DE9197T1 - Aminoglycoside derivatives, processes for their preparation and pharmaceutical compositions - Google Patents

Aminoglycoside derivatives, processes for their preparation and pharmaceutical compositions

Info

Publication number
DE9197T1
DE9197T1 DE1979103379 DE79103379T DE9197T1 DE 9197 T1 DE9197 T1 DE 9197T1 DE 1979103379 DE1979103379 DE 1979103379 DE 79103379 T DE79103379 T DE 79103379T DE 9197 T1 DE9197 T1 DE 9197T1
Authority
DE
Germany
Prior art keywords
general formula
group
compound
hydroxymethyl
aminoglycoside
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
Application number
DE1979103379
Other languages
German (de)
Original Assignee
Shionogi & Co., Ltd., Osaka (Japan) Elf: Igarashi, Kikuo, Itami, Hyogo; Sugawara, Tamio, Mino, Osaka; (Japan)
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
Application filed by Shionogi & Co., Ltd., Osaka (Japan) Elf: Igarashi, Kikuo, Itami, Hyogo; Sugawara, Tamio, Mino, Osaka; (Japan) filed Critical Shionogi & Co., Ltd., Osaka (Japan) Elf: Igarashi, Kikuo, Itami, Hyogo; Sugawara, Tamio, Mino, Osaka; (Japan)
Publication of DE9197T1 publication Critical patent/DE9197T1/en
Pending legal-status Critical Current

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Claims (9)

VOSSIUS ■ VOSSiUS · TAUCH NER ■ HEUNEMANN · RAUH PATENTANWÄLTE SIEBERTSTRASSE 4 ■ BOOO MÜNCHEN 86 ■ PHONE: (O89) 47 4O 75 CABLE: BENZOLPATENT MÖNCHEN TELEX 5-29453VOPAT D u.Z.: P 283 EP EP 79 IO3 379.8 Shionogi & Co., Ltd. Patentansprüche (deutsche Übersetzung nach Artikel 67 des Europäischen Patentübereinkommens)VOSSIUS ■ VOSSiUS · TAUCH NER ■ HEUNEMANN · RAUH PATENTANWÄLTE SIEBERTSTRASSE 4 ■ BOOO MÜNCHEN 86 ■ PHONE: (O89) 47 4O 75 CABLE: BENZOLPATENT MÖNCHEN TELEX 5-29453VOPAT D uZ: P 283 EP EP 79 IO3 379.8 & Co., Ltd. Shionogi & Co. Ltd . Claims (German translation according to Article 67 of the European Patent Convention) 1. Aminoglykosid-Derivate der allgemeine Formel I1. Aminoglycoside derivatives of the general formula I. in der R eine Hydroxyl- oder Aminogruppe bedeutet, ρin which R is a hydroxyl or amino group, ρ R ein Wasserstoffatom oder eine Hydroxylgruppe darstellt und
fr eine Hydroxymethyl- oder Carba moyloxymethylgruppeR represents a hydrogen atom or a hydroxyl group and
for a hydroxymethyl or carbamoyloxymethyl group bedeutet,
sowie ihre Salze mit Säuren.means,
as well as their salts with acids. 2. Verbindung nach Anspruch 1 der allgemeinen Formel I, in der R-5 eine Hydroxymethylgruppe bedeutet.2. A compound according to claim 1 of the general formula I, in which R- 5 is a hydroxymethyl group. 3· Verbindung nach Anspruch 1 der allgemeinen Formel I, in3 · Compound according to claim 1 of the general formula I, in 1 2 "5S1 2 " 5 p der R eine Aminogruppe, R ein Wasserstoffatom und R^ eine Hydroxymethylgruppe bedeutet.the R is an amino group, R is a hydrogen atom and R ^ is a Means hydroxymethyl group. L 030563/0003 J L 030563/0003 J. 4. Verfahren zur Herstellung der Verbindungen nach Anspruch 1 bis j5, dadurch gekennzeichnet, daß man ein zuvor geschütztes Aminoglykosid-Derivat der allgemeinen Formel II4. Process for the preparation of the compounds according to claim 1 to j5, characterized in that one previously protected Aminoglycoside derivative of the general formula II HOHO 1 21 2 in der R und R die in Anspruch 1 angegebene Bedeutung ha ben und der Rest A die Formel VI darstelltin which R and R have the meaning given in claim 1 and the radical A represents the formula VI in der R^ eine Hydroxymethyl- oder Carbamoyloxymethy]gruppe bedeutet, mit einer Carbonylverbindung aus der Gruppe Mesitylglyoxalj 3-Nitromesitylglyoxal und 3*5-Dinitromesitylglyoxal zu der entsprechenden Schiffschen Base umsetzt, diese durch Behandlung mit einer Base einer protoni'schen Umlagerung und anschließend einer Säurespaltung unterwirft, die erhaltene Verbindung der allgemeinen Formel IIIin which R ^ is a hydroxymethyl or carbamoyloxymethy] group, with a carbonyl compound from the group mesitylglyoxalj 3-nitromesitylglyoxal and 3 * 5-dinitromesitylglyoxal converts to the corresponding Schiff base, this by treatment with a base of a protonic rearrangement and then subjected to acid cleavage, the resulting compound of the general formula III CHO HO CHO HO (III)(III) dehydratisiert, wobei eine Verbindung der allgemeinen Formel IV erhalten wirddehydrated to give a compound of the general formula IV CHOCHO (IV)(IV) 0305 8 3/00030305 8 3/0003 welch letztere Verbindung einer Reduktions-Aminierung unterworfen wird, die Schutzgruppen entfernt sowie gegebenenfalls das erhaltene Aminoglykosid-Derivat durch Umsetzung mit einer anorganischen oder organischen Säure in das entsprechende Salz überführt.which latter compound is subjected to a reduction-amination, the protective groups are removed and, if applicable the aminoglycoside derivative obtained is converted into the corresponding salt by reaction with an inorganic or organic acid convicted. 5. Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß man als Carbonylverbindung Mesltylglyoxal einsetzt.5. The method according to claim 4, characterized in that Mesltylglyoxal is used as the carbonyl compound. 6. Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß man die prototropische Umlagerung mit 1,5-Diazabicyclo-/3.4.0/-nonen-5 durchführt.6. The method according to claim 4, characterized in that the prototropic rearrangement with 1,5-diazabicyclo- / 3.4.0 / -nonen-5 performs. 7· Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß7. The method according to claim 4, characterized in that man die Säurespaltung mit einer. Carbonsäure durchführt. 15acid cleavage with a. Carboxylic acid performs. 15th 8. Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß man die Reduktions-Aminierung mit einem Metallhydrid durchführt. 8. The method according to claim 4, characterized in that the reduction-amination is carried out with a metal hydride. 9. Pharmazeutische Zubereitung, enthaltend eine wirksame Menge einer Verbindung nach Anspruch 1 und pharmazeutisch verträgliche Trägerstoffe und/oder Verdünnungsmittel und/ oder Hilfsstoffe.9. A pharmaceutical preparation containing an effective amount of a compound according to claim 1 and pharmaceutical compatible carriers and / or diluents and / or auxiliaries. L 030563/0003 L 030563/0003
DE1979103379 1978-09-14 1979-09-10 Aminoglycoside derivatives, processes for their preparation and pharmaceutical compositions Pending DE9197T1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP11340478 1978-09-14

Publications (1)

Publication Number Publication Date
DE9197T1 true DE9197T1 (en) 1981-01-22

Family

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