CA2233925A1 - Propanolamine derivatives, processes for their preparation, pharmaceuticals comprising these compounds, and their use - Google Patents
Propanolamine derivatives, processes for their preparation, pharmaceuticals comprising these compounds, and their use Download PDFInfo
- Publication number
- CA2233925A1 CA2233925A1 CA002233925A CA2233925A CA2233925A1 CA 2233925 A1 CA2233925 A1 CA 2233925A1 CA 002233925 A CA002233925 A CA 002233925A CA 2233925 A CA2233925 A CA 2233925A CA 2233925 A1 CA2233925 A1 CA 2233925A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- compound
- fluorine
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 68
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 150000003152 propanolamines Chemical class 0.000 title claims abstract description 8
- 239000003814 drug Substances 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 11
- 230000000055 hyoplipidemic effect Effects 0.000 claims abstract description 4
- -1 keto compound Chemical class 0.000 claims description 25
- 239000011737 fluorine Substances 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000002466 imines Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 230000037356 lipid metabolism Effects 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 229930194542 Keto Natural products 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 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 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000012528 membrane Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 210000000110 microvilli Anatomy 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000011534 incubation Methods 0.000 description 8
- 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 7
- 229930195725 Mannitol Natural products 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000000594 mannitol Substances 0.000 description 7
- 235000010355 mannitol Nutrition 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 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 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
- 239000007995 HEPES buffer Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
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- 239000012074 organic phase Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 210000000813 small intestine Anatomy 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
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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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19713865.9 | 1997-04-04 | ||
| DE19713865 | 1997-04-04 | ||
| DE1998102530 DE19802530A1 (de) | 1998-01-26 | 1998-01-26 | Propanolaminderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| DE19802530.0 | 1998-01-26 |
Publications (1)
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|---|---|
| CA2233925A1 true CA2233925A1 (en) | 1998-10-04 |
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| CA002233925A Abandoned CA2233925A1 (en) | 1997-04-04 | 1998-04-03 | Propanolamine derivatives, processes for their preparation, pharmaceuticals comprising these compounds, and their use |
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|---|---|
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| EP (1) | EP0869121B1 (enExample) |
| JP (1) | JP4234805B2 (enExample) |
| KR (1) | KR19980081055A (enExample) |
| CN (1) | CN1185217C (enExample) |
| AR (1) | AR011210A1 (enExample) |
| AT (1) | ATE268758T1 (enExample) |
| AU (1) | AU730228B2 (enExample) |
| BR (1) | BR9801150A (enExample) |
| CA (1) | CA2233925A1 (enExample) |
| CZ (1) | CZ293758B6 (enExample) |
| DE (1) | DE59811528D1 (enExample) |
| DK (1) | DK0869121T3 (enExample) |
| ES (1) | ES2223091T3 (enExample) |
| HU (1) | HUP9800781A3 (enExample) |
| ID (1) | ID20137A (enExample) |
| IL (1) | IL123927A (enExample) |
| MY (1) | MY114944A (enExample) |
| NZ (1) | NZ330110A (enExample) |
| PL (1) | PL325699A1 (enExample) |
| PT (1) | PT869121E (enExample) |
| RU (1) | RU2198876C2 (enExample) |
| TR (1) | TR199800608A3 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19845402B4 (de) | 1998-10-02 | 2005-04-07 | Aventis Pharma Deutschland Gmbh | Mit Heterocyclen substituierte Propanolaminderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| US6417185B1 (en) | 1998-06-19 | 2002-07-09 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| US7045519B2 (en) | 1998-06-19 | 2006-05-16 | Chiron Corporation | Inhibitors of glycogen synthase kinase 3 |
| DE19845405C2 (de) | 1998-10-02 | 2000-07-13 | Aventis Pharma Gmbh | Arylsubstituierte Propanolaminderivate und deren Verwendung |
| DE19845406C2 (de) | 1998-10-02 | 2001-10-18 | Aventis Pharma Gmbh | Substituierte 1,3-Diaryl-2-pyridin-2-yl-3-(pyridin-2-ylamino)- propanolderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| DE19845403B4 (de) * | 1998-10-02 | 2005-02-10 | Aventis Pharma Deutschland Gmbh | Mit Gallensäuren verknüpfte Propanolaminderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| HRP20030501A2 (en) | 2000-12-21 | 2005-04-30 | Aventis Pharma Deutschland Gmbh | Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use |
