FR2546162A1 - PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES, ESPECIALLY FOR USE IN THE TREATMENT OF PSORIASIS - Google Patents
PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES, ESPECIALLY FOR USE IN THE TREATMENT OF PSORIASIS Download PDFInfo
- Publication number
- FR2546162A1 FR2546162A1 FR8406790A FR8406790A FR2546162A1 FR 2546162 A1 FR2546162 A1 FR 2546162A1 FR 8406790 A FR8406790 A FR 8406790A FR 8406790 A FR8406790 A FR 8406790A FR 2546162 A1 FR2546162 A1 FR 2546162A1
- Authority
- FR
- France
- Prior art keywords
- dihydroxy
- anthrone
- acyl
- acid chloride
- preparation
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
- C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
- C07C49/737—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
Abstract
LA PRESENTE INVENTION EST RELATIVE A UN PROCEDE POUR LA PREPARATION DE 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES. LA PREPARATION DE 1,8-DIHYDROXY-10-ACYL-9-ANTHRONE, REPRESENTEE PAR LA FORMULE CI-APRES : (CF DESSIN DANS BOPI) DANS LAQUELLE R EST UN GROUPE ALCOYLE AYANT 2 A 4 ATOMES DE CARBONE, EST EFFECTUEE EN UTILISANT, EN TANT QUE MATIERES DE DEPART, DE LA 1,8-DIHYDROXY-9-ANTHRONE REPRESENTEE PAR LA FORMULE CI-APRES : (CF DESSIN DANS BOPI) ET UN CHLORURE D'ACIDE AYANT LA FORMULE CI-APRES : RCOCL, OU R EST TEL QUE DEFINI PLUS HAUT, CARACTERISE EN CE QUE DE LA 2,6-DIMETHYLPYRIDINE EST UTILISEE DANS LE MELANGE REACTIONNEL. APPLICATION : TRAITEMENT DU PSORIASIS.THE PRESENT INVENTION RELATES TO A PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES. THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONE, REPRESENTED BY THE FOLLOWING FORMULA: (CF DRAWING IN BOPI) IN WHICH R IS AN ALCOHYL GROUP HAVING 2 TO 4 CARBON ATOMS, IS PERFORMED USING , AS STARTING MATERIALS, 1,8-DIHYDROXY-9-ANTHRONE REPRESENTED BY THE FOLLOWING FORMULA: (CF DRAWING IN BOPI) AND AN ACID CHLORIDE HAVING THE FOLLOWING FORMULA: RCOCL, OR R IS AS DEFINED ABOVE, CHARACTERIZED IN THAT 2,6-DIMETHYLPYRIDINE IS USED IN THE REACTION MIXTURE. APPLICATION: TREATMENT OF PSORIASIS.
Description
La présente invention est relative à un procédéThe present invention relates to a process
pour la préparation de l,8-dihydroxy-10-acyl-9-anthrones. for the preparation of 1,8-dihydroxy-10-acyl-9-anthrones.
On a utilisé des 1,8-dihydroxy-9-anthrones substituées en Substituted 1,8-dihydroxy-9-anthrones were used in
position 10 depuis quelques années pour remplacer le di- position 10 in recent years to replace the
thranol, connu depuis 1916 et utilisé pour le traitement thranol, known since 1916 and used for the treatment
du psoriasis et qui tache fortement la peau et les vête- psoriasis and that stains the skin and clothing
ments et induit de fortes inflammations cutanées. and induces severe skin inflammation.
La formule structurale des 1,8-dihydroxy-10- The structural formula of 1,8-dihydroxy-10-
acyl-9-anthrones est la suivanteacyl-9-anthrones is the following
HO O OHHO O OH
CO-R dans laquelle R est un groupe alcoyle ayant 2 à 4 atomes CO-R wherein R is an alkyl group having 2 to 4 atoms
de carbone On a préparé ces composés selon le Brevet Fin- These compounds have been prepared according to the
nois FI 57743 en faisant réagir de l'anthraline dans du benzène, à ébullition avec un chlorure d'acide, en présence de pyridine également Le chlorure d'acide est utilisé en un excès de 20 % Le mélange réactionnel est chauffé à No. 57743 by reacting anthralin in benzene, boiling with an acid chloride, in the presence of pyridine also. The acid chloride is used in excess of 20%.
reflux pendant 10 heures et le produit est séparé par cris- reflux for 10 hours and the product is separated by crys-
tallisation à partir de l'acide acétique Avec cette méthode from acetic acid using this method
le rendement n'est, par exemple, que de 25,50 %. the yield is, for example, only 25.50%.
La présente invention a pour objet de fournir un procédé permettant d'obtenir d'importants avantages La The object of the present invention is to provide a method which makes it possible to obtain important advantages.
température de réaction peut être réduite jusqu'à une va- reaction temperature can be reduced to a
leur aussi basse que -10 WC et dans tous les cas, il est their as low as -10 WC and in any case it is
possible d'utiliser de très faibles températures de réac- possible to use very low reaction temperatures
tion, par exemple, la température ambiante De plus, on temperature, for example, the ambient temperature.
peut éviter l'utilisation du benzène, fortement carcino- can avoid the use of benzene, which is strongly carcino-
gène et employer par exemple du toluène qui est moins nocif. gene and use for example toluene which is less harmful.
De plus, le rendement peut être doublé ou triplé par rap- In addition, the yield can be doubled or tripled
port à celui que donne la méthode du Brevet Finnois FI 57743. to that given by the method of Finnish Patent FI 57743.
On peut obtenir les avantages décrits plus haut, grâce au procédé conforme à la présente invention qui met The advantages described above can be obtained by means of the method according to the present invention which sets
en oeuvre de la 2,6-diméthyl-pyridine. of 2,6-dimethylpyridine.
La présente invention repose sur l'observation selon laquelle le remplacement de la pyridine par la 2,6- The present invention is based on the observation that the replacement of pyridine by 2,6-
diméthyl-pyridine permet d'abaisser la température de réac- dimethyl pyridine can lower the reaction temperature
tion, d'utiliser du toluène, du xylène ou des hydrocarbures chlorés, comme du dichlorométhane et du tétrachloroéthane à la place du benzène et même de tripler le rendement par rapport au rendement fourni par la méthode connue Si de plus, le chlorure d'acide est mis en oeuvre en un excès de use of toluene, xylene or chlorinated hydrocarbons, such as dichloromethane and tetrachloroethane instead of benzene and even triple the yield relative to the yield provided by the known method. In addition, the acid chloride is implemented in an excess of
%, la réaction peut être achevée en deux heures. %, the reaction can be completed in two hours.
Grâce à la faible température de réaction indi- Thanks to the low reaction temperature indi-
quée plus haut, qui peut par exemple, être comprise entre -10 C et + 20 C, il en résulte que la quantité d'impuretés above, which may for example be between -10 C and + 20 C, the result is that the amount of impurities
passant dans la l,8-dihydroxy- 10-acyl-9-anthrone, est fai- passing through 1,8-dihydroxy-10-acyl-9-anthrone, is
ble La purification est donc une procédure simple par Purification is therefore a simple procedure by
rapport à celle qui est impliquée dans la méthode connue. compared to the one involved in the known method.
On peut utiliser de l'acétonitrile ou du 2-propanol en tant que solvant de recristallisation, avec l'acide acétique ou Acetonitrile or 2-propanol can be used as a recrystallization solvent with acetic acid or
à la place de celui-ci.instead of it.
Les composés prépares conformément à la présente invention peuvent être utilisés, par exemple, dans des crèmes pour la peau, à base de vaseline ou de paraffine, à des concentrations de 0,5 à 5 %, dans des bâtons pour les soins de la peau, à des concentrations de, par exemple, The compounds prepared according to the present invention can be used, for example, in skin creams, based on petrolatum or paraffin, at concentrations of 0.5 to 5%, in poles for skin care. , at concentrations of, for example,
2 à 8 % et dans des gels et des solutions filmogènes. 2-8% and in gels and film-forming solutions.
EXEMPLE 1EXAMPLE 1
On ajoute du chlorure de butyryle à raison de 207 ml ( 213 g, 2,0 moles) en une période de deux heures, à une température inférieure à O C, à un mélange qui contient 207 ml (213 g, 2.0 moles) of butyryl chloride is added over a period of two hours at a temperature below 0 ° C to a mixture which contains
2500 ml de toluène, 226 g Xl,0 mole) de l,8-dihydroxy-9- 2500 ml of toluene, 226 g (1.0 mole) of 1,8-dihydroxy-9-
anthrone et 232 ml ( 214 g, 2,0 moles) de 2,6-diméthylpyri- anthrone and 232 ml (214 g, 2.0 moles) of 2,6-dimethylpyri-
dine. Le mélange est agité à une température inférieure dine. The mixture is stirred at a lower temperature
2546 1 622546 1 62
à O C, pendant 2 heures supplémentaires après l'addition. at 0 ° C for an additional 2 hours after addition.
Le mélange est chauffé ensuite à + 4 Q C, le chlo- The mixture is then heated to +4 ° C., the chlorine
rhydrate de la 2,6-diméthylpyridine est séparé par filtra- 2,6-dimethylpyridine hydrate is separated by filtration.
tion et la plus grande partie du toluène est évaporée sous pression réduite On ajoute 2300 ml d'isopropanol au résidu, on refroidit le mélange à -10 a C et récupère le précipité and most of the toluene is evaporated under reduced pressure. 2300 ml of isopropanol are added to the residue, the mixture is cooled to -10 ° C. and the precipitate is recovered.
en le filtrant Une recristallisation est effectuée à par- filtering it A recrystallization is carried out at
tir d'acétonitrile et fournit 222 g de 1,8-dihydroxy-10- acetonitrile and provides 222 g of 1,8-dihydroxy-10-
butyryl-9-anthrone Cela constitue un rendement de 75 %. butyryl-9-anthrone This constitutes a 75% yield.
EXEMPLE 2EXAMPLE 2
On répète la procédure qui est décrite dans l'Exemple 1, sauf que l'on utilise du xylène à la place du toluene Le rendement est le même que celui de l'Exemple 1, The procedure described in Example 1 is repeated except that xylene is used in place of toluene. The yield is the same as that of Example 1.
à savoir 75 %.namely 75%.
EXEMPLE 3EXAMPLE 3
Du chlorure de propionyle en une quantité de 86,9 ml ( 92,5 g, 1 mole) est ajouté en une période de 2 heures environ, à une température inférieure à O C, à un mélange contenant 1200 ml de toluène, 113 g ( 0,- 5 mole) de 1,8-dihydroxy-9-anthrone et 116 ml ( 107 g, 1 mole) de 2,6diméthylpyridine L'agitation est poursuivie pendant Propionyl chloride in an amount of 86.9 ml (92.5 g, 1 mole) is added over a period of about 2 hours, at a temperature below 0 ° C, to a mixture containing 1200 ml of toluene, 113 g ( 0.5 mol) of 1,8-dihydroxy-9-anthrone and 116 ml (107 g, 1 mole) of 2,6-dimethylpyridine. Stirring is continued for
2 heures supplémentaires après l'addition. 2 additional hours after the addition.
La 1,8-dihydroxy-10-propionyl-9-anthrone ainsi obtenue est séparée -slon la procédure qui est décrite dans The 1,8-dihydroxy-10-propionyl-9-anthrone thus obtained is separated -slon the procedure which is described in
l'Exemple 1 Le rendement est de 120 g ( 82 %). Example 1 The yield is 120 g (82%).
EXEMPLE 4EXAMPLE 4
A partir de 1,8-dihydroxy-9-anthrone et de chlo- From 1,8-dihydroxy-9-anthrone and chlo-
rure de valéryle en un excès de 100 % et en procédant par ailleurs selon la méthode qui est décrite dans l'Exemple 1, on obtient la 1,8-dihydroxy10-valéryl-9-anthrone avec un valence in a 100% excess and, by the method otherwise described in Example 1, yields 1,8-dihydroxy-valeryl-9-anthrone with
rendement de 53 %.53% yield.
EXEMPLE 5EXAMPLE 5
On préparé des compositions pharmaceutiques à Pharmaceutical compositions are prepared
partir des constituants suivants, avec les quantités indi- from the following constituents, with the quantities
quées.cated.
paraffine liquide 40 60 % paraffine solide 40 60 % cire microcristalline 0,5 5 % liquid paraffin 40 60% solid paraffin 40 60% microcrystalline wax 0.5 5%
De plus, on mélange environ 2 à 8 % de 1,8-dihy- In addition, about 2 to 8% of 1,8-dihydro-
droxy-10-butyryl-9-anthrone avec la composition support présentée cidessus On moule des bâtons conçus pour les soins de la peau à partir de ce mélange et l'on observe que les propriétés d'utilisation des bâtons sont bonnes et que de plus, le médicament contenu dans les bâtons demeure droxy-10-butyryl-9-anthrone with the carrier composition set forth above Skin care sticks are molded from this mixture and it is observed that the properties of use of the sticks are good and that moreover , the drug contained in the sticks remains
inchangé, en particulier, il n'est pas oxydé. unchanged, in particular, it is not oxidized.
Ainsi que cela ressort de ce qui précède, l'in- As is apparent from the foregoing, the
vention ne se limite nullement à ceux de ses modes de mise en oeuvre, de réalisation et d'application qui viennent d'être décrits de façon plus explicite; elle en embrasse au contraire toutes les variantes qui peuvent venir à l'esprit du technicien en la matière, sans s'écarter du cadre, ni de la portée, de la présente inventions This intervention is in no way limited to those of its modes of implementation, of realization and of application which have just been described more explicitly; on the contrary, it embraces all the variants that may come to the mind of the technician in the field, without departing from the scope or scope of the present inventions
Claims (5)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI831739A FI66585C (en) | 1983-05-18 | 1983-05-18 | FOERFARANDE FOER FRAMSTAELLNING AV SAERSKILT VID BEHANDLING AVSORIASIS ANVAENDBARA 1,8-DIHYDROXI-10-ACYL-9-ANTRONER |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2546162A1 true FR2546162A1 (en) | 1984-11-23 |
| FR2546162B1 FR2546162B1 (en) | 1987-01-30 |
Family
ID=8517222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8406790A Expired FR2546162B1 (en) | 1983-05-18 | 1984-05-02 | PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES, IN PARTICULAR FOR USE IN THE TREATMENT OF PSORIASIS |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS59212443A (en) |
| KR (1) | KR840009059A (en) |
| AU (1) | AU560079B2 (en) |
| BE (1) | BE899334A (en) |
| CA (1) | CA1212943A (en) |
| CH (1) | CH659464A5 (en) |
| CS (1) | CS256379B2 (en) |
| DD (1) | DD223702A5 (en) |
| DE (1) | DE3418382A1 (en) |
| DK (1) | DK154207C (en) |
| ES (1) | ES8505167A1 (en) |
| FI (1) | FI66585C (en) |
| FR (1) | FR2546162B1 (en) |
| GB (1) | GB2140007B (en) |
| GR (1) | GR79971B (en) |
| HU (1) | HUT36076A (en) |
| IL (1) | IL71446A (en) |
| IN (1) | IN156115B (en) |
| IS (1) | IS2902A7 (en) |
| IT (1) | IT1173473B (en) |
| LU (1) | LU85292A1 (en) |
| NL (1) | NL8401074A (en) |
| NO (1) | NO157099C (en) |
| NZ (1) | NZ207592A (en) |
| PH (1) | PH20038A (en) |
| PL (1) | PL141866B1 (en) |
| PT (1) | PT78603B (en) |
| SE (1) | SE453827B (en) |
| SU (1) | SU1240351A3 (en) |
| YU (1) | YU81784A (en) |
| ZA (1) | ZA842223B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2492372A1 (en) * | 1980-10-21 | 1982-04-23 | Cird | 1,8-DIHYDROXY-9-ANTHRONES SUBSTITUTED IN POSITION 10 AND THEIR USE IN HUMAN OR VETERINARY MEDICINE AND IN COSMETICS |
| FR2591222B1 (en) * | 1985-12-11 | 1988-07-22 | Cird | MONO, DI AND TRI-ESTERS OF 1,8-DIHYDROXY PHENYL-10 ANTHRONE-9 OR ANTHRANOL-9, THEIR PREPARATION PROCESS AND THEIR USE IN HUMAN OR VETERINARY MEDICINE AND IN COSMETICS |
| US4843097A (en) * | 1984-06-13 | 1989-06-27 | Groupement D'interet Economique Dit: Centre International De Recherches Dermatologiques C.I.R.D. | 10-aryl-1,8-dihydroxy-9-anthrones and their esters, process for preparing same, and use of same in human and veterinary medicine and in cosmetics |
| FR2566772B1 (en) * | 1984-06-29 | 1986-11-14 | Cird | DIACYLOXY-1,8 ACYL-10 ANTHRONES, THEIR PREPARATION PROCESS AND THEIR USE IN HUMAN OR VETERINARY MEDICINE AND IN COSMETICS |
| FR2580631B1 (en) * | 1985-04-17 | 1987-05-29 | Cird | HYDROXY-1 ACYLOXY-8 ACYL-10 ANTHRONES, THEIR PREPARATION PROCESS AND THEIR USE IN HUMAN OR VETERINARY MEDICINE AND IN COSMETICS |
| AU660718B2 (en) * | 1991-10-04 | 1995-07-06 | Fisher & Paykel Healthcare Limited | Improvements in or relating to humidifiers |
| DE4231636A1 (en) * | 1992-09-22 | 1994-03-24 | Beiersdorf Ag | New anthrone and anthracene derivatives substituted in the 10-position, processes for their preparation, pharmaceutical or cosmetic compositions containing these compounds and their use |
| US5426197A (en) * | 1993-07-19 | 1995-06-20 | Teva Pharmaceutical Industries, Ltd. | 10-substituted 1,8-dihydroxy-9(10H) anthracenone pharmaceuticals |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017420A1 (en) * | 1979-03-29 | 1980-10-15 | Orion-Yhtymä Oy | New dihydroxy-acylanthrones having anti-psoriatic activity, process for preparing them, pharmaceutical compositions comprising them, and their use as anti-psoriatic agents |
-
1983
- 1983-05-18 FI FI831739A patent/FI66585C/en not_active IP Right Cessation
-
1984
- 1984-03-22 NZ NZ207592A patent/NZ207592A/en unknown
- 1984-03-22 AU AU25998/84A patent/AU560079B2/en not_active Ceased
- 1984-03-23 IT IT20213/84A patent/IT1173473B/en active
- 1984-03-26 ZA ZA842223A patent/ZA842223B/en unknown
- 1984-03-29 IN IN209/CAL/84A patent/IN156115B/en unknown
- 1984-03-30 DK DK173584A patent/DK154207C/en active IP Right Grant
- 1984-04-04 GB GB08408666A patent/GB2140007B/en not_active Expired
- 1984-04-04 NL NL8401074A patent/NL8401074A/en not_active Application Discontinuation
- 1984-04-05 GR GR74318A patent/GR79971B/el unknown
- 1984-04-05 IL IL71446A patent/IL71446A/en not_active IP Right Cessation
- 1984-04-05 BE BE0/212698A patent/BE899334A/en not_active IP Right Cessation
- 1984-04-05 IS IS2902A patent/IS2902A7/en unknown
- 1984-04-06 LU LU85292A patent/LU85292A1/en unknown
- 1984-04-18 CS CS842911A patent/CS256379B2/en unknown
- 1984-04-18 ES ES531760A patent/ES8505167A1/en not_active Expired
- 1984-04-27 KR KR1019840002278A patent/KR840009059A/en not_active Application Discontinuation
- 1984-05-02 FR FR8406790A patent/FR2546162B1/en not_active Expired
- 1984-05-04 JP JP59090047A patent/JPS59212443A/en active Pending
- 1984-05-08 SU SU843735603A patent/SU1240351A3/en active
- 1984-05-10 YU YU00817/84A patent/YU81784A/en unknown
- 1984-05-16 SE SE8402649A patent/SE453827B/en not_active IP Right Cessation
- 1984-05-16 NO NO841965A patent/NO157099C/en unknown
- 1984-05-16 PH PH30686A patent/PH20038A/en unknown
- 1984-05-17 CH CH2431/84A patent/CH659464A5/en not_active IP Right Cessation
- 1984-05-17 PT PT78603A patent/PT78603B/en unknown
- 1984-05-17 DE DE19843418382 patent/DE3418382A1/en not_active Withdrawn
- 1984-05-17 PL PL1984247724A patent/PL141866B1/en unknown
- 1984-05-17 CA CA000454593A patent/CA1212943A/en not_active Expired
- 1984-05-17 DD DD84263131A patent/DD223702A5/en unknown
- 1984-05-17 HU HU841908A patent/HUT36076A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0017420A1 (en) * | 1979-03-29 | 1980-10-15 | Orion-Yhtymä Oy | New dihydroxy-acylanthrones having anti-psoriatic activity, process for preparing them, pharmaceutical compositions comprising them, and their use as anti-psoriatic agents |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 98, no. 16, 18 avril 1983, page 364, colonne 1, abrégé no. 132215g, Columbus, Ohio, US; A. SCHALTEGGER et al.: "On the stability of some antipsoriatic active anthralin (Dithranol) derivatives. A qualitative high-performance liquid chromatography investigation", & DERMATOLOGICA 1982, 165(4), 363-368 * |
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