CA1212943A - Method for the preparation of 1,8-dihydroxy-10-acyl-9- anthrones, especially for use in the treatment of psoriasis - Google Patents
Method for the preparation of 1,8-dihydroxy-10-acyl-9- anthrones, especially for use in the treatment of psoriasisInfo
- Publication number
- CA1212943A CA1212943A CA000454593A CA454593A CA1212943A CA 1212943 A CA1212943 A CA 1212943A CA 000454593 A CA000454593 A CA 000454593A CA 454593 A CA454593 A CA 454593A CA 1212943 A CA1212943 A CA 1212943A
- Authority
- CA
- Canada
- Prior art keywords
- dihydroxy
- anthrone
- acyl
- formula
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 201000004681 Psoriasis Diseases 0.000 title abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 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 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 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
- 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
- 239000000463 material Substances 0.000 abstract 1
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 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
- 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
- 238000001953 recrystallisation Methods 0.000 description 2
- UYKMGHUKSVDIFU-UHFFFAOYSA-N 1,8-dihydroxy-10-pentanoyl-10h-anthracen-9-one Chemical compound C1=CC=C2C(C(=O)CCCC)C3=CC=CC(O)=C3C(=O)C2=C1O UYKMGHUKSVDIFU-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 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
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012535 impurity 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
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229950011008 tetrachloroethylene 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI831739A FI66585C (fi) | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1212943A true CA1212943A (en) | 1986-10-21 |
Family
ID=8517222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000454593A Expired 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 |
Country Status (31)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2492372A1 (fr) * | 1980-10-21 | 1982-04-23 | Cird | Dihydroxy-1,8 anthrones-9 substituees en position 10 et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| 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 (fr) * | 1985-12-11 | 1988-07-22 | Cird | Mono, di et tri-esters de dihydroxy-1,8 phenyl-10 anthrone-9 ou anthranol-9, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| FR2566772B1 (fr) * | 1984-06-29 | 1986-11-14 | Cird | Diacyloxy-1,8 acyl-10 anthrones, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| FR2580631B1 (fr) * | 1985-04-17 | 1987-05-29 | Cird | Hydroxy-1 acyloxy-8 acyl-10 anthrones, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| DE69223723T2 (de) * | 1991-10-04 | 1998-04-16 | Fisher & Paykel | Luftbefeuchter |
| DE4231636A1 (de) * | 1992-09-22 | 1994-03-24 | Beiersdorf Ag | Neue in 10-Stellung substituierte Anthron- und Anthracen-Derivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende pharmazeutische oder kosmetische Mittel und deren Verwendung |
| 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 (fi) * | 1979-03-29 | 1980-10-10 | Orion Yhtymae Oy | Foerfarande foer framstaellning av nya 1,8-dihydroxi-10-acyl-9-antroner mot psoriasis |
-
1983
- 1983-05-18 FI FI831739A patent/FI66585C/fi not_active IP Right Cessation
-
1984
- 1984-03-22 NZ NZ207592A patent/NZ207592A/en unknown
- 1984-03-22 AU AU25998/84A patent/AU560079B2/en not_active Ceased
- 1984-03-23 IT IT20213/84A patent/IT1173473B/it active
- 1984-03-26 ZA ZA842223A patent/ZA842223B/xx unknown
- 1984-03-29 IN IN209/CAL/84A patent/IN156115B/en unknown
- 1984-03-30 DK DK173584A patent/DK154207C/da active IP Right Grant
- 1984-04-04 NL NL8401074A patent/NL8401074A/nl not_active Application Discontinuation
- 1984-04-04 GB GB08408666A patent/GB2140007B/en not_active Expired
- 1984-04-05 BE BE0/212698A patent/BE899334A/fr not_active IP Right Cessation
- 1984-04-05 IS IS2902A patent/IS2902A7/is unknown
- 1984-04-05 IL IL71446A patent/IL71446A/xx not_active IP Right Cessation
- 1984-04-05 GR GR74318A patent/GR79971B/el unknown
- 1984-04-06 LU LU85292A patent/LU85292A1/fr unknown
- 1984-04-18 ES ES531760A patent/ES8505167A1/es not_active Expired
- 1984-04-18 CS CS842911A patent/CS256379B2/cs unknown
- 1984-04-27 KR KR1019840002278A patent/KR840009059A/ko not_active Withdrawn
- 1984-05-02 FR FR8406790A patent/FR2546162B1/fr not_active Expired
- 1984-05-04 JP JP59090047A patent/JPS59212443A/ja active Pending
- 1984-05-08 SU SU843735603A patent/SU1240351A3/ru active
- 1984-05-10 YU YU00817/84A patent/YU81784A/xx unknown
- 1984-05-16 PH PH30686A patent/PH20038A/en unknown
- 1984-05-16 NO NO841965A patent/NO157099C/no unknown
- 1984-05-16 SE SE8402649A patent/SE453827B/sv not_active IP Right Cessation
- 1984-05-17 HU HU841908A patent/HUT36076A/hu unknown
- 1984-05-17 DD DD84263131A patent/DD223702A5/de unknown
- 1984-05-17 PT PT78603A patent/PT78603B/pt unknown
- 1984-05-17 CH CH2431/84A patent/CH659464A5/de not_active IP Right Cessation
- 1984-05-17 DE DE19843418382 patent/DE3418382A1/de not_active Withdrawn
- 1984-05-17 CA CA000454593A patent/CA1212943A/en not_active Expired
- 1984-05-17 PL PL1984247724A patent/PL141866B1/pl unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |