CH394492A - Procédé de préparation d'un nouvel antibiotique - Google Patents
Procédé de préparation d'un nouvel antibiotiqueInfo
- Publication number
- CH394492A CH394492A CH301360A CH301360A CH394492A CH 394492 A CH394492 A CH 394492A CH 301360 A CH301360 A CH 301360A CH 301360 A CH301360 A CH 301360A CH 394492 A CH394492 A CH 394492A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- product
- tetracycline
- hydroxyethyl
- penicillin
- Prior art date
Links
- 230000003115 biocidal effect Effects 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000004098 Tetracycline Substances 0.000 claims description 18
- 229930101283 tetracycline Natural products 0.000 claims description 18
- 229960002180 tetracycline Drugs 0.000 claims description 17
- 235000019364 tetracycline Nutrition 0.000 claims description 15
- 150000003522 tetracyclines Chemical class 0.000 claims description 14
- 229930195708 Penicillin V Natural products 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229940056367 penicillin v Drugs 0.000 claims description 11
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000004108 freeze drying Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 29
- 229930182555 Penicillin Natural products 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 12
- 229940049954 penicillin Drugs 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=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)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 8
- 241000295644 Staphylococcaceae Species 0.000 description 7
- 241000191967 Staphylococcus aureus Species 0.000 description 7
- 150000002960 penicillins Chemical class 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 108010087702 Penicillinase Proteins 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003899 bactericide agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 229950009506 penicillinase Drugs 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- PPJYSSNKSXAVDB-UHFFFAOYSA-N 3,3',5,5'-tetraiodothyroacetic acid Chemical compound IC1=CC(CC(=O)O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 PPJYSSNKSXAVDB-UHFFFAOYSA-N 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000000721 bacterilogical effect Effects 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 235000020075 ouzo Nutrition 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- -1 N2 (or 9 Chemical class 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241001312524 Streptococcus viridans Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- PCIUEQPBYFRTEM-UHFFFAOYSA-N perfluorodecanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PCIUEQPBYFRTEM-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008664 renal activity Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05B—SPRAYING APPARATUS; ATOMISING APPARATUS; NOZZLES
- B05B9/00—Spraying apparatus for discharge of liquids or other fluent material, without essentially mixing with gas or vapour
- B05B9/03—Spraying apparatus for discharge of liquids or other fluent material, without essentially mixing with gas or vapour characterised by means for supplying liquid or other fluent material
- B05B9/04—Spraying apparatus for discharge of liquids or other fluent material, without essentially mixing with gas or vapour characterised by means for supplying liquid or other fluent material with pressurised or compressible container; with pump
- B05B9/08—Apparatus to be carried on or by a person, e.g. of knapsack type
- B05B9/085—Apparatus to be carried on or by a person, e.g. of knapsack type with a liquid pump
- B05B9/0877—Apparatus to be carried on or by a person, e.g. of knapsack type with a liquid pump the pump being of pressure-accumulation type or being connected to a pressure accumulation chamber
-
- 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
- A61K31/65—Tetracyclines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10887/59A GB891004A (en) | 1959-03-31 | 1959-03-31 | Improvements in or relating to tetrocycline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH394492A true CH394492A (fr) | 1965-06-30 |
Family
ID=9976135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH301360A CH394492A (fr) | 1959-03-31 | 1960-03-17 | Procédé de préparation d'un nouvel antibiotique |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE588706A (en(2012)) |
| BR (1) | BR6018213D0 (en(2012)) |
| CH (1) | CH394492A (en(2012)) |
| DE (1) | DE1142170B (en(2012)) |
| ES (1) | ES256969A1 (en(2012)) |
| FR (2) | FR1586601A (en(2012)) |
| GB (1) | GB891004A (en(2012)) |
| SE (1) | SE303278B (en(2012)) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569728A (en(2012)) * | ||||
| DE1044806B (de) * | 1956-10-03 | 1958-11-27 | Hoechst Ag | Verfahren zur Herstellung von wasserloeslichen Derivaten der Tetracycline |
-
1959
- 1959-03-31 GB GB10887/59A patent/GB891004A/en not_active Expired
-
1960
- 1960-03-15 FR FR1586601D patent/FR1586601A/fr not_active Expired
- 1960-03-16 BE BE588706A patent/BE588706A/fr unknown
- 1960-03-17 CH CH301360A patent/CH394492A/fr unknown
- 1960-03-24 DE DES67727A patent/DE1142170B/de active Pending
- 1960-03-29 BR BR118213/60A patent/BR6018213D0/pt unknown
- 1960-03-29 SE SE3107/60A patent/SE303278B/xx unknown
- 1960-03-30 ES ES0256969A patent/ES256969A1/es not_active Expired
- 1960-08-17 FR FR835979A patent/FR521M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BE588706A (fr) | 1960-07-18 |
| GB891004A (en) | 1962-03-07 |
| FR1586601A (en(2012)) | 1970-02-27 |
| DE1142170B (de) | 1963-01-10 |
| FR521M (en(2012)) | 1961-05-23 |
| SE303278B (en(2012)) | 1968-08-26 |
| ES256969A1 (es) | 1960-10-16 |
| BR6018213D0 (pt) | 1973-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HUP0600533A2 (en) | Paclitaxel solvates | |
| FR2557878A1 (fr) | Compose antibiotique, procede pour le preparer et compositions le contenant | |
| BE487301A (en(2012)) | ||
| BE1000573A4 (fr) | Derives de 1-(hydroxystyryl)-5h-2,3-benzodiazepine, procede pour les preparer et compositions pharmaceutiques les contenant. | |
| FR2498931A1 (fr) | Medicament constitue par l'acide ethyl-1 fluoro-6 piperazinyl-7 oxo-4 dihydro-1,4 quinoleine-3 carboxylique et ses sels d'addition d'acides non toxiques pharmaceutiquement acceptables | |
| CH394492A (fr) | Procédé de préparation d'un nouvel antibiotique | |
| CA2730331A1 (fr) | Derives heterocycliques utiles dans le traitement de maladies neurodegeneratives | |
| CA1277240C (fr) | Medicament modulateur de l'immunite et son procede de preparation | |
| FR2742151A1 (fr) | Utilisation de derives de bicycles mono ou dicetoniques, nouveaux composes obtenus et leur application en therapeutique | |
| CH616937A5 (en) | Process for producing 9-hydroxyellepticine derivatives | |
| FR2485926A1 (fr) | Composition pharmaceutique comprenant un derive de l'acide aminobenzoique pour reguler les prostaglandines | |
| EP0006050A1 (fr) | Extrait de Stephania cepharantha, son procédé de préparation et son application en thérapeutique | |
| KR20060012316A (ko) | 알츠하이머병의 치료에 유용한 화합물과 그것들을 함유한제형 | |
| US3005024A (en) | 1:3:3-acetaldehyde-ammonia adducts of tetracycline and its analogs | |
| EP0034521B1 (fr) | Médicament analgésique contenant de la 1-(3'benzofuryl)-4-benzylpipérazine et son procédé de préparation | |
| EP0571520B1 (fr) | Utilisation en therapeutique de pycnogenols pour la preparation de medicaments a activite anti-inflammatoire | |
| US3903086A (en) | Nitrofuryl-triazolo{8 4,3b{9 pyridazine-amide compounds and bacteriostatic compositions | |
| FR2687574A1 (fr) | Nouvelle application therapeutique de derives du pyridylpyrrolothiazole carboxamide. | |
| JP2000264889A (ja) | ジオキソペニシラン酸誘導体の製造方法 | |
| JP4808853B2 (ja) | 新規抗腫瘍剤 | |
| BE887220A (fr) | Compositions antitumeurs | |
| DE2210382A1 (de) | 10'-(omega-n-/1,4-diazabizyklo/4,m, o/-alkanyl/acyl)-phenothiazine, ihre saeureadditionssalze und ihre quaternaeren salze, verfahren zu ihrer herstellung und ihre anwendung | |
| JPS5925795B2 (ja) | ピリド〔２，３−ｃ〕アクリジン−１−ヒドロキシ−２−カルボン酸及びその誘導体並びにその製法 | |
| WO1993000899A1 (fr) | Utilisation du (pyridyl-3)-3-1h,3h-pyrrolo (1,2-c) thiazole-carboxamide-7 pour le traitement des infections a retrovirus | |
| FR2499855A1 (fr) | Nouvelles substances a action carcinostatique et immuno-stimulante, procede pour les preparer a partir de bacteries du genre fusobacterium, et agent carcinostatique contenant de telles substances |