GB884623A - New triiodophenyl-propionic acids and x-ray contrast media comprising the same - Google Patents

New triiodophenyl-propionic acids and x-ray contrast media comprising the same

Info

Publication number
GB884623A
GB884623A GB7421/59A GB742159A GB884623A GB 884623 A GB884623 A GB 884623A GB 7421/59 A GB7421/59 A GB 7421/59A GB 742159 A GB742159 A GB 742159A GB 884623 A GB884623 A GB 884623A
Authority
GB
United Kingdom
Prior art keywords
propionic acid
triiodophenyl
compounds
amino
salts
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
GB7421/59A
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.)
Bayer Pharma AG
Original Assignee
Schering AG
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
Priority claimed from DESCH24255A external-priority patent/DE1076894B/en
Priority claimed from DESCH24639A external-priority patent/DE1080266B/en
Application filed by Schering AG filed Critical Schering AG
Publication of GB884623A publication Critical patent/GB884623A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/04—X-ray contrast preparations
    • A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
    • A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
    • A61K49/0495—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound intended for oral administration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/69—Benzenesulfonamido-pyrimidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom
    • C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/16—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
    • C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
    • C09B23/166—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing two or more nitrogen atoms

Abstract

The invention comprises compounds of the general formula <FORM:0884623/IV (b)/1> in which R is hydrogen, an alkyl radical of 1-6 carbon atoms or a cycloalkyl radical of 3-6 carbon atoms, and non-toxic salts of these compounds with inorganic and organic bases. These compounds may be used in the production of X-ray contrast media, and they may be used either as free acids or as non-toxic salts such as the sodium, lithium, ammonium, calcium, methylglucamine, ethanolamine, diethanolamine, ethylamine, diethylamine, and methylglucosamine salts. They may be obtained from the corresponding 2,4,6 - triiodo - 3 - amino - propionic acids by reaction with dimethyl formamide in presence of an acidic reaction promoter such as phosphorus oxychloride. In an example, a -ethyl-b -(3-amino-2,4,6-triiodo-phenyl) -propionic acid is dissolved in dimethylformamide and treated dropwise with phosphorus oxychloride, the reaction mass is treated with acetone, and the hydrochloride of the amidine which separates is dissolved in hot water and treated with caustic soda to form the internal salt of a - ethyl - b - (dimethylamino - methyleneamino - 2,4,6 - triiodophenyl) - propionic acid. The corresponding a -methyl compound is obtained in a similar manner. Compounds containing other alkyl substituents, e.g. n-propyl or n-butyl, in the a -position of the propionic acid are referred to. In another example, b -(3-amino-2,4,6-triiodophenyl)-propionic acid is dissolved in a mixture of dimethyl formamide and chloroform and treated with phosphorus oxychloride to obtain b -(3-dimethylamino-methylene-amino-2,4,6-triiodophenyl)-propionic acid.ALSO:Compounds of the formula <FORM:0884623/VI/1> in which R is hydrogen, an alkyl radical of 1-6 carbon atoms, or a cycloalkyl radical of 3-6 carbon atoms, and non-toxic salts of these compounds, are used together with a carrier material to form X-ray contrast media. Salts which may be used include the sodium, lithium, ammonium, calcium, methylglucamine, ethanolamine, ethylamine, and methyl-glucosamine salts. The media may be prepared in the form of tablets, capsules, or dragees, and may be administered intravenously, perorally, or intraduodenally. The active substances have low toxicity, and very good capacity for absorption and distribution. In an example: a -ethyl - b - (3 - dimethylamino - methylene - amino - 2,4,6 - triiodophenyl) - propionic acid is pasted with maize-starch paste, granulated and dried, then mixed with starch and magnesium stearate, and moulded into tablets. The corresponding compounds having methyl, n-propyl or n-butyl as substituent in the a -position of the propionic acid may be used. The granulated product may be formed into dragees by coating with sugar syrup and waxing. In another example, the calcium salt of b -(3-dimethylamino - methyleneamino - 2,4,6 - triiodophenyl)-propionic acid is mixed with sugar, sodium lauryl sulphonate, sodium carboxymethyl cellulose, and flavouring. The mixture may be taken with water. If the active substance is to be filled into gelatine capsules on a machine, it may first be worked up with liquid paraffin to a fluid paste.
GB7421/59A 1958-04-05 1959-03-03 New triiodophenyl-propionic acids and x-ray contrast media comprising the same Expired GB884623A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DESC023848 1958-04-05
DESCH24255A DE1076894B (en) 1958-06-20 1958-06-20 X-ray contrast media
DESCH24639A DE1080266B (en) 1958-06-20 1958-08-29 X-ray contrast media
DESC025189 1958-12-13

Publications (1)

Publication Number Publication Date
GB884623A true GB884623A (en) 1961-12-13

Family

ID=27437397

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7421/59A Expired GB884623A (en) 1958-04-05 1959-03-03 New triiodophenyl-propionic acids and x-ray contrast media comprising the same

Country Status (5)

Country Link
BE (1) BE577346A (en)
CH (1) CH381806A (en)
FR (1) FR195M (en)
GB (1) GB884623A (en)
NL (1) NL237800A (en)

Also Published As

Publication number Publication date
NL237800A (en) 1964-01-27
BE577346A (en) 1959-07-31
FR195M (en) 1961-02-20
CH381806A (en) 1964-09-15

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