LT3806B - Hyaluronic acid associates, composition containing them, process for preparing the composition, process for preparing zinc hyaluronate aqueous solution - Google Patents

Hyaluronic acid associates, composition containing them, process for preparing the composition, process for preparing zinc hyaluronate aqueous solution Download PDF

Info

Publication number: LT3806B
Authority: LT; Lithuania
Prior art keywords: hyaluronate; zinc; hyaluronic acid; solution; periodic table
Prior art date: 1989-02-24

Application number

LTIP1418A

Other languages

English (en)

Lithuanian (lt)

Inventor

Kalman Burger

Geza Takacsi-Nagy

Ivan Rethey-Prikkel

Janos Illes

Bela Stefko

Erzsebet Neszmelyi

Istvan Gebhardt

Istvan Racz

Gyongyver Kiraly

Viktoria Varkonyi

Original Assignee

Richter Gedeon Vegyeszet

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.)

1989-02-24

Filing date

1993-10-26

Publication date

1996-03-25

1993-10-26 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1995-05-25 Publication of LTIP1418A publication Critical patent/LTIP1418A/xx

1996-03-25 Publication of LT3806B publication Critical patent/LT3806B/lt

Links

VJVOFLWZDWLHNR-MRCUWXFGSA-N icosan-9-yl (z)-docos-13-enoate Chemical compound CCCCCCCCCCCC(CCCCCCCC)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC VJVOFLWZDWLHNR-MRCUWXFGSA-N 0.000 title claims abstract description 73
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 abstract description 36
239000000203 mixture Substances 0.000 title claims abstract description 34
239000007864 aqueous solution Substances 0.000 title claims description 30
229920002674 hyaluronan Polymers 0.000 title claims description 24
229960003160 hyaluronic acid Drugs 0.000 title claims description 24
238000004519 manufacturing process Methods 0.000 title claims 3
238000000034 method Methods 0.000 claims abstract description 23
229910021645 metal ion Inorganic materials 0.000 claims abstract description 20
230000000737 periodic effect Effects 0.000 claims abstract description 20
239000004480 active ingredient Substances 0.000 claims abstract description 8
239000002537 cosmetic Substances 0.000 claims abstract description 7
239000000969 carrier Substances 0.000 claims abstract description 3
239000000243 solution Substances 0.000 claims description 98
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 68
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 claims description 48
229920002385 Sodium hyaluronate Polymers 0.000 claims description 43
229940010747 sodium hyaluronate Drugs 0.000 claims description 42
239000011592 zinc chloride Substances 0.000 claims description 34
235000005074 zinc chloride Nutrition 0.000 claims description 34
229940014041 hyaluronate Drugs 0.000 claims description 33
WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 claims description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 9
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
239000002244 precipitate Substances 0.000 claims description 7
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
239000000654 additive Substances 0.000 claims description 4
-1 n-butanoyl Chemical group 0.000 claims description 4
238000009472 formulation Methods 0.000 claims description 3
239000007900 aqueous suspension Substances 0.000 claims description 2
229910001429 cobalt ion Inorganic materials 0.000 claims description 2
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 2
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
239000012050 conventional carrier Substances 0.000 claims 1
229910001510 metal chloride Inorganic materials 0.000 claims 1
230000008569 process Effects 0.000 abstract description 17
238000002360 preparation method Methods 0.000 abstract description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
239000011701 zinc Substances 0.000 description 19
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 17
239000012153 distilled water Substances 0.000 description 17
229910052725 zinc Inorganic materials 0.000 description 17
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
208000025865 Ulcer Diseases 0.000 description 13
239000007924 injection Substances 0.000 description 13
238000002347 injection Methods 0.000 description 13
231100000397 ulcer Toxicity 0.000 description 13
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 12
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 12
229910001415 sodium ion Inorganic materials 0.000 description 12
229960002920 sorbitol Drugs 0.000 description 12
238000011282 treatment Methods 0.000 description 12
150000002500 ions Chemical class 0.000 description 11
239000000600 sorbitol Substances 0.000 description 11
239000000644 isotonic solution Substances 0.000 description 10
230000003902 lesion Effects 0.000 description 10
238000005259 measurement Methods 0.000 description 9
CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 8
230000003204 osmotic effect Effects 0.000 description 8
239000004302 potassium sorbate Substances 0.000 description 8
235000010241 potassium sorbate Nutrition 0.000 description 8
229940069338 potassium sorbate Drugs 0.000 description 8
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 7
239000012154 double-distilled water Substances 0.000 description 7
239000008103 glucose Substances 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229910017052 cobalt Inorganic materials 0.000 description 6
239000010941 cobalt Substances 0.000 description 6
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 6
239000008367 deionised water Substances 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000011521 glass Substances 0.000 description 5
239000012528 membrane Substances 0.000 description 5
239000011148 porous material Substances 0.000 description 5
238000001556 precipitation Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
230000003993 interaction Effects 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 3
206010052428 Wound Diseases 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
230000008901 benefit Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000008859 change Effects 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
239000003871 white petrolatum Substances 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 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
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000009471 action Effects 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
229940074979 cetyl palmitate Drugs 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
230000035876 healing Effects 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
230000031700 light absorption Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
150000002772 monosaccharides Chemical class 0.000 description 2
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
230000017074 necrotic cell death Effects 0.000 description 2
229960005323 phenoxyethanol Drugs 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
239000000523 sample Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229950004959 sorbitan oleate Drugs 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000008961 swelling Effects 0.000 description 2
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 2
238000004448 titration Methods 0.000 description 2
229940045860 white wax Drugs 0.000 description 2
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
YOBWBLFILQYRFY-UHFFFAOYSA-N 2-hexadecylpyridine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCC1=CC=CC=[NH+]1 YOBWBLFILQYRFY-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
IWNWLPUNKAYUAW-UHFFFAOYSA-N Ethylendiamine dihydroiodide Chemical compound I.I.NCCN IWNWLPUNKAYUAW-UHFFFAOYSA-N 0.000 description 1
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
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 1
206010061218 Inflammation Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000736262 Microbiota Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
229910052768 actinide Inorganic materials 0.000 description 1
150000001255 actinides Chemical class 0.000 description 1
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 1
239000003513 alkali Substances 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
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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 1
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YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
SXYCCJAPZKHOLS-UHFFFAOYSA-N chembl2008674 Chemical compound [O-][N+](=O)C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3O)=C(O)C=C(S(O)(=O)=O)C2=C1 SXYCCJAPZKHOLS-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
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150000004700 cobalt complex Chemical class 0.000 description 1
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229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
231100000444 skin lesion Toxicity 0.000 description 1
206010040882 skin lesion Diseases 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1

