JP2005503353A5 - - Google Patents
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- Publication number
- JP2005503353A5 JP2005503353A5 JP2003500046A JP2003500046A JP2005503353A5 JP 2005503353 A5 JP2005503353 A5 JP 2005503353A5 JP 2003500046 A JP2003500046 A JP 2003500046A JP 2003500046 A JP2003500046 A JP 2003500046A JP 2005503353 A5 JP2005503353 A5 JP 2005503353A5
- Authority
- JP
- Japan
- Prior art keywords
- benzoic acid
- mercaptoethyl
- disease
- compound
- disorder
- 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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- 238000000034 method Methods 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 30
- 102000003958 Glutamate Carboxypeptidase II Human genes 0.000 claims 20
- 108090000369 Glutamate Carboxypeptidase II Proteins 0.000 claims 20
- -1 carbocycle Chemical group 0.000 claims 19
- 201000010099 disease Diseases 0.000 claims 16
- 208000035475 disorder Diseases 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 208000024891 symptom Diseases 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 6
- 208000012902 Nervous system disease Diseases 0.000 claims 6
- 230000005856 abnormality Effects 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 6
- 230000000694 effects Effects 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 230000002401 inhibitory effect Effects 0.000 claims 6
- 230000001537 neural effect Effects 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 208000019901 Anxiety disease Diseases 0.000 claims 4
- 208000016192 Demyelinating disease Diseases 0.000 claims 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 102000004887 Transforming Growth Factor beta Human genes 0.000 claims 4
- 108090001012 Transforming Growth Factor beta Proteins 0.000 claims 4
- 208000027418 Wounds and injury Diseases 0.000 claims 4
- 230000033115 angiogenesis Effects 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 230000006378 damage Effects 0.000 claims 4
- 229930195712 glutamate Natural products 0.000 claims 4
- 208000014674 injury Diseases 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 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 4
- 238000009007 Diagnostic Kit Methods 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- OXQGVOVVZPQKPI-UHFFFAOYSA-N [N+](=O)([O-])NS(=C=NN(C(=O)[N+]#[C-])SC#N)C#N Chemical compound [N+](=O)([O-])NS(=C=NN(C(=O)[N+]#[C-])SC#N)C#N OXQGVOVVZPQKPI-UHFFFAOYSA-N 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- JHZAARCNDQOKNX-UHFFFAOYSA-N 2-(3-carboxyphenyl)-5-(sulfanylmethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=CC(CS)=CC=2)C(O)=O)=C1 JHZAARCNDQOKNX-UHFFFAOYSA-N 0.000 claims 2
- FIILSNMCZCETMG-UHFFFAOYSA-N 2-(3-carboxyphenyl)-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(CCS)C=CC=2)C(O)=O)=C1 FIILSNMCZCETMG-UHFFFAOYSA-N 0.000 claims 2
- OHNLVUHVLUKNJW-UHFFFAOYSA-N 2-(carboxymethyl)-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)CC1=CC=CC(CCS)=C1C(O)=O OHNLVUHVLUKNJW-UHFFFAOYSA-N 0.000 claims 2
- QSADSFZTQWWKBI-UHFFFAOYSA-N 2-phenylmethoxy-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OCC1=CC=CC=C1 QSADSFZTQWWKBI-UHFFFAOYSA-N 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000029147 Collagen-vascular disease Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims 2
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 208000029028 brain injury Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 230000004663 cell proliferation Effects 0.000 claims 2
- 208000018631 connective tissue disease Diseases 0.000 claims 2
- 239000002872 contrast media Substances 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 210000000981 epithelium Anatomy 0.000 claims 2
- 210000002744 extracellular matrix Anatomy 0.000 claims 2
- 230000000893 fibroproliferative effect Effects 0.000 claims 2
- 239000012530 fluid Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 208000000509 infertility Diseases 0.000 claims 2
- 230000036512 infertility Effects 0.000 claims 2
- 231100000535 infertility Toxicity 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 238000002372 labelling Methods 0.000 claims 2
- 239000003550 marker Substances 0.000 claims 2
- 230000007074 memory dysfunction Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 210000002569 neuron Anatomy 0.000 claims 2
- 230000009689 neuronal regeneration Effects 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000001737 promoting effect Effects 0.000 claims 2
- 208000017497 prostate disease Diseases 0.000 claims 2
- 230000037390 scarring Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 210000000278 spinal cord Anatomy 0.000 claims 2
- 230000004936 stimulating effect Effects 0.000 claims 2
- 210000001519 tissue Anatomy 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- DTWDGPDSRKEHCJ-UHFFFAOYSA-N 2-(2-phenylethoxy)-5-(sulfanylmethyl)benzoic acid Chemical compound OC(=O)C1=CC(CS)=CC=C1OCCC1=CC=CC=C1 DTWDGPDSRKEHCJ-UHFFFAOYSA-N 0.000 claims 1
- CMTOUXWGWVVSPC-UHFFFAOYSA-N 2-(2-phenylethoxy)-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OCCC1=CC=CC=C1 CMTOUXWGWVVSPC-UHFFFAOYSA-N 0.000 claims 1
- OYNMQTZKBJYUNY-UHFFFAOYSA-N 2-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCS OYNMQTZKBJYUNY-UHFFFAOYSA-N 0.000 claims 1
- GCVZTUWBJFDDTO-UHFFFAOYSA-N 2-(3,3-dimethylbutoxy)-6-(2-sulfanylethyl)benzoic acid Chemical compound CC(C)(C)CCOC1=CC=CC(CCS)=C1C(O)=O GCVZTUWBJFDDTO-UHFFFAOYSA-N 0.000 claims 1
- FNGDTLHFUDHBBY-UHFFFAOYSA-N 2-(3-tert-butyl-5-carboxyphenyl)-6-(2-sulfanylethyl)benzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C=2C(=C(CCS)C=CC=2)C(O)=O)=C1 FNGDTLHFUDHBBY-UHFFFAOYSA-N 0.000 claims 1
- VWSHPCDVNPNFRR-UHFFFAOYSA-N 2-(4-carboxyphenyl)-6-(2-sulfanylethyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(CCS)=C1C(O)=O VWSHPCDVNPNFRR-UHFFFAOYSA-N 0.000 claims 1
- BIQSMXUNKYDABH-UHFFFAOYSA-N 2-(carboxymethoxy)-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)COC1=CC=CC(CCS)=C1C(O)=O BIQSMXUNKYDABH-UHFFFAOYSA-N 0.000 claims 1
- NFXCVHBDFZSXRN-UHFFFAOYSA-N 2-[(2-bromo-4-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound BrC1=CC(C(=O)O)=CC=C1COC1=CC=CC(CCS)=C1C(O)=O NFXCVHBDFZSXRN-UHFFFAOYSA-N 0.000 claims 1
- VCQWRZJUZJCILA-UHFFFAOYSA-N 2-[(2-bromo-5-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(COC=2C(=C(CCS)C=CC=2)C(O)=O)=C1 VCQWRZJUZJCILA-UHFFFAOYSA-N 0.000 claims 1
- DNGXAKZNDFQLGB-UHFFFAOYSA-N 2-[(2-carboxy-5-methoxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound COC1=CC=C(C(O)=O)C(COC=2C(=C(CCS)C=CC=2)C(O)=O)=C1 DNGXAKZNDFQLGB-UHFFFAOYSA-N 0.000 claims 1
- MBCMCTMNMJCOTM-UHFFFAOYSA-N 2-[(2-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1COC1=CC=CC(CCS)=C1C(O)=O MBCMCTMNMJCOTM-UHFFFAOYSA-N 0.000 claims 1
- TXZSPLMIDAWMIG-UHFFFAOYSA-N 2-[(2-chlorophenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OCC1=CC=CC=C1Cl TXZSPLMIDAWMIG-UHFFFAOYSA-N 0.000 claims 1
- JESPTZYSXLXHNT-UHFFFAOYSA-N 2-[(2-phenylphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OCC1=CC=CC=C1C1=CC=CC=C1 JESPTZYSXLXHNT-UHFFFAOYSA-N 0.000 claims 1
- NKDDTPCECDQJIB-UHFFFAOYSA-N 2-[(3-bromo-4-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound C1=C(Br)C(C(=O)O)=CC=C1COC1=CC=CC(CCS)=C1C(O)=O NKDDTPCECDQJIB-UHFFFAOYSA-N 0.000 claims 1
- NDJICRKBXRUNIR-UHFFFAOYSA-N 2-[(3-bromo-5-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC(Br)=CC(COC=2C(=C(CCS)C=CC=2)C(O)=O)=C1 NDJICRKBXRUNIR-UHFFFAOYSA-N 0.000 claims 1
- MIDALKZOSXVTFY-UHFFFAOYSA-N 2-[(3-bromophenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OCC1=CC=CC(Br)=C1 MIDALKZOSXVTFY-UHFFFAOYSA-N 0.000 claims 1
- WNGSUDAZCMZXMR-UHFFFAOYSA-N 2-[(3-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(COC=2C(=C(CCS)C=CC=2)C(O)=O)=C1 WNGSUDAZCMZXMR-UHFFFAOYSA-N 0.000 claims 1
- XGKZHONEOVBQGA-UHFFFAOYSA-N 2-[(3-chlorophenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OCC1=CC=CC(Cl)=C1 XGKZHONEOVBQGA-UHFFFAOYSA-N 0.000 claims 1
- ALHLZNUPUGNCMM-UHFFFAOYSA-N 2-[(3-tert-butyl-5-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC(C(C)(C)C)=CC(COC=2C(=C(CCS)C=CC=2)C(O)=O)=C1 ALHLZNUPUGNCMM-UHFFFAOYSA-N 0.000 claims 1
- JDMZCJIZVNLQBE-UHFFFAOYSA-N 2-[(4-bromo-3-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound C1=C(Br)C(C(=O)O)=CC(COC=2C(=C(CCS)C=CC=2)C(O)=O)=C1 JDMZCJIZVNLQBE-UHFFFAOYSA-N 0.000 claims 1
- HEIBSQNNDAZRCO-UHFFFAOYSA-N 2-[(4-bromophenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OCC1=CC=C(Br)C=C1 HEIBSQNNDAZRCO-UHFFFAOYSA-N 0.000 claims 1
- TUWCLXVAVRKNEK-UHFFFAOYSA-N 2-[(4-carboxy-2-methoxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1COC1=CC=CC(CCS)=C1C(O)=O TUWCLXVAVRKNEK-UHFFFAOYSA-N 0.000 claims 1
- ZZWRPQPITSHFMS-UHFFFAOYSA-N 2-[(4-carboxy-3-methoxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(COC=2C(=C(CCS)C=CC=2)C(O)=O)=C1 ZZWRPQPITSHFMS-UHFFFAOYSA-N 0.000 claims 1
- SOMMCYYRPOBUID-UHFFFAOYSA-N 2-[(4-carboxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1COC1=CC=CC(CCS)=C1C(O)=O SOMMCYYRPOBUID-UHFFFAOYSA-N 0.000 claims 1
- UBNPSMVUTWQKLI-UHFFFAOYSA-N 2-[(4-chlorophenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OCC1=CC=C(Cl)C=C1 UBNPSMVUTWQKLI-UHFFFAOYSA-N 0.000 claims 1
- RIIVDLLMKJAJQY-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound C1=CC(OC)=CC=C1COC1=CC=CC(CCS)=C1C(O)=O RIIVDLLMKJAJQY-UHFFFAOYSA-N 0.000 claims 1
- KYSZIAVVALRRLD-UHFFFAOYSA-N 2-[(4-methylphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound C1=CC(C)=CC=C1COC1=CC=CC(CCS)=C1C(O)=O KYSZIAVVALRRLD-UHFFFAOYSA-N 0.000 claims 1
- IZCYCFKPGUZZTQ-UHFFFAOYSA-N 2-[(4-tert-butylphenyl)methoxy]-6-(2-sulfanylethyl)benzoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1COC1=CC=CC(CCS)=C1C(O)=O IZCYCFKPGUZZTQ-UHFFFAOYSA-N 0.000 claims 1
- OFHSEDBMTAANJN-UHFFFAOYSA-N 2-anilino-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1NC1=CC=CC=C1 OFHSEDBMTAANJN-UHFFFAOYSA-N 0.000 claims 1
- SCYVARDCTHZMPJ-UHFFFAOYSA-N 2-methoxy-6-(2-sulfanylethyl)benzoic acid Chemical compound COC1=CC=CC(CCS)=C1C(O)=O SCYVARDCTHZMPJ-UHFFFAOYSA-N 0.000 claims 1
- YQDSSPFOTZPRTA-UHFFFAOYSA-N 2-phenoxy-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1OC1=CC=CC=C1 YQDSSPFOTZPRTA-UHFFFAOYSA-N 0.000 claims 1
- UNDWZTRFKAMJSE-UHFFFAOYSA-N 2-phenyl-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1C1=CC=CC=C1 UNDWZTRFKAMJSE-UHFFFAOYSA-N 0.000 claims 1
- FTQQEJZIHPJBRU-UHFFFAOYSA-N 2-phenylmethoxy-5-(sulfanylmethyl)benzoic acid Chemical compound OC(=O)C1=CC(CS)=CC=C1OCC1=CC=CC=C1 FTQQEJZIHPJBRU-UHFFFAOYSA-N 0.000 claims 1
- KQTSQTJPFCHXJQ-UHFFFAOYSA-N 2-phenylsulfanyl-6-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=C(CCS)C=CC=C1SC1=CC=CC=C1 KQTSQTJPFCHXJQ-UHFFFAOYSA-N 0.000 claims 1
- UEQGWGKEGNIPSH-UHFFFAOYSA-N 4-bromo-3-(sulfanylmethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(CS)=C1 UEQGWGKEGNIPSH-UHFFFAOYSA-N 0.000 claims 1
- PDOJUXILGCHPKG-UHFFFAOYSA-N 5-[(3-carboxyphenyl)methoxy]-2-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(COC=2C=C(C(CCS)=CC=2)C(O)=O)=C1 PDOJUXILGCHPKG-UHFFFAOYSA-N 0.000 claims 1
- OZAOBLPIHUCYFW-UHFFFAOYSA-N 5-[(4-carboxyphenyl)methoxy]-2-(2-sulfanylethyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1COC1=CC=C(CCS)C(C(O)=O)=C1 OZAOBLPIHUCYFW-UHFFFAOYSA-N 0.000 claims 1
- QGUQWAJNUMPFHE-UHFFFAOYSA-N 5-phenylmethoxy-2-(2-sulfanylethyl)benzoic acid Chemical compound C1=C(CCS)C(C(=O)O)=CC(OCC=2C=CC=CC=2)=C1 QGUQWAJNUMPFHE-UHFFFAOYSA-N 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29403601P | 2001-05-30 | 2001-05-30 | |
| US34274601P | 2001-12-28 | 2001-12-28 | |
| PCT/US2002/016971 WO2002096866A2 (en) | 2001-05-30 | 2002-05-30 | Thiolalkyl benzoic acid derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009011782A Division JP2009149657A (ja) | 2001-05-30 | 2009-01-22 | チオールアルキル安息香酸誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005503353A JP2005503353A (ja) | 2005-02-03 |
| JP2005503353A5 true JP2005503353A5 (enExample) | 2005-09-02 |
| JP4292471B2 JP4292471B2 (ja) | 2009-07-08 |
Family
ID=26968313
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003500046A Expired - Lifetime JP4292471B2 (ja) | 2001-05-30 | 2002-05-30 | チオールアルキル安息香酸誘導体 |
| JP2009011782A Pending JP2009149657A (ja) | 2001-05-30 | 2009-01-22 | チオールアルキル安息香酸誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009011782A Pending JP2009149657A (ja) | 2001-05-30 | 2009-01-22 | チオールアルキル安息香酸誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6740777B2 (enExample) |
| EP (2) | EP1406867B1 (enExample) |
| JP (2) | JP4292471B2 (enExample) |
| AT (1) | ATE419232T1 (enExample) |
| AU (1) | AU2002310202B2 (enExample) |
| CA (1) | CA2448089C (enExample) |
| CY (1) | CY1108893T1 (enExample) |
| DE (1) | DE60230624D1 (enExample) |
| DK (1) | DK1406867T3 (enExample) |
| ES (1) | ES2319509T3 (enExample) |
| MX (1) | MXPA03010859A (enExample) |
| PT (1) | PT1406867E (enExample) |
| WO (1) | WO2002096866A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001092273A2 (en) * | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Benzenedicarboxylic acid derivatives |
| PT1406867E (pt) * | 2001-05-30 | 2009-02-25 | Eisai Corp North America | Derivados do ácido tiolalquilbenzóico |
| WO2003057670A2 (en) * | 2001-12-28 | 2003-07-17 | Guilford Pharmaceuticals Inc. | Indoles as naaladase inhibitors |
| WO2004078180A2 (en) * | 2003-03-03 | 2004-09-16 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating opioid tolerance |
| US7125907B2 (en) * | 2003-03-03 | 2006-10-24 | Guilford Pharmaceuticals Inc. | Thiolactones |
| WO2004101483A1 (ja) * | 2003-05-14 | 2004-11-25 | Riken | 新規３置換ベンゼン誘導体、その製造方法、およびそれを含む医薬組成物 |
| US8198328B2 (en) | 2004-01-21 | 2012-06-12 | New York University | Treatment of cancer using benzoic acid derivatives |
| US7282590B2 (en) * | 2004-02-12 | 2007-10-16 | The Research Foundation Of State University Of New York | Drug conjugates |
| CA2726987C (en) * | 2008-06-04 | 2014-02-18 | Baylor College Of Medicine | Stat3 inhibitors |
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| US3053890A (en) * | 1960-03-31 | 1962-09-11 | California Research Corp | Reaction products of formaldehyde and o-mercaptomethylbenzoic acid |
| US4318846A (en) * | 1979-09-07 | 1982-03-09 | Syva Company | Novel ether substituted fluorescein polyamino acid compounds as fluorescers and quenchers |