| NZ531292A (en) * | 2001-08-22 | 2005-08-26 | Aventis Pharma Gmbh | Combination products of aryl-subsituted propanolamine derivatives with other active ingredients and the use thereof |
| TW200408393A (en) | 2002-10-03 | 2004-06-01 | Ono Pharmaceutical Co | Antagonist of lysophosphatidine acid receptor |
| GB0307918D0 (en) | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| JP4766384B2 (ja) * | 2003-12-19 | 2011-09-07 | 小野薬品工業株式会社 | リゾホスファチジン酸受容体拮抗作用を有する化合物およびその用途 |
| CN1869002A (zh) * | 2005-05-27 | 2006-11-29 | 中国科学院上海药物研究所 | 一类非甾体雄激素受体调节剂、其制备方法和用途 |
| LT2848610T (lt) * | 2006-11-15 | 2017-11-10 | Ym Biosciences Australia Pty Ltd | Kinazės aktyvumo inhibitoriai |
| EP3593802A3 (en) | 2010-05-26 | 2020-03-25 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| KR102051031B1 (ko) | 2011-10-28 | 2019-12-02 | 루메나 파마수티컬즈, 인코포레이티드 | 고담혈증 및 담즙 정체성 간 질환 치료용 담즙산 재순환 억제제 |
| BR112014010223B8 (pt) | 2011-10-28 | 2021-02-23 | Lumena Pharmaceuticals Llc | uso de uma composição compreendendo inibidores de reciclagem de ácido de bílis e forma de dosagem pediátrica |
| KR20160003664A (ko) | 2013-03-15 | 2016-01-11 | 루메나 파마수티컬즈, 인코포레이티드 | 바렛 식도 및 위식도 역류 질환 치료용 담즙산 재순환 억제제 |
| EP2968230A2 (en) | 2013-03-15 | 2016-01-20 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| CN105553262B (zh) * | 2015-08-24 | 2018-02-16 | 苏州瑞铬优电子科技有限公司 | 一种提高dc/dc升压变换器转换效率的方法 |
| CA3129826A1 (en) | 2019-02-12 | 2020-08-20 | Mirum Pharmaceuticals, Inc. | Methods for treating cholestasis |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI892341L (fi) * | 1988-06-10 | 1989-12-11 | Hoffmann La Roche | Propanolaminderivat. |
| NZ240846A (en) * | 1990-12-06 | 1994-04-27 | Hoechst Ag | Dimeric bile acid derivatives; preparatory processes and pharmaceutical compositions |
| DE4040026A1 (de) * | 1990-12-14 | 1992-06-17 | Bayer Ag | Substituierte pyridyl-dihydroxy-heptensaeure und deren salze |
| GB9203347D0 (en) * | 1992-02-17 | 1992-04-01 | Wellcome Found | Hypolipidaemic compounds |
| DE59305012D1 (de) * | 1992-02-22 | 1997-02-20 | Hoechst Ag | 4-Amino-2-ureido-pyrimidin-5-carbonsäureamide, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
-
1998
- 1998-03-24 AT AT98105256T patent/ATE268758T1/de not_active IP Right Cessation
- 1998-03-24 ES ES98105256T patent/ES2223091T3/es not_active Expired - Lifetime
- 1998-03-24 PT PT98105256T patent/PT869121E/pt unknown
- 1998-03-24 DK DK98105256T patent/DK0869121T3/da active
- 1998-03-24 DE DE59811528T patent/DE59811528D1/de not_active Expired - Lifetime
- 1998-03-24 EP EP98105256A patent/EP0869121B1/de not_active Expired - Lifetime
- 1998-04-02 AR ARP980101512A patent/AR011210A1/es unknown
- 1998-04-02 IL IL12392798A patent/IL123927A/xx active IP Right Grant
- 1998-04-02 NZ NZ330110A patent/NZ330110A/xx unknown
- 1998-04-02 ID IDP980494A patent/ID20137A/id unknown
- 1998-04-02 US US09/053,513 patent/US5874451A/en not_active Expired - Lifetime
- 1998-04-02 TR TR1998/00608A patent/TR199800608A3/tr unknown
- 1998-04-03 HU HU9800781A patent/HUP9800781A3/hu unknown
- 1998-04-03 CZ CZ19981025A patent/CZ293758B6/cs not_active IP Right Cessation
- 1998-04-03 PL PL98325699A patent/PL325699A1/xx not_active Application Discontinuation
- 1998-04-03 KR KR1019980011750A patent/KR19980081055A/ko not_active Abandoned
- 1998-04-03 MY MYPI98001488A patent/MY114944A/en unknown
- 1998-04-03 CA CA002233925A patent/CA2233925A1/en not_active Abandoned
- 1998-04-03 JP JP10716198A patent/JP4234805B2/ja not_active Expired - Fee Related
- 1998-04-03 RU RU98106112/04A patent/RU2198876C2/ru not_active IP Right Cessation
- 1998-04-03 AU AU60624/98A patent/AU730228B2/en not_active Ceased
- 1998-04-03 CN CNB981082521A patent/CN1185217C/zh not_active Expired - Fee Related
- 1998-04-06 BR BR9801150A patent/BR9801150A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE268758T1 (de) | 2004-06-15 |
| ID20137A (id) | 1998-10-08 |
| US5874451A (en) | 1999-02-23 |
| HUP9800781A2 (hu) | 1999-06-28 |
| TR199800608A2 (en) | 1998-10-21 |
| PL325699A1 (en) | 1998-10-12 |
| IL123927A (en) | 2001-01-28 |
| AU730228B2 (en) | 2001-03-01 |
| CZ293758B6 (cs) | 2004-07-14 |
| MY114944A (en) | 2003-02-28 |
| CN1199731A (zh) | 1998-11-25 |
| EP0869121A1 (de) | 1998-10-07 |
| JP4234805B2 (ja) | 2009-03-04 |
| CZ102598A3 (cs) | 1998-10-14 |
| EP0869121B1 (de) | 2004-06-09 |
| AR011210A1 (es) | 2000-08-02 |
| AU6062498A (en) | 1998-10-08 |
| BR9801150A (pt) | 2000-03-21 |
| ES2223091T3 (es) | 2005-02-16 |
| CN1185217C (zh) | 2005-01-19 |
| DE59811528D1 (de) | 2004-07-15 |
| HK1015789A1 (en) | 1999-10-22 |
| PT869121E (pt) | 2004-10-29 |
| DK0869121T3 (da) | 2004-09-20 |
| KR19980081055A (ko) | 1998-11-25 |
| TR199800608A3 (tr) | 1998-10-21 |
| NZ330110A (en) | 1999-03-29 |
| HUP9800781A3 (en) | 1999-07-28 |
| HU9800781D0 (en) | 1998-05-28 |
| RU2198876C2 (ru) | 2003-02-20 |
| JPH10287651A (ja) | 1998-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |