CH541622A - Verfahren zur Herstellung eines neuen fungiziden Antibiotikums - Google Patents
Verfahren zur Herstellung eines neuen fungiziden AntibiotikumsInfo
- Publication number
- CH541622A CH541622A CH1294067A CH1294067A CH541622A CH 541622 A CH541622 A CH 541622A CH 1294067 A CH1294067 A CH 1294067A CH 1294067 A CH1294067 A CH 1294067A CH 541622 A CH541622 A CH 541622A
- Authority
- CH
- Switzerland
- Prior art keywords
- antibiotic
- aliphatic
- concentrate
- carbon atoms
- solvent
- Prior art date
Links
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 37
- 230000000843 anti-fungal effect Effects 0.000 title abstract description 3
- 229940121375 antifungal agent Drugs 0.000 title abstract 2
- 241000993288 Oudemansiella Species 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 241000993286 Mucidula mucida Species 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 3
- 239000012141 concentrate Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- -1 aliphatic alcohols Chemical class 0.000 claims description 6
- 239000000287 crude extract Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 235000015097 nutrients Nutrition 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000000855 fermentation Methods 0.000 claims description 2
- 230000004151 fermentation Effects 0.000 claims description 2
- 229910052500 inorganic mineral Chemical class 0.000 claims description 2
- 239000011707 mineral Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000013375 chromatographic separation Methods 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000010828 elution Methods 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 abstract description 6
- 241000222120 Candida <Saccharomycetales> Species 0.000 abstract description 4
- 241000223238 Trichophyton Species 0.000 abstract description 3
- 241000228212 Aspergillus Species 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 238000002955 isolation Methods 0.000 abstract description 2
- 239000002674 ointment Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- LLRJCKLNDNKRTF-UHFFFAOYSA-N 5-[2-(2-methoxyphenyl)ethyl]-2-methylbenzene-1,3-diol Chemical compound COC1=CC=CC=C1CCC1=CC(O)=C(C)C(O)=C1 LLRJCKLNDNKRTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052593 corundum Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 239000012531 culture fluid Substances 0.000 abstract 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 abstract 1
- 235000019439 ethyl acetate Nutrition 0.000 abstract 1
- 238000000338 in vitro Methods 0.000 abstract 1
- 239000012046 mixed solvent Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 239000007921 spray Substances 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000013543 active substance Substances 0.000 description 10
- 238000000605 extraction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- YBZRLMLGUBIIDN-UHFFFAOYSA-N Spicamycin Chemical compound O1C(C(O)CO)C(NC(=O)CNC(=O)CCCCCCCCCCCCC(C)C)C(O)C(O)C1NC1=NC=NC2=C1NC=N2 YBZRLMLGUBIIDN-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 235000013325 dietary fiber Nutrition 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000335423 Blastomyces Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000222173 Candida parapsilosis Species 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- 241000223205 Coccidioides immitis Species 0.000 description 1
- 241000235646 Cyberlindnera jadinii Species 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000603729 Geotrichum sp. Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000285963 Kluyveromyces fragilis Species 0.000 description 1
- 235000014663 Kluyveromyces fragilis Nutrition 0.000 description 1
- 241000893980 Microsporum canis Species 0.000 description 1
- 241001558145 Mucor sp. Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000228168 Penicillium sp. Species 0.000 description 1
- 241001149963 Sporothrix schenckii Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000223229 Trichophyton rubrum Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- HAAYBYDROVFKPU-UHFFFAOYSA-N silver;azane;nitrate Chemical compound N.N.[Ag+].[O-][N+]([O-])=O HAAYBYDROVFKPU-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910000634 wood's metal Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/06—Fungi, e.g. yeasts
- A61K36/062—Ascomycota
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Mycology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Compounds Of Unknown Constitution (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS759265 | 1965-12-17 | ||
| CS43767 | 1967-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH541622A true CH541622A (de) | 1973-09-15 |
Family
ID=5336429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1294067A CH541622A (de) | 1965-12-17 | 1967-10-26 | Verfahren zur Herstellung eines neuen fungiziden Antibiotikums |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT273374B (forum.php) |
| BE (1) | BE704076A (forum.php) |
| BR (1) | BR6793356D0 (forum.php) |
| CH (1) | CH541622A (forum.php) |
| DE (1) | DE1643818B2 (forum.php) |
| DK (1) | DK115465B (forum.php) |
| ES (1) | ES345346A1 (forum.php) |
| FI (1) | FI44892C (forum.php) |
| FR (1) | FR93489E (forum.php) |
| GB (1) | GB1181892A (forum.php) |
| GR (1) | GR34447B (forum.php) |
| NL (1) | NL6712841A (forum.php) |
| SE (1) | SE363237B (forum.php) |
-
1967
- 1967-09-19 AT AT853167A patent/AT273374B/de active
- 1967-09-20 NL NL6712841A patent/NL6712841A/xx unknown
- 1967-09-20 BE BE704076D patent/BE704076A/xx unknown
- 1967-09-22 GB GB43245/67A patent/GB1181892A/en not_active Expired
- 1967-09-22 GR GR670134447A patent/GR34447B/el unknown
- 1967-09-22 ES ES345346A patent/ES345346A1/es not_active Expired
- 1967-09-26 FR FR122225A patent/FR93489E/fr not_active Expired
- 1967-09-27 FI FI672587A patent/FI44892C/fi active
- 1967-09-27 BR BR193356/67A patent/BR6793356D0/pt unknown
- 1967-10-03 DK DK489267AA patent/DK115465B/da not_active IP Right Cessation
- 1967-10-25 DE DE1967C0043652 patent/DE1643818B2/de active Granted
- 1967-10-26 CH CH1294067A patent/CH541622A/de not_active IP Right Cessation
- 1967-11-08 SE SE15333/67A patent/SE363237B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR93489E (fr) | 1969-04-04 |
| DE1643818B2 (de) | 1977-04-07 |
| FI44892C (fi) | 1972-02-10 |
| FI44892B (forum.php) | 1971-11-01 |
| SE363237B (forum.php) | 1974-01-14 |
| GR34447B (el) | 1968-05-07 |
| DK115465B (da) | 1969-10-13 |
| GB1181892A (en) | 1970-02-18 |
| AT273374B (de) | 1969-08-11 |
| BR6793356D0 (pt) | 1973-08-07 |
| NL6712841A (forum.php) | 1968-07-19 |
| BE704076A (forum.php) | 1968-03-20 |
| DE1643818A1 (de) | 1972-03-16 |
| ES345346A1 (es) | 1969-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |