CA2537942A1 - Compounds and methods for treating dyslipidemia - Google Patents
Compounds and methods for treating dyslipidemia Download PDFInfo
- Publication number
- CA2537942A1 CA2537942A1 CA002537942A CA2537942A CA2537942A1 CA 2537942 A1 CA2537942 A1 CA 2537942A1 CA 002537942 A CA002537942 A CA 002537942A CA 2537942 A CA2537942 A CA 2537942A CA 2537942 A1 CA2537942 A1 CA 2537942A1
- Authority
- CA
- Canada
- Prior art keywords
- trifluoromethyl
- cycloalkyl
- alkyl
- alkylaryl
- heterocyclic
- 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 28
- 238000000034 method Methods 0.000 title claims abstract 11
- 208000032928 Dyslipidaemia Diseases 0.000 title claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 21
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 10
- 125000004104 aryloxy group Chemical group 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- -1 C1-alkylcycloalkyl Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 238000008214 LDL Cholesterol Methods 0.000 claims 3
- 108010028554 LDL Cholesterol Proteins 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 claims 2
- 102100037637 Cholesteryl ester transfer protein Human genes 0.000 claims 2
- 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 108010023302 HDL Cholesterol Proteins 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000003828 downregulation Effects 0.000 claims 1
- LLEVICHHUOYYRX-UHFFFAOYSA-N ethyl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OCC)CCCC1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LLEVICHHUOYYRX-UHFFFAOYSA-N 0.000 claims 1
- HFURXXNCQGEELO-UHFFFAOYSA-N ethyl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-bromo-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(Br)=CC=C2N(C(=O)OCC)CCCC1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFURXXNCQGEELO-UHFFFAOYSA-N 0.000 claims 1
- SWKQBNNYQOEXGJ-UHFFFAOYSA-N ethyl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OCC)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SWKQBNNYQOEXGJ-UHFFFAOYSA-N 0.000 claims 1
- CRZNWWQCQMNPDQ-UHFFFAOYSA-N ethyl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-bromo-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(Br)=CC=C2N(C(=O)OCC)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CRZNWWQCQMNPDQ-UHFFFAOYSA-N 0.000 claims 1
- QZHRDXDOMBMPSR-UHFFFAOYSA-N ethyl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-methoxy-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(OC)=CC=C2N(C(=O)OCC)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QZHRDXDOMBMPSR-UHFFFAOYSA-N 0.000 claims 1
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- DNHBLWZQCXEDIO-UHFFFAOYSA-N propan-2-yl 4-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1C2=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)CCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DNHBLWZQCXEDIO-UHFFFAOYSA-N 0.000 claims 1
- RVRORVXTCVMLEC-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)C)C2=CC=CC=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RVRORVXTCVMLEC-UHFFFAOYSA-N 0.000 claims 1
- OJBVLLYNOIAHSN-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)C)C2=CC=C(C(F)(F)F)C=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OJBVLLYNOIAHSN-UHFFFAOYSA-N 0.000 claims 1
- XWMINHIEXQWWII-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-7-bromo-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)C)C2=CC=C(Br)C=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XWMINHIEXQWWII-UHFFFAOYSA-N 0.000 claims 1
- BXRMMCDXDYARCY-UHFFFAOYSA-N propan-2-yl 5-[[3,5-bis(trifluoromethyl)phenyl]methyl-methoxycarbonylamino]-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C1CCN(C(=O)OC(C)C)C2=CC(Cl)=CC=C2C1N(C(=O)OC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BXRMMCDXDYARCY-UHFFFAOYSA-N 0.000 claims 1
- CEOOTVIRKQRQCV-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=CC=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CEOOTVIRKQRQCV-UHFFFAOYSA-N 0.000 claims 1
- ZSUWCVWQMAHOLR-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-2-methyl-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)C(C)CCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZSUWCVWQMAHOLR-UHFFFAOYSA-N 0.000 claims 1
- RKCWETOXNKAHRO-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-4,4-dimethyl-7-(trifluoromethyl)-3,5-dihydro-2h-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)CCC(C)(C)C1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RKCWETOXNKAHRO-UHFFFAOYSA-N 0.000 claims 1
- MQIZICRKQSYLHY-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 MQIZICRKQSYLHY-UHFFFAOYSA-N 0.000 claims 1
- PTXMTGKCQWZCPM-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 PTXMTGKCQWZCPM-UHFFFAOYSA-N 0.000 claims 1
- WPZSUMUHYRSTFL-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-chloro-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC=C(Cl)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 WPZSUMUHYRSTFL-UHFFFAOYSA-N 0.000 claims 1
- KSYXXQMGFSWKMO-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-fluoro-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1-benzazepine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=C(F)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 KSYXXQMGFSWKMO-UHFFFAOYSA-N 0.000 claims 1
- UHTSGHIPBSIYOI-UHFFFAOYSA-N propan-2-yl 5-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-9-(trifluoromethyl)-3,4,5,6-tetrahydro-2h-1-benzazocine-1-carboxylate Chemical compound C1C2=CC=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)CCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UHTSGHIPBSIYOI-UHFFFAOYSA-N 0.000 claims 1
- QJFIGHFCPMTGDJ-UHFFFAOYSA-N propan-2-yl 6-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-8-(trifluoromethyl)-3,4,5,6-tetrahydro-2h-1-benzazocine-1-carboxylate Chemical compound C12=CC(C(F)(F)F)=CC=C2N(C(=O)OC(C)C)CCCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QJFIGHFCPMTGDJ-UHFFFAOYSA-N 0.000 claims 1
- UHJVAYAVHUGDDD-UHFFFAOYSA-N propan-2-yl 6-[acetyl-[[3,5-bis(trifluoromethyl)phenyl]methyl]amino]-9-(trifluoromethyl)-3,4,5,6-tetrahydro-2h-1-benzazocine-1-carboxylate Chemical compound C12=CC=C(C(F)(F)F)C=C2N(C(=O)OC(C)C)CCCCC1N(C(C)=O)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UHJVAYAVHUGDDD-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- 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
- A61P3/04—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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/32—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D225/00—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom
- C07D225/04—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D225/06—Heterocyclic compounds containing rings of more than seven members having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- C07D413/02—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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50973603P | 2003-10-08 | 2003-10-08 | |
| US60/509,736 | 2003-10-08 | ||
| PCT/US2004/030907 WO2005037796A1 (en) | 2003-10-08 | 2004-10-07 | Compounds and methods for treating dyslipidemia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2537942A1 true CA2537942A1 (en) | 2005-04-28 |
Family
ID=34465112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002537942A Abandoned CA2537942A1 (en) | 2003-10-08 | 2004-10-07 | Compounds and methods for treating dyslipidemia |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7749992B2 (enExample) |
| EP (2) | EP1670768B1 (enExample) |
| JP (1) | JP4773969B2 (enExample) |
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| EC (1) | ECSP066484A (enExample) |
| ES (1) | ES2332051T3 (enExample) |
| HR (1) | HRP20090581T1 (enExample) |
| IL (1) | IL173819A0 (enExample) |
| MA (1) | MA28268A1 (enExample) |
| MX (1) | MXPA06003927A (enExample) |
| NO (1) | NO20062074L (enExample) |
| PL (1) | PL1670768T3 (enExample) |
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| WO (1) | WO2005037796A1 (enExample) |
| ZA (1) | ZA200602888B (enExample) |
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| AU2005230915A1 (en) * | 2004-03-26 | 2005-10-20 | Eli Lilly And Company | Compounds and methods for treating dyslipidemia |
| JP2008504266A (ja) | 2004-06-24 | 2008-02-14 | イーライ リリー アンド カンパニー | 異脂肪血症を治療するための化合物及び方法 |
| US7790770B2 (en) | 2005-11-23 | 2010-09-07 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| US7652023B2 (en) | 2005-11-23 | 2010-01-26 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| AR077208A1 (es) | 2009-06-30 | 2011-08-10 | Lilly Co Eli | Derivados del acido trans-4-[[(5s)-5-[[[3,5-bis(trifluorometil) fenil] metil] (2-metil-2h-tetrazol-5-il) amino) -2,3,4,5-tetrahidro-7,9-dimetil-1h-1-benzazepin-1-il) metil)-ciclohexancarboxilico y sus formas cristalinas, composiciones farmaceuticas que los comprenden, su uso para preparar un medicam |
| CN103833636B (zh) * | 2014-03-31 | 2015-09-02 | 武汉武药制药有限公司 | 一种莫扎伐普坦中间体的合成方法 |
| WO2017023679A1 (en) * | 2015-07-31 | 2017-02-09 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| CN110291383B (zh) * | 2017-02-23 | 2021-12-28 | 株式会社Ihi | Oh自由基检测探测器、oh自由基测定装置以及oh自由基测定方法 |
| PE20211781A1 (es) | 2018-10-24 | 2021-09-08 | Viiv Healthcare Uk No 5 Ltd | Inhibidores de la replicacion del virus de la inmunodeficiencia humana |
| AU2021256166B2 (en) | 2020-04-15 | 2024-05-23 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| CN113636977B (zh) * | 2021-09-01 | 2022-12-20 | 温州大学 | 2-芳基苯并氮杂卓及其衍生物的合成方法 |
| CN117088814A (zh) * | 2023-02-16 | 2023-11-21 | 烟台大学 | 一种三氟甲硫化氮杂-8/9元环化合物的制备方法 |
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| JP2905909B2 (ja) * | 1991-04-19 | 1999-06-14 | 大塚製薬株式会社 | バソプレシン拮抗剤 |
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| PT751783E (pt) * | 1994-03-24 | 2000-05-31 | Merrell Pharma Inc | Derivados aminoacetilmercapto hipocolesterolemicos antiateroscleroticos e hipotrigliceridemicos |
| ATE360617T1 (de) * | 1994-06-15 | 2007-05-15 | Otsuka Pharma Co Ltd | Benzoheterocyclische verbindungen verwendbar als vasopressin- oder oxytocin-modulatoren |
| GB9523526D0 (en) * | 1995-11-17 | 1996-01-17 | Zeneca Ltd | Therapeutic compounds |
| JPH09214746A (ja) | 1996-02-02 | 1997-08-15 | Ricoh Co Ltd | 画像出力システム及び画像形成装置 |
| DE19627431A1 (de) | 1996-07-08 | 1998-01-15 | Bayer Ag | Heterocyclisch kondensierte Pyridine |
| US6207671B1 (en) | 1996-07-08 | 2001-03-27 | Bayer Aktiengesellschaft | Cycloalkano-pyridines |
| DE19627430A1 (de) | 1996-07-08 | 1998-01-15 | Bayer Ag | Bicyclisch kondensierte Pyridine |
| HRP970330B1 (en) | 1996-07-08 | 2004-06-30 | Bayer Ag | Cycloalkano pyridines |
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| DE19709125A1 (de) | 1997-03-06 | 1998-09-10 | Bayer Ag | Substituierte Chinoline |
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| JP2959765B2 (ja) * | 1997-12-12 | 1999-10-06 | 日本たばこ産業株式会社 | ３−ピペリジル−４−オキソキナゾリン誘導体及びそれを含有してなる医薬組成物 |
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| GT199900147A (es) | 1998-09-17 | 1999-09-06 | 1, 2, 3, 4- tetrahidroquinolinas 2-sustituidas 4-amino sustituidas. | |
| US6147089A (en) * | 1998-09-17 | 2000-11-14 | Pfizer Inc. | Annulated 4-carboxyamino-2-methyl-1,2,3,4,-tetrahydroquinolines |
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-
2004
- 2004-10-07 ES ES04793889T patent/ES2332051T3/es not_active Expired - Lifetime
- 2004-10-07 PL PL04793889T patent/PL1670768T3/pl unknown
- 2004-10-07 EP EP04793889A patent/EP1670768B1/en not_active Expired - Lifetime
- 2004-10-07 US US10/574,649 patent/US7749992B2/en not_active Expired - Fee Related
- 2004-10-07 HR HR20090581T patent/HRP20090581T1/hr unknown
- 2004-10-07 WO PCT/US2004/030907 patent/WO2005037796A1/en not_active Ceased
- 2004-10-07 CA CA002537942A patent/CA2537942A1/en not_active Abandoned
- 2004-10-07 DE DE602004023100T patent/DE602004023100D1/de not_active Expired - Lifetime
- 2004-10-07 PT PT04793889T patent/PT1670768E/pt unknown
- 2004-10-07 AU AU2004282101A patent/AU2004282101A1/en not_active Abandoned
- 2004-10-07 EP EP09157118A patent/EP2098512A1/en not_active Withdrawn
- 2004-10-07 CN CNA2004800295407A patent/CN1863778A/zh active Pending
- 2004-10-07 SI SI200431294T patent/SI1670768T1/sl unknown
- 2004-10-07 KR KR1020067006837A patent/KR20060085675A/ko not_active Ceased
- 2004-10-07 MX MXPA06003927A patent/MXPA06003927A/es not_active Application Discontinuation
- 2004-10-07 BR BRPI0414186-5A patent/BRPI0414186A/pt not_active Application Discontinuation
- 2004-10-07 EA EA200600737A patent/EA200600737A1/ru unknown
- 2004-10-07 AT AT04793889T patent/ATE442358T1/de active
- 2004-10-07 DK DK04793889T patent/DK1670768T3/da active
- 2004-10-07 JP JP2006533949A patent/JP4773969B2/ja not_active Expired - Fee Related
-
2006
- 2006-02-20 IL IL173819A patent/IL173819A0/en unknown
- 2006-04-05 EC EC2006006484A patent/ECSP066484A/es unknown
- 2006-04-07 ZA ZA200602888A patent/ZA200602888B/en unknown
- 2006-05-03 MA MA28999A patent/MA28268A1/fr unknown
- 2006-05-08 NO NO20062074A patent/NO20062074L/no not_active Application Discontinuation
-
2009
- 2009-11-05 CY CY20091101151T patent/CY1110537T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE442358T1 (de) | 2009-09-15 |
| IL173819A0 (en) | 2006-07-05 |
| PL1670768T3 (pl) | 2010-01-29 |
| PT1670768E (pt) | 2009-11-20 |
| US7749992B2 (en) | 2010-07-06 |
| WO2005037796A1 (en) | 2005-04-28 |
| CY1110537T1 (el) | 2015-04-29 |
| BRPI0414186A (pt) | 2006-10-31 |
| HRP20090581T1 (hr) | 2009-12-31 |
| ES2332051T3 (es) | 2010-01-25 |
| KR20060085675A (ko) | 2006-07-27 |
| ECSP066484A (es) | 2006-10-10 |
| ZA200602888B (en) | 2007-11-28 |
| EP1670768A1 (en) | 2006-06-21 |
| EP2098512A1 (en) | 2009-09-09 |
| EP1670768B1 (en) | 2009-09-09 |
| SI1670768T1 (sl) | 2010-01-29 |
| JP4773969B2 (ja) | 2011-09-14 |
| CN1863778A (zh) | 2006-11-15 |
| MXPA06003927A (es) | 2008-02-07 |
| EA200600737A1 (ru) | 2006-10-27 |
| JP2007508301A (ja) | 2007-04-05 |
| NO20062074L (no) | 2006-05-08 |
| AU2004282101A1 (en) | 2005-04-28 |
| DK1670768T3 (da) | 2009-11-09 |
| MA28268A1 (fr) | 2006-11-01 |
| DE602004023100D1 (de) | 2009-10-22 |
| US20070254869A1 (en) | 2007-11-01 |
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