HRP950024A2 - Crosslinked polymeric ammonium salts - Google Patents
Crosslinked polymeric ammonium salts Download PDFInfo
- Publication number
- HRP950024A2 HRP950024A2 HR08/202,395A HRP950024A HRP950024A2 HR P950024 A2 HRP950024 A2 HR P950024A2 HR P950024 A HRP950024 A HR P950024A HR P950024 A2 HRP950024 A2 HR P950024A2
- Authority
- HR
- Croatia
- Prior art keywords
- cross
- nitrogen atoms
- polymer
- polymeric ammonium
- linked
- Prior art date
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- 150000003863 ammonium salts Chemical class 0.000 title claims abstract description 105
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
- QAWTYRYXDYHQNU-UHFFFAOYSA-N diazathiane Chemical compound NSN QAWTYRYXDYHQNU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229930194542 Keto Natural products 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000000468 ketone group Chemical group 0.000 claims abstract description 9
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 8
- 229920000642 polymer Polymers 0.000 claims description 188
- 238000000034 method Methods 0.000 claims description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 98
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 80
- 239000002904 solvent Substances 0.000 claims description 67
- -1 poly(2-hydroxyethyl methacrylate) Polymers 0.000 claims description 64
- 239000003623 enhancer Substances 0.000 claims description 52
- 239000003613 bile acid Substances 0.000 claims description 49
- 229920000080 bile acid sequestrant Polymers 0.000 claims description 47
- 230000008569 process Effects 0.000 claims description 35
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
- CVTZKFWZDBJAHE-UHFFFAOYSA-N [N].N Chemical group [N].N CVTZKFWZDBJAHE-UHFFFAOYSA-N 0.000 claims description 33
- 230000027455 binding Effects 0.000 claims description 32
- 230000008961 swelling Effects 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 31
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical class C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 23
- 150000001412 amines Chemical class 0.000 claims description 21
- 235000012000 cholesterol Nutrition 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 19
- 210000002381 plasma Anatomy 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 17
- 230000001588 bifunctional effect Effects 0.000 claims description 17
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 17
- 150000002894 organic compounds Chemical class 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 16
- 150000004985 diamines Chemical class 0.000 claims description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 229920002472 Starch Polymers 0.000 claims description 10
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 235000010980 cellulose Nutrition 0.000 claims description 7
- 229920002678 cellulose Polymers 0.000 claims description 7
- 150000002334 glycols Chemical class 0.000 claims description 7
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 7
- 239000011118 polyvinyl acetate Substances 0.000 claims description 7
- 235000019698 starch Nutrition 0.000 claims description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229940099352 cholate Drugs 0.000 claims description 6
- BHQCQFFYRZLCQQ-OELDTZBJSA-M cholate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-M 0.000 claims description 6
- 229910052739 hydrogen Chemical group 0.000 claims description 6
- 239000001257 hydrogen Chemical group 0.000 claims description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000008107 starch Substances 0.000 claims description 6
- 229920000856 Amylose Polymers 0.000 claims description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 5
- 235000010987 pectin Nutrition 0.000 claims description 5
- 239000001814 pectin Substances 0.000 claims description 5
- 229920001277 pectin Polymers 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- OTVRYZXVVMZHHW-FNOPAARDSA-N (8s,9s,10r,13r,14s,17r)-3-chloro-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CC(Cl)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 OTVRYZXVVMZHHW-FNOPAARDSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 4
- 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 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 229920002494 Zein Polymers 0.000 claims description 4
- 235000010323 ascorbic acid Nutrition 0.000 claims description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 4
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 4
- 229920000609 methyl cellulose Polymers 0.000 claims description 4
- 239000001923 methylcellulose Substances 0.000 claims description 4
- 235000010981 methylcellulose Nutrition 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 4
- 229920001285 xanthan gum Polymers 0.000 claims description 4
- 239000000230 xanthan gum Substances 0.000 claims description 4
- 235000010493 xanthan gum Nutrition 0.000 claims description 4
- 229940082509 xanthan gum Drugs 0.000 claims description 4
- 239000005019 zein Substances 0.000 claims description 4
- 229940093612 zein Drugs 0.000 claims description 4
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 3
- ZFFFTNIZYWZUOG-UHFFFAOYSA-N 1,8-dibromo-3-ethyloctane Chemical compound BrCCC(CC)CCCCCBr ZFFFTNIZYWZUOG-UHFFFAOYSA-N 0.000 claims description 3
- DLYVTEULDNMQAR-SRNOMOOLSA-N Cholic Acid Methyl Ester Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCC(=O)OC)[C@@]2(C)[C@@H](O)C1 DLYVTEULDNMQAR-SRNOMOOLSA-N 0.000 claims description 3
- 239000001856 Ethyl cellulose Substances 0.000 claims description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 3
- 229920002148 Gellan gum Polymers 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 3
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 3
- 229920002310 Welan gum Polymers 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 150000002016 disaccharides Chemical class 0.000 claims description 3
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 3
- 229920001249 ethyl cellulose Polymers 0.000 claims description 3
- 230000014759 maintenance of location Effects 0.000 claims description 3
- 150000002772 monosaccharides Chemical class 0.000 claims description 3
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229920001592 potato starch Polymers 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229940100445 wheat starch Drugs 0.000 claims description 3
- WXHAZAOZCQDUFE-UHFFFAOYSA-N 1,18-dibromooctadecane Chemical compound BrCCCCCCCCCCCCCCCCCCBr WXHAZAOZCQDUFE-UHFFFAOYSA-N 0.000 claims description 2
- LVWSZGCVEZRFBT-UHFFFAOYSA-N 1,7-dibromoheptane Chemical compound BrCCCCCCCBr LVWSZGCVEZRFBT-UHFFFAOYSA-N 0.000 claims description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 2
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 claims description 2
- KZDTZHQLABJVLE-UHFFFAOYSA-N 1,8-diiodooctane Chemical compound ICCCCCCCCI KZDTZHQLABJVLE-UHFFFAOYSA-N 0.000 claims description 2
- WAJSPMCTLXYWMN-UHFFFAOYSA-N 1,9-dibromodecane Chemical compound CC(Br)CCCCCCCCBr WAJSPMCTLXYWMN-UHFFFAOYSA-N 0.000 claims description 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 2
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 240000008042 Zea mays Species 0.000 claims description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 229940072107 ascorbate Drugs 0.000 claims description 2
- 150000001841 cholesterols Chemical class 0.000 claims description 2
- 235000005822 corn Nutrition 0.000 claims description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 claims description 2
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 claims description 2
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000010492 gellan gum Nutrition 0.000 claims description 2
- 239000000216 gellan gum Substances 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 claims description 2
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 2
- 229960001860 salicylate Drugs 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 239000001509 sodium citrate Substances 0.000 claims 2
- 235000011083 sodium citrates Nutrition 0.000 claims 2
- 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 claims 1
- RBBNTRDPSVZESY-UHFFFAOYSA-N 1,10-dichlorodecane Chemical compound ClCCCCCCCCCCCl RBBNTRDPSVZESY-UHFFFAOYSA-N 0.000 claims 1
- CKJCTZAIDVFHCX-UHFFFAOYSA-N 1,10-diiododecane Chemical compound ICCCCCCCCCCI CKJCTZAIDVFHCX-UHFFFAOYSA-N 0.000 claims 1
- RNXPZVYZVHJVHM-UHFFFAOYSA-N 1,12-dichlorododecane Chemical compound ClCCCCCCCCCCCCCl RNXPZVYZVHJVHM-UHFFFAOYSA-N 0.000 claims 1
- YXCZCXPVHQBSEN-UHFFFAOYSA-N 1,18-diiodooctadecane Chemical compound ICCCCCCCCCCCCCCCCCCI YXCZCXPVHQBSEN-UHFFFAOYSA-N 0.000 claims 1
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 claims 1
- ZZHWQLNCPAJXJE-UHFFFAOYSA-N 1,7-diiodoheptane Chemical compound ICCCCCCCI ZZHWQLNCPAJXJE-UHFFFAOYSA-N 0.000 claims 1
- WXYMNDFVLNUAIA-UHFFFAOYSA-N 1,8-dichlorooctane Chemical compound ClCCCCCCCCCl WXYMNDFVLNUAIA-UHFFFAOYSA-N 0.000 claims 1
- WGAXVZXBFBHLMC-UHFFFAOYSA-N 1,9-dibromononane Chemical compound BrCCCCCCCCCBr WGAXVZXBFBHLMC-UHFFFAOYSA-N 0.000 claims 1
- CPWYLEUYMDFPNE-UHFFFAOYSA-N 1,9-dichlorodecane Chemical compound CC(Cl)CCCCCCCCCl CPWYLEUYMDFPNE-UHFFFAOYSA-N 0.000 claims 1
- WHUJHBWIJNLPKC-UHFFFAOYSA-N 1,9-diiododecane Chemical compound CC(I)CCCCCCCCI WHUJHBWIJNLPKC-UHFFFAOYSA-N 0.000 claims 1
- QVXLFUVDXDMDFE-UHFFFAOYSA-N 1,9-diiodononane Chemical compound ICCCCCCCCCI QVXLFUVDXDMDFE-UHFFFAOYSA-N 0.000 claims 1
- WULYPQWDDJZJDU-UHFFFAOYSA-N 3-ethyl-1,8-diiodooctane Chemical compound ICCC(CC)CCCCCI WULYPQWDDJZJDU-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 229940001468 citrate Drugs 0.000 claims 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical group C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims 1
- IZKZIDXHCDIZKY-UHFFFAOYSA-N heptane-1,1-diamine Chemical compound CCCCCCC(N)N IZKZIDXHCDIZKY-UHFFFAOYSA-N 0.000 claims 1
- 235000011181 potassium carbonates Nutrition 0.000 claims 1
- 239000001508 potassium citrate Substances 0.000 claims 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical class [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims 1
- 235000011082 potassium citrates Nutrition 0.000 claims 1
- 235000011182 sodium carbonates Nutrition 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical class [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 8
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical group N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 239000000203 mixture Substances 0.000 description 58
- 239000000499 gel Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 36
- 229920006037 cross link polymer Polymers 0.000 description 34
- 238000006116 polymerization reaction Methods 0.000 description 33
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- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
- A61K31/787—Polymers containing nitrogen containing heterocyclic rings having nitrogen as a ring hetero atom
-
- 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
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/0226—Quaternisation of polyalkylene(poly)amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polyethers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyamides (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18295494A | 1994-01-18 | 1994-01-18 | |
| US08/202,395 US5556619A (en) | 1992-08-20 | 1994-02-24 | Crosslinked polymeric ammonium salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP950024A2 true HRP950024A2 (en) | 1997-06-30 |
Family
ID=26878587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR08/202,395A HRP950024A2 (en) | 1994-01-18 | 1995-01-18 | Crosslinked polymeric ammonium salts |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5556619A (de) |
| EP (1) | EP0740679B1 (de) |
| JP (1) | JPH09507687A (de) |
| KR (1) | KR970700714A (de) |
| CN (1) | CN1143379A (de) |
| AT (1) | ATE204005T1 (de) |
| AU (1) | AU682930B2 (de) |
| BR (1) | BR9506636A (de) |
| CA (1) | CA2179712C (de) |
| CZ (1) | CZ194396A3 (de) |
| DE (1) | DE69522095T2 (de) |
| DK (1) | DK0740679T3 (de) |
| ES (1) | ES2160696T3 (de) |
| FI (1) | FI962881A0 (de) |
| GR (1) | GR3036589T3 (de) |
| HR (1) | HRP950024A2 (de) |
| HU (1) | HUT75944A (de) |
| IL (1) | IL112343A0 (de) |
| NO (1) | NO962985L (de) |
| NZ (1) | NZ279647A (de) |
| PL (1) | PL315580A1 (de) |
| PT (1) | PT740679E (de) |
| SK (1) | SK93696A3 (de) |
| WO (1) | WO1995019384A1 (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9602812A (es) * | 1994-01-18 | 1997-06-28 | Du Pont | Sales de amonio polimericas, reticuladas. |
| US5925379A (en) * | 1997-03-27 | 1999-07-20 | Geltex Pharmaceuticals, Inc. | Interpenetrating polymer networks for sequestration of bile acids |
| US6083497A (en) * | 1997-11-05 | 2000-07-04 | Geltex Pharmaceuticals, Inc. | Method for treating hypercholesterolemia with unsubstituted polydiallylamine polymers |
| US6271264B1 (en) * | 1998-12-01 | 2001-08-07 | Geltex Pharmaceuticals, Inc. | Polymers containing spirobicyclic ammonium moieties as bile acid sequestrants |
| AU2374800A (en) * | 1998-12-23 | 2000-07-31 | Geltex Pharmaceuticals, Inc. | Amine condensation polymer bile acid sequestrants |
| WO2002066015A1 (en) | 2001-02-16 | 2002-08-29 | Bristol-Myers Squibb Pharma Company | Use of polyalkylamine polymers in controlled release devices |
| ATE378360T1 (de) * | 2003-09-23 | 2007-11-15 | Akciju Sabiedriba Solainfarms | Polymere 3,5-dimethyl-1-adamantylammoniumsalze und deren verwendung in form von virustatika |
| US7335795B2 (en) | 2004-03-22 | 2008-02-26 | Ilypsa, Inc. | Crosslinked amine polymers |
| US7767768B2 (en) | 2003-11-03 | 2010-08-03 | Ilypsa, Inc. | Crosslinked amine polymers |
| US7608674B2 (en) | 2003-11-03 | 2009-10-27 | Ilypsa, Inc. | Pharmaceutical compositions comprising cross-linked small molecule amine polymers |
| US9181364B2 (en) | 2010-02-24 | 2015-11-10 | Relypsa, Inc. | Crosslinked polyvinylamine, polyallylamine, and polyethyleneimine for use as bile acid sequestrants |
| JP5553421B2 (ja) * | 2011-08-01 | 2014-07-16 | 株式会社ルネッサンス・エナジー・リサーチ | Ｃｏ２促進輸送膜及びその製造方法 |
| JP6124911B2 (ja) * | 2011-11-25 | 2017-05-10 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | アルコールの均一系接触アミノ化による親油性ポリアルキレンポリアミン |
| KR101631151B1 (ko) * | 2014-05-22 | 2016-06-27 | 한국과학기술연구원 | 탄화수소계열 전해질 고분자 합성 방법 및 이에 사용되는 중합 용매 |
| BR122021001914B1 (pt) * | 2014-12-10 | 2024-02-27 | Tricida, Inc | Processo para preparação de um polímero de amina reticulada |
| CN113583256B (zh) * | 2021-07-05 | 2022-10-25 | 南京理工大学 | 一种阳离子水凝胶材料的制备方法 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3383281A (en) * | 1961-09-22 | 1968-05-14 | Merck & Co Inc | Method for binding bile acids in vivo |
| US3332841A (en) * | 1961-10-04 | 1967-07-25 | Lilly Co Eli | Method of treating hyperacidity |
| US3499960A (en) * | 1965-01-25 | 1970-03-10 | Merck & Co Inc | Palatable coated particles of an anion exchange resin |
| US3803237A (en) * | 1969-11-03 | 1974-04-09 | Upjohn Co | Reaction products of polyethylenepolyamines and chlorohydrins or epoxy containing compounds |
| NL7017227A (de) * | 1969-12-27 | 1971-06-29 | ||
| US3778476A (en) * | 1970-05-11 | 1973-12-11 | California Inst Of Techn | Polymeric organic halogen salts |
| US3692895A (en) * | 1970-09-08 | 1972-09-19 | Norman A Nelson | Method of reducing hypercholesteremia in humans employing a copolymer of polyethylenepolyamine and a bifunctional substance, such as epichlorohydria |
| US3980770A (en) * | 1971-06-04 | 1976-09-14 | Pharmacia Aktiebolag | Polymerization products containing amino groups useful in serum cholesterol level control |
| US3974272A (en) * | 1972-09-01 | 1976-08-10 | Merck & Co., Inc. | Palatable cholestyramine coacervate compositions |
| US4027009A (en) * | 1973-06-11 | 1977-05-31 | Merck & Co., Inc. | Compositions and methods for depressing blood serum cholesterol |
| US4205064A (en) * | 1973-06-11 | 1980-05-27 | Merck & Co., Inc. | Bile acid sequestering composition containing poly[{alkyl-(3-ammoniopropyl)imino}-trimethylenedihalides] |
| US4147586A (en) * | 1974-09-14 | 1979-04-03 | Monsanto Company | Cellulosic paper containing the reaction product of a dihaloalkane alkylene diamine adduct and epihalohydrin |
| US4071478A (en) * | 1976-06-07 | 1978-01-31 | Merck & Co., Inc. | Controlled partially cross-linked 3,3-ionenes |
| JPS5566513A (en) * | 1978-11-14 | 1980-05-20 | Ono Pharmaceut Co Ltd | Drug for arteriosclerosis comprising high polymer compound as active constituent |
| US4374244A (en) * | 1979-04-13 | 1983-02-15 | Kewanee Industries, Inc. | Linear quaternary ammonium polymers |
| US4439419A (en) * | 1980-02-20 | 1984-03-27 | The Upjohn Company | Method of treating gastric hyperacidity in humans employing a copolymer of polyethylenepolyamine and a bifunctional substance as epichlorhydrin |
| JPS5879022A (ja) * | 1981-11-04 | 1983-05-12 | Bitamin Kenkyusho:Kk | 第四級窒素原子を含有する新規な金属架橋高分子化合物、その製法及び該高分子化合物を有効成分とする高脂血症治療剤 |
| US4604430A (en) * | 1984-05-11 | 1986-08-05 | Bristol-Myers Company | Novel bile sequestrant resin |
| SU1249031A1 (ru) * | 1984-10-15 | 1986-08-07 | Иркутский институт органической химии СО АН СССР | Способ получени полиионенов |
| US4593073A (en) * | 1985-04-23 | 1986-06-03 | The Royal Institution For The Advancement Of Learing (Mcgill Univ.) | Polymer resins with amino acid containing pendants for sorption of bile pigments and bile acids |
| IT1188184B (it) * | 1985-08-14 | 1988-01-07 | Texcontor Ets | Sali ammonici quaternari di polisaccaridi ad attivita' ipocolesterolemizzante |
| DE3609984A1 (de) * | 1986-03-25 | 1987-10-01 | Bayer Ag | Verfahren zur behandlung von fasermaterialien |
| US4877775A (en) * | 1986-06-16 | 1989-10-31 | E. I. Du Pont De Nemours And Company | Polymeric aminosaccharides as antihypercholesterolemic agents |
| IT1223362B (it) * | 1987-11-20 | 1990-09-19 | Texcontor Ets | Derivati cationizzati polisaccaridi ad attivita' ipocolesterolemizzante |
| GB8913823D0 (en) * | 1989-06-15 | 1989-08-02 | Smith Kline French Lab | Compounds |
| GB8829088D0 (en) * | 1988-12-13 | 1989-01-25 | Smith Kline French Lab | Compounds |
| GB8829835D0 (en) * | 1988-12-21 | 1989-02-15 | Smith Kline French Lab | Compounds |
| GB8904489D0 (en) * | 1989-02-28 | 1989-04-12 | Smith Kline French Lab | Compounds |
| IT1229133B (it) * | 1989-03-09 | 1991-07-22 | Farmhispania | Sali ammonici di policiclodestrine per l'impiego come agenti ipocolesterolemizzanti |
| IT1229754B (it) * | 1989-05-17 | 1991-09-10 | Farmhispania | Procedimento per la preparazione del chitosano e di suoi derivati contenenti gruppi di ammonio quaternario |
| GB8911719D0 (en) * | 1989-05-22 | 1989-07-05 | Smith Kline French Lab | Compounds |
| GB8912903D0 (en) * | 1989-06-05 | 1989-07-26 | Smith Kline French Lab | Compounds |
| GB8913700D0 (en) * | 1989-06-14 | 1989-08-02 | Smith Kline French Lab | Compounds |
| GB8913699D0 (en) * | 1989-06-14 | 1989-08-02 | Smith Kline French Lab | Compounds |
| US5236701A (en) * | 1989-07-19 | 1993-08-17 | Lowchol Scientific Inc. | Ingestible hydrophilic polymeric amines useful for lowering blood cholesterol |
