FI104892B - Diasetyylirheinin valmistusmenetelmä - Google Patents
Diasetyylirheinin valmistusmenetelmä 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
Links
- 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
- 229960004590 diacerein Drugs 0.000 title abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 39
- YDQWDHRMZQUTBA-UHFFFAOYSA-N Aloe emodin Chemical class C1=CC=C2C(=O)C3=CC(CO)=CC(O)=C3C(=O)C2=C1O YDQWDHRMZQUTBA-UHFFFAOYSA-N 0.000 claims abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 27
- 229930186851 sennoside Natural products 0.000 claims description 25
- -1 anthraquinone compounds Chemical class 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229940124513 senna glycoside Drugs 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 9
- 239000003495 polar organic solvent Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 150000008425 anthrones Chemical class 0.000 claims description 7
- 244000025254 Cannabis sativa Species 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 6
- IPQVTOJGNYVQEO-KGFNBKMBSA-N sennoside A Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(O)=O)C=C1[C@@H]2[C@H]1C2=CC(C(O)=O)=CC(O)=C2C(=O)C2=C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C=CC=C21 IPQVTOJGNYVQEO-KGFNBKMBSA-N 0.000 claims description 6
- 150000004359 1,8-dihydroxyanthraquinones Chemical class 0.000 claims description 5
- 238000000638 solvent extraction Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 239000000872 buffer Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 3
- 229940116333 ethyl lactate Drugs 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 238000011144 upstream manufacturing Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 238000001035 drying Methods 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract 1
- 238000000622 liquid--liquid extraction Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
- 238000011282 treatment Methods 0.000 description 19
- IPQVTOJGNYVQEO-UHFFFAOYSA-N 9-[2-carboxy-4-hydroxy-10-oxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9h-anthracen-9-yl]-4-hydroxy-10-oxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9h-anthracene-2-carboxylic acid Chemical class OC1C(O)C(O)C(CO)OC1OC1=CC=CC2=C1C(=O)C1=C(O)C=C(C(O)=O)C=C1C2C1C2=CC(C(O)=O)=CC(O)=C2C(=O)C2=C(OC3C(C(O)C(O)C(CO)O3)O)C=CC=C21 IPQVTOJGNYVQEO-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000012071 phase Substances 0.000 description 16
- 238000007254 oxidation reaction Methods 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 244000208060 Lawsonia inermis Species 0.000 description 8
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 8
- 229960002009 naproxen Drugs 0.000 description 8
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 8
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 230000021736 acetylation Effects 0.000 description 6
- 238000006640 acetylation reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 5
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 5
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 5
- 201000008482 osteoarthritis Diseases 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 235000019155 vitamin A Nutrition 0.000 description 5
- 239000011719 vitamin A Substances 0.000 description 5
- 229940045997 vitamin a Drugs 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229930182478 glucoside Natural products 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 230000009854 mucosal lesion Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000902 placebo Substances 0.000 description 4
- 229940068196 placebo Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000001509 sodium citrate Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000006693 Cassia laevigata Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 206010018691 Granuloma Diseases 0.000 description 3
- 241000522641 Senna Species 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 3
- 229940038773 trisodium citrate Drugs 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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 description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 240000001624 Espostoa lanata Species 0.000 description 2
- 235000009161 Espostoa lanata Nutrition 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 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 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 2
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 2
- 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 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- FOANPUVWJFUIQP-UHFFFAOYSA-N 1,2-diacetylanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(C(C)=O)C(C(=O)C)=CC=C3C(=O)C2=C1 FOANPUVWJFUIQP-UHFFFAOYSA-N 0.000 description 1
- FIHZWZBEAXASKA-UHFFFAOYSA-N Anthron Natural products COc1cc2Cc3cc(C)cc(O)c3C(=O)c2c(O)c1C=CC(C)C FIHZWZBEAXASKA-UHFFFAOYSA-N 0.000 description 1
- RBTVVLRQDWBHPD-UHFFFAOYSA-N C(C)(=O)[Rh] Chemical compound C(C)(=O)[Rh] RBTVVLRQDWBHPD-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 208000003947 Knee Osteoarthritis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 241000269799 Perca fluviatilis Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000219061 Rheum Species 0.000 description 1
- 241001249696 Senna alexandrina Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000002456 anti-arthritic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- FGBWQDUVIQQXRW-UHFFFAOYSA-N diacetylmercury Chemical compound CC(=O)[Hg]C(C)=O FGBWQDUVIQQXRW-UHFFFAOYSA-N 0.000 description 1
- MGRRGKWPEVFJSH-UHFFFAOYSA-N dianthrone Natural products C12=CC=CC=C2C(=O)C2=CC=CC=C2C1=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MGRRGKWPEVFJSH-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 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)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (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)
- Diaphragms For Electromechanical Transducers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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 (fi) | 2000-04-28 |
Family
ID=6434717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI922930A FI104892B (fi) | 1991-06-25 | 1992-06-24 | Diasetyylirheinin valmistusmenetelmä |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US5391775A (fr) |
| EP (1) | EP0520414B1 (fr) |
| JP (1) | JPH0825955B2 (fr) |
| AT (1) | ATE135341T1 (fr) |
| AU (1) | AU645208B2 (fr) |
| CA (1) | CA2072283C (fr) |
| CZ (1) | CZ194892A3 (fr) |
| DE (2) | DE4120989C2 (fr) |
| DK (1) | DK0520414T3 (fr) |
| ES (1) | ES2084877T3 (fr) |
| FI (1) | FI104892B (fr) |
| GR (1) | GR3019321T3 (fr) |
| HU (1) | HU220390B (fr) |
| IE (1) | IE72526B1 (fr) |
| PL (1) | PL168847B1 (fr) |
| RU (1) | RU2104996C1 (fr) |
| SK (1) | SK194892A3 (fr) |
| TW (1) | TW400333B (fr) |
| ZA (1) | ZA924644B (fr) |
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 (fi) * | 1993-12-17 | 1996-08-12 | Leiras Oy | Menetelmä sennosidien A ja B valmistamiseksi |
| 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 (fr) * | 2001-06-25 | 2003-01-03 | Arakis Ltd. | Utilisation de la rheine et de ses derives dans le traitement de la douleur |
| 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. |
| EP2364287B1 (fr) | 2008-12-09 | 2014-04-02 | Evultis S.A. | Procede de preparation de diacetylrheine (diacereine) non genotoxique et formulations comprenant de la diacetylrheine non genotoxique |
| EP2218707A1 (fr) | 2009-02-16 | 2010-08-18 | Evultis S.A. | Procédé pour la préparation de diacétylrhéine (diacéréine) non génotoxique |
| EP2196450A1 (fr) | 2008-12-09 | 2010-06-16 | Evultis S.A. | Procédé pour la préparation de diacétylrhéine (diacéréine) pure |
| WO2011099834A2 (fr) * | 2010-02-15 | 2011-08-18 | Interquim, S.A. De C.V. | Procédé de purification de diacéréine brute à l'aide de sel de potassium/diméthyl formamide |
| ITTO20110120A1 (it) | 2011-02-11 | 2012-08-12 | Icrom Spa | Un nuovo processo di purificazione per derivati antrachinonici |
| EP2872474B1 (fr) * | 2012-07-10 | 2022-01-19 | Georgia State University Research Foundation, Inc. | Analogues d'anthraquinone et leurs procédés de fabrication et d'utilisation |
| 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 RU SU5052409/04A patent/RU2104996C1/ru not_active IP Right Cessation
- 1992-06-24 CZ CS921948A patent/CZ194892A3/cs unknown
- 1992-06-24 DK DK92110652.2T patent/DK0520414T3/da active
- 1992-06-24 AU AU18484/92A patent/AU645208B2/en not_active Expired
- 1992-06-24 ES ES92110652T patent/ES2084877T3/es not_active Expired - Lifetime
- 1992-06-24 ZA ZA924644A patent/ZA924644B/xx unknown
- 1992-06-24 FI FI922930A patent/FI104892B/fi active
- 1992-06-24 HU HU9202108A patent/HU220390B/hu not_active IP Right Cessation
- 1992-06-24 EP EP92110652A patent/EP0520414B1/fr not_active Expired - Lifetime
- 1992-06-24 PL PL92295006A patent/PL168847B1/pl unknown
- 1992-06-24 SK SK1948-92A patent/SK194892A3/sk unknown
- 1992-06-24 JP JP4165960A patent/JPH0825955B2/ja not_active Expired - Lifetime
- 1992-06-24 AT AT92110652T patent/ATE135341T1/de not_active IP Right Cessation
- 1992-06-24 DE DE59205646T patent/DE59205646D1/de not_active Expired - Lifetime
- 1992-06-25 CA CA002072283A patent/CA2072283C/fr 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 |
|---|---|
| ES2084877T3 (es) | 1996-05-16 |
| AU645208B2 (en) | 1994-01-06 |
| US5391775A (en) | 1995-02-21 |
| TW400333B (en) | 2000-08-01 |
| HU9202108D0 (en) | 1992-10-28 |
| HUT61263A (en) | 1992-12-28 |
| EP0520414A1 (fr) | 1992-12-30 |
| DE4120989C2 (de) | 1995-07-27 |
| FI922930A (fi) | 1992-12-26 |
| JPH05186394A (ja) | 1993-07-27 |
| IE72526B1 (en) | 1997-04-23 |
| IE922046A1 (en) | 1992-12-30 |
| SK194892A3 (en) | 1995-02-08 |
| CA2072283C (fr) | 2000-10-24 |
| DE59205646D1 (de) | 1996-04-18 |
| RU2104996C1 (ru) | 1998-02-20 |
| DK0520414T3 (da) | 1996-04-01 |
| FI922930A0 (fi) | 1992-06-24 |
| DE4120989A1 (de) | 1993-01-07 |
| JPH0825955B2 (ja) | 1996-03-13 |
| CA2072283A1 (fr) | 1992-12-26 |
| GR3019321T3 (en) | 1996-06-30 |
| US6624192B1 (en) | 2003-09-23 |
| HU220390B (hu) | 2002-01-28 |
| AU1848492A (en) | 1993-03-11 |
| PL168847B1 (pl) | 1996-04-30 |
| ZA924644B (en) | 1993-03-31 |
| EP0520414B1 (fr) | 1996-03-13 |
| PL295006A1 (en) | 1993-02-22 |
| CZ194892A3 (en) | 1993-01-13 |
| ATE135341T1 (de) | 1996-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI104892B (fi) | Diasetyylirheinin valmistusmenetelmä | |
| CA2802154C (fr) | Procede de preparation d'une composition d'asiaticoside tres pure a partir de centella asiatica et son procede d'utilisation | |
| SK9498A3 (en) | Use of calendula glycosides for the treatment of psoriasis | |
| CA2334656C (fr) | Procede de preparation d'aloine par extraction | |
| FI104893B (fi) | Menetelmä diasetyylireiinin valmistamiseksi | |
| JP2705733B2 (ja) | センノシドａ，ｂおよびａ１を主成分とする混合物、その取得法及び該混合物を含有する緩下剤 | |
| JP3828163B2 (ja) | 抗炎症、抗かゆみ剤 | |
| JPH0128752B2 (fr) | ||
| WO2002069952A1 (fr) | Agents anti-inflammatoires contenant de nouveaux composes ou leurs derives | |
| BE879804A (fr) | Nouveaux derives indoliques pentacycliques, leur procede d'obtention et compositions pharmaceutiques les contenant |