JP2014512445A5 - - Google Patents

Info

Publication number

JP2014512445A5

JP2014512445A5 JP2014506754A JP2014506754A JP2014512445A5 JP 2014512445 A5 JP2014512445 A5 JP 2014512445A5 JP 2014506754 A JP2014506754 A JP 2014506754A JP 2014506754 A JP2014506754 A JP 2014506754A JP 2014512445 A5 JP2014512445 A5 JP 2014512445A5

Authority

JP

Japan

Prior art keywords

group

hyaluronan

derivative

process according

formula

Prior art date

2012-04-19

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

• 238000000034 method Methods 0.000 claims description 23
• 229920002674 hyaluronan Polymers 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 13
• 239000003102 growth factor Substances 0.000 claims description 6
• 229940079593 drug Drugs 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 238000013270 controlled release Methods 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• 102000004190 Enzymes Human genes 0.000 claims description 3
• 108090000790 Enzymes Proteins 0.000 claims description 3
• -1 antibacterials Substances 0.000 claims description 3
• 229920001222 biopolymer Polymers 0.000 claims description 3
• 102000004169 proteins and genes Human genes 0.000 claims description 3
• 108090000623 proteins and genes Proteins 0.000 claims description 3
• 229920001059 synthetic polymer Polymers 0.000 claims description 3
• 230000017423 tissue regeneration Effects 0.000 claims description 3
• 125000002723 alicyclic group Chemical group 0.000 claims description 2
• 125000001931 aliphatic group Chemical group 0.000 claims description 2
• 125000003118 aryl group Chemical group 0.000 claims description 2
• 230000000975 bioactive effect Effects 0.000 claims description 2
• 210000001612 chondrocyte Anatomy 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 238000002156 mixing Methods 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
• 235000010378 sodium ascorbate Nutrition 0.000 claims description 2
• 229960005055 sodium ascorbate Drugs 0.000 claims description 2
• PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 2
• PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 2
• KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(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-MNSSHETKSA-N 0.000 claims 15
• 229940099552 hyaluronan Drugs 0.000 claims 13
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims 4
• 150000003141 primary amines Chemical class 0.000 claims 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
• 239000008186 active pharmaceutical agent Substances 0.000 claims 2
• 229940088710 antibiotic agent Drugs 0.000 claims 2
• 230000008878 coupling Effects 0.000 claims 2
• 238000010168 coupling process Methods 0.000 claims 2
• 238000005859 coupling reaction Methods 0.000 claims 2
• 239000000539 dimer Substances 0.000 claims 2
• 238000002955 isolation Methods 0.000 claims 2
• 238000005580 one pot reaction Methods 0.000 claims 2
• 230000003647 oxidation Effects 0.000 claims 2
• 238000007254 oxidation reaction Methods 0.000 claims 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
• 150000003335 secondary amines Chemical group 0.000 claims 2
• SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 2
• RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims 1
• VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical group CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 claims 1
• OYBOVXXFJYJYPC-UHFFFAOYSA-N 3-azidopropan-1-amine Chemical compound NCCCN=[N+]=[N-] OYBOVXXFJYJYPC-UHFFFAOYSA-N 0.000 claims 1
• 239000005708 Sodium hypochlorite Substances 0.000 claims 1
• 206010052428 Wound Diseases 0.000 claims 1
• 208000027418 Wounds and injury Diseases 0.000 claims 1
• 229940035676 analgesics Drugs 0.000 claims 1
• 229940035674 anesthetics Drugs 0.000 claims 1
• 239000000730 antalgic agent Substances 0.000 claims 1
• 239000003242 anti bacterial agent Substances 0.000 claims 1
• 230000000844 anti-bacterial effect Effects 0.000 claims 1
• 239000002260 anti-inflammatory agent Substances 0.000 claims 1
• 239000002246 antineoplastic agent Substances 0.000 claims 1
• 229940088623 biologically active substance Drugs 0.000 claims 1
• 238000006352 cycloaddition reaction Methods 0.000 claims 1
• 239000000824 cytostatic agent Substances 0.000 claims 1
• 230000001085 cytostatic effect Effects 0.000 claims 1
• 238000004108 freeze drying Methods 0.000 claims 1
• 239000003193 general anesthetic agent Substances 0.000 claims 1
• 239000007788 liquid Substances 0.000 claims 1
• 230000007774 longterm Effects 0.000 claims 1
• GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 1
• PVDGXEIFXYECGU-UHFFFAOYSA-N n-azidoaniline Chemical compound [N-]=[N+]=NNC1=CC=CC=C1 PVDGXEIFXYECGU-UHFFFAOYSA-N 0.000 claims 1
• VMXAIJCDNKFKPO-UHFFFAOYSA-N n-ethynylaniline Chemical compound C#CNC1=CC=CC=C1 VMXAIJCDNKFKPO-UHFFFAOYSA-N 0.000 claims 1
• 229910052757 nitrogen Inorganic materials 0.000 claims 1
• 238000010899 nucleation Methods 0.000 claims 1
• 230000001590 oxidative effect Effects 0.000 claims 1
• JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims 1
• 239000011541 reaction mixture Substances 0.000 claims 1
• 239000003357 wound healing promoting agent Substances 0.000 claims 1
• 239000000463 material Substances 0.000 description 4
• 238000002360 preparation method Methods 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 238000009792 diffusion process Methods 0.000 description 1
• 230000007613 environmental effect Effects 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 229960003160 hyaluronic acid Drugs 0.000 description 1
• 239000000017 hydrogel Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1