BE836383R - USEFUL N-SUBSTITUTE PYRIDONE AND GENERAL PROCESS FOR PREPARING PYRIDONES - Google Patents

USEFUL N-SUBSTITUTE PYRIDONE AND GENERAL PROCESS FOR PREPARING PYRIDONES

Info

Publication number
BE836383R
BE836383R BE162532A BE162532A BE836383R BE 836383 R BE836383 R BE 836383R BE 162532 A BE162532 A BE 162532A BE 162532 A BE162532 A BE 162532A BE 836383 R BE836383 R BE 836383R
Authority
BE
Belgium
Prior art keywords
emi
pyridone
pharmaceutical composition
mammal
mucous membranes
Prior art date
Application number
BE162532A
Other languages
French (fr)
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 US05/530,684 external-priority patent/US3974281A/en
Application filed filed Critical
Application granted granted Critical
Publication of BE836383R publication Critical patent/BE836383R/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/62Oxygen or sulfur atoms
    • C07D213/63One oxygen atom
    • C07D213/64One oxygen atom attached in position 2 or 6
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

       

   <EMI ID=1.1> 

  
général de préparation de pyridones. 

  
La présente invention concerne de nouvelles compositions pharmaceutiques contenant comme ingrédient ac-

  
 <EMI ID=2.1> 

  
qui répond à la formule (I):

  

 <EMI ID=3.1> 


  
Dans le brevet principal, on a décrit et

  
 <EMI ID=4.1> 

  
possède également d'autres indications thérapeutiques intéressantes.

  
Ainsi, on a observé que le traitement par

  
 <EMI ID=5.1> 

  
cose du sérum (sucre du sang) dans les animaux d'essai.

  
 <EMI ID=6.1> 

  
peutiquement efficace pour protéger les membranes muqueuses

  
du système respiratoire, en particulier celles du naso-pharynx et des poumons contre les agents nuisibles. La protection contre le&#65533; maladies nuisibles locales de l'appareil respira-

  
 <EMI ID=7.1> 

  
a été démontrée lors d'un examen macroscopique des tissus de

  
 <EMI ID=8.1> 

  
de poumons de chiens après traitement avec "AI'iR-69". Des effets protecteurs spéciaux sur les muqueuses revêtant le système respiratoire ont été confirmés au cours d'essais sur les êtres humains, en particulier les personnes montrant des symptômes de sinusite, d'écoulement du rhino-pharynx, d'une rhinite chronique infectieuse, d'une rhinite allergique, de conjonctivite, de maux de tête, de maux d'oreilles ou de mal de gorge. L'efficacité thérapeutique du traitement par

  
 <EMI ID=9.1> 

  
piqûres d'insectes et l'action du sumac vénéneux, a également été démontrée.

  
Les nouvelles indications thérapeutiques du

  
 <EMI ID=10.1> 

  
suivants:

  
Réduction des taux de glucose du sérum

  
 <EMI ID=11.1> 

  
glucose du sérum ( taux de sucre du sang) a été démontré sur des groupes de 10 rats mâles et 10 rates femelles sevrés de la souche Car&#65533;ort&#65533; Farms CFE Strain, en suivant généralement le mode opératoire indiqué ci-dessus à propos de la réduction

  
 <EMI ID=12.1> 

  
 <EMI ID=13.1> 

  
par kg et par jour dans les aliments a montré une valeur

  
 <EMI ID=14.1> 

  
 <EMI ID=15.1>  pour 100 cm3; un groupe de rats mâles témoins, ne recevant

  
 <EMI ID=16.1> 

  
 <EMI ID=17.1> 

  
Un groupe de rates, qui a reçu 600 mg de

  
 <EMI ID=18.1> 

  
jour dans son alimentation a montré une valeur moyenne du

  
 <EMI ID=19.1> 

  
du taux de glucose de 173,0 mg %.

  
Protection des membranes muqueuses du naso-pharynx et des poumons contre les agents nocifs.