| GB8928278D0 (en) * | 1989-12-14 | 1990-02-21 | Smith Kline French Lab | Compounds |
| CA2040996A1 (en) * | 1990-05-02 | 1991-11-03 | Robert L. Albright | Composition and method for controlling cholesterol |
| US5091175A (en) * | 1990-05-14 | 1992-02-25 | Erbamont Inc. | Pharmaceutical composition containing bile acid sequestrant enclosed in a size-exclusion membrane |
| GB9011332D0 (en) * | 1990-05-21 | 1990-07-11 | Smith Kline French Lab | Compounds |
| CA2042870C (en) * | 1991-05-17 | 1996-11-26 | Leon Edward St. Pierre | Metal ion coordinated polyamine resins for the lowering of blood cholesterol |
| ATE168707T1 (de) * | 1992-08-20 | 1998-08-15 | Du Pont | Vernetzte polymerische ammoniumsalze |
-
1994
- 1994-02-24 US US08/202,395 patent/US5556619A/en not_active Expired - Lifetime
-
1995
- 1995-01-16 IL IL11234395A patent/IL112343A0/xx unknown
- 1995-01-18 CZ CZ961943A patent/CZ194396A3/cs unknown
- 1995-01-18 PL PL95315580A patent/PL315580A1/xx unknown
- 1995-01-18 DE DE69522095T patent/DE69522095T2/de not_active Expired - Lifetime
- 1995-01-18 HR HR08/202,395A patent/HRP950024A2/hr not_active Application Discontinuation
- 1995-01-18 SK SK936-96A patent/SK93696A3/sk unknown
- 1995-01-18 EP EP95908568A patent/EP0740679B1/de not_active Expired - Lifetime
- 1995-01-18 CN CN95191992A patent/CN1143379A/zh active Pending
- 1995-01-18 AU AU16834/95A patent/AU682930B2/en not_active Ceased
- 1995-01-18 NZ NZ279647A patent/NZ279647A/en unknown
- 1995-01-18 DK DK95908568T patent/DK0740679T3/da active
- 1995-01-18 PT PT95908568T patent/PT740679E/pt unknown
- 1995-01-18 ES ES95908568T patent/ES2160696T3/es not_active Expired - Lifetime
- 1995-01-18 CA CA002179712A patent/CA2179712C/en not_active Expired - Fee Related
- 1995-01-18 WO PCT/US1995/000713 patent/WO1995019384A1/en not_active Application Discontinuation
- 1995-01-18 HU HU9601950A patent/HUT75944A/hu unknown
- 1995-01-18 AT AT95908568T patent/ATE204005T1/de not_active IP Right Cessation
- 1995-01-18 BR BR9506636A patent/BR9506636A/pt not_active Application Discontinuation
- 1995-01-18 JP JP7519211A patent/JPH09507687A/ja active Pending
-
1996
- 1996-05-22 US US08/604,212 patent/US5726284A/en not_active Expired - Lifetime
- 1996-07-16 KR KR1019960703844A patent/KR970700714A/ko not_active Application Discontinuation
- 1996-07-17 FI FI962881A patent/FI962881A0/fi unknown
- 1996-07-17 NO NO962985A patent/NO962985L/no unknown
-
2001
- 2001-09-11 GR GR20010401446T patent/GR3036589T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1143379A (zh) | 1997-02-19 |
| BR9506636A (pt) | 1997-09-16 |
| CA2179712C (en) | 2001-11-27 |
| JPH09507687A (ja) | 1997-08-05 |
| FI962881A (fi) | 1996-07-17 |
| DE69522095T2 (de) | 2002-03-28 |
| WO1995019384A1 (en) | 1995-07-20 |
| ES2160696T3 (es) | 2001-11-16 |
| AU682930B2 (en) | 1997-10-23 |
| CZ194396A3 (en) | 1997-07-16 |
| DK0740679T3 (da) | 2001-10-22 |
| SK93696A3 (en) | 1997-04-09 |
| NO962985D0 (no) | 1996-07-17 |
| HU9601950D0 (en) | 1996-09-30 |
| CA2179712A1 (en) | 1995-07-20 |
| DE69522095D1 (de) | 2001-09-13 |
| FI962881A0 (fi) | 1996-07-17 |
| PL315580A1 (en) | 1996-11-12 |
| US5556619A (en) | 1996-09-17 |
| IL112343A0 (en) | 1995-03-30 |
| NZ279647A (en) | 1998-06-26 |
| AU1683495A (en) | 1995-08-01 |
| US5726284A (en) | 1998-03-10 |
| HUT75944A (en) | 1997-05-28 |
| GR3036589T3 (en) | 2001-12-31 |
| PT740679E (pt) | 2001-11-30 |
| KR970700714A (ko) | 1997-02-12 |
| EP0740679B1 (de) | 2001-08-08 |
| ATE204005T1 (de) | 2001-08-15 |
| EP0740679A1 (de) | 1996-11-06 |
| NO962985L (no) | 1996-09-17 |
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| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 19970118 Year of fee payment: 3 |
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| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
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