CA2475767A1 - Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds - Google Patents
Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds Download PDFInfo
- Publication number
- CA2475767A1 CA2475767A1 CA002475767A CA2475767A CA2475767A1 CA 2475767 A1 CA2475767 A1 CA 2475767A1 CA 002475767 A CA002475767 A CA 002475767A CA 2475767 A CA2475767 A CA 2475767A CA 2475767 A1 CA2475767 A1 CA 2475767A1
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- CA
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- Prior art keywords
- compound
- alkyl
- cycloalkyl
- aryl
- tert
- 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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- 102000003840 Opioid Receptors Human genes 0.000 title claims abstract description 35
- 108090000137 Opioid Receptors Proteins 0.000 title claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 250
- 238000000034 method Methods 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 208000002193 Pain Diseases 0.000 claims abstract description 16
- 230000036407 pain Effects 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 109
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 64
- -1 piperazino, pyrrolidino, piperidino, morpholino Chemical group 0.000 claims description 62
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 38
- 125000004423 acyloxy group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000001589 carboacyl group Chemical group 0.000 claims description 34
- 102000005962 receptors Human genes 0.000 claims description 32
- 108020003175 receptors Proteins 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000004429 atom Chemical group 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 15
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
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- LXPRIRPPEBBCBL-UHFFFAOYSA-N 3-(5-tert-butyl-2-methoxyphenyl)-4-(3-methoxyphenyl)-1,2,4-triazole Chemical compound COC1=CC=CC(N2C(=NN=C2)C=2C(=CC=C(C=2)C(C)(C)C)OC)=C1 LXPRIRPPEBBCBL-UHFFFAOYSA-N 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- LFWAVNRDCVJWNS-UHFFFAOYSA-N 3-(3-tert-butylphenyl)-4-(3-methoxyphenyl)-1,2,4-triazole Chemical compound COC1=CC=CC(N2C(=NN=C2)C=2C=C(C=CC=2)C(C)(C)C)=C1 LFWAVNRDCVJWNS-UHFFFAOYSA-N 0.000 claims description 4
- XAUBIRVVXYSHLW-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-(3-methoxyphenyl)-1,2,4-triazole Chemical compound COC1=CC=CC(N2C(=NN=C2)C=2C=CC(=CC=2)C(C)(C)C)=C1 XAUBIRVVXYSHLW-UHFFFAOYSA-N 0.000 claims description 4
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35499002P | 2002-02-07 | 2002-02-07 | |
| US60/354,990 | 2002-02-07 | ||
| PCT/US2003/003746 WO2003066050A1 (en) | 2002-02-07 | 2003-02-07 | Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2475767A1 true CA2475767A1 (en) | 2003-08-14 |
Family
ID=27734448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002475767A Abandoned CA2475767A1 (en) | 2002-02-07 | 2003-02-07 | Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US7045520B2 (enExample) |
| EP (1) | EP1485088B1 (enExample) |
| JP (1) | JP2005521676A (enExample) |
| AT (1) | ATE403426T1 (enExample) |
| AU (1) | AU2003210916B9 (enExample) |
| CA (1) | CA2475767A1 (enExample) |
| DE (1) | DE60322680D1 (enExample) |
| ES (1) | ES2311711T3 (enExample) |
| MX (1) | MXPA04007719A (enExample) |
| WO (1) | WO2003066050A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2475767A1 (en) * | 2002-02-07 | 2003-08-14 | The Curators Of The University Of Missouri | Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds |
| KR20140006070A (ko) | 2004-11-18 | 2014-01-15 | 신타 파마슈티칼스 코프. | Ｈｓｐ90 활성을 조절하는 트리아졸 화합물 |
| WO2006124687A1 (en) * | 2005-05-12 | 2006-11-23 | University Of Medicine And Dentistry Of New Jersey | Opioid receptor subtype-selective agents |
| WO2008064310A2 (en) * | 2006-11-22 | 2008-05-29 | University Of Medicine And Dentistry Of New Jersey | Mixed opioid receptor active compounds |
| WO2011069951A1 (en) | 2009-12-11 | 2011-06-16 | Glaxo Group Limited | Imidazolidinedione derivatives |
| KR101862375B1 (ko) | 2010-12-06 | 2018-05-29 | 오티포니 세라피틱스 리미티드 | Kv3 억제제로서 유용한 하이단토인 유도체 |
| EP3502236B1 (en) | 2011-02-18 | 2023-08-23 | The Scripps Research Institute | Directed differentiation of oligodendrocyte precursor cells to a myelinating cell fate |
| US9193704B2 (en) | 2011-06-07 | 2015-11-24 | Autifony Therapeutics Limited | Hydantoin derivatives as KV3 inhibitors |
| WO2013040321A1 (en) | 2011-09-15 | 2013-03-21 | University Of Kansas | Kappa opioid receptor effectors and uses thereof |
| EP2613277A1 (en) * | 2012-01-06 | 2013-07-10 | MathPharm GmbH | Method and system for indentifying compounds that bind and preferably activate a target opioid receptor in a pH-dependent manner |
| EP2822931B1 (en) | 2012-03-09 | 2017-05-03 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| BR112014028991A2 (pt) | 2012-05-22 | 2017-06-27 | Autifony Therapeutics Ltd | triazóis como inibidores de kv3 |
| BR112014028718A2 (pt) | 2012-05-22 | 2017-06-27 | Autifony Therapeutics Ltd | derivados de hidantoína como inibidores de kv3 |
| JP6404230B2 (ja) | 2012-12-20 | 2018-10-10 | インセプション ２、 インコーポレイテッド | トリアゾロン化合物およびその使用 |
| PT2953942T (pt) | 2013-02-06 | 2018-01-17 | Bayer Cropscience Ag | Derivados de pirazol substituídos com halogéneo como agentes pesticidas |
| CA2921420A1 (en) | 2013-09-06 | 2015-03-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| BR112016017527B1 (pt) | 2014-01-03 | 2021-01-05 | Bayer Animal Health Gmbh | compostos, usos de compostos, composições farmacêuticas, processo para produzir composições e método não terapêutico para controlar pragas |
| WO2016142394A1 (de) | 2015-03-10 | 2016-09-15 | Bayer Animal Health Gmbh | Pyrazolyl-derivate als schädlingsbekämpfungsmittel |
| EP3344997B1 (en) * | 2015-08-31 | 2020-11-18 | Regents of the University of Minnesota | Opioid receptor modulators and use thereof |
| CN111574368B (zh) * | 2020-05-15 | 2023-03-28 | 西安瑞联新材料股份有限公司 | 一种5-叔丁基-2-羟基苯甲酸甲酯的合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2269938A2 (en) | 1974-05-08 | 1975-12-05 | Delalande Sa | 5-Hydroxymethyl-3,4-diphenyl-1,2,4-triazoles - with anticholinergic, bronchodilator, antidepressant, analgesic, vasodilator activity, etc. |
| FR2488891A1 (fr) * | 1980-08-22 | 1982-02-26 | Roussel Uclaf | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
| US4481360A (en) * | 1983-08-26 | 1984-11-06 | The Upjohn Company | 4H-1,2,4-Triazol-3-yl compounds |
| US5108486A (en) * | 1990-02-09 | 1992-04-28 | Kanagawa Chemical Laboratory, Ltd. | Herbicidal substituted-phenyl-1,2,4-triazol-5(1H)-thiones and -ones |
| US5310724A (en) * | 1990-02-09 | 1994-05-10 | Fmc Corporation | Herbicidal substituted phenyl-1,2,4-triazol-5(1H)-thiones |
| AU9297798A (en) | 1997-09-16 | 1999-04-05 | G.D. Searle & Co. | Substituted 1,2,4-triazoles useful for inhibiting cholesteryl ester transfer protein activity |
| JP2000063363A (ja) | 1998-08-12 | 2000-02-29 | Yamanouchi Pharmaceut Co Ltd | 新規なトリアゾール誘導体 |
| HN1999000149A (es) * | 1998-09-09 | 2000-01-12 | Pfizer Prod Inc | Derivados de 4,4-biarilpiperidina |
| CA2475767A1 (en) * | 2002-02-07 | 2003-08-14 | The Curators Of The University Of Missouri | Opioid receptor active 4-(3-hydroxyphenyl) or 4-(3-alkoxyphenyl)-1,2,4-triazole compounds |
-
2003
- 2003-02-07 CA CA002475767A patent/CA2475767A1/en not_active Abandoned
- 2003-02-07 US US10/360,602 patent/US7045520B2/en not_active Expired - Fee Related
- 2003-02-07 WO PCT/US2003/003746 patent/WO2003066050A1/en not_active Ceased
- 2003-02-07 ES ES03737705T patent/ES2311711T3/es not_active Expired - Lifetime
- 2003-02-07 JP JP2003565474A patent/JP2005521676A/ja active Pending
- 2003-02-07 MX MXPA04007719A patent/MXPA04007719A/es active IP Right Grant
- 2003-02-07 EP EP03737705A patent/EP1485088B1/en not_active Expired - Lifetime
- 2003-02-07 AU AU2003210916A patent/AU2003210916B9/en not_active Ceased
- 2003-02-07 AT AT03737705T patent/ATE403426T1/de not_active IP Right Cessation
- 2003-02-07 DE DE60322680T patent/DE60322680D1/de not_active Expired - Fee Related
-
2006
- 2006-01-23 US US11/337,366 patent/US7294720B2/en not_active Expired - Fee Related
-
2007
- 2007-09-18 US US11/857,193 patent/US7776898B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20080070964A1 (en) | 2008-03-20 |
| DE60322680D1 (de) | 2008-09-18 |
| AU2003210916A1 (en) | 2003-09-02 |
| EP1485088B1 (en) | 2008-08-06 |
| AU2003210916B2 (en) | 2008-10-23 |
| US7045520B2 (en) | 2006-05-16 |
| ATE403426T1 (de) | 2008-08-15 |
| AU2003210916B9 (en) | 2008-12-18 |
| WO2003066050A1 (en) | 2003-08-14 |
| US7776898B2 (en) | 2010-08-17 |
| US20030225072A1 (en) | 2003-12-04 |
| MXPA04007719A (es) | 2005-09-08 |
| US7294720B2 (en) | 2007-11-13 |
| US20060128776A1 (en) | 2006-06-15 |
| JP2005521676A (ja) | 2005-07-21 |
| ES2311711T3 (es) | 2009-02-16 |
| EP1485088A1 (en) | 2004-12-15 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |