DE1142170B - Verfahren zur Herstellung einer neuen Verbindung des Phenoxymethylpenicillins - Google Patents
Verfahren zur Herstellung einer neuen Verbindung des PhenoxymethylpenicillinsInfo
- Publication number
- DE1142170B DE1142170B DES67727A DES0067727A DE1142170B DE 1142170 B DE1142170 B DE 1142170B DE S67727 A DES67727 A DE S67727A DE S0067727 A DES0067727 A DE S0067727A DE 1142170 B DE1142170 B DE 1142170B
- Authority
- DE
- Germany
- Prior art keywords
- tetracycline
- product
- phenoxymethylpenicillin
- hydroxyethyl
- penicillin
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 13
- 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 title claims description 12
- 229930195708 Penicillin V Natural products 0.000 title claims description 11
- 229940056367 penicillin v Drugs 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000004098 Tetracycline Substances 0.000 claims description 20
- 235000019364 tetracycline Nutrition 0.000 claims description 20
- 239000000047 product Substances 0.000 claims description 19
- 229960002180 tetracycline Drugs 0.000 claims description 19
- 229930101283 tetracycline Natural products 0.000 claims description 19
- 150000003522 tetracyclines Chemical class 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
- 238000006683 Mannich reaction Methods 0.000 claims description 3
- 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
- 229930182555 Penicillin Natural products 0.000 description 21
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical group 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 18
- 229940049954 penicillin Drugs 0.000 description 14
- 108010087702 Penicillinase Proteins 0.000 description 13
- 229950009506 penicillinase Drugs 0.000 description 13
- 241000191967 Staphylococcus aureus Species 0.000 description 11
- 230000000694 effects Effects 0.000 description 9
- 150000002960 penicillins Chemical class 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 7
- 230000003115 biocidal effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000295644 Staphylococcaceae Species 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- -1 β-hydroxyethyl Chemical group 0.000 description 4
- 235000014469 Bacillus subtilis Nutrition 0.000 description 3
- 229940056360 penicillin g Drugs 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000588770 Proteus mirabilis Species 0.000 description 2
- 240000004922 Vigna radiata Species 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 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 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 241000699670 Mus sp. Species 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000001851 biosynthetic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 208000001786 gonorrhea Diseases 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000009630 liquid culture Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000013558 reference substance Substances 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
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940040944 tetracyclines Drugs 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 |
|---|---|
| DE1142170B true DE1142170B (de) | 1963-01-10 |
Family
ID=9976135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES67727A Pending DE1142170B (de) | 1959-03-31 | 1960-03-24 | Verfahren zur Herstellung einer neuen Verbindung des Phenoxymethylpenicillins |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE588706A (enrdf_load_stackoverflow) |
| BR (1) | BR6018213D0 (enrdf_load_stackoverflow) |
| CH (1) | CH394492A (enrdf_load_stackoverflow) |
| DE (1) | DE1142170B (enrdf_load_stackoverflow) |
| ES (1) | ES256969A1 (enrdf_load_stackoverflow) |
| FR (2) | FR1586601A (enrdf_load_stackoverflow) |
| GB (1) | GB891004A (enrdf_load_stackoverflow) |
| SE (1) | SE303278B (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569728A (enrdf_load_stackoverflow) * | ||||
| 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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569728A (enrdf_load_stackoverflow) * | ||||
| DE1044806B (de) * | 1956-10-03 | 1958-11-27 | Hoechst Ag | Verfahren zur Herstellung von wasserloeslichen Derivaten der Tetracycline |
Also Published As
| Publication number | Publication date |
|---|---|
| BE588706A (fr) | 1960-07-18 |
| FR521M (enrdf_load_stackoverflow) | 1961-05-23 |
| FR1586601A (enrdf_load_stackoverflow) | 1970-02-27 |
| GB891004A (en) | 1962-03-07 |
| CH394492A (fr) | 1965-06-30 |
| SE303278B (enrdf_load_stackoverflow) | 1968-08-26 |
| ES256969A1 (es) | 1960-10-16 |
| BR6018213D0 (pt) | 1973-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3120460C2 (enrdf_load_stackoverflow) | ||
| DE2250993C2 (de) | Antibakterielles Mittel | |
| DE2332878C2 (de) | Salze von Cephalosporinen mit Arginin und Lysin, ihre Herstellung und injizierbare pharmazeutische Zubereitungen | |
| DE3149359A1 (de) | Pharmazeutische zubereitung zur behandlung und verhinderung von entzuendlichen darmkrankheiten, neue salze der 5,5'-azobissalicylsaeure und verfahren zur herstellung dieser salze | |
| DE2265641C2 (de) | 7-Iminocephalosporine | |
| DE2509260C3 (de) | a-(23,43,6-Penta-O-acetyl-D-gluconyl-thioureido)benzylpenicillin | |
| DE1595876A1 (de) | Verfahren zur Herstellung von Aminomethylderivaten von Rifamycin SV | |
| EP0122585B1 (de) | Neue Kristallmodifikation von Ceftazidim | |
| DE2942107A1 (de) | Pharmazeutische zubereitung mit einer antibakteriellen wirkung und ihre verwendung zur behandlung von durch grampositive und gram-negative krankheitserregende keime hervorgerufene infektionen | |
| DE1695375C3 (de) | 25-Desacetyl-rifamycin-SV-derivate u. Verfahren zu ihrer Herstellung | |
| DE1142170B (de) | Verfahren zur Herstellung einer neuen Verbindung des Phenoxymethylpenicillins | |
| DE2713683A1 (de) | Amidinopenicillanoyloxyalkylamoxycillinate, ihre herstellung und verwendung | |
| AT226367B (de) | Verfahren zur Herstellung eines neuen Tetracyclin-Penicillinates mit antibiotischer Wirkung | |
| AT362504B (de) | Verfahren zur herstellung von neuen clavulan- saeureaethern | |
| AT362503B (de) | Verfahren zur herstellung von neuen clavulan- saeureaethern und deren salzen | |
| DE2462073C2 (de) | Konservierungs- und Desinfektionsmittel | |
| DE1570031A1 (de) | Verfahren zur Herstellung neuer Mitosanverbindungen | |
| DE1445684A1 (de) | 7-Acylaminocephalosporansaeurederivate und Verfahren zu ihrer Herstellung | |
| DE2015076C3 (de) | Als Tolypomycin RB (B-2847 RB) bezeichnetes Antibiotikum und Verfahren zu seiner Herstellung | |
| AT230539B (de) | Verfahren zur Herstellung von neuen Produkten mit antibiotischer Wirkung | |
| DE1201848B (de) | Verfahren zur Herstellung von 3-[5'-Nitro-furyl-(2')]-5, 6-dihydro-imidazo[2, 1-b]thiazol und dessen Hydrohalogeniden | |
| AT303258B (de) | Verfahren zur Herstellung von neuen 6-Aminopenicillansäurederivaten | |
| DE1545835C3 (de) | Cephalosporansäurederivate, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE1793634C3 (de) | 2-Vinylpyromekonsäure und deren nicht giftige Salze sowie Verfahren zu deren Herstellung. Ausscheidung aus: 1518098 | |
| AT310355B (de) | Verfahren zur Herstellung von neuen Aminopenicillinsäurederivaten |