NO744715L - - Google Patents

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Publication number
NO744715L
NO744715L NO744715A NO744715A NO744715L NO 744715 L NO744715 L NO 744715L NO 744715 A NO744715 A NO 744715A NO 744715 A NO744715 A NO 744715A NO 744715 L NO744715 L NO 744715L
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Norway
Prior art keywords
methyl
formula
naphthyridine
ethyl
oxo
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NO744715A
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Norwegian (no)
Inventor
Z Meszaros
I Hermecz
L Vasvari
A Horvath
P Rittli
A Mandi
Original Assignee
Chinoin Gyogyszer Es Vegyeszet
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Priority claimed from HU73CI00001430A external-priority patent/HU171561B/en
Priority claimed from HU74CI00001521A external-priority patent/HU171868B/en
Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet
Publication of NO744715L publication Critical patent/NO744715L/no

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    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Fremgangsmåte ved fremstilling av nye 1,8-naftyridin-derivater. Procedure for the production of new 1,8-naphthyridine derivatives.

Foreliggende oppfinnelse vedrorer en fremgangsmåte ved fremstilling av nye 1,8-nafthyridin-derivater som kan anvendes som utgangs-materiale ved fremstilling av kjente l-alkyl-7-metyl-4-okso-1,4-dihydro-l,8 nafthyridin-3-karboksylsyrer som utviser antibakteriell virkning. Det er kjent at de siste forbindelser kan fremstilles ved alkylering med etterfolgende hydrolyse av 7-metyl-4-okso-3-alkoksy-karbonyl-l,4-dihydro-l,8-nafthyridiner (britisk patent nr. l.ooo.892). The present invention relates to a process for the production of new 1,8-naphthyridine derivatives which can be used as starting material in the production of known 1-alkyl-7-methyl-4-oxo-1,4-dihydro-1,8 naphthyridine- 3-carboxylic acids that exhibit antibacterial action. It is known that the latter compounds can be prepared by alkylation with subsequent hydrolysis of 7-methyl-4-oxo-3-alkoxy-carbonyl-1,4-dihydro-1,8-naphthyridines (British patent no. l.ooo.892 ).

De nye forbindelser som fremstilles i henhold til oppfinnelsen utviser ytterligere verdifulle herbicide og fungicide egenskaper og kan anvendes som plantevernmidler. The new compounds produced according to the invention exhibit further valuable herbicidal and fungicidal properties and can be used as plant protection agents.

Oppfinnelsen vedrorer en fremgangsmåte ved fremstilling av nye 1,8-nafthyridin-derivater av formel (I) The invention relates to a process for the production of new 1,8-naphthyridine derivatives of formula (I)

hvori R, betyr hydrogen eller en gruppe med formelen -(CH2)m-CH3>-(CH2)n-aryl eller -(CH2)-cykloalkyl, R2betyr en gruppe med formelen -(CI^^-CH^, -(CH2^n~aryl eller -(CH„) -cykloalkyl, wherein R, means hydrogen or a group of the formula -(CH2)m-CH3>-(CH2)n-aryl or -(CH2)-cycloalkyl, R2 means a group of the formula -(CI^^-CH^, -(CH2 n~aryl or -(CH„) -cycloalkyl,

zp zp

n, m og p ér et heltall i området o - 5,n, m and p are integers in the range o - 5,

Y betyr en tertiær nitrogenholdig aromatisk heterocyklisk ring bundet til nitrogenatomet, eller en li! trialkylaminogruppe, Y means a tertiary nitrogen-containing aromatic heterocyclic ring bonded to the nitrogen atom, or a li! trialkylamino group,

Z er et anion,Z is an anion,

j j

R 3 er hydrogen eller en C-^^-alkylgruppe,R 3 is hydrogen or a C 1-3 alkyl group,

I og fremgangsmåten er særpreget ved at:<!>In and the procedure is characterized by:<!>

a) en forbindelse av formel (III)a) a compound of formula (III)

hvori R^og R^har de tidligere angitte betydninger wherein R^ and R^ have the previously indicated meanings

og alkylgruppen inneholder 1-6 karbonatomer, omsettes med en aromatisk, tertiær base eller med et trialkylamin i nærvær av et halogen, eller and the alkyl group contains 1-6 carbon atoms, is reacted with an aromatic, tertiary base or with a trialkylamine in the presence of a halogen, or

b) omsetter en forbindelse av formel (II)b) reacts a compound of formula (II)

hvori X betyr halogen og alkylgruppen inneholder wherein X means halogen and the alkyl group contains

1-6 karbonatomer1-6 carbon atoms

med en aromatisk, tertiær base eller et trialkylamin, eller with an aromatic, tertiary base or a trialkylamine, or

c) omsetter en forbindelse av formel (IV)c) reacts a compound of formula (IV)

hvori R^og R_ har den oven angitte betydning, in which R^ and R_ have the meaning indicated above,

med en aromatisk, tertiær base eller et trialkylamin i nærvær av et halogen og hvis onsket alkylerer den erholdte forbindelse av formel (I) (hvori R^ betyr hydrogen), og hvis onsket, over-forer et således erholdt halogenid i et annet halogenid eller et terapeutisk egnet annet anion. with an aromatic, tertiary base or a trialkylamine in the presence of a halogen and, if desired, alkylates the resulting compound of formula (I) (wherein R 1 is hydrogen), and if desired, converts a halide thus obtained into another halide or a therapeutically suitable second anion.

<<

Z betyr fordelaktigst et halogenid-anion ( f.eks. jodid,Z most advantageously means a halide anion (e.g. iodide,

bromid eller klorid) eller et sulfat, fosfat, perklorat eller nitratanion. Y betyr fordelaktigtisk en 5- eller 6-leddete nitrogenholdigemonocykliske,heterocykliske ringer eller en bicyklisk, nitrogenholdig heterocyklisk ring (f.eks. pyridin, alkylsubstituerte pyridiner, f.eks. pikolin, quinaldin eller lepidin, kinolin etc). bromide or chloride) or a sulfate, phosphate, perchlorate or nitrate anion. Y advantageously means a 5- or 6-membered nitrogen-containing monocyclic heterocyclic ring or a bicyclic nitrogen-containing heterocyclic ring (eg pyridine, alkyl substituted pyridines, eg picoline, quinaldine or lepidin, quinoline etc).

I tilfelle R^betyr en alkylgruppe, står det for en rettkjedet eller forgrenet alkylgruppe med 1-6 karbonatomer (f.eks. metyl, etyl, n-propyl, isopropyl, isobutyl etc). In case R^ means an alkyl group, it stands for a straight-chain or branched alkyl group with 1-6 carbon atoms (e.g. methyl, ethyl, n-propyl, isopropyl, isobutyl, etc.).

Det anvendte uttrykket "alkylgruppe" omfatter grupper av formelen -(CH2)m-CH3(f.eks. etyl, nrpropyl etc). Med uttrykket "aralkylgruppen" er grupper av formel -(CH2)m-aryl ment. Uttrykket "cykloalkyl" omfatter grupper av formelen -(CHz „) p-cykloalkyl ( f.eks. cyklopentyl, cykloheksyl, cykloheksylmetyl etc.). I disse formler betyr m, n og p heltall i området 0 - 5. Cykloalkylgruppene kan inneholde 3-6 karbonatomer. Arylgruppene kan eventuelt ha en eller flere substituenter ( f.eks. halogen-atomer, alkyl eller alkoksygrupper). Med uttrykket "halogenatom" menes fluor-, klor-, brom- og jodatornet. The term "alkyl group" used includes groups of the formula -(CH2)m-CH3 (e.g. ethyl, n-propyl etc). By the term "aralkyl group" are meant groups of the formula -(CH2)m-aryl. The term "cycloalkyl" includes groups of the formula -(CHz„)p-cycloalkyl (eg cyclopentyl, cyclohexyl, cyclohexylmethyl, etc.). In these formulas, m, n and p mean integers in the range 0 - 5. The cycloalkyl groups can contain 3-6 carbon atoms. The aryl groups may optionally have one or more substituents (e.g. halogen atoms, alkyl or alkoxy groups). The term "halogen atom" means the fluorine, chlorine, bromine and iodine atoms.

Ifolge fremgangsmåtevariant a) blir en forbindelse av formel (II) 7 omsatt med en nitrogenholdig, aromatisk base eller et trialkylamin i nærvær av et halogen. Ifolge en foretrukket, utfbrelsesform av denne fremgangsmåten blir forbindelsen av formel.(II) omsatt med pyridin, picolin eller kinolin, According to method variant a), a compound of formula (II) 7 is reacted with a nitrogenous, aromatic base or a trialkylamine in the presence of a halogen. According to a preferred embodiment of this method, the compound of formula (II) is reacted with pyridine, picoline or quinoline,

spesielt pyridin, i nærvær av jod. Omsettingen kan utfores ved en temperatur på 2o - 26o°C, spesielt ved 8o - 15o°C. Reaksjonstiden avhenger av den anvendte base og reaksjonstemperaturen. Ved de ovenfor nevnte reaksjonsbetingelser foregår reaksjonen generelt innen lo -6o min. especially pyridine, in the presence of iodine. The reaction can be carried out at a temperature of 2o - 26o°C, especially at 8o - 15o°C. The reaction time depends on the base used and the reaction temperature. Under the above-mentioned reaction conditions, the reaction generally takes place within 10-60 min.

I IN

Ifolge fremgangsmåtevariant b) av fremgangsmåten ifolge opp-I finnelsen, blir en forbindelse av formel (II) omsatt med According to method variant b) of the method according to the invention, a compound of formula (II) is reacted with

en nitrogenholdig aromatisk tertiær base eller et trialkylamin. For dette formål kan pyridin anvendes med fordel. Reaksjons-temperatu ren er 2o - 2oo°C, fortrinnsvis 80- 15o°C. Reaksjonen blir fordelaktig gjennomfort i nærvær av et inert opplosningsmiddel. Reaksjonstiden avhenger av den anvendte base og reaksjonstemperaturen. Ved fremgangsmåtevariantene a) og b) kan et overskudd av den anvendte aromatiske nitrogenholdige base eller et trialkylmin t>jene som reaksjonsmedium. Andere, ved kvarternæriseringsreaksjoner vanlige opplosningsmidler kan også anvendes ( f.eks. dimetylformamid, nitrometan eller dimetylsulfoksyd.). a nitrogenous aromatic tertiary base or a trialkylamine. For this purpose, pyridine can be used with advantage. The reaction temperature is 2o - 2oo°C, preferably 80 - 15o°C. The reaction is advantageously carried out in the presence of an inert solvent. The reaction time depends on the base used and the reaction temperature. In the method variants a) and b), an excess of the used aromatic nitrogen-containing base or a trialkyl mine can serve as reaction medium. Other solvents common in quaternization reactions can also be used (e.g. dimethylformamide, nitromethane or dimethylsulfoxide.).

Ifolge fremgangsmåtevariant c) blir en forbindelse av formelAccording to method variant c) a compound of formula becomes

(IV) omsatt med en nitrogenholdig tertiær aromatisk base eller et trialkylamin i nærvær av et halogen. Reaksjonsbetingelsene og reaktantene ligner de i fremgangsmåtevariant a). Det blir erholdt forbindelser av formel d)/ hvori R^ er hydrogen. (IV) reacted with a nitrogenous tertiary aromatic base or a trialkylamine in the presence of a halogen. The reaction conditions and reactants are similar to those in method variant a). Compounds of formula d) are obtained in which R^ is hydrogen.

De erholdte forbindelser av formel (I), hvori R^ betyr hydrogen, kan hvis onsket underkastes en N-alkylering. N-alkyleringen kan gjennomfores på vanlig måte ved anvendelse av de vanlige alkyleringsmidler. For dette formål kan alkylhologenider (f.eks. etylklorid eller etyljodi), dialkylsulfater ( f.eks. dimetyl-sulfat eller dietylsulfat) , trie.tylfosfat, alkylbenzosulfonat (f.eks. etylbenzensulfonat) eller alkyl-p-toluensulfonater (f.eks. etyl-p-toluensulfonat) anvendes. Alkyleringen blir fordelaktigst utfort i nærvær av et syrebindende middel. For dette formål kan f.eks. alkalimetallkarbonater (f.eks. kaUunkarbonat eller natriumkarbonat), alkalimetallbikarbonater (f.eks. kalimbikarbonat eller natriumbikarbonat), alkalihydrok-syder ( f.eks. natriumhydroksyd) eller organiske baser (f.eks. pyridin eller trialkylamin, som f.eks. trietylamin) anvendes. The obtained compounds of formula (I), in which R 1 means hydrogen, can, if desired, be subjected to an N-alkylation. The N-alkylation can be carried out in the usual way by using the usual alkylating agents. For this purpose, alkyl halides (e.g. ethyl chloride or ethyl iodide), dialkyl sulfates (e.g. dimethyl sulfate or diethyl sulfate), triethyl phosphate, alkyl benzosulfonate (e.g. ethylbenzenesulfonate) or alkyl p-toluenesulfonates (e.g. .ethyl-p-toluenesulfonate) are used. The alkylation is most advantageously carried out in the presence of an acid-binding agent. For this purpose, e.g. alkali metal carbonates (e.g. calcium carbonate or sodium carbonate), alkali metal bicarbonates (e.g. potassium bicarbonate or sodium bicarbonate), alkali hydroxides (e.g. sodium hydroxide) or organic bases (e.g. pyridine or trialkylamine, such as triethylamine ) are used.

Omsetningen kan foregå i nærvær eller fravær av et organisk opplosningsmiddel. Som reaksjonsmedium kan dimetylformamid, dimetylsulfoksyd, nitrometan, acetonitril eller alkanol anvendes. Reaksjonstemperaturen avhenger av det anvendte alkylerings-middel. Det blir fordelaktigst arbeidet ved forhoyet temperatur. The reaction can take place in the presence or absence of an organic solvent. Dimethylformamide, dimethylsulfoxide, nitromethane, acetonitrile or alkanol can be used as reaction medium. The reaction temperature depends on the alkylating agent used. It is most advantageous to work at an elevated temperature.

Ifolge en fordelaktig utforelsesform av fremgangsmåten,According to an advantageous embodiment of the method,

blir etyleringen gjennomfort med trietylfosfat, eventuelt i i nærvær av et av de ovennevnte syrebindende midler. Reaksjonen kan gjennomfores i et inert opplosningsmiddel, eller fortrinnsvis i et overskudd av trietylfosfatet. the ethylation is carried out with triethyl phosphate, optionally in the presence of one of the above-mentioned acid-binding agents. The reaction can be carried out in an inert solvent, or preferably in an excess of the triethyl phosphate.

Anionet til et erholdt halogenid av formel (I) kan overforesThe anion of an obtained halide of formula (I) can be transferred

i et annet halogenid eller i et annet farmasoytisk egnet anion. Omsettningen kan foregå i et vandig medium ved omsetning av halogenidet med det tilsvarende,en syre inneholdende det onskede anion eller deres alkalimetall- eller jordalkalimetallsalter. Man kan også gå frem på'.den måte at man tilsetter halogenidet en ioneveksler som befinner seg i hydrogenfasen og eluerer den bundne base med en syre som inneholder det onskede anion. in another halide or in another pharmaceutically suitable anion. The reaction can take place in an aqueous medium by reacting the halide with the corresponding acid containing the desired anion or their alkali metal or alkaline earth metal salts. One can also proceed in such a way that one adds to the halide an ion exchanger which is in the hydrogen phase and elutes the bound base with an acid containing the desired anion.

Reaksjonsblandingen kan opparbeides på i og for seg kjent måte. Generelt skilles forbindelsene av formel (I) allerede ved avkjolingen av reaksjonsblandingen fra og kan isoleres ved filtrering eller sentrifugering eller ved inndamping av reaksjonsblandingen. The reaction mixture can be worked up in a manner known per se. In general, the compounds of formula (I) are already separated when the reaction mixture is cooled and can be isolated by filtration or centrifugation or by evaporation of the reaction mixture.

De.nye forbindelser av formel (I) kan overfores i de kjente, fra vår patentansokning nr. beskrevne 1-alkyl-7-metyl-4-okso-1,4-dihydro-l,8-nafthyridin-3-karboksylsyrer på den i patentansokningen krevede måte. The new compounds of formula (I) can be transferred into the known 1-alkyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acids described in our patent application no. manner required in the patent application.

Utgangsmaterialene for fremgangsmåten ifolge oppfinnelsen blir fremstilt på folgende måte: 2-amino-6-metyl-pyridin eller dets syreaddisjonssalter blir kondensert med en forbindelse av formel (V) Etter ringslutning av de erholdte, produkter av formel (VI) The starting materials for the method according to the invention are prepared in the following way: 2-amino-6-methyl-pyridine or its acid addition salts are condensed with a compound of formula (V) After cyclization of the obtained products of formula (VI)

dannes utgangsmaterialene av formel (IV). Ved N-alkylering av disse forbindelser blir utgangsmaterialene av formel (III) erholdt. Forbindelser av formel (II) kan fremstilles derved, the starting materials of formula (IV) are formed. By N-alkylation of these compounds, the starting materials of formula (III) are obtained. Compounds of formula (II) can be prepared thereby,

at man i ovenfornevnte metode anvender halogenderivatene av formel (V). that the halogen derivatives of formula (V) are used in the above-mentioned method.

De nye forbindelser av formel (I) har fungicide og herbicide egenskaper. The new compounds of formula (I) have fungicidal and herbicidal properties.

Oppfinnelsen vedrorer ytterligere plantevernmidler som inneholder som virksomt stoff en forbindelse av formel (I) og egnede, inerte faste eller flytende bærere. Disse preparater kan fremstilles på i og for seg kjent måte ved blanding av det virksomme stoff med inerte bærere og eventuelt med vanlige hjelpestoffer (f.eks. overflateaktive midler.) The invention further relates to pesticides which contain as active substance a compound of formula (I) and suitable, inert solid or liquid carriers. These preparations can be prepared in a manner known per se by mixing the active substance with inert carriers and possibly with common auxiliary substances (e.g. surfactants.)

Preparatene kan formes etter i plantevernmiddelindustrienThe preparations can be modeled after the pesticide industry

kjente metoder som sproytepulver, pulverblandinger, sproyte-væske, granalier, konsentrater, premixturer, etc. known methods such as spray powder, powder mixtures, spray liquid, granules, concentrates, premixtures, etc.

Oppfinnelsen blir i det etterfolgende belyst av eksempler. The invention is hereinafter illustrated by examples.

EKSEMPEL 1EXAMPLE 1

En blanding av 1,22 g l-etyl-7-metyl-3-propionyl-4-okso-1,4-dihydro-l,8-nafthyridin, lo ml pyridin og 1,27 g jod blir omrort ved loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Man erholder l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-naf thyridin-3-kar bo ny 1- (metyl-metyl-pyridinium)-jodid. A mixture of 1.22 g of 1-ethyl-7-methyl-3-propionyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pyridine and 1.27 g of iodine is stirred at 10°C , after which the reaction mixture is evaporated in vacuo. One obtains 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbo ny 1-(methyl-methyl-pyridinium)-iodide.

EKSEMPEL 2EXAMPLE 2

En blanding av 1,22 g l-etyl-7-metyl-3-propionyl-4-okso-l,4-dihydro-1,8-nafthyridin, lo mr pycolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir inndampet i vakuum. Man erholder l-etyl-7-metyl-4-okso-l,4-dihydro-1,8-nafthyridin-3-karbonyl-(metyl-metyl-pycolinium) -jodid. A mixture of 1.22 g of 1-ethyl-7-methyl-3-propionyl-4-oxo-1,4-dihydro-1,8-naphthyridine, lo mr pycoline and 1.27 g of iodine is heated on a water bath under constant agitation. The reaction mixture is evaporated in vacuo. One obtains 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(methyl-methyl-pycolinium)-iodide.

EKSEMPEL 3EXAMPLE 3

En blanding av 1,22 g l-etyl-7-metyl-3-propionyl-4-okso-l,4-dihydro-1, 8-naf thyridin, lo ml kinolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir inndampet i vakuum. Man erholder l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(metyl-metyl-kinolinium)-jodid. A mixture of 1.22 g of 1-ethyl-7-methyl-3-propionyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of quinoline and 1.27 g of iodine is heated on a water bath under constant agitation. The reaction mixture is evaporated in vacuo. 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(methyl-methyl-quinolinium)-iodide is obtained.

EKSEMPEL 4EXAMPLE 4

En blanding av 1,22 g l-etyl-7-metyl-3-propionyl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml isokinolin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Man erholder l-etyl-7-metyl-4-okso-l,4-dihydro-1,8-nafthyridin-3-karbonyl-(metyl-metyl-isokinolinium)-jodid. A mixture of 1.22 g of 1-ethyl-7-methyl-3-propionyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of isoquinoline and 1.27 g of iodine is stirred at 10°C , after which the reaction mixture is evaporated in vacuo. 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(methyl-methyl-isoquinolinium)-iodide is obtained.

EKSEMPEL 5EXAMPLE 5

En blanding av 1,29 g l-etyl-7-metyl-3-butiryl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml pyridin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Man erholder l-etyl-7-metyl-4-okso-l,4-dihydro-1-1,8-nafthyridin-3-karbonyl-(etyl-metyl-pyridinium)-jodid. A mixture of 1.29 g of 1-ethyl-7-methyl-3-butyryl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pyridine and 1.27 g of iodine is stirred at 10°C , after which the reaction mixture is evaporated in vacuo. One obtains 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1-1,8-naphthyridine-3-carbonyl-(ethyl-methyl-pyridinium)-iodide.

EKSEMPEL 6EXAMPLE 6

En blanding av 1,29 g l-etyl-7-metyl-3-butiryl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml pycolin og 1,27 g jod blir j omrort på loo°Cå hvoretter reaksjonsblandinge blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-1,8-nafthyridin-3-karbonyl-(etyl-metyl-pycolinium)-jodid. A mixture of 1.29 g of 1-ethyl-7-methyl-3-butyryl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pycoline and 1.27 g of iodine is stirred at loo° After which reaction mixtures are evaporated in vacuum. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(ethyl-methyl-pycolinium)-iodide.

EKSEMPEL 7EXAMPLE 7

En blanding av 1,29 g l-etyl-7-metyl-3-butiryl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml kinolin og 1,27 g. jod blir onrort på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-1,8-nafthyridin-3-karbonyl-(etyl-metyl-kinolinium)-jodid. A mixture of 1.29 g of 1-ethyl-7-methyl-3-butyryl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of quinoline and 1.27 g of iodine is stirred at 10° C, after which the reaction mixture is evaporated in vacuo. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(ethyl-methyl-quinolinium)-iodide.

EKSEMPEL 8EXAMPLE 8

En blanding av 1,29 l-etyl-7-metyl-3-butiryl-4-okso-l, 4-dihydro-1,8- nafthyridin, lo ml isokinolin og 1,27 g jod blir omrort ved loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(etyl-metyl-isokinolin)-jodid. A mixture of 1.29 l-ethyl-7-methyl-3-butyryl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of isoquinoline and 1.27 g of iodine is stirred at 10°C, after which the reaction mixture is evaporated in vacuo. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(ethyl-methyl-isoquinoline)-iodide.

EKSEMPEL 9EXAMPLE 9

En blanding av 1,36 g l-etyl-7-metyl-3-valeroyl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml pyridin og 1,27 gjod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir inndampet i vakuum. Som. produkt erholdes l-etyl-7-metyl-4-okso-^l, 4-dihydro-l, 8-nafthyridin-3-karbonyl- (propyl-metyl-pyridinium)-jodid. A mixture of 1.36 g of 1-ethyl-7-methyl-3-valeroyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pyridine and 1.27 g of iodine is heated on a water bath with constant stirring . The reaction mixture is evaporated in vacuo. As. product is obtained 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(propyl-methyl-pyridinium)-iodide.

EKSEMPEL loEXAMPLE lo

En blanding av 1,36 g l-etyl-7-metyl-3-valeroyl-4-okso-l, 4-dihydro-1,8-nafthyridin, lo ml pycolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(propyl-metyl-pycolinium)-jodid. A mixture of 1.36 g of 1-ethyl-7-methyl-3-valeroyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pycoline and 1.27 g of iodine is heated on a water bath under constant agitation. The reaction mixture is evaporated in vacuo. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(propyl-methyl-pycolinium)-iodide.

EKSEMPEL 11EXAMPLE 11

En blanding av 1,36 g l-etyl-7-metyl-3-valeroyl-4-okso-l,4- i dihydro-1,8-nafthyridin, lo ml kinolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(propyl-metyl-kinolinium)-jodid. A mixture of 1.36 g of 1-ethyl-7-methyl-3-valeroyl-4-oxo-1,4-in dihydro-1,8-naphthyridine, 10 ml of quinoline and 1.27 g of iodine is heated on a water bath under constant agitation. The reaction mixture is evaporated in vacuo. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(propyl-methyl-quinolinium)-iodide.

