AU2011220748B2 - Amine polymers for use as bile acid sequestrants - Google Patents
Amine polymers for use as bile acid sequestrants Download PDFInfo
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- AU2011220748B2 AU2011220748B2 AU2011220748A AU2011220748A AU2011220748B2 AU 2011220748 B2 AU2011220748 B2 AU 2011220748B2 AU 2011220748 A AU2011220748 A AU 2011220748A AU 2011220748 A AU2011220748 A AU 2011220748A AU 2011220748 B2 AU2011220748 B2 AU 2011220748B2
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- Australia
- Prior art keywords
- alkylene
- amine
- polymer
- groups
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000642 polymer Polymers 0.000 title claims abstract description 461
- 150000001412 amines Chemical class 0.000 title claims abstract description 314
- 229920000080 bile acid sequestrant Polymers 0.000 title description 10
- 229940096699 bile acid sequestrants Drugs 0.000 title description 7
- 239000003613 bile acid Substances 0.000 claims abstract description 190
- 239000003833 bile salt Substances 0.000 claims abstract description 53
- 229940093761 bile salts Drugs 0.000 claims abstract description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 310
- 239000000178 monomer Substances 0.000 claims description 273
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 162
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 148
- 238000004132 cross linking Methods 0.000 claims description 137
- 238000006243 chemical reaction Methods 0.000 claims description 120
- 238000003556 assay Methods 0.000 claims description 92
- 150000001408 amides Chemical class 0.000 claims description 91
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 70
- 125000000524 functional group Chemical group 0.000 claims description 69
- 150000002148 esters Chemical class 0.000 claims description 63
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 54
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 36
- 125000000732 arylene group Chemical group 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 33
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- 238000000338 in vitro Methods 0.000 claims description 27
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- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 13
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 13
- 210000002966 serum Anatomy 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims description 10
- RZTDESRVPFKCBH-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)benzene Chemical group C1=CC(C)=CC=C1C1=CC=C(C)C=C1 RZTDESRVPFKCBH-UHFFFAOYSA-N 0.000 claims description 9
- 238000008214 LDL Cholesterol Methods 0.000 claims description 9
- 229920006037 cross link polymer Polymers 0.000 claims description 9
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 8
- 125000001165 hydrophobic group Chemical group 0.000 claims description 8
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
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- 238000004519 manufacturing process Methods 0.000 claims description 3
- 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 116
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- 206010012735 Diarrhoea Diseases 0.000 abstract description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 abstract description 2
- 206010069703 Bile acid malabsorption Diseases 0.000 abstract 1
- 208000003251 Pruritus Diseases 0.000 abstract 1
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- -1 ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, decylene, undecylene, dodecylene, 3,3'-(1H-imidazole-3-ium-1,3-diyl)dipropyl Chemical group 0.000 description 110
- 239000000203 mixture Substances 0.000 description 101
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- 238000003786 synthesis reaction Methods 0.000 description 65
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 60
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 46
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 41
- 210000003608 fece Anatomy 0.000 description 40
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 230000014759 maintenance of location Effects 0.000 description 38
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 37
- 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 description 37
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 31
