HRP20040759A2 - Thiazolidine carboxamide derivatives as modulators of the prostaglandin f receptor - Google Patents

Info

Publication number

HRP20040759A2

HRP20040759A2 HRP20040759A HRP20040759A2 HR P20040759 A2 HRP20040759 A2 HR P20040759A2 HR P20040759 A HRP20040759 A HR P20040759A HR P20040759 A2 HRP20040759 A2 HR P20040759A2

Authority

HR

Croatia

Prior art keywords

carboxamide

thiazolidine

biphenyl

ylsulfonyl

phenylpropyl

Prior art date

2002-03-28

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• YDGXLVKDGGLWPF-UHFFFAOYSA-N 1,3-thiazolidine-2-carboxamide Chemical class NC(=O)C1NCCS1 YDGXLVKDGGLWPF-UHFFFAOYSA-N 0.000 title claims abstract description 50
• 108050008995 Prostaglandin F receptors Proteins 0.000 title description 13
• 102000000471 Prostaglandin F receptors Human genes 0.000 title description 13
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 208000006399 Premature Obstetric Labor Diseases 0.000 claims abstract description 9
• 208000005107 Premature Birth Diseases 0.000 claims abstract description 8
• 206010036590 Premature baby Diseases 0.000 claims abstract description 8
• 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 7
• 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 7
• 238000011321 prophylaxis Methods 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 192
• -1 ureido, sulfonylamino, sulfanyl Chemical group 0.000 claims description 148
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 79
• 238000000034 method Methods 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 69
• 238000002360 preparation method Methods 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 59
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 56
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 30
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 25
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 102000005962 receptors Human genes 0.000 claims description 20
• 108020003175 receptors Proteins 0.000 claims description 20
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
• 235000010290 biphenyl Nutrition 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 13
• 230000008569 process Effects 0.000 claims description 13
• 230000005764 inhibitory process Effects 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 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 9
• 102000015433 Prostaglandin Receptors Human genes 0.000 claims description 8
• 108010050183 Prostaglandin Receptors Proteins 0.000 claims description 8
• 239000004305 biphenyl Substances 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 206010036600 Premature labour Diseases 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 229940079593 drug Drugs 0.000 claims description 6
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
• 125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims description 5
• 125000004442 acylamino group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 208000026440 premature labor Diseases 0.000 claims description 5
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• BGGHFAFJRYNEEU-YCVJPRETSA-N [(3s)-3-phenyl-3-[[(2s)-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carbonyl]amino]propyl] (2s)-2-amino-3-methylbutanoate Chemical compound S([C@H]1C(=O)N[C@@H](CCOC(=O)[C@@H](N)C(C)C)C=2C=CC=CC=2)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BGGHFAFJRYNEEU-YCVJPRETSA-N 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• LZHDAJKGFYWMNF-UHFFFAOYSA-N n-[1-(2,6-difluorophenyl)-3-hydroxypropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound FC=1C=CC=C(F)C=1C(CCO)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LZHDAJKGFYWMNF-UHFFFAOYSA-N 0.000 claims description 4