Classifications

- 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
- 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
- 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
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/58—Metal complex; Coordination compounds

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Dermatology (AREA)
Molecular Biology (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Inorganic Chemistry (AREA)
Birds (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biochemistry (AREA)
Materials Engineering (AREA)
Polymers & Plastics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Thiazole And Isothizaole Compounds (AREA)

LTIP1418A 1989-02-24 1993-10-26 Hyaluronic acid associates, composition containing them, process for preparing the composition, process for preparing zinc hyaluronate aqueous solution LT3806B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU89891A HU203372B (en)	1989-02-24	1989-02-24	Process for producing hyaluronic associates and pharmaceutical compositions and cosmetics comprising such active ingredient

Publications (2)

Publication Number	Publication Date
LTIP1418A LTIP1418A (en)	1995-05-25
LT3806B true LT3806B (en)	1996-03-25

Family

ID=10951903

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
LTIP1418A LT3806B (en)	1989-02-24	1993-10-26	Hyaluronic acid associates, composition containing them, process for preparing the composition, process for preparing zinc hyaluronate aqueous solution
LTIP1474A LT3873B (en)	1989-02-24	1993-11-18	Compositions containing deprotonated hyaluronic acid associates and procrss for preparing same

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
LTIP1474A LT3873B (en)	1989-02-24	1993-11-18	Compositions containing deprotonated hyaluronic acid associates and procrss for preparing same

Country Status (33)

Country	Link
US (1)	US5554598A (pt)
EP (1)	EP0413016B1 (pt)
JP (1)	JP2571312B2 (pt)
KR (1)	KR960015624B1 (pt)
CN (2)	CN1024557C (pt)
AR (1)	AR243538A1 (pt)
AT (1)	ATE98964T1 (pt)
AU (1)	AU623232B2 (pt)
BG (1)	BG61515B2 (pt)
CA (1)	CA2027596C (pt)
CZ (1)	CZ281000B6 (pt)
DD (1)	DD292263A5 (pt)
DE (1)	DE69005394T2 (pt)
DK (1)	DK0413016T3 (pt)
ES (1)	ES2061016T3 (pt)
FI (1)	FI101707B (pt)
GE (2)	GEP19981358B (pt)
GR (1)	GR1000869B (pt)
HK (1)	HK1003003A1 (pt)
HU (2)	HU203372B (pt)
IE (1)	IE62408B1 (pt)
IL (1)	IL93489A (pt)
LT (2)	LT3806B (pt)
LV (2)	LV10112B (pt)
MY (1)	MY105168A (pt)
NO (1)	NO301169B1 (pt)
PL (1)	PL163417B1 (pt)
PT (1)	PT93237B (pt)
RU (2)	RU2099350C1 (pt)
SK (1)	SK279530B6 (pt)
UA (2)	UA26324A (pt)
WO (1)	WO1990010020A1 (pt)
ZA (1)	ZA901357B (pt)

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DE4115454A1 (de) *	1991-05-11	1992-11-12	Basf Ag	Eisen-(iii)-hyaluronate
US5531716A (en) *	1993-09-29	1996-07-02	Hercules Incorporated	Medical devices subject to triggered disintegration
IT1273742B (it) *	1994-08-01	1997-07-09	Lifegroup Spa	Composizioni ad elevata bioadesivita' e mucoadesivita' utili per il trattamento di epitali e mucose
CN1064372C (zh) *	1994-08-26	2001-04-11	顾其胜	透明质酸钠制剂的制备方法
US6368356B1 (en)	1996-07-11	2002-04-09	Scimed Life Systems, Inc.	Medical devices comprising hydrogel polymers having improved mechanical properties
HU225991B1 (en)	1997-04-29	2008-02-28	Richter Gedeon Nyrt	Use of the zinc hyaluronate associate (complex) for the preparation of pharmaceutical compositions for oral use against peptic ulcer
HU225329B1 (en) *	1996-09-12	2006-09-28	Richter Gedeon Vegyeszet	Use of zinc or cobalt hyaluronate associate for the manufacture of pharmaceutical compositions of antimicrobial activity
US6869938B1 (en)	1997-06-17	2005-03-22	Fziomed, Inc.	Compositions of polyacids and polyethers and methods for their use in reducing adhesions
US7192984B2 (en)	1997-06-17	2007-03-20	Fziomed, Inc.	Compositions of polyacids and polyethers and methods for their use as dermal fillers
US5906997A (en) *	1997-06-17	1999-05-25	Fzio Med, Inc.	Bioresorbable compositions of carboxypolysaccharide polyether intermacromolecular complexes and methods for their use in reducing surgical adhesions
JP2003089647A (ja) *	1999-03-10	2003-03-28	Takada Seiyaku Kk	関節性疾患治療剤
US6566345B2 (en)	2000-04-28	2003-05-20	Fziomed, Inc.	Polyacid/polyalkylene oxide foams and gels and methods for their delivery
US6913765B2 (en)	2001-03-21	2005-07-05	Scimed Life Systems, Inc.	Controlling resorption of bioresorbable medical implant material
CZ12015U1 (cs) *	2002-01-18	2002-02-25	Cpn Spol. S R.O.	Přípravek pro prevenci adheze bandáľe na ránu
RU2220729C2 (ru) *	2002-01-31	2004-01-10	Общество с ограниченной ответственностью "Научный Центр системных исследований и технологий 2000"	Гелевая композиция, используемая в стоматологии
US8461410B2 (en)	2002-09-11	2013-06-11	Ethicon, Inc.	Wound dressing materials comprising complexes of anionic polysaccharides with silver
GB2392913B (en) *	2002-09-11	2007-04-04	Johnson & Johnson Medical Ltd	Wound dressings comprising complexes of oxidised celluloses with silver
RU2227742C1 (ru) *	2002-09-25	2004-04-27	Представительство фирмы "Гедеон Рихтер" на Волге	Средство для профилактики послеоперационного спаечного процесса
HUP0303779A2 (en) *	2003-11-20	2006-02-28	Richter Gedeon Vegyeszet	Pharmaceutical compositions containing hyaluronan complex for the treatment of sclerosis multiplex
RU2280041C1 (ru) *	2005-04-21	2006-07-20	Общество с ограниченной ответственностью Научно-производственное предприятие "Тульская индустрия ЛТД"	Способ получения водорастворимых солевых комплексов гиалуроновой кислоты (варианты)
JPWO2006121210A1 (ja) *	2005-05-13	2008-12-18	高田製薬株式会社	皮膚状態改善剤
JPWO2006121209A1 (ja) *	2005-05-13	2008-12-18	高田製薬株式会社	湿疹・皮膚炎群治療剤
JP4220513B2 (ja) *	2005-12-01	2009-02-04	株式会社資生堂	カチオン化ヒアルロン酸
CN1329414C (zh) *	2005-12-02	2007-08-01	凌沛学	透明质酸铋钾及其制备方法和应用
CN100348621C (zh) *	2005-12-02	2007-11-14	凌沛学	透明质酸铋及其制备方法和应用
FR2918565B1 (fr) *	2007-07-12	2009-10-30	Biopharmex Holding Sa	Hydrogel de carboxyalkylamide de chitosan, sa preparation et son utilisation cosmetique et dermatologique
ES2326721B1 (es) *	2008-01-04	2010-07-16	Endor Nanotechnologies, S.L.	Conjugado de acido hialuronico para el tratamiento cosmetico y procedimiento de preparacion.
TWI516269B (zh)	2009-08-14	2016-01-11	禾伸堂生技股份有限公司	使用於炎症性腸疾病（ｉｂｄ）治療和預防之透明質酸混合物
TWI383796B (zh)	2009-08-14	2013-02-01	Holy Stone Healthcare Co Ltd	Use of hyaluronic acid mixture for the treatment and prevention of peptic ulcer and duodenal ulcer
HUP0900717A3 (en)	2009-11-18	2012-02-28	Richter Gedeon Nyrt	Pharmaceutical composition for urological use containing zinc hyaluronate
JP5728865B2 (ja)	2010-01-07	2015-06-03	株式会社リコー	放熱機構、及び放熱板の支え金具
CN102834417B (zh) *	2010-04-14	2015-11-25	丘比株式会社	透明质酸金属盐的制造方法、包含透明质酸金属盐的化妆品的制造方法以及透明质酸锌及其制造方法
ES2376680B8 (es)	2010-08-16	2013-04-30	Nylstar, S.A.	Fibra textil cosmética, procedimiento de obtención y su empleo.
CN102552309B (zh) *	2010-12-15	2013-06-05	北京理工大学	一种透明质酸金的用途及其制备方法
JP5763953B2 (ja) *	2011-03-31	2015-08-12	ロート製薬株式会社	外用組成物
CN102961396A (zh) *	2012-12-17	2013-03-13	程玉李	透明质酸金属盐在制备治疗皮肤病药物中的应用、其药物组合物及其制备方法
US10449254B2 (en)	2013-11-03	2019-10-22	The Regents Of The University Of California	Ionic liquids for transdermal drug delivery
JP6608620B2 (ja) *	2015-05-26	2019-11-20	ロート製薬株式会社	皮膚外用剤
CA3035414C (en) *	2016-08-29	2022-02-22	The Regents Of The University Of California	Topical formulations based on ionic species for skin treatment
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1989
- 1989-02-24 HU HU89891A patent/HU203372B/hu unknown
1990
- 1990-02-20 HK HK98102052A patent/HK1003003A1/en not_active IP Right Cessation
- 1990-02-20 UA UA4895005A patent/UA26324A/uk unknown
- 1990-02-20 DE DE69005394T patent/DE69005394T2/de not_active Expired - Lifetime
- 1990-02-20 KR KR1019900702327A patent/KR960015624B1/ko not_active Expired - Lifetime
- 1990-02-20 AT AT90903397T patent/ATE98964T1/de not_active IP Right Cessation
- 1990-02-20 UA UA94061636A patent/UA39174C2/uk unknown
- 1990-02-20 JP JP2503644A patent/JP2571312B2/ja not_active Expired - Lifetime
- 1990-02-20 DK DK90903397.9T patent/DK0413016T3/da not_active Application Discontinuation
- 1990-02-20 WO PCT/HU1990/000013 patent/WO1990010020A1/en not_active Ceased
- 1990-02-20 AU AU51088/90A patent/AU623232B2/en not_active Expired
- 1990-02-20 CA CA002027596A patent/CA2027596C/en not_active Expired - Lifetime
- 1990-02-20 RU SU904831382A patent/RU2099350C1/ru active
- 1990-02-20 ES ES90903397T patent/ES2061016T3/es not_active Expired - Lifetime
- 1990-02-20 EP EP90903397A patent/EP0413016B1/en not_active Expired - Lifetime
- 1990-02-22 PT PT93237A patent/PT93237B/pt active IP Right Grant
- 1990-02-22 MY MYPI90000280A patent/MY105168A/en unknown
- 1990-02-22 GR GR900100137A patent/GR1000869B/el not_active IP Right Cessation
- 1990-02-22 IL IL9348990A patent/IL93489A/en not_active IP Right Cessation
- 1990-02-22 CZ CS90857A patent/CZ281000B6/cs not_active IP Right Cessation
- 1990-02-22 SK SK857-90A patent/SK279530B6/sk not_active IP Right Cessation
- 1990-02-22 IE IE63790A patent/IE62408B1/en not_active IP Right Cessation
- 1990-02-22 ZA ZA901357A patent/ZA901357B/xx unknown
- 1990-02-22 DD DD90338061A patent/DD292263A5/de not_active IP Right Cessation
- 1990-02-23 AR AR90316230A patent/AR243538A1/es active
- 1990-02-23 CN CN90100904A patent/CN1024557C/zh not_active Expired - Lifetime
- 1990-02-23 PL PL90283942A patent/PL163417B1/pl unknown
- 1990-02-23 CN CN93109689A patent/CN1051228C/zh not_active Expired - Lifetime
- 1990-10-17 FI FI905109A patent/FI101707B/fi active IP Right Grant
- 1990-10-23 NO NO904584A patent/NO301169B1/no not_active IP Right Cessation
1991
- 1991-04-11 RU SU914895005A patent/RU2021304C1/ru active
1992
- 1992-08-10 US US07/928,154 patent/US5554598A/en not_active Expired - Lifetime
- 1992-12-30 LV LVP-92-687A patent/LV10112B/lv unknown
1993
- 1993-06-17 GE GEAP1993894A patent/GEP19981358B/en unknown
- 1993-06-29 LV LVP-93-747A patent/LV10965B/lv unknown
- 1993-08-12 GE GEAP19931400A patent/GEP19971015B/en unknown
- 1993-10-26 LT LTIP1418A patent/LT3806B/lt not_active IP Right Cessation
- 1993-11-18 LT LTIP1474A patent/LT3873B/lt not_active IP Right Cessation
1994
- 1994-03-01 BG BG098631A patent/BG61515B2/bg unknown
1995
- 1995-06-07 HU HU95P/P00167P patent/HU211465A9/hu unknown

