CA2335062A1 - Coadministration of acat and mmp inhibitors for the treatment of atherosclerotic lesions - Google Patents

Info

Publication number

CA2335062A1

CA2335062A1 CA002335062A CA2335062A CA2335062A1 CA 2335062 A1 CA2335062 A1 CA 2335062A1 CA 002335062 A CA002335062 A CA 002335062A CA 2335062 A CA2335062 A CA 2335062A CA 2335062 A1 CA2335062 A1 CA 2335062A1

Authority

CA

Canada

Prior art keywords

acid

methyl

phenyl

biphenyl

hydroxy

Prior art date

1998-07-21

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

• 229940124761 MMP inhibitor Drugs 0.000 title claims abstract description 24
• 230000003902 lesion Effects 0.000 title claims abstract description 22
• 230000003143 atherosclerotic effect Effects 0.000 title claims abstract description 12
• 241000124008 Mammalia Species 0.000 claims abstract description 9
• 230000002265 prevention Effects 0.000 claims abstract 2
• -1 carboxyalkyl ketone Chemical group 0.000 claims description 239
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 150
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 139
• 150000001408 amides Chemical class 0.000 claims description 118
• 150000001875 compounds Chemical class 0.000 claims description 105
• ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 99
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 97
• 125000000217 alkyl group Chemical group 0.000 claims description 93
• 239000001257 hydrogen Substances 0.000 claims description 77
• 229910052739 hydrogen Inorganic materials 0.000 claims description 77
• 125000004432 carbon atom Chemical group C* 0.000 claims description 73
• 229960003136 leucine Drugs 0.000 claims description 61
• 239000004395 L-leucine Substances 0.000 claims description 55
• 239000002253 acid Substances 0.000 claims description 55
• 229960004050 aminobenzoic acid Drugs 0.000 claims description 42
• 238000000034 method Methods 0.000 claims description 42
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 34
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 29
• 239000003112 inhibitor Substances 0.000 claims description 29
• LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 28
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 27
• WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 27
• FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 27
• GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 26
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
• 239000007983 Tris buffer Substances 0.000 claims description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 18
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
• SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 12
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 125000001424 substituent group Chemical group 0.000 claims description 11
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 11
• 239000005711 Benzoic acid Substances 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 10
• 235000010233 benzoic acid Nutrition 0.000 claims description 9
• 229940080818 propionamide Drugs 0.000 claims description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
• 150000003857 carboxamides Chemical class 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
• 125000004423 acyloxy group Chemical group 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• NOGORDCJKYDQLM-UHFFFAOYSA-N 3-[[3,3-dimethyl-1-(4-methylsulfinylanilino)-1-oxobutan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(S(=O)C)=CC=C1NC(=O)C(C(C)(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 NOGORDCJKYDQLM-UHFFFAOYSA-N 0.000 claims description 5
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• ZHPYMNKKCCXESP-ZIAGYGMSSA-N (1s,2r)-n-hydroxy-2-(2-phenylethylsulfonyl)cyclohexane-1-carboxamide Chemical compound ONC(=O)[C@@H]1CCCC[C@H]1S(=O)(=O)CCC1=CC=CC=C1 ZHPYMNKKCCXESP-ZIAGYGMSSA-N 0.000 claims description 4
• JEXXIZJVIRKSKT-MRVPVSSYSA-N (2r)-1-(pyrrolidine-1-carbonyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCN1C(=O)N1CCCC1 JEXXIZJVIRKSKT-MRVPVSSYSA-N 0.000 claims description 4
• DBCNBHNECRHFCK-INIZCTEOSA-N (2s)-2-[[4-(4-chlorophenoxy)phenyl]sulfonylamino]-3-methyl-3-(methyldisulfanyl)butanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@H](C(C)(C)SSC)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1 DBCNBHNECRHFCK-INIZCTEOSA-N 0.000 claims description 4
• HHTRSYDCDVHFPS-QFIPXVFZSA-N (2s)-3-(benzyldisulfanyl)-3-methyl-2-[(4-phenoxyphenyl)sulfonylamino]butanoic acid Chemical compound CC(C)([C@@H](NS(=O)(=O)C=1C=CC(OC=2C=CC=CC=2)=CC=1)C(O)=O)SSCC1=CC=CC=C1 HHTRSYDCDVHFPS-QFIPXVFZSA-N 0.000 claims description 4
• PJQZHYNPSVMRNI-INIZCTEOSA-N (2s)-3-methyl-3-(methyldisulfanyl)-2-[(4-phenoxyphenyl)sulfonylamino]butanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@H](C(C)(C)SSC)C(O)=O)=CC=C1OC1=CC=CC=C1 PJQZHYNPSVMRNI-INIZCTEOSA-N 0.000 claims description 4
• XWWXRQIQZOTQGF-UHFFFAOYSA-N 1-[2-[2-[4-(2,2-dimethylpropyl)phenyl]ethyl]-4,6-difluorophenyl]-3-heptylurea Chemical compound CCCCCCCNC(=O)NC1=C(F)C=C(F)C=C1CCC1=CC=C(CC(C)(C)C)C=C1 XWWXRQIQZOTQGF-UHFFFAOYSA-N 0.000 claims description 4
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
• RTLSTUZMDWRFGX-UHFFFAOYSA-N 2-[(1-anilino-3-hydroxy-3-methyl-1-oxobutan-2-yl)carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C=1C=CC=CC=1NC(=O)C(C(C)(O)C)NC(=O)C(C(O)=O)CCCCC(C=C1)=CC=C1C1=CC=CC=C1 RTLSTUZMDWRFGX-UHFFFAOYSA-N 0.000 claims description 4
• ZGRCRCCIFTVKPL-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfonylamino]-3-methyl-3-pyridin-2-ylsulfanylbutanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(C(O)=O)C(C)(C)SC1=CC=CC=N1 ZGRCRCCIFTVKPL-UHFFFAOYSA-N 0.000 claims description 4
• JWVUKQIGHDKNEA-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)piperazin-1-yl]sulfonylamino]-3-methyl-3-(pyridin-2-ylmethylsulfanyl)butanoic acid Chemical compound C1CN(C=2C=CC(Cl)=CC=2)CCN1S(=O)(=O)NC(C(O)=O)C(C)(C)SCC1=CC=CC=N1 JWVUKQIGHDKNEA-UHFFFAOYSA-N 0.000 claims description 4
• YEJXHLHPLHPLNS-UHFFFAOYSA-N 3,3-dimethyl-2-[(4-phenoxyphenyl)sulfonylmethyl]butanoic acid Chemical compound C1=CC(S(=O)(=O)CC(C(C)(C)C)C(O)=O)=CC=C1OC1=CC=CC=C1 YEJXHLHPLHPLNS-UHFFFAOYSA-N 0.000 claims description 4
• LJOJZOWQADAXBP-UHFFFAOYSA-N 3-(n-hydroxy-c-methylcarbonimidoyl)-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(CCCC(C(=NO)C)CC(O)=O)=CC=C1C1=CC=CC=C1 LJOJZOWQADAXBP-UHFFFAOYSA-N 0.000 claims description 4
• USNSRBLCMTZOAN-UHFFFAOYSA-N 3-[(1-hydroxy-3,3-dimethylpent-4-en-2-yl)carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(CCCC(C(=O)NC(CO)C(C)(C=C)C)CC(O)=O)=CC=C1C1=CC=CC=C1 USNSRBLCMTZOAN-UHFFFAOYSA-N 0.000 claims description 4
• OHTYCSMUYBUMDB-UHFFFAOYSA-N 3-[(2-hydroxycyclohexyl)carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound OC1CCCCC1NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 OHTYCSMUYBUMDB-UHFFFAOYSA-N 0.000 claims description 4
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 4
• ULBWONLLYBMACQ-UHFFFAOYSA-N 6-(4-phenylphenyl)-3-[[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamoyl]hexanoic acid Chemical compound OC1C(O)C(CO)OC(O)C1NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 ULBWONLLYBMACQ-UHFFFAOYSA-N 0.000 claims description 4
• HCNHIFFZTIRZJA-UHFFFAOYSA-N [3-[2-(2,6-dichlorophenyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=C(Cl)C=CC=C1Cl HCNHIFFZTIRZJA-UHFFFAOYSA-N 0.000 claims description 4
• 239000004202 carbamide Substances 0.000 claims description 4
• 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 4
• ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 4
• SWYZGLWCQFMQJW-UHFFFAOYSA-N phenoxy hypofluorite Chemical compound FOOC1=CC=CC=C1 SWYZGLWCQFMQJW-UHFFFAOYSA-N 0.000 claims description 4
• WRBRQLVAZQIDJJ-LEWJYISDSA-N (1r,2s)-2-[3-(4-phenylphenyl)propyl]cyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@H]1CCCC1=CC=C(C=2C=CC=CC=2)C=C1 WRBRQLVAZQIDJJ-LEWJYISDSA-N 0.000 claims description 3
• ZTURSOCJWSWDIF-UHFFFAOYSA-N 2-[[3,3-dimethyl-1-oxo-1-(pyridin-4-ylamino)butan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C=1C=NC=CC=1NC(=O)C(C(C)(C)C)NC(=O)C(C(O)=O)CCCCC(C=C1)=CC=C1C1=CC=CC=C1 ZTURSOCJWSWDIF-UHFFFAOYSA-N 0.000 claims description 3
• SEINETSKRAZANU-UHFFFAOYSA-N 2-methylsulfanyl-1h-indole Chemical compound C1=CC=C2NC(SC)=CC2=C1 SEINETSKRAZANU-UHFFFAOYSA-N 0.000 claims description 3
• ONNLYKOACNWWLT-UHFFFAOYSA-N 3,3-dimethyl-2-[(4-phenoxyphenyl)sulfanylmethyl]butanoic acid Chemical compound C1=CC(SCC(C(C)(C)C)C(O)=O)=CC=C1OC1=CC=CC=C1 ONNLYKOACNWWLT-UHFFFAOYSA-N 0.000 claims description 3
• IGJNBEBJECPONG-UHFFFAOYSA-N 4-[(1-methoxy-3-phenylpropan-2-yl)amino]-4-oxo-3-[3-(4-phenylphenyl)pyrrol-1-yl]butanoic acid Chemical compound C1=CC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=CN1C(CC(O)=O)C(=O)NC(COC)CC1=CC=CC=C1 IGJNBEBJECPONG-UHFFFAOYSA-N 0.000 claims description 3
• RQJMLGGTENDEFM-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-4-hydroxyiminobutanoic acid Chemical compound C1=CC(C(CCC(O)=O)=NO)=CC=C1C1=CC=C(Cl)C=C1 RQJMLGGTENDEFM-UHFFFAOYSA-N 0.000 claims description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
• 125000005518 carboxamido group Chemical group 0.000 claims description 3
• NPQWVLZCVMVSEX-UHFFFAOYSA-N n-[2,6-di(propan-2-yl)phenyl]-2-(2-dodecyltetrazol-5-yl)-2-phenylacetamide Chemical compound CCCCCCCCCCCCN1N=NC(C(C(=O)NC=2C(=CC=CC=2C(C)C)C(C)C)C=2C=CC=CC=2)=N1 NPQWVLZCVMVSEX-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000005544 phthalimido group Chemical group 0.000 claims description 3
• 239000011734 sodium Chemical class 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 239000012453 solvate Substances 0.000 claims description 3
• NNCXNAFAXHTBHL-RTBURBONSA-N (1S,2R)-2-[(4-phenylphenyl)methylsulfanyl]cyclohexane-1-carboxylic acid Chemical compound C1(=CC=C(C=C1)CS[C@H]1[C@@H](CCCC1)C(=O)O)C1=CC=CC=C1 NNCXNAFAXHTBHL-RTBURBONSA-N 0.000 claims description 2
• TUBMCKKTQQWJAN-CHWSQXEVSA-N (1S,2R)-2-benzylsulfanylcyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@H]1SCC1=CC=CC=C1 TUBMCKKTQQWJAN-CHWSQXEVSA-N 0.000 claims description 2
• JHQZXTYFJRLVEA-HXUWFJFHSA-N (2R)-2-hexyl-N-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]decanamide Chemical compound CC1=CC(=C(C(=N1)SC)NC([C@@H](CCCCCCCC)CCCCCC)=O)SC JHQZXTYFJRLVEA-HXUWFJFHSA-N 0.000 claims description 2
