JP2008520642A5 - - Google Patents
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- Publication number
- JP2008520642A5 JP2008520642A5 JP2007542152A JP2007542152A JP2008520642A5 JP 2008520642 A5 JP2008520642 A5 JP 2008520642A5 JP 2007542152 A JP2007542152 A JP 2007542152A JP 2007542152 A JP2007542152 A JP 2007542152A JP 2008520642 A5 JP2008520642 A5 JP 2008520642A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- phenyl
- isopropyl
- pyrazol
- dihydroxy
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 73
- 125000003118 aryl group Chemical group 0.000 claims 63
- 125000003710 aryl alkyl group Chemical group 0.000 claims 61
- 125000001072 heteroaryl group Chemical group 0.000 claims 47
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 45
- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 239000001257 hydrogen Substances 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 30
- 150000002431 hydrogen Chemical class 0.000 claims 30
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 27
- -1 (3R, 5R) -7- [2- (4-Fluoro-phenyl) -4-isopropyl-5- (2-methyl-benzylcarbamoyl) -2H-pyrazol-3-yl] -3,5-dihydroxy-heptane Chemical compound 0.000 claims 23
- 239000002253 acid Substances 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 230000000707 stereoselective effect Effects 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 claims 2
- YLAVHPQPEFUCRY-FLZRTACHSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(3-phenylpiperidine-1-carbonyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N(C1)CCCC1C1=CC=CC=C1 YLAVHPQPEFUCRY-FLZRTACHSA-N 0.000 claims 2
- LGIQZDCMCVISNA-IAGOWNOFSA-N (3r,5r)-7-[5-(ethylcarbamoyl)-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCC1=C(C(C)C)C(C(=O)NCC)=NN1C1=CC=C(F)C=C1 LGIQZDCMCVISNA-IAGOWNOFSA-N 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000003981 vehicle Substances 0.000 claims 2
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 claims 1
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 1
- FTWSRGZZXBAIMY-FCHUYYIVSA-N (3R,5R)-7-[5-(cyclohexylmethylcarbamoyl)-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NCC2CCCCC2)=NN1C1=CC=C(F)C=C1 FTWSRGZZXBAIMY-FCHUYYIVSA-N 0.000 claims 1
- BCESRJXZWFDATD-RBUKOAKNSA-N (3R,5R)-7-[5-(cyclopropylmethylcarbamoyl)-2-(4-fluorophenyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NCC2CC2)=NN1C1=CC=C(F)C=C1 BCESRJXZWFDATD-RBUKOAKNSA-N 0.000 claims 1
- WOIWYAXSQWDKMG-ZWKOTPCHSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-(propan-2-ylcarbamoyl)pyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NC(C)C)=NN1C1=CC=C(F)C=C1 WOIWYAXSQWDKMG-ZWKOTPCHSA-N 0.000 claims 1
- XKDOBGDKXJUWAH-QZTJIDSGSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-(propan-2-ylcarbamoyl)pyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCC1=C(C(C)C)C(C(=O)NC(C)C)=NN1C1=CC=C(F)C=C1 XKDOBGDKXJUWAH-QZTJIDSGSA-N 0.000 claims 1
- HSFWAGSFENDBQO-ZWKOTPCHSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-(propylcarbamoyl)pyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NCCC)=NN1C1=CC=C(F)C=C1 HSFWAGSFENDBQO-ZWKOTPCHSA-N 0.000 claims 1
- ACIPTBZVKPBAMM-QZTJIDSGSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-(propylcarbamoyl)pyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCC1=C(C(C)C)C(C(=O)NCCC)=NN1C1=CC=C(F)C=C1 ACIPTBZVKPBAMM-QZTJIDSGSA-N 0.000 claims 1
- GOPDJHRHNYXVBI-NHCUHLMSSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-(pyridin-2-ylmethylcarbamoyl)pyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1=CC=CC=N1 GOPDJHRHNYXVBI-NHCUHLMSSA-N 0.000 claims 1
- FOKZKVHFKJGDPQ-NHCUHLMSSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-[[5-(trifluoromethyl)pyridin-2-yl]methylcarbamoyl]pyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1=CC=C(C(F)(F)F)C=N1 FOKZKVHFKJGDPQ-NHCUHLMSSA-N 0.000 claims 1
- IKNGQNUFXFIYHT-RTMXWXTASA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-[[6-(trifluoromethyl)piperidin-3-yl]methylcarbamoyl]pyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1CCC(C(F)(F)F)NC1 IKNGQNUFXFIYHT-RTMXWXTASA-N 0.000 claims 1
- QUONIPBKORDMFV-WOJBJXKFSA-N (3r,5r)-7-[2-(4-fluorophenyl)-4-propan-2-yl-5-[[6-(trifluoromethyl)pyridin-3-yl]methylcarbamoyl]pyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1=CC=C(C(F)(F)F)N=C1 QUONIPBKORDMFV-WOJBJXKFSA-N 0.000 claims 1
- MCVRIAPNBNCEBZ-RTBURBONSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-methylpropylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCC1=C(C(C)C)C(C(=O)NCC(C)C)=NN1C1=CC=C(F)C=C1 MCVRIAPNBNCEBZ-RTBURBONSA-N 0.000 claims 1
- RPTHLXOOASOTAZ-DHIUTWEWSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-phenylethylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCCC1=CC=CC=C1 RPTHLXOOASOTAZ-DHIUTWEWSA-N 0.000 claims 1
- DGPVRQDECQBJDH-YFHSQZFMSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-phenylpiperidine-1-carbonyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N1CCCCC1C1=CC=CC=C1 DGPVRQDECQBJDH-YFHSQZFMSA-N 0.000 claims 1
- VPBKAPKIGWAXHB-DHIUTWEWSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-phenylpropan-2-ylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NC(C)(C)C1=CC=CC=C1 VPBKAPKIGWAXHB-DHIUTWEWSA-N 0.000 claims 1
- JDNNJMMIANDJER-AEAWWFNXSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(2-phenylpyrrolidine-1-carbonyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N1CCCC1C1=CC=CC=C1 JDNNJMMIANDJER-AEAWWFNXSA-N 0.000 claims 1
- PRDKLZUWWGIJKD-VQTJNVASSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(3-methylbutylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NCCC(C)C)=NN1C1=CC=C(F)C=C1 PRDKLZUWWGIJKD-VQTJNVASSA-N 0.000 claims 1
- ZVIGYIARKWWQTG-JKSUJKDBSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(methylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@@H](O)C=CC1=C(C(C)C)C(C(=O)NC)=NN1C1=CC=C(F)C=C1 ZVIGYIARKWWQTG-JKSUJKDBSA-N 0.000 claims 1
- UCPFWXTXESQPTQ-HZPDHXFCSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(methylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)CCC1=C(C(C)C)C(C(=O)NC)=NN1C1=CC=C(F)C=C1 UCPFWXTXESQPTQ-HZPDHXFCSA-N 0.000 claims 1
- QCBVKGXNVHZNLH-RTBURBONSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(morpholine-4-carbonyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N1CCOCC1 QCBVKGXNVHZNLH-RTBURBONSA-N 0.000 claims 1
- XNGHJMJEQHCIOC-LEWJYISDSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(phenylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(C=C[C@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NC1=CC=CC=C1 XNGHJMJEQHCIOC-LEWJYISDSA-N 0.000 claims 1
- PMJFIOMWVYRGGP-NHCUHLMSSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(phenylcarbamoyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NC1=CC=CC=C1 PMJFIOMWVYRGGP-NHCUHLMSSA-N 0.000 claims 1
- PHZAQTLVZUCQDQ-WOJBJXKFSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-(piperidine-1-carbonyl)-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N1CCCCC1 PHZAQTLVZUCQDQ-WOJBJXKFSA-N 0.000 claims 1
- CWNFWNFUXTYABU-FGZHOGPDSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[(2-fluorophenyl)methyl-methylcarbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N(C)CC1=CC=CC=C1F CWNFWNFUXTYABU-FGZHOGPDSA-N 0.000 claims 1
- BMAUPGGGUVOBPD-WELAQSEPSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[(2-hydroxy-1-phenylethyl)carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NC(CO)C1=CC=CC=C1 BMAUPGGGUVOBPD-WELAQSEPSA-N 0.000 claims 1
- CCBZZAWXLNARGV-XZOQPEGZSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[(2-methylphenyl)methylcarbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(C=C[C@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)NCC1=CC=CC=C1C CCBZZAWXLNARGV-XZOQPEGZSA-N 0.000 claims 1
- OQAJLGZZINRLJK-DHIUTWEWSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[(3-fluorophenyl)methyl-methylcarbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound CC(C)C1=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(C=2C=CC(F)=CC=2)N=C1C(=O)N(C)CC1=CC=CC(F)=C1 OQAJLGZZINRLJK-DHIUTWEWSA-N 0.000 claims 1
- WQGNWURCKXFIDD-DHIUTWEWSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[(3-methoxyphenyl)methyl-methylcarbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound COC1=CC=CC(CN(C)C(=O)C=2C(=C(CC[C@@H](O)C[C@@H](O)CC(O)=O)N(N=2)C=2C=CC(F)=CC=2)C(C)C)=C1 WQGNWURCKXFIDD-DHIUTWEWSA-N 0.000 claims 1
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- AEYTZQNRVNCKDQ-DHIUTWEWSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methyl-methylcarbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoic acid Chemical compound C1=CC(OC)=CC=C1CN(C)C(=O)C1=NN(C=2C=CC(F)=CC=2)C(CC[C@@H](O)C[C@@H](O)CC(O)=O)=C1C(C)C AEYTZQNRVNCKDQ-DHIUTWEWSA-N 0.000 claims 1
- LHZGPODOUGJZDT-FCHUYYIVSA-N (3r,5r)-7-[2-(4-fluorophenyl)-5-[(4-methoxyphenyl)methylcarbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=NN(C=2C=CC(F)=CC=2)C(C=C[C@H](O)C[C@@H](O)CC(O)=O)=C1C(C)C LHZGPODOUGJZDT-FCHUYYIVSA-N 0.000 claims 1
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| WO2007107843A1 (en) * | 2006-03-22 | 2007-09-27 | Pfizer Products Inc. | Methods of treatment with cetp inhibitors |
| US7834050B2 (en) | 2006-03-29 | 2010-11-16 | Duke University | Small molecule insulin mimetics absent quinones |
| WO2008059372A2 (en) * | 2006-11-17 | 2008-05-22 | Pfizer Products Inc. | Crystal form of (3r,5r)-7-[2-(4-fluoro-phenyl)-4-isopropyl-5-(4-metyl-benzylcarbamoyl)-2h-pyrazol-3-yl]-3,5-dihydroxy-heptanoic acid sodium salt |
| KR20130132816A (ko) * | 2010-10-21 | 2013-12-05 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 1-(헤테로시클릭 카르보닐) 피페리딘 |
| AR087701A1 (es) * | 2011-08-31 | 2014-04-09 | Japan Tobacco Inc | Derivados de pirazol con actividad inhibidora de sglt1 |
| CA3085086C (en) | 2011-12-06 | 2023-08-08 | Delta Faucet Company | Ozone distribution in a faucet |
| CN108463437B (zh) | 2015-12-21 | 2022-07-08 | 德尔塔阀门公司 | 包括消毒装置的流体输送系统 |
| MX2020010433A (es) * | 2018-04-04 | 2020-10-28 | Japan Tobacco Inc | Compuestos de pirazol sustituidos con heteroarilo y uso farmaceutico de los mismos. |
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-
2005
- 2005-11-14 WO PCT/IB2005/003461 patent/WO2006056845A1/en not_active Ceased
- 2005-11-14 AP AP2007003979A patent/AP2007003979A0/xx unknown
- 2005-11-14 MX MX2007005137A patent/MX2007005137A/es not_active Application Discontinuation
- 2005-11-14 KR KR1020077011587A patent/KR20070084455A/ko not_active Ceased
- 2005-11-14 AU AU2005308575A patent/AU2005308575A1/en not_active Abandoned
- 2005-11-14 JP JP2007542152A patent/JP2008520642A/ja active Pending
- 2005-11-14 EP EP05801166A patent/EP1819681B1/en not_active Expired - Lifetime
- 2005-11-14 AT AT05801166T patent/ATE439347T1/de not_active IP Right Cessation
- 2005-11-14 BR BRPI0518300-6A patent/BRPI0518300A2/pt not_active Application Discontinuation
- 2005-11-14 CA CA2590533A patent/CA2590533C/en not_active Expired - Fee Related
- 2005-11-14 DE DE602005016009T patent/DE602005016009D1/de not_active Expired - Lifetime
- 2005-11-14 ES ES05801166T patent/ES2328384T3/es not_active Expired - Lifetime
- 2005-11-14 EA EA200700875A patent/EA200700875A1/ru unknown
- 2005-11-18 US US11/283,264 patent/US7446121B2/en not_active Expired - Fee Related
- 2005-11-21 UY UY29220A patent/UY29220A1/es not_active Application Discontinuation
- 2005-11-21 AR ARP050104871A patent/AR052244A1/es unknown
- 2005-11-21 PE PE2005001361A patent/PE20061057A1/es not_active Application Discontinuation
- 2005-11-22 GT GT200500338A patent/GT200500338A/es unknown
- 2005-11-22 NL NL1030487A patent/NL1030487C2/nl not_active IP Right Cessation
- 2005-11-22 TW TW094140920A patent/TW200626556A/zh unknown
- 2005-11-23 PA PA20058653401A patent/PA8653401A1/es unknown
-
2007
- 2007-04-16 IL IL182569A patent/IL182569A0/en unknown
- 2007-05-03 CR CR9102A patent/CR9102A/es not_active Application Discontinuation
- 2007-05-22 TN TNP2007000202A patent/TNSN07202A1/fr unknown
- 2007-05-23 MA MA29934A patent/MA30108B1/fr unknown
-
2008
- 2008-10-08 US US12/247,434 patent/US20090170852A1/en not_active Abandoned
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