CH433308A - Process for preparing a new quinoline derivative - Google Patents

Process for preparing a new quinoline derivative

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Publication number
CH433308A
CH433308A CH980663A CH980663A CH433308A CH 433308 A CH433308 A CH 433308A CH 980663 A CH980663 A CH 980663A CH 980663 A CH980663 A CH 980663A CH 433308 A CH433308 A CH 433308A
Authority
CH
Switzerland
Prior art keywords
quinoline
propyl
isopropylidenedioxy
monoglyceride
carried out
Prior art date
Application number
CH980663A
Other languages
French (fr)
Inventor
Allais Andre
Meier Jean
Original Assignee
Roussel Uclaf
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
Priority claimed from FR907282A external-priority patent/FR1421229A/en
Application filed by Roussel Uclaf filed Critical Roussel Uclaf
Publication of CH433308A publication Critical patent/CH433308A/en

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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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified

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  • 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)
  • Quinoline Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

  

  



  Procédé de préparation d'un nouveau dérivé de la quinoléine
 La présente invention a pour objet un procédé de préparation de   ra-monoglycéride    de la   4- (2'-carboxy-      phénylamino)-7-chloro-quinoléine    de formule suivante :
EMI1.1     
 ainsi que ses sels pharmacologiquement compatibles et notamment le chlorhydrate.



   Certains dérives de la quinoléine, comme par exemple la   4-(2'-carbométhoxyphénylamino)-7-chloro-quino-      léine    ou la   4-(2'-carbobutoxyphénylamino)-7-chloro-    quinoléine décrits dans le brevet suisse No. 424 780, sont doués d'une activité anti-inflammatoire et   d'une    activité analgésique et ils peuvent être utilisés pour le traitement des algies musculaires, articulaires ou nerveuses, affections rhumatismales, douleurs dentaires, zona, migraines, états fébriles et infectieux.



   Or, on vient de trouver maintenant que   l'a-mono-    glycéride de la   4- (2'-carboxyphénylamino)-7-chloro-    quinoléine, obtenu par le procédé selon la présente invention, possède les mêmes propriétés pharmacologiques, mais qu'il se distingue notamment par une action antiinflammatoire remarquable et une action analgésique plus intense et plus régulière.



   La posologie utile s'échelonne entre 0, 100 g et 0, 200 g par prise et 0, 200 à 0, 500 g par jour chez l'adulte en fonction de la voie d'administration.



   Le procédé, objet de l'invention, est caractérisé en ce que   l'on    condense le chlorure   d'o-nitrobenzoyle    de formule II avec le 2,   2-diméthyl-4-hydroxyméthyl-1,    3dioxolane de formule III en présence d'une base organique tertiaire, réduit par hydrogénation catalytique   l'o-    nitrobenzoate de (2,   3-isopropylidènedioxy)-propyle    de formule IV résultant en anthranilate de (2, 3-isopropyl  idènedioxy)-propyle    de formule V, que l'on condense avec la 4,   7-dichloroquinoléine    de formule VI en milieu d'acide minéral, soumet le sel obtenu de   l'a-monogly-    céride de la   4-(2'-carboxyphénylamino)

  -7-chloro-quinolé-    ine de formule I à l'action d'un agent alcalin, obtient la base libre et la transforme, le cas échéant, en un sel pharmacologiquement compatible.



   Dans ses modes d'exécution, le procédé ci-dessus peut être encore caractérisé par les points suivants : -la base organique tertiaire dans laquelle on effectue la condensation du chlorure   d'o-nitrobenzoyle    de formule II avec le 2,   2-diméthyl-4-hydroxyméthyl-1,    3-di  oxolane    de formule III est la pyridine ; -le catalyseur employé pour l'hydrogénation de   l'o-    nitrobenzoate de (2,   3-isopropylidènedioxy)-propyle    de formule IV est le noir palladié, et on opère dans   l'éth-    anol ;

   -l'acide minéral dans lequel on effectue la condensation de   l'anthranilate    de (2,   3-isopropylidènedioxy)-    propyle de formule V avec la 4,   7-dichloroquinoléine    de formule VI est l'acide chlorhydrique ; -l'agent alcalin qui sert pour l'obtention de la base libre de   l'a-monoglycéride    de la 4-(2'-carboxyphényl  amino)-7-chloro-quinoléine    de formule I à partir du sel correspondant est l'ammoniaque.



   L'exemple suivant illustré par le schéma annexé fera mieux comprendre l'invention.



   Exemple
 Préparation de   l'a-monoglycéride    de la    4- (2'-carboxyphénylamino)-7-chloro-quinoléine   
 (formule I)
 Stade A
   Préparation de l'o-nitrobenzoate    de
 (2,   3-isopropylidène-dioxy)-propyle   
 On dissout sous agitation 59, 6 g do 2,   2-diméthyl-      4-hydroxyméthyl-1,    3-dioxolane dans 60 cms de pyridine anhydre, refroidit la solution à   +5  C    et y introduit lentement 86, 5 g de chlorure   d'o-nitrobenzoyle,    (pré paré par G. Lockermann et Col. Ber. 80, 488 (1947).



  On agite le mélange réactionnel pendant deux heures à température ambiante, puis on le verse dans 500   cm    d'éther. On filtre, lave le filtrat successivement par l'acide sulfurique 0, 5 N, par une solution aqueuse de bicarbonate de soude et finalement à l'eau jusqu'à neutraité. On sèche sur sulfate de sodium et filtre de   nou-    veau. Le filtrat est distillé à sec sous vide.



   On obtient 116, 5 g (soit un rendement de 92%)   d'orthonitrobenzoate    de (2,   3-isopropylidène-dioxy)-    propyle. Le produit se présente sous forme   d'une    huile jaune qui distille à   178-180  C sous    1 mm de pression.



  Analyse :   Cl3HrsOFN    = 281, 26
Calculé : C 55,   51"/o H5, 38"/. N4, 98"   
Trouvé : C 55,8% H 5, 4% N 5,0%
 Ce composé n'est pas décrit dans la littérature.



   Stade B
 Préparation de   l'anthranilate    de
 (2,   3-isopropylidène-dioxy)-propyle   
 On soumet à l'hydrogénation pendant une heure 80 g   d'o-nitrobenzoate    de (2,   3-isopropylidène-dioxy)-    propyle, obtenu comme décrit au stade A, dans 800 cm3 d'alcool absolu en présence de 2 g de noir palladié comme catalyseur.



   On filtre et évapore le filtrat sous vide. On obtient 70, 5 g (soit un rendement de 98,   5  /o) d'anthranilate    de (2,   3-isopropylidènedioxy)-propyle.   



   Le produit qui se présente sous la forme d'une huile jaune distille à   159-160  C sous    0, 5 mm de pression.



  Analyse :   Cl3Hl704N =    251, 28
Calculé : C 62, 13% H 6,82% N 5, 58     /o   
Trouvé :   C62, l o/. H6, 9"/o N5,    6  /o
 Ce composé   n'est    pas décrit dans la littérature.



   Stade C
 Préparation de   l'a-monoglycéride de    la    4-(2'-carboxy-phénylamino)-7-chloroquinoléine   
 On agite en chauffant au reflux un mélange de 48 g d'anthranilate de (2,   3-isopropylidène-dioxy)-    propyle, 36 g de 4, 7-dichloroquinolÚine, 36 cm3 d'acide chlorhydrique concentré et 300 cm3 d'eau pendant deux heures.



   On filtre, abandonne le filtrat à la température de   0  C    pendant trois heures, puis essore le chlorhydrate qu'on reprend dans 600 cm3 de méthanol à   50 O/o,    au reflux. La solution est alcalinisée par addition de 120 cm3 d'ammoniaque et glacée pendant une heure.



  Le précipité cristallin obtenu est essoré, lavé à l'eau et séché.



   On obtient 38, 5 g, soit un rendement de 56  /o d'a  monoglycéride    de la   4- (2'-carboxy-phénylamino)-7-    chloroquinolÚine, F. =   165  C.   



   Le produit se présente sous forme de prismes jaune pâle, insolubles dans   1'eau,    peu solubles dans l'alcool absolu, l'acétone, l'éther, le benzène et le chloroforme, solubles dans les acides et les alcalis dilués aqueux.



  Analyse :   C19Ht704N2C1    = 372, 8
Calculé : C 61, 21    /o    H 4,   59 O/o    N 7, 51% Cl 9, 51%
Trouvé : C 61,5% H 4,5% N 7,3% C 19,6%
 Ce composé   n'est    pas décrit dans la littérature.




  



  Process for preparing a new quinoline derivative
 The present invention relates to a process for the preparation of ra-monoglyceride of 4- (2'-carboxy-phenylamino) -7-chloro-quinoline of the following formula:
EMI1.1
 as well as its pharmacologically compatible salts and in particular the hydrochloride.



   Certain quinoline derivatives, such as, for example, 4- (2'-carbomethoxyphenylamino) -7-chloro-quinoline or 4- (2'-carbobutoxyphenylamino) -7-chloroquinoline described in Swiss patent No. 424 780, are endowed with anti-inflammatory and analgesic activity and they can be used for the treatment of muscle, joint or nerve pain, rheumatic ailments, dental pain, shingles, migraines, febrile and infectious conditions.



   Now, it has now been found that the α-monoglyceride of 4- (2'-carboxyphenylamino) -7-chloroquinoline, obtained by the process according to the present invention, has the same pharmacological properties, but that it is distinguished in particular by a remarkable anti-inflammatory action and a more intense and regular analgesic action.



   The useful dosage ranges between 0, 100 g and 0, 200 g per dose and 0, 200 to 0, 500 g per day in adults depending on the route of administration.



   The process, object of the invention, is characterized in that the o-nitrobenzoyl chloride of formula II is condensed with 2, 2-dimethyl-4-hydroxymethyl-1, 3dioxolane of formula III in the presence of a tertiary organic base, reduced by catalytic hydrogenation (2, 3-isopropylidenedioxy) -propyl o-nitrobenzoate of formula IV resulting in (2, 3-isopropyl idenedioxy) -propyl anthranilate of formula V, which is condensed with 4, 7-dichloroquinoline of formula VI in mineral acid medium, subject the salt obtained from the α-monoglyceride of 4- (2'-carboxyphenylamino)

  -7-Chloro-quinoline of formula I with the action of an alkaline agent, obtains the free base and converts it, if necessary, into a pharmacologically compatible salt.



   In its embodiments, the above process can be further characterized by the following points: the tertiary organic base in which the condensation of the o-nitrobenzoyl chloride of formula II with 2, 2-dimethyl- 4-hydroxymethyl-1,3-dioxolane of formula III is pyridine; the catalyst used for the hydrogenation of (2, 3-isopropylidenedioxy) -propyl o-nitrobenzoate of formula IV is palladium black, and the operation is carried out in eth- anol;

   the mineral acid in which the condensation of the (2, 3-isopropylidenedioxy) - propyl anthranilate of formula V with the 4, 7-dichloroquinoline of formula VI is carried out is hydrochloric acid; the alkaline agent which is used to obtain the free base of the α-monoglyceride of 4- (2'-carboxyphenyl amino) -7-chloro-quinoline of formula I from the corresponding salt is ammonia .



   The following example illustrated by the attached diagram will make the invention easier to understand.



   Example
 Preparation of 4- (2'-carboxyphenylamino) -7-chloro-quinoline α-monoglyceride
 (formula I)
 Stage A
   Preparation of o-nitrobenzoate
 (2, 3-isopropylidene-dioxy) -propyl
 59.6 g of 2, 2-dimethyl-4-hydroxymethyl-1, 3-dioxolane are dissolved with stirring in 60 cms of anhydrous pyridine, the solution is cooled to +5 C and slowly introduced into it 86.5 g of chloride. o-nitrobenzoyl, (prepared by G. Lockermann and Col. Ber. 80, 488 (1947).



  The reaction mixture is stirred for two hours at room temperature, then poured into 500 cm 3 of ether. Filtered, the filtrate washed successively with 0.5 N sulfuric acid, with an aqueous solution of sodium bicarbonate and finally with water until neutral. It is dried over sodium sulfate and filtered again. The filtrate is distilled to dryness under vacuum.



   116.5 g (ie a yield of 92%) of (2,3-isopropylidene-dioxy) -propyl orthonitrobenzoate are obtained. The product is in the form of a yellow oil which distils at 178-180 C under 1 mm of pressure.



  Analysis: Cl3HrsOFN = 281, 26
Calculated: C 55.51 "/ o H5.38" /. N4, 98 "
Found: C 55.8% H 5.4% N 5.0%
 This compound is not described in the literature.



   Stage B
 Preparation of anthranilate
 (2, 3-isopropylidene-dioxy) -propyl
 80 g of (2, 3-isopropylidene-dioxy) - propyl o-nitrobenzoate, obtained as described in Stage A, in 800 cm3 of absolute alcohol in the presence of 2 g of black are subjected to hydrogenation for one hour. palladium as a catalyst.



   The filtrate is filtered and evaporated in vacuo. 70.5 g (ie a yield of 98.5 / o) of (2,3-isopropylidenedioxy) -propyl anthranilate are obtained.



   The product, which is in the form of a yellow oil, distils at 159-160 C under 0.5 mm pressure.



  Analysis: Cl3H1704N = 251, 28
Calculated: C 62.13% H 6.82% N 5.58 / o
Found: C62, 10 /. H6.9 "/ o N5.6 / o
 This compound is not described in the literature.



   Stage C
 Preparation of 4- (2'-carboxy-phenylamino) -7-chloroquinoline α-monoglyceride
 A mixture of 48 g of (2, 3-isopropylidene-dioxy) - propyl anthranilate, 36 g of 4, 7-dichloroquinolÚine, 36 cm3 of concentrated hydrochloric acid and 300 cm3 of water is stirred while refluxing. two o'clock.



   Filtered, the filtrate is left at a temperature of 0 C for three hours, then the hydrochloride is filtered off, which is taken up in 600 cm3 of 50 O / o methanol, at reflux. The solution is made alkaline by adding 120 cm3 of ammonia and ice-cold for one hour.



  The crystalline precipitate obtained is filtered off, washed with water and dried.



   38.5 g are obtained, i.e. a yield of 56% of a monoglyceride of 4- (2'-carboxy-phenylamino) -7-chloroquinolÚine, M.p. = 165 C.



   The product is in the form of pale yellow prisms, insoluble in water, sparingly soluble in absolute alcohol, acetone, ether, benzene and chloroform, soluble in dilute aqueous acids and alkalis.



  Analysis: C19Ht704N2C1 = 372.8
Calculated: C 61.21 / o H 4.59 O / o N 7.51% Cl 9.51%
Found: C 61.5% H 4.5% N 7.3% C 19.6%
 This compound is not described in the literature.

Claims (1)

REVENDICATION Procédé de préparation d'un dérivé de la quinoléine, caractérisé en ce que l'on condense le chlorure d'onitrobenzoyle avec le 2, 2-dimÚthyl-4-hydroxymÚthyl1, 3-dioxolane, en présence d'une base organique tertiaire, réduit par hydrogénation catalytique l'o-nitro- benzoate de (2, 3-isopropylidènedioxy)-propyle résultant en anthranilate de (2, 3-isopropylidènedioxy)-propyle, que l'on condense avec la 4, 7-dichloro-quinoléine, en milieu d'acide minéral, soumet le produit résultant à un agent alcalin et obtient l'a-monoglycéride de la 4- (2'- carboxyphénylamino)-7-chloro-quinoléine. CLAIM Process for the preparation of a quinoline derivative, characterized in that one condenses the onitrobenzoyl chloride with 2, 2-dimÚthyl-4-hydroxymÚthyl1, 3-dioxolane, in the presence of a tertiary organic base, reduced by catalytic hydrogenation of (2, 3-isopropylidenedioxy) -propyl o-nitro-benzoate resulting in (2, 3-isopropylidenedioxy) -propyl anthranilate, which is condensed with 4, 7-dichloro-quinoline, in medium of mineral acid, subjecting the resulting product to an alkaline agent, and obtaining the α-monoglyceride of 4- (2'-carboxyphenylamino) -7-chloro-quinoline. SOUS-REVENDICATIONS 1. Procédé suivant la revendication, caractérisé en ce qu'on transforme le produit obtenu en un sel pharma cologiquement compatible. SUB-CLAIMS 1. Method according to claim, characterized in that the product obtained is converted into a pharmacologically compatible pharma salt. 2. Procédé suivant la revendication, caractérisé en ce que la base organique tertiaire dans laquelle on effectue la condensation du chlorure d'o-nitrobenzoyle avec le 2, 2-diméthyl-4-hydroxyméthyl-1, 3-dioxolane, est la pyridine. 2. Method according to claim, characterized in that the tertiary organic base in which the condensation of o-nitrobenzoyl chloride is carried out with 2, 2-dimethyl-4-hydroxymethyl-1, 3-dioxolane, is pyridine. 3. Procédé suivant la revendication, caractérisé en ce que le catalyseur employé pour l'hydrogénation de l'onitrobenzoate de (2, 3-isopropylidènedioxy)-propyle, est le noir palladié, et on opère dans l'Úthanol. 3. Method according to claim, characterized in that the catalyst used for the hydrogenation of (2,3-isopropylidenedioxy) -propyl onitrobenzoate is palladium black, and the operation is carried out in Úthanol. 4. Procédé suivant la revendication, caractérisé en ce que l'acide minéral dans lequel on effectue la condensation de l'anthranilate de (2, 3-isopropylid¯nedioxy)propyle avec la 4, 7-dichloro-quinoléine, est l'acide chlorhydrique. 4. Method according to claim, characterized in that the mineral acid in which the condensation of the anthranilate of (2, 3-isopropylid¯nedioxy) propyl with 4, 7-dichloro-quinoline is carried out, is the acid hydrochloric. 5. Procédé suivant la revendication, caractérisé en ce que l'agent alcalin qui sert pour l'obtention de la base libre, soit l'a-monoglycéride de la 4-(2'-carboxyphénylamino)-7-chloro-quinoléine, à partir du sel correspon- dant, est l'ammoniaque. 5. Method according to claim, characterized in that the alkaline agent which is used to obtain the free base, either the a-monoglyceride of 4- (2'-carboxyphenylamino) -7-chloro-quinoline, to from the corresponding salt, is ammonia.
CH980663A 1962-08-20 1963-08-08 Process for preparing a new quinoline derivative CH433308A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR907282A FR1421229A (en) 1962-08-20 1962-08-20 New quinoline derivative and method of preparation
FR28308A FR90364E (en) 1962-08-20 1965-08-13 New quinoline derivative and method of preparation

Publications (1)

Publication Number Publication Date
CH433308A true CH433308A (en) 1967-04-15

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CH980663A CH433308A (en) 1962-08-20 1963-08-08 Process for preparing a new quinoline derivative

Country Status (4)

Country Link
BR (1) BR6351757D0 (en)
CH (1) CH433308A (en)
FR (1) FR90364E (en)
GB (2) GB1043994A (en)

Also Published As

Publication number Publication date
BR6351757D0 (en) 1973-07-17
GB1043993A (en) 1966-09-28
GB1043994A (en) 1966-09-28
FR90364E (en) 1967-12-01

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