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
- OBIKJPORAZOZJB-UHFFFAOYSA-N 4-[2-(2,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(OC)=CC=C1C1=NC(C=2C=CN=CC=2)=C(C)N1 OBIKJPORAZOZJB-UHFFFAOYSA-N 0.000 description 3
- RBELHPREHFTVGX-UHFFFAOYSA-N 4-methoxy-3-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound COC1=CC=C(N)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 RBELHPREHFTVGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 3
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000003177 cardiotonic effect Effects 0.000 description 3
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 3
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- NZOAHNAANWDDPB-UHFFFAOYSA-N n-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]-3-nitrobenzamide Chemical compound CC=1N=C(C=2C(=CC=CC=2)NC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)NC=1C1=CC=CN=C1 NZOAHNAANWDDPB-UHFFFAOYSA-N 0.000 description 3
- XXPXDRVVRCJRGJ-UHFFFAOYSA-N n-[2-chloro-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound C1=C(Cl)C(NC(=O)C)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 XXPXDRVVRCJRGJ-UHFFFAOYSA-N 0.000 description 3
- REGJJEXGLHOFSZ-UHFFFAOYSA-N n-[2-chloro-4-methoxy-5-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound COC1=CC(Cl)=C(NC(C)=O)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 REGJJEXGLHOFSZ-UHFFFAOYSA-N 0.000 description 3
- BCDUUXGSMMXJOS-UHFFFAOYSA-N n-[2-chloro-5-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]-n-methylacetamide Chemical compound COC1=CC(N(C)C(C)=O)=C(Cl)C=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 BCDUUXGSMMXJOS-UHFFFAOYSA-N 0.000 description 3
- OEYGBQCAQONCKE-UHFFFAOYSA-N n-[3-methyl-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]acetamide Chemical compound CC1=CC(NC(=O)C)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 OEYGBQCAQONCKE-UHFFFAOYSA-N 0.000 description 3
- QWCFSNRJFKZIMX-UHFFFAOYSA-N n-[[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]carbamothioyl]benzamide Chemical compound CC=1N=C(C=2C(=CC=CC=2)NC(=S)NC(=O)C=2C=CC=CC=2)NC=1C1=CC=CN=C1 QWCFSNRJFKZIMX-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 210000004623 platelet-rich plasma Anatomy 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229960003975 potassium Drugs 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
- FWRRCABREPUNFM-UHFFFAOYSA-N 2-(5-methyl-4-pyridin-3-yl-1H-imidazol-2-yl)phenol Chemical compound CC=1N=C(C=2C(=CC=CC=2)O)NC=1C1=CC=CN=C1 FWRRCABREPUNFM-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- QETJCNVNNHOGBC-UHFFFAOYSA-N 2-[2-(2,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(OC)=CC=C1C1=NC(C=2N=CC=CC=2)=C(C)N1 QETJCNVNNHOGBC-UHFFFAOYSA-N 0.000 description 2
- XFDZNFLRNJQTEO-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)F)NC=1C1=CC=CC=N1 XFDZNFLRNJQTEO-UHFFFAOYSA-N 0.000 description 2
- NLQNFCAPSHVTJB-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)-1h-imidazol-5-yl]pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2N=CC=CC=2)=CN1 NLQNFCAPSHVTJB-UHFFFAOYSA-N 0.000 description 2
- MYRWWNQLDFSMKO-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2N=CC=CC=2)=C(C)N1 MYRWWNQLDFSMKO-UHFFFAOYSA-N 0.000 description 2
- LXIVRHBNYLQUKG-UHFFFAOYSA-N 2-chloro-5-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound COC1=CC(N)=C(Cl)C=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 LXIVRHBNYLQUKG-UHFFFAOYSA-N 0.000 description 2
- PCWHWEDCPJXKRO-UHFFFAOYSA-N 2-chloro-6-methoxy-4-(5-methyl-4-pyridin-3-yl-1H-imidazol-2-yl)phenol Chemical compound ClC1=C(O)C(OC)=CC(C=2NC(=C(C)N=2)C=2C=NC=CC=2)=C1 PCWHWEDCPJXKRO-UHFFFAOYSA-N 0.000 description 2
- LTLYPBYRQNYLTQ-UHFFFAOYSA-N 2-hydroxyimino-1-pyridin-4-ylpropan-1-one Chemical compound ON=C(C)C(=O)C1=CC=NC=C1 LTLYPBYRQNYLTQ-UHFFFAOYSA-N 0.000 description 2
- LYPWMOKSOCUVJP-UHFFFAOYSA-N 2-methoxy-4-(5-methyl-4-pyridin-3-yl-1H-imidazol-2-yl)phenol Chemical compound C1=C(O)C(OC)=CC(C=2NC(=C(C)N=2)C=2C=NC=CC=2)=C1 LYPWMOKSOCUVJP-UHFFFAOYSA-N 0.000 description 2
- AVYGQLCDDWPZLI-UHFFFAOYSA-N 2-methoxy-5-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenol Chemical compound C1=C(O)C(OC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 AVYGQLCDDWPZLI-UHFFFAOYSA-N 0.000 description 2
- CAQAIFUDUGDPFB-UHFFFAOYSA-N 3-(5-methyl-2-phenyl-1h-imidazol-4-yl)pyridine Chemical compound CC=1NC(C=2C=CC=CC=2)=NC=1C1=CC=CN=C1 CAQAIFUDUGDPFB-UHFFFAOYSA-N 0.000 description 2
- DSBZFWXEMSSTGL-UHFFFAOYSA-N 3-[2-(2,3-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC=CC(C=2NC(C)=C(N=2)C=2C=NC=CC=2)=C1OC DSBZFWXEMSSTGL-UHFFFAOYSA-N 0.000 description 2
- LWMNXNCPBIKHBP-UHFFFAOYSA-N 3-[2-(2,4-dichlorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC(Cl)=CC=2)Cl)NC=1C1=CC=CN=C1 LWMNXNCPBIKHBP-UHFFFAOYSA-N 0.000 description 2
- CXWYCHJWCBYUTK-UHFFFAOYSA-N 3-[2-(2,4-dimethoxyphenyl)-1,5-dimethylimidazol-4-yl]pyridine Chemical compound COC1=CC(OC)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1C CXWYCHJWCBYUTK-UHFFFAOYSA-N 0.000 description 2
- FNJWRHJOKVPZDX-UHFFFAOYSA-N 3-[2-(2,5-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC=C(OC)C(C=2NC(C)=C(N=2)C=2C=NC=CC=2)=C1 FNJWRHJOKVPZDX-UHFFFAOYSA-N 0.000 description 2
- RYTZHKHZPATUKL-UHFFFAOYSA-N 3-[2-(2,6-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC=CC(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 RYTZHKHZPATUKL-UHFFFAOYSA-N 0.000 description 2
- LQELMIXJEYHTDS-UHFFFAOYSA-N 3-[2-(2-chlorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)Cl)NC=1C1=CC=CN=C1 LQELMIXJEYHTDS-UHFFFAOYSA-N 0.000 description 2
- HPHSGKOQYNSIPE-UHFFFAOYSA-N 3-[2-(2-ethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CCOC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 HPHSGKOQYNSIPE-UHFFFAOYSA-N 0.000 description 2
- FNFPYCJQFLGACU-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)-1h-imidazol-5-yl]pyridine Chemical compound FC1=CC=CC=C1C1=NC(C=2C=NC=CC=2)=CN1 FNFPYCJQFLGACU-UHFFFAOYSA-N 0.000 description 2
- WZFVKDGSTSRYEQ-UHFFFAOYSA-N 3-[2-(2-fluorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=CC=C1F WZFVKDGSTSRYEQ-UHFFFAOYSA-N 0.000 description 2
- AGHAXENSJIRURG-UHFFFAOYSA-N 3-[2-(2-methoxy-3-nitrophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=CC=C([N+]([O-])=O)C(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 AGHAXENSJIRURG-UHFFFAOYSA-N 0.000 description 2
- GEVDCRVQZDKCRM-UHFFFAOYSA-N 3-[2-(2-methoxy-4-methylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(C)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 GEVDCRVQZDKCRM-UHFFFAOYSA-N 0.000 description 2
- JIPRLNQJXKMECW-UHFFFAOYSA-N 3-[2-(2-methoxy-4-nitrophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC([N+]([O-])=O)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 JIPRLNQJXKMECW-UHFFFAOYSA-N 0.000 description 2
- BNEVRWZTFSQLSX-UHFFFAOYSA-N 3-[2-(2-methoxy-5-nitrophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC=C([N+]([O-])=O)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 BNEVRWZTFSQLSX-UHFFFAOYSA-N 0.000 description 2
- ZBQGELDZCNODKO-UHFFFAOYSA-N 3-[2-(3,4-dichlorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C=C(Cl)C(Cl)=CC=2)NC=1C1=CC=CN=C1 ZBQGELDZCNODKO-UHFFFAOYSA-N 0.000 description 2
- IHEDSBIXZDEPHH-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 IHEDSBIXZDEPHH-UHFFFAOYSA-N 0.000 description 2
- NNFJGXZRJFOMPB-UHFFFAOYSA-N 3-[2-(3-chloro-4,5-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound ClC1=C(OC)C(OC)=CC(C=2NC(=C(C)N=2)C=2C=NC=CC=2)=C1 NNFJGXZRJFOMPB-UHFFFAOYSA-N 0.000 description 2
- SQYBKRXYISPERX-UHFFFAOYSA-N 3-[2-(3-chlorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C=C(Cl)C=CC=2)NC=1C1=CC=CN=C1 SQYBKRXYISPERX-UHFFFAOYSA-N 0.000 description 2
- QSTOPZGOCGPDBE-UHFFFAOYSA-N 3-[2-(3-methoxy-4-methylsulfanylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=C(SC)C(OC)=CC(C=2NC(C)=C(N=2)C=2C=NC=CC=2)=C1 QSTOPZGOCGPDBE-UHFFFAOYSA-N 0.000 description 2
- KTYQAUGFMIWFRQ-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C=CC(Cl)=CC=2)NC=1C1=CC=CN=C1 KTYQAUGFMIWFRQ-UHFFFAOYSA-N 0.000 description 2
- CTCSGFCHBIILGY-UHFFFAOYSA-N 3-[2-(4-ethoxy-2-methoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(OCC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 CTCSGFCHBIILGY-UHFFFAOYSA-N 0.000 description 2
- YIYUAJDHHFSGAS-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C=CC(F)=CC=2)NC=1C1=CC=CN=C1 YIYUAJDHHFSGAS-UHFFFAOYSA-N 0.000 description 2
- KJFOMKPHIDUSCD-UHFFFAOYSA-N 3-[2-(4-methoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=CC(OC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 KJFOMKPHIDUSCD-UHFFFAOYSA-N 0.000 description 2
- WWYJRJJQHZIWRH-UHFFFAOYSA-N 3-[2-(5-chloro-2,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 WWYJRJJQHZIWRH-UHFFFAOYSA-N 0.000 description 2
- AUCKAIPUUVONJO-UHFFFAOYSA-N 3-[2-(5-chloro-2-methoxy-4-methylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(C)=C(Cl)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 AUCKAIPUUVONJO-UHFFFAOYSA-N 0.000 description 2
- BIDQETBBEHLGPW-UHFFFAOYSA-N 3-[2-(5-chloro-2-methoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC=C(Cl)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 BIDQETBBEHLGPW-UHFFFAOYSA-N 0.000 description 2
- NUINAOSGRPFXQP-UHFFFAOYSA-N 3-[2-[2-[(4-chlorophenyl)methoxy]phenyl]-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)OCC=2C=CC(Cl)=CC=2)NC=1C1=CC=CN=C1 NUINAOSGRPFXQP-UHFFFAOYSA-N 0.000 description 2
- SSLUTFRSTOVHMT-UHFFFAOYSA-N 3-[3-hydroxy-2-(2-methoxy-4-methylphenyl)-5-methylimidazol-4-yl]pyridine Chemical compound COC1=CC(C)=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 SSLUTFRSTOVHMT-UHFFFAOYSA-N 0.000 description 2
- BPGXJBOJXKTYSQ-UHFFFAOYSA-N 3-[3-hydroxy-2-(2-methoxyphenyl)-5-methylimidazol-4-yl]pyridine Chemical compound COC1=CC=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 BPGXJBOJXKTYSQ-UHFFFAOYSA-N 0.000 description 2
- QMSWGLZWBYQRPU-UHFFFAOYSA-N 3-[5-methyl-2-(2,3,4-trimethoxyphenyl)-1h-imidazol-4-yl]pyridine Chemical compound COC1=C(OC)C(OC)=CC=C1C1=NC(C=2C=NC=CC=2)=C(C)N1 QMSWGLZWBYQRPU-UHFFFAOYSA-N 0.000 description 2
- MKHCEKDHRLKCGL-UHFFFAOYSA-N 3-[5-methyl-2-(2,4,5-trimethoxyphenyl)-1h-imidazol-4-yl]pyridine Chemical compound C1=C(OC)C(OC)=CC(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 MKHCEKDHRLKCGL-UHFFFAOYSA-N 0.000 description 2
- PNGQTKGIWPZMEE-UHFFFAOYSA-N 3-[5-methyl-2-(2,4,6-trimethoxyphenyl)-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(OC)=CC(OC)=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 PNGQTKGIWPZMEE-UHFFFAOYSA-N 0.000 description 2
- DVAYOJHBOJCMGA-UHFFFAOYSA-N 3-[5-methyl-2-(2-methylphenyl)-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)C)NC=1C1=CC=CN=C1 DVAYOJHBOJCMGA-UHFFFAOYSA-N 0.000 description 2
- ODVGVEOFZRJJJF-UHFFFAOYSA-N 3-[5-methyl-2-(2-methylsulfanylphenyl)-1h-imidazol-4-yl]pyridine Chemical compound CSC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 ODVGVEOFZRJJJF-UHFFFAOYSA-N 0.000 description 2
- WSSCGBBWFFJXNP-UHFFFAOYSA-N 3-[5-methyl-2-(2-prop-2-ynoxyphenyl)-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)OCC#C)NC=1C1=CC=CN=C1 WSSCGBBWFFJXNP-UHFFFAOYSA-N 0.000 description 2
- PNWRBHITYHSJFR-UHFFFAOYSA-N 3-[5-methyl-2-(2-propan-2-yloxyphenyl)-1h-imidazol-4-yl]pyridine Chemical compound CC(C)OC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 PNWRBHITYHSJFR-UHFFFAOYSA-N 0.000 description 2
- CYVVFSQVRFICDQ-UHFFFAOYSA-N 3-[5-methyl-2-(3,4,5-trimethoxyphenyl)-1h-imidazol-4-yl]pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2NC(C)=C(N=2)C=2C=NC=CC=2)=C1 CYVVFSQVRFICDQ-UHFFFAOYSA-N 0.000 description 2
- VFQMJKPLSNAVEK-UHFFFAOYSA-N 3-[5-methyl-2-[2-(trifluoromethyl)phenyl]-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)C(F)(F)F)NC=1C1=CC=CN=C1 VFQMJKPLSNAVEK-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- OZECHNNZGSCTFE-UHFFFAOYSA-N 3-methoxy-n-methyl-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound COC1=CC(NC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 OZECHNNZGSCTFE-UHFFFAOYSA-N 0.000 description 2
- NHBMHBBNQGPJBP-UHFFFAOYSA-N 4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)benzoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(O)=O)NC=1C1=CC=CN=C1 NHBMHBBNQGPJBP-UHFFFAOYSA-N 0.000 description 2
- TZXDMKKPHMZCNR-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound CC=1N=C(C=2C(=CC=CC=2)F)NC=1C1=CC=NC=C1 TZXDMKKPHMZCNR-UHFFFAOYSA-N 0.000 description 2
- ZNVRBSBSRGTNGZ-UHFFFAOYSA-N 4-[2-(2-methoxy-4-methylsulfanylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound COC1=CC(SC)=CC=C1C1=NC(C=2C=CN=CC=2)=C(C)N1 ZNVRBSBSRGTNGZ-UHFFFAOYSA-N 0.000 description 2
- NCHIABRVBGAFGH-UHFFFAOYSA-N 4-[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=NC=C1 NCHIABRVBGAFGH-UHFFFAOYSA-N 0.000 description 2
- GYRLCQSPTKSMSS-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC(C=2C=CN=CC=2)=C(C)N1 GYRLCQSPTKSMSS-UHFFFAOYSA-N 0.000 description 2
- WEKKUMKUBMEWJQ-UHFFFAOYSA-N 4-[2-(3-methoxy-4-methylsulfanylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine Chemical compound C1=C(SC)C(OC)=CC(C=2NC(C)=C(N=2)C=2C=CN=CC=2)=C1 WEKKUMKUBMEWJQ-UHFFFAOYSA-N 0.000 description 2
- OHBBGKCNWLNTLW-UHFFFAOYSA-N 4-methyl-n-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]benzenesulfonamide Chemical compound CC=1NC(C=2C(=CC=CC=2)NS(=O)(=O)C=2C=CC(C)=CC=2)=NC=1C1=CC=CN=C1 OHBBGKCNWLNTLW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 239000012448 Lithium borohydride Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- MLNYYDZNXXXZQP-UHFFFAOYSA-N [2-(2,4-dimethoxyphenyl)-4-pyridin-3-yl-1h-imidazol-5-yl]methanol Chemical compound COC1=CC(OC)=CC=C1C1=NC(C=2C=NC=CC=2)=C(CO)N1 MLNYYDZNXXXZQP-UHFFFAOYSA-N 0.000 description 2
- SMFSHIYQZQUWLN-UHFFFAOYSA-N [2-(2-methoxy-4-methylsulfanylphenyl)-4-pyridin-3-yl-1h-imidazol-5-yl]methanol Chemical compound COC1=CC(SC)=CC=C1C1=NC(C=2C=NC=CC=2)=C(CO)N1 SMFSHIYQZQUWLN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000000702 anti-platelet effect Effects 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 210000001715 carotid artery Anatomy 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 210000003191 femoral vein Anatomy 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- NLEUAYIASBSZJJ-UHFFFAOYSA-N methyl 4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 NLEUAYIASBSZJJ-UHFFFAOYSA-N 0.000 description 2
- VGOPWUMCYKRMGF-UHFFFAOYSA-N methyl n-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 VGOPWUMCYKRMGF-UHFFFAOYSA-N 0.000 description 2
- NSBNSZAXNUGWDJ-UHFFFAOYSA-O monopyridin-1-ium tribromide Chemical compound Br[Br-]Br.C1=CC=[NH+]C=C1 NSBNSZAXNUGWDJ-UHFFFAOYSA-O 0.000 description 2
- RJLDSGIYCIBIKQ-UHFFFAOYSA-N n-[2-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)phenyl]methanesulfonamide Chemical compound CC=1N=C(C=2C(=CC=CC=2)NS(C)(=O)=O)NC=1C1=CC=CN=C1 RJLDSGIYCIBIKQ-UHFFFAOYSA-N 0.000 description 2
- ZHHSFKDSFDIMRD-UHFFFAOYSA-N n-[5-methoxy-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)-2-nitrophenyl]acetamide Chemical compound COC1=CC(NC(C)=O)=C([N+]([O-])=O)C=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 ZHHSFKDSFDIMRD-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- XBVVXCYNLAIXKD-WTKFZEAQSA-N (z)-7-[(1r,4s,5r,6r)-5-[(e,3s)-3-hydroxyoct-1-enyl]-2,3-diazabicyclo[2.2.1]hept-2-en-6-yl]hept-5-enoic acid Chemical compound C1[C@H]2N=N[C@@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O XBVVXCYNLAIXKD-WTKFZEAQSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- XBIZCSDMSGCENW-UHFFFAOYSA-N 1-hydroxyimino-1-pyridin-3-ylbutan-2-one Chemical compound CCC(=O)C(=NO)C1=CC=CN=C1 XBIZCSDMSGCENW-UHFFFAOYSA-N 0.000 description 1
- AFHFHXVRHACYSR-UHFFFAOYSA-N 1-pyridin-4-ylpropan-1-one Chemical compound CCC(=O)C1=CC=NC=C1 AFHFHXVRHACYSR-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- FGLYFCYPXBFIRT-UHFFFAOYSA-N 2-(1,5-dimethyl-4-pyridin-3-ylimidazol-2-yl)aniline;dihydrochloride Chemical compound Cl.Cl.CN1C(C)=C(C=2C=NC=CC=2)N=C1C1=CC=CC=C1N FGLYFCYPXBFIRT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- AFUZHUWLNKKNSD-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2N=CC=CC=2)=C(C)N=C1C1=CC=CC=C1F AFUZHUWLNKKNSD-UHFFFAOYSA-N 0.000 description 1
- LTVGUCSNBWOPBL-UHFFFAOYSA-N 2-chloro-4-(1-hydroxy-4-methyl-5-pyridin-3-ylimidazol-2-yl)-6-methoxyphenol Chemical compound ClC=1C=C(C=C(C1O)OC)C=1N(C(=C(N1)C)C=1C=NC=CC1)O LTVGUCSNBWOPBL-UHFFFAOYSA-N 0.000 description 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- LNPLSWLMVZWLCW-UHFFFAOYSA-N 2-hydroxyimino-1-pyridin-2-ylbutan-1-one Chemical compound CCC(=NO)C(=O)C1=CC=CC=N1 LNPLSWLMVZWLCW-UHFFFAOYSA-N 0.000 description 1
- NIDZUKYOFGCSAV-UHFFFAOYSA-N 2-hydroxyimino-1-pyridin-4-ylbutan-1-one Chemical compound CCC(=NO)C(=O)C1=CC=NC=C1 NIDZUKYOFGCSAV-UHFFFAOYSA-N 0.000 description 1
- KVTOUUODKAHJCM-UHFFFAOYSA-N 2-methoxy-4-methylbenzaldehyde Chemical compound COC1=CC(C)=CC=C1C=O KVTOUUODKAHJCM-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- PZZRSEUDGCFXIH-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1h-imidazol-1-ium;iodide Chemical compound I.CSC1=NCCN1 PZZRSEUDGCFXIH-UHFFFAOYSA-N 0.000 description 1
- MTIMDGQILFWMJI-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1h-imidazole Chemical compound CSC1=NCCN1 MTIMDGQILFWMJI-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- WEVNFNNWTLMROG-UHFFFAOYSA-N 3-[2-(2,4-dichlorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=C(Cl)C=C1Cl WEVNFNNWTLMROG-UHFFFAOYSA-N 0.000 description 1
- JABYEJZOVCLDCO-UHFFFAOYSA-N 3-[2-(2,4-dimethoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine;dihydrochloride Chemical compound Cl.Cl.COC1=CC(OC)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 JABYEJZOVCLDCO-UHFFFAOYSA-N 0.000 description 1
- MPQVPLGHYVUNSK-UHFFFAOYSA-N 3-[2-(2,6-dimethoxyphenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound COC1=CC=CC(OC)=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 MPQVPLGHYVUNSK-UHFFFAOYSA-N 0.000 description 1
- IZAVAFMIUCXAPD-UHFFFAOYSA-N 3-[2-(2-chlorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=CC=C1Cl IZAVAFMIUCXAPD-UHFFFAOYSA-N 0.000 description 1
- WTCGUGJOCRDDQJ-UHFFFAOYSA-N 3-[2-(2-ethoxyphenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound CCOC1=CC=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 WTCGUGJOCRDDQJ-UHFFFAOYSA-N 0.000 description 1
- DCHATEOGMGYDMY-UHFFFAOYSA-N 3-[2-(2-methoxy-4-methylsulfinylphenyl)-5-methyl-1h-imidazol-4-yl]pyridine;dihydrochloride Chemical compound Cl.Cl.COC1=CC(S(C)=O)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 DCHATEOGMGYDMY-UHFFFAOYSA-N 0.000 description 1
- DGBBNSARGLDYCW-UHFFFAOYSA-N 3-[2-(2-methoxyphenyl)-5-methyl-1h-imidazol-4-yl]pyridine;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 DGBBNSARGLDYCW-UHFFFAOYSA-N 0.000 description 1
- FWIDRIAEFMEADJ-UHFFFAOYSA-N 3-[2-(3,4-dichlorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=C(Cl)C(Cl)=C1 FWIDRIAEFMEADJ-UHFFFAOYSA-N 0.000 description 1
- PVXBRYRQPALZEB-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 PVXBRYRQPALZEB-UHFFFAOYSA-N 0.000 description 1
- KSVVRMKNDULKDI-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)-5-ethyl-1h-imidazol-4-yl]pyridine Chemical compound CCC=1N=C(C=2C=C(OC)C(OC)=CC=2)NC=1C1=CC=CN=C1 KSVVRMKNDULKDI-UHFFFAOYSA-N 0.000 description 1
- PGABBSIPAIUNAQ-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)-5-ethyl-1h-imidazol-4-yl]pyridine;hydrochloride Chemical compound Cl.CCC=1N=C(C=2C=C(OC)C(OC)=CC=2)NC=1C1=CC=CN=C1 PGABBSIPAIUNAQ-UHFFFAOYSA-N 0.000 description 1
- DJLMSQNEJXFSMI-UHFFFAOYSA-N 3-[2-(3-chloro-4,5-dimethoxyphenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ClC1=C(OC)C(OC)=CC(C=2N(C(C=3C=NC=CC=3)=C(C)N=2)O)=C1 DJLMSQNEJXFSMI-UHFFFAOYSA-N 0.000 description 1
- AGWQWAIVBIDLCF-UHFFFAOYSA-N 3-[2-(3-chlorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=CC(Cl)=C1 AGWQWAIVBIDLCF-UHFFFAOYSA-N 0.000 description 1
- RXPFIVJVVYEFIF-UHFFFAOYSA-N 3-[2-(4-chloro-2-methoxy-5-nitrophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound COC1=CC(Cl)=C([N+]([O-])=O)C=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 RXPFIVJVVYEFIF-UHFFFAOYSA-N 0.000 description 1
- CUKLCQVYUMTLAH-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=C(Cl)C=C1 CUKLCQVYUMTLAH-UHFFFAOYSA-N 0.000 description 1
- PVWCUKLEOZWZKD-UHFFFAOYSA-N 3-[2-(4-ethoxy-2-methoxyphenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound COC1=CC(OCC)=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 PVWCUKLEOZWZKD-UHFFFAOYSA-N 0.000 description 1
- ZICWNFPYVVPIHD-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=C(F)C=C1 ZICWNFPYVVPIHD-UHFFFAOYSA-N 0.000 description 1
- GCRVTKLRBIROCD-UHFFFAOYSA-N 3-[2-(5-chloro-2,4-dimethoxyphenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound C1=C(Cl)C(OC)=CC(OC)=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 GCRVTKLRBIROCD-UHFFFAOYSA-N 0.000 description 1
- KUIXVWIFJPWROD-UHFFFAOYSA-N 3-[2-(5-chloro-2-methoxy-4-methylphenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound COC1=CC(C)=C(Cl)C=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 KUIXVWIFJPWROD-UHFFFAOYSA-N 0.000 description 1
- ZEALDHSYHDBPJV-UHFFFAOYSA-N 3-[2-(5-chloro-2-methoxyphenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound COC1=CC=C(Cl)C=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 ZEALDHSYHDBPJV-UHFFFAOYSA-N 0.000 description 1
- FQRCRLBWJDLYKW-UHFFFAOYSA-N 3-[2-[2-[(4-chlorophenyl)methoxy]phenyl]-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=CC=C1OCC1=CC=C(Cl)C=C1 FQRCRLBWJDLYKW-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- JEEJQDPPHDODCJ-UHFFFAOYSA-N 3-[3-hydroxy-2-(2-methoxy-4-phenylmethoxyphenyl)-5-methylimidazol-4-yl]pyridine Chemical compound C=1C=C(C=2N(C(C=3C=NC=CC=3)=C(C)N=2)O)C(OC)=CC=1OCC1=CC=CC=C1 JEEJQDPPHDODCJ-UHFFFAOYSA-N 0.000 description 1
- LYTZREHVLSTHFC-UHFFFAOYSA-N 3-[3-hydroxy-2-(3-methoxy-4-methylsulfanylphenyl)-5-methylimidazol-4-yl]pyridine Chemical compound C1=C(SC)C(OC)=CC(C=2N(C(C=3C=NC=CC=3)=C(C)N=2)O)=C1 LYTZREHVLSTHFC-UHFFFAOYSA-N 0.000 description 1
- DIUYNHXKVOMRJP-UHFFFAOYSA-N 3-[3-hydroxy-2-(4-methoxyphenyl)-5-methylimidazol-4-yl]pyridine Chemical compound C1=CC(OC)=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 DIUYNHXKVOMRJP-UHFFFAOYSA-N 0.000 description 1
- BCADLVFMQNJSTO-UHFFFAOYSA-N 3-[3-hydroxy-5-methyl-2-(2-nitrophenyl)imidazol-4-yl]pyridine Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=CC=C1[N+]([O-])=O BCADLVFMQNJSTO-UHFFFAOYSA-N 0.000 description 1
- LLKVUJJEBFXEAK-UHFFFAOYSA-N 3-methoxy-n,n-dimethyl-4-(5-methyl-4-pyridin-3-yl-1h-imidazol-2-yl)aniline Chemical compound COC1=CC(N(C)C)=CC=C1C1=NC(C)=C(C=2C=NC=CC=2)N1 LLKVUJJEBFXEAK-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- KIWUSDHHHBOIFI-UHFFFAOYSA-N 4-(1-hydroxy-4-methyl-5-pyridin-3-ylimidazol-2-yl)-3-methoxy-n,n-dimethylaniline Chemical compound COC1=CC(N(C)C)=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 KIWUSDHHHBOIFI-UHFFFAOYSA-N 0.000 description 1
- BBXVLMOJKITQNH-UHFFFAOYSA-N 4-(1-hydroxy-4-methyl-5-pyridin-3-ylimidazol-2-yl)benzoic acid Chemical compound ON1C(C=2C=NC=CC=2)=C(C)N=C1C1=CC=C(C(O)=O)C=C1 BBXVLMOJKITQNH-UHFFFAOYSA-N 0.000 description 1
- GCMPZKWRKBYDGA-UHFFFAOYSA-N 4-[1-hydroxy-2-(3-methoxy-4-methylsulfanylphenyl)-5-methylimidazol-4-yl]pyridine Chemical compound C1=C(SC)C(OC)=CC(C=2N(C(C)=C(N=2)C=2C=CN=CC=2)O)=C1 GCMPZKWRKBYDGA-UHFFFAOYSA-N 0.000 description 1
- CIXURZHMNWMZRX-UHFFFAOYSA-N 4-[2-(2-fluorophenyl)-3-hydroxy-5-methylimidazol-4-yl]pyridine Chemical compound ON1C(C=2C=CN=CC=2)=C(C)N=C1C1=CC=CC=C1F CIXURZHMNWMZRX-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- CISOUQDVWUZJER-UHFFFAOYSA-N 5-(1-hydroxy-4-methyl-5-pyridin-3-ylimidazol-2-yl)-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C(N1O)=NC(C)=C1C1=CC=CN=C1 CISOUQDVWUZJER-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- SGDKTJPVCKQTHK-UHFFFAOYSA-N 5-bromo-2-fluoro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC(Br)=CN=C1F SGDKTJPVCKQTHK-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical group CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical class OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005281 alkyl ureido group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 230000006502 antiplatelets effects Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005239 aroylamino group Chemical group 0.000 description 1
- 150000001509 aspartic acid derivatives Chemical class 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- XJMWHXZUIGHOBA-UHFFFAOYSA-N azane;propanoic acid Chemical compound N.CCC(O)=O XJMWHXZUIGHOBA-UHFFFAOYSA-N 0.000 description 1
- YNTQKXBRXYIAHM-UHFFFAOYSA-N azanium;butanoate Chemical compound [NH4+].CCCC([O-])=O YNTQKXBRXYIAHM-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- FLLNLJJKHKZKMB-UHFFFAOYSA-N boron;tetramethylazanium Chemical compound [B].C[N+](C)(C)C FLLNLJJKHKZKMB-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 229940062993 ferrous oxalate Drugs 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 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
- 125000006635 hexyloxycarbonylamino group Chemical group 0.000 description 1
- 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
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 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
- 239000004033 plastic Substances 0.000 description 1
- 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)
- Epoxy Resins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (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 (da) |
EP (1) | EP0257897A1 (da) |
KR (1) | KR880002840A (da) |
CN (1) | CN87105680A (da) |
AU (1) | AU7682587A (da) |
DK (1) | DK425887A (da) |
FI (1) | FI873509A (da) |
HU (1) | HUT44779A (da) |
IL (1) | IL83467A0 (da) |
NO (1) | NO873432L (da) |
OA (1) | OA08647A (da) |
PT (1) | PT85531B (da) |
Families Citing this family (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5916891A (en) * | 1992-01-13 | 1999-06-29 | Smithkline Beecham Corporation | Pyrimidinyl imidazoles |
IL104369A0 (en) * | 1992-01-13 | 1993-05-13 | Smithkline Beecham Corp | Novel 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 |
US5670527A (en) * | 1993-07-16 | 1997-09-23 | Smithkline Beecham Corporation | Pyridyl imidazole compounds and compositions |
US5620999A (en) * | 1994-07-28 | 1997-04-15 | Weier; Richard M. | Benzenesulfonamide subtituted imidazolyl compounds 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 |
US5616601A (en) * | 1994-07-28 | 1997-04-01 | Gd Searle & Co | 1,2-aryl and heteroaryl substituted 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 |
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 |
US6515014B2 (en) | 1995-06-02 | 2003-02-04 | G. D. Searle & Co. | Thiophene substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
WO1996038418A1 (en) | 1995-06-02 | 1996-12-05 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
US6512121B2 (en) | 1998-09-14 | 2003-01-28 | G.D. Searle & Co. | Heterocyclo substituted hydroxamic acid derivatives as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
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 |
US6369068B1 (en) | 1995-06-07 | 2002-04-09 | Smithkline Beecham Corporation | Amino substituted pyrimidine containing compounds |
ZA9610687B (en) | 1995-12-22 | 1997-09-29 | Smithkline Beecham Corp | Novel synthesis. |
US6046208A (en) * | 1996-01-11 | 2000-04-04 | Smithkline Beecham Corporation | Substituted imidazole compounds |
US5756499A (en) * | 1996-01-11 | 1998-05-26 | Smithkline Beecham Corporation | Substituted imidazole compounds |
AP9700912A0 (en) | 1996-01-11 | 1997-01-31 | Smithkline Beecham Corp | Novel cycloalkyl substituted imidazoles |
ZA97175B (en) * | 1996-01-11 | 1997-11-04 | Smithkline Beecham Corp | Novel substituted imidazole compounds. |
JP2000507558A (ja) * | 1996-03-25 | 2000-06-20 | スミスクライン・ビーチャム・コーポレイション | Cns損傷についての新規な治療 |
US6677364B2 (en) | 1998-04-20 | 2004-01-13 | G.D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
WO1998007425A1 (en) | 1996-08-21 | 1998-02-26 | Smithkline Beecham Corporation | Imidazole compounds, compositions and use |
US5929076A (en) * | 1997-01-10 | 1999-07-27 | Smithkline Beecham Corporation | Cycloalkyl substituted imidazoles |
CA2294057A1 (en) | 1997-06-13 | 1998-12-17 | Smithkline Beecham Corporation | Novel pyrazole and pyrazoline substituted compounds |
EP0994870A4 (en) | 1997-06-19 | 2002-10-23 | Smithkline Beecham | NEW IMIDAZOLE COMPOUNDS SUBSTITUTED BY AN ARYLOXYREST |
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 |
US6562832B1 (en) | 1997-07-02 | 2003-05-13 | Smithkline Beecham Corporation | Substituted imidazole compounds |
CA2295762A1 (en) | 1997-07-02 | 1999-01-14 | Ravi Shanker Garigipati | Novel cycloalkyl substituted imidazoles |
US6489325B1 (en) | 1998-07-01 | 2002-12-03 | Smithkline Beecham Corporation | Substituted imidazole compounds |
US7301021B2 (en) * | 1997-07-02 | 2007-11-27 | Smithkline Beecham Corporation | Substituted imidazole compounds |
TW517055B (en) | 1997-07-02 | 2003-01-11 | Smithkline Beecham Corp | Novel substituted imidazole compounds |
WO1999001128A1 (en) * | 1997-07-03 | 1999-01-14 | Neurogen Corporation | Certain diarylimidazole derivatives; a new class of npy specific ligands |
WO1999017776A1 (en) | 1997-10-08 | 1999-04-15 | Smithkline Beecham Corporation | Novel cycloalkenyl substituted compounds |
AR017219A1 (es) | 1997-12-19 | 2001-08-22 | Smithkline Beecham Corp | Derivados de imidazol 1,4,5 sustituidos, composiciones que los comprenden, procedimiento para la preparacion de dichos derivados, uso de los derivados parala manufactura de un medicamento |
AU760527C (en) | 1998-05-22 | 2004-05-06 | Smithkline Beecham Corporation | Novel 2-alkyl substituted imidazole compounds |
US6858617B2 (en) | 1998-05-26 | 2005-02-22 | Smithkline Beecham Corporation | Substituted imidazole compounds |
CA2341370A1 (en) * | 1998-08-20 | 2000-03-02 | Smithkline Beecham Corporation | Novel substituted triazole compounds |
ATE258055T1 (de) | 1998-11-04 | 2004-02-15 | Smithkline Beecham Corp | Pyridin-4-yl oder pyrimidin-4-yl substituierte pyrazine |
US6239279B1 (en) | 1998-12-16 | 2001-05-29 | Smithkline Beecham Corporation | Synthesis for 4-aryl-5-pyrimidine imidazole substituted derivatives |
US7053098B1 (en) | 1999-11-23 | 2006-05-30 | Smithkline Beecham Corporation | 3,4-Dihydro-(1H) quinazolin-2-one compounds as CSBP/P38 kinase inhibitors |
EP1235814B1 (en) | 1999-11-23 | 2004-11-03 | Smithkline Beecham Corporation | 3,4-DIHYDRO-(1H)QUINAZOLIN-2-ONE COMPOUNDS AS CSBP/p38 KINASE INHIBITORS |
US6759410B1 (en) * | 1999-11-23 | 2004-07-06 | Smithline Beecham Corporation | 3,4-dihydro-(1H)-quinazolin-2-ones and their use as CSBP/p38 kinase inhibitors |
WO2001038313A1 (en) | 1999-11-23 | 2001-05-31 | Smithkline Beecham Corporation | 3,4-DIHYDRO-(1H)QUINAZOLIN-2-ONE COMPOUNDS AS CSBP/p39 kINASE INHIBITORS |
MXPA02006016A (es) | 1999-12-16 | 2002-12-05 | Schering Corp | Imidazoles sustituidos, antagonistas de los receptores y5 del neuropeptido y. |
US7235551B2 (en) * | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
EP2404603A1 (en) * | 2000-10-23 | 2012-01-11 | Glaxosmithkline LLC | Novel trisubstituted-8H-pyrido[2,3-d]pyrimidin-7-one compounds for the treatment of CSBP/p38 kinase mediated diseases |
US20030105144A1 (en) | 2001-04-17 | 2003-06-05 | Ping Gao | Stabilized oral pharmaceutical composition |
US6673818B2 (en) | 2001-04-20 | 2004-01-06 | Pharmacia Corporation | Fluoro-substituted benzenesulfonyl compounds for the treatment of inflammation |
US7329401B2 (en) * | 2002-04-15 | 2008-02-12 | The Regents Of The University Of California | Cyclooxygenase-2 selective agents useful as imaging probes and related methods |
EP1532118A2 (en) * | 2002-07-05 | 2005-05-25 | Axxima Pharmaceuticals Aktiengesellschaft | Imidazole compounds for the treatment of hepatitis c virus infections |
ES2325687T3 (es) | 2002-09-18 | 2009-09-14 | Pfizer Products Inc. | Compuestos de imidazol novedosos como inhibidores del factor de crecimiento transformante (tgf). |
PA8595001A1 (es) | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
US20070043084A1 (en) * | 2003-05-08 | 2007-02-22 | Astellas Pharma Inc. | 1,2-Diarylimidazoles useful as inhibitors of cox |
PE20100737A1 (es) * | 2005-03-25 | 2010-11-27 | Glaxo Group Ltd | Nuevos compuestos |
US7479558B2 (en) * | 2005-03-25 | 2009-01-20 | Glaxo Group Limited | Process for preparing pyrido[2,3-d]pyrimidin-7-one and 3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one derivatives |
US7728027B2 (en) * | 2007-08-08 | 2010-06-01 | Bristol-Myers Squibb Company | Process for synthesizing compounds useful for treating hepatitis C |
PE20110843A1 (es) | 2008-09-22 | 2011-12-08 | Cayman Chem Co | Derivados de 5-(1h-imidazol-5-il)-2-fenilpirimidina, como inhibidores de prostaglandina d sintasa hematopoyetica |
CN106164065B (zh) * | 2014-03-28 | 2019-05-10 | 先正达参股股份有限公司 | 具有含硫取代基的杀有害生物活性杂环衍生物 |
KR102447094B1 (ko) * | 2014-08-13 | 2022-09-23 | 닛뽕소다 가부시키가이샤 | 디아릴이미다졸 화합물 및 유해 생물 방제제 |
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 (da) * | 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 US US07/084,862 patent/US4822805A/en not_active Expired - Fee Related
- 1987-08-13 PT PT85531A patent/PT85531B/pt unknown
- 1987-08-13 FI FI873509A patent/FI873509A/fi not_active Application Discontinuation
- 1987-08-14 KR KR1019870008953A patent/KR880002840A/ko not_active Application Discontinuation
- 1987-08-14 HU HU873676A patent/HUT44779A/hu unknown
- 1987-08-14 OA OA59177A patent/OA08647A/xx unknown
- 1987-08-14 NO NO873432A patent/NO873432L/no unknown
- 1987-08-14 DK DK425887A patent/DK425887A/da not_active Application Discontinuation
- 1987-08-14 CN CN198787105680A patent/CN87105680A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
OA08647A (fr) | 1988-11-30 |
PT85531B (en) | 1989-12-15 |
EP0257897A1 (en) | 1988-03-02 |
AU7682587A (en) | 1988-02-18 |
DK425887D0 (da) | 1987-08-14 |
FI873509A (fi) | 1988-02-16 |
DK425887A (da) | 1988-02-16 |
FI873509A0 (fi) | 1987-08-13 |
NO873432D0 (no) | 1987-08-14 |
US4822805A (en) | 1989-04-18 |
CN87105680A (zh) | 1988-04-27 |
KR880002840A (ko) | 1988-05-11 |
PT85531A (en) | 1987-09-01 |
HUT44779A (en) | 1988-04-28 |
IL83467A0 (en) | 1988-01-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO873432L (no) | Fremgangsmaate for fremstilling av imidazolforbindelser. | |
US7572914B2 (en) | Kinase inhibitors | |
KR100953251B1 (ko) | 치환된 디히드로 3-할로-1h-피라졸-5-카르복실레이트, 그의 제조 방법 및 용도 | |
ES2404034T3 (es) | Derivados de alquinilo como moduladores de receptores metabotrópicos de glutamato | |
US4382938A (en) | Imidazo[1,2-a] pyridine derivatives and their application as pharmaceuticals | |
US5219859A (en) | Indole derivatives, preparation processes and medicinal products containing them | |
US20070015809A1 (en) | Histone deacetylase inhibitors | |
EP1948614A2 (en) | Glucokinase activators | |
JP2008540574A (ja) | ヒストンデアセチラーゼ阻害剤 | |
JPH0625134B2 (ja) | 新規な複素環化合物 | |
JP2004506736A (ja) | タンパク質キナーゼ阻害剤としての縮合ピラゾール誘導体 | |
JP2008524246A (ja) | ヒストンデアセチラーゼ阻害剤 | |
NO840712L (no) | Fremgangsmaate for fremstilling av farmasoeytisk aktive imidazo-forbindelser | |
WO1992006088A1 (en) | Indole derivatives as antiallergy and antiinflammatory agents | |
JPS62471A (ja) | 新規2−アリ−ルイミダゾ−ル化合物 | |
KR20200028424A (ko) | Rock 억제제로서의 페닐아세트아미드 | |
EP0266558A2 (de) | 5-Alkylbenzimidazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
NO884231L (no) | Fremgangsmaate for fremstilling av terapeutisk aktive imidazopyridin-derivater. | |
US4782055A (en) | Imidazopyridine compounds useful in the treatment of ulcers | |
FI93444C (fi) | Menetelmä terapeuttisesti aktiivisten dihydropyridiinijohdannaisten valmistamiseksi | |
JPS61100582A (ja) | 4―アルコキシ‐ピリド[2,3‐d]ピリミジン誘導体、その調製方法、およびそれらを含む薬学的組成物 | |
JPS6354369A (ja) | イミダゾ−ル誘導体 | |
NO874780L (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolo-benzimidazol-derivater. | |
TW201315731A (zh) | 菸鹼乙醯膽鹼受體之新穎正向異位調節劑 | |
JPS62135473A (ja) | イミダゾ−ル縮合複素環化合物 |