DD223702A5 - PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES - Google Patents
PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES Download PDFInfo
- Publication number
- DD223702A5 DD223702A5 DD84263131A DD26313184A DD223702A5 DD 223702 A5 DD223702 A5 DD 223702A5 DD 84263131 A DD84263131 A DD 84263131A DD 26313184 A DD26313184 A DD 26313184A DD 223702 A5 DD223702 A5 DD 223702A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dihydroxy
- acyl
- acid chloride
- anthrones
- anthrone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims abstract description 10
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 229950011008 tetrachloroethylene Drugs 0.000 claims 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 201000004681 Psoriasis Diseases 0.000 description 2
- 229960002311 dithranol Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
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
Landscapes
- 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)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1,8-Dihydroxy-10-acyl-9-anthrone werden hergestellt, indem man 1,8-Dihydroxy-9-anthron mit einem Saeurechlorid in Gegenwart von 2,6-Dimethylpyridin umsetzt.1,8-Dihydroxy-10-acyl-9-anthrones are prepared by reacting 1,8-dihydroxy-9-anthrone with an acid chloride in the presence of 2,6-dimethylpyridine.
Description
Titel der Erfindung: . - . Title of the invention :. -.
Verfahren zur Herstellung von l,8-Dihydroxy-10-acyl-9-anthronen .Process for the preparation of l, 8-dihydroxy-10-acyl-9-anthrones.
Die Anwendung der vorliegenden Erfindung erfolgt auf dem Gebiet der Herstellung von L,8-Diyhdroxy-10-acyl-9-anthronen. ·The application of the present invention is in the field of production of L, 8-dihydroxy-10-acyl-9-anthrones. ·
Charakteristik der bekannten technischen Lösungen: Characteristic of the known technical solutions :
Die in der 10-Stellung substituierten 1,8-Dihydroxy-9-anthrone sind seit einigen Jahren als Ersatz von Dithranol verwendet worden, das seit 1916 . bekannt ist und zur Behandlung von Psoriasis verwendet wurde und das Haut und Kleidung stark fleckig macht 'und die Haut stark entzündet.The substituted in the 10-position, 1,8-dihydroxy-9-anthrones have been used for some years as a replacement of dithranol, since 1916. is known and used to treat psoriasis and makes the skin and clothing heavily stained 'and the skin is highly inflamed.
Die Strukturformel der l,8-Dihydroxy-10-acyl-9-anthrone ist wie folgt:The structural formula of the l, 8-dihydroxy-10-acyl-9-anthrone is as follows:
HO 0 OHHO 0 OH
O=C-R . . . ..O = C-R. , , ..
in welcher R eine Alkylgruppe mit 2 bis 4 Kohlenstoffatomen'ist. Die Verbindungen sind gemäß der FI-PS 57743 hergestellt worden, indem man Anthralin in siedendem Benzol mit einem Säurechlorid in Anwesenheit von Pyridin reagieren läßt. Das Säurechlorid wird in einem Überschuß von 20 % verwendet. Die Reaktionsmischung wird -unter Rückfluß 10 Stunden zum Sieden erhitzt,' und das Produkt wird aus Essigsäure kristallisiert. Die Ausbeute dieses Verfahrens beträgt jedoch nur z.3. 25,5 % d.Th.in which R is an alkyl group having 2 to 4 carbon atoms. The compounds were prepared according to FI-PS 57743 by reacting anthralin in boiling benzene with an acid chloride in the presence of pyridine. The acid chloride is used in an excess of 20%. The reaction mixture is refluxed for 10 hours, and the product is crystallized from acetic acid. However, the yield of this method is only z.3. 25.5% of theory
Ziel der Erfindung: Object of the invention :
•Ziel der Erfindung ist ein verbessertes Verfahren Z1Or Herstellung von 1,8-The object of the invention is an improved process Z 1 Or production of 1,8-
Dihydroxy-lQ-acyl-9-anthronen. ' .Dihydroxy-IQ-acyl-9-anthrones. '.
Darlegung des Wesens der Erfindung: : .', . Presentation of the essence of the invention :.
