CA2790999C - Crosslinked polyvinylamine, polyallylamine, and polyethyleneimine for use as bile acid sequestrants - Google Patents
Crosslinked polyvinylamine, polyallylamine, and polyethyleneimine for use as bile acid sequestrants Download PDFInfo
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- CA2790999C CA2790999C CA2790999A CA2790999A CA2790999C CA 2790999 C CA2790999 C CA 2790999C CA 2790999 A CA2790999 A CA 2790999A CA 2790999 A CA2790999 A CA 2790999A CA 2790999 C CA2790999 C CA 2790999C
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- polymer
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- amine
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- 229920000083 poly(allylamine) Polymers 0.000 title description 19
- 229920002873 Polyethylenimine Polymers 0.000 title description 16
- 229920000080 bile acid sequestrant Polymers 0.000 title description 6
- 229940096699 bile acid sequestrants Drugs 0.000 title description 5
- 229920000642 polymer Polymers 0.000 claims abstract description 375
- 239000003613 bile acid Substances 0.000 claims abstract description 114
- 150000001412 amines Chemical class 0.000 claims abstract description 86
- 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 compound 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 abstract description 62
- 239000003833 bile salt Substances 0.000 claims abstract description 51
- 229940093761 bile salts Drugs 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 15
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
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- 239000011324 bead Substances 0.000 claims description 15
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- RFDAIACWWDREDC-FRVQLJSFSA-N glycocholic acid 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)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 RFDAIACWWDREDC-FRVQLJSFSA-N 0.000 claims description 15
- WVULKSPCQVQLCU-BUXLTGKBSA-N glycodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 WVULKSPCQVQLCU-BUXLTGKBSA-N 0.000 claims description 15
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- VTAKZNRDSPNOAU-UHFFFAOYSA-M 2-(chloromethyl)oxirane;hydron;prop-2-en-1-amine;n-prop-2-enyldecan-1-amine;trimethyl-[6-(prop-2-enylamino)hexyl]azanium;dichloride Chemical compound Cl.[Cl-].NCC=C.ClCC1CO1.CCCCCCCCCCNCC=C.C[N+](C)(C)CCCCCCNCC=C VTAKZNRDSPNOAU-UHFFFAOYSA-M 0.000 claims description 10
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- PUNFIBHMZSHFKF-KTKRTIGZSA-N (z)-henicos-12-ene-1,2,3-triol Chemical compound CCCCCCCC\C=C/CCCCCCCCC(O)C(O)CO PUNFIBHMZSHFKF-KTKRTIGZSA-N 0.000 claims description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 9
- 239000005642 Oleic acid Substances 0.000 claims description 9
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 9
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 9
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- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 7
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- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims description 7
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- 229960003512 nicotinic acid Drugs 0.000 claims description 7
- 235000001968 nicotinic acid Nutrition 0.000 claims description 7
- 239000011664 nicotinic acid Substances 0.000 claims description 7
- 238000008214 LDL Cholesterol Methods 0.000 claims description 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 6
- 239000005557 antagonist Substances 0.000 claims description 6
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 6
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 5
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical class C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 5
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- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 4
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- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 4
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims description 4
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 4
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- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 claims description 3
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- 229940095064 tartrate Drugs 0.000 description 1
- BHTRKEVKTKCXOH-AYSJQVDDSA-N taurochenodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)C1C2C2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 BHTRKEVKTKCXOH-AYSJQVDDSA-N 0.000 description 1
- WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid 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)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 description 1
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- AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960003433 thalidomide Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- WRCITXQNXAIKLR-UHFFFAOYSA-N tiadenol Chemical compound OCCSCCCCCCCCCCSCCO WRCITXQNXAIKLR-UHFFFAOYSA-N 0.000 description 1
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
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- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
Landscapes
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- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US61/307,811 | 2010-02-24 | ||
| US61/307,814 | 2010-02-24 | ||
| PCT/US2011/026099 WO2011106542A2 (en) | 2010-02-24 | 2011-02-24 | Crosslinked polyvrnylamine, poly all ylamine, and polyethyleneimine for use as bile acid sequestrants |
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| CA2790901C (en) | 2010-02-24 | 2018-05-01 | Relypsa, Inc. | Amine polymers for use as bile acid sequestrants |
| WO2013087237A1 (en) * | 2011-12-13 | 2013-06-20 | Synthon Bv | Purification of sevelamer and related polyallylamines |
| CN104245745B (zh) | 2012-02-09 | 2017-03-29 | 生命技术公司 | 亲水性聚合物颗粒及其制备方法 |
| CA2906501A1 (en) * | 2013-03-15 | 2014-09-25 | Genzyme Corporation | Sequestrants of advanced glycation end product (age) precursors |
| ES2733493T3 (es) | 2013-06-05 | 2019-11-29 | Tricida Inc | Polímeros de unión a protones para la administración oral |
| US10435528B2 (en) | 2013-09-17 | 2019-10-08 | Aquanano Llc | High-capacity anion exchange materials |
| CN103585632A (zh) * | 2013-11-19 | 2014-02-19 | 韩源平 | 胆汁酸螯合剂或/和维生素d在制备防治非酒精性脂肪性肝病药物中的应用 |
| EP3164155B1 (en) | 2014-06-13 | 2022-02-09 | United Therapeutics Corporation | Treprostinil formulations |
| IL322207A (en) * | 2014-12-10 | 2025-09-01 | Tricida Inc | Proton-binding polymers for oral administration |
| MA41202A (fr) | 2014-12-18 | 2017-10-24 | Genzyme Corp | Copolymères polydiallymine réticulé pour le traitement du diabète de type 2 |
| EP3317314B1 (en) | 2015-07-02 | 2020-01-08 | Life Technologies Corporation | Polymer substrates formed from carboxy functional acrylamide |
| WO2017024237A1 (en) * | 2015-08-06 | 2017-02-09 | The Johns Hopkins University | Composition and method for treatment of metabolic disorders |
| MA44875A (fr) | 2016-05-06 | 2019-03-13 | Tricida Inc | Compositions pour le traitement de troubles acido-basiques |
| CN106309436A (zh) * | 2016-07-25 | 2017-01-11 | 宁波大学 | 可用作乙酰胆碱酯酶抑制剂的色胺衍生物及其用途 |
| WO2018124264A1 (ja) | 2016-12-28 | 2018-07-05 | 富士フイルム株式会社 | 窒素原子含有ポリマー又はその塩の乳化液、その製造方法、及び粒子の製造方法 |
| CA3079171C (en) | 2017-10-16 | 2023-09-12 | Fujifilm Corporation | Therapeutic agent for hyperphosphatemia and particles |
| JP6992084B2 (ja) | 2017-10-16 | 2022-01-13 | 富士フイルム株式会社 | 高リン血症治療剤 |
| WO2019090176A1 (en) | 2017-11-03 | 2019-05-09 | Tricida, Inc. | Compositions for and method of treating acid-base disorders |
| US11524029B2 (en) | 2018-08-13 | 2022-12-13 | Viscera Labs, Inc. | Therapeutic composition and methods |
| US11590161B2 (en) | 2018-08-13 | 2023-02-28 | Viscera Labs, Inc. | Therapeutic composition and methods |
| JP7539374B2 (ja) * | 2018-09-20 | 2024-08-23 | グライセンド, インコーポレイテッド | ボロン酸ポリマーおよび使用方法 |
| CN110511322B (zh) * | 2019-08-29 | 2020-10-02 | 西北大学 | 一种快速葡萄糖响应的互穿网络聚合物微凝胶及其制备方法 |
| CN114423768A (zh) | 2019-09-20 | 2022-04-29 | 格里森德公司 | 含取代的苯基硼酸的聚合物及使用方法 |
| CN116615488A (zh) * | 2020-12-18 | 2023-08-18 | 汉阳大学校产学协力团 | 新型基于聚芴的交联共聚物及制备其的方法和使用其的碱性燃料电池用阴离子交换膜 |
| CN119730861A (zh) * | 2022-08-22 | 2025-03-28 | 中美华世通生物医药科技(武汉)股份有限公司 | 铵盐聚合物及其制备方法和作为胆汁酸螯合剂的用途 |
| WO2024220742A1 (en) * | 2023-04-20 | 2024-10-24 | Vasorx, Inc. | Conjugated polyethyleneimine compounds and compositions, and uses thereof for the treatment of atherosclerosis, cardiovascular, and lung disease |
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| DE59307535D1 (de) * | 1992-07-22 | 1997-11-20 | Hoechst Ag | Hydrophile Zentren aufweisende Polyvinylamin-Derivate, Verfahren zu ihrer Herstellung sowie die Verwendung der Verbindungen als Arzneimittel, Wirkstoffträger und Nahrungsmittelhilfsstoff |
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- 2011-02-24 BR BR112012021444A patent/BR112012021444A2/pt not_active Application Discontinuation
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- 2011-02-24 JP JP2012555152A patent/JP5865847B2/ja not_active Expired - Fee Related
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|---|---|
| CN105017481A (zh) | 2015-11-04 |
| JP2015038225A (ja) | 2015-02-26 |
| WO2011106542A3 (en) | 2011-11-10 |
| CN105017481B (zh) | 2018-10-02 |
| EP2998329A3 (en) | 2016-04-06 |
| US10272103B2 (en) | 2019-04-30 |
| AU2011220742A1 (en) | 2012-09-13 |
| EP2539380B1 (en) | 2015-08-19 |
| EP2998329A2 (en) | 2016-03-23 |
| CA2790999A1 (en) | 2011-09-01 |
| AU2016203432A1 (en) | 2016-06-16 |
| ES2549513T3 (es) | 2015-10-28 |
| US20130022570A1 (en) | 2013-01-24 |
| EP2539380A2 (en) | 2013-01-02 |
| WO2011106542A2 (en) | 2011-09-01 |
| US9181364B2 (en) | 2015-11-10 |
| US20160051576A1 (en) | 2016-02-25 |
| JP2017048398A (ja) | 2017-03-09 |
| CN102858817B (zh) | 2015-09-02 |
| JP2013520561A (ja) | 2013-06-06 |
| CN102858817A (zh) | 2013-01-02 |
| BR112012021444A2 (pt) | 2016-05-31 |
| JP6247740B2 (ja) | 2017-12-13 |
| AU2011220742B2 (en) | 2016-02-25 |
| AU2016203432B2 (en) | 2018-07-26 |
| JP5865847B2 (ja) | 2016-02-17 |
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| Publication | Publication Date | Title |
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| CA2790999C (en) | Crosslinked polyvinylamine, polyallylamine, and polyethyleneimine for use as bile acid sequestrants | |
| EP3130343B1 (en) | Polyimidazoles for use as bile acid sequestrants | |
| US9655920B2 (en) | Amine polymers for use as bile acid sequestrants |
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