[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

DE2141418A1 - Aniline derivatives of nicotinic acid and their salts - Google Patents

Aniline derivatives of nicotinic acid and their salts

Info

Publication number
DE2141418A1
DE2141418A1 DE19712141418 DE2141418A DE2141418A1 DE 2141418 A1 DE2141418 A1 DE 2141418A1 DE 19712141418 DE19712141418 DE 19712141418 DE 2141418 A DE2141418 A DE 2141418A DE 2141418 A1 DE2141418 A1 DE 2141418A1
Authority
DE
Germany
Prior art keywords
halogen
nicotinic acid
salts
aniline derivatives
cooh
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.)
Pending
Application number
DE19712141418
Other languages
German (de)
Inventor
Pier Nello Dr. Buenos Aires. P Ferrari
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.)
Roemmers SAICF
Original Assignee
Roemmers SAICF
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
Application filed by Roemmers SAICF filed Critical Roemmers SAICF
Publication of DE2141418A1 publication Critical patent/DE2141418A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • C07D213/87—Hydrazides; Thio or imino analogues thereof in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

B e s c h r e i b u n g zu der Patentanmeldung Anilinderivate der Nikotinsäure und ihre Salze Die Erfindung betrifft Anilinderivate der Nikotinsäure und ihrer Salze sowie ein Verfahren zu ihrer Herstellung.D e c tio n to the patent application aniline derivatives of Nicotinic acid and its salts The invention relates to aniline derivatives of nicotinic acid and their salts and a process for their preparation.

Die Verbindungen besitzen analgetische und antiphlogistische therapeutische Wirksamkeit und können zur Behandlung von Rheumatismua; Polyarthrits, Phlebitis und ähnlichen Krankheiten Verwendung finden.The compounds have analgesic and anti-inflammatory therapeutic properties Efficacy and can be used to treat rheumatism; Polyarthritis, phlebitis and similar diseases are used.

Die erfindungsgemäß herstellbaren Änilinderivate der Nikotinsäure entsprechen der allgemeinen Formel worin R1 die Bedeutung H, COOH, COO-, OOOR5, CN, oder R² die Bedeutung H, Halogen, NO2, SO2NH2, NHR5, NR25, NH-CO-R5, oder NH2 hat und R3 und R4 für H, Halogen, CN, OH, OR5, COOH, NO2, CH2Halogen, CH(Halogen)2 und C(Halogen)3 stehen, wobei R eine Alkyl-, Alkylaryl- oder Arylgruppe ist.The aniline derivatives of nicotinic acid which can be prepared according to the invention correspond to the general formula where R1 is H, COOH, COO-, OOOR5, CN, or R² has the meaning H, halogen, NO2, SO2NH2, NHR5, NR25, NH-CO-R5, or NH2 and R3 and R4 for H, halogen, CN, OH, OR5, COOH, NO2, CH2 halogen, CH (halogen) 2 and C (halogen) 3, where R is an alkyl, alkylaryl or aryl group.

Zur Herstellung dieser neuen Verbindungsgruppe wird ein gegebenenfalls substituiertes 2-Halogen-nikotinsäurenitril (11) mit dem entsprechend substituierten Anilin(III) gegebenenf-alls in Gegenwart eines Katalysators wie Kupferpulver, Kupferacetat oder Kaliumjodid und in einem Lösungsmittel wie Toluol, Benzol, Xylol, Dimethylformamid, Dimethylsulfoxid, Chloroform usw. nach folgendem Reaktionsschema umgesetzt: worin X für ein Halogen steht, vorzugsweise für Chlor oder für Brom. Eine anschließende Behandlung der Verbindung (IV) mit den notwendigen Reaktionspartnern führt zu den durch die obige Strukturformel (I) widergegebenen Verbindungen.To prepare this new group of compounds, an optionally substituted 2-halo-nicotinic acid nitrile (11) with the correspondingly substituted aniline (III) is optionally used in the presence of a catalyst such as copper powder, copper acetate or potassium iodide and in a solvent such as toluene, benzene, xylene, dimethylformamide , Dimethyl sulfoxide, chloroform, etc. implemented according to the following reaction scheme: wherein X stands for a halogen, preferably for chlorine or for bromine. Subsequent treatment of the compound (IV) with the necessary reactants leads to the compounds represented by the structural formula (I) above.

So erhält man beispielsweise aus dem Nitril (IV) durch Hydrolyse-im alkalischen Medium und anschließendes Ansäuern die entsprechende Carbonsäure, Wird diese Nachbehandlung in der ersten Stufe unterbrochen, so erhält man das Salz; wird sie zu Ende geführt, so kommt man zu der Säure. For example, nitrile (IV) is obtained by hydrolysis alkaline medium and subsequent acidification of the corresponding carboxylic acid, Will If this aftertreatment is interrupted in the first stage, the salt is obtained; will when it is completed, one arrives at the acid.

Außer den Alkalisalzen, Erdalkalisalzen und Metallsalzen gelingt es, andere Verbindungen mit wirksamen Prinzipien zu erhalten, die wie Enzyme, Proteolyti-ka , Antihistaminika, Antibiotika usw. verträglich sind. Besides the alkali salts, alkaline earth salts and metal salts succeed it to get other compounds with effective principles, such as enzymes, proteolyti-ka , Antihistamines, antibiotics, etc. are tolerated.

Beispiel Die Synthese der Verbindungen- kann im-einzelnen wie folgt beschrieben werden: 1. Stufe 1 Mol 2-Chlornikotinsäurenitril und 1 Mol m-Trifluormethylanilin wurden in 500 cm³ Xylol bei 40°C zusammengegeben, das Gemisch auf 140°C erwärmt und 3 Stunden bei dieser Temperatur gehalten. Darauf wurde auf 30°C abgekühlt, filtriert und mit 10 cm3 kaltem Xylol und lp cm3 Petroläther und schließlich mit gewaschen. Der Rückstand wurde aus Äthanol umkristallisiert und das 2(3-Trifluormethylanilin)-3-nikotinsäurenitril erhalten0 2. Stufe 0,2 Mol Nitril aus der ersten Stufe wurden Wasser in 300 cm3 Äthanol gelöst, mit 100 g Natriumhydroxid, gelöst in 100 cm Wasser versetzt und 1 1/2 Stunden zum Sieden erhitzt. Die Lösung wurde abgekühlt, mit 500 cm2 Wasser versetzt und der pH-Wert mit Salzsäure sorgfältig auf 4 eingestellt. Der Niederschlag wurde abfiltriert und gereinigt. Erhalten wurde 2(3-Trifluormethylanilin)-3-nikotinsäure.Example The synthesis of the compounds can be described in detail as follows: 1st stage 1 mol of 2-chloronicotinic acid nitrile and 1 mol of m-trifluoromethylaniline were combined in 500 cm 3 of xylene at 40 ° C., the mixture was heated to 140 ° C. and kept at this temperature for 3 hours. It was then cooled to 30 ° C., filtered and washed with 10 cm3 of cold xylene and 1p cm3 of petroleum ether and finally with. The residue was recrystallized from ethanol and the 2 (3-trifluoromethylaniline) -3-nicotinic acid nitrile obtained0 2nd stage 0.2 mol of nitrile from the first stage was dissolved in water in 300 cm3 of ethanol, 100 g of sodium hydroxide dissolved in 100 cm of water were added and the mixture was heated to the boil for 11/2 hours. The solution was cooled, 500 cm2 of water were added and the pH was carefully adjusted to 4 with hydrochloric acid. The precipitate was filtered off and purified. 2 (3-Trifluoromethylaniline) -3-nicotinic acid was obtained.

3. Stufe Ein Gemisch aus 0,5 Mol 2(3-Trifluormethylanilin)-3-nikotinsäure und 0,5 Mol Natriumhydroxid -in 21 cm3 Wasser wurde 8 Stunden lang gerührt. Es wurde filtriert und darauf 40 g Aluminiuchlorid-hexahydrat in 500 cm3 Wasser zugegeben.3rd stage A mixture of 0.5 mol of 2 (3-trifluoromethylaniline) -3-nicotinic acid and 0.5 mol of sodium hydroxide in 21 cm3 of water was stirred for 8 hours. It was filtered and then 40 g of aluminum chloride hexahydrate in 500 cm3 of water were added.

Es kristallisierte das Aluminiumsalz der 2(3-Trifluormethylanilin)-3-nikotinsäure aus.The aluminum salt of 2 (3-trifluoromethylaniline) -3-nicotinic acid crystallized the end.

Das bei dieser Synthese als Ausgangsmaterial verwendete 2-Chlornikotinsäurenitril kann nach der in "Organic Synthesis" Vol. IV beschriebenen Arbeitsweise hergestellt werden; auf Seite 704 dieser Literaturstelle wird die. Herstellung von Nikotinamid-N-oxid aus Nikotinamid und auf der Seite 166 die Synthese von 2-Chlornikotinsäurenitril aus dem N-Oxid des Nikotinamids beschrieben. The 2-chloronicotinonitrile used as the starting material in this synthesis can be prepared according to the procedure described in "Organic Synthesis" Vol. IV will; on page 704 of this reference, the. Manufacture of nicotinamide N-oxide from nicotinamide and on page 166 the synthesis of 2-chloronicotinonitrile from the N-oxide of nicotinamide.

