JP4833072B2 - アミノ酸フェノキシエーテル - Google Patents
アミノ酸フェノキシエーテル Download PDFInfo
- Publication number
- JP4833072B2 JP4833072B2 JP2006536536A JP2006536536A JP4833072B2 JP 4833072 B2 JP4833072 B2 JP 4833072B2 JP 2006536536 A JP2006536536 A JP 2006536536A JP 2006536536 A JP2006536536 A JP 2006536536A JP 4833072 B2 JP4833072 B2 JP 4833072B2
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- JP
- Japan
- Prior art keywords
- amino
- compound
- general formula
- salt
- dione
- 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.)
- Expired - Fee Related
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- 150000001413 amino acids Chemical class 0.000 title claims description 7
- XQYMIMUDVJCMLU-UHFFFAOYSA-N phenoxyperoxybenzene Chemical compound C=1C=CC=CC=1OOOC1=CC=CC=C1 XQYMIMUDVJCMLU-UHFFFAOYSA-N 0.000 title 1
- -1 amino acid phenyl ethers Chemical class 0.000 claims abstract description 37
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 19
- 208000008589 Obesity Diseases 0.000 claims abstract description 18
- 235000020824 obesity Nutrition 0.000 claims abstract description 18
- 230000004054 inflammatory process Effects 0.000 claims abstract description 17
- 206010061218 Inflammation Diseases 0.000 claims abstract description 14
- 208000026278 immune system disease Diseases 0.000 claims abstract description 9
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims description 184
- 150000001875 compounds Chemical class 0.000 claims description 130
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 25
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 14
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 208000023275 Autoimmune disease Diseases 0.000 claims description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 11
- 239000008103 glucose Substances 0.000 claims description 11
- 235000001014 amino acid Nutrition 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
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- 108090001005 Interleukin-6 Proteins 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 8
- 206010022489 Insulin Resistance Diseases 0.000 claims description 8
- 235000004279 alanine Nutrition 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 230000021523 carboxylation Effects 0.000 claims description 7
- 238000006473 carboxylation reaction Methods 0.000 claims description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 7
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- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 5
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- 239000003937 drug carrier Substances 0.000 claims description 3
- OGXRFCWCSMPYKS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 OGXRFCWCSMPYKS-UHFFFAOYSA-N 0.000 claims description 3
- TWWVONQNEVLIIH-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 TWWVONQNEVLIIH-UHFFFAOYSA-N 0.000 claims description 3
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 235000021588 free fatty acids Nutrition 0.000 claims description 2
- 230000006698 induction Effects 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 7
- 241000255925 Diptera Species 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 3
- 206010003645 Atopy Diseases 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 159000000003 magnesium salts Chemical class 0.000 claims 1
- 150000004702 methyl esters Chemical group 0.000 claims 1
- 150000003667 tyrosine derivatives Chemical class 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 25
- 230000000694 effects Effects 0.000 abstract description 10
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- 208000025966 Neurological disease Diseases 0.000 abstract description 5
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- 102000004127 Cytokines Human genes 0.000 description 18
- 108090000695 Cytokines Proteins 0.000 description 18
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
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- LJCQEOGRMPCFTI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)F)=CC=C1CC1C(=O)NC(=O)O1 LJCQEOGRMPCFTI-UHFFFAOYSA-N 0.000 description 1
- CODCYMHHTBNREB-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-methylphenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C)=CC=C1CC1C(=O)NC(=O)O1 CODCYMHHTBNREB-UHFFFAOYSA-N 0.000 description 1
- PGUVBVMVOHNTGJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-2-nitrophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1CC1C(=O)NC(=O)O1 PGUVBVMVOHNTGJ-UHFFFAOYSA-N 0.000 description 1
- XMJVDOJWDCSGAM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3,5-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC(F)=C1CC1C(=O)NC(=O)O1 XMJVDOJWDCSGAM-UHFFFAOYSA-N 0.000 description 1
- TVPMPZYCRJLAFW-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1C(F)(F)F)=CC=C1CC1C(=O)NC(=O)O1 TVPMPZYCRJLAFW-UHFFFAOYSA-N 0.000 description 1
- PLFGIUSCVHVKOS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]-3-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC=C1CC1C(=O)NC(=O)O1 PLFGIUSCVHVKOS-UHFFFAOYSA-N 0.000 description 1
- MROIPHQFYPGLMQ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2,3-difluorophenyl]propanoate Chemical compound FC1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 MROIPHQFYPGLMQ-UHFFFAOYSA-N 0.000 description 1
- GPQMLUWMSJGVKH-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 GPQMLUWMSJGVKH-UHFFFAOYSA-N 0.000 description 1
- FCXZYYNRFATUSJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 FCXZYYNRFATUSJ-UHFFFAOYSA-N 0.000 description 1
- WXOLLQHWOZXMKM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 WXOLLQHWOZXMKM-UHFFFAOYSA-N 0.000 description 1
- OMPJEKQAPFHGLL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 OMPJEKQAPFHGLL-UHFFFAOYSA-N 0.000 description 1
- HYQIZYXZQSYDCJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3,5-difluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC(F)=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 HYQIZYXZQSYDCJ-UHFFFAOYSA-N 0.000 description 1
- MPFQVGALPSRHIA-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoate Chemical compound FC(F)(F)C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 MPFQVGALPSRHIA-UHFFFAOYSA-N 0.000 description 1
- CORWUWCGIXKJFS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]-3-fluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 CORWUWCGIXKJFS-UHFFFAOYSA-N 0.000 description 1
- OOAGJTGMKGAQOI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 OOAGJTGMKGAQOI-UHFFFAOYSA-N 0.000 description 1
- WQTSSWGQDUMQBL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2,3-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1F)F)=CC=C1C=C1C(=O)NC(=O)O1 WQTSSWGQDUMQBL-UHFFFAOYSA-N 0.000 description 1
- BAAZBUVOUCRIBR-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)O1 BAAZBUVOUCRIBR-UHFFFAOYSA-N 0.000 description 1
- XVINYCICGTVTNH-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-methylphenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C)=CC=C1C=C1C(=O)NC(=O)O1 XVINYCICGTVTNH-UHFFFAOYSA-N 0.000 description 1
- GFYDLBXGLDJUNT-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-2-nitrophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1C=C1C(=O)NC(=O)O1 GFYDLBXGLDJUNT-UHFFFAOYSA-N 0.000 description 1
- JPSREXAVJGNSTI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3,5-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC(F)=C1C=C1C(=O)NC(=O)O1 JPSREXAVJGNSTI-UHFFFAOYSA-N 0.000 description 1
- GKBHJRWEZJZORU-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)O1 GKBHJRWEZJZORU-UHFFFAOYSA-N 0.000 description 1
- YLEDUEGAAOPBIF-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]-3-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC=C1C=C1C(=O)NC(=O)O1 YLEDUEGAAOPBIF-UHFFFAOYSA-N 0.000 description 1
- JETAGVVACKUJMX-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2,3-difluorophenyl]propanoate Chemical compound FC1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 JETAGVVACKUJMX-UHFFFAOYSA-N 0.000 description 1
- NXBIIHZISQJJRE-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 NXBIIHZISQJJRE-UHFFFAOYSA-N 0.000 description 1
- CMNZTOYBERNPGD-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 CMNZTOYBERNPGD-UHFFFAOYSA-N 0.000 description 1
- FSCABNWMGYWGCG-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 FSCABNWMGYWGCG-UHFFFAOYSA-N 0.000 description 1
- KKVBUVXERMHOBV-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 KKVBUVXERMHOBV-UHFFFAOYSA-N 0.000 description 1
- AVYQFTIBNBIACA-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3,5-difluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC(F)=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 AVYQFTIBNBIACA-UHFFFAOYSA-N 0.000 description 1
- PBKXJYGUFLXAJS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoate Chemical compound FC(F)(F)C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 PBKXJYGUFLXAJS-UHFFFAOYSA-N 0.000 description 1
- UVDFUWKKHVEMSJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]-3-fluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 UVDFUWKKHVEMSJ-UHFFFAOYSA-N 0.000 description 1
- GAQWTIWBVKFNNE-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 GAQWTIWBVKFNNE-UHFFFAOYSA-N 0.000 description 1
- GEYHSNPJQXXUTH-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2,3-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1F)F)=CC=C1CC1C(=O)NC(=O)S1 GEYHSNPJQXXUTH-UHFFFAOYSA-N 0.000 description 1
- BWVSFAQOCHIQKO-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1CC1C(=O)NC(=O)S1 BWVSFAQOCHIQKO-UHFFFAOYSA-N 0.000 description 1
- OHRGYUROFCVMNL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)F)=CC=C1CC1C(=O)NC(=O)S1 OHRGYUROFCVMNL-UHFFFAOYSA-N 0.000 description 1
- JJBYDFLJMUHEMF-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methylphenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C)=CC=C1CC1C(=O)NC(=O)S1 JJBYDFLJMUHEMF-UHFFFAOYSA-N 0.000 description 1
- LQOFRSDZPNFATG-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-nitrophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1CC1C(=O)NC(=O)S1 LQOFRSDZPNFATG-UHFFFAOYSA-N 0.000 description 1
- LNXIYYYEFBIJMP-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-3,5-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC(F)=C1CC1C(=O)NC(=O)S1 LNXIYYYEFBIJMP-UHFFFAOYSA-N 0.000 description 1
- GUPWMRKXFIBJSD-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1C(F)(F)F)=CC=C1CC1C(=O)NC(=O)S1 GUPWMRKXFIBJSD-UHFFFAOYSA-N 0.000 description 1
- SJIUIVVHNVNIEV-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-3-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC=C1CC1C(=O)NC(=O)S1 SJIUIVVHNVNIEV-UHFFFAOYSA-N 0.000 description 1
- GJGYTLHGCWICCL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 GJGYTLHGCWICCL-UHFFFAOYSA-N 0.000 description 1
- ZIIYOFPXXRQIEA-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 ZIIYOFPXXRQIEA-UHFFFAOYSA-N 0.000 description 1
- OFULTZRBCZWYBV-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 OFULTZRBCZWYBV-UHFFFAOYSA-N 0.000 description 1
- MBSYURHGUNCPQY-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 MBSYURHGUNCPQY-UHFFFAOYSA-N 0.000 description 1
- SDZHNZRFCJBBOX-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-3,5-difluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC(F)=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 SDZHNZRFCJBBOX-UHFFFAOYSA-N 0.000 description 1
- MUOWZEKPCFZMCB-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoate Chemical compound FC(F)(F)C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 MUOWZEKPCFZMCB-UHFFFAOYSA-N 0.000 description 1
- DMBCGKJRKLTRTJ-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-3-fluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 DMBCGKJRKLTRTJ-UHFFFAOYSA-N 0.000 description 1
- USGKBRMYSUMVLX-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 USGKBRMYSUMVLX-UHFFFAOYSA-N 0.000 description 1
- GHCFECFAIHVFKI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2,3-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1F)F)=CC=C1C=C1C(=O)NC(=O)S1 GHCFECFAIHVFKI-UHFFFAOYSA-N 0.000 description 1
- SPSPQVIEQWMMAM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)S1 SPSPQVIEQWMMAM-UHFFFAOYSA-N 0.000 description 1
- IGONZXKWPXGJJN-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)F)=CC=C1C=C1C(=O)NC(=O)S1 IGONZXKWPXGJJN-UHFFFAOYSA-N 0.000 description 1
- DQOCRTXCKGTRGM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-methylphenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)C)=CC=C1C=C1C(=O)NC(=O)S1 DQOCRTXCKGTRGM-UHFFFAOYSA-N 0.000 description 1
- SSSCNHINVDTLTF-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-nitrophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C(=C1)[N+]([O-])=O)=CC=C1C=C1C(=O)NC(=O)S1 SSSCNHINVDTLTF-UHFFFAOYSA-N 0.000 description 1
- WJHASNZHBNHDLG-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-3,5-difluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC(F)=C1C=C1C(=O)NC(=O)S1 WJHASNZHBNHDLG-UHFFFAOYSA-N 0.000 description 1
- RQJHTLOJRHUWAP-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-3-(trifluoromethyl)phenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)S1 RQJHTLOJRHUWAP-UHFFFAOYSA-N 0.000 description 1
- VCSWLAKPJQFFCL-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-3-fluorophenoxy]phenyl]propanoate Chemical compound C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1F)=CC=C1C=C1C(=O)NC(=O)S1 VCSWLAKPJQFFCL-UHFFFAOYSA-N 0.000 description 1
- PQULEHSJUOJFFT-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2,3-difluorophenyl]propanoate Chemical compound FC1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 PQULEHSJUOJFFT-UHFFFAOYSA-N 0.000 description 1
- TWSFIKODCFHUIP-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2-(trifluoromethyl)phenyl]propanoate Chemical compound C1=C(C(F)(F)F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 TWSFIKODCFHUIP-UHFFFAOYSA-N 0.000 description 1
- FBCABQNGCOSCIR-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2-fluorophenyl]propanoate Chemical compound C1=C(F)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 FBCABQNGCOSCIR-UHFFFAOYSA-N 0.000 description 1
- RIQOOPZWTDWYPS-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2-methylphenyl]propanoate Chemical compound C1=C(C)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 RIQOOPZWTDWYPS-UHFFFAOYSA-N 0.000 description 1
- FPOKHDJYQNVUQK-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 FPOKHDJYQNVUQK-UHFFFAOYSA-N 0.000 description 1
- JIFOUHKXLHEKOI-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-3,5-difluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC(F)=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 JIFOUHKXLHEKOI-UHFFFAOYSA-N 0.000 description 1
- CGJPRWMVBLTWQM-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-3-(trifluoromethyl)phenyl]propanoate Chemical compound FC(F)(F)C1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 CGJPRWMVBLTWQM-UHFFFAOYSA-N 0.000 description 1
- NFBRNCTYXWMZOA-UHFFFAOYSA-N methyl 2-amino-3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]-3-fluorophenyl]propanoate Chemical compound FC1=CC(CC(N)C(=O)OC)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 NFBRNCTYXWMZOA-UHFFFAOYSA-N 0.000 description 1
- NQIFXJSLCUJHBB-UHFFFAOYSA-N methyl 3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CC(C)(C)OC(=O)NC(C(=O)OC)CC1=CC=C(O)C=C1 NQIFXJSLCUJHBB-UHFFFAOYSA-N 0.000 description 1
- USOQPLZEWYDGCA-UHFFFAOYSA-N methyl 3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-yl)methyl]phenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC(CC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)O1 USOQPLZEWYDGCA-UHFFFAOYSA-N 0.000 description 1
- ZMEMSCVLZHHICN-UHFFFAOYSA-N methyl 3-[4-[4-[(2,4-dioxo-1,3-oxazolidin-5-ylidene)methyl]phenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC(CC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)O1 ZMEMSCVLZHHICN-UHFFFAOYSA-N 0.000 description 1
- AWKFWEAITGHEBY-UHFFFAOYSA-N methyl 3-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=CC(CC(C(=O)OC)NC(=O)OC(C)(C)C)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 AWKFWEAITGHEBY-UHFFFAOYSA-N 0.000 description 1
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- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| US10/356,113 US6794401B2 (en) | 2003-01-17 | 2003-01-31 | Amino acid phenoxy ethers |
| US10/356,113 | 2003-01-31 | ||
| PCT/US2004/000790 WO2004066964A2 (en) | 2003-01-17 | 2004-01-13 | Amino acid phenoxy ethers |
Publications (3)
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| JP2007501288A JP2007501288A (ja) | 2007-01-25 |
| JP2007501288A5 JP2007501288A5 (https=) | 2008-12-11 |
| JP4833072B2 true JP4833072B2 (ja) | 2011-12-07 |
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| EP (1) | EP1583529B9 (https=) |
| JP (1) | JP4833072B2 (https=) |
| KR (1) | KR101085315B1 (https=) |
| AT (1) | ATE532510T1 (https=) |
| AU (1) | AU2004207449A1 (https=) |
| BR (1) | BRPI0406772B1 (https=) |
| CA (1) | CA2513496C (https=) |
| CY (1) | CY1112673T1 (https=) |
| DK (1) | DK1583529T3 (https=) |
| EA (1) | EA200501078A1 (https=) |
| ES (1) | ES2374724T3 (https=) |
| MA (1) | MA27658A1 (https=) |
| MX (1) | MXPA05007684A (https=) |
| NO (1) | NO330984B1 (https=) |
| NZ (1) | NZ541328A (https=) |
| PT (1) | PT1583529E (https=) |
| SI (1) | SI1583529T1 (https=) |
| TW (1) | TWI325420B (https=) |
| WO (1) | WO2004066964A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7521465B2 (en) * | 2003-01-17 | 2009-04-21 | Bexel Pharmaceuticals, Inc. | Diphenyl ether derivatives |
| US7781464B2 (en) * | 2003-01-17 | 2010-08-24 | Bexel Pharmaceuticals, Inc. | Heterocyclic diphenyl ethers |
| US7087576B2 (en) * | 2003-10-07 | 2006-08-08 | Bexel Pharmaceuticals, Inc. | Dipeptide phenyl ethers |
| US7592486B2 (en) * | 2004-09-16 | 2009-09-22 | Board Of Regents Of The University Of Nebraska | Anhydrous fluoride salts and reagents and methods for their production |
| KR20080025662A (ko) * | 2005-03-18 | 2008-03-21 | 오키드 케미칼즈 앤드 파마수티컬즈 리미티드 | 신규 티로신 유도체 |
| US20090203744A1 (en) * | 2005-07-29 | 2009-08-13 | Pande Y Surendrakumar Satyanarayan | Novel pyridine derivatives |
| WO2008019306A2 (en) * | 2006-08-04 | 2008-02-14 | Decode Genetics Ehf | Aryl amino acid derivatives as inhibitors of lta4h (leukotriene a4 hydrolase) for treating inflammation |
| CN101784269A (zh) * | 2007-06-26 | 2010-07-21 | 莱西肯医药有限公司 | 治疗由5-羟色胺介导的疾病和病症的方法 |
| CN101815534A (zh) | 2007-07-11 | 2010-08-25 | 莱西肯医药有限公司 | 用于治疗肺动脉高压以及相关疾病和病症的方法和组合物 |
| WO2009030968A1 (en) * | 2007-09-05 | 2009-03-12 | Orchid Research Laboratories Limited | Mao a inhibitors with a diphenyl ether-substructure. |
| ATE536347T1 (de) | 2008-05-20 | 2011-12-15 | Merck Sharp & Dohme | Effiziente herstellung heterologer proteine unter verwendung von mannosyltransferaseinhibitoren |
| US20140187594A1 (en) | 2010-07-28 | 2014-07-03 | Orchid Chemicals And Pharmaceuticals Ltd | Diphenyl ether compounds for the treatment of liver, lung disorders, diabetic complications and cardiovascular diseases |
| JP6014816B2 (ja) | 2011-05-10 | 2016-10-26 | 国立大学法人神戸大学 | Ras機能阻害作用を有するチオキソチアゾリジン誘導体 |
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- 2004-01-13 CA CA2513496A patent/CA2513496C/en not_active Expired - Fee Related
- 2004-01-13 EP EP04701752A patent/EP1583529B9/en not_active Expired - Lifetime
- 2004-01-13 AU AU2004207449A patent/AU2004207449A1/en not_active Abandoned
- 2004-01-13 SI SI200431804T patent/SI1583529T1/sl unknown
- 2004-01-13 KR KR1020057013193A patent/KR101085315B1/ko not_active Expired - Fee Related
- 2004-01-13 DK DK04701752.0T patent/DK1583529T3/da active
- 2004-01-13 AT AT04701752T patent/ATE532510T1/de active
- 2004-01-13 EA EA200501078A patent/EA200501078A1/ru unknown
- 2004-01-13 MX MXPA05007684A patent/MXPA05007684A/es active IP Right Grant
- 2004-01-13 PT PT04701752T patent/PT1583529E/pt unknown
- 2004-01-13 BR BRPI0406772A patent/BRPI0406772B1/pt not_active IP Right Cessation
- 2004-01-13 NZ NZ541328A patent/NZ541328A/en not_active IP Right Cessation
- 2004-01-13 WO PCT/US2004/000790 patent/WO2004066964A2/en not_active Ceased
- 2004-01-13 JP JP2006536536A patent/JP4833072B2/ja not_active Expired - Fee Related
- 2004-01-14 TW TW093100932A patent/TWI325420B/zh not_active IP Right Cessation
- 2004-09-21 US US10/947,047 patent/US20050096366A1/en not_active Abandoned
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2005
- 2005-08-01 NO NO20053714A patent/NO330984B1/no not_active IP Right Cessation
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2012
- 2012-02-09 CY CY20121100137T patent/CY1112673T1/el unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| NZ541328A (en) | 2008-11-28 |
| WO2004066964A2 (en) | 2004-08-12 |
| AU2004207449A1 (en) | 2004-08-12 |
| WO2004066964A3 (en) | 2005-02-24 |
| ES2374724T3 (es) | 2012-02-21 |
| EP1583529A2 (en) | 2005-10-12 |
| KR101085315B1 (ko) | 2011-11-22 |
| US6794401B2 (en) | 2004-09-21 |
| EP1583529B1 (en) | 2011-11-09 |
| BRPI0406772A (pt) | 2005-12-27 |
| CA2513496A1 (en) | 2004-08-12 |
| MA27658A1 (fr) | 2005-12-01 |
| EP1583529B9 (en) | 2012-04-04 |
| SI1583529T1 (sl) | 2012-02-29 |
| DK1583529T3 (da) | 2012-01-23 |
| CY1112673T1 (el) | 2016-02-10 |
| TW200418792A (en) | 2004-10-01 |
| ATE532510T1 (de) | 2011-11-15 |
| JP2007501288A (ja) | 2007-01-25 |
| MXPA05007684A (es) | 2006-03-10 |
| PT1583529E (pt) | 2012-02-13 |
| BRPI0406772B1 (pt) | 2016-08-23 |
| CA2513496C (en) | 2013-05-14 |
| NO330984B1 (no) | 2011-08-29 |
| EP1583529A4 (en) | 2007-07-04 |
| WO2004066964A9 (en) | 2004-09-02 |
| NO20053714D0 (no) | 2005-08-01 |
| EA200501078A1 (ru) | 2006-02-24 |
| KR20050092764A (ko) | 2005-09-22 |
| TWI325420B (en) | 2010-06-01 |
| NO20053714L (no) | 2005-10-11 |
| US20040142991A1 (en) | 2004-07-22 |
| US20050096366A1 (en) | 2005-05-05 |
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