CH330664A - Process for the preparation of therapeutically valuable aminosalicylic acid derivatives - Google Patents
Process for the preparation of therapeutically valuable aminosalicylic acid derivativesInfo
- Publication number
- CH330664A CH330664A CH330664DA CH330664A CH 330664 A CH330664 A CH 330664A CH 330664D A CH330664D A CH 330664DA CH 330664 A CH330664 A CH 330664A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminosalicylic acid
- water
- therapeutically valuable
- acid derivatives
- preparation
- Prior art date
Links
- NBGAYCYFNGPNPV-UHFFFAOYSA-N 2-aminooxybenzoic acid Chemical class NOC1=CC=CC=C1C(O)=O NBGAYCYFNGPNPV-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000012153 distilled water Substances 0.000 claims description 6
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical class C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 claims description 4
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 4
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- -1 2,3-dichloro-1,4-naphthoquinone-5 sulfonic acid sodium Chemical compound 0.000 claims description 2
- ANQWOEYKZJYUFB-UHFFFAOYSA-N [Na].NOC1=CC=CC=C1C(O)=O Chemical compound [Na].NOC1=CC=CC=C1C(O)=O ANQWOEYKZJYUFB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000005185 salting out Methods 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 230000001549 tubercolostatic effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung therapeutisch wertvoller Aminosalicylsäurederivate
Es wurde gefunden, dass man therapeutisch wertvolle Aminosalieylsäurederivate erhält, wenn man Dichlornaphtochinone, die wasserlöslich machende Gruppen enthalten, mit einer Aminosalicylsäure umsetzt. Als wasserlöslich machende Gruppen kommen dabei z. B. Sulfooder Carboxylgruppen in Betracht. Die erhaltenen Verbindungen zeichnen sich insbesondere durch tuberculostatische Wirkung aus.
Beispiel
In 450 Teilen destilliertem Wasser werden 33 Teile 2,3- dichlor -1,4 - naphtochinon-5 sulfonsaures Natrium mit 18 Teilen 13 aminosalicylsaurem Natrium bei Zimmertemperatur mehrere Stunden verrührt. Dann wird auf 900 erhitzt und die erhaltene Lösung filtriert.
Aus dem Filtrat scheidet sich das Kondensationsprodukt beim Erkalten ab. Es wird abfiltriert und mit wenig destilliertem Wasser gewaschen. Zur Reinigung kann es aus destilliertem Wasser umkristallisiert werden. Aus den Filtraten können durch Aussalzen weitere Mengen gewonnen werden.
Getrocknet stellt das Produkt ein tief dunkelbraunes, in Wasser leicht lösliches Pulver dar.
Die Reaktion verläuft nach folgender Glei chung:
EMI1.1
wobei im Endprodukt die Sulfonsäuregruppe die 5- oder 8-Stellung des Naphthalinkernes einnehmen kann.
PATENTANSPRUCH
Verfahren zur Herstellung therapeutisch wertvoller Aminosalicylsäurederivate, dadurch gekennzeichnet, dass man Dichlornaphto- chinone, die wasserlöslieh machende Gruppen enthalten, mit einer Aminosalicylsäure umsetzt.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of therapeutically valuable aminosalicylic acid derivatives
It has been found that therapeutically valuable aminosalicylic acid derivatives are obtained if dichloronaphthoquinones which contain water-solubilizing groups are reacted with an aminosalicylic acid. As water-solubilizing groups come z. B. sulfo or carboxyl groups. The compounds obtained are distinguished in particular by a tuberculostatic effect.
example
In 450 parts of distilled water, 33 parts of 2,3-dichloro-1,4-naphthoquinone-5 sulfonic acid sodium are stirred with 18 parts 13 aminosalicylic acid sodium at room temperature for several hours. It is then heated to 900 and the resulting solution is filtered.
The condensation product separates out of the filtrate on cooling. It is filtered off and washed with a little distilled water. It can be recrystallized from distilled water for cleaning. Further quantities can be obtained from the filtrates by salting out.
When dried, the product is a deep, dark brown powder that is easily soluble in water.
The reaction proceeds according to the following equation:
EMI1.1
where in the end product the sulfonic acid group can occupy the 5- or 8-position of the naphthalene nucleus.
PATENT CLAIM
Process for the production of therapeutically valuable aminosalicylic acid derivatives, characterized in that dichloronaphthoquinones which contain water-solubilizing groups are reacted with an aminosalicylic acid.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE330664X | 1953-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH330664A true CH330664A (en) | 1958-06-15 |
Family
ID=6191818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH330664D CH330664A (en) | 1953-04-30 | 1954-04-28 | Process for the preparation of therapeutically valuable aminosalicylic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH330664A (en) |
-
1954
- 1954-04-28 CH CH330664D patent/CH330664A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH330664A (en) | Process for the preparation of therapeutically valuable aminosalicylic acid derivatives | |
| DE2752287B2 (en) | Process for the production of salts of aspartic acid | |
| DE504646C (en) | Process for the preparation of anthraquinone and its offshoots | |
| AT218681B (en) | Process for the preparation of caffoyl esters of quinic acid | |
| AT216000B (en) | Process for the preparation of 6-chloro-7-sulfonamido-1,2,4-benzothiadiazine-1,1-dioxyden | |
| AT311974B (en) | Process for the production of new sulfanilamides | |
| AT233010B (en) | Process for the preparation of new benzo-dihydro-1, 2, 4-thiadiazine-1, 1-dioxyden | |
| AT368147B (en) | METHOD FOR PRODUCING NEW GLYOXYL ACID COMPOUNDS | |
| AT254391B (en) | Process for the production of new antibiotic substances of the Cephalosporin C series | |
| AT234681B (en) | Process for the preparation of new 1-methyl-1,2-di- [benzimidazolyl- (2 ')] - ethylene compounds | |
| AT214448B (en) | Process for the preparation of the new 10- (N-β-hydroxyethyl-piperazinyl-N'-propyl) -2-chloro-phenothiazine-5-oxide | |
| AT220766B (en) | Process for the preparation of 3β-acyloxy-Δ <5,16> -pregnadien-20-one | |
| AT230881B (en) | Process for the preparation of propionic acid-3,4-dichloroanilide | |
| DE841916C (en) | Process for the preparation of oxy compounds of the benzoxanthene series | |
| AT200133B (en) | Process for the preparation of new aromatic azonitroso compounds | |
| CH208531A (en) | Process for the production of a fluoranthendicarboxylic acid. | |
| DE598477C (en) | Process for the preparation of substituted aminopyridines | |
| DE825548C (en) | Process for the preparation of new diquartar salts of pyrimidylaminocinnolines | |
| CH349599A (en) | Process for the production of new antituberculotics | |
| CH264198A (en) | Process for the production of a vat dye. | |
| CH269401A (en) | Process for the representation of a basic ether. | |
| CH194997A (en) | Process for the preparation of N- (γ-diethylaminopropyl) -5-amino-m-phenanthroline. | |
| CH269409A (en) | Process for the representation of a basic ether. | |
| CH278134A (en) | Process for the preparation of p-ethyl-ureido-benzalthiosemicarbazone. | |
| CH205525A (en) | Process for the production of melamine. |