DE3632536A1 - Verfahren zur herstellung von 5-bromsalizyl-4'-chloranilid-o-glykosiden - Google Patents
Verfahren zur herstellung von 5-bromsalizyl-4'-chloranilid-o-glykosidenInfo
- Publication number
- DE3632536A1 DE3632536A1 DE19863632536 DE3632536A DE3632536A1 DE 3632536 A1 DE3632536 A1 DE 3632536A1 DE 19863632536 DE19863632536 DE 19863632536 DE 3632536 A DE3632536 A DE 3632536A DE 3632536 A1 DE3632536 A1 DE 3632536A1
- Authority
- DE
- Germany
- Prior art keywords
- chloranilide
- bromosalicyl
- sugar
- bromosalizyl
- chloroanilide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- -1 5-bromosalicyl-4'-chloranilide O-glycosides Chemical class 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 229930182473 O-glycoside Natural products 0.000 title abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 32
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000008096 xylene Substances 0.000 claims abstract description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012442 inert solvent Substances 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract 4
- 238000000605 extraction Methods 0.000 claims abstract 2
- 150000007524 organic acids Chemical class 0.000 claims abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- QBSGXIBYUQJHMJ-UHFFFAOYSA-N bromochlorosalicylanilide Chemical compound OC1=CC=C(Br)C=C1C(=O)NC1=CC=C(Cl)C=C1 QBSGXIBYUQJHMJ-UHFFFAOYSA-N 0.000 abstract 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 1
- 150000008444 O-glycosides Chemical class 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- JWDUFIUUDGFMTM-YTWAJWBKSA-N [(3r,4s,5r,6r)-4,5-diacetyloxy-6-chlorooxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@H](Cl)[C@H](OC(C)=O)[C@H]1OC(C)=O JWDUFIUUDGFMTM-YTWAJWBKSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229940121375 antifungal agent Drugs 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 206010000349 Acanthosis Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 206010012504 Dermatophytosis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 238000005858 glycosidation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 150000008136 β-glycosides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD28601586A DD292651A5 (de) | 1986-01-08 | 1986-01-08 | Verfahren zur herstellung von 5-bromsalizyl-4'-chloranilid-o-glykosiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3632536A1 true DE3632536A1 (de) | 1987-07-09 |
| DE3632536C2 DE3632536C2 (enExample) | 1989-04-06 |
Family
ID=5575737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863632536 Granted DE3632536A1 (de) | 1986-01-08 | 1986-09-25 | Verfahren zur herstellung von 5-bromsalizyl-4'-chloranilid-o-glykosiden |
Country Status (2)
| Country | Link |
|---|---|
| DD (1) | DD292651A5 (enExample) |
| DE (1) | DE3632536A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001074835A1 (en) * | 2000-03-30 | 2001-10-11 | Bristol-Myers Squibb Company | O-glucosylated benzamide sglt2 inhibitors and method |
| US6936590B2 (en) | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| CZ297581B6 (cs) * | 2005-05-26 | 2007-01-10 | Universita Karlova v Praze, Farmaceutická fakulta v Hradci Králové | Antimykotické a antimykobakteriální thiosalicylanilidy a způsob jejich přípravy |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD222031A1 (de) * | 1983-09-02 | 1985-05-08 | Adw Ddr | Verfahren zur herstellung von 5-bromsalizyl-4'-chloranilid-o-glykosiden |
-
1986
- 1986-01-08 DD DD28601586A patent/DD292651A5/de not_active IP Right Cessation
- 1986-09-25 DE DE19863632536 patent/DE3632536A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD222031A1 (de) * | 1983-09-02 | 1985-05-08 | Adw Ddr | Verfahren zur herstellung von 5-bromsalizyl-4'-chloranilid-o-glykosiden |
Non-Patent Citations (7)
| Title |
|---|
| Agric. Biol. Chem., 1983, 47(5), 1123-1125 * |
| Aust. J. Chem., 1955, 8, 403-408 * |
| Chem. Ber., 1933, 66, 378 * |
| Dermatologische Monatsschrift, 1984, 170, 38 * |
| Mykosen, 1982, 25, 487-496 * |
| OVEREND, W.G.: in The Carbohydrates, Hrg.: Pigman, W. und Horton, D., Bd. IA, 1972, Academic Press, New York, S.292-293 * |
| WP(DDR)150471 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001074835A1 (en) * | 2000-03-30 | 2001-10-11 | Bristol-Myers Squibb Company | O-glucosylated benzamide sglt2 inhibitors and method |
| US6555519B2 (en) | 2000-03-30 | 2003-04-29 | Bristol-Myers Squibb Company | O-glucosylated benzamide SGLT2 inhibitors and method |
| US6936590B2 (en) | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| CZ297581B6 (cs) * | 2005-05-26 | 2007-01-10 | Universita Karlova v Praze, Farmaceutická fakulta v Hradci Králové | Antimykotické a antimykobakteriální thiosalicylanilidy a způsob jejich přípravy |
Also Published As
| Publication number | Publication date |
|---|---|
| DD292651A5 (de) | 1991-08-08 |
| DE3632536C2 (enExample) | 1989-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SAECHSISCHES SERUMWERK GMBH, O-8010 DRESDEN, DE |
|
| 8339 | Ceased/non-payment of the annual fee |