MXPA06010049A - Derivados de oligosacaridos sulfatados. - Google Patents
Derivados de oligosacaridos sulfatados.Info
- Publication number
- MXPA06010049A MXPA06010049A MXPA06010049A MXPA06010049A MXPA06010049A MX PA06010049 A MXPA06010049 A MX PA06010049A MX PA06010049 A MXPA06010049 A MX PA06010049A MX PA06010049 A MXPA06010049 A MX PA06010049A MX PA06010049 A MXPA06010049 A MX PA06010049A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- aryl
- further characterized
- derivative
- alkyl
- Prior art date
Links
- 150000002482 oligosaccharides Chemical class 0.000 title abstract description 18
- 229920001542 oligosaccharide Polymers 0.000 title abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 101
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000008280 blood Substances 0.000 claims abstract description 14
- 210000004369 blood Anatomy 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 12
- -1 n-octyl Chemical group 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 230000033115 angiogenesis Effects 0.000 claims description 12
- 208000015181 infectious disease Diseases 0.000 claims description 12
- 206010027476 Metastases Diseases 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 230000009401 metastasis Effects 0.000 claims description 11
- 150000002772 monosaccharides Chemical group 0.000 claims description 11
- 206010061218 Inflammation Diseases 0.000 claims description 10
- 208000007536 Thrombosis Diseases 0.000 claims description 10
- 230000015271 coagulation Effects 0.000 claims description 10
- 238000005345 coagulation Methods 0.000 claims description 10
- 230000004054 inflammatory process Effects 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 230000000813 microbial effect Effects 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 206010014486 Elevated triglycerides Diseases 0.000 claims description 7
- 125000003435 aroyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 241000282414 Homo sapiens Species 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 206010003178 Arterial thrombosis Diseases 0.000 claims 1
- 206010051055 Deep vein thrombosis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000010378 Pulmonary Embolism Diseases 0.000 claims 1
- 206010038934 Retinopathy proliferative Diseases 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- 206010047249 Venous thrombosis Diseases 0.000 claims 1
- 208000023819 chronic asthma Diseases 0.000 claims 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000001732 thrombotic effect Effects 0.000 claims 1
- 108010037536 heparanase Proteins 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 12
- 239000003112 inhibitor Substances 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 8
- 230000005764 inhibitory process Effects 0.000 abstract description 7
- 239000003146 anticoagulant agent Substances 0.000 abstract description 6
- 230000001772 anti-angiogenic effect Effects 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 230000002001 anti-metastasis Effects 0.000 abstract description 3
- 230000000845 anti-microbial effect Effects 0.000 abstract description 3
- 229940127219 anticoagulant drug Drugs 0.000 abstract description 3
- 108091000314 heparan sulfate binding proteins Proteins 0.000 abstract description 3
- 102000036064 heparan sulfate binding proteins Human genes 0.000 abstract description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002785 anti-thrombosis Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 36
- 235000019439 ethyl acetate Nutrition 0.000 description 30
- IPOGMIXXMPIMID-RIWCUPLTSA-N [(2r,3r,4s,5s,6r)-6-[(2r,3s,4s,5r,6r)-2-[(2r,3s,4s,5r,6r)-2-[(2r,3r,4s,5s,6r)-3,5-disulfooxy-2-(sulfooxymethyl)-6-[(2r,3s,4r,5r,6r)-2,4,5-trisulfooxy-6-(sulfooxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-3,5-disulfooxy-6-(sulfooxymethyl)oxan-4-yl]oxy-3,5-disulfoox Chemical compound OS(=O)(=O)O[C@H]1[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@@H](COP(O)(=O)O)O[C@@H]1O[C@@H]1[C@H](OS(O)(=O)=O)[C@@H](O[C@@H]2[C@@H]([C@@H](O[C@@H]3[C@@H]([C@@H](O[C@H]4[C@H]([C@H](OS(O)(=O)=O)[C@@H](COS(O)(=O)=O)O[C@@H]4OS(O)(=O)=O)OS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@H]3OS(O)(=O)=O)OS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@H]2OS(O)(=O)=O)OS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@H]1OS(O)(=O)=O IPOGMIXXMPIMID-RIWCUPLTSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 19
- 239000012230 colorless oil Substances 0.000 description 17
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000003556 assay Methods 0.000 description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
- 229920002971 Heparan sulfate Polymers 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 102100024025 Heparanase Human genes 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003102 growth factor Substances 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000001540 azides Chemical class 0.000 description 10
- 230000027455 binding Effects 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 239000002808 molecular sieve Substances 0.000 description 10
- 150000003077 polyols Chemical class 0.000 description 10
- 102000004169 proteins and genes Human genes 0.000 description 10
- 108090000623 proteins and genes Proteins 0.000 description 10
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 239000003446 ligand Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 238000004108 freeze drying Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 150000004044 tetrasaccharides Chemical class 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 6
- 239000012300 argon atmosphere Substances 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229930182470 glycoside Natural products 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 5
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 5
- 150000004043 trisaccharides Chemical class 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 108090000386 Fibroblast Growth Factor 1 Proteins 0.000 description 4
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 241000235648 Pichia Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 102100030951 Tissue factor pathway inhibitor Human genes 0.000 description 4
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- 125000003342 alkenyl group Chemical group 0.000 description 4
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
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- IBUZGVQIKARDAF-PEBLQZBPSA-N [(2r,3r,4s,5s,6r)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](OC(=N)C(Cl)(Cl)Cl)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O IBUZGVQIKARDAF-PEBLQZBPSA-N 0.000 description 3
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 2
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- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- 125000005917 3-methylpentyl group Chemical group 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/04—Disaccharides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- 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
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- 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)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Virology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2004901103A AU2004901103A0 (en) | 2004-03-04 | Sulfated Oligosaccharide Derivatives | |
| PCT/AU2005/000314 WO2005085264A1 (en) | 2004-03-04 | 2005-03-04 | Sulfated oligosaccharide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06010049A true MXPA06010049A (es) | 2007-04-10 |
Family
ID=34916868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06010049A MXPA06010049A (es) | 2004-03-04 | 2005-03-04 | Derivados de oligosacaridos sulfatados. |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7875592B2 (OSRAM) |
| EP (1) | EP1720889B1 (OSRAM) |
| JP (1) | JP5139797B2 (OSRAM) |
| KR (1) | KR101156273B1 (OSRAM) |
| CN (3) | CN104119404A (OSRAM) |
| AU (1) | AU2005219456B2 (OSRAM) |
