CA2529662A1 - Aryl dicarboxamides - Google Patents

Info

Publication number

CA2529662A1

CA2529662A1 CA002529662A CA2529662A CA2529662A1 CA 2529662 A1 CA2529662 A1 CA 2529662A1 CA 002529662 A CA002529662 A CA 002529662A CA 2529662 A CA2529662 A CA 2529662A CA 2529662 A1 CA2529662 A1 CA 2529662A1

Authority

CA

Canada

Prior art keywords

amino

methyl

carbonyl

alkyl

aryl

Prior art date

2003-07-21

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 125000003118 aryl group Chemical group 0.000 title claims abstract description 74
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 32
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 28
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 22
• 239000001257 hydrogen Substances 0.000 claims abstract description 19
• 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 abstract description 17
• 239000008103 glucose Substances 0.000 claims abstract description 17
• 230000000694 effects Effects 0.000 claims abstract description 14
• 208000008589 Obesity Diseases 0.000 claims abstract description 13
• 235000020824 obesity Nutrition 0.000 claims abstract description 13
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims abstract description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
• 230000001404 mediated effect Effects 0.000 claims abstract description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
• 230000002265 prevention Effects 0.000 claims abstract description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 5
• 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 5
• 125000005418 aryl aryl group Chemical group 0.000 claims abstract description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
• 208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 5
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 5
• 229920001469 poly(aryloxy)thionylphosphazene Polymers 0.000 claims abstract 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 2
• -1 phenyl-thiazolyl Chemical group 0.000 claims description 172
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 149
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 86
• 238000000034 method Methods 0.000 claims description 83
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 76
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 58
• 239000005711 Benzoic acid Substances 0.000 claims description 47
• 235000010233 benzoic acid Nutrition 0.000 claims description 45
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 43
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 28
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 26
• 102100033001 Tyrosine-protein phosphatase non-receptor type 1 Human genes 0.000 claims description 21
• 102100028516 Receptor-type tyrosine-protein phosphatase U Human genes 0.000 claims description 20
• 101001087394 Homo sapiens Tyrosine-protein phosphatase non-receptor type 1 Proteins 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 230000005764 inhibitory process Effects 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 5
• 201000001421 hyperglycemia Diseases 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 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
• 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
• 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 2
• 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 2
• 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 2
• 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 2
• 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 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
• 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 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
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 4
• 125000006733 (C6-C15) alkyl group Chemical group 0.000 claims 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• YIFJGICTMLQRNV-UHFFFAOYSA-N 2-[4-[[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]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=CC=C(C(=O)NCC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=C1 YIFJGICTMLQRNV-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• VHKIBEQZLOZWSK-UHFFFAOYSA-N 2-hydroxy-5-[[2-[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C1=CC=C(C=2SC=C(CN(C(=O)C=3C=CC(=CC=3)C(F)(F)F)C=3C=C(C(O)=CC=3)C(O)=O)N=2)C=C1 VHKIBEQZLOZWSK-UHFFFAOYSA-N 0.000 claims 1
• OOEIVGDKMDSJFG-UHFFFAOYSA-N 2-hydroxy-5-[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-(3-phenylpropanoyl)amino]benzoic 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)CCC=2C=CC=CC=2)=C1 OOEIVGDKMDSJFG-UHFFFAOYSA-N 0.000 claims 1
• LFFPQQXFGADOTH-UHFFFAOYSA-N 2-hydroxy-5-[[2-[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]-1,3-thiazol-4-yl]methyl-[4-(trifluoromethyl)benzoyl]amino]benzoic 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)C(F)(F)F)=C1 LFFPQQXFGADOTH-UHFFFAOYSA-N 0.000 claims 1
• MTECPBSXTKXRMC-UHFFFAOYSA-N 2-hydroxy-5-[[3-methylbut-2-enoyl-[[4-[(4-pentylphenyl)methylcarbamoyl]phenyl]methyl]amino]methyl]benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1CNC(=O)C(C=C1)=CC=C1CN(C(=O)C=C(C)C)CC1=CC=C(O)C(C(O)=O)=C1 MTECPBSXTKXRMC-UHFFFAOYSA-N 0.000 claims 1
• LNEYSWBYZUJJPR-UHFFFAOYSA-N 2-hydroxy-5-[[4-[(4-phenoxyphenyl)methylcarbamoyl]-1,3-thiazol-2-yl]methyl-(3-phenylpropanoyl)amino]benzoic 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)CCC=2C=CC=CC=2)=C1 LNEYSWBYZUJJPR-UHFFFAOYSA-N 0.000 claims 1
• CISLRUUVLWUCHA-UHFFFAOYSA-N 2-hydroxy-5-[[4-[(4-phenoxyphenyl)methylcarbamoyl]phenyl]methyl-(3-phenylpropanoyl)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)CCC=2C=CC=CC=2)=C1 CISLRUUVLWUCHA-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• GXIYEKTVXBVWPW-UHFFFAOYSA-N 5-[(6-chloropyridine-3-carbonyl)-[[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=NC(Cl)=CC=3)C=3C=C(C(O)=CC=3)C(O)=O)N=2)C=C1 GXIYEKTVXBVWPW-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
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