BE884897R - PHARMACEUTICAL PREPARATIONS - Google Patents

PHARMACEUTICAL PREPARATIONS

Info

Publication number
BE884897R
BE884897R BE0/201846A BE201846A BE884897R BE 884897 R BE884897 R BE 884897R BE 0/201846 A BE0/201846 A BE 0/201846A BE 201846 A BE201846 A BE 201846A BE 884897 R BE884897 R BE 884897R
Authority
BE
Belgium
Prior art keywords
emi
compound
formula
general formula
group
Prior art date
Application number
BE0/201846A
Other languages
French (fr)
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Priority to BE0/201846A priority Critical patent/BE884897R/en
Application granted granted Critical
Publication of BE884897R publication Critical patent/BE884897R/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/88—Nitrogen atoms, e.g. allantoin

Description

       

  Préparations pharmaceutiques La présente invention est relative à une classe particulière de nouveaux dérivés d'urée du type décrit dans le brevet principal, à leur préparation et leur utilisation.

  
Les dérivés d'urée suivant l'invention répondent à la formule générale

  

 <EMI ID=1.1> 


  
 <EMI ID=2.1> 

  
position méta ou para par rapport au radical Ra, et où en outre Ra représente un groupe de formule
 <EMI ID=3.1> 
 où R<3> représente un alcoyle inférieur, Xa un

  
 <EMI ID=4.1> 

  
le radical

  

 <EMI ID=5.1> 


  
est,

  
soit (A) l'un des groupes

  

 <EMI ID=6.1> 


  
et R5 représente un hydrogène ou un alcoxy en C2 à

  
 <EMI ID=7.1> 

  
oxygène et R4a et R5a sont tous les deux méthyle.

  
L'expression " alcoyle inférieur " ainsi que l'expression " alcoxy inférieur " se rapportent à des radicaux hydrocarbonés à chaîne droite ou ramifiée ayant de préférence jusqu'à 4 atomes de carbone, comme le méthyle, l'éthyle, le n-propyle, l'isopropyle, le n-butyle, l'isobutyle, le sec-butyle, le t-butyle;

  
le méthoxy, l'éthoxy, le n-propoxy, l'isopropoxy, le n-butoxy, l'isobutoxy, le sec-butoxy, le t-butoxy. Halogène Il représente les 4 atomes d'halogène, c'està-dire le fluor, le chlore, le brome ou l'iode. 

  
 <EMI ID=8.1> 

  
en position 5.

  
Les nouveaux composés selon l'invention sont efficaces comme anti-androgènes; ils peuvent donc être utilisés comme médicaments, en particulier dans le traitement des maladies qui sont liées à une augmentation de l'activité androgène, comme par exemple l'acné, la séborrhée, l'hirsutisme et l'adénome de la prostate.

  
Quelques-uns des composés suivant l'invention sont également efficaces comme schistosomicides et peuvent donc être utilisés comme médicaments pour la prévention et le traitement de la bilharziose.

  
A cause de leur action anti-androgène et schistosomicide, on préfère ceux des nouveaux dérivés d'urée de formule Ia où Ra représente un groupe (ba), en

  
 <EMI ID=9.1> 

  
dire un dérivé d'hydantolne de formule la.

  
A cause de leur action anti-androgène, on préfère

  
 <EMI ID=10.1> 

  
présente un chlore, un fluor ou un trifluorométhyle, R2a un hydrogène, un chlore, un fluor ou un trifluoro-

  
 <EMI ID=11.1> 

  
un fluor ou un trifluorométhyle et Ra le 5,5-diméthyl3-hydantoyle. Comme nouveau composé de formule la préféré à cause de son action anti-androgène, il faut  <EMI ID=12.1> 

  
méthyl-4-chlorophényl )-carbamoyl7-2-méthylalanine .

  
Comme composés efficaces comme schistosomicides, il faut mentionner ceux des nouveaux dérivés d'urée

  
 <EMI ID=13.1> 

  
5,5-diméthyl-3-hydantoyle. Parmi les nouveaux composés de formule la actifs comme schistosomicides, on pré-

  
 <EMI ID=14.1> 

  
chlorophényl) -carbamoyl7-2-méthyla1 anine et la 3-(4f luorophényl )-5 , 5-diméthyl-hiydantoîne .

  
 <EMI ID=15.1> 

  
paration des composés de la formule la, caractérisé on ce que a) pour préparer un composé de formule la, où. Ra représente le groupe (a), on fait réagir un composé de formule générale
 <EMI ID=16.1> 
 dans des conditions anhydres avec un composé de formule générale

  

 <EMI ID=17.1> 


  
 <EMI ID=18.1> 

  
un amino et l'autre le groupe isocyanate -NCO, ou <EMI ID=19.1> 

  
représente le groupe (a), on soumet un composé de formule générale

  

 <EMI ID=20.1> 


  
 <EMI ID=21.1> 

  
 <EMI ID=22.1> 

  
alcoyle inférieur, à une alcoolyse en utilisant un alcool de formule R<3>0H, où R<3> a la signification donnée ci-dessus, ou c) pour préparer un composé de formule la, où

  
 <EMI ID=23.1> 

  
cyclise un composé de formule générale 
 <EMI ID=24.1> 
 <EMI ID=25.1> 

  
donnée ci-dessus et où Y représente le groupe -OR^ ou <EMI ID=26.1>  <EMI ID=27.1>  réagir un composé de formule générale

  

 <EMI ID=28.1> 


  
 <EMI ID=29.1> 

  
dessus, dans des conditions anhydres avec un composé de formule générale
 <EMI ID=30.1> 
 où R4a et R5a ont la signification donnée ci-dessus, eu e) pour préparer un composé de formule la, où Ra représente le groupe (ba) avec Xa = oxygène, on soumet à une hydrolyse un composé de formule générale
 <EMI ID=31.1> 
 <EMI ID=32.1> 

  
donnée ci-dessus, ou f) pour préparer un composé de formule Ia où R représente le groupe (a), on estérifie un composé de formule générale
 <EMI ID=33.1> 
 <EMI ID=34.1> 

  
avec des composés donneurs de groupes alcoyle inférieur ou

  
 <EMI ID=35.1> 

  
et/ou R2a représentent un nitro, on nitre un composé de formule



  Pharmaceutical preparations The present invention relates to a particular class of new urea derivatives of the type described in the main patent, to their preparation and to their use.

  
The urea derivatives according to the invention correspond to the general formula

  

 <EMI ID = 1.1>


  
 <EMI ID = 2.1>

  
meta or para position with respect to the radical Ra, and where in addition Ra represents a group of formula
 <EMI ID = 3.1>
 where R <3> represents a lower alkyl, Xa a

  
 <EMI ID = 4.1>

  
The radical

  

 <EMI ID = 5.1>


  
East,

  
either (A) one of the groups

  

 <EMI ID = 6.1>


  
and R5 represents a hydrogen or a C2-alkoxy

  
 <EMI ID = 7.1>

  
oxygen and R4a and R5a are both methyl.

  
The expression "lower alkyl" as well as the expression "lower alkoxy" refer to straight or branched chain hydrocarbon radicals preferably having up to 4 carbon atoms, such as methyl, ethyl, n-propyl , isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl;

  
methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy. Halogen It represents the 4 halogen atoms, ie fluorine, chlorine, bromine or iodine.

  
 <EMI ID = 8.1>

  
in position 5.

  
The new compounds according to the invention are effective as antiandrogens; they can therefore be used as medicaments, in particular in the treatment of diseases which are linked to an increase in androgenic activity, such as, for example, acne, seborrhea, hirsutism and prostate adenoma.

  
Some of the compounds according to the invention are also effective as schistosomicides and can therefore be used as medicaments for the prevention and treatment of bilharziasis.

  
Because of their anti-androgenic and schistosomicidal action, those of the new urea derivatives of formula Ia where Ra represents a group (ba) are preferred.

  
 <EMI ID = 9.1>

  
say a hydantoline derivative of formula la.

  
Because of their anti-androgenic action, we prefer

  
 <EMI ID = 10.1>

  
has chlorine, fluorine or trifluoromethyl, R2a hydrogen, chlorine, fluorine or trifluoro-

  
 <EMI ID = 11.1>

  
a fluorine or a trifluoromethyl and Ra the 5,5-dimethyl3-hydantoyl. As a new compound with the preferred formula because of its anti-androgenic action, <EMI ID = 12.1>

  
methyl-4-chlorophenyl) -carbamoyl7-2-methylalanine.

  
As effective compounds as schistosomicides, mention should be made of those of the new urea derivatives.

  
 <EMI ID = 13.1>

  
5,5-dimethyl-3-hydantoyl. Among the new compounds of formula la which are active as schistosomicides, there are

  
 <EMI ID = 14.1>

  
chlorophenyl) -carbamoyl7-2-methyla1 anine and 3- (4f luorophenyl) -5,5-dimethyl-hiydantoin.

  
 <EMI ID = 15.1>

  
paration of the compounds of formula la, characterized in that a) to prepare a compound of formula la, where. Ra represents group (a), a compound of general formula is reacted
 <EMI ID = 16.1>
 under anhydrous conditions with a compound of general formula

  

 <EMI ID = 17.1>


  
 <EMI ID = 18.1>

  
one amino and the other the isocyanate group -NCO, or <EMI ID = 19.1>

  
represents group (a), we submit a compound of general formula

  

 <EMI ID = 20.1>


  
 <EMI ID = 21.1>

  
 <EMI ID = 22.1>

  
lower alkyl, to an alcoholysis using an alcohol of formula R <3> 0H, where R <3> has the meaning given above, or c) to prepare a compound of formula la, where

  
 <EMI ID = 23.1>

  
cyclizes a compound of general formula
 <EMI ID = 24.1>
 <EMI ID = 25.1>

  
given above and where Y represents the group -OR ^ or <EMI ID = 26.1> <EMI ID = 27.1> react a compound of general formula

  

 <EMI ID = 28.1>


  
 <EMI ID = 29.1>

  
above, under anhydrous conditions with a compound of general formula
 <EMI ID = 30.1>
 where R4a and R5a have the meaning given above, e) to prepare a compound of formula la, where Ra represents the group (ba) with Xa = oxygen, a compound of general formula is subjected to hydrolysis
 <EMI ID = 31.1>
 <EMI ID = 32.1>

  
given above, or f) to prepare a compound of formula Ia where R represents group (a), a compound of general formula is esterified
 <EMI ID = 33.1>
 <EMI ID = 34.1>

  
with donor compounds of lower alkyl groups or

  
 <EMI ID = 35.1>

  
and / or R2a represent a nitro, a compound of formula is nitrated

Claims (3)

<EMI ID=36.1> <EMI ID=37.1> <EMI ID=38.1> La préparation des composés intermédiaires répondant aux formules IV et V est décrite dans le brevet principal, qui divulgue également des exemples de préparation des nouveaux dérivés d'urée de la formule Ia. L'invention concerne en outre des compositions pharmaceutiques, sous forme solide ou liquide, contenant comme ingrédient actif à propriétés anti-androgènes et/ou schistosomicides au moins un nouveau dérivé d'urée de la formule Ia, conjointement avec un excipient ou véhicule pharmaceutiquement acceptable tel que décrit dans le brevet principal. REVENDICATIONS<EMI ID = 36.1> <EMI ID = 37.1> <EMI ID = 38.1> The preparation of the intermediate compounds corresponding to formulas IV and V is described in the main patent, which also discloses examples of preparation of the new urea derivatives of formula Ia. The invention further relates to pharmaceutical compositions, in solid or liquid form, containing as active ingredient with anti-androgenic and / or schistosomicide properties at least one new urea derivative of formula Ia, together with a pharmaceutically acceptable excipient or vehicle as described in the main patent. CLAIMS 1. Nouveaux dérivés d'urée de la formule générale <EMI ID=39.1> <EMI ID=40.1> 1. New urea derivatives of the general formula  <EMI ID = 39.1>   <EMI ID = 40.1> halogène, un trifluorométhyle, un nitro ou un alcoxy halogen, trifluoromethyl, nitro or alkoxy <EMI ID=41.1>  <EMI ID = 41.1> Ra représente un groupe de formule Ra represents a group of formula <EMI ID=42.1>  <EMI ID = 42.1> <EMI ID=43.1>  <EMI ID = 43.1> oxygène ou un imino., R4a un alcoyle inférieur oxygen or an imino., R4 has lower alkyl et R5a un hydrogène ou un alcoyle inférieur, avec la précision que si Ra représente le groupe ba, and R5a a hydrogen or a lower alkyl, with the precision that if Ra represents the group ba, le. radical the. radical <EMI ID=44.1>  <EMI ID = 44.1> est, East, soit (A) l'un des groupes either (A) one of the groups <EMI ID=45.1>  <EMI ID = 45.1> <EMI ID=46.1>  <EMI ID = 46.1> 2. Procédé de préparation de dérivés d'urée de formule générale 2. Process for the preparation of urea derivatives of general formula <EMI ID=47.1>  <EMI ID = 47.1> où R t 3. représente un halogène, un trifluorométhyle, where R t 3. represents a halogen, a trifluoromethyl, <EMI ID=48.1>  <EMI ID = 48.1> halogène, un trifluorométhyle, un nitro ou un alcoxy halogen, trifluoromethyl, nitro or alkoxy <EMI ID=49.1>  <EMI ID = 49.1> <EMI ID=50.1>  <EMI ID = 50.1> représente un groupe de formule represents a group of formula <EMI ID=51.1>  <EMI ID = 51.1> <EMI ID=52.1>  <EMI ID = 52.1> oxygène ou un imino, R4a un alcoyle Inférieur oxygen or an imino, R4a a Lower alkyl et R5a un hydrogène ou un alcoyle inférieur, avec and R5 has hydrogen or lower alkyl, with <EMI ID=53.1>  <EMI ID = 53.1> le radical The radical <EMI ID=54.1>  <EMI ID = 54.1> est, East, soit (A) l'un des groupes <EMI ID=55.1> et R5areprésente un hydrogène ou un alcoxy en C2 à either (A) one of the groups  <EMI ID = 55.1>  and R5are represents a hydrogen or a C2 alkoxy to <EMI ID=56.1>  <EMI ID = 56.1> <EMI ID=57.1>  <EMI ID = 57.1> caractérisé en ce que characterized in that a) pour préparer un composé de formule la, où Ra représente le groupe (a), on fait réagir un composé de formule générale <EMI ID=58.1> dans des conditions anhydres avec un composé de formule générale a) to prepare a compound of formula la, where Ra represents the group (a), a compound of general formula is reacted  <EMI ID = 58.1>  under anhydrous conditions with a compound of general formula <EMI ID=59.1>  <EMI ID = 59.1> <EMI ID=60.1>  <EMI ID = 60.1> un amino et l'autre le groupe isocyanate -NCO, ou one amino and the other the isocyanate group -NCO, or b) pour préparer un composé de formule la, où Ra représente le groupe (a), on soumet un composé de formule générale <EMI ID=61.1> <EMI ID=62.1> b) to prepare a compound of formula la, where Ra represents group (a), a compound of general formula is subjected  <EMI ID = 61.1>   <EMI ID = 62.1> dessus et où R6 et R7 représentent tous deux un alcoyle inférieur, à une alcoolyse en utilisant un above and where R6 and R7 both represent lower alkyl, to alcoholysis using a <EMI ID=63.1>  <EMI ID = 63.1> donnée ci-dessus, ou given above, or c) pour préparer un composé de formule la, où Ra représente le groupe (ba) avec Xa = oxygène, on cyclise un composé de formule générale <EMI ID=64.1> <EMI ID=65.1> c) to prepare a compound of formula la, where Ra represents the group (ba) with Xa = oxygen, a compound of general formula is cyclized  <EMI ID = 64.1>  <EMI ID = 65.1> inférieur, ou lower, or d) pour préparer un composé de formule la, où Ra <EMI ID=66.1> d) to prepare a compound of formula la, where Ra <EMI ID = 66.1> réagir un composé de formule générale <EMI ID=67.1> <EMI ID=68.1> react a compound of general formula  <EMI ID = 67.1>   <EMI ID = 68.1> dessus, dans des conditions anhydres avec un composé de formule générale above, under anhydrous conditions with a compound of general formula <EMI ID=69.1>  <EMI ID = 69.1> où R4a et R5a ont la signification donnée ci-dessus, ou where R4a and R5a have the meaning given above, or e ) pour préparer un composé de formule la, où Ra e) to prepare a compound of formula la, where Ra <EMI ID=70.1>  <EMI ID = 70.1> à une hydrolyse un composé de formule générale <EMI ID=71.1> <EMI ID=72.1> at a hydrolysis a compound of general formula  <EMI ID = 71.1>  <EMI ID = 72.1> donnée ci-dessus, ou given above, or <EMI ID=73.1>  <EMI ID = 73.1> représente le groupe (a), on estérifie un composé de formule générale represents group (a), a compound of general formula is esterified <EMI ID=74.1>  <EMI ID = 74.1> <EMI ID=75.1>  <EMI ID = 75.1> avec des composés donneurs de groupes alcoyle inférieurs ou <EMI ID=76.1> with donor compounds from lower alkyl groups or <EMI ID = 76.1> <EMI ID=77.1>  <EMI ID = 77.1> de formule of formula <EMI ID=78.1>  <EMI ID = 78.1> <EMI ID=79.1>  <EMI ID = 79.1> 3. Compositions pharmaceutiques sous forme solide ou liquide, contenant comme ingrédient actif à pro- 3. Pharmaceutical compositions in solid or liquid form, containing as active ingredient to pro- <EMI ID=80.1>  <EMI ID = 80.1> moins un composé suivant la revendication 1, conjointement avec un excipient ou véhicule pharmaceutiquement acceptable tel que décrit dans le brevet principal. at least one compound according to claim 1, together with a pharmaceutically acceptable excipient or vehicle as described in the main patent.
BE0/201846A 1980-08-22 1980-08-22 PHARMACEUTICAL PREPARATIONS BE884897R (en)

Priority Applications (1)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995018794A1 (en) * 1994-01-05 1995-07-13 Roussel Uclaf Novel optionally substituted phenylimidazolidines, intermediates and process for their preparation, their use as drugs and pharmaceutical compositions containing them
FR2715402A1 (en) * 1994-01-05 1995-07-28 Roussel Uclaf New substd. phenyl-imidazolidine(s) which fix to androgen receptors
FR2724169A1 (en) * 1994-09-06 1996-03-08 Roussel Uclaf New substd. phenyl-imidazolidine(s) which fix to androgen receptors

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995018794A1 (en) * 1994-01-05 1995-07-13 Roussel Uclaf Novel optionally substituted phenylimidazolidines, intermediates and process for their preparation, their use as drugs and pharmaceutical compositions containing them
FR2715402A1 (en) * 1994-01-05 1995-07-28 Roussel Uclaf New substd. phenyl-imidazolidine(s) which fix to androgen receptors
FR2724169A1 (en) * 1994-09-06 1996-03-08 Roussel Uclaf New substd. phenyl-imidazolidine(s) which fix to androgen receptors

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Legal Events

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RE Patent lapsed

Owner name: F. HOFFMANN-LA ROCHE & CIE S.A.

Effective date: 19871031