GB599016A - Improvements in or relating to the production of ribitylaminobenzenes and triacyl derivatives thereof - Google Patents

Improvements in or relating to the production of ribitylaminobenzenes and triacyl derivatives thereof

Info

Publication number
GB599016A
GB599016A GB1284/45A GB128445A GB599016A GB 599016 A GB599016 A GB 599016A GB 1284/45 A GB1284/45 A GB 1284/45A GB 128445 A GB128445 A GB 128445A GB 599016 A GB599016 A GB 599016A
Authority
GB
United Kingdom
Prior art keywords
hydrogenated
ribopyranoside
raney nickel
lbs
yield
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
GB1284/45A
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.)
F Hoffmann La Roche AG
Hoffmann La Roche Inc
Original Assignee
F Hoffmann La Roche AG
Hoffmann La Roche Inc
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 F Hoffmann La Roche AG, Hoffmann La Roche Inc filed Critical F Hoffmann La Roche AG
Publication of GB599016A publication Critical patent/GB599016A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06—Aminosugars
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/16—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
    • 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
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Biotechnology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Ribitylaminobenzenes and triacyl derivatives thereof, of the probable general formula <FORM:0599016/IV/1> wherein R1 and R2 each represent hydrogen or lower alkyl and R3 represents hydrogen or an acyl residue of a lower fatty acid or of an aromatic acid of the benzene series are obtained by hydrogenating, preferably at pH 6 to 7, aromatic N-riboside or a complex salt thereof obtained by the process of Specification 599,013, in presence of a metal catalyst in a solvent. Reduction may be effected at atmospheric or superatmospheric pressures and at temperatures up to 100 DEG C. The terms "lower alkyl" and "lower fatty acid" refer to groups for compounds containing not more than 6 C atoms. Specified solvents are methanol, ethanol, water or dioxane; specified catalysts are Raney nickel, nickel-kieselguhr, palladium, palladium or carbon or other support platinum or platinum on suitable carriers. Advantageously the starting-material employed is a complex of the riboside and an alkali metal or ammonium salt. In example (of which (3) and (6) are for comparative purposes only): (1) a -xylidine-d-ribopyranoside, suspended in absolute alcohol containing Raney nickel is hydrogenated at 500 lbs. pressure at 60 DEG C. to produce N-ribityl-3 : 4-xylidine; (2) a -xylidine-d-ribopyranoside complex with sodium sulphate is hydrogenated as in (1) to yield the product of (1); (3) a -aniline-a -ribofuranoside is hydrogenated as in (1) to yield ribitylaniline; (4) a -aniline-N-d-ribopyranoside - sodium sulphate complex suspended in absolute alcohol containing Raney nickel is hydrogenated at 50 lbs. pressure at 65 DEG C. to yield ribitylaniline; (5) a -aniline-d-ribopyranoside suspended in dioxane containing Raney nickel, is hydrogenated at 65-75 DEG C. at 500 lbs. pressure to yield ribitylaniline; (6) a - 2 : 3 : 5 - tribenzoylaniline - N - d - ribofuranoside, in ethanol containing Raney nickel, is hydrogenated at 500 lbs. pressure at 60 DEG C.; (7) a - 2 : 3 : 4 - tribenzoylaniline - N - d - ribopyranoside is hydrogenated as in (6).
GB1284/45A 1943-09-30 1945-01-16 Improvements in or relating to the production of ribitylaminobenzenes and triacyl derivatives thereof Expired GB599016A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US248479XA 1943-09-30 1943-09-30

Publications (1)

Publication Number Publication Date
GB599016A true GB599016A (en) 1948-03-03

Family

ID=21822703

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1284/45A Expired GB599016A (en) 1943-09-30 1945-01-16 Improvements in or relating to the production of ribitylaminobenzenes and triacyl derivatives thereof
GB1281/45A Expired GB599013A (en) 1943-09-30 1945-01-16 Improvements in or relating to the production of aromatic amine n-pentosides

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB1281/45A Expired GB599013A (en) 1943-09-30 1945-01-16 Improvements in or relating to the production of aromatic amine n-pentosides

Country Status (3)

Country Link
CH (3) CH248480A (en)
GB (2) GB599016A (en)
NL (1) NL62054C (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54132239A (en) * 1978-04-06 1979-10-15 Kureha Chem Ind Co Ltd Anti-tumor agent
SE448602B (en) * 1978-04-06 1987-03-09 Kureha Chemical Ind Co Ltd Compsn. contg. para-amino-benzoic acid glycoside
US4569842A (en) * 1978-04-11 1986-02-11 Kureha Kagaku Kogyo Kabushiki Kaisha Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient
SE446299B (en) * 1978-04-11 1986-09-01 Kureha Chemical Ind Co Ltd MEDICAL COMPOSITION CONTAINING A DERIVATIVE OF PARA-AMINOBENOIC ACID AS ACTIVE INGREDIENT
US4637998A (en) * 1979-10-02 1987-01-20 Kureha Kagaku Kogyo Kabushiki Kaisha Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an active ingredient

Also Published As

Publication number Publication date
CH248480A (en) 1947-05-15
GB599013A (en) 1948-03-03
CH248479A (en) 1947-05-15
NL62054C (en)
CH255410A (en) 1948-06-30

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