FI104892B - Framställningsförfarande av diacetylrhein - Google Patents
Framställningsförfarande av diacetylrhein Download PDFInfo
- Publication number
- FI104892B FI104892B FI922930A FI922930A FI104892B FI 104892 B FI104892 B FI 104892B FI 922930 A FI922930 A FI 922930A FI 922930 A FI922930 A FI 922930A FI 104892 B FI104892 B FI 104892B
- Authority
- FI
- Finland
- Prior art keywords
- liquid
- diacetyl
- process according
- compounds
- carried out
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 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 abstract description 15
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- VXWSFRMTBJZULV-UHFFFAOYSA-H iron(3+) sulfate hydrate Chemical compound O.[Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VXWSFRMTBJZULV-UHFFFAOYSA-H 0.000 description 1
- 210000001503 joint Anatomy 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000554 physical therapy Methods 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 208000001413 spine osteoarthritis Diseases 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Developing Agents For Electrophotography (AREA)
- Holo Graphy (AREA)
- Electroluminescent Light Sources (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
Claims (15)
1. Förfarande för utvinning av diacetylrhein, kännetecknat därav, att aloe-emodinkomponenter innehällande diacetylrhein underkastas en vätske/vätske- 5 fördelning mellan ett endast delvis i vatten blandbart polärt organiskt lösnings-medel, och en vattenhaltig fas med pH-värdet 6,5 - 7,5 och diacetylrhein tas tillvara och eventuell kristalliseras pä nytt.
2. Förfarande för framställning av diacetylrhein, som är väsentligen fri fran 10 aloe-emodinkomponenter, kännetecknat därav, att i förfarandet a) aloe-emodinkomponenter innehällande rhein-9-antron-8-glukosid oxide-ras tili motsvarande antrakinonförening, b) glukosgruppen i antrakinonföreningens 8-ställning avspjälks i syrame-dium, 15 c) de erhällna 1,8-dihydroxiantrakinonföreningarna acetyleras och d) den erhällna produktens vätske/vätske-fördelning utförs med ett polärt, endast delvis i vatten blandbart organiskt lösningsmedel och den vattenhaltig fas med pH-värdet 6,5 - 7,5 och diacetylrhein tillvaratas och eventuell kristalliseras pä nytt. 20 ; .
3. Förfarande för framställning av diacetylrhein, som är väsentligen fri frän ; ‘: aloe-emodinkomponenter, kännetecknat därav, att i förfarandet I < :*·.· a) en sennosidblandning reduceras tili motsvarande antronförening, :T: b) de erhällna antronföreningarna oxideras tili motsvarande antrakinonföre- 25 ningar, :T: c) glukosgruppen i antrakinonföreningens 8-ställning avspjälks i syrame- dium, c) de erhällna 1,8-dihydroxiantrakinonföreningarna acetyleras och • · .;; d) den erhällna produktens vätske/vätske-fördelning utförs med ett polärt, . ’. 30 endast delvis i vatten blandbart organiskt lösningsmedel och den vatten- ‘' haltig fas med pH-värdet 6,5 - 7,5 och diacetylrhein tillvaratas och even tuell kristalliseras pä nytt. 104892
4. Förfarande enligt nagot av föregäende patentkrav, kännetecknat därav, att i vätske/vätske-fördelningen används som polärt organiskt lösningsmedel butan-2-on.
5 5. Förfarande enligt nagot av föregäende patentkrav, kännetecknat därav, att i vätske/vätske-fördelningen används med acetat buffrad vattenfas.
6. Förfarande enligt nagot av föregäende patentkrav, kännetecknat därav, att vätske/vätske-fördelningen utförs motströms. 10
7. Förfarande enligt nagot av patentkraven 2-6, kännetecknat därav, att som oxidationsmedel används ferrisalt.
8. Förfarande enligt patentkravet 7, kännetecknat därav, att ferrisaltet är 15 ferrisulfat.
9. Förfarande enligt patentkravet 3, kännetecknat därav, att sennosidbland-ningen kan erhällas genom extraktion av sennamedicin med vattenhaltig meta-nol. 20
10. Förfarande enligt patentkravet 9, kännetecknat därav, att extraktionen :' \: med metanol utförs i närvaro av en buffert. « · ♦ · • · · • · · • ·
11. Förfarande enligt nagot av patentkraven 3-10, kännetecknat därav, att i 25 steget a) används som reduktionsmedel alkalimetallditionit.
··· • · * • ♦ · ··· : 12. Förfarande enligt patentkravet 11, kännetecknat därav, att reduktionen « utförs vid pH-värdet 7-9. • · 1 « : . . 30
13. Förfarande enligt nagot av patentkraven 3-12, kännetecknat därav, att .;..; reduktionen utförs upprepat. 104892
14. Förfarande enligt nägot av föregaende patentkrav, kännetecknat därav, att den erhällna diacetylrhein kristalliseras pa nytt genom att omvandla diace-tylrhein till alkalimetallsalt, som löses i vattenhaltig C^^-alkohoI, och diacetylrhein utfälls pä nytt genom tillsättning av syra. 5
15. Förfarande enligt nägot av patentkraven 1-13, kännetecknat därav, att diacetylrhein kristalliseras pä nytt ur etyllaktat. • · • · · • · · • · • · · • · · • · · • · · • · · • · · • M • · · • · · « • · • · · • · · • · I « t < · < « • 1 • I I · I i
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4120989 | 1991-06-25 | ||
| DE4120989A DE4120989C2 (de) | 1991-06-25 | 1991-06-25 | Verfahren zur Herstellung von Diacetylrhein |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI922930A0 FI922930A0 (fi) | 1992-06-24 |
| FI922930A FI922930A (fi) | 1992-12-26 |
| FI104892B true FI104892B (sv) | 2000-04-28 |
Family
ID=6434717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI922930A FI104892B (sv) | 1991-06-25 | 1992-06-24 | Framställningsförfarande av diacetylrhein |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US5391775A (sv) |
| EP (1) | EP0520414B1 (sv) |
| JP (1) | JPH0825955B2 (sv) |
| AT (1) | ATE135341T1 (sv) |
| AU (1) | AU645208B2 (sv) |
| CA (1) | CA2072283C (sv) |
| CZ (1) | CZ194892A3 (sv) |
| DE (2) | DE4120989C2 (sv) |
| DK (1) | DK0520414T3 (sv) |
| ES (1) | ES2084877T3 (sv) |
| FI (1) | FI104892B (sv) |
| GR (1) | GR3019321T3 (sv) |
| HU (1) | HU220390B (sv) |
| IE (1) | IE72526B1 (sv) |
| PL (1) | PL168847B1 (sv) |
| RU (1) | RU2104996C1 (sv) |
| SK (1) | SK194892A3 (sv) |
| TW (1) | TW400333B (sv) |
| ZA (1) | ZA924644B (sv) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5710260A (en) * | 1991-06-25 | 1998-01-20 | Madaus Ag | Method of extracting sennosides A, B and A1 |
| IT1264545B1 (it) * | 1993-07-30 | 1996-10-02 | Medidom Lab | Procedimento per la preparazione della diacereina |
| FI96692C (sv) * | 1993-12-17 | 1996-08-12 | Leiras Oy | Förfarande för framställning av sennocid A och B |
| CH689279A5 (fr) * | 1995-02-07 | 1999-01-29 | Steba Beheer Bv | Procédé de purification de la diacétylrhéine. |
| US5652265A (en) * | 1995-03-29 | 1997-07-29 | Wisconsin Alumni Research Foundation | Production of rhein and rhein derivatives |
| WO2003000246A1 (en) * | 2001-06-25 | 2003-01-03 | Arakis Ltd. | The use of rhein and derivatives thereof in pain treatment |
| ITMI20022535A1 (it) * | 2002-11-29 | 2004-05-30 | Synteco Spa | Procedimento per la purificazione della diacereina. |
| MXPA03008622A (es) * | 2003-09-23 | 2005-03-30 | Interquim S A De C V | Metodo de purificacion de diacereina cruda por la via del tolueno. |
| EP2196450A1 (en) | 2008-12-09 | 2010-06-16 | Evultis S.A. | Process for the preparation of pure diacetylrhein (diacerein) |
| EP2364287B1 (en) * | 2008-12-09 | 2014-04-02 | Evultis S.A. | Process for the preparation of non-genotoxic diacetylrhein (diacerein) and formulations comprising non-genotoxic diacetylrhein |
| EP2218707A1 (en) | 2009-02-16 | 2010-08-18 | Evultis S.A. | Process for the preparation of non-genotoxic Diacetylrhein (Diacerein) |
