PH26025A - Esters of polyvalent alcohols of hyaluronic acid - Google Patents

Esters of polyvalent alcohols of hyaluronic acid Download PDF

Info

Publication number: PH26025A
Authority: PH; Philippines
Prior art keywords: linked; cross; groups; added; acetone
Prior art date: 1986-10-13

Application number

PH35917A

Other languages

English (en)

Inventor

Francesco Della Valle

Audrelio Romeo

Original Assignee

Fidia Spa

Priority date (The priority date 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 date listed.)

1986-10-13

Filing date

1987-10-12

Publication date

1992-01-29

1987-10-12 Application filed by Fidia Spa filed Critical Fidia Spa

1992-01-29 Publication of PH26025A publication Critical patent/PH26025A/en

Links

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 title claims description 160
229920002674 hyaluronan Polymers 0.000 title claims description 158
229960003160 hyaluronic acid Drugs 0.000 title claims description 156
150000002148 esters Chemical class 0.000 title claims description 82
150000001298 alcohols Chemical class 0.000 title description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 181
150000003839 salts Chemical class 0.000 claims description 64
-1 : hesane Chemical compound 0.000 claims description 63
150000001875 compounds Chemical class 0.000 claims description 48
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 33
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 31
125000001931 aliphatic group Chemical group 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 18
229910052757 nitrogen Chemical group 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
239000011734 sodium Substances 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 13
229910052708 sodium Inorganic materials 0.000 claims description 12
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 claims description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
239000013543 active substance Substances 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 7
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 7
229960004544 cortisone Drugs 0.000 claims description 7
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 5
150000002334 glycols Chemical class 0.000 claims description 5
125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
150000001342 alkaline earth metals Chemical class 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
150000003568 thioethers Chemical class 0.000 claims description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
150000001241 acetals Chemical class 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
229960003957 dexamethasone Drugs 0.000 claims description 3
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 3
229960000890 hydrocortisone Drugs 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
235000001508 sulfur Nutrition 0.000 claims description 3
229960005349 sulfur Drugs 0.000 claims description 3
150000007970 thio esters Chemical class 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
MKPDWECBUAZOHP-AFYJWTTESA-N Paramethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O MKPDWECBUAZOHP-AFYJWTTESA-N 0.000 claims description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229940092705 beclomethasone Drugs 0.000 claims description 2
NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims description 2
150000001720 carbohydrates Chemical class 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229960002842 clobetasol Drugs 0.000 claims description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
229960002858 paramethasone Drugs 0.000 claims description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
229960005205 prednisolone Drugs 0.000 claims description 2
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 3
229930194542 Keto Natural products 0.000 claims 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
125000000468 ketone group Chemical group 0.000 claims 2
239000001301 oxygen Substances 0.000 claims 2
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims 1
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 claims 1
241000360590 Erythrites Species 0.000 claims 1
102000006835 Lamins Human genes 0.000 claims 1
108010047294 Lamins Proteins 0.000 claims 1
235000007849 Lepidium sativum Nutrition 0.000 claims 1
244000211187 Lepidium sativum Species 0.000 claims 1
239000005864 Sulphur Chemical group 0.000 claims 1
CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 claims 1
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 claims 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims 1
229960003469 flumetasone Drugs 0.000 claims 1
WXURHACBFYSXBI-GQKYHHCASA-N flumethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-GQKYHHCASA-N 0.000 claims 1
229960003238 fluprednidene Drugs 0.000 claims 1
YVHXHNGGPURVOS-SBTDHBFYSA-N fluprednidene Chemical group O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@](C(=C)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 YVHXHNGGPURVOS-SBTDHBFYSA-N 0.000 claims 1
125000000524 functional group Chemical group 0.000 claims 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
210000005053 lamin Anatomy 0.000 claims 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
229960004618 prednisone Drugs 0.000 claims 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 329
235000019441 ethanol Nutrition 0.000 description 129
239000000243 solution Substances 0.000 description 113
229940022682 acetone Drugs 0.000 description 110
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 70
238000006243 chemical reaction Methods 0.000 description 61
238000000034 method Methods 0.000 description 58
125000004185 ester group Chemical group 0.000 description 57
239000002244 precipitate Substances 0.000 description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 43
239000003814 drug Substances 0.000 description 43
238000001914 filtration Methods 0.000 description 41
238000002360 preparation method Methods 0.000 description 39
230000000875 corresponding effect Effects 0.000 description 38
238000004458 analytical method Methods 0.000 description 37
238000004448 titration Methods 0.000 description 33
