CH493499A - Verfahren zur Herstellung von neuen O,N-Diphenyl-carbaminsäureestern - Google Patents
Verfahren zur Herstellung von neuen O,N-Diphenyl-carbaminsäureesternInfo
- Publication number
- CH493499A CH493499A CH651470A CH651470A CH493499A CH 493499 A CH493499 A CH 493499A CH 651470 A CH651470 A CH 651470A CH 651470 A CH651470 A CH 651470A CH 493499 A CH493499 A CH 493499A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- ester
- chlorophenyl
- carbamic acid
- dichlorophenoxy
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title description 83
- 230000000845 anti-microbial effect Effects 0.000 title description 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- -1 alkaline earth metal salts Chemical class 0.000 claims description 38
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 239000003429 antifungal agent Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
- 239000003826 tablet Substances 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 7
- 239000000454 talc Substances 0.000 description 7
- 229910052623 talc Inorganic materials 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- LQMWWRSOANZFNV-UHFFFAOYSA-N (3-methoxyphenyl)carbamic acid Chemical compound COC1=CC=CC(NC(O)=O)=C1 LQMWWRSOANZFNV-UHFFFAOYSA-N 0.000 description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 5
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 5
- 239000008298 dragée Substances 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 230000000968 intestinal effect Effects 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000004659 sterilization and disinfection Methods 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical class C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 210000001635 urinary tract Anatomy 0.000 description 4
- OAYMUOAVUHJSNG-UHFFFAOYSA-N (3-bromophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Br)=C1 OAYMUOAVUHJSNG-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
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
- 241001503016 Ctenomyces Species 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- RCFJOIDKQQRXHU-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=CC(C(F)(F)F)=C1 RCFJOIDKQQRXHU-UHFFFAOYSA-N 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000249 desinfective effect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- AOVLXBXJFYNQAZ-UHFFFAOYSA-N ethyl n-(3,4-dichlorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 AOVLXBXJFYNQAZ-UHFFFAOYSA-N 0.000 description 3
- 230000001408 fungistatic effect Effects 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 239000006916 nutrient agar Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 3
- UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 description 2
- GAWCRULEMQFHTI-UHFFFAOYSA-N (4-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(Cl)C=C1 GAWCRULEMQFHTI-UHFFFAOYSA-N 0.000 description 2
- VZQDNZQCQKJHNO-UHFFFAOYSA-N (4-methoxyphenyl)carbamic acid Chemical compound COC1=CC=C(NC(O)=O)C=C1 VZQDNZQCQKJHNO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
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- 244000215068 Acacia senegal Species 0.000 description 2
- 241001112577 Acrostalagmus Species 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
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- 241000191940 Staphylococcus Species 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- 239000000969 carrier Substances 0.000 description 2
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
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- KVEROPFXBPXHCI-UHFFFAOYSA-N (2,4,5-trichlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC(Cl)=C(Cl)C=C1Cl KVEROPFXBPXHCI-UHFFFAOYSA-N 0.000 description 1
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- CREZIHDFCDXCBT-UHFFFAOYSA-N (2,6-dimethylphenyl)carbamic acid Chemical compound CC1=CC=CC(C)=C1NC(O)=O CREZIHDFCDXCBT-UHFFFAOYSA-N 0.000 description 1
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- WOTADXXYCGPDFG-UHFFFAOYSA-N (2-methylphenyl)carbamothioic s-acid Chemical compound CC1=CC=CC=C1NC(S)=O WOTADXXYCGPDFG-UHFFFAOYSA-N 0.000 description 1
- CETFZQKQVLJYPD-UHFFFAOYSA-N (3,4-dichlorophenyl)carbamothioic s-acid Chemical compound SC(=O)NC1=CC=C(Cl)C(Cl)=C1 CETFZQKQVLJYPD-UHFFFAOYSA-N 0.000 description 1
