ZA200106584B - Triazole compounds with dopamine-D3-receptor affinity. - Google Patents
Triazole compounds with dopamine-D3-receptor affinity. Download PDFInfo
- Publication number
- ZA200106584B ZA200106584B ZA200106584A ZA200106584A ZA200106584B ZA 200106584 B ZA200106584 B ZA 200106584B ZA 200106584 A ZA200106584 A ZA 200106584A ZA 200106584 A ZA200106584 A ZA 200106584A ZA 200106584 B ZA200106584 B ZA 200106584B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- alkyl
- compound
- formula
- halogen
- Prior art date
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- -1 Triazole compounds Chemical class 0.000 title claims description 35
- 102000004073 Dopamine D3 Receptors Human genes 0.000 title description 4
- 108090000525 Dopamine D3 Receptors Proteins 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 69
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 229960003638 dopamine Drugs 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 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 description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 229940044551 receptor antagonist Drugs 0.000 claims description 3
- 239000002464 receptor antagonist Substances 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
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- 239000000018 receptor agonist Substances 0.000 claims 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Families Citing this family (53)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9810876D0 (en) | 1998-05-20 | 1998-07-22 | Smithkline Beecham Plc | Compounds |
PE20001088A1 (es) | 1998-10-08 | 2000-12-02 | Smithkline Beecham Plc | Compuestos derivados de tetrahidrobenzazepina |
TWI274750B (en) | 1999-01-12 | 2007-03-01 | Abbott Gmbh & Co Kg | Triazole compounds showing high affinity to dopamine D3 receptor and pharmaceutical composition comprising the same |
AU2001256733A1 (en) * | 2000-05-16 | 2001-11-26 | Takeda Chemical Industries Ltd. | Melanin-concentrating hormone antagonist |
IL155873A0 (en) | 2000-11-14 | 2003-12-23 | Smithkline Beecham Plc | Tetrahydrobenzazepine derivatives useful as modulators of dopamine d3 receptors (antipsychotic agents) |
HU227543B1 (en) * | 2001-09-28 | 2011-08-29 | Richter Gedeon Nyrt | N-[4-(2-piperazin- and 2-piperidin-1-yl-ethyl)-cyclohexyl]-sulfon- and sulfamides, process for their preparation, their use and pharmaceutical compositions containing them |
GB0130219D0 (en) * | 2001-12-18 | 2002-02-06 | Pfizer Ltd | Compounds for the treatment of sexual dysfunction |
JP2005518414A (ja) * | 2001-12-21 | 2005-06-23 | スミスクライン ビーチャム パブリック リミテッド カンパニー | ドーパミン受容体のモジュレーターとしての7−スルホニル−3−ベンゾアゼピン誘導体およびcns障害の治療のためのその使用 |
US7314937B2 (en) * | 2002-03-21 | 2008-01-01 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine H3 receptor antagonists, preparation and therapeutic uses |
MY133587A (en) | 2002-05-29 | 2007-11-30 | Glaxo Group Ltd | Aromatic sulfones and their medical use |
DE10304870A1 (de) * | 2003-02-06 | 2004-08-19 | Abbott Gmbh & Co. Kg | Triazolverbindungen und ihre therapeutische Verwendung |
ES2308157T3 (es) * | 2003-03-17 | 2008-12-01 | Bayer Healthcare Ag | Disgnosticos y tratamientos para enfermedades asociadas con el receptor de la dopamina d3 (drd3). |
US6919342B2 (en) | 2003-06-05 | 2005-07-19 | Abbott Gmbh & Co. Kg | Triazole compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor |
US20080207685A1 (en) * | 2003-11-20 | 2008-08-28 | Eli Lilly And Company | Heterocyclic Compounds As Modulators Of Peroxisome Proliferator Activated Receptors, Useful For The Treatment And/Or Prevention Of Disorders Modulated By A Ppar |
KR20050054084A (ko) * | 2003-12-03 | 2005-06-10 | 한국전자통신연구원 | 수신 환경에 기반한 위성 상태 데이터 분배 기능을 가지는위성관제 시스템 및 그 방법 |
SI1745040T1 (sl) | 2004-02-23 | 2010-04-30 | Venue Glaxo Group Ltd | Derivati azabiciklo(3.1.0)heksana, uporabni kot modulatorji dopaminskih receptorjev d3 |
EP1737851A1 (en) * | 2004-03-08 | 2007-01-03 | Glaxo Group Limited | Tetrahydrobenzazepine derivatives as modulators of dopamine d3 receptors (antipsychotic agents) |
WO2005090320A2 (en) * | 2004-03-12 | 2005-09-29 | Wyeth | Triazole derivatives and method of using the same to treat hiv infections |
GB0412314D0 (en) * | 2004-06-02 | 2004-07-07 | Glaxo Group Ltd | Compounds |
DE102004027358A1 (de) | 2004-06-04 | 2005-12-29 | Abbott Gmbh & Co. Kg | Pyrimidinverbindungen und ihre Verwendung |
GB0413879D0 (en) | 2004-06-21 | 2004-07-21 | Glaxo Group Ltd | Compounds |
GB0414795D0 (en) * | 2004-07-01 | 2004-08-04 | Glaxo Group Ltd | Compounds |
MX2007001530A (es) * | 2004-08-09 | 2007-04-23 | Abbott Gmbh & Co Kg | Compuestos de 4-piperazinil-pirimidina adecuados para tratar trastornos que responde a la modulacion del receptor dopamina d3. |
CA2577060A1 (en) * | 2004-08-13 | 2006-02-23 | Amgen Inc. | Substituted benzofused heterocycles |
US8101754B2 (en) | 2004-12-02 | 2012-01-24 | Abbott Gmbh & Co. Kg | Triazole compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor |
GB0507602D0 (en) * | 2005-04-14 | 2005-05-18 | Glaxo Group Ltd | Compounds |
GB0507680D0 (en) | 2005-04-15 | 2005-05-25 | Glaxo Group Ltd | Compounds |
JP5068747B2 (ja) * | 2005-06-14 | 2012-11-07 | グラクソ グループ リミテッド | ドーパミンd3受容体のモジュレーターとしてのアザビシクロ[3.1.0]ヘキサン誘導体 |
EP1928846B1 (en) | 2005-08-18 | 2014-06-04 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate hsp90 activity |
WO2007022933A1 (en) * | 2005-08-22 | 2007-03-01 | Glaxo Group Limited | Triazole derivatives as modulators of dopamine d3 receptors |
WO2007028145A2 (en) * | 2005-09-02 | 2007-03-08 | Dara Biosciences, Inc. | Agents and methods for reducing protein tyrosine phosphatase 1b activity in the central nervous system |
US20070293548A1 (en) * | 2006-03-31 | 2007-12-20 | Wang Eric Y | Inhibitors of semicarbazide-sensitive amine oxidase (SSAO) and VAP-1 mediated adhesion useful for treatment and prevention of diseases |
JP5523839B2 (ja) | 2007-02-08 | 2014-06-18 | シンタ ファーマシューティカルズ コーポレーション | 癌などの増殖障害の治療に有用なトリアゾール化合物 |
US8106083B2 (en) | 2008-08-08 | 2012-01-31 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
EP2354136B1 (en) | 2008-10-10 | 2016-02-24 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China | Novel dopamine d3 receptor ligands and preparation and medical uses of the same |
US9227944B2 (en) | 2008-10-10 | 2016-01-05 | Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China | Dopamine D3 receptor ligands and preparation and medical uses of the same |
US9326955B2 (en) * | 2008-10-31 | 2016-05-03 | Loyola University Chicago | Combination pharmaceuticals and methods thereof using proteinacious channels as treatments for medical conditions |
ES2523766T3 (es) * | 2009-12-22 | 2014-12-01 | Cephalon, Inc | Hexahidrocromeno[3,4-b]pirroles sustituidos con afinidad por la familia de los receptores de serotonina (5-HT) |
JPWO2012124744A1 (ja) * | 2011-03-14 | 2014-07-24 | 大正製薬株式会社 | 含窒素縮合複素環化合物 |
WO2013178572A1 (en) * | 2012-05-30 | 2013-12-05 | F. Hoffmann-La Roche Ag | Triazolo compounds as pde10 inhibitors |
RU2561063C1 (ru) * | 2014-07-01 | 2015-08-20 | Общество с ограниченной ответственностью "Научно-производственное объединение "Фарматрон" (НПО "Фарматрон") | Способ коррекции неврологических нарушений при хронической алкогольной интоксикации |
WO2016034673A1 (en) | 2014-09-03 | 2016-03-10 | Ctxt Pty Ltd | Tetrahydroisoquinoline derived prmt5-inhibitors |
WO2016034671A1 (en) | 2014-09-03 | 2016-03-10 | Ctxt Pty Ltd | Aminoindane-, aminotetrahydronaphthalene- and aminobenzocyclobutane-derived prmt5-inhibitors |
GB201415573D0 (en) | 2014-09-03 | 2014-10-15 | Cancer Therapeutics Crc Pty Ltd | Compounds |
GB201604031D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
GB201604029D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
GB201604022D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
GB201604027D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
GB201604030D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
GB201604020D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
JP7343170B2 (ja) * | 2017-05-12 | 2023-09-12 | ボード オブ トラスティーズ オブ ザ サザン イリノイ ユニバーシティ オン ビハーフ オブ サザン イリノイ ユニバーシティ エドワーズビル | 3,4,5-三置換-1,2,4-トリアゾールおよび3,4,5-三置換-3-チオ-1,2,4-トリアゾール、ならびにそれらの使用 |
US10941153B2 (en) * | 2018-05-31 | 2021-03-09 | Regents Of The University Of Minnesota | Substituted phenethylamine derivatives |
GB202117129D0 (en) * | 2021-11-26 | 2022-01-12 | Epidarex Exeed Ltd | Compounds |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4408049A (en) | 1980-09-17 | 1983-10-04 | The Upjohn Company | Substituted piperazinyl-1,2,4-triazoles |
US4338453A (en) * | 1980-09-17 | 1982-07-06 | The Upjohn Company | Aminoalkyl-1,2,4-triazoles |
US4577020A (en) * | 1983-01-25 | 1986-03-18 | The Upjohn Company | Aminoalkyl and aminoalkenyl triazoles as anti-psychotic agents |
FR2601952B1 (fr) * | 1986-07-23 | 1988-11-25 | Carpibem | Nouveaux derives amino alkyl thio de triazolopyridine ou triazoloquinoline, leurs procedes de preparation, medicaments les contenant, utiles notamment comme antalgiques |
AU644500B2 (en) * | 1990-12-20 | 1993-12-09 | Merrell Dow Pharmaceuticals Inc. | 3-aryl-5-alkylthio-4h-1,2,4-triazoles for treatment of hyperreflexia due to spinal trauma |
ES2103374T3 (es) | 1991-05-20 | 1997-09-16 | Upjohn Co | Derivados de carboxamido-(1,2n)-carbociclo-2-aminotetralina. |
WO1994025013A1 (en) | 1993-04-27 | 1994-11-10 | Smithkline Beecham Corporation | Endothelin receptor antagonists |
JP2667294B2 (ja) | 1991-11-05 | 1997-10-27 | スミスクライン・ビーチャム・コーポレイション | エンドセリン受容体拮抗剤 |
FR2687146B1 (fr) | 1992-02-12 | 1994-04-01 | Adir Cie | Nouveaux derives de pyrrolidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
DE4338396A1 (de) * | 1993-11-10 | 1995-05-11 | Basf Ag | N-Substituierte Azabicycloalkan-Derivate, ihre Herstellung und Verwendung |
FR2722194B1 (fr) | 1994-07-06 | 1996-08-23 | Adir | Nouveaux derives de benzopyrane, leur procede de preparation et les compositions pharmacuetiques qui les contiennent |
DE4425144A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Triazolverbindungen und deren Verwendung |
EP0793653A1 (en) * | 1994-11-23 | 1997-09-10 | Neurogen Corporation | Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands |
US6008219A (en) | 1995-03-27 | 1999-12-28 | Smithkline Beech P.L.C. | Bicyclic amine derivatives and their use as anti-psychotic agents |
WO1996031512A1 (en) * | 1995-04-06 | 1996-10-10 | Novo Nordisk A/S | Benzopyranopyrrole compounds, their preparation and use |
GB9518572D0 (en) | 1995-09-12 | 1995-11-15 | Smithkline Beecham Plc | Compounds |
JPH11515030A (ja) * | 1995-11-10 | 1999-12-21 | ノボ ノルディスク アクティーゼルスカブ | シス−ベンズ[e]インドール化合物のエナンチオマー、これらの製造、及びドーパミン−D3受容体選択的医薬としての利用 |
FR2742149B1 (fr) * | 1995-12-11 | 1998-02-13 | Inst Nat Sante Rech Med | Nouveaux derives de 2-naphtamides et leurs applications therapeutiques |
DE19600934A1 (de) * | 1996-01-12 | 1997-07-17 | Basf Ag | Substituierte Aza- und Diazacycloheptan- und Cyclooctanverbindungen und deren Verwendung |
US5688950A (en) | 1996-04-23 | 1997-11-18 | Neurogen Corporation | Tricyclic aminoalkylcarboxamides; novel dopamine D3 receptor subtype specific ligands |
PL329803A1 (en) * | 1996-05-11 | 1999-04-12 | Smithkline Beecham Plc | Derivatives of tetrahydroisoquinoline as modulators od dopamine d receptors |
CN1159292C (zh) * | 1996-05-31 | 2004-07-28 | 法玛西雅厄普约翰美国公司 | 用作选择性多巴胺d3配体的芳基取代的环胺类化合物 |
GB9612153D0 (en) | 1996-06-11 | 1996-08-14 | Smithkline Beecham Plc | Compounds |
WO1998006699A1 (en) | 1996-08-14 | 1998-02-19 | Smithkline Beecham Plc | Tetrahydroisoquinoline derivatives and their pharmaceutical use |
JPH10195056A (ja) * | 1996-11-12 | 1998-07-28 | Takeda Chem Ind Ltd | 縮合ベンゼン誘導体、その製造法および剤 |
TR199901883T2 (xx) | 1996-12-06 | 1999-12-21 | Abbott Laboratories | Benzopiranopirol ve benzopiranopiridin alfa-1 adrenerjik bile�ikleri. |
FR2760014B1 (fr) | 1997-02-27 | 1999-04-09 | Adir | Nouveaux composes de 2-amino indane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
GB9708694D0 (en) | 1997-04-30 | 1997-06-18 | Smithkline Beecham Plc | Compounds |
GB9708805D0 (en) | 1997-05-01 | 1997-06-25 | Smithkline Beecham Plc | Compounds |
TR199902724T2 (xx) * | 1997-05-03 | 2000-04-21 | Smithkline Beecham P.L.C. | Dopamine D3 resept�rleri mod�lat�rleri olarak tetrahidroisokuinolin t�revleri. |
GB9709303D0 (en) | 1997-05-09 | 1997-06-25 | Smithkline Beecham Plc | Compounds |
GB9710366D0 (en) * | 1997-05-20 | 1997-07-16 | Biocompatibles Ltd | Stent deployment device |
FR2764890B1 (fr) * | 1997-06-24 | 1999-08-27 | Adir | Nouveaux derives chromeniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
DE19728996A1 (de) * | 1997-07-07 | 1999-01-14 | Basf Ag | Triazolverbindungen und deren Verwendung |
TWI274750B (en) | 1999-01-12 | 2007-03-01 | Abbott Gmbh & Co Kg | Triazole compounds showing high affinity to dopamine D3 receptor and pharmaceutical composition comprising the same |
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2000
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