• YPJGAHQLXBJPAC-AWEZNQCLSA-N (2R)-3,3-dimethyl-2-[(4-pyridin-4-ylsulfanylpiperidin-1-yl)sulfonylamino]butanoic acid Chemical compound CC([C@H](C(=O)O)NS(=O)(=O)N1CCC(CC1)SC1=CC=NC=C1)(C)C YPJGAHQLXBJPAC-AWEZNQCLSA-N 0.000 claims description 2
• IKWXAXUODLNDFO-UNTBIKODSA-N (2r)-1-[4-(4-chlorophenyl)phenyl]sulfonyl-n-hydroxy-4-methylpiperazine-2-carboxamide;hydrochloride Chemical compound Cl.ONC(=O)[C@H]1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 IKWXAXUODLNDFO-UNTBIKODSA-N 0.000 claims description 2
• NPCDMLATOSDHFZ-GFCCVEGCSA-N (2r)-2-n-hydroxy-1-n-(2-phenylethyl)pyrrolidine-1,2-dicarboxamide Chemical compound ONC(=O)[C@H]1CCCN1C(=O)NCCC1=CC=CC=C1 NPCDMLATOSDHFZ-GFCCVEGCSA-N 0.000 claims description 2
• UVINDFAMLDFNEB-INIZCTEOSA-N (2r)-3,3-dimethyl-2-[(4-phenoxyphenyl)sulfonylamino]butanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@H](C(C)(C)C)C(O)=O)=CC=C1OC1=CC=CC=C1 UVINDFAMLDFNEB-INIZCTEOSA-N 0.000 claims description 2
• AKSCVVBLDIFJEW-IEBWSBKVSA-N (2r)-n'-hydroxy-n-[(1s)-2-hydroxy-1-(1h-imidazol-5-yl)ethyl]-2-[3-[4-(2-methyl-1,3-thiazol-4-yl)phenyl]propyl]butanediamide Chemical compound S1C(C)=NC(C=2C=CC(CCC[C@H](CC(=O)NO)C(=O)N[C@H](CO)C=3NC=NC=3)=CC=2)=C1 AKSCVVBLDIFJEW-IEBWSBKVSA-N 0.000 claims description 2
• UAOXFYYXEDABIZ-CLJLJLNGSA-N (2r)-n'-hydroxy-n-[(2r)-1-hydroxy-3-phenylpropan-2-yl]-2-[3-(4-phenylphenyl)propyl]butanediamide Chemical compound C([C@H](CO)NC(=O)[C@H](CCCC=1C=CC(=CC=1)C=1C=CC=CC=1)CC(=O)NO)C1=CC=CC=C1 UAOXFYYXEDABIZ-CLJLJLNGSA-N 0.000 claims description 2
• IQSGYEHAZRRXEX-RPBOFIJWSA-N (2r)-n'-hydroxy-n-[(2s)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]-2-[3-(4-phenylphenyl)propyl]butanediamide Chemical compound C([C@@H](CO)NC(=O)[C@H](CCCC=1C=CC(=CC=1)C=1C=CC=CC=1)CC(=O)NO)C1=CC=C(O)C=C1 IQSGYEHAZRRXEX-RPBOFIJWSA-N 0.000 claims description 2
• VYZHCUXKDWUJHA-RPBOFIJWSA-N (2r)-n'-hydroxy-n-[(2s)-1-hydroxy-3-pyridin-3-ylpropan-2-yl]-2-[3-(4-phenylphenyl)propyl]butanediamide Chemical compound C([C@@H](CO)NC(=O)[C@H](CCCC=1C=CC(=CC=1)C=1C=CC=CC=1)CC(=O)NO)C1=CC=CN=C1 VYZHCUXKDWUJHA-RPBOFIJWSA-N 0.000 claims description 2
• BYFVHNCQZSTKEH-AWEZNQCLSA-N (2r)-n-hydroxy-3,3-dimethyl-2-[(4-pyridin-4-ylsulfanylpiperidin-1-yl)sulfonylamino]butanamide Chemical compound C1CN(S(=O)(=O)N[C@H](C(C)(C)C)C(=O)NO)CCC1SC1=CC=NC=C1 BYFVHNCQZSTKEH-AWEZNQCLSA-N 0.000 claims description 2
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• KSTVSSYIAVSGAV-UHFFFAOYSA-N 3-[[1-cyclohexyl-2-[4-(2-hydroxyethylsulfamoyl)anilino]-2-oxoethyl]carbamoyl]-6-(4-pyridin-4-ylphenyl)hexanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(S(=O)(=O)NCCO)=CC=C1NC(=O)C(C1CCCCC1)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CN=CC=2)C=C1 KSTVSSYIAVSGAV-UHFFFAOYSA-N 0.000 claims description 2
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• JVYVYZMOQQLDBV-UHFFFAOYSA-N 3-[[3,3-dimethyl-1-(4-methylsulfonylanilino)-1-oxobutan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1NC(=O)C(C(C)(C)C)NC(=O)C(CC(O)=O)CCCC(C=C1)=CC=C1C1=CC=CC=C1 JVYVYZMOQQLDBV-UHFFFAOYSA-N 0.000 claims description 2
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• ZJSROEUUDDBKPW-UHFFFAOYSA-N 3-[[3,3-dimethyl-1-oxo-1-(pyridin-4-ylamino)butan-2-yl]carbamoyl]-2-hydroxy-5-methylhexanoic acid;hydrochloride Chemical compound Cl.CC(C)CC(C(O)C(O)=O)C(=O)NC(C(C)(C)C)C(=O)NC1=CC=NC=C1 ZJSROEUUDDBKPW-UHFFFAOYSA-N 0.000 claims description 2
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• MPNLGFCXEMPAGR-UHFFFAOYSA-N 6-(1-cyano-4-phenylcyclohexa-2,4-dien-1-yl)-3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]hexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCCC1(C#N)C=CC(C=2C=CC=CC=2)=CC1 MPNLGFCXEMPAGR-UHFFFAOYSA-N 0.000 claims description 2
• SKZYSUFOIITPHQ-UHFFFAOYSA-N 6-(3-fluoro-4-phenylphenyl)-3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]hexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C(F)=C1 SKZYSUFOIITPHQ-UHFFFAOYSA-N 0.000 claims description 2
• WIPAOMRNVZRQFV-UHFFFAOYSA-N 6-[4-(2-hydroxyethyl)phenyl]-3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]hexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(CCO)C=C1 WIPAOMRNVZRQFV-UHFFFAOYSA-N 0.000 claims description 2
• DMNLLHTZUSQGJR-UHFFFAOYSA-N 6-[4-(4-cyanophenyl)phenyl]-3-[[3-hydroxy-1-(4-methylsulfinylanilino)-1-oxobutan-2-yl]carbamoyl]hexanoic acid Chemical compound C=1C=C(S(C)=O)C=CC=1NC(=O)C(C(O)C)NC(=O)C(CC(O)=O)CCCC(C=C1)=CC=C1C1=CC=C(C#N)C=C1 DMNLLHTZUSQGJR-UHFFFAOYSA-N 0.000 claims description 2
• LJLAQHLSIQILJL-UHFFFAOYSA-N 6-[4-(4-hydroxyphenyl)phenyl]-3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]hexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC(O)=CC=2)C=C1 LJLAQHLSIQILJL-UHFFFAOYSA-N 0.000 claims description 2
• BCQICVFLSKNNQR-UHFFFAOYSA-N 6-benzylsulfonyl-n-hydroxycyclohexene-1-carboxamide Chemical compound ONC(=O)C1=CCCCC1S(=O)(=O)CC1=CC=CC=C1 BCQICVFLSKNNQR-UHFFFAOYSA-N 0.000 claims description 2
• QEJHMHDPCMFHCO-UHFFFAOYSA-N 6-cyclohexyl-6,7-dihydro-4-(2-oxo-2-phenylethyl)-2-(4-chlorophenyl)-4h-pyrazolo[1,5-a]pyrrolo[3,4-d]-pyrimidine-5,8-dione Chemical compound C1=CC(Cl)=CC=C1C1=NN2C(=O)C(CN(C3=O)C4CCCCC4)=C3N(CC(=O)C=3C=CC=CC=3)C2=C1 QEJHMHDPCMFHCO-UHFFFAOYSA-N 0.000 claims description 2
• AKJOLGWKEMOCMJ-UHFFFAOYSA-N 6-oxo-3-(4-phenoxyphenyl)sulfonyl-1,3-diazinane-4-carboxylic acid Chemical compound OC(=O)C1CC(=O)NCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 AKJOLGWKEMOCMJ-UHFFFAOYSA-N 0.000 claims description 2
• KIEGTROBAZLMEL-UHFFFAOYSA-N 8-[(3,4,5-triphenyl-1,2-dihydroimidazol-2-yl)oxy]octanoic acid Chemical compound OC(=O)CCCCCCCOC1NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1C1=CC=CC=C1 KIEGTROBAZLMEL-UHFFFAOYSA-N 0.000 claims description 2
• AOBUQUZGNPFVLB-UHFFFAOYSA-N 9-bromo-n-[2,6-di(propan-2-yl)phenyl]-6,11-dihydrobenzo[c][1]benzoxepine-11-carboxamide Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)C1C2=CC(Br)=CC=C2COC2=CC=CC=C21 AOBUQUZGNPFVLB-UHFFFAOYSA-N 0.000 claims description 2
• ZCUKZKQKQZXCLV-UHFFFAOYSA-N C1CCC(C(=O)O)=C1S(=O)(=O)CC1=CC=CC=C1 Chemical compound C1CCC(C(=O)O)=C1S(=O)(=O)CC1=CC=CC=C1 ZCUKZKQKQZXCLV-UHFFFAOYSA-N 0.000 claims description 2
• LDRJOJGGXOIOAY-UHFFFAOYSA-N CCCCCCCCC=CCCCCCCCC(NCCNC(CCN)=O)=O Chemical compound CCCCCCCCC=CCCCCCCCC(NCCNC(CCN)=O)=O LDRJOJGGXOIOAY-UHFFFAOYSA-N 0.000 claims description 2
• GXCSIMGMNYLKHL-UHFFFAOYSA-N COC(C1=CC=C(C=C1)NC(C(CC(C)C)NC(C(CCCC1=CC=C(C(=C1)O)C1=CC=CC=C1)CC(=O)O)=O)=O)=O Chemical compound COC(C1=CC=C(C=C1)NC(C(CC(C)C)NC(C(CCCC1=CC=C(C(=C1)O)C1=CC=CC=C1)CC(=O)O)=O)=O)=O GXCSIMGMNYLKHL-UHFFFAOYSA-N 0.000 claims description 2
• LAQUQCXKTJTSJX-UHFFFAOYSA-N COC1=CC=C(C=C1)NS(=O)(=O)C1CCN(CC1)S(=O)(=O)N1C(CCCC1)C(=O)O Chemical compound COC1=CC=C(C=C1)NS(=O)(=O)C1CCN(CC1)S(=O)(=O)N1C(CCCC1)C(=O)O LAQUQCXKTJTSJX-UHFFFAOYSA-N 0.000 claims description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
• NFVNYBJCJGKVQK-ZDUSSCGKSA-N N-[(Tert-butoxy)carbonyl]-L-tryptophan Chemical compound C1=CC=C2C(C[C@H](NC(=O)OC(C)(C)C)C(O)=O)=CNC2=C1 NFVNYBJCJGKVQK-ZDUSSCGKSA-N 0.000 claims description 2
• STCJOSRMUFDMGF-UHFFFAOYSA-N OC(=O)C1CCCCC1S(=O)(=O)CCCC1=CC=CC=C1 Chemical compound OC(=O)C1CCCCC1S(=O)(=O)CCCC1=CC=CC=C1 STCJOSRMUFDMGF-UHFFFAOYSA-N 0.000 claims description 2
• XSHIZJRVFDYQLE-UHFFFAOYSA-N OC(=O)C1CCCCC1SCC1=CC=C(N2C3=CC=CC=C3C=C2)C=C1 Chemical compound OC(=O)C1CCCCC1SCC1=CC=C(N2C3=CC=CC=C3C=C2)C=C1 XSHIZJRVFDYQLE-UHFFFAOYSA-N 0.000 claims description 2
• PHNDDUIJWBIKFY-RTBURBONSA-N OC(=O)[C@@H]1CCCC[C@H]1SCC(C=C1)=CC=C1OC1=CC=CC=C1 Chemical compound OC(=O)[C@@H]1CCCC[C@H]1SCC(C=C1)=CC=C1OC1=CC=CC=C1 PHNDDUIJWBIKFY-RTBURBONSA-N 0.000 claims description 2
• PCVSBMWYSWVMGR-UHFFFAOYSA-N OC1=CC=CC=C1OF Chemical compound OC1=CC=CC=C1OF PCVSBMWYSWVMGR-UHFFFAOYSA-N 0.000 claims description 2
• RPFCHZANSTXMQB-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-(2,2,2-triphenylacetyl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RPFCHZANSTXMQB-UHFFFAOYSA-N 0.000 claims description 2
• NVCAXWLFXNFPRF-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-(2-thiophen-2-ylacetyl)phenyl] sulfamate Chemical compound S1C(=CC=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C NVCAXWLFXNFPRF-UHFFFAOYSA-N 0.000 claims description 2
• RNYUYZOQGFPICG-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-(2,4,6-trimethoxyphenyl)acetyl]phenyl] sulfamate Chemical compound COC1=CC(OC)=CC(OC)=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C RNYUYZOQGFPICG-UHFFFAOYSA-N 0.000 claims description 2
• LXSBEGRJNHLGJI-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-(2,4,6-trimethylphenyl)acetyl]phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=C(C)C=C(C)C=C1C LXSBEGRJNHLGJI-UHFFFAOYSA-N 0.000 claims description 2
• FFHDHZYMGPGQLF-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-[2,4,6-tri(propan-2-yl)phenoxy]acetyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1OCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C FFHDHZYMGPGQLF-UHFFFAOYSA-N 0.000 claims description 2
• PZVXVEZHFRHQHE-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-[2-(trifluoromethyl)phenyl]acetyl]phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=CC=CC=C1C(F)(F)F PZVXVEZHFRHQHE-UHFFFAOYSA-N 0.000 claims description 2
• JXIWGHCSLXAJLL-UHFFFAOYSA-N [3-(2,2-diphenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JXIWGHCSLXAJLL-UHFFFAOYSA-N 0.000 claims description 2
• TVZUKCLORBYVAB-UHFFFAOYSA-N [3-(2-cyclohexylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1CCCCC1 TVZUKCLORBYVAB-UHFFFAOYSA-N 0.000 claims description 2
• MWMRVLOOUQKYSS-UHFFFAOYSA-N [3-(2-oxo-2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(=O)C1=CC=CC=C1 MWMRVLOOUQKYSS-UHFFFAOYSA-N 0.000 claims description 2
• LVUYWXXLGSVQEH-UHFFFAOYSA-N [3-(2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=CC=CC=C1 LVUYWXXLGSVQEH-UHFFFAOYSA-N 0.000 claims description 2
• WERGUDHVRRAQIA-UHFFFAOYSA-N [3-(2-phenylbutanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound C=1C=CC=CC=1C(CC)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C WERGUDHVRRAQIA-UHFFFAOYSA-N 0.000 claims description 2
• ONKLECGKWMBEJQ-UHFFFAOYSA-N [3-(2-phenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C)C1=CC=CC=C1 ONKLECGKWMBEJQ-UHFFFAOYSA-N 0.000 claims description 2
• WUHZAAZJJIQGBP-UHFFFAOYSA-N [3-(3,3-diphenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 WUHZAAZJJIQGBP-UHFFFAOYSA-N 0.000 claims description 2
• BKIZTHMHKWZOPD-UHFFFAOYSA-N [3-(3-methyl-2-phenylpentanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate;sodium Chemical compound [Na].C=1C=CC=CC=1C(C(C)CC)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C BKIZTHMHKWZOPD-UHFFFAOYSA-N 0.000 claims description 2
• YKPBDXIXQLCDMW-UHFFFAOYSA-N [3-(3-phenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CCC1=CC=CC=C1 YKPBDXIXQLCDMW-UHFFFAOYSA-N 0.000 claims description 2
• IEUKVMHUFHMJNZ-UHFFFAOYSA-N [3-(9h-fluorene-9-carbonyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C1C2=CC=CC=C2C2=CC=CC=C21 IEUKVMHUFHMJNZ-UHFFFAOYSA-N 0.000 claims description 2
• VUKGWEPYJTUIFU-UHFFFAOYSA-N [3-[2-(2,5-dimethoxyphenyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound COC1=CC=C(OC)C(CC(=O)C=2C(=C(OS(N)(=O)=O)C(C(C)C)=CC=2)C(C)C)=C1 VUKGWEPYJTUIFU-UHFFFAOYSA-N 0.000 claims description 2
• VWMCJIVWYXESEB-UHFFFAOYSA-N [3-[2-(2-methoxyphenyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound COC1=CC=CC=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C VWMCJIVWYXESEB-UHFFFAOYSA-N 0.000 claims description 2
• ODLHXSJZGOAYGM-UHFFFAOYSA-N [3-[2-[2,6-di(propan-2-yl)phenyl]acetyl]-2,4,6-tri(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1CC(=O)C1=C(C(C)C)C=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C ODLHXSJZGOAYGM-UHFFFAOYSA-N 0.000 claims description 2
• DXHYZVZSMDLNBQ-UHFFFAOYSA-N [3-decanoyl-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CCCCCCCCCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C DXHYZVZSMDLNBQ-UHFFFAOYSA-N 0.000 claims description 2
• SDKIUQCUWFKCBF-UHFFFAOYSA-N [3-dodecanoyl-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CCCCCCCCCCCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C SDKIUQCUWFKCBF-UHFFFAOYSA-N 0.000 claims description 2
• MTMLWLQNGIFHLK-UHFFFAOYSA-N [O-]C(CC(CCCC(C=C1)=CC=C1C1=CC=CC=C1)C(NC(C1CCCCC1)C(NCCC(C=C1)=CC=C1[S+]=O)=O)=O)=O Chemical compound [O-]C(CC(CCCC(C=C1)=CC=C1C1=CC=CC=C1)C(NC(C1CCCCC1)C(NCCC(C=C1)=CC=C1[S+]=O)=O)=O)=O MTMLWLQNGIFHLK-UHFFFAOYSA-N 0.000 claims description 2
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
• ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 2
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
• WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 claims description 2
• NOKQIUPXQUBSNO-UHFFFAOYSA-N dioxane-4-carboxylic acid Chemical compound OC(=O)C1CCOOC1 NOKQIUPXQUBSNO-UHFFFAOYSA-N 0.000 claims description 2
• TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 claims description 2
• KYRMDXAOVIMEEV-UHFFFAOYSA-N ethyl 2,2-dimethyl-5-[[3-(1-methylimidazol-2-yl)-2-propyl-3,4-dihydro-2h-chromen-6-yl]oxy]pentanoate Chemical compound CCCC1OC2=CC=C(OCCCC(C)(C)C(=O)OCC)C=C2CC1C1=NC=CN1C KYRMDXAOVIMEEV-UHFFFAOYSA-N 0.000 claims description 2
• WWNMZAVNIGAIGP-FSRHSHDFSA-N ethyl 2-[(3r)-4-[4-(4-chlorophenyl)phenyl]sulfonyl-3-(hydroxycarbamoyl)piperazin-1-yl]acetate;hydrochloride Chemical compound Cl.ONC(=O)[C@H]1CN(CC(=O)OCC)CCN1S(=O)(=O)C1=CC=C(C=2C=CC(Cl)=CC=2)C=C1 WWNMZAVNIGAIGP-FSRHSHDFSA-N 0.000 claims description 2
• LCMBCJFAKQBFGZ-UHFFFAOYSA-N ethyl 3-(1h-indol-3-yl)-2-(octadec-9-enoylamino)propanoate Chemical compound C1=CC=C2C(CC(NC(=O)CCCCCCCC=CCCCCCCCC)C(=O)OCC)=CNC2=C1 LCMBCJFAKQBFGZ-UHFFFAOYSA-N 0.000 claims description 2
• PSQWWHGMMWFQLX-UHFFFAOYSA-N ethyl 3-[[3,3-dimethyl-1-oxo-1-(pyridin-4-ylamino)butan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoate Chemical compound C=1C=NC=CC=1NC(=O)C(C(C)(C)C)NC(=O)C(CC(=O)OCC)CCCC(C=C1)=CC=C1C1=CC=CC=C1 PSQWWHGMMWFQLX-UHFFFAOYSA-N 0.000 claims description 2
• YABYZOPDZUVCSZ-UHFFFAOYSA-N methyl 4-[[2-[2-[2-(hydroxyamino)-2-oxoethyl]hexanoylamino]-3,3-dimethylbutanoyl]amino]benzoate Chemical compound CCCCC(CC(=O)NO)C(=O)NC(C(C)(C)C)C(=O)NC1=CC=C(C(=O)OC)C=C1 YABYZOPDZUVCSZ-UHFFFAOYSA-N 0.000 claims description 2
• BLGRCSGSFJERDA-UHFFFAOYSA-N methyl 4-[[2-[[(2e)-2-(hydroxyamino)-2-hydroxyiminoethyl]-(5-phenylpentanoyl)amino]-4-methylpentanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)N(CC(NO)=NO)C(=O)CCCCC1=CC=CC=C1 BLGRCSGSFJERDA-UHFFFAOYSA-N 0.000 claims description 2
• CEEASCNCHQSPKF-UHFFFAOYSA-N methyl 4-[[2-[[2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]benzoate Chemical compound COC(=O)C1=CC=C(NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)CC(=O)NO)C=C1 CEEASCNCHQSPKF-UHFFFAOYSA-N 0.000 claims description 2
• DNZJQDQGZOQHMP-UHFFFAOYSA-N methyl 4-[[2-[[2-[2-(hydroxyamino)-2-oxoethyl]-5-phenylpentanoyl]amino]-3,3-dimethylbutanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(C(C)(C)C)NC(=O)C(CC(=O)NO)CCCC1=CC=CC=C1 DNZJQDQGZOQHMP-UHFFFAOYSA-N 0.000 claims description 2
• PYBCJEOMAMTGDX-UHFFFAOYSA-N methyl 4-[[2-[[4-(hydroxyamino)-4-oxo-2-(2-phenylethyl)butanoyl]amino]-3,3-dimethylbutanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(C(C)(C)C)NC(=O)C(CC(=O)NO)CCC1=CC=CC=C1 PYBCJEOMAMTGDX-UHFFFAOYSA-N 0.000 claims description 2
• BHRJVWMRWKSKJS-UHFFFAOYSA-N methyl 4-[[2-[[4-(hydroxyamino)-4-oxo-2-phenylbutanoyl]amino]-4-methylpentanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(=O)NO)C1=CC=CC=C1 BHRJVWMRWKSKJS-UHFFFAOYSA-N 0.000 claims description 2
• STLVBUGEIQZAIO-UHFFFAOYSA-N methyl 4-[[2-cyclohexyl-2-[[2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoyl]amino]acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(NC(=O)C(CC(C)C)CC(=O)NO)C1CCCCC1 STLVBUGEIQZAIO-UHFFFAOYSA-N 0.000 claims description 2
• ROMCQIJIIDOULE-UHFFFAOYSA-N methyl 4-[[3-cyclohexyl-2-[[4-(hydroxyamino)-4-oxo-2-(2-phenylethyl)butyl]amino]propanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(NCC(CCC=1C=CC=CC=1)CC(=O)NO)CC1CCCCC1 ROMCQIJIIDOULE-UHFFFAOYSA-N 0.000 claims description 2
• WWRYTZUACREEON-UHFFFAOYSA-N methyl 4-[[3-cyclohexyl-2-[[4-(methoxyamino)-4-oxo-2-(2-phenylethyl)butyl]amino]propanoyl]amino]benzoate Chemical compound C1CCCCC1CC(C(=O)NC=1C=CC(=CC=1)C(=O)OC)NCC(CC(=O)NOC)CCC1=CC=CC=C1 WWRYTZUACREEON-UHFFFAOYSA-N 0.000 claims description 2
• DNHXPMMDJPFECJ-UHFFFAOYSA-N methyl 4-[[4-methyl-2-[[2-(nitromethyl)-5-phenylpentanoyl]amino]pentanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(C[N+]([O-])=O)CCCC1=CC=CC=C1 DNHXPMMDJPFECJ-UHFFFAOYSA-N 0.000 claims description 2
• OBJGVLPPCPARKH-UHFFFAOYSA-N methyl benzoate;methyl 4-[[2-cyclohexyl-2-[[4-(hydroxyamino)-4-oxo-2-(2-phenylethyl)butanoyl]amino]propanoyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1.C1=CC(C(=O)OC)=CC=C1NC(=O)C(C)(C1CCCCC1)NC(=O)C(CC(=O)NO)CCC1=CC=CC=C1 OBJGVLPPCPARKH-UHFFFAOYSA-N 0.000 claims description 2
• QAONMLVMLRPZSF-UHFFFAOYSA-N n'-hydroxy-2-[3-(4-phenylphenyl)propyl]-n-[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]butanediamide Chemical compound OC1C(O)C(CO)OC(O)C1NC(=O)C(CC(=O)NO)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 QAONMLVMLRPZSF-UHFFFAOYSA-N 0.000 claims description 2
• RWIUTHWKQHRQNP-UHFFFAOYSA-N n-(1-phenylethyl)octadeca-9,12-dienamide Chemical compound CCCCCC=CCC=CCCCCCCCC(=O)NC(C)C1=CC=CC=C1 RWIUTHWKQHRQNP-UHFFFAOYSA-N 0.000 claims description 2
• NRVHVSGGSGHTET-UHFFFAOYSA-N n-(2-phenylethyl)pyrrolidine-1-carbothioamide Chemical compound C1CCCN1C(=S)NCCC1=CC=CC=C1 NRVHVSGGSGHTET-UHFFFAOYSA-N 0.000 claims description 2
• DJBINNZKEHJIFK-UHFFFAOYSA-N n-(7-methoxy-4-oxo-2,3-dihydrochromen-8-yl)-2,2-dimethyldodecanamide Chemical compound O=C1CCOC2=C1C=CC(OC)=C2NC(=O)C(C)(C)CCCCCCCCCC DJBINNZKEHJIFK-UHFFFAOYSA-N 0.000 claims description 2
• SVGMOTIWBWNDFP-UHFFFAOYSA-N n-[2,6-di(propan-2-yl)phenyl]-2-octadecylsulfanylacetamide Chemical compound CCCCCCCCCCCCCCCCCCSCC(=O)NC1=C(C(C)C)C=CC=C1C(C)C SVGMOTIWBWNDFP-UHFFFAOYSA-N 0.000 claims description 2
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• DJXOOIAJQBERCP-UHFFFAOYSA-N 10-hydroxy-2,4a,6a,6b,9,10,12a-heptamethyl-4-octadecanoyloxy-1,3,4,5,6,6a,7,8,8a,9,11,12,13,14b-tetradecahydropicene-2-carboxylic acid Chemical compound CC12CCC(C)(O)C(C)C1CCC1(C)C2CC=C2C3CC(C)(C(O)=O)CC(OC(=O)CCCCCCCCCCCCCCCCC)C3(C)CCC21C DJXOOIAJQBERCP-UHFFFAOYSA-N 0.000 claims 1
• SVISWFVZGCSHEK-UHFFFAOYSA-N 2-[2,6-di(propan-2-yl)phenyl]-n-[[2,4,6-tri(propan-2-yl)phenyl]methylsulfonyl]acetamide Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CS(=O)(=O)NC(=O)CC1=C(C(C)C)C=CC=C1C(C)C SVISWFVZGCSHEK-UHFFFAOYSA-N 0.000 claims 1
• HTXOMGOYYMVLJD-UHFFFAOYSA-N 2-[2-(4-phenylphenyl)ethylsulfonyl]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1S(=O)(=O)CCC1=CC=C(C=2C=CC=CC=2)C=C1 HTXOMGOYYMVLJD-UHFFFAOYSA-N 0.000 claims 1
• XQQOUMBOSZHSLD-UHFFFAOYSA-N 2-[3-(1H-imidazol-5-yl)propyl]-N,N'-diphenylbutanediamide Chemical compound N1=CNC(=C1)CCCC(C(=O)NC1=CC=CC=C1)CC(=O)NC1=CC=CC=C1 XQQOUMBOSZHSLD-UHFFFAOYSA-N 0.000 claims 1
• JUGFTJPDPBDGSN-UHFFFAOYSA-N 2-[3-(3-naphthalen-2-ylpropyl)-2-oxooxolan-3-yl]acetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCCC1(CC(=O)O)CCOC1=O JUGFTJPDPBDGSN-UHFFFAOYSA-N 0.000 claims 1
• YDVKMNFOYQTQPX-UHFFFAOYSA-N 2-[3-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-4-(hydroxyamino)-2-methyl-4-oxobutan-2-yl]sulfanylacetic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)(SCC(O)=O)C)C(=O)NO)=CC=C1OC1=CC=C(F)C=C1 YDVKMNFOYQTQPX-UHFFFAOYSA-N 0.000 claims 1
• AGFJCEJGMPYKNC-UHFFFAOYSA-N 2-[[4-(2-fluorophenoxy)phenyl]sulfonylamino]-3,3-dimethylpent-4-enoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)(C=C)C)C(O)=O)=CC=C1OC1=CC=CC=C1F AGFJCEJGMPYKNC-UHFFFAOYSA-N 0.000 claims 1
• GJOCABIDMCKCEG-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)C)C(O)=O)=CC=C1C1=CC=C(Br)C=C1 GJOCABIDMCKCEG-UHFFFAOYSA-N 0.000 claims 1
• GWVWSQZTMVSSAQ-UHFFFAOYSA-N 2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-3-(2-hydroxyethylsulfanyl)-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)(SCCO)C)C(O)=O)=CC=C1OC1=CC=C(F)C=C1 GWVWSQZTMVSSAQ-UHFFFAOYSA-N 0.000 claims 1
• ZGWIOFHKEXLJPC-UHFFFAOYSA-N 2-[[4-(4-formylphenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)C)C(O)=O)=CC=C1C1=CC=C(C=O)C=C1 ZGWIOFHKEXLJPC-UHFFFAOYSA-N 0.000 claims 1
• QTBORBZHZRFVQM-UHFFFAOYSA-N 2-[[4-[4-(aminomethyl)phenyl]phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)C)C(O)=O)=CC=C1C1=CC=C(CN)C=C1 QTBORBZHZRFVQM-UHFFFAOYSA-N 0.000 claims 1
• WOIAZYSLWSXKKC-UHFFFAOYSA-N 2-[[4-[4-(hydroxymethyl)phenyl]phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)C)C(O)=O)=CC=C1C1=CC=C(CO)C=C1 WOIAZYSLWSXKKC-UHFFFAOYSA-N 0.000 claims 1
• AJLGIHBSQSODDV-UHFFFAOYSA-N 2-bromo-n-[2,6-di(propan-2-yl)phenyl]-6,11-dihydrobenzo[c][1]benzoxepine-11-carboxamide Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)C1C2=CC(Br)=CC=C2OCC2=CC=CC=C21 AJLGIHBSQSODDV-UHFFFAOYSA-N 0.000 claims 1
• IRHDUXDAKHYVPR-UHFFFAOYSA-N 3,3-dimethyl-2-[(4-pyridin-2-yloxyphenyl)sulfonylamino]butanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)(C)C)C(O)=O)=CC=C1OC1=CC=CC=N1 IRHDUXDAKHYVPR-UHFFFAOYSA-N 0.000 claims 1
• PRXAQPXGLRHKDN-UHFFFAOYSA-N 3,5-dimethyl-1-[5-[(3,4,5-triphenyl-1,2-dihydroimidazol-2-yl)sulfanyl]pentyl]pyrazole;sodium Chemical compound [Na].N1=C(C)C=C(C)N1CCCCCSC1N(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 PRXAQPXGLRHKDN-UHFFFAOYSA-N 0.000 claims 1
• BNEXCNMQQJDYHH-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-octyl-1-(2,3,4,5-tetrahydro-1-benzoxepin-5-yl)urea Chemical compound C1CCOC2=CC=CC=C2C1N(CCCCCCCC)C(=O)NC1=CC=C(F)C=C1F BNEXCNMQQJDYHH-UHFFFAOYSA-N 0.000 claims 1
• JUSUSTOFLQVKPM-UHFFFAOYSA-N 3-[(4,5-diphenyl-1h-imidazol-2-yl)sulfanylmethyl]-1-methylpiperidine Chemical compound C1N(C)CCCC1CSC1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 JUSUSTOFLQVKPM-UHFFFAOYSA-N 0.000 claims 1
• SAIXUIBHQBOBSO-UHFFFAOYSA-N 3-[1-[4-(4-cyanophenyl)phenyl]pyrrol-3-yl]-4-[[1-(1h-imidazol-2-yl)-3-methylbutyl]amino]-4-oxobutanoic acid Chemical compound N=1C=CNC=1C(CC(C)C)NC(=O)C(CC(O)=O)C(=C1)C=CN1C(C=C1)=CC=C1C1=CC=C(C#N)C=C1 SAIXUIBHQBOBSO-UHFFFAOYSA-N 0.000 claims 1
• FUTRWPCKBFESIA-UHFFFAOYSA-N 3-[3-[4-(4-carbamoylphenyl)phenyl]pyrrol-1-yl]-4-[(1-hydroxy-3-phenylpropan-2-yl)amino]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=C(C2=CN(C=C2)C(CC(O)=O)C(=O)NC(CO)CC=2C=CC=CC=2)C=C1 FUTRWPCKBFESIA-UHFFFAOYSA-N 0.000 claims 1
• XHVRIXLTCMRTFP-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]-6-[4-(2h-tetrazol-5-yl)phenyl]hexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C2=NNN=N2)C=C1 XHVRIXLTCMRTFP-UHFFFAOYSA-N 0.000 claims 1
• GWKVUDAJIWDWIM-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]-6-naphthalen-2-ylhexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=CC=C2)C2=C1 GWKVUDAJIWDWIM-UHFFFAOYSA-N 0.000 claims 1
• PNIDNVORUGGUIA-UHFFFAOYSA-N 3-[[1-(5,6-dichloro-1h-benzimidazol-2-yl)-3-methylbutyl]carbamoyl]-5-methyl-6-(4-phenylphenyl)hexanoic acid Chemical compound N=1C2=CC(Cl)=C(Cl)C=C2NC=1C(CC(C)C)NC(=O)C(CC(O)=O)CC(C)CC(C=C1)=CC=C1C1=CC=CC=C1 PNIDNVORUGGUIA-UHFFFAOYSA-N 0.000 claims 1
• CHTYJKNGZPLALD-UHFFFAOYSA-N 3-[[1-(5,6-dichloro-1h-benzimidazol-2-yl)-3-methylbutyl]carbamoyl]-5-methylhexanoic acid Chemical compound ClC1=C(Cl)C=C2NC(C(CC(C)C)NC(=O)C(CC(O)=O)CC(C)C)=NC2=C1 CHTYJKNGZPLALD-UHFFFAOYSA-N 0.000 claims 1
• NMNBHPGEZQETTC-UHFFFAOYSA-N 3-[[1-[3-(2-aminoethyl)anilino]-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C=1C=CC(CCN)=CC=1NC(=O)C(C(C)(C)C)NC(=O)C(CC(O)=O)CCCC(C=C1)=CC=C1C1=CC=CC=C1 NMNBHPGEZQETTC-UHFFFAOYSA-N 0.000 claims 1
• VIDZDRLGQRIFRS-UHFFFAOYSA-N 3-[[1-anilino-3-[(4-cyanophenyl)methylsulfanyl]-3-methyl-1-oxobutan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CCCC(CC(O)=O)C(=O)NC(C(=O)NC=1C=CC=CC=1)C(C)(C)SCC1=CC=C(C#N)C=C1 VIDZDRLGQRIFRS-UHFFFAOYSA-N 0.000 claims 1
• FCWBJACVFOEQEQ-UHFFFAOYSA-N 4-[4-(2-fluorophenoxy)phenyl]sulfonyl-n-hydroxy-2-oxothiomorpholine-3-carboxamide Chemical compound C1CSC(=O)C(C(=O)NO)N1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1F FCWBJACVFOEQEQ-UHFFFAOYSA-N 0.000 claims 1
• NEHLZQRKKVOFEG-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-3-n-hydroxy-1-n-methylpiperazine-1,3-dicarboxamide Chemical compound ONC(=O)C1CN(C(=O)NC)CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 NEHLZQRKKVOFEG-UHFFFAOYSA-N 0.000 claims 1
• HNZFMLNKCBKFQN-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-n-hydroxy-2,2-dimethylthiomorpholine-3-carboxamide Chemical compound ONC(=O)C1C(C)(C)SCCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 HNZFMLNKCBKFQN-UHFFFAOYSA-N 0.000 claims 1
• RAXPEBLSVFVDFD-UHFFFAOYSA-N 4-[4-[(1-carboxy-2-methylpropyl)sulfamoyl]phenyl]benzoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)C)C(O)=O)=CC=C1C1=CC=C(C(O)=O)C=C1 RAXPEBLSVFVDFD-UHFFFAOYSA-N 0.000 claims 1
• ZSSRAOCLWJZASZ-UHFFFAOYSA-N 4-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]amino]-4-oxo-3-phenylbutanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)C1=CC=CC=C1 ZSSRAOCLWJZASZ-UHFFFAOYSA-N 0.000 claims 1
• CRBBEPSKPQSRHZ-UHFFFAOYSA-N 4-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]amino]-4-oxo-3-thiophen-2-ylbutanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)C1=CC=CS1 CRBBEPSKPQSRHZ-UHFFFAOYSA-N 0.000 claims 1
• JOYDUCRIYCOQIJ-UHFFFAOYSA-N 4-[[3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]amino]-3-[1-(4-fluorophenyl)pyrrol-3-yl]-4-oxobutanoic acid Chemical compound C1=C(C(CC(O)=O)C(=O)NC(C(=O)NC)C(C)(C)C)C=CN1C1=CC=C(F)C=C1 JOYDUCRIYCOQIJ-UHFFFAOYSA-N 0.000 claims 1
• HGLFNRGXRCKGSW-UHFFFAOYSA-N 5-[(3,5-ditert-butyl-4-hydroxyanilino)-[[4-(2,2-dimethylpropyl)phenyl]methyl-hexylamino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1NC(=C1C(OC(C)(C)OC1=O)=O)N(CCCCCC)CC1=CC=C(CC(C)(C)C)C=C1 HGLFNRGXRCKGSW-UHFFFAOYSA-N 0.000 claims 1
• QNYXKETXZATWFI-UHFFFAOYSA-N 6-[4-[4-(2-aminoethoxy)phenyl]phenyl]-3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]hexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC(OCCN)=CC=2)C=C1 QNYXKETXZATWFI-UHFFFAOYSA-N 0.000 claims 1
• QHHFUUIWKQBDRC-UHFFFAOYSA-N C1(=CC=C(C=C1)CCCCC(C(=O)O)C(NC(C(NCCCN1CCOCC1)=O)C1CCCCC1)=O)C1=CC=CC=C1 Chemical compound C1(=CC=C(C=C1)CCCCC(C(=O)O)C(NC(C(NCCCN1CCOCC1)=O)C1CCCCC1)=O)C1=CC=CC=C1 QHHFUUIWKQBDRC-UHFFFAOYSA-N 0.000 claims 1
• OKUWDNJOBMLYPT-UHFFFAOYSA-N COC(C1=CC=C(C=C1)NC(C(CC(C)C)NC(C(CCCC1=CC=C(C=C1)C1=CC=CC=C1)NC(C)C(=O)O)=O)=O)=O Chemical compound COC(C1=CC=C(C=C1)NC(C(CC(C)C)NC(C(CCCC1=CC=C(C=C1)C1=CC=CC=C1)NC(C)C(=O)O)=O)=O)=O OKUWDNJOBMLYPT-UHFFFAOYSA-N 0.000 claims 1
• OHKRDGZAJWZVCG-UHFFFAOYSA-N COC=1C=C2CCN(CC2=CC1OC)C(CCCCCCCC=C/CCCCCCCC)=O Chemical compound COC=1C=C2CCN(CC2=CC1OC)C(CCCCCCCC=C/CCCCCCCC)=O OHKRDGZAJWZVCG-UHFFFAOYSA-N 0.000 claims 1
• NUYFKDBCHFKOBT-UHFFFAOYSA-N [1-(6-hydroxy-1-methoxy-8-methyl-12-oxo-10h-benzo[b][1,5]benzodioxocin-2-yl)-3-methylbutyl] acetate Chemical compound O1C2=C(O)C=C(C)C=C2COC(=O)C2=C1C=CC(C(CC(C)C)OC(C)=O)=C2OC NUYFKDBCHFKOBT-UHFFFAOYSA-N 0.000 claims 1
• BOGOAOVZHJYIRZ-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-(2-thiophen-3-ylacetyl)phenyl] sulfamate Chemical compound S1C=C(C=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C BOGOAOVZHJYIRZ-UHFFFAOYSA-N 0.000 claims 1
• WQRMTMWIXSZJNP-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[3-[2,4,6-tri(propan-2-yl)phenyl]prop-2-enoyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C=CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C WQRMTMWIXSZJNP-UHFFFAOYSA-N 0.000 claims 1
• KKSWLSQKFBJGQJ-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[3-[2,4,6-tri(propan-2-yl)phenyl]propanoyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C KKSWLSQKFBJGQJ-UHFFFAOYSA-N 0.000 claims 1
• FNQIZEQUAUEZSA-UHFFFAOYSA-N [2,6-diphenyl-3-[2-[2,4,6-tri(propan-2-yl)phenyl]acetyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)C(C(=C1OS(N)(=O)=O)C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 FNQIZEQUAUEZSA-UHFFFAOYSA-N 0.000 claims 1
• NWLFOBZKYXKBOF-UHFFFAOYSA-N [2-[[2,2-dimethylpropyl(nonyl)carbamoyl]amino]cyclohexyl] 3-[(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propanoate Chemical compound CCCCCCCCCN(CC(C)(C)C)C(=O)NC1CCCCC1OC(=O)CCNC(=O)C1C(C)(C)COC(C)(C)O1 NWLFOBZKYXKBOF-UHFFFAOYSA-N 0.000 claims 1
• QNRBLGKOBXBNQA-UHFFFAOYSA-N [3-(1-phenylcyclopentanecarbonyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C1(C=2C=CC=CC=2)CCCC1 QNRBLGKOBXBNQA-UHFFFAOYSA-N 0.000 claims 1
• OWQGQWCZHWFFBB-UHFFFAOYSA-N [3-(2,2-diphenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C)(C=1C=CC=CC=1)C1=CC=CC=C1 OWQGQWCZHWFFBB-UHFFFAOYSA-N 0.000 claims 1
• LHGJDLJINRPFDO-UHFFFAOYSA-N [3-(2-cyclohexyl-2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C=1C=CC=CC=1)C1CCCCC1 LHGJDLJINRPFDO-UHFFFAOYSA-N 0.000 claims 1
• QLCRUODBCQNCBH-UHFFFAOYSA-N [3-(3-methyl-2-phenylpentanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound C=1C=CC=CC=1C(C(C)CC)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C QLCRUODBCQNCBH-UHFFFAOYSA-N 0.000 claims 1
• LGCMWWNQMXOKTK-RBUKOAKNSA-N [3-[(1r,2r)-2-phenylcyclopropanecarbonyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)[C@H]1[C@H](C=2C=CC=CC=2)C1 LGCMWWNQMXOKTK-RBUKOAKNSA-N 0.000 claims 1
• COLDWNCECCAUKF-UHFFFAOYSA-N [3-[2-(1-adamantyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound C12(CC3CC(CC(C1)C3)C2)CC(=O)C=1C(=C(C(=CC=1)C(C)C)OS(N)(=O)=O)C(C)C COLDWNCECCAUKF-UHFFFAOYSA-N 0.000 claims 1
• XZJUPTJTXXIRGP-UHFFFAOYSA-N [3-[2-[2,6-di(propan-2-yl)phenoxy]acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1OCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C XZJUPTJTXXIRGP-UHFFFAOYSA-N 0.000 claims 1
• XBVKHCGXRZSBCL-UHFFFAOYSA-N [3-[2-[2,6-di(propan-2-yl)phenyl]acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C XBVKHCGXRZSBCL-UHFFFAOYSA-N 0.000 claims 1
• DDHOUTXDEJOEFF-UHFFFAOYSA-N [3-[2-fluoro-2-[2,4,6-tri(propan-2-yl)phenyl]acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C(F)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C DDHOUTXDEJOEFF-UHFFFAOYSA-N 0.000 claims 1
• 125000002252 acyl group Chemical group 0.000 claims 1
• WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 claims 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
• QRLXEVCFSGFUPY-UHFFFAOYSA-N ethyl 1-[3-[[3-(1-methylimidazol-2-yl)-2-(2-phenylethyl)-2h-chromen-6-yl]oxy]propyl]cyclopentane-1-carboxylate Chemical compound C=1C=C2OC(CCC=3C=CC=CC=3)C(C=3N(C=CN=3)C)=CC2=CC=1OCCCC1(C(=O)OCC)CCCC1 QRLXEVCFSGFUPY-UHFFFAOYSA-N 0.000 claims 1
• MFOWFPSBOORCPU-UHFFFAOYSA-N methyl 4-[[2-[[(2z)-2-amino-2-hydroxyiminoethyl]-(5-phenylpentanoyl)amino]-4-methylpentanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)N(CC(N)=NO)C(=O)CCCCC1=CC=CC=C1 MFOWFPSBOORCPU-UHFFFAOYSA-N 0.000 claims 1
• ZMTVODSCMDIXEJ-UHFFFAOYSA-N n'-hydroxy-n-(1-hydroxy-3-phenylmethoxybutan-2-yl)-2-[3-(4-phenylphenyl)propyl]butanediamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CCCC(CC(=O)NO)C(=O)NC(CO)C(C)OCC1=CC=CC=C1 ZMTVODSCMDIXEJ-UHFFFAOYSA-N 0.000 claims 1
• JBXUWZWQOALCHQ-UHFFFAOYSA-N n'-hydroxy-n-(1-hydroxy-3-phenylpropan-2-yl)-2-(2-methylpropyl)butanediamide Chemical compound ONC(=O)CC(CC(C)C)C(=O)NC(CO)CC1=CC=CC=C1 JBXUWZWQOALCHQ-UHFFFAOYSA-N 0.000 claims 1
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