- 125000000217 alkyl group Chemical group 0.000 description 28
- 239000003921 oil Substances 0.000 description 28
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 26
- 108010035713 Glycodeoxycholic Acid Proteins 0.000 description 24
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- 230000008961 swelling Effects 0.000 description 24
- 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 23
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- WBWWGRHZICKQGZ-HZAMXZRMSA-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-HZAMXZRMSA-N 0.000 description 23
- WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 description 22
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- 241000699800 Cricetinae Species 0.000 description 21
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 21
- LYBWJVKFJAIODE-UHFFFAOYSA-N n,n,n',n'-tetrakis(3-aminopropyl)butane-1,4-diamine Chemical group NCCCN(CCCN)CCCCN(CCCN)CCCN LYBWJVKFJAIODE-UHFFFAOYSA-N 0.000 description 21
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- 125000001931 aliphatic group Chemical group 0.000 description 20
- 230000002209 hydrophobic effect Effects 0.000 description 20
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic 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)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 19
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 125000003277 amino group Chemical group 0.000 description 18
- 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 18
- 238000011553 hamster model Methods 0.000 description 18
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 17
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Classifications
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| US9181364B2 (en) | 2010-02-24 | 2015-11-10 | Relypsa, Inc. | Crosslinked polyvinylamine, polyallylamine, and polyethyleneimine for use as bile acid sequestrants |
| WO2014029888A2 (en) * | 2012-08-24 | 2014-02-27 | Universite De Strasbourg | Branched or macrocyclic polyamines and uses thereof |
| WO2014163883A2 (en) * | 2013-03-13 | 2014-10-09 | Elevance Renewable Sciences | Natural oil derivatives including primary amine functional groups |
| ES2733493T3 (es) * | 2013-06-05 | 2019-11-29 | Tricida Inc | Polímeros de unión a protones para la administración oral |
| MA41202A (fr) * | 2014-12-18 | 2017-10-24 | Genzyme Corp | Copolymères polydiallymine réticulé pour le traitement du diabète de type 2 |
| CN107613986A (zh) | 2015-04-07 | 2018-01-19 | 英特塞普特医药品公司 | 用于组合疗法的药物组合物 |
| WO2017024237A1 (en) * | 2015-08-06 | 2017-02-09 | The Johns Hopkins University | Composition and method for treatment of metabolic disorders |
| CN105111089B (zh) * | 2015-09-07 | 2017-05-10 | 南京华威医药科技开发有限公司 | 吡沙洛姆中间体 |
| CN106176800B (zh) * | 2016-07-11 | 2019-12-06 | 韩源平 | 多聚阳离子树脂的制药应用 |
| GB201809627D0 (en) * | 2018-06-12 | 2018-07-25 | Biorelevant Com Ltd | Methods for preparing buffer solutions suitable for in vitro drug dissolution testing, drug solubility testing and/or drug profiling |
| 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 |
| 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 |
| 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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| EP2539389A1 (en) | 2013-01-02 |
| AU2016200700B2 (en) | 2017-08-17 |
| US20170258825A1 (en) | 2017-09-14 |
| MX2012009783A (es) | 2012-11-21 |
| CA2790901C (en) | 2018-05-01 |
| RU2012140432A (ru) | 2014-03-27 |
| BR112012021446A2 (pt) | 2016-05-31 |
| JP2017190464A (ja) | 2017-10-19 |
| JP6258586B2 (ja) | 2018-01-10 |
| WO2011106548A1 (en) | 2011-09-01 |
| US20140356316A1 (en) | 2014-12-04 |
| AU2016200700A1 (en) | 2016-02-25 |
| DE112011100657T5 (de) | 2013-02-28 |
| JP2013520563A (ja) | 2013-06-06 |
| GB2490855A (en) | 2012-11-14 |
| MX348821B (es) | 2017-06-30 |
| RU2612795C2 (ru) | 2017-03-13 |
| CN107266681A (zh) | 2017-10-20 |
| EP2539389B1 (en) | 2017-12-20 |
| CN102906159B (zh) | 2017-09-26 |
| AU2011220748A1 (en) | 2012-09-20 |
| CA2790901A1 (en) | 2011-09-01 |
| RU2017106587A (ru) | 2019-01-21 |
| GB201216820D0 (en) | 2012-11-07 |
| KR20120130227A (ko) | 2012-11-29 |
| JP6622760B2 (ja) | 2019-12-18 |
| CN102906159A (zh) | 2013-01-30 |
| KR101822608B1 (ko) | 2018-01-29 |
| JP2016130320A (ja) | 2016-07-21 |
| ES2661079T3 (es) | 2018-03-27 |
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