CA1089493A - Hydroxylated amines with bacteriostatic activity - Google Patents
Hydroxylated amines with bacteriostatic activityInfo
- Publication number
- CA1089493A CA1089493A CA245,905A CA245905A CA1089493A CA 1089493 A CA1089493 A CA 1089493A CA 245905 A CA245905 A CA 245905A CA 1089493 A CA1089493 A CA 1089493A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- hydroxy
- prepared
- radical
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001412 amines Chemical class 0.000 title claims description 5
- 230000003385 bacteriostatic effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 37
- -1 aliphatic radical Chemical class 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- YXVSILCKOXDORK-UHFFFAOYSA-N 1-amino-3-decoxypropan-2-ol;hydrobromide Chemical compound Br.CCCCCCCCCCOCC(O)CN YXVSILCKOXDORK-UHFFFAOYSA-N 0.000 claims 2
- JZGHZXCZUAJOSA-UHFFFAOYSA-N 1-amino-3-decoxypropan-2-ol;hydrochloride Chemical compound Cl.CCCCCCCCCCOCC(O)CN JZGHZXCZUAJOSA-UHFFFAOYSA-N 0.000 claims 2
- BIIUXLLBAVYARH-UHFFFAOYSA-N 1-amino-3-decylsulfanylpropan-2-ol;hydrochloride Chemical compound Cl.CCCCCCCCCCSCC(O)CN BIIUXLLBAVYARH-UHFFFAOYSA-N 0.000 claims 2
- QOTSPBHMMWIYOX-UHFFFAOYSA-N 1-amino-3-dodecoxypropan-2-ol;hydrochloride Chemical compound Cl.CCCCCCCCCCCCOCC(O)CN QOTSPBHMMWIYOX-UHFFFAOYSA-N 0.000 claims 2
- 229960000443 hydrochloric acid Drugs 0.000 claims 2
- 235000011167 hydrochloric acid Nutrition 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- GZIZSEZACLNKGZ-UHFFFAOYSA-N 1-amino-3-decoxypropan-2-ol Chemical compound CCCCCCCCCCOCC(O)CN GZIZSEZACLNKGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 abstract description 3
- 230000002421 anti-septic effect Effects 0.000 abstract description 2
- 229940064004 antiseptic throat preparations Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000003206 sterilizing agent Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000193830 Bacillus <bacterium> Species 0.000 description 3
- 235000014469 Bacillus subtilis Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 206010052428 Wound Diseases 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000010413 mother solution Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YIEWJUDIKXQGKF-UHFFFAOYSA-N 1-chloro-3-decoxypropan-2-ol Chemical compound CCCCCCCCCCOCC(O)CCl YIEWJUDIKXQGKF-UHFFFAOYSA-N 0.000 description 2
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 150000001804 chlorine Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KPPUKQWUXQODEH-UHFFFAOYSA-N 1-bromo-3-octoxypropan-2-ol Chemical compound CCCCCCCCOCC(O)CBr KPPUKQWUXQODEH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000100287 Membras Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 239000005864 Sulphur Chemical group 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 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 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000003330 sporicidal effect Effects 0.000 description 1
- 230000001647 sporostatic effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
- C12Q1/18—Testing for antimicrobial activity of a material
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Toxicology (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7505647A FR2301235A1 (fr) | 1975-02-24 | 1975-02-24 | Amines hydroxylees a activite bacteriostatique |
| FR7505647 | 1975-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1089493A true CA1089493A (en) | 1980-11-11 |
Family
ID=9151626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,905A Expired CA1089493A (en) | 1975-02-24 | 1976-02-17 | Hydroxylated amines with bacteriostatic activity |
Country Status (15)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2456475A2 (fr) * | 1979-05-16 | 1980-12-12 | Pharmascience Lab | Procede de sterilisation utilisant un adjuvant de l'action de la chaleur |
| US4843176A (en) * | 1980-06-19 | 1989-06-27 | Petrolite Corporation | Compounds containing sulfur and amino groups |
| GB8327911D0 (en) * | 1983-10-19 | 1983-11-23 | Ciba Geigy Ag | Salts as corrosion inhibitors |
| FR2557101B1 (fr) * | 1983-12-21 | 1986-06-27 | Pharmascience Lab | Nouveau procede de preparation de diamine-alcools |
| EP0233140B1 (de) * | 1986-01-10 | 1989-11-08 | Ciba-Geigy Ag | Schwefel-und stickstoffhaltige Schmiermittelzusätze |
| FR2635439B1 (fr) * | 1988-08-19 | 1991-05-10 | Produits Ind Cie Fse | Preparation d'un desinfectant propre a prevenir la mammite subclinique chez les ruminants |
| CA2001801A1 (en) * | 1988-11-10 | 1990-05-10 | Kathleen S. Laurenzo | Process for preparing hydroxylated amines |
| US4888138A (en) * | 1988-11-10 | 1989-12-19 | Ethyl Corporation | Substituted ammonium carbamates and method for preparing same |
| FR2667761B1 (fr) * | 1990-10-11 | 1993-01-08 | Produits Ind Cie Fse | Composition desinfectante pour l'industrie agro-alimentaire et la medecine veterinaire. |
| DE69714749T2 (de) * | 1996-09-18 | 2003-04-24 | Daiso Co., Ltd. | Verfahren zur herstellung von 3-amino-2-hydroxy-1-propylethern |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB276012A (en) * | 1926-08-13 | 1927-12-08 | Ig Farbenindustrie Ag | Manufacture of 1-amino-3-dialkylamino-2-propanols |
| DE680599C (de) * | 1933-04-13 | 1939-09-01 | Gerhard Domagk Dr | Verfahren zur Desinfektion und Konservierung |
| US3296146A (en) * | 1965-08-26 | 1967-01-03 | Atlantic Richfield Co | Alkylbenzene sulfonate detergent compositions containing 2-hydroxy-1-amino alkanes |
| DE2252487C3 (de) * | 1972-10-26 | 1979-07-19 | Th. Goldschmidt Ag, 4300 Essen | Propanolamin-Derivate und deren Verwendung als Mikrobicide |
-
1975
- 1975-02-24 FR FR7505647A patent/FR2301235A1/fr active Granted
-
1976
- 1976-02-16 IL IL49041A patent/IL49041A/xx unknown
- 1976-02-16 DE DE2606106A patent/DE2606106C2/de not_active Expired
- 1976-02-16 NL NLAANVRAGE7601573,A patent/NL177110C/xx not_active IP Right Cessation
- 1976-02-16 MX MX76334U patent/MX3615E/es unknown
- 1976-02-17 CA CA245,905A patent/CA1089493A/en not_active Expired
- 1976-02-20 IT IT09354/76A patent/IT1068369B/it active
- 1976-02-20 AT AT122976A patent/AT350195B/de not_active IP Right Cessation
- 1976-02-20 BE BE164476A patent/BE838758A/xx not_active IP Right Cessation
- 1976-02-23 LU LU74405A patent/LU74405A1/xx unknown
- 1976-02-24 GB GB7204/76A patent/GB1544935A/en not_active Expired
- 1976-02-24 ES ES445465A patent/ES445465A1/es not_active Expired
- 1976-02-24 CH CH226476A patent/CH616400A5/fr not_active IP Right Cessation
- 1976-02-24 JP JP51019817A patent/JPS51113810A/ja active Granted
- 1976-02-24 BR BR7601148A patent/BR7601148A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7601148A (pt) | 1976-09-14 |
| FR2301235B1 (enrdf_load_html_response) | 1979-08-31 |
| ES445465A1 (es) | 1977-06-01 |
| LU74405A1 (enrdf_load_html_response) | 1977-05-06 |
| IT1068369B (it) | 1985-03-21 |
| IL49041A (en) | 1980-03-31 |
| NL7601573A (nl) | 1976-08-26 |
| JPS6119620B2 (enrdf_load_html_response) | 1986-05-17 |
| NL177110C (nl) | 1985-08-01 |
| GB1544935A (en) | 1979-04-25 |
| FR2301235A1 (fr) | 1976-09-17 |
| BE838758A (fr) | 1976-08-20 |
| DE2606106C2 (de) | 1985-04-04 |
| MX3615E (es) | 1981-04-01 |
| AT350195B (de) | 1979-05-10 |
| ATA122976A (de) | 1978-10-15 |
| IL49041A0 (en) | 1976-04-30 |
| NL177110B (nl) | 1985-03-01 |
| DE2606106A1 (de) | 1976-09-02 |
| CH616400A5 (en) | 1980-03-31 |
| JPS51113810A (en) | 1976-10-07 |
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