CH636089A5 - Antimicrobial 1-(2-(halophenylthio)-4-(p-chloro- or -fluorophenyl)-n-butyl)imidazoles and their preparation - Google Patents
Antimicrobial 1-(2-(halophenylthio)-4-(p-chloro- or -fluorophenyl)-n-butyl)imidazoles and their preparation Download PDFInfo
- Publication number
- CH636089A5 CH636089A5 CH23678A CH23678A CH636089A5 CH 636089 A5 CH636089 A5 CH 636089A5 CH 23678 A CH23678 A CH 23678A CH 23678 A CH23678 A CH 23678A CH 636089 A5 CH636089 A5 CH 636089A5
- Authority
- CH
- Switzerland
- Prior art keywords
- chlorine
- butyl
- imidazole
- antimicrobial
- compounds
- Prior art date
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- 230000000845 anti-microbial effect Effects 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000002460 imidazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 102
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 67
- 239000000460 chlorine Substances 0.000 claims description 55
- 229910052801 chlorine Inorganic materials 0.000 claims description 55
- 150000003839 salts Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 36
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- -1 2,6-dichlorophenylthio Chemical group 0.000 claims description 33
- 229910052731 fluorine Chemical group 0.000 claims description 23
- 239000011737 fluorine Chemical group 0.000 claims description 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 229940121375 antifungal agent Drugs 0.000 claims description 7
- 239000004599 antimicrobial Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 239000003429 antifungal agent Substances 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 8
- XRVMTYYATIGTJQ-UHFFFAOYSA-N 1-[2-(2-bromophenyl)sulfanyl-4-(4-chlorophenyl)butyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CCC(SC=1C(=CC=CC=1)Br)CN1C=NC=C1 XRVMTYYATIGTJQ-UHFFFAOYSA-N 0.000 claims 1
- AMRVGKCQQKWJJI-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(2,4,6-trichlorophenyl)sulfanylbutyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CCC(SC=1C(=CC(Cl)=CC=1Cl)Cl)CN1C=NC=C1 AMRVGKCQQKWJJI-UHFFFAOYSA-N 0.000 claims 1
- BLDLNZNBHRVMID-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(2,5-dichlorophenyl)sulfanylbutyl]imidazole Chemical compound C1=CC(Cl)=CC=C1CCC(SC=1C(=CC=C(Cl)C=1)Cl)CN1C=NC=C1 BLDLNZNBHRVMID-UHFFFAOYSA-N 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 28
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
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- 239000002585 base Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/758,094 US4078071A (en) | 1976-03-08 | 1977-01-10 | Derivatives of substituted N-alkyl imidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH636089A5 true CH636089A5 (en) | 1983-05-13 |
Family
ID=25050465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH23678A CH636089A5 (en) | 1977-01-10 | 1978-01-10 | Antimicrobial 1-(2-(halophenylthio)-4-(p-chloro- or -fluorophenyl)-n-butyl)imidazoles and their preparation |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS53135976A (en, 2012) |
| CH (1) | CH636089A5 (en, 2012) |
| DE (1) | DE2800755A1 (en, 2012) |
| FR (1) | FR2376850A2 (en, 2012) |
| GB (1) | GB1567431A (en, 2012) |
| HK (1) | HK17681A (en, 2012) |
| IT (1) | IT1111401B (en, 2012) |
| MY (1) | MY8100370A (en, 2012) |
| NL (1) | NL184160C (en, 2012) |
| SE (1) | SE443783B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4213991A (en) * | 1978-05-30 | 1980-07-22 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles and compositions and methods containing the same |
| JPS55160767A (en) * | 1979-05-31 | 1980-12-13 | Idota Yutaka | Imidazole derivative |
| DE3369984D1 (en) * | 1982-07-12 | 1987-04-09 | Searle & Co | 1-(1h-imidazolyl), 1-n-morpholinyl and pyridyl compounds, their preparation and pharmaceutical compositions containing them |
| GB8316444D0 (en) * | 1983-06-16 | 1983-07-20 | Ici Plc | Heterocycle compounds |
| HUP0400270A3 (en) * | 2004-01-27 | 2007-09-28 | Richter Gedeon Nyrt | High purity butoconazole nitrate having a predetermined particle size and process for the production of the same |
| CN105263899B (zh) | 2013-01-21 | 2017-11-14 | 国立大学法人大阪大学 | 苯氧基烷基胺化合物 |
| EP3558304A2 (en) | 2016-12-23 | 2019-10-30 | Helmholtz Zentrum München - Deutsches Forschungszentrum für Gesundheit und Umwelt (GmbH) | Inhibitors of cytochrome p450 family 7 subfamily b member 1 (cyp7b1) for use in treating diseases |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
| MX3866E (es) * | 1975-07-28 | 1981-08-26 | Syntex Inc | Metodo mejorado para preparar derivados de imidazoles n-alquil sustituidos |
| JPS6028820A (ja) * | 1983-07-26 | 1985-02-14 | Daishiro Fujishima | 脱酸素剤 |
-
1978
- 1978-01-04 SE SE7800111A patent/SE443783B/sv not_active IP Right Cessation
- 1978-01-04 GB GB229/78A patent/GB1567431A/en not_active Expired
- 1978-01-04 NL NLAANVRAGE7800097,A patent/NL184160C/xx not_active IP Right Cessation
- 1978-01-09 IT IT67025/78A patent/IT1111401B/it active
- 1978-01-09 FR FR7800480A patent/FR2376850A2/fr active Granted
- 1978-01-09 JP JP107378A patent/JPS53135976A/ja active Granted
- 1978-01-09 DE DE19782800755 patent/DE2800755A1/de active Granted
- 1978-01-10 CH CH23678A patent/CH636089A5/de not_active IP Right Cessation
-
1981
- 1981-04-30 HK HK176/81A patent/HK17681A/xx unknown
- 1981-12-30 MY MY370/81A patent/MY8100370A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS635388B2 (en, 2012) | 1988-02-03 |
| FR2376850A2 (fr) | 1978-08-04 |
| DE2800755C2 (en, 2012) | 1989-09-07 |
| HK17681A (en) | 1981-05-08 |
| MY8100370A (en) | 1981-12-31 |
| GB1567431A (en) | 1980-05-14 |
| SE443783B (sv) | 1986-03-10 |
| IT1111401B (it) | 1986-01-13 |
| JPS53135976A (en) | 1978-11-28 |
| NL184160C (nl) | 1989-05-01 |
| NL7800097A (nl) | 1978-07-12 |
| SE7800111L (sv) | 1978-07-11 |
| DE2800755A1 (de) | 1978-07-13 |
| NL184160B (nl) | 1988-12-01 |
| IT7867025A0 (it) | 1978-01-09 |
| FR2376850B2 (en, 2012) | 1980-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SPCR | Supplementary protection certificate rejected |
Free format text: IKS 47573/860618, IKS 47574/860618, 960125 |
|
| PL | Patent ceased |