CH638791A5 - Verfahren zur herstellung bestimmter imidazolderivate und verwendung derselben. - Google Patents
Verfahren zur herstellung bestimmter imidazolderivate und verwendung derselben. Download PDFInfo
- Publication number
- CH638791A5 CH638791A5 CH1019276A CH1019276A CH638791A5 CH 638791 A5 CH638791 A5 CH 638791A5 CH 1019276 A CH1019276 A CH 1019276A CH 1019276 A CH1019276 A CH 1019276A CH 638791 A5 CH638791 A5 CH 638791A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- formula
- imidazole
- compound
- carbon atoms
- Prior art date
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- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 55
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 150000002460 imidazoles Chemical class 0.000 claims description 11
- -1 methoxy, ethoxy, acetoxy Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- GOIWZZQXWJVDOG-UHFFFAOYSA-N 2,2,2-trifluoroethyl trichloromethanesulfonate Chemical compound FC(F)(F)COS(=O)(=O)C(Cl)(Cl)Cl GOIWZZQXWJVDOG-UHFFFAOYSA-N 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- ZBBUBEXEJQMOLU-UHFFFAOYSA-N 4,5-diphenyl-2-(trifluoromethylsulfonyl)-1h-imidazole Chemical compound N1C(S(=O)(=O)C(F)(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ZBBUBEXEJQMOLU-UHFFFAOYSA-N 0.000 claims description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
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- 239000011737 fluorine Substances 0.000 claims 4
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
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- 241000251730 Chondrichthyes Species 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
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- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 238000002844 melting Methods 0.000 description 32
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- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
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- 239000003228 hemolysin Substances 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000003125 immunofluorescent labeling Methods 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
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- 208000015181 infectious disease Diseases 0.000 description 1
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940117615 mineral oil 5 mg/ml Drugs 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
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- 229960001412 pentobarbital Drugs 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000012258 stirred mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D233/66—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 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
- C07D233/84—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60365075A | 1975-08-11 | 1975-08-11 | |
| US69128276A | 1976-06-09 | 1976-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH638791A5 true CH638791A5 (de) | 1983-10-14 |
Family
ID=27084480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1019276A CH638791A5 (de) | 1975-08-11 | 1976-08-10 | Verfahren zur herstellung bestimmter imidazolderivate und verwendung derselben. |
Country Status (26)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK16778A (da) * | 1977-02-09 | 1978-08-10 | Du Pont | Imidazolderivater deres anvendelser og fremstilling |
| LU77703A1 (de) * | 1977-07-07 | 1979-03-26 | Ciba Geigy Ag | Verfahren zur herstellung von bicyclischen thia-diaza-verbindungen |
| EP0004648B1 (de) * | 1978-04-11 | 1982-08-25 | Ciba-Geigy Ag | Neue Mercaptoimidazolderivate, Verfahren zu deren Herstellung, Mercaptoimidazolderivate zur Behandlung entzündlicher Erkrankungen und diese enthaltende pharmazeutische Präparate |
| DE2823197A1 (de) | 1978-05-24 | 1979-11-29 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4308277A (en) * | 1978-08-10 | 1981-12-29 | Ciba-Geigy Corporation | 2,4,5-Trisubstituted imidazolines and pharmaceutical compositions containing same |
| US4188397A (en) * | 1978-09-22 | 1980-02-12 | Smithkline Corporation | 2,2-Alkyldiylbis(thio)bis(imidazoles) |
| US4215135A (en) * | 1979-06-08 | 1980-07-29 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2-substituted-1H-phenanthro[9,10-d]imidazoles |
| DE2856909A1 (de) * | 1978-12-28 | 1980-07-17 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| GB8907656D0 (en) * | 1989-04-05 | 1989-05-17 | May & Baker Ltd | New compositions of matter |
| CA2200316C (en) * | 1994-09-26 | 2004-09-21 | Hirohiko Sugimoto | Imidazole derivative |
| JP2002515915A (ja) * | 1997-06-30 | 2002-05-28 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | 炎症性疾患の治療で有用な２−置換イミダゾール類 |
| DE10222103A1 (de) * | 2002-05-17 | 2003-11-27 | Merckle Gmbh Chem Pharm Fabrik | 2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie |
| US7994204B2 (en) * | 2006-02-06 | 2011-08-09 | Taisho Pharmaceutical Co., Ltd | Binding inhibitor of sphingosine-1-phosphate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6614808A (enrdf_load_stackoverflow) * | 1965-10-21 | 1967-04-24 | ||
| US3651080A (en) * | 1969-11-07 | 1972-03-21 | Ciba Geigy Corp | Certain substituted 2-alkylmercaptoimidazole derivatives |
| US3636003A (en) * | 1969-11-17 | 1972-01-18 | Geigy Chem Corp | Substituted 2-mercaptoimidazole derivatives |
| US3714179A (en) * | 1970-09-08 | 1973-01-30 | Searle & Co | 1-alkyl-2-furfurylthioimidazoles and congeners |
| US3707475A (en) * | 1970-11-16 | 1972-12-26 | Pfizer | Antiinflammatory imidazoles |
-
1976
- 1976-07-02 SE SE7607615A patent/SE428686B/xx not_active IP Right Cessation
- 1976-08-05 MX MX762132U patent/MX3932E/es unknown
- 1976-08-09 CA CA258,690A patent/CA1074327A/en not_active Expired
- 1976-08-09 NO NO762754A patent/NO146571C/no unknown
- 1976-08-09 DD DD194248A patent/DD126244A5/xx unknown
- 1976-08-10 ES ES450601A patent/ES450601A1/es not_active Expired
- 1976-08-10 SU SU762388413A patent/SU640662A3/ru active
- 1976-08-10 NZ NZ181737A patent/NZ181731A/xx unknown
- 1976-08-10 AU AU16711/76A patent/AU508605B2/en not_active Expired
- 1976-08-10 FR FR7624400A patent/FR2320745A1/fr active Granted
- 1976-08-10 CH CH1019276A patent/CH638791A5/de not_active IP Right Cessation
- 1976-08-10 FI FI762290A patent/FI66177C/fi not_active IP Right Cessation
- 1976-08-10 HU HU76DU252A patent/HU174707B/hu unknown
- 1976-08-10 GB GB33286/76A patent/GB1516908A/en not_active Expired
- 1976-08-10 GR GR51440A patent/GR61145B/el unknown
- 1976-08-10 IL IL50230A patent/IL50230A/xx unknown
- 1976-08-10 DK DK361376A patent/DK361376A/da not_active Application Discontinuation
- 1976-08-10 DE DE19762635876 patent/DE2635876A1/de not_active Withdrawn
- 1976-08-10 PT PT65464A patent/PT65464B/pt unknown
- 1976-08-10 PH PH18773A patent/PH11857A/en unknown
- 1976-08-11 AR AR264308A patent/AR215591A1/es active
- 1976-08-11 JP JP51094991A patent/JPS6011702B2/ja not_active Expired
- 1976-08-11 NL NL7608915A patent/NL7608915A/xx not_active Application Discontinuation
- 1976-08-11 LU LU75578A patent/LU75578A1/xx unknown
- 1976-08-11 IE IE1775/76A patent/IE44019B1/en unknown
- 1976-08-11 YU YU01981/76A patent/YU198176A/xx unknown
-
1977
- 1977-07-28 ES ES461193A patent/ES461193A1/es not_active Expired
-
1978
- 1978-01-10 AR AR270672A patent/AR218054A1/es active
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