DE2221546A1 - Verfahren zur Herstellung von neuen Imidazolderivaten - Google Patents
Verfahren zur Herstellung von neuen ImidazolderivatenInfo
- Publication number
- DE2221546A1 DE2221546A1 DE19722221546 DE2221546A DE2221546A1 DE 2221546 A1 DE2221546 A1 DE 2221546A1 DE 19722221546 DE19722221546 DE 19722221546 DE 2221546 A DE2221546 A DE 2221546A DE 2221546 A1 DE2221546 A1 DE 2221546A1
- Authority
- DE
- Germany
- Prior art keywords
- pyridyl
- imidazole
- tert
- butyl
- phenyl
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 40
- 150000002460 imidazoles Chemical class 0.000 title claims description 12
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 46
- -1 Nxederalkyl Chemical group 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 39
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 32
- 229910021529 ammonia Inorganic materials 0.000 claims description 30
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 150000001204 N-oxides Chemical class 0.000 claims description 21
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000005594 diketone group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- CEOUDUCITJEQQT-UHFFFAOYSA-N 3-(2-tert-butyl-5-phenyl-1h-imidazol-4-yl)pyridine Chemical compound N1C(C(C)(C)C)=NC(C=2C=NC=CC=2)=C1C1=CC=CC=C1 CEOUDUCITJEQQT-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 150000001409 amidines Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- PPPFRZIIFYPMJA-UHFFFAOYSA-N C(C)(C)(C)C=1NC(=C([N+]=1[O-])C1=CC=C(C=C1)OC)C=1C=NC=CC=1 Chemical compound C(C)(C)(C)C=1NC(=C([N+]=1[O-])C1=CC=C(C=C1)OC)C=1C=NC=CC=1 PPPFRZIIFYPMJA-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- QWZSAEUNIBEKIZ-UHFFFAOYSA-N 4-(1h-imidazol-2-yl)pyridine Chemical compound C1=CNC(C=2C=CN=CC=2)=N1 QWZSAEUNIBEKIZ-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- 239000000243 solution Substances 0.000 description 50
- 239000000203 mixture Substances 0.000 description 44
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 18
- 239000013078 crystal Substances 0.000 description 17
- XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 16
- 239000012362 glacial acetic acid Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 13
- 239000005695 Ammonium acetate Substances 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
- 235000019257 ammonium acetate Nutrition 0.000 description 13
- 229940043376 ammonium acetate Drugs 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000155 melt Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229940064982 ethylnicotinate Drugs 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 229940015043 glyoxal Drugs 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 4
- 150000002916 oxazoles Chemical class 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- DJTBGLMHZLZQSG-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)-1-pyridin-3-ylethanone Chemical compound C1=CC(SC)=CC=C1CC(=O)C1=CC=CN=C1 DJTBGLMHZLZQSG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AJMBMMSXICPUFP-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-pyridin-3-ylethane-1,2-dione Chemical compound ClC1=CC=CC=C1C(=O)C(=O)C1=CC=CN=C1 AJMBMMSXICPUFP-UHFFFAOYSA-N 0.000 description 2
- MGIQQNDNVXQPOB-UHFFFAOYSA-N 1-(3-chlorophenyl)-2-pyridin-3-ylethane-1,2-dione Chemical compound ClC1=CC=CC(C(=O)C(=O)C=2C=NC=CC=2)=C1 MGIQQNDNVXQPOB-UHFFFAOYSA-N 0.000 description 2
- UZZWEDIEWRHCKB-UHFFFAOYSA-N 1-(3-methoxyphenyl)-2-pyridin-3-ylethane-1,2-dione Chemical compound COC1=CC=CC(C(=O)C(=O)C=2C=NC=CC=2)=C1 UZZWEDIEWRHCKB-UHFFFAOYSA-N 0.000 description 2
- NLEXOTYKQLKFJB-UHFFFAOYSA-N 1-(3-methylphenyl)-2-pyridin-3-ylethane-1,2-dione Chemical compound CC1=CC=CC(C(=O)C(=O)C=2C=NC=CC=2)=C1 NLEXOTYKQLKFJB-UHFFFAOYSA-N 0.000 description 2
- WMMVLTAOHSXXFG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyrazin-2-ylethane-1,2-dione Chemical compound C1=CC(OC)=CC=C1C(=O)C(=O)C1=CN=CC=N1 WMMVLTAOHSXXFG-UHFFFAOYSA-N 0.000 description 2
- PMPFTDCYCHEILF-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-pyridin-3-ylethane-1,2-dione Chemical compound C1=CC(OC)=CC=C1C(=O)C(=O)C1=CC=CN=C1 PMPFTDCYCHEILF-UHFFFAOYSA-N 0.000 description 2
- NBCBJEXDJGFDKO-UHFFFAOYSA-N 1-(4-methylphenyl)-2-pyridin-3-ylethane-1,2-dione Chemical compound C1=CC(C)=CC=C1C(=O)C(=O)C1=CC=CN=C1 NBCBJEXDJGFDKO-UHFFFAOYSA-N 0.000 description 2
- ARDGQYVTLGUJII-UHFFFAOYSA-N 2,2-dimethylpropanimidamide;hydrochloride Chemical compound Cl.CC(C)(C)C(N)=N ARDGQYVTLGUJII-UHFFFAOYSA-N 0.000 description 2
- NBIWKKRBJRQYME-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-pyridin-3-ylethanone Chemical compound ClC1=CC=CC=C1CC(=O)C1=CC=CN=C1 NBIWKKRBJRQYME-UHFFFAOYSA-N 0.000 description 2
- YVCWMYMJVPJFOI-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-pyridin-3-ylethanone Chemical compound ClC1=CC=CC(CC(=O)C=2C=NC=CC=2)=C1 YVCWMYMJVPJFOI-UHFFFAOYSA-N 0.000 description 2
- MCTYJNJITLRZKY-UHFFFAOYSA-N 2-(3-methoxyphenyl)-1-pyridin-3-ylethanone Chemical compound COC1=CC=CC(CC(=O)C=2C=NC=CC=2)=C1 MCTYJNJITLRZKY-UHFFFAOYSA-N 0.000 description 2
- DETWQKBBKMMNHC-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-pyridin-3-ylethanone Chemical compound C1=CC(Cl)=CC=C1CC(=O)C1=CC=CN=C1 DETWQKBBKMMNHC-UHFFFAOYSA-N 0.000 description 2
- RLFQYYQWEAFLSU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-pyridin-3-ylethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)C1=CC=CN=C1 RLFQYYQWEAFLSU-UHFFFAOYSA-N 0.000 description 2
- DWKAGCAGFPGSQM-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-1-pyridin-3-ylethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC(=O)C1=CC=CN=C1 DWKAGCAGFPGSQM-UHFFFAOYSA-N 0.000 description 2
- TZFYLDICGWHVGE-UHFFFAOYSA-N 2-oxo-2-pyridin-4-ylacetaldehyde Chemical compound O=CC(=O)C1=CC=NC=C1 TZFYLDICGWHVGE-UHFFFAOYSA-N 0.000 description 2
- GVEQCFMNUYFHOE-UHFFFAOYSA-N 2-phenyl-1-pyridin-3-ylethanone Chemical compound C=1C=CN=CC=1C(=O)CC1=CC=CC=C1 GVEQCFMNUYFHOE-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
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- MUANZYIPCHDGJH-UHFFFAOYSA-N ethyl 2-(2-chlorophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1Cl MUANZYIPCHDGJH-UHFFFAOYSA-N 0.000 description 1
- HTDQOYWJDUMNHX-UHFFFAOYSA-N ethyl 2-(2-methylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1C HTDQOYWJDUMNHX-UHFFFAOYSA-N 0.000 description 1
- SLNHJHHDMDGTGB-UHFFFAOYSA-N ethyl 2-(3-chlorophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(Cl)=C1 SLNHJHHDMDGTGB-UHFFFAOYSA-N 0.000 description 1
- RVIWPVAVHHVQIR-UHFFFAOYSA-N ethyl 2-(3-methylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(C)=C1 RVIWPVAVHHVQIR-UHFFFAOYSA-N 0.000 description 1
- UTWBWFXECVFDPZ-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(Cl)C=C1 UTWBWFXECVFDPZ-UHFFFAOYSA-N 0.000 description 1
- BTRGZBIXPLFVNK-UHFFFAOYSA-N ethyl 2-(4-methylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(C)C=C1 BTRGZBIXPLFVNK-UHFFFAOYSA-N 0.000 description 1
- ZLQPAONBGBXGFN-UHFFFAOYSA-N ethyl 2-(4-methylsulfanylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(SC)C=C1 ZLQPAONBGBXGFN-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 description 1
- 229960001238 methylnicotinate Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical class Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH687571A CH554415A (de) | 1970-06-01 | 1971-05-10 | Verfahren zur herstellung von zitronensaeure durch submerse gaerung. |
| CH696771A CH561202A5 (enrdf_load_stackoverflow) | 1971-05-10 | 1971-05-11 | |
| CH697571 | 1971-05-12 | ||
| CH425072A CH579072A5 (enrdf_load_stackoverflow) | 1971-05-10 | 1972-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2221546A1 true DE2221546A1 (de) | 1972-11-16 |
Family
ID=27428754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722221546 Withdrawn DE2221546A1 (de) | 1971-05-10 | 1972-05-03 | Verfahren zur Herstellung von neuen Imidazolderivaten |
Country Status (10)
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0045081A3 (en) * | 1980-07-25 | 1982-04-07 | Ciba-Geigy Ag | Trisubstituted imidazole derivatives, processes for preparing them, pharmaceutical compositions containing them, and their use |
| EP0074018A3 (en) * | 1981-09-01 | 1983-12-28 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Pyridine and pyrazine derivatives, process for the preparation of these compounds, fungicides containing these compounds as active substances, use of these compounds or fungicides to combat fungi in agriculture and in horticulture, and ketones and fungicides containing them |
| EP0257897A1 (en) * | 1986-08-15 | 1988-03-02 | Fujisawa Pharmaceutical Co., Ltd. | Imidazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same |
| WO1993014081A1 (en) * | 1992-01-13 | 1993-07-22 | Smithkline Beecham Corporation | Imidazole derivatives and their use as cytokine inhibitors |
| ES2053401A1 (es) * | 1992-01-13 | 1994-07-16 | Smithkline Beecham Corp | Compuestos de imidazol y procedimientos para su prepacion. |
| WO1996018626A1 (en) * | 1994-12-13 | 1996-06-20 | F. Hoffmann-La Roche Ag | Imidazole derivatives as protein kinase inhibitors in particular egf-r tyrosine kinase |
| US5656644A (en) * | 1994-07-20 | 1997-08-12 | Smithkline Beecham Corporation | Pyridyl imidazoles |
| WO1998047871A1 (en) * | 1997-04-18 | 1998-10-29 | Merck & Co., Inc. | Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors |
| US6127545A (en) * | 1997-04-18 | 2000-10-03 | Merck & Co., Inc. | Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors |
| US6130334A (en) * | 1998-04-15 | 2000-10-10 | Merck & Co., Inc. | Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors |
| US6268370B1 (en) | 1992-01-13 | 2001-07-31 | Smithkline Beecham Corporation | Compounds |
| WO2001062756A1 (en) * | 2000-02-21 | 2001-08-30 | Smithkline Beecham P.L.C. | Pyridinylimidazoles |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK513580A (da) * | 1980-01-07 | 1981-07-08 | Du Pont | Fremgangsmaade til fremstilling af 4,5-diaryl-alfa (polyhalogenalkyl)-1h-imidazol-2-methanoler |
| US4372964A (en) * | 1980-10-30 | 1983-02-08 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-1H-imidazole-2-methanols |
| WO1983002613A1 (en) * | 1981-07-20 | 1983-08-04 | Sallmann, Alfred | Trisubstituted oxazo compounds |
| EP0084756A1 (de) * | 1982-01-22 | 1983-08-03 | Ciba-Geigy Ag | Trisubstituierte Oxazaverbindungen |
| EP0084757A1 (de) * | 1982-01-25 | 1983-08-03 | Ciba-Geigy Ag | Trisubstituierte Diaza-Derivate |
| EP1306377A3 (en) * | 1993-11-08 | 2003-05-07 | Smithkline Beecham Corporation | Pyridyl-oxazoles and their use as cytokines inhibitors |
| US6426360B1 (en) * | 1994-07-28 | 2002-07-30 | G D Searle & Co. | 4,5-substituted imidazolyl compounds for the treatment of inflammation |
| US5620999A (en) * | 1994-07-28 | 1997-04-15 | Weier; Richard M. | Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation |
| ES2187473T3 (es) * | 1999-04-09 | 2003-06-16 | Smithkline Beecham Corp | Triarylimidazoles. |
| GB0007405D0 (en) | 2000-03-27 | 2000-05-17 | Smithkline Beecham Corp | Compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3192211A (en) * | 1962-05-03 | 1965-06-29 | Nl Combinatie Chem Ind | 5-phenyl-5-(2-pyrazyl)-hydantoin |
| US3538104A (en) * | 1969-02-28 | 1970-11-03 | Geigy Chem Corp | Pyridyl-2-imidazolones |
-
1971
- 1971-05-11 CH CH696771A patent/CH561202A5/xx not_active IP Right Cessation
- 1971-05-11 CH CH76775A patent/CH561716A5/xx not_active IP Right Cessation
- 1971-05-11 CH CH76875A patent/CH561717A5/xx not_active IP Right Cessation
- 1971-05-11 CH CH76975A patent/CH561718A5/xx not_active IP Right Cessation
-
1972
- 1972-03-22 CH CH425072A patent/CH579072A5/xx not_active IP Right Cessation
- 1972-04-27 SE SE7205565A patent/SE405731B/xx unknown
- 1972-04-28 GB GB1978172A patent/GB1381031A/en not_active Expired
- 1972-05-03 DE DE19722221546 patent/DE2221546A1/de not_active Withdrawn
- 1972-05-08 CA CA141,520A patent/CA1012148A/en not_active Expired
- 1972-05-09 AU AU42055/72A patent/AU472065B2/en not_active Expired
- 1972-05-10 NL NL7206346A patent/NL7206346A/xx not_active Application Discontinuation
- 1972-05-10 FR FR7216738A patent/FR2137740B1/fr not_active Expired
- 1972-05-10 AT AT386673A patent/AT319940B/de not_active IP Right Cessation
- 1972-05-10 BE BE783244A patent/BE783244A/xx not_active IP Right Cessation
- 1972-05-10 AT AT386773A patent/AT319941B/de not_active IP Right Cessation
- 1972-05-10 AT AT386573A patent/AT319939B/de not_active IP Right Cessation
- 1972-05-10 AT AT408972A patent/AT316544B/de not_active IP Right Cessation
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0045081A3 (en) * | 1980-07-25 | 1982-04-07 | Ciba-Geigy Ag | Trisubstituted imidazole derivatives, processes for preparing them, pharmaceutical compositions containing them, and their use |
| EP0074018A3 (en) * | 1981-09-01 | 1983-12-28 | F. Hoffmann-La Roche & Co. Aktiengesellschaft | Pyridine and pyrazine derivatives, process for the preparation of these compounds, fungicides containing these compounds as active substances, use of these compounds or fungicides to combat fungi in agriculture and in horticulture, and ketones and fungicides containing them |
| EP0257897A1 (en) * | 1986-08-15 | 1988-03-02 | Fujisawa Pharmaceutical Co., Ltd. | Imidazole compounds, processes for the preparation thereof and pharmaceutical composition comprising the same |
| EP0943616A1 (en) * | 1992-01-13 | 1999-09-22 | Smithkline Beecham Corporation | Substituted imidazole derivatives and their use as cytokine inhibitors |
| ES2053401A1 (es) * | 1992-01-13 | 1994-07-16 | Smithkline Beecham Corp | Compuestos de imidazol y procedimientos para su prepacion. |
| US5686455A (en) * | 1992-01-13 | 1997-11-11 | Smithkline Beecham Corporation | Imidazole derivatives and their use as cytokine inhibitors |
| WO1993014081A1 (en) * | 1992-01-13 | 1993-07-22 | Smithkline Beecham Corporation | Imidazole derivatives and their use as cytokine inhibitors |
| US6268370B1 (en) | 1992-01-13 | 2001-07-31 | Smithkline Beecham Corporation | Compounds |
| US5656644A (en) * | 1994-07-20 | 1997-08-12 | Smithkline Beecham Corporation | Pyridyl imidazoles |
| WO1996018626A1 (en) * | 1994-12-13 | 1996-06-20 | F. Hoffmann-La Roche Ag | Imidazole derivatives as protein kinase inhibitors in particular egf-r tyrosine kinase |
| US5959113A (en) * | 1994-12-13 | 1999-09-28 | Hoffmann-La Roche Inc. | Imidazol derivatives |
| WO1998047871A1 (en) * | 1997-04-18 | 1998-10-29 | Merck & Co., Inc. | Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors |
| US6127545A (en) * | 1997-04-18 | 2000-10-03 | Merck & Co., Inc. | Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors |
| US6130334A (en) * | 1998-04-15 | 2000-10-10 | Merck & Co., Inc. | Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors |
| WO2001062756A1 (en) * | 2000-02-21 | 2001-08-30 | Smithkline Beecham P.L.C. | Pyridinylimidazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| AU472065B2 (en) | 1976-05-13 |
| CA1012148A (en) | 1977-06-14 |
| FR2137740B1 (enrdf_load_stackoverflow) | 1975-08-01 |
| CH561716A5 (enrdf_load_stackoverflow) | 1975-05-15 |
| AT316544B (de) | 1974-07-10 |
| AT319941B (de) | 1975-01-10 |
| CH579072A5 (enrdf_load_stackoverflow) | 1976-08-31 |
| GB1381031A (en) | 1975-01-22 |
| AT319940B (de) | 1975-01-10 |
| SE405731B (sv) | 1978-12-27 |
| BE783244A (fr) | 1972-11-10 |
| FR2137740A1 (enrdf_load_stackoverflow) | 1972-12-29 |
| CH561717A5 (enrdf_load_stackoverflow) | 1975-05-15 |
| CH561718A5 (enrdf_load_stackoverflow) | 1975-05-15 |
| AU4205572A (en) | 1973-11-15 |
| NL7206346A (enrdf_load_stackoverflow) | 1972-11-14 |
| AT319939B (de) | 1975-01-10 |
| CH561202A5 (enrdf_load_stackoverflow) | 1975-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |