SK280819B6 - Deriváty kyseliny žlčovej, liečivo s ich obsahom a ich použitie - Google Patents
Deriváty kyseliny žlčovej, liečivo s ich obsahom a ich použitie Download PDFInfo
- Publication number
- SK280819B6 SK280819B6 SK585-93A SK58593A SK280819B6 SK 280819 B6 SK280819 B6 SK 280819B6 SK 58593 A SK58593 A SK 58593A SK 280819 B6 SK280819 B6 SK 280819B6
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- carbon atoms
- acid
- alkyl
- mmol
- Prior art date
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- 239000003814 drug Substances 0.000 title claims abstract description 13
- 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 class C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- -1 alkaline earth metal salts Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 238000001819 mass spectrum Methods 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 238000005949 ozonolysis reaction Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000000055 hyoplipidemic effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 30
- 238000010265 fast atom bombardment Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000003613 bile acid Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000012528 membrane Substances 0.000 description 8
- 230000032258 transport Effects 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- 210000000170 cell membrane Anatomy 0.000 description 7
- 238000011534 incubation Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 6
- 229930195725 Mannitol Natural products 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000000594 mannitol Substances 0.000 description 6
- 235000010355 mannitol Nutrition 0.000 description 6
- 210000000813 small intestine Anatomy 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- WBWWGRHZICKQGZ-HZAMXZRMSA-N taurocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 WBWWGRHZICKQGZ-HZAMXZRMSA-N 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
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- 239000000706 filtrate Substances 0.000 description 4
- 239000013049 sediment Substances 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000008280 blood Substances 0.000 description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
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- BHTRKEVKTKCXOH-BJLOMENOSA-N taurochenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 BHTRKEVKTKCXOH-BJLOMENOSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
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- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
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- ODURFHDFZAVGHC-KTKRTIGZSA-N (z)-2-aminooctadec-9-enoic acid Chemical class CCCCCCCC\C=C/CCCCCCC(N)C(O)=O ODURFHDFZAVGHC-KTKRTIGZSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
-
- 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
-
- 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
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Train Traffic Observation, Control, And Security (AREA)
- Motorcycle And Bicycle Frame (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4219274 | 1992-06-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK58593A3 SK58593A3 (en) | 1994-03-09 |
| SK280819B6 true SK280819B6 (sk) | 2000-08-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK585-93A SK280819B6 (sk) | 1992-06-12 | 1993-06-10 | Deriváty kyseliny žlčovej, liečivo s ich obsahom a ich použitie |
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| US (1) | US5428182A (cs) |
| EP (1) | EP0573848B1 (cs) |
| JP (1) | JP3403218B2 (cs) |
| KR (1) | KR100319562B1 (cs) |
| AT (1) | ATE160783T1 (cs) |
| AU (1) | AU663592B2 (cs) |
| CA (1) | CA2098256C (cs) |
| CY (1) | CY2117B1 (cs) |
| CZ (1) | CZ285104B6 (cs) |
| DE (1) | DE59307759D1 (cs) |
| DK (1) | DK0573848T3 (cs) |
| ES (1) | ES2111092T3 (cs) |
| FI (1) | FI106801B (cs) |
| GR (1) | GR3025799T3 (cs) |
| HU (1) | HU216636B (cs) |
| IL (1) | IL105980A (cs) |
| NO (1) | NO304653B1 (cs) |
| NZ (1) | NZ247827A (cs) |
| SK (1) | SK280819B6 (cs) |
| TW (1) | TW228004B (cs) |
| ZA (1) | ZA934150B (cs) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0624593A3 (de) * | 1993-05-08 | 1995-06-07 | Hoechst Ag | Gallensäurederivate, Verfahren zu ihrer Herstellung und Verwendung dieser Verbindungen als Arzneimittel. |
| DE4432708A1 (de) * | 1994-09-14 | 1996-03-21 | Hoechst Ag | Modifizierte Gallensäuren, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5840879A (en) * | 1996-12-06 | 1998-11-24 | Wang; Edge R. | Reagents and solid supports for improved synthesis and labeling of polynucleotides |
| GB2355009A (en) | 1999-07-30 | 2001-04-11 | Univ Glasgow | Peptides conjugated to bile acids/salts |
| GB0307918D0 (en) | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| US7674778B2 (en) | 2004-04-30 | 2010-03-09 | Alnylam Pharmaceuticals | Oligonucleotides comprising a conjugate group linked through a C5-modified pyrimidine |
| ES2318922B1 (es) * | 2005-05-30 | 2010-02-12 | Universidade De Santiago De Compostela | Nuevos dimeros derivados de acidos biliares funcionalizados en la posicion 3 del anillo a. metodo para la sintesis y aplicaciones. |
| KR100800312B1 (ko) * | 2006-01-25 | 2008-02-04 | (주)테크윙 | 테스트핸들러 및 테스트핸들러의 로딩방법 |
| CN101078006B (zh) | 2006-05-26 | 2012-06-06 | 上海凯信生物科技有限公司 | 一株高产四甲基吡嗪的短小芽孢杆菌 |
| EP2995317A1 (en) | 2010-05-26 | 2016-03-16 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| KR101890959B1 (ko) | 2010-11-04 | 2018-08-22 | 알비레오 에이비 | 간질환 치료를 위한 ｉｂａｔ 억제제 |
| CN103228270B (zh) | 2010-11-08 | 2016-02-10 | 阿尔比里奥公司 | 含ibat抑制剂和胆汁酸结合剂的药物组合 |
| MX369466B (es) | 2011-10-28 | 2019-11-08 | Lumena Pharmaceuticals Inc | Inhibidores de la recirculación de ácidos biliares para el tratamiento de enfermedades hepáticas colestásicas pediátricas. |
| KR20190135545A (ko) | 2011-10-28 | 2019-12-06 | 루메나 파마수티컬즈, 인코포레이티드 | 고담혈증 및 담즙 정체성 간 질환 치료용 담즙산 재순환 억제제 |
| JP2016514684A (ja) | 2013-03-15 | 2016-05-23 | ルメナ ファーマシューティカルズ エルエルシー | 原発性硬化性胆管炎および炎症性腸疾患の処置のための胆汁酸再循環阻害剤 |
| AU2014229050A1 (en) | 2013-03-15 | 2015-10-22 | Lumena Pharmaceuticals Llc | Bile acid recycling inhibitors for treatment of Barrett's esophagus and gastroesophageal reflux disease |
| JO3301B1 (ar) | 2013-04-26 | 2018-09-16 | Albireo Ab | تعديلات بلورية على إيلوبيكسيبات |
| KR102560954B1 (ko) | 2014-06-25 | 2023-07-31 | 이에이 파마 가부시키가이샤 | 고형 제제 및 그의 착색 방지 또는 착색 감소 방법 |
| EP3012252A1 (en) | 2014-10-24 | 2016-04-27 | Ferring BV | Crystal modifications of elobixibat |
| JP6954926B2 (ja) | 2016-02-09 | 2021-10-27 | アルビレオ・アクチボラグ | 経口コレスチラミン製剤及びその使用 |
| CA3011619C (en) | 2016-02-09 | 2024-01-02 | Albireo Ab | Oral cholestyramine formulation and use 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 |
| US10441604B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Cholestyramine pellets and methods for preparation thereof |
| CA3071182A1 (en) | 2017-08-09 | 2019-02-14 | Albireo Ab | Cholestyramine pellets, oral cholestyramine formulations and use thereof |
| WO2019032026A1 (en) | 2017-08-09 | 2019-02-14 | Albireo Ab | CHOLESTYRAMINE GRANULES, ORAL FORMULATIONS OF CHOLESTYRAMINE AND THEIR USE |
| US10793534B2 (en) | 2018-06-05 | 2020-10-06 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| TW202015699A (zh) | 2018-06-05 | 2020-05-01 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽汁酸調節劑之用途 |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| JP7504032B2 (ja) | 2018-06-20 | 2024-06-21 | アルビレオ・アクチボラグ | オデビキシバットの結晶変態 |
| 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 |
| US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| SG11202108566VA (en) | 2019-02-06 | 2021-09-29 | Albireo Ab | Benzothiadiazepine 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 |
| CA3127408A1 (en) | 2019-02-06 | 2020-08-13 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| US10975045B2 (en) | 2019-02-06 | 2021-04-13 | Aibireo AB | Benzothiazepine compounds and their use as bile acid modulators |
| JP7562546B2 (ja) | 2019-02-12 | 2024-10-07 | ミルム ファーマシューティカルズ インコーポレイテッド | 胆汁うっ滞性肝疾患を有する小児対象の成長を増加させる方法 |
| TWI871392B (zh) | 2019-12-04 | 2025-02-01 | 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 |
| WO2021110883A1 (en) | 2019-12-04 | 2021-06-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| WO2021110884A1 (en) | 2019-12-04 | 2021-06-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| AR120674A1 (es) | 2019-12-04 | 2022-03-09 | Albireo Ab | Compuestos de benzotiazepina y su uso como ácido biliar |
| WO2021110885A1 (en) | 2019-12-04 | 2021-06-10 | Albireo Ab | Benzothiadiazepine compounds and their use as bile acid modulators |
| BR112022010505A2 (pt) | 2019-12-04 | 2022-09-06 | Albireo Ab | Compostos de benzotia(di)azepina e seu uso como moduladores do ácido biliar |
| CN114761080B (zh) | 2019-12-04 | 2024-07-23 | 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 |
| JP7665620B2 (ja) | 2019-12-04 | 2025-04-21 | アルビレオ・アクチボラグ | ベンゾチアジアゼピン化合物及び胆汁酸モジュレータとしてのそれらの使用 |
| CN114786772B (zh) | 2019-12-04 | 2024-04-09 | 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 |
| US11014898B1 (en) | 2020-12-04 | 2021-05-25 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| WO2022029101A1 (en) | 2020-08-03 | 2022-02-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| CA3186857A1 (en) | 2020-08-03 | 2022-02-10 | Per-Goran Gillberg | Benzothia(di)azepine compounds and their use as bile acid modulators |
| 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 |
| BR112023010799A2 (pt) | 2020-12-04 | 2023-10-03 | Albireo Ab | Compostos de benzotia(di)azepina e seus usos como moduladores de ácidos biliares |
| 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 |
| US20230398125A1 (en) | 2022-06-09 | 2023-12-14 | Albireo Ab | Treating hepatitis |
| AU2023304672A1 (en) | 2022-07-05 | 2025-01-02 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| KR20250110930A (ko) | 2022-12-09 | 2025-07-21 | 알비레오 에이비 | 신장 질병 치료용 asbt 억제제 |
| WO2025146508A1 (en) | 2024-01-05 | 2025-07-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| WO2025146507A1 (en) | 2024-01-05 | 2025-07-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2931817A (en) * | 1956-05-31 | 1960-04-05 | Monsanto Chemicals | Steroid sulfite ester polymers |
| DE1768345B2 (de) * | 1968-05-03 | 1976-12-02 | Hoechst Ag, 6000 Frankfurt | Dimere steroid-21-alkylcarbonate und verfahren zu ihrer herstellung |
| US3916002A (en) * | 1973-12-17 | 1975-10-28 | Taubert Hans Dieter | Oligomeric steroid esters, process for their production, and therapeutic compositions containing the same |
| NL7415669A (nl) * | 1974-12-02 | 1976-06-04 | Akzo Nv | Werkwijze ter bereiding van een nieuwe ester van 19-nor-testosteron. |
| EP0489423B1 (de) * | 1990-12-06 | 1996-11-06 | Hoechst Aktiengesellschaft | Gallensäurederivate, Verfahren zu ihrer Herstellung und Verwendung dieser Verbindung als Arzneimittel |
| EP0548793A3 (en) * | 1991-12-20 | 1995-11-02 | Hoechst Ag | Ethylenic-unsaturated bile acid derivatives, process for their production and preliminary processes therefor |
| TW289021B (cs) * | 1993-05-08 | 1996-10-21 | Hoechst Ag |
-
1993
- 1993-05-27 EP EP93108559A patent/EP0573848B1/de not_active Expired - Lifetime
- 1993-05-27 AT AT93108559T patent/ATE160783T1/de not_active IP Right Cessation
- 1993-05-27 DE DE59307759T patent/DE59307759D1/de not_active Expired - Lifetime
- 1993-05-27 DK DK93108559T patent/DK0573848T3/da active
- 1993-05-27 ES ES93108559T patent/ES2111092T3/es not_active Expired - Lifetime
- 1993-06-05 TW TW082104487A patent/TW228004B/zh active
- 1993-06-09 NZ NZ247827A patent/NZ247827A/en unknown
- 1993-06-10 US US08/074,753 patent/US5428182A/en not_active Expired - Lifetime
- 1993-06-10 IL IL105980A patent/IL105980A/xx not_active IP Right Cessation
- 1993-06-10 CZ CZ931134A patent/CZ285104B6/cs not_active IP Right Cessation
- 1993-06-10 SK SK585-93A patent/SK280819B6/sk unknown
- 1993-06-10 FI FI932659A patent/FI106801B/fi active
- 1993-06-11 ZA ZA934150A patent/ZA934150B/xx unknown
- 1993-06-11 KR KR1019930010579A patent/KR100319562B1/ko not_active Expired - Fee Related
- 1993-06-11 HU HU9301716A patent/HU216636B/hu not_active IP Right Cessation
- 1993-06-11 AU AU40180/93A patent/AU663592B2/en not_active Ceased
- 1993-06-11 NO NO931379A patent/NO304653B1/no unknown
- 1993-06-11 JP JP14037593A patent/JP3403218B2/ja not_active Expired - Lifetime
- 1993-06-11 CA CA002098256A patent/CA2098256C/en not_active Expired - Lifetime
-
1997
- 1997-12-30 GR GR970403445T patent/GR3025799T3/el unknown
-
1998
- 1998-09-29 CY CY9800035A patent/CY2117B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU663592B2 (en) | 1995-10-12 |
| FI932659L (fi) | 1993-12-13 |
| HUT64772A (en) | 1994-02-28 |
| FI932659A0 (fi) | 1993-06-10 |
| DE59307759D1 (de) | 1998-01-15 |
| CA2098256A1 (en) | 1993-12-13 |
| KR100319562B1 (ko) | 2002-05-13 |
| JP3403218B2 (ja) | 2003-05-06 |
| EP0573848B1 (de) | 1997-12-03 |
| CZ113493A3 (en) | 1994-01-19 |
| IL105980A0 (en) | 1993-10-20 |
| CY2117B1 (en) | 2002-04-26 |
| EP0573848A3 (de) | 1995-06-07 |
| FI106801B (fi) | 2001-04-12 |
| HU9301716D0 (en) | 1993-09-28 |
| GR3025799T3 (en) | 1998-03-31 |
| JPH0687884A (ja) | 1994-03-29 |
| NO304653B1 (no) | 1999-01-25 |
| SK58593A3 (en) | 1994-03-09 |
| DK0573848T3 (da) | 1998-08-10 |
| ZA934150B (en) | 1994-01-13 |
| CA2098256C (en) | 2004-08-24 |
| HU216636B (hu) | 1999-07-28 |
| ATE160783T1 (de) | 1997-12-15 |
| ES2111092T3 (es) | 1998-03-01 |
| NO932159L (no) | 1993-12-13 |
| IL105980A (en) | 1997-11-20 |
| US5428182A (en) | 1995-06-27 |
| AU4018093A (en) | 1993-12-16 |
| EP0573848A2 (de) | 1993-12-15 |
| CZ285104B6 (cs) | 1999-05-12 |
| NZ247827A (en) | 1995-08-28 |
| NO932159D0 (no) | 1993-06-11 |
| TW228004B (cs) | 1994-08-11 |
| KR940005652A (ko) | 1994-03-22 |
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