DE293905C - - Google Patents
Info
- Publication number
- DE293905C DE293905C DENDAT293905D DE293905DA DE293905C DE 293905 C DE293905 C DE 293905C DE NDAT293905 D DENDAT293905 D DE NDAT293905D DE 293905D A DE293905D A DE 293905DA DE 293905 C DE293905 C DE 293905C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- cooh
- aceto
- cresotinic
- melts
- 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.)
- Active
Links
- 239000002253 acid Substances 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 5
- OMBVDKVVUYYGFR-UHFFFAOYSA-N 2,3-dioxoindole-1-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)C(=O)C(=O)C2=C1 OMBVDKVVUYYGFR-UHFFFAOYSA-N 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 8
- 239000000155 melt Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DLGBEGBHXSAQOC-UHFFFAOYSA-N 2-hydroxy-5-methylbenzoic acid Chemical compound CC1=CC=C(O)C(C(O)=O)=C1 DLGBEGBHXSAQOC-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-Methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
- C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVl 293905 -KLASSE \2p. GRUPPE - JVl 293905 - CLASS \ 2p. GROUP
Zusatz zum Patent 293467.Addendum to patent 293467.
Patentiert im Deutschen Reiche vom 14. Januar 1915 ab. Längste Dauer: 19. Februar 1929.Patented in the German Empire on January 14, 1915. Longest duration: February 19, 1929.
Durch das Hauptpatent 293467 ist ein Verfahren zur Darstellung der 2«4'-Oxyphenylchinolin-4 · 3-dicarbonsäure geschützt, welches unter anderem darin besteht, daß man die AcetosalicylsäureThe main patent 293467 describes a process for the preparation of 2 «4'-oxyphenylquinoline-4 · 3-dicarboxylic acid protected, which, among other things, consists of the Acetosalicylic acid
(OH: COCH3ICOOH = 1:4:2)(OH: COCH 3 ICOOH = 1: 4: 2)
mit Isatinsäure kondensiert. Diese Oxyphenylchinolindicarbonsäure besitzt therapeutisch wertvolle Eigenschaften.condensed with isatic acid. This oxyphenylquinoline dicarboxylic acid has therapeutic properties valuable properties.
Es wurde nun weiter gefunden, daß man in diesem Verfahren an Stelle der Acetosalicylsäure Acetokresotinsäuren verwenden kann; die so erhältlichen Oxytolylchinolindicarbonsäuren sind in ihren chemischen und therapeutischen Eigenschaften der Oxyphenylchinolindicarbonsäure sehr ähnlich.It has now been found that in this process, instead of acetosalicylic acid Can use acetocresotinic acids; the oxytolylquinolinedicarboxylic acids obtainable in this way are in their chemical and therapeutic properties of the oxyphenylquinolinedicarboxylic acid very similar.
Die vorerwähnten, bisher unbekannten Acetokresotinsäuren kann man durch Kondensation von Acetylchlorid mit o-, m- oder p-Kresotinsäure vermittels Aluminiumchlorids in Gegenwart von Schwefelkohlenstoff herstellen; Acetoo-kresotinsäure The previously unknown acetocresotinic acids mentioned above can be obtained by condensation of acetyl chloride with o-, m- or p-cresotinic acid by means of aluminum chloride in the presence manufacture of carbon disulfide; Acetoo-cresotinic acid
(OHVCOCH3ICOOHiCH3 = 1:4: 2:6)(OHVCOCH 3 ICOOHiCH 3 = 1: 4: 2: 6)
bildet weiße Nadeln, welche bei 212 ° schmelzen; Aceto-m-kresotinsäureforms white needles which melt at 212 °; Aceto-m-cresotinic acid
(OH :COCH3:COOH:CH3 = 1:4:2: 5)(OH: COCH 3 : COOH: CH 3 = 1: 4: 2: 5)
schmilzt bei 204°, ihr Methylester bei 85°; Aceto-p-kresotinsäuremelts at 204 °, its methyl ester at 85 °; Aceto-p-cresotinic acid
(OH: COCH3: COOH: CH3 = 1:6:2:4)
schmilzt bei 1390, ihr Methylester bei 630.(OH: COCH 3 : COOH: CH 3 = 1: 6: 2: 4)
melts at 139 0 , its methyl ester at 63 0 .
147 g Isatin werden in 600 g 33 prozentiger Kalilauge gelöst, sodann 194 g Aceto-o-kresotinsäure hinzugegeben und die Lösung mehrere Stunden auf dem Wasserbad erwärmt. Aus der Lösung wird die neue Säure147 g of isatin are dissolved in 600 g of 33 percent potassium hydroxide solution, then 194 g of aceto-o-cresotinic acid added and the solution warmed for several hours on the water bath. The solution becomes the new acid
COOHCOOH
CH,CH,
O-O HO-O H
COOHCOOH
nach Verdünnung mit Wasser durch Salzsäure gefällt; durch Auskochen mit Alkohol und Kristallisation ihres Natriumsalzes kann sie rein gewonnen werden und bildet dann ein gelbliches Pulver, das bei 276° unter Zersetzung schmilzt.after dilution with water, precipitated with hydrochloric acid; by boiling with alcohol and Crystallization of its sodium salt, it can be obtained pure and then forms yellowish powder which melts at 276 ° with decomposition.
In analoger Weise wird aus Aceto-m-kresotinsäure eine OxytolylchinolindicarbonsäureIn an analogous manner, aceto-m-cresotinic acid becomes an oxytolylquinolinedicarboxylic acid
COOHCOOH
OHOH
COOH,COOH,
welche bei 262 ° schmilzt, und aus Aceto-p- ! schäften der Oxytolylchinolmdicarbonsäure aus kresotinsäure eine isomere Säure I Aceto-o-kresotinsäure sehr ähnlich.which melts at 262 °, and from Aceto-p-! from the oxytolylquinol dicarboxylic acid cresotinic acid an isomeric acid I very similar to aceto-o-cresotinic acid.
COOHCOOH
I CI C
OHOH
■ —O'■ —O '
COOHCOOH
CH,CH,
gewonnen, deren Zersetzungspunkt bei etwa
280° liegt; beide Säuren sind in ihren Eigen-obtained whose decomposition point is about
280 °; both acids are in their own
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE293905C true DE293905C (en) |
Family
ID=548526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT293905D Active DE293905C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE293905C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1890993A2 (en) * | 2005-05-09 | 2008-02-27 | AstraZeneca AB | Benzoic acid derivatives that are modulators or antagonists of glyr |
-
0
- DE DENDAT293905D patent/DE293905C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1890993A2 (en) * | 2005-05-09 | 2008-02-27 | AstraZeneca AB | Benzoic acid derivatives that are modulators or antagonists of glyr |
| EP1890993A4 (en) * | 2005-05-09 | 2010-09-08 | Astrazeneca Ab | Benzoic acid derivatives that are modulators or antagonists of glyr |
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