JP2004524294A5 - - Google Patents
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- JP2004524294A5 JP2004524294A5 JP2002557903A JP2002557903A JP2004524294A5 JP 2004524294 A5 JP2004524294 A5 JP 2004524294A5 JP 2002557903 A JP2002557903 A JP 2002557903A JP 2002557903 A JP2002557903 A JP 2002557903A JP 2004524294 A5 JP2004524294 A5 JP 2004524294A5
- Authority
- JP
- Japan
- Prior art keywords
- alpha
- mercaptopropyl
- carboxy
- compound
- acid
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 27
- 239000008194 pharmaceutical composition Substances 0.000 claims 24
- 102000003958 Glutamate Carboxypeptidase II Human genes 0.000 claims 18
- 108090000369 Glutamate Carboxypeptidase II Proteins 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- -1 nitro, phenyl Chemical group 0.000 claims 17
- 201000010099 disease Diseases 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 208000035475 disorder Diseases 0.000 claims 12
- 230000000694 effects Effects 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 230000005856 abnormality Effects 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 102000004887 Transforming Growth Factor beta Human genes 0.000 claims 7
- 108090001012 Transforming Growth Factor beta Proteins 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 7
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 claims 7
- 208000012902 Nervous system disease Diseases 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 230000002401 inhibitory effect Effects 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 229930195712 glutamate Natural products 0.000 claims 5
- 208000024891 symptom Diseases 0.000 claims 5
- 230000033115 angiogenesis Effects 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 4
- 208000017497 prostate disease Diseases 0.000 claims 4
- JKPYNGWTXQIZFC-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)benzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(C(O)=O)=C1 JKPYNGWTXQIZFC-UHFFFAOYSA-N 0.000 claims 3
- 238000009007 Diagnostic Kit Methods 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 239000012530 fluid Substances 0.000 claims 3
- 238000003384 imaging method Methods 0.000 claims 3
- 239000003550 marker Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 230000001537 neural effect Effects 0.000 claims 3
- 210000002569 neuron Anatomy 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 210000001519 tissue Anatomy 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000016192 Demyelinating disease Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- MBRAISPPYRWIEP-UHFFFAOYSA-N 2-(1-carboxy-4-sulfanylbutoxy)benzoic acid Chemical compound SCCCC(C(=O)O)OC1=CC=CC=C1C(O)=O MBRAISPPYRWIEP-UHFFFAOYSA-N 0.000 claims 1
- AJRYUIBEXXWDCQ-UHFFFAOYSA-N 2-(2-carboxy-5-sulfanylpentyl)benzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC=C1C(O)=O AJRYUIBEXXWDCQ-UHFFFAOYSA-N 0.000 claims 1
- IPZDSCZXSXITRA-UHFFFAOYSA-N 2-(3,5-dimethoxyphenoxy)-5-sulfanylpentanoic acid Chemical compound COC1=CC(OC)=CC(OC(CCCS)C(O)=O)=C1 IPZDSCZXSXITRA-UHFFFAOYSA-N 0.000 claims 1
- SCEOWAMGFIJJCG-UHFFFAOYSA-N 2-(3-acetamidophenoxy)-5-sulfanylpentanoic acid Chemical compound CC(=O)NC1=CC=CC(OC(CCCS)C(O)=O)=C1 SCEOWAMGFIJJCG-UHFFFAOYSA-N 0.000 claims 1
- FNWKMVIZLRVPFM-UHFFFAOYSA-N 2-(3-acetylphenoxy)-5-sulfanylpentanoic acid Chemical compound CC(=O)C1=CC=CC(OC(CCCS)C(O)=O)=C1 FNWKMVIZLRVPFM-UHFFFAOYSA-N 0.000 claims 1
- NCNYBAYYAFRTGD-UHFFFAOYSA-N 2-(3-hydroxyphenoxy)-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)OC1=CC=CC(O)=C1 NCNYBAYYAFRTGD-UHFFFAOYSA-N 0.000 claims 1
- MAEHSMNJMWMSLR-UHFFFAOYSA-N 2-(4-acetylphenoxy)-5-sulfanylpentanoic acid Chemical compound CC(=O)C1=CC=C(OC(CCCS)C(O)=O)C=C1 MAEHSMNJMWMSLR-UHFFFAOYSA-N 0.000 claims 1
- BBCKAXJYWIDLIE-UHFFFAOYSA-N 2-(naphthalen-2-ylmethyl)-5-sulfanylpentanoic acid Chemical compound C1=CC=CC2=CC(CC(CCCS)C(=O)O)=CC=C21 BBCKAXJYWIDLIE-UHFFFAOYSA-N 0.000 claims 1
- VORQQRJSVLAQKA-UHFFFAOYSA-N 2-[(2,3,4,5,6-pentafluorophenyl)methyl]-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)CC1=C(F)C(F)=C(F)C(F)=C1F VORQQRJSVLAQKA-UHFFFAOYSA-N 0.000 claims 1
- VPXSPTBTKHLCQY-UHFFFAOYSA-N 2-[(2,5-dimethoxyphenyl)methyl]-5-sulfanylpentanoic acid Chemical compound COC1=CC=C(OC)C(CC(CCCS)C(O)=O)=C1 VPXSPTBTKHLCQY-UHFFFAOYSA-N 0.000 claims 1
- HCDFUWTYXMIYJA-UHFFFAOYSA-N 2-[(2-carbamoylphenyl)methyl]-5-sulfanylpentanoic acid Chemical compound NC(=O)C1=CC=CC=C1CC(CCCS)C(O)=O HCDFUWTYXMIYJA-UHFFFAOYSA-N 0.000 claims 1
- HGNBVXVFPLCFGS-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC=C1Cl HGNBVXVFPLCFGS-UHFFFAOYSA-N 0.000 claims 1
- PYQKBKPIINRFHX-UHFFFAOYSA-N 2-[(2-cyanophenyl)methyl]-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC=C1C#N PYQKBKPIINRFHX-UHFFFAOYSA-N 0.000 claims 1
- YGTHVCLIXDRTSW-UHFFFAOYSA-N 2-[(3-phenoxyphenyl)methyl]-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(OC=2C=CC=CC=2)=C1 YGTHVCLIXDRTSW-UHFFFAOYSA-N 0.000 claims 1
- KITPJWBAILLUCD-UHFFFAOYSA-N 2-[(3-phenylphenyl)methyl]-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(C=2C=CC=CC=2)=C1 KITPJWBAILLUCD-UHFFFAOYSA-N 0.000 claims 1
- JVYSQYAULLQAHP-UHFFFAOYSA-N 2-[(3-tert-butylphenyl)methyl]-5-sulfanylpentanoic acid Chemical compound CC(C)(C)C1=CC=CC(CC(CCCS)C(O)=O)=C1 JVYSQYAULLQAHP-UHFFFAOYSA-N 0.000 claims 1
- BGLKPRGXYUWMAQ-UHFFFAOYSA-N 2-[(4-acetamidophenyl)methyl]-5-sulfanylpentanoic acid Chemical compound CC(=O)NC1=CC=C(CC(CCCS)C(O)=O)C=C1 BGLKPRGXYUWMAQ-UHFFFAOYSA-N 0.000 claims 1
- URMIUKKJQBGPLB-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=C(O)C=C1 URMIUKKJQBGPLB-UHFFFAOYSA-N 0.000 claims 1
- QMOJKEADTCOMEJ-UHFFFAOYSA-N 2-[(4-methylsulfonylphenyl)methyl]-5-sulfanylpentanoic acid Chemical compound CS(=O)(=O)C1=CC=C(CC(CCCS)C(O)=O)C=C1 QMOJKEADTCOMEJ-UHFFFAOYSA-N 0.000 claims 1
- MIIIRKIXGXSNML-UHFFFAOYSA-N 2-[(4-phenylphenyl)methyl]-5-sulfanylpentanoic acid Chemical compound C1=CC(CC(CCCS)C(=O)O)=CC=C1C1=CC=CC=C1 MIIIRKIXGXSNML-UHFFFAOYSA-N 0.000 claims 1
- OWCSOMCOBIJMHW-UHFFFAOYSA-N 2-[3-(2-carboxy-5-sulfanylpentyl)phenoxy]benzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(OC=2C(=CC=CC=2)C(O)=O)=C1 OWCSOMCOBIJMHW-UHFFFAOYSA-N 0.000 claims 1
- WMNGUGVHZZFUSA-UHFFFAOYSA-N 2-[3-(2-carboxy-5-sulfanylpentyl)phenyl]benzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(C=2C(=CC=CC=2)C(O)=O)=C1 WMNGUGVHZZFUSA-UHFFFAOYSA-N 0.000 claims 1
- UIPBZNKBAOJQHA-UHFFFAOYSA-N 2-[3-(carboxymethyl)phenoxy]-5-sulfanylpentanoic acid Chemical compound OC(=O)CC1=CC=CC(OC(CCCS)C(O)=O)=C1 UIPBZNKBAOJQHA-UHFFFAOYSA-N 0.000 claims 1
- ZHWFQWFTXXLPSM-UHFFFAOYSA-N 2-[4-(2-carboxy-5-sulfanylpentyl)phenoxy]benzoic acid Chemical compound C1=CC(CC(CCCS)C(=O)O)=CC=C1OC1=CC=CC=C1C(O)=O ZHWFQWFTXXLPSM-UHFFFAOYSA-N 0.000 claims 1
- HYVADFIGJMMRLF-UHFFFAOYSA-N 2-[4-(carboxymethyl)phenoxy]-5-sulfanylpentanoic acid Chemical compound OC(=O)CC1=CC=C(OC(CCCS)C(O)=O)C=C1 HYVADFIGJMMRLF-UHFFFAOYSA-N 0.000 claims 1
- QKWJXRWWDNFRMK-UHFFFAOYSA-N 2-[[3-(benzylcarbamoyl)phenyl]methyl]-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(C(=O)NCC=2C=CC=CC=2)=C1 QKWJXRWWDNFRMK-UHFFFAOYSA-N 0.000 claims 1
- RSFRRAZDFPZZHT-UHFFFAOYSA-N 2-[[4-(2-cyanophenyl)phenyl]methyl]-5-sulfanylpentanoic acid Chemical compound C1=CC(CC(CCCS)C(=O)O)=CC=C1C1=CC=CC=C1C#N RSFRRAZDFPZZHT-UHFFFAOYSA-N 0.000 claims 1
- ULUAWVNJRKVRGR-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenyl]methyl]-5-sulfanylpentanoic acid Chemical compound OC(=O)CC1=CC=C(CC(CCCS)C(O)=O)C=C1 ULUAWVNJRKVRGR-UHFFFAOYSA-N 0.000 claims 1
- QTCRNIDSGWSKLN-UHFFFAOYSA-N 2-benzyl-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC=C1 QTCRNIDSGWSKLN-UHFFFAOYSA-N 0.000 claims 1
- WEFRBVOBYWNMNL-UHFFFAOYSA-N 2-bromo-4-(2-carboxy-5-sulfanylpentyl)benzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=C(C(O)=O)C(Br)=C1 WEFRBVOBYWNMNL-UHFFFAOYSA-N 0.000 claims 1
- NABZMSQIXDUMRM-UHFFFAOYSA-N 2-phenoxy-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)OC1=CC=CC=C1 NABZMSQIXDUMRM-UHFFFAOYSA-N 0.000 claims 1
- NGMNYTQZTGEAFW-UHFFFAOYSA-N 2-phenylsulfanyl-5-sulfanylpentanoic acid Chemical compound SCCCC(C(=O)O)SC1=CC=CC=C1 NGMNYTQZTGEAFW-UHFFFAOYSA-N 0.000 claims 1
- VVSWPNCZEUUAEH-UHFFFAOYSA-N 3-(1-carboxy-4-sulfanylbutoxy)-4-chlorobenzoic acid Chemical compound SCCCC(C(=O)O)OC1=CC(C(O)=O)=CC=C1Cl VVSWPNCZEUUAEH-UHFFFAOYSA-N 0.000 claims 1
- XCCFTWPWARLYSF-UHFFFAOYSA-N 3-(1-carboxy-4-sulfanylbutoxy)-4-fluorobenzoic acid Chemical compound SCCCC(C(=O)O)OC1=CC(C(O)=O)=CC=C1F XCCFTWPWARLYSF-UHFFFAOYSA-N 0.000 claims 1
- RMODAGPIACEGPS-UHFFFAOYSA-N 3-(1-carboxy-4-sulfanylbutoxy)-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC(CCCS)C(O)=O RMODAGPIACEGPS-UHFFFAOYSA-N 0.000 claims 1
- KUHQPVJMGPHXPD-UHFFFAOYSA-N 3-(1-carboxy-4-sulfanylbutoxy)benzoic acid Chemical compound SCCCC(C(=O)O)OC1=CC=CC(C(O)=O)=C1 KUHQPVJMGPHXPD-UHFFFAOYSA-N 0.000 claims 1
- YCOWYEFXMOFVIH-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylhexyl)benzoic acid Chemical compound CC(S)CCC(C(O)=O)CC1=CC=CC(C(O)=O)=C1 YCOWYEFXMOFVIH-UHFFFAOYSA-N 0.000 claims 1
- YQTWFQBGUQQUIS-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-2-chlorobenzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(C(O)=O)=C1Cl YQTWFQBGUQQUIS-UHFFFAOYSA-N 0.000 claims 1
- WYFGLPBEXWOGKD-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-2-phenylbenzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(C(O)=O)=C1C1=CC=CC=C1 WYFGLPBEXWOGKD-UHFFFAOYSA-N 0.000 claims 1
- YJZGGCGFCHKIDL-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-4-chlorobenzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC(C(O)=O)=CC=C1Cl YJZGGCGFCHKIDL-UHFFFAOYSA-N 0.000 claims 1
- YRXHZVLQYIPGME-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-4-fluorobenzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC(C(O)=O)=CC=C1F YRXHZVLQYIPGME-UHFFFAOYSA-N 0.000 claims 1
- YYJGYEDQOSRQAT-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1CC(CCCS)C(O)=O YYJGYEDQOSRQAT-UHFFFAOYSA-N 0.000 claims 1
- NKKCDHZUKWQWBD-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-4-nitrobenzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC(C(O)=O)=CC=C1[N+]([O-])=O NKKCDHZUKWQWBD-UHFFFAOYSA-N 0.000 claims 1
- FGXMYGFAXIKBMB-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-4-phenylbenzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1 FGXMYGFAXIKBMB-UHFFFAOYSA-N 0.000 claims 1
- HQUGOWHIKUHTBD-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-5-methoxybenzoic acid Chemical compound COC1=CC(CC(CCCS)C(O)=O)=CC(C(O)=O)=C1 HQUGOWHIKUHTBD-UHFFFAOYSA-N 0.000 claims 1
- OGHVHZRXBBGIOP-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-5-nitrobenzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 OGHVHZRXBBGIOP-UHFFFAOYSA-N 0.000 claims 1
- NKZPFOFFSSROEI-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-5-phenoxybenzoic acid Chemical compound OC(=O)C1=CC(CC(CCCS)C(=O)O)=CC(OC=2C=CC=CC=2)=C1 NKZPFOFFSSROEI-UHFFFAOYSA-N 0.000 claims 1
- HTJJVJJZOQVJER-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-5-phenylbenzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC(C(O)=O)=CC(C=2C=CC=CC=2)=C1 HTJJVJJZOQVJER-UHFFFAOYSA-N 0.000 claims 1
- XHGGKLYPJOFAKF-UHFFFAOYSA-N 3-(2-carboxy-5-sulfanylpentyl)-5-phenylmethoxybenzoic acid Chemical compound OC(=O)C1=CC(CC(CCCS)C(=O)O)=CC(OCC=2C=CC=CC=2)=C1 XHGGKLYPJOFAKF-UHFFFAOYSA-N 0.000 claims 1
- LKVVCKVANGJUPA-UHFFFAOYSA-N 3-[3-(2-carboxy-5-sulfanylpentyl)phenyl]benzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC=CC(C=2C=C(C=CC=2)C(O)=O)=C1 LKVVCKVANGJUPA-UHFFFAOYSA-N 0.000 claims 1
- LLZCWFWIOCCIAQ-UHFFFAOYSA-N 3-bromo-5-(2-carboxy-5-sulfanylpentyl)benzoic acid Chemical compound SCCCC(C(=O)O)CC1=CC(Br)=CC(C(O)=O)=C1 LLZCWFWIOCCIAQ-UHFFFAOYSA-N 0.000 claims 1
- LVHUJAJJDGLHQL-UHFFFAOYSA-N 3-tert-butyl-5-(1-carboxy-4-sulfanylbutoxy)benzoic acid Chemical compound CC(C)(C)C1=CC(OC(CCCS)C(O)=O)=CC(C(O)=O)=C1 LVHUJAJJDGLHQL-UHFFFAOYSA-N 0.000 claims 1
- GGVNQQHTCGBKLF-UHFFFAOYSA-N 3-tert-butyl-5-(1-carboxy-4-sulfanylbutyl)sulfanylbenzoic acid Chemical compound CC(C)(C)C1=CC(SC(CCCS)C(O)=O)=CC(C(O)=O)=C1 GGVNQQHTCGBKLF-UHFFFAOYSA-N 0.000 claims 1
- HKLMSSIZWZPLNJ-UHFFFAOYSA-N 3-tert-butyl-5-(2-carboxy-5-sulfanylhexyl)benzoic acid Chemical compound CC(S)CCC(C(O)=O)CC1=CC(C(O)=O)=CC(C(C)(C)C)=C1 HKLMSSIZWZPLNJ-UHFFFAOYSA-N 0.000 claims 1
- ZTTRAVPRWXCCDT-UHFFFAOYSA-N 3-tert-butyl-5-(2-carboxy-5-sulfanylpentyl)benzoic acid Chemical compound CC(C)(C)C1=CC(CC(CCCS)C(O)=O)=CC(C(O)=O)=C1 ZTTRAVPRWXCCDT-UHFFFAOYSA-N 0.000 claims 1
- RBOTZOZBOFRNAJ-UHFFFAOYSA-N 3-tert-butyl-5-[(1-carboxy-4-sulfanylbutyl)amino]benzoic acid Chemical compound CC(C)(C)C1=CC(NC(CCCS)C(O)=O)=CC(C(O)=O)=C1 RBOTZOZBOFRNAJ-UHFFFAOYSA-N 0.000 claims 1
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| US7105159B1 (en) * | 1992-11-05 | 2006-09-12 | Sloan-Kettering Institute For Cancer Research | Antibodies to prostate-specific membrane antigen |
| US6953668B1 (en) | 1992-11-05 | 2005-10-11 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen |
| US7070782B1 (en) * | 1992-11-05 | 2006-07-04 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen |
| US6569432B1 (en) * | 1995-02-24 | 2003-05-27 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen and uses thereof |
| ATE317435T1 (de) | 1995-02-24 | 2006-02-15 | Sloan Kettering Inst Cancer | Prostataspezifisches membranes antigen und seine anwendungen |
| US20040253246A1 (en) * | 1996-02-23 | 2004-12-16 | Israeli Ron S. | Prostate-specific membrane antigen and uses thereof |
| US6586623B2 (en) * | 2001-01-17 | 2003-07-01 | Guilford Pharmaceuticals Inc. | Thiol-based NAALADase inhibitors |
| WO2002098885A1 (en) | 2001-02-07 | 2002-12-12 | Beth Israel Deaconess Medical Center | Modified psma ligands and uses related thereto |
| WO2003057670A2 (en) * | 2001-12-28 | 2003-07-17 | Guilford Pharmaceuticals Inc. | Indoles as naaladase inhibitors |
| JP4773951B2 (ja) * | 2003-03-03 | 2011-09-14 | エーザイ インコーポレーテッド | チオラクトン |
| US20040186081A1 (en) * | 2003-03-03 | 2004-09-23 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating opioid tolerance |
| JP2008505884A (ja) | 2004-07-08 | 2008-02-28 | エヌエスティー・ニューロサバイバル・テクノロジーズ・リミテッド | 疾患を検出する方法および化合物 |
| US8019863B2 (en) | 2008-03-28 | 2011-09-13 | Ianywhere Solutions, Inc. | Synchronizing events between mobile devices and servers |
| US8023934B2 (en) * | 2008-03-28 | 2011-09-20 | Ianywhere Solutions, Inc. | Synchronizing communications and data between mobile devices and servers |
| US20110093619A1 (en) * | 2009-10-16 | 2011-04-21 | Ianywhere Solutions, Inc. | Synchronizing Tasks between Mobile Devices and Servers |
| US8434097B2 (en) * | 2009-12-30 | 2013-04-30 | Sybase, Inc. | Dynamic data binding for MBOs for container based application |
| DK3307262T3 (da) * | 2015-06-15 | 2021-08-09 | Nmd Pharma As | Forbindelser til anvendelse ved behandling af neuromuskulære lidelser |
| US11591284B2 (en) | 2017-12-14 | 2023-02-28 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US11147788B2 (en) | 2017-12-14 | 2021-10-19 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US11730714B2 (en) | 2017-12-14 | 2023-08-22 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US10385028B2 (en) | 2017-12-14 | 2019-08-20 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US12440477B2 (en) | 2017-12-14 | 2025-10-14 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
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| EP0994707A4 (en) * | 1997-05-27 | 2001-11-14 | Guilford Pharm Inc | INHIBITORS OF NAALADASE ENZYME ACTIVITY |
| ES2251204T3 (es) | 1998-07-06 | 2006-04-16 | Mgi Gp, Inc. | Inhibidores de naaladasa utiles como compuestos y composiciones farmaceuticas. |
| WO2001092273A2 (en) | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Benzenedicarboxylic acid derivatives |
| WO2001091738A2 (en) * | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating amyotrophic lateral sclerosis |
| WO2001092274A2 (en) * | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating retinal disorders and glaucoma |
| US6586623B2 (en) * | 2001-01-17 | 2003-07-01 | Guilford Pharmaceuticals Inc. | Thiol-based NAALADase inhibitors |
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