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 32
238000000265 homogenisation Methods 0.000 description 27
238000007127 saponification reaction Methods 0.000 description 26
239000011780 sodium chloride Substances 0.000 description 24
159000000000 sodium salts Chemical class 0.000 description 24
239000012299 nitrogen atmosphere Substances 0.000 description 23
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 20
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 17
230000009471 action Effects 0.000 description 16
229960005382 phenolphthalein Drugs 0.000 description 16
230000006870 function Effects 0.000 description 15
230000032050 esterification Effects 0.000 description 14
238000005886 esterification reaction Methods 0.000 description 14
238000007792 addition Methods 0.000 description 13
239000002537 cosmetic Substances 0.000 description 13
230000000694 effects Effects 0.000 description 13
239000000203 mixture Substances 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 12
229940079593 drug Drugs 0.000 description 12
239000012528 membrane Substances 0.000 description 12
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230000000144 pharmacologic effect Effects 0.000 description 11
239000000126 substance Substances 0.000 description 11
210000001519 tissue Anatomy 0.000 description 11
239000002904 solvent Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
230000000699 topical effect Effects 0.000 description 8
239000006071 cream Substances 0.000 description 7
150000005846 sugar alcohols Polymers 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
238000013019 agitation Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
150000007530 organic bases Chemical class 0.000 description 6
238000001356 surgical procedure Methods 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
239000004593 Epoxy Substances 0.000 description 5
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150000007513 acids Chemical class 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
229940088710 antibiotic agent Drugs 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
230000008901 benefit Effects 0.000 description 5
239000002775 capsule Substances 0.000 description 5
210000001520 comb Anatomy 0.000 description 5
229960001760 dimethyl sulfoxide Drugs 0.000 description 5
230000007717 exclusion Effects 0.000 description 5
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150000007529 inorganic bases Chemical class 0.000 description 5
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KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 4
HFVIYAZBVIGNAN-UHFFFAOYSA-N 1,1-dibromodecane Chemical compound CCCCCCCCCC(Br)Br HFVIYAZBVIGNAN-UHFFFAOYSA-N 0.000 description 4
STBMZSJLFYGOJU-UHFFFAOYSA-N 1,1-dibromooctane Chemical compound CCCCCCCC(Br)Br STBMZSJLFYGOJU-UHFFFAOYSA-N 0.000 description 4
206010052428 Wound Diseases 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
239000000654 additive Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
229940121363 anti-inflammatory agent Drugs 0.000 description 4
239000002260 anti-inflammatory agent Substances 0.000 description 4
239000003443 antiviral agent Substances 0.000 description 4
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238000005119 centrifugation Methods 0.000 description 4
230000007547 defect Effects 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
239000000499 gel Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
239000002304 perfume Substances 0.000 description 4
150000004804 polysaccharides Chemical class 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
210000003491 skin Anatomy 0.000 description 4
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150000003431 steroids Chemical class 0.000 description 4
229960003604 testosterone Drugs 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
238000000108 ultra-filtration Methods 0.000 description 4
OIQCMCUFGWKBBV-UHFFFAOYSA-N 2,3-diiodobutane Chemical compound CC(I)C(C)I OIQCMCUFGWKBBV-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000283986 Lepus Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
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JOMHSQGEWSNUKU-UHFFFAOYSA-N pipotiazine Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCC(CCO)CC1 JOMHSQGEWSNUKU-UHFFFAOYSA-N 0.000 description 1
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AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
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CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
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YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(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- Chemical compound [Na+].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 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
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DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
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KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
HTJXMOGUGMSZOG-UHFFFAOYSA-N tiaramide Chemical compound C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 HTJXMOGUGMSZOG-UHFFFAOYSA-N 0.000 description 1
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230000002936 tranquilizing effect Effects 0.000 description 1
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VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
- 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
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/28—Polysaccharides or their derivatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/06—At least partially resorbable materials
- A61L17/10—At least partially resorbable materials containing macromolecular materials
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/20—Polysaccharides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates

PH35917A 1986-10-13 1987-10-12 Esters of polyvalent alcohols of hyaluronic acid PH26025A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT48546/86A IT1198449B (it)	1986-10-13	1986-10-13	Esteri di alcoli polivalenti di acido ialuronico

Publications (1)

Publication Number	Publication Date
PH26025A true PH26025A (en)	1992-01-29

Family

ID=11267232

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH35917A PH26025A (en)	1986-10-13	1987-10-12	Esters of polyvalent alcohols of hyaluronic acid

Country Status (23)

Country	Link
US (1)	US4957744A (it)
EP (1)	EP0265116B1 (it)
JP (1)	JP2648308B2 (it)
KR (1)	KR920002702B1 (it)
CN (1)	CN1025035C (it)
AR (1)	AR247406A1 (it)
AT (1)	ATE163942T1 (it)
AU (1)	AU610087B2 (it)
CA (1)	CA1317287C (it)
DE (1)	DE3752176T2 (it)
DK (1)	DK536087A (it)
ES (1)	ES2115583T3 (it)
FI (1)	FI96610C (it)
HU (1)	HU204858B (it)
IE (1)	IE872618L (it)
IL (1)	IL84032A (it)
IN (1)	IN170801B (it)
IT (1)	IT1198449B (it)
NO (1)	NO175374C (it)
NZ (1)	NZ221994A (it)
PH (1)	PH26025A (it)
PT (1)	PT85908B (it)
ZA (1)	ZA877559B (it)

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US5202431A (en) *	1985-07-08	1993-04-13	Fidia, S.P.A.	Partial esters of hyaluronic acid
US4851521A (en) *	1985-07-08	1989-07-25	Fidia, S.P.A.	Esters of hyaluronic acid
US5227157A (en) *	1986-10-14	1993-07-13	Board Of Regents, The University Of Texas System	Delivery of therapeutic agents
US5403592A (en) *	1987-08-25	1995-04-04	Macnaught Pty Limited	Lubricant composition for rheumatism
IT1219587B (it) *	1988-05-13	1990-05-18	Fidia Farmaceutici	Polisaccaridi carbossiilici autoreticolati
US5470829A (en) *	1988-11-17	1995-11-28	Prisell; Per	Pharmaceutical preparation
US5783691A (en) *	1989-02-08	1998-07-21	Biomatrix, Inc.	Crosslinked hyaluronate gels, their use and method for producing them
CA1340994C (en) *	1989-09-21	2000-05-16	Rudolf Edgar Dr. Falk	Treatment of conditions and disease
US5824658A (en) *	1990-09-18	1998-10-20	Hyal Pharmaceutical Corporation	Topical composition containing hyaluronic acid and NSAIDS
US5990096A (en) *	1990-09-18	1999-11-23	Hyal Pharmaceutical Corporation	Formulations containing hyaluronic acid
CA2061703C (en) *	1992-02-20	2002-07-02	Rudolf E. Falk	Formulations containing hyaluronic acid
US5910489A (en) *	1990-09-18	1999-06-08	Hyal Pharmaceutical Corporation	Topical composition containing hyaluronic acid and NSAIDS
US5639738A (en) *	1992-02-20	1997-06-17	Hyal Pharmaceutical Corporation	Treatment of basal cell carcinoma and actinic keratosis employing hyaluronic acid and NSAIDs
US5410016A (en) *	1990-10-15	1995-04-25	Board Of Regents, The University Of Texas System	Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
US5626863A (en) *	1992-02-28	1997-05-06	Board Of Regents, The University Of Texas System	Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
US5462990A (en) *	1990-10-15	1995-10-31	Board Of Regents, The University Of Texas System	Multifunctional organic polymers
IT1247175B (it) *	1991-04-19	1994-12-12	Fidia Spa	Procedimento per la purificazione di acido ialuronico e frazione di acido ialuronico puro per uso oftalmico.
US5234914A (en) *	1991-06-11	1993-08-10	Patent Biopharmaceutics, Inc.	Methods of treating hemorrhoids and anorecial disease
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1986
- 1986-10-13 IT IT48546/86A patent/IT1198449B/it active
1987
- 1987-09-29 IL IL84032A patent/IL84032A/xx active IP Right Grant
- 1987-09-29 IE IE872618A patent/IE872618L/xx unknown
- 1987-09-30 NZ NZ221994A patent/NZ221994A/xx unknown
- 1987-10-06 AT AT87308863T patent/ATE163942T1/de not_active IP Right Cessation
- 1987-10-06 EP EP87308863A patent/EP0265116B1/en not_active Expired - Lifetime
- 1987-10-06 ES ES87308863T patent/ES2115583T3/es not_active Expired - Lifetime
- 1987-10-06 DE DE3752176T patent/DE3752176T2/de not_active Expired - Lifetime
- 1987-10-08 ZA ZA877559A patent/ZA877559B/xx unknown
- 1987-10-08 CA CA000548921A patent/CA1317287C/en not_active Expired - Fee Related
- 1987-10-09 IN IN787/CAL/87A patent/IN170801B/en unknown
- 1987-10-12 NO NO874251A patent/NO175374C/no not_active IP Right Cessation
- 1987-10-12 PH PH35917A patent/PH26025A/en unknown
- 1987-10-13 JP JP62258165A patent/JP2648308B2/ja not_active Expired - Lifetime
- 1987-10-13 AU AU79600/87A patent/AU610087B2/en not_active Ceased
- 1987-10-13 FI FI874504A patent/FI96610C/fi not_active IP Right Cessation
- 1987-10-13 CN CN87106919A patent/CN1025035C/zh not_active Expired - Fee Related
- 1987-10-13 US US07/106,658 patent/US4957744A/en not_active Expired - Lifetime
- 1987-10-13 DK DK536087A patent/DK536087A/da not_active Application Discontinuation
- 1987-10-13 AR AR87308948A patent/AR247406A1/es active
- 1987-10-13 HU HU874614A patent/HU204858B/hu not_active IP Right Cessation
- 1987-10-13 KR KR1019870011311A patent/KR920002702B1/ko not_active IP Right Cessation
- 1987-10-13 PT PT85908A patent/PT85908B/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS63105003A (ja)	1988-05-10
ES2115583T3 (es)	1998-07-01
FI874504A (fi)	1988-04-14
HUT45734A (en)	1988-08-29
FI96610B (fi)	1996-04-15
EP0265116A3 (en)	1989-02-08
EP0265116B1 (en)	1998-03-11
AU610087B2 (en)	1991-05-16
IL84032A (en)	1997-11-20
JP2648308B2 (ja)	1997-08-27
IT1198449B (it)	1988-12-21
ATE163942T1 (de)	1998-03-15
CA1317287C (en)	1993-05-04
PT85908B (pt)	1990-08-31
NO874251L (no)	1988-04-14
KR880005155A (ko)	1988-06-28
CN87106919A (zh)	1988-08-24
US4957744A (en)	1990-09-18
HU204858B (en)	1992-02-28
NO175374B (no)	1994-06-27
NO175374C (no)	1994-10-05
IN170801B (it)	1992-05-23
NO874251D0 (no)	1987-10-12
DK536087A (da)	1988-04-14
EP0265116A2 (en)	1988-04-27
DK536087D0 (da)	1987-10-13
IT8648546A0 (it)	1986-10-13
DE3752176D1 (de)	1998-04-16
NZ221994A (en)	1990-07-26
AU7960087A (en)	1988-04-21
AR247406A1 (es)	1994-12-29
FI874504A0 (fi)	1987-10-13
DE3752176T2 (de)	1998-10-29
IE872618L (en)	1988-04-13
PT85908A (en)	1987-11-01
FI96610C (fi)	1996-07-25
CN1025035C (zh)	1994-06-15
KR920002702B1 (ko)	1992-03-31
ZA877559B (en)	1988-04-13

Publication	Publication Date	Title
PH26025A (en)	1992-01-29	Esters of polyvalent alcohols of hyaluronic acid
CA1341603C (en)	2010-04-20	Acidic polysaccharide esters and process for their preparation
DE60104703T2 (de)	2005-07-14	Neue vernetzte derivate der hyaluronsäure.
EP0251905B1 (en)	1994-11-02	Esters of alginic acid
DE69922522T2 (de)	2005-12-15	Funktionalisierte hyaluronsäurederivate, bildung von hydrogelen und deren verwendung in situ
US5202431A (en)	1993-04-13	Partial esters of hyaluronic acid
AU2007296939B9 (en)	2012-07-19	Hyaluronic acid derivatives obtained via "click chemistry" crosslinking
EP1196179B1 (en)	2006-08-16	Hyaluronic acid esters for the treatment of normotrophic scarring of the skin
US5416205A (en)	1995-05-16	New esters of alginic acid
CA1338236C (en)	1996-04-09	Esters of alginic acid