CS272226B2 - Method of new lensofuran-2 ylimidazol derivatives production - Google Patents

Method of new lensofuran-2 ylimidazol derivatives production Download PDF

Info

Publication number: CS272226B2
Authority: CS; Czechoslovakia
Prior art keywords: group; formula; benzofuran; imidazole; compound
Prior art date: 1986-08-13

Application number

CS875978A

Other languages

Czech (cs)

English (en)

Other versions

CS597887A2 (en

Inventor

Vittorio Pestellini

Mario Ghelardoni

Danilo Giannotti

Alessandro Giolitti

Adriano Barzanti

Rossella Ciappi

Carlo Ortolani

Original Assignee

Menarini Sas

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-08-13

Filing date

1987-08-13

Publication date

1991-01-15

1987-08-13 Application filed by Menarini Sas filed Critical Menarini Sas

1990-03-14 Publication of CS597887A2 publication Critical patent/CS597887A2/cs

1991-01-15 Publication of CS272226B2 publication Critical patent/CS272226B2/cs

Links

238000000034 method Methods 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 42
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
VBFQIUOSXHUWCT-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-1h-imidazole Chemical class C1=CNC(C=2OC3=CC=CC=C3C=2)=N1 VBFQIUOSXHUWCT-UHFFFAOYSA-N 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
150000007524 organic acids Chemical class 0.000 claims 1
-1 acetamino group Chemical group 0.000 abstract description 18
125000000217 alkyl group Chemical group 0.000 abstract description 5
230000000843 anti-fungal effect Effects 0.000 abstract description 3
239000003242 anti bacterial agent Substances 0.000 abstract description 2
229940121375 antifungal agent Drugs 0.000 abstract description 2
125000004093 cyano group Chemical group *C#N 0.000 abstract 3
125000003277 amino group Chemical group 0.000 abstract 2
229910052736 halogen Inorganic materials 0.000 abstract 2
150000002367 halogens Chemical class 0.000 abstract 2
239000003429 antifungal agent Substances 0.000 abstract 1
125000003884 phenylalkyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
239000000047 product Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000003756 stirring Methods 0.000 description 5
MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000007789 gas 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
239000000543 intermediate Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
IJPZZRUJQUFAAM-UHFFFAOYSA-N (4-chlorophenyl)-(5,7-dichloro-1-benzofuran-2-yl)methanol Chemical compound C=1C2=CC(Cl)=CC(Cl)=C2OC=1C(O)C1=CC=C(Cl)C=C1 IJPZZRUJQUFAAM-UHFFFAOYSA-N 0.000 description 2
FDJFSQBODDLOFX-UHFFFAOYSA-N (5-bromo-1-benzofuran-2-yl)-(4-chlorophenyl)methanol Chemical compound C=1C2=CC(Br)=CC=C2OC=1C(O)C1=CC=C(Cl)C=C1 FDJFSQBODDLOFX-UHFFFAOYSA-N 0.000 description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
ACQXZXGZNHWVMK-UHFFFAOYSA-N 5,7-dichloro-2-[chloro-(4-chlorophenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC(Cl)=CC(Cl)=C2OC=1C(Cl)C1=CC=C(Cl)C=C1 ACQXZXGZNHWVMK-UHFFFAOYSA-N 0.000 description 2
AYOVPQORFBWFNO-UHFFFAOYSA-N 5-bromo-1-benzofuran Chemical compound BrC1=CC=C2OC=CC2=C1 AYOVPQORFBWFNO-UHFFFAOYSA-N 0.000 description 2
QGVSICQPIZUAKC-UHFFFAOYSA-N 5-bromo-2-[chloro-(4-chlorophenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC(Br)=CC=C2OC=1C(Cl)C1=CC=C(Cl)C=C1 QGVSICQPIZUAKC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
238000010992 reflux Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
WUASUUWIBALMGG-UHFFFAOYSA-N (2-chlorophenyl)-(7-methoxy-1-benzofuran-2-yl)methanol Chemical compound O1C=2C(OC)=CC=CC=2C=C1C(O)C1=CC=CC=C1Cl WUASUUWIBALMGG-UHFFFAOYSA-N 0.000 description 1
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
IRVOHCBKGFGSAE-UHFFFAOYSA-N (3-methyl-1-benzofuran-2-yl)-phenylmethanol Chemical compound O1C2=CC=CC=C2C(C)=C1C(O)C1=CC=CC=C1 IRVOHCBKGFGSAE-UHFFFAOYSA-N 0.000 description 1
FGQZVPZMZJBGIY-UHFFFAOYSA-N (5-bromo-1-benzofuran-2-yl)-phenylmethanol Chemical compound C=1C2=CC(Br)=CC=C2OC=1C(O)C1=CC=CC=C1 FGQZVPZMZJBGIY-UHFFFAOYSA-N 0.000 description 1
FIUREYXUADESFZ-UHFFFAOYSA-N (5-chloro-1-benzofuran-2-yl)-phenylmethanol Chemical compound C=1C2=CC(Cl)=CC=C2OC=1C(O)C1=CC=CC=C1 FIUREYXUADESFZ-UHFFFAOYSA-N 0.000 description 1
HJVDONGFOWJEMQ-UHFFFAOYSA-N (5-nitro-1-benzofuran-2-yl)-phenylmethanol Chemical compound C=1C2=CC([N+]([O-])=O)=CC=C2OC=1C(O)C1=CC=CC=C1 HJVDONGFOWJEMQ-UHFFFAOYSA-N 0.000 description 1
WGVYCXYGPNNUQA-UHFFFAOYSA-N 1-(bromomethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CBr WGVYCXYGPNNUQA-UHFFFAOYSA-N 0.000 description 1
UGJIHVMOPZRLPY-UHFFFAOYSA-N 1-[(2-chlorophenyl)-(5-methyl-1-benzofuran-2-yl)methyl]imidazole;hydrochloride Chemical compound Cl.C=1C2=CC(C)=CC=C2OC=1C(N1C=NC=C1)C1=CC=CC=C1Cl UGJIHVMOPZRLPY-UHFFFAOYSA-N 0.000 description 1
SFXSFFNFFGUAIY-UHFFFAOYSA-N 1-[(5-bromo-1-benzofuran-2-yl)-(2-chlorophenyl)methyl]imidazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)C1=CC2=CC(Br)=CC=C2O1 SFXSFFNFFGUAIY-UHFFFAOYSA-N 0.000 description 1
KMZJOBCVGQULHS-UHFFFAOYSA-N 1-[(5-chloro-1-benzofuran-2-yl)-(2-chlorophenyl)methyl]imidazole;hydrochloride Chemical compound Cl.C=1C2=CC(Cl)=CC=C2OC=1C(N1C=NC=C1)C1=CC=CC=C1Cl KMZJOBCVGQULHS-UHFFFAOYSA-N 0.000 description 1
XNLQAWKCIRZDDY-UHFFFAOYSA-N 1-[(5-chloro-1-benzofuran-2-yl)-phenylmethyl]imidazole Chemical compound C=1C2=CC(Cl)=CC=C2OC=1C(N1C=NC=C1)C1=CC=CC=C1 XNLQAWKCIRZDDY-UHFFFAOYSA-N 0.000 description 1
GXHPBBGIDNRSFQ-UHFFFAOYSA-N 1-[1-benzofuran-2-yl-[4-(2-phenylethenyl)phenyl]methyl]imidazole Chemical compound C=1C=CC=CC=1C=CC(C=C1)=CC=C1C(C=1OC2=CC=CC=C2C=1)N1C=CN=C1 GXHPBBGIDNRSFQ-UHFFFAOYSA-N 0.000 description 1
OCAPBUJLXMYKEJ-UHFFFAOYSA-N 1-[biphenyl-4-yl(phenyl)methyl]imidazole Chemical compound C1=NC=CN1C(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 OCAPBUJLXMYKEJ-UHFFFAOYSA-N 0.000 description 1
BHDJNYNPQFRNSX-UHFFFAOYSA-N 1-benzofuran-2-yl(phenyl)methanol Chemical compound C=1C2=CC=CC=C2OC=1C(O)C1=CC=CC=C1 BHDJNYNPQFRNSX-UHFFFAOYSA-N 0.000 description 1
RTQYXXOZKNFTFU-UHFFFAOYSA-N 1-benzofuran-2-yl-(2-methoxyphenyl)methanol Chemical compound COC1=CC=CC=C1C(O)C1=CC2=CC=CC=C2O1 RTQYXXOZKNFTFU-UHFFFAOYSA-N 0.000 description 1
OUQHVCOFXUKHNC-UHFFFAOYSA-N 1-benzofuran-2-yl-(2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1C(O)C1=CC2=CC=CC=C2O1 OUQHVCOFXUKHNC-UHFFFAOYSA-N 0.000 description 1
GYXISOAGDWYOIC-UHFFFAOYSA-N 1-benzofuran-2-yl-(2-phenylphenyl)methanol Chemical compound C=1C2=CC=CC=C2OC=1C(O)C1=CC=CC=C1C1=CC=CC=C1 GYXISOAGDWYOIC-UHFFFAOYSA-N 0.000 description 1
TVONMLOGRLGDHE-UHFFFAOYSA-N 1-benzofuran-2-yl-(4-methylphenyl)methanol Chemical compound C1=CC(C)=CC=C1C(O)C1=CC2=CC=CC=C2O1 TVONMLOGRLGDHE-UHFFFAOYSA-N 0.000 description 1
VPVXOXQYVCWECX-UHFFFAOYSA-N 1-benzofuran-2-yl-(4-nitrophenyl)methanol Chemical compound C=1C2=CC=CC=C2OC=1C(O)C1=CC=C([N+]([O-])=O)C=C1 VPVXOXQYVCWECX-UHFFFAOYSA-N 0.000 description 1
DUPOJTNSKNPNSV-UHFFFAOYSA-N 1-benzofuran-2-yl-[4-(2-phenylethenyl)phenyl]methanol Chemical compound C=1C2=CC=CC=C2OC=1C(O)C(C=C1)=CC=C1C=CC1=CC=CC=C1 DUPOJTNSKNPNSV-UHFFFAOYSA-N 0.000 description 1
OCQLRXQJOWTKFL-UHFFFAOYSA-N 2-[bromo-(4-chlorophenyl)methyl]-1-benzofuran Chemical compound C1=CC(Cl)=CC=C1C(Br)C1=CC2=CC=CC=C2O1 OCQLRXQJOWTKFL-UHFFFAOYSA-N 0.000 description 1
BPNQEUKXLYMIKP-UHFFFAOYSA-N 2-[chloro(phenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC=CC=C2OC=1C(Cl)C1=CC=CC=C1 BPNQEUKXLYMIKP-UHFFFAOYSA-N 0.000 description 1
ZPPIXCRZMMDMMR-UHFFFAOYSA-N 2-[chloro-(2-chlorophenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC=CC=C2OC=1C(Cl)C1=CC=CC=C1Cl ZPPIXCRZMMDMMR-UHFFFAOYSA-N 0.000 description 1
YRARTIBUSRQOMN-UHFFFAOYSA-N 2-[chloro-(2-chlorophenyl)methyl]-5-methyl-1-benzofuran Chemical compound C=1C2=CC(C)=CC=C2OC=1C(Cl)C1=CC=CC=C1Cl YRARTIBUSRQOMN-UHFFFAOYSA-N 0.000 description 1
YGDFKZGWOGAITK-UHFFFAOYSA-N 2-[chloro-(2-methoxyphenyl)methyl]-1-benzofuran Chemical compound COC1=CC=CC=C1C(Cl)C1=CC2=CC=CC=C2O1 YGDFKZGWOGAITK-UHFFFAOYSA-N 0.000 description 1
DCUVARVGSNBVCK-UHFFFAOYSA-N 2-[chloro-(2-phenylphenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC=CC=C2OC=1C(Cl)C1=CC=CC=C1C1=CC=CC=C1 DCUVARVGSNBVCK-UHFFFAOYSA-N 0.000 description 1
XMQFXPWJKMDPIE-UHFFFAOYSA-N 2-[chloro-(4-fluorophenyl)methyl]-1-benzofuran Chemical compound C1=CC(F)=CC=C1C(Cl)C1=CC2=CC=CC=C2O1 XMQFXPWJKMDPIE-UHFFFAOYSA-N 0.000 description 1
UQRKQFOKDFXEMY-UHFFFAOYSA-N 2-[chloro-(4-methylphenyl)methyl]-1-benzofuran Chemical compound C1=CC(C)=CC=C1C(Cl)C1=CC2=CC=CC=C2O1 UQRKQFOKDFXEMY-UHFFFAOYSA-N 0.000 description 1
BQOZCKYZFXUPCI-UHFFFAOYSA-N 2-[chloro-(4-nitrophenyl)methyl]-1-benzofuran Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(Cl)C1=CC2=CC=CC=C2O1 BQOZCKYZFXUPCI-UHFFFAOYSA-N 0.000 description 1
ZHTMBBTVFGQBMZ-UHFFFAOYSA-N 2-[chloro-[4-(2-phenylethenyl)phenyl]methyl]-1-benzofuran Chemical compound C=1C2=CC=CC=C2OC=1C(Cl)C(C=C1)=CC=C1C=CC1=CC=CC=C1 ZHTMBBTVFGQBMZ-UHFFFAOYSA-N 0.000 description 1
ZXQSQJZCPJVVJE-UHFFFAOYSA-N 2-acetyloctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(C)=O)C(O)=O ZXQSQJZCPJVVJE-UHFFFAOYSA-N 0.000 description 1
LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
CVNAFCXYJALQGV-UHFFFAOYSA-N 5,7-dichloro-1-benzofuran Chemical compound ClC1=CC(Cl)=C2OC=CC2=C1 CVNAFCXYJALQGV-UHFFFAOYSA-N 0.000 description 1
FDUJVAMTXLOLPZ-UHFFFAOYSA-N 5,7-dichloro-2-[chloro(phenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC(Cl)=CC(Cl)=C2OC=1C(Cl)C1=CC=CC=C1 FDUJVAMTXLOLPZ-UHFFFAOYSA-N 0.000 description 1
XKYZLRDKFRVCQM-UHFFFAOYSA-N 5-(1-benzofuran-2-yl)-2-benzyl-1h-imidazole Chemical class N=1C=C(C=2OC3=CC=CC=C3C=2)NC=1CC1=CC=CC=C1 XKYZLRDKFRVCQM-UHFFFAOYSA-N 0.000 description 1
IEBGBCWZBDAQPV-UHFFFAOYSA-N 5-bromo-2-[chloro(phenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC(Br)=CC=C2OC=1C(Cl)C1=CC=CC=C1 IEBGBCWZBDAQPV-UHFFFAOYSA-N 0.000 description 1
XWUSHARCEXDTJY-UHFFFAOYSA-N 5-bromo-2-[chloro-(2-chlorophenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC(Br)=CC=C2OC=1C(Cl)C1=CC=CC=C1Cl XWUSHARCEXDTJY-UHFFFAOYSA-N 0.000 description 1
BNOIXWVOUDVVCX-UHFFFAOYSA-N 5-chloro-2-[chloro(phenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC(Cl)=CC=C2OC=1C(Cl)C1=CC=CC=C1 BNOIXWVOUDVVCX-UHFFFAOYSA-N 0.000 description 1
CGUKYDZSIKRLRR-UHFFFAOYSA-N 5-chloro-2-[chloro-(2-chlorophenyl)methyl]-1-benzofuran Chemical compound C=1C2=CC(Cl)=CC=C2OC=1C(Cl)C1=CC=CC=C1Cl CGUKYDZSIKRLRR-UHFFFAOYSA-N 0.000 description 1
241001480043 Arthrodermataceae Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
201000007336 Cryptococcosis Diseases 0.000 description 1
241000221204 Cryptococcus neoformans Species 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
IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
206010017533 Fungal infection Diseases 0.000 description 1
241000233866 Fungi Species 0.000 description 1
UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
241000893980 Microsporum canis Species 0.000 description 1
241000893976 Nannizzia gypsea Species 0.000 description 1
DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
239000006057 Non-nutritive feed additive Substances 0.000 description 1
241000228143 Penicillium Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000223252 Rhodotorula Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010064899 Vulvovaginal mycotic infection Diseases 0.000 description 1
241000222126 [Candida] glabrata Species 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
229960002206 bifonazole Drugs 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
KBFBRIPYVVGWRS-UHFFFAOYSA-N cloridarol Chemical compound C=1C2=CC=CC=C2OC=1C(O)C1=CC=C(Cl)C=C1 KBFBRIPYVVGWRS-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000037304 dermatophytes Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000001174 endocardium Anatomy 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
208000024386 fungal infectious disease Diseases 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
229960002867 griseofulvin Drugs 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
210000004072 lung Anatomy 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
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
239000002541 mycostatic Substances 0.000 description 1
230000001557 mycostatic effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
230000021962 pH elevation Effects 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
ZYTJPPRBIGGXRO-UHFFFAOYSA-N propan-2-ylalumane Chemical compound C(C)(C)[AlH2] ZYTJPPRBIGGXRO-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
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 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
229940084106 spermaceti Drugs 0.000 description 1
239000012177 spermaceti Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (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)

CS875978A 1986-08-13 1987-08-13 Method of new lensofuran-2 ylimidazol derivatives production CS272226B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT8609461A IT1216256B (it)	1986-08-13	1986-08-13	(benzofuran-2-il) imidazoli, con attivita' farmacologica,loro sali e procedimenti di fabbricazione relativi.

Publications (2)

Publication Number	Publication Date
CS597887A2 CS597887A2 (en)	1990-03-14
CS272226B2 true CS272226B2 (en)	1991-01-15

Family

ID=11130481

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS875978A CS272226B2 (en)	1986-08-13	1987-08-13	Method of new lensofuran-2 ylimidazol derivatives production

Country Status (23)

Country	Link
US (1)	US4800208A (de)
EP (1)	EP0257171B1 (de)
JP (1)	JPS6372687A (de)
AR (1)	AR243181A1 (de)
AT (1)	ATE56008T1 (de)
AU (1)	AU604042B2 (de)
CA (1)	CA1325212C (de)
CS (1)	CS272226B2 (de)
DD (1)	DD270305A5 (de)
DE (1)	DE3673822D1 (de)
DK (1)	DK166917B1 (de)
ES (1)	ES2037011T3 (de)
GR (1)	GR3000903T3 (de)
HU (1)	HU202864B (de)
IE (1)	IE61019B1 (de)
IT (1)	IT1216256B (de)
MX (1)	MX7723A (de)
NO (1)	NO170085C (de)
PL (1)	PL149009B1 (de)
PT (1)	PT85491B (de)
SU (1)	SU1600630A3 (de)
YU (1)	YU46222B (de)
ZA (1)	ZA875908B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0574992A1 (de) *	1992-06-17	1993-12-22	Glaxo Group Limited	5-(1,2,4-Triazol-1-Ylmethyl)-3H-Isobenzofuran-1-Onderivate, ihre Herstellung und Verwendung als Aromatasinhibitoren
GB9212833D0 (en) *	1992-06-17	1992-07-29	Glaxo Group Ltd	Chemical compounds
US5426196A (en) *	1993-12-22	1995-06-20	Glaxo Inc.	Synthesis of diaryl methanes
IT1286866B1 (it) *	1996-10-28	1998-07-17	Menarini Farma Ind	Composti furano-eterociclici,loro preparazione ed uso come inibitori di aromatasi
US6503935B1 (en)	1998-08-07	2003-01-07	Abbott Laboratories	Imidazoles and related compounds as α1A agonists
RU2139872C1 (ru) *	1998-12-22	1999-10-20	Кубанский государственный технологический университет	2,4-диметил-3-(5-нитрофурфурил)-пиразол, обладающий способностью активировать прорастание семян пшеницы
GB0223915D0 (en) *	2002-10-15	2002-11-20	Univ Cardiff	Benzofuran derivatives formulations and uses thereof
CA2652280C (en)	2006-05-15	2014-01-28	Massachusetts Institute Of Technology	Polymers for functional particles
EP3424525A1 (de)	2007-10-12	2019-01-09	Massachusetts Institute Of Technology	Impfstoffnanotechnologie
US7762049B2 (en)	2008-12-31	2010-07-27	Black & Decker Inc.	Electric mower having two-motion activation system
CN112063532B (zh) *	2020-08-11	2022-05-24	浙江工业大学	林生地霉及其制备(s)-1-(2-三氟甲基苯基)乙醇的应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR6915465D0 (pt) *	1969-03-07	1973-01-04	Bayer Ag	Processo para preparar n-benzimidazois substituidos na posicao alfa por heterociclos penta-membrados com atividade antimicotica
DE2009020C3 (de) *	1970-02-26	1979-09-13	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von N-(l,l,l-trisubstituierten)-Methylazolen
US3928348A (en) *	1970-03-23	1975-12-23	Bayer Ag	N-methyl-imidazole derivatives and their production
IT1154888B (it) *	1980-11-12	1987-01-21	Menarini Sas	Derivati del benzofurano 2-sostituiti e relativi metodi di preparazione
DE3049542A1 (de) *	1980-12-31	1982-07-29	Basf Ag, 6700 Ludwigshafen	Azolylalkyl-2,3-dihydrobenzofurane, diese enthaltende fungizide und verfahren zu ihrer herstellung
ZA825413B (en) *	1981-08-26	1983-06-29	Pfizer	Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them
FI842502A7 (fi) *	1983-06-27	1984-12-28	Ciba Geigy Ag	Foerfarande foer framstaellning av nya 2-substituerade bensofuran derivat.
DE3413363A1 (de) *	1984-04-09	1985-10-17	Merz + Co GmbH & Co, 6000 Frankfurt	Benzofuran-2-yl-ethyl-imidazolderivate, verfahren zu ihrer herstellung und pharmazeutische mittel

1986
- 1986-08-13 IT IT8609461A patent/IT1216256B/it active
- 1986-12-11 ES ES198686830370T patent/ES2037011T3/es not_active Expired - Lifetime
- 1986-12-11 AT AT86830370T patent/ATE56008T1/de not_active IP Right Cessation
- 1986-12-11 EP EP86830370A patent/EP0257171B1/de not_active Expired - Lifetime
- 1986-12-11 DE DE8686830370T patent/DE3673822D1/de not_active Expired - Lifetime
1987
- 1987-07-30 AR AR87308306A patent/AR243181A1/es active
- 1987-08-05 PT PT85491A patent/PT85491B/pt not_active IP Right Cessation
- 1987-08-11 ZA ZA875908A patent/ZA875908B/xx unknown
- 1987-08-11 DK DK418187A patent/DK166917B1/da not_active IP Right Cessation
- 1987-08-11 DD DD87305902A patent/DD270305A5/de not_active IP Right Cessation
- 1987-08-12 CA CA000544286A patent/CA1325212C/en not_active Expired - Fee Related
- 1987-08-12 MX MX772387A patent/MX7723A/es unknown
- 1987-08-12 IE IE215387A patent/IE61019B1/en not_active IP Right Cessation
- 1987-08-12 HU HU873653A patent/HU202864B/hu not_active IP Right Cessation
- 1987-08-12 PL PL1987267298A patent/PL149009B1/pl unknown
- 1987-08-12 AU AU76799/87A patent/AU604042B2/en not_active Ceased
- 1987-08-12 NO NO873383A patent/NO170085C/no unknown
- 1987-08-12 SU SU874203231A patent/SU1600630A3/ru active
- 1987-08-13 JP JP62201044A patent/JPS6372687A/ja active Pending
- 1987-08-13 YU YU150787A patent/YU46222B/sh unknown
- 1987-08-13 CS CS875978A patent/CS272226B2/cs unknown
- 1987-08-13 US US07/085,067 patent/US4800208A/en not_active Expired - Fee Related
1990
- 1990-10-04 GR GR90400548T patent/GR3000903T3/el unknown

Also Published As

Publication number	Publication date
EP0257171A1 (de)	1988-03-02
MX7723A (es)	1993-12-01
DE3673822D1 (de)	1990-10-04
NO170085C (no)	1992-09-09
ES2037011T3 (es)	1993-06-16
SU1600630A3 (ru)	1990-10-15
PT85491B (pt)	1990-06-29
DK418187A (da)	1988-02-14
ATE56008T1 (de)	1990-09-15
YU150787A (en)	1988-10-31
DD270305A5 (de)	1989-07-26
YU46222B (sh)	1993-05-28
NO873383L (no)	1988-02-15
AU7679987A (en)	1988-02-18
GR3000903T3 (en)	1991-12-10
DK166917B1 (da)	1993-08-02
NO170085B (no)	1992-06-01
PT85491A (en)	1987-09-01
IT1216256B (it)	1990-02-22
IE61019B1 (en)	1994-09-07
US4800208A (en)	1989-01-24
DK418187D0 (da)	1987-08-11
NO873383D0 (no)	1987-08-12
JPS6372687A (ja)	1988-04-02
HU202864B (en)	1991-04-29
EP0257171B1 (de)	1990-08-29
IE872153L (en)	1988-02-13
IT8609461A0 (it)	1986-08-13
AR243181A1 (es)	1993-07-30
AU604042B2 (en)	1990-12-06
HUT46910A (en)	1988-12-28
PL267298A1 (en)	1988-12-08
ZA875908B (en)	1988-02-12
CS597887A2 (en)	1990-03-14
PL149009B1 (en)	1989-12-30
CA1325212C (en)	1993-12-14

Publication	Publication Date	Title
US3812142A (en)	1974-05-21	Imidazolyl ketones
US4328348A (en)	1982-05-04	Novel benzylimidazole derivatives
IL33918A (en)	1973-05-31	Substituted n-benzylimidazoles,their production and pharmaceutical compositions containing them
CS272226B2 (en)	1991-01-15	Method of new lensofuran-2 ylimidazol derivatives production
CN101434595B (zh)	2014-06-25	抗真菌剂-硫色满酮缩氨基(硫)脲系列物
US5110831A (en)	1992-05-05	Vinylogous hydroxamic acids and derivatives thereof as 5-lipoxygenase inhibitors
EP0198235B1 (de)	1989-08-23	Imidazolderivate mit antimykotischer und antibakterieller Wirkung, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
EP0133248B1 (de)	1991-11-21	1,2,4-Triazol-1-yl-Derivate
US4282230A (en)	1981-08-04	Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them
US4459412A (en)	1984-07-10	1-Benzylimidazole derivatives
US3790594A (en)	1974-02-05	Thienyl-imidazolyl alkanoic acids
JPH02243673A (ja)	1990-09-27	シクロプロピル置換アゾリルメチルカルビノール誘導体、その製造方法及び医薬としてのその用途
US5135943A (en)	1992-08-04	1H-imidazole derivative compounds and pharmaceutical compositions containing the same
JPS584023B2 (ja)	1983-01-24	イミダゾリルサクサンアミドノセイゾウホウホウ
US4904682A (en)	1990-02-27	Treating mycoses with triazolylalkanols
IL36487A (en)	1974-09-10	Derivatives of phenyl-imidazolyl (or 1,2,4-triazolyl) fatty acids,their production and their use as medicines
US4052409A (en)	1977-10-04	Disubstituted triphenylmethylimidazoles
HU186677B (en)	1985-09-30	Process for preparing substituted hydroxy-alkyl-imidazole and -triazole derivatives
JP3437695B2 (ja)	2003-08-18	アゾリルアミン誘導体
JP2798094B2 (ja)	1998-09-17	抗菌剤としてのジクロロ置換イミダゾール誘導体
JPS5823396B2 (ja)	1983-05-14	１−エチル−アゾ−ル化合物の製造方法
US3839576A (en)	1974-10-01	Thienyl-imidazolyl alkanoic acids as antimycotic agents
US3980780A (en)	1976-09-14	N-Methyl-imidazole derivatives for treating mycotic infections
NO144671B (no)	1981-07-06	Analogifremgangsmaate for fremstilling av farmakologisk aktive n-(p-fluorbenzoylpropyl)-4-piperidylamider
US3887556A (en)	1975-06-03	Antimycotic diphenyl-imidazolyl-pyrimidyl methanes