GB599013A - Improvements in or relating to the production of aromatic amine n-pentosides - Google Patents

Improvements in or relating to the production of aromatic amine n-pentosides

Info

Publication number
GB599013A
GB599013A GB1281/45A GB128145A GB599013A GB 599013 A GB599013 A GB 599013A GB 1281/45 A GB1281/45 A GB 1281/45A GB 128145 A GB128145 A GB 128145A GB 599013 A GB599013 A GB 599013A
Authority
GB
United Kingdom
Prior art keywords
pentosides
sodium
complexes
aromatic amine
ammonium
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
GB1281/45A
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 GB599013A publication Critical patent/GB599013A/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    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Aromatic amine N-pentosides of the probable general formula <FORM:0599013/IV/1> p wherein R represents an aryl residue of the benzene or naphthaline series which may be substituted by a further group or groups nonreactive with pentoses under the conditions of reaction, are obtained by treating a primary aromatic amine with a pentose in aqueous solution in presence of a water-miscible organic solvent, e.g. alcohol, substantially at room temperature and a pH between about 2 and 8, the preferred pH being around 4.0. Specified substituents are alkyl, alkoxy, hydroxy, nitro, halogen, carboxyl and carbalkoxy groups. The products are in part, especially characterised by their ability to form complexes with soluble salts of alkali metals or ammonium, which separate from aqueous alcoholic solutions the free pentosides being isolated by extracting the complexes with a suitable solvent, e.g. dioxane or pyridine. Moreover, the N-pentosides may be acylated to obtain triacyl derivatives corresponding to the probable general formula <FORM:0599013/IV/2> wherein R has the signification stated above, and R1 represents an acyl residue, such as formyl acetyl, propionyl, butyryl or benzoyl. The description includes 8 detailed examples, illustrating the formation of the pyranosides. Compounds mentioned are a -aniline-N-d-ribopyranoside and its sodium sulphate complex, a -3 : 4-dimethylaniline-N-d-ribopyranoxide-sodium sulphate complex, a -(b -naphththylamino)-N-d-ribopyranoxide. Complexes with sodium chloride, sodium citrate, ammonium chloride, ammonium acetate and sodium dehydrogen phosphate are also mentioned.
GB1281/45A 1943-09-30 1945-01-16 Improvements in or relating to the production of aromatic amine n-pentosides Expired GB599013A (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
GB599013A true GB599013A (en) 1948-03-03

Family

ID=21822703

Family Applications (2)

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
GB1284/45A Expired GB599016A (en) 1943-09-30 1945-01-16 Improvements in or relating to the production of ribitylaminobenzenes and triacyl derivatives thereof

Family Applications After (1)

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

Country Status (3)

Country Link
CH (3) CH248480A (en)
GB (2) GB599013A (en)
NL (1) NL62054C (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2914005A1 (en) * 1978-04-06 1979-10-18 Kureha Chemical Ind Co Ltd PHARMACEUTICAL PREPARATION WITH AN ORTHO-AMINOBENZOIC ACID DERIVATIVE AS THE ACTIVE SUBSTANCE
DE2914493A1 (en) * 1978-04-11 1979-10-25 Kureha Chemical Ind Co Ltd PHARMACEUTICAL PREPARATION WITH A PARA-AMINOBENZOIC ACID DERIVATIVE AS THE ACTIVE SUBSTANCE
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
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
US4708950A (en) * 1978-04-06 1987-11-24 Kureha Kagaku Kogyo Kabushiki Kaisha Pharmaceutical composition containing a derivative of orthoaminobenzoic acid as an active ingredient

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2914005A1 (en) * 1978-04-06 1979-10-18 Kureha Chemical Ind Co Ltd PHARMACEUTICAL PREPARATION WITH AN ORTHO-AMINOBENZOIC ACID DERIVATIVE AS THE ACTIVE SUBSTANCE
US4708950A (en) * 1978-04-06 1987-11-24 Kureha Kagaku Kogyo Kabushiki Kaisha Pharmaceutical composition containing a derivative of orthoaminobenzoic acid as an active ingredient
DE2914493A1 (en) * 1978-04-11 1979-10-25 Kureha Chemical Ind Co Ltd PHARMACEUTICAL PREPARATION WITH A PARA-AMINOBENZOIC ACID DERIVATIVE AS THE ACTIVE SUBSTANCE
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
US4874750A (en) * 1978-04-11 1989-10-17 Kureha Kagaku Kogyo Kabushiki Kaisha Pharmaceutical composition containing a derivative of para-aminobenzoic acid as an 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
NL62054C (en)
CH248480A (en) 1947-05-15
GB599016A (en) 1948-03-03
CH248479A (en) 1947-05-15
CH255410A (en) 1948-06-30

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