JP2002500183A - 脂肪結合性ポリマー - Google Patents
脂肪結合性ポリマーInfo
- Publication number
- JP2002500183A JP2002500183A JP2000527238A JP2000527238A JP2002500183A JP 2002500183 A JP2002500183 A JP 2002500183A JP 2000527238 A JP2000527238 A JP 2000527238A JP 2000527238 A JP2000527238 A JP 2000527238A JP 2002500183 A JP2002500183 A JP 2002500183A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- fat
- poly
- mol
- alkyl 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.)
- Pending
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 213
- 230000027455 binding Effects 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 93
- 241000124008 Mammalia Species 0.000 claims abstract description 18
- 208000008589 Obesity Diseases 0.000 claims abstract description 13
- 235000020824 obesity Nutrition 0.000 claims abstract description 13
- SIKWOTFNWURSAY-UHFFFAOYSA-N Lipstatin Natural products CCCCCCC1C(CC(CC=CCC=CCCCCC)C(=O)OC(CC(C)C)NC=O)OC1=O SIKWOTFNWURSAY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 7
- OQMAKWGYQLJJIA-CUOOPAIESA-N lipstatin Chemical compound CCCCCC[C@H]1[C@H](C[C@H](C\C=C/C\C=C/CCCCC)OC(=O)[C@H](CC(C)C)NC=O)OC1=O OQMAKWGYQLJJIA-CUOOPAIESA-N 0.000 claims abstract description 7
- 229940127470 Lipase Inhibitors Drugs 0.000 claims abstract description 6
- AHLBNYSZXLDEJQ-UHFFFAOYSA-N N-formyl-L-leucylester Natural products CCCCCCCCCCCC(OC(=O)C(CC(C)C)NC=O)CC1OC(=O)C1CCCCCC AHLBNYSZXLDEJQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010521 absorption reaction Methods 0.000 claims abstract description 6
- 235000013367 dietary fats Nutrition 0.000 claims abstract description 6
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims abstract description 6
- 229960001243 orlistat Drugs 0.000 claims abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 73
- 230000002209 hydrophobic effect Effects 0.000 claims description 61
- 150000001412 amines Chemical class 0.000 claims description 51
- 239000000178 monomer Substances 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 229920000083 poly(allylamine) Polymers 0.000 claims description 31
- 229940086609 Lipase inhibitor Drugs 0.000 claims description 20
- 229920002873 Polyethylenimine Polymers 0.000 claims description 19
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 18
- 229920001577 copolymer Polymers 0.000 claims description 16
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000003431 cross linking reagent Substances 0.000 claims description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 7
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims description 7
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 7
- 208000001162 steatorrhea Diseases 0.000 claims description 7
- 206010041969 Steatorrhoea Diseases 0.000 claims description 6
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 claims description 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical group C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- 229920002401 polyacrylamide Polymers 0.000 claims description 4
- 239000004971 Cross linker Substances 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 2
- UABZBFJRDPRXJR-UHFFFAOYSA-N 2-methylidenebutanoate;trimethylazanium Chemical compound C[NH+](C)C.CCC(=C)C([O-])=O UABZBFJRDPRXJR-UHFFFAOYSA-N 0.000 claims description 2
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 claims description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
- ZWAPMFBHEQZLGK-UHFFFAOYSA-N 5-(dimethylamino)-2-methylidenepentanamide Chemical compound CN(C)CCCC(=C)C(N)=O ZWAPMFBHEQZLGK-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004386 diacrylate group Chemical group 0.000 claims description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
- WGESLFUSXZBFQF-UHFFFAOYSA-N n-methyl-n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCN(C)CC=C WGESLFUSXZBFQF-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 1
- RNTIBYGPJVJCCJ-UHFFFAOYSA-N n,n-dimethylmethanamine;ethyl 2-methylprop-2-enoate Chemical compound CN(C)C.CCOC(=O)C(C)=C RNTIBYGPJVJCCJ-UHFFFAOYSA-N 0.000 claims 1
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 claims 1
- ZBKXCYSJSMCLHH-UHFFFAOYSA-N n-propylprop-2-enimidate;trimethylazanium Chemical compound C[NH+](C)C.CCCN=C([O-])C=C ZBKXCYSJSMCLHH-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 230000029087 digestion Effects 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 120
- 239000000203 mixture Substances 0.000 description 109
- 239000000243 solution Substances 0.000 description 107
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 80
- -1 ESTRA TM Substances 0.000 description 78
- 239000003925 fat Substances 0.000 description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 239000000047 product Substances 0.000 description 56
- 239000007787 solid Substances 0.000 description 54
- 238000002360 preparation method Methods 0.000 description 46
- 239000007864 aqueous solution Substances 0.000 description 39
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 28
- 239000000499 gel Substances 0.000 description 24
- 239000000843 powder Substances 0.000 description 24
- 239000000523 sample Substances 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 23
- TYVWBCMQECJNSK-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)butan-2-yl]azanium;chloride Chemical compound [Cl-].CC([NH3+])(C)C(C)OC(=O)C(C)=C TYVWBCMQECJNSK-UHFFFAOYSA-N 0.000 description 20
- 239000008367 deionised water Substances 0.000 description 20
- 229910021641 deionized water Inorganic materials 0.000 description 20
- 239000002245 particle Substances 0.000 description 20
- 239000012265 solid product Substances 0.000 description 19
- 229910001220 stainless steel Inorganic materials 0.000 description 19
- 239000010935 stainless steel Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 18
- 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 17
- 230000035484 reaction time Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000012043 crude product Substances 0.000 description 15
- 238000010908 decantation Methods 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 14
- 239000002168 alkylating agent Substances 0.000 description 13
- 229940100198 alkylating agent Drugs 0.000 description 13
- 235000013305 food Nutrition 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 11
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 9
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 8
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 8
- 108050006759 Pancreatic lipases Proteins 0.000 description 8
- 102000019280 Pancreatic lipases Human genes 0.000 description 8
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 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 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000003828 vacuum filtration Methods 0.000 description 8
- 239000004367 Lipase Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229920006037 cross link polymer Polymers 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000000269 nucleophilic effect Effects 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 6
- 102000004882 Lipase Human genes 0.000 description 6
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 6
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical group N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 235000019421 lipase Nutrition 0.000 description 6
- 229940116369 pancreatic lipase Drugs 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- PZNOBXVHZYGUEX-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine;hydrochloride Chemical compound Cl.C=CCNCC=C PZNOBXVHZYGUEX-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- QYOXLKAKUAASNA-UHFFFAOYSA-N 1-bromodocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCBr QYOXLKAKUAASNA-UHFFFAOYSA-N 0.000 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 235000012000 cholesterol Nutrition 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- 230000002550 fecal effect Effects 0.000 description 4
- 210000003608 fece Anatomy 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- OUUQCZGPVNCOIJ-UHFFFAOYSA-N hydroperoxyl Chemical compound O[O] OUUQCZGPVNCOIJ-UHFFFAOYSA-N 0.000 description 4
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- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000004006 olive oil Substances 0.000 description 4
- 235000008390 olive oil Nutrition 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- TURITJIWSQEMDB-UHFFFAOYSA-N 2-methyl-n-[(2-methylprop-2-enoylamino)methyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCNC(=O)C(C)=C TURITJIWSQEMDB-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
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- 239000011780 sodium chloride Substances 0.000 description 3
- 229920001059 synthetic polymer Polymers 0.000 description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 3
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 2
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- XLDYQTBLOUFNEQ-UHFFFAOYSA-N CC(=C)C(O)=O.NC(=O)C(C)=CCC=C(C)C(N)=O Chemical compound CC(=C)C(O)=O.NC(=O)C(C)=CCC=C(C)C(N)=O XLDYQTBLOUFNEQ-UHFFFAOYSA-N 0.000 description 2
- 229920001661 Chitosan Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
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- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- HADJJUAGACHKHO-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)butanamide Chemical compound CCCC(=O)NCC1CO1 HADJJUAGACHKHO-UHFFFAOYSA-N 0.000 description 1
- XKWWQHSAOSKPJC-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)hexanamide Chemical compound CCCCCC(=O)NCC1CO1 XKWWQHSAOSKPJC-UHFFFAOYSA-N 0.000 description 1
- UMLARORAEPLXTC-UHFFFAOYSA-N n-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine;2-methyl-1-phenylpropan-2-amine Chemical compound CC(C)(N)CC1=CC=CC=C1.CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 UMLARORAEPLXTC-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- OTTYFDRFBJPGRW-UHFFFAOYSA-N pent-2-enoyl chloride Chemical compound CCC=CC(Cl)=O OTTYFDRFBJPGRW-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229920000184 poly(octadecyl acrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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 1
- AWDRATDZQPNJFN-VAYUFCLWSA-N taurodeoxycholic 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)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 AWDRATDZQPNJFN-VAYUFCLWSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- 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
- A61K31/765—Polymers containing oxygen
-
- 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
- A61K31/765—Polymers containing oxygen
- A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
-
- 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
- A61K31/785—Polymers containing nitrogen
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Detergent Compositions (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US496398A | 1998-01-09 | 1998-01-09 | |
| US09/004,963 | 1998-01-09 | ||
| US09/166,453 US6264937B1 (en) | 1998-01-09 | 1998-10-05 | Fat-binding polymers |
| US09/166,453 | 1998-10-05 | ||
| PCT/US1999/000028 WO1999034787A2 (en) | 1998-01-09 | 1999-01-04 | Fat-binding polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002500183A true JP2002500183A (ja) | 2002-01-08 |
| JP2002500183A5 JP2002500183A5 (enExample) | 2006-02-23 |
Family
ID=26673719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000527238A Pending JP2002500183A (ja) | 1998-01-09 | 1999-01-04 | 脂肪結合性ポリマー |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1043981B1 (enExample) |
| JP (1) | JP2002500183A (enExample) |
| KR (2) | KR20060111741A (enExample) |
| CN (1) | CN1212123C (enExample) |
| AT (1) | ATE237349T1 (enExample) |
| AU (2) | AU740233B2 (enExample) |
| BR (1) | BR9907234A (enExample) |
| CA (1) | CA2318417A1 (enExample) |
| DE (1) | DE69906928T2 (enExample) |
| ES (1) | ES2200493T3 (enExample) |
| HU (1) | HUP0100890A3 (enExample) |
| IL (1) | IL137096A (enExample) |
| MX (1) | MX222446B (enExample) |
| NO (1) | NO20003510L (enExample) |
| NZ (2) | NZ505294A (enExample) |
| PL (1) | PL193452B1 (enExample) |
| RU (1) | RU2222335C2 (enExample) |
| WO (1) | WO1999034787A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007502811A (ja) * | 2003-08-21 | 2007-02-15 | フォルスカーパテント イー エスイーデー アーベー | 肥満の予防用の医薬組成物の製剤におけるコリパーゼ−リパーゼ阻害剤の使用 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6267952B1 (en) * | 1998-01-09 | 2001-07-31 | Geltex Pharmaceuticals, Inc. | Lipase inhibiting polymers |
| MXPA02000492A (es) * | 1999-07-14 | 2002-07-02 | Geltex Pharma Inc | Polimeros enlazantes de grasas, opcionalmente combinados con inhibidores de lipasas. |
| EP1219297A4 (en) * | 1999-10-01 | 2004-11-17 | Amato Pharm Prod Ltd | ACTIVE AGENTS AGAINST FATTY ADDICTION |
| KR100572785B1 (ko) | 2000-07-28 | 2006-04-19 | 에프. 호프만-라 로슈 아게 | 신규한 약학 조성물 |
| EP1379259A1 (en) | 2001-04-18 | 2004-01-14 | Genzyme Corporation | Methods of treating syndrome x with aliphatic polyamines |
| US8372430B2 (en) | 2002-12-17 | 2013-02-12 | The Procter & Gamble Company | Compositions, methods, and kits useful for the alleviation of gastrointestinal effects |
| CN106176800B (zh) * | 2016-07-11 | 2019-12-06 | 韩源平 | 多聚阳离子树脂的制药应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7017227A (enExample) * | 1969-12-27 | 1971-06-29 | ||
| US4211765A (en) * | 1971-10-12 | 1980-07-08 | Monsanto Company | Method for controlling obesity |
| US4432968A (en) * | 1980-10-20 | 1984-02-21 | The Dow Chemical Company | Weight control with fat imbibing polymers |
| CA1213397A (en) * | 1980-10-20 | 1986-10-28 | Judith L. Page | Weight control with alkyl styrene polymers |
| EP0354948A1 (fr) * | 1988-02-12 | 1990-02-21 | DE ZAEPFFEL, Brigitte | Copolymere hydrophile reticule a usage medical et paramedical |
| RU2066185C1 (ru) * | 1993-01-11 | 1996-09-10 | Институт пищевых веществ РАН | Гиполипидемический энтеросорбент |
| JP3507523B2 (ja) * | 1993-05-12 | 2004-03-15 | 積水化学工業株式会社 | 糖質吸収抑制剤 |
-
1999
- 1999-01-04 PL PL343898A patent/PL193452B1/pl unknown
- 1999-01-04 ES ES99900369T patent/ES2200493T3/es not_active Expired - Lifetime
- 1999-01-04 KR KR1020067021186A patent/KR20060111741A/ko not_active Ceased
- 1999-01-04 AU AU19505/99A patent/AU740233B2/en not_active Ceased
- 1999-01-04 JP JP2000527238A patent/JP2002500183A/ja active Pending
- 1999-01-04 CA CA002318417A patent/CA2318417A1/en not_active Abandoned
- 1999-01-04 IL IL137096A patent/IL137096A/en active IP Right Grant
- 1999-01-04 DE DE69906928T patent/DE69906928T2/de not_active Expired - Fee Related
- 1999-01-04 HU HU0100890A patent/HUP0100890A3/hu unknown
- 1999-01-04 RU RU2000120918/14A patent/RU2222335C2/ru not_active IP Right Cessation
- 1999-01-04 KR KR1020007007608A patent/KR100773625B1/ko not_active Expired - Fee Related
- 1999-01-04 NZ NZ505294A patent/NZ505294A/xx unknown
- 1999-01-04 BR BR9907234-3A patent/BR9907234A/pt not_active Application Discontinuation
- 1999-01-04 CN CNB998020311A patent/CN1212123C/zh not_active Expired - Fee Related
- 1999-01-04 WO PCT/US1999/000028 patent/WO1999034787A2/en not_active Ceased
- 1999-01-04 AT AT99900369T patent/ATE237349T1/de not_active IP Right Cessation
- 1999-01-04 EP EP99900369A patent/EP1043981B1/en not_active Expired - Lifetime
- 1999-01-04 NZ NZ523301A patent/NZ523301A/en unknown
-
2000
- 2000-07-06 MX MXPA00006681 patent/MX222446B/es active IP Right Grant
- 2000-07-07 NO NO20003510A patent/NO20003510L/no not_active Application Discontinuation
-
2002
- 2002-02-01 AU AU2002014755A patent/AU2002014755A1/xx not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007502811A (ja) * | 2003-08-21 | 2007-02-15 | フォルスカーパテント イー エスイーデー アーベー | 肥満の予防用の医薬組成物の製剤におけるコリパーゼ−リパーゼ阻害剤の使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1043981A2 (en) | 2000-10-18 |
| HK1034044A1 (en) | 2001-10-12 |
| KR100773625B1 (ko) | 2007-11-05 |
| DE69906928D1 (de) | 2003-05-22 |
| AU1950599A (en) | 1999-07-26 |
| KR20010034013A (ko) | 2001-04-25 |
| MX222446B (en) | 2004-09-01 |
| ES2200493T3 (es) | 2004-03-01 |
| PL193452B1 (pl) | 2007-02-28 |
| MXPA00006681A (es) | 2001-02-01 |
| CN1288381A (zh) | 2001-03-21 |
| CN1212123C (zh) | 2005-07-27 |
| NO20003510L (no) | 2000-09-07 |
| NZ505294A (en) | 2003-02-28 |
| KR20060111741A (ko) | 2006-10-27 |
| NO20003510D0 (no) | 2000-07-07 |
| AU2002014755A1 (en) | 2002-03-14 |
| HUP0100890A3 (en) | 2001-12-28 |
| IL137096A (en) | 2006-10-31 |
| HUP0100890A2 (hu) | 2001-08-28 |
| RU2222335C2 (ru) | 2004-01-27 |
| ATE237349T1 (en) | 2003-05-15 |
| CA2318417A1 (en) | 1999-07-15 |
| BR9907234A (pt) | 2000-10-10 |
| IL137096A0 (en) | 2001-06-14 |
| PL343898A1 (en) | 2001-09-10 |
| DE69906928T2 (de) | 2004-02-19 |
| AU740233B2 (en) | 2001-11-01 |
| NZ523301A (en) | 2005-11-25 |
| EP1043981B1 (en) | 2003-04-16 |
| WO1999034787A3 (en) | 2000-01-20 |
| WO1999034787A2 (en) | 1999-07-15 |
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