CA2565852C - 3- or 4-monosubstituted phenol and thiophenol derivatives useful as h3 ligands - Google Patents
3- or 4-monosubstituted phenol and thiophenol derivatives useful as h3 ligands Download PDFInfo
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- CA2565852C CA2565852C CA2565852A CA2565852A CA2565852C CA 2565852 C CA2565852 C CA 2565852C CA 2565852 A CA2565852 A CA 2565852A CA 2565852 A CA2565852 A CA 2565852A CA 2565852 C CA2565852 C CA 2565852C
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- alkyl
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- compound
- optionally substituted
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- -1 4-monosubstituted phenol Chemical class 0.000 title claims abstract 8
- 239000003446 ligand Substances 0.000 title claims abstract 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 title abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 5
- 208000026935 allergic disease Diseases 0.000 claims abstract 3
- 201000010099 disease Diseases 0.000 claims abstract 3
- 230000000172 allergic effect Effects 0.000 claims abstract 2
- 208000027866 inflammatory disease Diseases 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 73
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 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 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000003282 alkyl amino group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 239000005864 Sulphur Substances 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009137 Chronic sinusitis Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 208000027219 Deficiency disease Diseases 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 206010057671 Female sexual dysfunction Diseases 0.000 claims 1
- 229940124056 Histamine H1 receptor antagonist Drugs 0.000 claims 1
- 206010057672 Male sexual dysfunction Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 206010028735 Nasal congestion Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010039094 Rhinitis perennial Diseases 0.000 claims 1
- 208000036284 Rhinitis seasonal Diseases 0.000 claims 1
- 208000012886 Vertigo Diseases 0.000 claims 1
- 206010064948 Viral rhinitis Diseases 0.000 claims 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
- 230000008369 airway response Effects 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims 1
- 230000019771 cognition Effects 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 208000027744 congestion Diseases 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 208000002173 dizziness Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 239000000938 histamine H1 antagonist Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 201000003152 motion sickness Diseases 0.000 claims 1
- 208000037916 non-allergic rhinitis Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000005961 oxazepanyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 230000035882 stress Effects 0.000 claims 1
- 231100000889 vertigo Toxicity 0.000 claims 1
- 208000035475 disorder Diseases 0.000 abstract 2
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 208000023504 respiratory system disease Diseases 0.000 abstract 1
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- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
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- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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Applications Claiming Priority (5)
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| EP04291187A EP1593679A1 (en) | 2004-05-07 | 2004-05-07 | 3- Or 4-monosubstituted phenol derivatives useful as H3 ligands |
| EP04291187.5 | 2004-05-07 | ||
| GB0504564A GB0504564D0 (en) | 2005-03-04 | 2005-03-04 | New compounds |
| GB0504564.6 | 2005-03-04 | ||
| PCT/IB2005/001114 WO2005108384A1 (en) | 2004-05-07 | 2005-04-19 | 3- or 4-monosubstituted phenol and thiophenol derivatives useful as h3 ligands |
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| CA2565852A1 CA2565852A1 (en) | 2005-11-17 |
| CA2565852C true CA2565852C (en) | 2010-08-10 |
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| CA2565852A Expired - Fee Related CA2565852C (en) | 2004-05-07 | 2005-04-19 | 3- or 4-monosubstituted phenol and thiophenol derivatives useful as h3 ligands |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8329950B2 (en) | 2005-07-06 | 2012-12-11 | Sunovion Pharmaceuticals Inc. | Process for preparation of trans 4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1Napthalenamine |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
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| MY150088A (en) | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| WO2005066135A2 (en) | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole daao inhibitors |
| JP2006213674A (ja) * | 2005-02-07 | 2006-08-17 | Ube Ind Ltd | ４−ホルミルテトラヒドロピラン化合物の製法 |
| WO2007045989A1 (en) * | 2005-10-20 | 2007-04-26 | Pfizer Limited | Pyridyl derivatives useful as h3 ligands |
| JP5432526B2 (ja) | 2006-01-06 | 2014-03-05 | サノビオン ファーマシューティカルズ インク | モノアミン再取り込み阻害剤としてのシクロアルキルアミン |
| CA2636275C (en) | 2006-01-06 | 2013-02-12 | Sepracor Inc. | Tetralone-based monoamine reuptake inhibitors |
| US8097760B2 (en) | 2006-03-31 | 2012-01-17 | Sunovion Pharmacuticals Inc. | Preparation of chiral amides and amines |
| EP2007723A2 (en) | 2006-04-11 | 2008-12-31 | Novartis AG | Organic compounds |
| KR20090024811A (ko) | 2006-06-23 | 2009-03-09 | 아보트 러보러터리즈 | 히스타민 ｈ3 수용체 조절제로서의 사이클로프로필 아민 유도체 |
| US9108948B2 (en) * | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| US7884124B2 (en) | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| CN101610761A (zh) * | 2006-12-22 | 2009-12-23 | 诺瓦提斯公司 | 作为ddp-iv抑制剂的1-氨基甲基-l-苯基-环己烷衍生物 |
| US7902252B2 (en) | 2007-01-18 | 2011-03-08 | Sepracor, Inc. | Inhibitors of D-amino acid oxidase |
| EP3296289A3 (en) | 2007-05-31 | 2018-06-20 | Sunovion Pharmaceuticals Inc. | Phenyl substituted cycloalkylamines as monoamine reuptake inhibitors |
| TW201039822A (en) | 2009-02-06 | 2010-11-16 | Taisho Pharmaceutical Co Ltd | Dihydroquinolinone derivatives |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| SG186885A1 (en) | 2010-06-04 | 2013-02-28 | Albany Molecular Res Inc | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| US8853390B2 (en) | 2010-09-16 | 2014-10-07 | Abbvie Inc. | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| CN103906746B (zh) * | 2011-10-26 | 2015-12-09 | 辉瑞有限公司 | 用作钠通道调节剂的(4-苯基咪唑-2-基)乙胺衍生物 |
| WO2014095534A1 (en) * | 2012-12-19 | 2014-06-26 | Basf Se | New substituted triazoles and imidazoles and their use as fungicides |
| ES2647965T3 (es) * | 2013-01-09 | 2017-12-27 | Arena Pharmaceuticals, Inc. | Derivados de bifenil-etil-pirrolidina como moduladores del receptor de histamina H3 para el tratamiento de trastornos cognitivos |
| TWI663159B (zh) * | 2013-12-10 | 2019-06-21 | 美商健臻公司 | 原肌球蛋白相關之激酶（ｔｒｋ）抑制劑 |
| SG11201704872RA (en) | 2014-12-18 | 2017-07-28 | Genzyme Corp | Pharmaceutical formulations of tropomyosin related kinase (trk) inhibitors |
| CN113336715B (zh) * | 2021-08-04 | 2021-11-23 | 山东海利尔化工有限公司 | 一种含二氧戊环的三唑类化合物及其中间体的制备方法 |
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| DE3024836A1 (de) * | 1980-07-01 | 1982-01-28 | A. Nattermann & Cie GmbH, 5000 Köln | (3-alkylamino-2-hydroxy-propoxy)-benzylnitrile, verfahren zu deren herstellung und diese als wirkstof enthaltende arzneimittel |
| DK368687A (da) * | 1986-11-21 | 1988-05-22 | Cheminova As | Aminoalkylerede hydroxyforbindelser og deres anvendelse som fungicider |
| ATE372981T1 (de) * | 2000-07-13 | 2007-09-15 | Abbott Lab | 1,3-disubstituierte und 1,3,3-trisubstituierte pyrrolidine als liganden des histamin-3 rezeptors und ihre therapeutischen anwendungen |
| ES2282279T3 (es) * | 2000-08-08 | 2007-10-16 | Ortho-Mcneil Pharmaceutical, Inc. | No-imidazol ariloxipiperidina como ligandos del receptor h3. |
| CA2441080A1 (en) * | 2001-03-23 | 2002-10-03 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8329950B2 (en) | 2005-07-06 | 2012-12-11 | Sunovion Pharmaceuticals Inc. | Process for preparation of trans 4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1Napthalenamine |
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