NO873432L - Fremgangsmaate for fremstilling av imidazolforbindelser. - Google Patents
Fremgangsmaate for fremstilling av imidazolforbindelser.Info
- Publication number
- NO873432L NO873432L NO873432A NO873432A NO873432L NO 873432 L NO873432 L NO 873432L NO 873432 A NO873432 A NO 873432A NO 873432 A NO873432 A NO 873432A NO 873432 L NO873432 L NO 873432L
- Authority
- NO
- Norway
- Prior art keywords
- pyridyl
- methyl
- nujol
- melting point
- imidazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 35
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 50
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 81
- -1 nitro, amino, substituted amino, hydroxy Chemical group 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 62
- 125000003545 alkoxy group Chemical group 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004442 acylamino group Chemical group 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 238000002844 melting Methods 0.000 description 281
- 230000008018 melting Effects 0.000 description 281
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- 238000001819 mass spectrum Methods 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 68
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 150000002460 imidazoles Chemical class 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- 238000001816 cooling Methods 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 235000011054 acetic acid Nutrition 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- LDLJPVOBMJSVFC-UHFFFAOYSA-N 2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound CC=1N=C(C=2C(=CC=CC=2)N)NC=1C1=CC=CN=C1 LDLJPVOBMJSVFC-UHFFFAOYSA-N 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 238000010531 catalytic reduction reaction Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 239000003638 chemical reducing agent Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 230000002411 adverse Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- SZWIBPZNNPKBKB-UHFFFAOYSA-N 3-[2-(2-methoxy-4-methylsulfanylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(SC)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 SZWIBPZNNPKBKB-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000007522 mineralic acids Chemical class 0.000 description 5
- GZMDJFGGSUILDA-UHFFFAOYSA-N n-[2-chloro-5-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 GZMDJFGGSUILDA-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- VXYIFBJCMQUFME-UHFFFAOYSA-N 1-hydroxyimino-1-pyridin-3-ylpropan-2-one Chemical compound CC(=O)C(=NO)C1=CC=CN=C1 VXYIFBJCMQUFME-UHFFFAOYSA-N 0.000 description 4
- JTMQPIWQTLVTLP-UHFFFAOYSA-N 2-chloro-4-methoxy-5-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound COC1=CC(Cl)=C(N)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 JTMQPIWQTLVTLP-UHFFFAOYSA-N 0.000 description 4
- IEXWFKFVMYTVKZ-UHFFFAOYSA-N 2-chloro-5-methoxy-n-methyl-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound C1=C(Cl)C(NC)=CC(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 IEXWFKFVMYTVKZ-UHFFFAOYSA-N 0.000 description 4
- AVNRKEGUSALBSN-UHFFFAOYSA-N 3-[2-(2,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(OC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 AVNRKEGUSALBSN-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VDLSGWABQRFJOZ-UHFFFAOYSA-N n-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 VDLSGWABQRFJOZ-UHFFFAOYSA-N 0.000 description 4
- UQPXJHUMNXDDGA-UHFFFAOYSA-N n-[3-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound COC1=CC(NC(C)=O)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 UQPXJHUMNXDDGA-UHFFFAOYSA-N 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OEXRZZMPNACKSP-UHFFFAOYSA-N 1-methyl-3-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]thiourea Chemical compound CNC(=S)NC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 OEXRZZMPNACKSP-UHFFFAOYSA-N 0.000 description 3
- IFTYKUALNOLUPZ-UHFFFAOYSA-N 1-methyl-3-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]urea Chemical compound CNC(=O)NC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 IFTYKUALNOLUPZ-UHFFFAOYSA-N 0.000 description 3
- BXLCAZBQEADHJQ-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)-5-ethyl-1h-imidazol-4-yl]pyridine Chemical compound CCC=1NC(C=2C=C(OC)C(OC)=CC=2)=NC=1C1=CC=CC=N1 BXLCAZBQEADHJQ-UHFFFAOYSA-N 0.000 description 3
- GIBXUWRWLXXVEJ-UHFFFAOYSA-N 3-[2-(2,4-dimethoxyphenyl)-5-ethyl-1h-imidazol-4-yl]pyridine Chemical compound CCC=1N=C(C=2C(=CC(OC)=CC=2)OC)NC=1C1=CC=CN=C1 GIBXUWRWLXXVEJ-UHFFFAOYSA-N 0.000 description 3
- KORRLLBRODMOKX-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)F)NC=1C1=CC=CN=C1 KORRLLBRODMOKX-UHFFFAOYSA-N 0.000 description 3
- LZZKPPHJWYRXKH-UHFFFAOYSA-N 3-[2-(2-methoxy-4-methylsulfinylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(S(C)=O)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 LZZKPPHJWYRXKH-UHFFFAOYSA-N 0.000 description 3
- CHFSSUXKCICDPZ-UHFFFAOYSA-N 3-[2-(2-methoxy-4-methylsulfonylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(S(C)(=O)=O)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 CHFSSUXKCICDPZ-UHFFFAOYSA-N 0.000 description 3
- LAXFXVCOZXSTQL-UHFFFAOYSA-N 3-[2-(2-methoxy-4-phenylmethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C=1C=C(C=2NC(=C(C)N=2)C=2C=NC=CC=2)C(OC)=CC=1OCC1=CC=CC=C1 LAXFXVCOZXSTQL-UHFFFAOYSA-N 0.000 description 3
- QVNXLVKVZJSJMC-UHFFFAOYSA-N 3-[2-(2-methoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 QVNXLVKVZJSJMC-UHFFFAOYSA-N 0.000 description 3
- QRPGPBXSILZFFP-UHFFFAOYSA-N 3-[2-(4-chloro-2-methoxy-5-nitrophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(Cl)=C([N+]([O-])=O)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 QRPGPBXSILZFFP-UHFFFAOYSA-N 0.000 description 3
- VORQOUQLEKZGIZ-UHFFFAOYSA-N 3-[2-(4-chloro-2-methoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(Cl)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 VORQOUQLEKZGIZ-UHFFFAOYSA-N 0.000 description 3
- YJNFQAGBTGGRDN-UHFFFAOYSA-N 3-[2-(5-bromo-2,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=C(Br)C(OC)=CC(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 YJNFQAGBTGGRDN-UHFFFAOYSA-N 0.000 description 3
- NQYSBVGHSRVVJW-UHFFFAOYSA-N 3-[5-methyl-2-(2-nitrophenyl)-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)[N+]([O-])=O)NC=1C1=CC=CN=C1 NQYSBVGHSRVVJW-UHFFFAOYSA-N 0.000 description 3
- AZGSDCUHMZSAGB-UHFFFAOYSA-N 3-methoxy-4-(5-methyl-4-pyridin-3-yl-1H-imidazol-2-yl)phenol Chemical compound COC1=CC(O)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 AZGSDCUHMZSAGB-UHFFFAOYSA-N 0.000 description 3
- PBFMYDIMFVZMLC-UHFFFAOYSA-N 3-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound COC1=CC(N)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 PBFMYDIMFVZMLC-UHFFFAOYSA-N 0.000 description 3
- IIDYLOIANVDZJH-UHFFFAOYSA-N 4-[2-(2,4-dimethoxyphenyl)-5-ethyl-1h-imidazol-4-yl]pyridine Chemical compound CCC=1NC(C=2C(=CC(OC)=CC=2)OC)=NC=1C1=CC=NC=C1 IIDYLOIANVDZJH-UHFFFAOYSA-N 0.000 description 3
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
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- 125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
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- 210000002837 heart atrium Anatomy 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
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- 210000000548 hind-foot Anatomy 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
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- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- OWZIYWAUNZMLRT-UHFFFAOYSA-L iron(2+);oxalate Chemical compound [Fe+2].[O-]C(=O)C([O-])=O OWZIYWAUNZMLRT-UHFFFAOYSA-L 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 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
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- ZDRRWYKWNKGSPK-UHFFFAOYSA-N n,3-dimethyl-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound CC1=CC(NC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 ZDRRWYKWNKGSPK-UHFFFAOYSA-N 0.000 description 1
- YFTSXEONXVOMIY-UHFFFAOYSA-N n-(2-chloro-4-formyl-5-methoxyphenyl)acetamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C=O YFTSXEONXVOMIY-UHFFFAOYSA-N 0.000 description 1
- XGNDNYNNDNJPKV-UHFFFAOYSA-N n-[2-chloro-4-(1-hydroxy-4-methyl-5-pyridin-3-ylimidazol-2-yl)-5-methoxyphenyl]-n-methylacetamide Chemical compound COC1=CC(N(C)C(C)=O)=C(Cl)C=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 XGNDNYNNDNJPKV-UHFFFAOYSA-N 0.000 description 1
- HZCGSQHHWYQFSQ-UHFFFAOYSA-N n-[2-chloro-4-(1-hydroxy-4-methyl-5-pyridin-3-ylimidazol-2-yl)-5-methoxyphenyl]acetamide Chemical compound COC1=CC(NC(C)=O)=C(Cl)C=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 HZCGSQHHWYQFSQ-UHFFFAOYSA-N 0.000 description 1
- UXWBXXCPBJIPBB-UHFFFAOYSA-N n-[2-chloro-4-(1-hydroxy-4-methyl-5-pyridin-3-ylimidazol-2-yl)phenyl]acetamide Chemical compound C1=C(Cl)C(NC(=O)C)=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 UXWBXXCPBJIPBB-UHFFFAOYSA-N 0.000 description 1
- YEDFDODUJUPVEZ-UHFFFAOYSA-N n-[4-(1-hydroxy-4-methyl-5-pyridin-3-ylimidazol-2-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 YEDFDODUJUPVEZ-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000006634 pentyloxycarbonylamino group Chemical group 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
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- 229910003446 platinum oxide 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
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- WORJEOGGNQDSOE-ASTXPPQBSA-N trichloro(deuterio)methane;trideuterio(deuteriooxy)methane Chemical compound [2H]C(Cl)(Cl)Cl.[2H]OC([2H])([2H])[2H] WORJEOGGNQDSOE-ASTXPPQBSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Resins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB868619971A GB8619971D0 (en) | 1986-08-15 | 1986-08-15 | Imidazole compounds |
GB878715932A GB8715932D0 (en) | 1987-07-07 | 1987-07-07 | Imidazole compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
NO873432D0 NO873432D0 (no) | 1987-08-14 |
NO873432L true NO873432L (no) | 1988-02-16 |
Family
ID=26291182
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO873432A NO873432L (no) | 1986-08-15 | 1987-08-14 | Fremgangsmaate for fremstilling av imidazolforbindelser. |
Country Status (12)
Country | Link |
---|---|
US (1) | US4822805A (xx) |
EP (1) | EP0257897A1 (xx) |
KR (1) | KR880002840A (xx) |
CN (1) | CN87105680A (xx) |
AU (1) | AU7682587A (xx) |
DK (1) | DK425887A (xx) |
FI (1) | FI873509A (xx) |
HU (1) | HUT44779A (xx) |
IL (1) | IL83467A0 (xx) |
NO (1) | NO873432L (xx) |
OA (1) | OA08647A (xx) |
PT (1) | PT85531B (xx) |
Families Citing this family (61)
Publication number | Priority date | Publication date | Assignee | Title |
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IL104369A0 (en) * | 1992-01-13 | 1993-05-13 | Smithkline Beecham Corp | Novel compounds and compositions |
US5916891A (en) | 1992-01-13 | 1999-06-29 | Smithkline Beecham Corporation | Pyrimidinyl imidazoles |
US5670527A (en) * | 1993-07-16 | 1997-09-23 | Smithkline Beecham Corporation | Pyridyl imidazole compounds and compositions |
US5593992A (en) * | 1993-07-16 | 1997-01-14 | Smithkline Beecham Corporation | Compounds |
US5593991A (en) * | 1993-07-16 | 1997-01-14 | Adams; Jerry L. | Imidazole compounds, use and process of making |
US5616601A (en) * | 1994-07-28 | 1997-04-01 | Gd Searle & Co | 1,2-aryl and heteroaryl 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 |
US6613789B2 (en) | 1994-07-28 | 2003-09-02 | G. D. Searle & Co. | Heterocyclo-substituted imidazoles for the treatment of inflammation |
US6426360B1 (en) | 1994-07-28 | 2002-07-30 | G D Searle & Co. | 4,5-substituted imidazolyl compounds for the treatment of inflammation |
JP2636819B2 (ja) | 1994-12-20 | 1997-07-30 | 日本たばこ産業株式会社 | オキサゾール系複素環式芳香族化合物 |
US6512121B2 (en) | 1998-09-14 | 2003-01-28 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
CA2223154A1 (en) | 1995-06-02 | 1996-12-05 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US6515014B2 (en) | 1995-06-02 | 2003-02-04 | G. D. Searle & Co. | Thiophene substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US6369068B1 (en) | 1995-06-07 | 2002-04-09 | Smithkline Beecham Corporation | Amino substituted pyrimidine containing compounds |
US5739143A (en) * | 1995-06-07 | 1998-04-14 | Smithkline Beecham Corporation | Imidazole compounds and compositions |
US5658903A (en) * | 1995-06-07 | 1997-08-19 | Smithkline Beecham Corporation | Imidazole compounds, compositions and use |
ZA9610687B (en) * | 1995-12-22 | 1997-09-29 | Smithkline Beecham Corp | Novel synthesis. |
AP9700912A0 (en) | 1996-01-11 | 1997-01-31 | Smithkline Beecham Corp | Novel cycloalkyl substituted imidazoles |
JP2000503302A (ja) * | 1996-01-11 | 2000-03-21 | スミスクライン・ビーチャム・コーポレイション | 新規置換イミダゾール化合物 |
US6046208A (en) * | 1996-01-11 | 2000-04-04 | Smithkline Beecham Corporation | Substituted imidazole compounds |
ZA97175B (en) * | 1996-01-11 | 1997-11-04 | Smithkline Beecham Corp | Novel substituted imidazole compounds. |
EP0889888A4 (en) * | 1996-03-25 | 2003-01-08 | Smithkline Beecham Corp | NEW TREATMENT OF LESIONS IN THE CENTRAL NERVOUS SYSTEM |
US6677364B2 (en) * | 1998-04-20 | 2004-01-13 | G.D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
EP0956018A4 (en) | 1996-08-21 | 2000-01-12 | Smithkline Beecham Corp | IMIDAZOLE COMPOUNDS, COMPOSITIONS CONTAINING THEM AND THEIR USE |
US5929076A (en) * | 1997-01-10 | 1999-07-27 | Smithkline Beecham Corporation | Cycloalkyl substituted imidazoles |
AU7966198A (en) | 1997-06-13 | 1998-12-30 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
US6610695B1 (en) | 1997-06-19 | 2003-08-26 | Smithkline Beecham Corporation | Aryloxy substituted pyrimidine imidazole compounds |
US6489325B1 (en) | 1998-07-01 | 2002-12-03 | Smithkline Beecham Corporation | Substituted imidazole compounds |
CA2295762A1 (en) | 1997-07-02 | 1999-01-14 | Ravi Shanker Garigipati | Novel cycloalkyl substituted imidazoles |
AR016294A1 (es) * | 1997-07-02 | 2001-07-04 | Smithkline Beecham Corp | Compuesto de imidazol sustituido, composicion farmaceutica que la contiene, su uso en la fabricacion de un medicamento y procedimiento para supreparacion |
TW517055B (en) | 1997-07-02 | 2003-01-11 | Smithkline Beecham Corp | Novel substituted imidazole compounds |
US7301021B2 (en) * | 1997-07-02 | 2007-11-27 | Smithkline Beecham Corporation | Substituted imidazole compounds |
US6562832B1 (en) | 1997-07-02 | 2003-05-13 | Smithkline Beecham Corporation | Substituted imidazole compounds |
EP0996443A1 (en) * | 1997-07-03 | 2000-05-03 | Neurogen Corporation | Certain diarylimidazole derivatives; a new class of npy specific ligands |
EP1041989A4 (en) | 1997-10-08 | 2002-11-20 | Smithkline Beecham Corp | NEW SUBSTITUTED CYCLOALCENYL COMPOUNDS |
WO1999032121A1 (en) | 1997-12-19 | 1999-07-01 | Smithkline Beecham Corporation | Compounds of heteroaryl substituted imidazole, their pharmaceutical compositions and uses |
KR20010025087A (ko) | 1998-05-22 | 2001-03-26 | 스튜어트 알. 수터 | 신규한 2-알킬 치환된 이미다졸 화합물 |
US6858617B2 (en) | 1998-05-26 | 2005-02-22 | Smithkline Beecham Corporation | Substituted imidazole compounds |
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Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3707475A (en) * | 1970-11-16 | 1972-12-26 | Pfizer | Antiinflammatory imidazoles |
US3929807A (en) * | 1971-05-10 | 1975-12-30 | Ciba Geigy Corp | 2-Substituted-4(5)-(aryl)-5(4)-(2,3 or -4-pyridyl)-imidazoles |
CH561718A5 (xx) * | 1971-05-10 | 1975-05-15 | Ciba Geigy Ag | |
US4440774A (en) * | 1975-03-03 | 1984-04-03 | Merck & Co., Inc. | 3-Amino-2-hydroxypropoxyaryl imidazole derivatives |
SE7601713L (sv) * | 1975-03-03 | 1976-09-06 | Merck & Co Inc | Nya, substituerad imidazoler |
-
1987
- 1987-08-06 IL IL83467A patent/IL83467A0/xx unknown
- 1987-08-07 EP EP87307051A patent/EP0257897A1/en not_active Withdrawn
- 1987-08-12 AU AU76825/87A patent/AU7682587A/en not_active Abandoned
- 1987-08-13 FI FI873509A patent/FI873509A/fi not_active Application Discontinuation
- 1987-08-13 PT PT85531A patent/PT85531B/pt unknown
- 1987-08-13 US US07/084,862 patent/US4822805A/en not_active Expired - Fee Related
- 1987-08-14 KR KR1019870008953A patent/KR880002840A/ko not_active Application Discontinuation
- 1987-08-14 OA OA59177A patent/OA08647A/xx unknown
- 1987-08-14 HU HU873676A patent/HUT44779A/hu unknown
- 1987-08-14 DK DK425887A patent/DK425887A/da not_active Application Discontinuation
- 1987-08-14 CN CN198787105680A patent/CN87105680A/zh active Pending
- 1987-08-14 NO NO873432A patent/NO873432L/no unknown
Also Published As
Publication number | Publication date |
---|---|
FI873509A0 (fi) | 1987-08-13 |
IL83467A0 (en) | 1988-01-31 |
DK425887A (da) | 1988-02-16 |
AU7682587A (en) | 1988-02-18 |
PT85531A (en) | 1987-09-01 |
CN87105680A (zh) | 1988-04-27 |
OA08647A (fr) | 1988-11-30 |
NO873432D0 (no) | 1987-08-14 |
FI873509A (fi) | 1988-02-16 |
EP0257897A1 (en) | 1988-03-02 |
HUT44779A (en) | 1988-04-28 |
DK425887D0 (da) | 1987-08-14 |
KR880002840A (ko) | 1988-05-11 |
US4822805A (en) | 1989-04-18 |
PT85531B (en) | 1989-12-15 |
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