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Also Published As

Publication number	Publication date
HU211465A9 (en)	1995-11-28
UA39174C2 (uk)	2001-06-15
GEP19971015B (en)	1997-05-30
PT93237A (pt)	1990-08-31
KR960015624B1 (ko)	1996-11-18
SK85790A3 (en)	1998-12-02
GR1000869B (el)	1993-03-16
FI101707B1 (fi)	1998-08-14
LV10112A (lv)	1994-05-10
FI905109A0 (fi)	1990-10-17
IE62408B1 (en)	1995-01-25
EP0413016A1 (en)	1991-02-20
DE69005394D1 (de)	1994-02-03
LV10112B (en)	1995-02-20
LV10965B (en)	1996-08-20
AR243538A1 (es)	1993-08-31
CA2027596C (en)	2001-01-02
ZA901357B (en)	1990-11-28
FI101707B (fi)	1998-08-14
EP0413016B1 (en)	1993-12-22
CN1051228C (zh)	2000-04-12
LTIP1418A (en)	1995-05-25
ATE98964T1 (de)	1994-01-15
CA2027596A1 (en)	1990-08-25
MY105168A (en)	1994-08-30
CZ281000B6 (cs)	1996-05-15
UA26324A (uk)	1999-08-30
ES2061016T3 (es)	1994-12-01
DE69005394T2 (de)	1994-07-28
AU623232B2 (en)	1992-05-07
CZ85790A3 (en)	1995-02-15
SK279530B6 (sk)	1998-12-02
CN1045394A (zh)	1990-09-19
JPH03505231A (ja)	1991-11-14
NO301169B1 (no)	1997-09-22
IE900637L (en)	1990-08-24
DK0413016T3 (da)	1994-02-14
PL163417B1 (pl)	1994-03-31
WO1990010020A1 (en)	1990-09-07
KR920700231A (ko)	1992-02-19
NO904584D0 (no)	1990-10-23
LTIP1474A (en)	1995-06-26
AU5108890A (en)	1990-09-26
US5554598A (en)	1996-09-10
PT93237B (pt)	1996-01-31
LV10965A (lv)	1995-12-20
IL93489A (en)	1994-05-30
RU2021304C1 (ru)	1994-10-15
DD292263A5 (de)	1991-07-25
LT3873B (en)	1996-04-25
RU2099350C1 (ru)	1997-12-20
BG61515B2 (bg)	1997-10-31
GEP19981358B (en)	1998-08-25
PL283942A1 (en)	1991-01-28
NO904584L (no)	1990-12-21
HK1003003A1 (en)	1998-09-30
JP2571312B2 (ja)	1997-01-16
CN1024557C (zh)	1994-05-18
CN1086422A (zh)	1994-05-11
HUT53128A (en)	1990-09-28
GR900100137A (en)	1991-06-28
HU203372B (en)	1991-07-29

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Date	Code	Title	Description
2013-11-25	MK9A	Expiry of a patent	Effective date: 20131026

Publication	Publication Date	Title
RU2021304C1 (ru)	1994-10-15	Способ получения биологически активной композиции
JP2969584B2 (ja)	1999-11-02	眼の治療用組成物
HK1003003B (en)	1998-09-30	Novel compositions containing hyaluronic acid associates and a process for preparing same
DE69323442T2 (de)	1999-06-24	Flüssige pharmazeutische Formulierung mit verlängerter Wirkstoffabgabe
DE69124109T2 (de)	1997-06-19	Gelbildende flüssigträger-zusammensetzung
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EP1126881B1 (de)	2004-06-16	Mucoadhäsive polymere, deren verwendung sowie deren herstellungsverfahren
US6458774B1 (en)	2002-10-01	Compositions containing hyaluronic acid associates and a process for preparing same
DE602004006024T2 (de)	2007-12-27	Pharmazeutische zusammensetzung mit einem zink/hyaluronat-komplex zur behandlung von multipler sklerose
US5472950A (en)	1995-12-05	Compositions containing cobalt hyaluronic acid complex
EP3250181B1 (en)	2020-06-03	Minoxidil-based pharmaceutical formulation for the topical use and kit thereof
DE2714676C2 (de)	1987-03-19	Augentropfenlösung
HRP930063A2 (en)	1995-10-31	Novel compositions containing hyaluronic acid associates and a process for preparing the same
SI9010671A (en)	1997-06-30	Novel compositions containing complexes of the hyaluronic acid and the procedure for their preparation
DE2201669C3 (de)	1981-05-07	Pyrogenfreier Blutplasmaersatz
JP2873847B2 (ja)	1999-03-24	エタノール溶液の製造法と該エタノール溶液を使用する化粧料
JPS6340166B2 (pt)	1988-08-10