CA2335062A1 - Coadministration of acat and mmp inhibitors for the treatment of atherosclerotic lesions - Google Patents
Coadministration of acat and mmp inhibitors for the treatment of atherosclerotic lesions Download PDFInfo
- 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
- 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
- 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
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- 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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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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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- 229940081974 saccharin Drugs 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9363998P | 1998-07-21 | 1998-07-21 | |
US60/093,639 | 1998-07-21 | ||
PCT/US1999/013948 WO2000004892A2 (en) | 1998-07-21 | 1999-06-18 | Coadministration of acat and mmp inhibitors for the treatment of atherosclerotic lesions |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2335062A1 true CA2335062A1 (en) | 2000-02-03 |
Family
ID=22239992
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002335062A Abandoned CA2335062A1 (en) | 1998-07-21 | 1999-06-18 | Coadministration of acat and mmp inhibitors for the treatment of atherosclerotic lesions |
Country Status (25)
Country | Link |
---|---|
EP (1) | EP1098662A2 (no) |
JP (1) | JP2002521328A (no) |
KR (1) | KR20010083134A (no) |
CN (1) | CN1310629A (no) |
AP (1) | AP2001002035A0 (no) |
AU (1) | AU4701799A (no) |
BG (1) | BG105162A (no) |
BR (1) | BR9912296A (no) |
CA (1) | CA2335062A1 (no) |
CZ (1) | CZ2001126A3 (no) |
EA (1) | EA200100153A1 (no) |
EE (1) | EE200100046A (no) |
HR (1) | HRP20010055A2 (no) |
HU (1) | HUP0102880A3 (no) |
ID (1) | ID30030A (no) |
IL (1) | IL140982A0 (no) |
IS (1) | IS5809A (no) |
NO (1) | NO20010291D0 (no) |
OA (1) | OA11584A (no) |
PL (1) | PL346011A1 (no) |
SK (1) | SK502001A3 (no) |
TR (1) | TR200100205T2 (no) |
WO (1) | WO2000004892A2 (no) |
YU (1) | YU3501A (no) |
ZA (1) | ZA200100294B (no) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2382676A1 (en) * | 1999-11-05 | 2001-05-17 | Warner-Lambert Company | Prevention of plaque rupture by acat inhibitors |
GT200000203A (es) | 1999-12-01 | 2002-05-24 | Compuestos, composiciones y metodos para estimular el crecimiento y elongacion de neuronas. | |
AU2268301A (en) * | 1999-12-17 | 2001-06-25 | Versicor Inc | Novel urea compounds, compositions and methods of use and preparation |
AU2001282541B2 (en) * | 2000-09-01 | 2004-06-24 | Sankyo Company, Limited | Medicinal compositions |
GB0100761D0 (en) | 2001-01-11 | 2001-02-21 | Biocompatibles Ltd | Drug delivery from stents |
ATE399012T1 (de) * | 2002-04-03 | 2008-07-15 | Topotarget Uk Ltd | Carbaminsäurederivate enthaltend eine piperazin verknüpfung als hdac-inhibitoren |
AU2003267991B2 (en) * | 2002-07-11 | 2009-10-08 | Vicuron Pharmaceuticals, Inc. | N-hydroxyamide derivatives possessing antibacterial activity |
WO2011092284A1 (en) * | 2010-01-29 | 2011-08-04 | Euroscreen S.A. | Novel amino acid derivatives and their use as gpr43 receptor modulators |
CN104211695B (zh) * | 2013-06-04 | 2017-04-12 | 中国医学科学院医药生物技术研究所 | 一组胺甲酰基苯磺酰类化合物的用途 |
EP3244883A1 (en) * | 2015-01-15 | 2017-11-22 | Biocant - Associação De Transferência De Tecnologia | Treatment of hutchinson-gilford progeria syndrome and diseases related to vascular ageing |
CN106831697B (zh) * | 2017-03-15 | 2019-11-05 | 深圳市康道生物有限公司 | 川榛有效提取成分及其在防治动脉粥样硬化中的应用 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5366987A (en) * | 1991-08-22 | 1994-11-22 | Warner-Lambert Company | Isoxazolyl-substituted alkyl amide ACAT inhibitors |
US5491172A (en) * | 1993-05-14 | 1996-02-13 | Warner-Lambert Company | N-acyl sulfamic acid esters (or thioesters), N-acyl sulfonamides, and N-sulfonyl carbamic acid esters (or thioesters) as hypercholesterolemic agents |
EA002435B1 (ru) * | 1995-08-04 | 2002-04-25 | Варнер-Ламберт Компани | Способ снижения уровня липопротеина (а) в сыворотке или в плазме крови млекопитающих |
SK282863B6 (sk) * | 1996-05-17 | 2002-12-03 | Warner-Lambert Company | Bifenylsulfonamidy, ich použitie a farmaceutické prostriedky na ich báze |
EP0931045A1 (en) * | 1996-09-04 | 1999-07-28 | Warner-Lambert Company | Matrix metalloproteinase inhibitors and their therapeutic uses |
-
1999
- 1999-06-18 KR KR1020017000930A patent/KR20010083134A/ko not_active Application Discontinuation
- 1999-06-18 JP JP2000560885A patent/JP2002521328A/ja active Pending
- 1999-06-18 AP APAP/P/2001/002035A patent/AP2001002035A0/en unknown
- 1999-06-18 EA EA200100153A patent/EA200100153A1/ru unknown
- 1999-06-18 EP EP99930483A patent/EP1098662A2/en not_active Withdrawn
- 1999-06-18 ID IDW20010333A patent/ID30030A/id unknown
- 1999-06-18 CN CN99808958A patent/CN1310629A/zh active Pending
- 1999-06-18 YU YU3501A patent/YU3501A/sh unknown
- 1999-06-18 BR BR9912296-0A patent/BR9912296A/pt not_active IP Right Cessation
- 1999-06-18 WO PCT/US1999/013948 patent/WO2000004892A2/en not_active Application Discontinuation
- 1999-06-18 TR TR2001/00205T patent/TR200100205T2/xx unknown
- 1999-06-18 SK SK50-2001A patent/SK502001A3/sk unknown
- 1999-06-18 CZ CZ2001126A patent/CZ2001126A3/cs unknown
- 1999-06-18 PL PL99346011A patent/PL346011A1/xx unknown
- 1999-06-18 HU HU0102880A patent/HUP0102880A3/hu unknown
- 1999-06-18 IL IL14098299A patent/IL140982A0/xx unknown
- 1999-06-18 CA CA002335062A patent/CA2335062A1/en not_active Abandoned
- 1999-06-18 OA OA1200100022A patent/OA11584A/en unknown
- 1999-06-18 AU AU47017/99A patent/AU4701799A/en not_active Abandoned
- 1999-06-18 EE EEP200100046A patent/EE200100046A/xx unknown
-
2001
- 2001-01-10 ZA ZA200100294A patent/ZA200100294B/en unknown
- 2001-01-12 IS IS5809A patent/IS5809A/is unknown
- 2001-01-17 BG BG105162A patent/BG105162A/xx unknown
- 2001-01-18 NO NO20010291A patent/NO20010291D0/no not_active Application Discontinuation
- 2001-01-19 HR HR20010055A patent/HRP20010055A2/hr not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
AU4701799A (en) | 2000-02-14 |
EE200100046A (et) | 2002-06-17 |
HRP20010055A2 (en) | 2002-04-30 |
SK502001A3 (en) | 2002-06-04 |
CN1310629A (zh) | 2001-08-29 |
IS5809A (is) | 2001-01-12 |
HUP0102880A3 (en) | 2002-11-28 |
NO20010291L (no) | 2001-01-18 |
EA200100153A1 (ru) | 2001-08-27 |
KR20010083134A (ko) | 2001-08-31 |
JP2002521328A (ja) | 2002-07-16 |
ID30030A (id) | 2001-11-01 |
EP1098662A2 (en) | 2001-05-16 |
BG105162A (en) | 2001-12-29 |
PL346011A1 (en) | 2002-01-14 |
NO20010291D0 (no) | 2001-01-18 |
TR200100205T2 (tr) | 2001-05-21 |
ZA200100294B (en) | 2002-01-10 |
HUP0102880A2 (en) | 2002-06-29 |
CZ2001126A3 (cs) | 2002-01-16 |
WO2000004892A2 (en) | 2000-02-03 |
WO2000004892A3 (en) | 2000-05-18 |
IL140982A0 (en) | 2002-02-10 |
BR9912296A (pt) | 2001-04-17 |
YU3501A (sh) | 2005-06-10 |
OA11584A (en) | 2004-07-20 |
AP2001002035A0 (en) | 2001-03-31 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |