LU82185A1 - NOVEL HYDROXYLATED PYRIMIDINE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC USE - Google Patents
NOVEL HYDROXYLATED PYRIMIDINE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC USE Download PDFInfo
- Publication number
- LU82185A1 LU82185A1 LU82185A LU82185A LU82185A1 LU 82185 A1 LU82185 A1 LU 82185A1 LU 82185 A LU82185 A LU 82185A LU 82185 A LU82185 A LU 82185A LU 82185 A1 LU82185 A1 LU 82185A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- preparation
- pyrimidine
- therapeutic use
- pyrimidine derivatives
- hydroxylated
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
-1--1-
La présente invention concerne les dérivés hydroxylés de 1'isopropylamino-2 pyrimidine de formule générale : v / \ /CH3 K r—The present invention relates to the hydroxylated derivatives of 2-isopropylamino pyrimidine of general formula: v / \ / CH3 K r—
>--N> - N
dans laquelle A^, A^ et Ag représentent chacun : - un atome d'hydrogène, 5 - un radical hydroxy, avec la restriction qu'au moins l'un des substituants A^, A,. et Ag n'est pas un atome d'hydrogène.in which A ^, A ^ and Ag each represent: - a hydrogen atom, 5 - a hydroxy radical, with the restriction that at least one of the substituents A ^, A ,. and Ag is not a hydrogen atom.
Ces composés sont particulièrement intéressants pour leur action dans le domaine de la régénération nerveuse et 10 pour le traitement des dystrophies musculaires.These compounds are particularly interesting for their action in the field of nerve regeneration and for the treatment of muscular dystrophies.
Ces composés peuvent être préparés, par exemple, en faisant réagir la thiométhyle-2 pyrimidine correspondante sur l'isopropylamine dans un solvant non-polaire à la température de 100-120°C, sous pression, selon le schéma suiVant :These compounds can be prepared, for example, by reacting the corresponding 2-thiomethyl pyrimidine on isopropylamine in a non-polar solvent at the temperature of 100-120 ° C., under pressure, according to the following scheme:
A4 VA4 V
)="Ν\ /CH3 \ ^ch3) = "Ν \ / CH3 \ ^ ch3
V \cH \CHV \ cH \ CH
A/--N 3 A6/—« CH3 15 La présente invention sera mieux comprise grâce aux exemples suivants ;A / - N 3 A6 / - "CH3 15 The present invention will be better understood from the following examples;
Exemple 1 : hydroxy-4 isopropylamino-2 pyrimidineExample 1: 4-hydroxy-2-isopropylamino pyrimidine
Le méthyle thiouracile de départ est obtenu en faisant réagir l'iodure de méthyle sur le thiouracile en présence 20 de méthanolate de sodium. Les 20 g (0,14 mole) ainsi obtenus sont placés dans un réacteur pressurisé d'un litre avec -2- 200 ml de toluène sec et 200 ml d'isopropylamine. La réaction s'effectue en 24 heures, sous pression, à 110-120°C. Le mélange qui en résulte est évaporé jusqu'à siccité, traité avec de l'acétone et de l'éther diëthylique (50/50), filtré, 5 lavé avec de l'eau et recristallisé dans de l'acétate d'iso-propyle. On obtient 17 g (rendement 84%) de cristaux blancs fondant à 140°C, dont l'analysé montre une bonne correspondance avec la formule C^H^N^O. Son chlorhydrate (point de fusion 233-234°C - Tottoli) est également un produit cris-10 tallisé blanc ; les caractéristiques de Spectre UV de la base et du chlorhydrate sont les suivantes îThe starting methyl thiouracil is obtained by reacting methyl iodide on the thiouracil in the presence of sodium methanolate. The 20 g (0.14 mol) thus obtained are placed in a pressurized reactor of one liter with -2-200 ml of dry toluene and 200 ml of isopropylamine. The reaction is carried out in 24 hours, under pressure, at 110-120 ° C. The resulting mixture is evaporated to dryness, treated with acetone and ethyl ether (50/50), filtered, washed with water and recrystallized from iso- acetate. propyl. 17 g (84% yield) of white crystals, melting at 140 ° C., are obtained, the analysis of which shows a good correspondence with the formula C ^ H ^ N ^ O. Its hydrochloride (melting point 233-234 ° C - Tottoli) is also a white Cris-10 tallized product; the UV spectrum characteristics of the base and of the hydrochloride are as follows:
Dans l'eau (pour le chlorhydrate) „ λ ï 266 nm e}* = 210 15 max 1cm λ : 217 nm ΕΓ* = 740 max 1cm λ : 290 nm 20 maxIn water (for the hydrochloride) „λ ï 266 nm e} * = 210 15 max 1cm λ: 217 nm ΕΓ * = 740 max 1cm λ: 290 nm 20 max
Dans le méthanol (pour la base) λ ; 293 nm E?% = 510 max 1 cm ; 25 : 222 nm E** =* 730 max 1cm . La base (poids moléculaire 153,18) est insoluble dans l'eau, mais soluble dans le chloroforme.In methanol (for the base) λ; 293 nm E?% = 510 max 1 cm; 25: 222 nm E ** = * 730 max 1cm. The base (molecular weight 153.18) is insoluble in water, but soluble in chloroform.
30 Exemple 2 : hydroxy-5 isopropylamino-2 pyrimidineExample 2: 5-hydroxy-2-isopropylamino pyrimidine
On répète la méthode de l'exemple 1, mais en utilisant 1'hydroxy-5 isopropylamino-2 pyrimidine. Rendement 83%. La température de réaction était de 105°C. Point de fusion 161°C (Tottoli). Spectre UV dans l'eau 60/méthanol 40 ; • ^5 1% : 341 nm E,* = 205 max lem 40 λ : 241 nm eJ% = 1210 mâx 1cm -3-The method of Example 1 is repeated, but using 5-hydroxy-2-isopropylamino pyrimidine. Yield 83%. The reaction temperature was 105 ° C. Melting point 161 ° C (Tottoli). UV spectrum in water 60 / methanol 40; • ^ 5 1%: 341 nm E, * = 205 max lem 40 λ: 241 nm eJ% = 1210 mx 1cm -3-
Exemple 3 : dihydroxy-4,6 isopropylamino-2 pyrimidineExample 3: 4,6-dihydroxy-isopropylamino-2 pyrimidine
On répète la méthode de 1'exemple 1, mais en utilisant la dihydro-4,6 thiométhyle-2 pyrimidine. Rendement 67%. Température de réaction 110°C. Point de fusion 215-220°C, 5 avec décomposition (Tottoli) pour le chlorhydrate répondant à la formule C^H^^N^02HC£, qui est un produit cristallisé blanc insoluble dans l'eau à température ambiante.The method of Example 1 is repeated, but using 4,6-dihydro-2-thiomethyl pyrimidine. Yield 67%. Reaction temperature 110 ° C. Melting point 215-220 ° C, 5 with decomposition (Tottoli) for the hydrochloride corresponding to the formula C ^ H ^^ N ^ 02HC £, which is a white crystalline product insoluble in water at room temperature.
TOXICITETOXICITY
La toxicité aigue (mg/kg) des composés de l'invention a été déterminée sur des souris i.p. et per os et les valeurs sont reportées dans le tableau suivant : composé voie^^^^-«-_ Ex. 1 Ex. 2 Ex. 3 i.p. 200 240 260 per os 205 355 285 PHARMACOLOGIE tThe acute toxicity (mg / kg) of the compounds of the invention was determined in i.p. mice. and per os and the values are given in the following table: compound track ^^^^ - "-_ Ex. 1 Ex. 2 Ex. 3 i.p. 200 240 260 per os 205 355 285 PHARMACOLOGY t
On a recherché l'activité pharmacologique des composés 15 selon l'invention en effectuant une expérimentation comparative sur la régénération du nerf sciatique du rat mâle adulte » (Wistar).The pharmacological activity of the compounds according to the invention was investigated by carrying out a comparative experiment on the regeneration of the sciatic nerve of the adult male rat "(Wistar).
On crée une lésion du nerf sciatique des rats, en appliquant sur le nerf, pendant 20 minutes, une thermosonde. Les 20 rats sont alors traités i.p. avec le produit en référence ou les composés de la présente invention pour une durée prédéterminée. A la fin du traitement, les rats sont tués, les . nerfs sciatiques sont séparés et mis en contact avec une % série de 70 fils parallèles en platine (intervalle 1 mm) très 25 fins et un signal électrique, appliqué en amont du point de lésion, est recherché sur les fils de platine : le fil le plus distant, où le signal peut être capté, donne la longueur régénérée.A lesion of the sciatic nerve of rats is created by applying a thermoprobe to the nerve for 20 minutes. The 20 rats are then treated i.p. with the reference product or the compounds of the present invention for a predetermined period. At the end of the treatment, the rats are killed, the. sciatic nerves are separated and brought into contact with a% series of 70 parallel platinum wires (interval 1 mm) very fine and an electrical signal, applied upstream of the point of injury, is sought on the platinum wires: the wire the more distant, where the signal can be received, gives the regenerated length.
-4--4-
Pour chaque composé testé et chaque durée de traitement, on utilise un lot de 8 rats.For each compound tested and each treatment duration, a batch of 8 rats is used.
Quatre composés ont été testés par voie i.p. : le composé de l'exemple 1, le composé de l'exemple 2, le composé - de 1'exemple 3, tous à la dose de 10 mg/kg et, comme référen ce, un mélange de vitamines B1 (500 mg/kg), B6 (500 mg/kg) et B12 (5 mg/kg), ce qui est connu pour être la composition la plus efficace dans ce domaine. Les animaux-témoins n'ont reçu aucun traitement.Four compounds were tested i.p. : the compound of Example 1, the compound of Example 2, the compound - of Example 3, all at a dose of 10 mg / kg and, as reference, a mixture of vitamins B1 (500 mg / kg), B6 (500 mg / kg) and B12 (5 mg / kg), which is known to be the most effective composition in this area. Control animals received no treatment.
Cinq lots de 8 animaux ont été utilisés pour chaque période (7, 11, 14, 17 et 21 jours) soit pour des témoins, soit pour les composés 1, 2, 3 ou pour le mélange de référence .Five batches of 8 animals were used for each period (7, 11, 14, 17 and 21 days) either for controls, or for compounds 1, 2, 3 or for the reference mixture.
Les résultats de cette expérimentation sont résumés dans le tableau suivant, avec les chiffres obtenus pour les animaux-témoins ; les longueurs des nerfs régénérés sont indiquées dans les colonnes respectives des jours comme valeur moyenne des longueurs mesurées pour tous les animaux de chaque lot. Lorsqu'aucun chiffre n'apparaît (17 et 21 jours), cela signifie que la longueur régénérée excédait la longueur de l'échantillon prélevé. « ---_I)urëe (jours)The results of this experiment are summarized in the following table, with the figures obtained for the control animals; the lengths of the regenerated nerves are indicated in the respective columns of the days as the average value of the lengths measured for all the animals in each batch. When no figure appears (17 and 21 days), this means that the regenerated length exceeded the length of the sample taken. "---_ I) urea (days)
Composé et dose~TTp7---------7 n 14 17 21 Références 5,1 10,2 12,8 17,8 22,4 10¾1_^14^ __ 1¾2____ iHg/kg3__6.7 15,6 26,7 - 500 mg/kg, 500 mg/kg et 5 mgAg 8,8 13,4 15,8 20,4 23,7 -5-Compound and dose ~ TTp7 --------- 7 n 14 17 21 References 5.1 10.2 12.8 17.8 22.4 10¾1_ ^ 14 ^ __ 1¾2 ____ iHg / kg3__6.7 15.6 26 .7 - 500 mg / kg, 500 mg / kg and 5 mg Ag 8.8 13.4 15.8 20.4 23.7 -5-
PRESENTATION - POSOLOGIEPRESENTATION - DOSAGE
Ces dérivés peuvent être présentés sous toute forme thérapeutiquement acceptable, et, par exemple, en comprimés ou en gélules contenant 5 mg par unité de dosage avec un excipient ; en ce qui concerne la forme injectable, le produit peut être présenté dans des ampoules contenant au moins 1 mg de produit actif sous la forme de son chlorhydrate dissout dans l'eau. Quant à la posologie en thérapeutique humaine, les doses vont de 20 mg à 1 g par jour par voie orale et de 1 mg à 50 mg par jour, par voie injectable.These derivatives can be presented in any therapeutically acceptable form, and, for example, in tablets or capsules containing 5 mg per dosage unit with an excipient; as regards the injectable form, the product can be presented in ampoules containing at least 1 mg of active product in the form of its hydrochloride dissolved in water. As for the dosage in human therapy, the doses range from 20 mg to 1 g per day by the oral route and from 1 mg to 50 mg per day by the injectable route.
Un exemple de la forme comprimé est donné ci-dessous : - Composé de l'un des exemples 5 mg - Lactose 70 mg - Talc 20 mg - Stéarate de magnésium 5 mg „ 100 mg ( « a.An example of the tablet form is given below: - Composed of one of the examples 5 mg - Lactose 70 mg - Talc 20 mg - Magnesium stearate 5 mg „100 mg (“ a.
nnot
Claims (3)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB7908494 | 1979-03-10 | ||
GB7908494 | 1979-03-10 | ||
GB7914987 | 1979-04-30 | ||
GB7914987 | 1979-04-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
LU82185A1 true LU82185A1 (en) | 1980-06-06 |
Family
ID=26270867
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LU82185A LU82185A1 (en) | 1979-03-10 | 1980-02-20 | NOVEL HYDROXYLATED PYRIMIDINE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC USE |
Country Status (24)
Country | Link |
---|---|
JP (1) | JPS55122768A (en) |
AR (1) | AR222691A1 (en) |
AU (1) | AU533547B2 (en) |
BE (1) | BE881752A (en) |
CA (1) | CA1132561A (en) |
CH (1) | CH644368A5 (en) |
DE (3) | DE3050999C2 (en) |
EG (1) | EG14282A (en) |
FI (1) | FI66357C (en) |
FR (2) | FR2451370A1 (en) |
GB (1) | GB2045756B (en) |
HK (1) | HK55383A (en) |
IE (1) | IE49547B1 (en) |
IN (1) | IN153791B (en) |
LU (1) | LU82185A1 (en) |
MX (1) | MX6218E (en) |
MY (1) | MY8400200A (en) |
NL (1) | NL184833C (en) |
NO (1) | NO154054C (en) |
NZ (1) | NZ192927A (en) |
OA (1) | OA06484A (en) |
PT (1) | PT70882A (en) |
SE (1) | SE435180B (en) |
SG (1) | SG22683G (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE894517A (en) * | 1981-10-16 | 1983-01-17 | Sod Conseils Rech Applic | NEW ISOPROPYLAMINO PYRIMIDINE DERIVATIVE, ITS PREPARATION AND THERAPEUTIC COMPOSITION BASED ON ITS COMPOUNDS |
US4673677A (en) * | 1983-10-03 | 1987-06-16 | Pfizer Inc. | Method for treatment of gastrointestinal disorders |
US4554276A (en) * | 1983-10-03 | 1985-11-19 | Pfizer Inc. | 2-Amino-5-hydroxy-4-methylpyrimidine derivatives |
US4711888A (en) | 1985-07-24 | 1987-12-08 | Pfizer Inc. | Hydroxy and alkoxy pyrimidines |
WO1989000423A1 (en) * | 1987-07-09 | 1989-01-26 | Pfizer Inc. | 2-amino-5-hydroxy-4-pyrimidones |
US4910204A (en) * | 1988-06-28 | 1990-03-20 | Pfizer Inc. | 2-amino-5-hydroxy-4-pyrimidones |
US5264435A (en) * | 1988-12-29 | 1993-11-23 | Mitsui Petrochemical Industries, Ltd. | Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines |
HU206337B (en) * | 1988-12-29 | 1992-10-28 | Mitsui Petrochemical Ind | Process for producing pyrimidine derivatives and pharmaceutical compositions |
US4940712A (en) * | 1989-05-26 | 1990-07-10 | Pfizer Inc. | Derivatives of hydroxyprimidines as leukotriene synthesis inhibitors |
US5270319A (en) * | 1991-09-09 | 1993-12-14 | Warner-Lambert Company | 5-hydroxy-2-pyrimidinylmethylene derivatives useful as antiinflammatory agents |
US5196431A (en) * | 1992-02-24 | 1993-03-23 | Warner-Lambert Company | 2-substituted amino-4, 6-di-tertiary-buthyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents |
US5220025A (en) * | 1992-02-24 | 1993-06-15 | Warner-Lambert Company | 2-substituted amino-4, 6-di-tertiary-butyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents |
US9133212B1 (en) * | 2005-06-15 | 2015-09-15 | Vanderbilt University | Inhibitors of hemeprotein-catalyzed lipid peroxidation |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB741667A (en) * | 1952-12-05 | 1955-12-07 | Ici Ltd | New pyrimidine derivatives |
GB756189A (en) * | 1954-02-01 | 1956-08-29 | Ici Ltd | New pyrimidine derivatives |
ZA711152B (en) * | 1970-03-02 | 1971-11-24 | Ici Ltd | Manufacture of pyrimidines |
GB1525995A (en) * | 1976-02-18 | 1978-09-27 | Soc D Etudes Prod Chimique | Aminopyrimidine salt |
-
1980
- 1980-02-12 IN IN103/DEL/80A patent/IN153791B/en unknown
- 1980-02-15 BE BE0/199421A patent/BE881752A/en not_active IP Right Cessation
- 1980-02-20 NZ NZ192927A patent/NZ192927A/en unknown
- 1980-02-20 LU LU82185A patent/LU82185A1/en unknown
- 1980-02-26 FI FI800566A patent/FI66357C/en not_active IP Right Cessation
- 1980-02-27 AR AR280106A patent/AR222691A1/en active
- 1980-02-29 PT PT70882A patent/PT70882A/en unknown
- 1980-03-03 CH CH165080A patent/CH644368A5/en not_active IP Right Cessation
- 1980-03-04 CA CA346,981A patent/CA1132561A/en not_active Expired
- 1980-03-04 NL NLAANVRAGE8001289,A patent/NL184833C/en not_active IP Right Cessation
- 1980-03-07 AU AU56248/80A patent/AU533547B2/en not_active Ceased
- 1980-03-07 IE IE477/80A patent/IE49547B1/en unknown
- 1980-03-07 GB GB8007908A patent/GB2045756B/en not_active Expired
- 1980-03-07 NO NO800664A patent/NO154054C/en unknown
- 1980-03-07 SE SE8001812A patent/SE435180B/en not_active IP Right Cessation
- 1980-03-09 EG EG131/80A patent/EG14282A/en active
- 1980-03-10 DE DE3050999A patent/DE3050999C2/en not_active Expired
- 1980-03-10 MX MX808702U patent/MX6218E/en unknown
- 1980-03-10 FR FR8005278A patent/FR2451370A1/en active Granted
- 1980-03-10 FR FR8005277A patent/FR2451191A1/en active Granted
- 1980-03-10 JP JP2931280A patent/JPS55122768A/en active Granted
- 1980-03-10 DE DE3009071A patent/DE3009071C2/en not_active Expired
- 1980-03-10 OA OA57049A patent/OA06484A/en unknown
- 1980-04-30 DE DE19803016752 patent/DE3016752A1/en active Granted
-
1983
- 1983-04-28 SG SG226/83A patent/SG22683G/en unknown
- 1983-11-17 HK HK553/83A patent/HK55383A/en unknown
-
1984
- 1984-12-30 MY MY200/84A patent/MY8400200A/en unknown
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