EKSEMPEL 12EXAMPLE 12

En blanding av 1,36 g l-etyl-7-metyl-3-valeroyl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml isokinolin og 1,27 g jod blir oppvarmet på vannbad under stadig "otmroring. Reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(propyl-metyl-isokinolinium)-jodid. A mixture of 1.36 g of 1-ethyl-7-methyl-3-valeroyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of isoquinoline and 1.27 g of iodine is heated on a water bath under constant stirring. The reaction mixture is evaporated in vacuo. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(propyl-methyl-isoquinolinium)-iodide.

EKSEMPEL 13EXAMPLE 13

En blanding av 1,53 g l-etyl-7-metyl-3-fenacetyl-4-okso-l, 4-dihydro-1,8-nafthyridin, lo ml pyridin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-1,8-nafthyridin-3-karbonyl-(fenyl-metyl-pyridinium)^jodid. A mixture of 1.53 g of 1-ethyl-7-methyl-3-phenacetyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pyridine and 1.27 g of iodine is stirred at 10°C , after which the reaction mixture is evaporated in vacuo. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(phenyl-methyl-pyridinium)-iodide.

EKSEMPEL 14EXAMPLE 14

En blanding av 1,53 g l-etyl-7-metyl-3-fenacetyl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml pycolin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir opparbeidet med vanlige metoder. Som produkt blir l-etyl-7-metyl-4-okso-1,4-dihydro-l,8-nafthyridin-3-karbonyl-(fenyl-metyl-pycolinium)-jodid. A mixture of 1.53 g of 1-ethyl-7-methyl-3-phenacetyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pycoline and 1.27 g of iodine is stirred at 10°C , after which the reaction mixture is worked up using usual methods. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(phenyl-methyl-pycolinium)-iodide.

EKSEMPEL 15EXAMPLE 15

En blanding av 1,53 g l-etyl-7-metyl-3-fenacetyl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml kinolin bg 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-1,4wdihydro-l,8-nafthyridin-3-karbonyl-(fenyl-metyl-kino-linium)-jodid. A mixture of 1.53 g of 1-ethyl-7-methyl-3-phenacetyl-4-oxo-1,4-dihydro-1,8-naphthyridine, lo ml of quinoline bg 1.27 g of iodine is heated on a water bath under constant agitation. The reaction mixture is evaporated in vacuo. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4wdihydro-1,8-naphthyridine-3-carbonyl-(phenyl-methyl-quinolinium)-iodide.

i in

EKSEMPEL 16EXAMPLE 16

En blanding av 1,53 g l-etyl-7-metyl-3-fenacetyl-4-okso-l,4-dihydro-1,8-nafthyridin, lo ml isokinolin og 1,27 g jod blir oppvarmet under stadig omroring på vannbad. Reaksjonsblandingen blir opparbeidet med de vanlige metoder. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(fenyl-metyl-isokinolinium)-jodid. A mixture of 1.53 g of 1-ethyl-7-methyl-3-phenacetyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of isoquinoline and 1.27 g of iodine is heated with constant stirring on water bath. The reaction mixture is worked up using the usual methods. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(phenyl-methyl-isoquinolinium)-iodide.

EKSEMPEL 17EXAMPLE 17

En blanding av 1,6o g l-etyl-7-metyl-3-(3-fenyl-propionyl)-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml pyridin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir opparbeidet etter vanlige metoder. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-)benzyl-metyl-pyridinium)-jodid. A mixture of 1.60 g of 1-ethyl-7-methyl-3-(3-phenyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pyridine and 1.27 g of iodine is heated in a water bath with constant stirring. The reaction mixture is prepared according to usual methods. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl (benzyl-methyl-pyridinium)-iodide.

EKSEMPEL 18EXAMPLE 18

En blanding av 1,6o g l-etyl-7-metyl-3-(3-fenyl-propionyl)-4-okso-l, 4' dihydro-1, 8-naf thyridin, lo ml pycolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir inndampet i vaktium. Som produkt erholdes l-etyl-7-metyl-4-okso-l, 4-dihydro-l, 8-nafthyridin-3-karbonyl-(benzyl-metyl-pycolinium)-jodid. A mixture of 1.60 g of 1-ethyl-7-methyl-3-(3-phenyl-propionyl)-4-oxo-1,4' dihydro-1,8-naphthyridine, 10 ml of pycoline and 1.27 g iodine is heated in a water bath with constant stirring. The reaction mixture is evaporated in vacuo. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(benzyl-methyl-pycolinium)-iodide.

EKSEMPEL 19EXAMPLE 19

En blanding av 1,6 g l-etyl-7-metyl-3-(3-fenyl-propionyl)-4-okso-1, 4-idihydro-l, 8-naftyridin, lo ml kinolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir opparbeidet med vanlige metoder. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3- karbonyl-(benzyl-metyl-kinolinium)-jodid. A mixture of 1.6 g of 1-ethyl-7-methyl-3-(3-phenyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of quinoline and 1.27 g of iodine is heated in a water bath with constant stirring. The reaction mixture is worked up using usual methods. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(benzyl-methyl-quinolinium)-iodide.

EKSEMPEL 2oEXAMPLE 2o

En blanding av 1,6o g l-etyl-7-metyl-3-(3-fenyl-propionyl)-4- okso-l,4-dihydro-l,8-nafthyridin, lo ml isokinolin og 1,27 g jod blir oppvarmet på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbon-ul-(benzyl-metyl-isokinolinium)-jodid. A mixture of 1.60 g of 1-ethyl-7-methyl-3-(3-phenyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of isoquinoline and 1.27 g of iodine is heated to loo°C, after which the reaction mixture is evaporated in vacuo. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbon-1-(benzyl-methyl-isoquinolinium)-iodide.

r r

EKSEMPEL 21EXAMPLE 21

En blanding av 1,56 g l-etyl-7-metyl-3-cykloheksyl-acetyl- i 4-okso-l,4-dihydro-l,8-nafthyridin, lo ml pyridin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandinge.i blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-1,4-dihydro-l,8-nafthyridin-3-karbonyl-(cykloheksyl-metyl-pyridinium) - jodid. A mixture of 1.56 g of 1-ethyl-7-methyl-3-cyclohexyl-acetyl-1 4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pyridine and 1.27 g of iodine is stirred on loo°C, after which the reaction mixture is evaporated in vacuo. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(cyclohexyl-methyl-pyridinium)-iodide.

EKSEMPEL 22EXAMPLE 22

En blanding av 1,56 g l-etyl-7-metyl-3-cykloheksyl-acetyl-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml pycolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir opparbeidet med vanlige metoder. A mixture of 1.56 g of 1-ethyl-7-methyl-3-cyclohexyl-acetyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pycoline and 1.27 g of iodine is heated on a water bath under constant stirring. The reaction mixture is worked up using usual methods.

Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(cykloheksyl-metyl-pycolinium)-jodid. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(cyclohexyl-methyl-pycolinium)-iodide.

EKSEMPEL 23EXAMPLE 23

En blanding av 1,56 g l-etyl-7-metyl-3-cykloheksyl-acetyl-4-okso-1,4-dihydro-l,8-nafthyridin, lo ml kinolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir opparbeidet med'vanlige metoder. Som. produkt blir erholdt l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3- karbonyl-(cykloheksyl-metyl-kinolinium)-jodid. A mixture of 1.56 g of 1-ethyl-7-methyl-3-cyclohexyl-acetyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of quinoline and 1.27 g of iodine is heated on a water bath under constant stirring. The reaction mixture is worked up using usual methods. As. product is obtained 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(cyclohexyl-methyl-quinolinium)-iodide.

EKSEMPEL 24EXAMPLE 24

En blanding av 1,56 g l-etyl-7-metyl-3-cykloheksyl-acetyl-4- okso-l,4-dihydro-l,8-nafthyridin, lo ml isokinolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring. Reaksjonsblandingen blir opparbeidet med vanlige metoder. A mixture of 1.56 g of 1-ethyl-7-methyl-3-cyclohexyl-acetyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of isoquinoline and 1.27 g of iodine is heated on a water bath under constant stirring. The reaction mixture is worked up using usual methods.

Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(cykloheksyl-metyl-isokinolinium)-jodid. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(cyclohexyl-methyl-isoquinolinium)-iodide.

EKSEMPEL 2 5EXAMPLE 2 5

En blanding av 1,63 l-etyl-7-metyl-3-(3-cykloheksyl-propionyl)-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml pyridin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-1, 4-dihydro-l, 8-naf thyridin-3-karbonyl -,/Tcykloheksyl-metyl)-metyl-pyridinium/-jodid. A mixture of 1.63 l-ethyl-7-methyl-3-(3-cyclohexyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pyridine and 1.27 g of iodine is stirred at 10°C, after which the reaction mixture is evaporated in vacuo. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl -(((Tcyclohexyl-methyl)-methyl-pyridinium)-iodide.

EKSEMPEL 26EXAMPLE 26

En blanding av 1,63 g l-etyl-7-metyl-3-(3-cykloheksyl-propinyl)-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml pycolin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes 1-r etyl-7-mety 1-4-okso-1,4-dihydro-l,8-nafthyridin-3-karbonyl-/Tcykloheksyl-metyl)-metyl-pycolinium7-jodid. A mixture of 1.63 g of 1-ethyl-7-methyl-3-(3-cyclohexyl-propynyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pycoline and 1.27 g of iodine is stirred at 10°C, after which the reaction mixture is evaporated in vacuo. The product obtained is 1-r-ethyl-7-methyl 1-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl ((T-cyclohexyl-methyl)-methyl-pycolinium-7-iodide).

EKSEMPEL 27EXAMPLE 27

En blanding av 1,63 g l-etyl-7-metyl-3-(3-cykloheksyl-propionyl)-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml kinolin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-1,4-dihydro-l,8-nafthyridin-3-karbonyl-^Tcykloheksyl-metyl)-metyl-kinolinium7-jodid. A mixture of 1.63 g of 1-ethyl-7-methyl-3-(3-cyclohexyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of quinoline and 1.27 g of iodine is stirred at 10°C, after which the reaction mixture is evaporated in vacuo. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-((Tcyclohexyl-methyl)-methyl-quinolinium-7-iodide).

EKSEMPEL 28EXAMPLE 28

En blanding av 1,63 g l-etyl-7-metyl-3-(3-cykloheksyl-propinoyl)-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml iso-konolin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-/Tcykloheksyl-metyl)-metyl-dsokinoliniumj-jodid. A mixture of 1.63 g of 1-ethyl-7-methyl-3-(3-cyclohexyl-propinoyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of iso-conoline and 1.27 g of iodine is stirred at 10°C, after which the reaction mixture is evaporated in vacuo. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-((Tcyclohexyl-methyl)-methyl-disoquinolinium iodide).

EKSEMPEL 29EXAMPLE 29

En blanding av 1,29 g l-etyl-7-metyl-3-(2-metyl-propionyl)-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml pyridin og 1,27 g jod blir omrort på loo°C, hvoretter reaksjonsblandingen blir opparbeidet med vanlige metoder. Som produkt erholdes 1-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(dimetyl-metyl-pyridinium)-jodid. A mixture of 1.29 g of 1-ethyl-7-methyl-3-(2-methyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of pyridine and 1.27 g of iodine is stirred at loo°C, after which the reaction mixture is worked up by usual methods. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(dimethyl-methyl-pyridinium)-iodide.

EKSEMPEL 3oEXAMPLE 3o

En blanding av 1,29 l-etyl-7-metyl-3-(3-metyl-propionyl)-4-okso-1, 4a)dihydro-l, 8-naf thyridin, lo ml pycolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring, hvoretter reaksjonsblandingen blir opparbeidet med vanlige metoder. Som produkt erholder man l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(dimetyl-metyl-pycolinium)-jodid. A mixture of 1.29 l-ethyl-7-methyl-3-(3-methyl-propionyl)-4-oxo-1,4a)dihydro-1,8-naphthyridine, lo ml pycoline and 1.27 g iodine is heated on a water bath with constant stirring, after which the reaction mixture is worked up using usual methods. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(dimethyl-methyl-pycolinium)-iodide.

EKSEMPEL 31EXAMPLE 31

En blanding av 1,29 g l-etyl-7-metyl-3-(2-metyl-propionyl)-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml kinolin og 1,27 g jod blir oppvarmet på vannbad under stadig omroring, hvoretter reaksjonsblandingen blir opparbeidet med vanlige metoder. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(dimetyl-metyl-kinolinium)-jodid. A mixture of 1.29 g of 1-ethyl-7-methyl-3-(2-methyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of quinoline and 1.27 g of iodine is heated on a water bath with constant stirring, after which the reaction mixture is worked up using usual methods. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(dimethyl-methyl-quinolinium)-iodide.

