JP2006528157A5

JP2006528157A5 -

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Publication number: JP2006528157A5
Authority: JP; Japan
Prior art keywords: amino; methyl; carbonyl; alkyl; aryl
Prior art date: 2004-07-20
Legal status : Withdrawn

Application number

JP2006520836A

Other languages

English (en)

Japanese (ja)

Other versions

JP2006528157A (ja

Filing date

2004-07-20

Publication date

2007-09-13

2004-07-20 Application filed filed Critical

2004-07-20 Priority claimed from PCT/EP2004/051558 external-priority patent/WO2005011685A1/en

2006-12-14 Publication of JP2006528157A publication Critical patent/JP2006528157A/ja

2007-09-13 Publication of JP2006528157A5 publication Critical patent/JP2006528157A5/ja

Status Withdrawn legal-status Critical Current

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-1 C 1 -C 6 alkyl Chemical group 0.000 claims description 132
125000003118 aryl group Chemical group 0.000 claims description 66
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 63
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 46
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
125000001072 heteroaryl group Chemical group 0.000 claims description 36
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
206010012601 diabetes mellitus Diseases 0.000 claims description 29
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
125000000753 cycloalkyl group Chemical group 0.000 claims description 23
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 21
101001087394 Homo sapiens Tyrosine-protein phosphatase non-receptor type 1 Proteins 0.000 claims description 20
102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
206010022489 Insulin Resistance Diseases 0.000 claims description 18
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 17
239000008103 glucose Substances 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
208000008589 Obesity Diseases 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 13
230000000694 effects Effects 0.000 claims description 13
235000020824 obesity Nutrition 0.000 claims description 13
125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 11
230000005764 inhibitory process Effects 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
201000010065 polycystic ovary syndrome Diseases 0.000 claims description 11
239000005711 Benzoic acid Substances 0.000 claims description 10
235000010233 benzoic acid Nutrition 0.000 claims description 10
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
WUTVNBPTVYUJJL-UHFFFAOYSA-N 5-[3-cyclopentylpropanoyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)CCC2CCCC2)=C1 WUTVNBPTVYUJJL-UHFFFAOYSA-N 0.000 claims description 8
230000001404 mediated effect Effects 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
229960004889 salicylic acid Drugs 0.000 claims description 6
125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
238000010511 deprotection reaction Methods 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
201000001421 hyperglycemia Diseases 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
208000035150 Hypercholesterolemia Diseases 0.000 claims description 4
208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000005418 aryl aryl group Chemical group 0.000 claims description 4
208000030159 metabolic disease Diseases 0.000 claims description 4
CXBFVXKWGMJURV-UHFFFAOYSA-N 2-[4-[[[2-(dimethylamino)acetyl]-[[2-[4-(4-phenylbutylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl]amino]methyl]phenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C=CC=1CN(C(=O)CN(C)C)CC(N=1)=CSC=1C(C=C1)=CC=C1C(=O)NCCCCC1=CC=CC=C1 CXBFVXKWGMJURV-UHFFFAOYSA-N 0.000 claims description 3
CKYRYIQTDPFWJP-XQNSMLJCSA-N 2-[4-[[[2-[4-(4-phenylbutylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-[(e)-3-phenylprop-2-enoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)\C=C\C=1C=CC=CC=1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCCCCC=2C=CC=CC=2)=N1 CKYRYIQTDPFWJP-XQNSMLJCSA-N 0.000 claims description 3
FCAHBLZPXKOXRN-UHFFFAOYSA-N 2-[4-[[[2-[4-(4-phenylbutylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCCCCC=2C=CC=CC=2)=N1 FCAHBLZPXKOXRN-UHFFFAOYSA-N 0.000 claims description 3
XEKRVDVNLZIACS-UHFFFAOYSA-N 2-[4-[[[2-[4-(octylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-(3-phenylpropanoyl)amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1C1=NC(CN(CC=2C=CC(OCC(O)=O)=CC=2)C(=O)CCC=2C=CC=CC=2)=CS1 XEKRVDVNLZIACS-UHFFFAOYSA-N 0.000 claims description 3
VPNTWIBYNXNTNZ-UHFFFAOYSA-N 2-[4-[[[2-[4-(octylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1C1=NC(CN(CC=2C=CC(OCC(O)=O)=CC=2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=CS1 VPNTWIBYNXNTNZ-UHFFFAOYSA-N 0.000 claims description 3
BXEAQJQDKQWBGN-UHFFFAOYSA-N 2-[4-[[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-(3-phenylpropanoyl)amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(CC=3C=CC(OCC(O)=O)=CC=3)C(=O)CCC=3C=CC=CC=3)N=2)C=C1 BXEAQJQDKQWBGN-UHFFFAOYSA-N 0.000 claims description 3
BUPXKSCADCTEOY-JJIBRWJFSA-N 2-[4-[[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-[(e)-3-phenylprop-2-enoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(CC=3C=CC(OCC(O)=O)=CC=3)C(=O)\C=C\C=3C=CC=CC=3)N=2)C=C1 BUPXKSCADCTEOY-JJIBRWJFSA-N 0.000 claims description 3
YDTQKULHEUEFEF-UHFFFAOYSA-N 2-[4-[[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-(3-phenylpropanoyl)amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)CCC=1C=CC=CC=1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 YDTQKULHEUEFEF-UHFFFAOYSA-N 0.000 claims description 3
HXHLJIMPJZGDJR-UHFFFAOYSA-N 2-[4-[[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 HXHLJIMPJZGDJR-UHFFFAOYSA-N 0.000 claims description 3
DDFGQZNGPZNWFS-UHFFFAOYSA-N 2-[4-[[cyclohexanecarbonyl-[[2-[4-(4-phenylbutylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)C1CCCCC1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCCCCC=2C=CC=CC=2)=N1 DDFGQZNGPZNWFS-UHFFFAOYSA-N 0.000 claims description 3
MLLJUCAPOORHDS-UHFFFAOYSA-N 2-hydroxy-5-[(2-phenoxyacetyl)-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)COC=2C=CC=CC=2)=C1 MLLJUCAPOORHDS-UHFFFAOYSA-N 0.000 claims description 3
RIEGSJMQHPNZED-UHFFFAOYSA-N 2-hydroxy-5-[3-methylbut-2-enoyl-[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(C(=O)C=C(C)C)C=3C=C(C(O)=CC=3)C(O)=O)N=2)C=C1 RIEGSJMQHPNZED-UHFFFAOYSA-N 0.000 claims description 3
DZDSZFDDLDHYAH-PXLXIMEGSA-N 2-hydroxy-5-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl-[(e)-3-phenylprop-2-enoyl]amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)\C=C\C=2C=CC=CC=2)=C1 DZDSZFDDLDHYAH-PXLXIMEGSA-N 0.000 claims description 3
WWVMZQLVQAQTTO-UHFFFAOYSA-N 2-hydroxy-5-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 WWVMZQLVQAQTTO-UHFFFAOYSA-N 0.000 claims description 3
OKPWVHBHJMKTOA-CAPFRKAQSA-N 2-hydroxy-5-[[[4-(octylcarbamoyl)phenyl]methyl-[(e)-3-phenylprop-2-enoyl]amino]methyl]benzoic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1CN(C(=O)\C=C\C=1C=CC=CC=1)CC1=CC=C(O)C(C(O)=O)=C1 OKPWVHBHJMKTOA-CAPFRKAQSA-N 0.000 claims description 3
ONJDTUVILNQEGM-UHFFFAOYSA-N 2-hydroxy-5-[[[4-(octylcarbamoyl)phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]benzoic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CC=C(O)C(C(O)=O)=C1 ONJDTUVILNQEGM-UHFFFAOYSA-N 0.000 claims description 3
FCHTYMWDWQRHPP-FBMGVBCBSA-N 2-hydroxy-5-[[[4-[(4-pentylphenyl)methylcarbamoyl]-1,3-thiazol-2-yl]methyl-[(e)-3-phenylprop-2-enoyl]amino]methyl]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CSC(CN(CC=2C=C(C(O)=CC=2)C(O)=O)C(=O)\C=C\C=2C=CC=CC=2)=N1 FCHTYMWDWQRHPP-FBMGVBCBSA-N 0.000 claims description 3
UKVJDXJZZBQSJY-UHFFFAOYSA-N 2-hydroxy-5-[[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-(2-phenoxyacetyl)amino]methyl]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C(=O)COC=1C=CC=CC=1)CC1=CC=C(O)C(C(O)=O)=C1 UKVJDXJZZBQSJY-UHFFFAOYSA-N 0.000 claims description 3
OSFADAFKTPSSCV-UHFFFAOYSA-N 5-[(4-cyanobenzoyl)-[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(C(=O)C=3C=CC(=CC=3)C#N)C=3C=C(C(O)=CC=3)C(O)=O)N=2)C=C1 OSFADAFKTPSSCV-UHFFFAOYSA-N 0.000 claims description 3
ITHCHQGSZLSDRL-UHFFFAOYSA-N 5-[3-cyclopentylpropanoyl-[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2N=C(SC=2)C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)CCC2CCCC2)=C1 ITHCHQGSZLSDRL-UHFFFAOYSA-N 0.000 claims description 3
HFNIKNFPOBJFOV-UHFFFAOYSA-N 5-[[3-cyclopentylpropanoyl-[[4-(4-phenylbutylcarbamoyl)phenyl]methyl]amino]methyl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(CN(CC=2C=CC(=CC=2)C(=O)NCCCCC=2C=CC=CC=2)C(=O)CCC2CCCC2)=C1 HFNIKNFPOBJFOV-UHFFFAOYSA-N 0.000 claims description 3
