JP2008540520A5 - - Google Patents
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- JP2008540520A5 JP2008540520A5 JP2008511081A JP2008511081A JP2008540520A5 JP 2008540520 A5 JP2008540520 A5 JP 2008540520A5 JP 2008511081 A JP2008511081 A JP 2008511081A JP 2008511081 A JP2008511081 A JP 2008511081A JP 2008540520 A5 JP2008540520 A5 JP 2008540520A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- butyl
- tert
- methyl
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 208000004296 neuralgia Diseases 0.000 claims 10
- -1 —OH Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 7
- 239000002904 solvent Substances 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 208000006011 Stroke Diseases 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 208000021722 neuropathic pain Diseases 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 208000011580 syndromic disease Diseases 0.000 claims 5
- UHHCAOIDYYAISM-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2,4,5-trichlorophenyl)sulfonylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl UHHCAOIDYYAISM-UHFFFAOYSA-N 0.000 claims 4
- 208000004998 Abdominal Pain Diseases 0.000 claims 4
- 208000007848 Alcoholism Diseases 0.000 claims 4
- 206010002383 Angina Pectoris Diseases 0.000 claims 4
- 208000008035 Back Pain Diseases 0.000 claims 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims 4
- 208000002881 Colic Diseases 0.000 claims 4
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 4
- 206010012667 Diabetic glaucoma Diseases 0.000 claims 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 4
- 208000001640 Fibromyalgia Diseases 0.000 claims 4
- 201000005569 Gout Diseases 0.000 claims 4
- 206010019196 Head injury Diseases 0.000 claims 4
- 208000013016 Hypoglycemia Diseases 0.000 claims 4
- 206010021143 Hypoxia Diseases 0.000 claims 4
- 206010061218 Inflammation Diseases 0.000 claims 4
- 206010065390 Inflammatory pain Diseases 0.000 claims 4
- 208000008930 Low Back Pain Diseases 0.000 claims 4
- 208000019695 Migraine disease Diseases 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 208000004550 Postoperative Pain Diseases 0.000 claims 4
- 206010037779 Radiculopathy Diseases 0.000 claims 4
- 206010038419 Renal colic Diseases 0.000 claims 4
- 208000017442 Retinal disease Diseases 0.000 claims 4
- 206010038923 Retinopathy Diseases 0.000 claims 4
- 208000034189 Sclerosis Diseases 0.000 claims 4
- 201000007930 alcohol dependence Diseases 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 4
- 206010003246 arthritis Diseases 0.000 claims 4
- 201000011529 cardiovascular cancer Diseases 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 206010013663 drug dependence Diseases 0.000 claims 4
- 201000002545 drug psychosis Diseases 0.000 claims 4
- 208000001130 gallstones Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 230000002218 hypoglycaemic effect Effects 0.000 claims 4
- 230000007954 hypoxia Effects 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 4
- 208000037906 ischaemic injury Diseases 0.000 claims 4
- 230000005906 menstruation Effects 0.000 claims 4
- 206010027599 migraine Diseases 0.000 claims 4
- 230000002981 neuropathic effect Effects 0.000 claims 4
- 201000008482 osteoarthritis Diseases 0.000 claims 4
- 208000020016 psychiatric disease Diseases 0.000 claims 4
- 238000010992 reflux Methods 0.000 claims 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 4
