DD143608A5 - Verfahren zur herstellung von 4'-substituierten 2,4-dichlor-alpha-(imidazol-n-ylmethyl)-dibenzylaethern - Google Patents

Verfahren zur herstellung von 4'-substituierten 2,4-dichlor-alpha-(imidazol-n-ylmethyl)-dibenzylaethern Download PDF

Info

Publication number: DD143608A5
Authority: DD; German Democratic Republic
Prior art keywords: imidazol; ylmethyl; substituted; dichloro; general formula
Prior art date: 1978-05-18

Application number

DD79212866A

Other languages

German (de)

English (en)

Inventor

Dante Nardi

Elena Massarani

Alberto Tajana

Mario Veronese

Original Assignee

Recordati Chem Pharm

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.)

1978-05-18

Filing date

1979-05-14

Publication date

1980-09-03

1979-05-14 Application filed by Recordati Chem Pharm filed Critical Recordati Chem Pharm

1980-09-03 Publication of DD143608A5 publication Critical patent/DD143608A5/de

Links

-1 IMIDAZOLE-N-YLMETHYL Chemical class 0.000 title claims abstract description 44
238000004519 manufacturing process Methods 0.000 title description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 26
239000002904 solvent Substances 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 8
BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical group [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
150000007513 acids Chemical class 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 16
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
238000009833 condensation Methods 0.000 claims description 13
230000005494 condensation Effects 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000006277 halobenzyl group Chemical group 0.000 claims description 4
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 claims description 3
229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzylether Substances C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 abstract description 38
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 12
240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 12
241000894006 Bacteria Species 0.000 abstract description 7
230000001988 toxicity Effects 0.000 abstract description 7
231100000419 toxicity Toxicity 0.000 abstract description 7
230000000144 pharmacologic effect Effects 0.000 abstract description 6
239000004305 biphenyl Substances 0.000 abstract description 2
WSLSNIMNEMCJPK-UHFFFAOYSA-N 1-(bromomethyl)-4-phenylsulfanylbenzene Chemical compound C1=CC(CBr)=CC=C1SC1=CC=CC=C1 WSLSNIMNEMCJPK-UHFFFAOYSA-N 0.000 abstract 1
235000015047 pilsener Nutrition 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
239000000243 solution Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
150000001875 compounds Chemical class 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
241000233866 Fungi Species 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
239000000047 product Substances 0.000 description 10
239000002585 base Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
229960002509 miconazole Drugs 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229910002651 NO3 Inorganic materials 0.000 description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
239000002609 medium Substances 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000002054 inoculum Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
UKVLTPAGJIYSGN-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)CN1C=CN=C1 UKVLTPAGJIYSGN-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 3
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 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000013558 reference substance Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
241000228245 Aspergillus niger Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
201000007336 Cryptococcosis Diseases 0.000 description 2
241000221204 Cryptococcus neoformans Species 0.000 description 2
241000192125 Firmicutes Species 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
241000699670 Mus sp. Species 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
229940121375 antifungal agent Drugs 0.000 description 2
239000003429 antifungal agent Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229960004022 clotrimazole Drugs 0.000 description 2
VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 2
239000007376 cm-medium Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
244000005700 microbiome Species 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
208000017520 skin disease Diseases 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
RLFHPRWHJYDGSD-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylsulfanylbenzene Chemical compound C1=CC(CCl)=CC=C1SC1=CC=CC=C1 RLFHPRWHJYDGSD-UHFFFAOYSA-N 0.000 description 1
XHEPANNURIQWRM-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)ethanol Chemical compound ClCC(O)C1=CC=C(Cl)C=C1Cl XHEPANNURIQWRM-UHFFFAOYSA-N 0.000 description 1
DXTLBEQSVNRVKT-UHFFFAOYSA-N 2-thiocyanatoethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCSC#N DXTLBEQSVNRVKT-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
BSXJOVBDERGUCS-UHFFFAOYSA-N C(C1=CC=CC=C1)OCC1=CC=CC=C1.[N+](=O)(O)[O-] Chemical compound C(C1=CC=CC=C1)OCC1=CC=CC=C1.[N+](=O)(O)[O-] BSXJOVBDERGUCS-UHFFFAOYSA-N 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
206010007134 Candida infections Diseases 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
241001480036 Epidermophyton floccosum Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000228150 Penicillium chrysogenum Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000295644 Staphylococcaceae 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
241000223229 Trichophyton rubrum Species 0.000 description 1
102000004142 Trypsin Human genes 0.000 description 1
108090000631 Trypsin Proteins 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
241001148470 aerobic bacillus Species 0.000 description 1
239000008272 agar Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
235000010290 biphenyl Nutrition 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
201000003984 candidiasis Diseases 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
230000029087 digestion Effects 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
ROAYSRAUMPWBQX-UHFFFAOYSA-N ethanol;sulfuric acid Chemical compound CCO.OS(O)(=O)=O ROAYSRAUMPWBQX-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- 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)
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)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

DD79212866A 1978-05-18 1979-05-14 Verfahren zur herstellung von 4'-substituierten 2,4-dichlor-alpha-(imidazol-n-ylmethyl)-dibenzylaethern DD143608A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT23546/78A IT1096361B (it)	1978-05-18	1978-05-18	Dibenzileteri sostituiti terapeuticamente attivi

Publications (1)

Publication Number	Publication Date
DD143608A5 true DD143608A5 (de)	1980-09-03

Family

ID=11208025

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79212866A DD143608A5 (de)	1978-05-18	1979-05-14	Verfahren zur herstellung von 4'-substituierten 2,4-dichlor-alpha-(imidazol-n-ylmethyl)-dibenzylaethern

Country Status (29)

Country	Link
JP (1)	JPS605592B2 (da)
AR (1)	AR219596A1 (da)
AT (1)	AT372950B (da)
AU (1)	AU523053B2 (da)
CA (1)	CA1115718A (da)
CH (1)	CH639075A5 (da)
DD (1)	DD143608A5 (da)
DE (1)	DE2917244C2 (da)
DK (1)	DK153838C (da)
EG (1)	EG14345A (da)
ES (1)	ES480552A1 (da)
FI (1)	FI71309C (da)
FR (1)	FR2426047A1 (da)
GB (1)	GB2025395B (da)
GR (1)	GR68396B (da)
HU (1)	HU182565B (da)
IE (1)	IE48372B1 (da)
IL (1)	IL57245A (da)
IT (1)	IT1096361B (da)
MX (1)	MX5927E (da)
NL (2)	NL189255C (da)
NO (1)	NO152840C (da)
NZ (1)	NZ190412A (da)
PH (1)	PH14782A (da)
PT (1)	PT69537A (da)
SE (1)	SE444812B (da)
SU (1)	SU816399A3 (da)
YU (1)	YU112279A (da)
ZA (1)	ZA792015B (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1155853A (en) *	1980-06-06	1983-10-25	Joseph A. Martin	Imidazole derivatives and preparation thereof
FR2541114B1 (fr) *	1983-02-23	1986-04-11	Sanofi Sa	Compositions pharmaceutiques antifongiques utilisables par voie orale contenant de l'omoconazole
EP0117811A3 (fr) *	1983-02-23	1987-06-03	Sanofi S.A.	Compositions pharmaceutiques antifongiques utilisables par voie orale
CA1250586A (en) *	1984-02-02	1989-02-28	Manuel Raga	1h-imidazole derivatives and process for their production
DE3413365A1 (de) *	1984-04-09	1985-12-19	Merz + Co GmbH & Co, 6000 Frankfurt	Substituierte phenylethylderivate, verfahren zu ihrer herstellung und pharmazeutische mittel
IT1200422B (it) *	1985-03-19	1989-01-18	Ripari Gero Ist Farm Biolog	Composto con attivita' antimicrobia,sua preparazione e composizioni farmaceutiche che lo contengono
ES2249992B1 (es) *	2004-09-13	2007-03-01	Ferrer Internacional, S.A.	Un procedimiento para fabricar compuestos enantiomericos del imidazol.

Family Cites Families (2)

* 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
GB1475271A (en) *	1975-04-30	1977-06-01	Pfizer Ltd	1-aryl-2-1-imidazolyl-alkyl ethers and thioethers and their use as antifungal agents

1978
- 1978-05-18 IT IT23546/78A patent/IT1096361B/it active Protection Beyond IP Right Term
1979
- 1979-04-24 PT PT69537A patent/PT69537A/pt unknown
- 1979-04-26 ZA ZA792015A patent/ZA792015B/xx unknown
- 1979-04-27 DE DE2917244A patent/DE2917244C2/de not_active Expired
- 1979-04-29 EG EG250/79A patent/EG14345A/xx active
- 1979-05-07 HU HU79RE645A patent/HU182565B/hu unknown
- 1979-05-07 AR AR276430A patent/AR219596A1/es active
- 1979-05-07 GR GR59034A patent/GR68396B/el unknown
- 1979-05-09 AT AT0345079A patent/AT372950B/de not_active IP Right Cessation
- 1979-05-10 PH PH22475A patent/PH14782A/en unknown
- 1979-05-10 IL IL57245A patent/IL57245A/xx unknown
- 1979-05-10 NZ NZ190412A patent/NZ190412A/xx unknown
- 1979-05-11 CA CA327,426A patent/CA1115718A/en not_active Expired
- 1979-05-14 GB GB7916670A patent/GB2025395B/en not_active Expired
- 1979-05-14 DK DK196579A patent/DK153838C/da not_active IP Right Cessation
- 1979-05-14 NO NO791599A patent/NO152840C/no unknown
- 1979-05-14 ES ES480552A patent/ES480552A1/es not_active Expired
- 1979-05-14 DD DD79212866A patent/DD143608A5/de unknown
- 1979-05-14 YU YU01122/79A patent/YU112279A/xx unknown
- 1979-05-15 FI FI791543A patent/FI71309C/fi not_active IP Right Cessation
- 1979-05-16 CH CH456979A patent/CH639075A5/fr not_active IP Right Cessation
- 1979-05-16 JP JP54060971A patent/JPS605592B2/ja not_active Expired
- 1979-05-16 NL NLAANVRAGE7903872,A patent/NL189255C/xx not_active IP Right Cessation
- 1979-05-17 SE SE7904319A patent/SE444812B/sv not_active IP Right Cessation
- 1979-05-17 AU AU47149/79A patent/AU523053B2/en not_active Expired
- 1979-05-17 SU SU792771698A patent/SU816399A3/ru active
- 1979-05-17 FR FR7912638A patent/FR2426047A1/fr active Granted
- 1979-05-18 MX MX797989U patent/MX5927E/es unknown
- 1979-08-08 IE IE958/79A patent/IE48372B1/en not_active IP Right Cessation
1993
- 1993-02-19 NL NL930014C patent/NL930014I2/nl unknown

Also Published As

Publication number	Publication date
NL930014I1 (nl)	1993-05-03
DK153838C (da)	1989-01-30
PT69537A (fr)	1979-05-01
FI791543A7 (fi)	1979-11-19
IL57245A0 (en)	1979-09-30
DE2917244A1 (de)	1979-11-22
IE790958L (en)	1979-11-18
JPS54151974A (en)	1979-11-29
ATA345079A (de)	1983-04-15
DK153838B (da)	1988-09-12
FI71309B (fi)	1986-09-09
SU816399A3 (ru)	1981-03-23
NL189255C (nl)	1993-02-16
DE2917244C2 (de)	1985-09-05
NL7903872A (nl)	1979-11-20
IL57245A (en)	1983-02-23
GB2025395B (en)	1982-07-28
GR68396B (da)	1981-12-29
NO152840B (no)	1985-08-19
ES480552A1 (es)	1980-04-01
NO791599L (no)	1979-11-20
DK196579A (da)	1979-11-19
SE444812B (sv)	1986-05-12
EG14345A (en)	1983-09-30
FI71309C (fi)	1986-12-19
CH639075A5 (fr)	1983-10-31
IE48372B1 (en)	1984-12-26
NZ190412A (en)	1981-03-16
SE7904319L (sv)	1979-11-19
HU182565B (en)	1984-02-28
AU4714979A (en)	1979-11-22
JPS605592B2 (ja)	1985-02-12
AT372950B (de)	1983-11-25
NO152840C (no)	1985-11-27
AR219596A1 (es)	1980-08-29
YU112279A (en)	1983-01-21
FR2426047B1 (da)	1982-11-05
FR2426047A1 (fr)	1979-12-14
IT1096361B (it)	1985-08-26
GB2025395A (en)	1980-01-23
IT7823546A0 (it)	1978-05-18
CA1115718A (en)	1982-01-05
NL930014I2 (nl)	1993-09-16
PH14782A (en)	1981-12-09
ZA792015B (en)	1980-04-30
AU523053B2 (en)	1982-07-08
MX5927E (es)	1984-08-29

Publication	Publication Date	Title
AT407832B (de)	2001-06-25	Fungizides mittel, eine verbindung hierfür, verfahren zu ihrer herstellung und verfahren zu ihrer verwendung
DE1940388C3 (de)	1978-05-11	l-(ß-Aryl) äthylimidazolderivate, ihre Herstellung und diese enthaltende fungizide und bakterizide Mittel
DE2037610C3 (da)	1979-07-12
EP0041673B1 (de)	1984-10-10	Imidazolderivate, deren Herstellung sowie diese enthaltende Präparate
EP0011769B1 (de)	1982-04-14	Hydroxyethyl-azole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE2041771B2 (de)	1978-11-23	derivate
EP0011768B1 (de)	1981-10-21	Hydroxypropyl-triazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
CH646693A5 (de)	1984-12-14	Benzylimidazol-derivate.
DE2839388A1 (de)	1980-03-27	Imidazolylvinylaether und deren verwendung
EP0003796B1 (de)	1980-10-15	Substituierte Diphenyl-imidazolyl-methane, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel
DE2917244C2 (de)	1985-09-05	1-[[2-(2,4-Dichlorphenyl)-2-benzyloxy]-äthyl]-imidazole, Verfahren zu deren Herstellung sowie solche enthaltende Arzneimittel
DE2920437A1 (de)	1980-11-27	Geometrische isomere von 4,4- dimethyl-1-phenyl-2-(1,2,4-triazol-1-yl)- 1-penten-3-olen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2811916A1 (de)	1979-09-27	Antimikrobielle mittel
DE3010093A1 (de)	1981-10-01	1,1-diphenyl-2-(1.2.4-triazol-1-yl)-aethan-1-ole, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel
EP0088874A2 (de)	1983-09-21	Azolyl-phenoxy-tetrahydrofuran-2-yliden-methane, Verfahren zu ihrer Herstellung sowie antimikrobielle Mittel, die diese Stoffe enthalten
DD270305A5 (de)	1989-07-26	Verfahren zur herstellung von neuen benzofuron-2-yl-imidozol-derivaten
DE2242454A1 (de)	1974-03-07	1-aethyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE69500329T2 (de)	1997-10-30	Neue Triazol-Verbindung mit fungizider Wirkung, deren Herstellung und Verwendung
EP0370300A2 (de)	1990-05-30	Cyclopropyl-Substituierte Azolylmethylcarbinole, Verfarhren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0533056A2 (de)	1993-03-24	Substituierte Aminopropane, Verfahren zu ihrer Herstellung und ihre Verwendung als Antimykutiku
EP0022969B1 (de)	1983-05-25	Antimykotische Mittel, die Azolyl-alkenole enthalten und ihre Herstellung
DE2013793C2 (de)	1983-02-03	N-Methyl-imidazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0276466A2 (de)	1988-08-03	Aminoazolderivate, Verfahren zu deren Herstellung und deren Verwendung als antimykotische Mittel
DE2059949B2 (de)	1979-04-05	Thienyl-fettsäurederivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
EP0037049A1 (de)	1981-10-07	Biphenylyl-imidazolylethan-Derivate, Verfahren zu ihrer Herstellung und diese Verbindingungen enthaltende Arzneimittel