| BR (1) | BRPI0508144A (OSRAM) |
| CA (1) | CA2557989C (OSRAM) |
| ES (1) | ES2531880T3 (OSRAM) |
| HK (1) | HK1199263A1 (OSRAM) |
| IL (1) | IL177870A (OSRAM) |
| MX (1) | MXPA06010049A (OSRAM) |
| NO (1) | NO338461B1 (OSRAM) |
| RU (1) | RU2392281C2 (OSRAM) |
| TW (1) | TWI426080B (OSRAM) |
| WO (1) | WO2005085264A1 (OSRAM) |
| ZA (1) | ZA200607057B (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7875592B2 (en) * | 2004-03-04 | 2011-01-25 | Progen Pharmaceuticals Limited | Sulfated oligosaccharide derivatives |
| WO2006102717A1 (en) * | 2005-04-01 | 2006-10-05 | Christopher Richard Parish | Modulating angiogenesis with nod factors such as glucosamine oligosaccharides |
| ES2584927T7 (es) * | 2007-10-16 | 2020-11-05 | Progen Pg500 Series Pty Ltd | Derivados de oligosacáridos sulfatados novedosos |
| WO2010003023A2 (en) * | 2008-07-01 | 2010-01-07 | Zacharon Pharmaceuticals, Inc. | Heparan sulfate inhibitors |
| EP2149580A1 (en) | 2008-07-15 | 2010-02-03 | Istituto Scientifico di Chimica E Biochimica "G Ronzoni | Mimetics of sulfated oligosaccharides |
| CN101591401A (zh) * | 2009-02-27 | 2009-12-02 | 江南大学 | 一种制备高活性低分子量肝素的方法 |
| JP5701498B2 (ja) * | 2009-12-01 | 2015-04-15 | 公益財団法人微生物化学研究会 | 炎症性細胞からのヘパラナーゼの放出抑制剤、抗炎症剤、及び薬用組成物 |
| CN103547270A (zh) * | 2011-06-09 | 2014-01-29 | 基亚生物科技股份有限公司 | 用于抑制肝癌复发、恶化或转移之医药组成物 |
| CA2940579A1 (en) | 2014-03-13 | 2015-09-17 | Universitaet Basel | Carbohydrate ligands that bind to igm antibodies against myelin-associated glycoprotein |
| CN105017341B (zh) * | 2014-04-22 | 2018-05-15 | 华东师范大学 | 硫酸化岩藻-半乳四糖及其制备方法和应用 |
| CN104876979B (zh) * | 2015-06-19 | 2018-10-09 | 天津红日药业股份有限公司 | 一种具有抗Xa因子活性的磺酸化五糖化合物 |
| CN105001278B (zh) * | 2015-06-19 | 2018-07-06 | 天津红日药业股份有限公司 | 一种磺达肝癸钠二糖中间体片段的合成方法 |
| AU2016323377B2 (en) | 2015-09-16 | 2021-04-15 | Universität Basel | Carbohydrate ligands that bind to antibodies against glycoepitopes of glycosphingolipids |
| JP2016199579A (ja) * | 2016-07-08 | 2016-12-01 | 基亜生物科技股▲ふん▼有限公司Ｍｅｄｉｇｅｎ Ｂｉｏｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐ． | 肝癌の再発、悪化または転移の抑制に用いる医薬組成物 |
| CN109069523B (zh) * | 2016-12-10 | 2022-05-06 | 扬州蓝色生物医药科技有限公司 | 甘露寡聚糖类化合物及其作为抗rna病毒药物的应用 |
| US11787783B2 (en) | 2016-12-13 | 2023-10-17 | Beta Therapeutics Pty Ltd | Heparanase inhibitors and use thereof |
| CA3046997A1 (en) | 2016-12-13 | 2018-06-21 | Beta Therapeutics Pty Ltd | Heparanase inhibitors and use thereof |
| WO2018107244A1 (en) | 2016-12-15 | 2018-06-21 | Progen Pg500 Series Pty Ltd | Composition and uses thereof |
| US10842804B2 (en) * | 2017-03-01 | 2020-11-24 | Medigen Biotechnology Corporation | Muparfostat for use in treating patients with hepatitis virus-related hepatocellular carcinoma after surgical resection |
| KR102377358B1 (ko) | 2017-10-16 | 2022-03-23 | 삼성전자주식회사 | 반도체 메모리 소자 및 그 제조 방법 |
| BR112020013714A2 (pt) | 2017-12-15 | 2020-12-01 | The Australian National University | compostos para tratamento e prevenção de patologias mediadas por histona extracelular |
| JP6619830B2 (ja) * | 2018-02-22 | 2019-12-11 | 基亜生物科技股▲ふん▼有限公司Ｍｅｄｉｇｅｎ Ｂｉｏｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐ． | 肝癌の再発、悪化または転移の抑制に用いる医薬組成物 |
| CN109762032A (zh) * | 2019-01-16 | 2019-05-17 | 天津科技大学 | 一种磺酸化路易斯x三糖及其合成方法和应用 |
| JP2022530732A (ja) * | 2019-02-25 | 2022-07-01 | ジ・オーストラリアン・ナショナル・ユニヴァーシティ | Ｎｅｔ関連合併症を処置及び予防するための化合物 |
| CN116813675B (zh) * | 2023-08-23 | 2023-11-24 | 北京远大九和药业有限公司 | 一种化合物晶型及其制备、组合物和用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989003684A1 (fr) | 1987-10-30 | 1989-05-05 | Chugai Seiyaku Kabushiki Kaisha | Agent anti-vih |
| FR2704226B1 (fr) * | 1993-04-22 | 1995-07-21 | Sanofi Elf | 3-desoxy oligosaccharides, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5739115A (en) * | 1993-10-07 | 1998-04-14 | Glycomed Incorporated | Sulfated maltooligosaccharides with heparin-like properties |
| EP0722326A4 (en) * | 1993-10-07 | 1999-10-06 | Glycomed Inc | HIGHLY SULFATED MALTOOLIGOSSACCHARIDES WITH HEPARIN-LIKE PROPERTIES |
| AUPN261895A0 (en) | 1995-04-28 | 1995-05-18 | Australian National University, The | Preparation and use of sulfated oligosaccharides |
| WO1996034004A1 (en) * | 1995-04-28 | 1996-10-31 | Takara Shuzo Co., Ltd. | Sugar compounds |
| JPH09183789A (ja) * | 1995-10-31 | 1997-07-15 | Sanwa Kagaku Kenkyusho Co Ltd | 新規な硫酸化及び燐酸化糖誘導体、その製法及び用途 |
| IL120722A (en) * | 1996-05-08 | 1999-07-14 | Akzo Nobel Nv | Polysulfated tetrasaccharide derivatives and pharmaceutical compositions containing them |
| AUPO556297A0 (en) | 1997-03-11 | 1997-04-10 | Australian National University, The | Sulfated oligosaccharides having anticoagulant/ antithrombotic activity |
| IL126893A (en) * | 1997-11-19 | 2003-05-29 | Akzo Nobel Nv | Sulfated pentasaccharide derivatives and pharmaceutical compositions containing them |
| FR2773801B1 (fr) * | 1998-01-19 | 2000-05-12 | Sanofi Sa | Nouveaux pentasaccharides, procedes pour leurs preparations et compositions pharmaceutiques les contenant |
| CN1450075A (zh) * | 2002-04-11 | 2003-10-22 | 中国科学院生态环境研究中心 | 一类寡糖及其硫酸化产物和它们的制备方法及含该寡糖的药物组合物 |
| US7875592B2 (en) * | 2004-03-04 | 2011-01-25 | Progen Pharmaceuticals Limited | Sulfated oligosaccharide derivatives |
-
2005
- 2005-03-04 US US10/591,577 patent/US7875592B2/en not_active Expired - Fee Related
- 2005-03-04 ES ES05706346.3T patent/ES2531880T3/es not_active Expired - Lifetime
- 2005-03-04 AU AU2005219456A patent/AU2005219456B2/en not_active Ceased
- 2005-03-04 TW TW094106609A patent/TWI426080B/zh not_active IP Right Cessation
- 2005-03-04 RU RU2006134972/04A patent/RU2392281C2/ru not_active IP Right Cessation
- 2005-03-04 BR BRPI0508144-0A patent/BRPI0508144A/pt not_active Application Discontinuation
- 2005-03-04 EP EP05706346.3A patent/EP1720889B1/en not_active Expired - Lifetime
- 2005-03-04 MX MXPA06010049A patent/MXPA06010049A/es active IP Right Grant
- 2005-03-04 KR KR1020067020704A patent/KR101156273B1/ko not_active Expired - Fee Related
- 2005-03-04 CA CA2557989A patent/CA2557989C/en not_active Expired - Fee Related
- 2005-03-04 CN CN201410353750.7A patent/CN104119404A/zh active Pending
- 2005-03-04 CN CNA2005800068338A patent/CN1989146A/zh active Pending
- 2005-03-04 WO PCT/AU2005/000314 patent/WO2005085264A1/en not_active Ceased
- 2005-03-04 JP JP2007501068A patent/JP5139797B2/ja not_active Expired - Fee Related
- 2005-03-04 CN CN201410042932.2A patent/CN103788141B/zh not_active Expired - Fee Related
-
2006
- 2006-08-23 ZA ZA2006/07057A patent/ZA200607057B/en unknown
- 2006-09-03 IL IL177870A patent/IL177870A/en active IP Right Grant
- 2006-10-03 NO NO20064489A patent/NO338461B1/no not_active IP Right Cessation
-
2007
- 2007-12-19 HK HK14112830.3A patent/HK1199263A1/xx unknown
-
2010
- 2010-12-03 US US12/960,145 patent/US8173606B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1989146A (zh) | 2007-06-27 |
| CA2557989A1 (en) | 2005-09-15 |
| CA2557989C (en) | 2013-04-23 |
| BRPI0508144A (pt) | 2007-07-24 |
| EP1720889A1 (en) | 2006-11-15 |
| JP5139797B2 (ja) | 2013-02-06 |
| TWI426080B (zh) | 2014-02-11 |
| RU2392281C2 (ru) | 2010-06-20 |
| KR101156273B1 (ko) | 2012-06-13 |
| CN104119404A (zh) | 2014-10-29 |
| ZA200607057B (en) | 2008-04-30 |
| JP2007526257A (ja) | 2007-09-13 |
| CN103788141B (zh) | 2016-08-17 |
| NO338461B1 (no) | 2016-08-15 |
| IL177870A0 (en) | 2006-12-31 |
| US8173606B2 (en) | 2012-05-08 |
| TW200602351A (en) | 2006-01-16 |
| KR20070007815A (ko) | 2007-01-16 |
| AU2005219456A1 (en) | 2005-09-15 |
| HK1199263A1 (en) | 2015-06-26 |
| IL177870A (en) | 2011-08-31 |
| AU2005219456B2 (en) | 2011-04-07 |
| EP1720889A4 (en) | 2008-03-19 |
| CN103788141A (zh) | 2014-05-14 |
| RU2006134972A (ru) | 2008-04-10 |
| ES2531880T3 (es) | 2015-03-20 |
| US7875592B2 (en) | 2011-01-25 |
| EP1720889B1 (en) | 2014-11-26 |
| US20070185037A1 (en) | 2007-08-09 |
| US20110130354A1 (en) | 2011-06-02 |
| WO2005085264A1 (en) | 2005-09-15 |
| NO20064489L (no) | 2006-11-27 |
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