- 208000011117 substance-related disease Diseases 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 4
- FQLCGAGYZZHGJO-UHFFFAOYSA-N 3-tert-butyl-5-[(2,3-difluorophenyl)methylsulfanyl]-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SCC1=CC=CC(F)=C1F FQLCGAGYZZHGJO-UHFFFAOYSA-N 0.000 claims 3
- 206010010904 Convulsion Diseases 0.000 claims 3
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- QVCYGHZDLQNEBV-UHFFFAOYSA-N 2,6-dihydroxy-3,5-di(propan-2-yl)benzoic acid Chemical compound CC(C)C1=CC(C(C)C)=C(O)C(C(O)=O)=C1O QVCYGHZDLQNEBV-UHFFFAOYSA-N 0.000 claims 2
- PJPFXTWZRXRDQV-UHFFFAOYSA-N 2-hydroxy-3-methyl-5-(4-methylphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC(C)=C(O)C(C(O)=O)=C1 PJPFXTWZRXRDQV-UHFFFAOYSA-N 0.000 claims 2
- XQOUIFOFSHOCSZ-UHFFFAOYSA-N 2-hydroxy-3-methyl-5-(4-nitrophenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C)=CC(SC=2C=CC(=CC=2)[N+]([O-])=O)=C1 XQOUIFOFSHOCSZ-UHFFFAOYSA-N 0.000 claims 2
- GJYOCXYIVUXRKG-UHFFFAOYSA-N 2-hydroxy-3-methyl-5-(4-nitrophenyl)sulfinylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C)=CC(S(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 GJYOCXYIVUXRKG-UHFFFAOYSA-N 0.000 claims 2
- PADOUNKWNXJDJZ-UHFFFAOYSA-N 2-hydroxy-3-methyl-5-(4-nitrophenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C)=CC(S(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 PADOUNKWNXJDJZ-UHFFFAOYSA-N 0.000 claims 2
- CDGTXPQHFRZVDR-UHFFFAOYSA-N 2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfanyl-3-propan-2-ylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)C)=CC(SC=2C=CC(=CC=2)[N+]([O-])=O)=C1C CDGTXPQHFRZVDR-UHFFFAOYSA-N 0.000 claims 2
- VPGFTXAMIWRKLD-UHFFFAOYSA-N 2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfinyl-3-propan-2-ylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)C)=CC(S(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1C VPGFTXAMIWRKLD-UHFFFAOYSA-N 0.000 claims 2
- GEDOJZVPHKBPGK-UHFFFAOYSA-N 2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfonyl-3-propan-2-ylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)C)=CC(S(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1C GEDOJZVPHKBPGK-UHFFFAOYSA-N 0.000 claims 2
- CHHACTDDJLPLMF-UHFFFAOYSA-N 2-hydroxy-6-methyl-5-naphthalen-1-ylsulfonyl-3-propan-2-ylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)C)=CC(S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)=C1C CHHACTDDJLPLMF-UHFFFAOYSA-N 0.000 claims 2
- FCCFJFNKHFXPRE-UHFFFAOYSA-N 3,5-ditert-butyl-2-chloro-6-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(Cl)C(C(O)=O)=C1O FCCFJFNKHFXPRE-UHFFFAOYSA-N 0.000 claims 2
- PYFVJHRYPYYPMT-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-5-(4-nitrophenyl)sulfanylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)(C)C)=CC(SC=2C=CC(=CC=2)[N+]([O-])=O)=C1 PYFVJHRYPYYPMT-UHFFFAOYSA-N 0.000 claims 2
- VJGOLFJCUHYYBA-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-5-(4-nitrophenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=C(O)C(C(C)(C)C)=CC(S(=O)(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 VJGOLFJCUHYYBA-UHFFFAOYSA-N 0.000 claims 2
- YXJGMECZFLCKQN-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-5-[(3-methoxyphenyl)methylsulfanyl]-6-methylbenzoic acid Chemical compound COC1=CC=CC(CSC=2C(=C(C(O)=O)C(O)=C(C=2)C(C)(C)C)C)=C1 YXJGMECZFLCKQN-UHFFFAOYSA-N 0.000 claims 2
- YNXAIBACHXTZSL-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-5-iodo-6-methylbenzoic acid Chemical group CC1=C(I)C=C(C(C)(C)C)C(O)=C1C(O)=O YNXAIBACHXTZSL-UHFFFAOYSA-N 0.000 claims 2
- OXOVVFWNAYRMON-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-5-isoquinolin-4-yl-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CN=CC2=CC=CC=C12 OXOVVFWNAYRMON-UHFFFAOYSA-N 0.000 claims 2
- BYTPSFUJMHGNTJ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2,4,5-trichlorophenyl)sulfanylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SC1=CC(Cl)=C(Cl)C=C1Cl BYTPSFUJMHGNTJ-UHFFFAOYSA-N 0.000 claims 2
- KDHSZYPAINZMPY-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2,4,5-trichlorophenyl)sulfinylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)C1=CC(Cl)=C(Cl)C=C1Cl KDHSZYPAINZMPY-UHFFFAOYSA-N 0.000 claims 2
- NGTRHORNWVHSRK-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2-methylphenyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC(C(C)(C)C)=C(O)C(C(O)=O)=C1C NGTRHORNWVHSRK-UHFFFAOYSA-N 0.000 claims 2
- TXGPKJYQYLPBNW-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2-methylpropylsulfanyl)benzoic acid Chemical compound CC(C)CSC1=CC(C(C)(C)C)=C(O)C(C(O)=O)=C1C TXGPKJYQYLPBNW-UHFFFAOYSA-N 0.000 claims 2
- KCXNTJGKJXQQPT-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2-nitrophenyl)sulfanylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SC1=CC=CC=C1[N+]([O-])=O KCXNTJGKJXQQPT-UHFFFAOYSA-N 0.000 claims 2
- WPSOUSYGCMJXAG-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2-nitrophenyl)sulfonylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)C1=CC=CC=C1[N+]([O-])=O WPSOUSYGCMJXAG-UHFFFAOYSA-N 0.000 claims 2
- SMOZISLPIDREMI-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2-phenyl-2-phenylsulfanylacetyl)benzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C(=O)C(C=1C=CC=CC=1)SC1=CC=CC=C1 SMOZISLPIDREMI-UHFFFAOYSA-N 0.000 claims 2
- XZHXDDBHLPUXCF-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2-phenylacetyl)benzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C(=O)CC1=CC=CC=C1 XZHXDDBHLPUXCF-UHFFFAOYSA-N 0.000 claims 2
- VSHAMFRLTFQLCI-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(2-phenylethylsulfanyl)benzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SCCC1=CC=CC=C1 VSHAMFRLTFQLCI-UHFFFAOYSA-N 0.000 claims 2
- SLPNUHDUYLAPLO-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(3-nitrophenyl)sulfanylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SC1=CC=CC([N+]([O-])=O)=C1 SLPNUHDUYLAPLO-UHFFFAOYSA-N 0.000 claims 2
- DRFZYAGTNQUQNP-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(3-nitrophenyl)sulfonylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 DRFZYAGTNQUQNP-UHFFFAOYSA-N 0.000 claims 2
- XBLUURAQDMHRSN-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-methylphenyl)sulfanylbenzoic acid Chemical compound C1=CC(C)=CC=C1SC1=CC(C(C)(C)C)=C(O)C(C(O)=O)=C1C XBLUURAQDMHRSN-UHFFFAOYSA-N 0.000 claims 2
- FKROIQQETZKCQO-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-methylphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CC(C(C)(C)C)=C(O)C(C(O)=O)=C1C FKROIQQETZKCQO-UHFFFAOYSA-N 0.000 claims 2
- XKFMEKWWFJHFFW-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-morpholin-4-ylphenyl)benzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CC=C(N2CCOCC2)C=C1 XKFMEKWWFJHFFW-UHFFFAOYSA-N 0.000 claims 2
- FTDDOXPBPJVHSS-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfanylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SC1=CC=C([N+]([O-])=O)C=C1 FTDDOXPBPJVHSS-UHFFFAOYSA-N 0.000 claims 2
- NTFYOZMLRFFCCO-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfinylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)C1=CC=C([N+]([O-])=O)C=C1 NTFYOZMLRFFCCO-UHFFFAOYSA-N 0.000 claims 2
- MYBHIAGMFYKNOD-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(4-nitrophenyl)sulfonylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 MYBHIAGMFYKNOD-UHFFFAOYSA-N 0.000 claims 2
- IPYFOABVDCNLTG-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(oxan-2-ylmethylsulfanyl)benzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SCC1OCCCC1 IPYFOABVDCNLTG-UHFFFAOYSA-N 0.000 claims 2
- WORPHFONQSOGGY-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(pyridin-2-ylmethylsulfonyl)benzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)CC1=CC=CC=N1 WORPHFONQSOGGY-UHFFFAOYSA-N 0.000 claims 2
- RSTINTUMSSNHSA-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(pyridin-3-ylmethylsulfanyl)benzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SCC1=CC=CN=C1 RSTINTUMSSNHSA-UHFFFAOYSA-N 0.000 claims 2
- BXLXIWJXEWISRK-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-(pyridin-4-ylmethylsulfanyl)benzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SCC1=CC=NC=C1 BXLXIWJXEWISRK-UHFFFAOYSA-N 0.000 claims 2
- MCYHGTSUMCYTGP-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-[(3-methylphenyl)methylsulfanyl]benzoic acid Chemical compound CC1=CC=CC(CSC=2C(=C(C(O)=O)C(O)=C(C=2)C(C)(C)C)C)=C1 MCYHGTSUMCYTGP-UHFFFAOYSA-N 0.000 claims 2
- OSEDZHDSKKKFMR-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-[(3-methylphenyl)methylsulfonyl]benzoic acid Chemical compound CC1=CC=CC(CS(=O)(=O)C=2C(=C(C(O)=O)C(O)=C(C=2)C(C)(C)C)C)=C1 OSEDZHDSKKKFMR-UHFFFAOYSA-N 0.000 claims 2
- POWIKJOOYKGVKB-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-[4-(trifluoromethoxy)phenyl]sulfonylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 POWIKJOOYKGVKB-UHFFFAOYSA-N 0.000 claims 2
- USCADIULGBDFBJ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-[[2-(trifluoromethyl)phenyl]methylsulfanyl]benzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SCC1=CC=CC=C1C(F)(F)F USCADIULGBDFBJ-UHFFFAOYSA-N 0.000 claims 2
- STOMIRHERCGZMF-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-[[2-(trifluoromethyl)phenyl]methylsulfonyl]benzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)CC1=CC=CC=C1C(F)(F)F STOMIRHERCGZMF-UHFFFAOYSA-N 0.000 claims 2
- YTZBJKMUFNXILO-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-naphthalen-1-ylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CC=CC2=CC=CC=C12 YTZBJKMUFNXILO-UHFFFAOYSA-N 0.000 claims 2
- OFFCQLUAICHYFW-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-naphthalen-2-ylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CC=C(C=CC=C2)C2=C1 OFFCQLUAICHYFW-UHFFFAOYSA-N 0.000 claims 2
- KVVFZAICRXSJTK-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-phenylsulfanylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SC1=CC=CC=C1 KVVFZAICRXSJTK-UHFFFAOYSA-N 0.000 claims 2
- PFSKJKDVBIEFNC-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-pyridin-4-ylsulfanylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SC1=CC=NC=C1 PFSKJKDVBIEFNC-UHFFFAOYSA-N 0.000 claims 2
- QRXGEPQCABDVTM-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-quinolin-3-ylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CN=C(C=CC=C2)C2=C1 QRXGEPQCABDVTM-UHFFFAOYSA-N 0.000 claims 2
- HNJJNKTZBVMTQA-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-quinolin-5-ylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CC=CC2=NC=CC=C12 HNJJNKTZBVMTQA-UHFFFAOYSA-N 0.000 claims 2
- KCBDWQDMQPFHMG-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-quinolin-6-ylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CC=C(N=CC=C2)C2=C1 KCBDWQDMQPFHMG-UHFFFAOYSA-N 0.000 claims 2
- ZAIOVJLQRBXGGE-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-quinolin-8-ylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CC=CC2=CC=CN=C12 ZAIOVJLQRBXGGE-UHFFFAOYSA-N 0.000 claims 2
- IVLBNPYDNXCOTN-UHFFFAOYSA-N 3-tert-butyl-5-(2,3-dichlorophenyl)sulfonyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)C1=CC=CC(Cl)=C1Cl IVLBNPYDNXCOTN-UHFFFAOYSA-N 0.000 claims 2
- HYAONOPIXVVDFU-UHFFFAOYSA-N 3-tert-butyl-5-(2,4-dichlorophenyl)-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CC=C(Cl)C=C1Cl HYAONOPIXVVDFU-UHFFFAOYSA-N 0.000 claims 2
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- GFZHSJZTEABGSH-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-phenylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=CC=CC=C1 GFZHSJZTEABGSH-UHFFFAOYSA-N 0.000 claims 1
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- VUYPOUVLPKVKMG-UHFFFAOYSA-N 3-tert-butyl-5-(4-chloro-2-fluorobenzoyl)-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C(=O)C1=CC=C(Cl)C=C1F VUYPOUVLPKVKMG-UHFFFAOYSA-N 0.000 claims 1
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- RRHIDAMWLVCQSM-UHFFFAOYSA-N 3-tert-butyl-5-(4-chloro-n-methylanilino)-2-hydroxy-6-methylbenzoic acid Chemical compound C=1C(C(C)(C)C)=C(O)C(C(O)=O)=C(C)C=1N(C)C1=CC=C(Cl)C=C1 RRHIDAMWLVCQSM-UHFFFAOYSA-N 0.000 claims 1
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- YQZRCTDSYNTKBB-UHFFFAOYSA-N 3-tert-butyl-5-(4-fluorobenzoyl)-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C(=O)C1=CC=C(F)C=C1 YQZRCTDSYNTKBB-UHFFFAOYSA-N 0.000 claims 1
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- WBVIOPXOIKQBQO-UHFFFAOYSA-N 3-tert-butyl-5-(5-tert-butyl-4-hydroxy-3-methoxycarbonyl-2-methylphenyl)-2-hydroxy-6-methylbenzoic acid Chemical compound CC(C)(C)C1=C(O)C(C(=O)OC)=C(C)C(C=2C(=C(C(O)=O)C(O)=C(C=2)C(C)(C)C)C)=C1 WBVIOPXOIKQBQO-UHFFFAOYSA-N 0.000 claims 1
- NNHVJIDLKUNIPT-UHFFFAOYSA-N 3-tert-butyl-5-[(4-chlorophenyl)-ethoxymethyl]-2-hydroxy-6-methylbenzoic acid Chemical compound C=1C(C(C)(C)C)=C(O)C(C(O)=O)=C(C)C=1C(OCC)C1=CC=C(Cl)C=C1 NNHVJIDLKUNIPT-UHFFFAOYSA-N 0.000 claims 1
- BTIUYUUVQQZVPI-UHFFFAOYSA-N 3-tert-butyl-5-[(4-chlorophenyl)methylsulfanyl]-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SCC1=CC=C(Cl)C=C1 BTIUYUUVQQZVPI-UHFFFAOYSA-N 0.000 claims 1
- IOVQTPPAJRNZSY-UHFFFAOYSA-N 3-tert-butyl-5-[5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl]-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C1=NOC(C=2C=CC(Cl)=CC=2)=N1 IOVQTPPAJRNZSY-UHFFFAOYSA-N 0.000 claims 1
- RFGFRWQAMUQWRY-UHFFFAOYSA-N 3-tert-butyl-5-[C-(4-chlorophenyl)-N-hydroxycarbonimidoyl]-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C(=NO)C1=CC=C(Cl)C=C1 RFGFRWQAMUQWRY-UHFFFAOYSA-N 0.000 claims 1
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- AVVRFPIKWNTYSZ-UHFFFAOYSA-N 5-anilino-3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1NC1=CC=CC=C1 AVVRFPIKWNTYSZ-UHFFFAOYSA-N 0.000 claims 1
- QHMIFCQYKYRHKX-UHFFFAOYSA-N 5-benzoyl-3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1C(=O)C1=CC=CC=C1 QHMIFCQYKYRHKX-UHFFFAOYSA-N 0.000 claims 1
- DIERFEPJKJDVAU-UHFFFAOYSA-N 5-benzylsulfanyl-3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound C1=C(C(C)(C)C)C(O)=C(C(O)=O)C(C)=C1SCC1=CC=CC=C1 DIERFEPJKJDVAU-UHFFFAOYSA-N 0.000 claims 1
- ZJZKWZRRHSAWQI-UHFFFAOYSA-N 5-benzylsulfinyl-3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)CC1=CC=CC=C1 ZJZKWZRRHSAWQI-UHFFFAOYSA-N 0.000 claims 1
- KEPNVCWDRUYJFX-UHFFFAOYSA-N 5-benzylsulfonyl-3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1S(=O)(=O)CC1=CC=CC=C1 KEPNVCWDRUYJFX-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
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- 208000009205 Tinnitus Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
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- 208000002982 auditory neuropathy Diseases 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000012039 electrophile Substances 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
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| EP2068871B1 (en) | 2006-09-25 | 2013-12-25 | PTC Therapeutics, Inc. | Hydroxylated 1,2,4-oxadiazole benzoic acid compounds, compositions thereof and the use for nonsense suppression |
| JP2010100552A (ja) * | 2008-10-22 | 2010-05-06 | Tosoh Corp | １，３，５−トリアジン化合物の製造方法 |
| WO2010114896A1 (en) | 2009-03-31 | 2010-10-07 | Arqule, Inc. | Substituted indolo-pyridinone compounds |
| JP5761971B2 (ja) * | 2010-11-26 | 2015-08-12 | 興和株式会社 | 二環性アリール環又は二環性へテロアリール環を有するピラジン誘導体 |
| CN103142569B (zh) * | 2013-02-27 | 2016-01-20 | 南京医科大学 | 2,6-二异丙基苯甲酸及其衍生物作为神经保护剂的应用 |
| ES2886641T3 (es) | 2014-08-11 | 2021-12-20 | Angion Biomedica Corp | Inhibidores de citocromo P450 y sus usos |
| US10287282B2 (en) | 2014-12-31 | 2019-05-14 | Angion Biomedica Corp. | Methods and agents for treating disease |
| CN109942427B (zh) * | 2019-04-17 | 2022-02-18 | 云南农业大学 | 一种单萜酚类衍生物及其合成方法和在农药中的应用 |
| CN114540844B (zh) * | 2022-02-24 | 2024-02-20 | 青岛科技大学 | 一种电催化下苯并噻吩衍生物的制备方法 |
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| US3198799A (en) * | 1965-08-03 | Ohj cooh | ||
| DE293905C (enExample) * | ||||
| DE716599C (de) * | 1939-07-11 | 1942-01-24 | Ig Farbenindustrie Ag | Verfahren zum Schuetzen von keratinhaltigem Material vor dem Angriff von Textilschaedlingen |
| BE795722A (fr) * | 1972-02-24 | 1973-06-18 | Fabre Sa Pierre | Nouveaux derives a activite anti-inflammatoire et antalgique |
| DE2431360A1 (de) * | 1974-06-29 | 1976-01-15 | Castaigne Sa | O-thymotinsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen |
| GB1493375A (en) * | 1974-09-20 | 1977-11-30 | Ici Ltd | Salicylanilide derivatives |
| US4005218A (en) * | 1975-03-18 | 1977-01-25 | Janssen Pharmaceutica N.V. | Antiparasitic salicylanilide derivatives |
| JPS5826728B2 (ja) * | 1976-01-05 | 1983-06-04 | ウェルファイド株式会社 | 抗動脈硬化症剤 |
| US4301159A (en) * | 1980-06-20 | 1981-11-17 | Shionogi & Co., Ltd. | N-(Diethylaminoethyl)-2-alkoxy-benzamide derivatives |
| WO2004041256A2 (en) * | 2002-11-08 | 2004-05-21 | Novo Nordisk A/S | Safe chemical uncouplers for the treatment of obesity |
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- 2006-05-08 US US11/912,552 patent/US20090192190A1/en not_active Abandoned
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- 2006-05-08 CA CA002607938A patent/CA2607938A1/en not_active Abandoned
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- 2006-05-08 EP EP06733399A patent/EP1890993A4/en not_active Withdrawn
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2007
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