专利摘要:
The invention relates to a method for the preparation of 1,8-dihydroxy-10-acyl-9-anthrones, especially for use in the treatment of psoriasis, having the formula: <IMAGE> where R is an alkyl group having 2-4 carbon atoms, by using as the initial material, 1,8-dihydroxy-9-anthrone and an acid chloride having the formula RCOC2, where R represents the same as above. In accordance with the invention, harmful benzene is replaced with, for example toluene; this replacing is possible because pyridine is replaced with 2,6-dimethyl pyridine.
公开号:SU1240351A3
申请号:SU843735603
申请日:1984-05-08
公开日:1986-06-23
发明作者:Юхани Каирисало Пекка;Килликки Пиппури Айно;Юхани Хонканен Эркки
申请人:Орион-Ихтюмя Ой (Фирма);
IPC主号:
专利说明:

This invention relates to a process for the preparation of 1 .b-dioxy-10-acyl-2-anti-rna for the treatment of psoriasis. 1,8-Dioxy-9-anthron, substituted at position 10, has been used for a number of years instead of ditraion, which has been known since 1916 and has been used to treat psoriasis, but it strongly paints the skin and has a strong skin irritant.
. The aim of the invention is to increase the yield of the target product.
Example 1 Butyryl chloride in the amount of 207 MP (213 g, 2.0 mol (100% I3; excess) is added over two hours to a mixture containing 2500 ml of toluene, 226 g (1.0 mol), 1 , 8-dioxy-9-anthron and 232 ml (214 g 2.0 mol) 2,: 6-diketipyridine, keeping the reaction temperature below 0 ° C. After that, the reaction mixture is stirred at a temperature below for another two hours.
The mixture is then heated to 40 ° C, the hydrochloride 2, b of dimethylpyridine is filtered off, and the bulk of the toluene is removed under iris pressure. 2300 ml of isopropanol are added to the residue, the mixture is cooled to -lO c, the precipitated precipitate is filtered off. Recrystallization from acetonitrile is carried out, resulting in 222: g of 1,8-dioxy-10-butyrch-9-anthro. This is 75% of theoretical yield.
Example 2: Reaction procedure. completely analogous
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described in example 1, but xylene is used instead of toluene. The reaction yield is the same as in example 1, i.e. 75%.
Example 3. Chloride propio NIL in the amount of 86.9 ml (92.5 g
1 mol) - 100% excess - for
2 h, at a temperature below, are added to a mixture containing 1200 ml of toluene, 113 g (0.5 mol) of 1,8-dioxy-9-anthrone and 116 ml (107 g, 1) of 2,6-dimethylpyridine. Then stirred for another two hours.
The result is 1,8-dioxyl-. The -10-propionyl-9-anthron, which is separated as in Example 1. The yield is (120 kg) 82% of the result. retic.
Example 4. Based on the same 8-DIOXI-9-anthron and acid chloride valery of a new acid and using a 100% excess of lerite acid chloride using the same procedure as described in Example 1, 1,8-DIOXY is obtained -10-valerial-9-anthron, the reaction yield is 53%.
Example 5. The procedure of Example 1 is repeated, but dichloromethane is used as the solvent. Yield 68% of theoretical.
Example 6. The procedure of Example 1 is repeated, but the reaction temperature is increased to. The yield of 66% of theory.
Example 7. The procedure of Example 1 is repeated, but 1,2g-dichloroethane is used as a solvent. .Outlet 67% of theories.
权利要求:
Claims (2)
[1]
METHOD FOR PRODUCING 1,8-DIOXY-10-Acyl-9-ANTHROA of the general formula he is about he is where n is an alkyl group containing
[2]
2-4 carbon atoms, by reaction of 1.8 h-dihydroxy-9-AnTrop of formula with a carboxylic acid chloride. general formula
R СОС1 where R - has the indicated meaning; in the presence of an organic amine in a solvent medium; I mean that, in order to increase the yield of the target product, 2,6-dimethylpyridine is used as an organic amine, and toluene, xylene or chlorinated hydrocarbons, such as dichloromethane, dichloroethane, are used as a solvent, and the process is carried out at a temperature from - 10 to + 20 ° C with a 100% excess of carboxylic acid chloride.
SIU 1240351 AZ
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引用文献:
公开号 | 申请日 | 公开日 | 申请人 | 专利标题

FI57743C|1979-03-29|1980-10-10|Orion Yhtymae Oy|FREQUENCY REQUIREMENT FOR NYA 1,8-DIHYDROXI-10-ACYL-9-ANTRONER MOT PSORIASIS|FR2492372B1|1980-10-21|1983-07-18|Cird|
US4843097A|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|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|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|
FR2591222B1|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|
DE69223723T2|1991-10-04|1998-04-16|Fisher & Paykel|humidifier|
DE4231636A1|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|1993-07-19|1995-06-20|Teva Pharmaceutical Industries, Ltd.|10-substituted 1,8-dihydroxy-9 anthracenone pharmaceuticals|
法律状态:
优先权:
申请号 | 申请日 | 专利标题
FI831739A|FI66585C|1983-05-18|1983-05-18|FOERFARANDE FOER FRAMSTAELLNING AV SAERSKILT VID BEHANDLING AVSORIASIS ANVAENDBARA 1,8-DIHYDROXI-10-ACYL-9-ANTRONER|
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