CN105017481B - 用作胆汁酸螯合剂的交联聚乙烯胺、聚烯丙胺和乙烯亚胺 - Google Patents
用作胆汁酸螯合剂的交联聚乙烯胺、聚烯丙胺和乙烯亚胺 Download PDFInfo
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- CN105017481B CN105017481B CN201510370335.7A CN201510370335A CN105017481B CN 105017481 B CN105017481 B CN 105017481B CN 201510370335 A CN201510370335 A CN 201510370335A CN 105017481 B CN105017481 B CN 105017481B
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- alkyl
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- imidazoles
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- 229920000083 poly(allylamine) Polymers 0.000 title description 18
- 229920000080 bile acid sequestrant Polymers 0.000 title description 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 273
- 150000001412 amines Chemical class 0.000 claims abstract description 70
- 150000001408 amides Chemical class 0.000 claims abstract description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 297
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 110
- 125000000623 heterocyclic group Chemical group 0.000 claims description 103
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 87
- 239000003446 ligand Substances 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 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 claims description 60
- -1 benzo [d] thiophenes Azoles Chemical class 0.000 claims description 45
- 150000002148 esters Chemical class 0.000 claims description 44
- 239000003431 cross linking reagent Substances 0.000 claims description 43
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 40
- 125000001118 alkylidene group Chemical group 0.000 claims description 39
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 37
- 125000000524 functional group Chemical group 0.000 claims description 36
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 34
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical class CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 25
- QSDIXCHNEBIQHJ-UHFFFAOYSA-N 3-methyl-1,2-dihydroimidazole Chemical class CN1CNC=C1 QSDIXCHNEBIQHJ-UHFFFAOYSA-N 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 229910021529 ammonia Inorganic materials 0.000 claims description 23
- 230000003252 repetitive effect Effects 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 19
- 229920002873 Polyethylenimine Polymers 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 16
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 16
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 16
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical class CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 claims description 14
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- PEPIOVUNFZBCIB-UHFFFAOYSA-N 1-Decylimidazole Chemical class CCCCCCCCCCN1C=CN=C1 PEPIOVUNFZBCIB-UHFFFAOYSA-N 0.000 claims description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
- 150000003851 azoles Chemical class 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
- 229930192474 thiophene Natural products 0.000 claims description 7
- YUHYOFOYFVGEMY-UHFFFAOYSA-N 2,3-dimethyl-1,2-dihydroimidazole Chemical class CC1NC=CN1C YUHYOFOYFVGEMY-UHFFFAOYSA-N 0.000 claims description 6
- OAYYKPVBFJNKIX-UHFFFAOYSA-N 3-decyl-1,2-dihydroimidazole Chemical class CCCCCCCCCCN1CNC=C1 OAYYKPVBFJNKIX-UHFFFAOYSA-N 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical class CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 claims description 5
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 5
- BKFRZOZNMWIFLH-UHFFFAOYSA-N 1-decyl-2-methylimidazole Chemical class CCCCCCCCCCN1C=CN=C1C BKFRZOZNMWIFLH-UHFFFAOYSA-N 0.000 claims description 5
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical compound CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
- 125000006611 nonyloxy group Chemical group 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 4
- QBRFAFGCHZMCPZ-UHFFFAOYSA-N 3-butyl-1,2-dihydroimidazole Chemical class CCCCN1CNC=C1 QBRFAFGCHZMCPZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- ZENKESXKWBIZCV-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-1,3-benzodioxin-6-amine Chemical group O1C(F)(F)OC(F)(F)C2=CC(N)=CC=C21 ZENKESXKWBIZCV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims description 2
- TZQCQEXEARDLTB-UHFFFAOYSA-N 3-decyl-2-methyl-1,2-dihydroimidazole Chemical class C(CCCCCCCCC)N1C(NC=C1)C TZQCQEXEARDLTB-UHFFFAOYSA-N 0.000 claims 2
- VJROPLWGFCORRM-UHFFFAOYSA-N 2-methylbutan-1-amine Chemical compound CCC(C)CN VJROPLWGFCORRM-UHFFFAOYSA-N 0.000 claims 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
- 239000003613 bile acid Substances 0.000 abstract description 76
- 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 abstract description 71
- 239000003833 bile salt Substances 0.000 abstract description 41
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 56
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Landscapes
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| 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 |
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| 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 |
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| CN105017481A (zh) | 2015-11-04 |
| JP2015038225A (ja) | 2015-02-26 |
| WO2011106542A3 (en) | 2011-11-10 |
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| ES2549513T3 (es) | 2015-10-28 |
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| 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 |
| CA2790999C (en) | 2019-05-14 |
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