JP2015508118A5 - - Google Patents

Info

Publication number

JP2015508118A5

JP2015508118A5 JP2014557995A JP2014557995A JP2015508118A5 JP 2015508118 A5 JP2015508118 A5 JP 2015508118A5 JP 2014557995 A JP2014557995 A JP 2014557995A JP 2014557995 A JP2014557995 A JP 2014557995A JP 2015508118 A5 JP2015508118 A5 JP 2015508118A5

Authority

JP

Japan

Prior art keywords

formula

general formula

hyaluronic acid

group

diyl

Prior art date

2013-02-26

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

• Espacenet
• Global Dossier
• Discuss

• -1 1H indole-3,5-diyl Chemical group 0.000 claims description 14
• 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 class 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 11
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
• 239000005977 Ethylene Substances 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 150000001875 compounds Chemical class 0.000 claims description 6
• NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• 238000006243 chemical reaction Methods 0.000 claims description 4
• 229920002674 hyaluronan Polymers 0.000 claims description 4
• 229960003160 hyaluronic acid Drugs 0.000 claims description 4
• 239000003446 ligand Substances 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 4
• 239000000010 aprotic solvent Substances 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 239000002243 precursor Substances 0.000 claims description 3
• 125000006850 spacer group Chemical group 0.000 claims description 3
• UXBLSWOMIHTQPH-UHFFFAOYSA-N 4-acetamido-TEMPO Chemical compound CC(=O)NC1CC(C)(C)N([O])C(C)(C)C1 UXBLSWOMIHTQPH-UHFFFAOYSA-N 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 239000003814 drug Substances 0.000 claims description 2
• MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
• QHXLIQMGIGEHJP-UHFFFAOYSA-N picoline - borane complex Substances [B].CC1=CC=CC=N1 QHXLIQMGIGEHJP-UHFFFAOYSA-N 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims 5
• 238000009472 formulation Methods 0.000 claims 4
• 239000000203 mixture Substances 0.000 claims 4
• 108010001336 Horseradish Peroxidase Proteins 0.000 claims 3
• 239000000017 hydrogel Substances 0.000 claims 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
• KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 2
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
• 210000001519 tissue Anatomy 0.000 claims 2
• LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 claims 1
• 229940000681 5-hydroxytryptophan Drugs 0.000 claims 1
• 208000020084 Bone disease Diseases 0.000 claims 1
• 206010061762 Chondropathy Diseases 0.000 claims 1
• 108010015133 Galactose oxidase Proteins 0.000 claims 1
• 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 claims 1
• 108010015776 Glucose oxidase Proteins 0.000 claims 1
• 239000004366 Glucose oxidase Substances 0.000 claims 1
• 208000031737 Tissue Adhesions Diseases 0.000 claims 1
• DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims 1
• 206010052428 Wound Diseases 0.000 claims 1
• 208000027418 Wounds and injury Diseases 0.000 claims 1
• 239000007864 aqueous solution Substances 0.000 claims 1
• 208000024429 articular cartilage disease Diseases 0.000 claims 1
• 230000003416 augmentation Effects 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 claims 1
• 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 claims 1
• 239000011248 coating agent Substances 0.000 claims 1
• 238000000576 coating method Methods 0.000 claims 1
• 239000002537 cosmetic Substances 0.000 claims 1
• 238000004132 cross linking Methods 0.000 claims 1
• 230000007547 defect Effects 0.000 claims 1
• 239000000945 filler Substances 0.000 claims 1
• 229930182830 galactose Natural products 0.000 claims 1
• 239000008103 glucose Substances 0.000 claims 1
• 229940116332 glucose oxidase Drugs 0.000 claims 1
• 235000019420 glucose oxidase Nutrition 0.000 claims 1
• 239000000463 material Substances 0.000 claims 1
• LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 claims 1
• 239000003223 protective agent Substances 0.000 claims 1
• 230000001172 regenerating effect Effects 0.000 claims 1
• 229940076279 serotonin Drugs 0.000 claims 1
• 210000004872 soft tissue Anatomy 0.000 claims 1
• RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims 1
• 229960003732 tyramine Drugs 0.000 claims 1
• DZGWFCGJZKJUFP-UHFFFAOYSA-O tyraminium Chemical compound [NH3+]CCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-O 0.000 claims 1
• 0 C*O[C@@](C([C@]1O[C@@](C(C([C@@]2*(C)C)O)O)OC2C(O)=O)NC(C)=O)OC(CO)[C@]1O Chemical compound C*O[C@@](C([C@]1O[C@@](C(C([C@@]2*(C)C)O)O)OC2C(O)=O)NC(C)=O)OC(CO)[C@]1O 0.000 description 1
• 150000001735 carboxylic acids Chemical group 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1