GUJCLAIIBPUHNV-UHFFFAOYSA-N 5-[[3-cyclopentylpropanoyl-[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl]amino]methyl]-2-hydroxybenzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C(=O)CCC1CCCC1)CC1=CC=C(O)C(C(O)=O)=C1 GUJCLAIIBPUHNV-UHFFFAOYSA-N 0.000 claims description 3
ANCVOGMIGBIFOS-UHFFFAOYSA-N 5-[benzoyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]-1,3-thiazol-2-yl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2SC=C(N=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C=2C=CC=CC=2)=C1 ANCVOGMIGBIFOS-UHFFFAOYSA-N 0.000 claims description 3
OQIRIDMPHWDPFH-UHFFFAOYSA-N 5-[cyclohexanecarbonyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C2CCCCC2)=C1 OQIRIDMPHWDPFH-UHFFFAOYSA-N 0.000 claims description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
208000006575 hypertriglyceridemia Diseases 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000001105 regulatory effect Effects 0.000 claims description 3
NPFIUHQJRZGQPG-UHFFFAOYSA-N 2-[4-[[(2-phenoxyacetyl)-[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)COC=1C=CC=CC=1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 NPFIUHQJRZGQPG-UHFFFAOYSA-N 0.000 claims description 2
QJUKKIDACQSTIB-UHFFFAOYSA-N 2-[4-[[[2-[4-(4-phenylbutylcarbamoyl)phenyl]-1,3-thiazol-4-yl]methyl-(3-phenylpropanoyl)amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)CCC=1C=CC=CC=1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCCCCC=2C=CC=CC=2)=N1 QJUKKIDACQSTIB-UHFFFAOYSA-N 0.000 claims description 2
FLAZSTIQEPUNAY-UHFFFAOYSA-N 2-[4-[[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(CC=3C=CC(OCC(O)=O)=CC=3)C(=O)C=3C=CC(=CC=3)C(F)(F)F)N=2)C=C1 FLAZSTIQEPUNAY-UHFFFAOYSA-N 0.000 claims description 2
NLRKTELPGSKBOH-UHFFFAOYSA-N 2-[4-[[cyclohexanecarbonyl-[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1CN(C(=O)C1CCCCC1)CC1=CSC(C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 NLRKTELPGSKBOH-UHFFFAOYSA-N 0.000 claims description 2
APFLCNKRXAFAEF-UHFFFAOYSA-N 2-hydroxy-4-[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C=1C=C(O)C(C(O)=O)=CC=1)C(=O)C1=CC=C(C(F)(F)F)C=C1 APFLCNKRXAFAEF-UHFFFAOYSA-N 0.000 claims description 2
QKWWJYFHQBOYSJ-UHFFFAOYSA-N 2-hydroxy-5-[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-(2-phenoxyacetyl)amino]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(C(=O)COC=3C=CC=CC=3)C=3C=C(C(O)=CC=3)C(O)=O)N=2)C=C1 QKWWJYFHQBOYSJ-UHFFFAOYSA-N 0.000 claims description 2
WFCDPJZDVJLUAU-UHFFFAOYSA-N 2-hydroxy-5-[[[4-(octylcarbamoyl)phenyl]methyl-(2-phenoxyacetyl)amino]methyl]benzoic acid Chemical compound C1=CC(C(=O)NCCCCCCCC)=CC=C1CN(C(=O)COC=1C=CC=CC=1)CC1=CC=C(O)C(C(O)=O)=C1 WFCDPJZDVJLUAU-UHFFFAOYSA-N 0.000 claims description 2
KUWSGDRFKSTVEE-UHFFFAOYSA-N 2-hydroxy-5-[[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl-[4-(trifluoromethyl)benzoyl]amino]methyl]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)CC1=CC=C(O)C(C(O)=O)=C1 KUWSGDRFKSTVEE-UHFFFAOYSA-N 0.000 claims description 2
RKNBTHBSFSYOJU-UHFFFAOYSA-N 5-[3-cyclopentylpropanoyl-[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C=1C=C(C(O)=CC=1)C(O)=O)C(=O)CCC1CCCC1 RKNBTHBSFSYOJU-UHFFFAOYSA-N 0.000 claims description 2
SJBHRGLXGLBOBY-UHFFFAOYSA-N 5-[benzoyl-[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl]amino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(N(CC=2N=C(SC=2)C=2C=CC(=CC=2)C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(=O)C=2C=CC=CC=2)=C1 SJBHRGLXGLBOBY-UHFFFAOYSA-N 0.000 claims description 2
235000019789 appetite Nutrition 0.000 claims description 2
230000036528 appetite Effects 0.000 claims description 2
230000006806 disease prevention Effects 0.000 claims description 2
125000005217 alkenylheteroaryl group Chemical group 0.000 claims 2
SOVZDLBJJPAIHR-UHFFFAOYSA-N 2-hydroxy-5-[3-methylbut-2-enoyl-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl]amino]benzoic acid Chemical compound C=1C=C(O)C(C(O)=O)=CC=1N(C(=O)C=C(C)C)CC(C=C1)=CC=C1C(=O)NCC(C=C1)=CC=C1OC1=CC=CC=C1 SOVZDLBJJPAIHR-UHFFFAOYSA-N 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 140
238000000034 method Methods 0.000 description 82
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
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JP2006520836A 2003-07-21 2004-07-20 アリールジカルボキシアミド Withdrawn JP2006528157A (ja)