SU640662A3 - Способ получени производных имидазола или их солей - Google Patents
Способ получени производных имидазола или их солейInfo
- Publication number
- SU640662A3 SU640662A3 SU762388413A SU2388413A SU640662A3 SU 640662 A3 SU640662 A3 SU 640662A3 SU 762388413 A SU762388413 A SU 762388413A SU 2388413 A SU2388413 A SU 2388413A SU 640662 A3 SU640662 A3 SU 640662A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- imidazole
- bis
- mixture
- calculated
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 150000003839 salts Chemical class 0.000 title description 2
- 150000002460 imidazoles Chemical class 0.000 title 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 229960001701 chloroform Drugs 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- -1 2,2,2-trifluoroethyltrichloromethane sulfate Chemical compound 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 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 2
- XUOAKFNMJMYKBY-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-1h-imidazole Chemical compound N1C(S(=O)(=O)C(F)(F)C(F)F)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 XUOAKFNMJMYKBY-UHFFFAOYSA-N 0.000 description 2
- FHXLHLWLQXKOEG-UHFFFAOYSA-N 4,5-diphenyl-2-(2,2,2-trifluoroethylsulfonyl)-1h-imidazole Chemical compound N1C(S(=O)(=O)CC(F)(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 FHXLHLWLQXKOEG-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 1
- NCTOWTQQOFYIEP-UHFFFAOYSA-N 1-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]propan-2-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCC(C)=O)=N1 NCTOWTQQOFYIEP-UHFFFAOYSA-N 0.000 description 1
- NHUNLDQEFDSCBB-UHFFFAOYSA-N 1-chlorobutane;hexane Chemical compound CCCCCl.CCCCCC NHUNLDQEFDSCBB-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- RVLRDPZRAXCGKZ-UHFFFAOYSA-N 4,5-bis(2-methoxyphenyl)-1,3-dihydroimidazole-2-thione Chemical compound COC1=CC=CC=C1C1=C(C=2C(=CC=CC=2)OC)NC(S)=N1 RVLRDPZRAXCGKZ-UHFFFAOYSA-N 0.000 description 1
- JYEPJLSKZAHYCG-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-1,3-dihydroimidazole-2-thione Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)NC(=S)N1 JYEPJLSKZAHYCG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WOSUEQAPJZGKGP-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-(2,2,2-trifluoroethylsulfonyl)-1h-imidazole Chemical compound N1C(S(=O)(=O)CC(F)(F)F)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 WOSUEQAPJZGKGP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VRGHZDFUCKFVBQ-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-(2,2,2-trifluoroethylsulfonyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)(=O)CC(F)(F)F)=N1 VRGHZDFUCKFVBQ-UHFFFAOYSA-N 0.000 description 1
- PLXXJXRFXLCRDL-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-(methylsulfanylmethylsulfanyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCSC)=N1 PLXXJXRFXLCRDL-UHFFFAOYSA-N 0.000 description 1
- GOJZJBQGEIQCIL-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-(methylsulfanylmethylsulfinyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)CSC)=N1 GOJZJBQGEIQCIL-UHFFFAOYSA-N 0.000 description 1
- XFQPBHGOXAISLH-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-(methylsulfinylmethylsulfanyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCS(C)=O)=N1 XFQPBHGOXAISLH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QRBSRNQOZJZBHS-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-prop-2-enylsulfanyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCC=C)=N1 QRBSRNQOZJZBHS-UHFFFAOYSA-N 0.000 description 1
- CKEJADKVJUSWJK-UHFFFAOYSA-N 4,5-bis[4-[(2-methylpropan-2-yl)oxy]phenyl]-2-(1,1,2,2-tetrafluoroethylsulfonyl)-1h-imidazole Chemical compound C1=CC(OC(C)(C)C)=CC=C1C1=C(C=2C=CC(OC(C)(C)C)=CC=2)NC(S(=O)(=O)C(F)(F)C(F)F)=N1 CKEJADKVJUSWJK-UHFFFAOYSA-N 0.000 description 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 description 1
- HRKFATZEMKPDKK-UHFFFAOYSA-N 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)-1h-imidazole Chemical compound N1C(S(=O)(=O)C(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HRKFATZEMKPDKK-UHFFFAOYSA-N 0.000 description 1
- HGKZQDDHRMMIIQ-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-1h-imidazol-5-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=C(C=2C=CC(O)=CC=2)NC(S(=O)(=O)C(F)(F)C(F)F)=N1 HGKZQDDHRMMIIQ-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 101150043532 CISH gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (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 |
|---|---|
| SU640662A3 true SU640662A3 (ru) | 1978-12-30 |
Family
ID=27084480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762388413A SU640662A3 (ru) | 1975-08-11 | 1976-08-10 | Способ получени производных имидазола или их солей |
Country Status (26)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2157368C2 (ru) * | 1994-09-26 | 2000-10-10 | Сионоги Энд Ко., Лтд. | Производные имидазола и фармацевтическая композиция на их основе |
| RU2395499C2 (ru) * | 2006-02-06 | 2010-07-27 | Тайсо Фармасьютикал Ко., Лтд. | Ингибитор связывания сфингозин-1-фосфата |
Families Citing this family (11)
| 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 |
| CY1302A (en) * | 1978-04-11 | 1985-12-06 | Ciba Geigy Ag | Mercapto-imidazole derivatives,their preparation,their pharmaceutical compositions and applications |
| 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 |
| WO1999003837A1 (en) * | 1997-06-30 | 1999-01-28 | Ortho-Mcneil Pharmaceutical, Inc. | 2-substituted imidazoles useful in the treatment of inflammatory diseases |
| DE10222103A1 (de) * | 2002-05-17 | 2003-11-27 | Merckle Gmbh Chem Pharm Fabrik | 2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1155580A (en) * | 1965-10-21 | 1969-06-18 | Geigy Ag J R | New Imidazole Derivatives their Production and Use |
| 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 NO NO762754A patent/NO146571C/no unknown
- 1976-08-09 DD DD194248A patent/DD126244A5/xx unknown
- 1976-08-09 CA CA258,690A patent/CA1074327A/en not_active Expired
- 1976-08-10 ES ES450601A patent/ES450601A1/es not_active Expired
- 1976-08-10 GR GR51440A patent/GR61145B/el unknown
- 1976-08-10 DE DE19762635876 patent/DE2635876A1/de not_active Withdrawn
- 1976-08-10 CH CH1019276A patent/CH638791A5/de not_active IP Right Cessation
- 1976-08-10 DK DK361376A patent/DK361376A/da not_active Application Discontinuation
- 1976-08-10 PH PH18773A patent/PH11857A/en unknown
- 1976-08-10 GB GB33286/76A patent/GB1516908A/en not_active Expired
- 1976-08-10 FR FR7624400A patent/FR2320745A1/fr active Granted
- 1976-08-10 NZ NZ181737A patent/NZ181731A/xx unknown
- 1976-08-10 HU HU76DU252A patent/HU174707B/hu unknown
- 1976-08-10 IL IL50230A patent/IL50230A/xx unknown
- 1976-08-10 PT PT65464A patent/PT65464B/pt unknown
- 1976-08-10 SU SU762388413A patent/SU640662A3/ru active
- 1976-08-10 AU AU16711/76A patent/AU508605B2/en not_active Expired
- 1976-08-10 FI FI762290A patent/FI66177C/fi not_active IP Right Cessation
- 1976-08-11 JP JP51094991A patent/JPS6011702B2/ja not_active Expired
- 1976-08-11 IE IE1775/76A patent/IE44019B1/en unknown
- 1976-08-11 YU YU01981/76A patent/YU198176A/xx unknown
- 1976-08-11 LU LU75578A patent/LU75578A1/xx unknown
- 1976-08-11 AR AR264308A patent/AR215591A1/es active
- 1976-08-11 NL NL7608915A patent/NL7608915A/xx not_active Application Discontinuation
-
1977
- 1977-07-28 ES ES461193A patent/ES461193A1/es not_active Expired
-
1978
- 1978-01-10 AR AR270672A patent/AR218054A1/es active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2157368C2 (ru) * | 1994-09-26 | 2000-10-10 | Сионоги Энд Ко., Лтд. | Производные имидазола и фармацевтическая композиция на их основе |
| RU2395499C2 (ru) * | 2006-02-06 | 2010-07-27 | Тайсо Фармасьютикал Ко., Лтд. | Ингибитор связывания сфингозин-1-фосфата |
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