DE2605467A1 - PYRIDINE COMPOUNDS - Google Patents

PYRIDINE COMPOUNDS

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Publication number
DE2605467A1
DE2605467A1 DE19762605467 DE2605467A DE2605467A1 DE 2605467 A1 DE2605467 A1 DE 2605467A1 DE 19762605467 DE19762605467 DE 19762605467 DE 2605467 A DE2605467 A DE 2605467A DE 2605467 A1 DE2605467 A1 DE 2605467A1
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Germany
Prior art keywords
deep
parts
formula
compounds
mixture
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
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DE19762605467
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German (de)
Inventor
Gunther Dipl Chem Dr Lamm
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BASF SE
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BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DE19762605467 priority Critical patent/DE2605467A1/en
Priority to FR7703299A priority patent/FR2340934A1/en
Priority to GB565777A priority patent/GB1572613A/en
Priority to IT2018977A priority patent/IT1075559B/en
Priority to JP1353477A priority patent/JPS5297975A/en
Publication of DE2605467A1 publication Critical patent/DE2605467A1/en
Pending legal-status Critical Current

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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
    • C07D213/78—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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
    • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Die Erfindung betrifft Verbindungen der Formel I in der einThe invention relates to compounds of the formula I. in the one

R Chlor und das andereR chlorine and the other

R Wasserstoff oder einen gegebenenfalls substituierten Rest eines primären Amins undR is hydrogen or an optionally substituted radical of a primary amine and

X Cyan oder Carbamoyl bedeuten.X is cyano or carbamoyl.

Gegebenenfalls substituierte Aminreste sind z.B. C[tief]1 -C[tief]18 Alkylamino, das durch Sauerstoff unterbrochen und durch Hydroxy, C[tief]1 - bis C[tief]8 - Alkoxy, Cyan, Phenyl, Tolyl, Phenoxy oder Cyclohexyl substituiert sein kann, Cyclohexylamino, Norbornylamino oder gegebenenfalls durch Methyl, Methoxy, Chlor, Brom, Amino und Sulfo substituiertes Phenylamino.Optionally substituted amine radicals are, for example, C [deep] 1 -C [deep] 18 alkylamino, which is interrupted by oxygen and by hydroxy, C [deep] 1 - to C [deep] 8 - alkoxy, cyano, phenyl, tolyl, phenoxy or cyclohexyl may be substituted, cyclohexylamino, norbornylamino or phenylamino optionally substituted by methyl, methoxy, chlorine, bromine, amino and sulfo.

Einzelne Reste sind neben den bereits genannten:Individual remnants are in addition to those already mentioned:

NH[tief]2, CH[tief]3 NH-, C[tief]2 H[tief]5 NH-, (n)C[tief]3 H[tief]7 NH-, (i)C[tief]3 H[tief]7 NH-, NH [deep] 2, CH [deep] 3 NH-, C [deep] 2 H [deep] 5 NH-, (n) C [deep] 3 H [deep] 7 NH-, (i) C [deep] 3 H [deep] 7 NH-,

(n)C[tief]4 H[tief]9 NH-, (i)C[tief]4 H[tief]9 NH-, C[tief]2 H[tief]11 NH-, (n)C[tief]6 H[tief]13 NH-, (i)C[tief]6 H[tief]13 NH-, (n)C[tief]7 H[tief]13 NH-, (i)C[tief]7 H[tief]15 NH-, (n)C[tief]8 H[tief]17 NH-, (n) C [deep] 4 H [deep] 9 NH-, (i) C [deep] 4 H [deep] 9 NH-, C [deep] 2 H [deep] 11 NH-, (n) C [ deep] 6 H [deep] 13 NH-, (i) C [deep] 6 H [deep] 13 NH-, (n) C [deep] 7 H [deep] 13 NH-, (i) C [deep] 7 H [deep] 15 NH-, (n) C [deep] 8 H [deep] 17 NH-,

(i)C[tief]13 H[tief]27, (i)C[tief]8 H[tief]17 NH-, C[tief]9 H[tief]19 NH-, C[tief]10 H[tief]21 NH-, C[tief]12 H[tief]25 NH-, C[tief[14 H[tief]29 NH-, C[tief]15 H[tief]31 NH-, C[tief]16 H[tief]33 NH-, C[tief]17 H[tief]35 NH-, C[tief]18 N[tief]37 NH-, CH[tief]3 OC[tief]2 H[tief]4 NH-, C[tief]2 H[tief]5 OC[tief]2 H[tief]4 NH-, C[tief]2 H[tief]5 OC[tief]2 H[tief]4 NH-, C[tief]3 H[tief]7 OC[tief]2 H[tief]4 NH-, C[tief]4 H[tief]9 C[tief]2 H[tief]4 NH-, CH[tief]3 OC[tief]3 H[tief]6 NH-, C[tief]2 H[tief]5 OC[tief]3 H[tief]6 NH-,(i) C [deep] 13 H [deep] 27, (i) C [deep] 8 H [deep] 17 NH-, C [deep] 9 H [deep] 19 NH-, C [deep] 10 H [ deep] 21 NH-, C [deep] 12 H [deep] 25 NH-, C [deep [14 H [deep] 29 NH-, C [deep] 15 H [deep] 31 NH-, C [deep] 16 H [deep] 33 NH-, C [deep] 17 H [deep] 35 NH-, C [deep] 18 N [deep] 37 NH-, CH [deep] 3 OC [deep] 2 H [deep] 4 NH -, C [deep] 2 H [deep] 5 OC [deep] 2 H [deep] 4 NH-, C [deep] 2 H [deep] 5 OC [deep] 2 H [deep] 4 NH-, C [ deep] 3 H [deep] 7 OC [deep] 2 H [deep] 4 NH-, C [deep] 4 H [deep] 9 C [deep] 2 H [deep] 4 NH-, CH [deep] 3 OC [deep] 3 H [deep] 6 NH-, C [deep] 2 H [deep] 5 OC [deep] 3 H [deep] 6 NH-,

(n)C[tief]3 H[tief]7 OC[tief]3 H[tief]6 NH-, (i)C[tief]3 H[tief]7 OC[tief]3 H[tief]6 NH-, (n)C[tief]4 H[tief]9 OC[tief]3 H[tief]6 NH-, (i)C[tief]4 H[tief]9 OC[tief]3 H[tief]6 NH-, (n)C[tief]5 H[tief]11 OC[tief]3 H[tief]6 NH-, (n)C[tief]6 H[tief]13 OC[tief]3 H[tief]6 NH-, (i)C[tief]6 H[tief]13 OC[tief]3 H[tief]6 NH-, (n) C [deep] 3 H [deep] 7 OC [deep] 3 H [deep] 6 NH-, (i) C [deep] 3 H [deep] 7 OC [deep] 3 H [deep] 6 NH -, (n) C [deep] 4 H [deep] 9 OC [deep] 3 H [deep] 6 NH-, (i) C [deep] 4 H [deep] 9 OC [deep] 3 H [deep] 6 NH-, (n) C [deep] 5 H [deep] 11 OC [deep] 3 H [deep] 6 NH-, (n) C [deep] 6 H [deep] 13 OC [deep] 3 H [ deep] 6 NH-, (i) C [deep] 6 H [deep] 13 OC [deep] 3 H [deep] 6 NH-,

HOC[tief]2 H[tief]4 NH-, HOC[tief]3 H[tief]6 NH-, HOC [deep] 2 H [deep] 4 NH-, HOC [deep] 3 H [deep] 6 NH-,

HOC[tief]4 H[tief]8 NH-, HOC[tief]6 H[tief]12 NH-, HOC [deep] 4 H [deep] 8 NH-, HOC [deep] 6 H [deep] 12 NH-,

HOC[tief]4 H[tief]8 OC[tief]3 H[tief]6 NH-, HOC[tief]2 H[tief]4 OC[tief]3 H[tief]6 NH-, HOC[tief]2 H[tief]4 OC[tief]2 H[tief]4 NH-, HOC [deep] 4 H [deep] 8 OC [deep] 3 H [deep] 6 NH-, HOC [deep] 2 H [deep] 4 OC [deep] 3 H [deep] 6 NH-, HOC [deep] 2 H [deep] 4 OC [deep] 2 H [deep] 4 NH-,

NCC[tief]2 H[tief]4 NH-, NC-C[tief]4 H[tief]8 NH-, NC-C[tief]6 H[tief]12 NH-, NC-C[tief]7 H[tief]14 NH-, (n)C[tief]4 H[tief]9 OC[tief]2 H[tief]4 OC[tief]3 H[tief]6 NH- oder (n)C[tief]4 H[tief]9 OC[tief]3 H[tief]6(i)OC[tief]3 H[tief]6 NH-.NCC [deep] 2 H [deep] 4 NH-, NC-C [deep] 4 H [deep] 8 NH-, NC-C [deep] 6 H [deep] 12 NH-, NC-C [deep] 7 H [deep] 14 NH-, (n) C [deep] 4 H [deep] 9 OC [deep] 2 H [deep] 4 OC [deep] 3 H [deep] 6 NH- or (n) C [deep ] 4 H [deep] 9 OC [deep] 3 H [deep] 6 (i) OC [deep] 3 H [deep] 6 NH-.

Von besonderer technischer Bedeutung sind Verbindungen der Formel Ia in der einCompounds of the formula Ia are of particular industrial importance in the one

R[hoch]1 Chlor und das andereR [high] 1 chlorine and the other

R[hoch]1 Amino undR [high] 1 amino and

X Cyan oder Carbamoyl sind.X are cyan or carbamoyl.

Von den Isomeren der Formel Ia sind die der Formel Ib in derOf the isomers of the formula Ia are those of the formula Ib in the

X Cyan oder Carbamoyl ist, bevorzugt.X is cyano or carbamoyl is preferred.

Zur Herstellung der Verbindungen der Formel I kann man Verbindungen der Formel II mit Ammoniak oder Aminen der FormelTo prepare the compounds of the formula I, compounds of the formula II can be used with ammonia or amines of the formula

RNH[tief]2RNH [deep] 2

umsetzen.realize.

Die Verbindungen mit X = CONH[tief]2 erhält man aus der Cyanverbindung durch Hydrolyse, z.B. mit Schwefelsäure.The compounds with X = CONH [deep] 2 are obtained from the cyano compound by hydrolysis, e.g. with sulfuric acid.

Durch Umsetzung der Verbindungen der Formel I, z.B. mit Ammoniak, primären oder sekundären Aminen unter Austausch des Chloratoms erhält man wertvolle Kupplungskomponenten.Valuable coupling components are obtained by reacting the compounds of the formula I, e.g. with ammonia, primary or secondary amines, by exchanging the chlorine atom.

In den folgenden Beispielen beziehen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht.In the following examples, parts and percentages are based on weight, unless otherwise stated.

Beispiel 1example 1

200 Teile 2,6-Dichlornicotinsäurenitril der Formel werden mit 700 Raumteilen 22 bis 25prozentiger wässriger Ammoniaklösung im Autoklaven 10 Stunden bei 75 bis 85°C gerührt. Dann lässt man das Gemisch erkalten, saugt den ausgefallenen Niederschlag ab, wäscht mit Wasser und trocknet bei 70°C.200 parts of 2,6-dichloronicotinonitrile of the formula are stirred with 700 parts by volume of 22 to 25 percent aqueous ammonia solution in an autoclave for 10 hours at 75 to 85 ° C. The mixture is then allowed to cool, the precipitate which has separated out is filtered off with suction, washed with water and dried at 70.degree.

Man erhält ca. 155 Teile eines schwach gelblichen Pulvers, das bei 192°C schmilzt. Das Produkt ist ein Isomerengemisch der Formeln About 155 parts of a pale yellowish powder which melts at 192 ° C. are obtained. The product is a mixture of isomers of the formulas

Beispiel 2Example 2

76 Teile des in Beispiel 1 beschriebenen Isomerengemisches der Formeln werden bei Raumtemperatur in 210 Teile konzentrierte Schwefelsäure eingerührt. Dann erhitzt man das Gemisch auf 60°C, rührt 5 Stunden bei dieser Temperatur und lässt es nach dem Erkalten unter Rühren in 800 bis 1000 Teile Eiswasser einlaufen. Der ausgefallene Niederschlag wird abfiltriert und mit Wasser gewaschen. Das so erhaltene, schwach gelbliche Produkt ist ein Isomerengemisch der Formeln das nach dem Neutralisieren und Umkristallisieren aus Wasser bei 216 bis 218°C schmilzt. Ausbeute: 70 Teile.76 parts of the isomer mixture of the formulas described in Example 1 are stirred into 210 parts of concentrated sulfuric acid at room temperature. The mixture is then heated to 60 ° C., stirred for 5 hours at this temperature and, after cooling, allowed to run into 800 to 1000 parts of ice water with stirring. The deposited precipitate is filtered off and washed with water. The pale yellowish product obtained in this way is an isomer mixture of the formulas which, after neutralization and recrystallization from water, melts at 216 to 218 ° C. Yield: 70 parts.

