HRP20000552A2 - Inhibitors of phospholipase enzymes - Google Patents

Info

Publication number

HRP20000552A2

HRP20000552A2 HR20000552A HRP20000552A HRP20000552A2 HR P20000552 A2 HRP20000552 A2 HR P20000552A2 HR 20000552 A HR20000552 A HR 20000552A HR P20000552 A HRP20000552 A HR P20000552A HR P20000552 A2 HRP20000552 A2 HR P20000552A2

Authority

HR

Croatia

Prior art keywords

alkyl

methyl

phenyl

cooh

pharmaceutically acceptable

Prior art date

1998-02-25

Links

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• 108010064785 Phospholipases Proteins 0.000 title claims description 16
• 102000015439 Phospholipases Human genes 0.000 title claims description 16
• 239000003112 inhibitor Substances 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims description 198
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 189
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 178
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 137
• -1 -O-phenyl Chemical group 0.000 claims description 123
• 229910052736 halogen Inorganic materials 0.000 claims description 107
• 150000003839 salts Chemical class 0.000 claims description 106
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 105
• 150000002367 halogens Chemical class 0.000 claims description 103
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 100
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 77
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 72
• 239000002253 acid Substances 0.000 claims description 71
• 238000000034 method Methods 0.000 claims description 65
• 125000001424 substituent group Chemical group 0.000 claims description 58
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 50
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 50
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 39
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 229910052717 sulfur Inorganic materials 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 31
• 239000008194 pharmaceutical composition Substances 0.000 claims description 31
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
• 125000004076 pyridyl group Chemical group 0.000 claims description 28
• 125000002541 furyl group Chemical group 0.000 claims description 26
• 125000001544 thienyl group Chemical group 0.000 claims description 26
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 24
• 239000005711 Benzoic acid Substances 0.000 claims description 23
• 235000010233 benzoic acid Nutrition 0.000 claims description 23
• 150000003536 tetrazoles Chemical class 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
• 102000004190 Enzymes Human genes 0.000 claims description 21
• 108090000790 Enzymes Proteins 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 19
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
• 125000005979 2-naphthyloxy group Chemical group 0.000 claims description 14
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 13
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• 230000009471 action Effects 0.000 claims description 8
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 125000005493 quinolyl group Chemical group 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 230000028709 inflammatory response Effects 0.000 claims description 7
• ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 claims description 6
• NZCFTJZVKYXWNR-UHFFFAOYSA-N 3-[4-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]butanoylamino]propanoic acid Chemical compound C12=CC(OCC=3C=CC=CC=3)=CC=C2N(CCCC(=O)NCCC(=O)O)C(COC=2C=C3C=CC=CC3=CC=2)=C1C(=O)C1=CC=CC=C1 NZCFTJZVKYXWNR-UHFFFAOYSA-N 0.000 claims description 6
• SMGCYQDSONQOAB-UHFFFAOYSA-N 4-[[5-(butylcarbamoylamino)-3-chloro-2-(naphthalen-2-ylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1SCC1=C(Cl)C2=CC(NC(=O)NCCCC)=CC=C2N1CC1=CC=C(C(O)=O)C=C1 SMGCYQDSONQOAB-UHFFFAOYSA-N 0.000 claims description 6
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
• 239000000654 additive Substances 0.000 claims description 6
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 230000000996 additive effect Effects 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 5
• UTKOISXFZCRTMM-UHFFFAOYSA-N 4-[[3-chloro-2-(naphthalen-2-ylsulfanylmethyl)-5-(thiophene-3-carbonylamino)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C3=CSC=C3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 UTKOISXFZCRTMM-UHFFFAOYSA-N 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 4
• 125000005647 linker group Chemical group 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• OEXARBJNOQARFV-UHFFFAOYSA-N 2-[4-[[3-(naphthalene-1-carbonyl)-5-phenylmethoxyindol-1-yl]methyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C=2C3=CC=CC=C3C=CC=2)=C1 OEXARBJNOQARFV-UHFFFAOYSA-N 0.000 claims description 3
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 3
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 3
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
• AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 3
• VHRWSJSYNRPCDJ-UHFFFAOYSA-N 3-[[1-[(4-carboxyphenyl)methyl]-3-chloro-2-(naphthalen-2-ylsulfanylmethyl)indol-5-yl]carbamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C=3C=C(C=CC=3)C(O)=O)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 VHRWSJSYNRPCDJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 3
• DWJDTJAHMKFBOY-UHFFFAOYSA-N 4-[[5-acetamido-3-chloro-2-(naphthalen-2-ylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1SCC1=C(Cl)C2=CC(NC(=O)C)=CC=C2N1CC1=CC=C(C(O)=O)C=C1 DWJDTJAHMKFBOY-UHFFFAOYSA-N 0.000 claims description 3
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 3
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 3
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 3
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 3
• 239000000126 substance Substances 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• SODNQSQGAIFUJN-UHFFFAOYSA-N 2-[3-(2-methylpropanoyl)-2-(naphthalen-2-ylsulfanylmethyl)-5-phenylmethoxyindol-1-yl]acetic acid Chemical compound C1=C2C(C(=O)C(C)C)=C(CSC=3C=C4C=CC=CC4=CC=3)N(CC(O)=O)C2=CC=C1OCC1=CC=CC=C1 SODNQSQGAIFUJN-UHFFFAOYSA-N 0.000 claims description 2
• BAEMDODKDIQWKC-UHFFFAOYSA-N 2-[3-[[3-acetyl-2-(naphthalen-2-ylsulfanylmethyl)-5-phenylmethoxyindol-1-yl]methyl]benzoyl]-1,3-benzothiazole-6-carboxylic acid Chemical compound C1=C2C(C(=O)C)=C(CSC=3C=C4C=CC=CC4=CC=3)N(CC=3C=C(C=CC=3)C(=O)C=3SC4=CC(=CC=C4N=3)C(O)=O)C2=CC=C1OCC1=CC=CC=C1 BAEMDODKDIQWKC-UHFFFAOYSA-N 0.000 claims description 2
• PLJCHEFJWIQVNJ-UHFFFAOYSA-N 2-[3-acetyl-2-(naphthalen-2-ylsulfanylmethyl)-5-phenylmethoxyindol-1-yl]acetic acid Chemical compound C1=C2C(C(=O)C)=C(CSC=3C=C4C=CC=CC4=CC=3)N(CC(O)=O)C2=CC=C1OCC1=CC=CC=C1 PLJCHEFJWIQVNJ-UHFFFAOYSA-N 0.000 claims description 2
• PXWGBEVVBHLZAD-UHFFFAOYSA-N 2-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]acetic acid Chemical compound C12=CC(OCC=3C=CC=CC=3)=CC=C2N(CC(=O)O)C(COC=2C=C3C=CC=CC3=CC=2)=C1C(=O)C1=CC=CC=C1 PXWGBEVVBHLZAD-UHFFFAOYSA-N 0.000 claims description 2
• AEMVESKVBNFDCE-UHFFFAOYSA-N 2-[4-[[3-(naphthalene-2-carbonyl)-5-phenylmethoxyindol-1-yl]methyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C=2C=C3C=CC=CC3=CC=2)=C1 AEMVESKVBNFDCE-UHFFFAOYSA-N 0.000 claims description 2
• NRNLBPVRUUVAMS-UHFFFAOYSA-N 3-[4-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]butanoylamino]-n-(trifluoromethylsulfonyl)benzamide Chemical compound FC(F)(F)S(=O)(=O)NC(=O)C1=CC=CC(NC(=O)CCCN2C3=CC=C(OCC=4C=CC=CC=4)C=C3C(C(=O)C=3C=CC=CC=3)=C2COC=2C=C3C=CC=CC3=CC=2)=C1 NRNLBPVRUUVAMS-UHFFFAOYSA-N 0.000 claims description 2
• DINYDBMUCYPEFQ-UHFFFAOYSA-N 3-[5-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]pentanoylamino]-n-(trifluoromethylsulfonyl)benzamide Chemical compound FC(F)(F)S(=O)(=O)NC(=O)C1=CC=CC(NC(=O)CCCCN2C3=CC=C(OCC=4C=CC=CC=4)C=C3C(C(=O)C=3C=CC=CC=3)=C2COC=2C=C3C=CC=CC3=CC=2)=C1 DINYDBMUCYPEFQ-UHFFFAOYSA-N 0.000 claims description 2
• TWJSPFAVMDKSJP-UHFFFAOYSA-N 3-[5-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]pentanoylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)CCCCN2C3=CC=C(OCC=4C=CC=CC=4)C=C3C(C(=O)C=3C=CC=CC=3)=C2COC=2C=C3C=CC=CC3=CC=2)=C1 TWJSPFAVMDKSJP-UHFFFAOYSA-N 0.000 claims description 2
• TXVCEJJUAUTMAW-UHFFFAOYSA-N 3-[[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CN2C3=CC=C(OCC=4C=CC=CC=4)C=C3C(C(=O)C=3C=CC=CC=3)=C2COC=2C=C3C=CC=CC3=CC=2)=C1 TXVCEJJUAUTMAW-UHFFFAOYSA-N 0.000 claims description 2
• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• KWIVRAVCZJXOQC-UHFFFAOYSA-N 3h-oxathiazole Chemical compound N1SOC=C1 KWIVRAVCZJXOQC-UHFFFAOYSA-N 0.000 claims description 2
• IUZNJJRTTUBGFY-UHFFFAOYSA-N 4-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]-n-(2-methylphenyl)sulfonylbutanamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(=O)CCCN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C=2C=CC=CC=2)=C1COC1=CC=C(C=CC=C2)C2=C1 IUZNJJRTTUBGFY-UHFFFAOYSA-N 0.000 claims description 2
• DEXNZZBGNNYILT-UHFFFAOYSA-N 4-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]butanoic acid Chemical compound C12=CC(OCC=3C=CC=CC=3)=CC=C2N(CCCC(=O)O)C(COC=2C=C3C=CC=CC3=CC=2)=C1C(=O)C1=CC=CC=C1 DEXNZZBGNNYILT-UHFFFAOYSA-N 0.000 claims description 2
• ICFWZFLWNXUVIM-UHFFFAOYSA-N 4-[4-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]butanoylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)CCCN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C=2C=CC=CC=2)=C1COC1=CC=C(C=CC=C2)C2=C1 ICFWZFLWNXUVIM-UHFFFAOYSA-N 0.000 claims description 2
• HCHSFVKTMDUFAW-UHFFFAOYSA-N 4-[5-(cyclopentanecarbonylamino)-2-(naphthalen-2-yloxymethyl)-3-(pyrrolidine-1-carbonyl)indol-1-yl]butanoic acid Chemical compound C12=CC(NC(=O)C3CCCC3)=CC=C2N(CCCC(=O)O)C(COC=2C=C3C=CC=CC3=CC=2)=C1C(=O)N1CCCC1 HCHSFVKTMDUFAW-UHFFFAOYSA-N 0.000 claims description 2
• JRPGINQCHXBODX-UHFFFAOYSA-N 4-[[2-(naphthalen-2-ylsulfanylmethyl)-5-phenylmethoxy-3-(2,2,2-trifluoroacetyl)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C(F)(F)F)=C1CSC1=CC=C(C=CC=C2)C2=C1 JRPGINQCHXBODX-UHFFFAOYSA-N 0.000 claims description 2
• UPAKXIZEBPINMX-UHFFFAOYSA-N 4-[[3-(2-methylpropanoyl)-2-(naphthalen-2-ylsulfanylmethyl)-5-phenylmethoxyindol-1-yl]methyl]benzoic acid Chemical compound C12=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C(C)C)=C(CSC=2C=C3C=CC=CC3=CC=2)N1CC1=CC=C(C(O)=O)C=C1 UPAKXIZEBPINMX-UHFFFAOYSA-N 0.000 claims description 2
• KYQUWARGMDCPDH-UHFFFAOYSA-N 4-[[3-acetyl-2-(naphthalen-2-ylsulfanylmethyl)-5-phenylmethoxyindol-1-yl]methyl]benzoic acid Chemical compound C12=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C)=C(CSC=2C=C3C=CC=CC3=CC=2)N1CC1=CC=C(C(O)=O)C=C1 KYQUWARGMDCPDH-UHFFFAOYSA-N 0.000 claims description 2
• JKQJELDRSIXSBZ-UHFFFAOYSA-N 4-[[3-chloro-2-(naphthalen-2-ylsulfanylmethyl)-5-(3-phenylpropanoylamino)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)CCC=3C=CC=CC=3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 JKQJELDRSIXSBZ-UHFFFAOYSA-N 0.000 claims description 2
• HBOTTWFEEVYQLG-UHFFFAOYSA-N 4-[[3-chloro-2-(naphthalen-2-ylsulfanylmethyl)-5-(oxolane-3-carbonylamino)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C3COCC3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 HBOTTWFEEVYQLG-UHFFFAOYSA-N 0.000 claims description 2
• XRRBNPCLUPEJCB-UHFFFAOYSA-N 4-[[3-chloro-2-(naphthalen-2-ylsulfanylmethyl)-5-(quinoxaline-2-carbonylamino)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C=3N=C4C=CC=CC4=NC=3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 XRRBNPCLUPEJCB-UHFFFAOYSA-N 0.000 claims description 2
• JUULVKDNGIGWNY-UHFFFAOYSA-N 4-[[3-chloro-2-(naphthalen-2-ylsulfanylmethyl)-5-[(3-phenoxyphenyl)methylamino]indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NCC=3C=C(OC=4C=CC=CC=4)C=CC=3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 JUULVKDNGIGWNY-UHFFFAOYSA-N 0.000 claims description 2
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