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 |
|---|---|---|---|
| EP14190290.8A EP3012252A1 (en) | 2014-10-24 | 2014-10-24 | Crystal modifications of elobixibat |
| EP14190290.8 | 2014-10-24 | ||
| 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 |
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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 (cg-RX-API-DMAC7.html) |
| EP (3) | EP3012252A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6700263B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102498539B1 (cg-RX-API-DMAC7.html) |
| CN (2) | CN107001301A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2015334883B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2959760C (cg-RX-API-DMAC7.html) |
| ES (1) | ES2874573T3 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2017114109A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016062848A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT3023102T (lt) | 2010-11-04 | 2018-09-25 | Albireo Ab | Ibat inhibitoriai, skirti kepenų ligų gydymui |
| KR20220082931A (ko) | 2014-06-25 | 2022-06-17 | 이에이 파마 가부시키가이샤 | 고형 제제 및 그의 착색 방지 또는 착색 감소 방법 |
| 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 |
| CA3071285A1 (en) | 2017-08-09 | 2019-02-14 | 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 |
| KR102740080B1 (ko) * | 2018-03-09 | 2024-12-06 | 엘로빅스 아베 | 엘로빅시바트의 제조 방법 |
| US10793534B2 (en) | 2018-06-05 | 2020-10-06 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| CN112449637B (zh) | 2018-06-05 | 2024-03-19 | 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 |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| PL3810581T3 (pl) | 2018-06-20 | 2025-04-28 | Albireo Ab | Modyfikacje kryształu odewiksibatu |
| US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11549878B2 (en) | 2018-08-09 | 2023-01-10 | Albireo Ab | In vitro method for determining the adsorbing capacity of an insoluble adsorbant |
| US10975045B2 (en) | 2019-02-06 | 2021-04-13 | Aibireo AB | Benzothiazepine compounds and their use as bile acid modulators |
| SMT202300020T1 (it) | 2019-02-06 | 2023-03-17 | Albireo Ab | Composti di benzotiadiazepine e loro uso come modulatori degli acidi biliari |
| US10941127B2 (en) | 2019-02-06 | 2021-03-09 | Albireo Ab | Benzothiadiazepine compounds and their use as bile acid modulators |
| WO2021049311A1 (ja) * | 2019-09-09 | 2021-03-18 | エロビクス・アーベー | １，５－ベンゾチアゼピン化合物を製造するための方法 |
| CR20220315A (es) | 2019-12-04 | 2022-10-26 | Albireo Ab | Compuestos de benzoti(di)azepina y su uso como moduladores del ácido biliar |
| CA3158276A1 (en) | 2019-12-04 | 2021-06-10 | Per-Goran Gillberg | Benzothia(di)azepine compounds and their use as bile acid modulators |
| CA3158181A1 (en) | 2019-12-04 | 2021-06-10 | 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 |
| 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) |
| CA3196488A1 (en) | 2020-11-12 | 2022-05-19 | Albireo Ab | Odevixibat for treating progressive familial intrahepatic cholestasis (pfic) |
| EP4255565A1 (en) | 2020-12-04 | 2023-10-11 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| 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 |
| WO2024027013A1 (zh) * | 2022-08-02 | 2024-02-08 | 上海皓元医药股份有限公司 | 一种依洛西巴特晶型ii及其制备方法 |
| WO2024094841A1 (en) | 2022-11-03 | 2024-05-10 | Albireo Ab | Treating alagille syndrome (algs) |
| 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 |
| DE3066728D1 (en) | 1979-04-30 | 1984-03-29 | Max Planck Gesellschaft | Tyrosine derivatives, process for their production and their use in the synthesis of peptides |
| 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 |
| DE59108326D1 (de) | 1990-12-06 | 1996-12-12 | Hoechst Ag | Gallensäurederivate, Verfahren zu ihrer Herstellung und Verwendung dieser Verbindung als Arzneimittel |
| AU653658B2 (en) | 1991-12-20 | 1994-10-06 | Hoechst Aktiengesellschaft | Polymers and oligomers of bile acid derivatives, process for their preparation and their use as pharmaceuticals |
| 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 | |
| ES2111092T3 (es) | 1992-06-12 | 1998-03-01 | Hoechst Ag | Derivados de acidos biliares, procedimiento para su preparacion y utilizacion de estos compuestos como medicamentos. |
| 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 |
| ZA941003B (en) | 1993-02-15 | 1995-08-14 | Wellcome Found | Hypolipidaemic compounds |
| PT621032E (pt) | 1993-04-23 | 2001-01-31 | Novartis Ag | Dispositivo de distribuicao de libertacao controlada de farmaco |
| TW289757B (cg-RX-API-DMAC7.html) | 1993-05-08 | 1996-11-01 | Hoechst Ag | |
| EP0624593A3 (de) | 1993-05-08 | 1995-06-07 | Hoechst Ag | Gallensäurederivate, Verfahren zu ihrer Herstellung und Verwendung dieser Verbindungen als Arzneimittel. |
| TW289021B (cg-RX-API-DMAC7.html) | 1993-05-08 | 1996-10-21 | Hoechst Ag | |
| TW289020B (cg-RX-API-DMAC7.html) | 1993-05-08 | 1996-10-21 | Hoechst Sktiengesellschaft | |
| ZA956647B (en) | 1994-08-10 | 1997-02-10 | Wellcome Found | Hypolipidaemic compounds. |
| 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 |
| 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 |
| AU700557B2 (en) | 1994-09-13 | 1999-01-07 | Monsanto Company | Novel benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| 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 |
| 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 |
| AU724620B2 (en) | 1996-01-16 | 2000-09-28 | Sokol, Ronald J Dr. | Use of antioxidant agents to treat cholestatic liver disease |
| HUP9903047A3 (en) | 1996-03-11 | 2002-12-28 | G D Searle & Co Chicago | Novel benzothiazepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| EP0912861B1 (de) | 1996-07-24 | 2000-11-29 | 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 |
| SK125099A3 (en) | 1997-03-11 | 2001-02-12 | Searle & Co | Combination of ileal bile acid transport inhibiting benzothiepines and hmg co-a reductase inhibitors |
| EP0864582B1 (en) | 1997-03-14 | 2003-06-04 | Aventis Pharma Deutschland GmbH | Hypolipidemic 1,4-benzothiazepine-1,-dioxides |
| 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 |
| ES2195428T3 (es) | 1997-12-19 | 2003-12-01 | Searle & Co | Metodo para preparar oxidos de tetrahidrobenzotiepina enriquecidos enantiometricamente. |
| GB9800428D0 (en) | 1998-01-10 | 1998-03-04 | Glaxo Group Ltd | Chemical compounds |
| JP2002513013A (ja) | 1998-04-24 | 2002-05-08 | 藤沢薬品工業株式会社 | グアニジン誘導体 |
| 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 |
| AU5194999A (en) | 1998-08-07 | 2000-02-28 | Takeda Chemical Industries Ltd. | Benzothiepin derivatives, process for the preparation of the same and uses thereof |
| ES2200587T3 (es) | 1998-12-23 | 2004-03-01 | G.D. Searle Llc | Combinaciones de inhibidors del transporte de acidos biliares del ileon e inhibidores de la proteina de transferencia de colesteril ester para indicaciones cardiovasculares. |
| CZ20012344A3 (cs) | 1998-12-23 | 2002-01-16 | G. D. Searle Llc | Kombinace pro kardiovaskulární indikace |
| DK1140189T3 (da) | 1998-12-23 | 2003-09-15 | Searle Llc | Kombinationer af ileal galdesyre-transportinhibitorer og fibrinsyrederivater til cardiovaskulære indikationer |
| BR9916567A (pt) | 1998-12-23 | 2001-12-11 | Searle Llc | Combinações de inibidores do transporte ácido dabile ileal e derivados do ácido nicotìnico paraindicações cardiovasculares |
| MXPA01006470A (es) | 1998-12-23 | 2003-06-06 | Searle Llc | Combinaciones de inhibidores de transporte de acido biliar ileal y agentes de secuentro de acido biliar para indicaciones cardiovasculares. |
| CA2362147A1 (en) | 1999-02-12 | 2000-08-17 | Steve A. Kolodziej | 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 |
| AU784722B2 (en) | 2000-02-18 | 2006-06-01 | 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 |
| US6586434B2 (en) | 2000-03-10 | 2003-07-01 | G.D. Searle, Llc | 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 |
| JP4265911B2 (ja) | 2000-07-28 | 2009-05-20 | エフ．ホフマン−ラ ロシュ アーゲー | 新規医薬組成物 |
| 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 |
| MY131995A (en) | 2001-09-08 | 2007-09-28 | Astrazeneca Ab | Benzothiazepine and benzothiadiazepine derivatives with illeal bile acid transport (ibat) inhibitory activity for the treatment hyperlipidaemia |
| WO2003022804A2 (en) | 2001-09-12 | 2003-03-20 | G.D. Searle Llc | Method for the preparation of crystalline tetrahydrobenzothiepines |
| GB0314079D0 (en) | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| SE0104334D0 (sv) | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0229931D0 (en) | 2002-12-21 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| WO2003059378A2 (en) | 2001-12-29 | 2003-07-24 | Novo Nordisk A/S | Combined use of a glp-1 compound and another drug for treating dyslipidemia |
| 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 |
| US7312208B2 (en) | 2002-08-28 | 2007-12-25 | Asahi Kasei Pharma Corporation | Quaternary ammonium compounds |
| WO2004020421A1 (ja) | 2002-08-28 | 2004-03-11 | Asahi Kasei Pharma Corporation | 新規な４級アンモニウム化合物 |
| GB0304194D0 (en) | 2003-02-25 | 2003-03-26 | Astrazeneca Ab | Chemical compounds |
| WO2004108067A2 (en) | 2003-04-03 | 2004-12-16 | Sun Pharmaceutical Industries Limited | Programmed drug delivery system |
| GB0307918D0 (en) | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| JP4711953B2 (ja) | 2004-02-27 | 2011-06-29 | 旭化成ファーマ株式会社 | 新規なベンゾチアゼピン及びベンゾチエピン化合物 |
| 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 |
| TWI354569B (en) | 2004-05-28 | 2011-12-21 | Bristol Myers Squibb Co | Coated tablet formulation and method |
| 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 |
| BRPI0616195A2 (pt) | 2005-09-20 | 2011-06-14 | Novartis Ag | uso de um inibidor de dpp-iv para reduzir eventos hipoglicÊmicos |
| US20100286122A1 (en) | 2006-04-10 | 2010-11-11 | Kevin Belyk | CGRP Antagonist Salt |
| GB0607534D0 (en) | 2006-04-13 | 2006-05-24 | Univ London Pharmacy | Colonic drug delivery formulation |
| WO2008058631A1 (de) | 2006-11-14 | 2008-05-22 | Sanofi-Aventis Deutschland Gmbh | Neue 1,4-benzothiepin-1,1-dioxidderivate mit verbesserten eigenschaften, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| 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 |
| 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 |
| PL2200588T3 (pl) | 2007-09-25 | 2019-09-30 | Solubest Ltd. | Kompozycje zawierające lipofilowe związki aktywne i sposób ich wytwarzania |
| KR20110059750A (ko) | 2008-09-02 | 2011-06-03 | 유에스브이 리미티드 | 가교 폴리머 |
| US9339480B2 (en) | 2008-11-26 | 2016-05-17 | 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 |
| ES2552657T3 (es) | 2010-05-26 | 2015-12-01 | Satiogen Pharmaceuticals, Inc. | Inhibidores del reciclado de ácidos biliares y saciógenos para el tratamiento de diabetes, obesidad, y afecciones gastrointestinales inflamatorias |
| LT3023102T (lt) | 2010-11-04 | 2018-09-25 | Albireo Ab | Ibat inhibitoriai, skirti kepenų ligų gydymui |
| MY176863A (en) | 2010-11-08 | 2020-08-24 | Albireo Ab | Ibat inhibitors for treatment of metabolic disorders and related conditions |
| US20120114588A1 (en) | 2010-11-08 | 2012-05-10 | Albireo Ab | Ibat inhibitors for treatment of metabolic disorders and related conditions |
| CA2815698C (en) | 2010-11-08 | 2019-04-30 | Albireo Ab | A pharmaceutical combination comprising an ibat inhibitor and a bile acid binder |
| EA201891154A1 (ru) | 2011-10-28 | 2019-02-28 | ЛУМЕНА ФАРМАСЬЮТИКАЛС ЭлЭлСи | Ингибиторы рециклинга желчных кислот при лечении холестатических заболеваний печени у детей |
| EA038594B1 (ru) | 2011-10-28 | 2021-09-21 | Шайр Хьюман Дженетик Терапис, Инк. | Ингибиторы рециркуляции желчных кислот для лечения гиперхолемии и холестатического заболевания печени |
| JO3301B1 (ar) | 2013-04-26 | 2018-09-16 | Albireo Ab | تعديلات بلورية على إيلوبيكسيبات |
| WO2015193788A1 (en) | 2014-06-16 | 2015-12-23 | Valpharma International S.P.A. | Formulation for oral administration containing mesalazine |
| CA2952405A1 (en) | 2014-06-25 | 2015-12-30 | Ea Pharma Co., Ltd. | Solid formulation and method for stabilizing the same |
| KR20220082931A (ko) | 2014-06-25 | 2022-06-17 | 이에이 파마 가부시키가이샤 | 고형 제제 및 그의 착색 방지 또는 착색 감소 방법 |
| US9684018B2 (en) | 2014-11-19 | 2017-06-20 | Texas Instruments Incorporated | Current sense circuit that operates over a wide range of currents |
| US10441605B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| 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 |
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2014
- 2014-10-24 EP EP14190290.8A patent/EP3012252A1/en not_active Withdrawn
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2015
- 2015-10-23 EP EP15784385.5A patent/EP3209649B1/en active Active
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- 2015-10-23 ES ES15784385T patent/ES2874573T3/es active Active
- 2015-10-23 EP EP21167339.7A patent/EP3904344A1/en not_active Withdrawn
- 2015-10-23 WO PCT/EP2015/074573 patent/WO2016062848A1/en not_active Ceased
- 2015-10-23 KR KR1020177012754A patent/KR102498539B1/ko active Active
- 2015-10-23 CN CN201580055918.9A patent/CN107001301A/zh active Pending
- 2015-10-23 JP JP2017519487A patent/JP6700263B2/ja active Active
- 2015-10-23 RU RU2017114109A patent/RU2017114109A/ru unknown
- 2015-10-23 US US15/519,808 patent/US10183920B2/en active Active
- 2015-10-23 CN CN202011101686.5A patent/CN112375044A/zh active Pending
- 2015-10-23 AU AU2015334883A patent/AU2015334883B2/en active Active
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2018
- 2018-12-27 US US16/234,364 patent/US10519120B2/en active Active
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| Publication number | Publication date |
|---|---|
| US20190177286A1 (en) | 2019-06-13 |
| JP6700263B2 (ja) | 2020-05-27 |
| KR20170072908A (ko) | 2017-06-27 |
| CN112375044A (zh) | 2021-02-19 |
| AU2015334883B2 (en) | 2019-10-24 |
| US10519120B2 (en) | 2019-12-31 |
| US20170240516A1 (en) | 2017-08-24 |
| EP3904344A1 (en) | 2021-11-03 |
| RU2017114109A3 (cg-RX-API-DMAC7.html) | 2019-04-30 |
| EP3012252A1 (en) | 2016-04-27 |
| EP3209649A1 (en) | 2017-08-30 |
| KR102498539B1 (ko) | 2023-02-09 |
| WO2016062848A1 (en) | 2016-04-28 |
| JP2017537061A (ja) | 2017-12-14 |
| ES2874573T3 (es) | 2021-11-05 |
| EP3209649B1 (en) | 2021-04-21 |
| CN107001301A (zh) | 2017-08-01 |
| US10183920B2 (en) | 2019-01-22 |
| AU2015334883A1 (en) | 2017-03-23 |
| CA2959760A1 (en) | 2016-04-28 |
| RU2017114109A (ru) | 2018-11-26 |
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