CH629169A5 - Process for the preparation of compounds which have antimicrobial activity and epidermal tolerability from wastes from the synthesis of 4-chloro-2-methylphenol - Google Patents

Process for the preparation of compounds which have antimicrobial activity and epidermal tolerability from wastes from the synthesis of 4-chloro-2-methylphenol Download PDF

Info

Publication number: CH629169A5
Authority: CH; Switzerland
Prior art keywords: methylphenol; chloro; cmb; synthesis; wound
Prior art date: 1976-03-15

Application number

CH320977A

Other languages

German (de)

English (en)

Inventor

Axel Kramer

Eberhard Dr Schroetter

Erich Gruenert

Wolfgang Prof Dr Dr Weuffen

Hiltrud Hoeppe

Original Assignee

Jenapharm Veb

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.)

1976-03-15

Filing date

1977-03-15

Publication date

1982-04-15

1977-03-15 Application filed by Jenapharm Veb filed Critical Jenapharm Veb

1982-04-15 Publication of CH629169A5 publication Critical patent/CH629169A5/de

Links

RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 title claims description 17
150000001875 compounds Chemical class 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 8
230000015572 biosynthetic process Effects 0.000 title claims description 6
238000003786 synthesis reaction Methods 0.000 title claims description 6
239000002699 waste material Substances 0.000 title claims description 3
230000000845 anti-microbial effect Effects 0.000 title description 2
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 32
YPNZJHFXFVLXSE-UHFFFAOYSA-N 2-chloro-6-methylphenol Chemical compound CC1=CC=CC(Cl)=C1O YPNZJHFXFVLXSE-UHFFFAOYSA-N 0.000 claims description 12
238000004821 distillation Methods 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000002425 crystallisation Methods 0.000 claims description 3
230000008025 crystallization Effects 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical group C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 2
101100167062 Caenorhabditis elegans chch-3 gene Chemical group 0.000 claims description 2
238000005660 chlorination reaction Methods 0.000 claims description 2
238000002485 combustion reaction Methods 0.000 claims description 2
239000002994 raw material Substances 0.000 claims description 2
230000007797 corrosion Effects 0.000 claims 1
238000005260 corrosion Methods 0.000 claims 1
230000007547 defect Effects 0.000 claims 1
238000003912 environmental pollution Methods 0.000 claims 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 36
206010052428 Wound Diseases 0.000 description 32
208000027418 Wounds and injury Diseases 0.000 description 32
238000012360 testing method Methods 0.000 description 32
239000000203 mixture Substances 0.000 description 28
239000004094 surface-active agent Substances 0.000 description 21
239000000344 soap Substances 0.000 description 20
QFVAWNPSRQWSDU-UHFFFAOYSA-N Dibenzthion Chemical compound C1N(CC=2C=CC=CC=2)C(=S)SCN1CC1=CC=CC=C1 QFVAWNPSRQWSDU-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
229960002999 sulbentine Drugs 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
230000002421 anti-septic effect Effects 0.000 description 12
239000000460 chlorine Substances 0.000 description 12
239000000126 substance Substances 0.000 description 12
206010028851 Necrosis Diseases 0.000 description 11
230000017074 necrotic cell death Effects 0.000 description 11
241000700198 Cavia Species 0.000 description 10
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
241001465754 Metazoa Species 0.000 description 9
230000000694 effects Effects 0.000 description 8
239000002674 ointment 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
230000029663 wound healing Effects 0.000 description 7
230000001408 fungistatic effect Effects 0.000 description 6
230000035876 healing Effects 0.000 description 6
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 6
241000233866 Fungi Species 0.000 description 5
206010070834 Sensitisation Diseases 0.000 description 5
206010059516 Skin toxicity Diseases 0.000 description 5
206010048038 Wound infection Diseases 0.000 description 5
230000003385 bacteriostatic effect Effects 0.000 description 5
235000019445 benzyl alcohol Nutrition 0.000 description 5
150000003938 benzyl alcohols Chemical class 0.000 description 5
239000003814 drug 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
231100000438 skin toxicity Toxicity 0.000 description 5
239000000243 solution Substances 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
206010053716 Wound necrosis Diseases 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
235000010299 hexamethylene tetramine Nutrition 0.000 description 4
231100000225 lethality Toxicity 0.000 description 4
229960004011 methenamine Drugs 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
238000003756 stirring Methods 0.000 description 4
239000003981 vehicle Substances 0.000 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 description 3
-1 4-chloro-2-ethylphenyl ester Chemical class 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
241000222122 Candida albicans Species 0.000 description 3
201000004624 Dermatitis Diseases 0.000 description 3
VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 3
206010040880 Skin irritation Diseases 0.000 description 3
206010070835 Skin sensitisation Diseases 0.000 description 3
208000010668 atopic eczema Diseases 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
150000005524 benzylchlorides 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
230000007717 exclusion Effects 0.000 description 3
230000007794 irritation Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
231100000475 skin irritation Toxicity 0.000 description 3
230000036556 skin irritation Effects 0.000 description 3
231100000370 skin sensitisation Toxicity 0.000 description 3
235000010339 sodium tetraborate Nutrition 0.000 description 3
150000003440 styrenes Chemical class 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 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
206010007134 Candida infections Diseases 0.000 description 2
241000561734 Celosia cristata Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
206010015150 Erythema Diseases 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
229940121375 antifungal agent Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000006399 behavior Effects 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
210000001520 comb Anatomy 0.000 description 2
210000000795 conjunctiva Anatomy 0.000 description 2
231100000321 erythema Toxicity 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000004312 hexamethylene tetramine Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
230000001235 sensitizing effect Effects 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
229960002447 thiram Drugs 0.000 description 2
231100000820 toxicity test Toxicity 0.000 description 2
210000000689 upper leg Anatomy 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
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 description 1
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 description 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 description 1
235000001674 Agaricus brunnescens Nutrition 0.000 description 1
241001480043 Arthrodermataceae Species 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
FBZAJTXIEOKQDV-UHFFFAOYSA-N CC1=C(C=CC=C1)O.[Cl] Chemical compound CC1=C(C=CC=C1)O.[Cl] FBZAJTXIEOKQDV-UHFFFAOYSA-N 0.000 description 1
241000282465 Canis Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010010726 Conjunctival oedema Diseases 0.000 description 1
208000028006 Corneal injury Diseases 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
208000010201 Exanthema Diseases 0.000 description 1
238000003547 Friedel-Crafts alkylation reaction Methods 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
208000007514 Herpes zoster Diseases 0.000 description 1
206010020565 Hyperaemia Diseases 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
208000005230 Leg Ulcer Diseases 0.000 description 1
241000219470 Mirabilis Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
208000007027 Oral Candidiasis Diseases 0.000 description 1
206010039509 Scab Diseases 0.000 description 1
206010040914 Skin reaction Diseases 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
241000223230 Trichosporon Species 0.000 description 1
241000287411 Turdidae Species 0.000 description 1
208000000260 Warts Diseases 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
210000000577 adipose tissue Anatomy 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
ZDINGUUTWDGGFF-UHFFFAOYSA-N antimony(5+) Chemical compound [Sb+5] ZDINGUUTWDGGFF-UHFFFAOYSA-N 0.000 description 1
239000002543 antimycotic Substances 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
230000001580 bacterial effect Effects 0.000 description 1
244000000007 bacterial human pathogen Species 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
235000013330 chicken meat Nutrition 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
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
210000004087 cornea Anatomy 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
239000000839 emulsion Substances 0.000 description 1
201000010063 epididymitis Diseases 0.000 description 1
201000005884 exanthem Diseases 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
208000024386 fungal infectious disease Diseases 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
208000001786 gonorrhea Diseases 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 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
230000017066 negative regulation of growth Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
244000052769 pathogen Species 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
239000011505 plaster Substances 0.000 description 1
239000013641 positive control Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
206010037844 rash Diseases 0.000 description 1
230000035484 reaction time Effects 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
229910001961 silver nitrate Inorganic materials 0.000 description 1
201000010153 skin papilloma Diseases 0.000 description 1
231100000430 skin reaction Toxicity 0.000 description 1
230000035483 skin reaction Effects 0.000 description 1
239000008149 soap solution Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000006379 syphilis Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
238000005303 weighing Methods 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)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (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)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH320977A 1976-03-15 1977-03-15 Process for the preparation of compounds which have antimicrobial activity and epidermal tolerability from wastes from the synthesis of 4-chloro-2-methylphenol CH629169A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
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 (1)

Publication Number	Publication Date
CH629169A5 true CH629169A5 (en)	1982-04-15

Family

ID=5503919

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH320977A CH629169A5 (en)	1976-03-15	1977-03-15	Process for the preparation of compounds which have antimicrobial activity and epidermal tolerability from wastes from the synthesis of 4-chloro-2-methylphenol

Country Status (13)

Country	Link
JP (1)	JPS52144659A (fr)
AT (1)	AT346320B (fr)
BE (1)	BE852389A (fr)
CH (1)	CH629169A5 (fr)
DD (1)	DD131746A1 (fr)
DE (1)	DE2706747C2 (fr)
DK (1)	DK147621C (fr)
FI (1)	FI65772C (fr)
GB (1)	GB1509520A (fr)
IT (1)	IT1115841B (fr)
NL (1)	NL7702773A (fr)
SE (1)	SE441671B (fr)
SU (1)	SU672189A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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
GB2154879A (en) *	1984-02-29	1985-09-18	Coalite Group Plc	Foliage desiccant or defoliant
EP0155783A1 (fr) *	1984-02-29	1985-09-25	Coalite Group Plc	Dessiccatif de feuillage ou agent de défoliation
CN103261138B (zh) *	2010-12-21	2015-08-12	高露洁-棕榄公司	作为抗菌剂的卤代联苯酚

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2077780B1 (fr) *	1970-02-13	1973-03-16	Inst Rech Chim Biolog

1976
- 1976-03-15 DD DD7600191842A patent/DD131746A1/xx 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 BE BE175729A patent/BE852389A/fr not_active IP Right Cessation
- 1977-03-11 SU SU772460620A patent/SU672189A1/ru active
- 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 AT AT174877A patent/AT346320B/de not_active IP Right Cessation
- 1977-03-15 JP JP2852777A patent/JPS52144659A/ja active Pending
- 1977-03-15 CH CH320977A patent/CH629169A5/de not_active IP Right Cessation
- 1977-03-15 NL NL7702773A patent/NL7702773A/xx not_active Application Discontinuation
- 1977-03-15 FI FI770825A patent/FI65772C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK147621B (da)	1984-10-22
SU672189A1 (ru)	1979-07-05
DK108577A (da)	1977-09-16
AT346320B (de)	1978-11-10
DE2706747C2 (de)	1982-07-01
DD131746A1 (de)	1978-07-19
FI770825A7 (fr)	1977-09-16
DK147621C (da)	1985-07-22
FI65772B (fi)	1984-03-30
DE2706747A1 (de)	1977-09-22
JPS52144659A (en)	1977-12-02
NL7702773A (nl)	1977-09-19
GB1509520A (en)	1978-05-04
SE441671B (sv)	1985-10-28
ATA174877A (de)	1978-03-15
BE852389A (fr)	1977-09-12
FI65772C (fi)	1984-07-10
IT1115841B (it)	1986-02-10
SE7702880L (sv)	1977-09-16

Legal Events

Date	Code	Title	Description
1987-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
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DE3900102C2 (fr)	1991-04-18
DE3339196A1 (de)	1985-05-09	Antimikrobielles konservierungs- und desinfektionsmittel
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