AU2005266162A1 - Kynurenic acid amide derivatives as NR2B receptor antagonists - Google Patents
Kynurenic acid amide derivatives as NR2B receptor antagonists Download PDFInfo
- Publication number
- AU2005266162A1 AU2005266162A1 AU2005266162A AU2005266162A AU2005266162A1 AU 2005266162 A1 AU2005266162 A1 AU 2005266162A1 AU 2005266162 A AU2005266162 A AU 2005266162A AU 2005266162 A AU2005266162 A AU 2005266162A AU 2005266162 A1 AU2005266162 A1 AU 2005266162A1
- Authority
- AU
- Australia
- Prior art keywords
- hydroxy
- formula
- piperidine
- meaning
- carbonyl
- 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.)
- Abandoned
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- HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 title claims description 46
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
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- 150000003839 salts Chemical class 0.000 claims description 15
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- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 2
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- 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 description 2
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- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
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- 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
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- SSJDBSJQJBTTBE-UHFFFAOYSA-N methyl 2,8-dioxo-1,5-dihydro-[1,3]oxazolo[4,5-g]quinoline-6-carboxylate Chemical compound C1=C2NC(C(=O)OC)=CC(=O)C2=CC2=C1OC(=O)N2 SSJDBSJQJBTTBE-UHFFFAOYSA-N 0.000 description 1
- XSRWQTDEIOHXSL-UHFFFAOYSA-N methyl quinoline-6-carboxylate Chemical compound N1=CC=CC2=CC(C(=O)OC)=CC=C21 XSRWQTDEIOHXSL-UHFFFAOYSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 108091008589 nuclear estrogen receptors Proteins 0.000 description 1
- 108091008757 nuclear thyroid hormone receptors Proteins 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 230000002385 psychotomimetic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PESXGULMKCKJCC-UHFFFAOYSA-M sodium;4-methoxycarbonylphenolate Chemical compound [Na+].COC(=O)C1=CC=C([O-])C=C1 PESXGULMKCKJCC-UHFFFAOYSA-M 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 210000001055 substantia gelatinosa Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FLIHFLFEJNHHDE-UHFFFAOYSA-N tert-butyl 4-(4-chlorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=C(Cl)C=C1 FLIHFLFEJNHHDE-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000003151 transfection method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000009529 traumatic brain injury Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
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- A—HUMAN NECESSITIES
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P31/12—Antivirals
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Virology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- AIDS & HIV (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
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 |
| HUP0401525 | 2004-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005266162A1 true AU2005266162A1 (en) | 2006-02-02 |
Family
ID=89985410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005266162A Abandoned AU2005266162A1 (en) | 2004-07-29 | 2005-07-21 | Kynurenic acid amide derivatives as NR2B receptor antagonists |
Country Status (19)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007002781A2 (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 |
| EP2520567A3 (en) | 2006-02-23 | 2012-12-12 | 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 |
| CA2784119A1 (en) * | 2009-12-15 | 2011-06-23 | Neurop, Inc. | Compounds for the treatment of neurologic disorders |
| KR20120123089A (ko) | 2010-02-16 | 2012-11-07 | 화이자 인코포레이티드 | 5-ＨＴ₄ 수용체의 부분 효능제인 (Ｒ)-4-((4-((4-(테트라히드로푸란-3-일옥시)벤조［ｄ］이속사졸-3-일옥시)메틸)피페리딘-1-일)메틸)테트라히드로-2Ｈ-피란-4-올 |
| HU230366B1 (hu) * | 2010-06-29 | 2016-03-29 | Szegedi Tudományegyetem | Kinurénsavamid származékok alkalmazása Huntington-kór kezelésére |
| AU2013251079B2 (en) | 2012-04-20 | 2017-03-23 | 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 MX MX2007001057A patent/MX2007001057A/es not_active Application Discontinuation
- 2005-07-21 BR BRPI0513912-0A patent/BRPI0513912A/pt not_active IP Right Cessation
- 2005-07-21 AU AU2005266162A patent/AU2005266162A1/en not_active Abandoned
- 2005-07-21 CA CA002574167A patent/CA2574167A1/en not_active Abandoned
- 2005-07-21 EA EA200700364A patent/EA011636B1/ru not_active IP Right Cessation
- 2005-07-21 GE GEAP20059895A patent/GEP20084493B/en unknown
- 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 WO PCT/HU2005/000080 patent/WO2006010967A1/en not_active Ceased
- 2005-07-21 AP AP2006003842A patent/AP2006003842A0/xx unknown
- 2005-07-21 KR KR1020077000265A patent/KR20070043965A/ko not_active Withdrawn
- 2005-07-21 EP EP05764169A patent/EP1771436A1/en not_active Withdrawn
- 2005-07-21 JP JP2007523163A patent/JP2008508250A/ja not_active Withdrawn
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| TNSN07015A1 (en) | 2008-06-02 |
| ZA200700321B (en) | 2008-05-28 |
| GEP20084493B (en) | 2008-09-25 |
| KR20070043965A (ko) | 2007-04-26 |
| WO2006010967A8 (en) | 2007-01-18 |
| AP2006003842A0 (en) | 2006-12-31 |
| JP2008508250A (ja) | 2008-03-21 |
| HU226977B1 (en) | 2010-04-28 |
| NO20071111L (no) | 2007-02-27 |
| EP1771436A1 (en) | 2007-04-11 |
| HU0401525D0 (en) | 2004-09-28 |
| US20090012118A1 (en) | 2009-01-08 |
| CN1989127A (zh) | 2007-06-27 |
| CA2574167A1 (en) | 2006-02-02 |
| MX2007001057A (es) | 2007-04-16 |
| WO2006010967A1 (en) | 2006-02-02 |
| MA28819B1 (fr) | 2007-08-01 |
| HUP0401525A2 (en) | 2006-11-28 |
| EA200700364A1 (ru) | 2007-06-29 |
| EA011636B1 (ru) | 2009-04-28 |
| BRPI0513912A (pt) | 2008-05-20 |
| IL179487A0 (en) | 2007-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |