ZA200400404B - 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
- ZA200400404B ZA200400404B ZA200400404A ZA200400404A ZA200400404B ZA 200400404 B ZA200400404 B ZA 200400404B ZA 200400404 A ZA200400404 A ZA 200400404A ZA 200400404 A ZA200400404 A ZA 200400404A ZA 200400404 B ZA200400404 B ZA 200400404B
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- ZA
- South Africa
- Prior art keywords
- compound
- optionally substituted
- phenyl
- hydrogen
- alkyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims description 7
- 230000003647 oxidation Effects 0.000 title claims description 7
- 238000007254 oxidation reaction Methods 0.000 title claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 6
- 229930195729 fatty acid Natural products 0.000 title claims description 6
- 239000000194 fatty acid Substances 0.000 title claims description 6
- 150000004665 fatty acids Chemical class 0.000 title claims description 6
- 150000004885 piperazines Chemical class 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- -1 2-methylbenzo-1,3-thiazol-5-yl Chemical group 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 206010002383 Angina Pectoris Diseases 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 206010022562 Intermittent claudication Diseases 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 4
- 208000007718 Stable Angina Diseases 0.000 claims description 4
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- 210000002027 skeletal muscle Anatomy 0.000 claims description 3
- 210000001519 tissue Anatomy 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 description 40
- 125000003118 aryl group Chemical group 0.000 description 32
- 125000004181 carboxyalkyl group Chemical group 0.000 description 19
- 125000004093 cyano group Chemical group *C#N 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 17
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 description 11
- 125000002252 acyl group Chemical group 0.000 description 7
- 125000004442 acylamino group Chemical group 0.000 description 7
- 125000004423 acyloxy group Chemical group 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
- 229930194542 Keto Natural products 0.000 description 6
- 125000000033 alkoxyamino group Chemical group 0.000 description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 6
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 description 6
- 125000005368 heteroarylthio group Chemical group 0.000 description 6
- 125000004470 heterocyclooxy group Chemical group 0.000 description 6
- 125000004468 heterocyclylthio group Chemical group 0.000 description 6
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 6
- 125000000468 ketone group Chemical group 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 description 6
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- XKLMZUWKNUAPSZ-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide Chemical compound COC1=CC=CC=C1OCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 XKLMZUWKNUAPSZ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229960000213 ranolazine Drugs 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000001746 atrial effect Effects 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- HGUZQMQXAHVIQC-UHFFFAOYSA-N n-methylethenamine Chemical group CNC=C HGUZQMQXAHVIQC-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P19/00—Drugs for skeletal disorders
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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
-
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
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- 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
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Transplantation (AREA)
- Endocrinology (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Lubricants (AREA)
- Paper (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30662101P | 2001-07-19 | 2001-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200400404B true ZA200400404B (en) | 2004-10-14 |
Family
ID=23186103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200400404A ZA200400404B (en) | 2001-07-19 | 2004-01-19 | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6930111B2 (no) |
| EP (1) | EP1406898B1 (no) |
| JP (1) | JP2004537554A (no) |
| KR (1) | KR100919141B1 (no) |
| CN (1) | CN1533388A (no) |
| AT (1) | ATE292633T1 (no) |
| AU (1) | AU2008202958A1 (no) |
| CA (1) | CA2454059A1 (no) |
| DE (1) | DE60203623T2 (no) |
| DK (1) | DK1406898T3 (no) |
| ES (1) | ES2236557T3 (no) |
| HK (1) | HK1064374A1 (no) |
| HU (1) | HUP0402088A3 (no) |
| IL (1) | IL159897A0 (no) |
| MX (1) | MXPA04000565A (no) |
| NO (1) | NO327635B1 (no) |
| NZ (1) | NZ530705A (no) |
| PL (1) | PL368529A1 (no) |
| PT (1) | PT1406898E (no) |
| RU (1) | RU2300533C2 (no) |
| WO (1) | WO2003008411A1 (no) |
| ZA (1) | ZA200400404B (no) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7001909B2 (en) * | 2001-07-19 | 2006-02-21 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| CA2486712C (en) * | 2002-05-21 | 2012-01-03 | Cv Therapeutics, Inc. | Method of treating diabetes |
| US8822473B2 (en) | 2002-05-21 | 2014-09-02 | Gilead Sciences, Inc. | Method of treating diabetes |
| MXPA05001592A (es) * | 2002-08-09 | 2005-05-05 | Astrazeneca Ab | Oxadiazoles como moduladores de receptor-5 de glutamato metabotropico. |
| WO2004014881A2 (en) | 2002-08-09 | 2004-02-19 | Astra Zeneca Ab | '1,2,4'oxadiazoles as modulators of metabotropic glutamate receptor-5 |
| CA2495179A1 (en) | 2002-08-09 | 2004-02-19 | Astrazeneca Ab | Compounds having an activity at metabotropic glutamate receptors |
| CA2508608A1 (en) * | 2002-12-05 | 2004-06-24 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| EP1806346B1 (en) * | 2002-12-05 | 2009-07-22 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| CA2512261A1 (en) | 2003-01-03 | 2004-07-29 | 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 |
| CA2530376A1 (en) * | 2003-06-23 | 2005-01-06 | Cv Therapeutics, Inc. | Urea derivatives of piperazines and piperidines as fatty acid oxidation inhibitors |
| US7115610B2 (en) | 2003-12-18 | 2006-10-03 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| US7959659B2 (en) * | 2004-01-02 | 2011-06-14 | Advanced Cardiovascular Systems, Inc. | High-density lipoprotein coated medical devices |
| AU2005282492A1 (en) * | 2004-09-08 | 2006-03-16 | Gilead Palo Alto, 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 |
| PT3135672T (pt) | 2008-10-10 | 2020-04-02 | Vm Discovery Inc | Composições e métodos para o tratamento distúrbios de utilização de álcool, dor e outras doenças |
| US20100292217A1 (en) * | 2009-05-14 | 2010-11-18 | Gilead Palo Alto, 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 |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1133989A (en) * | 1964-12-08 | 1968-11-20 | Chugai Pharmaceutical Co Ltd | Theophylline derivatives, their salts and process for preparing the same |
| DE2834114A1 (de) * | 1978-08-01 | 1980-02-14 | Schering Ag | Polyalkoxyphenylpyrrolidone iii, verfahren zu ihrer herstellung und ihre verwendung |
| 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 |
| DE3723648A1 (de) * | 1987-07-17 | 1989-01-26 | Sandoz Ag | Indol-derivate, ihre herstellung und sie enthaltende arzneimittel |
| JPH0699399B2 (ja) * | 1988-10-06 | 1994-12-07 | 三井東圧化学株式会社 | 新規複素環化合物およびそれを有効成分として含有する製癌剤効果増強剤 |
| JPH02268162A (ja) * | 1989-04-10 | 1990-11-01 | Fujisawa Pharmaceut Co Ltd | ジフェニルピリジン誘導体 |
| MX9308025A (es) * | 1992-12-22 | 1994-08-31 | Lilly Co Eli | Compuestos inhibidores de la proteasa del virus dela inmunodeficiencia humana, procedimiento para supreparacion y formulacion farmaceutica que los contiene. |
| 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 |
| CN1196708C (zh) * | 1999-09-13 | 2005-04-13 | 惠氏公司 | 2－(4－羟基－苯基)－1－[4－(2－氨－1－基－乙氧基)－苄基]－1h－吲哚－5－酚的吡喃葡糖苷轭合物 |
| SE9904765D0 (sv) * | 1999-12-23 | 1999-12-23 | Astra Ab | Pharmaceutically-useful compounds |
| JP3980885B2 (ja) * | 2000-02-22 | 2007-09-26 | スィーヴィー セラピューティクス インコーポレイテッド | 置換ピペラジン化合物 |
| US6451798B2 (en) * | 2000-02-22 | 2002-09-17 | Cv Therapeutics, Inc. | Substituted alkyl piperazine derivatives |
| US6638970B2 (en) * | 2000-02-22 | 2003-10-28 | Cv Therapeutics, Inc. | Substituted alkylene diamine compounds |
| AU2001238590A1 (en) * | 2000-02-22 | 2001-09-03 | Cv Therapeutics, Inc. | Substituted piperazine compounds |
| US6552023B2 (en) * | 2000-02-22 | 2003-04-22 | Cv Therapeutics, Inc. | Aralkyl substituted piperazine compounds |
| SE0003795D0 (sv) * | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Pharmaceutically useful compounds |
| US6573264B1 (en) * | 2000-10-23 | 2003-06-03 | Cv Therapeutics, Inc. | Heteroaryl alkyl piperazine derivatives |
-
2002
- 2002-07-18 EP EP02756522A patent/EP1406898B1/en not_active Expired - Lifetime
- 2002-07-18 WO PCT/US2002/022897 patent/WO2003008411A1/en active IP Right Grant
- 2002-07-18 HU HU0402088A patent/HUP0402088A3/hu unknown
- 2002-07-18 RU RU2004104951/04A patent/RU2300533C2/ru not_active IP Right Cessation
- 2002-07-18 ES ES02756522T patent/ES2236557T3/es not_active Expired - Lifetime
- 2002-07-18 DE DE60203623T patent/DE60203623T2/de not_active Expired - Fee Related
- 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 JP JP2003513970A patent/JP2004537554A/ja not_active Ceased
- 2002-07-18 KR KR1020047000898A patent/KR100919141B1/ko not_active IP Right Cessation
- 2002-07-18 CA CA002454059A patent/CA2454059A1/en not_active Abandoned
- 2002-07-18 US US10/198,237 patent/US6930111B2/en not_active Expired - Fee Related
- 2002-07-18 DK DK02756522T patent/DK1406898T3/da active
- 2002-07-18 AT AT02756522T patent/ATE292633T1/de not_active IP Right Cessation
- 2002-07-18 MX MXPA04000565A patent/MXPA04000565A/es active IP Right Grant
- 2002-07-18 NZ NZ530705A patent/NZ530705A/en not_active IP Right Cessation
- 2002-07-18 CN CNA02814371XA patent/CN1533388A/zh active Pending
-
2004
- 2004-01-19 ZA ZA200400404A patent/ZA200400404B/en unknown
- 2004-01-19 NO NO20040234A patent/NO327635B1/no not_active IP Right Cessation
- 2004-09-15 HK HK04107045A patent/HK1064374A1/xx not_active IP Right Cessation
-
2008
- 2008-07-03 AU AU2008202958A patent/AU2008202958A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1406898A1 (en) | 2004-04-14 |
| IL159897A0 (en) | 2004-06-20 |
| KR20040029374A (ko) | 2004-04-06 |
| DK1406898T3 (da) | 2005-05-30 |
| AU2002322527B2 (en) | 2008-04-17 |
| DE60203623T2 (de) | 2006-01-19 |
| AU2002322527A2 (en) | 2003-03-03 |
| DE60203623D1 (de) | 2005-05-12 |
| CA2454059A1 (en) | 2003-01-30 |
| PL368529A1 (en) | 2005-04-04 |
| PT1406898E (pt) | 2005-08-31 |
| RU2300533C2 (ru) | 2007-06-10 |
| ATE292633T1 (de) | 2005-04-15 |
| WO2003008411A1 (en) | 2003-01-30 |
| US20030181352A1 (en) | 2003-09-25 |
| RU2004104951A (ru) | 2005-06-27 |
| EP1406898B1 (en) | 2005-04-06 |
| KR100919141B1 (ko) | 2009-09-25 |
| AU2008202958A1 (en) | 2008-07-31 |
| HUP0402088A2 (hu) | 2005-02-28 |
| NO20040234L (no) | 2004-03-18 |
| ES2236557T3 (es) | 2005-07-16 |
| HUP0402088A3 (en) | 2010-03-29 |
| NZ530705A (en) | 2005-08-26 |
| HK1064374A1 (en) | 2005-01-28 |
| JP2004537554A (ja) | 2004-12-16 |
| CN1533388A (zh) | 2004-09-29 |
| MXPA04000565A (es) | 2005-06-17 |
| US6930111B2 (en) | 2005-08-16 |
| NO327635B1 (no) | 2009-09-07 |
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