WO1992016496A1 - N-[[4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl]carbonyl]amino acids useful in the therapy of osteoarticular affections - Google Patents
N-[[4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl]carbonyl]amino acids useful in the therapy of osteoarticular affections Download PDFInfo
- Publication number
- WO1992016496A1 WO1992016496A1 PCT/EP1992/000479 EP9200479W WO9216496A1 WO 1992016496 A1 WO1992016496 A1 WO 1992016496A1 EP 9200479 W EP9200479 W EP 9200479W WO 9216496 A1 WO9216496 A1 WO 9216496A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compounds
- dioxo
- dihydro
- osteoarticular
- affections
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
- C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Definitions
- the present invention relates to compounds of general formula (I)
- X is selected from H and OH; R is a residue which, linked to the -CH-NH- group,
- COOH forms an amino acid; the enantiomers and racemic mixtures thereof; and the pharmaceutically acceptable salts thereof.
- Particularly preferred are those compounds in which R is a residue which, linked to the -CH-NH- group, forms a natural amino acid.
- the compounds of the invention derive from rhein, which has some therapeutical properties; particularly known is the antiarthrosic activity of diacerhein, which is the rhein diacetyl derivative.
- the derivatives of rhein with natural amino acids which are the object of the present invention, proved to have interesting pharmacological activities which make them useful for the treatment of articular pathologies.
- preliminary pharmacological researches evidenced a marked inhibiting action on the elastase activity of human leukocytes, as well as an inhibiting activity on free radical formation.
- the compounds of the invention are prepared according to conventional methods. Condensation of diacetylrhein with a compound of formula R-CH-COOR ,
- NH 2 wherein R is a C.-C 4 alkyl group is carried out in anhydrous solvents such as methylene chloride, and in the presence of acid-binding agents, for example triethylamine.
- acid-binding agents for example triethylamine.
- the 4,5-hydroxy groups, and optionally the 8-hydroxy group, on the aromatic ring, and the carboxy group on the amino acidic portion are restored by means of hydrolysis of the corresponding esters.
- An embodiment of the invention comprises the use of diacetylrhein chloride.
- 9,10-dioxo-2-anthracenecarboxylic acid chloride are added under stirring to a solution of dichloromethane
- reaction mixture is washed with water, the organic phase is separated and solvent is evaporated off under reduced pressure and the residue is taken up into 50 ml of methanol and a solution of 5 g of potassium hydroxide in 50 ml of water, to obtain a purple solution. After about 30 minutes, the solution is acidified with 8% hydrochloric acid and filtered.
- the compounds of the invention due to the above mentioned pharmacological properties thereof, can be used as active ingredients in pharmaceutical forms prepared according to known techniques.
- Examples of pharmaceutical forms are tablets, capsules, powders, syrups, injectable forms, suppositories.
- the dosage unit will range from 5 to 500 mg of active ingredient per dose.
- the posology will depend on the severity of the disease to treat and the patient's conditions.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
N-[[4,5-dihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl]carbonyl] amino acids having anti-inflammatory action, of general formula (I) wherein: X is selected from H and OH; R is a residue which, linked to the group α, forms an amino acid; a process for the preparation thereof and the use thereof in human therapy.
Description
N-[[4 ,5-DIHYDROXY- AND 4,5,8-TRIHYDROXY-9.10-DIHYDRO- 9.10-DIOXO-2-ANTHRACENE-YL]CARBONYL]AMINO ACIDS USEFUL IN THE THERAPY OF OSTEOARTICULAR AFFECTIONS
The present invention relates to compounds of general formula (I)
wherein:
X is selected from H and OH; R is a residue which, linked to the -CH-NH- group,
COOH forms an amino acid; the enantiomers and racemic mixtures thereof; and the pharmaceutically acceptable salts thereof. Particularly preferred are those compounds in which R is a residue which, linked to the -CH-NH- group, forms a natural amino acid. COOH
The compounds of the invention derive from rhein, which has some therapeutical properties; particularly known is the antiarthrosic activity of diacerhein, which is the rhein diacetyl derivative.
The derivatives of rhein with natural amino acids, which are the object of the present invention, proved to have interesting pharmacological activities which make them useful for the treatment of articular pathologies. In fact, preliminary pharmacological researches evidenced a marked inhibiting action on the
elastase activity of human leukocytes, as well as an inhibiting activity on free radical formation.
The compounds of the invention are prepared according to conventional methods. Condensation of diacetylrhein with a compound of formula R-CH-COOR ,
NH2 wherein R is a C.-C4 alkyl group, is carried out in anhydrous solvents such as methylene chloride, and in the presence of acid-binding agents, for example triethylamine. The 4,5-hydroxy groups, and optionally the 8-hydroxy group, on the aromatic ring, and the carboxy group on the amino acidic portion are restored by means of hydrolysis of the corresponding esters. An embodiment of the invention comprises the use of diacetylrhein chloride.
The following examples further illustrate the invention.
EXAMPLE 2-[[4,5-Dihydroxy-9,10-dihydro-9 ,lO-dioxo-2-anthracene- yl]carbonyl3amino-4-methyl-pentanoic aci .
3.1 g (8 mmoles) of 4,5-dihydroxy-9,10-dihydro-
9,10-dioxo-2-anthracenecarboxylic acid chloride are added under stirring to a solution of dichloromethane
(70 ml) containing 1.8 g (10 mmoles) of methyl 2-amino- 4-methyl-pentanoate hydrochloride, 50 mg of p-N,N- dimethylamino-pyridine and 2.4 ml (16 mmoles) of triethylamine. The mixture is refluxed for 5 minutes, then it is left under stirring at room temperature for a night. The reaction is controlled by means of thin layer chromatography on silica gel plates, using as eluent
dichloromethane-diethyl ether in a 10:1 ratio.
At the end of reaction, the reaction mixture is washed with water, the organic phase is separated and solvent is evaporated off under reduced pressure and the residue is taken up into 50 ml of methanol and a solution of 5 g of potassium hydroxide in 50 ml of water, to obtain a purple solution. After about 30 minutes, the solution is acidified with 8% hydrochloric acid and filtered.
The precipitate is crystallized from an acetone- diethyl ether mixture, to obtain about 1,4 g of a product with m.p. = 204°-206βC Elementary analysis for C21HlgN0- calculated % found %
C 63.47 63.40 H 4.81 4.77 N 3.52 3.56
I.R. in agreement H N.M.R. in agreement. Analogously, the following compounds were prepared: Ex. N. R Formula M.p.
2 (CH3)2CH- C20H17NO7 >210βC
3 CH3S(CH2)2- C20H17 O-S
The elementary analysis and the IR and H-NMR spectra are in agreement with the formulae and structures.
The compounds of the invention, due to the above mentioned pharmacological properties thereof, can be
used as active ingredients in pharmaceutical forms prepared according to known techniques.
Examples of pharmaceutical forms are tablets, capsules, powders, syrups, injectable forms, suppositories.
The dosage unit will range from 5 to 500 mg of active ingredient per dose. The posology will depend on the severity of the disease to treat and the patient's conditions.
Claims
1. Compounds of general formula (I)
wherein: 
X is selected from H and OH;
R is a residue which, linked to the -CH-COOH group,
I NH2 forms an amino acid; the enantiomers and racemic mixtures thereof, and the pharmaceutically acceptable salts thereof.
2. Compounds of claim 1 wherein R is a residue which, linked to the -CH-COOH group, forms a natural amino
I NH2 acid.
3. Compounds of claim 1 wherein R is isobutyl, isopropyl, methylthioethyl and wherein the carbon atom substituted with the -NH-, -COOH, -R groups has absolute configuration (R) .
4. A process for the preparation of the compounds of claims 1-3, characterized in that diacetylrhein or the
8-acetoxy derivative thereof are reacted with the compound of formula R-CH-COOR wherein R is a C -C4
NH2 alkyl residue and the ester groups are subsequently hydrolyzed.
5. A process for the preparation of the compounds of claims 1-3 characterized in that 4 , 5-dicarbometoxy- 9 , 10-dihydro-9 , 10-dioxo-2-anthracenecarboxylic acid chloride is reacted with the compound of formula
R-CH-COOR wherein R has the above defined meanings
I NH2 and the ester groups are subsequently hydrolyzed.
6. The use of the compounds of claims 1-3 as therapeutical agents.
7. Pharmaceutical compositions containing the compounds of claims 1-3 as the active ingredients in admixture with pharmaceutically acceptable carriers and excipients.
8. The use of compounds of claims 1-3 in the preparation of a medicament for the treatment of osteoarticular affections.
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9803011A HU219346B (en) | 1991-03-12 | 1992-03-04 | N-[(4,5-dihydroxi-9,10-dihydro-9,10-dioxo-2-anthracenyl)-carbonyl]-amino acids and pharmaceutical compositions containing the same |
| AU13596/92A AU661475B2 (en) | 1991-03-12 | 1992-03-04 | N-((4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl) carbonyl)amino acids useful in the therapy of osteoarticular affections |
| RU93057732A RU2111959C1 (en) | 1991-03-12 | 1992-03-04 | N-[(4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-di- -oxo-2-anthracenyl)carbonyl]-amino acids, method of their synthesis and pharmaceutical composition based on thereof |
| JP4505494A JP2979054B2 (en) | 1991-03-12 | 1992-03-04 | N-[{4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracen-yl} carbonyl] amino acids useful for the treatment of osteoarticular diseases |
| DE69208464T DE69208464T2 (en) | 1991-03-12 | 1992-03-04 | N - ((4,5-DIHYDROXY- AND 4,5,8-TRIHYDROXY-9,10-DIHYDRO-9,10-DIOXO-2-ANTHRACEN-YL) CARBONYL) AMINO ACID FOR THERAPY OSTEOARTICULAR Suffering |
| KR1019930702709A KR100224330B1 (en) | 1991-03-12 | 1992-03-04 | N- 4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl)carbonyl)amino acids |
| CA002105683A CA2105683C (en) | 1991-03-12 | 1992-03-04 | N-¬¬4,5-dihydroxy-and 4,5,8-trihydroxy-9,10-dihydro-9, 10-dioxo-2-anthracene-yl|carbonyl|amino acids useful in the therapy of osteoarticular affections |
| EP92905647A EP0588797B1 (en) | 1991-03-12 | 1992-03-04 | N- 4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl]carbonyl]amino acids useful in the therapy of osteoarticular affections |
| SK947-93A SK280134B6 (en) | 1991-03-12 | 1992-03-04 | N-[[4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo- -2-anthracene-yl]carbonyl]amino acids, process for their preparation and pharmaceutical compositions them containing |
| CS931829A CZ282997B6 (en) | 1991-03-12 | 1992-03-04 | N-/(4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro - 9,10-dioxo-2-anthracenyl)carbonyl/ amino acids, process of their preparation and pharmaceutical preparations in which they are comprised |
| US08/117,065 US5451606A (en) | 1991-03-12 | 1992-03-04 | Anthraquinone compounds useful to treat osteoarticular conditions, pharmaceutical compositions and method of treatment |
| FI933925A FI113167B (en) | 1991-03-12 | 1993-09-08 | Process for the preparation of useful N - [(4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracenyl) carbonyl] amino acids useful for the treatment of osteoarticular diseases |
| NO933241A NO304592B1 (en) | 1991-03-12 | 1993-09-10 | Amino acids useful in the therapy of osteoarticular effects, pharmaceutical mixtures and their use |
| GR960400457T GR3019069T3 (en) | 1991-03-12 | 1996-02-22 | N- 4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl)carbonyl)amino acids useful in the therapy of osteoarticular affections |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI910658A IT1244773B (en) | 1991-03-12 | 1991-03-12 | N- (4,5-DIIDROSSI-E 4,5,8-TRIIDROSSI-9,10-DIIDRO-9,10-DIOSSO-2- ANTRACEN-IL) CARBONYL) AMINO ACIDS USABLE IN THE THERAPY OF OSTEOARTICULAR AFFECTIONS |
| ITMI91A000658 | 1991-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1992016496A1 true WO1992016496A1 (en) | 1992-10-01 |
Family
ID=11359001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1992/000479 WO1992016496A1 (en) | 1991-03-12 | 1992-03-04 | N-[[4,5-dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracene-yl]carbonyl]amino acids useful in the therapy of osteoarticular affections |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5451606A (en) |
| EP (1) | EP0588797B1 (en) |
| JP (1) | JP2979054B2 (en) |
| KR (1) | KR100224330B1 (en) |
| AT (1) | ATE134363T1 (en) |
| AU (1) | AU661475B2 (en) |
| CA (1) | CA2105683C (en) |
| CZ (1) | CZ282997B6 (en) |
| DE (1) | DE69208464T2 (en) |
| DK (1) | DK0588797T3 (en) |
| ES (1) | ES2084348T3 (en) |
| FI (1) | FI113167B (en) |
| GR (1) | GR3019069T3 (en) |
| HU (1) | HU215436B (en) |
| IT (1) | IT1244773B (en) |
| MX (1) | MX9201055A (en) |
| NO (1) | NO304592B1 (en) |
| PT (1) | PT100216B (en) |
| RU (1) | RU2111959C1 (en) |
| SK (1) | SK280134B6 (en) |
| WO (1) | WO1992016496A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5480873A (en) * | 1992-02-28 | 1996-01-02 | Lilly Industries Limited | Pharmaceutical compounds |
| WO1997000675A1 (en) * | 1995-06-23 | 1997-01-09 | Boonville Limited | Mono- and disulfo-substituted anthraquinones and their use for the treatment of bone matrix disorders |
| US5668172A (en) * | 1994-08-24 | 1997-09-16 | Lilly Industries Limited | Anthraquinone pharmaceutical compounds and uses therefor |
| GB2398780A (en) * | 2003-02-26 | 2004-09-01 | Arakis Ltd | 1,8-dihydroxyanthraquinone-6-carboxamide derivatives as inhibitors of T-cell proliferation for treatment of autoimmune or inflammatory conditions |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060809B (en) * | 2009-05-01 | 2015-05-20 | 常州高新技术产业开发区三维工业技术研究所有限公司 | Rhein derivatives and preparation and application thereof |
| CN102225913B (en) * | 2011-04-07 | 2013-09-04 | 栗进才 | Rheinic acid derivatives and treatment application thereof |
| RU2466134C1 (en) * | 2011-06-24 | 2012-11-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Иркутский государственный университет" | Method of obtaining cationic palladium complexes |
| CN104557603A (en) * | 2014-12-08 | 2015-04-29 | 石河子大学 | Rhein compounds, and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508798A1 (en) * | 1976-03-16 | 1983-01-07 | Proter Spa | ANTHRAQUINONIC DERIVATIVES FOR THE TREATMENT OF ARTHRITIS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4966918A (en) * | 1989-01-27 | 1990-10-30 | Sloan-Kettering Institute For Cancer Research | Derivatives of chryosphanol |
-
1991
- 1991-03-12 IT ITMI910658A patent/IT1244773B/en active IP Right Grant
-
1992
- 1992-03-04 AU AU13596/92A patent/AU661475B2/en not_active Ceased
- 1992-03-04 EP EP92905647A patent/EP0588797B1/en not_active Expired - Lifetime
- 1992-03-04 DK DK92905647.1T patent/DK0588797T3/en active
- 1992-03-04 CA CA002105683A patent/CA2105683C/en not_active Expired - Fee Related
- 1992-03-04 DE DE69208464T patent/DE69208464T2/en not_active Expired - Fee Related
- 1992-03-04 CZ CS931829A patent/CZ282997B6/en not_active IP Right Cessation
- 1992-03-04 RU RU93057732A patent/RU2111959C1/en not_active IP Right Cessation
- 1992-03-04 AT AT92905647T patent/ATE134363T1/en not_active IP Right Cessation
- 1992-03-04 WO PCT/EP1992/000479 patent/WO1992016496A1/en active IP Right Grant
- 1992-03-04 HU HU9302510A patent/HU215436B/en not_active IP Right Cessation
- 1992-03-04 KR KR1019930702709A patent/KR100224330B1/en not_active IP Right Cessation
- 1992-03-04 SK SK947-93A patent/SK280134B6/en unknown
- 1992-03-04 JP JP4505494A patent/JP2979054B2/en not_active Expired - Fee Related
- 1992-03-04 US US08/117,065 patent/US5451606A/en not_active Expired - Fee Related
- 1992-03-04 ES ES92905647T patent/ES2084348T3/en not_active Expired - Lifetime
- 1992-03-09 PT PT100216A patent/PT100216B/en active IP Right Grant
- 1992-03-11 MX MX9201055A patent/MX9201055A/en not_active IP Right Cessation
-
1993
- 1993-09-08 FI FI933925A patent/FI113167B/en not_active IP Right Cessation
- 1993-09-10 NO NO933241A patent/NO304592B1/en not_active IP Right Cessation
-
1996
- 1996-02-22 GR GR960400457T patent/GR3019069T3/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2508798A1 (en) * | 1976-03-16 | 1983-01-07 | Proter Spa | ANTHRAQUINONIC DERIVATIVES FOR THE TREATMENT OF ARTHRITIS |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5480873A (en) * | 1992-02-28 | 1996-01-02 | Lilly Industries Limited | Pharmaceutical compounds |
| US5668172A (en) * | 1994-08-24 | 1997-09-16 | Lilly Industries Limited | Anthraquinone pharmaceutical compounds and uses therefor |
| US5792797A (en) * | 1994-08-24 | 1998-08-11 | Lilly Industries Limited | Pharmaceutical compounds |
| WO1997000675A1 (en) * | 1995-06-23 | 1997-01-09 | Boonville Limited | Mono- and disulfo-substituted anthraquinones and their use for the treatment of bone matrix disorders |
| US5856358A (en) * | 1995-06-23 | 1999-01-05 | Boonville Limited | Mono- and disulfo-substituted anthraquinones and their use for the treatment of bone matrix disorders |
| GB2398780A (en) * | 2003-02-26 | 2004-09-01 | Arakis Ltd | 1,8-dihydroxyanthraquinone-6-carboxamide derivatives as inhibitors of T-cell proliferation for treatment of autoimmune or inflammatory conditions |
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