BE633522A - - Google Patents
Info
- Publication number
- BE633522A BE633522A BE633522DA BE633522A BE 633522 A BE633522 A BE 633522A BE 633522D A BE633522D A BE 633522DA BE 633522 A BE633522 A BE 633522A
- Authority
- BE
- Belgium
- Prior art keywords
- esters
- organic
- antibiotic
- organic solvent
- ester
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 claims description 33
- 230000003115 biocidal effect Effects 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 20
- 239000004098 Tetracycline Substances 0.000 claims description 16
- 229960002180 tetracycline Drugs 0.000 claims description 16
- 229930101283 tetracycline Natural products 0.000 claims description 16
- 235000019364 tetracycline Nutrition 0.000 claims description 16
- 150000003522 tetracyclines Chemical class 0.000 claims description 16
- 239000003242 anti bacterial agent Substances 0.000 claims description 14
- 229940088710 antibiotic agent Drugs 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 238000000746 purification Methods 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- -1 2-ethylhexyl Chemical group 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 2
- QAXKHFJPTMUUOV-UHFFFAOYSA-N dinonyl hydrogen phosphate Chemical compound CCCCCCCCCOP(O)(=O)OCCCCCCCCC QAXKHFJPTMUUOV-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 15
- 238000000605 extraction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000001963 growth medium Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 229960005322 streptomycin Drugs 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000969 carrier Substances 0.000 description 6
- 150000002895 organic esters Chemical class 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 108010093965 Polymyxin B Proteins 0.000 description 5
- 229940043232 butyl acetate Drugs 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000000855 fermentation Methods 0.000 description 5
- 230000004151 fermentation Effects 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 229920000024 polymyxin B Polymers 0.000 description 5
- 229960005266 polymyxin b Drugs 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- 108010040201 Polymyxins Proteins 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 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 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 1
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- SEGLCEQVOFDUPX-UHFFFAOYSA-N di-(2-ethylhexyl)phosphoric acid Chemical compound CCCCC(CC)COP(O)(=O)OCC(CC)CCCC SEGLCEQVOFDUPX-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- KECOWKBVYCBTPB-UHFFFAOYSA-M sodium;dinonyl phosphate Chemical compound [Na+].CCCCCCCCCOP([O-])(=O)OCCCCCCCCC KECOWKBVYCBTPB-UHFFFAOYSA-M 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22584/62A GB979887A (en) | 1962-06-12 | 1962-06-12 | Improvements in or relating to the recovery and purification of amphoteric and basic antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE633522A true BE633522A (d) | 1963-12-12 |
Family
ID=10181798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE633522D BE633522A (d) | 1962-06-12 | 1963-06-12 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3376339A (d) |
| BE (1) | BE633522A (d) |
| DK (1) | DK103288C (d) |
| ES (1) | ES288950A1 (d) |
| GB (1) | GB979887A (d) |
| SE (1) | SE326794B (d) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2002705A4 (en) | 2006-03-21 | 2013-11-27 | Cromasa Identificacion Electronica S A | BRAND FOR IDENTIFYING ANIMALS |
| SK287315B6 (sk) * | 2006-06-02 | 2010-06-07 | Biotika, A. S. | Spôsob izolácie polymyxínu B z vyfermentovanej pôdy |
| SK287293B6 (sk) * | 2006-06-15 | 2010-05-07 | Biotika, A. S. | Spôsob fermentácie polymyxínu B pomocou produkčného mikroorganizmu Bacillus polymyxa |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121714A (en) * | 1961-07-31 | 1964-02-18 | Pfizer & Co C | Antibiotic recovery process |
-
1962
- 1962-06-12 GB GB22584/62A patent/GB979887A/en not_active Expired
-
1963
- 1963-06-10 US US286451A patent/US3376339A/en not_active Expired - Lifetime
- 1963-06-10 DK DK273863AA patent/DK103288C/da active
- 1963-06-11 ES ES0288950A patent/ES288950A1/es not_active Expired
- 1963-06-12 SE SE06524/63A patent/SE326794B/xx unknown
- 1963-06-12 BE BE633522D patent/BE633522A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES288950A1 (es) | 1963-10-16 |
| SE326794B (d) | 1970-08-03 |
| GB979887A (en) | 1965-01-06 |
| US3376339A (en) | 1968-04-02 |
| DK103288C (da) | 1965-12-13 |
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