DE1468178A1 - Verfahren zur Isolierung des Antibiotikums Fusidinsaeure aus Fermentationsbruehen durch Extraktion - Google Patents
Verfahren zur Isolierung des Antibiotikums Fusidinsaeure aus Fermentationsbruehen durch ExtraktionInfo
- Publication number
- DE1468178A1 DE1468178A1 DE19611468178 DE1468178A DE1468178A1 DE 1468178 A1 DE1468178 A1 DE 1468178A1 DE 19611468178 DE19611468178 DE 19611468178 DE 1468178 A DE1468178 A DE 1468178A DE 1468178 A1 DE1468178 A1 DE 1468178A1
- Authority
- DE
- Germany
- Prior art keywords
- antibiotic
- acid
- extraction
- extracted
- isolated
- 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.)
- Pending
Links
- 230000003115 biocidal effect Effects 0.000 title claims description 59
- 238000000605 extraction Methods 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 14
- IECPWNUMDGFDKC-UHFFFAOYSA-N Fusicsaeure Natural products C12C(O)CC3C(=C(CCC=C(C)C)C(O)=O)C(OC(C)=O)CC3(C)C1(C)CCC1C2(C)CCC(O)C1C IECPWNUMDGFDKC-UHFFFAOYSA-N 0.000 title claims description 12
- 229960004675 fusidic acid Drugs 0.000 title claims description 12
- IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical compound O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-N 0.000 title claims description 12
- 238000000855 fermentation Methods 0.000 title description 5
- 230000004151 fermentation Effects 0.000 title description 5
- 238000002955 isolation Methods 0.000 title description 4
- 235000010633 broth Nutrition 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000001963 growth medium Substances 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- -1 amine salts Chemical class 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 229940088710 antibiotic agent Drugs 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- 241000711981 Sais Species 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- SEVPGNFKEDEULZ-UHFFFAOYSA-M 1-pyridin-1-ium-1-ylethanone;chloride Chemical compound [Cl-].CC(=O)[N+]1=CC=CC=C1 SEVPGNFKEDEULZ-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012531 culture fluid Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 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
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3247960A GB930786A (en) | 1960-09-21 | 1960-09-21 | Improvements in or relating to antibiotics containing a cyclopentanophenanthrene nucleus |
| GB2172161 | 1961-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1468178A1 true DE1468178A1 (de) | 1969-02-13 |
Family
ID=26255477
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19611468178 Pending DE1468178A1 (de) | 1960-09-21 | 1961-09-21 | Verfahren zur Isolierung des Antibiotikums Fusidinsaeure aus Fermentationsbruehen durch Extraktion |
| DE19611467986 Pending DE1467986A1 (de) | 1960-09-21 | 1961-09-21 | Verfahren zur Isolierung des Antibiotikums Fusidinsaeure durch selektive Adsorption |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19611467986 Pending DE1467986A1 (de) | 1960-09-21 | 1961-09-21 | Verfahren zur Isolierung des Antibiotikums Fusidinsaeure durch selektive Adsorption |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH458624A (cs) |
| DE (2) | DE1468178A1 (cs) |
| DK (2) | DK114542B (cs) |
| ES (1) | ES270607A1 (cs) |
| FR (1) | FR1651M (cs) |
| SE (2) | SE334435B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007051468A3 (en) * | 2005-10-31 | 2007-10-04 | Leo Pharma As | Preparation of an antibiotic crystalline fusidic acid |
-
1961
- 1961-09-18 CH CH1077561A patent/CH458624A/de unknown
- 1961-09-19 ES ES270607A patent/ES270607A1/es not_active Expired
- 1961-09-21 DE DE19611468178 patent/DE1468178A1/de active Pending
- 1961-09-21 DE DE19611467986 patent/DE1467986A1/de active Pending
- 1961-12-13 FR FR881781A patent/FR1651M/fr not_active Expired
-
1962
- 1962-08-14 DK DK356762AA patent/DK114542B/da unknown
- 1962-08-14 DK DK356862AA patent/DK114682B/da unknown
- 1962-12-27 SE SE13982/62A patent/SE334435B/xx unknown
- 1962-12-27 SE SE13983/62A patent/SE334436B/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007051468A3 (en) * | 2005-10-31 | 2007-10-04 | Leo Pharma As | Preparation of an antibiotic crystalline fusidic acid |
| RU2418806C2 (ru) * | 2005-10-31 | 2011-05-20 | Лео Фарма А/С | Получение кристаллического антибиотика |
| US8933063B2 (en) | 2005-10-31 | 2015-01-13 | Leo Pharma A/S | Preparation of a crystalline antibiotic substance |
Also Published As
| Publication number | Publication date |
|---|---|
| DK114682B (da) | 1969-07-28 |
| FR1651M (fr) | 1963-01-14 |
| DE1467986A1 (de) | 1969-03-13 |
| ES270607A1 (es) | 1962-09-16 |
| CH458624A (de) | 1968-06-30 |
| SE334436B (cs) | 1971-04-26 |
| SE334435B (cs) | 1971-04-26 |
| DK114542B (da) | 1969-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |