LU87298A1 - Nouveau derive de diosmine et sa preparation - Google Patents
Nouveau derive de diosmine et sa preparation Download PDFInfo
- Publication number
- LU87298A1 LU87298A1 LU87298A LU87298A LU87298A1 LU 87298 A1 LU87298 A1 LU 87298A1 LU 87298 A LU87298 A LU 87298A LU 87298 A LU87298 A LU 87298A LU 87298 A1 LU87298 A1 LU 87298A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- diosmin
- preparation
- sulfur trioxide
- derivative
- reaction
- Prior art date
Links
- GZSOSUNBTXMUFQ-YFAPSIMESA-N diosmin Chemical class C1=C(O)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)O1 GZSOSUNBTXMUFQ-YFAPSIMESA-N 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 9
- GZSOSUNBTXMUFQ-NJGQXECBSA-N 5,7,3'-Trihydroxy-4'-methoxyflavone 7-O-rutinoside Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](Oc2cc(O)c3C(=O)C=C(c4cc(O)c(OC)cc4)Oc3c2)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 GZSOSUNBTXMUFQ-NJGQXECBSA-N 0.000 claims description 19
- 229960004352 diosmin Drugs 0.000 claims description 19
- IGBKNLGEMMEWKD-UHFFFAOYSA-N diosmin Natural products COc1ccc(cc1)C2=C(O)C(=O)c3c(O)cc(OC4OC(COC5OC(C)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 IGBKNLGEMMEWKD-UHFFFAOYSA-N 0.000 claims description 19
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- MBPDDAGACPZDAA-UHFFFAOYSA-K aluminum hydrogen sulfate sulfuric acid sulfate Chemical compound [Al+3].OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS([O-])(=O)=O.[O-]S([O-])(=O)=O MBPDDAGACPZDAA-UHFFFAOYSA-K 0.000 claims description 6
- 230000001180 sulfating effect Effects 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 238000005670 sulfation reaction Methods 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- YYHPEVZFVMVUNJ-UHFFFAOYSA-N n,n-diethylethanamine;sulfur trioxide Chemical compound O=S(=O)=O.CCN(CC)CC YYHPEVZFVMVUNJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000448369 Vizcaya Species 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NNCOOIBIVIODKO-UHFFFAOYSA-N aluminum;hypochlorous acid Chemical compound [Al].ClO NNCOOIBIVIODKO-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 210000001156 gastric mucosa Anatomy 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- -1 sterol sulfate esters Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- 240000008213 Brosimum alicastrum Species 0.000 description 1
- 125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000013475 authorization Methods 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical compound CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000005828 ramon Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES554841 | 1986-05-09 | ||
| ES554841A ES8707969A1 (es) | 1986-05-09 | 1986-05-09 | Procedimiento de preparacion de una mezcla estandar de o-(b-hidroxietil)-diosminas |
| ES8702270 | 1987-07-31 | ||
| ES8702270A ES2004465A6 (es) | 1986-05-09 | 1987-07-31 | Procedimiento de preparcion de un nuevo derivado de diosmina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87298A1 true LU87298A1 (fr) | 1989-02-02 |
Family
ID=39671968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87298A LU87298A1 (fr) | 1986-05-09 | 1988-07-27 | Nouveau derive de diosmine et sa preparation |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4894449A (de) |
| EP (1) | EP0302155B1 (de) |
| DE (1) | DE3715447C2 (de) |
| ES (2) | ES8707969A1 (de) |
| FR (1) | FR2598415B1 (de) |
| IT (1) | IT1215471B (de) |
| LU (1) | LU87298A1 (de) |
| NL (1) | NL8801840A (de) |
| PT (2) | PT82827B (de) |
| SE (1) | SE8802755L (de) |
| ZA (1) | ZA885264B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5202123A (en) * | 1990-04-20 | 1993-04-13 | Somerville Technology Group, Inc. | Surface modified aluminum and aluminum-zirconium salts |
| ES2041216B1 (es) * | 1992-02-25 | 1994-06-16 | Espanola Prod Quimicos | Procedimiento de preparacion de un nuevo derivado sulfatado de diosmina. |
| ES2158774B1 (es) * | 1999-04-12 | 2002-03-16 | Faes Fabrica Espanola De Produ | Nuevo procedimiento para la preparacion industrial de dosmalfato en povo. |
| US7034054B2 (en) * | 2000-12-15 | 2006-04-25 | Galileo Pharmaceuticals, Inc. | Methods for the prevention and treatment of cerebral ischemia using non-alpha tocopherols |
| US6384271B1 (en) * | 2001-05-04 | 2002-05-07 | E.I. Du Pont De Nemours And Company | Sulfonation, sulfation and sulfamation |
| CN103408621B (zh) * | 2013-08-16 | 2015-09-30 | 李玉山 | 一种海曲司明的合成工艺 |
| CN108992456B (zh) * | 2018-07-19 | 2021-05-04 | 湘北威尔曼制药股份有限公司 | 含有香叶木苷硫酸酯衍生物的药物组合物及其应用 |
| WO2020224452A1 (zh) | 2019-05-05 | 2020-11-12 | 广州新创忆药物临床研究有限公司 | 一种调节人体体重失衡的化合物、其组合物及其应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3432489A (en) * | 1965-11-05 | 1969-03-11 | Chugai Pharmaceutical Co Ltd | Disaccharide polysulfate aluminium compound and method |
| FR6967M (de) * | 1968-01-22 | 1969-05-19 | ||
| ES469101A1 (es) * | 1978-04-25 | 1978-11-16 | Espanola Prod Quimicos | Procedimiento de obtencion de eteres hidrosolubles de hidro-xiflavonas. |
| US4334058A (en) * | 1979-07-31 | 1982-06-08 | American Cyanamid Company | Rutin poly(H--)sulfate salts and related compounds |
| CH644374A5 (en) * | 1981-05-18 | 1984-07-31 | Espanola Prod Quimicos | Water-soluble hydroxyflavone ethers and medicaments containing them |
| US4342753A (en) * | 1981-06-15 | 1982-08-03 | American Cyanamid Company | Carboxyalkyl derivatives of rutin poly(H-)sulfate |
| EP0075626A1 (de) * | 1981-09-29 | 1983-04-06 | American Cyanamid Company | Salze von Nona- und Deca(H-)rutinsulfat, Verfahren zur Herstellung der Salze und Verwendung der Salze als Komplement-Inhibitor |
-
1986
- 1986-05-09 ES ES554841A patent/ES8707969A1/es not_active Expired
- 1986-06-23 PT PT82827A patent/PT82827B/pt unknown
-
1987
- 1987-05-07 FR FR8706508A patent/FR2598415B1/fr not_active Expired - Lifetime
- 1987-05-08 DE DE3715447A patent/DE3715447C2/de not_active Expired - Fee Related
- 1987-05-08 IT IT8720444A patent/IT1215471B/it active
- 1987-07-31 ES ES8702270A patent/ES2004465A6/es not_active Expired
- 1987-07-31 EP EP87500053A patent/EP0302155B1/de not_active Expired - Lifetime
-
1988
- 1988-07-20 ZA ZA885264A patent/ZA885264B/xx unknown
- 1988-07-20 NL NL8801840A patent/NL8801840A/nl not_active Application Discontinuation
- 1988-07-27 LU LU87298A patent/LU87298A1/fr unknown
- 1988-07-28 US US07/225,544 patent/US4894449A/en not_active Expired - Fee Related
- 1988-07-29 PT PT88158A patent/PT88158B/pt not_active IP Right Cessation
- 1988-07-29 SE SE8802755A patent/SE8802755L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2004465A6 (es) | 1989-01-01 |
| ES8707969A1 (es) | 1987-10-01 |
| US4894449A (en) | 1990-01-16 |
| PT88158A (pt) | 1989-06-30 |
| EP0302155B1 (de) | 1993-10-27 |
| FR2598415A1 (fr) | 1987-11-13 |
| PT82827A (en) | 1986-07-01 |
| DE3715447C2 (de) | 1998-09-03 |
| SE8802755L (sv) | 1989-02-01 |
| EP0302155A1 (de) | 1989-02-08 |
| PT82827B (pt) | 1988-04-21 |
| ZA885264B (en) | 1989-07-26 |
| IT8720444A0 (it) | 1987-05-08 |
| PT88158B (pt) | 1995-03-01 |
| DE3715447A1 (de) | 1988-02-11 |
| FR2598415B1 (fr) | 1994-05-27 |
| NL8801840A (nl) | 1989-02-16 |
| SE8802755D0 (sv) | 1988-07-29 |
| IT1215471B (it) | 1990-02-14 |
| ES554841A0 (es) | 1987-10-01 |
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