JP2007502265A5 - - Google Patents
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- JP2007502265A5 JP2007502265A5 JP2006523069A JP2006523069A JP2007502265A5 JP 2007502265 A5 JP2007502265 A5 JP 2007502265A5 JP 2006523069 A JP2006523069 A JP 2006523069A JP 2006523069 A JP2006523069 A JP 2006523069A JP 2007502265 A5 JP2007502265 A5 JP 2007502265A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- dihydroxy
- pyrrol
- heptanoic acid
- fluoro
- 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.)
- Withdrawn
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- 125000000217 alkyl group Chemical group 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 14
- 150000001408 amides Chemical class 0.000 claims 11
- 150000002148 esters Chemical class 0.000 claims 11
- -1 trifluoro Pyridinyl Chemical group 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 239000000460 chlorine Chemical group 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 239000011737 fluorine Substances 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 229940002612 prodrug Drugs 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- GZJKOCTWBFFTJJ-JWQCQUIFSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-[(2-hydroxyphenyl)sulfamoyl]-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C(=CC=CC=2)O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 GZJKOCTWBFFTJJ-JWQCQUIFSA-N 0.000 claims 2
- XVDTXKNUSWJVBR-CLJLJLNGSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-5-propan-2-yl-4-[(4-sulfamoylphenyl)sulfamoyl]pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C=CC(=CC=2)S(N)(=O)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 XVDTXKNUSWJVBR-CLJLJLNGSA-N 0.000 claims 2
- ROFPYOAUHCRAIY-NHCUHLMSSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-iodo-3-phenyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(I)C(C=2C=CC=CC=2)=C1C1=CC=C(F)C=C1 ROFPYOAUHCRAIY-NHCUHLMSSA-N 0.000 claims 2
- XLVZRBHNHHAPDT-JWQCQUIFSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-morpholin-4-ylsulfonyl-3-phenyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)N2CCOCC2)C(C=2C=CC=CC=2)=C1C1=CC=C(F)C=C1 XLVZRBHNHHAPDT-JWQCQUIFSA-N 0.000 claims 2
- MCMLQAIONNZRDS-CZNDPXEESA-N (3r,5r)-7-[4-(4-benzylpiperidin-1-yl)sulfonyl-2-(4-fluorophenyl)-3-phenyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)N2CCC(CC=3C=CC=CC=3)CC2)C(C=2C=CC=CC=2)=C1C1=CC=C(F)C=C1 MCMLQAIONNZRDS-CZNDPXEESA-N 0.000 claims 2
- IYYNBGFAAGBIAX-KAYWLYCHSA-N (3r,5r)-7-[4-[(4-carbamoylphenyl)sulfamoyl]-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C=CC(=CC=2)C(N)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 IYYNBGFAAGBIAX-KAYWLYCHSA-N 0.000 claims 2
- YPIBHYNTGIQRFM-CZNDPXEESA-N (3r,5r)-7-[4-[benzyl(methyl)sulfamoyl]-2-(4-fluorophenyl)-3-naphthalen-2-yl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)N(C)CC=2C=CC=CC=2)C(C=2C=C3C=CC=CC3=CC=2)=C1C1=CC=C(F)C=C1 YPIBHYNTGIQRFM-CZNDPXEESA-N 0.000 claims 2
- BJCCVBSMTSQCBU-UHFFFAOYSA-N 7-[2,3-bis(4-fluorophenyl)-4-(3-hydroxypyrrolidin-1-yl)sulfonyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N2CC(O)CC2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 BJCCVBSMTSQCBU-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- KIVKPQGMDSCRCP-CLJLJLNGSA-N (3r,5r)-3,5-dihydroxy-7-[2-methyl-4,5-diphenyl-3-(phenylcarbamoyl)pyrrol-1-yl]heptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C(=O)NC1=CC=CC=C1 KIVKPQGMDSCRCP-CLJLJLNGSA-N 0.000 claims 1
- JNRWXTCRKDLOMP-DHIUTWEWSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-(2-hydroxyethylsulfamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NCCO)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 JNRWXTCRKDLOMP-DHIUTWEWSA-N 0.000 claims 1
- IBOSEKWSKZSPPO-FGZHOGPDSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-(methylsulfamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CNS(=O)(=O)C1=C(C(C)C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 IBOSEKWSKZSPPO-FGZHOGPDSA-N 0.000 claims 1
- GGTAZNWAYMFTSE-KAYWLYCHSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-(phenylsulfamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C=CC=CC=2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 GGTAZNWAYMFTSE-KAYWLYCHSA-N 0.000 claims 1
- SEZZCGWOOAGCDK-JWQCQUIFSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-[(2-fluorophenyl)sulfamoyl]-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C(=CC=CC=2)F)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 SEZZCGWOOAGCDK-JWQCQUIFSA-N 0.000 claims 1
- LAGMRFZEFTXAGD-KAYWLYCHSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-[(3-hydroxyphenyl)sulfamoyl]-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C=C(O)C=CC=2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 LAGMRFZEFTXAGD-KAYWLYCHSA-N 0.000 claims 1
- FQUFLKAWHATDII-DNQXCXABSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-[(3-methoxy-3-oxopropyl)sulfamoyl]-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound COC(=O)CCNS(=O)(=O)C1=C(C(C)C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 FQUFLKAWHATDII-DNQXCXABSA-N 0.000 claims 1
- CSGHRHYBJXXPIT-JWQCQUIFSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-[(4-methoxy-4-oxobutyl)sulfamoyl]-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound COC(=O)CCCNS(=O)(=O)C1=C(C(C)C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 CSGHRHYBJXXPIT-JWQCQUIFSA-N 0.000 claims 1
- JIPPVESEOYOSQW-KAYWLYCHSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-4-[(4-methylphenyl)sulfonylcarbamoyl]-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C(F)C=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JIPPVESEOYOSQW-KAYWLYCHSA-N 0.000 claims 1
- XCGWFMICIDDNOQ-FGZHOGPDSA-N (3r,5r)-7-[2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=CC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 XCGWFMICIDDNOQ-FGZHOGPDSA-N 0.000 claims 1
- UHPJSPZLMCUGMI-NHCUHLMSSA-N (3r,5r)-7-[2,5-dimethyl-3-(4-methylphenyl)-4-(2-methylpropylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)CNC(=O)C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C1=CC=C(C)C=C1 UHPJSPZLMCUGMI-NHCUHLMSSA-N 0.000 claims 1
- OIHTYCOSFLUBKF-JWQCQUIFSA-N (3r,5r)-7-[2,5-dimethyl-3-(4-methylphenyl)-4-(2-phenylethylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C(C)C=CC=1C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C(=O)NCCC1=CC=CC=C1 OIHTYCOSFLUBKF-JWQCQUIFSA-N 0.000 claims 1
- HGPSQDGTVKOWKB-CLJLJLNGSA-N (3r,5r)-7-[2,5-dimethyl-3-naphthalen-2-yl-4-(phenylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C(=O)NC1=CC=CC=C1 HGPSQDGTVKOWKB-CLJLJLNGSA-N 0.000 claims 1
- ZBAMCHZYDOFVFN-DNQXCXABSA-N (3r,5r)-7-[2,5-dimethyl-3-phenyl-4-(2-phenylethylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C(=O)NCCC1=CC=CC=C1 ZBAMCHZYDOFVFN-DNQXCXABSA-N 0.000 claims 1
- NAQZFJOPXABEQR-DNQXCXABSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-(phenylcarbamoyl)-3,5-di(propan-2-yl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C=1N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=C(C(C)C)C=1C(=O)NC1=CC=CC=C1 NAQZFJOPXABEQR-DNQXCXABSA-N 0.000 claims 1
- ZFOXOHPQJBQYLF-KAYWLYCHSA-N (3r,5r)-7-[2-benzyl-5-methyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(CC=2C=CC=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C(=O)NC1=CC=CC=C1 ZFOXOHPQJBQYLF-KAYWLYCHSA-N 0.000 claims 1
- IZIWAEKCFRLORN-RTBURBONSA-N (3r,5r)-7-[2-ethyl-4-(2-methoxyethylcarbamoyl)-3-(4-methoxyphenyl)-5-methylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound COCCNC(=O)C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C1C1=CC=C(OC)C=C1 IZIWAEKCFRLORN-RTBURBONSA-N 0.000 claims 1
- WVMDYKTXAYMSCR-VSGBNLITSA-N (3r,5r)-7-[2-ethyl-5-(4-fluorophenyl)-3-(phenylcarbamoyl)-4-(2-phenylethyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1CCC1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C1C(=O)NC1=CC=CC=C1 WVMDYKTXAYMSCR-VSGBNLITSA-N 0.000 claims 1
- SZXFALVZBQSUDK-DHIUTWEWSA-N (3r,5r)-7-[2-ethyl-5-(4-fluorophenyl)-3-(phenylcarbamoyl)-4-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C1C(=O)NC1=CC=CC=C1 SZXFALVZBQSUDK-DHIUTWEWSA-N 0.000 claims 1
- LKSZESMDAQOSJH-NHCUHLMSSA-N (3r,5r)-7-[2-ethyl-5-methyl-3-(4-methylphenyl)-4-(2-methylpropylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)CNC(=O)C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C1C1=CC=C(C)C=C1 LKSZESMDAQOSJH-NHCUHLMSSA-N 0.000 claims 1
- KRQMLAMKUIEIGP-FGZHOGPDSA-N (3r,5r)-7-[2-ethyl-5-methyl-3-(4-methylphenyl)-4-[(5-methylpyridin-2-yl)carbamoyl]pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC=1N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C(C=2C=CC(C)=CC=2)C=1C(=O)NC1=CC=C(C)C=N1 KRQMLAMKUIEIGP-FGZHOGPDSA-N 0.000 claims 1
- BEXXKAGSYPLZFT-FGZHOGPDSA-N (3r,5r)-7-[2-ethyl-5-methyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC=1N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C(C=2C=CC=CC=2)C=1C(=O)NC1=CC=CC=C1 BEXXKAGSYPLZFT-FGZHOGPDSA-N 0.000 claims 1
- WWBJUTMZVHLGQR-JWQCQUIFSA-N (3r,5r)-7-[2-ethyl-5-methyl-4-[(5-methylpyridin-2-yl)carbamoyl]-3-naphthalen-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC=1N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C(C=2C=C3C=CC=CC3=CC=2)C=1C(=O)NC1=CC=C(C)C=N1 WWBJUTMZVHLGQR-JWQCQUIFSA-N 0.000 claims 1
- NVGBGYPNRGPJDD-JWQCQUIFSA-N (3r,5r)-7-[3-(3,4-difluorophenyl)-2-(4-fluorophenyl)-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C(F)C(F)=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 NVGBGYPNRGPJDD-JWQCQUIFSA-N 0.000 claims 1
- AEXLOHRFUYQDSN-KAYWLYCHSA-N (3r,5r)-7-[3-(4-bromophenyl)-2-(4-fluorophenyl)-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C(Br)C=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 AEXLOHRFUYQDSN-KAYWLYCHSA-N 0.000 claims 1
- HVFWSYIJLMLDCD-DHIUTWEWSA-N (3r,5r)-7-[3-(4-chlorophenyl)-2-methyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C(Cl)C=CC=1C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 HVFWSYIJLMLDCD-DHIUTWEWSA-N 0.000 claims 1
- JRXVKOOTECVCMY-VSGBNLITSA-N (3r,5r)-7-[3-(4-cyanophenyl)-2-(4-fluorophenyl)-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C(C#N)C=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 JRXVKOOTECVCMY-VSGBNLITSA-N 0.000 claims 1
- TZAIZWPNWWYRRF-DNQXCXABSA-N (3r,5r)-7-[3-(benzylcarbamoyl)-2,5-dimethyl-4-(4-methylphenyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C(C)C=CC=1C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C(=O)NCC1=CC=CC=C1 TZAIZWPNWWYRRF-DNQXCXABSA-N 0.000 claims 1
