BE871335A - SOLUBLE DERIVATIVES OF 2-ANILINO-ARYL-CARBOXYLIC ACIDS SUBSTITUTED BY THE ORAL ROUTE AS ANTI-INFLAMMATORY AGENTS. - Google Patents

SOLUBLE DERIVATIVES OF 2-ANILINO-ARYL-CARBOXYLIC ACIDS SUBSTITUTED BY THE ORAL ROUTE AS ANTI-INFLAMMATORY AGENTS.

Info

Publication number
BE871335A
BE871335A BE2057359A BE2057359A BE871335A BE 871335 A BE871335 A BE 871335A BE 2057359 A BE2057359 A BE 2057359A BE 2057359 A BE2057359 A BE 2057359A BE 871335 A BE871335 A BE 871335A
Authority
BE
Belgium
Prior art keywords
emi
aryl
carboxylic acids
anilino
inflammatory agents
Prior art date
Application number
BE2057359A
Other languages
French (fr)
Original Assignee
Bago Sa Labor
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 Bago Sa Labor filed Critical Bago Sa Labor
Priority to BE2057359A priority Critical patent/BE871335A/en
Publication of BE871335A publication Critical patent/BE871335A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

       

   <EMI ID=1.1>  

  
La présente invention est relative à des dérivés ! 

  
 <EMI ID=2.1> 

  

 <EMI ID=3.1> 


  
 <EMI ID=4.1> 

  
 <EMI ID=5.1> 

  

 <EMI ID=6.1> 
 

  
Des composés caractéristiques de ce type, définis par la 

  
 <EMI ID=7.1> 

  

 <EMI ID=8.1> 


  
Durant le premier 'stade de ce procède, la réaction entre .;les '

  
 <EMI ID=9.1>  le i-déoxy-l-(méthylàmino)-D-giucitol et le composé formé est réalisée dans le- même, milieu réactionnel où. le premier stade 

  
 <EMI ID=10.1> 

  
 <EMI ID=11.1> 

  
Les solvants polaires utilisés de préférence sont- les. alcools 

  
 <EMI ID=12.1>  <EMI ID=13.1> 

  
 <EMI ID=14.1> 

  
tués, composés qui sont très solubles dans l'eau et. dans les  alcools aliphatiques en C,-Cq. et à partir desquels ils sont  . difficilement cristallisés . Pour effectuer leur cristallisation,! il est nécessaire d'éliminer préalablement l'alcool utilisé et  <EMI ID=15.1> 

  
 <EMI ID=16.1> 

  
 <EMI ID=17.1> 
-utilisé, sont. des points fondamentaux pour parvenir à une éli-  <EMI ID=18.1> 

  
que inférieur. utilisé doit être présent en une quantité  suffisante, en premier lieu, pour permettre à la réaction entre 

  
 <EMI ID=19.1>  <EMI ID=20.1> 

  
formule 1 peuvent être le dichlorométhahe, le tétrachlorure  <EMI ID=21.1> 

  
D'autres types de solvant n'entraînent.pas la cristallisation  de ces nouveaux dérivés-de la formule I . 

  
Le principal avantage de l'obtention de dérivés   <EMI ID=22.1>  <EMI ID=23.1> 

  
rendements de 'synthèse et d'éviter des opérations de filtration 

  
 <EMI ID=24.1> 

  
 <EMI ID=25.1> 

  
pour synthétiser les dérivés de ces acides avec une activité

  
 <EMI ID=26.1> 

  
 <EMI ID=27.1> 

  
et :de bismuth, ont aussi été synthétisés (brevet argentin

  
 <EMI ID=28.1>   <EMI ID=29.1> 

  
 <EMI ID=30.1> 

  
substitués possédant des propriétés analgésiques et anti-in-  flammâtoires, sans aucun effet ulcérogène. 

  
 <EMI ID=31.1> 

  
 <EMI ID=32.1>  <EMI ID=33.1> 

  
 <EMI ID=34.1> 

  
 <EMI ID=35.1> 

  
 <EMI ID=36.1> 

  
 <EMI ID=37.1> 

  
 <EMI ID=38.1> 

  
 <EMI ID=39.1> 

  
 <EMI ID=40.1> 

  
 <EMI ID=41.1>   <EMI ID=42.1> 

  
 <EMI ID=43.1>  <EMI ID=44.1> 

  

 <EMI ID=45.1> 


  
 <EMI ID=46.1>  constamment agité, le mélange est chauffé à une température de

  
 <EMI ID=47.1>  <EMI ID=48.1>  la réaction, indiquée par une chute nette de la .température,:. 

  
 <EMI ID=49.1>  <EMI ID=50.1>  .. entièrement la suspension. Du carbone décolorant et de la  terre d'infusoires sont ajoutés; la suspension résultante, est / <EMI ID=51.1> 

  
 <EMI ID=52.1>  <EMI ID=53.1>  <EMI ID=54.1> 

  
 <EMI ID=55.1> 

  
tion de se produire. Le.composé cristallisé est filtré et lavé avec,.60 ml de chloroforme. Le gâteau est séché sous vide.

  
 <EMI ID=56.1> 

  
d'éthanol et lorsque la. dissolution est achevée, la solution résultante est filtrée'au. moyen de carbone: décolorant. Apres .

  
 <EMI ID=57.1> 

  
 <EMI ID=58.1> 

  
:., Le ; système est agité pendant 30 minutes pour per- , 

  
 <EMI ID=59.1> 

  
 <EMI ID=60.1>  <EMI ID=61.1> 

  
 <EMI ID=62.1> 

  
 <EMI ID=63.1>  <EMI ID=64.1>  <EMI ID=65.1> 

  
 <EMI ID=66.1> 
 <EMI ID=67.1> 
 
 <EMI ID=68.1> 
 <EMI ID=69.1> 
 <EMI ID=70.1> 
 <EMI ID=71.1>  <EMI ID=72.1> 
 <EMI ID=73.1> 
 <EMI ID=74.1>   <EMI ID=75.1> 

  

 <EMI ID=76.1> 


  
 <EMI ID=77.1> 

  

 <EMI ID=78.1> 




   <EMI ID = 1.1>

  
The present invention relates to derivatives!

  
 <EMI ID = 2.1>

  

 <EMI ID = 3.1>


  
 <EMI ID = 4.1>

  
 <EMI ID = 5.1>

  

 <EMI ID = 6.1>
 

  
Characteristic compounds of this type, defined by

  
 <EMI ID = 7.1>

  

 <EMI ID = 8.1>


  
During the first 'stage of this process, the reaction enters.; The'

  
 <EMI ID = 9.1> i-deoxy-l- (methylàmino) -D-giucitol and the compound formed is carried out in the same reaction medium where. the first stage

  
 <EMI ID = 10.1>

  
 <EMI ID = 11.1>

  
The polar solvents preferably used are. alcohols

  
 <EMI ID = 12.1> <EMI ID = 13.1>

  
 <EMI ID = 14.1>

  
killed, compounds which are very soluble in water and. in C, -Cq aliphatic alcohols. and from which they are. hardly crystallized. To effect their crystallization ,! it is necessary to first remove the alcohol used and <EMI ID = 15.1>

  
 <EMI ID = 16.1>

  
 <EMI ID = 17.1>
-used, are. fundamental points to achieve eli- <EMI ID = 18.1>

  
than lower. used must be present in a sufficient quantity, in the first place, to allow the reaction between

  
 <EMI ID = 19.1> <EMI ID = 20.1>

  
formula 1 can be dichloromethane, tetrachloride <EMI ID = 21.1>

  
Other types of solvent do not result in crystallization of these new derivatives of formula I.

  
The main advantage of obtaining derivatives <EMI ID = 22.1> <EMI ID = 23.1>

  
synthesis yields and avoid filtration operations

  
 <EMI ID = 24.1>

  
 <EMI ID = 25.1>

  
to synthesize the derivatives of these acids with an activity

  
 <EMI ID = 26.1>

  
 <EMI ID = 27.1>

  
and: bismuth, have also been synthesized (Argentinian patent

  
 <EMI ID = 28.1> <EMI ID = 29.1>

  
 <EMI ID = 30.1>

  
substituted with analgesic and anti-inflammatory properties, without any ulcerogenic effect.

  
 <EMI ID = 31.1>

  
 <EMI ID = 32.1> <EMI ID = 33.1>

  
 <EMI ID = 34.1>

  
 <EMI ID = 35.1>

  
 <EMI ID = 36.1>

  
 <EMI ID = 37.1>

  
 <EMI ID = 38.1>

  
 <EMI ID = 39.1>

  
 <EMI ID = 40.1>

  
 <EMI ID = 41.1> <EMI ID = 42.1>

  
 <EMI ID = 43.1> <EMI ID = 44.1>

  

 <EMI ID = 45.1>


  
 <EMI ID = 46.1> constantly stirred, the mixture is heated to a temperature of

  
 <EMI ID = 47.1> <EMI ID = 48.1> the reaction, indicated by a sharp drop in temperature,:.

  
 <EMI ID = 49.1> <EMI ID = 50.1> .. fully suspend. Bleaching carbon and diatomaceous earth are added; the resulting suspension, is / <EMI ID = 51.1>

  
 <EMI ID = 52.1> <EMI ID = 53.1> <EMI ID = 54.1>

  
 <EMI ID = 55.1>

  
tion to occur. The crystallized compound is filtered off and washed with 60 ml of chloroform. The cake is dried under vacuum.

  
 <EMI ID = 56.1>

  
ethanol and when the. dissolution is complete, the resulting solution is filtered with water. carbon medium: bleach. After.

  
 <EMI ID = 57.1>

  
 <EMI ID = 58.1>

  
:., The ; system is stirred for 30 minutes to per-,

  
 <EMI ID = 59.1>

  
 <EMI ID = 60.1> <EMI ID = 61.1>

  
 <EMI ID = 62.1>

  
 <EMI ID = 63.1> <EMI ID = 64.1> <EMI ID = 65.1>

  
 <EMI ID = 66.1>
 <EMI ID = 67.1>
 
 <EMI ID = 68.1>
 <EMI ID = 69.1>
 <EMI ID = 70.1>
 <EMI ID = 71.1> <EMI ID = 72.1>
 <EMI ID = 73.1>
 <EMI ID = 74.1> <EMI ID = 75.1>

  

 <EMI ID = 76.1>


  
 <EMI ID = 77.1>

  

 <EMI ID = 78.1>

Claims (1)

<EMI ID=79.1> <EMI ID = 79.1> <EMI ID=80.1> <EMI ID = 80.1> <EMI ID=81.1> <EMI ID=82.1> <EMI ID = 81.1> <EMI ID = 82.1> 6.- Dérivés:solubles des acides 2-anilinp-aryl- carboxyliques substitués utiles par la voie buccale comme <EMI ID=83.1> 6.- Derivatives: soluble substituted 2-anilinp-aryl-carboxylic acids useful by the buccal route as <EMI ID = 83.1>
BE2057359A 1978-10-18 1978-10-18 SOLUBLE DERIVATIVES OF 2-ANILINO-ARYL-CARBOXYLIC ACIDS SUBSTITUTED BY THE ORAL ROUTE AS ANTI-INFLAMMATORY AGENTS. BE871335A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BE2057359A BE871335A (en) 1978-10-18 1978-10-18 SOLUBLE DERIVATIVES OF 2-ANILINO-ARYL-CARBOXYLIC ACIDS SUBSTITUTED BY THE ORAL ROUTE AS ANTI-INFLAMMATORY AGENTS.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
BE871335 1978-10-18
BE2057359A BE871335A (en) 1978-10-18 1978-10-18 SOLUBLE DERIVATIVES OF 2-ANILINO-ARYL-CARBOXYLIC ACIDS SUBSTITUTED BY THE ORAL ROUTE AS ANTI-INFLAMMATORY AGENTS.

Publications (1)

Publication Number Publication Date
BE871335A true BE871335A (en) 1979-04-18

Family

ID=25658693

Family Applications (1)

Application Number Title Priority Date Filing Date
BE2057359A BE871335A (en) 1978-10-18 1978-10-18 SOLUBLE DERIVATIVES OF 2-ANILINO-ARYL-CARBOXYLIC ACIDS SUBSTITUTED BY THE ORAL ROUTE AS ANTI-INFLAMMATORY AGENTS.

Country Status (1)

Country Link
BE (1) BE871335A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2499980A1 (en) * 1981-02-16 1982-08-20 Ciba Geigy Ag (O- (2,6-DICHLORANILINO)) -N-METHYL-D-GLUCAMMONIUM PHENYLACETATE, ITS OBTAINING AND PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME
FR2500751A1 (en) * 1981-02-24 1982-09-03 Ciba Geigy Ag TOPICAL ANTI-INFLAMMATORY PHARMACEUTICAL COMPOSITIONS BASED ON CARBOXYLIC ACID SALTS, NEW CARBOXYLIC ACID SALTS AND THEIR PREPARATION
DE3700172A1 (en) * 1986-01-03 1987-07-09 Therapicon Srl WATER-SOLUBLE N- (METHYL) -GLUCAMINE AND GLUCAMINE SALTS, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THE SAME

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2499980A1 (en) * 1981-02-16 1982-08-20 Ciba Geigy Ag (O- (2,6-DICHLORANILINO)) -N-METHYL-D-GLUCAMMONIUM PHENYLACETATE, ITS OBTAINING AND PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME
WO1982002889A1 (en) * 1981-02-16 1982-09-02 Geigy Ag Ciba Ammonium salts of a substituted carbonic acid,preparation method thereof,utilization and medicinal preparations containing them
FR2500751A1 (en) * 1981-02-24 1982-09-03 Ciba Geigy Ag TOPICAL ANTI-INFLAMMATORY PHARMACEUTICAL COMPOSITIONS BASED ON CARBOXYLIC ACID SALTS, NEW CARBOXYLIC ACID SALTS AND THEIR PREPARATION
DE3700172A1 (en) * 1986-01-03 1987-07-09 Therapicon Srl WATER-SOLUBLE N- (METHYL) -GLUCAMINE AND GLUCAMINE SALTS, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THE SAME

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Legal Events

Date Code Title Description
RE Patent lapsed

Owner name: LABORATORIOS BAGO S.A.

Effective date: 19891031