ES2549513T3 - Polivinilamina, polialilamina y polietilenimina reticuladas para uso como secuestradores de ácidos biliares - Google Patents
Polivinilamina, polialilamina y polietilenimina reticuladas para uso como secuestradores de ácidos biliares Download PDFInfo
- Publication number
- ES2549513T3 ES2549513T3 ES11707038.3T ES11707038T ES2549513T3 ES 2549513 T3 ES2549513 T3 ES 2549513T3 ES 11707038 T ES11707038 T ES 11707038T ES 2549513 T3 ES2549513 T3 ES 2549513T3
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- oxocmalkyl
- alkylene
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- 229920002873 Polyethylenimine Polymers 0.000 title description 16
- 229920000083 poly(allylamine) Polymers 0.000 title description 16
- 229920000080 bile acid sequestrant Polymers 0.000 title description 4
- 229940096699 bile acid sequestrants Drugs 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 306
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 119
- 239000000178 monomer Substances 0.000 claims abstract description 119
- 239000000203 mixture Substances 0.000 claims abstract description 77
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 76
- 125000003118 aryl group Chemical group 0.000 claims abstract description 70
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 63
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 61
- 150000001412 amines Chemical class 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 150000001408 amides Chemical class 0.000 claims abstract description 45
- 150000002148 esters Chemical class 0.000 claims abstract description 44
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 40
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 39
- 125000000524 functional group Chemical group 0.000 claims abstract description 37
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 17
- 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 abstract description 12
- 239000003613 bile acid Substances 0.000 claims description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- 238000012360 testing method Methods 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 30
- 239000000843 powder Substances 0.000 claims description 24
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- 230000009477 glass transition Effects 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
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- -1 1-methylpyrrolidinium-1-yl Chemical group 0.000 description 159
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 148
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 67
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
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- 239000002904 solvent Substances 0.000 description 33
- 238000000034 method Methods 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 28
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 210000003608 fece Anatomy 0.000 description 26
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 23
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
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- 235000012000 cholesterol Nutrition 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic 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)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 16
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- 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 group 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 description 15
- RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 description 15
- 208000002881 Colic Diseases 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229960001091 chenodeoxycholic acid Drugs 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 208000035150 Hypercholesterolemia Diseases 0.000 description 14
- 150000003839 salts Chemical group 0.000 description 14
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 13
- 108010035713 Glycodeoxycholic Acid Proteins 0.000 description 13
- 239000011324 bead Substances 0.000 description 13
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- 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 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 108010007979 Glycocholic Acid Proteins 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 12
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic 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)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 12
- 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 description 12
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- 241000282414 Homo sapiens Species 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 10
- 125000003282 alkyl amino group Chemical group 0.000 description 10
- 125000002704 decyl 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])* 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 10
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic 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)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 description 10
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- 125000005208 trialkylammonium group Chemical group 0.000 description 10
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 9
- 241000699800 Cricetinae Species 0.000 description 9
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- 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
-
- 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
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- 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)
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- Medicinal Preparation (AREA)
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| US307811P | 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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| 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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| ES2598500T3 (es) | 2010-02-24 | 2017-01-27 | Relypsa, Inc. | Poliimidazoles para su uso como secuestrantes de ácidos biliares |
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| WO2011106542A3 (en) | 2011-11-10 |
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| CN102858817B (zh) | 2015-09-02 |
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| 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 |
| CA2790999C (en) | 2019-05-14 |
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