AU2004207764C1 - Substituted heterocyclic compounds - Google Patents
Substituted heterocyclic compounds Download PDFInfo
- Publication number
- AU2004207764C1 AU2004207764C1 AU2004207764A AU2004207764A AU2004207764C1 AU 2004207764 C1 AU2004207764 C1 AU 2004207764C1 AU 2004207764 A AU2004207764 A AU 2004207764A AU 2004207764 A AU2004207764 A AU 2004207764A AU 2004207764 C1 AU2004207764 C1 AU 2004207764C1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- yloxy
- propan
- methylbenzothiazol
- piperazinyl
- 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.)
- Ceased
Links
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 336
- -1 2-methylbenzothiazol-5-yl Chemical group 0.000 claims description 244
- 125000004193 piperazinyl group Chemical group 0.000 claims description 94
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 125000001072 heteroaryl group Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 52
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- HECYZXSVAWURCF-UHFFFAOYSA-N 1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound CC(O)COC1=CC=C2SC(C)=NC2=C1 HECYZXSVAWURCF-UHFFFAOYSA-N 0.000 claims description 12
- 206010002383 Angina Pectoris Diseases 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 210000001519 tissue Anatomy 0.000 claims description 7
- 206010022562 Intermittent claudication Diseases 0.000 claims description 6
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 6
- 208000010125 myocardial infarction Diseases 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- WXQZGMFZSUJXEE-JOCHJYFZSA-N (2r)-1-[4-[[3-(4-tert-butylphenyl)-1,2,4-oxadiazol-5-yl]methyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(ON=1)=NC=1C1=CC=C(C(C)(C)C)C=C1 WXQZGMFZSUJXEE-JOCHJYFZSA-N 0.000 claims description 5
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
- 208000007718 Stable Angina Diseases 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000035939 shock Effects 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- VCNBCLDATFDNLA-DOTOQJQBSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[(3-thiophen-2-yl-1,2,4-oxadiazol-5-yl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](N(CC1)C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)C)N1CC(ON=1)=NC=1C1=CC=CS1 VCNBCLDATFDNLA-DOTOQJQBSA-N 0.000 claims description 3
- CKMUYZOEMJMTIC-OXJNMPFZSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(3s)-3-methyl-4-[[5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H]1C)N(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CCN1CC(N=1)=NOC=1C1=CC=C(C(F)(F)F)C=C1 CKMUYZOEMJMTIC-OXJNMPFZSA-N 0.000 claims description 3
- DHCRXTRJCGTSHC-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[5-(2-methylphenyl)-1,2,4-oxadiazol-3-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(N=1)=NOC=1C1=CC=CC=C1C DHCRXTRJCGTSHC-LJQANCHMSA-N 0.000 claims description 3
- QQKJIZOFAXRQPI-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(N=1)=NOC=1C1=CC=C(C(F)(F)F)C=C1 QQKJIZOFAXRQPI-LJQANCHMSA-N 0.000 claims description 3
- ZQUCUQUABZECCX-GHTZIAJQSA-N (2r)-1-[(2s)-4-[[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]methyl]-2-methylpiperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=NOC(CN2C[C@H](C)N(C[C@@H](O)COC=3C=C4N=C(C)SC4=CC=3)CC2)=C1 ZQUCUQUABZECCX-GHTZIAJQSA-N 0.000 claims description 3
- CPOHQYINAICFMH-FXAWDEMLSA-N (2r)-1-[(2s)-4-[[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl]-2-methylpiperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C(O1)=NN=C1CN1C[C@H](C)N(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 CPOHQYINAICFMH-FXAWDEMLSA-N 0.000 claims description 3
- RNZHYYIGCHVHSY-HTAPYJJXSA-N (2r)-1-[(3s)-4-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]-3-methylpiperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H]1C)N(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CCN1CC(N=1)=CSC=1C1=CC=C(Cl)C=C1 RNZHYYIGCHVHSY-HTAPYJJXSA-N 0.000 claims description 3
- PDMBJTHLKZUGND-QGZVFWFLSA-N (2r)-1-[4-[[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(N=1)=NOC=1C1=CC=CC=C1F PDMBJTHLKZUGND-QGZVFWFLSA-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 3
- 206010002388 Angina unstable Diseases 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- 208000007814 Unstable Angina Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- 210000002027 skeletal muscle Anatomy 0.000 claims description 3
- ZUSOOVLXGYOCBV-GHTZIAJQSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[(3-phenyl-1,2-oxazol-5-yl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](N(CC1)C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)C)N1CC(ON=1)=CC=1C1=CC=CC=C1 ZUSOOVLXGYOCBV-GHTZIAJQSA-N 0.000 claims description 2
- TWWOADAMWUWGJJ-PGRDOPGGSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[(5-phenyl-1,2-oxazol-3-yl)methyl]piperazin-1-yl]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=C1 TWWOADAMWUWGJJ-PGRDOPGGSA-N 0.000 claims description 2
- BHYFHEOILJADFK-GBXCKJPGSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[(5-phenyl-1,3-benzoxazol-2-yl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](N(CC1)C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)C)N1CC(OC1=CC=2)=NC1=CC=2C1=CC=CC=C1 BHYFHEOILJADFK-GBXCKJPGSA-N 0.000 claims description 2
- NYKXUBDFFURVOY-PGRDOPGGSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(3s)-3-methyl-4-[(2-phenyl-1,3-thiazol-4-yl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H]1C)N(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CCN1CC(N=1)=CSC=1C1=CC=CC=C1 NYKXUBDFFURVOY-PGRDOPGGSA-N 0.000 claims description 2
- KGEGGVBYJAWADY-HTAPYJJXSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(3s)-3-methyl-4-[[2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H]1C)N(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CCN1CC(N=1)=CSC=1C1=CC=C(C(F)(F)F)C=C1 KGEGGVBYJAWADY-HTAPYJJXSA-N 0.000 claims description 2
- LKWWXRBXCVROKU-OAQYLSRUSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(N=1)=COC=1C1=CC=C(C(F)(F)F)C=C1 LKWWXRBXCVROKU-OAQYLSRUSA-N 0.000 claims description 2
- UXSSVYXASPLXNG-HXUWFJFHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(O1)=NN=C1C1=CC=C(C)C=C1 UXSSVYXASPLXNG-HXUWFJFHSA-N 0.000 claims description 2
- YRRXMFURJGMFCR-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(N=1)=NOC=1C1=CC=CC(C(F)(F)F)=C1 YRRXMFURJGMFCR-LJQANCHMSA-N 0.000 claims description 2
- SPJSAUKGKYMVBM-MAUKXSAKSA-N (2r)-1-[(2s)-4-[[3-(2,4-dichlorophenyl)-1,2,4-oxadiazol-5-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(ON=1)=NC=1C1=CC=C(Cl)C=C1Cl SPJSAUKGKYMVBM-MAUKXSAKSA-N 0.000 claims description 2
- JAEIVXBXBAMXQD-FXAWDEMLSA-N (2r)-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-FXAWDEMLSA-N 0.000 claims description 2
- XPDIPTLOYCVSRV-WMZHIEFXSA-N (2r)-1-[(2s)-4-[[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-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(O1)=NN=C1C1=CC=C(C(C)(C)C)C=C1 XPDIPTLOYCVSRV-WMZHIEFXSA-N 0.000 claims description 2
- MZJIFCJZYDLYGT-QGZVFWFLSA-N (2r)-1-[4-[[3-(2-chlorophenyl)-1,2,4-oxadiazol-5-yl]methyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(ON=1)=NC=1C1=CC=CC=C1Cl MZJIFCJZYDLYGT-QGZVFWFLSA-N 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 2
- NDSHQTCYWXQASZ-GHTZIAJQSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](N(CC1)C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)C)N1CC(O1)=NN=C1C1=CC=C(C)C=C1 NDSHQTCYWXQASZ-GHTZIAJQSA-N 0.000 claims 1
- KPVYGVIZUZUPPC-OXJNMPFZSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[[5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](N(CC1)C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)C)N1CC(N=1)=NOC=1C1=CC=CC(C(F)(F)F)=C1 KPVYGVIZUZUPPC-OXJNMPFZSA-N 0.000 claims 1
- JGSGMZISZMLHJT-RBISFHTESA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(3s)-3-methyl-4-[[5-(4-phenylphenyl)-1,2-oxazol-3-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H]1C)N(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CCN1CC(=NO1)C=C1C(C=C1)=CC=C1C1=CC=CC=C1 JGSGMZISZMLHJT-RBISFHTESA-N 0.000 claims 1
- BQZWPOOITGBNEH-HSZRJFAPSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[(5-naphthalen-2-yl-1,3,4-oxadiazol-2-yl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=CC=CC2=CC(C3=NN=C(O3)CN3CCN(CC3)C[C@@H](O)COC=3C=C4N=C(SC4=CC=3)C)=CC=C21 BQZWPOOITGBNEH-HSZRJFAPSA-N 0.000 claims 1
- GXVJMUZVAJGXFO-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(O1)=NN=C1C1=CC=CC=C1 GXVJMUZVAJGXFO-LJQANCHMSA-N 0.000 claims 1
- CEMUEODTOMXPLI-RUZDIDTESA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[5-(4-phenylphenyl)-1,3,4-oxadiazol-2-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(O1)=NN=C1C(C=C1)=CC=C1C1=CC=CC=C1 CEMUEODTOMXPLI-RUZDIDTESA-N 0.000 claims 1
- MYZTUCDTQOUYHW-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[5-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]methyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(O1)=NN=C1C1=CC=CC(C(F)(F)F)=C1 MYZTUCDTQOUYHW-LJQANCHMSA-N 0.000 claims 1
- ZQUCUQUABZECCX-WIYYLYMNSA-N (2r)-1-[(2r)-4-[[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]methyl]-2-methylpiperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=NOC(CN2C[C@@H](C)N(C[C@@H](O)COC=3C=C4N=C(C)SC4=CC=3)CC2)=C1 ZQUCUQUABZECCX-WIYYLYMNSA-N 0.000 claims 1
- IUQUTXQBQHHBDK-OXJNMPFZSA-N (2r)-1-[(2s)-4-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-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(O1)=NN=C1C1=CC=C(Cl)C=C1 IUQUTXQBQHHBDK-OXJNMPFZSA-N 0.000 claims 1
- NAELTLBRZMDVTG-PGRDOPGGSA-N (2r)-1-[(2s)-4-[[5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazol-2-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(O1)=NN=C1C1=CC=C(N(C)C)C=C1 NAELTLBRZMDVTG-PGRDOPGGSA-N 0.000 claims 1
- SPNSEIHFSBHQCS-MAUKXSAKSA-N (2r)-1-[(3s)-4-[[5-(2,4-dichlorophenyl)-1,2,4-oxadiazol-3-yl]methyl]-3-methylpiperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H]1C)N(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CCN1CC(N=1)=NOC=1C1=CC=C(Cl)C=C1Cl SPNSEIHFSBHQCS-MAUKXSAKSA-N 0.000 claims 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/00—Drugs for disorders of the metabolism
- 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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- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
-
- 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
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- 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
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- 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
- C07D413/08—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 carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
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- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/346,684 | 2003-01-17 | ||
| US10/346,684 US7001909B2 (en) | 2001-07-19 | 2003-01-17 | Substituted heterocyclic compounds |
| PCT/US2004/001096 WO2004067506A2 (en) | 2003-01-17 | 2004-01-16 | Substituted heterocyclic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2004207764A1 AU2004207764A1 (en) | 2004-08-12 |
| AU2004207764B2 AU2004207764B2 (en) | 2009-03-26 |
| AU2004207764C1 true AU2004207764C1 (en) | 2009-10-22 |
Family
ID=32823684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004207764A Ceased AU2004207764C1 (en) | 2003-01-17 | 2004-01-16 | Substituted heterocyclic compounds |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7001909B2 (enExample) |
| EP (1) | EP1583760A2 (enExample) |
| JP (1) | JP2006516036A (enExample) |
| KR (1) | KR20050092421A (enExample) |
| AU (1) | AU2004207764C1 (enExample) |
| CA (1) | CA2513641A1 (enExample) |
| NZ (1) | NZ541307A (enExample) |
| WO (1) | WO2004067506A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004209522A1 (en) * | 2003-01-17 | 2004-08-19 | Gilead Palo Alto, Inc. | Substituted heterocyclic compounds useful in the treatment of cardiovascular diseases |
| CA2550257A1 (en) | 2003-12-18 | 2005-07-07 | Cv Therapeutics, Inc. | 1-akan-2-ol substituted piperazine and piperidine compounds |
| WO2006029179A2 (en) * | 2004-09-08 | 2006-03-16 | Cv Therapeutics, Inc. | Substituted piperazine compounds and their use as fatty acid oxidation inhibitors |
| CN106496212B (zh) * | 2016-10-12 | 2019-11-15 | 贵州大学 | 一种吡唑联噁二唑硫醚类化合物及其制备方法与应用 |
Family Cites Families (11)
| 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 |
| US4567264A (en) * | 1983-05-18 | 1986-01-28 | Syntex (U.S.A.) Inc. | Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry |
| US4723014A (en) * | 1986-11-19 | 1988-02-02 | Warner-Lambert Company | Process for the preparation of 2-substituted-1,4-dihydropyridines |
| JPH02268162A (ja) * | 1989-04-10 | 1990-11-01 | Fujisawa Pharmaceut Co Ltd | ジフェニルピリジン誘導体 |
| SE9904765D0 (sv) * | 1999-12-23 | 1999-12-23 | Astra Ab | Pharmaceutically-useful compounds |
| WO2001062749A1 (en) * | 2000-02-22 | 2001-08-30 | Cv Therapeutics, Inc. | Substituted piperazine 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 |
| BR0108592A (pt) | 2000-02-22 | 2004-06-29 | Cv Therapeutics Inc | Compostos de piperazina substituìda |
| US6573264B1 (en) * | 2000-10-23 | 2003-06-03 | Cv Therapeutics, Inc. | Heteroaryl alkyl piperazine derivatives |
| ATE292633T1 (de) * | 2001-07-19 | 2005-04-15 | Cv Therapeutics Inc | Substituierte piperazinderivate und ihre verwendung als fettsaüreoxidationsinhibitoren |
-
2003
- 2003-01-17 US US10/346,684 patent/US7001909B2/en not_active Expired - Fee Related
-
2004
- 2004-01-16 EP EP04702915A patent/EP1583760A2/en not_active Withdrawn
- 2004-01-16 WO PCT/US2004/001096 patent/WO2004067506A2/en not_active Ceased
- 2004-01-16 AU AU2004207764A patent/AU2004207764C1/en not_active Ceased
- 2004-01-16 KR KR1020057013173A patent/KR20050092421A/ko not_active Ceased
- 2004-01-16 CA CA002513641A patent/CA2513641A1/en not_active Abandoned
- 2004-01-16 JP JP2006502846A patent/JP2006516036A/ja active Pending
- 2004-01-16 NZ NZ541307A patent/NZ541307A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004207764A1 (en) | 2004-08-12 |
| WO2004067506A2 (en) | 2004-08-12 |
| KR20050092421A (ko) | 2005-09-21 |
| AU2004207764B2 (en) | 2009-03-26 |
| JP2006516036A (ja) | 2006-06-15 |
| EP1583760A2 (en) | 2005-10-12 |
| US7001909B2 (en) | 2006-02-21 |
| US20030176447A1 (en) | 2003-09-18 |
| CA2513641A1 (en) | 2004-08-12 |
| NZ541307A (en) | 2008-11-28 |
| WO2004067506A3 (en) | 2004-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DA2 | Applications for amendment section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 29 MAY 2009. |
|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 29 MAY 2009 |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |