JP2013503111A5 - - Google Patents
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- JP2013503111A5 JP2013503111A5 JP2012525824A JP2012525824A JP2013503111A5 JP 2013503111 A5 JP2013503111 A5 JP 2013503111A5 JP 2012525824 A JP2012525824 A JP 2012525824A JP 2012525824 A JP2012525824 A JP 2012525824A JP 2013503111 A5 JP2013503111 A5 JP 2013503111A5
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- JP
- Japan
- Prior art keywords
- group
- trifluoromethyl
- hydrogen
- ethyl
- halogen
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 28
- 244000005700 microbiome Species 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000002883 imidazolyl group Chemical group 0.000 claims description 18
- 241000233866 Fungi Species 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- -1 Benzyl aralkyl ether compounds Chemical class 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
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- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical group [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 6
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
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- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052794 bromium Inorganic materials 0.000 claims description 5
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- UOPYUOMFMOGFLM-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-[(4-phenylphenyl)methoxy]ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C=CC(=CC=1)C=1C=CC=CC=1)CN1C=NC=C1 UOPYUOMFMOGFLM-UHFFFAOYSA-N 0.000 claims description 4
- FUAHXHWSMYFWGE-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-[[4-(trifluoromethyl)phenyl]methoxy]ethyl]imidazole Chemical compound C1=CC(C(F)(F)F)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 FUAHXHWSMYFWGE-UHFFFAOYSA-N 0.000 claims description 4
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- ZXIUYIXNXBBCNT-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-[[4-(trifluoromethyl)phenyl]methoxy]ethyl]-1,2,4-triazole Chemical compound C1=CC(C(F)(F)F)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 ZXIUYIXNXBBCNT-UHFFFAOYSA-N 0.000 claims description 2
- VYLNCPLIHRVCQO-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)-2-[[4-(trifluoromethyl)phenyl]methoxy]ethyl]-1,3-dihydro-1,2,4-triazole Chemical compound C1=CC(C(F)(F)F)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CNC1 VYLNCPLIHRVCQO-UHFFFAOYSA-N 0.000 claims description 2
- MSFQEZBRFPAFEX-UHFFFAOYSA-N 4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1 MSFQEZBRFPAFEX-UHFFFAOYSA-N 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
- LVRCEUVOXCJYSV-UHFFFAOYSA-N CN(C)S(=O)=O Chemical compound CN(C)S(=O)=O LVRCEUVOXCJYSV-UHFFFAOYSA-N 0.000 claims description 2
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- PYYRNLDFMZVKCV-UHFFFAOYSA-N (2-nitrophenyl)methanamine Chemical compound NCC1=CC=CC=C1[N+]([O-])=O PYYRNLDFMZVKCV-UHFFFAOYSA-N 0.000 claims 1
- BUSGQNFYMRKXMQ-UHFFFAOYSA-N 1-[2-[[4-(4-chlorophenyl)phenyl]methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound C1=CC(Cl)=CC=C1C(C=C1)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BUSGQNFYMRKXMQ-UHFFFAOYSA-N 0.000 claims 1
- PXEXWSODTIAPRE-UHFFFAOYSA-N 2-[amino-di(propan-2-yl)silyl]propane Chemical compound CC(C)[Si](N)(C(C)C)C(C)C PXEXWSODTIAPRE-UHFFFAOYSA-N 0.000 claims 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BRPI0904249-0 | 2009-08-28 | ||
| BRPI0904249-0A BRPI0904249B1 (pt) | 2009-08-28 | 2009-08-28 | Compostos éteres aralquil benzílicos, processo de preparação dos mesmos, uso dos referidos compostos, composição farmacêutica |
| PCT/BR2010/000276 WO2011022798A1 (pt) | 2009-08-28 | 2010-08-27 | Compostos éteres aralquil benzílicos, processo de preparação dos mesmos, compostos intermediários, uso dos referidos compostos, método de tratamento e/ou prevenção, composição farmacêutica e medicamento contendo os mesmos |
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| JP2013503111A JP2013503111A (ja) | 2013-01-31 |
| JP2013503111A5 true JP2013503111A5 (https=) | 2013-10-10 |
| JP5718334B2 JP5718334B2 (ja) | 2015-05-13 |
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| EP (1) | EP2471781B1 (https=) |
| JP (1) | JP5718334B2 (https=) |
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| CN (1) | CN102625800A (https=) |
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| AU (1) | AU2010286266B2 (https=) |
| BR (1) | BRPI0904249B1 (https=) |
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Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102579829B (zh) * | 2012-03-06 | 2013-09-18 | 康莉 | 一种治疗牛放线菌病的中药组合物及其制备方法 |
| CN104016837B (zh) * | 2014-05-26 | 2016-08-24 | 武汉有机实业有限公司 | 4,4’-二甲基二苄基醚的制备方法 |
| RU2603622C1 (ru) * | 2015-06-25 | 2016-11-27 | Федеральное государственное бюджетное научное учреждение "Прикаспийский зональный научно-исследовательский ветеринарный институт" | Комплексный метод лечения тейлериоза мелкого рогатого скота |
| CN108047147A (zh) * | 2017-12-08 | 2018-05-18 | 长江大学 | 一类三唑类化合物以及作为杀菌剂的用途 |
| KR101983575B1 (ko) * | 2017-12-21 | 2019-06-03 | 대한민국 | 신균주 세라토바시디움 속 js1289 및 이의 용도 |
| WO2021034627A1 (en) * | 2019-08-16 | 2021-02-25 | Purdue Research Foundation | Small molecule stimulators of the core particle of the proteasome |
| JP2023057423A (ja) * | 2021-10-11 | 2023-04-21 | 国立大学法人 熊本大学 | ムコール症治療薬 |
| CN117945867A (zh) * | 2024-01-12 | 2024-04-30 | 海南师范大学 | 一种抗菌活性苄基苯醚类衍生物及其制备方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1170188A (en) | 1967-09-15 | 1969-11-12 | Bayer Ag | N-trityl-imidazoles and salts and uses thereof |
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
| DE2333354C2 (de) * | 1973-06-30 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | 2-Aryloxy-2-(imidazol-1-yl)-äthanole sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| GB1475271A (en) | 1975-04-30 | 1977-06-01 | Pfizer Ltd | 1-aryl-2-1-imidazolyl-alkyl ethers and thioethers and their use as antifungal agents |
| DE2556319A1 (de) * | 1975-12-13 | 1977-06-23 | Basf Ag | Substituierte triazol-aether |
| US4144346A (en) | 1977-01-31 | 1979-03-13 | Janssen Pharmaceutica N.V. | Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles |
| US4218458A (en) | 1978-06-23 | 1980-08-19 | Janssen Pharmaceutica, N.V. | Heterocyclic derivatives of (4-aryloxy-methyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles |
| US4277475A (en) * | 1979-01-11 | 1981-07-07 | Syntex (U.S.A.) Inc. | Contraceptive methods employing 1-substituted imidazole derivatives |
| BE885957A (nl) | 1980-10-31 | 1981-04-30 | Amylum Graanderivaten Raff | Inrichting voor de continue bereiding van zetmeellijm |
| US4368186A (en) * | 1981-05-07 | 1983-01-11 | Syntex (U.S.A.) Inc. | Methods and compositions for intravaginal contraception |
| DE3314738A1 (de) * | 1983-04-23 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | Azolylethyl-benzyl-ether-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| US5278175A (en) | 1990-02-02 | 1994-01-11 | Pfizer Inc. | Triazole antifungal agents |
| JP2875140B2 (ja) * | 1993-08-16 | 1999-03-24 | 明治製菓株式会社 | 抗ｍｒｓａ組成物 |
| US5461068A (en) * | 1993-09-29 | 1995-10-24 | Corwood Laboratories, Inc. | Imidazole derivative tincture and method of manufacture |
| US5750147A (en) * | 1995-06-07 | 1998-05-12 | Emisphere Technologies, Inc. | Method of solubilizing and encapsulating itraconazole |
| WO2006081327A2 (en) * | 2005-01-25 | 2006-08-03 | University Of Vermont And State Agricultural College | Small molecules that reduce fungal growth |
| US20080233053A1 (en) * | 2005-02-07 | 2008-09-25 | Pharmalight Inc. | Method and Device for Ophthalmic Administration of Active Pharmaceutical Ingredients |
| GB0714226D0 (en) * | 2007-07-20 | 2007-08-29 | Therapeutics Ltd E | anti-bacterial combination therapy |
| GB0724996D0 (en) * | 2007-12-21 | 2008-01-30 | Therapeutics Ltd E | Antibacterial combination therapy for the treatment of gram positive bacterial infections |
| GB0813211D0 (en) * | 2008-07-18 | 2008-08-27 | E Therapeutics Plc | Antibacterial combination therapy for the treatment of gram positive bacterial infections |
| EP2331094A4 (en) * | 2008-08-29 | 2011-10-26 | Uab Research Foundation | NOVEL AGENT AGAINST ARTHHYTHMIA |
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