ES419364A1 - Pseudodi- and trisaccharides and methods for their preparation - Google Patents

Pseudodi- and trisaccharides and methods for their preparation

Info

Publication number
ES419364A1
ES419364A1 ES419364A ES419364A ES419364A1 ES 419364 A1 ES419364 A1 ES 419364A1 ES 419364 A ES419364 A ES 419364A ES 419364 A ES419364 A ES 419364A ES 419364 A1 ES419364 A1 ES 419364A1
Authority
ES
Spain
Prior art keywords
hydroxy
group
amino
hydrogen
alcohol
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
Application number
ES419364A
Other languages
Spanish (es)
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.)
Scherico Ltd
Original Assignee
Scherico Ltd
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 Scherico Ltd filed Critical Scherico Ltd
Publication of ES419364A1 publication Critical patent/ES419364A1/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
    • C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
    • C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
    • C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Procedure for the preparation of pseudotrisaccharides active as antibiotics that have the general formula and its pharmaceutically acceptable acid addition salts and Schiffs base oxazolidine derivatives, wherein in the formula R2 represents hydrogen or hydroxy; R3 represents hydroxy, amino or lower alcohol-monosubstituted amino; R4 represents hydrogen or lower alcohol; and R5 represents hydroxy, amino or monosubstituted lower-amino alcohol, with the conditions: (a) that when R2 is hydroxy, R4 is hydrogen or methyl and R3 is amino, then R5 is hydroxy or monosubstituted lower-amino alcohol and (b) that when both R2 and R3 are hydroxy, and R4 is hydrogen or methyl, then R5 is hydroxy or lower-amino-monosubstituted alcohol, which comprises condensing a selectively blocked garamine of general formula II **(See formula)** where each R12 represents an amino protecting group, and each R11 represents hydrogen or a hydroxy protecting group, and where R12 in position 3'together with R11 in position 4' can represent a protecting group; with a monosaccharide that has the general formula **(See formula)** where R4 is as defined above, hal represents halogen, R14 is -OR13, R15 represents hydrogen or -OR13, X represents -OR13, -NRR12 or an azido group and Y represents -OR13, -NRR12 or a nitrous group, R being hydrogen or lower alcohol, R12 being an amino protecting group and R13 being a hydroxy protecting group and, when necessary, subjecting the pseudotrisaccharide formed to one or two of the following steps (a) to (c) in any order Appropriate: (a) converting an oximino group at the 2'position to a -NHR group and/or converting an azido group at the 6' position to -NH2, R being as defined above; (b) converting an oximino group at position 2'to hydroxy; and (c) converting a group -OR13 in position 6'to a group -NHR, R being as defined above, and subjecting to the pseudotrisaccharide obtained from the condensation or from one or two of steps (a) to (c) to removal of all protecting groups present in the molecule, and, if desired, preparing a pharmaceutically acceptable acid addition salt or an oxazolidinic derivative of Schiffs base of the compound of formula I thus obtained. (Machine-translation by Google Translate, not legally binding)
ES419364A 1972-10-10 1973-10-05 Pseudodi- and trisaccharides and methods for their preparation Expired ES419364A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US29643472A 1972-10-10 1972-10-10
US30806172A 1972-11-20 1972-11-20
US39191473A 1973-08-27 1973-08-27

Publications (1)

Publication Number Publication Date
ES419364A1 true ES419364A1 (en) 1976-07-16

Family

ID=27404431

Family Applications (1)

Application Number Title Priority Date Filing Date
ES419364A Expired ES419364A1 (en) 1972-10-10 1973-10-05 Pseudodi- and trisaccharides and methods for their preparation

Country Status (8)

Country Link
JP (1) JPS49100052A (en)
BG (1) BG21607A3 (en)
DE (1) DE2349974A1 (en)
ES (1) ES419364A1 (en)
FR (1) FR2201872B1 (en)
GB (1) GB1420879A (en)
IL (1) IL43368A0 (en)
NL (1) NL7313668A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2860513D1 (en) * 1977-06-24 1981-04-09 Scherico Ltd Process for preparing aminoglycoside derivatives, novel derivatives obtained and pharmaceutical compositions containing such derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH79A (en) * 1889-01-09 Adam Sautter Johann Movement for pocket watches with an open barrel, new gear pusher system and simplified movement fastening
CH551965A (en) * 1970-06-22 1974-07-31 Scherico Ltd PROCESS FOR PRODUCING ANTIBIOTICALLY ACTIVE COMPOUNDS.
BE787758A (en) * 1971-11-08 1973-02-19 Scherico Ltd PROCESS FOR THE PREPARATION OF A SUBSTANCE WITH ANTIBIOTIC ACTIVITY CONTAINING A NEW ANTIBIOTIC, AND OF DERIVATIVES THEREOF

Also Published As

Publication number Publication date
FR2201872B1 (en) 1977-01-28
AU6107173A (en) 1975-04-10
NL7313668A (en) 1974-04-16
FR2201872A1 (en) 1974-05-03
JPS49100052A (en) 1974-09-20
IL43368A0 (en) 1974-01-14
DE2349974A1 (en) 1974-04-18
BG21607A3 (en) 1976-07-20
GB1420879A (en) 1976-01-14

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