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- JJEWAISZYKKDEY-UHFFFAOYSA-N (4-chlorophenyl)carbamothioic s-acid Chemical compound OC(=S)NC1=CC=C(Cl)C=C1 JJEWAISZYKKDEY-UHFFFAOYSA-N 0.000 description 1
- QVVJZHVEBUNKBZ-UHFFFAOYSA-N (4-fluorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(F)C=C1 QVVJZHVEBUNKBZ-UHFFFAOYSA-N 0.000 description 1
- MSMJEQQYVMQBSR-UHFFFAOYSA-N (4-hydroxyphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(O)C=C1 MSMJEQQYVMQBSR-UHFFFAOYSA-N 0.000 description 1
- HCRLLKWHMZNNKR-UHFFFAOYSA-N (4-methylphenyl)carbamothioic s-acid Chemical compound CC1=CC=C(NC(S)=O)C=C1 HCRLLKWHMZNNKR-UHFFFAOYSA-N 0.000 description 1
- BIAQHGJHCDEDSE-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidin-2-amine Chemical class NC1NCC=CN1 BIAQHGJHCDEDSE-UHFFFAOYSA-N 0.000 description 1
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 1
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 241000590020 Achromobacter Species 0.000 description 1
- 241000588813 Alcaligenes faecalis Species 0.000 description 1
- 241000094558 Antrodia sinuosa Species 0.000 description 1
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- 241000193830 Bacillus <bacterium> Species 0.000 description 1
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- 241000221204 Cryptococcus neoformans Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 241000123284 Daedalea Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
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- WPKCDZWJIHOQDZ-UHFFFAOYSA-N O=C(Cl)[ClH]C(C=CC=C1)=C1OC1=CC=CC=C1 Chemical class O=C(Cl)[ClH]C(C=CC=C1)=C1OC1=CC=CC=C1 WPKCDZWJIHOQDZ-UHFFFAOYSA-N 0.000 description 1
- 241001236817 Paecilomyces <Clavicipitaceae> Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000228150 Penicillium chrysogenum Species 0.000 description 1
- 241000228153 Penicillium citrinum Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
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- 241000635201 Pumilus Species 0.000 description 1
- 241000235546 Rhizopus stolonifer Species 0.000 description 1
- QMLSRZPPXQJUPF-UHFFFAOYSA-N S=C(Cl)[ClH]C(C=C(C=C1)Cl)=C1OC(C=CC(Cl)=C1)=C1Cl Chemical compound S=C(Cl)[ClH]C(C=C(C=C1)Cl)=C1OC(C=CC(Cl)=C1)=C1Cl QMLSRZPPXQJUPF-UHFFFAOYSA-N 0.000 description 1
- 241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
- 241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 description 1
- 241000577483 Salmonella enterica subsp. enterica serovar Paratyphi B Species 0.000 description 1
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000192023 Sarcina Species 0.000 description 1
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- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 241000607764 Shigella dysenteriae Species 0.000 description 1
- 206010040550 Shigella infections Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000186652 Sporosarcina ureae Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000514831 Stemphylium botryosum Species 0.000 description 1
- 241000222355 Trametes versicolor Species 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 241000607477 Yersinia pseudotuberculosis Species 0.000 description 1
- PMFLGOZZXFJAJQ-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PMFLGOZZXFJAJQ-UHFFFAOYSA-N 0.000 description 1
- TWEGEHYKNNBDIU-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]carbamothioic S-acid Chemical compound OC(=S)Nc1cccc(c1)C(F)(F)F TWEGEHYKNNBDIU-UHFFFAOYSA-N 0.000 description 1
- CXQYJPUBFUDFGQ-UHFFFAOYSA-N [4-chloro-3-(trifluoromethyl)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 CXQYJPUBFUDFGQ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940005347 alcaligenes faecalis Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 229940091771 aspergillus fumigatus Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 229940056450 brucella abortus Drugs 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000001064 degrader Substances 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 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
- 239000003883 ointment base Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229940007046 shigella dysenteriae Drugs 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- PYBOTXJDCXMILP-ICYLSCGJSA-M sodium;(z,12r)-12-hydroxy-2-sulfooctadec-9-enoate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCC(C([O-])=O)S(O)(=O)=O PYBOTXJDCXMILP-ICYLSCGJSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH651470A CH493499A (de) | 1969-01-31 | 1969-01-31 | Verfahren zur Herstellung von neuen O,N-Diphenyl-carbaminsäureestern |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH152169A CH503460A (de) | 1969-01-31 | 1969-01-31 | Verfahren zum antimikrobiellen Ausrüsten bzw. zum Schützen von Textilfasern gegen Mikroorganismen |
| CH651470A CH493499A (de) | 1969-01-31 | 1969-01-31 | Verfahren zur Herstellung von neuen O,N-Diphenyl-carbaminsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH493499A true CH493499A (de) | 1970-07-15 |
Family
ID=4212381
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH651470A CH493499A (de) | 1969-01-31 | 1969-01-31 | Verfahren zur Herstellung von neuen O,N-Diphenyl-carbaminsäureestern |
| CH152169A CH503460A (de) | 1969-01-31 | 1969-01-31 | Verfahren zum antimikrobiellen Ausrüsten bzw. zum Schützen von Textilfasern gegen Mikroorganismen |
| CH651570A CH493480A (de) | 1969-01-31 | 1969-01-31 | Verfahren zur Herstellung von neuen O,N-Diphenyl-carbaminsäureestern |
| CH152169D CH152169A4 (is") | 1969-01-31 | 1969-01-31 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH152169A CH503460A (de) | 1969-01-31 | 1969-01-31 | Verfahren zum antimikrobiellen Ausrüsten bzw. zum Schützen von Textilfasern gegen Mikroorganismen |
| CH651570A CH493480A (de) | 1969-01-31 | 1969-01-31 | Verfahren zur Herstellung von neuen O,N-Diphenyl-carbaminsäureestern |
| CH152169D CH152169A4 (is") | 1969-01-31 | 1969-01-31 |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4828897B1 (is") |
| AU (1) | AU1080470A (is") |
| BE (1) | BE745213A (is") |
| BR (1) | BR7016472D0 (is") |
| CH (4) | CH493499A (is") |
| DE (1) | DE2004302A1 (is") |
| ES (3) | ES376045A1 (is") |
| FR (1) | FR2034515B1 (is") |
| GB (1) | GB1270901A (is") |
| NL (1) | NL7001392A (is") |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6552214B1 (en) | 2000-05-04 | 2003-04-22 | General Electric Company | Antimicrobial compound |
| BRPI0514466A (pt) * | 2004-08-19 | 2008-06-10 | Icos Corp | composto, composição, e, métodos de inibir a quinase 1 do ponto de controle em uma célula, de sensibilizar células, e de inibir a proliferação celular aberrante |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3142646A (en) | 1960-04-11 | 1964-07-28 | Monsanto Co | Antiseptic detergent formulations containing halogenated carbanilates |
| CH436207A (de) | 1965-03-02 | 1967-11-15 | Ciba Geigy | Verfahren zum antimikrobiellen Ausrüsten und Schützen von Textilien gegen schädliche Mikroorganismen |
| CH477172A (de) | 1965-05-18 | 1969-08-31 | Agripat Sa | Beifuttermittel |
| FR1493102A (fr) | 1965-05-18 | 1967-08-25 | Agripat Sa | Esters carbamiques et thiocarbamiques et leur préparation |
-
1969
- 1969-01-31 CH CH651470A patent/CH493499A/de not_active IP Right Cessation
- 1969-01-31 CH CH152169A patent/CH503460A/de not_active IP Right Cessation
- 1969-01-31 CH CH651570A patent/CH493480A/de not_active IP Right Cessation
- 1969-01-31 CH CH152169D patent/CH152169A4/xx unknown
-
1970
- 1970-01-30 FR FR7003316A patent/FR2034515B1/fr not_active Expired
- 1970-01-30 BR BR21647270A patent/BR7016472D0/pt unknown
- 1970-01-30 BE BE745213D patent/BE745213A/xx unknown
- 1970-01-30 NL NL7001392A patent/NL7001392A/xx unknown
- 1970-01-30 GB GB446670A patent/GB1270901A/en not_active Expired
- 1970-01-30 ES ES376045A patent/ES376045A1/es not_active Expired
- 1970-01-30 DE DE19702004302 patent/DE2004302A1/de not_active Ceased
- 1970-01-30 JP JP840570A patent/JPS4828897B1/ja active Pending
- 1970-01-30 ES ES376046A patent/ES376046A1/es not_active Expired
- 1970-01-30 ES ES376044A patent/ES376044A1/es not_active Expired
- 1970-01-30 AU AU10804/70A patent/AU1080470A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7001392A (is") | 1970-08-04 |
| JPS4828897B1 (is") | 1973-09-05 |
| FR2034515B1 (is") | 1973-04-06 |
| FR2034515A1 (is") | 1970-12-11 |
| CH152169A4 (is") | 1970-11-13 |
| DE2004302A1 (de) | 1970-08-06 |
| AU1080470A (en) | 1971-08-02 |
| GB1270901A (en) | 1972-04-19 |
| CH503460A (de) | 1970-11-13 |
| ES376046A1 (es) | 1972-04-16 |
| BR7016472D0 (pt) | 1973-04-12 |
| BE745213A (fr) | 1970-07-30 |
| CH493480A (de) | 1970-07-15 |
| ES376044A1 (es) | 1972-06-01 |
| ES376045A1 (es) | 1972-04-16 |
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