SK502001A3 - 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 PDF

Info

Publication number: SK502001A3
Authority: SK; Slovakia
Prior art keywords: acid; methyl; phenyl; biphenyl; hydroxy
Prior art date: 1998-07-21

Application number

SK50-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Thomas Michael Andrew Bocan

Original Assignee

Warner Lambert Co

Priority date (The priority date 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 date listed.)

1998-07-21

Filing date

1999-06-18

Publication date

2002-06-04

1999-06-18 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2002-06-04 Publication of SK502001A3 publication Critical patent/SK502001A3/sk

Links

229940124761 MMP inhibitor Drugs 0.000 title claims abstract description 43
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 6
230000002265 prevention Effects 0.000 claims abstract description 5
-1 carboxylalkyl ketone Chemical class 0.000 claims description 986
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 159
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 106
150000001875 compounds Chemical class 0.000 claims description 105
125000000217 alkyl group Chemical group 0.000 claims description 96
150000001408 amides Chemical class 0.000 claims description 90
239000002253 acid Substances 0.000 claims description 76
239000001257 hydrogen Substances 0.000 claims description 74
229910052739 hydrogen Inorganic materials 0.000 claims description 74
125000004432 carbon atom Chemical group C* 0.000 claims description 72
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 72
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
125000001424 substituent group Chemical group 0.000 claims description 53
239000003112 inhibitor Substances 0.000 claims description 49
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 43
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 43
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 41
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 39
150000002431 hydrogen Chemical class 0.000 claims description 37
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 29
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 26
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 26
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 24
150000002367 halogens Chemical class 0.000 claims description 24
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 23
125000000753 cycloalkyl group Chemical group 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 20
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 16
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
239000005711 Benzoic acid Substances 0.000 claims description 14
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 14
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
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
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 12
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
GENNWAXPOVPMKR-UHFFFAOYSA-N phenyl(propan-2-yl)sulfamic acid Chemical compound CC(C)N(S(O)(=O)=O)C1=CC=CC=C1 GENNWAXPOVPMKR-UHFFFAOYSA-N 0.000 claims description 11
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 10
125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims description 10
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
LGUSPHYTWOJRIU-UHFFFAOYSA-N phenyl n-propan-2-ylsulfamate Chemical compound CC(C)NS(=O)(=O)OC1=CC=CC=C1 LGUSPHYTWOJRIU-UHFFFAOYSA-N 0.000 claims description 10
239000011734 sodium Substances 0.000 claims description 10
229910052708 sodium Inorganic materials 0.000 claims description 10
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 9
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 9
235000010233 benzoic acid Nutrition 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
159000000000 sodium salts Chemical class 0.000 claims description 8
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
229960004050 aminobenzoic acid Drugs 0.000 claims description 7
125000001246 bromo group Chemical group Br* 0.000 claims description 7
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
XOIYZMDJFLKIEI-UHFFFAOYSA-N (hydroxysulfonimidoyl)oxybenzene Chemical compound NS(=O)(=O)OC1=CC=CC=C1 XOIYZMDJFLKIEI-UHFFFAOYSA-N 0.000 claims description 6
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 description 6
SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims description 5
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
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
239000007983 Tris buffer Substances 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
150000004702 methyl esters Chemical class 0.000 claims description 5
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
MHKSVFZDORJGNL-TVKKRMFBSA-N (2R)-1-(1-phenylethylcarbamoyl)pyrrolidine-2-carboxylic acid Chemical compound C=1C=CC=CC=1C(C)NC(=O)N1CCC[C@@H]1C(O)=O MHKSVFZDORJGNL-TVKKRMFBSA-N 0.000 claims description 4
CQPXVQDUGJYNSM-LJQANCHMSA-N (2r)-1-[4-(4-imidazol-1-ylphenoxy)piperidin-1-yl]sulfonylpiperidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCCN1S(=O)(=O)N1CCC(OC=2C=CC(=CC=2)N2C=NC=C2)CC1 CQPXVQDUGJYNSM-LJQANCHMSA-N 0.000 claims description 4
PCSRHMRNMQQORE-GSVOUGTGSA-N (2s)-2-(methylsulfanylamino)-3-sulfanylpropanoic acid Chemical compound CSN[C@H](CS)C(O)=O PCSRHMRNMQQORE-GSVOUGTGSA-N 0.000 claims description 4
125000004191 (C1-C6) alkoxy group Chemical group 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
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 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
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 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
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 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
XZFSRMBQSOGHPB-UHFFFAOYSA-N 3-(3-hydroxypiperidine-1-carbonyl)-6-(4-phenylphenyl)hexanoic acid Chemical compound C1C(O)CCCN1C(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 XZFSRMBQSOGHPB-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
JUSZZVIIBCNGQA-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonyl-2,2-dimethylthiomorpholine-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C(C(O)=O)C(C)(C)SCC1 JUSZZVIIBCNGQA-UHFFFAOYSA-N 0.000 claims description 4
IEEFWEPSXSWNNX-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-2,2-dimethylthiomorpholine-3-carboxylic acid Chemical compound OC(=O)C1C(C)(C)SCCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 IEEFWEPSXSWNNX-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
KMAVAHOWUQJKOD-UHFFFAOYSA-N C1CCN(C(C1)C(=O)O)S(=O)(=O)C2=CC=CC=C2OC3=CC=C(C=C3)Br Chemical compound C1CCN(C(C1)C(=O)O)S(=O)(=O)C2=CC=CC=C2OC3=CC=C(C=C3)Br KMAVAHOWUQJKOD-UHFFFAOYSA-N 0.000 claims description 4
YYQLAXTXNFJPMY-HXUWFJFHSA-N CC(C)([C@@H](C(=O)O)NS(=O)(=O)C1=CC=C(C=C1)OC2=CC=C(C=C2)Br)SC3=CC=CC=N3 Chemical compound CC(C)([C@@H](C(=O)O)NS(=O)(=O)C1=CC=C(C=C1)OC2=CC=C(C=C2)Br)SC3=CC=CC=N3 YYQLAXTXNFJPMY-HXUWFJFHSA-N 0.000 claims description 4
XUJNEKJLAYXESH-UWTATZPHSA-N D-Cysteine Chemical compound SC[C@@H](N)C(O)=O XUJNEKJLAYXESH-UWTATZPHSA-N 0.000 claims description 4
229930195710 D‐cysteine Natural products 0.000 claims description 4
239000004202 carbamide Substances 0.000 claims description 4
JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
KYSMABGEZNVPJF-HXUWFJFHSA-N (2r)-2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-3-methyl-3-pyridin-2-ylsulfanylbutanoic acid Chemical compound CC(C)([C@H](NS(=O)(=O)C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1)C(O)=O)SC1=CC=CC=N1 KYSMABGEZNVPJF-HXUWFJFHSA-N 0.000 claims description 3
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 3
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 description 3
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
TUBMCKKTQQWJAN-UHFFFAOYSA-N 2-benzylsulfanylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1SCC1=CC=CC=C1 TUBMCKKTQQWJAN-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
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 3
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 3
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 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
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 3
GJPCBZZAGGGVES-OAQYLSRUSA-N CC1=CC=C(C=C1)OC2=CC=C(C=C2)S(=O)(=O)N[C@H](C(=O)O)C(C)(C)S(=O)(=O)C3=CC=CC=N3 Chemical compound CC1=CC=C(C=C1)OC2=CC=C(C=C2)S(=O)(=O)N[C@H](C(=O)O)C(C)(C)S(=O)(=O)C3=CC=CC=N3 GJPCBZZAGGGVES-OAQYLSRUSA-N 0.000 claims description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000005544 phthalimido group Chemical group 0.000 claims description 3
239000012453 solvate Substances 0.000 claims description 3
KMSCERSHAPLCBB-ZIAGYGMSSA-N (1s,2r)-2-(2-phenylethylsulfonyl)cyclohexane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCC[C@H]1S(=O)(=O)CCC1=CC=CC=C1 KMSCERSHAPLCBB-ZIAGYGMSSA-N 0.000 claims description 2
PFVQTLVDWFDABZ-UHFFFAOYSA-N (2,4,6-trifluorophenyl)urea Chemical compound NC(=O)NC1=C(F)C=C(F)C=C1F PFVQTLVDWFDABZ-UHFFFAOYSA-N 0.000 claims description 2
SVCKOHQNSPOXRM-HXUWFJFHSA-N (2R)-2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-3-methyl-3-pyridin-3-ylsulfanylbutanoic acid Chemical compound CC(C)([C@H](NS(=O)(=O)C=1C=CC(OC=2C=CC(F)=CC=2)=CC=1)C(O)=O)SC1=CC=CN=C1 SVCKOHQNSPOXRM-HXUWFJFHSA-N 0.000 claims description 2
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CBYVKUVINLGICB-HXUWFJFHSA-N (2R)-2-[[4-(4-iodophenoxy)phenyl]sulfonylamino]-3-methyl-3-pyridin-2-ylsulfonylbutanoic acid Chemical compound IC1=CC=C(OC2=CC=C(C=C2)S(=O)(=O)N[C@H](C(=O)O)C(C)(S(=O)(=O)C2=NC=CC=C2)C)C=C1 CBYVKUVINLGICB-HXUWFJFHSA-N 0.000 claims description 2
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BYUDLSQJYHNHRI-UHFFFAOYSA-N 2-[[4-(4-bromophenoxy)phenyl]sulfonylamino]-3-methyl-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]butanoic acid Chemical compound O1C(C)=CC(CSC(C)(C)C(NS(=O)(=O)C=2C=CC(OC=3C=CC(Br)=CC=3)=CC=2)C(O)=O)=N1 BYUDLSQJYHNHRI-UHFFFAOYSA-N 0.000 claims description 2
YTSLULHGBPSVJQ-UHFFFAOYSA-N 2-[[4-(4-chlorophenoxy)phenyl]sulfonylamino]-3,3-dimethylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)(C)C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1 YTSLULHGBPSVJQ-UHFFFAOYSA-N 0.000 claims description 2
CISQPJUDSHOGSA-UHFFFAOYSA-N 2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-3,3-dimethyl-5-phenylpent-4-enoic acid Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1S(=O)(=O)NC(C(O)=O)C(C)(C)C=CC1=CC=CC=C1 CISQPJUDSHOGSA-UHFFFAOYSA-N 0.000 claims description 2
OOIBNLHVYPZUII-UHFFFAOYSA-N 2-[[4-(4-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=C(F)C=C1 OOIBNLHVYPZUII-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
IJUNEFKYCJHJQF-UHFFFAOYSA-N 2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-3-(3-methoxy-3-oxopropyl)sulfanyl-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)(C)SCCC(=O)OC)C(O)=O)=CC=C1OC1=CC=C(F)C=C1 IJUNEFKYCJHJQF-UHFFFAOYSA-N 0.000 claims description 2
QTXVPZVVAMBWOC-UHFFFAOYSA-N 2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-3-methyl-3-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]butanoic acid Chemical compound O1C(C)=CC(CSC(C)(C)C(NS(=O)(=O)C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)C(O)=O)=N1 QTXVPZVVAMBWOC-UHFFFAOYSA-N 0.000 claims description 2
XCFBACFYVCYJCG-UHFFFAOYSA-N 2-amino-3-cyclohexyl-N-methylpropanamide Chemical compound CNC(=O)C(N)CC1CCCCC1 XCFBACFYVCYJCG-UHFFFAOYSA-N 0.000 claims description 2
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 2
NIWBHCCYLKXVLY-UHFFFAOYSA-N 2-bromo-6,11-dihydrobenzo[c][1]benzoxepine-11-carboxylic acid Chemical compound C1OC2=CC=C(Br)C=C2C(C(=O)O)C2=CC=CC=C21 NIWBHCCYLKXVLY-UHFFFAOYSA-N 0.000 claims description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
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 description 2
BNJMOFJFDHXJDA-UHFFFAOYSA-N 3-(1,3-dihydroxybutan-2-ylcarbamoyl)-6-(4-phenylphenyl)hexanoic acid Chemical compound CC(C(CO)NC(=O)C(CCCC1=CC=C(C=C1)C2=CC=CC=C2)CC(=O)O)O BNJMOFJFDHXJDA-UHFFFAOYSA-N 0.000 claims description 2
AYGSECNNEDIEJL-UHFFFAOYSA-N 3-(1h-imidazol-5-yl)-n-(2-phenylethyl)propanamide Chemical compound C=1C=CC=CC=1CCNC(=O)CCC1=CN=CN1 AYGSECNNEDIEJL-UHFFFAOYSA-N 0.000 claims description 2
TVXOXGBTADZYCZ-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-[5-[(4,5-diphenyl-1h-imidazol-2-yl)sulfanyl]pentyl]-1-heptylurea Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CCCCCSC(N1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 TVXOXGBTADZYCZ-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
KDOYRGSXQJFSDM-UHFFFAOYSA-N 3-(2-methyl-1,3-thiazol-4-yl)-n-(2-phenylethyl)propanamide Chemical compound S1C(C)=NC(CCC(=O)NCCC=2C=CC=CC=2)=C1 KDOYRGSXQJFSDM-UHFFFAOYSA-N 0.000 claims description 2
YTLONNKDHMRKKI-UHFFFAOYSA-N 3-(carboxymethylsulfanyl)-2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)(SCC(O)=O)C)C(O)=O)=CC=C1OC1=CC=C(F)C=C1 YTLONNKDHMRKKI-UHFFFAOYSA-N 0.000 claims description 2
HKGOWEWMNCYQGY-UHFFFAOYSA-N 3-[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]-5-methylhexanoic acid Chemical compound CC(C)CC(CC(O)=O)C(=O)NC(CO)CC1=CC=CC=C1 HKGOWEWMNCYQGY-UHFFFAOYSA-N 0.000 claims description 2
MMCGQVNYJAZTMO-UHFFFAOYSA-N 3-[2-(hydroxymethyl)-1h-imidazol-5-yl]-n-(2-phenylethyl)propanamide Chemical compound N1C(CO)=NC=C1CCC(=O)NCCC1=CC=CC=C1 MMCGQVNYJAZTMO-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
RABKTNKWIDGVTC-UHFFFAOYSA-N 3-[[1-(3-amino-4-methoxycarbonylphenyl)-4-methyl-1-oxopentan-2-yl]carbamoyl]-5-(1h-indol-2-yl)pentanoic acid Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCC1=CC2=CC=CC=C2N1 RABKTNKWIDGVTC-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
SZTYNSBZLWKZQY-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-5-methylhexanoic acid Chemical compound COC(=O)C1=CC=C(NC(=O)C(NC(=O)C(CC(C)C)CC(O)=O)C(C)(C)C)C=C1 SZTYNSBZLWKZQY-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 description 2
OGGUSWZGVPWOML-UHFFFAOYSA-N 3-[[1-(4-methoxycarbonylanilino)-4-methyl-1-oxopentan-2-yl]carbamoyl]-6-[4-(4-sulfamoylphenyl)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(C=2C=CC(=CC=2)S(N)(=O)=O)C=C1 OGGUSWZGVPWOML-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
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 description 2
WVEDEOVPSDYQHT-UHFFFAOYSA-N 3-[[1-[4-(2-hydroxyethylsulfamoyl)anilino]-4-methyl-1-oxopentan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C=1C=C(S(=O)(=O)NCCO)C=CC=1NC(=O)C(CC(C)C)NC(=O)C(CC(O)=O)CCCC(C=C1)=CC=C1C1=CC=CC=C1 WVEDEOVPSDYQHT-UHFFFAOYSA-N 0.000 claims description 2
RLFAYOXSOPKVGA-UHFFFAOYSA-N 3-[[1-[n-(2-hydroxyethylsulfamoyl)anilino]-3,3-dimethyl-1-oxobutan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C=1C=CC=CC=1N(S(=O)(=O)NCCO)C(=O)C(C(C)(C)C)NC(=O)C(CC(O)=O)CCCC(C=C1)=CC=C1C1=CC=CC=C1 RLFAYOXSOPKVGA-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
LYPYNEOUONCVMF-UHFFFAOYSA-N 3-[[1-cyclohexyl-2-(4-methoxycarbonylanilino)-2-oxoethyl]carbamoyl]-5-methylhexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(NC(=O)C(CC(C)C)CC(O)=O)C1CCCCC1 LYPYNEOUONCVMF-UHFFFAOYSA-N 0.000 claims description 2
MTGYMDNEYMJUKU-UHFFFAOYSA-N 3-[[1-cyclohexyl-2-(4-methoxycarbonylanilino)-2-oxoethyl]carbamoyl]-6-phenylhexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(C1CCCCC1)NC(=O)C(CC(O)=O)CCCC1=CC=CC=C1 MTGYMDNEYMJUKU-UHFFFAOYSA-N 0.000 claims description 2
OUNQHTFCPILXSS-UHFFFAOYSA-N 3-[[1-cyclohexyl-2-[4-(2-hydroxyethylsulfamoyl)anilino]-2-oxoethyl]carbamoyl]-6-(4-pyridin-4-ylphenyl)hexanoic acid Chemical compound 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 OUNQHTFCPILXSS-UHFFFAOYSA-N 0.000 claims description 2
PNZNNYUTRLUNBL-UHFFFAOYSA-N 3-[[3,3-dimethyl-1-(4-methylsulfanylanilino)-1-oxobutan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(SC)=CC=C1NC(=O)C(C(C)(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 PNZNNYUTRLUNBL-UHFFFAOYSA-N 0.000 claims description 2
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
AQIJFXDPLOJWJA-UHFFFAOYSA-N 3-[[3,3-dimethyl-1-[4-(methylsulfamoyl)anilino]-1-oxobutan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1NC(=O)C(C(C)(C)C)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 AQIJFXDPLOJWJA-UHFFFAOYSA-N 0.000 claims description 2
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
ODRFUCAPZCRZGO-UHFFFAOYSA-N 3-[[3,3-dimethyl-1-oxo-1-(pyridin-4-ylamino)butan-2-yl]carbamoyl]-5-methylhexanoic acid Chemical compound CC(C)CC(CC(O)=O)C(=O)NC(C(C)(C)C)C(=O)NC1=CC=NC=C1 ODRFUCAPZCRZGO-UHFFFAOYSA-N 0.000 claims description 2
VJEYMPDBISHUMC-UHFFFAOYSA-N 3-[[3-hydroxy-3-methyl-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)O)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 VJEYMPDBISHUMC-UHFFFAOYSA-N 0.000 claims description 2
IRTHGDCQZWCJHJ-UHFFFAOYSA-N 3-[[4,5-dihydroxy-1-(4-methoxycarbonylanilino)-1-oxopentan-2-yl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(CC(O)CO)NC(=O)C(CC(O)=O)CCCC1=CC=C(C=2C=CC=CC=2)C=C1 IRTHGDCQZWCJHJ-UHFFFAOYSA-N 0.000 claims description 2
RJMVJXBLZVKSHQ-UHFFFAOYSA-N 3-[[[2-cyclohexyl-1-(4-methoxycarbonylanilino)-1-oxopropan-2-yl]amino]methyl]-5-phenylpentanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(C)(C1CCCCC1)NCC(CC(O)=O)CCC1=CC=CC=C1 RJMVJXBLZVKSHQ-UHFFFAOYSA-N 0.000 claims description 2
VSAWGHKNHDEJIW-UHFFFAOYSA-N 3-[[[3-cyclohexyl-1-(4-methoxycarbonylanilino)-1-oxopropan-2-yl]amino]methyl]-5-phenylpentanoic acid Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(NCC(CCC=1C=CC=CC=1)CC(O)=O)CC1CCCCC1 VSAWGHKNHDEJIW-UHFFFAOYSA-N 0.000 claims description 2
GQQCJBKKKYACNM-UHFFFAOYSA-N 3-[cyclohexylmethyl-[[4-(2-hydroxyethylsulfamoyl)phenyl]carbamoyl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(S(=O)(=O)NCCO)=CC=C1NC(=O)N(C(=O)C(CCCC=1C=CC(=CC=1)C=1C=CC=CC=1)CC(O)=O)CC1CCCCC1 GQQCJBKKKYACNM-UHFFFAOYSA-N 0.000 claims description 2
SEERMNMZUHISGZ-UHFFFAOYSA-N 3-[cyclohexylmethyl-[[4-[2-(dimethylamino)ethylsulfamoyl]phenyl]carbamoyl]carbamoyl]-6-(4-phenylphenyl)hexanoic acid Chemical compound C1=CC(S(=O)(=O)NCCN(C)C)=CC=C1NC(=O)N(C(=O)C(CCCC=1C=CC(=CC=1)C=1C=CC=CC=1)CC(O)=O)CC1CCCCC1 SEERMNMZUHISGZ-UHFFFAOYSA-N 0.000 claims description 2
LLJRXVHJOJRCSM-UHFFFAOYSA-N 3-pyridin-4-yl-1H-indole Chemical group C=1NC2=CC=CC=C2C=1C1=CC=NC=C1 LLJRXVHJOJRCSM-UHFFFAOYSA-N 0.000 claims description 2
FRSWYOWTNAWATQ-UHFFFAOYSA-N 4-(1H-indol-2-ylsulfonyl)thiomorpholine-3-carboxylic acid Chemical compound OC(=O)C1CSCCN1S(=O)(=O)C1=CC2=CC=CC=C2N1 FRSWYOWTNAWATQ-UHFFFAOYSA-N 0.000 claims description 2
RFTUHYGDLMRPJB-UHFFFAOYSA-N 4-(4-methoxyphenyl)sulfonylthiomorpholine-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C(C(O)=O)CSCC1 RFTUHYGDLMRPJB-UHFFFAOYSA-N 0.000 claims description 2
CCVFLYDNGCBSHW-UHFFFAOYSA-N 4-(4-phenoxyphenyl)sulfonylthiomorpholine-3-carboxylic acid Chemical compound OC(=O)C1CSCCN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 CCVFLYDNGCBSHW-UHFFFAOYSA-N 0.000 claims description 2
QXWKHSSBFQDQPR-UHFFFAOYSA-N 4-(hexadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 QXWKHSSBFQDQPR-UHFFFAOYSA-N 0.000 claims description 2
SOCISSVUMZUFSG-UHFFFAOYSA-N 4-(methylamino)-4-oxo-3-[3-(4-pyridin-4-ylphenyl)pyrrol-1-yl]butanoic acid Chemical compound CNC(=O)C(CC(O)=O)N1C=CC(C=2C=CC(=CC=2)C=2C=CN=CC=2)=C1 SOCISSVUMZUFSG-UHFFFAOYSA-N 0.000 claims description 2
OIYBBOLLJOLRTP-UHFFFAOYSA-N 4-[(1-hydroxy-3-phenylpropan-2-yl)amino]-4-oxo-3-[1-(4-phenylphenyl)pyrrol-3-yl]butanoic acid Chemical compound C1=CN(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1C(CC(O)=O)C(=O)NC(CO)CC1=CC=CC=C1 OIYBBOLLJOLRTP-UHFFFAOYSA-N 0.000 claims description 2
PLPOXERTYPNNOI-UHFFFAOYSA-N 4-[(1-hydroxy-3-phenylpropan-2-yl)amino]-4-oxo-3-[4-(4-phenylphenyl)pyrazol-1-yl]butanoic acid Chemical compound C1=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=NN1C(CC(O)=O)C(=O)NC(CO)CC1=CC=CC=C1 PLPOXERTYPNNOI-UHFFFAOYSA-N 0.000 claims description 2
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 2
JQSKHNILDYHDCS-UHFFFAOYSA-N 4-[(5-methyl-2-oxohexan-3-yl)amino]-4-oxo-3-[3-(4-phenylphenyl)pyrrol-1-yl]butanoic acid Chemical compound CC(C)CC(C(C)=O)NC(=O)C(CC(O)=O)N1C=CC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 JQSKHNILDYHDCS-UHFFFAOYSA-N 0.000 claims description 2
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RDMDTXAHXYVSKO-UHFFFAOYSA-N 4-[[1-(3-amino-4-methoxycarbonylphenyl)-4-methyl-1-oxopentan-2-yl]amino]-4-oxo-3-phenylbutanoic acid Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)C(CC(C)C)NC(=O)C(CC(O)=O)C1=CC=CC=C1 RDMDTXAHXYVSKO-UHFFFAOYSA-N 0.000 claims description 2
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CVNOHLJIBANEHF-UHFFFAOYSA-N O=C(C(C)C1=CC=CC=C1)N(S(O)(=O)=O)C1=C(C=CC=C1C(C)C)C(C)C Chemical compound O=C(C(C)C1=CC=CC=C1)N(S(O)(=O)=O)C1=C(C=CC=C1C(C)C)C(C)C CVNOHLJIBANEHF-UHFFFAOYSA-N 0.000 claims description 2
AQDXNOKXJICISO-UHFFFAOYSA-N O=[S]C1=CC=CC=N1 Chemical compound O=[S]C1=CC=CC=N1 AQDXNOKXJICISO-UHFFFAOYSA-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
PEUVKXDRVYWEJZ-UHFFFAOYSA-N OC(=O)C1CCCCN1S(=O)(=O)N1CCC(SC=2C=CC(=CC=2)N2C=NC=C2)CC1 Chemical compound OC(=O)C1CCCCN1S(=O)(=O)N1CCC(SC=2C=CC(=CC=2)N2C=NC=C2)CC1 PEUVKXDRVYWEJZ-UHFFFAOYSA-N 0.000 claims description 2
AULWUKYPIURLMH-UHFFFAOYSA-N OC(=O)C1CCCCN1S(=O)(=O)N1CCN(CC=2C=CC=CC=2)CC1 Chemical compound OC(=O)C1CCCCN1S(=O)(=O)N1CCN(CC=2C=CC=CC=2)CC1 AULWUKYPIURLMH-UHFFFAOYSA-N 0.000 claims description 2
LQLAJCXFQSUOBJ-UHFFFAOYSA-N OC(=O)C1CCOCC1SCCC1=CC=C(C=2C=CC=CC=2)C=C1 Chemical compound OC(=O)C1CCOCC1SCCC1=CC=C(C=2C=CC=CC=2)C=C1 LQLAJCXFQSUOBJ-UHFFFAOYSA-N 0.000 claims description 2
WQMAKUWCYSZMSW-UHFFFAOYSA-N OC(=O)C1CSCCN1S(=O)(=O)c1ccccc1Oc1ccc(F)cc1 Chemical compound OC(=O)C1CSCCN1S(=O)(=O)c1ccccc1Oc1ccc(F)cc1 WQMAKUWCYSZMSW-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
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
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 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 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
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
150000001993 dienes Chemical class 0.000 claims description 2
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 claims description 2
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 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
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
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000004404 heteroalkyl group Chemical group 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 2
125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
AFIOMDUVJXAUEG-UHFFFAOYSA-N methyl 2-amino-4-[2-[[4-(hydroxyamino)-4-oxo-2-phenylbutanoyl]amino]-4-methylpentanoyl]benzoate Chemical compound COC(C1=C(C=C(C=C1)C(C(CC(C)C)NC(C(C1=CC=CC=C1)CC(=O)NO)=O)=O)N)=O AFIOMDUVJXAUEG-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
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 description 2
OAIDITBEUBUZQS-UHFFFAOYSA-N methyl 4-[[2-[[2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(NC(=O)C(CC(C)C)CC(=O)NO)CC1=CNC2=CC=CC=C12 OAIDITBEUBUZQS-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
KCYFUXKMDULBRY-UHFFFAOYSA-N methyl 4-[[2-[[5-(hydroxyamino)-3-(3-phenylpropyl)-2,4-dihydropyrrole-3-carbonyl]amino]-4-methylpentanoyl]amino]benzoate Chemical compound COC(=O)C1=CC=C(NC(=O)C(CC(C)C)NC(=O)C2(CCCC3=CC=CC=C3)CN=C(C2)NO)C=C1 KCYFUXKMDULBRY-UHFFFAOYSA-N 0.000 claims description 2
ZGVAKHOTZNJEFL-UHFFFAOYSA-N methyl 4-[[2-[[5-(hydroxyamino)-3-pentan-3-yl-2,4-dihydropyrrole-3-carbonyl]amino]-4-methylpentanoyl]amino]benzoate Chemical compound CCC(CC)C1(CN=C(C1)NO)C(=O)NC(CC(C)C)C(=O)NC1=CC=C(C=C1)C(=O)OC ZGVAKHOTZNJEFL-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
JBWFRNLCWGJFFM-UHFFFAOYSA-N methyl 4-[[2-cyclohexyl-2-[[4-(hydroxyamino)-4-oxo-2-(2-phenylethyl)butanoyl]amino]propanoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(C)(C1CCCCC1)NC(=O)C(CC(=O)NO)CCC1=CC=CC=C1 JBWFRNLCWGJFFM-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
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
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
BFVSYQGIAMNOKW-UHFFFAOYSA-N n-hydroxy-1-(3-phenylpropyl)pyrrolidine-2-carboxamide Chemical compound ONC(=O)C1CCCN1CCCC1=CC=CC=C1 BFVSYQGIAMNOKW-UHFFFAOYSA-N 0.000 claims description 2
OIDRZRLFHSBEBK-UHFFFAOYSA-N n-hydroxy-2-(1-phenylethyl)benzamide Chemical compound C=1C=CC=C(C(=O)NO)C=1C(C)C1=CC=CC=C1 OIDRZRLFHSBEBK-UHFFFAOYSA-N 0.000 claims description 2
PBHMZBPUFFPILG-UHFFFAOYSA-N n-hydroxy-2-[3-(3-hydroxyphenyl)propyl]benzamide Chemical compound ONC(=O)C1=CC=CC=C1CCCC1=CC=CC(O)=C1 PBHMZBPUFFPILG-UHFFFAOYSA-N 0.000 claims description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
235000021313 oleic acid Nutrition 0.000 claims description 2
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 claims description 2
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 2
HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 2
XIMBESZRBTVIOD-UHFFFAOYSA-N piperidine-2-carboxamide Chemical compound NC(=O)C1CCCCN1 XIMBESZRBTVIOD-UHFFFAOYSA-N 0.000 claims description 2
229940080818 propionamide Drugs 0.000 claims description 2
URXNOJQCVQXMCT-UHFFFAOYSA-N pyrrolidine-1-carbothioic s-acid Chemical compound SC(=O)N1CCCC1 URXNOJQCVQXMCT-UHFFFAOYSA-N 0.000 claims description 2
239000001632 sodium acetate Substances 0.000 claims description 2
235000017281 sodium acetate Nutrition 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
GJOCABIDMCKCEG-INIZCTEOSA-N (2s)-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound 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 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
PTQXTEKSNBVPQJ-UHFFFAOYSA-N Avasimibe Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C PTQXTEKSNBVPQJ-UHFFFAOYSA-N 0.000 claims 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
HLXRVYRVLWFWRM-HXUWFJFHSA-N (2R)-2-[[4-(4-iodophenoxy)phenyl]sulfonylamino]-3-methyl-3-pyridin-2-ylsulfanylbutanoic acid Chemical compound CC(C)([C@@H](C(=O)O)NS(=O)(=O)C1=CC=C(C=C1)OC2=CC=C(C=C2)I)SC3=CC=CC=N3 HLXRVYRVLWFWRM-HXUWFJFHSA-N 0.000 claims 1
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 1
GJOCABIDMCKCEG-MRXNPFEDSA-N (2r)-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(Br)C=C1 GJOCABIDMCKCEG-MRXNPFEDSA-N 0.000 claims 1
LDYKRMJEFNIWLO-INIZCTEOSA-N (2r)-2-[[4-(4-fluorophenoxy)phenyl]sulfonylamino]-3,3-dimethylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@H](C(C)(C)C)C(O)=O)=CC=C1OC1=CC=C(F)C=C1 LDYKRMJEFNIWLO-INIZCTEOSA-N 0.000 claims 1
GKLQOPGOSKTMDW-QFIPXVFZSA-N (2s)-2-(9h-fluoren-2-ylsulfonylamino)-4-phenylbutanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2C(C3=CC=CC=C3C2)=CC=1)CC1=CC=CC=C1 GKLQOPGOSKTMDW-QFIPXVFZSA-N 0.000 claims 1
IFIMFQCOUJBVCU-INIZCTEOSA-N (2s)-2-[[4-(3,4-dibromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(Br)C(Br)=C1 IFIMFQCOUJBVCU-INIZCTEOSA-N 0.000 claims 1
NEOOWKPSCAQYPI-INIZCTEOSA-N (2s)-2-[[4-(3-bromophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC(Br)=C1 NEOOWKPSCAQYPI-INIZCTEOSA-N 0.000 claims 1
WJFKRCVNGHZYFA-INIZCTEOSA-N (2s)-2-[[4-(3-fluorophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC(F)=C1 WJFKRCVNGHZYFA-INIZCTEOSA-N 0.000 claims 1
UWHPJOBPMXNVII-INIZCTEOSA-N (2s)-2-[[4-(4-bromo-2-fluorophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(Br)C=C1F UWHPJOBPMXNVII-INIZCTEOSA-N 0.000 claims 1
QVNUOLHHXUUNEH-KRWDZBQOSA-N (2s)-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-4-methylpentanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](CC(C)C)C(O)=O)=CC=C1C1=CC=C(Br)C=C1 QVNUOLHHXUUNEH-KRWDZBQOSA-N 0.000 claims 1
UJVIDDIDLMDARE-JTQLQIEISA-N (2s)-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]propanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C)C(O)=O)=CC=C1C1=CC=C(Br)C=C1 UJVIDDIDLMDARE-JTQLQIEISA-N 0.000 claims 1
PTONAIKVYGVBIS-INIZCTEOSA-N (2s)-2-[[4-(4-chlorophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(Cl)C=C1 PTONAIKVYGVBIS-INIZCTEOSA-N 0.000 claims 1
AGRDSOUIPBKOKQ-KRWDZBQOSA-N (2s)-2-[[4-(4-cyanophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(C#N)C=C1 AGRDSOUIPBKOKQ-KRWDZBQOSA-N 0.000 claims 1
INVXSBCIDABVMG-INIZCTEOSA-N (2s)-2-[[4-(4-fluorophenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(F)C=C1 INVXSBCIDABVMG-INIZCTEOSA-N 0.000 claims 1
MDWFJTBWOFNAQX-KRWDZBQOSA-N (2s)-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)C=C1 MDWFJTBWOFNAQX-KRWDZBQOSA-N 0.000 claims 1
HXNNABWLGZRTMD-INIZCTEOSA-N (2s)-3-methyl-2-[[4-[4-(trifluoromethyl)phenyl]phenyl]sulfonylamino]butanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=C(C(F)(F)F)C=C1 HXNNABWLGZRTMD-INIZCTEOSA-N 0.000 claims 1
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JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 1
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XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
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125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
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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
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
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JTNXQVCPQMQLHK-UHFFFAOYSA-N thioacetone Chemical compound CC(C)=S JTNXQVCPQMQLHK-UHFFFAOYSA-N 0.000 description 1
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JPZXHKDZASGCLU-LBPRGKRZSA-N β-(2-naphthyl)-alanine Chemical compound C1=CC=CC2=CC(C[C@H](N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-LBPRGKRZSA-N 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)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (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)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Indole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Furan Compounds (AREA)
Pyridine Compounds (AREA)
Pyrane Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Quinoline Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

SK50-2001A 1998-07-21 1999-06-18 Coadministration of acat and mmp inhibitors for the treatment of atherosclerotic lesions SK502001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US9363998P	1998-07-21	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
SK502001A3 true SK502001A3 (en)	2002-06-04

Family

ID=22239992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK50-2001A SK502001A3 (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 (is)
JP (1)	JP2002521328A (is)
KR (1)	KR20010083134A (is)
CN (1)	CN1310629A (is)
AP (1)	AP2001002035A0 (is)
AU (1)	AU4701799A (is)
BG (1)	BG105162A (is)
BR (1)	BR9912296A (is)
CA (1)	CA2335062A1 (is)
CZ (1)	CZ2001126A3 (is)
EA (1)	EA200100153A1 (is)
EE (1)	EE200100046A (is)
HR (1)	HRP20010055A2 (is)
HU (1)	HUP0102880A3 (is)
ID (1)	ID30030A (is)
IL (1)	IL140982A0 (is)
IS (1)	IS5809A (is)
NO (1)	NO20010291L (is)
OA (1)	OA11584A (is)
PL (1)	PL346011A1 (is)
SK (1)	SK502001A3 (is)
TR (1)	TR200100205T2 (is)
WO (1)	WO2000004892A2 (is)
YU (1)	YU3501A (is)
ZA (1)	ZA200100294B (is)

