WO1999028312A1 - Nouveaux glycosides anticoagulants et leurs compositions pharmaceutiques - Google Patents
Nouveaux glycosides anticoagulants et leurs compositions pharmaceutiques Download PDFInfo
- Publication number
- WO1999028312A1 WO1999028312A1 PCT/HU1998/000099 HU9800099W WO9928312A1 WO 1999028312 A1 WO1999028312 A1 WO 1999028312A1 HU 9800099 W HU9800099 W HU 9800099W WO 9928312 A1 WO9928312 A1 WO 9928312A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dithio
- arabinopyranoside
- formula
- compound
- mixture
- Prior art date
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- 239000003146 anticoagulant agent Substances 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 5
- 229930182470 glycoside Natural products 0.000 title description 13
- 150000002338 glycosides Chemical class 0.000 title description 13
- 229940127219 anticoagulant drug Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- -1 cyano, nitro, aminothiocarbonyl Chemical group 0.000 claims abstract description 17
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 22
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 15
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 abstract description 4
- 230000001225 therapeutic effect Effects 0.000 abstract description 4
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- 230000002429 anti-coagulating effect Effects 0.000 abstract 1
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- 238000000034 method Methods 0.000 description 44
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- 125000003118 aryl group Chemical group 0.000 description 27
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- 239000007858 starting material Substances 0.000 description 21
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- 239000008121 dextrose Substances 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002002 slurry 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003569 thioglycosides Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000002328 two-dimensional heteronuclear correlation spectroscopy Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical compound [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/08—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium
- C07H5/10—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to sulfur, selenium or tellurium to sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
L'invention concerne de nouveaux 1,5-dithio-L- et D-arabinopyrannosides de formule (I), dans laquelle R représente un cyano, nitro, aminothiocarbonyle, aminido ou un groupe acétamide et leurs sels d'addition d'acide formés, de préférence, avec des acides organiques ou inorganiques et des compositions pharmaceutiques les contenant. Les composés possèdent des propriétés thérapeutiques et plus spécifiquement anticoagulantes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU13467/99A AU1346799A (en) | 1997-12-04 | 1998-12-03 | Novel anticoagulant glycosides and pharmaceutical compositions thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP9702348 | 1997-12-04 | ||
| HU97023489702348A HUP9702348A3 (en) | 1997-12-04 | 1997-12-04 | New anticoagulant glycosides and pharmaceutical conew anticoagulant glycosides and pharmaceutical compositions containing them mpositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1999028312A1 true WO1999028312A1 (fr) | 1999-06-10 |
Family
ID=89995815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/HU1998/000099 WO1999028312A1 (fr) | 1997-12-04 | 1998-12-03 | Nouveaux glycosides anticoagulants et leurs compositions pharmaceutiques |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU1346799A (fr) |
| HU (1) | HUP9702348A3 (fr) |
| WO (1) | WO1999028312A1 (fr) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015125572A1 (fr) * | 2014-02-19 | 2015-08-27 | 富士フイルム株式会社 | Composé thiopyranose et son procédé de production |
| US9884882B2 (en) | 2014-02-18 | 2018-02-06 | Fujifilm Corporation | Method for producing thiolane skeleton-type glycoconjugate, and thiolane skeleton-type glycoconjugate |
| US9896471B2 (en) | 2012-03-28 | 2018-02-20 | Fujifilm Corporation | Salt of 1-(2-deoxy-2-fluoro-4-thio-β-D-arabinofuranosyl)cytosine |
| US10059734B2 (en) | 2014-10-31 | 2018-08-28 | Fujifilm Corporation | Thionucleoside derivative or salt thereof, and pharmaceutical composition |
| US10093645B2 (en) | 2012-08-13 | 2018-10-09 | Fujifilm Corporation | Synthetic intermediate of 1-(2-deoxy-2-fluoro-4-thio-β-D-arabinofuranosyl)cytosine, synthetic intermediate of thionucleoside, and method for producing the same |
| US11141421B2 (en) | 2018-01-29 | 2021-10-12 | Fujifilm Corporation | Antitumor agent for biliary tract cancer and method for treating biliary tract cancer |
| US11369625B2 (en) | 2016-08-31 | 2022-06-28 | Fujifilm Corporation | Anti-tumor agent, anti-tumor effect enhancer, and anti-tumor kit |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4454123A (en) * | 1980-12-09 | 1984-06-12 | Seikagaku Kogyo Co. Ltd. | O-xylopyranoside series compounds and methods of use |
| EP0365397A2 (fr) * | 1988-10-18 | 1990-04-25 | Fournier Industrie Et Sante | Nouveaux beta-D-phényl-thioxylosides, leur procédé de préparation et leur utilisation en thérapeutique |
-
1997
- 1997-12-04 HU HU97023489702348A patent/HUP9702348A3/hu unknown
-
1998
- 1998-12-03 WO PCT/HU1998/000099 patent/WO1999028312A1/fr active Application Filing
- 1998-12-03 AU AU13467/99A patent/AU1346799A/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4454123A (en) * | 1980-12-09 | 1984-06-12 | Seikagaku Kogyo Co. Ltd. | O-xylopyranoside series compounds and methods of use |
| EP0365397A2 (fr) * | 1988-10-18 | 1990-04-25 | Fournier Industrie Et Sante | Nouveaux beta-D-phényl-thioxylosides, leur procédé de préparation et leur utilisation en thérapeutique |
Non-Patent Citations (2)
| Title |
|---|
| E. BOZO ET. AL.: "Synthesis of 4-cyanophenyl 4-azido-4-deoxy- 1,5-dithio- beta-D-Xylopyranoside", CARBOHYDRATE RESEARCH, vol. 302, 1997, pages 149-162, XP004093557 * |
| E. BOZO ET. AL.: "Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio L- and D-arabinopyranosides possessing antithrombotic activity.", CARBOHYDRATE RESEARCH, vol. 311, 1998, pages 191 - 202, XP004141931 * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9896471B2 (en) | 2012-03-28 | 2018-02-20 | Fujifilm Corporation | Salt of 1-(2-deoxy-2-fluoro-4-thio-β-D-arabinofuranosyl)cytosine |
| US10570112B2 (en) | 2012-08-13 | 2020-02-25 | Fujifilm Corporation | Synthetic intermediate of 1-(2-deoxy-2-fluoro-4-thio-β-D-arabinofuranosyl)cytosine, synthetic intermediate of thionucleoside, and method for producing the same |
| US10093645B2 (en) | 2012-08-13 | 2018-10-09 | Fujifilm Corporation | Synthetic intermediate of 1-(2-deoxy-2-fluoro-4-thio-β-D-arabinofuranosyl)cytosine, synthetic intermediate of thionucleoside, and method for producing the same |
| US9884882B2 (en) | 2014-02-18 | 2018-02-06 | Fujifilm Corporation | Method for producing thiolane skeleton-type glycoconjugate, and thiolane skeleton-type glycoconjugate |
| EP3109246A4 (fr) * | 2014-02-19 | 2017-04-26 | Fujifilm Corporation | Composé thiopyranose et son procédé de production |
| US9815812B2 (en) | 2014-02-19 | 2017-11-14 | Fujifilm Corporation | Thiopyranose compound and method for producing same |
| WO2015125572A1 (fr) * | 2014-02-19 | 2015-08-27 | 富士フイルム株式会社 | Composé thiopyranose et son procédé de production |
| EP3109246A1 (fr) * | 2014-02-19 | 2016-12-28 | Fujifilm Corporation | Composé thiopyranose et son procédé de production |
| JP2015155380A (ja) * | 2014-02-19 | 2015-08-27 | 富士フイルム株式会社 | チオピラノース化合物およびその製造方法 |
| US10059734B2 (en) | 2014-10-31 | 2018-08-28 | Fujifilm Corporation | Thionucleoside derivative or salt thereof, and pharmaceutical composition |
| US10385089B2 (en) | 2014-10-31 | 2019-08-20 | Fujifilm Corporation | Thionucleoside derivative or salt thereof, and pharmaceutical composition |
| US11369625B2 (en) | 2016-08-31 | 2022-06-28 | Fujifilm Corporation | Anti-tumor agent, anti-tumor effect enhancer, and anti-tumor kit |
| US11141421B2 (en) | 2018-01-29 | 2021-10-12 | Fujifilm Corporation | Antitumor agent for biliary tract cancer and method for treating biliary tract cancer |
Also Published As
| Publication number | Publication date |
|---|---|
| AU1346799A (en) | 1999-06-16 |
| HU9702348D0 (en) | 1998-03-02 |
| HUP9702348A2 (hu) | 1999-08-30 |
| HUP9702348A3 (en) | 2000-12-28 |
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