NO791597L - Imidazolderivater, samt fremgangsmaate til deres fremstilling - Google Patents
Imidazolderivater, samt fremgangsmaate til deres fremstillingInfo
- Publication number
- NO791597L NO791597L NO791597A NO791597A NO791597L NO 791597 L NO791597 L NO 791597L NO 791597 A NO791597 A NO 791597A NO 791597 A NO791597 A NO 791597A NO 791597 L NO791597 L NO 791597L
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- compound according
- hydrogen
- compound
- halogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000003839 salts Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- OZRLINSKTFKPDY-UHFFFAOYSA-N 2-(3-benzyl-5-chloro-2-phenylimidazol-4-yl)acetic acid Chemical compound C=1C=CC=CC=1CN1C(CC(=O)O)=C(Cl)N=C1C1=CC=CC=C1 OZRLINSKTFKPDY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- LJENXNLQPYSJJB-UHFFFAOYSA-N 2-[3-benzyl-5-chloro-2-[4-(dimethylamino)phenyl]imidazol-4-yl]acetic acid Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(Cl)=C(CC(O)=O)N1CC1=CC=CC=C1 LJENXNLQPYSJJB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy Chemical group 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZNXSUWSNVODENE-UHFFFAOYSA-N 2-amino-3,3-dichloroprop-2-enenitrile Chemical compound N#CC(N)=C(Cl)Cl ZNXSUWSNVODENE-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000001077 hypotensive effect Effects 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- FKXQRILOGWZJKP-UHFFFAOYSA-N 2-(3-benzyl-5-chloro-2-phenylimidazol-4-yl)acetonitrile Chemical compound C=1C=CC=CC=1CN1C(CC#N)=C(Cl)N=C1C1=CC=CC=C1 FKXQRILOGWZJKP-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PBVGLRJEJIAMAV-UHFFFAOYSA-N (3-benzyl-5-chloro-2-phenylimidazol-4-yl)methanol Chemical compound C=1C=CC=CC=1CN1C(CO)=C(Cl)N=C1C1=CC=CC=C1 PBVGLRJEJIAMAV-UHFFFAOYSA-N 0.000 description 2
- FNVBNEJDEPWRNL-UHFFFAOYSA-N 2-[3-benzyl-5-chloro-2-[4-(dimethylamino)phenyl]imidazol-4-yl]acetonitrile Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(Cl)=C(CC#N)N1CC1=CC=CC=C1 FNVBNEJDEPWRNL-UHFFFAOYSA-N 0.000 description 2
- URFALHBVKUMQOE-UHFFFAOYSA-N 3-benzyl-5-chloro-2-phenylimidazole-4-carbaldehyde Chemical compound C=1C=CC=CC=1CN1C(C=O)=C(Cl)N=C1C1=CC=CC=C1 URFALHBVKUMQOE-UHFFFAOYSA-N 0.000 description 2
- CCXUATWKEDQRMP-UHFFFAOYSA-N 5-chloro-2-phenyl-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(Cl)NC(C=2C=CC=CC=2)=N1 CCXUATWKEDQRMP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- PSMMNEWEDNHJGY-UHFFFAOYSA-N ethyl 2-(3-benzyl-5-chloro-2-phenylimidazol-4-yl)acetate Chemical compound C=1C=CC=CC=1CN1C(CC(=O)OCC)=C(Cl)N=C1C1=CC=CC=C1 PSMMNEWEDNHJGY-UHFFFAOYSA-N 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GQZILHANXWXTIW-UHFFFAOYSA-N (3-benzylimidazol-4-yl)methanol Chemical compound OCC1=CN=CN1CC1=CC=CC=C1 GQZILHANXWXTIW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVYZHTLJCWHSCH-UHFFFAOYSA-N 1-benzyl-4-chloro-5-(chloromethyl)-2-phenylimidazole Chemical compound C=1C=CC=CC=1CN1C(CCl)=C(Cl)N=C1C1=CC=CC=C1 PVYZHTLJCWHSCH-UHFFFAOYSA-N 0.000 description 1
- GQOQUUCIZBMRMZ-UHFFFAOYSA-N 1-benzyl-5-(chloromethyl)imidazole Chemical compound ClCC1=CN=CN1CC1=CC=CC=C1 GQOQUUCIZBMRMZ-UHFFFAOYSA-N 0.000 description 1
- ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical class O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 description 1
- VWCAOXXEWCHTCU-UHFFFAOYSA-N 2-(4-butoxyphenyl)-5-chloro-1h-imidazole-4-carbaldehyde Chemical compound C1=CC(OCCCC)=CC=C1C1=NC(Cl)=C(C=O)N1 VWCAOXXEWCHTCU-UHFFFAOYSA-N 0.000 description 1
- MHHHKMCAVMIJKM-UHFFFAOYSA-N 2-[3-[(4-aminophenyl)methyl]-5-chloro-2-phenylimidazol-4-yl]acetic acid Chemical compound C1=CC(N)=CC=C1CN1C(C=2C=CC=CC=2)=NC(Cl)=C1CC(O)=O MHHHKMCAVMIJKM-UHFFFAOYSA-N 0.000 description 1
- AORPUAOXEZGFPW-UHFFFAOYSA-N 2-[3-benzyl-5-chloro-2-(4-methoxyphenyl)imidazol-4-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NC(Cl)=C(CC(O)=O)N1CC1=CC=CC=C1 AORPUAOXEZGFPW-UHFFFAOYSA-N 0.000 description 1
- NPQCNODMSZUVRB-UHFFFAOYSA-N 2-[3-benzyl-5-chloro-2-(4-methoxyphenyl)imidazol-4-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=NC(Cl)=C(CC#N)N1CC1=CC=CC=C1 NPQCNODMSZUVRB-UHFFFAOYSA-N 0.000 description 1
- GBSWQVPCESLARD-UHFFFAOYSA-N 2-[5-chloro-3-[(4-nitrophenyl)methyl]-2-phenylimidazol-4-yl]acetic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1CN1C(CC(=O)O)=C(Cl)N=C1C1=CC=CC=C1 GBSWQVPCESLARD-UHFFFAOYSA-N 0.000 description 1
- PNPQGXZMDBNGDM-UHFFFAOYSA-N 3,3-dichloro-2-[[4-(dimethylamino)phenyl]methylideneamino]prop-2-enenitrile Chemical compound CN(C)C1=CC=C(C=NC(C#N)=C(Cl)Cl)C=C1 PNPQGXZMDBNGDM-UHFFFAOYSA-N 0.000 description 1
- MUPUILNKBXTUGA-UHFFFAOYSA-N 3-benzyl-5-chloro-2-(4-methoxyphenyl)imidazole-4-carbaldehyde Chemical compound C1=CC(OC)=CC=C1C1=NC(Cl)=C(C=O)N1CC1=CC=CC=C1 MUPUILNKBXTUGA-UHFFFAOYSA-N 0.000 description 1
- QONDAZCJAPQGRX-UHFFFAOYSA-N 3-benzylimidazole-4-carbaldehyde Chemical compound O=CC1=CN=CN1CC1=CC=CC=C1 QONDAZCJAPQGRX-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- XHWMNHADTZZHGI-UHFFFAOYSA-N 4-butoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C=C1 XHWMNHADTZZHGI-UHFFFAOYSA-N 0.000 description 1
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 1
- NWFDQXWAOAZISF-UHFFFAOYSA-N 5-chloro-2-[4-(dimethylamino)phenyl]-1h-imidazole-4-carbaldehyde Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(Cl)=C(C=O)N1 NWFDQXWAOAZISF-UHFFFAOYSA-N 0.000 description 1
- HZBNABLXOCGJGU-UHFFFAOYSA-N 5-chloro-3-[(4-nitrophenyl)methyl]-2-phenylimidazole-4-carbaldehyde Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1C(C=2C=CC=CC=2)=NC(Cl)=C1C=O HZBNABLXOCGJGU-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FNLXNIXTURNHIM-UHFFFAOYSA-N [3-benzyl-5-chloro-2-(4-methoxyphenyl)imidazol-4-yl]methanol Chemical compound C1=CC(OC)=CC=C1C1=NC(Cl)=C(CO)N1CC1=CC=CC=C1 FNLXNIXTURNHIM-UHFFFAOYSA-N 0.000 description 1
- RTAXFPFPPNOFRX-UHFFFAOYSA-N [3-benzyl-5-chloro-2-[4-(dimethylamino)phenyl]imidazol-4-yl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(Cl)=C(CO)N1CC1=CC=CC=C1 RTAXFPFPPNOFRX-UHFFFAOYSA-N 0.000 description 1
- DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-N iron;hydrochloride Chemical compound Cl.[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- JOQGJRQKCIJIDB-UHFFFAOYSA-N tin;hydrochloride Chemical compound Cl.[Sn] JOQGJRQKCIJIDB-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
- C07D233/68—Halogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5791278A JPS54148788A (en) | 1978-05-15 | 1978-05-15 | 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791597L true NO791597L (no) | 1979-11-16 |
Family
ID=13069193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791597A NO791597L (no) | 1978-05-15 | 1979-05-14 | Imidazolderivater, samt fremgangsmaate til deres fremstilling |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4207324A (de) |
| EP (1) | EP0005528B1 (de) |
| JP (1) | JPS54148788A (de) |
| AU (1) | AU526302B2 (de) |
| CA (1) | CA1124244A (de) |
| DE (1) | DE2965062D1 (de) |
| DK (1) | DK197279A (de) |
| ES (1) | ES480542A1 (de) |
| GR (1) | GR68432B (de) |
| NO (1) | NO791597L (de) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5671074A (en) * | 1979-11-12 | 1981-06-13 | Takeda Chem Ind Ltd | 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative |
| JPS5671073A (en) * | 1979-11-12 | 1981-06-13 | Takeda Chem Ind Ltd | Imidazole derivative |
| US4338453A (en) * | 1980-09-17 | 1982-07-06 | The Upjohn Company | Aminoalkyl-1,2,4-triazoles |
| GB2092569B (en) * | 1981-02-05 | 1984-09-19 | Farmos Oy | Substituted imidazole derivatives and their preparation and use |
| DE3106150A1 (de) * | 1981-02-13 | 1982-09-16 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | "verfahren zur herstellung von imidazolessigsaeurederivaten" |
| CA1181082A (en) * | 1981-11-20 | 1985-01-15 | Toni Dockner | Substituted benzylimidazolium salts and microbicides containing these compounds |
| JPS58157768A (ja) * | 1982-03-16 | 1983-09-19 | Takeda Chem Ind Ltd | ４−クロロ−２−フエニルイミダゾ−ル−５−酢酸誘導体 |
| US5138069A (en) * | 1986-07-11 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| US5189048A (en) * | 1988-01-07 | 1993-02-23 | E. I. Du Pont De Nemours And Company | Substituted 1,2,3 triazole angiotensin II antagonists |
| US5081127A (en) * | 1988-01-07 | 1992-01-14 | E. I. Du Pont De Nemours And Company | Substituted 1,2,3-triazole angiotensin II antagonists |
| US5210079A (en) * | 1988-01-07 | 1993-05-11 | E. I. Du Pont De Nemours And Company | Treatment of chronic renal failure with imidazole angiotensin-II receptor antagonists |
| US5015651A (en) * | 1988-01-07 | 1991-05-14 | E. I. Du Pont De Nemours And Company | Treatment of hypertension with 1,2,4-angiotensin II antagonists |
| US5315013A (en) * | 1988-01-07 | 1994-05-24 | E. I. Du Pont De Nemours And Company | Substituted pyrazole angiotensin II antagonists |
| CA1338238C (en) | 1988-01-07 | 1996-04-09 | David John Carini | Angiotensin ii receptor blocking imidazoles and combinations thereof with diuretics and nsaids |
| US4880804A (en) * | 1988-01-07 | 1989-11-14 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking benzimidazoles |
| US5093346A (en) * | 1988-01-07 | 1992-03-03 | E. I. Du Pont De Nemours And Company | Substituted 1,2,4-triazole angiotensin II antagonists |
| US5354867A (en) * | 1988-12-06 | 1994-10-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| US4916129A (en) * | 1989-01-19 | 1990-04-10 | E. I. Du Pont De Nemours And Company | Combination β-blocking/angiotensin II blocking antihypertensives |
| US5064825A (en) * | 1989-06-01 | 1991-11-12 | Merck & Co., Inc. | Angiotensin ii antagonists |
