NO791945L - Fremgangsmaate for fremstilling av n-fenetylimidazolderivater - Google Patents

Fremgangsmaate for fremstilling av n-fenetylimidazolderivater

Info

Publication number: NO791945L
Authority: NO; Norway
Prior art keywords: imidazole; phenethyl; dichloro; formula; compound
Prior art date: 1978-06-12

Application number

NO79791945A

Other languages

English (en)

Norwegian (no)

Inventor

Paolo Cozzi

Antonio Pillan

Sergio Maggiori

Ivo De Carneri

Franca Trane

Original Assignee

Erba Farmitalia

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.)

1978-06-12

Filing date

1979-06-11

Publication date

1979-12-13

1978-06-12 Priority claimed from IT24426/78A external-priority patent/IT1096639B/it

1979-04-18 Priority claimed from IT2194079A external-priority patent/IT1165037B/it

1979-05-03 Priority claimed from IT2231979A external-priority patent/IT1113931B/it

1979-06-11 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1979-12-13 Publication of NO791945L publication Critical patent/NO791945L/no

Links

238000000034 method Methods 0.000 title claims description 12
CXZWSVDDOCSOIT-UHFFFAOYSA-N 1-(4-ethoxyphenyl)imidazole Chemical class C1=CC(OCC)=CC=C1N1C=NC=C1 CXZWSVDDOCSOIT-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 63
239000000460 chlorine Substances 0.000 claims description 58
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
125000004953 trihalomethyl group Chemical group 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
150000001768 cations Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052727 yttrium Inorganic materials 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 182
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 85
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
238000002844 melting Methods 0.000 description 28
230000008018 melting Effects 0.000 description 27
238000000921 elemental analysis Methods 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000003480 eluent Substances 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
-1 n-octyl Chemical group 0.000 description 17
239000000243 solution Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
235000019441 ethanol Nutrition 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
235000011114 ammonium hydroxide Nutrition 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
239000006210 lotion Substances 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000006071 cream Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000003795 chemical substances by application Substances 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
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
125000004649 C2-C8 alkynyl group Chemical group 0.000 description 2
241000222120 Candida <Saccharomycetales> Species 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
241000233866 Fungi Species 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000223238 Trichophyton Species 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
230000000843 anti-fungal effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
150000002460 imidazoles 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
239000002075 main ingredient Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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229910052698 phosphorus Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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229940093430 polyethylene glycol 1500 Drugs 0.000 description 2
229940068918 polyethylene glycol 400 Drugs 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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238000013207 serial dilution Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
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238000004809 thin layer chromatography Methods 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
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NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
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XMCRWEBERCXJCH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1Cl XMCRWEBERCXJCH-UHFFFAOYSA-N 0.000 description 1
SSENHTOBLYRWKU-UHFFFAOYSA-N 1-(2-phenylethyl)imidazole Chemical class C=1C=CC=CC=1CCN1C=CN=C1 SSENHTOBLYRWKU-UHFFFAOYSA-N 0.000 description 1
QVEAVDHTWIVBSX-UHFFFAOYSA-N 1-(3-bromopropoxy)-4-chlorobenzene Chemical compound ClC1=CC=C(OCCCBr)C=C1 QVEAVDHTWIVBSX-UHFFFAOYSA-N 0.000 description 1
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DCXSESONVKYUMI-UHFFFAOYSA-N 1-phenyl-2-(4-phenylimidazol-1-yl)ethanone Chemical compound C=1C=CC=CC=1C(=O)CN(C=1)C=NC=1C1=CC=CC=C1 DCXSESONVKYUMI-UHFFFAOYSA-N 0.000 description 1
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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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
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239000000377 silicon dioxide Substances 0.000 description 1
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229910052814 silicon oxide Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
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239000008117 stearic acid Substances 0.000 description 1
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235000002906 tartaric acid Nutrition 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
229940071127 thioglycolate Drugs 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
230000009466 transformation Effects 0.000 description 1
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229940035339 tri-chlor Drugs 0.000 description 1
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229920002554 vinyl polymer Polymers 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO79791945A 1978-06-12 1979-06-11 Fremgangsmaate for fremstilling av n-fenetylimidazolderivater NO791945L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IT24426/78A IT1096639B (it)	1978-06-12	1978-06-12	Derivati n-fenetilimidazolici e procedimento per la loro preparazione
IT2194079A IT1165037B (it)	1979-04-18	1979-04-18	Derivati n-fenetilimidazolici e procedimento per la loro preparazione
IT2231979A IT1113931B (it)	1979-05-03	1979-05-03	Derivati n-fenetilimidazolici e,procedimento per la loro preparazione

Publications (1)

Publication Number	Publication Date
NO791945L true NO791945L (no)	1979-12-13

Family

ID=27273228

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO79791945A NO791945L (no)	1978-06-12	1979-06-11	Fremgangsmaate for fremstilling av n-fenetylimidazolderivater

Country Status (9)

Country	Link
DE (1)	DE2922883A1 (da)
DK (1)	DK243079A (da)
FR (1)	FR2428633A1 (da)
GB (1)	GB2023141A (da)
IL (1)	IL57440A0 (da)
NL (1)	NL7904596A (da)
NO (1)	NO791945L (da)
SE (1)	SE7905077L (da)
YU (1)	YU134179A (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ194829A (en) *	1979-09-06	1984-10-19	Bristol Myers Co	1-phenethylimidazole derivatives;antibacterial and fungicidal compositions
DE3310830A1 (de) *	1983-03-24	1984-09-27	Bayer Ag, 5090 Leverkusen	Substituierte phenethyl-triazolyl-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU557755A3 (ru) *	1968-08-19	1977-05-05	Янссен Фармасьютика Н.В. (Фирма)	Способ получени производных имидазола

1979
- 1979-05-30 IL IL57440A patent/IL57440A0/xx unknown
- 1979-06-06 DE DE19792922883 patent/DE2922883A1/de active Pending
- 1979-06-07 YU YU01341/79A patent/YU134179A/xx unknown
- 1979-06-11 GB GB7920196A patent/GB2023141A/en not_active Withdrawn
- 1979-06-11 NO NO79791945A patent/NO791945L/no unknown
- 1979-06-11 DK DK243079A patent/DK243079A/da unknown
- 1979-06-11 SE SE7905077A patent/SE7905077L/xx not_active Application Discontinuation
- 1979-06-12 NL NL7904596A patent/NL7904596A/xx not_active Application Discontinuation
- 1979-06-12 FR FR7915025A patent/FR2428633A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
SE7905077L (sv)	1979-12-13
IL57440A0 (en)	1979-09-30
GB2023141A (en)	1979-12-28
NL7904596A (nl)	1979-12-14
FR2428633A1 (fr)	1980-01-11
DK243079A (da)	1979-12-13
DE2922883A1 (de)	1979-12-20
YU134179A (en)	1983-01-21

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AT390732B (de)	1990-06-25	Pharmazeutika enthaltend pyrazole
HU180555B (en)	1983-03-28	Process for preparing new derivatives of 1-phenyl-2-/acyl-amido/-3-fluoro-1-propanol derivatives
NO980055L (no)	1998-03-06	Antisoppmiddel, forbindelse derfor og fremgangsmåte for fremstilling derav
CA2787248C (en)	2016-03-01	Piperazine compound having a pgds inhibitory effect
GB2025946A (en)	1980-01-30	Imidazole derivative
US20200079727A1 (en)	2020-03-12	2-(substituted benzene matrix) aromatic formate fto inhibitor, preparation method therefor, and applications thereof
DK173892B1 (da)	2002-02-04	Aminderivater, fremgangsmåde til fremstilling af disse, fungicider indeholdende sådanne aminderivater og deres anvendelse som virksom bestanddel til fremstilling af et lægemiddel med antifungal aktivitet
BR112021012950A2 (pt)	2021-09-14	Métodos e materiais para aumentar os níveis de polipeptídeo do fator de transcrição eb
EP0165422B1 (de)	1988-03-09	Neue substituierte Bis(4-aminophenyl)sulfone, ihre Herstellung und ihre Verwendung als Arzneimittel
US5239084A (en)	1993-08-24	Substituted aminoalkyl biphenyl compounds
WO2005047270A2 (en)	2005-05-26	Substituted triazoles as sodium channel blockers
NO742361L (da)	1975-01-27
NO791945L (no)	1979-12-13	Fremgangsmaate for fremstilling av n-fenetylimidazolderivater
US4831151A (en)	1989-05-16	Antimicrobial imidazolium derivatives
WO2025190333A1 (zh)	2025-09-18	一类靶向cyp51的唑类化合物及其用途
JPH0372061B2 (da)	1991-11-15
JPH0251909B2 (da)	1990-11-08
EP0000693B1 (de)	1980-07-23	Aminophenoxymethyl-2-morpholinderivate, ihre Herstellung und sie enthaltende Arzneimittel
US5629332A (en)	1997-05-13	Triazole compound and use thereof
WO1995019336A1 (de)	1995-07-20	Phenylethanolaminether und ihre verwendung als beta-adrenorezeptor-agonisten
US3741951A (en)	1973-06-26	1-(p-benzamido)-3-methyl-triazenes
EP0370300A2 (de)	1990-05-30	Cyclopropyl-Substituierte Azolylmethylcarbinole, Verfarhren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0284914A1 (de)	1988-10-05	Benzofuranderivate und diese enthaltende therapeutische Mittel