| WO2011099834A2 (es) * | 2010-02-15 | 2011-08-18 | Interquim, S.A. De C.V. | Procedimiento para la purificación de diacereina cruda vía sal de potasio/dimetil formamida |
| ITTO20110120A1 (it) | 2011-02-11 | 2012-08-12 | Icrom Spa | Un nuovo processo di purificazione per derivati antrachinonici |
| AU2013290277B2 (en) * | 2012-07-10 | 2016-07-21 | Children's Healthcare Of Atlanta, Inc. | Anthraquinone analogs and methods of making and using thereof |
| CN105985242A (zh) * | 2015-01-27 | 2016-10-05 | 邵阳学院 | 双醋瑞因制备方法 |
Family Cites Families (3)
| 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 |
| DE3200131A1 (de) * | 1982-01-05 | 1983-07-14 | Madaus & Co Dr | "verfahren zur gewinnung von laxativen verbindungen aus sennadroge" |
| IT1189097B (it) * | 1986-05-02 | 1988-01-28 | Proter Spa | Sali di diacetilreina e loro impiego terapeutico nel trattamento dell'artrosi |
-
1991
- 1991-06-25 DE DE4120989A patent/DE4120989C2/de not_active Expired - Fee Related
-
1992
- 1992-06-24 ES ES92110652T patent/ES2084877T3/es not_active Expired - Lifetime
- 1992-06-24 AU AU18484/92A patent/AU645208B2/en not_active Expired
- 1992-06-24 AT AT92110652T patent/ATE135341T1/de not_active IP Right Cessation
- 1992-06-24 DK DK92110652.2T patent/DK0520414T3/da active
- 1992-06-24 CZ CS921948A patent/CZ194892A3/cs unknown
- 1992-06-24 ZA ZA924644A patent/ZA924644B/xx unknown
- 1992-06-24 JP JP4165960A patent/JPH0825955B2/ja not_active Expired - Lifetime
- 1992-06-24 EP EP92110652A patent/EP0520414B1/de not_active Expired - Lifetime
- 1992-06-24 RU SU5052409/04A patent/RU2104996C1/ru not_active IP Right Cessation
- 1992-06-24 HU HU9202108A patent/HU220390B/hu not_active IP Right Cessation
- 1992-06-24 PL PL92295006A patent/PL168847B1/pl unknown
- 1992-06-24 SK SK1948-92A patent/SK194892A3/sk unknown
- 1992-06-24 DE DE59205646T patent/DE59205646D1/de not_active Expired - Lifetime
- 1992-06-24 FI FI922930A patent/FI104892B/sv active
- 1992-06-25 CA CA002072283A patent/CA2072283C/en not_active Expired - Fee Related
- 1992-07-01 IE IE922046A patent/IE72526B1/en not_active IP Right Cessation
- 1992-12-07 TW TW081109789A patent/TW400333B/zh not_active IP Right Cessation
-
1994
- 1994-04-29 US US08/236,682 patent/US5391775A/en not_active Expired - Lifetime
- 1994-11-02 US US08/333,202 patent/US6624192B1/en not_active Expired - Lifetime
-
1996
- 1996-03-14 GR GR960400633T patent/GR3019321T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE922046A1 (en) | 1992-12-30 |
| JPH0825955B2 (ja) | 1996-03-13 |
| DE4120989C2 (de) | 1995-07-27 |
| EP0520414A1 (de) | 1992-12-30 |
| DE59205646D1 (de) | 1996-04-18 |
| EP0520414B1 (de) | 1996-03-13 |
| PL168847B1 (pl) | 1996-04-30 |
| HU220390B (hu) | 2002-01-28 |
| PL295006A1 (en) | 1993-02-22 |
| FI922930A0 (fi) | 1992-06-24 |
| ATE135341T1 (de) | 1996-03-15 |
| TW400333B (en) | 2000-08-01 |
| CA2072283C (en) | 2000-10-24 |
| JPH05186394A (ja) | 1993-07-27 |
| AU1848492A (en) | 1993-03-11 |
| US5391775A (en) | 1995-02-21 |
| ES2084877T3 (es) | 1996-05-16 |
| FI922930A (fi) | 1992-12-26 |
| SK194892A3 (en) | 1995-02-08 |
| CA2072283A1 (en) | 1992-12-26 |
| DK0520414T3 (da) | 1996-04-01 |
| GR3019321T3 (en) | 1996-06-30 |
| DE4120989A1 (de) | 1993-01-07 |
| HU9202108D0 (en) | 1992-10-28 |
| HUT61263A (en) | 1992-12-28 |
| CZ194892A3 (en) | 1993-01-13 |
| IE72526B1 (en) | 1997-04-23 |
| RU2104996C1 (ru) | 1998-02-20 |
| AU645208B2 (en) | 1994-01-06 |
| US6624192B1 (en) | 2003-09-23 |
| ZA924644B (en) | 1993-03-31 |
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