- YYPQKQMTXKFVFM-KAYWLYCHSA-N (3r,5r)-7-[3-(benzylcarbamoyl)-2,5-dimethyl-4-naphthalen-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C(=O)NCC1=CC=CC=C1 YYPQKQMTXKFVFM-KAYWLYCHSA-N 0.000 claims 1
- JIEFNAVRIXAHAZ-DHIUTWEWSA-N (3r,5r)-7-[3-(benzylcarbamoyl)-2,5-dimethyl-4-phenylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C)=C1C(=O)NCC1=CC=CC=C1 JIEFNAVRIXAHAZ-DHIUTWEWSA-N 0.000 claims 1
- UZSIVXWLNHWLJI-DNQXCXABSA-N (3r,5r)-7-[3-(benzylcarbamoyl)-2-ethyl-5-(4-fluorophenyl)-4-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C1C(=O)NCC1=CC=CC=C1 UZSIVXWLNHWLJI-DNQXCXABSA-N 0.000 claims 1
- WUMJOAABPZYWCH-DNQXCXABSA-N (3r,5r)-7-[3-cyclopropyl-2-(4-fluorophenyl)-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C1CC1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 WUMJOAABPZYWCH-DNQXCXABSA-N 0.000 claims 1
- OYNDDZPZIGAPOU-DNQXCXABSA-N (3r,5r)-7-[4-(benzylcarbamoyl)-2-ethyl-5-methyl-3-(4-methylphenyl)pyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC=1N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C(C=2C=CC(C)=CC=2)C=1C(=O)NCC1=CC=CC=C1 OYNDDZPZIGAPOU-DNQXCXABSA-N 0.000 claims 1
- YFTOJHNOFHMDOD-KAYWLYCHSA-N (3r,5r)-7-[4-(benzylcarbamoyl)-2-ethyl-5-methyl-3-naphthalen-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC=1N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C(C=2C=C3C=CC=CC3=CC=2)C=1C(=O)NCC1=CC=CC=C1 YFTOJHNOFHMDOD-KAYWLYCHSA-N 0.000 claims 1
- GQTVZLUUKTVVSM-DHIUTWEWSA-N (3r,5r)-7-[4-(benzylcarbamoyl)-2-ethyl-5-methyl-3-phenylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC=1N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(CC)=C(C=2C=CC=CC=2)C=1C(=O)NCC1=CC=CC=C1 GQTVZLUUKTVVSM-DHIUTWEWSA-N 0.000 claims 1
- HSCBDNLELBVHGZ-VSGBNLITSA-N (3r,5r)-7-[4-(benzylsulfamoyl)-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NCC=2C=CC=CC=2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 HSCBDNLELBVHGZ-VSGBNLITSA-N 0.000 claims 1
- TWLYCNYHZSEOGO-JWQCQUIFSA-N (3r,5r)-7-[4-[(2,4-difluorophenyl)sulfamoyl]-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C(=CC(F)=CC=2)F)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 TWLYCNYHZSEOGO-JWQCQUIFSA-N 0.000 claims 1
- PJKOCENLPLSPMH-FIRIVFDPSA-N (3r,5r)-7-[4-[[4-(diethylcarbamoyl)phenyl]carbamoyl]-2-(4-fluorophenyl)-3-phenyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1NC(=O)C1=C(C(C)C)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=CC=C1 PJKOCENLPLSPMH-FIRIVFDPSA-N 0.000 claims 1
- CPCXUELBVSHIEL-FQLXRVMXSA-N (3r,5r)-7-[4-[[4-(dimethylcarbamoyl)phenyl]carbamoyl]-2-(4-fluorophenyl)-3-phenyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=C(C(=O)N(C)C)C=C1 CPCXUELBVSHIEL-FQLXRVMXSA-N 0.000 claims 1
- WOVMFAYOKUVUBG-FQLXRVMXSA-N (3r,5r)-7-[4-[benzyl(methyl)sulfamoyl]-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)N(C)CC=2C=CC=CC=2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 WOVMFAYOKUVUBG-FQLXRVMXSA-N 0.000 claims 1
- DPJYUKITYJCXFR-LOYHVIPDSA-N (3r,5r)-7-[4-[benzyl(methyl)sulfamoyl]-2-(4-fluorophenyl)-3-(4-methylphenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)N(C)CC=2C=CC=CC=2)C(C=2C=CC(C)=CC=2)=C1C1=CC=C(F)C=C1 DPJYUKITYJCXFR-LOYHVIPDSA-N 0.000 claims 1
- OYRGSYOYPNIAOP-NHCUHLMSSA-N (3r,5r)-7-[4-carbamoyl-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(C(N)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 OYRGSYOYPNIAOP-NHCUHLMSSA-N 0.000 claims 1
- MQMZSTRGZBTIOD-CLJLJLNGSA-N 1-[1-[(3r,5r)-6-carboxy-3,5-dihydroxyhexyl]-4,5-bis(4-fluorophenyl)-2-propan-2-ylpyrrol-3-yl]sulfonylpiperidine-4-carboxylic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)N2CCC(CC2)C(O)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 MQMZSTRGZBTIOD-CLJLJLNGSA-N 0.000 claims 1
- GHBFJWDEPVRHRO-KAYWLYCHSA-N 4-[[1-[(3r,5r)-6-carboxy-3,5-dihydroxyhexyl]-4,5-bis(4-fluorophenyl)-2-propan-2-ylpyrrol-3-yl]sulfonylamino]benzoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCN1C(C(C)C)=C(S(=O)(=O)NC=2C=CC(=CC=2)C(O)=O)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 GHBFJWDEPVRHRO-KAYWLYCHSA-N 0.000 claims 1
- WKMANDQIEZJPPF-KAYWLYCHSA-N 4-[[1-[(3r,5r)-6-carboxy-3,5-dihydroxyhexyl]-5-(4-fluorophenyl)-4-phenyl-2-propan-2-ylpyrrole-3-carbonyl]amino]benzoic acid Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=C(C(O)=O)C=C1 WKMANDQIEZJPPF-KAYWLYCHSA-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
- VZTBEFJGMWJRAX-UHFFFAOYSA-N 7-[2,3-bis(4-fluorophenyl)-4-(3-phenylpyrrolidin-1-yl)sulfonyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N2CC(CC2)C=2C=CC=CC=2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 VZTBEFJGMWJRAX-UHFFFAOYSA-N 0.000 claims 1
- CHQBMRGZFGYNIT-UHFFFAOYSA-N 7-[2,3-bis(4-fluorophenyl)-4-(4-hydroxypiperidin-1-yl)sulfonyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N2CCC(O)CC2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 CHQBMRGZFGYNIT-UHFFFAOYSA-N 0.000 claims 1
- XVVOCWSNJNTFPT-UHFFFAOYSA-N 7-[2,3-bis(4-fluorophenyl)-5-propan-2-yl-4-pyrrolidin-1-ylsulfonylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N2CCCC2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 XVVOCWSNJNTFPT-UHFFFAOYSA-N 0.000 claims 1
- IKPHTPMSGDEMSI-UHFFFAOYSA-N 7-[2,3-bis(4-fluorophenyl)-5-propan-2-yl-4-thiomorpholin-4-ylsulfonylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N2CCSCC2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 IKPHTPMSGDEMSI-UHFFFAOYSA-N 0.000 claims 1
- XRDUMVZFAPCQLQ-UHFFFAOYSA-N 7-[4-(2,6-dimethylmorpholin-4-yl)sulfonyl-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N2CC(C)OC(C)C2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 XRDUMVZFAPCQLQ-UHFFFAOYSA-N 0.000 claims 1
- BHXXJVSXVOEACS-UHFFFAOYSA-N 7-[4-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-ylsulfonyl)-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N2CC3CCCCC3CC2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 BHXXJVSXVOEACS-UHFFFAOYSA-N 0.000 claims 1
- OJSUFHURMKEJKK-UHFFFAOYSA-N 7-[4-(3-azaspiro[5.5]undecan-3-ylsulfonyl)-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N2CCC3(CCCCC3)CC2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 OJSUFHURMKEJKK-UHFFFAOYSA-N 0.000 claims 1
- IDEMXDXAGMQPOR-UHFFFAOYSA-N 7-[4-(diphenylsulfamoyl)-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)CC(O)CC(O)CCN1C(C(C)C)=C(S(=O)(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 IDEMXDXAGMQPOR-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| US49421603P | 2003-08-11 | 2003-08-11 | |
| PCT/IB2004/002540 WO2005014539A2 (en) | 2003-08-11 | 2004-07-30 | Pyrrole-based hmg-coa reductase inhibitors |
Publications (2)
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| JP2007502265A JP2007502265A (ja) | 2007-02-08 |
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| EP (1) | EP1656132A2 (enExample) |
