JP2013510106A5 - - Google Patents
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- Publication number
- JP2013510106A5 JP2013510106A5 JP2012537324A JP2012537324A JP2013510106A5 JP 2013510106 A5 JP2013510106 A5 JP 2013510106A5 JP 2012537324 A JP2012537324 A JP 2012537324A JP 2012537324 A JP2012537324 A JP 2012537324A JP 2013510106 A5 JP2013510106 A5 JP 2013510106A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- indole
- carboxylic acid
- alkyl
- phenyl
- 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
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 239000003112 inhibitor Substances 0.000 claims 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 9
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 235000000346 sugar Nutrition 0.000 claims 8
- 229940124597 therapeutic agent Drugs 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 108010088350 Lactate Dehydrogenase 5 Proteins 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- BALGRYSMSQXEFI-UHFFFAOYSA-N 1-hydroxy-3-methyl-6-phenyl-4-(trifluoromethyl)indole-2-carboxylic acid Chemical compound C=1C(C(F)(F)F)=C2C(C)=C(C(O)=O)N(O)C2=CC=1C1=CC=CC=C1 BALGRYSMSQXEFI-UHFFFAOYSA-N 0.000 claims 4
- FRNMLTUFRZNRMN-UHFFFAOYSA-N 1-hydroxy-4-(4-phenyltriazol-1-yl)indole-2-carboxylic acid Chemical compound C1=CC=C2N(O)C(C(=O)O)=CC2=C1N(N=N1)C=C1C1=CC=CC=C1 FRNMLTUFRZNRMN-UHFFFAOYSA-N 0.000 claims 4
- RABDZGXLKUNVIO-UHFFFAOYSA-N 1-hydroxy-5,6-diphenylindole-2-carboxylic acid Chemical compound C=1C=CC=CC=1C=1C=C2N(O)C(C(=O)O)=CC2=CC=1C1=CC=CC=C1 RABDZGXLKUNVIO-UHFFFAOYSA-N 0.000 claims 4
- KGMNEXZTTRCDBJ-UHFFFAOYSA-N 1-hydroxy-5-(4-methoxyphenyl)indole-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(O)C(=C2)C(O)=O)C2=C1 KGMNEXZTTRCDBJ-UHFFFAOYSA-N 0.000 claims 4
- RTQWCTDOAZOGRH-UHFFFAOYSA-N 1-hydroxy-5-phenylindole-2-carboxylic acid Chemical compound C=1C=C2N(O)C(C(=O)O)=CC2=CC=1C1=CC=CC=C1 RTQWCTDOAZOGRH-UHFFFAOYSA-N 0.000 claims 4
- QCRXVEVTMSISGH-UHFFFAOYSA-N 1-hydroxy-6-(2h-tetrazol-5-yl)indole-2-carboxylic acid Chemical compound C1=C2N(O)C(C(=O)O)=CC2=CC=C1C=1N=NNN=1 QCRXVEVTMSISGH-UHFFFAOYSA-N 0.000 claims 4
- JKKGPYGQPYFSNR-UHFFFAOYSA-N 1-hydroxy-6-(4-methoxyphenyl)indole-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=C(C(O)=O)N2O)C2=C1 JKKGPYGQPYFSNR-UHFFFAOYSA-N 0.000 claims 4
- JTVQZHGFLRTDFC-UHFFFAOYSA-N 1-hydroxy-6-[3-(trifluoromethoxy)phenyl]indole-2-carboxylic acid Chemical compound C1=C2N(O)C(C(=O)O)=CC2=CC=C1C1=CC=CC(OC(F)(F)F)=C1 JTVQZHGFLRTDFC-UHFFFAOYSA-N 0.000 claims 4
- AGAPSTOEFWRRAQ-UHFFFAOYSA-N 1-hydroxy-6-[4-(trifluoromethyl)phenyl]indole-2-carboxylic acid Chemical compound C1=C2N(O)C(C(=O)O)=CC2=CC=C1C1=CC=C(C(F)(F)F)C=C1 AGAPSTOEFWRRAQ-UHFFFAOYSA-N 0.000 claims 4
- WMFMSPXVBCJHRS-UHFFFAOYSA-N 1-hydroxy-6-[methyl-[4-(trifluoromethyl)phenyl]sulfamoyl]indole-2-carboxylic acid Chemical compound C=1C=C2C=C(C(O)=O)N(O)C2=CC=1S(=O)(=O)N(C)C1=CC=C(C(F)(F)F)C=C1 WMFMSPXVBCJHRS-UHFFFAOYSA-N 0.000 claims 4
- ROZRSECOCQXQFF-UHFFFAOYSA-N 1-hydroxy-6-naphthalen-2-ylindole-2-carboxylic acid Chemical compound C1=CC=CC2=CC(C3=CC=C4C=C(N(C4=C3)O)C(=O)O)=CC=C21 ROZRSECOCQXQFF-UHFFFAOYSA-N 0.000 claims 4
- KGXDBNBXAPVUIM-UHFFFAOYSA-N 1-hydroxy-6-phenyl-4-(trifluoromethyl)indole-2-carboxylic acid Chemical compound C1=C2N(O)C(C(=O)O)=CC2=C(C(F)(F)F)C=C1C1=CC=CC=C1 KGXDBNBXAPVUIM-UHFFFAOYSA-N 0.000 claims 4
- JPTIDBKFQSCJSC-UHFFFAOYSA-N 1-hydroxy-6-phenylindole-2-carboxylic acid Chemical compound C1=C2N(O)C(C(=O)O)=CC2=CC=C1C1=CC=CC=C1 JPTIDBKFQSCJSC-UHFFFAOYSA-N 0.000 claims 4
- NMBOQCDQTOCORB-UHFFFAOYSA-N 6-[(4-fluorophenyl)-methylsulfamoyl]-1-hydroxyindole-2-carboxylic acid Chemical compound C=1C=C2C=C(C(O)=O)N(O)C2=CC=1S(=O)(=O)N(C)C1=CC=C(F)C=C1 NMBOQCDQTOCORB-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 108090000790 Enzymes Proteins 0.000 claims 3
- 102000004190 Enzymes Human genes 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 102100034671 L-lactate dehydrogenase A chain Human genes 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- RHQSTHZCUWNEGJ-UHFFFAOYSA-N 1-hydroxy-3-oxidobenzimidazol-3-ium-2-carboxylic acid Chemical compound C1=CC=C2[N+]([O-])=C(C(=O)O)N(O)C2=C1 RHQSTHZCUWNEGJ-UHFFFAOYSA-N 0.000 claims 2
- IHROBPZWETYCBZ-UHFFFAOYSA-N 1-hydroxybenzimidazole-2-carboxylic acid Chemical compound C1=CC=C2N(O)C(C(=O)O)=NC2=C1 IHROBPZWETYCBZ-UHFFFAOYSA-N 0.000 claims 2
- -1 4- (trifluoromethoxy) phenyl Chemical group 0.000 claims 2
- UPTYCYWTFGTCCG-UHFFFAOYSA-N 5-(1-piperazinylsulfonyl)isoquinoline Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCNCC1 UPTYCYWTFGTCCG-UHFFFAOYSA-N 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- MJELXUILFCDHAV-UHFFFAOYSA-N C=1C=C2[N+]([O-])=C(C(=O)O)N(O)C2=CC=1C1=CC=CC=C1 Chemical compound C=1C=C2[N+]([O-])=C(C(=O)O)N(O)C2=CC=1C1=CC=CC=C1 MJELXUILFCDHAV-UHFFFAOYSA-N 0.000 claims 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims 2
- TZRYSIGUFZYTHT-UHFFFAOYSA-N ClC1=CC=C2[N+]([O-])=C(C(=O)O)N(O)C2=C1 Chemical compound ClC1=CC=C2[N+]([O-])=C(C(=O)O)N(O)C2=C1 TZRYSIGUFZYTHT-UHFFFAOYSA-N 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010025323 Lymphomas Diseases 0.000 claims 2
- 208000003445 Mouth Neoplasms Diseases 0.000 claims 2
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims 2
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 201000010881 cervical cancer Diseases 0.000 claims 2
- 150000008266 deoxy sugars Chemical class 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 125000002791 glucosyl group Chemical class C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 201000004792 malaria Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229920001542 oligosaccharide Polymers 0.000 claims 2
- 150000002482 oligosaccharides Chemical class 0.000 claims 2
- 201000008968 osteosarcoma Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 150000008163 sugars Chemical class 0.000 claims 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000012830 cancer therapeutic Substances 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITPI2009A000140 | 2009-11-09 | ||
| IT000140A ITPI20090140A1 (it) | 2009-11-09 | 2009-11-09 | Composto inibitore dell'enzima lattato deidrogenasi (ldh) e composizione farmaceutica che comprende tale composto |
| PCT/EP2010/006740 WO2011054525A1 (en) | 2009-11-09 | 2010-11-05 | Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013510106A JP2013510106A (ja) | 2013-03-21 |
| JP2013510106A5 true JP2013510106A5 (enExample) | 2013-12-26 |
Family
ID=42244578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012537324A Pending JP2013510106A (ja) | 2009-11-09 | 2010-11-05 | 乳酸脱水素酵素（ｌｄｈ）の阻害化合物およびこれらの化合物を含む医薬組成物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20120309794A1 (enExample) |
| EP (1) | EP2499114A1 (enExample) |
| JP (1) | JP2013510106A (enExample) |
| CN (1) | CN102639497A (enExample) |
| AU (1) | AU2010314367A1 (enExample) |
| BR (1) | BR112012010868A2 (enExample) |
| CA (1) | CA2780136A1 (enExample) |
| EA (1) | EA201290316A1 (enExample) |
| IT (1) | ITPI20090140A1 (enExample) |
| WO (1) | WO2011054525A1 (enExample) |
| ZA (1) | ZA201203993B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITPI20110143A1 (it) * | 2011-12-20 | 2013-06-21 | Univ Pisa | Agenti terapeutici in grado di ridurre la produzione cellulare di acido lattico e composizioni farmaceutiche che comprendono tali composti |
| WO2014115764A1 (ja) * | 2013-01-25 | 2014-07-31 | 国立大学法人岡山大学 | 乳酸脱水素酵素阻害剤およびそれを含有する医薬品 |
| US9750761B2 (en) | 2014-05-21 | 2017-09-05 | University Of Rochester | LDH inhibitors as treatment for fibrosis and fibrotic-related disorders |
| FR3030516B1 (fr) * | 2014-12-19 | 2019-12-27 | Galderma Research & Development | Derives sulfonamides bicycles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t) |
| JP6681072B2 (ja) * | 2015-02-09 | 2020-04-15 | 国立大学法人 岡山大学 | 乳酸脱水素酵素阻害剤およびそれを含有する抗てんかん剤 |
| CA3029489A1 (en) * | 2016-06-29 | 2018-01-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | 1h-pyrazol-1-yl-thiazoles as inhibitors of lactate dehydrogenase and methods of use thereof |
| EP4306108A1 (en) * | 2022-07-11 | 2024-01-17 | Theodossis Theodossiou | 5-aminolevulinic acid, or an ester thereof for use in treatment of cancer based on the inhibition of lactate dehydrogenase |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1923481A1 (de) * | 1969-05-08 | 1970-11-12 | Hoechst Ag | Verfahren zur Herstellung von Amiden und Estern der 1-Hydroxy-benzimidazol-2-carbonsaeure |
| DE2060199A1 (de) * | 1970-12-08 | 1972-07-06 | Bayer Ag | 1-Hydroxy-2-carbonamido-benzimidazol-3-oxide sowie deren Alkalisalze |
| GB2065098A (en) * | 1979-12-07 | 1981-06-24 | Erba Farmitalia | N-substituted Thiazolyl Derivatives of 7-amino- cephalosporanic Acid |
| US4950602A (en) * | 1987-02-20 | 1990-08-21 | Cornell Research Foundation, Inc. | Inhibition of lactate production by pyruvate adducts |
| US4762870A (en) * | 1987-04-13 | 1988-08-09 | The Firestone Tire & Rubber Company | Rubber compositions modified with hydroxy-benz-imidazole oxides |
| JPH0331257A (ja) * | 1989-06-28 | 1991-02-12 | Kissei Pharmaceut Co Ltd | インドール誘導体の製造方法 |
| JPH0525140A (ja) * | 1991-07-22 | 1993-02-02 | Sankyo Co Ltd | ベンズイミダゾール誘導体 |
| US6169107B1 (en) * | 1993-04-28 | 2001-01-02 | Sumitomo Pharmaceutical Co., Ltd. | Indoloylguanidine derivatives |
| DE69533714T2 (de) | 1994-12-20 | 2005-03-24 | Unilever N.V. | Lactat-dehydrogenase Inhibitoren in kosmetischen Mitteln |
| JP2935102B2 (ja) * | 1996-07-04 | 1999-08-16 | 大塚化学株式会社 | インドール−２−カルボン酸エステル誘導体及び該誘導体を有効成分とする農園芸用殺菌剤 |
| WO1998036774A1 (en) | 1996-12-18 | 1998-08-27 | The Johns Hopkins University School Of Medicine | Method of treating a lactate dehydrogenase-a (ldh-a)-associated disorder |
| CA2562763A1 (en) * | 2004-04-23 | 2006-07-20 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
| WO2006017494A2 (en) | 2004-08-02 | 2006-02-16 | Elizabeth Mazzio | Inhibition of anaerobic glucose metabolism |
| JP2009020453A (ja) * | 2007-07-13 | 2009-01-29 | Fujifilm Corp | 感光性組成物、硬化性組成物、カラーフィルタ用硬化性組成物、カラーフィルタ及びその製造方法、並びに、平版印刷版原版 |
| US8278436B2 (en) | 2008-07-30 | 2012-10-02 | Wisconsin Alumni Research Foundation | Glycosylated warfarin analogs and uses thereof |
-
2009
- 2009-11-09 IT IT000140A patent/ITPI20090140A1/it unknown
-
2010
- 2010-11-05 WO PCT/EP2010/006740 patent/WO2011054525A1/en not_active Ceased
- 2010-11-05 JP JP2012537324A patent/JP2013510106A/ja active Pending
- 2010-11-05 EP EP10785332A patent/EP2499114A1/en not_active Withdrawn
- 2010-11-05 BR BR112012010868A patent/BR112012010868A2/pt not_active IP Right Cessation
- 2010-11-05 US US13/508,473 patent/US20120309794A1/en not_active Abandoned
- 2010-11-05 CN CN2010800516087A patent/CN102639497A/zh active Pending
- 2010-11-05 CA CA2780136A patent/CA2780136A1/en not_active Abandoned
- 2010-11-05 AU AU2010314367A patent/AU2010314367A1/en not_active Abandoned
- 2010-11-05 EA EA201290316A patent/EA201290316A1/ru unknown
-
2012
- 2012-05-31 ZA ZA2012/03993A patent/ZA201203993B/en unknown
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