CA2959760C - Crystal modifications of elobixibat - Google Patents
Crystal modifications of elobixibat Download PDFInfo
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- CA2959760C CA2959760C CA2959760A CA2959760A CA2959760C CA 2959760 C CA2959760 C CA 2959760C CA 2959760 A CA2959760 A CA 2959760A CA 2959760 A CA2959760 A CA 2959760A CA 2959760 C CA2959760 C CA 2959760C
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- elobixibat
- radiation
- cuka1
- crystalline
- xrpd pattern
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- XFLQIRAKKLNXRQ-UUWRZZSWSA-N elobixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)NCC(O)=O)C=3C=CC=CC=3)C=C2S(=O)(=O)CC(CCCC)(CCCC)CN1C1=CC=CC=C1 XFLQIRAKKLNXRQ-UUWRZZSWSA-N 0.000 title claims abstract description 62
- 229950000820 elobixibat Drugs 0.000 title claims abstract description 56
- 108010007192 elobixibat Proteins 0.000 title claims abstract description 56
- 239000013078 crystal Substances 0.000 title description 92
- 238000012986 modification Methods 0.000 title description 78
- 230000004048 modification Effects 0.000 title description 77
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 63
- 150000004683 dihydrates Chemical group 0.000 claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 238000011321 prophylaxis Methods 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 208000035475 disorder Diseases 0.000 claims description 12
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 12
- 206010008635 Cholestasis Diseases 0.000 claims description 10
- 206010010774 Constipation Diseases 0.000 claims description 10
- 239000003613 bile acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 210000004185 liver Anatomy 0.000 claims description 9
- 206010019708 Hepatic steatosis Diseases 0.000 claims description 8
- 230000007870 cholestasis Effects 0.000 claims description 8
- 231100000359 cholestasis Toxicity 0.000 claims description 8
- 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 claims description 7
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 7
- 210000003445 biliary tract Anatomy 0.000 claims description 6
- 230000007547 defect Effects 0.000 claims description 5
- 208000019423 liver disease Diseases 0.000 claims description 5
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 4
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 4
- 208000004930 Fatty Liver Diseases 0.000 claims description 4
- 206010023126 Jaundice Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 4
- 201000002150 Progressive familial intrahepatic cholestasis Diseases 0.000 claims description 4
- 208000003251 Pruritus Diseases 0.000 claims description 4
- 108091022863 bile acid binding Proteins 0.000 claims description 4
- 102000030904 bile acid binding Human genes 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 208000010706 fatty liver disease Diseases 0.000 claims description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
- 230000035935 pregnancy Effects 0.000 claims description 4
- 231100000240 steatosis hepatitis Toxicity 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 3
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 201000011374 Alagille syndrome Diseases 0.000 claims description 2
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 2
- 206010004637 Bile duct stone Diseases 0.000 claims description 2
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 claims description 2
- 201000009331 Choledocholithiasis Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 206010012735 Diarrhoea Diseases 0.000 claims description 2
- 206010072268 Drug-induced liver injury Diseases 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 208000027761 Hepatic autoimmune disease Diseases 0.000 claims description 2
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 2
- 206010019728 Hepatitis alcoholic Diseases 0.000 claims description 2
- 206010019799 Hepatitis viral Diseases 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 206010022489 Insulin Resistance Diseases 0.000 claims description 2
- 206010065973 Iron Overload Diseases 0.000 claims description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 102100036325 Sterol 26-hydroxylase, mitochondrial Human genes 0.000 claims description 2
- 201000004525 Zellweger Syndrome Diseases 0.000 claims description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
- 208000002353 alcoholic hepatitis Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000001088 cerebrotendinous xanthomatosis Diseases 0.000 claims description 2
- 201000001883 cholelithiasis Diseases 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 201000008865 drug-induced hepatitis Diseases 0.000 claims description 2
- 208000009866 extrahepatic cholestasis Diseases 0.000 claims description 2
- 230000004129 fatty acid metabolism Effects 0.000 claims description 2
- 208000001130 gallstones Diseases 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 208000006454 hepatitis Diseases 0.000 claims description 2
- 231100000283 hepatitis Toxicity 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 230000003516 hyperlipidaemic effect Effects 0.000 claims description 2
- 208000016245 inborn errors of metabolism Diseases 0.000 claims description 2
- 208000015978 inherited metabolic disease Diseases 0.000 claims description 2
- 208000001024 intrahepatic cholestasis Diseases 0.000 claims description 2
- 230000036210 malignancy Effects 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 208000007232 portal hypertension Diseases 0.000 claims description 2
- 230000000750 progressive effect Effects 0.000 claims description 2
- 208000010157 sclerosing cholangitis Diseases 0.000 claims description 2
- 238000006748 scratching Methods 0.000 claims description 2
- 230000002393 scratching effect Effects 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 201000001862 viral hepatitis Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000002002 slurry Substances 0.000 description 16
- 239000012453 solvate Substances 0.000 description 15
- 239000000843 powder Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 230000008859 change Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 150000004682 monohydrates Chemical group 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000001179 sorption measurement Methods 0.000 description 8
- 208000024891 symptom Diseases 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 238000003795 desorption Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229940125922 IBAT inhibitor Drugs 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- -1 tert-butoxyl ester Chemical class 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 description 1
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 102100034605 Atrial natriuretic peptide receptor 3 Human genes 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 description 1
- 240000001973 Ficus microcarpa Species 0.000 description 1
- 102100025353 G-protein coupled bile acid receptor 1 Human genes 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101000924488 Homo sapiens Atrial natriuretic peptide receptor 3 Proteins 0.000 description 1
- 101000857733 Homo sapiens G-protein coupled bile acid receptor 1 Proteins 0.000 description 1
- 229940123993 Incretin mimetic Drugs 0.000 description 1
- 229940126033 PPAR agonist Drugs 0.000 description 1
- 208000017855 Progressive familial intrahepatic cholestasis type 1 Diseases 0.000 description 1
- 229940123934 Reductase inhibitor Drugs 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000010431 corundum Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012886 linear function Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 201000002162 progressive familial intrahepatic cholestasis 1 Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940075993 receptor modulator Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14190290.8 | 2014-10-24 | ||
| EP14190290.8A EP3012252A1 (en) | 2014-10-24 | 2014-10-24 | Crystal modifications of elobixibat |
| PCT/EP2015/074573 WO2016062848A1 (en) | 2014-10-24 | 2015-10-23 | Crystal modifications of elobixibat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2959760A1 CA2959760A1 (en) | 2016-04-28 |
| CA2959760C true CA2959760C (en) | 2023-10-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2959760A Active CA2959760C (en) | 2014-10-24 | 2015-10-23 | Crystal modifications of elobixibat |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US10183920B2 (enExample) |
| EP (3) | EP3012252A1 (enExample) |
| JP (1) | JP6700263B2 (enExample) |
| KR (1) | KR102498539B1 (enExample) |
| CN (2) | CN107001301A (enExample) |
| AU (1) | AU2015334883B2 (enExample) |
| CA (1) | CA2959760C (enExample) |
| ES (1) | ES2874573T3 (enExample) |
| RU (1) | RU2017114109A (enExample) |
| WO (1) | WO2016062848A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5889321B2 (ja) | 2010-11-04 | 2016-03-22 | アルビレオ アクチエボラグ | 肝疾患の処置用のｉｂａｔ阻害剤 |
| JP6751020B2 (ja) | 2014-06-25 | 2020-09-02 | Ｅａファーマ株式会社 | 固形製剤及びその着色防止又は着色低減方法 |
| US10441604B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Cholestyramine pellets and methods for preparation thereof |
| US10786529B2 (en) | 2016-02-09 | 2020-09-29 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10441605B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| KR101844184B1 (ko) * | 2017-07-21 | 2018-04-02 | 씨제이헬스케어 주식회사 | 아미노알킬벤조티아제핀 유도체의 용도 |
| EP3664781A1 (en) | 2017-08-09 | 2020-06-17 | Albireo AB | Cholestyramine granules, oral cholestyramine formulations and use thereof |
| US10428109B1 (en) | 2018-03-09 | 2019-10-01 | Elobix Ab | Process for the preparation of 1,5-benzothiazepine compounds |
| EP3762370A1 (en) * | 2018-03-09 | 2021-01-13 | Elobix Ab | Process for the preparation of elobixibat |
| EP3802504B1 (en) | 2018-06-05 | 2023-01-18 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| US10793534B2 (en) | 2018-06-05 | 2020-10-06 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| WO2019245448A1 (en) | 2018-06-20 | 2019-12-26 | Albireo Ab | Crystal modifications of odevixibat |
| US11549878B2 (en) | 2018-08-09 | 2023-01-10 | Albireo Ab | In vitro method for determining the adsorbing capacity of an insoluble adsorbant |
| US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10975045B2 (en) | 2019-02-06 | 2021-04-13 | Aibireo AB | Benzothiazepine compounds and their use as bile acid modulators |
| US10941127B2 (en) | 2019-02-06 | 2021-03-09 | Albireo Ab | Benzothiadiazepine compounds and their use as bile acid modulators |
| RS63899B1 (sr) | 2019-02-06 | 2023-02-28 | Albireo Ab | Benzotiadiazepinska jedinjenja i njihova upotreba kao modulatora žučnih kiselina |
| US12344589B2 (en) | 2019-09-09 | 2025-07-01 | Elobix Ab | Method for producing a 1,5-benzothiazepin compound |
| EP4069359B1 (en) | 2019-12-04 | 2024-01-03 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| EP4069361B1 (en) | 2019-12-04 | 2024-01-03 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| US11014898B1 (en) | 2020-12-04 | 2021-05-25 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| CN114761018B (zh) | 2019-12-04 | 2025-12-02 | 阿尔比里奥公司 | 苯并硫杂二氮杂环庚三烯化合物及其作为胆汁酸调节剂的用途 |
| MX2022006731A (es) | 2019-12-04 | 2022-06-09 | Albireo Ab | Compuestos de benzoti(di)azepina y su uso como moduladores del acido biliar. |
| EP4188541B1 (en) | 2020-08-03 | 2024-12-25 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| WO2022101379A1 (en) | 2020-11-12 | 2022-05-19 | Albireo Ab | Odevixibat for treating progressive familial intrahepatic cholestasis (pfic) |
| JP2023549226A (ja) | 2020-11-12 | 2023-11-22 | アルビレオ エービー | 進行性家族性肝内胆汁うっ滞症（ｐｆｉｃ）を処置するためのオデビキシバット |
| KR20230117393A (ko) | 2020-12-04 | 2023-08-08 | 알비레오 에이비 | 벤조티아(디)아제핀 화합물 및 담즙산 조절제로서의용도 |
| TW202313579A (zh) | 2021-06-03 | 2023-04-01 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽酸調節劑之用途 |
| KR20250040737A (ko) * | 2022-08-02 | 2025-03-24 | 상하이 하오위안 케멕스프레스 컴퍼니, 리미티드 | 엘로빅시바트의 결정형 ii 및 이의 제조 방법 |
| KR20250088781A (ko) | 2022-11-03 | 2025-06-17 | 알비레오 에이비 | 알라질 증후군(algs) 치료 |
| WO2025093760A1 (en) | 2023-11-03 | 2025-05-08 | Albireo Ab | Treating pfic2 with odevixibat |
Family Cites Families (115)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539380A (en) | 1968-01-08 | 1970-11-10 | Upjohn Co | Methylcellulose and polyalkylene glycol coating of solid medicinal dosage forms |
| GB1530201A (en) | 1976-04-14 | 1978-10-25 | Pfizer Ltd | Process for the preparation of aminoglycoside antibiotics and intermediates therefor |
| GB1566609A (en) | 1977-03-10 | 1980-05-08 | Reckitt & Colmann Prod Ltd | Pharmaceutical compositions containing cholestyramine and alginic acid |
| EP0019115B1 (de) | 1979-04-30 | 1983-01-12 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Pankreozymin-Cholezystokinin aktive Peptide, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| US4900757A (en) | 1988-12-08 | 1990-02-13 | Merrell Dow Pharmaceuticals Inc. | Hypocholesterolemic and antiatherosclerotic uses of bix(3,5-di-tertiary-butyl-4-hydroxyphenylthio)methane |
| DE3930168A1 (de) | 1989-09-09 | 1991-03-14 | Knoll Ag | Verbesserte verabreichungsform fuer colestyramin |
| IL95574A (en) | 1989-09-09 | 1994-11-11 | Knoll Ag | Colestyramine preparation |
| FI106800B (fi) | 1990-12-06 | 2001-04-12 | Hoechst Ag | Menetelmä uusien terapeuttisesti käyttökelpoisten dimeeristen sappihappojohdannaisten valmistamiseksi |
| ATE135380T1 (de) | 1991-12-20 | 1996-03-15 | Hoechst Ag | Polymere und oligomere von gallensäurederivaten, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| JPH05186357A (ja) | 1991-12-31 | 1993-07-27 | Shigeo Ochi | 飲食物消化分解産物吸収抑制手段 |
| GB9203347D0 (en) | 1992-02-17 | 1992-04-01 | Wellcome Found | Hypolipidaemic compounds |
| IT1257793B (it) | 1992-05-18 | 1996-02-13 | Composizione farmaceutica a base di acidi biliari in microgranuli a rilascio controllato | |
| DK0573848T3 (da) | 1992-06-12 | 1998-08-10 | Hoechst Ag | Galdesyrederivater, fremgangsmåde til deres fremstilling og anvendelse af disse forbindelser som lægemidler |
| US5350584A (en) | 1992-06-26 | 1994-09-27 | Merck & Co., Inc. | Spheronization process using charged resins |
| IL108634A0 (en) | 1993-02-15 | 1994-05-30 | Wellcome Found | Hypolipidaemic heterocyclic compounds, their prepatation and pharmaceutical compositions containing them |
| IL108633A (en) | 1993-02-15 | 1998-07-15 | Wellcome Found | History of Benzothiazepine Hypolipidemic Preparation and Pharmaceutical Preparations Containing Them |
| DE69425453T2 (de) | 1993-04-23 | 2001-04-12 | Novartis Ag, Basel | Wirkstoffabgabevorrichtung mit gesteuerter Freigabe |
| EP0624593A3 (de) | 1993-05-08 | 1995-06-07 | Hoechst Ag | Gallensäurederivate, Verfahren zu ihrer Herstellung und Verwendung dieser Verbindungen als Arzneimittel. |
| TW289021B (enExample) | 1993-05-08 | 1996-10-21 | Hoechst Ag | |
| TW289020B (enExample) | 1993-05-08 | 1996-10-21 | Hoechst Sktiengesellschaft | |
| TW289757B (enExample) | 1993-05-08 | 1996-11-01 | Hoechst Ag | |
| ZA956647B (en) | 1994-08-10 | 1997-02-10 | Wellcome Found | Hypolipidaemic compounds. |
| BR9508916A (pt) | 1994-09-13 | 1997-12-30 | Monsanto Co | "Novas benzotiepinas tendo atividade como inibidores de transporte do ácido biliar ileal e absorção de taurocolato" |
| US6262277B1 (en) | 1994-09-13 | 2001-07-17 | G.D. Searle And Company | Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| US5994391A (en) | 1994-09-13 | 1999-11-30 | G.D. Searle And Company | Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| US6642268B2 (en) | 1994-09-13 | 2003-11-04 | G.D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors |
| GB9423172D0 (en) | 1994-11-17 | 1995-01-04 | Wellcom Foundation The Limited | Hypolipidemic benzothiazepines |
| US5811388A (en) | 1995-06-07 | 1998-09-22 | Cibus Pharmaceutical, Inc. | Delivery of drugs to the lower GI tract |
| CA2242991C (en) | 1996-01-16 | 2007-07-24 | University Technology Corporation | Use of antioxidant agents to treat cholestatic liver disease |
| IL126038A0 (en) | 1996-03-11 | 1999-05-09 | Searle & Co | Novel benzothiepines and derivatives thereof and pharmaceutical compositions comprising them |
| ATE197842T1 (de) | 1996-07-24 | 2000-12-15 | Zumtobel Staff Gmbh | Adapter für ein haltemittel, welches zum befestigen einer einbauleuchte in einer einbauöffnung bestimmt ist, oder haltemittel oder einbauleuchte mit einem solchen adapter |
| DE19633268A1 (de) | 1996-08-19 | 1998-02-26 | Hoechst Ag | Polymere Gallensäure-Resorptionsinhibitoren mit gleichzeitiger Gallensäure-Adsorberwirkung |
| GB9704208D0 (en) | 1997-02-28 | 1997-04-16 | Glaxo Group Ltd | Chemical compounds |
| IL131872A0 (en) | 1997-03-11 | 2001-03-19 | Searle & Co | Composition comprising an ileal bile acid transport inhibiting benzothiepines and hmg co-a reductase inhibitors |
| PT864582E (pt) | 1997-03-14 | 2003-10-31 | Aventis Pharma Gmbh | 1,4-benzotiazepina-1,1-dioxidos hipolipidemicos |
| US6635280B2 (en) | 1997-06-06 | 2003-10-21 | Depomed, Inc. | Extending the duration of drug release within the stomach during the fed mode |
| AUPO763197A0 (en) | 1997-06-30 | 1997-07-24 | Sigma Pharmaceuticals Pty Ltd | Health supplement |
| BR9814300A (pt) | 1997-12-19 | 2002-02-05 | Searle & Co | Método de preparação de óxidos de tetraidrobenzotiepina enanciomericamente enriquecidos |
| GB9800428D0 (en) | 1998-01-10 | 1998-03-04 | Glaxo Group Ltd | Chemical compounds |
| CA2325736A1 (en) | 1998-04-24 | 1999-11-04 | Fujisawa Pharmaceutical Co., Ltd. | Guanidine derivatives |
| DE19825804C2 (de) | 1998-06-10 | 2000-08-24 | Aventis Pharma Gmbh | 1,4-Benzothiepin-1,1-dioxidderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US6221897B1 (en) | 1998-06-10 | 2001-04-24 | Aventis Pharma Deutschland Gmbh | Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use |
| WO2000008018A1 (en) | 1998-08-07 | 2000-02-17 | Takeda Chemical Industries, Ltd. | Benzothiepin derivatives, process for the preparation of the same and uses thereof |
| NZ512533A (en) | 1998-12-23 | 2004-02-27 | G | A combination of IBAT inhibitor and nicotinic acid derivative to treat hypercholesterolemia, hyperlipidemic or atherosclerotic conditions |
| DE69907960T2 (de) | 1998-12-23 | 2004-02-26 | G.D. Searle Llc, Chicago | Kombinationen von ileumgallensäuretransports inhibitoren und fibronsäure derivaten für kardiovaskuläre indikationen |
| NZ512536A (en) | 1998-12-23 | 2003-11-28 | G | Combinations of ileal bile acid transport inhibitors and cholesteryl ester transfer protein inhibitors for cardiovascular indications |
| WO2000038725A1 (en) | 1998-12-23 | 2000-07-06 | G.D. Searle Llc | Combinations for cardiovascular indications |
| PT1140190E (pt) | 1998-12-23 | 2003-02-28 | Searle Llc | Combinacoes de inibidores do transporte ileal dos acidos biliares e agentes sequestrantes dos acidos biliares usadas para problemas cardiovasculares |
| EP1155007A2 (en) | 1999-02-12 | 2001-11-21 | G.D. Searle LLC | 1,2-benzothiazepines for the treatment of hyperlipidemic diseases |
| DE19916108C1 (de) | 1999-04-09 | 2001-01-11 | Aventis Pharma Gmbh | Mit Zuckerresten substituierte 1,4-Benzothiazepin-1,1-dioxidderivate, Verfahren zu deren Herstellung und deren Verwendung |
| SE9901387D0 (sv) | 1999-04-19 | 1999-04-19 | Astra Ab | New pharmaceutical foromaulations |
| US6287609B1 (en) | 1999-06-09 | 2001-09-11 | Wisconsin Alumni Research Foundation | Unfermented gel fraction from psyllium seed husks |
| CA2400021A1 (en) | 2000-02-18 | 2001-08-23 | Merck & Co., Inc. | Aryloxyacetic acids for diabetes and lipid disorders |
| SE0000772D0 (sv) | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | Chemical compounds |
| US20020061888A1 (en) | 2000-03-10 | 2002-05-23 | Keller Bradley T. | Combination therapy for the prophylaxis and treatment of hyperlipidemic conditions and disorders |
| US6794544B2 (en) | 2000-03-10 | 2004-09-21 | Pharmacia Corporation | Method for the preparation of tetrahydrobenzothiepines |
| TWI241195B (en) | 2000-04-10 | 2005-10-11 | Shionogi & Co | Preventive agent for bile acidic diarrhea |
| US20020183307A1 (en) | 2000-07-26 | 2002-12-05 | Tremont Samuel J. | Novel 1,4-benzothiazephine and 1,5-benzothiazepine compounds as inhibitors of apical sodium co-dependent bile acid transport and taurocholate uptake |
| AU2001289699B2 (en) | 2000-07-28 | 2006-06-01 | Cheplapharm Arzneimittel Gmbh | New pharmaceutical composition |
| FR2812886B1 (fr) | 2000-08-08 | 2002-11-08 | Assist Publ Hopitaux De Paris | Depistage d'un nouveau syndrome hepatique et ses applications |
| SE0003766D0 (sv) | 2000-10-18 | 2000-10-18 | Astrazeneca Ab | Novel formulation |
| EG26979A (en) | 2000-12-21 | 2015-03-01 | Astrazeneca Ab | Chemical compounds |
| WO2002053548A1 (fr) | 2000-12-27 | 2002-07-11 | Banyu Pharmaceutical Co.,Ltd. | Derives de la benzothiazepine |
| US6506921B1 (en) | 2001-06-29 | 2003-01-14 | Virginia Tech Intellectual Properties, Inc. | Amine compounds and curable compositions derived therefrom |
| GB0121337D0 (en) | 2001-09-04 | 2001-10-24 | Astrazeneca Ab | Chemical compounds |
| GB0121621D0 (en) | 2001-09-07 | 2001-10-31 | Astrazeneca Ab | Chemical compounds |
| GB0121622D0 (en) | 2001-09-07 | 2001-10-31 | Astrazeneca Ab | Chemical compounds |
| MXPA04002179A (es) | 2001-09-08 | 2004-06-29 | Astrazeneca Ab | Derivados de benzotiazepina y benzotiadiazepina con actividad inhibidora de transporte del acido ileal biliar (ibat) para tratar hiperlipidemia. |
| MXPA04002455A (es) | 2001-09-12 | 2004-06-29 | Searle Llc | Metodo para la preparacion de tetrahidrobenzotiepinas cristalinas. |
| GB0314079D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| GB0229931D0 (en) | 2002-12-21 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| SE0104334D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| JP2005518408A (ja) | 2001-12-29 | 2005-06-23 | ノボ ノルディスク アクティーゼルスカブ | 異常脂肪血症を治療するための、ｇｌｐ−１化合物と他の薬物との組み合わせ使用 |
| GB0201850D0 (en) | 2002-01-26 | 2002-03-13 | Astrazeneca Ab | Therapeutic treatment |
| GB0209467D0 (en) | 2002-04-25 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| GB0213669D0 (en) | 2002-06-14 | 2002-07-24 | Astrazeneca Ab | Chemical compounds |
| GB0216321D0 (en) | 2002-07-13 | 2002-08-21 | Astrazeneca Ab | Therapeutic treatment |
| CA2497345C (en) | 2002-08-28 | 2008-10-14 | Asahi Kasei Pharma Corporation | Novel quaternary ammonium compounds |
| US7312208B2 (en) | 2002-08-28 | 2007-12-25 | Asahi Kasei Pharma Corporation | Quaternary ammonium compounds |
| GB0304194D0 (en) | 2003-02-25 | 2003-03-26 | Astrazeneca Ab | Chemical compounds |
| US20060210633A1 (en) | 2003-04-03 | 2006-09-21 | Sun Pharmaceutical Industries Limited | Programmed drug delivery system |
| GB0307918D0 (en) | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| KR20070026392A (ko) | 2004-02-27 | 2007-03-08 | 아사히 가세이 파마 가부시키가이샤 | 신규 벤조티아제핀 및 벤조티에핀 화합물 |
| WO2005082414A2 (en) | 2004-03-02 | 2005-09-09 | Astellas Pharma Inc. | Concomitant drugs of a sulfonamide and another therapeutic agent |
| EP1593671A1 (en) | 2004-03-05 | 2005-11-09 | Graffinity Pharmaceuticals AG | DPP-IV inhibitors |
| TWI415635B (zh) | 2004-05-28 | 2013-11-21 | 必治妥施貴寶公司 | 加衣錠片調製物及製備彼之方法 |
| JP4896480B2 (ja) | 2004-10-01 | 2012-03-14 | 第一三共ヘルスケア株式会社 | 陰イオン交換樹脂の粒子状組成物 |
| WO2006121861A2 (en) | 2005-05-05 | 2006-11-16 | Microbia, Inc. | Biphenylazetidinone cholesterol absorption inhibitors |
| DE102005033099A1 (de) | 2005-07-15 | 2007-01-18 | Sanofi-Aventis Deutschland Gmbh | Neues 1,4-Benzothiazepin-1,1-Dioxidderivat mit verbesserten Eigenschaften, Verfahren zu dessen Herstellung, diese Verbindung enthaltende Arzneimittel und dessen Verwendung |
| DE102005033100B3 (de) | 2005-07-15 | 2007-01-25 | Sanofi-Aventis Deutschland Gmbh | Neues 1,4-Benzothiazepin-1,1-Dioxidderivat mit verbesserten Eigenschaften, diese Verbindung enthaltene Arzneimittel und Verfahren zu deren Herstellung |
| KR101368525B1 (ko) | 2005-09-20 | 2014-03-06 | 노파르티스 아게 | 저혈당 증상을 저하시키기 위한 ｄｐｐ-ⅳ 억제제의 용도 |
| AU2007238896A1 (en) | 2006-04-10 | 2007-10-25 | Merck Sharp & Dohme Corp. | CGRP antagonist salt |
| GB0607534D0 (en) | 2006-04-13 | 2006-05-24 | Univ London Pharmacy | Colonic drug delivery formulation |
| DE102006053637B4 (de) | 2006-11-14 | 2011-06-30 | Sanofi-Aventis Deutschland GmbH, 65929 | Neue mit Fluor substituierte 1,4-Benzothiepin-1,1-Dioxidderivate, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| ATE493992T1 (de) | 2006-11-14 | 2011-01-15 | Sanofi Aventis Deutschland | Neue 1,4-benzothiepin-1,1-dioxidderivate mit verbesserten eigenschaften, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| DE102006053635B4 (de) | 2006-11-14 | 2011-06-30 | Sanofi-Aventis Deutschland GmbH, 65929 | Neue mit Benzylresten substituierte 1,4-Benzothiepin-1,1-Dioxidderivate, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| EP2200588B1 (en) | 2007-09-25 | 2019-03-20 | Solubest Ltd. | Compositions comprising lipophilic active compounds and method for their preparation |
| US20110159087A1 (en) | 2008-09-02 | 2011-06-30 | Dhananjay Govind Sathe | Crosslinked Polymers |
| WO2010062861A2 (en) | 2008-11-26 | 2010-06-03 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of obesity and diabetes |
| JO3131B1 (ar) | 2010-04-27 | 2017-09-20 | Glaxosmithkline Llc | مركبات كيميائية |
| EP4137137A1 (en) | 2010-05-26 | 2023-02-22 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| JP5889321B2 (ja) | 2010-11-04 | 2016-03-22 | アルビレオ アクチエボラグ | 肝疾患の処置用のｉｂａｔ阻害剤 |
| BR112013011249A2 (pt) | 2010-11-08 | 2017-11-14 | Albireo Ab | inibidores de ibat para tratamento de distúrbios metabólicos e condições relacionadas |
| WO2012064267A1 (en) | 2010-11-08 | 2012-05-18 | Albireo Ab | A pharmaceutical combination comprising an ibat inhibitor and a bile acid binder |
| US20120114588A1 (en) | 2010-11-08 | 2012-05-10 | Albireo Ab | Ibat inhibitors for treatment of metabolic disorders and related conditions |
| MX363161B (es) | 2011-10-28 | 2019-03-13 | Lumena Pharmaceuticals Inc | Inhibidores de la recirculación de ácidos biliares para el tratamiento de hipercolemia y enfermedad hepática colestásica. |
| WO2013063512A1 (en) | 2011-10-28 | 2013-05-02 | Lumena Pharmaceuticals, Inc | Bile acid recycling inhibitors for treatment of pediatric cholestatic liver diseases |
| JO3301B1 (ar) * | 2013-04-26 | 2018-09-16 | Albireo Ab | تعديلات بلورية على إيلوبيكسيبات |
| EP3154523B1 (en) | 2014-06-16 | 2018-11-21 | Valpharma International S.P.A. | Formulation for oral administration containing mesalazine |
| JP6751020B2 (ja) | 2014-06-25 | 2020-09-02 | Ｅａファーマ株式会社 | 固形製剤及びその着色防止又は着色低減方法 |
| KR102296314B1 (ko) | 2014-06-25 | 2021-09-01 | 이에이 파마 가부시키가이샤 | 고형 제제 및 그의 안정화 방법 |
| US9684018B2 (en) | 2014-11-19 | 2017-06-20 | Texas Instruments Incorporated | Current sense circuit that operates over a wide range of currents |
| US10441604B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Cholestyramine pellets and methods for preparation thereof |
| US10786529B2 (en) | 2016-02-09 | 2020-09-29 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10441605B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Oral cholestyramine formulation and use thereof |
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2014
- 2014-10-24 EP EP14190290.8A patent/EP3012252A1/en not_active Withdrawn
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2015
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- 2015-10-23 WO PCT/EP2015/074573 patent/WO2016062848A1/en not_active Ceased
- 2015-10-23 EP EP15784385.5A patent/EP3209649B1/en active Active
- 2015-10-23 JP JP2017519487A patent/JP6700263B2/ja active Active
- 2015-10-23 CN CN201580055918.9A patent/CN107001301A/zh active Pending
- 2015-10-23 CA CA2959760A patent/CA2959760C/en active Active
- 2015-10-23 US US15/519,808 patent/US10183920B2/en active Active
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- 2015-10-23 AU AU2015334883A patent/AU2015334883B2/en active Active
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- 2015-10-23 CN CN202011101686.5A patent/CN112375044A/zh active Pending
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2018
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| Publication number | Publication date |
|---|---|
| EP3209649A1 (en) | 2017-08-30 |
| CA2959760A1 (en) | 2016-04-28 |
| EP3012252A1 (en) | 2016-04-27 |
| US20170240516A1 (en) | 2017-08-24 |
| KR102498539B1 (ko) | 2023-02-09 |
| CN107001301A (zh) | 2017-08-01 |
| EP3904344A1 (en) | 2021-11-03 |
| WO2016062848A1 (en) | 2016-04-28 |
| RU2017114109A3 (enExample) | 2019-04-30 |
| RU2017114109A (ru) | 2018-11-26 |
| AU2015334883B2 (en) | 2019-10-24 |
| KR20170072908A (ko) | 2017-06-27 |
| EP3209649B1 (en) | 2021-04-21 |
| US10519120B2 (en) | 2019-12-31 |
| AU2015334883A1 (en) | 2017-03-23 |
| ES2874573T3 (es) | 2021-11-05 |
| JP6700263B2 (ja) | 2020-05-27 |
| CN112375044A (zh) | 2021-02-19 |
| JP2017537061A (ja) | 2017-12-14 |
| US10183920B2 (en) | 2019-01-22 |
| US20190177286A1 (en) | 2019-06-13 |
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