Der Erfindung liegt die Aufgabe zugrunde., l,8-Dihydro-10-acYl-9-anthrone in höheren Ausbeuten als gemäß-der FI-PS 57743 herzustellen. So kann die Ausbeute auf das Zwei- bis Dreifache erhöht werden. Außerdem kann bei niedrigen, Reaktionstemperaturen, z.B. nur -100C, gearbeitet werden. Die Anwendung von nur Raumtemperatur ist ebenfalls geeignet. Weiterhin kann auf die Verwendung von Benzol, das karzinogen ist, verzichtet und das weniger schädliche Toluol eingesetzt werden.The invention is based on the object., L, 8-dihydro-10-acyl-9-anthrones in higher yields than according to the FI-PS 57743 produce. Thus, the yield can be increased to two to three times. In addition, you can work at low, reaction temperatures, for example, only -10 0 C. The application of only room temperature is also suitable. Furthermore, the use of benzene, which is carcinogenic, can be dispensed with and the less harmful toluene can be used.
Die Erfindung betrifft ein Verfahren zur Herstellung von 1,8-DihydroxylO-acyl-9-anthronen der folgenden Formel:The invention relates to a process for the preparation of 1,8-dihydroxyl-O-acyl-9-anthrones of the following formula:
HO Ö QH .HO Ö QH.
' . O=C-R '. O = C-R
in welcher R für eine Alkylgruppe mit.;2 bis.4 Kohlenstoffatomen steht, durch Umsetzung von :l,8-Dihydroxy-9-anthron der Formel: in which R is an alkyl group having .2 to 4 carbon atoms, by reacting: 1,8-dihydroxy-9-anthrone of the formula:
HQ- Q; pH' . ' : . ' . ,: Z^-HQ-Q ; pH '. ':. '. , : Z ^ -
einem Säurechlorid der Formel RCOCfI, in welcher R dieselbe Bedeutung wie oben hat, das dadurch gekennzeichnet ist, daß in der Reaktionsmischung 2,6-Dimethylpyridin verwendet wird. . · .. ' ' '. ' ·an acid chloride of the formula RCOCfI, in which R has the same meaning as above, which is characterized in that 2,6-dimethylpyridine is used in the reaction mixture. , · .. '' '. '·
Bevorzugte Lösungsmittel sind Toluol, Xylol oder chlorierte7Kohlenwasserstoffe, wie Dichlormethan oder Tetraghlofethen. Vorzugsweise -verwendet man das Säurechlorid in einem Überschuß.bis zu 100 %. Bei.einem' 100' %-igen·: Überschuß an Säurechlorid kann die Reaktion in 2 Stunden beendet-werden. Es wird bevorzugt die Reaktion bei -10 bis 2O0C durchzuführen,'wobei' man das Säurechlorid im Verlauf von.2 Stunden zufügt und dann noch 2 Stunden weitergerührt wird. ' · .Preferred solvents are toluene, xylene or chlorinated 7 hydrocarbons, such as dichloromethane or Tetraghlofethen. Preferably, the acid chloride is used in excess. Up to 100%. Bei.einem '100'% strength ·: excess of acid chloride, the reaction-be finished in 2 hours. It is preferred to carry out the reaction at -10 to 2O 0 C, 'wherein' adding the acid chloride in the course of 2 hours and then stirring is continued for 2 hours. '·.
Aufgrund der oben genannten niedrigen -Reaktionstemperatur ist die Menge an Verunreinigungen, die in das fertige l,8-DihydroxvT-10-acyl-9-anthron eingehen, gering. Daher ist die Reinigung im Vergleich zum bekannten Verfahren einfach. Acetonitril oder 2-Propanol sind zur Verwendung als ümkristalli-Due to the above-mentioned low reaction temperature, the amount of impurities entering the final l, 8-dihydroxy T -10-acyl-9-anthrone is low. Therefore, the cleaning is easy compared to the known method. Acetonitrile or 2-propanol are for use as supracrystalline
_ 3 sationslösungsmittel zusammen mit oder anstelle von Essigsäure geeignet.3 tion solvents together with or instead of acetic acid.
Die erfindungsgemäß hergestellten Verbindungen können z.B. in Hautcremes auf Vaselin- oder Paraffinbasis in Konzentrationen von 0,5 bis 5 %, in zur Hautpflege bestimmten Stiften in Konzentrationen z.B. von 2 bis 8 % und in Gelen und fumbildenden Lösungen verwendet werden. Die erfindungsgemäß hergestellten Verbindungen sind besonders zur Behandlung von Psoriasis geeignet. ' ' . .The compounds prepared according to the invention may e.g. in vaseline or paraffin based skin creams in concentrations of 0.5 to 5%, in sticks intended for skin care in concentrations e.g. from 2 to 8% and used in gels and fumishing solutions. The compounds according to the invention are particularly suitable for the treatment of psoriasis. ''. ,
ι ι
Die folgenden Ausführungsbeispiele veranschaulichen die Erfindung im Detail. ·The following embodiments illustrate the invention in detail. ·
Ausführungsbeispiele:EXAMPLES '' \ '' \
Butyrylchlorid in einer Menge von 207 ml (213 g 2,0 Mol) wurde im Verlauf von 2 h bei einer Temperatur unter 00C zu einer Mischung zugefügt, die 2500 ml Toluol, 226 g (1,0 Mol) l,8-Dihydroxy-9-anthron und 232^ ml (214 g, 2,0 Mol) 2,6-Dimethylpyridin enthielt. Butyryl chloride in an amount of 207 ml (213 g 2.0 mol) was added over 2 hours at a temperature below 0 0 C to a mixture containing 2500 ml of toluene, 226 g (1.0 mol) l, 8- Dihydroxy-9-anthrone and 232 ^ ml (214 g, 2.0 mol) of 2,6-dimethylpyridine.
Die Mischung wurde nach'der Zugabe weitere 2 h bei einer Temperatur unter 00C gerührt. -The mixture was stirred after 'additional 2 h at a temperature below 0 0 C for. -
• Danach wurde die Mischung auf +400C erwärmt, das Hydrochloric des 2,6-Diinethylpyridins wurde abfiltriert, und der größte Teil des ToIuoIs wurde bei vermindertem Druck abgedampft. 2300 ml Isopropanol wurden zum Rückstand zugefügt, die Mischung wurde auf -1O0C abgekühlt, und der Niederschlag wurde durch Filtration gewonnen. Die Umkrista,!!isation erfolgte aus Acetonitril, wodurch man eine Ausbeute von 222 g l>8-Dihydroxy-10-butvryl-9^anthr.on erhielt. Dies entsprach 75 % d.Th. '• Then the mixture to +40 0 C was heated, the Hydrochloric of 2,6-Diinethylpyridins was filtered, and most of the ToIuoIs was evaporated under reduced pressure. 2300 ml of isopropanol was added to the residue, the mixture was cooled to -1O 0 C, and the precipitate was recovered by filtration. The reaction was carried out from acetonitrile to give a yield of 222 g of 8-dihydroxy-10-butyryl-9H-anthron. This corresponded to 75% of the theoretical value. '
Beispiel 2 ' Example 2 '
Das Verfahren_entsprach Beispiel 1, wobei jedoch anstelle von Toluol Xylol verwendet wurde. Die Ausbeute war dieselbe wie in Beispiel 1, d.h. 75 %.' 'The procedure was analogous to Example 1 except that xylene was used instead of toluene. The yield was the same as in Example 1, i. 75%. ' '
Pröpionylchlorid in einer Menge von 86,9 ml (92,5 g, 1 Mol) wurde im Verlauf von etwa 2 h bei einer Temperatur unter O0C zu einer Mischung zugefügt, die 1200 ml Toluol, 113 g (0,5 Mol) 1,8-DLhydroxy-9-anthron und . 116 ml (107 g, 1 Mol) 2,6-Dimethylpyridin enthielt. Das Rühren wurde nach der Zugabe weitere 2 h fortgesetzt.Propionyl chloride in an amount of 86.9 ml (92.5 g, 1 mol) was added over about 2 hours at a temperature below 0 ° C. to a mixture containing 1200 ml of toluene, 113 g (0.5 mol). 1,8-DL-hydroxy-9-anthrone and. 116 ml (107 g, 1 mol) of 2,6-dimethylpyridine contained. Stirring was continued for an additional 2 hours after the addition.
Das so erhaltene. l78-Dihydrc«y--10-prGpipnyl-9-anthron wurde nach dem in Beispiel 1 dargestellten Verfahren abgetrennt. Die Ausbeute betrug : (120 g) 82 % d.Th.The thus obtained. l 7 8-Dihydrc "y - 10 prGpipnyl-9-anthrone was separated according to the example shown in Example 1. The yield was: (120 g) 82% of theory
Be i spie 1 4Be i spie 1 4
Ausgehend von 1,8-Dihydroxy-9-anthron und Valerylchlorid und unter Verwendung, von Valerylchlorid in,einem Überschuß von 100 % erhielt, man nach dem Verfahren von Beispiel 1 l,8-Dihydroxy-10-valeryl-9-anthron, wobei die Ausbeute 53 % betrug. . ' ..- Starting from 1,8-dihydroxy-9-anthrone and valeryl chloride and using, in excess of 100%, valeryl chloride, one obtained, by the method of Example 1, l, 8-dihydroxy-10-valeryl-9-anthrone, wherein the yield was 53%. , '..-
Verwendung der erfindungsgemäß hergestellten Verbindungen: Unter Verwendung der folgenden Bestandteile und Mengen wurden pharmazeutische Zusammensetzungen hergestellt: Use of the Compounds Prepared According to the Invention: Using the following ingredients and amounts, pharmaceutical compositions were prepared:
flüssiges Paraffin . > 40 bis 60 % ; .liquid paraffin. > 40 to 60%; ,
festes Paraffin . . : . '40 bis 60 %solid paraffin. , :. '40 to 60%
mikrokristallines Wachs . 0,5 bis 5 % .- . ,microcrystalline wax. 0.5 to 5% .-. .
Weiterhin wurden etwa 2 bis 8 % l,8-Dihydroxy-lÖ^butyryl-9-anthron mit der oben dargestellten Trägerzusanrnensetzung gemischt. Aus der Mischung wurden für die Hautpflege bestirrmte Stifte geformt; es wurde festgestellt, daß die Verwendungseigenschaf ten der Stifte gut'war und daß das Arzneimittel in den Stiften unverändert, insbesondere unoxidiert, blieb. Further, about 2 to 8% of l, 8-dihydroxy-lÖ-butyryl-9-anthrone was mixed with the carrier composition set forth above. From the mixture were molded for the skin care messy pins; it was noted that the use properties of the sticks were good and that the drug remained unchanged in the sticks, especially unoxidized.
Claims (2)
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 (1)
| Publication Number | Publication Date |
|---|---|
| DD223702A5 true DD223702A5 (en) | 1985-06-19 |
Family
ID=8517222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84263131A DD223702A5 (en) | 1983-05-18 | 1984-05-17 | PROCESS FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9-ANTHRONES |
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 |
| 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 |
| 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 |
| 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 |
Family Cites Families (1)
| 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 |
-
1983
- 1983-05-18 FI FI831739A patent/FI66585C/en not_active IP Right Cessation
-
1984
- 1984-03-22 AU AU25998/84A patent/AU560079B2/en not_active Ceased
- 1984-03-22 NZ NZ207592A patent/NZ207592A/en unknown
- 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 NL NL8401074A patent/NL8401074A/en not_active Application Discontinuation
- 1984-04-04 GB GB08408666A patent/GB2140007B/en not_active Expired
- 1984-04-05 BE BE0/212698A patent/BE899334A/en not_active IP Right Cessation
- 1984-04-05 IL IL71446A patent/IL71446A/en not_active IP Right Cessation
- 1984-04-05 IS IS2902A patent/IS2902A7/en unknown
- 1984-04-05 GR GR74318A patent/GR79971B/el 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 Withdrawn
- 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 PH PH30686A patent/PH20038A/en unknown
- 1984-05-16 SE SE8402649A patent/SE453827B/en not_active IP Right Cessation
- 1984-05-16 NO NO841965A patent/NO157099C/en unknown
- 1984-05-17 CA CA000454593A patent/CA1212943A/en not_active Expired
- 1984-05-17 PT PT78603A patent/PT78603B/en unknown
- 1984-05-17 DD DD84263131A patent/DD223702A5/en unknown
- 1984-05-17 HU HU841908A patent/HUT36076A/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 CH CH2431/84A patent/CH659464A5/en not_active IP Right Cessation
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