JPH027577B2 - - Google Patents
Info
- Publication number
- JPH027577B2 JPH027577B2 JP62015574A JP1557487A JPH027577B2 JP H027577 B2 JPH027577 B2 JP H027577B2 JP 62015574 A JP62015574 A JP 62015574A JP 1557487 A JP1557487 A JP 1557487A JP H027577 B2 JPH027577 B2 JP H027577B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfate
- polysaccharide
- agent according
- natural
- therapeutic agent
- 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.)
- Expired - Lifetime
Links
- 229920001282 polysaccharide Polymers 0.000 claims description 56
- 239000005017 polysaccharide Substances 0.000 claims description 56
- 208000030507 AIDS Diseases 0.000 claims description 24
- 229920001542 oligosaccharide Polymers 0.000 claims description 24
- 150000002482 oligosaccharides Chemical class 0.000 claims description 24
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 229920000669 heparin Polymers 0.000 claims description 14
- -1 polysaccharide sulfate Chemical class 0.000 claims description 14
- 229920002683 Glycosaminoglycan Polymers 0.000 claims description 12
- 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 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 12
- 229960002897 heparin Drugs 0.000 claims description 12
- 229940124597 therapeutic agent Drugs 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229960000633 dextran sulfate Drugs 0.000 claims description 11
- 208000015181 infectious disease Diseases 0.000 claims description 11
- KXCLCNHUUKTANI-RBIYJLQWSA-N keratan Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O[C@@H](O[C@H]3[C@H]([C@@H](COS(O)(=O)=O)O[C@@H](O)[C@@H]3O)O)[C@H](NC(C)=O)[C@H]2O)COS(O)(=O)=O)O[C@H](COS(O)(=O)=O)[C@@H]1O KXCLCNHUUKTANI-RBIYJLQWSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 229920001525 carrageenan Polymers 0.000 claims description 8
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 8
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
- 229920001287 Chondroitin sulfate Polymers 0.000 claims description 6
- 229920000288 Keratan sulfate Polymers 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 5
- 229920002567 Chondroitin Polymers 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- DLGJWSVWTWEWBJ-HGGSSLSASA-N chondroitin Chemical compound CC(O)=N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@H](O)C=C(C(O)=O)O1 DLGJWSVWTWEWBJ-HGGSSLSASA-N 0.000 claims description 5
- 229940059329 chondroitin sulfate Drugs 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 5
- 229920002674 hyaluronan Polymers 0.000 claims description 5
- 229960003160 hyaluronic acid Drugs 0.000 claims description 5
- 244000005700 microbiome Species 0.000 claims description 5
- 235000000346 sugar Nutrition 0.000 claims description 5
- 229920002101 Chitin Polymers 0.000 claims description 4
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 4
- 235000010418 carrageenan Nutrition 0.000 claims description 4
- 239000000679 carrageenan Substances 0.000 claims description 4
- 229940113118 carrageenan Drugs 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 229920001661 Chitosan Polymers 0.000 claims description 3
- 229920000045 Dermatan sulfate Polymers 0.000 claims description 3
- 229920000615 alginic acid Polymers 0.000 claims description 3
- 235000010443 alginic acid Nutrition 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 206010061598 Immunodeficiency Diseases 0.000 claims description 2
- 229920001491 Lentinan Polymers 0.000 claims description 2
- 229920001218 Pullulan Polymers 0.000 claims description 2
- 239000004373 Pullulan Substances 0.000 claims description 2
- AVJBPWGFOQAPRH-FWMKGIEWSA-L dermatan sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS([O-])(=O)=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](C([O-])=O)O1 AVJBPWGFOQAPRH-FWMKGIEWSA-L 0.000 claims description 2
- 229940051593 dermatan sulfate Drugs 0.000 claims description 2
- 230000007813 immunodeficiency Effects 0.000 claims description 2
- 229940115286 lentinan Drugs 0.000 claims description 2
- 235000019423 pullulan Nutrition 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims 19
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- OEANUJAFZLQYOD-CXAZCLJRSA-N (2r,3s,4r,5r,6r)-6-[(2r,3r,4r,5r,6r)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-4,5-dihydroxy-3-methoxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](OC)O[C@H](CO)[C@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](OC)[C@H](C(O)=O)O1 OEANUJAFZLQYOD-CXAZCLJRSA-N 0.000 claims 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 1
- 229940072056 alginate Drugs 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical group [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 52
- 238000012360 testing method Methods 0.000 description 41
- 150000004804 polysaccharides Chemical class 0.000 description 31
- 241000700605 Viruses Species 0.000 description 30
- 230000000694 effects Effects 0.000 description 23
- 239000000126 substance Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 230000035755 proliferation Effects 0.000 description 10
- 150000002772 monosaccharides Chemical class 0.000 description 8
- 230000004083 survival effect Effects 0.000 description 8
- 206010001513 AIDS related complex Diseases 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000004659 sterilization and disinfection Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 6
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 241001430294 unidentified retrovirus Species 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 102100034343 Integrase Human genes 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- KXKPYJOVDUMHGS-OSRGNVMNSA-N chondroitin sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O1 KXKPYJOVDUMHGS-OSRGNVMNSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 241001529453 unidentified herpesvirus Species 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 229920000715 Mucilage Polymers 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229920003045 dextran sodium sulfate Polymers 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 210000004400 mucous membrane Anatomy 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000001180 sulfating effect Effects 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 244000215068 Acacia senegal Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-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
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 2
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 2
- 208000008771 Lymphadenopathy Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000714205 Woolly monkey sarcoma virus Species 0.000 description 2
- ZNOZWUKQPJXOIG-XSBHQQIPSA-L [(2r,3s,4r,5r,6s)-6-[[(1r,3s,4r,5r,8s)-3,4-dihydroxy-2,6-dioxabicyclo[3.2.1]octan-8-yl]oxy]-4-[[(1r,3r,4r,5r,8s)-8-[(2s,3r,4r,5r,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-sulfonatooxyoxan-2-yl]oxy-4-hydroxy-2,6-dioxabicyclo[3.2.1]octan-3-yl]oxy]-5-hydroxy-2-( Chemical compound O[C@@H]1[C@@H](O)[C@@H](OS([O-])(=O)=O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H]2OC[C@H]1O[C@H](O[C@H]1[C@H]([C@@H](CO)O[C@@H](O[C@@H]3[C@@H]4OC[C@H]3O[C@H](O)[C@@H]4O)[C@@H]1O)OS([O-])(=O)=O)[C@@H]2O ZNOZWUKQPJXOIG-XSBHQQIPSA-L 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
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- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
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- 230000000840 anti-viral effect Effects 0.000 description 2
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- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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- 150000002337 glycosamines Chemical class 0.000 description 2
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- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- IAJILQKETJEXLJ-KLVWXMOXSA-N (2s,3r,4r,5r)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid Chemical compound O=C[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-KLVWXMOXSA-N 0.000 description 1
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JP23336388A Division JPH01151521A (ja) | 1986-04-04 | 1988-09-16 | レトロウイルス性疾患処置剤 |
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JPS6345223A JPS6345223A (ja) | 1988-02-26 |
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JP2626892B2 (ja) * | 1987-07-07 | 1997-07-02 | 味の素株式会社 | 新規な抗ウィルス剤 |
DE3734962C1 (de) * | 1987-10-15 | 1989-01-05 | Luitpold Werk Chem Pharm | Verwendung von Chondroitinpolysulfat zur vorbeugenden,lindernden oder heilenden Behandlung von AIDS und ARC |
JPH0725802B2 (ja) * | 1988-11-28 | 1995-03-22 | 味の素株式会社 | カードランまたはレンチナンの硫酸エステルまたはその塩の製造方法 |
ATE130516T1 (de) * | 1989-02-10 | 1995-12-15 | Taiho Pharmaceutical Co Ltd | Anti-hiv-heilmittel. |
CA1340994C (en) * | 1989-09-21 | 2000-05-16 | Rudolf Edgar Dr. Falk | Treatment of conditions and disease |
US5248675A (en) * | 1990-03-15 | 1993-09-28 | Tanabe Seiyaku Co., Ltd. | Polysulfate of cyclodextrin derivative and process for preparing the same |
DK0447171T3 (da) * | 1990-03-15 | 1994-12-12 | Tanabe Seiyaku Co | Polysulfat af cyclodextrinderivat og fremgangsmåde til fremstilling deraf |
JPH0491027A (ja) * | 1990-08-02 | 1992-03-24 | Taiho Yakuhin Kogyo Kk | 抗ヒト免疫不全症ウィルス剤 |
US5639738A (en) * | 1992-02-20 | 1997-06-17 | Hyal Pharmaceutical Corporation | Treatment of basal cell carcinoma and actinic keratosis employing hyaluronic acid and NSAIDs |
US6022866A (en) * | 1991-07-03 | 2000-02-08 | Hyal Pharmaceutical Corporation | Use of hyaluronic acid and forms to prevent arterial restenosis |
US5990095A (en) * | 1991-07-03 | 1999-11-23 | Hyal Pharmaceutical Corporation | Use of hyaluronic acid and forms to prevent arterial restenosis |
US6103704A (en) * | 1991-07-03 | 2000-08-15 | Hyal Pharmaceutical Corporation | Therapeutic methods using hyaluronic acid |
US5817644A (en) * | 1991-07-03 | 1998-10-06 | Hyal Pharmaceutical Corporation | Targeting of dosages of medicine and therapeutic agents |
JP2556236B2 (ja) * | 1991-08-29 | 1996-11-20 | 田辺製薬株式会社 | β−シクロデキストリン誘導体のポリ硫酸エステル及びその製法 |
US5942498A (en) * | 1992-02-20 | 1999-08-24 | Hyal Pharmaceutical Corporation | Formulations containing hyaluronic acid |
EP0957107B1 (en) | 1996-05-16 | 2004-07-21 | Nissin Food Products Co., Ltd. | Novel compounds having antiviral activity |
JP4686756B2 (ja) * | 2004-03-31 | 2011-05-25 | 独立行政法人産業技術総合研究所 | 動物臓器から抽出した水溶性画分、その製造方法、逆転写反応阻害剤、逆転写酵素阻害剤、ウイルス増殖阻害剤及び医薬組成物 |
JP5976628B2 (ja) * | 2013-12-18 | 2016-08-23 | 日本薬品株式会社 | コンドロイチン硫酸オリゴ糖を含む免疫賦活剤及びその製造方法 |
JP2016164179A (ja) * | 2016-04-11 | 2016-09-08 | 日本薬品株式会社 | コンドロイチン硫酸オリゴ糖を含む免疫賦活剤及びその製造方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5141083A (ja) * | 1974-10-04 | 1976-04-06 | Shigeo Suzuki | Kodonoseibutsukatsuseiojusurudekisutoranhoririnsanesuteru no seizoho |
JPS58918A (ja) * | 1981-05-15 | 1983-01-06 | ライカ−・ラボラトリ−ス・インコ−ポレ−テツド | 抗疱疹ウイルス剤 |
JPS62215529A (ja) * | 1986-01-16 | 1987-09-22 | マツクス−プランク−ゲゼルシヤフト・ツア・フエルデルンク・デア・ヴイツセンシヤフテン・エ−・フアウ | 逆転写酵素阻害剤を含む医薬組成物 |
-
1987
- 1987-01-26 JP JP1557487A patent/JPS6345223A/ja active Granted
- 1987-04-01 ZA ZA872359A patent/ZA872359B/xx unknown
- 1987-04-03 ZM ZM3087A patent/ZM3087A1/xx unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5141083A (ja) * | 1974-10-04 | 1976-04-06 | Shigeo Suzuki | Kodonoseibutsukatsuseiojusurudekisutoranhoririnsanesuteru no seizoho |
JPS58918A (ja) * | 1981-05-15 | 1983-01-06 | ライカ−・ラボラトリ−ス・インコ−ポレ−テツド | 抗疱疹ウイルス剤 |
JPS62215529A (ja) * | 1986-01-16 | 1987-09-22 | マツクス−プランク−ゲゼルシヤフト・ツア・フエルデルンク・デア・ヴイツセンシヤフテン・エ−・フアウ | 逆転写酵素阻害剤を含む医薬組成物 |
Also Published As
Publication number | Publication date |
---|---|
ZM3087A1 (en) | 1989-07-28 |
ZA872359B (en) | 1988-04-27 |
JPS6345223A (ja) | 1988-02-26 |
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