CA2448089C - Thiolalkyl benzoic acid derivatives - Google Patents
Thiolalkyl benzoic acid derivatives Download PDFInfo
- Publication number
- CA2448089C CA2448089C CA2448089A CA2448089A CA2448089C CA 2448089 C CA2448089 C CA 2448089C CA 2448089 A CA2448089 A CA 2448089A CA 2448089 A CA2448089 A CA 2448089A CA 2448089 C CA2448089 C CA 2448089C
- Authority
- CA
- Canada
- Prior art keywords
- mercaptoethyl
- benzoic acid
- compound
- disease
- methoxy
- 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 - Lifetime
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- 150000001558 benzoic acid derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 143
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 83
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- 102000003958 Glutamate Carboxypeptidase II Human genes 0.000 claims abstract description 48
- 208000035475 disorder Diseases 0.000 claims abstract description 42
- 201000010099 disease Diseases 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 30
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 24
- 208000033808 peripheral neuropathy Diseases 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- -1 carbocycle Chemical group 0.000 claims description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 241001465754 Metazoa Species 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 241000124008 Mammalia Species 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
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- 239000000203 mixture Substances 0.000 claims description 12
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- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 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 description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
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- OYNMQTZKBJYUNY-UHFFFAOYSA-N 2-(2-sulfanylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCS OYNMQTZKBJYUNY-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
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- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
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- 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 8
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- 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
- 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
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Applications Claiming Priority (5)
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| US29403601P | 2001-05-30 | 2001-05-30 | |
| US60/294,036 | 2001-05-30 | ||
| US34274601P | 2001-12-28 | 2001-12-28 | |
| US60/342,746 | 2001-12-28 | ||
| PCT/US2002/016971 WO2002096866A2 (en) | 2001-05-30 | 2002-05-30 | Thiolalkyl benzoic acid derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2448089A1 CA2448089A1 (en) | 2002-12-05 |
| CA2448089C true CA2448089C (en) | 2010-10-19 |
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| CA2448089A Expired - Lifetime CA2448089C (en) | 2001-05-30 | 2002-05-30 | Thiolalkyl benzoic acid derivatives |
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| EP (2) | EP1406867B1 (enExample) |
| JP (2) | JP4292471B2 (enExample) |
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| 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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| EP1406867A2 (en) | 2004-04-14 |
| US20040198824A1 (en) | 2004-10-07 |
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| AU2002310202B2 (en) | 2008-05-15 |
| EP2025666A2 (en) | 2009-02-18 |
| EP2025666A3 (en) | 2010-03-31 |
| WO2002096866A2 (en) | 2002-12-05 |
| WO2002096866A3 (en) | 2004-01-15 |
| ES2319509T3 (es) | 2009-05-08 |
| JP2009149657A (ja) | 2009-07-09 |
| DE60230624D1 (en) | 2009-02-12 |
| CY1108893T1 (el) | 2014-07-02 |
| EP1406867B1 (en) | 2008-12-31 |
| CA2448089A1 (en) | 2002-12-05 |
| JP4292471B2 (ja) | 2009-07-08 |
| JP2005503353A (ja) | 2005-02-03 |
| US7138543B2 (en) | 2006-11-21 |
| ATE419232T1 (de) | 2009-01-15 |
| DK1406867T3 (da) | 2009-04-06 |
| US20030100607A1 (en) | 2003-05-29 |
| US6740777B2 (en) | 2004-05-25 |
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