| US5089388A (en) | 1983-04-19 | 1992-02-18 | Syntex (U.S.A.) Inc. | Antibodies for salicylate and their preparation |
| US5314918A (en) * | 1987-06-24 | 1994-05-24 | Smithkline Beecham Corporation | Leukotriene antagonists |
| US5204358A (en) | 1987-11-25 | 1993-04-20 | Merck Frosst Canada, Inc. | Hetaryl styryl quinolines as leukotriene inhibitors |
| US5258551A (en) | 1991-12-18 | 1993-11-02 | Shionogi & Co., Ltd. | Process for producing α-ketoamide derivative |
| US5409780A (en) | 1992-02-13 | 1995-04-25 | Chemtrak, Inc. | Aniline analogs for hydrogen peroxide detection |
| US5316887A (en) | 1992-07-31 | 1994-05-31 | Polaroid Corporation | Thermally developable photosensitive material |
| US5453502A (en) | 1994-03-16 | 1995-09-26 | Eli Lilly And Company | 1,3,4 substituted and bicyclic derivatives of 2-azetidinones and processes for preparation thereof |
| AR006793A1 (es) | 1996-04-26 | 1999-09-29 | Ishihara Sangyo Kaisha | Compuestos pirazol o sus sales y herbicidas conteniendo los mismos |
| US6025344A (en) * | 1996-06-17 | 2000-02-15 | Guilford Pharmaceuticals Inc. | Certain dioic acid derivatives useful as NAALADase inhibitors |
| IL120531A (en) | 1997-03-26 | 2006-12-31 | Yissum Res Dev Co | Nitric oxide donors and pharmaceutical compositions containing them |
| US6265609B1 (en) | 1998-07-06 | 2001-07-24 | Guilford Pharmaceuticals Inc. | Thio-substituted pentanedioic acid derivatives |
| EP1093453B1 (en) * | 1998-07-06 | 2005-09-28 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors useful as pharmaceutical compounds and compositions |
| US6479470B1 (en) * | 1999-04-28 | 2002-11-12 | Georgetown University | Ligands for metabotropic glutamate receptors and inhibitors of NAALAdase |
| AU6661901A (en) * | 2000-05-30 | 2001-12-11 | Guilford Pharm Inc | Naaladase inhibitors for treating retinal disorders and glaucoma |
| WO2001091738A2 (en) * | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating amyotrophic lateral sclerosis |
| WO2001092273A2 (en) * | 2000-05-30 | 2001-12-06 | Guilford Pharmaceuticals Inc. | Benzenedicarboxylic acid derivatives |
| PT1406867E (pt) * | 2001-05-30 | 2009-02-25 | Eisai Corp North America | Derivados do ácido tiolalquilbenzóico |
-
2002
- 2002-05-30 PT PT02737263T patent/PT1406867E/pt unknown
- 2002-05-30 DK DK02737263T patent/DK1406867T3/da active
- 2002-05-30 AU AU2002310202A patent/AU2002310202B2/en not_active Expired
- 2002-05-30 AT AT02737263T patent/ATE419232T1/de active
- 2002-05-30 JP JP2003500046A patent/JP4292471B2/ja not_active Expired - Lifetime
- 2002-05-30 EP EP02737263A patent/EP1406867B1/en not_active Expired - Lifetime
- 2002-05-30 WO PCT/US2002/016971 patent/WO2002096866A2/en not_active Ceased
- 2002-05-30 US US10/156,880 patent/US6740777B2/en not_active Expired - Lifetime
- 2002-05-30 CA CA2448089A patent/CA2448089C/en not_active Expired - Lifetime
- 2002-05-30 EP EP08019550A patent/EP2025666A3/en not_active Withdrawn
- 2002-05-30 ES ES02737263T patent/ES2319509T3/es not_active Expired - Lifetime
- 2002-05-30 MX MXPA03010859A patent/MXPA03010859A/es active IP Right Grant
- 2002-05-30 DE DE60230624T patent/DE60230624D1/de not_active Expired - Lifetime
-
2004
- 2004-04-07 US US10/819,146 patent/US7138543B2/en not_active Expired - Lifetime
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2009
- 2009-01-22 JP JP2009011782A patent/JP2009149657A/ja active Pending
- 2009-03-20 CY CY20091100316T patent/CY1108893T1/el unknown
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