JP2008508250A5 - - Google Patents
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- Publication number
- JP2008508250A5 JP2008508250A5 JP2007523163A JP2007523163A JP2008508250A5 JP 2008508250 A5 JP2008508250 A5 JP 2008508250A5 JP 2007523163 A JP2007523163 A JP 2007523163A JP 2007523163 A JP2007523163 A JP 2007523163A JP 2008508250 A5 JP2008508250 A5 JP 2008508250A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- formula
- carbonyl
- quinolin
- group
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 230000003287 optical effect Effects 0.000 claims 5
- 241000725303 Human immunodeficiency virus Species 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- -1 hydroxy, amino Chemical group 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010058019 Cancer Pain Diseases 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 206010011878 Deafness Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 241000282412 Homo Species 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000013016 Hypoglycemia Diseases 0.000 claims 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 208000007101 Muscle Cramp Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000005392 Spasm Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 208000009205 Tinnitus Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 229940126574 aminoglycoside antibiotic Drugs 0.000 claims 2
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 229960003920 cocaine Drugs 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003995 emulsifying agent Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 239000000796 flavoring agent Substances 0.000 claims 2
- 235000013355 food flavoring agent Nutrition 0.000 claims 2
- 239000003205 fragrance Substances 0.000 claims 2
- 230000010370 hearing loss Effects 0.000 claims 2
- 231100000888 hearing loss Toxicity 0.000 claims 2
- 208000016354 hearing loss disease Diseases 0.000 claims 2
- 230000002218 hypoglycaemic effect Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 231100000878 neurological injury Toxicity 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 230000003204 osmotic effect Effects 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 210000001525 retina Anatomy 0.000 claims 2
- 210000000278 spinal cord Anatomy 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 231100000886 tinnitus Toxicity 0.000 claims 2
- 230000008736 traumatic injury Effects 0.000 claims 2
- 238000009736 wetting Methods 0.000 claims 2
- 239000000080 wetting agent Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- UMURLIQHQSKULR-UHFFFAOYSA-N 1,3-oxazolidine-2-thione Chemical compound S=C1NCCO1 UMURLIQHQSKULR-UHFFFAOYSA-N 0.000 claims 1
- KKRIBHRZSNFQDW-UHFFFAOYSA-N 2-(4-benzyl-4-hydroxypiperidine-1-carbonyl)-6-hydroxy-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(O)=CC=C2NC=1C(=O)N(CC1)CCC1(O)CC1=CC=CC=C1 KKRIBHRZSNFQDW-UHFFFAOYSA-N 0.000 claims 1
- GFGQSYKVLAPXSK-UHFFFAOYSA-N 2-(4-benzyl-4-hydroxypiperidine-1-carbonyl)-7-hydroxy-1h-quinolin-4-one Chemical compound C=1C(O)=CC=C(C(C=2)=O)C=1NC=2C(=O)N(CC1)CCC1(O)CC1=CC=CC=C1 GFGQSYKVLAPXSK-UHFFFAOYSA-N 0.000 claims 1
- WSQIXOAHSYKTPB-UHFFFAOYSA-N 2-(4-benzylpiperidine-1-carbonyl)-6-hydroxy-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(O)=CC=C2NC=1C(=O)N(CC1)CCC1CC1=CC=CC=C1 WSQIXOAHSYKTPB-UHFFFAOYSA-N 0.000 claims 1
- SFVDRVNMUZDDKU-UHFFFAOYSA-N 2-[4-(4-chlorophenoxy)piperidine-1-carbonyl]-6-hydroxy-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(O)=CC=C2NC=1C(=O)N(CC1)CCC1OC1=CC=C(Cl)C=C1 SFVDRVNMUZDDKU-UHFFFAOYSA-N 0.000 claims 1
- NOZNBDRZICFUMG-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]piperidine-1-carbonyl]-6-hydroxy-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(O)=CC=C2NC=1C(=O)N(CC1)CCC1CC1=CC=C(Cl)C=C1 NOZNBDRZICFUMG-UHFFFAOYSA-N 0.000 claims 1
- LKPBNPWHIMZYIV-UHFFFAOYSA-N 2-[4-[(4-fluorophenyl)methyl]piperidine-1-carbonyl]-6-hydroxy-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(O)=CC=C2NC=1C(=O)N(CC1)CCC1CC1=CC=C(F)C=C1 LKPBNPWHIMZYIV-UHFFFAOYSA-N 0.000 claims 1
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 1
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical group O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 claims 1
- HCVJMMUWUHUCPH-UHFFFAOYSA-N 6-(4-benzylpiperidine-1-carbonyl)-1,5-dihydro-[1,3]oxazolo[4,5-g]quinoline-2,8-dione Chemical compound C=1C(=O)C2=CC=3NC(=O)OC=3C=C2NC=1C(=O)N(CC1)CCC1CC1=CC=CC=C1 HCVJMMUWUHUCPH-UHFFFAOYSA-N 0.000 claims 1
- VQNLGRLAIHYCGG-UHFFFAOYSA-N 6-hydroxy-2-(4-phenoxypiperidine-1-carbonyl)-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(O)=CC=C2NC=1C(=O)N(CC1)CCC1OC1=CC=CC=C1 VQNLGRLAIHYCGG-UHFFFAOYSA-N 0.000 claims 1
- YQEAAHXKUSMKLA-UHFFFAOYSA-N 6-hydroxy-2-(4-phenylmethoxypiperidine-1-carbonyl)-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(O)=CC=C2NC=1C(=O)N(CC1)CCC1OCC1=CC=CC=C1 YQEAAHXKUSMKLA-UHFFFAOYSA-N 0.000 claims 1
- XNCXZLFRTYDNRY-UHFFFAOYSA-N 6-hydroxy-2-[4-(4-methylphenoxy)piperidine-1-carbonyl]-1h-quinolin-4-one Chemical compound C1=CC(C)=CC=C1OC1CCN(C(=O)C=2NC3=CC=C(O)C=C3C(=O)C=2)CC1 XNCXZLFRTYDNRY-UHFFFAOYSA-N 0.000 claims 1
- ZBCDSXQAMHZQGM-UHFFFAOYSA-N 6-hydroxy-2-[4-(phenoxymethyl)piperidine-1-carbonyl]-1h-quinolin-4-one Chemical compound C=1C(=O)C2=CC(O)=CC=C2NC=1C(=O)N(CC1)CCC1COC1=CC=CC=C1 ZBCDSXQAMHZQGM-UHFFFAOYSA-N 0.000 claims 1
- NRKFXELBKOAUIH-UHFFFAOYSA-N 6-hydroxy-2-[4-[(4-methylphenyl)methyl]piperidine-1-carbonyl]-1h-quinolin-4-one Chemical compound C1=CC(C)=CC=C1CC1CCN(C(=O)C=2NC3=CC=C(O)C=C3C(=O)C=2)CC1 NRKFXELBKOAUIH-UHFFFAOYSA-N 0.000 claims 1
- 102100022630 Glutamate receptor ionotropic, NMDA 2B Human genes 0.000 claims 1
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims 1
- 102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 108010038912 Retinoid X Receptors Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
- IMWUREPEYPRYOR-UHFFFAOYSA-N pyrrolidine-2-thione Chemical compound S=C1CCCN1 IMWUREPEYPRYOR-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0401525A HU226977B1 (en) | 2004-07-29 | 2004-07-29 | Kynurenic acid amide derivatives, pharmaceutical compositions containing them and process for producing them |
| PCT/HU2005/000080 WO2006010967A1 (en) | 2004-07-29 | 2005-07-21 | Kynurenic acid amide derivatives as nr2b receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008508250A JP2008508250A (ja) | 2008-03-21 |
| JP2008508250A5 true JP2008508250A5 (enExample) | 2008-05-15 |
Family
ID=89985410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007523163A Withdrawn JP2008508250A (ja) | 2004-07-29 | 2005-07-21 | Ｎｒ２ｂ受容体アンタゴニストとしてのキヌレン酸アミド誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20090012118A1 (enExample) |
| EP (1) | EP1771436A1 (enExample) |
| JP (1) | JP2008508250A (enExample) |
| KR (1) | KR20070043965A (enExample) |
| CN (1) | CN1989127A (enExample) |
| AP (1) | AP2006003842A0 (enExample) |
| AU (1) | AU2005266162A1 (enExample) |
| BR (1) | BRPI0513912A (enExample) |
| CA (1) | CA2574167A1 (enExample) |
| EA (1) | EA011636B1 (enExample) |
| GE (1) | GEP20084493B (enExample) |
| HU (1) | HU226977B1 (enExample) |
| IL (1) | IL179487A0 (enExample) |
| MA (1) | MA28819B1 (enExample) |
| MX (1) | MX2007001057A (enExample) |
| NO (1) | NO20071111L (enExample) |
| TN (1) | TNSN07015A1 (enExample) |
| WO (1) | WO2006010967A1 (enExample) |
| ZA (1) | ZA200700321B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2608476A1 (en) * | 2005-06-28 | 2007-01-04 | Bausch & Lomb Incorporated | Preparations comprising arylazine substituted with a carbonylic moiety to increase the activity of gelatinase a in ocular cells |
| US7935706B2 (en) | 2006-02-23 | 2011-05-03 | Shionogi & Co., Ltd. | Nitrogen-containing heterocycle derivatives substituted with cyclic group |
| US8008253B2 (en) | 2007-07-03 | 2011-08-30 | Andrew Tasker | Treatment for anxiety |
| US9051296B2 (en) | 2009-11-16 | 2015-06-09 | Raqualia Pharma Inc. | Aryl carboxamide derivatives as TTX-S blockers |
| JP2013514379A (ja) * | 2009-12-15 | 2013-04-25 | ニユーロツプ・インコーポレイテツド | 神経障害の治療のための化合物 |
| CN102762554A (zh) | 2010-02-16 | 2012-10-31 | 辉瑞大药厂 | 5-ht4受体的部分激动剂(r)-4-((4-((4-(四氢呋喃-3-基氧基)苯并[d]异*唑-3-基氧基)甲基)哌啶-1-基)甲基)四氢-2h-吡喃-4-醇 |
| HU230366B1 (hu) * | 2010-06-29 | 2016-03-29 | Szegedi Tudományegyetem | Kinurénsavamid származékok alkalmazása Huntington-kór kezelésére |
| CA2869216A1 (en) | 2012-04-20 | 2013-10-24 | Ucb Pharma S.A. | Methods for treating parkinson's disease |
| HUP1600179A2 (hu) | 2016-03-04 | 2017-09-28 | Univ Szegedi | Új típusú C-3 szubsztituált kinurénsavszármazékok hatékonyabb neuroprotektív aktivitással |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6713490B2 (en) * | 2002-04-26 | 2004-03-30 | Pfizer, Inc. | 3,4-dihydroquinolin-2(1H)-one compounds as NR2B receptor antagonists |
-
2004
- 2004-07-29 HU HU0401525A patent/HU226977B1/hu unknown
-
2005
- 2005-07-21 CA CA002574167A patent/CA2574167A1/en not_active Abandoned
- 2005-07-21 AU AU2005266162A patent/AU2005266162A1/en not_active Abandoned
- 2005-07-21 EP EP05764169A patent/EP1771436A1/en not_active Withdrawn
- 2005-07-21 BR BRPI0513912-0A patent/BRPI0513912A/pt not_active IP Right Cessation
- 2005-07-21 AP AP2006003842A patent/AP2006003842A0/xx unknown
- 2005-07-21 JP JP2007523163A patent/JP2008508250A/ja not_active Withdrawn
- 2005-07-21 GE GEAP20059895A patent/GEP20084493B/en unknown
- 2005-07-21 EA EA200700364A patent/EA011636B1/ru not_active IP Right Cessation
- 2005-07-21 US US11/658,690 patent/US20090012118A1/en not_active Abandoned
- 2005-07-21 CN CNA2005800247588A patent/CN1989127A/zh active Pending
- 2005-07-21 KR KR1020077000265A patent/KR20070043965A/ko not_active Withdrawn
- 2005-07-21 MX MX2007001057A patent/MX2007001057A/es not_active Application Discontinuation
- 2005-07-21 WO PCT/HU2005/000080 patent/WO2006010967A1/en not_active Ceased
-
2006
- 2006-11-22 IL IL179487A patent/IL179487A0/en unknown
-
2007
- 2007-01-11 ZA ZA200700321A patent/ZA200700321B/en unknown
- 2007-01-17 TN TNP2007000015A patent/TNSN07015A1/en unknown
- 2007-02-22 MA MA29706A patent/MA28819B1/fr unknown
- 2007-02-27 NO NO20071111A patent/NO20071111L/no not_active Application Discontinuation
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