FR283M - Medicinal product based on 7 alpha, 17-dimethyltestosterone, for therapeutic hormonal treatment. - Google Patents
Medicinal product based on 7 alpha, 17-dimethyltestosterone, for therapeutic hormonal treatment. Download PDFInfo
- Publication number
- FR283M FR283M FR836741A FR836741A FR283M FR 283 M FR283 M FR 283M FR 836741 A FR836741 A FR 836741A FR 836741 A FR836741 A FR 836741A FR 283 M FR283 M FR 283M
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- FR
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- Prior art keywords
- alpha
- dimethyltestosterone
- hexanes
- acetone
- product based
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
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- IVFYLRMMHVYGJH-VLOLGRDOSA-N Bolasterone Chemical compound C1C[C@]2(C)[C@](O)(C)CC[C@H]2[C@@H]2[C@H](C)CC3=CC(=O)CC[C@]3(C)[C@H]21 IVFYLRMMHVYGJH-VLOLGRDOSA-N 0.000 title description 9
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 230000003054 hormonal effect Effects 0.000 title description 2
- 229940126601 medicinal product Drugs 0.000 title 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 230000001195 anabolic effect Effects 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 4
- 239000000391 magnesium silicate Substances 0.000 description 4
- 229910052919 magnesium silicate Inorganic materials 0.000 description 4
- 235000019792 magnesium silicate Nutrition 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- BRQAXEKVGOTNJM-HLXURNFRSA-N 17alpha-Methyl-17beta-hydroxyandrosta-4,6-dien-3-one Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 BRQAXEKVGOTNJM-HLXURNFRSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001548 androgenic effect Effects 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001456 gonadotroph Effects 0.000 description 3
- 229940088597 hormone Drugs 0.000 description 3
- 239000005556 hormone Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000002547 new drug Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WRWBCPJQPDHXTJ-DTMQFJJTSA-N Methandriol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 WRWBCPJQPDHXTJ-DTMQFJJTSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- -1 methyl-magnesium halide Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical group [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Description
RÉPUBLIQUE FRANÇAISEFRENCH REPUBLIC
MINISTERE DE L'INDUSTRIEMINISTRY OF INDUSTRY
SERVICE de la PROPRIÉTÉ INDUSTRIELLEINDUSTRIAL PROPERTY SERVICE
BREVET SPÉCIAL DE MÉDICAMENTSPECIAL MEDICINAL PATENT
P.V. n° 836.741 Classification internationale :P.V. n ° 836.741 International Classification:
N° 283 M A 61 k — C 07 cN ° 283 M A 61 k - C 07 c
Médicament à base de 7 alpha, 17-diméthyltestostérone, pour , le traitement thérapeutique hormonal.Drug based on 7 alpha, 17-dimethyltestosterone, for, therapeutic hormonal treatment.
Société dite : THE UPJOHN COMPANY résidant aux États-Unis d'Amérique.Company known as: THE UPJOHN COMPANY residing in the United States of America.
Demandé le 25 août 1960, à 16h 20m, à Paris.Requested on August 25, 1960, at 4:20 p.m., in Paris.
Délivré par arrêté du 13 mars 1961.Issued by decree of March 13, 1961.
fBulletin officiel de la Propriété industrielle [5.5.M.], n° 8 de 1961.)fOfficial Bulletin of Industrial Property [5.5.M.], No. 8 of 1961.)
(Demande de brevet déposée aux Etats-Unis d'Amérique le 6 juin 1958, sous le n" 740.194, aux noms de MM. J. Allan Campbell et John Claude Babcock.)(Patent application filed in the United States of America on June 6, 1958, under No. 740,194, in the names of Messrs. J. Allan Campbell and John Claude Babcock.)
(Brevet résultant de la division de la demande de brevet d'invention, P.V. n° 796.251, déposée le Tr juin 1959.)(Patent resulting from division of invention patent application, P.V. No. 796,251, filed June Tr, 1959.)
La présente invention est relative à un nouveau composé stéroïde pharmaceutique.The present invention relates to a novel steroid pharmaceutical compound.
Le nouveau composé pharmaceutique est la 7-alpha, 17-diméthyltestostérone et il a la formule développée suivante :The new pharmaceutical compound is 7-alpha, 17-dimethyltestosterone and it has the following structural formula:
oh ch3oh ch3
ch3ch3
•cha• cha
gh3gh3
La 7 alpha, 17-diméthyltestostérone est un solide cristallin blanc ayant un point de fusion de 163 à 165 °C. et un poids moléculaire de 316.47.7 alpha, 17-dimethyltestosterone is a white crystalline solid with a melting point of 163-165 ° C. and a molecular weight of 316.47.
On peut préparer commodément la 7 alpha, 17-diméthyltestostérone en isomérisant le 17 alpha-méthyl-5-androstène-3 béta, 17 béta-diol, composé connu, en 6-déhydro-17-méthyltestostérone, en faisant réagir ce dernier composé avec un halogénure de méthyl-magnésium en présence d'un agent favorisant une addition en positions 1 et 6, par exemple du chlorure cuivreux, et en séparant le mélange d'épimères 6 alpha et 6 béta ainsi obtenus.Conveniently, 7 alpha, 17-dimethyltestosterone can be prepared by isomerizing 17 alpha-methyl-5-androstene-3 beta, 17 beta-diol, known compound, to 6-dehydro-17-methyltestosterone, by reacting the latter compound with a methyl-magnesium halide in the presence of an agent promoting addition in positions 1 and 6, for example cuprous chloride, and by separating the mixture of 6 alpha and 6 beta epimers thus obtained.
Exemple. — On distille une solution de 40 g de 17 alpha-méthyl-5-androstène-3-béta, 17 béta-diol et de 170 g de para-quinone dans 1,3 litre de toluène jusqu'à ce qu'on ait recueilli 250 ml de distillât. A la solution restante, on ajoute, tout en agitant, une solution de 32 g de butylate tertiaire d'aluminium dans 100 ml de toluène sec. On chauffe le mélange au reflux durant cinquante minutes puis on évapore environ la moitié du toluène sous un courant d'azote. On ajoute de l'éther et on lave la solution avec une solution aqueuse d'hydroxyde de sodium puis avec de l'eau. On extrait les phases aqueuses avec de l'éther que l'on réunit à la phase éthérée, on sèche ensuite le tout et on évapore le solvant. Le résidu, dissous dans des hexanes, est chromatographié sur une colonne de 300 g de silicate de magnésium (« Florisil ») que l'on développe avec des portions de 250 ml de solvant ayant la composition suivante et pris dans l'ordre indiqué : deux portions d'hexanes, 7 portions d'hexanes additionnés de 2 % d'acétone; 4 portions d'hexanes additionnés de 4 % d'acétone; 8 portions d'hexanes additionnés de 6 % d'acétone, 5 portions d'hexanes additionnés de 10 % d'acétone, 11 portions d'hexanes additionnés de 12 % d'acétone et 4 portions d'hexanes additionnés de 20 % d'acétone. On réunit les fractions 22 à 26 et on les recristallise dans un mélange d'hexanes additionnés d'acétone pour obtenir 6,5 g de 6-déhydro-17-méthyl-testostérone ayant un point de fusion de 182° à 191 °C (aipha) n = + 21 0 (chloroforme). Le spectre d'absorption dans l'ultra-violet du composé (en solution dans de l'étha-nol) présente un maximum à 284 millimicrons (a-M = 22 725).Example. - A solution of 40 g of 17 alpha-methyl-5-androstene-3-beta, 17 beta-diol and 170 g of para-quinone in 1.3 liters of toluene is distilled until it has been collected. 250 ml of distillate. To the remaining solution is added, while stirring, a solution of 32 g of tertiary aluminum butoxide in 100 ml of dry toluene. The mixture is heated under reflux for fifty minutes and then approximately half of the toluene is evaporated off under a stream of nitrogen. Ether is added and the solution is washed with an aqueous solution of sodium hydroxide and then with water. The aqueous phases are extracted with ether which is combined with the ether phase, the whole is then dried and the solvent is evaporated off. The residue, dissolved in hexanes, is chromatographed on a 300 g column of magnesium silicate ("Florisil") which is developed with 250 ml portions of solvent having the following composition and taken in the order indicated: two portions of hexanes, 7 portions of hexanes with the addition of 2% acetone; 4 portions of hexanes with 4% acetone added; 8 portions of hexanes with the addition of 6% acetone, 5 portions of hexanes with the addition of 10% of acetone, 11 portions of hexanes with the addition of 12% of acetone and 4 portions of hexanes with the addition of 20% of acetone. Fractions 22 to 26 are combined and recrystallized from a mixture of hexanes mixed with acetone to obtain 6.5 g of 6-dehydro-17-methyl-testosterone having a melting point of 182 ° to 191 ° C ( aipha) n = + 21 0 (chloroform). The ultra-violet absorption spectrum of the compound (in solution in ethanol) shows a maximum at 284 millimicrons (a-M = 22,725).
Analyse :Analysis:
Calculé pour C20H28O2 :Calculated for C20H28O2:
C, 79,95 %; H, 9,39 %C, 79.95%; H, 9.39%
Trouvé :Find :
C, 79,60 %; H, 9,55 %C, 79.60%; H, 9.55%
On agite un mélange de 0,4 g de chlorure cuivreux, 20 ml de bromure de méthyl-magnésium 4 M dans de l'éther et 60 ml de tétrahydrofuranne redistillé; on refroidit ce mélange dans un bain de glace durant l'addition d'un mélange de 2 g de 6 - déhydro -17 - méthyltestostérone (préparée comme décrit ci-dessus), 60 ml de tétrahydrofuranne redistillé et 0,2 g de chlorure cuivreux. OnA mixture of 0.4 g of cuprous chloride, 20 ml of 4M methyl-magnesium bromide in ether and 60 ml of redistilled tetrahydrofuran is stirred; this mixture is cooled in an ice bath during the addition of a mixture of 2 g of 6 - dehydro -17 - methyltestosterone (prepared as described above), 60 ml of redistilled tetrahydrofuran and 0.2 g of cuprous chloride . We
1 - 415011 - 41501
Prix du fascicule : 1 NFPrice of the booklet: 1 NF
[283 M] —[283 M] -
retire le bain de gîace et on poursuit l'agitation durant quatre heures. On ajoute ensuite avec précaution de la glace et de l'eau, on acidifie la solution avec de l'acide chlorhydrique 3 N et on extrait plusieurs fois à l'éther. On réunit les extraits éthé-rés et on les lave avec une solution de saumure et de carbonate de sodium puis avec une saumure, puis on sèche les extraits sur du sulfate de magnésium anhydre. On filtre la solution séchée et on verse le filtrat sur une colonne de 75 g de silicate de magnésium (« Florisil ») garnie à l'état humide avec des hexanes (« Skellysolve B ») On élue la colonne avec 250 ml d'hexanes, 0,5 litre d'hexane additionnés de 2 % d'acétone, 2 litres d'hexanes additionnés de 4 % d'acétone et 3,5 litres d'hexanes additionnés de 6 % d'acétone. On recueille quatre fractions de 250 ml puis des fractions de 150 ml. On réunit les résidus des fractions 8 à 16 et on les rechromatographie sur une colonne de 125 g de silicate de magnésium. On élue la colonne avec des hexanes additionnés de 6 % d'acétone et on recueille l'éluat en portions de 150 ml. On réunit les fractions 18 à 29 et on les dissout dans de l'acétone, on décolore au noir animal et on recristallise dans l'acétone. On obtient ainsi un gramme d'un mélange cristallin des 7-épimères de la 7,17-diméthylstesto-stérone ayant un point de fusion de 120° à 140° C, On chauffe ce mélange au reflux avec 1 g de chlo-ranile dans 30 ml d'alcool butyiique tertiaire durant une heure quarante minutes. On évapore lè mélange réactionnel à siccité sous pression réduite. On chromatographie le résidu sur une colonne de 125 g de silicate de magnésium (« Florisil ») et on élue la colonne avec des hexanes additionnés de 5 % d'acétone. On réunit les premières fractions on les évapore, et on recristallise le résidu dans de l'acétone. On obtient ainsi la 7 alpha, 17-diméthyltestostérone sous la forme d'un solide cristallin ayant un point de fusion de 163° à 165 °C; (alpha)D = + 90 0 (chloroforme). Le spectre dans l'ultra-violet du composé (en solution dans l'éthanol) présente un maximum à 243 millimicrons (am = 16 250).the ice bath is removed and stirring is continued for four hours. Ice and water are then carefully added, the solution acidified with 3N hydrochloric acid and extracted several times with ether. The ethereal extracts are combined and washed with a solution of brine and sodium carbonate and then with brine, then the extracts are dried over anhydrous magnesium sulfate. The dried solution is filtered and the filtrate is poured onto a column of 75 g of magnesium silicate ("Florisil") packed in the wet state with hexanes ("Skellysolve B") The column is eluted with 250 ml of hexanes. , 0.5 liter of hexane added with 2% acetone, 2 liters of hexanes added with 4% acetone and 3.5 liters of hexanes added with 6% acetone. Four 250 ml fractions are collected, followed by 150 ml fractions. The residues of fractions 8 to 16 are combined and rechromatographed on a column of 125 g of magnesium silicate. The column was eluted with hexanes supplemented with 6% acetone and the eluate was collected in portions of 150 ml. Fractions 18 to 29 are combined and dissolved in acetone, decolorized with animal charcoal and recrystallized from acetone. This gives one gram of a crystalline mixture of 7-epimers of 7,17-dimethylstestosterone having a melting point of 120 ° to 140 ° C. This mixture is heated to reflux with 1 g of chloranil in 30 ml of tertiary butyl alcohol for one hour and forty minutes. The reaction mixture is evaporated to dryness under reduced pressure. The residue is chromatographed on a column of 125 g of magnesium silicate ("Florisil") and the column is eluted with hexanes supplemented with 5% acetone. The first fractions are combined, evaporated, and the residue is recrystallized from acetone. There is thus obtained 7 alpha, 17-dimethyltestosterone in the form of a crystalline solid having a melting point of 163 ° to 165 ° C; (alpha) D = +90 0 (chloroform). The ultra-violet spectrum of the compound (in solution in ethanol) shows a maximum at 243 millimicrons (am = 16,250).
Analyse :Analysis:
Calculé pour C21H32O2 :Calculated for C21H32O2:
C, 79,69 %, H, 10,19%C, 79.69%, H, 10.19%
Trouvé :Find :
C, 79,22 %, H, 9,91 %C, 79.22%, H, 9.91%
On peut administrer la 7 alpha, 17-diméthyltestostérone à des patients par voie orale ou parenté-raie. Pour une administration orale le nouveau composé se formule sous forme de tablette, de comprimé, de poudre, de pilule ou de capsule en utilisant des excipients inertes acceptables en phar-- macie et connus dans la technique. Pour une administration parentérale, on formule le nouveau composé sous forme d'une solution ou d'une suspension en utilisant des excipients inertes acceptables en pharmacie et connus dans la technique.7 alpha, 17-dimethyltestosterone can be administered to patients orally or by parentage. For oral administration the new compound is formulated as a tablet, tablet, powder, pill or capsule using inert, pharmaceutically acceptable excipients known in the art. For parenteral administration, the new compound is formulated as a solution or a suspension using inert, pharmaceutically acceptable excipients known in the art.
Propriétés pharmacologiques.Pharmacological properties.
Activité anabolique. — La 7 alpha, 17-diméthyltestostérone présente une activité anabolique marquée après administration orale ou parentérale.Anabolic activity. - 7 alpha, 17-dimethyltestosterone exhibits marked anabolic activity after oral or parenteral administration.
Activité androgène. — La 7 alpha,17-diméthyl-testostérone présente une activité androgène marquée après administration orale ou parentérale.Androgenic activity. - 7 alpha, 17-dimethyl-testosterone exhibits marked androgenic activity after oral or parenteral administration.
Activité d'inhibition des hormones gonadotropes. — La 7 alpha,17-diméthyltestostérone présente une activité d'inhibition des hormones gonadotropes chez les femmes.Gonadotropic hormone inhibition activity. - 7 alpha, 17-dimethyltestosterone shows gonadotropic hormone inhibition activity in women.
Applications thérapeutiques.Therapeutic applications.
Réponse anabolique. — En se basant sur des résultats obtenus chez des singes, on peut utiliser une dose de 5 à 10 mg de 7 alpha,17-diméthyltestostérone par jour, administrée par voie orale sous forme de comprimés, pour produire une réponse anabolique satisfaisante chez des patients.Anabolic response. - Based on results obtained in monkeys, a dose of 5 to 10 mg of 7 alpha, 17-dimethyltestosterone per day, administered orally in tablet form, can be used to produce a satisfactory anabolic response in patients. .
RÉSUMÉABSTRACT
À titre de nouveau médicament utile en thérapeutique hormonale, la 7 alpha,17-diméthyltestostérone caractérisée par les points suivants :As a new drug useful in hormonal therapy, 7 alpha, 17-dimethyltestosterone characterized by the following points:
1° Sa formule développée est :1 ° Its structural formula is:
OHOH
2° On a constaté que ses propriétés pharmacologiques sont :2 ° It has been found that its pharmacological properties are:
a. Une activité anabolique;at. Anabolic activity;
b. Une activité androgène;b. Androgenic activity;
c. Une activité d'inhibition des hormones gonadotropes.vs. Gonadotropic hormone inhibition activity.
3° On peut utiliser le nouveau médicament pour produire une réponse anabolique.3 ° The new drug can be used to produce an anabolic response.
4° On peut administrer le nouveau médicament :4 ° The new drug can be administered:
a. Oralement sous forme de comprimés, en mélange avec des excipients inertes acceptables en pharmacie et connus dans la technique;at. Orally in the form of tablets, in admixture with inert excipients acceptable in pharmacies and known in the art;
b. Par voie parentérale sous forme de solution ou de suspension en utilisant des excipients inertes acceptables en pharmacie et connus dans la technique.b. Parenterally in the form of a solution or a suspension using inert excipients acceptable in pharmacies and known in the art.
Société dite : THE UPJOHN COMPANY Par procuration :Company known as: THE UPJOHN COMPANY By proxy:
Simonnot, Rinuy et BltjndellSimonnot, Rinuy and Bltjndell
Pour la vente des fascicules, s'adresser à I'Impbimehie Nationale, 27, rue de la Convention, Paris (15e).For the sale of the booklets, contact the Impbimehie Nationale, 27, rue de la Convention, Paris (15th).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79625159A | 1959-06-01 | 1959-06-01 | |
| US74019467A | 1967-03-20 | 1967-03-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR283M true FR283M (en) | 1961-02-24 |
Family
ID=55662182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR836741A Expired FR283M (en) | 1959-06-01 | 1960-08-25 | Medicinal product based on 7 alpha, 17-dimethyltestosterone, for therapeutic hormonal treatment. |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR283M (en) |
-
1960
- 1960-08-25 FR FR836741A patent/FR283M/en not_active Expired
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