CS256379B2 - Method of 1,8-dihydroxy-10-acyl-9-anthrones production - Google Patents
Method of 1,8-dihydroxy-10-acyl-9-anthrones production Download PDFInfo
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- CS256379B2 CS256379B2 CS842911A CS291184A CS256379B2 CS 256379 B2 CS256379 B2 CS 256379B2 CS 842911 A CS842911 A CS 842911A CS 291184 A CS291184 A CS 291184A CS 256379 B2 CS256379 B2 CS 256379B2
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- dihydroxy
- acyl
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- anthrones
- acid chloride
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- 238000000034 method Methods 0.000 title claims abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 27
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical group CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 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 8
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 201000004681 Psoriasis Diseases 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- AHZXFRRDQXXPJD-UHFFFAOYSA-N 10-butanoyl-1,8-dihydroxy-10h-anthracen-9-one Chemical compound C1=CC=C2C(C(=O)CCC)C3=CC=CC(O)=C3C(=O)C2=C1O AHZXFRRDQXXPJD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- VQTRJTVHFJIZMI-UHFFFAOYSA-N 1,2-dihydroxy-10h-anthracen-9-one Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3CC2=C1 VQTRJTVHFJIZMI-UHFFFAOYSA-N 0.000 description 1
- KRTYVWKREPCSNP-UHFFFAOYSA-N 1,8-dihydroxy-10-propanoyl-10h-anthracen-9-one Chemical compound C1=CC=C2C(C(=O)CC)C3=CC=CC(O)=C3C(=O)C2=C1O KRTYVWKREPCSNP-UHFFFAOYSA-N 0.000 description 1
- SUJBUFGFNUEIRB-UHFFFAOYSA-N 2,6-dimethylpyridin-1-ium;chloride Chemical compound Cl.CC1=CC=CC(C)=N1 SUJBUFGFNUEIRB-UHFFFAOYSA-N 0.000 description 1
- 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
- 229960002311 dithranol Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 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
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation 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
- 238000000746 purification Methods 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002792 vascular Effects 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
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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)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Vynález se týká způsobu výroby 1,8-dihydroxy-10-acyl-9-anthronů.The present invention relates to a process for the preparation of 1,8-dihydroxy-10-acyl-9-anthrons.
l,8-dihydroxy-9-anthrony·substituované v poloze 10 se používají po dobu několika málo let к náhradě dithranolu, který je znám od.roku 1916 a je používán к léčbě psoriázy a který intenzívně zbarvuje pokožku a oděv a má silně zánětlivý účinek na pokožku.1,8-dihydroxy-9-anthrones substituted in position 10 are used for a few years to replace dithranol, known since 1916 and used to treat psoriasis, which intensely stains skin and clothing and has a highly inflammatory effect on the skin.
1,8-dihydroxy-10-acyl-9-anthrony, jejichž výroby se-vynález týká, mají obecný vzorec IThe 1,8-dihydroxy-10-acyl-9-anthrones of the present invention have the general formula I
(I) kde R značí alkylovou skupinu se 2 až 4 atomy uhlíku. Tyto sloučeniny byly připraveny podle finského patentového spisu č. 57 743 reakčí anthralinu s příslušným chloridem kyseliny ve vroucím benzenu za přítomnosti pyridinu. Chloridu kyseliny se používá v nadbytku 20 %.(I) wherein R represents a C 2 -C 4 alkyl group. These compounds were prepared according to Finnish Patent 57,743 by reacting anthraline with the appropriate acid chloride in boiling benzene in the presence of pyridine. The acid chloride is used in an excess of 20%.
Reakční směs se vaří pod zpětným chladičem·, po dobu 10 hodin a produkt se krystalizuje z kyseliny octové. Výtěžek tohoto způsobu bývá například jen 25,5 % teorie.The reaction mixture is refluxed for 10 hours and the product is crystallized from acetic acid. The yield of this method is, for example, only 25.5% of theory.
Nyní byl nalezen způsob, kterým je možno dosáhnout četných výhod. Reakční teplotu lze snížit až na -10 °C, a v každém případě je možné používat velice nízkých reakčních teplot, například teploty místnosti. Kromě toho je možné vyhnout se použití benzenu, který je významně karcinogenní, a používat například toluenu, který je méně škodlivý. Dále lze zvýšit výtěžek na dvojnásobek až trojnásobek ve srovnání s postupem podle finského patentového spisu č. 57 743.We have now found a way in which numerous advantages can be achieved. The reaction temperature can be lowered to -10 ° C, and in any case very low reaction temperatures, such as room temperature, can be used. In addition, it is possible to avoid the use of benzene, which is significantly carcinogenic, and to use, for example, toluene, which is less harmful. Further, the yield can be increased by two to three times that of Finnish Patent Application 57,743.
Předmětem vynálezu je způsob výroby 1,8-dihydroxy-10-acyl-9-anthronů obecného vzorce I, reakcí 1,8-dihydroxy-9-anthronu vzorce IIThe present invention provides a process for the preparation of 1,8-dihydroxy-10-acyl-9-anthrones of formula I by reacting 1,8-dihydroxy-9-anthrone of formula II
HO o OHHO o OH
a chloridu kyseliny obecného vzorce IIIand an acid chloride of formula III
RCOC1 (III) kde R má shora uvedený význam, vyznačující se tím, že se reakce provádí v toluenu, xylenu nebo chlorovaném uhlovodíku při teplotě od -10 do +20 °C za přítomnosti 2,6-dimetylpyridinu v reakční směsi.RCOC1 (III) wherein R is as defined above, characterized in that the reaction is carried out in toluene, xylene or a chlorinated hydrocarbon at a temperature of from -10 to +20 ° C in the presence of 2,6-dimethylpyridine in the reaction mixture.
Vynález je založen na pozorování, že náhrada pyridinu 2,6-dimetylpyridinem umožňuje snížit reakční teplotu, použít toluenu, xylenu nebo chlorovaných uhlovodíků, například dichlormetanu nebo tetratrochlorethenu, místo benzenu, a ve srovnání se známým způsobem dokonce ztrojnásobit výtěžek.The invention is based on the observation that substitution of pyridine with 2,6-dimethylpyridine makes it possible to lower the reaction temperature, use toluene, xylene or chlorinated hydrocarbons, for example dichloromethane or tetratrochlorethene, instead of benzene, and even triple the yield compared to the known method.
Použije-li se navíc chloridu kyseliny ve 100% molárním přebytku lze reakci provést během dvou hodin.In addition, if a 100% molar excess of the acid chloride is used, the reaction can be carried out within two hours.
Důsledkem výše uvedené nízké reakční teploty, která může být například -10 až +20 °C, je, že množství nečistot v připraveném 1,8-dihydroxy-10-acyl-9-anthronu je malé. Tím se čištění stává jednoduchým postupem ve srovnání s postupem podle známého způsobu. Jako rekrystalizačních rozpouštědel je možno spolu s kyselinou octovou nebo místo ní používat acetonitrilu nebo 2-propanolu.As a result of the above low reaction temperature, which can be, for example, -10 to +20 ° C, the amount of impurities in the prepared 1,8-dihydroxy-10-acyl-9-anthrone is small. Thus, the purification becomes a simple process as compared to the known process. Acetonitrile or 2-propanol can be used as recrystallization solvents together with or instead of acetic acid.
Sloučenin připravených podle vynálezu lze používat například v kožních krémech s vaseli3 novým nebo parafinovým základem v koncentracích 0,5 až 5 %, v tyčinkách určených к ošetřování pokožky v koncentracích například 2 až 8 %, v gelech a filmotvorných roztocích.The compounds prepared according to the invention can be used, for example, in vascular or paraffin-based skin creams at concentrations of 0.5 to 5%, in sticks intended for skin treatment at concentrations of, for example, 2 to 8%, in gels and film-forming solutions.
Následující příklady ilustrují podrobněji vynález.The following examples illustrate the invention in more detail.
Přikladl .He did.
Butyrylchlorid v množství 207 ml /213 g, 2,0 mol/ byl přidán během doby dvou hodin při t&plotě nižší než 0 °C ke směsi, která obsahovala 2 500 ml toluenu, 226 g /1,0 mol/Butyryl chloride in an amount of 207 ml (213 g, 2.0 mol) was added over two hours at a temperature below 0 ° C to a mixture containing 2500 ml toluene, 226 g (1.0 mol)
1,8-dihydroxy-9-anthronu a 232 ml /214 g, 2,0 mol/ 2,6-dimetylpyridinu.Of 1,8-dihydroxy-9-anthrone and 232 mL (214 g, 2.0 mol) of 2,6-dimethylpyridine.
Směs byla míchána při teplotě nižší než 0 °C po dobu dalších dvou hodin po přidání.The mixture was stirred at a temperature below 0 ° C for an additional two hours after addition.
Reakční směs byla potom zahřívána na teplotu +40 °C, hydrochlorid 2,6-dimetylpyridinu byl odfiltrován a většina toluenu byla odpařena za sníženého tlaku. К odparku bylo přidáno 2 300 ml isopropylalkoholu, reakční směs byla ochlazena na teplotu -10 °C a sraženina byla odfiltrována. Překrystalování bylo provedeno z acetonitrilu, čímž bylo získáno 222 g 1,8-dihydroxy-10-butyryl-9-anthronu. Tento výtěžek činil 75 % teorie.The reaction mixture was then heated to +40 ° C, 2,6-dimethylpyridine hydrochloride was filtered off and most of the toluene was evaporated under reduced pressure. 2300 ml of isopropanol was added to the residue, the reaction mixture was cooled to -10 ° C and the precipitate was filtered off. Recrystallization was performed from acetonitrile to give 222 g of 1,8-dihydroxy-10-butyryl-9-anthrone. This yield was 75% of theory.
Příklad 2Example 2
Způsob provedení byl zcelá analogický jako v příkladu 1, s tou výjimkou, že místo toluenu byl použit xylen. Bylo dosaženo stejného výtěžku jako v příkladu 1, tj. 75 %.The procedure was completely analogous to Example 1, except that xylene was used instead of toluene. The same yield as in Example 1 was achieved, i.e. 75%.
Příklad 3Example 3
Propionylphlorid v množství 86,9 ml /92,5 g, 1 mol/ byl přidán během dvou hodin při teplotě, nižší než 0 °C, ke směsi která obsahovala 1 200 ml toluenu, 113 g /0,5 mol/ 1,8-dihydroxy-9-anthronu a 116 ml /107 g, 1 mol/ 2,6-dimetylpyridinu. Po přidání bylo pokračováno další dvě hodiny v míchání. Získaný 1,8-dihydroxy-l0-propionyl-9-anthron byl izolován jako v příkladu 1. Výtěžek byl 120 g, tj. 80 tj. teorie.Propionyl chloride in an amount of 86.9 ml (92.5 g, 1 mol) was added over two hours at a temperature below 0 ° C to a mixture containing 1200 ml of toluene, 113 g (0.5 mol) 1.8 of di-hydroxy-9-anthrone and 116 ml (107 g, 1 mol) of 2,6-dimethylpyridine. After the addition, stirring was continued for another two hours. The obtained 1,8-dihydroxy-10-propionyl-9-anthrone was isolated as in Example 1. The yield was 120 g, i.e. 80, ie theory.
Příklad 4Example 4
Za použití 1,8-dihydroxy-9-anthronu a valerylchloridu, který byl použit ve 100% přebytku, a způsobem jako v příkladu 1, byl získán 1,8-dihydroxy-10-valeryl-9-anthran, přičemž výtěžek činil 53 %.Using 1,8-dihydroxy-9-anthrone and valeryl chloride, which was used in 100% excess, and as in Example 1, 1,8-dihydroxy-10-valeryl-9-anthran was obtained in a yield of 53% .
Příklad5Example5
Za použití následujících složek a množství byly připraveny farmaceutické přípravky:Pharmaceutical preparations were prepared using the following ingredients and amounts:
tekutý parafin 40 až 60 % , pevný parafin 40 až 60 % mikrokrystalický vosk 0,5 až 5 %.liquid paraffin 40 to 60%, solid paraffin 40 to 60% microcrystalline wax 0.5 to 5%.
Kromě toho bylo s nosičem, uvedeným výše, smícháno asi 2 až 8 % 1,8-dihydroxy-10-butyryl-9-anthronu. Ze směsi byly vytvarovány tyčinky určené к ošetření pokožky a bylo pozorováno, že užitné vlastnosti tyčinek byly dobré a dále, že léčivo v tyčinkách zůstávalo nezměněno, zejména že neoxidovalo.In addition, about 2 to 8% of 1,8-dihydroxy-10-butyryl-9-anthrone was mixed with the above carrier. Sticks intended to treat the skin were formed from the mixture and it was observed that the utility properties of the sticks were good and that the drug in the sticks remained unchanged, in particular that it did not oxidize.
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 (2)
| Publication Number | Publication Date |
|---|---|
| CS291184A2 CS291184A2 (en) | 1987-08-13 |
| CS256379B2 true CS256379B2 (en) | 1988-04-15 |
Family
ID=8517222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS842911A CS256379B2 (en) | 1983-05-18 | 1984-04-18 | Method of 1,8-dihydroxy-10-acyl-9-anthrones production |
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| 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 |
| 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 |
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| 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 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
- 1984-04-05 BE BE0/212698A patent/BE899334A/en not_active IP Right Cessation
- 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 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 PT PT78603A patent/PT78603B/en unknown
- 1984-05-17 DE DE19843418382 patent/DE3418382A1/en not_active Withdrawn
- 1984-05-17 CH CH2431/84A patent/CH659464A5/en not_active IP Right Cessation
- 1984-05-17 PL PL1984247724A patent/PL141866B1/en unknown
- 1984-05-17 CA CA000454593A patent/CA1212943A/en not_active Expired
- 1984-05-17 HU HU841908A patent/HUT36076A/en unknown
- 1984-05-17 DD DD84263131A patent/DD223702A5/en unknown
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