DE2635876A1 - Imidazolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Imidazolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2635876A1 DE2635876A1 DE19762635876 DE2635876A DE2635876A1 DE 2635876 A1 DE2635876 A1 DE 2635876A1 DE 19762635876 DE19762635876 DE 19762635876 DE 2635876 A DE2635876 A DE 2635876A DE 2635876 A1 DE2635876 A1 DE 2635876A1
- Authority
- DE
- Germany
- Prior art keywords
- imidazole
- compounds according
- bis
- compounds
- alkyl
- 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.)
- Withdrawn
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 49
- 238000000034 method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 13
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 67
- 206010003246 arthritis Diseases 0.000 claims description 23
- -1 CF 3 Inorganic materials 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- ZMPAPJBFYQSNFM-UHFFFAOYSA-N 1-sulfanylimidazole Chemical class SN1C=CN=C1 ZMPAPJBFYQSNFM-UHFFFAOYSA-N 0.000 claims 1
- XVLMMLFVASDPEI-UHFFFAOYSA-N 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)-1h-imidazole Chemical compound N1C(SC(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XVLMMLFVASDPEI-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 241000700159 Rattus Species 0.000 description 30
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- 210000004027 cell Anatomy 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
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- 239000003814 drug Substances 0.000 description 15
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- 238000000921 elemental analysis Methods 0.000 description 15
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 14
- 239000002671 adjuvant Substances 0.000 description 13
- 230000002917 arthritic effect Effects 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 208000009386 Experimental Arthritis Diseases 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 210000004989 spleen cell Anatomy 0.000 description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
- 239000006285 cell suspension Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 244000215068 Acacia senegal Species 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 229960004397 cyclophosphamide Drugs 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 229960000905 indomethacin Drugs 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 210000000548 hind-foot Anatomy 0.000 description 6
- 150000002460 imidazoles Chemical class 0.000 description 6
- 210000004698 lymphocyte Anatomy 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- OGXVKPBGIGLUEO-UHFFFAOYSA-N 4,5-diphenyl-2-(2,2,2-trifluoroethylsulfanyl)-1h-imidazole Chemical compound N1C(SCC(F)(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OGXVKPBGIGLUEO-UHFFFAOYSA-N 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 210000003298 dental enamel Anatomy 0.000 description 5
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
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- 206010039073 rheumatoid arthritis Diseases 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 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 description 4
- NZKLDYYRLVFZCE-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-1,3-dihydroimidazole-2-thione Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S)=N1 NZKLDYYRLVFZCE-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000002949 hemolytic effect Effects 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229960002895 phenylbutazone Drugs 0.000 description 4
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
- XJXSIQHSQFQXPU-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-methylsulfanyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC)=N1 XJXSIQHSQFQXPU-UHFFFAOYSA-N 0.000 description 3
- GMTAWLUJHGIUPU-UHFFFAOYSA-N 4,5-diphenyl-1,3-dihydroimidazole-2-thione Chemical compound N1C(S)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GMTAWLUJHGIUPU-UHFFFAOYSA-N 0.000 description 3
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- HNGYYQNAHYULOJ-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-(2,2,2-trifluoroethylsulfanyl)-1h-imidazole Chemical compound N1C(SCC(F)(F)F)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 HNGYYQNAHYULOJ-UHFFFAOYSA-N 0.000 description 2
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- 238000002560 therapeutic procedure Methods 0.000 description 1
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- 230000008736 traumatic injury Effects 0.000 description 1
- RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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 |
|---|---|
| DE2635876A1 true DE2635876A1 (de) | 1977-03-03 |
Family
ID=27084480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762635876 Withdrawn DE2635876A1 (de) | 1975-08-11 | 1976-08-10 | Imidazolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Country Status (26)
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0004648A3 (en) * | 1978-04-11 | 1979-11-14 | Ciba-Geigy Ag | Mercapto-imidazole derivatives, their preparation, their pharmaceutical compositions and applications |
| EP0005545A3 (en) * | 1978-05-24 | 1980-01-09 | Schering Aktiengesellschaft Berlin Und Bergkamen | Imidazole derivatives, process for their preparation and pharmaceutical compositions containing them |
| EP0008073A1 (de) * | 1978-08-10 | 1980-02-20 | Ciba-Geigy Ag | Thiosubstituierte Diazacycloalkene, Verfahren zu ihrer Herstellung und pharmazeutische Präparate |
| EP0013732A3 (en) * | 1978-12-28 | 1980-11-12 | Schering Aktiengesellschaft Berlin Und Bergkamen | Imidazole derivatives and intermediates, processes for their preparation and pharmaceutical compositions containing these imidazole derivatives |
| EP0019688A1 (de) * | 1977-07-07 | 1980-12-10 | Ciba-Geigy Ag | Diazaverbindungen und Verfahren zu deren Herstellung |
| EP0010361B1 (en) * | 1978-09-22 | 1983-04-27 | Smithkline Beckman Corporation | Bis-imidazoles, their preparation and pharmaceutical compositions containing them |
| EP0391796A1 (en) * | 1989-04-05 | 1990-10-10 | Rhone-Poulenc Sante | New imidazole derivatives, process for their production and pharmaceutical compositions containing them |
| WO1999003837A1 (en) * | 1997-06-30 | 1999-01-28 | Ortho-Mcneil Pharmaceutical, Inc. | 2-substituted imidazoles useful in the treatment of inflammatory diseases |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK16778A (da) * | 1977-02-09 | 1978-08-10 | Du Pont | Imidazolderivater deres anvendelser og fremstilling |
| 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 |
| CA2200316C (en) * | 1994-09-26 | 2004-09-21 | Hirohiko Sugimoto | Imidazole derivative |
| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505350A (en) * | 1965-10-21 | 1970-04-07 | Geigy Chem Corp | Certain substituted 2-mercaptoimidazole derivatives |
| US3636003A (en) * | 1969-11-17 | 1972-01-18 | Geigy Chem Corp | Substituted 2-mercaptoimidazole derivatives |
| US3651080A (en) * | 1969-11-07 | 1972-03-21 | Ciba Geigy Corp | Certain substituted 2-alkylmercaptoimidazole derivatives |
| US3707475A (en) * | 1970-11-16 | 1972-12-26 | Pfizer | Antiinflammatory imidazoles |
| US3714179A (en) * | 1970-09-08 | 1973-01-30 | Searle & Co | 1-alkyl-2-furfurylthioimidazoles and congeners |
-
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
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505350A (en) * | 1965-10-21 | 1970-04-07 | Geigy Chem Corp | Certain substituted 2-mercaptoimidazole derivatives |
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| SU 487073, Chem. Abstr. 84, 59472t * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019688A1 (de) * | 1977-07-07 | 1980-12-10 | Ciba-Geigy Ag | Diazaverbindungen und Verfahren zu deren Herstellung |
| EP0004648A3 (en) * | 1978-04-11 | 1979-11-14 | Ciba-Geigy Ag | Mercapto-imidazole derivatives, their preparation, their pharmaceutical compositions and applications |
| EP0005545A3 (en) * | 1978-05-24 | 1980-01-09 | Schering Aktiengesellschaft Berlin Und Bergkamen | Imidazole derivatives, process for their preparation and pharmaceutical compositions containing them |
| US4269847A (en) | 1978-05-24 | 1981-05-26 | Schering Aktiengesellschaft | Antiinflammatory-4,5-diphenyl-2-substituted-thio-imidazoles and their corresponding sulfoxides and sulfones |
| US4355039A (en) | 1978-05-24 | 1982-10-19 | Schering, Aktiengesellschaft | Antiinflammatory-4,5-diaryl-2-substituted-thio-imidazoles and their corresponding sulfoxides and sulfones |
| US4440776A (en) * | 1978-05-24 | 1984-04-03 | Schering Aktiengesellschaft | Antiinflammatory 4,5-diphenyl-2-substituted-thio-imidazoles and their corresponding sulfoxides and sulfones |
| EP0008073A1 (de) * | 1978-08-10 | 1980-02-20 | Ciba-Geigy Ag | Thiosubstituierte Diazacycloalkene, Verfahren zu ihrer Herstellung und pharmazeutische Präparate |
| EP0010361B1 (en) * | 1978-09-22 | 1983-04-27 | Smithkline Beckman Corporation | Bis-imidazoles, their preparation and pharmaceutical compositions containing them |
| EP0013732A3 (en) * | 1978-12-28 | 1980-11-12 | Schering Aktiengesellschaft Berlin Und Bergkamen | Imidazole derivatives and intermediates, processes for their preparation and pharmaceutical compositions containing these imidazole derivatives |
| US4272543A (en) | 1978-12-28 | 1981-06-09 | Schering, Aktiengesellschaft | Pharmacologically active 4,5-diaryl-2-substituted-imidazoles |
| EP0391796A1 (en) * | 1989-04-05 | 1990-10-10 | Rhone-Poulenc Sante | New imidazole derivatives, process for their production and pharmaceutical compositions containing them |
| WO1999003837A1 (en) * | 1997-06-30 | 1999-01-28 | Ortho-Mcneil Pharmaceutical, Inc. | 2-substituted imidazoles useful in the treatment of inflammatory diseases |
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Legal Events
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| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |