DE19705963A1 - Vernetzte Vinylpolymere mit Gallensäure-Adsorberwirkung - Google Patents
Vernetzte Vinylpolymere mit Gallensäure-AdsorberwirkungInfo
- Publication number
- DE19705963A1 DE19705963A1 DE19705963A DE19705963A DE19705963A1 DE 19705963 A1 DE19705963 A1 DE 19705963A1 DE 19705963 A DE19705963 A DE 19705963A DE 19705963 A DE19705963 A DE 19705963A DE 19705963 A1 DE19705963 A1 DE 19705963A1
- Authority
- DE
- Germany
- Prior art keywords
- independently
- compounds
- nhr
- mixture
- solution
- 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.)
- Withdrawn
Links
- 239000003613 bile acid Substances 0.000 title claims description 37
- 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 claims description 26
- 229920002554 vinyl polymer Polymers 0.000 title claims description 9
- 230000000694 effects Effects 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 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 claims description 34
- 239000003814 drug Substances 0.000 claims description 19
- 150000003254 radicals Chemical class 0.000 claims description 16
- 238000010521 absorption reaction Methods 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 14
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 230000009885 systemic effect Effects 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 238000006845 Michael addition reaction Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 230000001315 anti-hyperlipaemic effect Effects 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 16
- 150000001450 anions Chemical class 0.000 abstract description 2
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003524 antilipemic agent Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 239000000203 mixture Substances 0.000 description 73
- 239000000243 solution Substances 0.000 description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 125000001931 aliphatic group Chemical group 0.000 description 41
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 23
- LBSPZZSGTIBOFG-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;dihydrochloride Chemical compound Cl.Cl.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LBSPZZSGTIBOFG-UHFFFAOYSA-N 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 18
- -1 bile acid anions Chemical class 0.000 description 16
- 239000011780 sodium chloride Substances 0.000 description 16
- 238000000921 elemental analysis Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 230000009102 absorption Effects 0.000 description 14
- 239000000499 gel Substances 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 13
- 238000000108 ultra-filtration Methods 0.000 description 13
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000012528 membrane Substances 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 210000004185 liver Anatomy 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 238000005342 ion exchange Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229920001268 Cholestyramine Polymers 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 235000012000 cholesterol Nutrition 0.000 description 8
- 210000000936 intestine Anatomy 0.000 description 8
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 108010068815 steroid hormone 7-alpha-hydroxylase Proteins 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 210000001589 microsome Anatomy 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 239000012465 retentate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- IUKIMAXMUXWYTA-UHFFFAOYSA-N 1-(bromomethyl)-4-[2-[4-(bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]benzene Chemical compound C=1C=C(CBr)C=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(CBr)C=C1 IUKIMAXMUXWYTA-UHFFFAOYSA-N 0.000 description 5
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 5
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 5
- OYXZMSRRJOYLLO-UHFFFAOYSA-N 7alpha-Hydroxycholesterol Natural products OC1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 OYXZMSRRJOYLLO-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- RWTFQMCKUUGWLI-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ylbenzene dihydrobromide Chemical compound FC(C(C(F)(F)F)C1=CC=CC=C1)(F)F.Br.Br RWTFQMCKUUGWLI-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229920000858 Cyclodextrin Polymers 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 4
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 4
- 230000010235 enterohepatic circulation Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
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- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 239000012089 stop solution Substances 0.000 description 4
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosan acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 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 3
- OYXZMSRRJOYLLO-RVOWOUOISA-N 7alpha-hydroxycholesterol Chemical compound C([C@H]1O)=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 OYXZMSRRJOYLLO-RVOWOUOISA-N 0.000 description 3
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 3
- 239000004380 Cholic acid Substances 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
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- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- YDLYQMBWCWFRAI-UHFFFAOYSA-N n-Hexatriacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC YDLYQMBWCWFRAI-UHFFFAOYSA-N 0.000 description 3
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 3
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- 235000011152 sodium sulphate Nutrition 0.000 description 3
- OLTHARGIAFTREU-UHFFFAOYSA-N triacontane Natural products CCCCCCCCCCCCCCCCCCCCC(C)CCCCCCCC OLTHARGIAFTREU-UHFFFAOYSA-N 0.000 description 3
- SAWCWRKKWROPRB-UHFFFAOYSA-N 1,1-dibromohexane Chemical compound CCCCCC(Br)Br SAWCWRKKWROPRB-UHFFFAOYSA-N 0.000 description 2
- SDENLXLNLFKRAR-UHFFFAOYSA-N 1,14-dibromotetradecane Chemical compound BrCCCCCCCCCCCCCCBr SDENLXLNLFKRAR-UHFFFAOYSA-N 0.000 description 2
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- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 2
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- 210000003608 fece Anatomy 0.000 description 2
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- ODBLHEXUDAPZAU-UHFFFAOYSA-N isocitric acid Chemical compound OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- GUAQVFRUPZBRJQ-UHFFFAOYSA-N n-(3-aminopropyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCN GUAQVFRUPZBRJQ-UHFFFAOYSA-N 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
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Classifications
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- 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
- C08F271/00—Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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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
- 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
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- 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
- 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
- C08F22/10—Esters
- C08F22/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
-
- 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
- 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
- C08F22/36—Amides or imides
- C08F22/38—Amides
- C08F22/385—Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polymers & Plastics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19705963A DE19705963A1 (de) | 1997-02-17 | 1997-02-17 | Vernetzte Vinylpolymere mit Gallensäure-Adsorberwirkung |
| TR1999/01978T TR199901978T2 (xx) | 1997-02-17 | 1998-02-17 | Safra asidini emme etkili �apraz ba�lant�l� vinil polimerleri. |
| PL98335106A PL335106A1 (en) | 1997-02-17 | 1998-02-17 | Crosslinked vinyl polymers exhibiting bile acids absorbing properties |
| AU64983/98A AU728985B2 (en) | 1997-02-17 | 1998-02-17 | Crosslinked vinyl polymers having bile acid adsorber action |
| BR9807408-3A BR9807408A (pt) | 1997-02-17 | 1998-02-17 | Polìmeros de vinila reticulados tendo ação de absorvente do ácido biliar |
| CA002281602A CA2281602A1 (en) | 1997-02-17 | 1998-02-17 | Cross-linked vinyl polymers with bile acid adsorbing effect |
| HU0001012A HUP0001012A3 (en) | 1997-02-17 | 1998-02-17 | Cross-linked vinyl polymers with bile acid adsorbing effect |
| CZ992932A CZ293299A3 (cs) | 1997-02-17 | 1998-02-17 | Zesítěné vinylpolymery s adsorpčním účinkem na kyseliny žlučové, jejich monomery, způsob jejich výroby, léčiva tyto látky obsahující a jejich použití |
| JP53537598A JP2002515930A (ja) | 1997-02-17 | 1998-02-17 | 胆汁酸吸着作用を有する架橋結合性ビニルポリマー |
| EP98910693A EP0960141A1 (de) | 1997-02-17 | 1998-02-17 | Vernetzte vinylpolymere mit gallensäure-adsorberwirkung |
| RU99119911/04A RU99119911A (ru) | 1997-02-17 | 1998-02-17 | Сшитые виниловые полимеры, способные адсорбировать желчные кислоты, исходные соединения, способы их получения, смеси полимеров и лекарственное средство |
| CN98803685A CN1251112A (zh) | 1997-02-17 | 1998-02-17 | 具有胆汁酸吸收作用的交联乙烯基聚合物 |
| PCT/EP1998/000898 WO1998036002A1 (de) | 1997-02-17 | 1998-02-17 | Vernetzte vinylpolymere mit gallensäure-adsorberwirkung |
| KR1019997007457A KR20000071167A (ko) | 1997-02-17 | 1998-02-17 | 담즙산 흡착 효과를 갖는 가교결합된 비닐 중합체 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19705963A DE19705963A1 (de) | 1997-02-17 | 1997-02-17 | Vernetzte Vinylpolymere mit Gallensäure-Adsorberwirkung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19705963A1 true DE19705963A1 (de) | 1998-08-20 |
Family
ID=7820445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19705963A Withdrawn DE19705963A1 (de) | 1997-02-17 | 1997-02-17 | Vernetzte Vinylpolymere mit Gallensäure-Adsorberwirkung |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0960141A1 (cs) |
| JP (1) | JP2002515930A (cs) |
| KR (1) | KR20000071167A (cs) |
| CN (1) | CN1251112A (cs) |
| AU (1) | AU728985B2 (cs) |
| BR (1) | BR9807408A (cs) |
| CA (1) | CA2281602A1 (cs) |
| CZ (1) | CZ293299A3 (cs) |
| DE (1) | DE19705963A1 (cs) |
| HU (1) | HUP0001012A3 (cs) |
| PL (1) | PL335106A1 (cs) |
| RU (1) | RU99119911A (cs) |
| TR (1) | TR199901978T2 (cs) |
| WO (1) | WO1998036002A1 (cs) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000000526A1 (de) * | 1998-06-30 | 2000-01-06 | Linkies, Adolf, Heinz | Neues verfahren zur herstellung vernetzter vinylpolymere auf der basis quartärer ammoniumgruppen mit gallensäure-adsorberwirkung |
| EP1505092A3 (en) * | 2003-08-07 | 2005-03-02 | Mitsubishi Gas Chemical Company, Inc. | Gas barrier (meth)acrylate resin cured product |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6958212B1 (en) | 1999-02-01 | 2005-10-25 | Eidgenossische Technische Hochschule Zurich | Conjugate addition reactions for the controlled delivery of pharmaceutically active compounds |
| DK1181323T3 (da) | 1999-02-01 | 2011-10-17 | Eidgenoess Tech Hochschule | Biomaterialer dannet med nukleofil additionsreaktion med konjugerede uimættede grupper |
| US7291673B2 (en) | 2000-06-02 | 2007-11-06 | Eidgenossiche Technische Hochschule Zurich | Conjugate addition reactions for the controlled delivery of pharmaceutically active compounds |
| US8282912B2 (en) | 2002-03-22 | 2012-10-09 | Kuros Biosurgery, AG | Compositions for tissue augmentation |
| WO2008125655A1 (en) | 2007-04-13 | 2008-10-23 | Kuros Biosurgery Ag | Polymeric tissue sealant |
| JP6126498B2 (ja) * | 2013-02-15 | 2017-05-10 | 富士フイルム株式会社 | 高分子機能性膜及びその製造方法 |
| JP6071957B2 (ja) * | 2014-03-07 | 2017-02-01 | 富士フイルム株式会社 | イオン交換性ポリマーおよびその製造方法、電解質膜およびその製造方法ならびにイオン交換性ポリマー製造用組成物 |
| WO2017038328A1 (ja) * | 2015-08-31 | 2017-03-09 | 富士フイルム株式会社 | イオン交換ポリマー、硬化性組成物、硬化物、部材、及び、装置 |
| WO2019054797A1 (ko) | 2017-09-15 | 2019-03-21 | 주식회사 엘지화학 | 중합성 조성물, 고분자 캡슐 및 이를 포함하는 섬유 유연제 조성물 |
| CN110317588A (zh) * | 2018-03-29 | 2019-10-11 | 中国石油化工股份有限公司 | 一种阳离子表面活性剂及其制备方法和起泡剂及其应用 |
| IT201900020949A1 (it) * | 2019-11-12 | 2021-05-12 | Univ Degli Studi Di Trieste | Monomero fotopolimerizzabile antibatterico |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR206115A1 (es) * | 1973-06-11 | 1976-06-30 | Merck & Co Inc | Procedimiento para preparar un polimero lineal no ramificado y no reticulado |
| GB9123683D0 (en) * | 1991-11-07 | 1992-01-02 | Sandoz Ltd | Improvements in or relating to organic compounds |
| DE69307112T2 (de) * | 1992-07-06 | 1997-04-17 | Otsuka Kagaku Kk | Polymerisierbares monomer, polymere und verfahren zu seiner herstellung |
| DE59307535D1 (de) * | 1992-07-22 | 1997-11-20 | Hoechst Ag | Hydrophile Zentren aufweisende Polyvinylamin-Derivate, Verfahren zu ihrer Herstellung sowie die Verwendung der Verbindungen als Arzneimittel, Wirkstoffträger und Nahrungsmittelhilfsstoff |
| US5618530A (en) * | 1994-06-10 | 1997-04-08 | Geltex Pharmaceuticals, Inc. | Hydrophobic amine polymer sequestrant and method of cholesterol depletion |
| US5624963A (en) * | 1993-06-02 | 1997-04-29 | Geltex Pharmaceuticals, Inc. | Process for removing bile salts from a patient and compositions therefor |
-
1997
- 1997-02-17 DE DE19705963A patent/DE19705963A1/de not_active Withdrawn
-
1998
- 1998-02-17 HU HU0001012A patent/HUP0001012A3/hu unknown
- 1998-02-17 CZ CZ992932A patent/CZ293299A3/cs unknown
- 1998-02-17 CA CA002281602A patent/CA2281602A1/en not_active Abandoned
- 1998-02-17 TR TR1999/01978T patent/TR199901978T2/xx unknown
- 1998-02-17 CN CN98803685A patent/CN1251112A/zh active Pending
- 1998-02-17 JP JP53537598A patent/JP2002515930A/ja active Pending
- 1998-02-17 BR BR9807408-3A patent/BR9807408A/pt not_active Application Discontinuation
- 1998-02-17 AU AU64983/98A patent/AU728985B2/en not_active Ceased
- 1998-02-17 EP EP98910693A patent/EP0960141A1/de not_active Withdrawn
- 1998-02-17 WO PCT/EP1998/000898 patent/WO1998036002A1/de not_active Application Discontinuation
- 1998-02-17 RU RU99119911/04A patent/RU99119911A/ru not_active Application Discontinuation
- 1998-02-17 KR KR1019997007457A patent/KR20000071167A/ko not_active Withdrawn
- 1998-02-17 PL PL98335106A patent/PL335106A1/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000000526A1 (de) * | 1998-06-30 | 2000-01-06 | Linkies, Adolf, Heinz | Neues verfahren zur herstellung vernetzter vinylpolymere auf der basis quartärer ammoniumgruppen mit gallensäure-adsorberwirkung |
| EP1505092A3 (en) * | 2003-08-07 | 2005-03-02 | Mitsubishi Gas Chemical Company, Inc. | Gas barrier (meth)acrylate resin cured product |
| US7087695B2 (en) | 2003-08-07 | 2006-08-08 | Mitsubishi Gas Chemical Company, Inc. | Gas barrier(meth)acrylate resin cured product |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9807408A (pt) | 2000-03-14 |
| AU6498398A (en) | 1998-09-08 |
| PL335106A1 (en) | 2000-04-10 |
| CZ293299A3 (cs) | 1999-12-15 |
| AU728985B2 (en) | 2001-01-25 |
| EP0960141A1 (de) | 1999-12-01 |
| JP2002515930A (ja) | 2002-05-28 |
| CA2281602A1 (en) | 1998-08-20 |
| HUP0001012A3 (en) | 2001-11-28 |
| CN1251112A (zh) | 2000-04-19 |
| TR199901978T2 (xx) | 2000-06-21 |
| HUP0001012A2 (hu) | 2000-09-28 |
| RU99119911A (ru) | 2001-06-27 |
| KR20000071167A (ko) | 2000-11-25 |
| WO1998036002A1 (de) | 1998-08-20 |
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