USRE14216E - Z-naphthylqttinolin-x-carboxylic acids - Google Patents
Z-naphthylqttinolin-x-carboxylic acids Download PDFInfo
- Publication number
- USRE14216E USRE14216E US RE14216 E USRE14216 E US RE14216E
- Authority
- US
- United States
- Prior art keywords
- carboxylic acids
- naphthylqttinolin
- alcohol
- naphthylquinolin
- parts
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- JXDYKVIHCLTXOP-UHFFFAOYSA-N Isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- LLMCWSJMTWWINZ-UHFFFAOYSA-N 2-naphthalen-2-ylquinoline-4-carboxylic acid Chemical class C1=CC=CC2=CC(C=3C=C(C4=CC=CC=C4N=3)C(=O)O)=CC=C21 LLMCWSJMTWWINZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000001225 therapeutic Effects 0.000 description 4
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 2
- 206010072736 Rheumatic disease Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 beta-naphthyl Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 201000005569 gout Diseases 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
Definitions
- This invention relates to the manufacture of the. hitherto unknown 2-naphthylquinolin- 4-carboxylic acids, which correspond to the formula c 11. meaning alphaor beta-naphthyl) and possess valuable therapeutic properties,
- xample 1 80 parts of isatin are disi solved in 500 parts of alcohol and 300 parts of potash lye (33 per cent.) and heated on the water bath for some hours with 90 parts of 'alpha-acetonaphton. The alcohol is then distilled OE and the solution is neutralized with dilute hydrochloric acid. The product of reaction thus, formed is precipitated from a solution of sodium carbonate and recrystallized from dilute alcohol.
- the 2.1 80 parts of isatin are disi solved in 500 parts of alcohol and 300 parts of potash lye (33 per cent.) and heated on the water bath for some hours with 90 parts of 'alpha-acetonaphton. The alcohol is then distilled OE and the solution is neutralized with dilute hydrochloric acid. The product of reaction thus, formed is precipitated from a solution of sodium carbonate and recrystallized from dilute alcohol.
Description
UNITED STATES (V0311. E. SCHERING),
PATENT OFFICE.
xsx nomui', or BERLIN, onnmm, assmnon 'ro cnnmiscnn ranmx AU]? A'CTIEN I O1 BERLIN, GERMANY.
2-NAPH'IHYLQUINOLIN-4-CARBOXYLIC ACIDS.
- Specification of Beissued Letters Iatent. Reissued Nov, 21, 1916, :9.
11o Drawing. Original No. 1,197,482, dated September 5, 1916, Serial No. 33,261, filed June 10, 1915.
Application for reissue filed October 7,1918. Serial No. 124,820).
To all whom it may concern Be it known that I, MAX DonRN, doctor of philosophy, chemist, citizen of the German Empire, residing at Berlin, German Empire,
have invented a new and useful Improvement in 2 Naphthylquinolin-4-Carboxylic Acids, of which the following is a specification.
This invention relates to the manufacture of the. hitherto unknown 2-naphthylquinolin- 4-carboxylic acids, which correspond to the formula c 11. meaning alphaor beta-naphthyl) and possess valuable therapeutic properties,
being especially good remedies against gout and rheumatism. These acids are crystalline compounds, being soluble in alcohol and alkalis, unsoluble in benzene.
- naphthylquinolini-carboxylic acid crystaladded to the-boiling solution. The mixture of reaction'is further heated for sometime 1 and the 2.1-naphthylquinolin-4-carboxylic acid is purified in the known manner.
By starting with beta-naphthylaldehyde the 2.2'-n'aphthylquinolih-4-carboxylic acid is obtained in an analogous way.
I claim, as my invention:
As new products the 2-naphthylquinolin- 4-carboxylic acids having the formula COOK The process for preparing the new compounds consists in condensing isatin with' acetonaphtons in alkaline solution or in condensing' an-ilin with pyroracemic acid and naphthylaldehydes. In carrying out the processes I proceed as follows, the partsbeini lby weight:
xample 1: 80 parts of isatin are disi solved in 500 parts of alcohol and 300 parts of potash lye (33 per cent.) and heated on the water bath for some hours with 90 parts of 'alpha-acetonaphton. The alcohol is then distilled OE and the solution is neutralized with dilute hydrochloric acid. The product of reaction thus, formed is precipitated from a solution of sodium carbonate and recrystallized from dilute alcohol. The 2.1
' C H, meaning alphaor beta-naphth l) being soluble in alcohol and alkalis, insolu 1e in benzene, and possessing valuable therapeutic properties, substantially as described. In testimony whereof I have hereunto set my signature in the presence of two sub scribing witnesses.
i DR. MAX DOHRN.
Witnesses:
HENRY HAsrnn, WOLDEMAR Haur'r.
Family
ID=
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