  
 <EMI ID=20.1> 

  
 <EMI ID=21.1> 

  
nuisibles localement à l'appareil respiratoire (pétéchie, oedème, hémorragie, infection locale, etc.) a été démontrée par examen macroscopique des tissus du poumon de rats et examen microscopique des tissus du poumon de chiens après trai-

  
 <EMI ID=22.1> 

  
spéciaux sur les muqueuses revêtant l'appareil respiratoire ont été confirmés dans des essais cliniques sur les êtres humains. Les essais ont été effectués sur des personnes présentant au moins l'un des symptômes suivants: sinusite, écoulement dans le rhino-pharynx, rhinite chronique infectieuse, rhinite allergique, conjonctivite, maux de tête, maux d'oreille et maux de gorge. La composition pharmaceutique a été administrée oralement sous forme de capsules, ces capsules étant

  
 <EMI ID=23.1> 

  
 <EMI ID=24.1>  

  
Dans ces essais, on a arrêté et soulagé l'effet nuisible des infections aiguës et chroniques du naso-pharynx, des sinus crâniens, comme le montre la cessation de la congestion des sinus, la disparition de l'érythène des membranes muqueuses, l'assèchement des sinus et l'élimination de l'écoulement du rhino-pharynx. Le signe d'un soulagement des symptômes a été observé dans les 30 à 60 minutes qui ont suivi l'ingestion de la capsule.

  
Effet sur les états de la peau.

  
 <EMI ID=25.1> 

  
les états de la peau comme la dèrmatite ou la démangeai son 

  
 <EMI ID=26.1> 

  
neux a été également démontrée sur les êtres humains présen-

  
 <EMI ID=27.1> 

  
toire du paragraphe précédent. Le soulagement du symptôme a été rapide dans chaque cas. On a observé dans le cas d'une dermatite de contact, comme le contact avec du sumac vénéneux, que l'application de "AHR-69" sous forme de poudre directement sur les zones affectées de la peau assure un soulagement 'sensiblement immédiat de la démangeaison caractéristique et

  
 <EMI ID=28.1> 

  
 <EMI ID=29.1> 

  
Comme déjà montré dans ce mémoire et dans le

  
 <EMI ID=30.1> 

  
d'un comportement thérapeutique très efficace et d'un niveau très faible de toxicité. De la description ci-après, il res-

  
 <EMI ID=31.1>   <EMI ID=32.1> 

  
le comportement thérapeutique ainsi que les caractéristiques de toxicité.

  
Pour l'activité antalgique ou analgésique,

  
 <EMI ID=33.1> 

  
brevet principal, la dose antalgique moyenne orale DE 50 de

  
 <EMI ID=34.1> 

  
 <EMI ID=35.1> 

  
 <EMI ID=36.1> 

  
senté une sédation marquée, une dépression du système nerveux central, une perte de l'efficacité respiratoire, de l'ataxie

  
 <EMI ID=37.1> 

  
samment faible pour éviter une dépression du système nerveux central, il n'a pas été possible de démontrer "l'effet antal-

  
 <EMI ID=38.1> 

  
saignements aigus du nez, et une autopsie a révélé de multiples hémorragies et de l'oedème des poumons. La dose efficace

  
 <EMI ID=39.1> 

  
soit environ le tiers ou le quart de l'activité de "AMR-69" par voie orale.

  
En ce qui concerne l'activité anti-inflammatoire, comme déjà indiqué dans le brevet principal, la dose efficace

  
 <EMI ID=40.1> 

  
elle s'accompagne d'effets secondaires inopportuns, comme noté ci-dessus à propos de ce composé. On n'a observé aucun

  
 <EMI ID=41.1> 

  
orale de 600 mg/kg. 

  
 <EMI ID=42.1> 

  
chez les lapins a été notée dans le brevet principal. L'ad-

  
 <EMI ID=43.1> 

  
la fièvre induite, ce qui n'a pas été considéré comme statistiquement significatif, mais l'on a observé des convulsions sur deux des quatre animaux d'essai et l'on a noté un abais-

  
 <EMI ID=44.1> 

  
les animaux n'ont pas eu de fièvre provoquée expérimentalement. Aucune activité antipyrétique importante n'a été obser-

  
 <EMI ID=45.1> 

  
On a noté, dans des essais effectués sur des rats et sur des chiens, l'abaissement des taux d'acide urique

  
 <EMI ID=46.1> 

  
n'ont pas montré de variations importantes du taux d'acide urique du sérum.

  
En outre, dans des essais destinés à montrer la protection des membranes muqueuses du naso-pharynx et des

  
 <EMI ID=47.1> 

  
 <EMI ID=48.1> 

  
 <EMI ID=49.1> 

  
a eu les effets secondaires inopportuns dans ce dernier cas. On n'a pas observé d'effets délétères aigus sur le système

  
 <EMI ID=50.1> 

  
action protectrice.

  
 <EMI ID=51.1> 

  
dans les divers essais s'est accompgné d'effets secondaires nuisibles. De tels effets secondaires n'ont pas été observés

  
 <EMI ID=52.1> 

  
importante.



   <EMI ID = 1.1>

  
general preparation of pyridones.

  
The present invention relates to novel pharmaceutical compositions containing as active ingredient

  
 <EMI ID = 2.1>

  
which corresponds to formula (I):

  

 <EMI ID = 3.1>


  
In the main patent, it was described and

  
 <EMI ID = 4.1>

  
also has other interesting therapeutic indications.

  
Thus, it was observed that treatment with

  
 <EMI ID = 5.1>

  
cose of serum (blood sugar) in test animals.

  
 <EMI ID = 6.1>

  
possibly effective in protecting mucous membranes

  
respiratory system, especially those of the nasopharynx and lungs against harmful agents. Protection against &#65533; local harmful diseases of the respiratory system

  
 <EMI ID = 7.1>

  
has been shown on gross examination of the tissues of

  
 <EMI ID = 8.1>

  
lungs of dogs after treatment with "AI'iR-69". Special protective effects on the mucous membranes lining the respiratory system have been confirmed in tests on humans, especially people showing symptoms of sinusitis, nasopharyngeal discharge, chronic infectious rhinitis, 'allergic rhinitis, conjunctivitis, headache, earache or sore throat. The therapeutic efficacy of treatment with

  
 <EMI ID = 9.1>

  
insect bites and the action of poison ivy, has also been demonstrated.

  
New therapeutic indications for

  
 <EMI ID = 10.1>

  
following:

  
Reduction of serum glucose levels

  
 <EMI ID = 11.1>

  
Serum glucose (blood sugar level) was demonstrated in groups of 10 male rats and 10 female rats weaned from the Car &#65533; ort &#65533; Farms CFE Strain, generally following the procedure outlined above for reduction

  
 <EMI ID = 12.1>

  
 <EMI ID = 13.1>

  
per kg per day in food showed a value

  
 <EMI ID = 14.1>

  
 <EMI ID = 15.1> for 100 cm3; a group of control male rats, not receiving

  
 <EMI ID = 16.1>

  
 <EMI ID = 17.1>

  
A group of female rats, which received 600 mg of

  
 <EMI ID = 18.1>

  
day in his diet showed an average value of

  
 <EMI ID = 19.1>

  
of the glucose level of 173.0 mg%.

  
Protection of the mucous membranes of the nasopharynx and lungs from harmful agents.

  
 <EMI ID = 20.1>

  
 <EMI ID = 21.1>

  
locally harmful to the respiratory system (petechiae, edema, hemorrhage, local infection, etc.) has been demonstrated by macroscopic examination of rat lung tissue and microscopic examination of dog lung tissue after treatment.

  
 <EMI ID = 22.1>

  
Special features on the mucous membranes lining the respiratory system have been confirmed in clinical trials in humans. The tests were performed on people with at least one of the following symptoms: sinusitis, nasopharyngeal discharge, chronic infectious rhinitis, allergic rhinitis, conjunctivitis, headache, earache and sore throat. The pharmaceutical composition was administered orally in capsule form, these capsules being

  
 <EMI ID = 23.1>

  
 <EMI ID = 24.1>

  
In these trials, the detrimental effect of acute and chronic infections of the nasopharynx, cranial sinuses, as evidenced by cessation of sinus congestion, disappearance of erythene from mucous membranes, disappearance of erythene from mucous membranes, and Drying of the sinuses and elimination of discharge from the nasopharynx. The sign of symptom relief was seen within 30 to 60 minutes of ingestion of the capsule.

  
Effect on skin conditions.

  
 <EMI ID = 25.1>

  
skin conditions like dermatitis or itchy

  
 <EMI ID = 26.1>

  
neux has also been demonstrated in human beings present

  
 <EMI ID = 27.1>

  
cover of the previous paragraph. Relief of the symptom was rapid in each case. In contact dermatitis, such as contact with poison ivy, it has been observed that application of "AHR-69" in powder form directly to the affected areas of the skin provides substantially immediate relief of pain. the characteristic itch and

  
 <EMI ID = 28.1>

  
 <EMI ID = 29.1>

  
As already shown in this memoir and in the

  
 <EMI ID = 30.1>

  
very effective therapeutic behavior and a very low level of toxicity. From the description below, it remains

  
 <EMI ID = 31.1> <EMI ID = 32.1>

  
therapeutic behavior as well as toxicity characteristics.

  
For analgesic or analgesic activity,

  
 <EMI ID = 33.1>

  
principal patent, the average oral analgesic dose DE 50 of

  
 <EMI ID = 34.1>

  
 <EMI ID = 35.1>

  
 <EMI ID = 36.1>

  
felt marked sedation, central nervous system depression, loss of respiratory efficiency, ataxia

  
 <EMI ID = 37.1>

  
sufficiently weak to avoid central nervous system depression, it has not been possible to demonstrate the "antal-

  
 <EMI ID = 38.1>

  
acute nosebleeds, and an autopsy revealed multiple hemorrhages and edema of the lungs. The effective dose

  
 <EMI ID = 39.1>

  
or about a third or a quarter of the activity of "AMR-69" by the oral route.

  
With regard to anti-inflammatory activity, as already stated in the main patent, the effective dose

  
 <EMI ID = 40.1>

  
it is accompanied by unwelcome side effects, as noted above with respect to this compound. No

  
 <EMI ID = 41.1>

  
oral 600 mg / kg.

  
 <EMI ID = 42.1>

  
in rabbits has been noted in the main patent. The D-

  
 <EMI ID = 43.1>

  
induced fever, which was not considered statistically significant, but convulsions were observed in two of the four test animals and a reduction was noted

  
 <EMI ID = 44.1>

  
the animals did not have an experimentally induced fever. No significant antipyretic activity was observed.

  
 <EMI ID = 45.1>

  
In tests with rats and dogs, lower uric acid levels have been noted.

  
 <EMI ID = 46.1>

  
did not show significant variations in serum uric acid levels.

  
In addition, in tests intended to show the protection of the mucous membranes of the nasopharynx and

  
 <EMI ID = 47.1>

  
 <EMI ID = 48.1>

  
 <EMI ID = 49.1>

  
had untimely side effects in the latter case. No acute deleterious effects on the system have been observed.

  
 <EMI ID = 50.1>

  
protective action.

  
 <EMI ID = 51.1>

  
in the various trials was accompanied by harmful side effects. Such side effects have not been observed

  
 <EMI ID = 52.1>

  
important.


    

Claims (1)

<EMI ID=53.1> <EMI ID = 53.1> 1.- Composition pharmaceutique destinée à réduire le taux de glucose du sérum d'un mammifère, caractérisée en 1.- Pharmaceutical composition intended to reduce the glucose level of the serum of a mammal, characterized in <EMI ID=54.1> <EMI ID = 54.1> phényl-2-(lH)-pyridone avec un excipient acceptable du point de vue pharmaceutique. phenyl-2- (1H) -pyridone with a pharmaceutically acceptable excipient. 2.- Composition pharmaceutique destinée à protéger les membranes muqueuses du naso-pharynx et des poumons d'un mammifère contre des agents nuisibles, caractérisée en ce 2.- Pharmaceutical composition intended to protect the mucous membranes of the nasopharynx and lungs of a mammal against harmful agents, characterized in that <EMI ID=55.1> <EMI ID = 55.1> 2-(lH)-pyridone avec un excipient acceptable du point de vue pharmaceutique. 2- (1H) -pyridone with a pharmaceutically acceptable excipient. 3.- Composition pharmaceutique suivant la revendication 2, caractérisée en ce qu'elle est destinée à traiter 3.- Pharmaceutical composition according to claim 2, characterized in that it is intended to treat un mammifère présentant, dans la région des muqueuses de l'appareil respiratoire, au poins l'un dee symptômes de sinusite, d'écoulement rhino-pharyngique, de rhinite chronique infectieuse, de rhinite allergique, de conjonctivite, de maux de tête, de maux d'oreille et de maux de gorge. a mammal exhibiting, in the region of the mucous membranes of the respiratory system, one of the symptoms of sinusitis, nasopharyngeal discharge, chronic infectious rhinitis, allergic rhinitis, conjunctivitis, headache, earache and sore throat. 4.- Composition pharmaceutique destinée à traiter 4.- Pharmaceutical composition intended to treat un mammifère dont la peau présente au moins l'un des symptômes a mammal whose skin shows at least one of the symptoms <EMI ID=56.1> <EMI ID = 56.1> excipient acceptable du point de vue pharmaceutique. pharmaceutically acceptable excipient.
BE162532A 1973-07-19 1975-12-08 USEFUL N-SUBSTITUTE PYRIDONE AND GENERAL PROCESS FOR PREPARING PYRIDONES BE836383R (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US38065573A 1973-07-19 1973-07-19
US05/530,684 US3974281A (en) 1972-12-18 1974-12-09 5-Methyl-1-phenyl-2-(1H)-pyridone compositions and methods of use

Publications (1)

Publication Number Publication Date
BE836383R true BE836383R (en) 1976-04-01

Family

ID=27009076

Family Applications (1)

Application Number Title Priority Date Filing Date
BE162532A BE836383R (en) 1973-07-19 1975-12-08 USEFUL N-SUBSTITUTE PYRIDONE AND GENERAL PROCESS FOR PREPARING PYRIDONES

Country Status (1)

Country Link
BE (1) BE836383R (en)

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