CH534687A - 2-oxo-1,2-dihydroquinoline derivs - Google Patents

2-oxo-1,2-dihydroquinoline derivs

Info

Publication number
CH534687A
CH534687A CH1402571A CH1402571A CH534687A CH 534687 A CH534687 A CH 534687A CH 1402571 A CH1402571 A CH 1402571A CH 1402571 A CH1402571 A CH 1402571A CH 534687 A CH534687 A CH 534687A
Authority
CH
Switzerland
Prior art keywords
sep
lower alkyl
formula
hydrogen
oxo
Prior art date
Application number
CH1402571A
Other languages
German (de)
Inventor
Rudi Dr Beyerle
Adolf Dr Stachel
Rolf-Eberhard Dr Med Nitz
Klaus Dr Resag
Original Assignee
Cassella Farbwerke Mainkur Ag
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 Cassella Farbwerke Mainkur Ag filed Critical Cassella Farbwerke Mainkur Ag
Priority to CH1402571A priority Critical patent/CH534687A/en
Publication of CH534687A publication Critical patent/CH534687A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

2-Oxo-1,2-dihydroquinoline derivs. G3a. Of formula: (where R is H or lower alkyl; R1 is H, lower alkyl, alkenyl, aralkyl, aryl, dialkylaminoalkyl, in which the alkyl group on the N atom may be joined directly or via a hetero atom to a 5,6 or 7-membered ring; R2 is H, lower alkyl or aryl; R3 is lower alkoxy; X is H, halogen or lower alkyl; m = 1,2 or 3; A1 and A2 are straight-chain or branched alkylene radicals with 2-4C atoms; and Y is H, OH or Uses:- have a specific, coronary-dilatory action. They may be used in tablet form or as injections.

Description

  

  
 



   Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung wertvoller Derivate des 2-Oxo-1,2-dihydrochinolins der Formel
EMI1.1     
 worin R Wasserstoff oder niederes Alkyl,   Rl    Wasserstoff, niederes Alkyl, Alkenyl, Aralkyl, Aryl, Dialkylaminoalkyl, wobei die am N-Atom stehenden Alkylgruppen direkt oder über ein Heteroatom zu einem Fünf-, Sechs- oder Siebenring verbunden sein können, R2 Wasserstoff, niederes Alkyl oder Aryl,   R3    niederes Alkoxy, X Wasserstoff, Halogen oder niederes Alkyl,   m    die Zahlen 1, 2 oder 3, Al und A2 einen geradkettigen oder verzweigten Alkylenrest mit 2 bis 4 C-Atomen und Y Wasserstoff, eine Hydroxylgruppe oder den Rest
EMI1.2     
 bedeuten.

  Das erfindungsgemässe Verfahren zur Herstellung der genannten Derivate ist nun dadurch gekennzeichnet, dass man Derivate des   7-Hydroxy-2-oxo- 1, 2-dihydro-chinolins    der Formel
EMI1.3     
 mit einem Piperazinderivat der Formel
EMI1.4     
 oder dessen Hydrochlorid, worin Hal für ein Halogenatom steht, gegebenenfalls in Anwesenheit eines säurebindenden Mittels, umsetzt.



   Als Niederalkylreste R,   R1,    R2 und X und Alkoxyreste R3 kommen insbesondere solche mit 1 bis 4 C-Atomen in Frage.



   Die Verbindung der Formel I kann, falls Y die OH-Gruppe bedeutet, mit einer Alkoxybenzoesäure der Formel
EMI1.5     
 worin R3 und m die angegebene Bedeutung haben, oder mit einem funktionellen Derivat, z.B. mit 3,4,5-Trimethoxyben   zoylchlorid,    acyliert werden.



   Die erfindungsgemäss herstellbaren Derivate des 2-Oxo1,2-dihydro-chinolins sind wertvolle Arzneimittel; sie besitzen z.B. eine spezifische, coronargefässerweiternde Wirkung und sind in dieser Hinsicht bekannten Stoffen dieser Art überlegen.



  Ihre Salze sind farblose, kristalline, in Wasser leicht lösliche Substanzen.



   Beispiel
23,1 g (0,1 Mol) 3 -n-Butyl-4-methyl-7-hydroxy2-oxo-1 ,2-dihydro-chinolin werden unter Rühren in 220 ml Dimethylsulfoxyd gelöst und mit 33,6 g (0,3 Mol) Kalium-tert.-butylat versetzt. Diese Suspension wird 15 Min. bei Zimmertemperatur gerührt und dann portionsweise mit 48,7 g (0,1 Mol)   1-(P-3,4,5 -Tnmethoxybenzoxyäthyl)-4- (y-chlor- ss-hydroxypropyl)-piperazin-dihydrochlorid    (hergestellt durch Umsetzung des   N-(ss-3,4,5-Trimethoxy-benzoxyäthyl)-piperazins    mit Epichlorhydrin) versetzt. Anschliessend rührt man 12 Stunden bei Zimmertemperatur und giesst dann das Reaktionsgemisch in Wasser. Das sich ölig abscheidende Reaktionsprodukt nimmt man in Essigester auf und wäscht einige Male  mit verdünnter Natronlauge. Dann wird die Essigester-Lösung über geglühtem Natriumsulfat getrocknet.

  Durch Einleiten von trockenem Chlorwasserstoff-Gas erhält man das Dihydrochlorind des 3-n-Butyl-4-methyl-7-   {γ-[4'-(ss-3,4,5-    trimethoxybenzoxyäthyl)-piperazino[1]]-    l-hydroxypropoxy}-2-oxo- 1,2-dihydrochinolins    in Form farbloser Nadeln vom Zers.P. 1800.



  Ausbeute: 41 g = 60% der Theorie.



   In analoger Weise können gemäss der Erfindung folgende Verbindungen der Formel I hergestellt werden, worin   Rt,      R2,    Y und A2 die angegebene Bedeutung haben:
EMI2.1     

EMI2.2     


<tb> Rl <SEP> R2 <SEP> Y <SEP> A2 <SEP> bzw. <SEP> Zers.P.
<tb>



   <SEP> des <SEP> Dihydro
<tb>  <SEP> chlorids:
<tb> nC4Hs <SEP> CH2 <SEP> OH <SEP> -CH2-CH(CH3)- <SEP> 187 
<tb> CH2 <SEP> CH3 <SEP> OH <SEP> -CH2-CH2-CH2-CH2- <SEP> 2070
<tb>  <SEP> C2H5 <SEP> C6Hs <SEP> OH <SEP> -CH2-CH2- <SEP> 169 
<tb> C2H5 <SEP> C6Hs <SEP> OH <SEP> -CH2-CU(CH3)- <SEP> 1800
<tb> nC4Hs <SEP> n-CH <SEP> OH <SEP> -CH2-CH2- <SEP> 145 
<tb>  <SEP> nC4Hs <SEP> n- <SEP> C3H7 <SEP> OH <SEP> -CH2-CH(CH3)- <SEP> 127 
<tb> (C2H5)2N <SEP> - <SEP> CH2 <SEP> - <SEP> CH2 <SEP> - <SEP> CH3 <SEP> OH <SEP> - <SEP> CH2 <SEP> - <SEP> CH2 <SEP> - <SEP> 154"
<tb>  <SEP> (Trihydrochlorid)
<tb>  <SEP> HN-CH2-CH2- <SEP> CH3 <SEP> OH <SEP> -CH2-CH2- <SEP> 1370
<tb> (Trihydrochlorid)
<tb>  <SEP> HN-CH2-CH2- <SEP> CH3 <SEP> OH <SEP> -CH2-CH2-CH2- <SEP> 1280
<tb>  <SEP> (Trihydrochlorid)
<tb>  <SEP> - <SEP> CH2- <SEP> CH2 <SEP> - <SEP> CH3 <SEP> OH <SEP> -CH2-CH(CH3)- <SEP> 149  <SEP>  

   drochlorid)
<tb>  <SEP> N
<tb>  <SEP> OCH3
<tb> CH2=CH-CH2- <SEP> CH3 <SEP> -O-CO-C3 <SEP> OCH3 <SEP> -CH2-CH2- <SEP> 116 
<tb>  <SEP> LOCHS
<tb>  <SEP> OCH3
<tb> CH2=CH-CH2- <SEP> CH3 <SEP> -O-CO-q <SEP> OCH3 <SEP> -CH2-CH2-CH2- <SEP> 113 
<tb>  <SEP> OCH3
<tb>    R1 R2 Y A2 Fp. bzw. Zers. P.



   des Dihydro chlorids:
EMI3.1     
   129  1300    (Trihydrochlorid)    145      (Trihydrochlorid)   125     (Trihydrochlorid)   103      (Trihydrochlorid)   140     (Trihydrochlorid) 134  (Trihydrochlorid)     Rt    R2 Y A2 Fp. bzw.   Zers.    P.



   des   Dihydro    chlorids:
EMI4.1     
   155     (Trihydrochlorid)   100"    (Trihydrochlorid)   133     (Trihydrochlorid) 



  
 



   The present invention relates to a process for the preparation of valuable derivatives of 2-oxo-1,2-dihydroquinoline of the formula
EMI1.1
 wherein R is hydrogen or lower alkyl, Rl is hydrogen, lower alkyl, alkenyl, aralkyl, aryl, dialkylaminoalkyl, where the alkyl groups on the N atom can be linked directly or via a heteroatom to form a five, six or seven ring, R2 is hydrogen, lower alkyl or aryl, R3 lower alkoxy, X hydrogen, halogen or lower alkyl, m the numbers 1, 2 or 3, Al and A2 a straight-chain or branched alkylene radical with 2 to 4 carbon atoms and Y hydrogen, a hydroxyl group or the radical
EMI1.2
 mean.

  The process according to the invention for the preparation of the derivatives mentioned is now characterized in that derivatives of 7-hydroxy-2-oxo-1,2-dihydroquinoline of the formula
EMI1.3
 with a piperazine derivative of the formula
EMI1.4
 or its hydrochloride, in which Hal stands for a halogen atom, optionally in the presence of an acid-binding agent.



   Particularly suitable lower alkyl radicals R, R1, R2 and X and alkoxy radicals R3 are those with 1 to 4 carbon atoms.



   The compound of the formula I can, if Y denotes the OH group, with an alkoxybenzoic acid of the formula
EMI1.5
 where R3 and m are as defined, or with a functional derivative, e.g. with 3,4,5-trimethoxybenzoyl chloride, acylated.



   The derivatives of 2-oxo1,2-dihydroquinoline which can be prepared according to the invention are valuable medicaments; they have e.g. have a specific, coronary vasodilator effect and are superior in this respect to known substances of this type.



  Their salts are colorless, crystalline substances that are easily soluble in water.



   example
23.1 g (0.1 mol) of 3 -n-butyl-4-methyl-7-hydroxy2-oxo-1,2-dihydro-quinoline are dissolved in 220 ml of dimethyl sulfoxide with stirring and 33.6 g (0, 3 mol) of potassium tert-butoxide were added. This suspension is stirred for 15 minutes at room temperature and then mixed in portions with 48.7 g (0.1 mol) of 1- (P-3,4,5-methoxybenzoxyethyl) -4- (γ-chloro-ss-hydroxypropyl) piperazine Dihydrochloride (prepared by reacting N- (ss-3,4,5-trimethoxy-benzoxyethyl) piperazine with epichlorohydrin). The mixture is then stirred for 12 hours at room temperature and the reaction mixture is then poured into water. The oily reaction product is taken up in ethyl acetate and washed a few times with dilute sodium hydroxide solution. Then the ethyl acetate solution is dried over calcined sodium sulfate.

  The dihydrochloride of 3-n-butyl-4-methyl-7- {γ - [4 '- (ss-3,4,5-trimethoxybenzoxyethyl) -piperazino [1]] - is obtained by introducing dry hydrogen chloride gas. l-hydroxypropoxy} -2-oxo-1,2-dihydroquinolines in the form of colorless needles from Zers.P. 1800.



  Yield: 41 g = 60% of theory.



   In an analogous manner, the following compounds of the formula I can be prepared according to the invention, in which Rt, R2, Y and A2 have the meaning given:
EMI2.1

EMI2.2


<tb> Rl <SEP> R2 <SEP> Y <SEP> A2 <SEP> or <SEP> Zers.P.
<tb>



   <SEP> of the <SEP> Dihydro
<tb> <SEP> chlorides:
<tb> nC4Hs <SEP> CH2 <SEP> OH <SEP> -CH2-CH (CH3) - <SEP> 187
<tb> CH2 <SEP> CH3 <SEP> OH <SEP> -CH2-CH2-CH2-CH2- <SEP> 2070
<tb> <SEP> C2H5 <SEP> C6Hs <SEP> OH <SEP> -CH2-CH2- <SEP> 169
<tb> C2H5 <SEP> C6Hs <SEP> OH <SEP> -CH2-CU (CH3) - <SEP> 1800
<tb> nC4Hs <SEP> n-CH <SEP> OH <SEP> -CH2-CH2- <SEP> 145
<tb> <SEP> nC4Hs <SEP> n- <SEP> C3H7 <SEP> OH <SEP> -CH2-CH (CH3) - <SEP> 127
<tb> (C2H5) 2N <SEP> - <SEP> CH2 <SEP> - <SEP> CH2 <SEP> - <SEP> CH3 <SEP> OH <SEP> - <SEP> CH2 <SEP> - <SEP> CH2 <SEP> - <SEP> 154 "
<tb> <SEP> (trihydrochloride)
<tb> <SEP> HN-CH2-CH2- <SEP> CH3 <SEP> OH <SEP> -CH2-CH2- <SEP> 1370
<tb> (trihydrochloride)
<tb> <SEP> HN-CH2-CH2- <SEP> CH3 <SEP> OH <SEP> -CH2-CH2-CH2- <SEP> 1280
<tb> <SEP> (trihydrochloride)
<tb> <SEP> - <SEP> CH2- <SEP> CH2 <SEP> - <SEP> CH3 <SEP> OH <SEP> -CH2-CH (CH3) - <SEP> 149 <SEP>

   hydrochloride)
<tb> <SEP> N
<tb> <SEP> OCH3
<tb> CH2 = CH-CH2- <SEP> CH3 <SEP> -O-CO-C3 <SEP> OCH3 <SEP> -CH2-CH2- <SEP> 116
<tb> <SEP> HOLES
<tb> <SEP> OCH3
<tb> CH2 = CH-CH2- <SEP> CH3 <SEP> -O-CO-q <SEP> OCH3 <SEP> -CH2-CH2-CH2- <SEP> 113
<tb> <SEP> OCH3
<tb> R1 R2 Y A2 Fp. or dec. P.



   of the dihydrochloride:
EMI3.1
   129 1300 (trihydrochloride) 145 (trihydrochloride) 125 (trihydrochloride) 103 (trihydrochloride) 140 (trihydrochloride) 134 (trihydrochloride) Rt R2 Y A2 mp or dec. P.



   of the dihydrochloride:
EMI4.1
   155 (trihydrochloride) 100 "(trihydrochloride) 133 (trihydrochloride)

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von Derivaten des 2-Oxo-1,2-dihydrochinolins der Formel EMI4.2 worin R Wasserstoff oder niederes Alkyl, Rt Wasserstoff, niederes Alkyl, Alkenyl, Aralkyl, Aryl, Dialkylaminoalkyl, wobei die am N-Atom stehenden Alkylgruppen direkt oder über ein Heteroatom zu einem Fünf-, Sechs- oder Siebenring verbunden sein können, R2 Wasserstoff, niederes Alkyl oder Aryl, R3 niederes Alkoxy, X Wasserstoff, Halogen oder niederes Alkyl, m die Zahlen 1, 2 oder 3, Al und A2 einen geradkettigen oder verzweigten Alkylenrest mit 2 bis 4 C-Atomen, und Y Wasserstoff, eine Hydroxylgruppe oder den Rest EMI4.3 bedeuten, dadurch gekennzeichnet, dass man Derivate des 7 Hydroxy-2-oxo-1,2-dihydrochinolins der Formel EMI4.4 mit einem Piperazinderivat der Formel EMI4.5 oder dessen Dihydrochlorid, PATENT CLAIM Process for the preparation of derivatives of 2-oxo-1,2-dihydroquinoline of the formula EMI4.2 where R is hydrogen or lower alkyl, Rt is hydrogen, lower alkyl, alkenyl, aralkyl, aryl, dialkylaminoalkyl, where the alkyl groups on the N atom can be linked directly or via a heteroatom to form a five, six or seven ring, R2 is hydrogen, lower alkyl or aryl, R3 lower alkoxy, X hydrogen, halogen or lower alkyl, m the numbers 1, 2 or 3, Al and A2 a straight-chain or branched alkylene radical with 2 to 4 carbon atoms, and Y hydrogen, a hydroxyl group or the rest EMI4.3 mean, characterized in that derivatives of 7-hydroxy-2-oxo-1,2-dihydroquinoline of the formula EMI4.4 with a piperazine derivative of the formula EMI4.5 or its dihydrochloride, worin Hal für ein Halogenatom steht, umsetzt. wherein Hal stands for a halogen atom. UNTERANSPRÜCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet. SUBCLAIMS 1. The method according to claim, characterized. dass man die Umsetzung in Gegenwart eines säurebindenden Mittels durchführt. that the reaction is carried out in the presence of an acid-binding agent. 2. Verfahren nach Patentanspruch oder Unteranspruch 1. 2. Method according to claim or dependent claim 1. dadurch gekennzeichnet, dass man erhaltene Verbindungen der Formel I, worin Y die OH-Gruppe bedeutet, mit einer Alkoxybenzoesäure der Formel EMI5.1 worin R. und m die angegebene Bedeutung haben, oder einem funktionellen Derivat davon, acyliert. characterized in that the compounds of the formula I in which Y is the OH group are obtained with an alkoxybenzoic acid of the formula EMI5.1 wherein R. and m have the meaning given, or a functional derivative thereof, acylated.
CH1402571A 1968-07-05 1968-07-05 2-oxo-1,2-dihydroquinoline derivs CH534687A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1402571A CH534687A (en) 1968-07-05 1968-07-05 2-oxo-1,2-dihydroquinoline derivs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1010668A CH514611A (en) 1968-07-05 1968-07-05 Process for the preparation of derivatives of 2-oxo-1,2-dihydro-quinoline
CH1402571A CH534687A (en) 1968-07-05 1968-07-05 2-oxo-1,2-dihydroquinoline derivs

Publications (1)

Publication Number Publication Date
CH534687A true CH534687A (en) 1973-03-15

Family

ID=4359412

Family Applications (3)

Application Number Title Priority Date Filing Date
CH1402571A CH534687A (en) 1968-07-05 1968-07-05 2-oxo-1,2-dihydroquinoline derivs
CH1402671A CH523899A (en) 1968-07-05 1968-07-05 2-oxo-1,2-dihydroquinoline derivs
CH1010668A CH514611A (en) 1968-07-05 1968-07-05 Process for the preparation of derivatives of 2-oxo-1,2-dihydro-quinoline

Family Applications After (2)

Application Number Title Priority Date Filing Date
CH1402671A CH523899A (en) 1968-07-05 1968-07-05 2-oxo-1,2-dihydroquinoline derivs
CH1010668A CH514611A (en) 1968-07-05 1968-07-05 Process for the preparation of derivatives of 2-oxo-1,2-dihydro-quinoline

Country Status (6)

Country Link
BE (1) BE735694A (en)
CH (3) CH534687A (en)
DE (1) DE1932384A1 (en)
FR (1) FR2012421A1 (en)
GB (1) GB1212174A (en)
NL (1) NL6909748A (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS517672B2 (en) * 1972-04-13 1976-03-10
JPS54130587A (en) * 1978-03-30 1979-10-09 Otsuka Pharmaceut Co Ltd Carbostyryl derivative
DE2960178D1 (en) * 1978-06-06 1981-04-09 Hoechst Ag New substituted phenylpiperazine derivatives, pharmaceutical compositions containing them and process for their preparation
DE2827566A1 (en) * 1978-06-23 1980-01-10 Boehringer Mannheim Gmbh 1,2-DIHYDRO-CHINOLIN-2-ON DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF
GB2379284A (en) 2001-09-01 2003-03-05 Zarlink Semiconductor Ltd Multiple level photolithography
GB2379796A (en) 2001-09-14 2003-03-19 Zarlink Semiconductor Ltd A method of forming a low resistance contact
EP3133065A1 (en) 2015-08-21 2017-02-22 Merck Patent GmbH Compounds for optically active devices
EP3133066A1 (en) * 2015-08-21 2017-02-22 Merck Patent GmbH Hydrophilic compounds for optically active devices
EP3363793A1 (en) 2017-02-15 2018-08-22 Merck Patent GmbH Hydrophobic compounds for optically active devices
EP3363786A1 (en) 2017-02-15 2018-08-22 Merck Patent GmbH Compounds for optically active devices

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE723211A (en) * 1967-11-03 1969-04-30

Also Published As

Publication number Publication date
FR2012421A1 (en) 1970-03-20
DE1932384A1 (en) 1970-01-15
NL6909748A (en) 1970-01-07
CH514611A (en) 1971-10-31
GB1212174A (en) 1970-11-11
BE735694A (en) 1970-01-05
CH523899A (en) 1972-06-15

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