EKSEMPEL 32EXAMPLE 32

En blanding av 1,29 g l-etyl-7-metyl-3-(2-metyl-propionyl)-4-okso-l,4-dihydro-l,8-nafthyridin, lo ml isokinolin og 1,27 g. jod blir oppvarmet på vannbad under stadig roring. Reaksjonsblandingen blir opparbeidet med vanlige metoder. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl- (dimetyl-metyl-isokinolinium) - jodid. A mixture of 1.29 g of 1-ethyl-7-methyl-3-(2-methyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine, 10 ml of isoquinoline and 1.27 g. iodine is heated in a water bath with constant stirring. The reaction mixture is worked up using usual methods. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(dimethyl-methyl-isoquinolinium)-iodide.

EKSEMPEL 33EXAMPLE 33

En blanding av l,o8 g 7-mety1-3-propionyl-4-okso-1,4-dihydro-1,8-nafthyridin, 5o ml pyridin og 1,27 g jod blir oppvarmet i 5 timer på vannbad, hvoretter reaksjonsblandingen henstår i 2 dager ved romtemperatur. De utfelite krystaller blir frafiltrert, vasket med litt etanol. Man erholder 7-metyl-4-okso-1,4-dihydro-l,8-nafthyridin-3-karbonyl-(metyl-metyl-pyridinium)-jodid. A mixture of 1.08 g of 7-methyl-3-propionyl-4-oxo-1,4-dihydro-1,8-naphthyridine, 50 ml of pyridine and 1.27 g of iodine is heated for 5 hours on a water bath, after which the reaction mixture leave for 2 days at room temperature. The precipitated crystals are filtered off, washed with a little ethanol. 7-Methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(methyl-methyl-pyridinium)-iodide is obtained.

EKSEMPEL 34EXAMPLE 34

1,69 g l-etyl-7-metyl-3-(2-brom-2-metyl-propionyl)-4-okso-1,4-dihydro-l,8-nafthyridin blir kokt i 5o ml pyridin, hvoretter reaksjonsblandingen blir inndampet i vakuum. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(dimetyl-metyl-pyridinium)-bromid. 1.69 g of 1-ethyl-7-methyl-3-(2-bromo-2-methyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine is boiled in 50 ml of pyridine, after which the reaction mixture is evaporated in a vacuum. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(dimethyl-methyl-pyridinium)-bromide.

EKSEMPEL 35EXAMPLE 35

1,69 g l-etyl-7-metyl-3-(2-brom-2-metyl-propionyl)-4-okso-1,4-dihydro-l,8-nafthyridin blir opplost og oppvarmet i 4o ml pyridin. Til den erholdte opplosning blir lo ml pyridin tilsatt. Reaksjonsblandingen blir kokt og inndampet i vakuum. Som produkt erholder man l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(dimetyl-metyl-pyridinium)-bromid. 1.69 g of 1-ethyl-7-methyl-3-(2-bromo-2-methyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine are dissolved and heated in 40 ml of pyridine. To the solution obtained, 10 ml of pyridine is added. The reaction mixture is boiled and evaporated in vacuo. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(dimethyl-methyl-pyridinium)-bromide.

EKSEMPEL 36EXAMPLE 36

1,69 g l-etyl-7-metyl-3-(2-brom-2-metyl-propionyl)-4-okso-1, 4-dihydro-l, 8-naf thyridin blir kokt i loo ml trietylamin, hvoretter reaksjonsblandingen blir inndampet i vakuum. 1.69 g of 1-ethyl-7-methyl-3-(2-bromo-2-methyl-propionyl)-4-oxo-1,4-dihydro-1,8-naphthyridine is boiled in 10 ml of triethylamine, after which the reaction mixture is evaporated in vacuo.

Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-naf thyridin-3-karbonyl-/dimetyl-metyl- (trietyl-ammoni,um)_7-bromid. The product obtained is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl/dimethyl-methyl-(triethylammonium)-7-bromide.

EKSEMPEL 37EXAMPLE 37

2,11 g 7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(metyl-metyl-pyridinium)-jodid blir kokt med 4, 55 g trietylfosfat i nærvær av o,7 g kalimkårbonat. Reaksjonsblandingen blir opparbeidet med de vanlige metoder. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(metyl-metyl-pyridinium)-jodid. 2.11 g of 7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(methyl-methyl-pyridinium)-iodide is boiled with 4.55 g of triethyl phosphate in the presence of o, 7 g kalimkårbonate. The reaction mixture is worked up using the usual methods. The product is 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(methyl-methyl-pyridinium)-iodide.

EKSEMPEL 38EXAMPLE 38

2,11 g 7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-(metyl-metyl-pyridinium)-jodid blir oppvarmet og opplost i vann. Til den erholdte opplosning blir lo ml 7o%'ig perklorsyre tiJsatt, hvoretter opplosningen blir avkjolt til romtemperatur. De utfelite krystaller blir avfiltrert, vasket med vann og torket. Som produkt erholdes 7-metyl-4-okso-l,. 4-dihydro-l, 8-nafthyridin-3-karbonyl-(metyl-metyl-pyridinium)-perklorat. 2.11 g of 7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-(methyl-methyl-pyridinium)-iodide is heated and dissolved in water. To the solution obtained, 10 ml of 70% perchloric acid is added, after which the solution is cooled to room temperature. The precipitated crystals are filtered off, washed with water and dried. The product is 7-methyl-4-oxo-1,. 4-Dihydro-1,8-naphthyridine-3-carbonyl-(methyl-methyl-pyridinium)-perchlorate.

EKSEMPEL 39EXAMPLE 39

2,o8 g l-etyl-7-metyl-4-okso-l,4-diklor-l,8-nafthyridin-3-karbonyl-,/dimetyl-metyl(trietyl-ammonium)^-bromid blir oppvarmet og opplost i vann. Til den erholdte opplosning blir lo ml 7o%'iger perklorsyre tilsatt og opplosningen blir avkjolt til romtemperatur. De utfelite krystaller blir frafiltrert, vasket med vann og torket. Som produkt erholdes l-etyl-7-metyl-4-okso-l,4-dihydro-l,8-nafthyridin-3-karbonyl-/dimetyl-metyl- (trietyl-ammoniumj_7-perklorat • 2.08 g of 1-ethyl-7-methyl-4-oxo-1,4-dichloro-1,8-naphthyridine-3-carbonyl-,/dimethyl-methyl(triethyl-ammonium)^-bromide is heated and dissolved in water. To the solution obtained, 10 ml of 70% perchloric acid is added and the solution is cooled to room temperature. The precipitated crystals are filtered off, washed with water and dried. As a product, 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbonyl-/dimethyl-methyl-(triethyl-ammonium j_7-perchlorate •

Claims (8)

1. Fremgangsmåte for fremstilling av nye 1,8-nafthyridin-derivater av formel (I) 1. Process for the preparation of new 1,8-naphthyridine derivatives of formula (I) hvori ■ R^ betyr hydrogen eller en gruppe av formelen -(CH„) -CH- , -(CH_) -aryl eller -(CH_) -cykloalkyl, z m j 2nJ 2 p R_ betyr en gruppe med formelen -(CH„) -CH_, -(CH ) - aryl eller -(CH_) -cykloalkyl, z p n, m og p er et heltall i området o - 5, Y betyr en tertiær nitrogenholdig aromatisk heterocyklisk ring bundet til nitrogenatomet, eller en trialkylaminogruppe, Z er et anion, R- er hydrogen eller en ^-alkylgruppe, karakterisert ved at man ....a) omsetter en forbindelse av formel (III) wherein ■ R^ means hydrogen or a group of the formula -(CH„) -CH- , -(CH_) -aryl or -(CH_) -cycloalkyl, z m j 2nJ 2 p R_ means a group of the formula -(CH„) -CH_, -(CH ) - aryl or -( CH_) -cycloalkyl, z p n, m and p are an integer in the range o - 5, Y means a tertiary nitrogen-containing aromatic heterocyclic ring attached to the nitrogen atom, or a trialkylamino group, Z is an anion, R- is hydrogen or a ^-alkyl group, characterized in that one ....a) reacts a compound of formula (III) hvori R^ og R2 har de tidligere angitte betydninger og alkylgruppen inneholder 1-6 karbonatomer med en aromatisk, tertiær base eller et trialkylamin i nærvær av et halogen, eller Ib) omsetter en forbindelse av formel (II) in which R 1 and R 2 have the previously stated meanings and the alkyl group contains 1-6 carbon atoms with an aromatic, tertiary base or a trialkylamine in the presence of a halogen, or Ib) reacts a compound of formula (II) hvori X betyr halogen og alkylgruppen inneholder 1-6 karbonatomer, med en aromatisk, tertiær base eller et trialkylamin, ellerc) omsette en forbindelse med formel (IV) in which X means halogen and the alkyl group contains 1-6 carbon atoms, with an aromatic, tertiary base or a trialkylamine, orc) react a compound of formula (IV) hvori og R^ har oven angitte betydninger med en aromatisk, tertiær base eller et trialkylamin i nærvær av et halogen og hvis onsket alkylere den erholdte forbindelse av formel (I) (hvori R^ betyr hydrogen, og hvis onsket overfore et således erholdt halogenid i et annet halogenid eller et terapeutisk egnet andre anion.wherein and R^ have the meanings given above with an aromatic, tertiary base or a trialkylamine in the presence of a halogen and if desired alkylating the obtained compound of formula (I) (wherein R^ means hydrogen, and, if desired, transfer a halide thus obtained into a other halide or a therapeutically suitable second anion. 2. Fremgangsmåte ifolge krav 1, karakterisert ved at man gjennomforer omsetningen ved en temperatur på 2o - 2oo°C, fordelaktig- ved 8o - 15o°C.2. Method according to claim 1, characterized in that the reaction is carried out at a temperature of 2o - 2oo°C, advantageously - at 8o - 15o°C. 3. Fremgangsmåte ifolge ett av kravene 1-2, karakterisert ved at anionet er et jodid, bromid, klorid, sulfat, fosfat, perklorat eller nitratanion.3. Method according to one of claims 1-2, characterized in that the anion is an iodide, bromide, chloride, sulphate, phosphate, perchlorate or nitrate anion. 4. Fremgangsmåte ifolge ett av kravene 1-3, karakterisert ved at man som tertiær base anvender pyridin, kinolin, alkylsubstituert pyridin, fordel aktig picolin, quinaldin eller lepidin eller et trialkylamin, fordelaktig trietylamin.4. Method according to one of claims 1-3, characterized in that pyridine, quinoline, alkyl-substituted pyridine, advantage such as picoline, quinaldine or lepidin or a trialkylamine, advantageously triethylamine. 5. Fremgangsmåte ifolge krav lc, karakterisert ved at man gjennomforer alkyleringen av forbindelsene av formel I, hvori R-. er hydrogen, med et alkylhalogenid, dialkyl-sulfat eller trialkylfosfat.5. Process according to claim 1c, characterized in that the alkylation of the compounds of formula I is carried out, in which R-. is hydrogen, with an alkyl halide, dialkyl sulfate or trialkyl phosphate. 6. Fremgangsmåte ifolge krav 5, karakterisert ved at man gjennomforer alkyleringen med trietylfosfat.6. Method according to claim 5, characterized in that the alkylation is carried out with triethyl phosphate. 7. Plantevernmiddel, karakterisert ved at det som virksomt stoff inneholder en forbindelse av formel I og inerte, faste eller flytende bærere.7. Plant protection product, characterized in that the active substance contains a compound of formula I and inert, solid or liquid carriers. 8. Fremgangsmåte ved fremstilling av plantevernmiddel, karakterisert ved at man blander en forbindelse av formel I med egnede inerte, faste eller flytende bærere.8. Process for the production of a pesticide, characterized in that a compound of formula I is mixed with suitable inert, solid or liquid carriers.
NO744715A 1973-12-29 1974-12-27 NO744715L (en)

Applications Claiming Priority (3)

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HU73CI00001430A HU171561B (en) 1973-12-29 1973-12-29 Process for producing 1,8-naphtiridine derivatives
JP49007604A JPS50100092A (en) 1973-12-29 1974-01-17
HU74CI00001521A HU171868B (en) 1974-01-17 1974-12-04 Process for preparing new derivatives of 1,8-naphthyridine

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