P a t e n t a n s p r ü c h eP a t e n t a n s p r ü c h e

Claims (2)

Patentansprüche ; Anilinderivate der Nikotinsäure und ihrer Salze der allgemeinen Formel worin R¹ für H, COOH, COO-, COOR5, CN, und R' für H, Halogen, NO2, S02, S02NH2, NHR@, NR@, NH-OO-R5, OR5 und NH2 steht und R³ und R die Bedeutung H, Halogen, CN, OH, OR5, COOH, 5NO2, CH2-Halogen, CH(Halogen)2 und C(Halogen)3 haben, wobei R5 für eine Alkyl-, Alkylaryloder. Arylgruppe steht.Claims; Aniline derivatives of nicotinic acid and its salts of the general formula wherein R¹ is H, COOH, COO-, COOR5, CN, and R 'stands for H, halogen, NO2, S02, S02NH2, NHR @, NR @, NH-OO-R5, OR5 and NH2 and R³ and R mean H, halogen, CN, OH, OR5, COOH, 5NO2, CH2-halogen, CH (halogen) 2 and C (halogen) 3, where R5 is an alkyl, alkylaryl or. Aryl group. 2. Verwendung der Verbindung nach Anspruch 1 als Analgetica und entzündunghemmende Mittel, insbesondere bei der Behandlung von Rheumatismus, Polyarthritis, Phlebitis.2. Use of the compound according to claim 1 as analgesics and anti-inflammatory agents Means, especially in the treatment of rheumatism, polyarthritis, phlebitis.
DE19712141418 1970-08-18 1971-08-18 Aniline derivatives of nicotinic acid and their salts Pending DE2141418A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AR23071570 1970-08-18
AR23335971 1971-01-07
AR23457871 1971-03-19

Publications (1)

Publication Number Publication Date
DE2141418A1 true DE2141418A1 (en) 1972-03-09

Family

ID=32965844

Family Applications (2)

Application Number Title Priority Date Filing Date
DE19712141418 Pending DE2141418A1 (en) 1970-08-18 1971-08-18 Aniline derivatives of nicotinic acid and their salts
DE19712153311 Pending DE2153311A1 (en) 1970-08-18 1971-10-26 2-anilino-pyridine-carboxylic acid derivs prodn - - analgesics and antiinflammatories

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE19712153311 Pending DE2153311A1 (en) 1970-08-18 1971-10-26 2-anilino-pyridine-carboxylic acid derivs prodn - - analgesics and antiinflammatories

Country Status (1)

Country Link
DE (2) DE2141418A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0000816A1 (en) * 1977-08-06 1979-02-21 Beecham Group Plc Substituted amino-pyridine derivatives, processes for their preparation and pharmaceutical compositions containing them

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0000816A1 (en) * 1977-08-06 1979-02-21 Beecham Group Plc Substituted amino-pyridine derivatives, processes for their preparation and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
DE2153311A1 (en) 1972-09-21

Similar Documents

Publication Publication Date Title
DE2205815A1 (en) N-(oxazolin-2-yl)-piperazine - with antitussive activity
DE3500577A1 (en) METHOD FOR PRODUCING 1,2-BENZISOTHIAZOLONES
DE2233889C3 (en) Process for the production of dimethyl maleic anhydride
CH623845A5 (en)
DE2141418A1 (en) Aniline derivatives of nicotinic acid and their salts
DE2426267C2 (en) (1,3) -Thiazolo [4,3-a] isoquinolines, processes for their preparation and preparations containing these compounds
CH638525A5 (en) 3- (TETRAZOL-5-YL) -1-AZAXANTHONE AND METHOD FOR THE PRODUCTION THEREOF.
DE1470070B1 (en) Process for the preparation of benzimidazole derivatives
DE2406972C3 (en) Process for the preparation of 5-sulfamoylanthranilic acids
DE1670933A1 (en) Process for the preparation of sulfonyl semicarbazides
CH513180A (en) Process for the production of anti-diabetic sulfonamides
EP0102318A2 (en) Preparation of beta-amino-alpha,beta-unsaturated carboxylic-acid esters
DE2059949A1 (en) Thienyl fatty acid derivatives, processes for their preparation and their use as pharmaceuticals
DE1930842A1 (en) Process for the production of naphthalenic acid derivatives
DE2811361A1 (en) NEW ISOCHINOLINALDEHYDE AND THE METHOD OF MANUFACTURING IT
DE2334973A1 (en) NEW BIPHENYL DERIVATIVES
AT354432B (en) METHOD FOR PRODUCING 3-INDOLYLESSIC ACIDS
DE2065719C2 (en) 1-lower alkyl substituted 6,7-methylenedioxy-4 (1H) -oxocinnoline-3-carbonitriles
AT241441B (en) Process for the preparation of N- (2,3-dimethylphenyl) anthranilic acid and its salts
AT212838B (en) Process for the preparation of the new sulfamyl-3,4-dihydro-pyrido [2,3-e] -1,2,4-thiadiazine-1,1-dioxyde
DE932674C (en) Process for the preparation of N-alkoxyphenyl-pseudothiohydantoins
DE1770271A1 (en) Piperanzine derivatives and processes for their preparation
AT204048B (en) Process for the preparation of new phenazine derivatives
DE2724038A1 (en) IMPROVEMENTS TO OR RELATING TO ORGANIC COMPOUNDS
AT275525B (en) Process for the preparation of new pyridyl-dihydroisoquinolines and their salts