Beispiel 3Example 3

52 Teile 2,6-Dichlornicotinsäurenitril werden mit 60 Raumteilen N-Methylpyrrolidon, 33 Teilen Anilin und 36 Teilen Triäthylamin 8 Stunden bei 100°C gerührt. Dann wird das Gemisch abgekühlt, mit 500 Raumteilen Wasser versetzt und mit konzentrierter Salzsäure auf pH 1-2 angesäuert. Die kristalline Fällung wird abgesaugt, das Produkt mit Wasser gewaschen und bei 70°C getrocknet. Man erhält 67 Teile des Produktes der Formel das einen geringen Anteil des Produktes der Formel enthält.52 parts of 2,6-dichloronicotinonitrile are stirred with 60 parts by volume of N-methylpyrrolidone, 33 parts of aniline and 36 parts of triethylamine at 100 ° C. for 8 hours. The mixture is then cooled, 500 parts by volume of water are added and the mixture is acidified to pH 1-2 with concentrated hydrochloric acid. The crystalline precipitate is filtered off with suction, the product is washed with water and dried at 70.degree. 67 parts of the product of the formula are obtained that a small proportion of the product of the formula contains.

Der Schmelzpunkt des Gemisches ist 155°C.The melting point of the mixture is 155 ° C.

Beispiel 4Example 4

44 Teile 2,6-Dichlornicotinsäurenitril werden mit 50 Teilen des Amins der Formel 44 parts of 2,6-dichloronicotinonitrile are mixed with 50 parts of the amine of the formula

50 Raumteilen Methanol und 30 Teilen Triäthylamin versetzt. Man rührt 6 Stunden bei 45 bis 50°C, säuert mit Salzsäure auf pH 1 an und setzt 200 Teile Eiswasser zu.50 parts by volume of methanol and 30 parts of triethylamine are added. The mixture is stirred for 6 hours at 45 to 50 ° C., acidified to pH 1 with hydrochloric acid and 200 parts of ice water are added.

Das ausgefallene Öl wird mit Essigester extrahiert. Nach Abdestillieren des Essigesters erhält man 68 Teile eines zähflüssigen Öls der Formel das noch einen kleinen Anteil des Isomeren der Formel enthält.The precipitated oil is extracted with ethyl acetate. After distilling off the ethyl acetate, 68 parts of a viscous oil of the formula are obtained that is still a small proportion of the isomer of the formula contains.

Cl ber.: 11,8%Cl ber .: 11.8%

Cl gef.: 11,4%.Cl found: 11.4%.

Beispiel 5Example 5

70 Teile 2,6-Dichlor-nicotinsäurenitril werden bei 30 bis 35°C mit 100 Raumteilen Methanol und dann mit 55 Teilen kleines beta-Phenyläthylamin versetzt. Nach Zugabe von 45 Teilen Triäthylamin rührt man noch 5 Stunden bei 30 bis 35°C, säuert nach dem Erkalten mit Salzsäure auf pH 0,5-1 an und fällt das Reaktionsprodukt durch Zugabe von 550 Teilen Eis aus. Nach dem Absaugen, Waschen mit Wasser und Trocknen erhält man 105 Teile des Produktes der Formel das noch einen kleineren Anteil des Isomeren der Formel70 parts of 2,6-dichloro-nicotinic acid nitrile are mixed with 100 parts by volume of methanol at 30 to 35 ° C. and then with 55 parts of small beta-phenylethylamine. After adding 45 parts of triethylamine, the mixture is stirred for a further 5 hours at 30 to 35 ° C., after cooling it is acidified with hydrochloric acid to pH 0.5-1 and the reaction product is precipitated by adding 550 parts of ice. After filtering off with suction, washing with water and drying, 105 parts of the product of the formula are obtained that still has a smaller proportion of the isomer of the formula

enthält. Der Misch-Schmelzpunkt des Rohproduktes beträgt 95°C. contains. The mixed melting point of the crude product is 95 ° C.

Cl ber.: 13,8%Cl ber .: 13.8%

Cl gef.: 13,4%.Cl found: 13.4%.

Beispiel 6Example 6

28 Teile 2,6-Dichlor-nicotinsäurenitril werden bei 30°C mit 100 Raumteilen Propanolamin-1,3 versetzt und 4 Stunden bei 30°C gerührt. Anschließend wird das Gemisch mit Salzsäure angesäuert und mit 500 Raumteilen Eiswasser versetzt. Der ausgefallene Niederschlag wird abfiltriert und mit Wasser neutral gewaschen. Man erhält 20 Teile des Produktes der Formel das noch einen kleineren Anteil des Isomeren der Formel enthält.28 parts of 2,6-dichloro-nicotinic acid nitrile are mixed with 100 parts by volume of 1,3-propanolamine at 30.degree. C. and the mixture is stirred at 30.degree. C. for 4 hours. The mixture is then acidified with hydrochloric acid and 500 parts by volume of ice water are added. The deposited precipitate is filtered off and washed neutral with water. 20 parts of the product of the formula are obtained that still has a smaller proportion of the isomer of the formula contains.

Der Mischschmelzpunkt beträgt 116°C.The mixed melting point is 116 ° C.

Analog zu der in den Beispielen beschriebenen Arbeitsweise werden die in der folgenden Tabelle aufgeführten Produkte hergestellt. Angegeben ist jeweils nur das Hauptisomere.The products listed in the table below are prepared analogously to the procedure described in the examples. Only the main isomer is given in each case.

Tabelle 1 Table 1

Tabelle 2 Table 2

Claims (5)

1. Pyridinverbindungen der Formel in der ein1. Pyridine compounds of the formula in the one R Chlor und das andereR chlorine and the other R Wasserstoff oder ein gegebenenfalls substituierter Rest eines primären Amins undR is hydrogen or an optionally substituted radical of a primary amine and X Cyan oder Carbamoyl sind.X are cyan or carbamoyl. 2. Verbindungen gemäß Anspruch 1, wobei R ein sulfogruppenhaltiger Aminoaryl-, insbesondere Aminophenylrest ist.2. Compounds according to claim 1, wherein R is a sulfo-containing aminoaryl, in particular aminophenyl radical. 3. Verbindungen gemäß Anspruch 1 der Formel in der ein3. Compounds according to claim 1 of the formula in the one R[hoch]1 Chlor und das andereR [high] 1 chlorine and the other R[hoch]1 Amino undR [high] 1 amino and X Cyan oder Carbamoyl sind.X are cyan or carbamoyl. 4. Verfahren zur Herstellung von Verbindungen gemäß Anspruch 1, dadurch gekennzeichnet, dass man Verbindungen der Formel 4. Process for the preparation of compounds according to Claim 1, characterized in that compounds of the formula mit Aminen der Formelwith amines of the formula RNH[tief]2RNH [deep] 2 umsetzt.implements. 5. Die Verwendung der Verbindungen gemäß Anspruch 1 zur Herstellung von Kupplungskomponenten für Farbstoffe.5. The use of the compounds according to claim 1 for the preparation of coupling components for dyes.
DE19762605467 1976-02-12 1976-02-12 PYRIDINE COMPOUNDS Pending DE2605467A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DE19762605467 DE2605467A1 (en) 1976-02-12 1976-02-12 PYRIDINE COMPOUNDS
FR7703299A FR2340934A1 (en) 1976-02-12 1977-02-07 DERIVATIVES OF PYRIDINE, THEIR PREPARATION AND THEIR USES
GB565777A GB1572613A (en) 1976-02-12 1977-02-11 Pyridine compounds
IT2018977A IT1075559B (en) 1976-02-12 1977-02-11 PYRIDINE COMPOUNDS
JP1353477A JPS5297975A (en) 1976-02-12 1977-02-12 Pyridine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19762605467 DE2605467A1 (en) 1976-02-12 1976-02-12 PYRIDINE COMPOUNDS

Publications (1)

Publication Number Publication Date
DE2605467A1 true DE2605467A1 (en) 1977-08-18

Family

ID=5969647

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19762605467 Pending DE2605467A1 (en) 1976-02-12 1976-02-12 PYRIDINE COMPOUNDS

Country Status (5)

Country Link
JP (1) JPS5297975A (en)
DE (1) DE2605467A1 (en)
FR (1) FR2340934A1 (en)
GB (1) GB1572613A (en)
IT (1) IT1075559B (en)

Families Citing this family (2)

* 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
JP2001302639A (en) * 2000-04-28 2001-10-31 Nippon Fine Chem Co Ltd Method for producing aminocyanopyridine

Also Published As

Publication number Publication date
FR2340934B3 (en) 1979-10-05
IT1075559B (en) 1985-04-22
JPS5297975A (en) 1977-08-17
FR2340934A1 (en) 1977-09-09
GB1572613A (en) 1980-07-30

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