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DE2509260B2 - a-(23,4,5,6-Penta-O-acetyI- D-gluconyl-thioureido)benzylpenicillin - Google Patents

a-(23,4,5,6-Penta-O-acetyI- D-gluconyl-thioureido)benzylpenicillin

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Publication number
DE2509260B2
DE2509260B2 DE2509260A DE2509260A DE2509260B2 DE 2509260 B2 DE2509260 B2 DE 2509260B2 DE 2509260 A DE2509260 A DE 2509260A DE 2509260 A DE2509260 A DE 2509260A DE 2509260 B2 DE2509260 B2 DE 2509260B2
Authority
DE
Germany
Prior art keywords
gluconyl
penta
thioureido
acetyi
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.)
Granted
Application number
DE2509260A
Other languages
English (en)
Other versions
DE2509260C3 (de
DE2509260A1 (de
Inventor
Haruo Ogura
Hiroshi Takahashi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
OGURA HARUO TOKIO
Original Assignee
OGURA HARUO TOKIO
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP2510874A external-priority patent/JPS5714353B2/ja
Priority claimed from JP11163174A external-priority patent/JPS5143742A/ja
Application filed by OGURA HARUO TOKIO filed Critical OGURA HARUO TOKIO
Publication of DE2509260A1 publication Critical patent/DE2509260A1/de
Publication of DE2509260B2 publication Critical patent/DE2509260B2/de
Application granted granted Critical
Publication of DE2509260C3 publication Critical patent/DE2509260C3/de
Expired legal-status Critical Current

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    • 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

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  • 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 «-(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)-
benzylpenicillin (Verbindung gemäß Erfindung);
B: Carbenicillin («-Carboxybenzylpenicillin als Vergleichssubstanz);
C: D-«((3-Methylsulfonyl-imidazolidin-2-on-l-yl)-carbonylamino)-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.
Tabelle 1
Proteus-Arten MIC (mcg/ml)
Verbin- Verbin- Verbin
dung A dung B dung C
Proteus vulgaris 3,12
OX-19
Proteus sp. C 73-22 6,25
Proteus sp. C 72-23 12,5
Proteus sp. C 73-24 25
Proteus sp. C 73-25 0,78
Proteus sp. C 73-34 1,56
Proteus morganii 0,20
kono
100
>100
>100
12,5
0,78
12,5
12,5
100
100
100
12,5
3,13
6,25
12.5
Aus Tabelle 1 ergibt sich klar, daß die erfindungsge· mäße 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 be der Unterdrückung verschiedener weiterer Bakterier erhalten wurden. Auch hier wurden die Werte nach derr Standard-Reihenverdünnungsverfahren unter Verwendung von Hirn-Herz-Infusionsbrühe bei 37°C ermittelt wobei die Bestimmung 24 Stunden nach der Inkubatior erfolgte. Der LDso-Wert für die erfindungsgemäße Verbindung bei oraler Anwendung bei Mäusen isl ebenfalls in Tabelle 2 gezeigt.
Tabelle 2
MIC (mcg/ml)
Erfindungs- Ampicillin
gemäße (Vergleich)
Verbindung
Staphylococcus aureus 209 P 0,78 0,1
Impfmenge 3,8 ■ ΙΟ5
Staphylococcus aureus Nr. 26 > 100 > 100
Impfmenge 2,3 ■ ΙΟ5
Salmonella typhi 0-901-W 50 0,39
Impf menge 3,5 · ΙΟ5
Klebsieila pneumoniae >100 1,56
Impfmenge 1,3 · 105
Escherichia coli IAM-1264 >100 3,12
Impf menge 1,9 · 105
Pseudomonas aeruginosa >100 > 100
IAM-1007
Impfmenge 1,3 · 105
Proteus vulgaris OX 19 1,56 100
Impfmenge 1,2 · 105
LD50 - mg/kg >1000 >1000
Die erfindungsgemäße Verbindung erhält man ir einem Einstufenverfahren durch Additionsreaktion de: entsprechenden Isothiocyanats von Glucose odei Gluconsäure mit Ampicillin.
Die Umsetzung wird vorteilhafterweise unter wasserfreien Bedingungen, insbesondere in einem nichtpolarer Lösungsmittel wie Kohlenwasserstoffen, z. B. Benzol Toluol und/oder Xylol, oder in Äthern, wie Tetrahydrofuran, durchgeführt.
Beispiel
Zur Herstellung von <x-(2,3,4,5,6-Penta-O-acetyl-D-gluconyl-thioureido)-benzylpenicillin wurden zu 30 ml wasserfreiem Tetrahydrofuran 447 mg (1 mMol) 2,3,4,5,6-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-':3550(-COOH), 1740 (COOCH3), 700, 740 (Phenyl).

Claims (2)

Patentansprüche:
1. ix-(2,3,4,5,6-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.
DE2509260A 1974-03-06 1975-03-04 a-(23,43,6-Penta-O-acetyl-D-gluconyl-thioureido)benzylpenicillin Expired DE2509260C3 (de)

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 true DE2509260B2 (de) 1978-09-14
DE2509260C3 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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
CA1039715A (en) 1978-10-03
FR2287445A1 (fr) 1976-05-07
FR2262968B1 (de) 1980-02-15
DE2509260C3 (de) 1979-05-03
FR2262968A1 (de) 1975-10-03
GB1463282A (en) 1977-02-02
DE2509260A1 (de) 1975-10-02
US4025622A (en) 1977-05-24
FR2287445B1 (de) 1981-12-31

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