SK281699B6 - Spôsob prípravy diacereínu - Google Patents
Spôsob prípravy diacereínu Download PDFInfo
- Publication number
- SK281699B6 SK281699B6 SK44-95A SK4495A SK281699B6 SK 281699 B6 SK281699 B6 SK 281699B6 SK 4495 A SK4495 A SK 4495A SK 281699 B6 SK281699 B6 SK 281699B6
- Authority
- SK
- Slovakia
- Prior art keywords
- diacerein
- dimethylacetamide
- crystallization
- mol
- acetic anhydride
- Prior art date
Links
- TYNLGDBUJLVSMA-UHFFFAOYSA-N 4,5-diacetyloxy-9,10-dioxo-2-anthracenecarboxylic acid Chemical compound O=C1C2=CC(C(O)=O)=CC(OC(C)=O)=C2C(=O)C2=C1C=CC=C2OC(=O)C TYNLGDBUJLVSMA-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229960004590 diacerein Drugs 0.000 claims abstract description 62
- 238000002425 crystallisation Methods 0.000 claims abstract description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 27
- 230000008025 crystallization Effects 0.000 claims abstract description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000000746 purification Methods 0.000 claims abstract description 22
- AFHJQYHRLPMKHU-XXWVOBANSA-N Aloin Natural products O=C1c2c(O)cc(CO)cc2[C@H]([C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)c2c1c(O)ccc2 AFHJQYHRLPMKHU-XXWVOBANSA-N 0.000 claims abstract description 12
- AFHJQYHRLPMKHU-UHFFFAOYSA-N isobarbaloin Natural products OC1C(O)C(O)C(CO)OC1C1C2=CC(CO)=CC(O)=C2C(=O)C2=C(O)C=CC=C21 AFHJQYHRLPMKHU-UHFFFAOYSA-N 0.000 claims abstract description 12
- CPUHNROBVJNNPW-UHFFFAOYSA-N aloin A Natural products OC1C(O)C(O)C(CO)OC1OC1C2=CC(CO)=CC(O)=C2C(=O)C2=C(O)C=CC=C21 CPUHNROBVJNNPW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000021736 acetylation Effects 0.000 claims abstract description 10
- 238000006640 acetylation reaction Methods 0.000 claims abstract description 10
- 230000003647 oxidation Effects 0.000 claims abstract description 9
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- AFHJQYHRLPMKHU-WEZNYRQKSA-N aloin B Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1[C@H]1C2=CC(CO)=CC(O)=C2C(=O)C2=C(O)C=CC=C21 AFHJQYHRLPMKHU-WEZNYRQKSA-N 0.000 claims abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 66
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 229960000583 acetic acid Drugs 0.000 claims description 13
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical group O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000012345 acetylating agent Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 239000001632 sodium acetate Substances 0.000 claims description 4
- 235000017281 sodium acetate Nutrition 0.000 claims description 4
- 229940008102 alloin Drugs 0.000 claims description 3
- AFHJQYHRLPMKHU-CGISPIQUSA-N aloin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1C2=CC(CO)=CC(O)=C2C(=O)C2=C(O)C=CC=C21 AFHJQYHRLPMKHU-CGISPIQUSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229940117975 chromium trioxide Drugs 0.000 claims description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract description 25
- 239000000047 product Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000003643 water by type Substances 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- AFHJQYHRLPMKHU-OSYMLPPYSA-N aloin A Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1[C@@H]1C2=CC(CO)=CC(O)=C2C(=O)C2=C(O)C=CC=C21 AFHJQYHRLPMKHU-OSYMLPPYSA-N 0.000 description 9
- YDQWDHRMZQUTBA-UHFFFAOYSA-N Aloe emodin Chemical compound C1=CC=C2C(=O)C3=CC(CO)=CC(O)=C3C(=O)C2=C1O YDQWDHRMZQUTBA-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000523 sample Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- -1 aliphatic amines Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 230000003505 mutagenic effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FCDLCPWAQCPTKC-UHFFFAOYSA-N Rhein Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC(O)=C3C(=O)C2=C1O FCDLCPWAQCPTKC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical group O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 235000017399 Caesalpinia tinctoria Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000010282 Emodin Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000388430 Tara Species 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000002456 anti-arthritic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000008141 laxative Substances 0.000 description 1
- 230000002475 laxative effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cephalosporin Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT93MI001741A IT1264545B1 (it) | 1993-07-30 | 1993-07-30 | Procedimento per la preparazione della diacereina |
| DE69409722T DE69409722T2 (de) | 1993-07-30 | 1994-07-07 | Verfahren zur Herstellung von Diacerein |
| DK94110551T DK0636602T3 (da) | 1993-07-30 | 1994-07-07 | Fremgangsmåde til fremstilling af diacerein |
| AT94110551T ATE165335T1 (de) | 1993-07-30 | 1994-07-07 | Verfahren zur herstellung von diacerein |
| ES94110551T ES2115814T3 (es) | 1993-07-30 | 1994-07-07 | Procedimiento para la preparacion de diacerein. |
| EP94110551A EP0636602B1 (fr) | 1993-07-30 | 1994-07-07 | Procédé de préparation de la diacérein |
| JP19269394A JP3850458B2 (ja) | 1993-07-30 | 1994-07-26 | ジアセラインの製造プロセス |
| SK44-95A SK281699B6 (sk) | 1993-07-30 | 1995-01-12 | Spôsob prípravy diacereínu |
| CZ199590A CZ286702B6 (en) | 1993-07-30 | 1995-01-12 | Process for preparing diacerein |
| HU9500188A HU221980B1 (hu) | 1993-07-30 | 1995-01-23 | Eljárás diacerein előállítására és új acilezett aloin intermedier |
| US08/376,722 US5670695A (en) | 1993-07-30 | 1995-01-23 | Process for the preparation of diacerein |
| CA002141247A CA2141247C (fr) | 1993-07-30 | 1995-01-27 | Mode de preparation de la diacereine |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT93MI001741A IT1264545B1 (it) | 1993-07-30 | 1993-07-30 | Procedimento per la preparazione della diacereina |
| SK44-95A SK281699B6 (sk) | 1993-07-30 | 1995-01-12 | Spôsob prípravy diacereínu |
| CZ199590A CZ286702B6 (en) | 1993-07-30 | 1995-01-12 | Process for preparing diacerein |
| HU9500188A HU221980B1 (hu) | 1993-07-30 | 1995-01-23 | Eljárás diacerein előállítására és új acilezett aloin intermedier |
| US08/376,722 US5670695A (en) | 1993-07-30 | 1995-01-23 | Process for the preparation of diacerein |
| CA002141247A CA2141247C (fr) | 1993-07-30 | 1995-01-27 | Mode de preparation de la diacereine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK4495A3 SK4495A3 (en) | 1996-08-07 |
| SK281699B6 true SK281699B6 (sk) | 2001-07-10 |
Family
ID=27543486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK44-95A SK281699B6 (sk) | 1993-07-30 | 1995-01-12 | Spôsob prípravy diacereínu |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5670695A (fr) |
| EP (1) | EP0636602B1 (fr) |
| JP (1) | JP3850458B2 (fr) |
| AT (1) | ATE165335T1 (fr) |
| CA (1) | CA2141247C (fr) |
| CZ (1) | CZ286702B6 (fr) |
| DE (1) | DE69409722T2 (fr) |
| DK (1) | DK0636602T3 (fr) |
| ES (1) | ES2115814T3 (fr) |
| HU (1) | HU221980B1 (fr) |
| IT (1) | IT1264545B1 (fr) |
| SK (1) | SK281699B6 (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH689279A5 (fr) * | 1995-02-07 | 1999-01-29 | Steba Beheer Bv | Procédé de purification de la diacétylrhéine. |
| IT1283772B1 (it) * | 1996-07-31 | 1998-04-30 | Medidom Lab | Procedimento per la preparazione di reina e diacereina |
| IT1283771B1 (it) * | 1996-07-31 | 1998-04-30 | Medidom Lab | Procedimento per la preparazione di derivati della reina |
| IT1292132B1 (it) * | 1997-06-11 | 1999-01-25 | Synteco S R L | Procedimento per la preparazione di diacereina |
| IT1297038B1 (it) * | 1997-12-30 | 1999-08-03 | Medidom Lab | Procedimento per la preparazione di reina e suoi diacilderivati |
| US6797289B2 (en) | 1998-02-13 | 2004-09-28 | Nutramax Laboratories, Inc. | Use of anabolic agents, anti-catabolic agents, antioxidant agents, and analgesics for protection, treatment and repair of connective tissues in humans and animals |
| US20070141181A1 (en) | 1998-02-13 | 2007-06-21 | Nutramax Laboratories, Inc. | Use of anabolic agents, anti-catabolic agents, antioxidant agents, and analgesics for protection, treatment and repair of connective tissues in humans and animals |
| US6451771B1 (en) | 1999-02-12 | 2002-09-17 | Nutramax Laboratories, Inc. | Use of anabolic agents anti-catabolic agents and antioxidant agents for protection treatment and repair of connective tissues in humans and animals |
| IT1312309B1 (it) * | 1999-05-07 | 2002-04-15 | Synteco Spa | Procedimento per la purificazione di diacereina |
| AR026801A1 (es) | 2000-01-12 | 2003-02-26 | Medidom Lab | Sustancias para uso en el tratamiento de la psoriasis |
| IT1318574B1 (it) * | 2000-06-13 | 2003-08-27 | Synteco Spa | Procedimento per la purificazione di diacereina. |
| ITMI20022535A1 (it) * | 2002-11-29 | 2004-05-30 | Synteco Spa | Procedimento per la purificazione della diacereina. |
| EP2060562A1 (fr) | 2007-11-16 | 2009-05-20 | Laboratoire Medidom S.A. | Dérivés de sulfonate de dioxoanthracène |
| WO2009106909A1 (fr) * | 2008-02-29 | 2009-09-03 | Laboratoire Medidom S.A. | Processus de purification de diacéréine |
| WO2009106908A1 (fr) | 2008-02-29 | 2009-09-03 | Laboratoire Medidom S.A. | Processus de préparation de rhéine |
| WO2011030350A1 (fr) | 2009-09-08 | 2011-03-17 | Lupin Limited | Procédé respectueux de l'environnement permettant l'oxydation catalytique par l'air de l'aloé-émodine en rheinal |
| CN101696164A (zh) * | 2009-10-19 | 2010-04-21 | 黄再新 | 一步法用芦荟甙合成双醋瑞因粗品的方法 |
| ITTO20110120A1 (it) | 2011-02-11 | 2012-08-12 | Icrom Spa | Un nuovo processo di purificazione per derivati antrachinonici |
| CN104774150B (zh) * | 2014-01-14 | 2017-04-12 | 北京万生药业有限责任公司 | 一种双醋瑞因晶体及其制备方法 |
| CN112279767B (zh) * | 2020-10-29 | 2023-02-03 | 陕西嘉禾生物科技股份有限公司 | 一种双醋瑞因的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA761627B (en) * | 1976-03-16 | 1978-01-25 | C Friedmann | Improvements in or relating to the treatment of arthritis |
| IT1189097B (it) * | 1986-05-02 | 1988-01-28 | Proter Spa | Sali di diacetilreina e loro impiego terapeutico nel trattamento dell'artrosi |
| DE4120989C2 (de) * | 1991-06-25 | 1995-07-27 | Madaus Ag | Verfahren zur Herstellung von Diacetylrhein |
| US5393898A (en) * | 1991-06-25 | 1995-02-28 | Madaus Ag | Method of preparing diacetyl rhein |
-
1993
- 1993-07-30 IT IT93MI001741A patent/IT1264545B1/it active IP Right Grant
-
1994
- 1994-07-07 ES ES94110551T patent/ES2115814T3/es not_active Expired - Lifetime
- 1994-07-07 EP EP94110551A patent/EP0636602B1/fr not_active Expired - Lifetime
- 1994-07-07 AT AT94110551T patent/ATE165335T1/de active
- 1994-07-07 DE DE69409722T patent/DE69409722T2/de not_active Expired - Lifetime
- 1994-07-07 DK DK94110551T patent/DK0636602T3/da active
- 1994-07-26 JP JP19269394A patent/JP3850458B2/ja not_active Expired - Lifetime
-
1995
- 1995-01-12 CZ CZ199590A patent/CZ286702B6/cs not_active IP Right Cessation
- 1995-01-12 SK SK44-95A patent/SK281699B6/sk not_active IP Right Cessation
- 1995-01-23 US US08/376,722 patent/US5670695A/en not_active Expired - Lifetime
- 1995-01-23 HU HU9500188A patent/HU221980B1/hu active IP Right Grant
- 1995-01-27 CA CA002141247A patent/CA2141247C/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69409722D1 (de) | 1998-05-28 |
| CA2141247A1 (fr) | 1996-07-28 |
| ES2115814T3 (es) | 1998-07-01 |
| IT1264545B1 (it) | 1996-10-02 |
| EP0636602A1 (fr) | 1995-02-01 |
| JP3850458B2 (ja) | 2006-11-29 |
| ITMI931741A1 (it) | 1995-01-30 |
| SK4495A3 (en) | 1996-08-07 |
| DK0636602T3 (da) | 1999-01-11 |
| JPH0753462A (ja) | 1995-02-28 |
| EP0636602B1 (fr) | 1998-04-22 |
| HU221980B1 (hu) | 2003-03-28 |
| CZ9095A3 (en) | 1996-07-17 |
| HUT73498A (en) | 1996-08-28 |
| CZ286702B6 (en) | 2000-06-14 |
| US5670695A (en) | 1997-09-23 |
| CA2141247C (fr) | 2004-08-31 |
| ITMI931741A0 (it) | 1993-07-30 |
| HU9500188D0 (en) | 1995-03-28 |
| ATE165335T1 (de) | 1998-05-15 |
| DE69409722T2 (de) | 1998-08-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20150112 |