CA1141892A - Anionic ion exchange resins with cholesterol decreasing properties - Google Patents
Anionic ion exchange resins with cholesterol decreasing propertiesInfo
- Publication number
- CA1141892A CA1141892A CA000332338A CA332338A CA1141892A CA 1141892 A CA1141892 A CA 1141892A CA 000332338 A CA000332338 A CA 000332338A CA 332338 A CA332338 A CA 332338A CA 1141892 A CA1141892 A CA 1141892A
- Authority
- CA
- Canada
- Prior art keywords
- resins
- cross
- concentration
- meq
- weight
- 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.)
- Expired
Links
- 125000000129 anionic group Chemical group 0.000 title claims abstract description 7
- 239000003456 ion exchange resin Substances 0.000 title claims abstract description 7
- 229920003303 ion-exchange polymer Polymers 0.000 title claims abstract description 7
- 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 title description 18
- 235000012000 cholesterol Nutrition 0.000 title description 9
- 230000003247 decreasing effect Effects 0.000 title description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229920000642 polymer Polymers 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000010521 absorption reaction Methods 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- -1 divinyl compound Chemical class 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 7
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 7
- 238000004132 cross linking Methods 0.000 claims abstract description 7
- 239000003822 epoxy resin Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 7
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 4
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract 9
- 231100000252 nontoxic Toxicity 0.000 claims abstract 2
- 230000003000 nontoxic effect Effects 0.000 claims abstract 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 16
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 12
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 12
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 12
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 2
- 229920005990 polystyrene resin Polymers 0.000 claims 2
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 229920005792 styrene-acrylic resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 abstract description 66
- 229920005989 resin Polymers 0.000 abstract description 66
- 230000000694 effects Effects 0.000 description 20
- 239000003613 bile acid Substances 0.000 description 12
- 150000001412 amines Chemical group 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 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 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000013019 agitation Methods 0.000 description 5
- 229940099352 cholate Drugs 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- 239000001828 Gelatine Substances 0.000 description 4
- 208000035150 Hypercholesterolemia Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000440 bentonite Substances 0.000 description 4
- 229910000278 bentonite Inorganic materials 0.000 description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000029142 excretion Effects 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002550 fecal effect Effects 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229920001268 Cholestyramine Polymers 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920000715 Mucilage Polymers 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 238000004176 ammonification Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940012017 ethylenediamine Drugs 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].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 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZJQIXGGEADDPQB-UHFFFAOYSA-N 1,2-bis(ethenyl)-3,4-dimethylbenzene Chemical group CC1=CC=C(C=C)C(C=C)=C1C ZJQIXGGEADDPQB-UHFFFAOYSA-N 0.000 description 1
- LBQJCDLKJGOHEA-UHFFFAOYSA-N 2-ethenylbut-3-enylbenzene Chemical compound C=CC(C=C)CC1=CC=CC=C1 LBQJCDLKJGOHEA-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 101100119771 Caenorhabditis elegans fat-6 gene Proteins 0.000 description 1
- 208000009447 Cardiac Edema Diseases 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 239000004470 DL Methionine Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010020601 Hyperchlorhydria Diseases 0.000 description 1
- 206010021036 Hyponatraemia Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 201000005577 familial hyperlipidemia Diseases 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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])[H] 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 235000006109 methionine Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 1
- MJFJKKXQDNNUJF-UHFFFAOYSA-N metixene Chemical compound C1N(C)CCCC1CC1C2=CC=CC=C2SC2=CC=CC=C21 MJFJKKXQDNNUJF-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 150000003431 steroids Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
-
- 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
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyethers (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2601478A IT1097396B (it) | 1978-07-24 | 1978-07-24 | Resine scambiatrici di ioni del tipo anionico con proprieta' ipocolesterolemizzanti |
| IT26014A/78 | 1978-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1141892A true CA1141892A (en) | 1983-02-22 |
Family
ID=11218412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000332338A Expired CA1141892A (en) | 1978-07-24 | 1979-07-23 | Anionic ion exchange resins with cholesterol decreasing properties |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5521480A (en, 2012) |
| AU (1) | AU529979B2 (en, 2012) |
| BE (1) | BE877101A (en, 2012) |
| CA (1) | CA1141892A (en, 2012) |
| DE (1) | DE2924893C2 (en, 2012) |
| ES (1) | ES482755A1 (en, 2012) |
| FR (1) | FR2432032A1 (en, 2012) |
| GB (1) | GB2026501B (en, 2012) |
| IT (1) | IT1097396B (en, 2012) |
| NL (1) | NL182568C (en, 2012) |
| NZ (1) | NZ190878A (en, 2012) |
| YU (1) | YU179079A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1213397A (en) * | 1980-10-20 | 1986-10-28 | Judith L. Page | Weight control with alkyl styrene polymers |
| US5230885A (en) * | 1987-12-23 | 1993-07-27 | Smith Kline & French Laboratories Limited | Polystyrene anion exchange polymer pharmaceutical composition |
| GB8730010D0 (en) * | 1987-12-23 | 1988-02-03 | Smith Kline French Lab | Compounds |
| GB8911719D0 (en) * | 1989-05-22 | 1989-07-05 | Smith Kline French Lab | Compounds |
| GB8913700D0 (en) * | 1989-06-14 | 1989-08-02 | Smith Kline French Lab | Compounds |
| GB8913699D0 (en) * | 1989-06-14 | 1989-08-02 | Smith Kline French Lab | Compounds |
| GB8928278D0 (en) * | 1989-12-14 | 1990-02-21 | Smith Kline French Lab | Compounds |
-
1978
- 1978-07-24 IT IT2601478A patent/IT1097396B/it active
-
1979
- 1979-02-14 FR FR7903703A patent/FR2432032A1/fr active Granted
- 1979-04-25 GB GB7914457A patent/GB2026501B/en not_active Expired
- 1979-06-19 BE BE0/195841A patent/BE877101A/xx not_active IP Right Cessation
- 1979-06-20 DE DE2924893A patent/DE2924893C2/de not_active Expired
- 1979-06-25 AU AU48341/79A patent/AU529979B2/en not_active Ceased
- 1979-06-29 NZ NZ190878A patent/NZ190878A/xx unknown
- 1979-07-09 NL NLAANVRAGE7905353,A patent/NL182568C/xx not_active IP Right Cessation
- 1979-07-23 YU YU01790/79A patent/YU179079A/xx unknown
- 1979-07-23 CA CA000332338A patent/CA1141892A/en not_active Expired
- 1979-07-23 ES ES482755A patent/ES482755A1/es not_active Expired
- 1979-07-23 JP JP9270379A patent/JPS5521480A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2432032A1 (fr) | 1980-02-22 |
| JPS6218218B2 (en, 2012) | 1987-04-22 |
| IT1097396B (it) | 1985-08-31 |
| NL182568C (nl) | 1988-04-05 |
| GB2026501A (en) | 1980-02-06 |
| DE2924893C2 (de) | 1983-08-04 |
| NL182568B (nl) | 1987-11-02 |
| AU4834179A (en) | 1980-02-07 |
| BE877101A (fr) | 1979-10-15 |
| DE2924893A1 (de) | 1980-02-14 |
| JPS5521480A (en) | 1980-02-15 |
| AU529979B2 (en) | 1983-06-30 |
| ES482755A1 (es) | 1980-04-16 |
| YU179079A (en) | 1982-10-31 |
| NZ190878A (en) | 1982-05-31 |
| GB2026501B (en) | 1982-12-08 |
| FR2432032B1 (en, 2012) | 1983-11-18 |
| IT7826014A0 (it) | 1978-07-24 |
| NL7905353A (nl) | 1980-01-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4393145A (en) | Anionic ion exchange resins with cholesterol-decreasing properties | |
| KR100346766B1 (ko) | 경구투여를위한포스페이트결합중합체 | |
| US4046750A (en) | Ionene modified small polymeric beads | |
| US4198395A (en) | Novel hypocholesterolemic resin | |
| US4737560A (en) | Polymer beads | |
| EP0354909B1 (en) | Variable crosslinked polymeric supports | |
| JP5074838B2 (ja) | 陰イオン結合性ポリマーとその利用 | |
| CA1141892A (en) | Anionic ion exchange resins with cholesterol decreasing properties | |
| FR2460968A1 (fr) | Nouveaux polymeres basiques reticules | |
| CA1045291A (en) | Method for preparation of amphoteric ion exchangers with the hydrophilic polymeric matrix | |
| Flach et al. | Polymeric surfactant systems in the asymmetric hydrogenation of amino acid precursors with a rhodium complex | |
| EP0179133A4 (en) | METHOD FOR PRODUCING ION EXCHANGE RESINS USING THE NUCLEAR POLYMERIZATION TECHNOLOGY. | |
| Sahiner et al. | Soft hydrogel particles with high functional value | |
| Lele et al. | Molecularly imprinted polymer mimics of chymotrypsin: 2. Functional monomers and hydrolytic activity | |
| WO2001025291A1 (en) | Sugar binding polymers and the use thereof | |
| US4374206A (en) | Synthesis of base-stable aliphatic anion exchange polymers | |
| KR20040091385A (ko) | 자성 음이온 교환수지 및 그 제조방법 | |
| JP3059251B2 (ja) | アミノリン酸型キレート樹脂の製造方法 | |
| JP3232699B2 (ja) | 多孔性アニオン交換樹脂及びその製造方法 | |
| EP0045824A1 (en) | Ion exchange material, its preparation and use | |
| Rembaum | Ionene modified small polymeric beads | |
| Ciaccio | Bifunctional interpenetrating polymer networks: synthesis and investigation of the microenvironmental effect | |
| Strumia et al. | A new gel as support for ionic exchanger: a copolymer of butadiene-acrylic acid with tannic acid and 2-hydroxyethyl methacrylate grafting | |
| JP6835529B2 (ja) | チオール基含有イオン性高分子化合物及びその製造方法 | |
| CA2058993A1 (en) | Molded body of water-absorbing resin, process for producing molded body, use thereof, and process for preparing water-absorbing resin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |