AU2008202958A1 - Substituted piperazine compounds and their use as fatty acid oxidation inhibitors - Google Patents
Substituted piperazine compounds and their use as fatty acid oxidation inhibitors Download PDFInfo
- Publication number
- AU2008202958A1 AU2008202958A1 AU2008202958A AU2008202958A AU2008202958A1 AU 2008202958 A1 AU2008202958 A1 AU 2008202958A1 AU 2008202958 A AU2008202958 A AU 2008202958A AU 2008202958 A AU2008202958 A AU 2008202958A AU 2008202958 A1 AU2008202958 A1 AU 2008202958A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- methyl
- methylbenzothiazol
- yloxy
- propan
- 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
- 230000003647 oxidation Effects 0.000 title description 34
- 238000007254 oxidation reaction Methods 0.000 title description 34
- 235000014113 dietary fatty acids Nutrition 0.000 title description 19
- 239000000194 fatty acid Substances 0.000 title description 19
- 229930195729 fatty acid Natural products 0.000 title description 19
- 150000004665 fatty acids Chemical class 0.000 title description 18
- 239000003112 inhibitor Substances 0.000 title description 14
- 150000004885 piperazines Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 259
- -1 2-methylbenzothiazol-5-yl Chemical group 0.000 claims description 140
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 125000004193 piperazinyl group Chemical group 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- BNRANURXPKRRKP-UHFFFAOYSA-N 1-[tert-butyl-[(4-methylphenyl)methyl]amino]-3-(1H-indol-4-yloxy)propan-2-ol Chemical compound Cc1ccc(CN(CC(O)COc2cccc3[nH]ccc23)C(C)(C)C)cc1 BNRANURXPKRRKP-UHFFFAOYSA-N 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- AXLOCHLTNQDFFS-BESJYZOMSA-N azastene Chemical compound C([C@H]1[C@@H]2CC[C@@]([C@]2(CC[C@@H]1[C@@]1(C)C2)C)(O)C)C=C1C(C)(C)C1=C2C=NO1 AXLOCHLTNQDFFS-BESJYZOMSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- JAEIVXBXBAMXQD-PXNSSMCTSA-N (2s)-1-[(2s)-4-[[5-(2-chlorophenyl)-1,2-oxazol-3-yl]methyl]-2-methylpiperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](N(CC1)C[C@H](O)COC=2C=C3N=C(C)SC3=CC=2)C)N1CC(=NO1)C=C1C1=CC=CC=C1Cl JAEIVXBXBAMXQD-PXNSSMCTSA-N 0.000 claims 1
- MNOULQLXILYKNV-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]-1h-pyrazole Chemical group C1=CC(C(F)(F)F)=CC=C1C1=CC=NN1 MNOULQLXILYKNV-UHFFFAOYSA-N 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 22
- 201000010099 disease Diseases 0.000 abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 10
- 241000124008 Mammalia Species 0.000 abstract description 6
- 230000001746 atrial effect Effects 0.000 abstract description 6
- 206010022562 Intermittent claudication Diseases 0.000 abstract description 5
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 5
- 208000021156 intermittent vascular claudication Diseases 0.000 abstract description 5
- 206010003130 Arrhythmia supraventricular Diseases 0.000 abstract description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 abstract description 4
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 4
- 208000007718 Stable Angina Diseases 0.000 abstract description 4
- 206010047281 Ventricular arrhythmia Diseases 0.000 abstract description 4
- 208000010125 myocardial infarction Diseases 0.000 abstract description 4
- 206010002388 Angina unstable Diseases 0.000 abstract description 2
- 208000007814 Unstable Angina Diseases 0.000 abstract description 2
- 201000004332 intermediate coronary syndrome Diseases 0.000 abstract description 2
- 230000036470 plasma concentration Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 67
- 238000006243 chemical reaction Methods 0.000 description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- 239000000243 solution Substances 0.000 description 53
- 125000001424 substituent group Chemical group 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
- 238000002360 preparation method Methods 0.000 description 48
- 125000003118 aryl group Chemical group 0.000 description 44
- 239000002904 solvent Substances 0.000 description 44
- 238000000034 method Methods 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 37
- 230000002829 reductive effect Effects 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 28
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 26
- 239000008103 glucose Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- 125000004093 cyano group Chemical group *C#N 0.000 description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 24
- 125000004181 carboxyalkyl group Chemical group 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 22
- 239000012442 inert solvent Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 125000000753 cycloalkyl group Chemical group 0.000 description 20
- 125000003342 alkenyl group Chemical group 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 19
- 239000004615 ingredient Substances 0.000 description 19
- 239000003826 tablet Substances 0.000 description 19
- 125000000392 cycloalkenyl group Chemical group 0.000 description 18
- 125000000304 alkynyl group Chemical group 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 230000010412 perfusion Effects 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 229930194542 Keto Natural products 0.000 description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 10
- 125000004423 acyloxy group Chemical group 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 description 10
- 125000000468 ketone group Chemical group 0.000 description 10
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 10
- 150000003573 thiols Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 125000004442 acylamino group Chemical group 0.000 description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 9
- 125000005110 aryl thio group Chemical group 0.000 description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 9
- 230000000747 cardiac effect Effects 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 125000005368 heteroarylthio group Chemical group 0.000 description 9
- 125000004470 heterocyclooxy group Chemical group 0.000 description 9
- 125000004468 heterocyclylthio group Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000000547 substituted alkyl group Chemical group 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 125000000033 alkoxyamino group Chemical group 0.000 description 8
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 8
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- 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
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Transplantation (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Lubricants (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Paper (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30662101P | 2001-07-19 | 2001-07-19 | |
| US60/306,621 | 2001-07-19 | ||
| AU2002322527A AU2002322527C1 (en) | 2001-07-19 | 2002-07-18 | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| PCT/US2002/022897 WO2003008411A1 (en) | 2001-07-19 | 2002-07-18 | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002322527A Division AU2002322527C1 (en) | 2001-07-19 | 2002-07-18 | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2008202958A1 true AU2008202958A1 (en) | 2008-07-31 |
Family