• ZQEHPYZSCTXXOE-WEZIJMHWSA-N (2s)-n-[(1s)-3-[benzyl(methyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S([C@H]1C(=O)N[C@@H](CCN(C)CC=2C=CC=CC=2)C=2C=CC=CC=2)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZQEHPYZSCTXXOE-WEZIJMHWSA-N 0.000 claims description 3
• ZOUFHCKTBUNDJB-WEZIJMHWSA-N (2s)-n-[(1s)-3-[methyl(2-pyridin-2-ylethyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S([C@H]1C(=O)N[C@@H](CCN(C)CCC=2N=CC=CC=2)C=2C=CC=CC=2)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZOUFHCKTBUNDJB-WEZIJMHWSA-N 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• CPZYKYIJSVWQCQ-RWPDHJIBSA-N [(3s)-3-(2,6-difluorophenyl)-3-[[(2s)-3-[4-(2-fluorophenyl)phenyl]sulfonyl-1,3-thiazolidine-2-carbonyl]amino]propyl] (2s)-2-amino-3-methylbutanoate Chemical compound S([C@H]1C(=O)N[C@@H](CCOC(=O)[C@@H](N)C(C)C)C=2C(=CC=CC=2F)F)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1F CPZYKYIJSVWQCQ-RWPDHJIBSA-N 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• VHAHFCFZDJNEOX-WNJJXGMVSA-N methyl 2-[methyl-[(3s)-3-phenyl-3-[[(2s)-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carbonyl]amino]propyl]amino]acetate Chemical compound S([C@H]1C(=O)N[C@@H](CCN(C)CC(=O)OC)C=2C=CC=CC=2)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 VHAHFCFZDJNEOX-WNJJXGMVSA-N 0.000 claims description 3
• PUYNBBNYEUAGLL-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NCC1=CC=CO1 PUYNBBNYEUAGLL-UHFFFAOYSA-N 0.000 claims description 3
• BRMOFIIHYYFXJU-UHFFFAOYSA-N n-[1-(1,3-benzodioxol-5-yl)-3-hydroxypropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=C2OCOC2=CC=1C(CCO)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BRMOFIIHYYFXJU-UHFFFAOYSA-N 0.000 claims description 3
• MJSZRROXXJMYQA-UHFFFAOYSA-N n-[3-(1,3-dioxoisoindol-2-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(CCN1C(C2=CC=CC=C2C1=O)=O)C1=CC=CC=C1 MJSZRROXXJMYQA-UHFFFAOYSA-N 0.000 claims description 3
• JSGYJIPRUMGAER-UHFFFAOYSA-N n-[3-(dimethylamino)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(CCN(C)C)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 JSGYJIPRUMGAER-UHFFFAOYSA-N 0.000 claims description 3
• NPMZFYKZMHGJCJ-UHFFFAOYSA-N n-[3-[(2-hydroxycyclohexyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound OC1CCCCC1NCCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 NPMZFYKZMHGJCJ-UHFFFAOYSA-N 0.000 claims description 3
• VQENEPXPGACVEV-UHFFFAOYSA-N n-[3-[(3-hydroxy-3-phenylpropyl)-methylamino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCN(C)CCC(O)C1=CC=CC=C1 VQENEPXPGACVEV-UHFFFAOYSA-N 0.000 claims description 3
• VGXYUNQQIFNCMO-UHFFFAOYSA-N n-[[6-(dimethylamino)pyridin-3-yl]-phenylmethyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1=NC(N(C)C)=CC=C1C(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 VGXYUNQQIFNCMO-UHFFFAOYSA-N 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• DPNGHXILFFWKIP-IRLDBZIGSA-N (2s)-3-(4-iodophenyl)sulfonyl-n-[(r)-phenyl(pyridin-2-yl)methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(I)=CC=C1S(=O)(=O)N1[C@H](C(=O)N[C@H](C=2C=CC=CC=2)C=2N=CC=CC=2)SCC1 DPNGHXILFFWKIP-IRLDBZIGSA-N 0.000 claims description 2
• KTNPHZXLUABWFB-UNMCSNQZSA-N (2s)-3-(4-tert-butylphenyl)sulfonyl-n-[(1s)-3-hydroxy-1-phenylpropyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1[C@H](C(=O)N[C@@H](CCO)C=2C=CC=CC=2)SCC1 KTNPHZXLUABWFB-UNMCSNQZSA-N 0.000 claims description 2
• BQUPZAGCRBOKHE-IAPPQJPRSA-N (2s)-3-[4-(2-fluorophenyl)phenyl]sulfonyl-n-[(r)-phenyl(pyridin-4-yl)methyl]-1,3-thiazolidine-2-carboxamide Chemical compound FC1=CC=CC=C1C1=CC=C(S(=O)(=O)N2[C@@H](SCC2)C(=O)N[C@H](C=2C=CC=CC=2)C=2C=CN=CC=2)C=C1 BQUPZAGCRBOKHE-IAPPQJPRSA-N 0.000 claims description 2
• XSKWWUPIAQUJKB-PXJZQJOASA-N (2s)-3-[4-(2-fluorophenyl)phenyl]sulfonyl-n-[(s)-(1-methylpiperidin-4-yl)-phenylmethyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1CN(C)CCC1[C@@H](C=1C=CC=CC=1)NC(=O)[C@H]1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C(=CC=CC=2)F)CCS1 XSKWWUPIAQUJKB-PXJZQJOASA-N 0.000 claims description 2
• KABQYCGEOUKVSE-PBVYKCSPSA-N (2s)-3-phenyl-2-[[3-(5-pyridin-2-ylthiophen-2-yl)sulfonyl-1,3-thiazolidine-2-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)C1N(CCS1)S(=O)(=O)C=1SC(=CC=1)C=1N=CC=CC=1)C1=CC=CC=C1 KABQYCGEOUKVSE-PBVYKCSPSA-N 0.000 claims description 2
• LSFMYWQLUYQROF-XCZPVHLTSA-N (2s)-n-[(1s)-3-[2-hydroxyethyl(methyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S([C@H]1C(=O)N[C@@H](CCN(CCO)C)C=2C=CC=CC=2)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LSFMYWQLUYQROF-XCZPVHLTSA-N 0.000 claims description 2
• ORTWOTJYLQNIAD-SMCANUKXSA-N (2s)-n-[(1s)-3-[furan-2-ylmethyl(methyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S([C@H]1C(=O)N[C@@H](CCN(C)CC=2OC=CC=2)C=2C=CC=CC=2)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ORTWOTJYLQNIAD-SMCANUKXSA-N 0.000 claims description 2
• IXWMHQDEATVGAB-GMAHTHKFSA-N (2s)-n-[(1s)-3-hydroxy-1-phenylpropyl]-3-[4-(2-methylbutan-2-yl)phenyl]sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(C(C)(C)CC)=CC=C1S(=O)(=O)N1[C@H](C(=O)N[C@@H](CCO)C=2C=CC=CC=2)SCC1 IXWMHQDEATVGAB-GMAHTHKFSA-N 0.000 claims description 2
• FKYXCPHVEPGKKM-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-n-(pyridin-2-ylmethyl)-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C(=O)NCC=2N=CC=CC=2)SCC1 FKYXCPHVEPGKKM-UHFFFAOYSA-N 0.000 claims description 2
• ATWAEQFQJUPXHV-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-n-[[4-[(2-ethylhexylcarbamoylamino)methyl]phenyl]methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(CNC(=O)NCC(CC)CCCC)=CC=C1CNC(=O)C1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CCS1 ATWAEQFQJUPXHV-UHFFFAOYSA-N 0.000 claims description 2
• KTWQIOKKFYBIAT-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-n-[[4-[(2-phenylethylcarbamoylamino)methyl]phenyl]methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C(=O)NCC=2C=CC(CNC(=O)NCCC=3C=CC=CC=3)=CC=2)SCC1 KTWQIOKKFYBIAT-UHFFFAOYSA-N 0.000 claims description 2
• WEBPQUSCSPARHM-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-n-[[4-[[(4-methylphenyl)methylcarbamoylamino]methyl]phenyl]methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(C)=CC=C1CNC(=O)NCC(C=C1)=CC=C1CNC(=O)C1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CCS1 WEBPQUSCSPARHM-UHFFFAOYSA-N 0.000 claims description 2
• HAVLLVRJCVWXSR-UHFFFAOYSA-N 3-(4-iodophenyl)sulfonyl-n-[[4-[[(4-methylphenyl)methylcarbamoylamino]methyl]phenyl]methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(C)=CC=C1CNC(=O)NCC(C=C1)=CC=C1CNC(=O)C1N(S(=O)(=O)C=2C=CC(I)=CC=2)CCS1 HAVLLVRJCVWXSR-UHFFFAOYSA-N 0.000 claims description 2
• RVBLVBKXLYHZFZ-UHFFFAOYSA-N 3-(4-phenylphenyl)sulfonyl-n-(1-phenyl-2-pyrrolidin-1-ylethyl)-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CN1CCCC1 RVBLVBKXLYHZFZ-UHFFFAOYSA-N 0.000 claims description 2
• LJFGPSNJPOWGJE-UHFFFAOYSA-N 3-(4-phenylphenyl)sulfonyl-n-(1-phenyl-3-piperazin-1-ylpropyl)-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCN1CCNCC1 LJFGPSNJPOWGJE-UHFFFAOYSA-N 0.000 claims description 2
• XNAZQHDLXFPWGC-UHFFFAOYSA-N 3-(4-phenylphenyl)sulfonyl-n-(1-phenyl-3-pyrrolidin-1-ylpropyl)-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCN1CCCC1 XNAZQHDLXFPWGC-UHFFFAOYSA-N 0.000 claims description 2
• IIXQBJXAQSCKGH-UHFFFAOYSA-N 3-(4-phenylphenyl)sulfonyl-n-[1-phenyl-3-(2-piperidin-1-ylethylamino)propyl]-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCNCCN1CCCCC1 IIXQBJXAQSCKGH-UHFFFAOYSA-N 0.000 claims description 2
• XYTHQBWYNYKWAB-UHFFFAOYSA-N 3-(4-phenylphenyl)sulfonyl-n-[1-phenyl-3-(2-pyridin-2-ylethylamino)propyl]-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCNCCC1=CC=CC=N1 XYTHQBWYNYKWAB-UHFFFAOYSA-N 0.000 claims description 2
• FHCAYDQYSMUQIC-UHFFFAOYSA-N 3-(4-phenylphenyl)sulfonyl-n-[1-phenyl-3-(4-pyrrolidin-1-ylpiperidin-1-yl)propyl]-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCN(CC1)CCC1N1CCCC1 FHCAYDQYSMUQIC-UHFFFAOYSA-N 0.000 claims description 2
• JCPGIYJHORAFLM-UHFFFAOYSA-N 3-(4-phenylphenyl)sulfonyl-n-[1-phenyl-3-(pyridin-2-ylmethylamino)propyl]-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCNCC1=CC=CC=N1 JCPGIYJHORAFLM-UHFFFAOYSA-N 0.000 claims description 2
• MMUOUJZHGQQBPF-UHFFFAOYSA-N 3-(4-phenylphenyl)sulfonyl-n-[1-phenyl-3-(pyridin-3-ylmethylamino)propyl]-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCNCC1=CC=CN=C1 MMUOUJZHGQQBPF-UHFFFAOYSA-N 0.000 claims description 2
• LKFFDZGSDJRMPJ-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-n-[1-(1h-indol-3-yl)propan-2-yl]-1,3-thiazolidine-2-carboxamide Chemical compound C=1NC2=CC=CC=C2C=1CC(C)NC(=O)C1SCCN1S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 LKFFDZGSDJRMPJ-UHFFFAOYSA-N 0.000 claims description 2
• BHWXLUJDLLBBPW-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-n-[[1-(4-chlorophenyl)cyclopropyl]methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)N1C(C(=O)NCC2(CC2)C=2C=CC(Cl)=CC=2)SCC1 BHWXLUJDLLBBPW-UHFFFAOYSA-N 0.000 claims description 2
• IFTRUYLMLKSHDS-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-n-[[4-[3-(dimethylamino)propoxy]phenyl]methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(OCCCN(C)C)=CC=C1CNC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C(C)(C)C)CCS1 IFTRUYLMLKSHDS-UHFFFAOYSA-N 0.000 claims description 2
• UEJBBBHIWAEAOE-UHFFFAOYSA-N 3-(benzenesulfonyl)-n-[[4-[(hexylcarbamoylamino)methyl]phenyl]methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(CNC(=O)NCCCCCC)=CC=C1CNC(=O)C1N(S(=O)(=O)C=2C=CC=CC=2)CCS1 UEJBBBHIWAEAOE-UHFFFAOYSA-N 0.000 claims description 2
• ATXRKTIUNMHFFR-UHFFFAOYSA-N 3-[4-(3,4-dichlorophenyl)phenyl]sulfonyl-n-[1-(furan-2-yl)-3-hydroxypropyl]-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=COC=1C(CCO)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C(Cl)=C1 ATXRKTIUNMHFFR-UHFFFAOYSA-N 0.000 claims description 2
• JZGLJXIFCRBXRG-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)phenyl]sulfonyl-n-[1-(furan-2-yl)-3-hydroxypropyl]-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=COC=1C(CCO)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 JZGLJXIFCRBXRG-UHFFFAOYSA-N 0.000 claims description 2
• LSPLZPQYAXHWSY-UHFFFAOYSA-N 3-[5-(1,2-oxazol-3-yl)thiophen-2-yl]sulfonyl-n-[[4-[(2-phenylethylcarbamoylamino)methyl]phenyl]methyl]-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=C(CNC(=O)C2N(CCS2)S(=O)(=O)C=2SC(=CC=2)C2=NOC=C2)C=CC=1CNC(=O)NCCC1=CC=CC=C1 LSPLZPQYAXHWSY-UHFFFAOYSA-N 0.000 claims description 2
• WQKVQXFHBPFXBP-QHSFNAQHSA-N 3-[[(3s)-3-phenyl-3-[[3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carbonyl]amino]propyl]sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NCC[C@H](NC(=O)C2N(CCS2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 WQKVQXFHBPFXBP-QHSFNAQHSA-N 0.000 claims description 2
• NKJPPDDILIFMKN-RWPDHJIBSA-N [(3s)-3-(2,6-difluorophenyl)-3-[[(2s)-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carbonyl]amino]propyl] (2s)-2-amino-3-methylbutanoate Chemical compound S([C@H]1C(=O)N[C@@H](CCOC(=O)[C@@H](N)C(C)C)C=2C(=CC=CC=2F)F)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 NKJPPDDILIFMKN-RWPDHJIBSA-N 0.000 claims description 2
• GXTUZPCUVCYIKF-YCVJPRETSA-N [(3s)-3-[[(2s)-3-[4-(2-fluorophenyl)phenyl]sulfonyl-1,3-thiazolidine-2-carbonyl]amino]-3-phenylpropyl] (2s)-2-amino-3-methylbutanoate Chemical compound S([C@H]1C(=O)N[C@@H](CCOC(=O)[C@@H](N)C(C)C)C=2C=CC=CC=2)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1F GXTUZPCUVCYIKF-YCVJPRETSA-N 0.000 claims description 2
• 125000005217 alkenylheteroaryl group Chemical group 0.000 claims description 2
• 125000000539 amino acid group Chemical group 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• LPKPLSFLGRVOMX-DITALETJSA-N ethyl 2-[4-[(3s)-3-phenyl-3-[[(2s)-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carbonyl]amino]propyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC[C@@H](C=1C=CC=CC=1)NC(=O)[C@H]1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 LPKPLSFLGRVOMX-DITALETJSA-N 0.000 claims description 2
• VMCKYVFBARFVGQ-UHFFFAOYSA-N n-(2,2-diphenylethyl)-3-quinolin-8-ylsulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C1C(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 VMCKYVFBARFVGQ-UHFFFAOYSA-N 0.000 claims description 2
• TZZSZUVBBRLHIT-UHFFFAOYSA-N n-[(1,5-dimethylpyrrol-2-yl)methyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound CN1C(C)=CC=C1CNC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 TZZSZUVBBRLHIT-UHFFFAOYSA-N 0.000 claims description 2
• CGACPOITWZEKAO-UHFFFAOYSA-N n-[(1-oxidopyridin-1-ium-2-yl)methyl]-1-oxo-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound [O-][N+]1=CC=CC=C1CNC(=O)C1S(=O)CCN1S(=O)(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 CGACPOITWZEKAO-UHFFFAOYSA-N 0.000 claims description 2
• YOYQLOQWIUNNDG-UHFFFAOYSA-N n-[(2,5-difluorophenyl)methyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound FC1=CC=C(F)C(CNC(=O)C2N(CCS2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 YOYQLOQWIUNNDG-UHFFFAOYSA-N 0.000 claims description 2
• QIZLGAZAAHOVFS-UHFFFAOYSA-N n-[(3,4-difluorophenyl)methyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1=C(F)C(F)=CC=C1CNC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 QIZLGAZAAHOVFS-UHFFFAOYSA-N 0.000 claims description 2
• DNOXAIIFMBCVIY-VETVTEPKSA-N n-[(r)-[6-[2-(dimethylamino)ethoxy]pyridin-2-yl]-phenylmethyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound CN(C)CCOC1=CC=CC([C@H](NC(=O)C2N(CCS2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 DNOXAIIFMBCVIY-VETVTEPKSA-N 0.000 claims description 2
• BMTHTMKUWUBFJV-UHFFFAOYSA-N n-[1-(1-benzofuran-2-yl)-3-hydroxypropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C2=CC=CC=C2OC=1C(CCO)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BMTHTMKUWUBFJV-UHFFFAOYSA-N 0.000 claims description 2
• GGJPJWKCGQDYGD-UHFFFAOYSA-N n-[1-(3,4-dichlorophenyl)-3-hydroxypropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(CCO)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GGJPJWKCGQDYGD-UHFFFAOYSA-N 0.000 claims description 2
• AZAGEADOLOVTON-UHFFFAOYSA-N n-[1-(furan-2-yl)-3-hydroxypropyl]-3-[4-(4-methoxyphenyl)phenyl]sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)N2C(SCC2)C(=O)NC(CCO)C=2OC=CC=2)C=C1 AZAGEADOLOVTON-UHFFFAOYSA-N 0.000 claims description 2
• ATJNYCGOVMLZLA-UHFFFAOYSA-N n-[1-(furan-2-yl)-3-hydroxypropyl]-3-[4-(4-methylphenyl)phenyl]sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=CC=C(S(=O)(=O)N2C(SCC2)C(=O)NC(CCO)C=2OC=CC=2)C=C1 ATJNYCGOVMLZLA-UHFFFAOYSA-N 0.000 claims description 2
• QYKJIRWDHJUYQI-UHFFFAOYSA-N n-[1-phenyl-3-(2-phenylethylamino)propyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCNCCC1=CC=CC=C1 QYKJIRWDHJUYQI-UHFFFAOYSA-N 0.000 claims description 2
• BZJPZOPXVBRONH-UHFFFAOYSA-N n-[1-phenyl-3-(2-phenylpropylamino)propyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(C)CNCCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BZJPZOPXVBRONH-UHFFFAOYSA-N 0.000 claims description 2
• WGDOYBXKPPJWDC-UHFFFAOYSA-N n-[3-(1-adamantylmethylamino)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(CCNCC12CC3CC(CC(C3)C1)C2)C1=CC=CC=C1 WGDOYBXKPPJWDC-UHFFFAOYSA-N 0.000 claims description 2
• CYEBVOSGMNUSCB-UHFFFAOYSA-N n-[3-(2,5-dihydropyrrol-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCN1CC=CC1 CYEBVOSGMNUSCB-UHFFFAOYSA-N 0.000 claims description 2
• DFFMSHPAFONHFF-UHFFFAOYSA-N n-[3-(2-hydroxyethylamino)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(CCNCCO)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 DFFMSHPAFONHFF-UHFFFAOYSA-N 0.000 claims description 2
• QDYPMNSCKKIMBO-UHFFFAOYSA-N n-[3-(2-hydroxypropylamino)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(CCNCC(O)C)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QDYPMNSCKKIMBO-UHFFFAOYSA-N 0.000 claims description 2
• AEVJQENKGKQCBA-UHFFFAOYSA-N n-[3-(3,5-dimethylpiperidin-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1C(C)CC(C)CN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 AEVJQENKGKQCBA-UHFFFAOYSA-N 0.000 claims description 2
• HBCZFNMZHVOJGB-UHFFFAOYSA-N n-[3-(3,6-dihydro-2h-pyridin-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCN1CCC=CC1 HBCZFNMZHVOJGB-UHFFFAOYSA-N 0.000 claims description 2
• MOLWSWGXSYTDHC-UHFFFAOYSA-N n-[3-(3-hydroxypiperidin-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1C(O)CCCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 MOLWSWGXSYTDHC-UHFFFAOYSA-N 0.000 claims description 2
• COZYPLYHOCUHNY-UHFFFAOYSA-N n-[3-(3-hydroxypropylamino)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(CCNCCCO)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 COZYPLYHOCUHNY-UHFFFAOYSA-N 0.000 claims description 2
• PGLBUNVBHPEMIN-UHFFFAOYSA-N n-[3-(3-hydroxypyrrolidin-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1C(O)CCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 PGLBUNVBHPEMIN-UHFFFAOYSA-N 0.000 claims description 2
• SNEBNRKSHQBBQZ-UHFFFAOYSA-N n-[3-(3-methylpiperidin-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1C(C)CCCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 SNEBNRKSHQBBQZ-UHFFFAOYSA-N 0.000 claims description 2
• FLKNQVJKSBYQLH-UHFFFAOYSA-N n-[3-(4-acetylpiperazin-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1CN(C(=O)C)CCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 FLKNQVJKSBYQLH-UHFFFAOYSA-N 0.000 claims description 2
• MZHFWMHZXKBXKT-UHFFFAOYSA-N n-[3-(4-benzyl-4-hydroxypiperidin-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1CN(CCC(NC(=O)C2N(CCS2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1(O)CC1=CC=CC=C1 MZHFWMHZXKBXKT-UHFFFAOYSA-N 0.000 claims description 2
• FFNNRUCFQZYEKF-UHFFFAOYSA-N n-[3-(4-hydroxypiperidin-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1CC(O)CCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 FFNNRUCFQZYEKF-UHFFFAOYSA-N 0.000 claims description 2
• FYHFPDWMJGQFBE-UHFFFAOYSA-N n-[3-(azepan-1-yl)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCN1CCCCCC1 FYHFPDWMJGQFBE-UHFFFAOYSA-N 0.000 claims description 2
• JMEOYLWCYQSSNK-UHFFFAOYSA-N n-[3-(furan-2-ylmethylamino)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCNCC1=CC=CO1 JMEOYLWCYQSSNK-UHFFFAOYSA-N 0.000 claims description 2
• VXELDQDIAIXCGX-UHFFFAOYSA-N n-[3-(oxolan-2-ylmethylamino)-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCNCC1CCCO1 VXELDQDIAIXCGX-UHFFFAOYSA-N 0.000 claims description 2
• WXTZSYZVSZDNQN-UHFFFAOYSA-N n-[3-[(2-hydroxy-2-phenylethyl)-methylamino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(O)CN(C)CCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 WXTZSYZVSZDNQN-UHFFFAOYSA-N 0.000 claims description 2
• BVVKSEDCBGXLBR-UHFFFAOYSA-N n-[3-[(2-hydroxy-2-phenylethyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(O)CNCCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BVVKSEDCBGXLBR-UHFFFAOYSA-N 0.000 claims description 2
• APXVSXSYCPLVSN-CUVAOJNPSA-N n-[3-[(2r)-2-(anilinomethyl)pyrrolidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C([C@H]1CCCN1CCC(NC(=O)C1N(CCS1)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)NC1=CC=CC=C1 APXVSXSYCPLVSN-CUVAOJNPSA-N 0.000 claims description 2
• NZTBACSWSGBKPT-OMJZMDCHSA-N n-[3-[(2r)-2-(hydroxymethyl)pyrrolidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound OC[C@H]1CCCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 NZTBACSWSGBKPT-OMJZMDCHSA-N 0.000 claims description 2
• QFAKZJQVANSJGZ-PDQRKSTBSA-N n-[3-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound COC[C@H]1CCCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 QFAKZJQVANSJGZ-PDQRKSTBSA-N 0.000 claims description 2
• APXVSXSYCPLVSN-KCIPMGJTSA-N n-[3-[(2s)-2-(anilinomethyl)pyrrolidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C([C@@H]1CCCN1CCC(NC(=O)C1N(CCS1)S(=O)(=O)C=1C=CC(=CC=1)C=1C=CC=CC=1)C=1C=CC=CC=1)NC1=CC=CC=C1 APXVSXSYCPLVSN-KCIPMGJTSA-N 0.000 claims description 2
• QFAKZJQVANSJGZ-JLTFQNRBSA-N n-[3-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound COC[C@@H]1CCCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 QFAKZJQVANSJGZ-JLTFQNRBSA-N 0.000 claims description 2
• QADPFZBRBLKEKI-UHFFFAOYSA-N n-[3-[(3,5-difluorophenyl)methylamino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound FC1=CC(F)=CC(CNCCC(NC(=O)C2N(CCS2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QADPFZBRBLKEKI-UHFFFAOYSA-N 0.000 claims description 2
• XTLDWIQNVCEPGM-BVHOSPSZSA-N n-[3-[(3r)-3-(hydroxymethyl)-3,4-dihydro-1h-isoquinolin-2-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C([C@@H]1CO)C2=CC=CC=C2CN1CCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 XTLDWIQNVCEPGM-BVHOSPSZSA-N 0.000 claims description 2
• PGLBUNVBHPEMIN-KZEUERNQSA-N n-[3-[(3r)-3-hydroxypyrrolidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1[C@H](O)CCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 PGLBUNVBHPEMIN-KZEUERNQSA-N 0.000 claims description 2
• XTLDWIQNVCEPGM-MVDSBDBVSA-N n-[3-[(3s)-3-(hydroxymethyl)-3,4-dihydro-1h-isoquinolin-2-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C([C@H]1CO)C2=CC=CC=C2CN1CCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 XTLDWIQNVCEPGM-MVDSBDBVSA-N 0.000 claims description 2
• QFQCSLXXAFHSEL-UHFFFAOYSA-N n-[3-[(4-fluorophenyl)methylamino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(F)=CC=C1CNCCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 QFQCSLXXAFHSEL-UHFFFAOYSA-N 0.000 claims description 2
• PMSXMCPTIPYIJO-UHFFFAOYSA-N n-[3-[2-(hydroxymethyl)piperidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound OCC1CCCCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 PMSXMCPTIPYIJO-UHFFFAOYSA-N 0.000 claims description 2
• LSFMYWQLUYQROF-UHFFFAOYSA-N n-[3-[2-hydroxyethyl(methyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(CCN(CCO)C)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LSFMYWQLUYQROF-UHFFFAOYSA-N 0.000 claims description 2
• KYANYSOGMLXGNT-UHFFFAOYSA-N n-[3-[3-(dimethylamino)propyl-methylamino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(CCN(C)CCCN(C)C)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 KYANYSOGMLXGNT-UHFFFAOYSA-N 0.000 claims description 2
• YTAOVOCPDAVOHN-UHFFFAOYSA-N n-[3-[3-(hydroxymethyl)piperidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1C(CO)CCCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 YTAOVOCPDAVOHN-UHFFFAOYSA-N 0.000 claims description 2
• NFSCYLVCYHUDST-UHFFFAOYSA-N n-[3-[4-(2-hydroxyethyl)piperidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1CC(CCO)CCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 NFSCYLVCYHUDST-UHFFFAOYSA-N 0.000 claims description 2
• DDDIARUCORQSRK-UHFFFAOYSA-N n-[3-[4-(hydroxymethyl)piperidin-1-yl]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1CC(CO)CCN1CCC(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 DDDIARUCORQSRK-UHFFFAOYSA-N 0.000 claims description 2
• VXELDQDIAIXCGX-SNKUFMAISA-N n-[3-[[(2s)-oxolan-2-yl]methylamino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S1CCN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C1C(=O)NC(C=1C=CC=CC=1)CCNC[C@@H]1CCCO1 VXELDQDIAIXCGX-SNKUFMAISA-N 0.000 claims description 2
• ZQEHPYZSCTXXOE-UHFFFAOYSA-N n-[3-[benzyl(methyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1CN(C)CCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZQEHPYZSCTXXOE-UHFFFAOYSA-N 0.000 claims description 2
• GFMLWTWLYHOPCG-UHFFFAOYSA-N n-[3-[methyl(2-phenylethyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=CC=1CCN(C)CCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GFMLWTWLYHOPCG-UHFFFAOYSA-N 0.000 claims description 2
• ZOUFHCKTBUNDJB-UHFFFAOYSA-N n-[3-[methyl(2-pyridin-2-ylethyl)amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C=1C=CC=NC=1CCN(C)CCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 ZOUFHCKTBUNDJB-UHFFFAOYSA-N 0.000 claims description 2
• BPRYOBNOJKLBJI-JLMQRPCNSA-N n-[3-[methyl-[(1r)-1-phenylethyl]amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound CN([C@H](C)C=1C=CC=CC=1)CCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BPRYOBNOJKLBJI-JLMQRPCNSA-N 0.000 claims description 2
• BPRYOBNOJKLBJI-CKEWUSPSSA-N n-[3-[methyl-[(1s)-1-phenylethyl]amino]-1-phenylpropyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound CN([C@@H](C)C=1C=CC=CC=1)CCC(C=1C=CC=CC=1)NC(=O)C1SCCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 BPRYOBNOJKLBJI-CKEWUSPSSA-N 0.000 claims description 2
• ZXMCBFMHJDCWKT-UHFFFAOYSA-N n-[3-hydroxy-1-(4-methoxyphenyl)propyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C(CCO)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 ZXMCBFMHJDCWKT-UHFFFAOYSA-N 0.000 claims description 2
• LVEQLYSCLPNIPQ-UHFFFAOYSA-N n-[[4-[(hexylcarbamoylamino)methyl]phenyl]methyl]-3-[5-(1,2-oxazol-3-yl)thiophen-2-yl]sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1=CC(CNC(=O)NCCCCCC)=CC=C1CNC(=O)C1N(S(=O)(=O)C=2SC(=CC=2)C2=NOC=C2)CCS1 LVEQLYSCLPNIPQ-UHFFFAOYSA-N 0.000 claims description 2
• LFBGIOCTHJKIMZ-UHFFFAOYSA-N n-[[5-[2-(dimethylamino)ethoxy]pyridin-2-yl]-phenylmethyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound N1=CC(OCCN(C)C)=CC=C1C(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 LFBGIOCTHJKIMZ-UHFFFAOYSA-N 0.000 claims description 2
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
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• YUVASQBTMRYWQG-DHLKQENFSA-N (2s)-n-[(1s)-1-(2,6-difluorophenyl)-3-hydroxypropyl]-3-[4-(2-fluorophenyl)phenyl]sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound S([C@H]1C(=O)N[C@@H](CCO)C=2C(=CC=CC=2F)F)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1F YUVASQBTMRYWQG-DHLKQENFSA-N 0.000 claims 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
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• XVZPSBQCANWLQQ-LLMLAESMSA-N n-[[1-[(2s)-2-amino-3-methylbutanoyl]piperidin-4-yl]-phenylmethyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide Chemical compound C1CN(C(=O)[C@@H](N)C(C)C)CCC1C(C=1C=CC=CC=1)NC(=O)C1N(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCS1 XVZPSBQCANWLQQ-LLMLAESMSA-N 0.000 claims 1
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