SK6562002A3 - Beta-d-5-thioxylose derivatives, preparation method and therapeutic use - Google Patents
Beta-d-5-thioxylose derivatives, preparation method and therapeutic use Download PDFInfo
- Publication number
- SK6562002A3 SK6562002A3 SK656-2002A SK6562002A SK6562002A3 SK 6562002 A3 SK6562002 A3 SK 6562002A3 SK 6562002 A SK6562002 A SK 6562002A SK 6562002 A3 SK6562002 A3 SK 6562002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- carbon atoms
- benzopyran
- oxo
- thio
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000002009 alkene group Chemical group 0.000 claims abstract description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 9
- 230000002785 anti-thrombosis Effects 0.000 claims abstract description 6
- 239000003146 anticoagulant agent Substances 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- -1 4-methyl-2-oxo-2H-1-benzopyran-7-yl-5-thio-β-D-xylopyranoside compound Chemical class 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 238000003763 carbonization Methods 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- JRHNIQQUVJOPQC-AQNFWKISSA-N 4-methyl-7-[(2r,3r,4s,5s)-3,4,5-trihydroxythian-2-yl]oxychromen-2-one Chemical compound C1=CC=2C(C)=CC(=O)OC=2C=C1O[C@@H]1SC[C@@H](O)[C@H](O)[C@H]1O JRHNIQQUVJOPQC-AQNFWKISSA-N 0.000 claims description 3
- 230000017531 blood circulation Effects 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 208000007536 Thrombosis Diseases 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 235000010300 dimethyl dicarbonate Nutrition 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010047249 Venous thrombosis Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YJYAGNPMQVHYAH-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxyethanol Chemical compound CC(C)(C)[Si](C)(C)OCCO YJYAGNPMQVHYAH-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- NDYYWMXJZWHRLZ-UHFFFAOYSA-N 2-methoxyethyl carbonochloridate Chemical group COCCOC(Cl)=O NDYYWMXJZWHRLZ-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- 125000004746 2-methylpropyloxycarbonyl group Chemical group CC(COC(=O)*)C 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 108010074860 Factor Xa Proteins 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020608 Hypercoagulation Diseases 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 208000034158 bleeding Diseases 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical group CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 230000003027 hypercoagulation Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940127215 low-molecular weight heparin Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical group ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 201000002282 venous insufficiency Diseases 0.000 description 1
- 238000005303 weighing Methods 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
- C07H17/075—Benzo[b]pyran-2-ones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9914445A FR2801055B1 (fr) | 1999-11-17 | 1999-11-17 | Derives de beta-d-5-thioxylose, procede de preparation et utilisation en therapeutique |
| PCT/FR2000/003174 WO2001036437A1 (fr) | 1999-11-17 | 2000-11-15 | DERIVES DE β-D-5-THIOXYLOSE, PROCEDE DE PREPARATION ET UTILISATION EN THERAPEUTIQUE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK6562002A3 true SK6562002A3 (en) | 2002-08-06 |
Family
ID=9552208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK656-2002A SK6562002A3 (en) | 1999-11-17 | 2000-11-15 | Beta-d-5-thioxylose derivatives, preparation method and therapeutic use |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6602899B1 (de) |
| EP (1) | EP1230252B1 (de) |
| JP (1) | JP2003514826A (de) |
| KR (1) | KR20020050282A (de) |
| CN (1) | CN1224626C (de) |
| AT (1) | ATE264338T1 (de) |
| AU (1) | AU777920B2 (de) |
| CA (1) | CA2391100A1 (de) |
| CZ (1) | CZ20021589A3 (de) |
| DE (1) | DE60009945T2 (de) |
| DK (1) | DK1230252T3 (de) |
| ES (1) | ES2219419T3 (de) |
| FR (1) | FR2801055B1 (de) |
| HK (1) | HK1049341A1 (de) |
| HU (1) | HUP0203468A3 (de) |
| IL (1) | IL149620A0 (de) |
| MX (1) | MXPA02004916A (de) |
| NO (1) | NO20022279D0 (de) |
| NZ (1) | NZ518864A (de) |
| PL (1) | PL356208A1 (de) |
| PT (1) | PT1230252E (de) |
| SK (1) | SK6562002A3 (de) |
| TR (1) | TR200400907T4 (de) |
| WO (1) | WO2001036437A1 (de) |
| ZA (1) | ZA200203570B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003254903B9 (en) * | 2002-08-09 | 2008-08-21 | Taisho Pharmaceutical Co., Ltd. | Method for selective preparation of aryl 5-thio-beta-D-aldohexopyranosides |
| FR2860234B1 (fr) * | 2003-09-25 | 2005-12-23 | Fournier Lab Sa | Nouveaux derives 666 du thioxylose |
| UY29237A1 (es) * | 2004-12-01 | 2006-05-31 | Glaxo Group Ltd | Metodos detratamiento y prevencion |
| TW200640449A (en) * | 2005-02-18 | 2006-12-01 | Smithkline Beecham Corp | Pharmaceutical compositions and methods |
| FR2883561B1 (fr) * | 2005-03-25 | 2009-03-20 | Fournier S A Sa Lab | Nouveaux composes derives du 5-thioxylose et leur utilisation therapeutique |
| FR2903698B1 (fr) * | 2006-07-13 | 2009-01-30 | Fournier S A Sa Lab | Nouveaux derives de 5-thioxylopyranose. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0421829T3 (da) * | 1989-09-22 | 1995-01-16 | Fournier Ind & Sante | Nye benzopyranon-beta-D-thioxylosider, fremgangsmåde til deres fremstilling og deres terapeutiske anvendelse |
-
1999
- 1999-11-17 FR FR9914445A patent/FR2801055B1/fr not_active Expired - Fee Related
-
2000
- 2000-11-15 DK DK00979738T patent/DK1230252T3/da active
- 2000-11-15 CN CNB008158495A patent/CN1224626C/zh not_active Expired - Fee Related
- 2000-11-15 SK SK656-2002A patent/SK6562002A3/sk unknown
- 2000-11-15 PT PT00979738T patent/PT1230252E/pt unknown
- 2000-11-15 PL PL00356208A patent/PL356208A1/xx unknown
- 2000-11-15 ES ES00979738T patent/ES2219419T3/es not_active Expired - Lifetime
- 2000-11-15 AU AU17131/01A patent/AU777920B2/en not_active Ceased
- 2000-11-15 CZ CZ20021589A patent/CZ20021589A3/cs unknown
- 2000-11-15 HK HK03101549.1A patent/HK1049341A1/zh unknown
- 2000-11-15 DE DE60009945T patent/DE60009945T2/de not_active Expired - Fee Related
- 2000-11-15 MX MXPA02004916A patent/MXPA02004916A/es active IP Right Grant
- 2000-11-15 NZ NZ518864A patent/NZ518864A/en unknown
- 2000-11-15 HU HU0203468A patent/HUP0203468A3/hu unknown
- 2000-11-15 JP JP2001538926A patent/JP2003514826A/ja active Pending
- 2000-11-15 US US10/129,899 patent/US6602899B1/en not_active Expired - Fee Related
- 2000-11-15 EP EP00979738A patent/EP1230252B1/de not_active Expired - Lifetime
- 2000-11-15 IL IL14962000A patent/IL149620A0/xx unknown
- 2000-11-15 TR TR2004/00907T patent/TR200400907T4/xx unknown
- 2000-11-15 KR KR1020027006185A patent/KR20020050282A/ko not_active Withdrawn
- 2000-11-15 CA CA002391100A patent/CA2391100A1/fr not_active Abandoned
- 2000-11-15 AT AT00979738T patent/ATE264338T1/de not_active IP Right Cessation
- 2000-11-15 WO PCT/FR2000/003174 patent/WO2001036437A1/fr not_active Ceased
-
2002
- 2002-05-06 ZA ZA200203570A patent/ZA200203570B/xx unknown
- 2002-05-14 NO NO20022279A patent/NO20022279D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1224626C (zh) | 2005-10-26 |
| NZ518864A (en) | 2005-07-29 |
| CN1391578A (zh) | 2003-01-15 |
| MXPA02004916A (es) | 2002-09-18 |
| AU1713101A (en) | 2001-05-30 |
| PL356208A1 (en) | 2004-06-14 |
| NO20022279L (no) | 2002-05-14 |
| EP1230252A1 (de) | 2002-08-14 |
| HUP0203468A2 (hu) | 2003-02-28 |
| NO20022279D0 (no) | 2002-05-14 |
| DE60009945T2 (de) | 2005-04-07 |
| IL149620A0 (en) | 2002-11-10 |
| WO2001036437A1 (fr) | 2001-05-25 |
| JP2003514826A (ja) | 2003-04-22 |
| AU777920B2 (en) | 2004-11-04 |
| DK1230252T3 (da) | 2004-08-02 |
| KR20020050282A (ko) | 2002-06-26 |
| DE60009945D1 (de) | 2004-05-19 |
| HUP0203468A3 (en) | 2003-03-28 |
| FR2801055B1 (fr) | 2002-02-08 |
| FR2801055A1 (fr) | 2001-05-18 |
| CA2391100A1 (fr) | 2001-05-25 |
| ES2219419T3 (es) | 2004-12-01 |
| CZ20021589A3 (cs) | 2002-07-17 |
| HK1049341A1 (zh) | 2003-05-09 |
| US6602899B1 (en) | 2003-08-05 |
| ATE264338T1 (de) | 2004-04-15 |
| ZA200203570B (en) | 2003-07-30 |
| TR200400907T4 (tr) | 2004-07-21 |
| EP1230252B1 (de) | 2004-04-14 |
| PT1230252E (pt) | 2004-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2232155C2 (ru) | Производные 1,4-бензотиазепин-1,1-диоксида, замещенные остатками сахаров, способ их получения, лекарственное средство на их основе и способ его получения | |
| EP0579681A1 (de) | Kristallines tiagabinehydrochlorid-monohydrat, seine herstellung und verwendung | |
| KR0178794B1 (ko) | 산화형 글루타티온 알킬 에스테르 | |
| EP0350878B1 (de) | Konjugierte Oxybutenolide zur Behandlung von Ulcera | |
| JPH05247078A (ja) | 糖化合物、シアル酸含有糖鎖類生合成阻害剤、その製造方法、並びに新規な中間体 | |
| US6602899B1 (en) | β-D-5 thioxylose derivatives, preparation method and therapeutic use | |
| AU723267B2 (en) | Modified form of the R(-)-N-(4,4-di(3-methylthien-2-yl) but-3-enyl)-nipecotic acid hydrochloride | |
| CA1175421A (en) | TREATMENT OF MALIGNANT TUMORS WITH 2-.beta.-D- RIBOFURANOSYLTHIAZOLE-4-CARBOXAMIDE AND RELATED COMPOUNDS | |
| EP0418655B1 (de) | Konjugierte gamma-Hydroxybutenolid-Derivate und sie als aktiver Wirkstoff enthaltende Mittel gegen Magengeschwüre | |
| EP1163217B1 (de) | Salz des (2r,3r,4r)-3,4-dihydroxy-2-hydroxmethylpyrrolidins | |
| ES2202212T3 (es) | Benzofenona-a-d.glicopiranosidos, preparacion y uso terapeutico. | |
| CA2257931C (en) | Modified form of the r(-)-n-(4,4-di(3-methylthien-2-yl)but-3-enyl)-nipecotic acid hydrochloride | |
| TW202130619A (zh) | 硝羥喹啉前藥及其用途 | |
| WO2004043983A1 (fr) | Derive du 4-methyl-2-oxo-2h-1-benzopyran-7yl 5-thio-beta-d-xylopyranoside, son procede de preparation et composition pharmaceutique le contenant | |
| JPS5892637A (ja) | 新規なシス―ビシクロ［３．３．０］オクタン誘導体、当該誘導体を含有する血小板凝集抑制剤および血圧降下剤ならびに当該誘導体の製造方法 | |
| CZ12566U1 (cs) | Amlodipinhemimaleát a farmaceutický prostředek |