GB487378A - Process for the preparation of new soluble aromatic amino compounds of therapeutic value - Google Patents

Process for the preparation of new soluble aromatic amino compounds of therapeutic value

Info

Publication number
GB487378A
GB487378A GB3444936A GB3444936A GB487378A GB 487378 A GB487378 A GB 487378A GB 3444936 A GB3444936 A GB 3444936A GB 3444936 A GB3444936 A GB 3444936A GB 487378 A GB487378 A GB 487378A
Authority
GB
United Kingdom
Prior art keywords
sulphonamide
bisulphite
sodium
aldehyde
aldehydes
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
GB3444936A
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Societe des Usines Chimiques Rhone Poulenc SA
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 Rhone Poulenc SA, Societe des Usines Chimiques Rhone Poulenc SA filed Critical Rhone Poulenc SA
Priority to GB3444936A priority Critical patent/GB487378A/en
Priority to ES0143990A priority patent/ES143990A1/en
Publication of GB487378A publication Critical patent/GB487378A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Sulphonamides of therapeutic value are prepared by treating p-aminobenzene-sulphonamide with aliphatic unsaturated aldehydes, aromatic aldehydes, or aryl-aliphatic aldehydes which are saturated or unsaturated in the aliphatic side chain, in the presence of an alkali metal bisulphite. When the aldehydes are saturated, the three reactants are employed in equimolecular proportions, but when the aldehydes are unsaturated an additional molecular proportion of bisulphite is necessary for each double bond. The products, which contain sulphonic acid groups in the aldehyde residue attached to the nuclear amino group, are water-soluble. The process may be varied by reacting the sulphonamide with bisulphite compounds of the aldehydes, or by treating with bisulphite the condensation products of the sulphonamide and aldehyde. Examples are given of the preparation of (1) sodium p-benzylaminobenzene-sulphonamide-o -sulphonate from benzaldehyde, p-aminobenzene-sulphonamide and sodium bisulphite, or from benzaldehyde-sodium bisulphite and p-aminobenzene-sulphonamide, or benzylidene-amino-benzene-sulphonamide (prepared by condensing benzaldehyde with the sulphonamide) and sodium bisulphite, in each case using equimolecular proportions; (2) sodium p-(b -phenylethylamino) - benzene - sulphonamide - a - sulphonate from phenylacetaldehyde, p-aminobenzene-sulphonamide and sodium bisulphite in equimolecular proportions; (3) sodium p-(g -phenylpropylamino) - benzene - sulphonamide - a : g -disulphonate from sodium bisulphite, cinnamic aldehyde and p-aminobenzene-sulphonamide in the molecular proportions of 2 : 1 : 1; the Schiff's base prepared from the aldehyde and sulphonamide or the bisulphite compound of the aldehyde may also be used, and in place of cinnamic aldehyde, acrylic or crotonic aldehyde may be employed. Specifications 462,765 and 470,462 are referred to. The Provisional Specification also describes the use of nuclear-substituted derivatives of the sulphonamide.
GB3444936A 1936-12-15 1936-12-15 Process for the preparation of new soluble aromatic amino compounds of therapeutic value Expired GB487378A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB3444936A GB487378A (en) 1936-12-15 1936-12-15 Process for the preparation of new soluble aromatic amino compounds of therapeutic value
ES0143990A ES143990A1 (en) 1936-12-15 1937-12-15 A PROCEDURE FOR THE PREPARATION OF ANIMATED COMPOUNDS, SOLUBLE AROMATICS, EQUIPPED WITH A THERAPEUTIC VALUE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3444936A GB487378A (en) 1936-12-15 1936-12-15 Process for the preparation of new soluble aromatic amino compounds of therapeutic value

Publications (1)

Publication Number Publication Date
GB487378A true GB487378A (en) 1938-06-15

Family

ID=10365796

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3444936A Expired GB487378A (en) 1936-12-15 1936-12-15 Process for the preparation of new soluble aromatic amino compounds of therapeutic value

Country Status (2)

Country Link
ES (1) ES143990A1 (en)
GB (1) GB487378A (en)

Also Published As

Publication number Publication date
ES143990A1 (en) 1938-02-16

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