GB994215A - Isophthalic acid derivatives and process for preparing same - Google Patents
Isophthalic acid derivatives and process for preparing sameInfo
- Publication number
- GB994215A GB994215A GB29941/61A GB2994161A GB994215A GB 994215 A GB994215 A GB 994215A GB 29941/61 A GB29941/61 A GB 29941/61A GB 2994161 A GB2994161 A GB 2994161A GB 994215 A GB994215 A GB 994215A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- amino
- lower alkyl
- ester
- nitro
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of general formula <FORM:0994215/C2/1> wherein R1 and R2 are independently hydrogen atoms or lower (i.e. 1-6 C) alkyl groups, and R3 is a hydrogen atom or a lower alkanoyl group; and the non-toxic pharmaceutically acceptable lower alkyl esters and salts thereof; and their preparation by processes which broadly comprise (1) obtaining compounds wherein R3 is alkanoyl by acylation of the corresponding amino compounds; (2) reacting a 5-nitro-isophthalic acid monolower alkyl ester with ammonium hydroxide or a lower alkylamine to form the corresponding salt of a 5 - nitro - isophthalic acid monoamide, converting this to the acid, reducing the nitro group to 5-amino, and iodinating the product; (3) reacting a 3-carboalkoxy-5-nitrobenzoyl halide with ammonium hydroxide or a mono- or di-lower alkyl amine to form the corresponding lower alkyl ester of a 5-nitro-isophthalic acid monoamide, hydrolysing this to the acid, reducing the nitro group to 5-amino, and iodinating the product; (4) reacting a 5-amino-isophthalic acid mono-lower alkyl ester with ammonium hydroxide or a mono- or di-lower alkylamine, forming the isophthalamic acid derivative and iodinating this; (5) obtaining the lower alkyl esters by reacting a salts of the acids with an alkylating agent in a substantially anhydrous solvent. Other processes mentioned for preparing intermediates are reaction of 5-aminoisophthalic acid monoesters with thionyl chloride, the 3-carbalkoxy - 5 - thionylaminobenzoyl chloride formed yielding, with ammonium hydroxide or a mono- or die alkylamine, a 5-aminoisophthalamic acid. 5 - Nitroisophthalic acid monomethyl ester is prepared by partial hydrolysis of the dimethyl ester, and with phosphorus pentachloride yields 3 - chloroformyl - 5 - nitrobenzoic acid methyl ester.ALSO:Compositions for use as X-ray contrast media contain 5 - amino - triiodoisophthalamic acid derivatives of general formula <FORM:0994215/A5-A6/1> wherein R1 and R2 are independently hydrogen atoms or lower (i.e. 1-6 C) alkyl groups and R3 is a hydrogen atom or a lower alkanoyl group and their nontoxic pharmaceutically acceptable lower alkyl esters and their salts (e.g. sodium and N-methyl glucamine salts); solutions are exemplified.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5178660A | 1960-08-25 | 1960-08-25 | |
| US119287A US3145197A (en) | 1961-06-26 | 1961-06-26 | 5-acetamido-nu-alkyl-2, 4, 6-trhodoiso-phthalamic acid compounds |
| US12138861A | 1961-07-03 | 1961-07-03 | |
| US12537361A | 1961-07-20 | 1961-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB994215A true GB994215A (en) | 1965-06-02 |
Family
ID=27489435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29941/61A Expired GB994215A (en) | 1960-08-25 | 1961-08-18 | Isophthalic acid derivatives and process for preparing same |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE607551A (en) |
| CH (1) | CH424751A (en) |
| DE (1) | DE1443297C3 (en) |
| ES (1) | ES270024A1 (en) |
| FR (1) | FR1589M (en) |
| GB (1) | GB994215A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4801661B2 (en) * | 2005-03-18 | 2011-10-26 | マナック株式会社 | Method for acetylating 5-amino-2,4,6-triiodoisophthalic acid derivative |
-
1961
- 1961-08-18 GB GB29941/61A patent/GB994215A/en not_active Expired
- 1961-08-21 ES ES0270024A patent/ES270024A1/en not_active Expired
- 1961-08-22 DE DE1443297A patent/DE1443297C3/en not_active Expired
- 1961-08-24 CH CH990261A patent/CH424751A/en unknown
- 1961-08-25 BE BE607551A patent/BE607551A/en unknown
- 1961-11-09 FR FR878387A patent/FR1589M/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4801661B2 (en) * | 2005-03-18 | 2011-10-26 | マナック株式会社 | Method for acetylating 5-amino-2,4,6-triiodoisophthalic acid derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| ES270024A1 (en) | 1962-01-01 |
| BE607551A (en) | 1962-02-26 |
| FR1589M (en) | 1962-11-26 |
| DE1443297B2 (en) | 1974-08-29 |
| DE1443297A1 (en) | 1972-01-13 |
| CH424751A (en) | 1966-11-30 |
| DE1443297C3 (en) | 1975-04-17 |
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