JP2005519958A5 - - Google Patents
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- Publication number
- JP2005519958A5 JP2005519958A5 JP2003575901A JP2003575901A JP2005519958A5 JP 2005519958 A5 JP2005519958 A5 JP 2005519958A5 JP 2003575901 A JP2003575901 A JP 2003575901A JP 2003575901 A JP2003575901 A JP 2003575901A JP 2005519958 A5 JP2005519958 A5 JP 2005519958A5
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- methyl
- methylpropanamide
- methylpropyl
- propyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 455
- -1 and cycloheteroalkyl Chemical group 0.000 claims description 207
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000001424 substituent group Chemical group 0.000 claims description 62
- VSNDXBUJNXNURF-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)-2-methylhexanamide Chemical compound CCCCC(C)(C(N)=O)OC1=CC(Cl)=CC(Cl)=C1 VSNDXBUJNXNURF-UHFFFAOYSA-N 0.000 claims description 52
- 150000001408 amides Chemical class 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- ASFIPARRHCLIOR-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-(4-fluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(F)C=C1 ASFIPARRHCLIOR-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 15
- 208000008589 Obesity Diseases 0.000 claims description 15
- 235000014632 disordered eating Nutrition 0.000 claims description 15
- 235000020824 obesity Nutrition 0.000 claims description 15
- WADFFGDAIJGNFH-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC(Cl)=C1 WADFFGDAIJGNFH-UHFFFAOYSA-N 0.000 claims description 14
- JQWPFJSGBASENO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-pyridin-3-ylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=NC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 JQWPFJSGBASENO-UHFFFAOYSA-N 0.000 claims description 14
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 14
- DDETYHPHEUZUCX-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-(3-fluorophenyl)butan-2-yl]-2-(3,5-difluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(F)C=CC=1)C(C)NC(=O)C(C)(C)OC1=CC(F)=CC(F)=C1 DDETYHPHEUZUCX-UHFFFAOYSA-N 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- MRECCTXLXCELBU-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-(3,5-difluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC(F)=CC(F)=C1 MRECCTXLXCELBU-UHFFFAOYSA-N 0.000 claims description 13
- KSKXQOGPSBZBSW-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-methyl-2-pyridin-2-yloxypropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC=N1 KSKXQOGPSBZBSW-UHFFFAOYSA-N 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- KJLZSBFYCZPSJB-UHFFFAOYSA-N 2-(3-chloro-5-fluorophenoxy)-n-[4-(4-chlorophenyl)-3-(3-fluorophenyl)butan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(F)C=CC=1)C(C)NC(=O)C(C)(C)OC1=CC(F)=CC(Cl)=C1 KJLZSBFYCZPSJB-UHFFFAOYSA-N 0.000 claims description 12
- UFQVTGSROPGOQC-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(C=CC=1)C#N)C(C)NC(=O)C(C)(C)OC1=CC=CC(Cl)=C1 UFQVTGSROPGOQC-UHFFFAOYSA-N 0.000 claims description 12
- RGCCRDDNINAOKY-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(4-cyanophenyl)-3-phenylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(C#N)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC(Cl)=C1 RGCCRDDNINAOKY-UHFFFAOYSA-N 0.000 claims description 12
- VTTREAPVLCATHS-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-pyridin-2-ylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1N=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 VTTREAPVLCATHS-UHFFFAOYSA-N 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 208000030814 Eating disease Diseases 0.000 claims description 12
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 230000037406 food intake Effects 0.000 claims description 12
- 235000012631 food intake Nutrition 0.000 claims description 12
- JRBXUPSPFIMRED-UHFFFAOYSA-N methyl 4-[3-[[2-(4-fluorophenoxy)-2-methylpropanoyl]amino]-2-phenylbutyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(F)C=C1 JRBXUPSPFIMRED-UHFFFAOYSA-N 0.000 claims description 12
- HAMLZAXSMZZNHH-UHFFFAOYSA-N n-[3,4-bis(4-chlorophenyl)butan-2-yl]-2-(4-chlorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC(Cl)=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 HAMLZAXSMZZNHH-UHFFFAOYSA-N 0.000 claims description 12
- HFHWAGKVYAUKHZ-UHFFFAOYSA-N n-[3,4-bis(4-chlorophenyl)butan-2-yl]-2-(4-fluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC(Cl)=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(F)C=C1 HFHWAGKVYAUKHZ-UHFFFAOYSA-N 0.000 claims description 12
- SCGDHVOMGFBTMI-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-(3-fluorophenyl)butan-2-yl]-2-methyl-2-pyridin-2-yloxypropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(F)C=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC=N1 SCGDHVOMGFBTMI-UHFFFAOYSA-N 0.000 claims description 12
- UYTUXABSUBMTPQ-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-(5-chloropyridin-3-yl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(Cl)C=NC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(C(F)(F)F)C=N1 UYTUXABSUBMTPQ-UHFFFAOYSA-N 0.000 claims description 12
- OXJWNDULCQMQGA-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-pyridin-3-ylbutan-2-yl]-2-(3,5-difluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=NC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC(F)=CC(F)=C1 OXJWNDULCQMQGA-UHFFFAOYSA-N 0.000 claims description 12
- AFCBFUABPBPHLV-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-pyridin-3-ylbutan-2-yl]-2-(3-fluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=NC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC(F)=C1 AFCBFUABPBPHLV-UHFFFAOYSA-N 0.000 claims description 12
- KYYIJERVQWQVHB-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[2-(4-chlorophenoxy)-2-(4-chlorophenyl)ethyl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1OC(C=1C=CC(Cl)=CC=1)CNC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KYYIJERVQWQVHB-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- GPGIORBDLOZMBV-UHFFFAOYSA-N n-[3,4-bis(4-chlorophenyl)butan-2-yl]-2-methyl-2-(6-methylpyridin-3-yl)oxypropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC(Cl)=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(C)N=C1 GPGIORBDLOZMBV-UHFFFAOYSA-N 0.000 claims description 11
- OJIWFBIZHVEQBL-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-(3,4-difluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(F)C(F)=C1 OJIWFBIZHVEQBL-UHFFFAOYSA-N 0.000 claims description 11
- PAHGBCUEXOTPIT-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-(3-fluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC(F)=C1 PAHGBCUEXOTPIT-UHFFFAOYSA-N 0.000 claims description 11
- UVFJWLJLMVGLGK-UHFFFAOYSA-N 2-(3,5-difluorophenoxy)-2-methylhexanamide Chemical compound C(CC)CC(C(=O)N)(C)OC1=CC(=CC(=C1)F)F UVFJWLJLMVGLGK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- PJNUOTNCBCRWHQ-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-(3,5-difluorophenyl)butan-2-yl]-2-(3,5-difluorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(F)C=C(F)C=1)C(C)NC(=O)C(C)(C)OC1=CC(F)=CC(F)=C1 PJNUOTNCBCRWHQ-UHFFFAOYSA-N 0.000 claims description 10
- QLYKJCMUNUWAGO-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(C=CC=1)C#N)C(C)NC(=O)C(C)(C)OC1=CC=C(C(F)(F)F)C=N1 QLYKJCMUNUWAGO-UHFFFAOYSA-N 0.000 claims description 10
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 10
- VBIHTHXHJPLTBR-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-(3-fluorophenyl)butan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(F)C=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC(Cl)=C1 VBIHTHXHJPLTBR-UHFFFAOYSA-N 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 230000001404 mediated effect Effects 0.000 claims description 9
- 102000005962 receptors Human genes 0.000 claims description 9
- 108020003175 receptors Proteins 0.000 claims description 9
- CFCFDFUEJMXRLW-UHFFFAOYSA-N 2-(3-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-pyridin-3-ylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=NC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC(Cl)=C1 CFCFDFUEJMXRLW-UHFFFAOYSA-N 0.000 claims description 8
- PICQEYPJHIMZHP-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[3-(2-chlorophenyl)-4-phenylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=CC=CC=1CC(C=1C(=CC=CC=1)Cl)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 PICQEYPJHIMZHP-UHFFFAOYSA-N 0.000 claims description 8
- BBGPOWKMPKCETL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[3-(4-chlorophenyl)-4-phenylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=CC=CC=1CC(C=1C=CC(Cl)=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 BBGPOWKMPKCETL-UHFFFAOYSA-N 0.000 claims description 8
- FITSQWWWCJRSMA-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-(3,5-difluorophenyl)butan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(F)C=C(F)C=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 FITSQWWWCJRSMA-UHFFFAOYSA-N 0.000 claims description 8
- FGJHUABKMGQONH-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-(3-fluorophenyl)butan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(F)C=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 FGJHUABKMGQONH-UHFFFAOYSA-N 0.000 claims description 8
- SZTZUGGWPZIINA-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 SZTZUGGWPZIINA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 8
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims description 8
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 8
- ZBFSKHCQHWULCZ-UHFFFAOYSA-N n-[3,4-bis(4-chlorophenyl)butan-2-yl]-2-methyl-2-phenoxypropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC(Cl)=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC=C1 ZBFSKHCQHWULCZ-UHFFFAOYSA-N 0.000 claims description 8
- NJSONKDWRVNYCL-UHFFFAOYSA-N n-[3-(3-cyanophenyl)-4-cyclobutylbutan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide Chemical compound C1CCC1CC(C=1C=C(C=CC=1)C#N)C(C)NC(=O)C(C)(C)OC1=CC=C(C(F)(F)F)C=N1 NJSONKDWRVNYCL-UHFFFAOYSA-N 0.000 claims description 8
- TZYRPDAFSAFZSQ-UHFFFAOYSA-N n-[3-(3-cyanophenyl)-4-cyclopentylbutan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide Chemical compound C1CCCC1CC(C=1C=C(C=CC=1)C#N)C(C)NC(=O)C(C)(C)OC1=CC=C(C(F)(F)F)C=N1 TZYRPDAFSAFZSQ-UHFFFAOYSA-N 0.000 claims description 8
- OFJSMCUUQUZKND-UHFFFAOYSA-N n-[3-(4-chloro-2-fluorophenyl)-3-(4-chlorophenyl)butan-2-yl]-2-(4-chlorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1C(C)(C=1C(=CC(Cl)=CC=1)F)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OFJSMCUUQUZKND-UHFFFAOYSA-N 0.000 claims description 8
- BINCMSJEDLRTJN-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-(3-methylphenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=C(C)C=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(C(F)(F)F)C=N1 BINCMSJEDLRTJN-UHFFFAOYSA-N 0.000 claims description 8
- IROBMYGWVLTDFP-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-methyl-2-phenoxypropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC=C1 IROBMYGWVLTDFP-UHFFFAOYSA-N 0.000 claims description 8
- JTCSTBJLAUGXMC-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-3-pyridin-3-ylbutan-2-yl]-2-(3,5-dichlorophenoxy)-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=NC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC(Cl)=CC(Cl)=C1 JTCSTBJLAUGXMC-UHFFFAOYSA-N 0.000 claims description 8
- WDRZQEUNPQWHSG-UHFFFAOYSA-N n-[3-(3-cyanophenyl)-4-cyclohexylbutan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide Chemical compound C1CCCCC1CC(C=1C=C(C=CC=1)C#N)C(C)NC(=O)C(C)(C)OC1=CC=C(C(F)(F)F)C=N1 WDRZQEUNPQWHSG-UHFFFAOYSA-N 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- QXLRCSNJDDZHMP-UHFFFAOYSA-N 2-(2-chlorophenoxy)-n-[4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=CC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=CC=C1Cl QXLRCSNJDDZHMP-UHFFFAOYSA-N 0.000 claims description 6
- HIFGCYYBGHLQMV-HTAPYJJXSA-N 2-(3-chloro-4-fluorophenoxy)-n-[(2s,3s)-4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-methylpropanamide Chemical compound N([C@@H](C)[C@@H](CC=1C=CC(Cl)=CC=1)C=1C=CC=CC=1)C(=O)C(C)(C)OC1=CC=C(F)C(Cl)=C1 HIFGCYYBGHLQMV-HTAPYJJXSA-N 0.000 claims description 6
- YDJYVTJJCOWWAN-UHFFFAOYSA-N 2-(3-chloro-5-fluorophenoxy)-n-[4-(4-chlorophenyl)-3-pyridin-3-ylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1CC(C=1C=NC=CC=1)C(C)NC(=O)C(C)(C)OC1=CC(F)=CC(Cl)=C1 YDJYVTJJCOWWAN-UHFFFAOYSA-N 0.000 claims description 6
- DHMCZTXHSCFLCI-HTAPYJJXSA-N 2-(4-chloro-3-fluorophenoxy)-n-[(2s,3s)-4-(4-chlorophenyl)-3-phenylbutan-2-yl]-2-methylpropanamide Chemical compound N([C@@H](C)[C@@H](CC=1C=CC(Cl)=CC=1)C=1C=CC=CC=1)C(=O)C(C)(C)OC1=CC=C(Cl)C(F)=C1 DHMCZTXHSCFLCI-HTAPYJJXSA-N 0.000 claims description 6
- VGAKJPBJPLSUNB-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-n-(5-methyl-3-phenylhexan-2-yl)propanamide Chemical compound C=1C=CC=CC=1C(CC(C)C)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 VGAKJPBJPLSUNB-UHFFFAOYSA-N 0.000 claims description 6
- HLQRTQRYEWMHSE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[3-(4-chlorophenyl)-3-(4-chlorophenyl)sulfanylbutan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=CC=1SC(C)(C=1C=CC(Cl)=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 HLQRTQRYEWMHSE-UHFFFAOYSA-N 0.000 claims description 6
- SAAXYWSPRMMLPA-UHFFFAOYSA-N 2-(4-chlorophenoxy)-n-[3-(4-chlorophenyl)-4-(2,4-dichlorophenyl)butan-2-yl]-2-methylpropanamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1CC(C=1C=CC(Cl)=CC=1)C(C)NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 SAAXYWSPRMMLPA-UHFFFAOYSA-N 0.000 claims description 6
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-
2006
- 2006-04-07 JP JP2006105912A patent/JP5025980B2/ja not_active Expired - Fee Related
-
2008
- 2008-02-01 US US12/012,463 patent/US7550489B2/en not_active Expired - Fee Related
-
2009
- 2009-04-16 US US12/386,336 patent/US7816534B2/en not_active Expired - Fee Related
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