AU2003303676A1 - Substituted heterocyclic compounds - Google Patents
Substituted heterocyclic compounds Download PDFInfo
- Publication number
- AU2003303676A1 AU2003303676A1 AU2003303676A AU2003303676A AU2003303676A1 AU 2003303676 A1 AU2003303676 A1 AU 2003303676A1 AU 2003303676 A AU2003303676 A AU 2003303676A AU 2003303676 A AU2003303676 A AU 2003303676A AU 2003303676 A1 AU2003303676 A1 AU 2003303676A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- optionally substituted
- piperazinyl
- hydroxy
- acetamide
- 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
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
- 206010022562 Intermittent claudication Diseases 0.000 claims abstract description 6
- 208000021156 intermittent vascular claudication Diseases 0.000 claims abstract description 6
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 6
- 206010002388 Angina unstable Diseases 0.000 claims abstract description 5
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims abstract description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 5
- 208000007718 Stable Angina Diseases 0.000 claims abstract description 5
- 208000007814 Unstable Angina Diseases 0.000 claims abstract description 5
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims abstract description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims abstract description 5
- -1 2,6-dimethylphenyl Chemical group 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 33
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Chemical group 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- HLDIMPPROXLTPE-UHFFFAOYSA-N n-[3-[4-[2-(2,6-dimethylanilino)-2-oxoethyl]piperazin-1-yl]-2-hydroxypropyl]-2-fluorobenzamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CNC(=O)C=2C(=CC=CC=2)F)CC1 HLDIMPPROXLTPE-UHFFFAOYSA-N 0.000 claims description 5
- JZSNTCGOYYADPW-UHFFFAOYSA-N 2-[4-(3-cyclohexyl-2-hydroxypropyl)piperazin-1-yl]-n-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CC2CCCCC2)CC1 JZSNTCGOYYADPW-UHFFFAOYSA-N 0.000 claims description 4
- DFSUANUJDOVNHF-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[3-hydroxy-4-(2-methoxyphenyl)butyl]piperazin-1-yl]acetamide Chemical compound COC1=CC=CC=C1CC(O)CCN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 DFSUANUJDOVNHF-UHFFFAOYSA-N 0.000 claims description 4
- PCAAEZSZRIGXJR-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[3-hydroxy-4-(4-methoxyphenyl)butyl]piperazin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(O)CCN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 PCAAEZSZRIGXJR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical group CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- MJEIWFUFTJGOOI-UHFFFAOYSA-N 4-[4-[2-(2,6-dimethylanilino)-2-oxoethyl]piperazin-1-yl]-n-(2-fluorophenyl)-3-hydroxybutanamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CC(O)CC(=O)NC=2C(=CC=CC=2)F)CC1 MJEIWFUFTJGOOI-UHFFFAOYSA-N 0.000 claims description 2
- 210000002027 skeletal muscle Anatomy 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 230000001746 atrial effect Effects 0.000 abstract description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 59
- 239000000203 mixture Substances 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 51
- 125000001424 substituent group Chemical group 0.000 description 45
- 125000003118 aryl group Chemical group 0.000 description 44
- 125000004193 piperazinyl group Chemical group 0.000 description 43
- 238000002360 preparation method Methods 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 230000003647 oxidation Effects 0.000 description 29
- 238000007254 oxidation reaction Methods 0.000 description 29
- 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 27
- 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 27
- 239000004480 active ingredient Substances 0.000 description 26
- 125000003545 alkoxy group Chemical group 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
- 239000008103 glucose Substances 0.000 description 25
- 229910052736 halogen Inorganic materials 0.000 description 25
- 150000002367 halogens Chemical class 0.000 description 25
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 24
- 125000004093 cyano group Chemical group *C#N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 125000000623 heterocyclic group Chemical group 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 125000004181 carboxyalkyl group Chemical group 0.000 description 20
- 125000000753 cycloalkyl group Chemical group 0.000 description 20
- 239000004615 ingredient Substances 0.000 description 20
- 125000003342 alkenyl group Chemical group 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 19
- NJKRFQIWDJSYOK-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-piperazin-1-ylacetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCNCC1 NJKRFQIWDJSYOK-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 description 17
- 125000000304 alkynyl group Chemical group 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 150000004665 fatty acids Chemical class 0.000 description 15
- 230000010412 perfusion Effects 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000003826 tablet Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 150000002118 epoxides Chemical class 0.000 description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 238000004587 chromatography analysis Methods 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 229930194542 Keto Natural products 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 9
- 125000004442 acylamino group Chemical group 0.000 description 9
- 125000004423 acyloxy group Chemical group 0.000 description 9
- 125000005110 aryl thio group Chemical group 0.000 description 9
- 125000004104 aryloxy group Chemical group 0.000 description 9
- 230000000747 cardiac effect Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 230000034659 glycolysis Effects 0.000 description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 description 9
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 125000000468 ketone group Chemical group 0.000 description 9
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- 239000000843 powder Substances 0.000 description 9
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- 125000000033 alkoxyamino group Chemical group 0.000 description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 8
- 125000005368 heteroarylthio group Chemical group 0.000 description 8
- 125000004470 heterocyclooxy group Chemical group 0.000 description 8
- 125000004468 heterocyclylthio group Chemical group 0.000 description 8
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
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- OAMHIPWEVQNONQ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-(4-hydroxy-4-phenylbutyl)piperazin-1-yl]acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CCCC(O)C=2C=CC=CC=2)CC1 OAMHIPWEVQNONQ-UHFFFAOYSA-N 0.000 description 6
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 5
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- 125000003710 aryl alkyl group Chemical group 0.000 description 4
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- 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
- 238000005481 NMR spectroscopy Methods 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
-
- 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
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43786003P | 2003-01-03 | 2003-01-03 | |
| US60/437,860 | 2003-01-03 | ||
| PCT/US2003/040607 WO2004063180A1 (en) | 2003-01-03 | 2003-12-19 | Substituted heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2003303676A1 true AU2003303676A1 (en) | 2004-08-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003303676A Abandoned AU2003303676A1 (en) | 2003-01-03 | 2003-12-19 | Substituted heterocyclic compounds |
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| Country | Link |
|---|---|
| US (3) | US7205303B2 (enExample) |
| EP (1) | EP1578737B1 (enExample) |
| JP (1) | JP2006514066A (enExample) |
| KR (1) | KR20050086956A (enExample) |
| AT (1) | ATE443058T1 (enExample) |
| AU (1) | AU2003303676A1 (enExample) |
| CA (1) | CA2512261A1 (enExample) |
| DE (1) | DE60329323D1 (enExample) |
| ES (1) | ES2329997T3 (enExample) |
| NZ (1) | NZ541069A (enExample) |
| WO (1) | WO2004063180A1 (enExample) |
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| US7205303B2 (en) * | 2003-01-03 | 2007-04-17 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| JP5767205B2 (ja) * | 2009-04-02 | 2015-08-19 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | オートタキシン阻害剤としての複素環式化合物 |
| US20120220603A1 (en) * | 2009-09-04 | 2012-08-30 | Zalicus Pharmaceuticals Ltd. | Substituted heterocyclic derivatives for the treatment of pain and epilepsy |
| EP2961403A4 (en) | 2013-03-01 | 2016-11-30 | Zalicus Pharmaceuticals Ltd | HETEROCYCLIC INHIBITORS OF SODIUM CHANNEL |
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| US729499A (en) * | 1901-08-12 | 1903-05-26 | John Machaffie | Igniter for gas-engines. |
| US4766125A (en) | 1981-06-23 | 1988-08-23 | Janssen Pharmaceutica N.V. | N-aryl-piperazinealkanamides useful for protecting hearts from myocardial injury caused by ischaemia, anoxia or hypoxia |
| JPS584774A (ja) * | 1981-06-23 | 1983-01-11 | ジヤンセン・フア−マシユ−チカ・ナ−ムロ−ゼ・フエンノ−トシヤツプ | Ｎ−アリ−ル−ピペラジンアルカンアミド類 |
| US4558129A (en) | 1983-05-18 | 1985-12-10 | Syntex (U.S.A.) Inc. | Benzodioxanyl-hydroxyethylene-piperazinyl acetanilides which effect calcium entry and β-blockade |
| US4567264A (en) * | 1983-05-18 | 1986-01-28 | Syntex (U.S.A.) Inc. | Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry |
| US4588129A (en) * | 1983-09-06 | 1986-05-13 | Hudson Oxygen Therapy Sales Company | Nebulizer |
| NZ247044A (en) | 1989-06-23 | 1997-04-24 | Syntex Usa Inc Substituted For | Use of ranolazine and related piperazine derivatives to treat tissue affected by muscle and neuronal damage, including transplant tissue |
| JPH03141258A (ja) | 1989-10-25 | 1991-06-17 | Kowa Co | 新規なピペラジン誘導体 |
| HU209723B (en) | 1990-10-31 | 1994-10-28 | Richter Gedeon Vegyeszet | Process for producing of piperazine derivatives |
| US5455045A (en) | 1993-05-13 | 1995-10-03 | Syntex (U.S.A.) Inc. | High dose formulations |
| AU2001238590A1 (en) | 2000-02-22 | 2001-09-03 | Cv Therapeutics, Inc. | Substituted piperazine compounds |
| US6677336B2 (en) | 2000-02-22 | 2004-01-13 | Cv Therapeutics, Inc. | Substituted piperazine compounds |
| US6638970B2 (en) | 2000-02-22 | 2003-10-28 | Cv Therapeutics, Inc. | Substituted alkylene diamine compounds |
| MXPA02008213A (es) * | 2000-02-22 | 2004-04-05 | Cv Therapeutics Inc | Compuestos piperazina sustituidos. |
| 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 |
| US6693099B2 (en) * | 2000-10-17 | 2004-02-17 | The Procter & Gamble Company | Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance |
| 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 |
| DE60203623T2 (de) | 2001-07-19 | 2006-01-19 | CV Therapeutics, Inc., Palo Alto | Substituierte piperazinderivate und ihre verwendung als fettsaüre-oxidationsinhibitoren |
| CN1181065C (zh) * | 2002-05-08 | 2004-12-22 | 上海医药工业研究院 | 芳烷甲酰烷基哌嗪衍生物及其作为脑神经保护剂的应用 |
| DE60314662T2 (de) * | 2002-12-05 | 2008-03-13 | CV Therapeutics, Inc., Palo Alto | Substituierte piperazinverbindungen und deren verwendung als fettsäureoxidationsinhibitoren |
| US7205303B2 (en) * | 2003-01-03 | 2007-04-17 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
-
2003
- 2003-12-19 US US10/745,224 patent/US7205303B2/en not_active Expired - Lifetime
- 2003-12-19 AU AU2003303676A patent/AU2003303676A1/en not_active Abandoned
- 2003-12-19 JP JP2004566575A patent/JP2006514066A/ja active Pending
- 2003-12-19 NZ NZ541069A patent/NZ541069A/en unknown
- 2003-12-19 KR KR1020057012518A patent/KR20050086956A/ko not_active Ceased
- 2003-12-19 AT AT03808498T patent/ATE443058T1/de not_active IP Right Cessation
- 2003-12-19 CA CA002512261A patent/CA2512261A1/en not_active Abandoned
- 2003-12-19 EP EP03808498A patent/EP1578737B1/en not_active Expired - Lifetime
- 2003-12-19 WO PCT/US2003/040607 patent/WO2004063180A1/en not_active Ceased
- 2003-12-19 DE DE60329323T patent/DE60329323D1/de not_active Expired - Lifetime
- 2003-12-19 ES ES03808498T patent/ES2329997T3/es not_active Expired - Lifetime
-
2007
- 2007-03-08 US US11/683,917 patent/US20070155728A1/en not_active Abandoned
-
2008
- 2008-07-09 US US12/170,199 patent/US7566717B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US7205303B2 (en) | 2007-04-17 |
| ES2329997T3 (es) | 2009-12-03 |
| NZ541069A (en) | 2008-09-26 |
| HK1085467A1 (en) | 2006-08-25 |
| DE60329323D1 (de) | 2009-10-29 |
| US20070155728A1 (en) | 2007-07-05 |
| US20040176356A1 (en) | 2004-09-09 |
| KR20050086956A (ko) | 2005-08-30 |
| JP2006514066A (ja) | 2006-04-27 |
| WO2004063180A1 (en) | 2004-07-29 |
| CA2512261A1 (en) | 2004-07-29 |
| ATE443058T1 (de) | 2009-10-15 |
| US7566717B2 (en) | 2009-07-28 |
| EP1578737B1 (en) | 2009-09-16 |
| US20080275238A1 (en) | 2008-11-06 |
| EP1578737A1 (en) | 2005-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |