FI65772C - Foerfarande foer framstaellning av antimikrobiellt verksamma av huden foerdragbara 2-klor-6-metyl-4-aralkylfenoler - Google Patents
Foerfarande foer framstaellning av antimikrobiellt verksamma av huden foerdragbara 2-klor-6-metyl-4-aralkylfenoler Download PDFInfo
- Publication number
- FI65772C FI65772C FI770825A FI770825A FI65772C FI 65772 C FI65772 C FI 65772C FI 770825 A FI770825 A FI 770825A FI 770825 A FI770825 A FI 770825A FI 65772 C FI65772 C FI 65772C
- Authority
- FI
- Finland
- Prior art keywords
- chloro
- methylphenol
- wound
- methyl
- cmb
- Prior art date
Links
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 30
- YPNZJHFXFVLXSE-UHFFFAOYSA-N 2-chloro-6-methylphenol Chemical compound CC1=CC=CC(Cl)=C1O YPNZJHFXFVLXSE-UHFFFAOYSA-N 0.000 claims description 14
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 7
- -1 4-chloro-2-methylphenol lipid Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 229940073608 benzyl chloride Drugs 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- ZNNPQQQAYCQFHP-UHFFFAOYSA-N 4-benzyl-2-chloro-6-methylphenol Chemical compound ClC1=C(O)C(C)=CC(CC=2C=CC=CC=2)=C1 ZNNPQQQAYCQFHP-UHFFFAOYSA-N 0.000 claims description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 claims description 2
- UWWQCUHBWAZHSH-UHFFFAOYSA-N 2-chloro-4-[(3,4-dichlorophenyl)methyl]-6-methylphenol Chemical compound ClC1=C(O)C(C)=CC(CC=2C=C(Cl)C(Cl)=CC=2)=C1 UWWQCUHBWAZHSH-UHFFFAOYSA-N 0.000 claims description 2
- DYXKYMJKNVPIQX-UHFFFAOYSA-N 2-chloro-4-[(4-chlorophenyl)methyl]-6-methylphenol Chemical compound ClC1=C(O)C(C)=CC(CC=2C=CC(Cl)=CC=2)=C1 DYXKYMJKNVPIQX-UHFFFAOYSA-N 0.000 claims description 2
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 claims 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 206010052428 Wound Diseases 0.000 description 40
- 208000027418 Wounds and injury Diseases 0.000 description 40
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 33
- 239000000344 soap Substances 0.000 description 21
- 239000004094 surface-active agent Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- 230000002421 anti-septic effect Effects 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 206010028851 Necrosis Diseases 0.000 description 10
- 230000017074 necrotic cell death Effects 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241000700198 Cavia Species 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
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- 206010070834 Sensitisation Diseases 0.000 description 5
- 206010048038 Wound infection Diseases 0.000 description 5
- 230000000843 anti-fungal effect Effects 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 230000003179 granulation Effects 0.000 description 5
- 238000005469 granulation Methods 0.000 description 5
- 230000008313 sensitization Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000029663 wound healing Effects 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 208000010201 Exanthema Diseases 0.000 description 4
- 206010053716 Wound necrosis Diseases 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 230000007682 dermal toxicity Effects 0.000 description 4
- 201000005884 exanthem Diseases 0.000 description 4
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 4
- 229960000349 nitrofural Drugs 0.000 description 4
- 206010037844 rash Diseases 0.000 description 4
- 231100000438 skin toxicity Toxicity 0.000 description 4
- 206010006803 Burns third degree Diseases 0.000 description 3
- 241000222122 Candida albicans Species 0.000 description 3
- 206010015150 Erythema Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910052774 Proactinium Inorganic materials 0.000 description 3
- 206010040880 Skin irritation Diseases 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 150000003938 benzyl alcohols Chemical class 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000009422 growth inhibiting effect Effects 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 231100000475 skin irritation Toxicity 0.000 description 3
- 230000036556 skin irritation Effects 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 3
- XQACWEBGSZBLRG-UHFFFAOYSA-N 1-bromo-4-isothiocyanatobenzene Chemical compound BrC1=CC=C(N=C=S)C=C1 XQACWEBGSZBLRG-UHFFFAOYSA-N 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 206010007134 Candida infections Diseases 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- QFVAWNPSRQWSDU-UHFFFAOYSA-N Dibenzthion Chemical compound C1N(CC=2C=CC=CC=2)C(=S)SCN1CC1=CC=CC=C1 QFVAWNPSRQWSDU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010070835 Skin sensitisation Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000005524 benzylchlorides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 201000003984 candidiasis Diseases 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 210000000795 conjunctiva Anatomy 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 2
- ORMNPSYMZOGSSV-UHFFFAOYSA-N dinitrooxymercury Chemical compound [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 231100000370 skin sensitisation Toxicity 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WJQZZLQMLJPKQH-UHFFFAOYSA-N 2,4-dichloro-6-methylphenol Chemical compound CC1=CC(Cl)=CC(Cl)=C1O WJQZZLQMLJPKQH-UHFFFAOYSA-N 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KLHYPYAETJWSBK-UHFFFAOYSA-J Cl[Zn](Cl)(Cl)Cl Chemical compound Cl[Zn](Cl)(Cl)Cl KLHYPYAETJWSBK-UHFFFAOYSA-J 0.000 description 1
- 206010010726 Conjunctival oedema Diseases 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- 241000984642 Cura Species 0.000 description 1
- 241000223233 Cutaneotrichosporon cutaneum Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 208000007027 Oral Candidiasis Diseases 0.000 description 1
- 206010040943 Skin Ulcer Diseases 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 241000287411 Turdidae Species 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 208000018756 Variant Creutzfeldt-Jakob disease Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000002942 anti-growth Effects 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000012435 aralkylating agent Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 244000000007 bacterial human pathogen Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 208000005881 bovine spongiform encephalopathy Diseases 0.000 description 1
- 208000034526 bruise Diseases 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000816 effect on animals Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004362 fungal culture Methods 0.000 description 1
- 208000001786 gonorrhea Diseases 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000012528 membrane Substances 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
- 239000013642 negative control Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 231100000202 sensitizing Toxicity 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000121 skin sensitizing Toxicity 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000006379 syphilis Diseases 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD19184276 | 1976-03-15 | ||
| DD7600191842A DD131746A1 (de) | 1976-03-15 | 1976-03-15 | Verfahren zur herstellung antimikrobiell wirksamer,epidermal vertraeglicher verbindungen aus abfaellen der 4-chlor-2-methylphenol-synthese |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI770825A7 FI770825A7 (de) | 1977-09-16 |
| FI65772B FI65772B (fi) | 1984-03-30 |
| FI65772C true FI65772C (fi) | 1984-07-10 |
Family
ID=5503919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI770825A FI65772C (fi) | 1976-03-15 | 1977-03-15 | Foerfarande foer framstaellning av antimikrobiellt verksamma av huden foerdragbara 2-klor-6-metyl-4-aralkylfenoler |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS52144659A (de) |
| AT (1) | AT346320B (de) |
| BE (1) | BE852389A (de) |
| CH (1) | CH629169A5 (de) |
| DD (1) | DD131746A1 (de) |
| DE (1) | DE2706747C2 (de) |
| DK (1) | DK147621C (de) |
| FI (1) | FI65772C (de) |
| GB (1) | GB1509520A (de) |
| IT (1) | IT1115841B (de) |
| NL (1) | NL7702773A (de) |
| SE (1) | SE441671B (de) |
| SU (1) | SU672189A1 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI68498C (fi) * | 1981-06-25 | 1985-10-10 | Web Berlin Chemie | Blandning foer bekaempning av fytopatogeniska svampar och bakterier |
| YU110082A (en) * | 1981-07-08 | 1985-03-20 | Jenapharm Veb | Process for obtaining phenol derivatives of antimicrobial activity |
| EP0155783A1 (de) * | 1984-02-29 | 1985-09-25 | Coalite Group Plc | Laubtrocknungs- oder Entblätterungsmittel |
| GB2154879A (en) * | 1984-02-29 | 1985-09-18 | Coalite Group Plc | Foliage desiccant or defoliant |
| BR112013015973B1 (pt) * | 2010-12-21 | 2018-12-11 | Colgate-Palmolive Company | bifenóis halogenados como agentes antibacterianos. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2077780B1 (de) * | 1970-02-13 | 1973-03-16 | Inst Rech Chim Biolog |
-
1976
- 1976-03-15 DD DD7600191842A patent/DD131746A1/de unknown
-
1977
- 1977-02-17 DE DE2706747A patent/DE2706747C2/de not_active Expired
- 1977-03-08 GB GB9710/77A patent/GB1509520A/en not_active Expired
- 1977-03-09 IT IT48389/77A patent/IT1115841B/it active
- 1977-03-11 SU SU772460620A patent/SU672189A1/ru active
- 1977-03-11 BE BE175729A patent/BE852389A/xx not_active IP Right Cessation
- 1977-03-14 SE SE7702880A patent/SE441671B/xx not_active IP Right Cessation
- 1977-03-14 DK DK108577A patent/DK147621C/da not_active IP Right Cessation
- 1977-03-15 JP JP2852777A patent/JPS52144659A/ja active Pending
- 1977-03-15 AT AT174877A patent/AT346320B/de not_active IP Right Cessation
- 1977-03-15 FI FI770825A patent/FI65772C/fi not_active IP Right Cessation
- 1977-03-15 NL NL7702773A patent/NL7702773A/xx not_active Application Discontinuation
- 1977-03-15 CH CH320977A patent/CH629169A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA174877A (de) | 1978-03-15 |
| NL7702773A (nl) | 1977-09-19 |
| DD131746A1 (de) | 1978-07-19 |
| AT346320B (de) | 1978-11-10 |
| SU672189A1 (ru) | 1979-07-05 |
| JPS52144659A (en) | 1977-12-02 |
| FI65772B (fi) | 1984-03-30 |
| DE2706747C2 (de) | 1982-07-01 |
| DK147621B (da) | 1984-10-22 |
| DK147621C (da) | 1985-07-22 |
| CH629169A5 (en) | 1982-04-15 |
| SE7702880L (sv) | 1977-09-16 |
| FI770825A7 (de) | 1977-09-16 |
| GB1509520A (en) | 1978-05-04 |
| IT1115841B (it) | 1986-02-10 |
| DE2706747A1 (de) | 1977-09-22 |
| SE441671B (sv) | 1985-10-28 |
| BE852389A (fr) | 1977-09-12 |
| DK108577A (da) | 1977-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: VEB JENAPHARM |