JP6258586B2 - 胆汁酸捕捉剤として使用するためのアミンポリマー - Google Patents

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Publication number

JP6258586B2

JP6258586B2 JP2012555155A JP2012555155A JP6258586B2 JP 6258586 B2 JP6258586 B2 JP 6258586B2 JP 2012555155 A JP2012555155 A JP 2012555155A JP 2012555155 A JP2012555155 A JP 2012555155A JP 6258586 B2 JP6258586 B2 JP 6258586B2

Authority

JP

Japan

Prior art keywords

alkylene

alkyl

polymer

amine

group

Prior art date

2010-02-24

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.)

Expired - Fee Related

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• 229920000642 polymer Polymers 0.000 title claims description 638
• 150000001412 amines Chemical class 0.000 title claims description 482
• 239000003613 bile acid Substances 0.000 title claims description 142
• 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 title description 57
• 125000002947 alkylene group Chemical group 0.000 claims description 430
• 125000000217 alkyl group Chemical group 0.000 claims description 399
• -1 hydroxyl - group amide Chemical class 0.000 claims description 300
• 239000000178 monomer Substances 0.000 claims description 264
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 186
• 238000004132 cross linking Methods 0.000 claims description 127
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 127
• 150000001408 amides Chemical group 0.000 claims description 112
• 125000003118 aryl group Chemical group 0.000 claims description 94
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 89
• 125000003282 alkyl amino group Chemical group 0.000 claims description 81
• 125000000524 functional group Chemical group 0.000 claims description 78
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 76
• 150000002148 esters Chemical class 0.000 claims description 76
• 239000000243 solution Substances 0.000 claims description 73
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 71
• 239000002245 particle Substances 0.000 claims description 59
• 238000003556 assay Methods 0.000 claims description 51
• ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 45
• 125000000732 arylene group Chemical group 0.000 claims description 42
• 108010035713 Glycodeoxycholic Acid Proteins 0.000 claims description 34
• WVULKSPCQVQLCU-UHFFFAOYSA-N Glycodeoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 WVULKSPCQVQLCU-UHFFFAOYSA-N 0.000 claims description 34
• 125000001931 aliphatic group Chemical group 0.000 claims description 34
• 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 34
• 241001465754 Metazoa Species 0.000 claims description 31
• 150000001875 compounds Chemical class 0.000 claims description 31
• 238000006116 polymerization reaction Methods 0.000 claims description 29
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 229910019142 PO4 Inorganic materials 0.000 claims description 23
• 239000007795 chemical reaction product Substances 0.000 claims description 23
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 22
• 239000010452 phosphate Substances 0.000 claims description 22
• 108010007979 Glycocholic Acid Proteins 0.000 claims description 19
• RFDAIACWWDREDC-UHFFFAOYSA-N Na salt-Glycocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 RFDAIACWWDREDC-UHFFFAOYSA-N 0.000 claims description 19
• 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 19
• 229940099347 glycocholic acid Drugs 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 210000002966 serum Anatomy 0.000 claims description 18
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 16
• 125000004414 alkyl thio group Chemical group 0.000 claims description 16
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 16
• AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 13
• 238000000099 in vitro assay Methods 0.000 claims description 13
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 12
• 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 12
• CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 claims description 12
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 12
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 12
• 239000005642 Oleic acid Substances 0.000 claims description 12
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 12
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 12
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 12
• LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical group O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 10
• 210000000813 small intestine Anatomy 0.000 claims description 10
• 239000000654 additive Substances 0.000 claims description 9
• 238000001914 filtration Methods 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
• 125000001165 hydrophobic group Chemical group 0.000 claims description 9
• 239000012085 test solution Substances 0.000 claims description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• 238000008214 LDL Cholesterol Methods 0.000 claims description 7
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
• 238000004811 liquid chromatography Methods 0.000 claims description 7
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 230000006870 function Effects 0.000 claims description 6
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
• 150000002500 ions Chemical class 0.000 claims description 6
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
• 125000005188 oxoalkyl group Chemical group 0.000 claims description 6
• 238000005119 centrifugation Methods 0.000 claims description 5
• 125000001475 halogen functional group Chemical group 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• 239000006228 supernatant Substances 0.000 claims description 5
• 239000004593 Epoxy Chemical group 0.000 claims description 4
• 230000000996 additive effect Effects 0.000 claims description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
• 150000001299 aldehydes Chemical class 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 150000002576 ketones Chemical class 0.000 claims description 3
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
• 238000000034 method Methods 0.000 description 106
• 239000000203 mixture Substances 0.000 description 61
• 238000006243 chemical reaction Methods 0.000 description 57
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
• 239000003833 bile salt Substances 0.000 description 48
• 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 48
• 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 47
• 239000003446 ligand Substances 0.000 description 46
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 42
• 229910052757 nitrogen Inorganic materials 0.000 description 39
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
• 238000000338 in vitro Methods 0.000 description 35
• 239000007787 solid Substances 0.000 description 35
• 239000002904 solvent Substances 0.000 description 35
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 238000011282 treatment Methods 0.000 description 32
• 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 30
• 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 30
• 239000004380 Cholic acid Substances 0.000 description 30
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 230000015572 biosynthetic process Effects 0.000 description 30
• 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 30
• 229960001091 chenodeoxycholic acid Drugs 0.000 description 30
• 235000019416 cholic acid Nutrition 0.000 description 30
• 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 30
• 229960002471 cholic acid Drugs 0.000 description 30
• 238000003786 synthesis reaction Methods 0.000 description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 29
• 239000000047 product Substances 0.000 description 29
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 29
• 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 28
• 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 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• 229940093761 bile salts Drugs 0.000 description 25
• 239000003795 chemical substances by application Substances 0.000 description 25
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
• 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
• 235000021317 phosphate Nutrition 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 239000007853 buffer solution Substances 0.000 description 20
• 230000002496 gastric effect Effects 0.000 description 20
• 230000002829 reductive effect Effects 0.000 description 20
• 230000002550 fecal effect Effects 0.000 description 19
• 238000005259 measurement Methods 0.000 description 19
• 150000003839 salts Chemical group 0.000 description 19
• 239000004971 Cross linker Substances 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• 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 18
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• 239000003112 inhibitor Substances 0.000 description 18
• 230000014759 maintenance of location Effects 0.000 description 18
• 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 description 17
• 229920002905 Colesevelam Polymers 0.000 description 17
• SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 description 17
• 210000001035 gastrointestinal tract Anatomy 0.000 description 17
• 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 17
• 235000012000 cholesterol Nutrition 0.000 description 16
• 210000003608 fece Anatomy 0.000 description 16
• 239000000499 gel Substances 0.000 description 16
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 15
• 239000000523 sample Substances 0.000 description 15
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
• 230000002411 adverse Effects 0.000 description 14
• 125000003277 amino group Chemical group 0.000 description 14
• 206010012601 diabetes mellitus Diseases 0.000 description 14
• 229960004198 guanidine Drugs 0.000 description 14
• 238000001727 in vivo Methods 0.000 description 14
• KMJXUDRFFXCAHZ-YEKFLHDCSA-N (8S,9S,10R,13S,14S,17R)-13-methyl-16-oxo-17-[(2R)-pentan-2-yl]-1,2,3,4,5,6,7,8,9,11,12,14,15,17-tetradecahydrocyclopenta[a]phenanthrene-10-carboxylic acid Chemical compound O=C1[C@@H]([C@]2(CC[C@@H]3[C@]4(CCCCC4CC[C@H]3[C@@H]2C1)C(=O)O)C)[C@H](C)CCC KMJXUDRFFXCAHZ-YEKFLHDCSA-N 0.000 description 13
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• 230000008961 swelling Effects 0.000 description 13
• 238000012360 testing method Methods 0.000 description 13
• 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 description 12
• 108010007622 LDL Lipoproteins Proteins 0.000 description 12
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• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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• 208000035150 Hypercholesterolemia Diseases 0.000 description 11
• 239000002253 acid Substances 0.000 description 11
• 239000003431 cross linking reagent Substances 0.000 description 11
• 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 11
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• 239000000706 filtrate Substances 0.000 description 11
• 238000011553 hamster model Methods 0.000 description 11
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
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• 208000032928 Dyslipidaemia Diseases 0.000 description 9
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 229960000674 colesevelam hydrochloride Drugs 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 230000029142 excretion Effects 0.000 description 9
• 150000003141 primary amines Chemical group 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 8
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• 239000000463 material Substances 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• 230000008569 process Effects 0.000 description 8
• ZNSIZMQNQCNRBW-UHFFFAOYSA-N sevelamer Chemical compound NCC=C.ClCC1CO1 ZNSIZMQNQCNRBW-UHFFFAOYSA-N 0.000 description 8
• 229960003693 sevelamer Drugs 0.000 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• HFVIYAZBVIGNAN-UHFFFAOYSA-N 1,1-dibromodecane Chemical group CCCCCCCCCC(Br)Br HFVIYAZBVIGNAN-UHFFFAOYSA-N 0.000 description 7
• GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 7
• JWOTWWORMYMZCR-UHFFFAOYSA-N 1-methyl-4-[3-(1-methylpiperidin-4-yl)propyl]piperidine Chemical compound C1CN(C)CCC1CCCC1CCN(C)CC1 JWOTWWORMYMZCR-UHFFFAOYSA-N 0.000 description 7
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