NL7908331A - Imidazoolderivaten met anti-depressieve werking. - Google Patents
Imidazoolderivaten met anti-depressieve werking. Download PDFInfo
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- NL7908331A NL7908331A NL7908331A NL7908331A NL7908331A NL 7908331 A NL7908331 A NL 7908331A NL 7908331 A NL7908331 A NL 7908331A NL 7908331 A NL7908331 A NL 7908331A NL 7908331 A NL7908331 A NL 7908331A
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- formula
- group
- compound
- compounds
- alkyl
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- 230000001430 anti-depressive effect Effects 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- -1 carbonyl sulfonyl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000011800 void material Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 5
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000000891 anti-reserpine Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 5
- 229960003147 reserpine Drugs 0.000 description 5
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 230000002269 spontaneous effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 208000020401 Depressive disease Diseases 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- SIOJLMNJHNNNKW-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-ethylimidazole Chemical compound CCC1=NC=CN1C1=CC=C(Cl)C(Cl)=C1 SIOJLMNJHNNNKW-UHFFFAOYSA-N 0.000 description 3
- XUUHHUAOQCPPLW-UHFFFAOYSA-N 2-methyl-5-(2-methylimidazol-1-yl)aniline Chemical compound CC1=NC=CN1C1=CC=C(C)C(N)=C1 XUUHHUAOQCPPLW-UHFFFAOYSA-N 0.000 description 3
- HCOWOSINIWWAAE-UHFFFAOYSA-N 4-(2-ethylimidazol-1-yl)aniline Chemical compound CCC1=NC=CN1C1=CC=C(N)C=C1 HCOWOSINIWWAAE-UHFFFAOYSA-N 0.000 description 3
- IEZCMVRWKNEHJB-UHFFFAOYSA-N 4-(2-methylimidazol-1-yl)aniline Chemical compound CC1=NC=CN1C1=CC=C(N)C=C1 IEZCMVRWKNEHJB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000234282 Allium Species 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 3
- 230000001665 lethal effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000004899 motility Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- UWSAMZTWGCUCOJ-UHFFFAOYSA-N [1-(4-methyl-3-nitrophenyl)imidazol-2-yl]methanol Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1N1C(CO)=NC=C1 UWSAMZTWGCUCOJ-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
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- 229960003638 dopamine Drugs 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 description 1
- HJQHINQZCOXIGG-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-2-methylimidazole Chemical compound CC1=NC=CN1C1=CC=C(C)C(C)=C1 HJQHINQZCOXIGG-UHFFFAOYSA-N 0.000 description 1
- GUAYQMPSWPFZSA-UHFFFAOYSA-N 1-(4-methyl-3-nitrophenyl)imidazole Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1N1C=NC=C1 GUAYQMPSWPFZSA-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- LLSZMUSXQITSSJ-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)aniline Chemical compound CC1=NC=CN1C1=CC=CC=C1N LLSZMUSXQITSSJ-UHFFFAOYSA-N 0.000 description 1
- FDDPCTLWHSZGDU-UHFFFAOYSA-N 2-(chloromethyl)-1-(4-methyl-3-nitrophenyl)imidazole Chemical compound C1=C([N+]([O-])=O)C(C)=CC=C1N1C(CCl)=NC=C1 FDDPCTLWHSZGDU-UHFFFAOYSA-N 0.000 description 1
- OFMZDYDHETWLMA-UHFFFAOYSA-N 2-ethyl-1,3-oxazole-4-carboxylic acid Chemical compound CCC1=NC(C(O)=O)=CO1 OFMZDYDHETWLMA-UHFFFAOYSA-N 0.000 description 1
- IARMCEYEYXXEOS-UHFFFAOYSA-N 2-methyl-1,3-oxazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=CO1 IARMCEYEYXXEOS-UHFFFAOYSA-N 0.000 description 1
- GSDHPOQTEXEBDN-UHFFFAOYSA-N 2-methyl-1-(4-nitrophenyl)imidazole Chemical compound CC1=NC=CN1C1=CC=C([N+]([O-])=O)C=C1 GSDHPOQTEXEBDN-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- ZDHNDCMKVXWWLA-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)aniline Chemical compound CC1=NC=CN1C1=CC=CC(N)=C1 ZDHNDCMKVXWWLA-UHFFFAOYSA-N 0.000 description 1
- RYARAKWEDQQRGL-UHFFFAOYSA-N 4-(2,4-dimethylimidazol-1-yl)aniline Chemical compound CC1=NC(C)=CN1C1=CC=C(N)C=C1 RYARAKWEDQQRGL-UHFFFAOYSA-N 0.000 description 1
- FKHUITJYEBXJCO-UHFFFAOYSA-N 4-(2-methylimidazol-1-yl)-2-(trifluoromethyl)aniline Chemical compound CC1=NC=CN1C1=CC=C(N)C(C(F)(F)F)=C1 FKHUITJYEBXJCO-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
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- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
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- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
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- 239000007884 disintegrant Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229940079593 drug Drugs 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
- 239000000706 filtrate Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- RKQGJELNTGGIKM-UHFFFAOYSA-N n,n-dimethyl-4-(2-methylimidazol-1-yl)aniline Chemical compound C1=CC(N(C)C)=CC=C1N1C(C)=NC=C1 RKQGJELNTGGIKM-UHFFFAOYSA-N 0.000 description 1
- LHTWHACIHJYDLR-UHFFFAOYSA-N n-butyl-4-(2-methylimidazol-1-yl)aniline Chemical compound C1=CC(NCCCC)=CC=C1N1C(C)=NC=C1 LHTWHACIHJYDLR-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13932578 | 1978-11-14 | ||
| JP13932578A JPS5566562A (en) | 1978-11-14 | 1978-11-14 | Novel imidazole derivative and antidepressant containing the same |
| JP14281378A JPS5569567A (en) | 1978-11-21 | 1978-11-21 | Novel imidazole compound, and antidepressant containing the same |
| JP14281378 | 1978-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7908331A true NL7908331A (nl) | 1980-05-19 |
Family
ID=26472162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7908331A NL7908331A (nl) | 1978-11-14 | 1979-11-14 | Imidazoolderivaten met anti-depressieve werking. |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US4301169A (it) |
| CA (1) | CA1126272A (it) |
| CH (1) | CH642635A5 (it) |
| DE (1) | DE2946020A1 (it) |
| FR (1) | FR2441616B1 (it) |
| GB (1) | GB2044754B (it) |
| IT (1) | IT1127223B (it) |
| NL (1) | NL7908331A (it) |
| SE (1) | SE447653B (it) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE447653B (sv) * | 1978-11-14 | 1986-12-01 | Eisai Co Ltd | Imidazolderivat samt farmaceutisk komposition innehallande sadant derivat |
| US4353905A (en) * | 1981-09-17 | 1982-10-12 | Warner-Lambert Company | Substituted 4,5-dihydro-6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones and 6-[4-(1H-imidazol-1-yl)phenyl]-3(2H)-pyridazinones |
| US5138069A (en) * | 1986-07-11 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| CA1334092C (en) * | 1986-07-11 | 1995-01-24 | David John Carini | Angiotensin ii receptor blocking imidazoles |
| US4851526A (en) * | 1987-09-04 | 1989-07-25 | Schering A.G. | 1-(4-Substituted phenyl)-1H-imidazoles compounds |
| US5210079A (en) * | 1988-01-07 | 1993-05-11 | E. I. Du Pont De Nemours And Company | Treatment of chronic renal failure with imidazole angiotensin-II receptor antagonists |
| DE122007000050I1 (de) * | 1990-02-19 | 2007-11-08 | Novartis Ag | Acylverbindungen |
| KR910021381A (ko) * | 1990-02-20 | 1991-12-20 | 모리 히데오 | 4-3급 부틸이미다졸 유도체, 및 이의 제조방법 및 용도 |
| US5179113A (en) * | 1990-03-20 | 1993-01-12 | E. I. Du Pont De Nemours And Company | Treatment of central nervous disorders with imidazole compounds |
| US5137906A (en) * | 1990-03-20 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Treatment of central nervous system disorders with benzimidazole angiotensin-II receptor antagonists |
| US5140037A (en) * | 1990-03-20 | 1992-08-18 | E. I. Du Pont De Nemours And Company | Treatment of central nervous system disorders with imidazole angiotensin-ii receptor antagonists |
| US5173494A (en) * | 1990-03-20 | 1992-12-22 | E. I. Du Pont De Nemours And Company | Specific inhibition of angiotensin-II binding to angiotensin-II receptor subtype-2 |
| US5155126A (en) * | 1990-03-20 | 1992-10-13 | E. I. Du Pont De Nemours And Company | Treatment of central nervous system disorders with pyrazole, pyrrole and triazole angiotensin-II receptor antagonists |
| CA2036148A1 (en) * | 1990-06-29 | 1991-12-30 | Hiroki Tomioka | A 1-phenylimidazole derivative and its production and use |
| US6008368A (en) * | 1993-04-28 | 1999-12-28 | G. D. Searle & Co. | Pharmaceutical compositions for treatment of circulatory disorders using N-substituted (α-imidazolyl-toluyl) pyrrole aniotensin II antagonists |
| US5187271A (en) * | 1991-02-28 | 1993-02-16 | G. D. Searle & Co. | N-substituted (α-imidazolyl-toluyl) pyrrole compounds for treatment of circulatory disorders |
| US5451597A (en) * | 1993-05-27 | 1995-09-19 | G.D. Searle & Co. | Treatment of circulatory disorders using n-substituted (α-imidazolyl-toluyl) pyrrole angiotensin II antagonists |
| CA2189068A1 (en) * | 1994-04-27 | 1995-11-02 | Nobuo Mochizuki | Imidazole derivative and process for producing the same |
| WO2000006550A1 (en) | 1998-07-31 | 2000-02-10 | Nippon Soda Co., Ltd. | Phenylazole compounds, process for producing the same and drugs for hyperlipemia |
| AUPQ319899A0 (en) | 1999-10-01 | 1999-10-28 | Fujisawa Pharmaceutical Co., Ltd. | Amide compounds |
| US6627647B1 (en) | 2000-03-23 | 2003-09-30 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)imidazoles and their use as anti-inflammatory agents |
| WO2005012293A1 (ja) * | 2003-08-01 | 2005-02-10 | Nippon Soda Co., Ltd. | フェニルアゾール化合物、製造法および抗酸化薬 |
| EP1858879B1 (en) * | 2005-01-14 | 2012-06-06 | Gilead Connecticut, Inc. | 1,3-diaryl substituted ureas as modulators of kinase activity |
| EP1858877B1 (en) * | 2005-01-14 | 2014-03-12 | Gilead Connecticut, Inc. | 1,3 substituted diaryl ureas as modulators of kinase activity |
| WO2007024294A2 (en) * | 2005-05-03 | 2007-03-01 | Cgi Pharmaceuticals, Inc. | Certain substituted ureas, as modulators of kinase activity |
| US20080076770A1 (en) * | 2006-09-25 | 2008-03-27 | Arete Therapeutics, Inc. | Soluble epoxide hydrolase inhibitors |
| US20080200444A1 (en) * | 2006-10-20 | 2008-08-21 | Arete Therapeutics, Inc. | Soluble epoxide hydrolase inhibitors |
| CA2883373A1 (en) | 2012-08-28 | 2014-03-06 | 3M Innovative Properties Company | Chlorhexidine gluconate compositions, resin systems and articles |
| US20210139453A1 (en) * | 2018-04-06 | 2021-05-13 | Nippon Soda Co., Ltd. | (hetero)aryl sulfonamide compound and formulation for controlling harmful organisms |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1578644A (it) * | 1967-09-02 | 1969-08-14 | ||
| US3637731A (en) * | 1968-07-18 | 1972-01-25 | Du Pont | 1-(alkylsubstituted phenyl)imidazoles useful in acth reserve assay |
| US4172947A (en) * | 1977-01-07 | 1979-10-30 | Westwood Pharmaceuticals, Inc. | 1-(2-Acylaminophenyl)imidazoles |
| US4284641A (en) * | 1977-08-26 | 1981-08-18 | Burroughs Wellcome Co. | Pharmaceutically active imidazole derivatives |
| US4431815A (en) * | 1977-08-26 | 1984-02-14 | Burroughs Wellcome Co. | 1-[3-(2,4-Dichlorophenyl)propyl]imidazole and salts thereof |
| SE447653B (sv) * | 1978-11-14 | 1986-12-01 | Eisai Co Ltd | Imidazolderivat samt farmaceutisk komposition innehallande sadant derivat |
-
1979
- 1979-11-13 SE SE7909371A patent/SE447653B/sv not_active IP Right Cessation
- 1979-11-13 GB GB7939283A patent/GB2044754B/en not_active Expired
- 1979-11-13 US US06/093,469 patent/US4301169A/en not_active Expired - Lifetime
- 1979-11-14 DE DE19792946020 patent/DE2946020A1/de not_active Withdrawn
- 1979-11-14 CH CH1014979A patent/CH642635A5/fr not_active IP Right Cessation
- 1979-11-14 FR FR7928099A patent/FR2441616B1/fr not_active Expired
- 1979-11-14 CA CA339,861A patent/CA1126272A/en not_active Expired
- 1979-11-14 IT IT27268/79A patent/IT1127223B/it active
- 1979-11-14 NL NL7908331A patent/NL7908331A/nl not_active Application Discontinuation
-
1981
- 1981-04-09 US US06/252,674 patent/US4402966A/en not_active Expired - Fee Related
-
1983
- 1983-02-25 US US06/469,548 patent/US4533669A/en not_active Expired - Fee Related
-
1985
- 1985-06-06 US US06/741,935 patent/US4602031A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2044754A (en) | 1980-10-22 |
| GB2044754B (en) | 1983-05-05 |
| FR2441616A1 (fr) | 1980-06-13 |
| US4602031A (en) | 1986-07-22 |
| CH642635A5 (fr) | 1984-04-30 |
| DE2946020A1 (de) | 1980-05-29 |
| US4533669A (en) | 1985-08-06 |
| SE7909371L (sv) | 1980-05-15 |
| IT1127223B (it) | 1986-05-21 |
| FR2441616B1 (fr) | 1986-05-09 |
| IT7927268A0 (it) | 1979-11-14 |
| SE447653B (sv) | 1986-12-01 |
| CA1126272A (en) | 1982-06-22 |
| US4402966A (en) | 1983-09-06 |
| US4301169A (en) | 1981-11-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |