N diethyl 2-[2-[3-methyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)C(C=C1C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 RQTRHOJDEWHFRL-UHFFFAOYSA-N 0.000 claims description 9
- JXDJXXNXUMYJAM-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2,4-bis(trifluoromethyl)benzoyl]amino]-3-(dimethylcarbamoyl)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1C(F)(F)F JXDJXXNXUMYJAM-UHFFFAOYSA-N 0.000 claims description 9
- XVWQQOWBXHBGER-UHFFFAOYSA-N diethyl 2-phenyl-2-[2-[4-[2-[4-(trifluoromethyl)phenyl]benzoyl]oxybenzoyl]oxyethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)C(C=C1)=CC=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 XVWQQOWBXHBGER-UHFFFAOYSA-N 0.000 claims description 9
- ZIEUWIULPTZRJN-UHFFFAOYSA-N diethyl 2-phenyl-2-[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoyl]oxyethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZIEUWIULPTZRJN-UHFFFAOYSA-N 0.000 claims description 9
- VLJGRMJIKDOEFT-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VLJGRMJIKDOEFT-UHFFFAOYSA-N 0.000 claims description 9
- OZJKOVUQNPNXAQ-UHFFFAOYSA-N methyl 5-[2-[3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropoxy]-2-oxoethyl]-2-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)OC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 OZJKOVUQNPNXAQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
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- WEUZMSLVMQPRIK-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 3,5-dichloro-4-[2-[4-(trifluoromethyl)phenyl]benzoyl]oxybenzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)C(C=C1Cl)=CC(Cl)=C1OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WEUZMSLVMQPRIK-UHFFFAOYSA-N 0.000 claims description 8
- OJYSEEYBKKNIQZ-UHFFFAOYSA-N [4-oxo-3-phenyl-4-(propylamino)-3-(propylcarbamoyl)butyl] 2-[3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)(C(=O)NCCC)CCOC(=O)CC(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 OJYSEEYBKKNIQZ-UHFFFAOYSA-N 0.000 claims description 8
- MUYGQRZCXIRFRU-UHFFFAOYSA-N [5-(ethylamino)-4-(ethylcarbamoyl)-5-oxo-4-phenylpentyl] 2-[2-methyl-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCCOC(=O)CC(C=1C)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 MUYGQRZCXIRFRU-UHFFFAOYSA-N 0.000 claims description 8
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- BWHGOSZWMINABQ-UHFFFAOYSA-N diethyl 2-phenyl-2-[2-[2-[3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 BWHGOSZWMINABQ-UHFFFAOYSA-N 0.000 claims description 8
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- BGGDJPVNKQYVSQ-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-(2-methoxyphenyl)propanedioate Chemical compound C=1C=CC=C(OC)C=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 BGGDJPVNKQYVSQ-UHFFFAOYSA-N 0.000 claims description 6
- UVHXVZOIYJACHE-UHFFFAOYSA-N diethyl 2-phenyl-2-[2-[2-[2-propan-2-yloxy-3-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)CC(C=1OC(C)C)=CC=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UVHXVZOIYJACHE-UHFFFAOYSA-N 0.000 claims description 6
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- IUGQFMIATSVYLK-UHFFFAOYSA-N benzyl 2-(4-hydroxyphenyl)acetate Chemical compound C1=CC(O)=CC=C1CC(=O)OCC1=CC=CC=C1 IUGQFMIATSVYLK-UHFFFAOYSA-N 0.000 claims description 5
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- FYBXRCFPOTXTJF-UHFFFAOYSA-N carteolol hydrochloride Chemical compound [Cl-].N1C(=O)CCC2=C1C=CC=C2OCC(O)C[NH2+]C(C)(C)C FYBXRCFPOTXTJF-UHFFFAOYSA-N 0.000 claims description 5
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- IQOMYCGTGFGDFN-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 IQOMYCGTGFGDFN-UHFFFAOYSA-N 0.000 claims description 3
- 229940122355 Insulin sensitizer Drugs 0.000 claims description 3
- LSJLNLNWHYUKJR-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[2-oxo-3-[2-[4-(trifluoromethyl)phenyl]benzoyl]-1,3-benzoxazol-6-yl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1OC2=O)=CC=C1N2C(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 LSJLNLNWHYUKJR-UHFFFAOYSA-N 0.000 claims description 3
- VJHHHBDLWMIOMA-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-methyl-4-[[2-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C)=CC=C1NC(=O)C1=CC=CN=C1C1=CC=C(C(F)(F)F)C=C1 VJHHHBDLWMIOMA-UHFFFAOYSA-N 0.000 claims description 3
- CUHMEEJBZYGMNF-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[(2-benzoylbenzoyl)amino]-3-(dimethylcarbamoyl)phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 CUHMEEJBZYGMNF-UHFFFAOYSA-N 0.000 claims description 3
- YAUAWEWFZGWJAX-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[(2-butoxybenzoyl)amino]phenyl]acetate Chemical compound CCCCOC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CC(=O)OCC(C(=O)NCC)(C(=O)NCC)C1=CC=CC=C1 YAUAWEWFZGWJAX-UHFFFAOYSA-N 0.000 claims description 3
- MXYXPBBVTRTDGP-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[(2-cyclohexylbenzoyl)amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1CCCCC1 MXYXPBBVTRTDGP-UHFFFAOYSA-N 0.000 claims description 3
- NWCPRIHQBYCHFI-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[(2-phenoxybenzoyl)amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 NWCPRIHQBYCHFI-UHFFFAOYSA-N 0.000 claims description 3
- IYFOZRJGCONHSL-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]pyridine-3-carbonyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1C1=CC=C(C(F)(F)F)C=C1 IYFOZRJGCONHSL-UHFFFAOYSA-N 0.000 claims description 3
- LGIWMMZXYVYWLD-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[4-[[2-methyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C=1SC(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 LGIWMMZXYVYWLD-UHFFFAOYSA-N 0.000 claims description 3
- DTGAQZLPDGVICO-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 4-[[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]methyl]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)C(C=C1)=CC=C1CNC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DTGAQZLPDGVICO-UHFFFAOYSA-N 0.000 claims description 3
- AZZGVQVTSSWDMP-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(2,2,2-trifluoroethylamino)-2-(2,2,2-trifluoroethylcarbamoyl)propyl] 2-[4-[(2-butoxybenzoyl)amino]phenyl]acetate Chemical compound CCCCOC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CC(=O)OCC(C(=O)NCC(F)(F)F)(C(=O)NCC(F)(F)F)C1=CC=CC=C1 AZZGVQVTSSWDMP-UHFFFAOYSA-N 0.000 claims description 3
- IWYLIQWGGFNCJX-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(2,2,2-trifluoroethylamino)-2-(2,2,2-trifluoroethylcarbamoyl)propyl] 2-[4-[(2-phenoxybenzoyl)amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC(F)(F)F)(C(=O)NCC(F)(F)F)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 IWYLIQWGGFNCJX-UHFFFAOYSA-N 0.000 claims description 3
- FVZWNGCZEFEFPP-UHFFFAOYSA-N [3-oxo-2-phenyl-3-(propylamino)-2-(propylcarbamoyl)propyl] 2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC)(C(=O)NCCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FVZWNGCZEFEFPP-UHFFFAOYSA-N 0.000 claims description 3
- FTSDHRXEBBGYLK-UHFFFAOYSA-N [4-(ethylamino)-3-(ethylcarbamoyl)-4-oxo-3-phenylbutyl] 3-[[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]methyl]benzoate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)CCOC(=O)C(C=1)=CC=CC=1CNC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FTSDHRXEBBGYLK-UHFFFAOYSA-N 0.000 claims description 3
- BBUZYIVSENWEQE-UHFFFAOYSA-N [4-[2-oxo-2-[3-oxo-2-phenyl-3-(2,2,2-trifluoroethylamino)-2-(2,2,2-trifluoroethylcarbamoyl)propoxy]ethyl]phenyl] 2-butoxybenzoate Chemical compound CCCCOC1=CC=CC=C1C(=O)OC(C=C1)=CC=C1CC(=O)OCC(C(=O)NCC(F)(F)F)(C(=O)NCC(F)(F)F)C1=CC=CC=C1 BBUZYIVSENWEQE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- AHEJHFCCIIXDLZ-UHFFFAOYSA-N diethyl 2-[2-[4-(2-benzoylbenzoyl)oxybenzoyl]oxyethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)C(C=C1)=CC=C1OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 AHEJHFCCIIXDLZ-UHFFFAOYSA-N 0.000 claims description 3
- GHULWLVRNBPYGI-UHFFFAOYSA-N diethyl 2-[[2-[2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzimidazol-1-yl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CN(C1=CC=C2)C(C)=NC1=C2NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 GHULWLVRNBPYGI-UHFFFAOYSA-N 0.000 claims description 3
- JDYPGORKZUILES-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[(2-phenoxybenzoyl)amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 JDYPGORKZUILES-UHFFFAOYSA-N 0.000 claims description 3
- OMGOECIYVOQHEI-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-(trifluoromethyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C(F)(F)F OMGOECIYVOQHEI-UHFFFAOYSA-N 0.000 claims description 3
- BYWLAFOFYPDVEN-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[3-(trifluoromethyl)anilino]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 BYWLAFOFYPDVEN-UHFFFAOYSA-N 0.000 claims description 3
- CNSUYALGSDGSSC-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenoxy]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=C(C(F)(F)F)C=C1 CNSUYALGSDGSSC-UHFFFAOYSA-N 0.000 claims description 3
- OFUDQCHXORBKIQ-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-prop-1-en-2-yl-4-(trifluoromethyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1C(C)=C OFUDQCHXORBKIQ-UHFFFAOYSA-N 0.000 claims description 3
- AVNPLYVXSZMDCK-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-propan-2-yl-4-(trifluoromethyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1C(C)C AVNPLYVXSZMDCK-UHFFFAOYSA-N 0.000 claims description 3
- TUFCFZKRAVFRTK-UHFFFAOYSA-N diethyl 2-[[2-[4-(9h-fluorene-1-carbonylamino)phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=C(NC(=O)C=2C3=C(C4=CC=CC=C4C3)C=CC=2)C=CC=1CC(=O)OCC(C(=O)OCC)(C(=O)OCC)C1=CC=CC=C1 TUFCFZKRAVFRTK-UHFFFAOYSA-N 0.000 claims description 3
- LLGYUDLFSGRVNF-UHFFFAOYSA-N diethyl 2-[[2-[4-[(2-benzoylbenzoyl)amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 LLGYUDLFSGRVNF-UHFFFAOYSA-N 0.000 claims description 3
- GBRSVHZJYHCQSL-UHFFFAOYSA-N diethyl 2-[[2-[4-[(2-benzylbenzoyl)amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1CC1=CC=CC=C1 GBRSVHZJYHCQSL-UHFFFAOYSA-N 0.000 claims description 3
- ZTDIJXOABCWAEX-UHFFFAOYSA-N diethyl 2-[[2-[4-[(2-butoxybenzoyl)amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound CCCCOC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CC(=O)OCC(C(=O)OCC)(C(=O)OCC)C1=CC=CC=C1 ZTDIJXOABCWAEX-UHFFFAOYSA-N 0.000 claims description 3
- QBDAFLZDGLFINO-UHFFFAOYSA-N diethyl 2-[[2-[4-[(2-butoxycarbonylbenzoyl)amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)NC(C=C1)=CC=C1CC(=O)OCC(C(=O)OCC)(C(=O)OCC)C1=CC=CC=C1 QBDAFLZDGLFINO-UHFFFAOYSA-N 0.000 claims description 3
- ALCCRPRDCBCQKW-UHFFFAOYSA-N diethyl 2-[[2-[4-[(2-phenoxybenzoyl)amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 ALCCRPRDCBCQKW-UHFFFAOYSA-N 0.000 claims description 3
- TXJZLTZBWILVJQ-UHFFFAOYSA-N diethyl 2-[[2-[4-[(9-oxofluorene-1-carbonyl)amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=C(NC(=O)C=2C=3C(=O)C4=CC=CC=C4C=3C=CC=2)C=CC=1CC(=O)OCC(C(=O)OCC)(C(=O)OCC)C1=CC=CC=C1 TXJZLTZBWILVJQ-UHFFFAOYSA-N 0.000 claims description 3
- PVGQAMQFNQDXKM-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-(4-fluorobenzoyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 PVGQAMQFNQDXKM-UHFFFAOYSA-N 0.000 claims description 3
- UACPWMGZHIMZAC-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-methyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C=1SC(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 UACPWMGZHIMZAC-UHFFFAOYSA-N 0.000 claims description 3
- ZUMZISWSTGEFNI-UHFFFAOYSA-N diethyl 2-phenyl-2-[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]cyclohexanecarbonyl]oxyethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)CCOC(=O)C(CC1)CCC1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZUMZISWSTGEFNI-UHFFFAOYSA-N 0.000 claims description 3
- ZVHYDADAYOFBLZ-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[(2-propan-2-ylbenzoyl)amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C(C)C ZVHYDADAYOFBLZ-UHFFFAOYSA-N 0.000 claims description 3
- OGCIACUCDXTBFI-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[(2-thiophen-3-ylbenzoyl)amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C=1C=CSC=1 OGCIACUCDXTBFI-UHFFFAOYSA-N 0.000 claims description 3
- SXUZRPFZYIIPOL-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[(3-phenylbenzoyl)amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 SXUZRPFZYIIPOL-UHFFFAOYSA-N 0.000 claims description 3
- XBTNYNBNOGFFNV-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[2-(trifluoromethyl)benzoyl]oxyphenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1OC(=O)C1=CC=CC=C1C(F)(F)F XBTNYNBNOGFFNV-UHFFFAOYSA-N 0.000 claims description 3
- YRKWCSSPYLPOIG-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[[2-(trifluoromethyl)benzoyl]amino]phenyl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C(F)(F)F YRKWCSSPYLPOIG-UHFFFAOYSA-N 0.000 claims description 3
- VXFMDJPXDXGORS-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]benzimidazol-1-yl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CN(C1=CC=C2)C=NC1=C2NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 VXFMDJPXDXGORS-UHFFFAOYSA-N 0.000 claims description 3
- CKMLTAAXHVBNRX-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]indol-1-yl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CN(C1=CC=C2)C=CC1=C2NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 CKMLTAAXHVBNRX-UHFFFAOYSA-N 0.000 claims description 3
- UNVODLXOVPZMJQ-UHFFFAOYSA-N diethyl 2-phenyl-2-[[2-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]piperidin-1-yl]acetyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CN(CC1)CCC1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 UNVODLXOVPZMJQ-UHFFFAOYSA-N 0.000 claims description 3
- DTUGERSGFRQBQT-UHFFFAOYSA-N diethyl 2-phenyl-2-[[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]cyclohexanecarbonyl]oxymethyl]propanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)C(CC1)CCC1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 DTUGERSGFRQBQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000007902 hard capsule Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000007901 soft capsule Substances 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- UOKSKZNYBWHXON-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(dimethylcarbamoyl)-4-[(2-phenoxybenzoyl)amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 UOKSKZNYBWHXON-UHFFFAOYSA-N 0.000 claims description 2
- BYDQPEFBPAESBC-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(dimethylcarbamoyl)-4-[[2-(trifluoromethyl)benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C(F)(F)F BYDQPEFBPAESBC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000883 anti-obesity agent Substances 0.000 claims description 2
- 229940125710 antiobesity agent Drugs 0.000 claims description 2
- VMBFKPDGSCGSKF-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[3-(trifluoromethyl)phenoxy]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1OC1=CC=CC(C(F)(F)F)=C1 VMBFKPDGSCGSKF-UHFFFAOYSA-N 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims 5
- WKRMIJRNLKAIQU-UHFFFAOYSA-N [3-(ethylamino)-2-(ethylcarbamoyl)-3-oxo-2-phenylpropyl] 2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC)(C(=O)NCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 WKRMIJRNLKAIQU-UHFFFAOYSA-N 0.000 claims 3
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- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- CBHDOQMGCANZAI-UHFFFAOYSA-N triethyl 2-[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxyethane-1,1,1-tricarboxylate Chemical compound CN(C)C(=O)C1=CC(CC(=O)OCC(C(=O)OCC)(C(=O)OCC)C(=O)OCC)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 CBHDOQMGCANZAI-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
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- 239000011712 vitamin K Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003053869A JP3662566B2 (ja) | 2002-02-28 | 2003-02-28 | エステル化合物及びその医薬用途 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002-53876 | 2002-02-28 | ||
| JP2002053876 | 2002-02-28 | ||
| JP2003053869A JP3662566B2 (ja) | 2002-02-28 | 2003-02-28 | エステル化合物及びその医薬用途 |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005019739A Division JP4397829B2 (ja) | 2002-02-28 | 2005-01-27 | エステル化合物及びその医薬用途 |
| JP2005019579A Division JP2005194281A (ja) | 2002-02-28 | 2005-01-27 | エステル化合物及びその医薬用途 |
| JP2005020179A Division JP4472541B2 (ja) | 2002-02-28 | 2005-01-27 | エステル化合物及びその医薬用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003321424A JP2003321424A (ja) | 2003-11-11 |
| JP3662566B2 true JP3662566B2 (ja) | 2005-06-22 |
| JP2003321424A5 JP2003321424A5 (enExample) | 2005-06-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003053869A Expired - Fee Related JP3662566B2 (ja) | 2002-02-28 | 2003-02-28 | エステル化合物及びその医薬用途 |
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| Country | Link |
|---|---|
| JP (1) | JP3662566B2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200502496B (en) | 2002-02-28 | 2005-10-12 | Japan Tobacco Inc | Ester compound and medicinal use thereof. |
| MX2007000397A (es) * | 2003-02-28 | 2007-03-30 | Japan Tobacco Inc | Agente para el tratamiento o prevencion de diabetes, obesidad o arteriosclerosis. |
| EP1669345A4 (en) | 2003-08-29 | 2008-02-20 | Japan Tobacco Inc | ESTER DERIVATIVE AND MEDICAL USE THEREOF |
| PT1725234E (pt) | 2004-03-05 | 2013-03-04 | Univ Pennsylvania | Métodos com efeitos secundários reduzidos para tratamento de patologias ou doenças associadas a hiperlipidemia e hipercolesterolemia |
| US8101774B2 (en) | 2004-10-18 | 2012-01-24 | Japan Tobacco Inc. | Ester derivatives and medicinal use thereof |
| KR20070072888A (ko) * | 2004-10-25 | 2007-07-06 | 니뽄 다바코 산교 가부시키가이샤 | 용해성 및 안정성이 개선된 고형 제제 및 그의 제조 방법 |
| KR101129456B1 (ko) | 2004-10-25 | 2012-03-28 | 니뽄 다바코 산교 가부시키가이샤 | 용해성 및 안정성이 개선된 고형 제제 및 그의 제조 방법 |
| BR112023000808A2 (pt) | 2020-07-29 | 2023-02-07 | Amryt Pharmaceuticals Inc | Lomitapida para uso em métodos para tratar hiperlipidemia e hipercolesterolemia em pacientes pediátricos |
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2003
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| JP2003321424A (ja) | 2003-11-11 |
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