CH534687A - 2-oxo-1,2-dihydroquinoline derivs - Google Patents
2-oxo-1,2-dihydroquinoline derivsInfo
- 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS48103590A (en) * | 1972-04-13 | 1973-12-25 | ||
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 |
EP3363786A1 (en) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Compounds for optically active devices |
EP3363793A1 (en) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Hydrophobic compounds for optically active devices |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE723211A (en) * | 1967-11-03 | 1969-04-30 |
-
1968
- 1968-07-05 CH CH1402571A patent/CH534687A/en not_active IP Right Cessation
- 1968-07-05 CH CH1402671A patent/CH523899A/en not_active IP Right Cessation
- 1968-07-05 CH CH1010668A patent/CH514611A/en not_active IP Right Cessation
-
1969
- 1969-06-25 NL NL6909748A patent/NL6909748A/xx unknown
- 1969-06-26 DE DE19691932384 patent/DE1932384A1/en active Pending
- 1969-07-04 GB GB3386069A patent/GB1212174A/en not_active Expired
- 1969-07-04 BE BE735694D patent/BE735694A/xx unknown
- 1969-07-07 FR FR6922940A patent/FR2012421A1/fr not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
GB1212174A (en) | 1970-11-11 |
CH523899A (en) | 1972-06-15 |
FR2012421A1 (en) | 1970-03-20 |
BE735694A (en) | 1970-01-05 |
DE1932384A1 (en) | 1970-01-15 |
NL6909748A (en) | 1970-01-07 |
CH514611A (en) | 1971-10-31 |
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Legal Events
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PL | Patent ceased |