| JP (1) | JP2007502265A (enExample) |
| BR (1) | BRPI0413468A (enExample) |
| CA (1) | CA2534494A1 (enExample) |
| MX (1) | MXPA06001721A (enExample) |
| WO (1) | WO2005014539A2 (enExample) |
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| SG141430A1 (en) | 2003-05-30 | 2008-04-28 | Ranbaxy Lab Ltd | Substituted pyrrole derivatives and their use as hmg-co inhibitors |
| US7163945B2 (en) * | 2004-04-29 | 2007-01-16 | Pharmix Corp. | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US20050282883A1 (en) * | 2004-04-29 | 2005-12-22 | John Griffin | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US20060084695A1 (en) * | 2004-04-29 | 2006-04-20 | John Griffin | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US20050272770A1 (en) * | 2004-04-29 | 2005-12-08 | John Griffin | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US7199126B2 (en) | 2004-04-29 | 2007-04-03 | Pharmix Corporation | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US7183285B2 (en) * | 2004-04-29 | 2007-02-27 | Pharmix Corp. | Compositions and treatments for inhibiting kinase and/or HMG-CoA reductase |
| US20060111436A1 (en) * | 2004-11-23 | 2006-05-25 | John Griffin | Compositions and treatments for modulating kinase and/or HMG-CoA reductase |
| ES2328384T3 (es) * | 2004-11-23 | 2009-11-12 | Warner-Lambert Company Llc | Derivados del acido 7-(2h-pirazol-3-il)-3,5-dihidroxi-heptanoico como inhibidores de hmg co-a reductasa para el tratamiento de la lipidemia. |
| WO2007042910A1 (en) * | 2005-10-14 | 2007-04-19 | Pfizer Products Inc. | Imidazoles and their use as hmg-coa reductase inhibitors |
| BRPI0618379A2 (pt) * | 2005-11-08 | 2011-08-30 | Ranbaxy Lab Ltd | processo para preparação do hemi-sal de cálcio do ácido (3r,5r) -7-[2-(4-fluorofenil)-5-isopropil-3-fenil-4-[(4-hidroxime tilfenilamino) carbonil]-pirrol-1-il] -3, 5-diidroxi heptanóico |
| NZ574028A (en) | 2006-07-05 | 2010-10-29 | Fibrotech Therapeutics Pty Ltd | Tranilast analogues (substituted cinnamoyl anthranilate compounds) for treatment of conditions associated with firbrosis |
| ES2289945B1 (es) * | 2006-07-21 | 2008-12-16 | Ercros Industrial, S.A | Procedimiento para la obtencion de dos intermedios avanzados y su uso para la obtencion de atorvastatina calcica amorfa. |
| SG10201506526QA (en) * | 2007-12-21 | 2015-09-29 | Fibrotech Therapeutics Pty Ltd | Halogenated analogues of anti-fibrotic agents |
| WO2009120783A1 (en) * | 2008-03-25 | 2009-10-01 | The Johns Hopkins University | High affinity inhibitors of hepatitis c virus ns3/4a protease |
| EP2947073B1 (en) | 2009-10-22 | 2019-04-03 | Fibrotech Therapeutics Pty Ltd | Fused ring analogues of anti-fibrotic agents |
| US9107983B2 (en) | 2010-10-27 | 2015-08-18 | Warsaw Orthopedic, Inc. | Osteoconductive matrices comprising statins |
| US8877221B2 (en) | 2010-10-27 | 2014-11-04 | Warsaw Orthopedic, Inc. | Osteoconductive matrices comprising calcium phosphate particles and statins and methods of using the same |
| EP2511263A1 (en) | 2011-04-14 | 2012-10-17 | Phenex Pharmaceuticals AG | Pyrrolo sulfonamide compounds for modulation of orphan nuclear receptor RAR-related orphan receptor-gamma (RORgamma, NR1F3) activity and for the treatment of chronic inflammatory and autoimmune diseases |
| US9308190B2 (en) | 2011-06-06 | 2016-04-12 | Warsaw Orthopedic, Inc. | Methods and compositions to enhance bone growth comprising a statin |
| WO2016122325A1 (en) | 2015-01-30 | 2016-08-04 | Rijksuniversiteit Groningen | Methods for providing intermediates in the synthesis of atorvastatin. |
| JP2020502064A (ja) * | 2016-11-29 | 2020-01-23 | エピザイム，インコーポレイティド | スルホン酸基を含むｋａｔ阻害剤としての化合物 |
| EP3577103A1 (en) | 2017-02-03 | 2019-12-11 | Certa Therapeutics Pty Ltd. | Anti-fibrotic compounds |
| CN108250194A (zh) * | 2018-02-12 | 2018-07-06 | 李化绪 | 一种二氟苯并噻唑类化合物及其在降血脂药物中的应用 |
| US12139461B1 (en) | 2024-04-22 | 2024-11-12 | King Saud University | Piperidine compounds as PDE5 inhibitors |
| CN119462750A (zh) * | 2025-01-08 | 2025-02-18 | 浙江先锋科技集团股份有限公司 | 一种阿托伐他汀钙衍生物及其制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5612114B2 (enExample) | 1974-06-07 | 1981-03-18 | ||
| US4049495A (en) | 1974-06-07 | 1977-09-20 | Sankyo Company Limited | Physiologically active substances and fermentative process for producing the same |
| US4137322A (en) | 1976-11-02 | 1979-01-30 | Sankyo Company Limited | ML-236B carboxylic acid derivatives and their use as antihyperlipemic agents |
| JPS53147073A (en) | 1977-05-24 | 1978-12-21 | Sankyo Co Ltd | Mevalonolactone derivatives |
| JPS5559180A (en) | 1978-10-30 | 1980-05-02 | Sankyo Co Ltd | 4-hydroxy-2-pyrone ring compound, its preparation, and remedy for hyperlipemia comprising it as active constituent |
| US4375475A (en) | 1979-08-17 | 1983-03-01 | Merck & Co., Inc. | Substituted pyranone inhibitors of cholesterol synthesis |
| AU598775B2 (en) | 1985-10-25 | 1990-07-05 | Sandoz Ag | Heterocyclic analogs of mevalonolactone |
| US4851427A (en) | 1985-10-25 | 1989-07-25 | Sandoz Pharm. Corp. | Pyrrole analogs of mevalonolactone, derivatives thereof and pharmaceutical use |
| US4681893A (en) | 1986-05-30 | 1987-07-21 | Warner-Lambert Company | Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis |
| DE3722806A1 (de) | 1987-07-10 | 1989-01-19 | Hoechst Ag | 7-(1h-pyrrol-3-yl)-substituierte 3,5-dihydroxy-hept-6-ensaeuren, 7-(1h-pyrrol-3-yl)-substituierte 3,5-dihydroxy-heptansaeuren, ihre entsprechenden (delta)-lactone und salze, verfahren zu ihrer herstellung ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte |
| DE3832570A1 (de) | 1988-09-24 | 1990-03-29 | Hoechst Ag | 7-substituierte derivate der 3,5-dihydroxyhept-6-insaeure, verfahren zur ihrer herstellung, ihre verwendung als arzneimittel, sowie zwischenprodukte |
| US5385929A (en) | 1994-05-04 | 1995-01-31 | Warner-Lambert Company | [(Hydroxyphenylamino) carbonyl] pyrroles |
| US6376476B1 (en) | 1996-12-13 | 2002-04-23 | Zymogenetics Corporation | Isoprenoid pathway inhibitors for stimulating bone growth |
| CA2417277A1 (en) * | 2000-07-27 | 2002-02-07 | F. Hoffmann-La Roche Ag | 3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3.beta. |
| US7078430B2 (en) | 2002-07-08 | 2006-07-18 | Ranbaxy Laboratories Limited | HMG CoA-reductase inhibitors |
-
2004
- 2004-06-07 US US10/862,844 patent/US7250444B2/en not_active Expired - Fee Related
- 2004-07-30 WO PCT/IB2004/002540 patent/WO2005014539A2/en not_active Ceased
- 2004-07-30 MX MXPA06001721A patent/MXPA06001721A/es not_active Application Discontinuation
- 2004-07-30 EP EP04769110A patent/EP1656132A2/en not_active Withdrawn
- 2004-07-30 CA CA002534494A patent/CA2534494A1/en not_active Abandoned
- 2004-07-30 BR BRPI0413468-0A patent/BRPI0413468A/pt not_active IP Right Cessation
- 2004-07-30 JP JP2006523069A patent/JP2007502265A/ja not_active Withdrawn
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