ZA200100294B - Coadministration of ACAT and MMP inhibitors for the treatment of atherosclerotic lesions. - Google Patents

Info

Publication number

ZA200100294B

ZA200100294B ZA200100294A ZA200100294A ZA200100294B ZA 200100294 B ZA200100294 B ZA 200100294B ZA 200100294 A ZA200100294 A ZA 200100294A ZA 200100294 A ZA200100294 A ZA 200100294A ZA 200100294 B ZA200100294 B ZA 200100294B

Authority

ZA

South Africa

Prior art keywords

acid

methyl

phenyl

biphenyl

hydroxy

Prior art date

1998-07-21

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• 229940124761 MMP inhibitor Drugs 0.000 title claims description 47
• 230000003902 lesion Effects 0.000 title claims description 19
• 230000003143 atherosclerotic effect Effects 0.000 title claims description 11
• 150000001875 compounds Chemical class 0.000 claims description 98
• 238000000034 method Methods 0.000 claims description 84
• -1 carboxyalkyl ketone Chemical class 0.000 claims description 74
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
• 239000002253 acid Substances 0.000 claims description 37
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 36
• 239000003112 inhibitor Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 25
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 17
• 150000004702 methyl esters Chemical class 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
• 241000124008 Mammalia Species 0.000 claims description 13
• 150000001408 amides Chemical class 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 150000002148 esters Chemical class 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 239000005711 Benzoic acid Substances 0.000 claims description 9
• 235000010233 benzoic acid Nutrition 0.000 claims description 8
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 230000001737 promoting effect Effects 0.000 claims description 4
• 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 description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims 44
• 239000000203 mixture Substances 0.000 claims 41
• 239000000126 substance Substances 0.000 claims 41
• 125000000217 alkyl group Chemical group 0.000 claims 38
• 125000004432 carbon atom Chemical group C* 0.000 claims 18
• 229910052799 carbon Inorganic materials 0.000 claims 13
• 150000002431 hydrogen Chemical group 0.000 claims 13
• 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 13
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 12
• 239000007983 Tris buffer Substances 0.000 claims 10
• 229960004050 aminobenzoic acid Drugs 0.000 claims 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims 10
• QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 8
• 125000003545 alkoxy group Chemical group 0.000 claims 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
• 125000001589 carboacyl group Chemical group 0.000 claims 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
• 229910052760 oxygen Inorganic materials 0.000 claims 6
• WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
• SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims 5
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 5
• FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 5
• 239000001301 oxygen Substances 0.000 claims 5
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 5
• 239000004202 carbamide Substances 0.000 claims 4
• 229910052736 halogen Inorganic materials 0.000 claims 4
• 125000005843 halogen group Chemical group 0.000 claims 4
• 150000002367 halogens Chemical class 0.000 claims 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
• 229940080818 propionamide Drugs 0.000 claims 4
• 150000003839 salts Chemical class 0.000 claims 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
• GJOCABIDMCKCEG-INIZCTEOSA-N (2s)-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical group C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(Br)C=C1 GJOCABIDMCKCEG-INIZCTEOSA-N 0.000 claims 3
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 3
• 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 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
• 125000004423 acyloxy group Chemical group 0.000 claims 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
• 229910052794 bromium Inorganic materials 0.000 claims 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
• 239000000460 chlorine Substances 0.000 claims 3
• 229910052801 chlorine Inorganic materials 0.000 claims 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims 3
• 229910052731 fluorine Inorganic materials 0.000 claims 3
• 239000011737 fluorine Substances 0.000 claims 3
• 229960003136 leucine Drugs 0.000 claims 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
• 125000001424 substituent group Chemical group 0.000 claims 3
• 229910052717 sulfur Inorganic materials 0.000 claims 3
• 239000011593 sulfur Substances 0.000 claims 3
• 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 2
• 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 2
• 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 2
• UILJVUAZNKPODH-UHFFFAOYSA-N 1-[[1-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidine-2-carboxylic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)N1C(C(O)=O)CCC1 UILJVUAZNKPODH-UHFFFAOYSA-N 0.000 claims 2
• WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• SEINETSKRAZANU-UHFFFAOYSA-N 2-methylsulfanyl-1h-indole Chemical compound C1=CC=C2NC(SC)=CC2=C1 SEINETSKRAZANU-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims 2
• 150000003857 carboxamides Chemical class 0.000 claims 2
• 125000005518 carboxamido group Chemical group 0.000 claims 2
• 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 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• SWYZGLWCQFMQJW-UHFFFAOYSA-N phenoxy hypofluorite Chemical compound FOOC1=CC=CC=C1 SWYZGLWCQFMQJW-UHFFFAOYSA-N 0.000 claims 2
• 125000005544 phthalimido group Chemical group 0.000 claims 2
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
• 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 1
• 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 1
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• 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 1
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• LGXAATFEMPXRKP-SFHVURJKSA-N (2r)-n-hydroxy-2-[[4-(4-imidazol-1-ylphenoxy)piperidin-1-yl]sulfonylamino]-3,3-dimethylbutanamide Chemical compound C1CN(S(=O)(=O)N[C@H](C(C)(C)C)C(=O)NO)CCC1OC1=CC=C(N2C=NC=C2)C=C1 LGXAATFEMPXRKP-SFHVURJKSA-N 0.000 claims 1
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• DEEYWQGRLIJZHD-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-1-oxopent-4-en-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC=C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 DEEYWQGRLIJZHD-UHFFFAOYSA-N 0.000 claims 1
• HMFNVMWTJGHITR-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-5-phenylpentanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(C(C)(C)C)NC(=O)C(CC(O)=O)CCC1=CC=CC=C1 HMFNVMWTJGHITR-UHFFFAOYSA-N 0.000 claims 1
• PZQDPLPZNOJDQB-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-6-phenylhexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(C(C)(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=CC=C1 PZQDPLPZNOJDQB-UHFFFAOYSA-N 0.000 claims 1
• HYNIDHKAVGIKBF-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]-5-methylhexanoic acid Chemical compound COC(=O)C1=CC=C(NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)CC(O)=O)C=C1 HYNIDHKAVGIKBF-UHFFFAOYSA-N 0.000 claims 1
• HGQWAXDIVNYTBX-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]-6-(4-pyridin-4-ylphenyl)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=CN=CC=2)C=C1 HGQWAXDIVNYTBX-UHFFFAOYSA-N 0.000 claims 1
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• 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
• LTAWRSLQSBXDLI-UHFFFAOYSA-N 3-[[1-anilino-3-[(4-methoxyphenyl)methylsulfanyl]-3-methyl-1-oxobutan-2-yl]carbamoyl]-5-methylhexanoic acid Chemical compound C1=CC(OC)=CC=C1CSC(C)(C)C(NC(=O)C(CC(C)C)CC(O)=O)C(=O)NC1=CC=CC=C1 LTAWRSLQSBXDLI-UHFFFAOYSA-N 0.000 claims 1
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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 1
• 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 1
• 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 1
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