CS241468B2 - Method of 1h-imidazole and 1h-1,2,4-triazole new derivatives production - Google Patents

Method of 1h-imidazole and 1h-1,2,4-triazole new derivatives production Download PDF

Info

Publication number: CS241468B2
Authority: CS; Czechoslovakia
Prior art keywords: phenyl; triazol; piperazinyl; parts; formula
Prior art date: 1978-06-23

Application number

CS794087A

Other languages

Czech (cs)

English (en)

Other versions

CS408779A2 (en

Inventor

Jan Heeres

Leo J J Backx

Original Assignee

Janssen Pharmaceutica Nv

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.)

1978-06-23

Filing date

1979-06-13

Publication date

1986-03-13

1979-06-13 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1985-08-15 Publication of CS408779A2 publication Critical patent/CS408779A2/cs

1986-03-13 Publication of CS241468B2 publication Critical patent/CS241468B2/cs

Links

238000000034 method Methods 0.000 title claims description 15
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title description 4
RAXXELZNTBOGNW-MQIHXRCWSA-N 1h-imidazole Chemical compound C1=C[15NH]C=[15N]1 RAXXELZNTBOGNW-MQIHXRCWSA-N 0.000 title 1
-1 halothienyl Chemical group 0.000 claims abstract description 175
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 172
150000001875 compounds Chemical class 0.000 claims description 54
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
150000002148 esters Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 32
230000000844 anti-bacterial effect Effects 0.000 abstract description 3
UGUAAAKGQBAZBF-UHFFFAOYSA-N 2-(1,3-dioxolan-4-yl)ethanesulfonic acid Chemical class OS(=O)(=O)CCC1COCO1 UGUAAAKGQBAZBF-UHFFFAOYSA-N 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000001188 haloalkyl group Chemical group 0.000 abstract 1
125000001544 thienyl group Chemical group 0.000 abstract 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 64
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
239000000203 mixture Substances 0.000 description 51
239000000047 product Substances 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 32
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 29
238000003756 stirring Methods 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
239000000243 solution Substances 0.000 description 17
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
239000007858 starting material Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000003054 catalyst Substances 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
229960001701 chloroform Drugs 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
241000700159 Rattus Species 0.000 description 7
239000006185 dispersion Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
238000010898 silica gel chromatography Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
239000003480 eluent Substances 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
238000005187 foaming Methods 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
241000222122 Candida albicans Species 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000233866 Fungi Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000286209 Phasianidae Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
229940095731 candida albicans Drugs 0.000 description 4
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
PXIWVQOMRFOFBG-UHFFFAOYSA-N 3-methyl-4-(4-nitrophenyl)-1h-1,2,4-triazol-5-one Chemical compound CC1=NNC(=O)N1C1=CC=C([N+]([O-])=O)C=C1 PXIWVQOMRFOFBG-UHFFFAOYSA-N 0.000 description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000013543 active substance Substances 0.000 description 3
230000000843 anti-fungal effect Effects 0.000 description 3
230000000845 anti-microbial effect Effects 0.000 description 3
229940121375 antifungal agent Drugs 0.000 description 3
238000001035 drying Methods 0.000 description 3
WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 3
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 3
244000005700 microbiome Species 0.000 description 3
239000000376 reactant Substances 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000000126 substance Substances 0.000 description 3
ZVRXDYHMCJQEFP-UHFFFAOYSA-N 1-(4-isothiocyanatophenyl)-4-(4-methoxyphenyl)piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(=CC=2)N=C=S)CC1 ZVRXDYHMCJQEFP-UHFFFAOYSA-N 0.000 description 2
AVCKOFMRPAJEPN-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-(4-nitrophenyl)piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(=CC=2)[N+]([O-])=O)CC1 AVCKOFMRPAJEPN-UHFFFAOYSA-N 0.000 description 2
KOTUQWHVKPWTFS-UHFFFAOYSA-N 1-(4-nitrophenyl)-5-propyl-1,2,4-triazole;hydrochloride Chemical compound Cl.CCCC1=NC=NN1C1=CC=C([N+]([O-])=O)C=C1 KOTUQWHVKPWTFS-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
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
WZIJMPVPOMTRNM-UHFFFAOYSA-N 4-[4-(4-aminophenyl)piperazin-1-yl]phenol Chemical compound C1=CC(N)=CC=C1N1CCN(C=2C=CC(O)=CC=2)CC1 WZIJMPVPOMTRNM-UHFFFAOYSA-N 0.000 description 2
VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 2
JIDHCLKADLPSJT-UHFFFAOYSA-N 5-ethyl-3-methylsulfanyl-1-(4-nitrophenyl)-1,2,4-triazole Chemical compound CCC1=NC(SC)=NN1C1=CC=C([N+]([O-])=O)C=C1 JIDHCLKADLPSJT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
238000007126 N-alkylation reaction Methods 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000003819 basic metal compounds Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
125000000068 chlorophenyl group Chemical group 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
235000013305 food Nutrition 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000000464 thioxo group Chemical group S=* 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 description 1
LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 description 1
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235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940024986 topical antifungal imidazole and triazole derivative Drugs 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CS794087A 1978-06-23 1979-06-13 Method of 1h-imidazole and 1h-1,2,4-triazole new derivatives production CS241468B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US91933378A	1978-06-23	1978-06-23

Publications (2)

Publication Number	Publication Date
CS408779A2 CS408779A2 (en)	1985-08-15
CS241468B2 true CS241468B2 (en)	1986-03-13

Family

ID=25441906

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS794087A CS241468B2 (en)	1978-06-23	1979-06-13	Method of 1h-imidazole and 1h-1,2,4-triazole new derivatives production

Country Status (6)

Country	Link
KR (1)	KR820001889B1 (pl)
CS (1)	CS241468B2 (pl)
LV (1)	LV5017A3 (pl)
PL (1)	PL117988B1 (pl)
SU (1)	SU1069625A3 (pl)
ZA (1)	ZA793128B (pl)

1979
- 1979-06-13 KR KR7901926A patent/KR820001889B1/ko not_active Expired
- 1979-06-13 CS CS794087A patent/CS241468B2/cs unknown
- 1979-06-22 ZA ZA793128A patent/ZA793128B/xx unknown
- 1979-06-22 SU SU792782151A patent/SU1069625A3/ru active
- 1979-06-23 PL PL1979216555A patent/PL117988B1/pl unknown
1992
- 1992-11-09 LV LV920188A patent/LV5017A3/xx unknown

Also Published As

Publication number	Publication date
KR820001889B1 (ko)	1982-10-18
PL216555A1 (pl)	1980-03-24
SU1069625A3 (ru)	1984-01-23
ZA793128B (en)	1981-02-25
PL117988B1 (en)	1981-09-30
CS408779A2 (en)	1985-08-15
LV5017A3 (lv)	1993-06-10

Publication	Publication Date	Title
CA1149386A (en)	1983-07-05	Heterocyclic derivatives of (4-phenyl- piperazin-1-ylaryloxymethyl-1,3-dioxolan- 2-yl)methyl-1h-imidazoles and 1h-1,2,4-triazoles
JP2574656B2 (ja)	1997-01-22	置換（４−フエニル−１−ピペラジニル）フエノール誘導体及びその製造方法
US4916134A (en)	1990-04-10	4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-azolylmethyl)-1,3-dioxolan-4-yl]me]phenyl]-1-piperazinyl]phenyl]triazolones
FI62836C (fi)	1983-03-10	Foerfarande foer framstaellning av heterocykliska derivat av bakterier och svampar foerstoerande 1-(1,3-dioxolan-2-ylmetyl)-1h-imidazoler och -1h-1,2,4-triazoler
FI89798B (fi)	1993-08-13	Framstaellning av 4-/4-/4-/4-//2-(2,4-difluorfenyl)-2-(1h-azolylmetyl)-1,3-dioxolan-4-yl/metoxi/fenyl/-1-piperazinyl/fenyl/triazoloner
JPH05246999A (ja)	1993-09-24	置換フエニル誘導体
CZ195696A3 (en)	1997-02-12	Azoles, process of their preparation and pharmaceutical compositions based thereon
FI96031C (fi)	1996-04-25	Menetelmä terapeuttisesti aktiivisten 4-/4-/4-/4-/2-(2,4-difluorifenyyli)-2-(1H-atsolyylimetyyli)-1,3-dioksolan-4-yyli/metoksi/fenyyli/-1-piperatsinyyli/fenyylisubstituoitujen triatsolonien ja imidatsolonien valmistamiseksi
NZ305869A (en)	1998-08-26	2-[4-[4-[4-[[2-(triazolyl-alkyl or imidazolyl-alkyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl] -2,4-dihydro-3h-1,2,4-triazol-3-one derivatives, intermediates and medicaments
US4490530A (en)	1984-12-25	Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)-methyl-1H-imidazoles and 1H-1,2,4-triazoles
US4368200A (en)	1983-01-11	Heterocyclic derivatives of (4-phenyl-piperazine-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)-methyl-1H-imidazoles and 1H-1,2,4-triazoles
CS241468B2 (en)	1986-03-13	Method of 1h-imidazole and 1h-1,2,4-triazole new derivatives production
US4229460A (en)	1980-10-21	Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazoles having antifungal and antibacterial properties
US4244964A (en)	1981-01-13	Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazoles
US4232034A (en)	1980-11-04	Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
US4268680A (en)	1981-05-19	Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles and 1H-1,2,4-triazoles
BG60430B2 (bg)	1995-03-31	Хетероциклични производни на (4-фенилпиперазин-1-ил-арилокси- метил-1,3-диоксолан-2-ил)-метил-1н-имидазоли и 1н-1,2,4-триа- золи,методи за тяхното получаване и състави,които ги съдържат
KR810000676B1 (ko)	1981-06-20	디옥소란의 헤테로 고리치환체 제조방법
HU184845B (en)	1984-10-29	Process for producing 1-bracket-1,3-dioxol-2-nyl-methyl-bracket closed-1h-1,2,4-triazole derivatives
HK1012186B (en)	2002-02-22	Triazolones as apolipoprotein-b synthesis inhibitors
JPH01211561A (ja)	1989-08-24	含窒素複素環基置換フエニルピペラジニルフエノール及びその製造方法