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
- AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic 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)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 description 1
- QBYUNVOYXHFVKC-GBURMNQMSA-N taurolithocholic 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)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 QBYUNVOYXHFVKC-GBURMNQMSA-N 0.000 description 1
- AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
- IOKGWQZQCNXXLD-UHFFFAOYSA-N tert-butyl n-(3-bromopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCBr IOKGWQZQCNXXLD-UHFFFAOYSA-N 0.000 description 1
- XCAQIUOFDMREBA-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(=O)OC(C)(C)C XCAQIUOFDMREBA-UHFFFAOYSA-N 0.000 description 1
- 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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- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 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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- 229960000834 vinyl ether Drugs 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
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- 229940046009 vitamin E Drugs 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
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Classifications
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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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- C08F222/38—Amides
- C08F222/385—Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
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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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- Chemical & Material Sciences (AREA)
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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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Hydrogenated Pyridines (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US61/307,814 | 2010-02-24 | ||
| US61/307,811 | 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 |
Publications (2)
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| CA2790999A1 CA2790999A1 (en) | 2011-09-01 |
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| JP6258586B2 (ja) | 2010-02-24 | 2018-01-10 | レリプサ， インコーポレイテッド | 胆汁酸捕捉剤として使用するためのアミンポリマー |
| WO2013087237A1 (en) * | 2011-12-13 | 2013-06-20 | Synthon Bv | Purification of sevelamer and related polyallylamines |
| KR102081560B1 (ko) | 2012-02-09 | 2020-02-25 | 라이프 테크놀로지스 코포레이션 | 친수성 중합체성 입자 및 그의 제조 방법 |
| PE20151766A1 (es) * | 2013-03-15 | 2015-12-11 | Genzyme Corp | Agentes quelantes de precursores de producto final de glicacion avanzada (age) |
| LT3003327T (lt) | 2013-06-05 | 2017-12-27 | Tricida Inc. | Protonus surišantys polimerai, skirti geriamajam vartojimui |
| 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 |
| ES2908142T3 (es) | 2014-06-13 | 2022-04-27 | United Therapeutics Corp | Formulaciones de treprostinil |
| CN113855703B (zh) | 2014-12-10 | 2025-11-25 | 特里赛达公司 | 用于口服施用的质子结合聚合物 |
| MA41202A (fr) | 2014-12-18 | 2017-10-24 | Genzyme Corp | Copolymères polydiallymine réticulé pour le traitement du diabète de type 2 |
| EP3702383B1 (en) | 2015-07-02 | 2023-12-27 | Life Technologies Corporation | Polymer substrates formed from carboxy functional acrylamide |
| EP3331499A4 (en) * | 2015-08-06 | 2019-04-10 | The Johns Hopkins University | COMPOSITION AND METHOD FOR THE TREATMENT OF METABOLISM DISEASES |
| WO2017193024A1 (en) | 2016-05-06 | 2017-11-09 | Tricida, Inc. | Hcl-binding compositions for and method of treating acid-base disorders |
| 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 |
| JP6792640B2 (ja) | 2016-12-28 | 2020-11-25 | 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 |
| CN111246857A (zh) | 2017-10-16 | 2020-06-05 | 富士胶片株式会社 | 高磷血症治疗剂及粒子 |
| EP3698799B1 (en) | 2017-10-16 | 2022-01-26 | FUJIFILM Corporation | Hyperphosphatemia treatment agent |
| AU2018360867B2 (en) | 2017-11-03 | 2024-12-12 | Tricida, Inc. | Compositions for and method of treating acid-base disorders |
| US11590161B2 (en) | 2018-08-13 | 2023-02-28 | Viscera Labs, Inc. | Therapeutic composition and methods |
| US11524029B2 (en) | 2018-08-13 | 2022-12-13 | Viscera Labs, Inc. | Therapeutic composition and methods |
| US20210403625A1 (en) * | 2018-09-20 | 2021-12-30 | Glyscend, Inc. | Boronic acid polymers and methods of use |
| 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 |
| EP4031553A4 (en) | 2019-09-20 | 2023-11-01 | Glyscend, Inc. | POLYMERS WITH SUBSTITUTED PHENYLBORONIC ACID AND METHOD OF USE |
| US20240317951A1 (en) * | 2020-12-18 | 2024-09-26 | Iucf-Hyu (Industry-University Cooperation Foundation Hanyang University) | Novel polyfluorene-based cross-linked copolymer, method for producing same, and anion exchange membrane for alkaline fuel cell using same |
| JP2025528899A (ja) * | 2022-08-22 | 2025-09-02 | ウォーターストーン ファーマシューティカルズ（ウーハン）カンパニー，リミティド | アンモニウム塩ポリマー、同ポリマーを調製する方法、および胆汁酸隔離剤としてのその使用 |
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| US5236701A (en) | 1989-07-19 | 1993-08-17 | Lowchol Scientific Inc. | Ingestible hydrophilic polymeric amines useful for lowering blood cholesterol |
| JPH066667A (ja) | 1992-06-22 | 1994-01-14 | Canon Inc | ぶれ検出装置及びぶれ補正装置 |
| ATE159262T1 (de) * | 1992-07-22 | 1997-11-15 | Hoechst Ag | Hydrophile zentren aufweisende polyvinylamin- derivate, verfahren zu ihrer herstellung sowie die verwendung der verbindungen als arzneimittel, wirkstoffträger und nahrungsmittelhilfsstoff |
| DK0580079T3 (da) | 1992-07-22 | 1997-06-30 | Hoechst Ag | Tværbundne, nitrogenholdige vinylcopolymerer, fremgangsmåde til deres fremstilling samt anvendelse af disse forbindelser |
| US5556619A (en) * | 1992-08-20 | 1996-09-17 | The Du Pont Merck Pharmaceutical Company | Crosslinked polymeric ammonium salts |
| US5607669A (en) | 1994-06-10 | 1997-03-04 | Geltex Pharmaceuticals, Inc. | Amine polymer sequestrant and method of cholesterol depletion |
| US5618530A (en) * | 1994-06-10 | 1997-04-08 | Geltex Pharmaceuticals, Inc. | Hydrophobic amine polymer sequestrant and method of cholesterol depletion |
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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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| CN105017481B (zh) | 2018-10-02 |
| US10272103B2 (en) | 2019-04-30 |
| EP2539380A2 (en) | 2013-01-02 |
| WO2011106542A3 (en) | 2011-11-10 |
| JP2015038225A (ja) | 2015-02-26 |
| JP2017048398A (ja) | 2017-03-09 |
| WO2011106542A2 (en) | 2011-09-01 |
| JP2013520561A (ja) | 2013-06-06 |
| AU2016203432B2 (en) | 2018-07-26 |
| BR112012021444A2 (pt) | 2016-05-31 |
| AU2011220742B2 (en) | 2016-02-25 |
| US20130022570A1 (en) | 2013-01-24 |
| JP5865847B2 (ja) | 2016-02-17 |
| CN105017481A (zh) | 2015-11-04 |
| US9181364B2 (en) | 2015-11-10 |
| EP2998329A2 (en) | 2016-03-23 |
| US20160051576A1 (en) | 2016-02-25 |
| AU2016203432A1 (en) | 2016-06-16 |
| CA2790999A1 (en) | 2011-09-01 |
| JP6247740B2 (ja) | 2017-12-13 |
| CN102858817A (zh) | 2013-01-02 |
| CN102858817B (zh) | 2015-09-02 |
| EP2539380B1 (en) | 2015-08-19 |
| ES2549513T3 (es) | 2015-10-28 |
| AU2011220742A1 (en) | 2012-09-13 |
| EP2998329A3 (en) | 2016-04-06 |
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