CA2346083A1 - Propanolamine derivatives substituted with heterocyclic compounds, methods for their production, pharmaceutical compositions containing said compounds and the use thereof - Google Patents
Propanolamine derivatives substituted with heterocyclic compounds, methods for their production, pharmaceutical compositions containing said compounds and the use thereof Download PDFInfo
- Publication number
- CA2346083A1 CA2346083A1 CA002346083A CA2346083A CA2346083A1 CA 2346083 A1 CA2346083 A1 CA 2346083A1 CA 002346083 A CA002346083 A CA 002346083A CA 2346083 A CA2346083 A CA 2346083A CA 2346083 A1 CA2346083 A1 CA 2346083A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- phenyl
- pyridyl
- fluorine
- compound
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 title description 9
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical group NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 title description 2
- 150000002391 heterocyclic compounds Chemical group 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000004076 pyridyl group Chemical group 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 239000011737 fluorine Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- -1 quinoyl Chemical group 0.000 claims description 15
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 10
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 230000037356 lipid metabolism Effects 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 125000005545 phthalimidyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 3
- ZIODHUMVFOUCOM-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,2-benzoxazole Chemical compound C1CCCC2=C1C=NO2 ZIODHUMVFOUCOM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 229910006069 SO3H Inorganic materials 0.000 claims 3
- 150000003152 propanolamines Chemical class 0.000 abstract description 2
- 239000003524 antilipemic agent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- 239000012528 membrane Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 210000000110 microvilli Anatomy 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- 238000009472 formulation Methods 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229930195725 Mannitol Natural products 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000594 mannitol Substances 0.000 description 6
- 235000010355 mannitol Nutrition 0.000 description 6
- 239000002244 precipitate 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-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
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- 239000000047 product Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 239000000470 constituent Substances 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
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- 230000005764 inhibitory process Effects 0.000 description 4
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- 210000000813 small intestine Anatomy 0.000 description 4
- 239000011734 sodium Substances 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
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
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- 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 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
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- 229920000084 Gum arabic Polymers 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- 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
-
- 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
- C07D417/14—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 three or more hetero rings
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- 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
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19845402A DE19845402B4 (de) | 1998-10-02 | 1998-10-02 | Mit Heterocyclen substituierte Propanolaminderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| DE19845402.3 | 1998-10-02 | ||
| PCT/EP1999/006932 WO2000020410A1 (de) | 1998-10-02 | 1999-09-18 | Mit heterocyclen substituierte propanolaminderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2346083A1 true CA2346083A1 (en) | 2000-04-13 |
Family
ID=7883184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002346083A Abandoned CA2346083A1 (en) | 1998-10-02 | 1999-09-18 | Propanolamine derivatives substituted with heterocyclic compounds, methods for their production, pharmaceutical compositions containing said compounds and the use thereof |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6303639B1 (https=) |
| EP (1) | EP1117661B1 (https=) |
| JP (1) | JP2002526539A (https=) |
| KR (1) | KR100611030B1 (https=) |
| CN (1) | CN1150185C (https=) |
| AR (1) | AR021843A1 (https=) |
| AT (1) | ATE267825T1 (https=) |
| AU (1) | AU760412B2 (https=) |
| BR (1) | BR9914266A (https=) |
| CA (1) | CA2346083A1 (https=) |
| DE (2) | DE19845402B4 (https=) |
| DK (1) | DK1117661T3 (https=) |
| ES (1) | ES2219065T3 (https=) |
| HK (1) | HK1040249B (https=) |
| HU (1) | HUP0103893A3 (https=) |
| PL (1) | PL347105A1 (https=) |
| PT (1) | PT1117661E (https=) |
| RU (1) | RU2219176C2 (https=) |
| TR (1) | TR200100895T2 (https=) |
| WO (1) | WO2000020410A1 (https=) |
| ZA (1) | ZA200102589B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2002231688A1 (en) | 2000-12-21 | 2002-07-01 | Sanofi-Aventis Deutschland Gmbh | Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use |
| DE10064402A1 (de) * | 2000-12-21 | 2002-06-27 | Aventis Pharma Gmbh | Diphenylazetidinonderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| PL366855A1 (en) * | 2001-08-22 | 2005-02-07 | Aventis Pharma Deutschland Gmbh | Combination preparations of aryl substituted propanolamine derivatives with other active ingredients and the use thereof |
| US7161008B2 (en) * | 2002-05-03 | 2007-01-09 | Sanofi - Aventis Deutschland GmbH | Optically active β-aminoketones, optically active 1,3-amino alcohols and processes for preparing them |
| DE10219987A1 (de) * | 2002-05-03 | 2004-04-08 | Aventis Pharma Deutschland Gmbh | Optisch aktive β-Aminoketone, optisch aktive 1,3-Aminoalkohole und Verfahren zu deren Herstellung |
| GB0307918D0 (en) | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| RU2363699C2 (ru) * | 2005-02-28 | 2009-08-10 | Джапан Тобакко Инк. | Новое производное аминопиридина с ингибиторной активностью в отношении syk. |
| CA2794018C (en) * | 2010-03-24 | 2016-05-10 | Medical University Of South Carolina | Compositions and methods for the treatment of degenerative diseases |
| EP2575821B1 (en) | 2010-05-26 | 2015-08-12 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| CN104023727B (zh) | 2011-10-28 | 2017-04-05 | 鲁美纳医药公司 | 用于治疗小儿胆汁淤积性肝病的胆汁酸再循环抑制剂 |
| CA2852957C (en) | 2011-10-28 | 2020-08-04 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of hypercholemia and cholestatic liver disease |
| CN105228615A (zh) | 2013-03-15 | 2016-01-06 | 鲁美纳医药公司 | 用于治疗巴雷特食管和胃食管返流疾病的胆汁酸再循环抑制剂 |
| US20140275090A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| US11238759B1 (en) | 2015-10-29 | 2022-02-01 | Ward-Kraft, Inc. | Single ply wristband with printable coating |
| US11232719B1 (en) | 2019-09-04 | 2022-01-25 | Ward-Kraft, Inc. | Single ply wristband with printable coating |
| PL3923943T3 (pl) | 2019-02-12 | 2024-12-09 | Mirum Pharmaceuticals, Inc. | Zależna od genotypu i dawki odpowiedź na asbti u pacjentów z niedoborem pompy eksportu soli żółciowych |
| USD988404S1 (en) | 2020-02-14 | 2023-06-06 | Rekon, Llc | Wristband label form with single strap wristbands |
| USD941917S1 (en) | 2020-02-18 | 2022-01-25 | Ward-Kraft, Inc. | Combination wristband label form with extender |
| USD967253S1 (en) | 2020-02-26 | 2022-10-18 | Ward-Kraft, Inc. | Wristband form with extender |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1194273A3 (ru) * | 1981-02-09 | 1985-11-23 | Пфайзер Инк (Фирма) | Способ получени пирбутерола или его аналогов |
| FI892341A7 (fi) * | 1988-06-10 | 1989-12-11 | Hoffmann La Roche | Propanoliamiinijohdannaisia |
| DE19704243A1 (de) * | 1997-02-05 | 1998-08-06 | Bayer Ag | Neue 2-Amino-substituierte Pyridine |
| DK0869121T3 (da) | 1997-04-04 | 2004-09-20 | Aventis Pharma Gmbh | Hypolipidæmiske propanolaminderivater |
-
1998
- 1998-10-02 DE DE19845402A patent/DE19845402B4/de not_active Expired - Fee Related
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1999
- 1999-09-18 DK DK99948790T patent/DK1117661T3/da active
- 1999-09-18 AU AU61925/99A patent/AU760412B2/en not_active Ceased
- 1999-09-18 CN CNB998116351A patent/CN1150185C/zh not_active Expired - Fee Related
- 1999-09-18 TR TR2001/00895T patent/TR200100895T2/xx unknown
- 1999-09-18 WO PCT/EP1999/006932 patent/WO2000020410A1/de not_active Ceased
- 1999-09-18 JP JP2000574523A patent/JP2002526539A/ja active Pending
- 1999-09-18 HK HK02102007.5A patent/HK1040249B/zh not_active IP Right Cessation
- 1999-09-18 KR KR1020017004129A patent/KR100611030B1/ko not_active Expired - Fee Related
- 1999-09-18 EP EP99948790A patent/EP1117661B1/de not_active Expired - Lifetime
- 1999-09-18 BR BR9914266-0A patent/BR9914266A/pt not_active Application Discontinuation
- 1999-09-18 AT AT99948790T patent/ATE267825T1/de not_active IP Right Cessation
- 1999-09-18 RU RU2001111815/04A patent/RU2219176C2/ru not_active IP Right Cessation
- 1999-09-18 PL PL99347105A patent/PL347105A1/xx not_active Application Discontinuation
- 1999-09-18 ES ES99948790T patent/ES2219065T3/es not_active Expired - Lifetime
- 1999-09-18 PT PT99948790T patent/PT1117661E/pt unknown
- 1999-09-18 HU HU0103893A patent/HUP0103893A3/hu unknown
- 1999-09-18 DE DE59909609T patent/DE59909609D1/de not_active Expired - Lifetime
- 1999-09-18 CA CA002346083A patent/CA2346083A1/en not_active Abandoned
- 1999-09-29 US US09/407,973 patent/US6303639B1/en not_active Expired - Lifetime
- 1999-09-30 AR ARP990104958A patent/AR021843A1/es unknown
-
2001
- 2001-03-29 ZA ZA200102589A patent/ZA200102589B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK1117661T3 (da) | 2004-08-30 |
| US6303639B1 (en) | 2001-10-16 |
| HK1040249B (zh) | 2005-04-01 |
| JP2002526539A (ja) | 2002-08-20 |
| DE59909609D1 (de) | 2004-07-01 |
| ZA200102589B (en) | 2002-02-27 |
| ES2219065T3 (es) | 2004-11-16 |
| PT1117661E (pt) | 2004-09-30 |
| HUP0103893A3 (en) | 2002-10-28 |
| HUP0103893A2 (hu) | 2002-05-29 |
| EP1117661B1 (de) | 2004-05-26 |
| CN1321154A (zh) | 2001-11-07 |
| ATE267825T1 (de) | 2004-06-15 |
| EP1117661A1 (de) | 2001-07-25 |
| DE19845402B4 (de) | 2005-04-07 |
| DE19845402A1 (de) | 2000-04-13 |
| HK1040249A1 (en) | 2002-05-31 |
| BR9914266A (pt) | 2001-11-06 |
| KR20010103593A (ko) | 2001-11-23 |
| TR200100895T2 (tr) | 2001-12-21 |
| AU6192599A (en) | 2000-04-26 |
| KR100611030B1 (ko) | 2006-08-10 |
| CN1150185C (zh) | 2004-05-19 |
| RU2219176C2 (ru) | 2003-12-20 |
| WO2000020410A1 (de) | 2000-04-13 |
| AU760412B2 (en) | 2003-05-15 |
| PL347105A1 (en) | 2002-03-25 |
| AR021843A1 (es) | 2002-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |