JP2006516036A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006516036A5 JP2006516036A5 JP2006502846A JP2006502846A JP2006516036A5 JP 2006516036 A5 JP2006516036 A5 JP 2006516036A5 JP 2006502846 A JP2006502846 A JP 2006502846A JP 2006502846 A JP2006502846 A JP 2006502846A JP 2006516036 A5 JP2006516036 A5 JP 2006516036A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- yloxy
- propan
- piperazinyl
- methylbenzothiazol
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 33
- -1 2-methyl-benzothiazol-5-yl Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 4
- TUYCYESPUCOVGB-HTAPYJJXSA-N (2r)-1-[(2s)-4-[[5-(4-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=C(Cl)C=C1 TUYCYESPUCOVGB-HTAPYJJXSA-N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 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 1
- RJKBOQFQCANMGI-YADARESESA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[(5-naphthalen-2-yl-1,3,4-oxadiazol-2-yl)methyl]piperazin-1-yl]propan-2-ol Chemical compound C1=C2SC(C)=NC2=CC(OC[C@H](O)CN2CCN(CC=3OC(=NN=3)C=3C=C4C=CC=CC4=CC=3)C[C@@H]2C)=C1 RJKBOQFQCANMGI-YADARESESA-N 0.000 claims 1
- IKEWPSAPIZVTAL-FXAWDEMLSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[(5-phenyl-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=CC=C1 IKEWPSAPIZVTAL-FXAWDEMLSA-N 0.000 claims 1
- JSNVQPBGRONSNK-LAUBAEHRSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[[2-[4-(trifluoromethyl)phenyl]-1,3-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(O1)=CN=C1C1=CC=C(C(F)(F)F)C=C1 JSNVQPBGRONSNK-LAUBAEHRSA-N 0.000 claims 1
- 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
- LNCXVSZKKRYSSX-HFZDXXHNSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[[5-(4-phenylphenyl)-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=C1C(C=C1)=CC=C1C1=CC=CC=C1 LNCXVSZKKRYSSX-HFZDXXHNSA-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
- URKMPPOPIUNMJF-OXJNMPFZSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[[5-[3-(trifluoromethyl)phenyl]-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=CC(C(F)(F)F)=C1 URKMPPOPIUNMJF-OXJNMPFZSA-N 0.000 claims 1
- AICXVAPPRIPRMH-OXJNMPFZSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[[5-[4-(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=C(C(F)(F)F)C=C1 AICXVAPPRIPRMH-OXJNMPFZSA-N 0.000 claims 1
- XDFFMCMLTUBMSI-OXJNMPFZSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(2s)-2-methyl-4-[[5-[4-(trifluoromethyl)phenyl]-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(F)(F)F)C=C1 XDFFMCMLTUBMSI-OXJNMPFZSA-N 0.000 claims 1
- 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 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
- 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 1
- UYQLICCQQPOQNJ-HTAPYJJXSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[(3s)-3-methyl-4-[[5-[4-(trifluoromethyl)phenyl]-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=C1C1=CC=C(C(F)(F)F)C=C1 UYQLICCQQPOQNJ-HTAPYJJXSA-N 0.000 claims 1
- VDXGMOFLRLHAQM-OAQYLSRUSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[(2-phenyl-1,3-thiazol-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)=CSC=1C1=CC=CC=C1 VDXGMOFLRLHAQM-OAQYLSRUSA-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
- ZGHVIIJLPOFJJM-HSZRJFAPSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[(5-phenyl-1,3-benzoxazol-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(OC1=CC=2)=NC1=CC=2C1=CC=CC=C1 ZGHVIIJLPOFJJM-HSZRJFAPSA-N 0.000 claims 1
- 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 1
- YMMHPNLFOKKVJQ-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[3-(2-methylphenyl)-1,2,4-oxadiazol-5-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(ON=1)=NC=1C1=CC=CC=C1C YMMHPNLFOKKVJQ-LJQANCHMSA-N 0.000 claims 1
- 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 1
- 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 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
- 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 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
- 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 1
- PYUAONCDAVXNNW-OAQYLSRUSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[5-[4-(trifluoromethyl)phenyl]-1,2-oxazol-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(=NO1)C=C1C1=CC=C(C(F)(F)F)C=C1 PYUAONCDAVXNNW-OAQYLSRUSA-N 0.000 claims 1
- YVINUCTXLVXVHS-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[[5-[4-(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=C(C(F)(F)F)C=C1 YVINUCTXLVXVHS-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
- 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 1
- 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 1
- 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 1
- MMGFFJCZGMMREQ-FUHWJXTLSA-N (2r)-1-[(2s)-4-[[5-(2-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=CC=C1Cl MMGFFJCZGMMREQ-FUHWJXTLSA-N 0.000 claims 1
- WVFQHFYKKPXEJI-OXJNMPFZSA-N (2r)-1-[(2s)-4-[[5-(3,4-dichlorophenyl)-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=C(Cl)C(Cl)=C1 WVFQHFYKKPXEJI-OXJNMPFZSA-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
- 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 1
- MKHPIPHQPZWINC-GHTZIAJQSA-N (2r)-1-[(3s)-4-[[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]methyl]-3-methylpiperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=NOC(CN2[C@H](CN(C[C@@H](O)COC=3C=C4N=C(C)SC4=CC=3)CC2)C)=C1 MKHPIPHQPZWINC-GHTZIAJQSA-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
- BQWKKBAHGCPBKS-FXAWDEMLSA-N (2r)-1-[(3s)-4-[[5-(2-chlorophenyl)-1,2-oxazol-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(=NO1)C=C1C1=CC=CC=C1Cl BQWKKBAHGCPBKS-FXAWDEMLSA-N 0.000 claims 1
- YVXKOKIBCYGIIP-OXJNMPFZSA-N (2r)-1-[(3s)-4-[[5-(3,4-dichlorophenyl)-1,2-oxazol-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(=NO1)C=C1C1=CC=C(Cl)C(Cl)=C1 YVXKOKIBCYGIIP-OXJNMPFZSA-N 0.000 claims 1
- CUIODTSNCRPHNZ-HTAPYJJXSA-N (2r)-1-[(3s)-4-[[5-(4-chlorophenyl)-1,2-oxazol-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(=NO1)C=C1C1=CC=C(Cl)C=C1 CUIODTSNCRPHNZ-HTAPYJJXSA-N 0.000 claims 1
- IQTJYNABDCLEEH-OAQYLSRUSA-N (2r)-1-[4-[[2-(4-chlorophenyl)-1,3-thiazol-4-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)=CSC=1C1=CC=C(Cl)C=C1 IQTJYNABDCLEEH-OAQYLSRUSA-N 0.000 claims 1
- OSSJCLRFMVPXOU-QGZVFWFLSA-N (2r)-1-[4-[[3-(2,4-dichlorophenyl)-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(Cl)C=C1Cl OSSJCLRFMVPXOU-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- LRCLREIUBOJVPA-QGZVFWFLSA-N (2r)-1-[4-[[3-(2-fluorophenyl)-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=C1F LRCLREIUBOJVPA-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- OSGFHFZOYQIKPL-QGZVFWFLSA-N (2r)-1-[4-[[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-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(O1)=NN=C1C1=CC=CC=C1Cl OSGFHFZOYQIKPL-QGZVFWFLSA-N 0.000 claims 1
- 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 1
- WYDWTECDFUFLJT-OAQYLSRUSA-N (2r)-1-[4-[[5-(4-chlorophenyl)-1,2-oxazol-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(=NO1)C=C1C1=CC=C(Cl)C=C1 WYDWTECDFUFLJT-OAQYLSRUSA-N 0.000 claims 1
- YAFKHHYOOIBEMK-LJQANCHMSA-N (2r)-1-[4-[[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-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(O1)=NN=C1C1=CC=C(Cl)C=C1 YAFKHHYOOIBEMK-LJQANCHMSA-N 0.000 claims 1
- JLICQZZTJAHOOF-LJQANCHMSA-N (2r)-1-[4-[[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C(O1)=NN=C1CN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 JLICQZZTJAHOOF-LJQANCHMSA-N 0.000 claims 1
- PCWGBLKAGJPHPN-JOCHJYFZSA-N (2r)-1-[4-[[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-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(O1)=NN=C1C1=CC=C(C(C)(C)C)C=C1 PCWGBLKAGJPHPN-JOCHJYFZSA-N 0.000 claims 1
- VFVIRYSVZLPKMG-OAQYLSRUSA-N (2r)-1-[4-[[5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazol-2-yl]methyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=CC(N(C)C)=CC=C1C(O1)=NN=C1CN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 VFVIRYSVZLPKMG-OAQYLSRUSA-N 0.000 claims 1
- WVFQHFYKKPXEJI-JXFKEZNVSA-N (2s)-1-[(2s)-4-[[5-(3,4-dichlorophenyl)-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=C(Cl)C(Cl)=C1 WVFQHFYKKPXEJI-JXFKEZNVSA-N 0.000 claims 1
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 1
- QQKJIZOFAXRQPI-UHFFFAOYSA-N 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=1C=C2SC(C)=NC2=CC=1OCC(O)CN(CC1)CCN1CC(N=1)=NOC=1C1=CC=C(C(F)(F)F)C=C1 QQKJIZOFAXRQPI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WXQZGMFZSUJXEE-UHFFFAOYSA-N 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=1C=C2SC(C)=NC2=CC=1OCC(O)CN(CC1)CCN1CC(ON=1)=NC=1C1=CC=C(C(C)(C)C)C=C1 WXQZGMFZSUJXEE-UHFFFAOYSA-N 0.000 claims 1
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000029549 Muscle injury Diseases 0.000 claims 1
- 229910000752 Prince's Metal Inorganic materials 0.000 claims 1
- 208000007718 Stable Angina Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 230000035939 shock Effects 0.000 claims 1
- 210000002027 skeletal muscle Anatomy 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2006516036A JP2006516036A (ja) | 2006-06-15 |
| JP2006516036A5 true JP2006516036A5 (cg-RX-API-DMAC10.html) | 2007-03-01 |
Family
ID=32823684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006502846A Pending JP2006516036A (ja) | 2003-01-17 | 2004-01-16 | 置換ヘテロ環式化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7001909B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1583760A2 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2006516036A (cg-RX-API-DMAC10.html) |
| KR (1) | KR20050092421A (cg-RX-API-DMAC10.html) |
| AU (1) | AU2004207764C1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2513641A1 (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ541307A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2004067506A2 (cg-RX-API-DMAC10.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004069818A1 (en) * | 2003-01-17 | 2004-08-19 | Cv Therapeutics 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 |
| US7271169B2 (en) * | 2004-09-08 | 2007-09-18 | Cv Therapeutics, Inc. | Substituted heterocyclic compounds |
| 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 |
| NZ520782A (en) | 2000-02-22 | 2004-03-26 | Cv Therapeutics Inc | Substituted piperazine compounds that are partial fatty acid oxidation inhibitors |
| 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 |
| AU2001238590A1 (en) * | 2000-02-22 | 2001-09-03 | Cv Therapeutics, Inc. | Substituted piperazine compounds |
| US6573264B1 (en) * | 2000-10-23 | 2003-06-03 | Cv Therapeutics, Inc. | Heteroaryl alkyl piperazine derivatives |
| MXPA04000565A (es) * | 2001-07-19 | 2005-06-17 | Cv Therapeutics Inc | Compuestos de piperazina sustituidos y su uso como inhibidores de oxidacion de acidos grasos. |
-
2003
- 2003-01-17 US US10/346,684 patent/US7001909B2/en not_active Expired - Fee Related
-
2004
- 2004-01-16 KR KR1020057013173A patent/KR20050092421A/ko not_active Ceased
- 2004-01-16 AU AU2004207764A patent/AU2004207764C1/en not_active Ceased
- 2004-01-16 WO PCT/US2004/001096 patent/WO2004067506A2/en not_active Ceased
- 2004-01-16 JP JP2006502846A patent/JP2006516036A/ja active Pending
- 2004-01-16 EP EP04702915A patent/EP1583760A2/en not_active Withdrawn
- 2004-01-16 NZ NZ541307A patent/NZ541307A/en unknown
- 2004-01-16 CA CA002513641A patent/CA2513641A1/en not_active Abandoned