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CN1414848A (zh) *	1999-11-05	2003-04-30	沃尼尔·朗伯公司	Acat抑制剂对斑块破裂的预防
CO5261615A1 (es)	1999-12-01	2003-03-31	Agouron Pharma	Compuestos, composiciones y metodos para estimular el crecimiento y elongacion de neuronas
JP2003534239A (ja) *	1999-12-17	2003-11-18	ヴァージコア・インコーポレーテッド	新規なスクシナート化合物、組成物、並びに使用及び調製方法
MXPA03001857A (es) *	2000-09-01	2003-06-04	Sankyo Co	Composicones medicinales.
GB0100761D0 (en)	2001-01-11	2001-02-21	Biocompatibles Ltd	Drug delivery from stents
DE60321775D1 (de) *	2002-04-03	2008-08-07	Topotarget Uk Ltd	Carbaminsäurederivate enthaltend eine piperazin verknüpfung als hdac-inhibitoren
KR101011373B1 (ko) *	2002-07-11	2011-01-28	비큐론 파마슈티컬스 인코포레이티드	항균작용을 갖는 ｎ-히드록시아미드 유도체
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
US20180000817A1 (en) *	2015-01-15	2018-01-04	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
WO2025224168A1 (en)	2024-04-24	2025-10-30	Idorsia Pharmaceuticals Ltd	Aryl sulfone and sulfanone derivatives as orexin receptor modulators

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* Cited by examiner, † Cited by third party
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
CZ26198A3 (cs) *	1995-08-04	1998-07-15	Warner-Lambert Company	Použití derivátů kyseliny amidosírové, acyl-sulfonamidů nebo sulfonyl-karbamatů pro výrobu léčiva s účinky snížení hladin lipoproteinů
ES2167733T3 (es) *	1996-05-17	2002-05-16	Warner Lambert Co	Inhibidores de metaloproteinasa matricial de bifenilsulfonamida.
CA2256716A1 (en) *	1996-09-04	1998-03-12	Warner-Lambert Company	Matrix metalloproteinase inhibitors and their therapeutic uses

1999
- 1999-06-18 CZ CZ2001126A patent/CZ2001126A3/cs unknown
- 1999-06-18 AU AU47017/99A patent/AU4701799A/en not_active Abandoned
- 1999-06-18 SK SK50-2001A patent/SK502001A3/sk unknown
- 1999-06-18 HR HR20010055A patent/HRP20010055A2/hr not_active Application Discontinuation
- 1999-06-18 JP JP2000560885A patent/JP2002521328A/ja active Pending
- 1999-06-18 PL PL99346011A patent/PL346011A1/xx unknown
- 1999-06-18 HU HU0102880A patent/HUP0102880A3/hu unknown
- 1999-06-18 EP EP99930483A patent/EP1098662A2/en not_active Withdrawn
- 1999-06-18 EA EA200100153A patent/EA200100153A1/ru unknown
- 1999-06-18 KR KR1020017000930A patent/KR20010083134A/ko not_active Withdrawn
- 1999-06-18 TR TR2001/00205T patent/TR200100205T2/xx unknown
- 1999-06-18 EE EEP200100046A patent/EE200100046A/xx unknown
- 1999-06-18 ID IDW20010333A patent/ID30030A/id unknown
- 1999-06-18 AP APAP/P/2001/002035A patent/AP2001002035A0/en unknown
- 1999-06-18 IL IL14098299A patent/IL140982A0/xx unknown
- 1999-06-18 YU YU3501A patent/YU3501A/sh unknown
- 1999-06-18 CA CA002335062A patent/CA2335062A1/en not_active Abandoned
- 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 Ceased
- 1999-06-18 OA OA1200100022A patent/OA11584A/en unknown
- 1999-06-18 CN CN99808958A patent/CN1310629A/zh active Pending
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/NO20010291L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
YU3501A (sh)	2005-06-10
ZA200100294B (en)	2002-01-10
OA11584A (en)	2004-07-20
AP2001002035A0 (en)	2001-03-31
NO20010291D0 (no)	2001-01-18
PL346011A1 (en)	2002-01-14
HRP20010055A2 (en)	2002-04-30
HUP0102880A2 (en)	2002-06-29
WO2000004892A2 (en)	2000-02-03
CZ2001126A3 (cs)	2002-01-16
CN1310629A (zh)	2001-08-29
WO2000004892A3 (en)	2000-05-18
EA200100153A1 (ru)	2001-08-27
IL140982A0 (en)	2002-02-10
EP1098662A2 (en)	2001-05-16
KR20010083134A (ko)	2001-08-31
JP2002521328A (ja)	2002-07-16
BR9912296A (pt)	2001-04-17
EE200100046A (et)	2002-06-17
ID30030A (id)	2001-11-01
AU4701799A (en)	2000-02-14
BG105162A (en)	2001-12-29
HUP0102880A3 (en)	2002-11-28
TR200100205T2 (tr)	2001-05-21
IS5809A (is)	2001-01-12
CA2335062A1 (en)	2000-02-03
NO20010291L (no)	2001-01-18

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