| SG50669A1 (en) * | 1989-06-30 | 1998-07-20 | Du Pont | Fused-ring aryl subtituted imidazoles |
| EP0409332A3 (en) * | 1989-07-19 | 1991-08-07 | Merck & Co. Inc. | Substituted triazoles as angiotensin ii antagonists |
| US5073566A (en) * | 1989-11-30 | 1991-12-17 | Eli Lilly And Company | Angiotensin ii antagonist 1,3-imidazoles and use thereas |
| US5166206A (en) * | 1990-03-30 | 1992-11-24 | Merck & Co., Inc. | Substituted pyrimidines, pyrimidinones and pyridopyrimidines |
| JPH0441481A (ja) * | 1990-06-05 | 1992-02-12 | Nippon Synthetic Chem Ind Co Ltd:The | イミダゾール類のハロゲン化方法 |
| US5374615A (en) * | 1990-10-31 | 1994-12-20 | E. R. Squibb & Sons, Inc. | Indole- and benzimidazole-substituted imidazole and benzimidazole derivatives |
| US5153347A (en) * | 1991-01-31 | 1992-10-06 | E. R. Squibb & Sons, Inc. | Phosphonate, phosphinate derivatives useful as antihypertensive agents |
| US5191086A (en) * | 1991-03-19 | 1993-03-02 | E.R. Squibb & Sons, Inc. | Imidazole and benzimidazole derivatives |
| US5177074A (en) | 1991-03-26 | 1993-01-05 | Merck & Co., Inc. | Angiotensin ii antagonists incorporating a substituted thiophene or furan |
| US5506361A (en) * | 1991-05-08 | 1996-04-09 | Theupjohn Company | Imidazobenzoquinones and composition for preventing or treating hypertension or congestive heart failure containing the same |
| GB9110636D0 (en) * | 1991-05-16 | 1991-07-03 | Glaxo Group Ltd | Chemical compounds |
| US5332820A (en) * | 1991-05-20 | 1994-07-26 | E. I. Du Pont De Nemours And Company | Dibenzobicyclo(2.2.2) octane angiotensin II antagonists |
| US5294722A (en) * | 1992-04-16 | 1994-03-15 | E. R. Squibb & Sons, Inc. | Process for the preparation of imidazoles useful in angiotensin II antagonism |
| US5401851A (en) * | 1992-06-03 | 1995-03-28 | Eli Lilly And Company | Angiotensin II antagonists |
| US5612360A (en) * | 1992-06-03 | 1997-03-18 | Eli Lilly And Company | Angiotensin II antagonists |
| US5721264A (en) * | 1993-04-07 | 1998-02-24 | Nissan Chemical Industries, Ltd. | Pyrazole derivatives |
| DE4343613A1 (de) * | 1993-12-21 | 1995-06-22 | Bayer Ag | N-substituierte Aryl-trifluormethylimidazole |
| WO1995033730A1 (fr) * | 1994-06-09 | 1995-12-14 | Nippon Soda Co., Ltd. | Derive d'imidazole, procede de production et herbicide |
| US6080870A (en) * | 1996-04-03 | 2000-06-27 | Merck & Co., Inc. | Biaryl substituted imidazole compounds useful as farnesyl-protein transferase inhibitors |
| US5859035A (en) * | 1996-04-03 | 1999-01-12 | Merck & Co., Inc. | Arylheteroaryl inhibitors of farnesyl-protein transferase |
| JP2000504024A (ja) * | 1996-04-03 | 2000-04-04 | メルク エンド カンパニー インコーポレーテッド | ファルネシル―タンパク質トランスフェラーゼ阻害剤 |
| US6063930A (en) * | 1996-04-03 | 2000-05-16 | Merck & Co., Inc. | Substituted imidazole compounds useful as farnesyl-protein transferase inhibitors |
| IT1295405B1 (it) | 1997-09-30 | 1999-05-12 | Merck Sharp & Dohme Italia S P | Uso di un antagonista recettoriale di angiotensina ii per la preparazione di farmaci per aumentare il tasso di sopravvivenza di |
| WO2006110037A2 (en) * | 2005-04-15 | 2006-10-19 | Dishman Pharmaceuticals And Chemicals Ltd. | Preparation of 2-substituted 4-chl0r0-5-f0rmylimidaz0les by vilsmeier reaction of the condensation product of glycine and an imido ester with a formamide in the presence of a triflate (trifluormethanξsulphonate) catalyst |
| CA3089569C (en) | 2007-06-04 | 2023-12-05 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| EP2321341B1 (de) | 2008-07-16 | 2017-02-22 | Synergy Pharmaceuticals Inc. | Zur behandlung von erkrankungen des magen-darm-trakts, entzündlichen erkrankungen, krebs und anderen erkrankungen geeignete agonisten von guanylatcyclase |
| WO2010014739A2 (en) * | 2008-07-29 | 2010-02-04 | Kalypsys, Inc. | Heterocyclic modulators of tgr5 |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| EP2970384A1 (de) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonisten der guanylatcyclase und deren verwendungen |
| JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
| RS65632B1 (sr) | 2013-06-05 | 2024-07-31 | Bausch Health Ireland Ltd | Ultra-prečišćeni agonisti guanilat-ciklaze c, postupak njihove pripreme i upotrebe |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH159795A (de) * | 1931-12-19 | 1933-01-31 | Hoffmann La Roche | Verfahren zur Darstellung von Dijodimidazolessigsäure. |
| US3354173A (en) * | 1964-04-16 | 1967-11-21 | Janssen Pharmaceutica Nv | Imidazole carboxylates |
| CH528514A (de) * | 1969-05-22 | 1972-09-30 | Bayer Ag | Verfahren zur Herstellung von Acylimidazolen |
| US4042702A (en) * | 1973-08-16 | 1977-08-16 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Halogen pyrazole derivatives, a method for producing these halogen pyrazole derivatives, medicaments containing and methods of using them |
| US3932445A (en) * | 1974-06-26 | 1976-01-13 | Mcneil Laboratories, Incorporated | 2-Aryl-4-(R-methyl)-5-methylimidazoles |
| US4038286A (en) * | 1975-03-10 | 1977-07-26 | Janssen Pharmaceutica N.V. | Racemates and optical isomers of 1-(1-phenylethyl)-1h-imidazole-5-carboylic acid derivatives |
| US3991072A (en) * | 1975-03-10 | 1976-11-09 | Janssen Pharmaceutica N.V. | Racemization of lower alkyl imidazole carboxylates |
-
1978
- 1978-05-15 JP JP5791278A patent/JPS54148788A/ja active Granted
-
1979
- 1979-05-01 AU AU46573/79A patent/AU526302B2/en not_active Expired - Fee Related
- 1979-05-07 GR GR59035A patent/GR68432B/el unknown
- 1979-05-07 US US06/036,645 patent/US4207324A/en not_active Expired - Lifetime
- 1979-05-09 CA CA327,260A patent/CA1124244A/en not_active Expired
- 1979-05-14 NO NO791597A patent/NO791597L/no unknown
- 1979-05-14 DK DK197279A patent/DK197279A/da unknown
- 1979-05-14 EP EP79101460A patent/EP0005528B1/de not_active Expired
- 1979-05-14 ES ES480542A patent/ES480542A1/es not_active Expired
- 1979-05-14 DE DE7979101460T patent/DE2965062D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU526302B2 (en) | 1983-01-06 |
| AU4657379A (en) | 1979-11-22 |
| JPS54148788A (en) | 1979-11-21 |
| CA1124244A (en) | 1982-05-25 |
| DE2965062D1 (en) | 1983-04-28 |
| GR68432B (de) | 1981-12-30 |
| EP0005528A3 (en) | 1980-01-09 |
| EP0005528B1 (de) | 1983-03-23 |
| ES480542A1 (es) | 1980-04-01 |
| EP0005528A2 (de) | 1979-11-28 |
| US4207324A (en) | 1980-06-10 |
| DK197279A (da) | 1979-11-16 |
| JPS611022B2 (de) | 1986-01-13 |
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