ES2587942T3 - Compuestos de fenilimidazol - Google Patents
Compuestos de fenilimidazol Download PDFInfo
- Publication number
- ES2587942T3 ES2587942T3 ES10738531.2T ES10738531T ES2587942T3 ES 2587942 T3 ES2587942 T3 ES 2587942T3 ES 10738531 T ES10738531 T ES 10738531T ES 2587942 T3 ES2587942 T3 ES 2587942T3
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- hydrogen atom
- methoxyphenyl
- halogen
- alkyl groups
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- 150000004841 phenylimidazoles Chemical class 0.000 title 1
- -1 Phenylimidazole compound Chemical class 0.000 abstract description 20
- 125000005843 halogen group Chemical group 0.000 abstract description 17
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 229910052736 halogen Chemical group 0.000 abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
- 125000001424 substituent group Chemical group 0.000 abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 5
- 125000003884 phenylalkyl group Chemical group 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 125000002541 furyl group Chemical group 0.000 abstract description 2
- 125000001544 thienyl group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HURXMBPASSKQJH-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-5-(2-methoxy-4-phenylmethoxyphenyl)-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=C(Cl)C(Cl)=CC=2)C(OC)=CC=1OCC1=CC=CC=C1 HURXMBPASSKQJH-UHFFFAOYSA-N 0.000 description 1
- XYCDDKWRTSXPSB-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-5-(2-methoxy-4-phenylmethoxyphenyl)-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=C(F)C(F)=CC=2)C(OC)=CC=1OCC1=CC=CC=C1 XYCDDKWRTSXPSB-UHFFFAOYSA-N 0.000 description 1
- YUSUZWXUZFPIDR-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(3-methoxy-4-phenylmethoxyphenyl)-5-methyl-1h-imidazole Chemical compound COC1=CC(C2=C(NC(=N2)C=2C=CC(F)=CC=2)C)=CC=C1OCC1=CC=CC=C1 YUSUZWXUZFPIDR-UHFFFAOYSA-N 0.000 description 1
- CQRVICGKHQANQB-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(2-methoxy-4-phenylmethoxyphenyl)-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(F)=CC=2)C(OC)=CC=1OCC1=CC=CC=C1 CQRVICGKHQANQB-UHFFFAOYSA-N 0.000 description 1
- BHVSSNXGBSWVHK-UHFFFAOYSA-N 4-[[3-methoxy-4-[2-[3-(trifluoromethyl)phenyl]-1h-imidazol-5-yl]phenoxy]methyl]benzonitrile Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=C(C=CC=2)C(F)(F)F)C(OC)=CC=1OCC1=CC=C(C#N)C=C1 BHVSSNXGBSWVHK-UHFFFAOYSA-N 0.000 description 1
- BFASJSUTJWMVLH-UHFFFAOYSA-N 4-[[3-methoxy-4-[2-[4-(trifluoromethyl)phenyl]-1h-imidazol-5-yl]phenoxy]methyl]benzonitrile Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=1OCC1=CC=C(C#N)C=C1 BFASJSUTJWMVLH-UHFFFAOYSA-N 0.000 description 1
- XWHCDAQMNOZFIV-UHFFFAOYSA-N 4-[[4-[2-(4-fluorophenyl)-1h-imidazol-5-yl]-3-methoxyphenoxy]methyl]benzonitrile Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(F)=CC=2)C(OC)=CC=1OCC1=CC=C(C#N)C=C1 XWHCDAQMNOZFIV-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- FBHIXFITZMADQD-UHFFFAOYSA-N 5-(3-methoxy-4-phenylmethoxyphenyl)-2-thiophen-3-yl-1h-imidazole Chemical compound COC1=CC(C=2N=C(NC=2)C2=CSC=C2)=CC=C1OCC1=CC=CC=C1 FBHIXFITZMADQD-UHFFFAOYSA-N 0.000 description 1
- JCNNBKDYTFOWMV-UHFFFAOYSA-N 5-[4-[(4-bromo-2-fluorophenyl)methoxy]-2-methoxyphenyl]-2-(4-chlorophenyl)-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(Cl)=CC=2)C(OC)=CC=1OCC1=CC=C(Br)C=C1F JCNNBKDYTFOWMV-UHFFFAOYSA-N 0.000 description 1
- QYICZFINTIHZSF-UHFFFAOYSA-N 5-[4-[(4-bromo-2-fluorophenyl)methoxy]-2-methoxyphenyl]-2-(4-fluorophenyl)-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(F)=CC=2)C(OC)=CC=1OCC1=CC=C(Br)C=C1F QYICZFINTIHZSF-UHFFFAOYSA-N 0.000 description 1
- QWVHHWPNQDGVIK-UHFFFAOYSA-N 5-[4-[(4-bromo-2-fluorophenyl)methoxy]-2-methoxyphenyl]-2-(4-methylphenyl)-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(C)=CC=2)C(OC)=CC=1OCC1=CC=C(Br)C=C1F QWVHHWPNQDGVIK-UHFFFAOYSA-N 0.000 description 1
- HUFOVWVMOZNQKZ-UHFFFAOYSA-N 5-[4-[(4-bromo-2-fluorophenyl)methoxy]-2-methoxyphenyl]-2-[4-(trifluoromethyl)phenyl]-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=1OCC1=CC=C(Br)C=C1F HUFOVWVMOZNQKZ-UHFFFAOYSA-N 0.000 description 1
- YKQVUAOIHSRBBZ-UHFFFAOYSA-N 5-[4-[(4-bromo-2-fluorophenyl)methoxy]-3-methoxyphenyl]-2-(4-fluorophenyl)-1h-imidazole Chemical compound COC1=CC(C=2N=C(NC=2)C=2C=CC(F)=CC=2)=CC=C1OCC1=CC=C(Br)C=C1F YKQVUAOIHSRBBZ-UHFFFAOYSA-N 0.000 description 1
- PXKOPJZTLWWINV-UHFFFAOYSA-N 5-[4-[(4-bromo-2-fluorophenyl)methoxy]-3-methoxyphenyl]-2-[4-(trifluoromethyl)phenyl]-1h-imidazole Chemical compound COC1=CC(C=2N=C(NC=2)C=2C=CC(=CC=2)C(F)(F)F)=CC=C1OCC1=CC=C(Br)C=C1F PXKOPJZTLWWINV-UHFFFAOYSA-N 0.000 description 1
- HVDNEYWNWJEKBD-UHFFFAOYSA-N 5-[4-[(4-bromo-2-fluorophenyl)methoxy]-3-methoxyphenyl]-2-thiophen-2-yl-1h-imidazole Chemical compound COC1=CC(C=2N=C(NC=2)C=2SC=CC=2)=CC=C1OCC1=CC=C(Br)C=C1F HVDNEYWNWJEKBD-UHFFFAOYSA-N 0.000 description 1
- IPXCVYWPWXDDRE-UHFFFAOYSA-N 5-[4-[(4-chlorophenyl)methoxy]-2-methoxyphenyl]-2-(3,4-difluorophenyl)-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=C(F)C(F)=CC=2)C(OC)=CC=1OCC1=CC=C(Cl)C=C1 IPXCVYWPWXDDRE-UHFFFAOYSA-N 0.000 description 1
- KQODHDIANJMZEX-UHFFFAOYSA-N 5-[4-[(4-chlorophenyl)methoxy]-2-methoxyphenyl]-2-(4-fluorophenyl)-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(F)=CC=2)C(OC)=CC=1OCC1=CC=C(Cl)C=C1 KQODHDIANJMZEX-UHFFFAOYSA-N 0.000 description 1
- ZLRCDNFSTGXWAJ-UHFFFAOYSA-N 5-[4-[(4-chlorophenyl)methoxy]-2-methoxyphenyl]-2-[4-(trifluoromethyl)phenyl]-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=1OCC1=CC=C(Cl)C=C1 ZLRCDNFSTGXWAJ-UHFFFAOYSA-N 0.000 description 1
- UWPYCDVRYKJAOA-UHFFFAOYSA-N 5-[4-[(4-chlorophenyl)methoxy]-2-methoxyphenyl]-2-thiophen-3-yl-1h-imidazole Chemical compound C=1C=C(C=2N=C(NC=2)C2=CSC=C2)C(OC)=CC=1OCC1=CC=C(Cl)C=C1 UWPYCDVRYKJAOA-UHFFFAOYSA-N 0.000 description 1
- CDDVMNUYYNTYPE-UHFFFAOYSA-N 5-[4-[(4-chlorophenyl)methoxy]-3-methoxyphenyl]-2-[4-(trifluoromethyl)phenyl]-1h-imidazole Chemical compound COC1=CC(C=2N=C(NC=2)C=2C=CC(=CC=2)C(F)(F)F)=CC=C1OCC1=CC=C(Cl)C=C1 CDDVMNUYYNTYPE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 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
- A61K31/4164—1,3-Diazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
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- 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
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
Compuesto de fenilimidazol representado por la siguiente fórmula general (1):**Fórmula** en la que R1 representa un átomo de hidrógeno, un grupo fenilalquilo C1-6 o un grupo piridilalquilo C1-6, y el anillo de benceno y el anillo de piridina están opcionalmente sustituidos con 1 o 2 sustituyentes seleccionados del grupo que consiste en átomos de halógeno, grupo ciano y grupos alquilo C1-6 sustituidos con halógeno ; uno de R2 y R3 representa un átomo de hidrógeno y el otro representa un grupo alcoxilo C1-6; R4 representa un grupo alquilo C1-6, un grupo furilo, un grupo tienilo o un grupo fenilo opcionalmente sustituido con 1 o 2 sustituyentes seleccionados del grupo que consiste en grupos alquilo C1-6, grupos alcoxilo C1-6, átomos de halógeno, grupo carboxilo, grupos alcoxicarbonilo C1-6 y grupos alquilo C1-6 sustituidos con halógeno; R5 y R6 son iguales o diferentes, y representan un átomo de hidrógeno o un grupo alquilo C1-6; R7 y R8 son iguales o diferentes, y representan un átomo de hidrógeno o un grupo alcoxilo C1-6; sin embargo, cuando R1 representa un grupo fenilalquilo C1-6 no sustituido, R2 representa un grupo alcoxilo C1-6, R3 representa un átomo de hidrógeno, R4 representa un grupo fenilo no sustituido o un grupo fenilo que tiene 1 o 2 grupos alquilo C1-6 sustituidos con halógeno, y R5 representa un átomo de hidrógeno, R6 no es un átomo de hidrógeno.
Description
5
15
25
35
45
55
65
átomos de halógeno, grupo carboxilo, grupos alcoxicarbonilo inferior y grupos alquilo inferior sustituidos con halógeno. Un R4 más preferible es un grupo furilo, un grupo tienilo o un grupo fenilo opcionalmente sustituido con 1 o 2 sustituyentes seleccionados del grupo que consiste en grupos alquilo inferior, grupos alcoxilo inferior, átomos de halógeno, grupos alcoxicarbonilo inferior y grupos alquilo inferior sustituidos con halógeno.
Los ejemplos específicos de R4 preferible incluyen 2-tienilo, 3-tienilo, 3-furilo, fenilo, 4-fluorofenilo, 3-fluorofenilo, 3fluoro-4-metilfenilo, 3,4-difluorofenilo, 4-trifluorometilfenilo, 3-trifluorometilfenilo, 2-trifluorometilfenilo, 4-clorofenilo, 3clorofenilo, 3,4-diclorofenilo, 3,5-diclorofenilo, 3-cloro-4-fluorofenilo, 3-metoxifenilo, 4-metoxifenilo, 3,4-dimetoxifenilo 4-metoxicarbonilfenilo, 4-carboxifenilo, 4-(1,1-dimetiletil)fenilo, 1-metiletilo, 4-metilfenilo, etc. Los ejemplos específicos de R4 más preferible incluyen 2-tienilo, 3-tienilo, 3-furilo, fenilo, 4-fluorofenilo, 3-fluorofenilo, 3,4difluorofenilo, 4-trifluorometilfenilo, 3-trifluorometilfenilo, 2-trifluorometilfenilo, 4-clorofenilo, 3-clorofenilo, 3,4diclorofenilo, 3,5-diclorofenilo, 3-cloro-4-fluorofenilo, 3-metoxifenilo, 4-metoxicarbonilfenilo, 4-(1,1-dimetiletil)fenilo, 1metiletilo, 4-metilfenilo, etc.
En la fórmula general (1), R4 y R5 preferibles son átomos de hidrógeno.
En la fórmula general (1), R7 y R8 preferibles son átomos de hidrógeno.
Un compuesto de fenilimidazol preferible representado por la fórmula general (1) es a compuesto en el que R1 es un grupo seleccionado del grupo que consiste en bencilo, 4-clorobencilo y 4-bromo-2-fluorobencilo; y R4 es un grupo seleccionado del grupo que consiste en 4-trifluorometilfenilo, 4-fluorofenilo, 3,4-difluorofenilo, 4-clorofenilo, 3,4diclorofenilo y 4-metilfenilo.
Los ejemplos específicos de un compuesto de fenilimidazol más preferible representado por la fórmula general (1) incluyen los siguientes compuestos:
- •
- 4-[4-(4-bromo-2-fluorobenciloxi)-3-metoxifenil]-2-[4-(trifluorometil)fenil]-1H-imidazol
- •
- 4-[4-(4-cianobenciloxi)-2-metoxifenil]-2-[4-(trifluorometil)fenil]-1H-imidazol
- •
- 4-[4-(4-bromo-2-fluorobenciloxi)-2-metoxifenil]-2-[4-(trifluorometil)fenil]-1H-imidazol
- •
- 4-[4-(4-clorobenciloxi)-2-metoxifenil]-2-[4-(trifluorometil)fenil]-1H-imidazol
- •
- 4-(4-benciloxi-3-metoxifenil)-2-(3-tienil)-1H-imidazol
- •
- 4-(4-benciloxi-2-metoxifenil)-2-(4-fluorofenil)-1H-imidazol
- •
- 4-(4-benciloxi-3-metoxifenil)-2-(4-fluorofenil)-5-metil-1H-imidazol
- •
- 4-[4-(4-clorobenciloxi)-2-metoxifenil]-2-(4-fluorofenil)-1H-imidazol
- •
- 4-[4-(4-clorobenciloxi)-3-metoxifenil]-2-[4-(trifluorometil)fenil]-1H-imidazol
- •
- 4-[4-(4-cianobenciloxi)-2-metoxifenil]-2-(4-fluorofenil)-1H-imidazol
- •
- 4-[4-(4-bromo-2-fluorobenciloxi)-3-metoxifenil]-2-(4-fluorofenil)-1H-imidazol
- •
- 4-[4-(4-bromo-2-fluorobenciloxi)-2-metoxifenil]-2-(4-fluorofenil)-1H-imidazol
- •
- 4-[4-(4-bromo-2-fluorobenciloxi)-2-metoxifenil]-2-(4-clorofenil)-1H-imidazol
- •
- 4-[4-(4-bromo-2-fluorobenciloxi)-3-metoxifenil]-2-(2-tienil)-1H-imidazol
- •
- 4-[4-(4-clorobenciloxi)-2-metoxifenil]-2-(3-tienil)-1H-imidazol
- •
- 4-[4-(4-cianobenciloxi)-2-metoxifenil]-2-[3-(trifluorometil)fenil]-1H-imidazol
- •
- 4-[4-(4-bromo-2-fluorobenciloxi)-2-metoxifenil]-2-(4-metilfenil)-1H-imidazol
- •
- 4-[4-(4-clorobenciloxi)-2-metoxifenil]-2-(3,4-difluorofenil)-1H-imidazol
- •
- 4-(4-benciloxi-2-metoxifenil)-2-(3,4-difluorofenil)-1H-imidazol
- •
- 4-(4-benciloxi-2-metoxifenil)-2-(3,4-diclorofenil)-1H-imidazol.
8
[Fórmula 3]
en la que, R1, R2, R3, R5, R7, R8 y X1 son tal como se definieron anteriormente.
5 El compuesto deseado (2) puede obtenerse haciendo reaccionar el compuesto (4) y trihaluro de trimetilfenilamonio (5), por ejemplo, en un disolvente inerte tal como tetrahidrofurano (THF), 1,4-dioxano, etc., a de 0 ºC a 50 ºC durante de 5 a 20 horas. Se usan de 1 a 1,3 moles de trihaluro de trimetilfenilamonio (5) por mol de compuesto (4).
10 Además, en el esquema de reacción-2, el compuesto (4a) incluido en el compuesto (4) usado como material de partida es un compuesto en el que R1 es un grupo fenilalquilo inferior opcionalmente sustituido con 1 o 2 sustituyentes seleccionados del grupo que consiste en átomos de halógeno, grupo ciano y grupos alquilo inferior sustituidos con halógeno; y el compuesto (4b) incluido en el compuesto (4) es un compuesto en el que R1 es un grupo piridilalquilo inferior opcionalmente sustituido con 1 o 2 sustituyentes seleccionados del grupo que consiste en
15 átomos de halógeno, grupo ciano y grupos alquilo inferior sustituidos con halógeno. Estos compuestos (4a) y (4b) pueden producirse mediante los métodos mostrados en el esquema de reacción-3 y el esquema de reacción-4 a continuación, respectivamente.
[Esquema de reacción-3] 20
seleccionados del grupo que consiste en átomos de halógeno, grupo ciano y grupos alquilo inferior sustituidos con
25 halógeno, o un grupo piridilalquilo inferior opcionalmente sustituido con 1 o 2 sustituyentes seleccionados del grupo que consiste en átomos de halógeno, grupo ciano y grupos alquilo inferior sustituidos con halógeno; y R2, R3, R5, R7 y R8 son tal como se definieron anteriormente. X2 representa un átomo de halógeno.
El compuesto (6) conocido mencionado anteriormente puede convertirse en el compuesto (4a) haciéndolo
30 reaccionar con haluro (7). La reacción se lleva a cabo en un disolvente inerte tal como N,N-dimetilformamida (DMF), N,N-dimetilacetamida (DMA), dimetilsulfóxido (DMSO), etc., en presencia de un álcali tal como carbonato de potasio, carbonato de sodio, etc., y se completa a una temperatura ambiente a 100 ºC en de aproximadamente 5 a aproximadamente 30 horas. Se usan de 1 a 2 moles de haluro (7) por mol de compuesto (6), y se usan de 1 a 3 moles de álcali por mol de compuesto (6).
35 [Esquema de reacción-4]
[Fórmula 5]
10
[Tabla 3]
15
17
19
21
26
[Tabla 6]
29
Claims (1)
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imagen1 imagen2 imagen3
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