FI59992C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-(fenoxialkyltio)-imidazoler - Google Patents

Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-(fenoxialkyltio)-imidazoler Download PDF

Info

Publication number: FI59992C
Authority: FI; Finland
Prior art keywords: parts; formula; alk; methyl; compound
Prior art date: 1973-01-22

Application number

FI159/74A

Other languages

English (en)

Finnish (fi)

Other versions

FI59992B (fi

Inventor

Robert Christopher Tweit

Original Assignee

Searle & Co

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.)

1973-01-22

Filing date

1974-01-21

Publication date

1981-11-10

1974-01-21 Application filed by Searle & Co filed Critical Searle & Co

1979-09-03 Priority to FI792727A priority Critical patent/FI59994C/fi

1979-09-03 Priority to FI792728A priority patent/FI59995C/fi

1981-07-31 Publication of FI59992B publication Critical patent/FI59992B/fi

1981-11-10 Application granted granted Critical

1981-11-10 Publication of FI59992C publication Critical patent/FI59992C/fi

Links

230000000144 pharmacologic effect Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 40
-1 cyano, formyl Chemical group 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
239000000460 chlorine Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
150000002460 imidazoles Chemical class 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
150000004703 alkoxides Chemical class 0.000 claims 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 30
239000000243 solution Substances 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000002609 medium Substances 0.000 description 12
238000005292 vacuum distillation Methods 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
125000000446 sulfanediyl group Chemical group *S* 0.000 description 8
PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
ZMPAPJBFYQSNFM-UHFFFAOYSA-N 1-sulfanylimidazole Chemical compound SN1C=CN=C1 ZMPAPJBFYQSNFM-UHFFFAOYSA-N 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000008272 agar Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
XFHTVCMRNSBQCF-UHFFFAOYSA-N 4-(2-bromoethoxy)benzaldehyde Chemical compound BrCCOC1=CC=C(C=O)C=C1 XFHTVCMRNSBQCF-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
241000224527 Trichomonas vaginalis Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
230000000842 anti-protozoal effect Effects 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
NGHCZLIYHYHPSI-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-(dimethoxymethyl)benzene Chemical compound BrCCOC1=CC=C(C=C1)C(OC)OC NGHCZLIYHYHPSI-UHFFFAOYSA-N 0.000 description 2
XYOBIVYDGVADPM-UHFFFAOYSA-N 1-methyl-2-(4-phenoxybutylsulfanyl)imidazole;hydrobromide Chemical group Br.CN1C=CN=C1SCCCCOC1=CC=CC=C1 XYOBIVYDGVADPM-UHFFFAOYSA-N 0.000 description 2
125000006016 2-bromoethoxy group Chemical group 0.000 description 2
IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 2
QAFABILEXKEFJK-UHFFFAOYSA-N 5-bromo-3-[5-bromo-3-formyl-2-(3-methylpentyl)phenoxy]-2-(3-methylpentyl)benzaldehyde Chemical compound BrC=1C=C(C(=C(C=1)OC1=C(C(=CC(=C1)Br)C=O)CCC(CC)C)CCC(CC)C)C=O QAFABILEXKEFJK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
244000026610 Cynodon dactylon var. affinis Species 0.000 description 2
241000588652 Neisseria gonorrhoeae Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
241000223892 Tetrahymena Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002015 acyclic group Chemical group 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
230000000635 anti-gonococcal effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
YDPZWUMQKMLLHC-UHFFFAOYSA-N 1,5-dibromo-3-methylpentane Chemical compound BrCCC(C)CCBr YDPZWUMQKMLLHC-UHFFFAOYSA-N 0.000 description 1
LVWSZGCVEZRFBT-UHFFFAOYSA-N 1,7-dibromoheptane Chemical compound BrCCCCCCCBr LVWSZGCVEZRFBT-UHFFFAOYSA-N 0.000 description 1
QMXCOUDFAICZHW-UHFFFAOYSA-N 1-(7-bromoheptyl)-3-[3-(7-bromoheptyl)-2-nitrophenoxy]-2-nitrobenzene Chemical compound BrCCCCCCCC=1C(=C(C=CC=1)OC1=C(C(=CC=C1)CCCCCCCBr)[N+](=O)[O-])[N+](=O)[O-] QMXCOUDFAICZHW-UHFFFAOYSA-N 0.000 description 1
SZSHKOYMLVVNKI-UHFFFAOYSA-N 1-methyl-2-(2-phenoxyethylsulfanyl)imidazole Chemical compound CN1C=CN=C1SCCOC1=CC=CC=C1 SZSHKOYMLVVNKI-UHFFFAOYSA-N 0.000 description 1
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
QWVHQBUYHWVJRS-UHFFFAOYSA-N 2-benzylsulfonyl-1-methyl-5-nitroimidazole Chemical compound CN1C([N+]([O-])=O)=CN=C1S(=O)(=O)CC1=CC=CC=C1 QWVHQBUYHWVJRS-UHFFFAOYSA-N 0.000 description 1
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IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
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RCJRHCFNVBGSRP-UHFFFAOYSA-N 3-hexyl-1h-imidazole-2-thione Chemical compound CCCCCCN1C=CN=C1S RCJRHCFNVBGSRP-UHFFFAOYSA-N 0.000 description 1
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239000002585 base Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
BZLVOUTZDHRJPD-UHFFFAOYSA-N ethyl 4-(2-bromoethoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(OCCBr)C=C1 BZLVOUTZDHRJPD-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
230000004083 survival 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
150000003568 thioethers Chemical class 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Classifications

- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Catalysts (AREA)

FI159/74A 1973-01-22 1974-01-21 Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-(fenoxialkyltio)-imidazoler FI59992C (fi)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
FI792727A FI59994C (fi)	1973-01-22	1979-09-03	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-(fenoxialkyltio)-5-nitroimidazoler
FI792728A FI59995C (fi)	1973-01-22	1979-09-03	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-(fenoxialkylsulfinyl eller -sulfonyl)-imidazoler

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US00325223A US3842097A (en)	1973-01-22	1973-01-22	2-(phenoxyalkylthio)imidazoles and congeners
US32522373		1973-01-22

Publications (2)

Publication Number	Publication Date
FI59992B FI59992B (fi)	1981-07-31
FI59992C true FI59992C (fi)	1981-11-10

Family

ID=23266954

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI159/74A FI59992C (fi)	1973-01-22	1974-01-21	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-(fenoxialkyltio)-imidazoler

Country Status (24)

Country	Link
US (1)	US3842097A (de)
JP (1)	JPS49108076A (de)
AR (3)	AR199944A1 (de)
AT (1)	AT333271B (de)
BE (1)	BE809980A (de)
CA (1)	CA1033744A (de)
CH (1)	CH601254A5 (de)
DE (1)	DE2402672A1 (de)
DK (1)	DK136469B (de)
EG (1)	EG11033A (de)
ES (2)	ES422472A1 (de)
FI (1)	FI59992C (de)
FR (1)	FR2214481B1 (de)
GB (1)	GB1413262A (de)
GT (1)	GT197431632A (de)
HU (1)	HU167963B (de)
IE (1)	IE39153B1 (de)
IL (1)	IL44045A (de)
NL (1)	NL7400782A (de)
NO (3)	NO141208C (de)
OA (1)	OA04682A (de)
PH (1)	PH10212A (de)
SE (3)	SE405116B (de)
ZA (1)	ZA74140B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2333355C2 (de) *	1973-06-30	1984-01-19	Bayer Ag, 5090 Leverkusen	Antimikrobielle Mittel
EG12284A (en) *	1975-07-12	1978-09-30	Hoechst Ag	Process for the preparation of 1-methyl-2-(phenyl 6 oxymethyl)-5-nitro-imidazoles
US4098824A (en) *	1975-10-02	1978-07-04	Laboratoire L. Lafon	Benzhydrylsulphinyl derivatives
LU77703A1 (de) *	1977-07-07	1979-03-26	Ciba Geigy Ag	Verfahren zur herstellung von bicyclischen thia-diaza-verbindungen
DE2823197A1 (de) *	1978-05-24	1979-11-29	Schering Ag	Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
DE2856909A1 (de) *	1978-12-28	1980-07-17	Schering Ag	Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate
IT1248528B (it) *	1991-06-21	1995-01-19	Pierrel Spa	Derivati di eteri e tioeteri (etero) aromatici aventi attivita` antiiperlipidemica, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono.
US5179117A (en) *	1991-12-20	1993-01-12	Du Pont Merck Pharmaceutical Company	Antihypercholesterolemic 2-substituted imidazoles
JP4728000B2 (ja) *	2005-01-17	2011-07-20	セイコーインスツル株式会社	携帯時計

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3636003A (en) *	1969-11-17	1972-01-18	Geigy Chem Corp	Substituted 2-mercaptoimidazole derivatives
US3714179A (en) *	1970-09-08	1973-01-30	Searle & Co	1-alkyl-2-furfurylthioimidazoles and congeners

1973
- 1973-01-22 US US00325223A patent/US3842097A/en not_active Expired - Lifetime
1974
- 1974-01-08 ZA ZA00740140A patent/ZA74140B/xx unknown
- 1974-01-16 GT GT197431632A patent/GT197431632A/es unknown
- 1974-01-21 CA CA190,547A patent/CA1033744A/en not_active Expired
- 1974-01-21 AR AR252002A patent/AR199944A1/es active
- 1974-01-21 DK DK31374AA patent/DK136469B/da unknown
- 1974-01-21 IL IL44045A patent/IL44045A/en unknown
- 1974-01-21 NO NO740184A patent/NO141208C/no unknown
- 1974-01-21 BE BE140019A patent/BE809980A/xx unknown
- 1974-01-21 SE SE7400739A patent/SE405116B/xx unknown
- 1974-01-21 FI FI159/74A patent/FI59992C/fi active
- 1974-01-21 EG EG17/74A patent/EG11033A/xx active
- 1974-01-21 IE IE118/74A patent/IE39153B1/xx unknown
- 1974-01-21 PH PH15432*A patent/PH10212A/en unknown
- 1974-01-21 DE DE2402672A patent/DE2402672A1/de not_active Withdrawn
- 1974-01-21 ES ES422472A patent/ES422472A1/es not_active Expired
- 1974-01-21 NL NL7400782A patent/NL7400782A/xx not_active Application Discontinuation
- 1974-01-21 AT AT48374*#A patent/AT333271B/de not_active IP Right Cessation
- 1974-01-21 GB GB274274A patent/GB1413262A/en not_active Expired
- 1974-01-22 OA OA55103A patent/OA04682A/xx unknown
- 1974-01-22 HU HUSE1707A patent/HU167963B/hu unknown
- 1974-01-22 CH CH82274A patent/CH601254A5/xx not_active IP Right Cessation
- 1974-01-22 JP JP49009669A patent/JPS49108076A/ja active Pending
- 1974-01-22 FR FR7402126A patent/FR2214481B1/fr not_active Expired
- 1974-09-18 AR AR255634A patent/AR202044A1/es active
- 1974-09-18 AR AR255635A patent/AR201787A1/es active
1976
- 1976-03-16 ES ES446126A patent/ES446126A1/es not_active Expired
- 1976-08-11 SE SE7608958A patent/SE421312B/xx unknown
- 1976-08-11 SE SE7608956A patent/SE421313B/xx unknown
1978
- 1978-01-12 NO NO780122A patent/NO140629C/no unknown
- 1978-01-12 NO NO780121A patent/NO140468C/no unknown

Also Published As

Publication number	Publication date
AR199944A1 (es)	1974-10-08
CH601254A5 (de)	1978-06-30
NO140629B (no)	1979-07-02
PH10212A (en)	1976-09-29
NO740184L (no)	1974-07-23
NO140468B (no)	1979-05-28
BE809980A (fr)	1974-07-22
GT197431632A (es)	1975-07-10
US3842097A (en)	1974-10-15
NO140468C (no)	1979-09-05
AU6469474A (en)	1975-07-24
SE7608956L (sv)	1976-08-11
FI59992B (fi)	1981-07-31
HU167963B (de)	1976-01-28
SE421313B (sv)	1981-12-14
DE2402672A1 (de)	1974-07-25
OA04682A (fr)	1980-07-31
SE7608958L (sv)	1976-08-11
SE405116B (sv)	1978-11-20
IL44045A (en)	1976-09-30
NO141208C (no)	1980-01-30
GB1413262A (en)	1975-11-12
ZA74140B (en)	1975-08-27
AR201787A1 (es)	1975-04-15
AT333271B (de)	1976-11-10
FR2214481B1 (de)	1977-04-22
IE39153L (en)	1974-07-22
CA1033744A (en)	1978-06-27
ATA48374A (de)	1976-03-15
NO780122L (no)	1974-07-23
NO141208B (no)	1979-10-22
JPS49108076A (de)	1974-10-14
DK136469C (de)	1978-03-13
NO780121L (no)	1974-07-23
NL7400782A (de)	1974-07-24
NO140629C (no)	1979-10-10
IE39153B1 (en)	1978-08-16
DK136469B (da)	1977-10-17
FR2214481A1 (de)	1974-08-19
AR202044A1 (es)	1975-05-09
ES422472A1 (es)	1976-10-01
SE421312B (sv)	1981-12-14
IL44045A0 (en)	1974-05-16
EG11033A (en)	1976-10-31
ES446126A1 (es)	1977-12-01

Publication	Publication Date	Title
EP0045081B1 (de)	1986-01-08	Neue trisubstituierte Imidazolderivate, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate und ihre Verwendung
Godefroi et al.	1965	DL-1-(1-arylalkyl) imidazole-5-carboxylate esters. A novel type of hypnotic agents
US4034010A (en)	1977-07-05	Bis-(meta-amidinophenoxy)-compounds and pharmacologically acceptable acid addition salts thereof
FI59992B (fi)	1981-07-31	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-(fenoxialkyltio)-imidazoler
FI65992B (fi)	1984-04-30	Foerfarande foer framstaellning av nya antimykotiska hydroxipropyl-triazolderivat
JPH0629279B2 (ja)	1994-04-20	ヨードプロパルギルエーテル類、それらの製造法およびそれらの使用
US3956262A (en)	1976-05-11	Triazenoimidazoles
US3957812A (en)	1976-05-18	Derivatives of 2-phenoxyacetamido-5-nitro-thiazole
US4478846A (en)	1984-10-23	2-(1-Alkyl-5-nitro)-imidazolyl-1-(2-hydroxy-5-alkyl)-phenyl carbinols and pharmaceutical compositions containing them
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
FI59994C (fi)	1981-11-10	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-(fenoxialkyltio)-5-nitroimidazoler
CA1115718A (en)	1982-01-05	Therapeutically active substituted dibenzyl ethers
US3600399A (en)	1971-08-17	Certain 2-amino-5-imidazol-2-yl-1,3,4-thiadiazoles
US4169205A (en)	1979-09-25	Imidazole derivatives of 6,11-dihydrodibenz[b,e]oxepines and 6,11-dihydrodibenz[b,e]thiepines
US4228177A (en)	1980-10-14	2,3-Dihydro-3-(1H-imidazol-1-ylmethylene)-4H-1-benzothiopyran-4-ones
US3828065A (en)	1974-08-06	2-methyl-5-nitro-1-(2-phenylthioethyl)imidazoles
US4376788A (en)	1983-03-15	Basic ethers of 4-hydroxy-benzophenones acting as beta-blocking agents
US3692794A (en)	1972-09-19	1,2,4-thiadiazoles
US3995046A (en)	1976-11-30	Esters of 5-n-butylpyridine-2 carboxylic acid and pharmaceutical compositions containing these compounds
US3790587A (en)	1974-02-05	Antimycotic benzisothiazoline derivatives
FI62096C (fi)	1982-11-10	Foerfarande foer framstaellning av nya 1- och d1-6-(m-(isotiazol-5-karboxiamido)fenyl)-2,3,5,6-tetrahydroimidazo(2,1-b)tiazolderivat vilka anvaends som maskmedel
CN117550979B (zh)	2025-03-11	香草酸衍生物及其制备方法与应用
NO126321B (de)	1973-01-22
CH493525A (de)	1970-07-15	Verfahren zur Herstellung von Nitroimidazolen
US4243596A (en)	1981-01-06	(5-Nitro-2-furyl)vinylene-2-trimethylammonium bromide and method of preparing same