SE453827B - PROCEDURE FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9 ANTRONES - Google Patents
PROCEDURE FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9 ANTRONESInfo
- Publication number
- SE453827B SE453827B SE8402649A SE8402649A SE453827B SE 453827 B SE453827 B SE 453827B SE 8402649 A SE8402649 A SE 8402649A SE 8402649 A SE8402649 A SE 8402649A SE 453827 B SE453827 B SE 453827B
- Authority
- SE
- Sweden
- Prior art keywords
- dihydroxy
- anthron
- acyl
- procedure
- preparation
- Prior art date
Links
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)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
827 2 Ovanstående fördelar uppnås enligt det förfarande vars kännetecken anges i bifogade kravet 1. 827 2 The above advantages are achieved according to the process the characteristics of which are set out in appended claim 1.
Uppfinningen bygger på iakttagelsen att ett utbyte av pyridin mot 2,6~dimetylpyridin gör det möjligt att sänka reaktionstemperaturen, att använda toluen, xylen eller klorerade kolväten såsom diklorometan eller tetrakloroeten istället för bensen, och att till och med tredubbla utby- tet jâmfört med den kända metoden. Om vidare syrakloriden användes i ett överskott av 100% kan reaktionen vara avslu- tad inom 2 timmar.The invention is based on the observation that an exchange of pyridine for 2,6-dimethylpyridine makes it possible to lower the reaction temperature, to use toluene, xylene or chlorinated hydrocarbons such as dichloromethane or tetrachloroethylene instead of benzene, and even to triple the yield compared with the known method. Furthermore, if the acid chloride is used in an excess of 100%, the reaction may be completed within 2 hours.
Den ovan angivna låga reaktionstemperaturen, som till exem- pel kan vara -10°C till +20°C, medför att mängden förore- ningar som gâr in i den färdiga 1,8-dihydroxi-10-acyl-9- antronen är liten. Reningen är således ett enkelt förfa- rande jämfört med motsvarande förfarande i den kända meto- den. Acetonitril eller 2-propanol är lämpliga att använda som omkristalliseringslösningsmedel tillsammans med eller istället för ättiksyra.The above-mentioned low reaction temperature, which may be -10 ° C to + 20 ° C, for example, means that the amount of impurities entering the finished 1,8-dihydroxy-10-acyl-9-anthron is small. . The purification is thus a simple procedure compared with the corresponding procedure in the known method. Acetonitrile or 2-propanol are suitable for use as recrystallization solvent together with or instead of acetic acid.
Föreningarna som framställts enligt uppfinningen kan använ- das i till exempel vaselin- eller paraffinbaserade hudkrämer i koncentrationer av 0,5-5%, i stänger avsedda för hudvård i koncentrationer av till exempel 2-8%, och i geler och i filmbildande lösningar.The compounds prepared according to the invention can be used in, for example, Vaseline or paraffin-based skin creams in concentrations of 0.5-5%, in rods intended for skin care in concentrations of, for example, 2-8%, and in gels and in film-forming solutions.
Uppfinningen åskådliggöres närmare genom följande exempel.The invention is further illustrated by the following examples.
Exempel 1 Butyrylklorid i en mängd av 207 ml (213 g, 2,0 mol) sattes inom loppet av 2 timmar vid en temperatur under OOC till en blandning som innehöll 2500 ml toluen, 226 g (1,0 mol) 1,8-dihydroxi-9-antron och 232 ml (214 g, 2,0 mol) 2,6- dimetylpyridin. 3 453 827 Blandningen omrördes vid en temperatur under 0°C i ytter- ligare två timmar efter tillsatsen.Example 1 Butyryl chloride in an amount of 207 ml (213 g, 2.0 mol) was added within 2 hours at a temperature below 0 ° C to a mixture containing 2500 ml of toluene, 226 g (1.0 mol) of 1.8 dihydroxy-9-anthron and 232 ml (214 g, 2.0 mol) of 2,6-dimethylpyridine. The mixture was stirred at a temperature below 0 ° C for a further two hours after the addition.
Blandningen upphettades därefter till +40°C, vätekloriden av 2,6-dimetylpyridin avfiltrerades och huvuddelen av tolue- nen avdunstades vid reducerat tryck. 2300 ml isopropanol sattes till återstoden, blandningen kylaes till -1o°c een fällningen återvanns genom filtrering. Omkristallisation utfördes ur acetonitril, varigenom erhölls ett utbyte av 222 g 1,8-dihydroxi-10-butyryl-9-antron. Detta var 75% av det teoretiska värdet.The mixture was then heated to + 40 ° C, the hydrochloride of 2,6-dimethylpyridine was filtered off and most of the toluene was evaporated under reduced pressure. 2300 ml of isopropanol were added to the residue, the mixture was cooled to -10 ° C and the precipitate was recovered by filtration. Recrystallization was carried out from acetonitrile to give 222 g of 1,8-dihydroxy-10-butyryl-9-anthron. This was 75% of the theoretical value.
Exempel 2 Förfarandet var fullständigt analogt med det i exempel 1, förutom att xylen användes istället för toluen. Utbytet var detsamma som i exempel 1, dvs. 75%.Example 2 The procedure was completely analogous to that of Example 1, except that xylene was used instead of toluene. The yield was the same as in Example 1, i.e. 75%.
Exempel 3 Propionylklorid i en mängd av 86,9 ml (92,5 g, 1 mol) sat- tes inom loppet av cirka två timmar vid en temperatur under o°c till en blandning som innehöll 1200 ml tolnen, 113 g (0,5 mol) 1,8-dihydroxi-9-antron och 116 ml (107 g, 1 mol) 2,6-dimetylpydirin. Omröringen fortsattes i ytterligare tvâ timmar efter tillsatsen. 1,8-dihydroxi-10-propionyl-9-antron som erhölls som slut- produkt separerades genom förfarandet som angivits i exempel 1. Utbytet var 82% (120 g) av det teoretiska värdet.Example 3 Propionyl chloride in an amount of 86.9 ml (92.5 g, 1 mol) was added within about two hours at a temperature below 0 ° C to a mixture containing 1200 ml of toluene, 113 g (0, 5 mol) 1,8-dihydroxy-9-anthron and 116 ml (107 g, 1 mol) 2,6-dimethylpydirine. Stirring was continued for another two hours after the addition. The 1,8-dihydroxy-10-propionyl-9-anthron obtained as a final product was separated by the procedure set forth in Example 1. The yield was 82% (120 g) of the theoretical value.
Exempel 4_ Om man utgår från 1,8-dihydroxi-9-antron och valerylklorid, varvid valerylklorid användes i ett överskott av 100%, och för övrigt förfar så som i exempel 1 erhölls 1,8-dihydroxi- -valeryl-9-antron i ett utbyte av 53%. 453 827 Exemgel 5 Farmaceutiska kompositioner framställdes genom användning av följande beståndsdelar och mängder: flytande paraffin 40 - 60 % fast paraffin 40 - 60 % mikrokristallint vax 0,5 - 5 % Vidare blandades cirka 2-8% 1,8-dihydroxi-10-butyryl-9- antron med den ovan angivna bärarkompositionen. Stänger avsedda för hudvård formades av blandningen, och man noterade att användningsegenskaperna hos stängerna var goda och att vidare läkemedlet i stängerna förblev oför- ändrat, speciellt icke oxiderat. ÄExample 4 - Starting from 1,8-dihydroxy-9-anthron and valeryl chloride, valeryl chloride being used in an excess of 100%, and otherwise proceeding as in Example 1, 1,8-dihydroxy -valeryl-9-anthron was obtained in a yield of 53%. 453 827 Exemgel 5 Pharmaceutical compositions were prepared using the following ingredients and amounts: liquid paraffin 40 - 60% solid paraffin 40 - 60% microcrystalline wax 0.5 - 5% Furthermore, about 2-8% 1,8-dihydroxy-10- were mixed. butyryl-9-anthron with the above carrier composition. Rods intended for skin care were formed from the mixture, and it was noted that the use properties of the rods were good and that furthermore the drug in the rods remained unchanged, especially not oxidized. Ä
Claims (4)
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 (3)
| Publication Number | Publication Date |
|---|---|
| SE8402649D0 SE8402649D0 (en) | 1984-05-16 |
| SE8402649L SE8402649L (en) | 1984-11-19 |
| SE453827B true SE453827B (en) | 1988-03-07 |
Family
ID=8517222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8402649A SE453827B (en) | 1983-05-18 | 1984-05-16 | PROCEDURE FOR THE PREPARATION OF 1,8-DIHYDROXY-10-ACYL-9 ANTRONES |
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) | ES531760A0 (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 GB GB08408666A patent/GB2140007B/en not_active Expired
- 1984-04-04 NL NL8401074A patent/NL8401074A/en not_active Application Discontinuation
- 1984-04-05 IS IS2902A patent/IS2902A7/en 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 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/ES531760A0/en active Granted
- 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 PH PH30686A patent/PH20038A/en unknown
- 1984-05-16 NO NO841965A patent/NO157099C/en unknown
- 1984-05-17 PT PT78603A patent/PT78603B/en unknown
- 1984-05-17 CH CH2431/84A patent/CH659464A5/en not_active IP Right Cessation
- 1984-05-17 DD DD84263131A patent/DD223702A5/en unknown
- 1984-05-17 CA CA000454593A patent/CA1212943A/en not_active Expired
- 1984-05-17 DE DE19843418382 patent/DE3418382A1/en not_active Withdrawn
- 1984-05-17 PL PL1984247724A patent/PL141866B1/en unknown
- 1984-05-17 HU HU841908A patent/HUT36076A/en unknown
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| NUG | Patent has lapsed |
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