DE2509260C3 - a-(23,43,6-Penta-O-acetyl-D-gluconyl-thioureido)benzylpenicillin - Google Patents
a-(23,43,6-Penta-O-acetyl-D-gluconyl-thioureido)benzylpenicillinInfo
- Publication number
- DE2509260C3 DE2509260C3 DE2509260A DE2509260A DE2509260C3 DE 2509260 C3 DE2509260 C3 DE 2509260C3 DE 2509260 A DE2509260 A DE 2509260A DE 2509260 A DE2509260 A DE 2509260A DE 2509260 C3 DE2509260 C3 DE 2509260C3
- Authority
- DE
- Germany
- Prior art keywords
- gluconyl
- penta
- acetyl
- thioureido
- proteus
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C327/54—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
- C07C335/26—Y being a hydrogen or a carbon atom, e.g. benzoylthioureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
Die Erfindung betrifft ein neues <x-(2,3,4,5,6- Penta-O-acetyl-D-gluconyl-thioureidoJ-benzylpenicillin
und sein Triäthylammoniumsalz, welche zur therapeutischen Behandlung von Infektionen durch grampositive und
gramnegative Bakterien geeignet sind. Die Erfindung betrifft weiterhin pharmazeutische Zusammensetzungen,
die die erfindungsgemäße Verbindung in Kombination mit einem Trägermaterial oder Verdünnungsmittel
enthalten.
Die Art der Zusammensetzung des pharmazeutischen Trägers oder Verdünnungsmittels hängt von der
vorgesehenen Anwendung, z. B. oral oder parenteral, ab. Im allgemeinen liegen die Zusammensetzungen in
einer für eine orale Anwendung geeigneten Form vor, z. B. in Form von Kapseln, Tabletten, Pulvern oder
Granulaten.
Zum Nachweis der überlegenen Wirkung der erfindungsgemäßen Verbindung wurde die minimale
Hemmkonzentration (mcg/ml) der nachfolgend näher bezeichneten drei Verbindungen A, B und C gegenüber
verschiedenen ebenfalls im folgenden näher bezeichneten Proteus-Arten nach der Standardmethode der
seriellen Verdünnung unter Verwendung einer Hirn-Herz-infusionsbrühe
als Medium bei 37°C untersucht.
Die Bestimmung erfolgte jeweils nach 24stündiger Bebrütung. Die Ergebnisse sind in der folgenden Tabelle
1 zusammengestellt.
Untersuchte Verbindungen:
A: «-(2,3,4,5,6-Penta-O-acetyl-D-gluconyl-thioureido)-
Untersuchte Verbindungen:
A: «-(2,3,4,5,6-Penta-O-acetyl-D-gluconyl-thioureido)-
benzylpenicillin (Verbindung gemäß Erfindung);
B: Carbenicillin («-Carboxybenzylpenicillin als Vergleichssubstanz);
B: Carbenicillin («-Carboxybenzylpenicillin als Vergleichssubstanz);
C: D-<x((3-Methylsulfonyl-imidazolidin-2-on-1 -yl)-carbony|amino)-benzylpenicillin-natrium
(Verbindung von Beispiel 4 der DE-OS 21 52 967 zum Vergleich).
Bei Verwendung der in der folgenden Tabelle genannten Proteus-Arten wurden die Ergebnisse erzielt,
die in den drei rechten Spalten der Tabelle zusammengestellt sind.
Proteus-Arten MIC (mcg/ml)
Verbin- Verbin- Verbindung A dung B dung C
Proteus vulgaris 3,12 100 100
OX-19
OX-19
Proteus sp. C 73-22 6,25 >100 100
Proteus sp. C 72-23 12,5 >100 100
Proteus sp. C 73-24 25 12,5 12,5
Proteus sp. C 73-25 0,78 0,78 3,13
Proteus sp. C 73-34 1,56 12,5 6,25
Proteus morganii 0,20 12,5 12,5
Aus Tabelle 1 ergibt sich klar, daß die erfindungsgemäße
Verbindung eine wesentlich höhere Wirkung gegen verschiedene Proteus-Arten zeigt als Carbenicillin
und die Verbindung von Beispiel 4 der DE-OS 21 52 967.
In der Tabelle 2 sind die Ergebnisse zusammengestellt,
die beim Vergleich der Wirkung der erfindungsgemäßen Verbindung mit Ampicillin als Bezugsgröße bei
der Unterdrückung verschiedener weiterer Bakterien erhalten wurden. Auch hier wurden die Werte nach dem
Standard-Reihenverdünnungsverfahren unter Verwendung von Hirn-Herz-Infusionsbrühe bei 37CC ermittelt,
wobei die Bestimmung 24 Stunden nach der Inkubation erfolgte. Der LDso-Wert für die erfindungsgemäße
Verbindung bei oraler Anwendung bei Mäusen ist ebenfalls in Tabelle 2 gezeigt
MIC (mcg/ml)
■Γι
Erfindungs- Ampicillin
gemäße (Vergleich)
Verbindung
gemäße (Vergleich)
Verbindung
Staphylococcus aureus 209 P 0,78 0,1
Impfmenge 3,8 · 105
Staphylococcus aureus Nr. 26 > 100 > 100
Impfmenge 2,3 · 105
Salmonella typhi 0-901-W 50 0,39
Impfmenge 3,5 · 105
Klebsieila pneumoniae >100 1,56
Impfmenge 1,3 · 105
Escherichia coli IAM-1264 > 100 3,12
Impfmenge 1,9 · 105
Pseudomonas aeruginosa >100 >100
IAM-1007
Impf menge 1,3 · lO5
Proteus vulgaris OX 19 1,56 100
Impfmenge 1,2 · 105
LD50 - mg/kg >1000 >1000
Die erfindungsgemäße Verbindung erhält man in einem Einstufenverfahren durch Additionsreaktion des
entsprechenden Isothiocyanats von Glucose oder Gluconsäure mit Ampicillin.
Die Umsetzung wird vorteilhafterweise unter wasserfreien Bedingungen, insbesondere in einem nichtpolaren
Lösungsmittel wie Kohlenwasserstoffen, z. B. Benzol, Toluol und/oder Xylol, oder in Äthern, wie Tetrahydrofuran,
durchgeführt.
Zur Herstellung von «-(23,4A6-Penta-O-acetyl-D-gluconyl-thioureido)-benzylpenicillin
wurden zu 30 ml wasserfreiem Tetrahydrofuran 447 mg (1 mMol) 23,4,5,6-Penta-O-acetyl-D-gluconylisothiocyanat und
376 mg (1 mMol) Ampicillin gegeben und die Mischung bei Raumtemperatur 24 Stunden gerührt Danach wurde
das Lösungsmittel unter verringertem Druck abdestilliert und der Rückstand durch Zugabe von
Dimethylformamid zum Kristallisieren gebracht. Nach dem Umkristallisieren aus Dimethylformamid lag das
Produkt in einer Menge von 780 mg (95%) vor.
Rf: 0,63 (Chloroform zu Methanol = 5:1).
IR ,™' cm-1:3550 (-COOH)11740(COOCH3), 700,
740 (Phenyl).
Claims (2)
- Patentansprüche:l.a-(23,4A6-Penta-O-acetyl-D-gluconyl-thioureido)-benzylpenicillin und sein Triäthylammoniumsalz.
- 2. Pharmazeutische Zusammensetzung, bestehend aus der Verbindung gemäß Anspruch 1 und einem pharmazeutischen Trägermaterial oder einem Verdünnungsmittel
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2510874A JPS5714353B2 (de) | 1974-03-06 | 1974-03-06 | |
JP11163174A JPS5143742A (ja) | 1974-09-30 | 1974-09-30 | Tansonukureoshidojudotai no seizoho |
Publications (3)
Publication Number | Publication Date |
---|---|
DE2509260A1 DE2509260A1 (de) | 1975-10-02 |
DE2509260B2 DE2509260B2 (de) | 1978-09-14 |
DE2509260C3 true DE2509260C3 (de) | 1979-05-03 |
Family
ID=26362700
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2509260A Expired DE2509260C3 (de) | 1974-03-06 | 1975-03-04 | a-(23,43,6-Penta-O-acetyl-D-gluconyl-thioureido)benzylpenicillin |
Country Status (5)
Country | Link |
---|---|
US (1) | US4025622A (de) |
CA (1) | CA1039715A (de) |
DE (1) | DE2509260C3 (de) |
FR (2) | FR2262968B1 (de) |
GB (1) | GB1463282A (de) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5639018A (en) * | 1979-08-17 | 1981-04-14 | Kemisaiensu Kk | Remedy for cancer |
IT1127208B (it) * | 1979-11-09 | 1986-05-21 | Simes | Nuovi derivati penicillanici e cefalosporanici,procedimento per la loro preparazione e relative composizioni farmaceutiche |
US4491660A (en) * | 1980-01-10 | 1985-01-01 | Abbott Laboratories | Matrix polymers for binding endotoxins |
US4321363A (en) * | 1980-02-21 | 1982-03-23 | Nippon Soda Company Limited | Adsorbent for urokinase containing agarose |
DE3341018A1 (de) * | 1983-11-12 | 1985-05-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von acylierten zuckern mit glycosidisch gebundener isothiocyanatgruppe |
DE3344257A1 (de) * | 1983-12-07 | 1985-06-13 | Bayer Ag, 5090 Leverkusen | Substituierte o-acyl-glycosylamide, verfahren zu iherer herstellung sowie ihre verwendung |
DE3429432A1 (de) * | 1984-08-10 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Acylierte zucker mit glykosidisch gebundener isocyaniddichloridgruppe und ihre herstellung |
GB0128943D0 (en) * | 2001-12-04 | 2002-01-23 | Novo Pharmaceuticals De Ltd | Bacterial enzyme inhibitors |
EP2545923A1 (de) * | 2005-12-22 | 2013-01-16 | Alchemia Limited | Antibakterielle Wirkstoffe |
CN102690228B (zh) * | 2012-06-15 | 2013-10-02 | 中国农业大学 | 一种含吡啶结构的苯甲酰基硫脲类化合物及其制备方法和应用 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2612497A (en) * | 1948-01-24 | 1952-09-30 | Hendrik W Meijer | Process for manufacture of hexose ureides and thioureides |
US3027364A (en) * | 1958-07-17 | 1962-03-27 | Spiess C F & Sohn | Fatty acid esters of aldose-semicarbazones and aldose-thioureide |
US2967859A (en) * | 1959-05-22 | 1961-01-10 | Grace W R & Co | Process for diglucose ureide |
US3135748A (en) * | 1960-05-27 | 1964-06-02 | Little Inc A | Heterocyclic substituted carbodhmides and method of preparation |
CH396013A (de) * | 1960-06-21 | 1965-07-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen Derivaten des Glucosamins |
US3149033A (en) * | 1961-02-06 | 1964-09-15 | Universal Drug And Res Lab Inc | Method of administering aldohexoseurea hypoglycemic compounds to animals |
-
1975
- 1975-02-26 US US05/553,121 patent/US4025622A/en not_active Expired - Lifetime
- 1975-03-04 DE DE2509260A patent/DE2509260C3/de not_active Expired
- 1975-03-04 GB GB895575A patent/GB1463282A/en not_active Expired
- 1975-03-05 FR FR7506827A patent/FR2262968B1/fr not_active Expired
- 1975-03-21 CA CA222,735A patent/CA1039715A/en not_active Expired
- 1975-12-31 FR FR7540240A patent/FR2287445A1/fr active Granted
Also Published As
Publication number | Publication date |
---|---|
DE2509260A1 (de) | 1975-10-02 |
CA1039715A (en) | 1978-10-03 |
GB1463282A (en) | 1977-02-02 |
FR2287445A1 (fr) | 1976-05-07 |
FR2262968B1 (de) | 1980-02-15 |
US4025622A (en) | 1977-05-24 |
DE2509260B2 (de) | 1978-09-14 |
FR2287445B1 (de) | 1981-12-31 |
FR2262968A1 (de) | 1975-10-03 |
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Date | Code | Title | Description |
---|---|---|---|
C3 | Grant after two publication steps (3rd publication) | ||
8339 | Ceased/non-payment of the annual fee |