FI66585C - FOERFARANDE FOER FRAMSTAELLNING AV SAERSKILT VID BEHANDLING AVSORIASIS ANVAENDBARA 1,8-DIHYDROXI-10-ACYL-9-ANTRONER - Google Patents

FOERFARANDE FOER FRAMSTAELLNING AV SAERSKILT VID BEHANDLING AVSORIASIS ANVAENDBARA 1,8-DIHYDROXI-10-ACYL-9-ANTRONER Download PDF

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FI66585C
FI66585C FI831739A FI831739A FI66585C FI 66585 C FI66585 C FI 66585C FI 831739 A FI831739 A FI 831739A FI 831739 A FI831739 A FI 831739A FI 66585 C FI66585 C FI 66585C
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Prior art keywords
acyl
avsoriasis
antroner
dihydroxi
saerskilt
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FI831739A
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Finnish (fi)
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FI831739A0 (en
FI66585B (en
Inventor
Pekka Juhani Kairisalo
Aino Kyllikki Pippuri
Erkki Juhani Honkanen
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Orion Yhtymae Oy
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Publication of FI831739A0 publication Critical patent/FI831739A0/en
Priority to FI831739A priority Critical patent/FI66585C/en
Priority to NZ207592A priority patent/NZ207592A/en
Priority to AU25998/84A priority patent/AU560079B2/en
Priority to IT20213/84A priority patent/IT1173473B/en
Priority to ZA842223A priority patent/ZA842223B/en
Priority to IN209/CAL/84A priority patent/IN156115B/en
Priority to DK173584A priority patent/DK154207C/en
Priority to GB08408666A priority patent/GB2140007B/en
Priority to NL8401074A priority patent/NL8401074A/en
Priority to IL71446A priority patent/IL71446A/en
Priority to BE0/212698A priority patent/BE899334A/en
Priority to IS2902A priority patent/IS2902A7/en
Priority to GR74318A priority patent/GR79971B/el
Priority to LU85292A priority patent/LU85292A1/en
Priority to CS842911A priority patent/CS256379B2/en
Priority to ES531760A priority patent/ES8505167A1/en
Priority to KR1019840002278A priority patent/KR840009059A/en
Priority to FR8406790A priority patent/FR2546162B1/en
Priority to JP59090047A priority patent/JPS59212443A/en
Priority to SU843735603A priority patent/SU1240351A3/en
Priority to YU00817/84A priority patent/YU81784A/en
Priority to SE8402649A priority patent/SE453827B/en
Priority to PH30686A priority patent/PH20038A/en
Priority to NO841965A priority patent/NO157099C/en
Priority to PL1984247724A priority patent/PL141866B1/en
Priority to PT78603A priority patent/PT78603B/en
Priority to CH2431/84A priority patent/CH659464A5/en
Priority to HU841908A priority patent/HUT36076A/en
Priority to DE19843418382 priority patent/DE3418382A1/en
Priority to CA000454593A priority patent/CA1212943A/en
Priority to DD84263131A priority patent/DD223702A5/en
Application granted granted Critical
Publication of FI66585B publication Critical patent/FI66585B/en
Publication of FI66585C publication Critical patent/FI66585C/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/723Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
    • C07C49/727Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
    • C07C49/737Unsaturated 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs 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)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dermatology (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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)

Description

1 665851 66585

Menetelmä erityisesti psoriasiksen hoitoon käytettävien 1,fl-dihydroksi-10-asyyli-9_antronien valmistamiseksi Tämä keksintö koskee menetelmää 1,Θ-dihydroksi-10-asyyli-5 9-antronien valmistamiseksi. 10-asemassa substituoituja 1.8- dihydroksi-9-antroneja on käytetty muutamien vuosien ajan korvaamaan jo vuodesta 1916 tunnettu psoriasiksen hoitoon käytetty, voimakkaasti ihoa ja vaatteita värjäävä ja ihoa voimakkaasti tulehduttava ditranoli.The present invention relates to a process for the preparation of 1,1'-dihydroxy-10-acyl-59-anthrones. 10-Substituted 1,8-dihydroxy-9-anthrons have been used for several years to replace ditranol, which has been known since 1916 for the treatment of psoriasis and is a strong skin and clothing dye and highly inflamed skin.

10 1.8- dihydroksi-10-asyyli~9-antronin rakennekaava on seuraava:The structural formula of 1,8-dihydroxy-10-acyl-9-anthrone is as follows:

CO-RCO-R

20 jossa R on 2-4 hiiliatomia sisältävä alkyyli ryhmä. Yhdisteitä on valmistettu suomalaisen patenttijulkaisun FI 57743 mukaan saattamalla antraliini reagoimaan kiehuvassa bent-seenissä happokloridin kanssa, jolloin läsnä on myös pyri-diiniä. Happokloridia käytetään 20 %:n ylimäärä. Reaktio-25 seosta keitetään palautusjäähdyttäen 10 tunnin ajan ja tuote kiteytetään etikkahaposta. Saanto on kyseessä olevassa menetelmässä esim. vain 25,5 % teoreettisesta.20 wherein R is an alkyl group having 2 to 4 carbon atoms. The compounds have been prepared according to Finnish patent publication FI 57743 by reacting anthralin in boiling Bentene with an acid chloride, in which case pyridine is also present. An excess of 20% of acid chloride is used. The reaction mixture is refluxed for 10 hours and the product is crystallized from acetic acid. The yield in the method in question is, for example, only 25.5% of theory.

Tämän keksinnön tarkoituksena on aikaansaada menetelmä, 30 jonka avulla voidaan saavuttaa huomattavia etuja. Reaktio-lämpötila voidaan alentaa jopa -10°C:een ja joka tapauksessa voidaan käyttää varsin alhaisia reaktio lämpötiloja, esimerkiksi huoneenlämpötilaa. Lisäksi voidaan välttää voimakkaasti karsinogeenista bentseeniä ja käyttää esimer-35 kiksi vähemmän haitallista tolueenia. Vielä saadaan saanto nousemaan 2-3-kertaiseksi suomalaisen patentin FI 57743 menetelmään verrattuna.It is an object of the present invention to provide a method by which considerable advantages can be obtained. The reaction temperature can be reduced to as low as -10 ° C, and in any case, rather low reaction temperatures, for example room temperature, can be used. In addition, highly carcinogenic benzene can be avoided and less harmful toluene, for example, can be used. The yield is further increased 2-3 times compared to the method of the Finnish patent FI 57743.

2 665852 66585

Edellä mainitut edut on saavutettu menetelmällä, jonka tunnusomaiset piirteet on annettu oheisessa patenttivaatimuksessa 1.The above advantages are achieved by a method, the characteristic features of which are given in the appended claim 1.

5 Keksintö perustuu siihen huomioon, että pyridiinin korvaaminen 2,6-dimetyylipyridiinillä aikaansaa sen, että reaktio-lämpötilaa voidaan alentaa, että bentseenin tilalla voidaan käyttää tolueenia, ksyleeniä tai kloorattuja hiilivetyjä, kuten dikloorimetaania tai tetrakloorieteeniä ja että saanto 10 jopa kolminkertaistuu tunnettuun menetelmään verrattuna. Jos lisäksi happokloridia käytetään 100 %:n ylimäärä, saadaan reaktio menemään loppuun kahdessa tunnissa.The invention is based on the fact that the replacement of pyridine with 2,6-dimethylpyridine makes it possible to lower the reaction temperature, to use toluene, xylene or chlorinated hydrocarbons such as dichloromethane or tetrachlorethylene instead of benzene and to even triple the yield compared to the known process. In addition, if 100% excess of acid chloride is used, the reaction is completed in two hours.

Edellä mainitusta alhaisesta reaktiolämpötilasta, joka voi 15 olla esimerkiksi -10°C - +20°C, seuraa, että valmiiseen 1,8-dihydroksi-10-asyyli-9-antroniin joutuvien epäpuhtauksien määrä on vähäinen. Niinpä puhdistus on yksinkertainen toimenpide verrattuna tunnetun menetelmän vastaavaan toimenpiteeseen. Uudelleenkiteytysliuottimena sopivat käytettä-20 väksi etikkahapon ohessa tai sijasta asetonitriili tai 2-propanoli.It follows from the above-mentioned low reaction temperature, which may be, for example, -10 ° C to + 20 ° C, that the amount of impurities entering the finished 1,8-dihydroxy-10-acyl-9-anthrone is small. Thus, the purification is a simple operation as compared with the corresponding operation of the known method. Suitable recrystallization solvents are acetonitrile or 2-propanol in addition to or instead of acetic acid.

Keksinnön mukaisesti valmistettuja yhdisteitä voidaan käyttää esimerkiksi vaseliini- tai paraffiinipohjaisissa 25 ihovoiteissa 0,5 - 5 %sn pitoisuuksina, ihonhoitoon tarkoitetuissa puikoissa esim 2 - Θ %:n pitoisuuksina ja geeleissä sekä kalvon muodostavissa liuoksissa.The compounds according to the invention can be used, for example, in petrolatum or paraffin-based skin creams in concentrations of 0.5 to 5% sn, in skin care needles, for example in concentrations of 2 to Θ%, and in gels and film-forming solutions.

Seuraavat esimerkit kuvaavat keksintöä tarkemmin.The following examples illustrate the invention in more detail.

3030

Esimerkki 1Example 1

Seokseen, jossa oli 2500 ml tolueenia, 225 g (1,0 mol) 1,B-dihydroksi-9-antronia ja 232 ml (214 g, 2,0 mol) 35 2,6-dimetyylipyridiiniä, lisättiin alle 0°C lämpötilassa 3 66585 2 tunnin aikana 207 ml (213 g, 2,0 mol) voihappokloridia. Seosta sekoitettiin alle 0 C lämpötilassa lisäyksen jälkeen vielä kahden tunnin ajan.To a mixture of 2500 ml of toluene, 225 g (1.0 mol) of 1,2-dihydroxy-9-anthrone and 232 ml (214 g, 2.0 mol) of 2,6-dimethylpyridine were added below 0 ° C. 3,66585 207 mL (213 g, 2.0 mol) of butyric chloride over 2 hours. The mixture was stirred at a temperature below 0 ° C after the addition for a further two hours.

5 Seos lämmitettiin tämän jälkeen +40oC:een, 2,6-dimBtyylipyridiinin hydrokloridi suodatettiin pois ja pääosa tolueenista haihdutettiin pois alennetussa paineessa. Jäännökseen lisättiin 2300 ml isopropanolia, seos jäähdytettiin -10°C:een ja sakka otettiin talteen suodattamalla. Suori-10 tettiin uudelleenkiteytys ase tönitrii1 istä, jolloin saannoksi saatiin 222 g 1,8-dihydroksi-10-butyryyli-9-antronia. Tämä oli 75 % teoreettisesta.The mixture was then warmed to + 40 ° C, the 2,6-dimethylpyridine hydrochloride was filtered off and most of the toluene was evaporated off under reduced pressure. 2300 ml of isopropanol were added to the residue, the mixture was cooled to -10 ° C and the precipitate was collected by filtration. Recrystallization from acetonitrile was carried out to give 222 g of 1,8-dihydroxy-10-butyryl-9-anthrone. This was 75% of theory.

Esimerkki 2 15Example 2 15

Meneteltiin täysin analogisella tavalla kuin esimerkissä 1, mutta tolueenin sijasta käytettiin ksyleeniä. Saanto oli sama kuin esimerkissä 1 eli 75 %.The procedure was completely analogous to Example 1, but xylene was used instead of toluene. The yield was the same as in Example 1, i.e. 75%.

20 Esimerkki 320 Example 3

Seokseen, jossa oli 1200 ml tolueenia, 113 g (0,5 mol) 1.8- dihydroksi-9-antronia ja 116 ml (107 g, 1 mol) 2,6-dimetyylipyridiiniä lisättiin alle 0°C lämpötilassa noin 25 2 tunnin aikana 86,9 ml (92,5 g, 1 mol) propionyylikloridia.To a mixture of 1200 mL of toluene, 113 g (0.5 mol) of 1,8-dihydroxy-9-anthrone and 116 mL (107 g, 1 mol) of 2,6-dimethylpyridine was added below 0 ° C over about 2 hours 86 , 9 mL (92.5 g, 1 mol) of propionyl chloride.

Sekoittamista jatkettiin lisäyksen jälkeen vielä kaksi tun tia.Stirring was continued for another two hours after the addition.

Tuloksena saadun 1,B-dihydroksi-10-propionyyli-9-antronin 30 erottaminen suoritettiin esimerkissä 1 esitetyllä tavalla. Saanto oli (120 g) 82 % teoreettisesta.Separation of the resulting 1,2β-dihydroxy-10-propionyl-9-anthrone 30 was performed as described in Example 1. The yield (120 g) was 82% of theory.

Esimerkki 4 35 Lähtien 1,8~dihydroksi-9-antronista ja valeryylikloridista ja käyttäen valeryylikloridia 100 % ylimäärin, sekä menetellen muuten samoin kuin esimerkissä 1, saatiin tuloksena 1.8- dihy droksi - 10-valeryyli-9-antronia, jolloin saanto oli 53 %.Example 4 Starting from 1,8-dihydroxy-9-anthrone and valeryl chloride and using 100% excess valeryl chloride, and proceeding otherwise as in Example 1, 1,8-dihydroxy-10-valeryl-9-anthrone was obtained in 53% yield. .

Claims (3)

6658566585 1. Menetelmä erityisesti psoriasiksen hoitoon käytettävän 1,8-dihydroksi-10-asyyli-9-antronin, jonka kaava on 5 HO 0 OHA method of using 1,8-dihydroxy-10-acyl-9-anthrone of the formula 5 HO 0 OH, in particular for the treatment of psoriasis 10 COR jossa R on 2-4 hiiliatomia sisältävä aryyliryhmä, valmistamiseksi käyttäen lähtöaineena 1,8-dihydroksi-9-antronia, jonka kaava on 1 5 HO 0 OH [Qj^Jo) 20 ja happokloridia, jonka kaava on RC0C1, jossa R merkitsee samaa kuin yllä, tunnettu siitä, että reaktio suoritetaan tolueenissa, ksyleenissä tai klooratussa hiilivedyssä -10 - +20°C lämpötilassa, jolloin reaktio-25 seoksessa käytetään myös 2,6-dimetyylipyridiiniä.10 COR wherein R is an aryl group having 2 to 4 carbon atoms, starting from 1,8-dihydroxy-9-anthrone of the formula 15 HO 0 OH [Q 2 ^ Jo] 2 O and an acid chloride of the formula RCOCl, wherein R is same as above, characterized in that the reaction is carried out in toluene, xylene or a chlorinated hydrocarbon at a temperature of -10 to + 20 ° C, in which case 2,6-dimethylpyridine is also used in the reaction mixture. 2. Patenttivaatimuksen 1 mukainen menetelmä, tunnet-t u siitä, että happokloridia käytetään 100 %:n ylimäärä.Process according to Claim 1, characterized in that a 100% excess of acid chloride is used. 3. Patenttivaatimuksen 1 mukainen menetelmä, tunnet- t u siitä, että happokloridi lisätään kahden tunnin aikana ja että sekoitusta jatketaan vielä kaksi tuntia.Process according to Claim 1, characterized in that the acid chloride is added over a period of two hours and the stirring is continued for a further two hours.
FI831739A 1983-05-18 1983-05-18 FOERFARANDE FOER FRAMSTAELLNING AV SAERSKILT VID BEHANDLING AVSORIASIS ANVAENDBARA 1,8-DIHYDROXI-10-ACYL-9-ANTRONER FI66585C (en)

Priority Applications (31)

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
NZ207592A NZ207592A (en) 1983-05-18 1984-03-22 Method for the production of 1,8-dihydroxy-10-acyl-9-anthrone,and pharmaceutical compositions
AU25998/84A AU560079B2 (en) 1983-05-18 1984-03-22 1,8-dihydroxy-10-acyl-9-anthrones
IT20213/84A IT1173473B (en) 1983-05-18 1984-03-23 PROCEDURE FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTRONES, IN PARTICULAR FOR USE IN THE TREATMENT OF PSORIASIS
ZA842223A ZA842223B (en) 1983-05-18 1984-03-26 Method for the preparation of 1,8-dihydroxy-10-acyl-9-anthrones,especially for use in the treatment of psoriasis
IN209/CAL/84A IN156115B (en) 1983-05-18 1984-03-29
DK173584A DK154207C (en) 1983-05-18 1984-03-30 METHOD FOR PREPARING 1,8-DIHYDROXY-10-ACYL-9 ANTHRONS
GB08408666A GB2140007B (en) 1983-05-18 1984-04-04 1,8-dihydroxy-10-acyl-9-anthrones
NL8401074A NL8401074A (en) 1983-05-18 1984-04-04 PROCESS FOR PREPARING 1,8-DIHYDROXY-10-ACYL-9 ANTHRONES, ESPECIALLY FOR USE IN THE TREATMENT OF PSORIASIS.
IL71446A IL71446A (en) 1983-05-18 1984-04-05 Process for the preparation of 1,8-dihydroxy-10-alkanoyl-9-anthrones
BE0/212698A BE899334A (en) 1983-05-18 1984-04-05 PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES, PARTICULARLY FOR USE IN THE TREATMENT OF PSORIASIS.
IS2902A IS2902A7 (en) 1983-05-18 1984-04-05 Method for the preparation of 1,8-dihydroxy-10-acyl-9-anthrones, especially for the treatment of psoriasis
GR74318A GR79971B (en) 1983-05-18 1984-04-05
LU85292A LU85292A1 (en) 1983-05-18 1984-04-06 PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES, IN PARTICULAR FOR USE IN THE TREATMENT OF PSORIASIS
CS842911A CS256379B2 (en) 1983-05-18 1984-04-18 Method of 1,8-dihydroxy-10-acyl-9-anthrones production
ES531760A ES8505167A1 (en) 1983-05-18 1984-04-18 1,8-dihydroxy-10-acyl-9-anthrones
KR1019840002278A KR840009059A (en) 1983-05-18 1984-04-27 Manufacturing method of 1,8-dihydroxy-10-acyl-9-anthrones
FR8406790A 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
JP59090047A JPS59212443A (en) 1983-05-18 1984-05-04 Manufacture of 1,8-dihydroxy-10-acyl-9-anthrone
SU843735603A SU1240351A3 (en) 1983-05-18 1984-05-08 Method of producing 1,8-dioxy-10-acyl-9-anthrone
YU00817/84A YU81784A (en) 1983-05-18 1984-05-10 Process for making 1,8-dihydroxy-10-acyl-9-antrone, active against psoriasis
SE8402649A SE453827B (en) 1983-05-18 1984-05-16 PROCEDURE FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9 ANTRONES
PH30686A PH20038A (en) 1983-05-18 1984-05-16 A process for the preparation of 1,8-dihydroxy-10-acyl-9-anthrone
NO841965A NO157099C (en) 1983-05-18 1984-05-16 PROCESS FOR THE MANUFACTURE OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRON DERIVATIVES.
PL1984247724A PL141866B1 (en) 1983-05-18 1984-05-17 Method of obtaining 1,8-dihydroxy-10-ocyl-9-antrones
PT78603A PT78603B (en) 1983-05-18 1984-05-17 Process for preparing 1,8-dihidroxy-10-acyl-9-anthrones especially for use in the treatment of psoriasis
CH2431/84A CH659464A5 (en) 1983-05-18 1984-05-17 METHOD FOR PRODUCING 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES.
HU841908A HUT36076A (en) 1983-05-18 1984-05-17 Improved process for production of 1,8-dihidroxi-10-acil-9-antrons
DE19843418382 DE3418382A1 (en) 1983-05-18 1984-05-17 METHOD FOR THE PRODUCTION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES
CA000454593A CA1212943A (en) 1983-05-18 1984-05-17 Method for the preparation of 1,8-dihydroxy-10-acyl-9- anthrones, especially for use in the treatment of psoriasis
DD84263131A DD223702A5 (en) 1983-05-18 1984-05-17 PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES

Applications Claiming Priority (2)

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
FI831739 1983-05-18

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FI831739A0 FI831739A0 (en) 1983-05-18
FI66585B FI66585B (en) 1984-07-31
FI66585C true FI66585C (en) 1984-11-12

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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)

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* Cited by examiner, † Cited by third party
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
DE69223723T2 (en) * 1991-10-04 1998-04-16 Fisher & Paykel humidifier
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

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI57743C (en) * 1979-03-29 1980-10-10 Orion Yhtymae Oy FREQUENCY REQUIREMENT FOR NYA 1,8-DIHYDROXI-10-ACYL-9-ANTRONER MOT PSORIASIS

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AU2599884A (en) 1984-11-22
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IL71446A (en) 1987-01-30
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ES531760A0 (en) 1985-05-16
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BE899334A (en) 1984-07-31
FR2546162A1 (en) 1984-11-23
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CS256379B2 (en) 1988-04-15
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FI831739A0 (en) 1983-05-18
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IT1173473B (en) 1987-06-24
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CS291184A2 (en) 1987-08-13
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AU560079B2 (en) 1987-03-26
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GB2140007B (en) 1986-04-09
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GB2140007A (en) 1984-11-21

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