ID=23186103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008202958A Abandoned AU2008202958A1 (en) | 2001-07-19 | 2008-07-03 | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6930111B2 (enExample) |
| EP (1) | EP1406898B1 (enExample) |
| JP (1) | JP2004537554A (enExample) |
| KR (1) | KR100919141B1 (enExample) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2023023995A1 (zh) * | 2021-08-25 | 2023-03-02 | 苏州大学 | 一种防治心肌缺血后心功能衰竭的药物及其应用 |
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| US7001909B2 (en) * | 2001-07-19 | 2006-02-21 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| NZ536678A (en) | 2002-05-21 | 2007-01-26 | Cv Therapeutics Inc | Administration of a partial fatty acid inhibitor such as ranolazine for the treatment of diabetes |
| US8822473B2 (en) * | 2002-05-21 | 2014-09-02 | Gilead Sciences, Inc. | Method of treating diabetes |
| PL375256A1 (en) | 2002-08-09 | 2005-11-28 | Astra Zeneca Ab | 1,2,4-oxadiazoles as modulators of metabotropic glutamate receptor-5 |
| AU2003264018A1 (en) * | 2002-08-09 | 2004-02-25 | Astrazeneca Ab | Compounds having an activity at metabotropic glutamate receptors |
| US20040132726A1 (en) * | 2002-08-09 | 2004-07-08 | Astrazeneca Ab And Nps Pharmaceuticals, Inc. | New compounds |
| US7125876B2 (en) * | 2002-12-05 | 2006-10-24 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| EP1806346B1 (en) * | 2002-12-05 | 2009-07-22 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| EP1578737B1 (en) | 2003-01-03 | 2009-09-16 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| AU2004209522A1 (en) * | 2003-01-17 | 2004-08-19 | Gilead Palo Alto, Inc. | Substituted heterocyclic compounds useful in the treatment of cardiovascular diseases |
| KR20060065586A (ko) * | 2003-06-23 | 2006-06-14 | 씨브이 쎄러퓨틱스, 인코포레이티드 | 지방산 산화 저해제로서의, 피페라진 및 피페리딘의 우레아유도체 |
| CA2550257A1 (en) * | 2003-12-18 | 2005-07-07 | Cv Therapeutics, Inc. | 1-akan-2-ol substituted piperazine and piperidine compounds |
| WO2005068020A1 (en) * | 2004-01-02 | 2005-07-28 | Advanced Cardiovascular Systems, Inc. | High-density lipoprotein coated medical devices |
| WO2006029179A2 (en) * | 2004-09-08 | 2006-03-16 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| WO2008023248A2 (en) | 2006-08-24 | 2008-02-28 | Wockhardt Research Centre | Novel macrolides and ketolides having antimicrobial activity |
| US8088920B2 (en) * | 2008-03-31 | 2012-01-03 | Hoffmann-La Roche Inc. | 3-trifluoromethyl-pyrazine-2-carboxylic acid amide derivatives as HDL-cholesterol raising agents |
| SI3135672T1 (sl) * | 2008-10-10 | 2020-07-31 | Vm Discovery, Inc. | Sestavki in postopki za zdravljenje motenj, bolečin in drugih bolezni povezanih z uporabo alkohola |
| AU2010248948A1 (en) * | 2009-05-14 | 2011-12-01 | Gilead Sciences, Inc. | Ranolazine for the treatment of CNS disorders |
| WO2011115150A1 (ja) * | 2010-03-18 | 2011-09-22 | 興和株式会社 | ベンゾチアジン化合物の製造方法 |
| CN111285819A (zh) * | 2018-12-07 | 2020-06-16 | 江苏恩华药业股份有限公司 | 一种苯并噁唑类化合物及其应用 |
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| GB1133989A (en) * | 1964-12-08 | 1968-11-20 | Chugai Pharmaceutical Co Ltd | Theophylline derivatives, their salts and process for preparing the same |
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| US4567264A (en) * | 1983-05-18 | 1986-01-28 | Syntex (U.S.A.) Inc. | Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry |
| JPS6137765A (ja) * | 1984-07-19 | 1986-02-22 | サンド・アクチエンゲゼルシヤフト | ３‐アミノプロポキシアリール誘導体 |
| US4723014A (en) * | 1986-11-19 | 1988-02-02 | Warner-Lambert Company | Process for the preparation of 2-substituted-1,4-dihydropyridines |
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| WO1998021190A1 (en) * | 1996-11-14 | 1998-05-22 | American Home Products Corporation | Substituted tetrahydro-1,3,5-triazin-2[1h]-thiones as anti-atherosclerotic agents |
| TWI287018B (en) * | 1999-09-13 | 2007-09-21 | Wyeth Corp | Glucopyranosides conjugates of 2-(4-hydroxy-phenyl)-3-methyl-1-[4-(2-amin-1-yl-ethoxy)-benzyl]-1H-indol-5-ols |
| SE9904765D0 (sv) * | 1999-12-23 | 1999-12-23 | Astra Ab | Pharmaceutically-useful compounds |
| US6552023B2 (en) * | 2000-02-22 | 2003-04-22 | Cv Therapeutics, Inc. | Aralkyl substituted piperazine compounds |
| US6451798B2 (en) * | 2000-02-22 | 2002-09-17 | Cv Therapeutics, Inc. | Substituted alkyl piperazine derivatives |
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-
2002
- 2002-07-18 AT AT02756522T patent/ATE292633T1/de not_active IP Right Cessation
- 2002-07-18 CA CA002454059A patent/CA2454059A1/en not_active Abandoned
- 2002-07-18 MX MXPA04000565A patent/MXPA04000565A/es active IP Right Grant
- 2002-07-18 KR KR1020047000898A patent/KR100919141B1/ko not_active Expired - Fee Related
- 2002-07-18 DK DK02756522T patent/DK1406898T3/da active
- 2002-07-18 DE DE60203623T patent/DE60203623T2/de not_active Expired - Fee Related
- 2002-07-18 WO PCT/US2002/022897 patent/WO2003008411A1/en not_active Ceased
- 2002-07-18 HU HU0402088A patent/HUP0402088A3/hu unknown
- 2002-07-18 ES ES02756522T patent/ES2236557T3/es not_active Expired - Lifetime
- 2002-07-18 EP EP02756522A patent/EP1406898B1/en not_active Expired - Lifetime
- 2002-07-18 JP JP2003513970A patent/JP2004537554A/ja not_active Ceased
- 2002-07-18 IL IL15989702A patent/IL159897A0/xx unknown
- 2002-07-18 PT PT02756522T patent/PT1406898E/pt unknown
- 2002-07-18 PL PL02368529A patent/PL368529A1/xx not_active Application Discontinuation
- 2002-07-18 RU RU2004104951/04A patent/RU2300533C2/ru not_active IP Right Cessation
- 2002-07-18 NZ NZ530705A patent/NZ530705A/en not_active IP Right Cessation
- 2002-07-18 CN CNA02814371XA patent/CN1533388A/zh active Pending
- 2002-07-18 US US10/198,237 patent/US6930111B2/en not_active Expired - Fee Related
-
2004
- 2004-01-19 ZA ZA200400404A patent/ZA200400404B/en unknown
- 2004-01-19 NO NO20040234A patent/NO327635B1/no not_active IP Right Cessation
-
2008
- 2008-07-03 AU AU2008202958A patent/AU2008202958A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023023995A1 (zh) * | 2021-08-25 | 2023-03-02 | 苏州大学 | 一种防治心肌缺血后心功能衰竭的药物及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2454059A1 (en) | 2003-01-30 |
| EP1406898A1 (en) | 2004-04-14 |
| HUP0402088A2 (hu) | 2005-02-28 |
| AU2002322527A2 (en) | 2003-03-03 |
| NO327635B1 (no) | 2009-09-07 |
| HK1064374A1 (en) | 2005-01-28 |
| US6930111B2 (en) | 2005-08-16 |
| IL159897A0 (en) | 2004-06-20 |
| NZ530705A (en) | 2005-08-26 |
| MXPA04000565A (es) | 2005-06-17 |
| HUP0402088A3 (en) | 2010-03-29 |
| ES2236557T3 (es) | 2005-07-16 |
| KR100919141B1 (ko) | 2009-09-25 |
| DE60203623T2 (de) | 2006-01-19 |
| JP2004537554A (ja) | 2004-12-16 |
| PT1406898E (pt) | 2005-08-31 |
| NO20040234L (no) | 2004-03-18 |
| DK1406898T3 (da) | 2005-05-30 |
| DE60203623D1 (de) | 2005-05-12 |
| EP1406898B1 (en) | 2005-04-06 |
| ZA200400404B (en) | 2004-10-14 |
| RU2300533C2 (ru) | 2007-06-10 |
| KR20040029374A (ko) | 2004-04-06 |
| RU2004104951A (ru) | 2005-06-27 |
| ATE292633T1 (de) | 2005-04-15 |
| PL368529A1 (en) | 2005-04-04 |
| CN1533388A (zh) | 2004-09-29 |
| AU2002322527B2 (en) | 2008-04-17 |
| WO2003008411A1 (en) | 2003-01-30 |
| US20030181352A1 (en) | 2003-09-25 |
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Legal Events
| Date | Code | Title | Description |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |