ZA200607491B - Tetrahydrocarbazoles and derivatives - Google Patents
Tetrahydrocarbazoles and derivatives Download PDFInfo
- Publication number
- ZA200607491B ZA200607491B ZA200607491A ZA200607491A ZA200607491B ZA 200607491 B ZA200607491 B ZA 200607491B ZA 200607491 A ZA200607491 A ZA 200607491A ZA 200607491 A ZA200607491 A ZA 200607491A ZA 200607491 B ZA200607491 B ZA 200607491B
- Authority
- ZA
- South Africa
- Prior art keywords
- tetrahydro
- benzenesulfonyl
- chloro
- fluoro
- methyl
- Prior art date
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- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 136
- 150000001875 compounds Chemical class 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 60
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- -1 -OR" Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 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 description 24
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 102000004311 liver X receptors Human genes 0.000 claims description 17
- 108090000865 liver X receptors Proteins 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 108010023302 HDL Cholesterol Proteins 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 7
- 101000603962 Homo sapiens Oxysterols receptor LXR-alpha Proteins 0.000 claims description 7
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 7
- 102100038476 Oxysterols receptor LXR-alpha Human genes 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 239000000556 agonist Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 230000001225 therapeutic effect Effects 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 108010028554 LDL Cholesterol Proteins 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 238000008214 LDL Cholesterol Methods 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 6
- QGRVHWHTSMJVAO-ASSNKEHSSA-N 2-[(s)-benzenesulfonyl-[(2r)-7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl]-fluoromethyl]-5-methyl-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1[C@@](F)(S(=O)(=O)C=1C=CC=CC=1)[C@@H]1CC(C2=CC(Cl)=CC=C2N2)=C2C1 QGRVHWHTSMJVAO-ASSNKEHSSA-N 0.000 claims 2
- HHZARSUSZWXWSW-UHFFFAOYSA-N 4-[5-[(3-bromophenyl)sulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,3,4-oxadiazol-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN=C(C(F)(C2CC=3C4=CC(Cl)=CC=C4NC=3C2)S(=O)(=O)C=2C=C(Br)C=CC=2)O1 HHZARSUSZWXWSW-UHFFFAOYSA-N 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- TUCXLHQHQHEHBR-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoroacetate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 TUCXLHQHQHEHBR-UHFFFAOYSA-N 0.000 claims 2
- QOBDEGBTZBXABV-UHFFFAOYSA-N 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoro-2-(3-fluorophenyl)sulfonyl-n-methylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)NC)S(=O)(=O)C1=CC=CC(F)=C1 QOBDEGBTZBXABV-UHFFFAOYSA-N 0.000 claims 1
- VCOOISFXECVQHF-UHFFFAOYSA-N 2-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-2-fluoro-2-(3-fluorophenyl)sulfonyl-n,n-dimethylacetamide Chemical compound C1C=2NC3=CC=C(Cl)C=C3C=2CC1C(F)(C(=O)N(C)C)S(=O)(=O)C1=CC=CC(F)=C1 VCOOISFXECVQHF-UHFFFAOYSA-N 0.000 claims 1
- KQLRHPOTEHVMLF-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoro-n,n-dimethylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)N(C)C)S(=O)(=O)C1=CC=CC=C1 KQLRHPOTEHVMLF-UHFFFAOYSA-N 0.000 claims 1
- CLGCDBZWUTZXRX-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoro-n-[[3-(hydroxymethyl)phenyl]methyl]-n-methylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(=O)N(C)CC1=CC=CC(CO)=C1 CLGCDBZWUTZXRX-UHFFFAOYSA-N 0.000 claims 1
- GCERQXUDTVICGM-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoroacetic acid Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)O)S(=O)(=O)C1=CC=CC=C1 GCERQXUDTVICGM-UHFFFAOYSA-N 0.000 claims 1
- FASYQVKGESCKCC-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-n-[(2-cyanophenyl)methyl]-2-fluoro-n-methylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(=O)N(C)CC1=CC=CC=C1C#N FASYQVKGESCKCC-UHFFFAOYSA-N 0.000 claims 1
- CONFWTSTTAJTDM-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-n-[(3,5-difluorophenyl)methyl]-2-fluoro-n-methylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(=O)N(C)CC1=CC(F)=CC(F)=C1 CONFWTSTTAJTDM-UHFFFAOYSA-N 0.000 claims 1
- RAZKNXOGBBKEBS-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-n-[(3-cyanophenyl)methyl]-2-fluoro-n-methylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(=O)N(C)CC1=CC=CC(C#N)=C1 RAZKNXOGBBKEBS-UHFFFAOYSA-N 0.000 claims 1
- RHOGTWGVJNVZGO-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-n-[(4-cyanophenyl)methyl]-2-fluoro-n-methylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(=O)N(C)CC1=CC=C(C#N)C=C1 RHOGTWGVJNVZGO-UHFFFAOYSA-N 0.000 claims 1
- WIEYQOIYFJKIDH-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanoic acid Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(C(O)=O)S(=O)(=O)C1=CC=CC=C1 WIEYQOIYFJKIDH-UHFFFAOYSA-N 0.000 claims 1
- BFYUQMRXKJDRDJ-UHFFFAOYSA-N 2-(benzenesulfonyl)-2-(6-methyl-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanenitrile Chemical compound C1CC=2C3=CC(C)=CC=C3NC=2CC1C(C)(C#N)S(=O)(=O)C1=CC=CC=C1 BFYUQMRXKJDRDJ-UHFFFAOYSA-N 0.000 claims 1
- SLBMJJLZSBJZJZ-UHFFFAOYSA-N 2-(benzenesulfonyl)-n-[(4-bromophenyl)methyl]-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoro-n-methylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(=O)N(C)CC1=CC=C(Br)C=C1 SLBMJJLZSBJZJZ-UHFFFAOYSA-N 0.000 claims 1
- ZRFMAKALMBLQOP-UHFFFAOYSA-N 2-(benzenesulfonyl)-n-benzyl-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoro-n-methylacetamide Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(=O)N(C)CC1=CC=CC=C1 ZRFMAKALMBLQOP-UHFFFAOYSA-N 0.000 claims 1
- MMYGEIKOXPZDAC-UHFFFAOYSA-N 2-[(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-(3-ethynylphenyl)sulfonyl-fluoromethyl]-5-methyl-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1C(F)(S(=O)(=O)C=1C=C(C=CC=1)C#C)C1CC(C2=CC(Cl)=CC=C2N2)=C2C1 MMYGEIKOXPZDAC-UHFFFAOYSA-N 0.000 claims 1
- RRFFAESVDVAGHZ-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-1-methoxypropan-2-yl]-6-chloro-2,3,4,9-tetrahydro-1h-carbazole Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(COC)S(=O)(=O)C1=CC=CC=C1 RRFFAESVDVAGHZ-UHFFFAOYSA-N 0.000 claims 1
- QMUHQZQFQDHZKT-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-1-methoxypropan-2-yl]-7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indole Chemical compound C1C=2NC3=CC=C(Cl)C=C3C=2CC1C(C)(COC)S(=O)(=O)C1=CC=CC=C1 QMUHQZQFQDHZKT-UHFFFAOYSA-N 0.000 claims 1
- CFUZTSAXUMEULS-UHFFFAOYSA-N 2-[benzenesulfonyl(pyridin-2-yl)methyl]-7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indole Chemical compound C1C=2C3=CC(Cl)=CC=C3NC=2CC1C(S(=O)(=O)C=1C=CC=CC=1)C1=CC=CC=N1 CFUZTSAXUMEULS-UHFFFAOYSA-N 0.000 claims 1
- UCFKOVIDHXKOCX-UHFFFAOYSA-N 2-[benzenesulfonyl-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-fluoromethyl]-5-cyclopropyl-1,3,4-oxadiazole Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(O1)=NN=C1C1CC1 UCFKOVIDHXKOCX-UHFFFAOYSA-N 0.000 claims 1
- KHOFJNNSYWWAJZ-UHFFFAOYSA-N 2-[benzenesulfonyl-(7-bromo-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-5-methyl-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1C(F)(S(=O)(=O)C=1C=CC=CC=1)C1CC(C2=CC(Br)=CC=C2N2)=C2C1 KHOFJNNSYWWAJZ-UHFFFAOYSA-N 0.000 claims 1
- OCNQETXEXWAWCF-UHFFFAOYSA-N 2-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,3-benzothiazole Chemical compound C1C=2NC3=CC=C(Cl)C=C3C=2CC1C(F)(C=1SC2=CC=CC=C2N=1)S(=O)(=O)C1=CC=CC=C1 OCNQETXEXWAWCF-UHFFFAOYSA-N 0.000 claims 1
- PXVOXBIHPNGQOQ-UHFFFAOYSA-N 2-benzyl-5-[(3-bromophenyl)sulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,3,4-oxadiazole Chemical compound C1C=2NC3=CC=C(Cl)C=C3C=2CC1C(F)(S(=O)(=O)C=1C=C(Br)C=CC=1)C(O1)=NN=C1CC1=CC=CC=C1 PXVOXBIHPNGQOQ-UHFFFAOYSA-N 0.000 claims 1
- AGOFVDPBYRFJRT-UHFFFAOYSA-N 3-[[[2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoroacetyl]-methylamino]methyl]benzoic acid Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C(=O)N(C)CC1=CC=CC(C(O)=O)=C1 AGOFVDPBYRFJRT-UHFFFAOYSA-N 0.000 claims 1
- DHSAOTRBEPOPBO-UHFFFAOYSA-N 4-[5-[(3-bromophenyl)sulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,3,4-oxadiazol-2-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=NN=C(C(F)(C2CC=3C4=CC(Cl)=CC=C4NC=3C2)S(=O)(=O)C=2C=C(Br)C=CC=2)O1 DHSAOTRBEPOPBO-UHFFFAOYSA-N 0.000 claims 1
- SWQWNTVYRMHVCQ-UHFFFAOYSA-N 4-[5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,3,4-oxadiazol-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NN=C(C(F)(C2CC=3C4=CC(Cl)=CC=C4NC=3C2)S(=O)(=O)C=2C=CC=CC=2)O1 SWQWNTVYRMHVCQ-UHFFFAOYSA-N 0.000 claims 1
- KUGVSWWEVJUUPC-UHFFFAOYSA-N 5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,2,4-oxadiazole-3-carbonitrile Chemical compound C1C=2NC3=CC=C(Cl)C=C3C=2CC1C(F)(S(=O)(=O)C=1C=CC=CC=1)C1=NC(C#N)=NO1 KUGVSWWEVJUUPC-UHFFFAOYSA-N 0.000 claims 1
- SEFPCAMXTNBCQK-UHFFFAOYSA-N 5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,2,4-oxadiazole-3-carboxamide Chemical compound NC(=O)C1=NOC(C(F)(C2CC=3C4=CC(Cl)=CC=C4NC=3C2)S(=O)(=O)C=2C=CC=CC=2)=N1 SEFPCAMXTNBCQK-UHFFFAOYSA-N 0.000 claims 1
- LYOPXVTXMBSHNL-UHFFFAOYSA-N 5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,2,4-oxadiazole-3-carboxylic acid Chemical compound OC(=O)C1=NOC(C(F)(C2CC=3C4=CC(Cl)=CC=C4NC=3C2)S(=O)(=O)C=2C=CC=CC=2)=N1 LYOPXVTXMBSHNL-UHFFFAOYSA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- NOBSKIVRQHEZKU-UHFFFAOYSA-N [4-[5-[(3-bromophenyl)sulfonyl-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-fluoromethyl]-1,3,4-oxadiazol-2-yl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1=NN=C(C(F)(C2CC=3C4=CC(Cl)=CC=C4NC=3C2)S(=O)(=O)C=2C=C(Br)C=CC=2)O1 NOBSKIVRQHEZKU-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004125 inden-2-yl group Chemical group [H]C1=C(*)C([H])([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 1
- GVGFPQNEINNGIL-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)sulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanoate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1Cl GVGFPQNEINNGIL-UHFFFAOYSA-N 0.000 claims 1
- WACTZNSXFZIPBA-UHFFFAOYSA-N methyl 2-(3-bromophenyl)sulfonyl-2-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)propanoate Chemical compound C1C=2NC3=CC=C(Cl)C=C3C=2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC(Br)=C1 WACTZNSXFZIPBA-UHFFFAOYSA-N 0.000 claims 1
- KPQLWJWAGXJIST-UHFFFAOYSA-N methyl 2-(3-chlorophenyl)sulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoroacetate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC(Cl)=C1 KPQLWJWAGXJIST-UHFFFAOYSA-N 0.000 claims 1
- YJSNRRWHVBEGIG-UHFFFAOYSA-N methyl 2-(3-chlorophenyl)sulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanoate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC(Cl)=C1 YJSNRRWHVBEGIG-UHFFFAOYSA-N 0.000 claims 1
- MTRFPHKOVNDQRZ-UHFFFAOYSA-N methyl 2-(3-chlorophenyl)sulfonyl-2-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-2-fluoroacetate Chemical compound C1C=2NC3=CC=C(Cl)C=C3C=2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC(Cl)=C1 MTRFPHKOVNDQRZ-UHFFFAOYSA-N 0.000 claims 1
- BTPZEKNBUOMQCT-UHFFFAOYSA-N methyl 2-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-methylsulfonylacetate Chemical compound N1C2=CC=C(Br)C=C2C2=C1CC(C(C(=O)OC)S(C)(=O)=O)CC2 BTPZEKNBUOMQCT-UHFFFAOYSA-N 0.000 claims 1
- WUCULNIWKNLKMF-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-(3,4-dichlorophenyl)sulfonylpropanoate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 WUCULNIWKNLKMF-UHFFFAOYSA-N 0.000 claims 1
- ORESGCGBQFGSGO-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-(3,4-difluorophenyl)sulfonyl-2-fluoroacetate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=C(F)C(F)=C1 ORESGCGBQFGSGO-UHFFFAOYSA-N 0.000 claims 1
- UANUNXOUIAZTOY-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-(3-methoxyphenyl)sulfonylpropanoate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC(OC)=C1 UANUNXOUIAZTOY-UHFFFAOYSA-N 0.000 claims 1
- NOXZNUOXAFSAEG-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-(3-methylphenyl)sulfonylpropanoate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC(C)=C1 NOXZNUOXAFSAEG-UHFFFAOYSA-N 0.000 claims 1
- BUJFSGHBPYJFOP-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-(4-fluorophenyl)sulfonylpropanoate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=C(F)C=C1 BUJFSGHBPYJFOP-UHFFFAOYSA-N 0.000 claims 1
- TUWUXPOHUVIUKC-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoro-2-(3-fluorophenyl)sulfonylacetate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC(F)=C1 TUWUXPOHUVIUKC-UHFFFAOYSA-N 0.000 claims 1
- BTWGWYUQYJMEGS-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoro-2-(4-fluorophenyl)sulfonylacetate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=C(F)C=C1 BTWGWYUQYJMEGS-UHFFFAOYSA-N 0.000 claims 1
- PTLZKSAXJYTCBV-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoro-2-pyridin-3-ylsulfonylacetate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CN=C1 PTLZKSAXJYTCBV-UHFFFAOYSA-N 0.000 claims 1
- BFDOVVGJTCJQIK-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-naphthalen-1-ylsulfonylpropanoate Chemical compound C1=CC=C2C(S(=O)(=O)C(C)(C3CC4=C(C5=CC(Cl)=CC=C5N4)CC3)C(=O)OC)=CC=CC2=C1 BFDOVVGJTCJQIK-UHFFFAOYSA-N 0.000 claims 1
- NNWLUNKWIRAWOS-UHFFFAOYSA-N methyl 2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-naphthalen-2-ylsulfonylpropanoate Chemical compound C1=CC=CC2=CC(S(=O)(=O)C(C)(C3CC4=C(C5=CC(Cl)=CC=C5N4)CC3)C(=O)OC)=CC=C21 NNWLUNKWIRAWOS-UHFFFAOYSA-N 0.000 claims 1
- ZNPXOJRRNKSUSI-UHFFFAOYSA-N methyl 2-(7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-2-(3,4-difluorophenyl)sulfonyl-2-fluoroacetate Chemical compound C1C=2NC3=CC=C(Cl)C=C3C=2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=C(F)C(F)=C1 ZNPXOJRRNKSUSI-UHFFFAOYSA-N 0.000 claims 1
- PXXVFPAQDFVHTH-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoroacetate Chemical compound C1CC(C2=CC(Br)=CC=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 PXXVFPAQDFVHTH-UHFFFAOYSA-N 0.000 claims 1
- JMDMEOXTISINNV-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-bromo-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanoate Chemical compound C1CC(C2=CC(Br)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 JMDMEOXTISINNV-UHFFFAOYSA-N 0.000 claims 1
- UNMQKTCIEULXFQ-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-bromo-5-fluoro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoroacetate Chemical compound C1CC(C2=C(F)C(Br)=CC=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 UNMQKTCIEULXFQ-UHFFFAOYSA-N 0.000 claims 1
- USZTXVJWMTWRSG-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-bromo-7-fluoro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoroacetate Chemical compound C1CC(C2=CC(Br)=C(F)C=C2N2)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 USZTXVJWMTWRSG-UHFFFAOYSA-N 0.000 claims 1
- XBENKGZUPQRPCI-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)acetate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 XBENKGZUPQRPCI-UHFFFAOYSA-N 0.000 claims 1
- OOHNTBVZENBABG-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-chloro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanoate Chemical compound C1CC(C2=CC(Cl)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 OOHNTBVZENBABG-UHFFFAOYSA-N 0.000 claims 1
- WWWJMPAWRRENME-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-cyano-2,3,4,9-tetrahydro-1h-carbazol-2-yl)-2-fluoroacetate Chemical compound C1CC(C2=CC(=CC=C2N2)C#N)=C2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 WWWJMPAWRRENME-UHFFFAOYSA-N 0.000 claims 1
- FWUAOPZEDQFGAE-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-cyano-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanoate Chemical compound C1CC(C2=CC(=CC=C2N2)C#N)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 FWUAOPZEDQFGAE-UHFFFAOYSA-N 0.000 claims 1
- JZPFZLYQBHZNFM-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-fluoro-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanoate Chemical compound C1CC(C2=CC(F)=CC=C2N2)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 JZPFZLYQBHZNFM-UHFFFAOYSA-N 0.000 claims 1
- FNWWIRLBAZDKFO-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(6-methylsulfonyl-2,3,4,9-tetrahydro-1h-carbazol-2-yl)propanoate Chemical compound C1CC(C2=CC(=CC=C2N2)S(C)(=O)=O)=C2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 FNWWIRLBAZDKFO-UHFFFAOYSA-N 0.000 claims 1
- IYZAFSNXFFNKDY-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(7-bromo-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)propanoate Chemical compound C1C=2NC3=CC=C(Br)C=C3C=2CC1C(C)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 IYZAFSNXFFNKDY-UHFFFAOYSA-N 0.000 claims 1
- NHALLFMVQCIZFS-UHFFFAOYSA-N methyl 2-(benzenesulfonyl)-2-(7-bromo-6-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)-2-fluoroacetate Chemical compound C1C=2NC3=CC(F)=C(Br)C=C3C=2CC1C(F)(C(=O)OC)S(=O)(=O)C1=CC=CC=C1 NHALLFMVQCIZFS-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- C07D413/14—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
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- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Gastroenterology & Hepatology (AREA)
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- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| EP04101252 | 2004-03-26 |
Publications (1)
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| ZA200607491B true ZA200607491B (en) | 2008-06-25 |
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| ZA200607491A ZA200607491B (en) | 2004-03-26 | 2006-09-07 | Tetrahydrocarbazoles and derivatives |
Country Status (27)
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| EP (1) | EP1732892B1 (ja) |
| JP (1) | JP4705630B2 (ja) |
| KR (1) | KR100803478B1 (ja) |
| CN (1) | CN1938273B (ja) |
| AR (1) | AR048334A1 (ja) |
| AT (1) | ATE408599T1 (ja) |
| AU (1) | AU2005225524B2 (ja) |
| BR (1) | BRPI0509275A (ja) |
| CA (1) | CA2560700A1 (ja) |
| DE (1) | DE602005009811D1 (ja) |
| DK (1) | DK1732892T3 (ja) |
| ES (1) | ES2314633T3 (ja) |
| HK (1) | HK1101911A1 (ja) |
| HR (1) | HRP20080651T3 (ja) |
| IL (1) | IL177704A (ja) |
| MX (1) | MXPA06010815A (ja) |
| MY (1) | MY140874A (ja) |
| NO (1) | NO20064820L (ja) |
| NZ (1) | NZ549396A (ja) |
| PL (1) | PL1732892T3 (ja) |
| PT (1) | PT1732892E (ja) |
| RU (1) | RU2382770C2 (ja) |
| SI (1) | SI1732892T1 (ja) |
| TW (1) | TW200539870A (ja) |
| WO (1) | WO2005092856A1 (ja) |
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Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2098515B1 (en) | 2006-11-30 | 2012-02-08 | Kowa Company, Ltd. | Substituted carbinol compound |
| FR2913886B1 (fr) | 2007-03-22 | 2012-03-02 | Guerbet Sa | Utilisation de nanoparticules metalliques dans le diagnostique de la maladie d'alzheimer |
| US7919509B2 (en) * | 2008-02-29 | 2011-04-05 | Kowa Company, Ltd. | 2-oxochromene derivatives |
| CN101970479A (zh) * | 2008-03-17 | 2011-02-09 | 弗·哈夫曼-拉罗切有限公司 | Lxr配体结合结构域(lxr lbd)晶体 |
| EP2264029A4 (en) * | 2008-03-31 | 2011-08-24 | Kowa Co | 1,3-dihydroisobenzofuran DERIVATIVE |
| WO2009133692A1 (ja) | 2008-04-30 | 2009-11-05 | 興和株式会社 | キノリン化合物 |
| BRPI0913212A2 (pt) * | 2008-05-29 | 2019-09-24 | Kowa Co | composto de carbinol, remédio, regulador de lxr, composição farmacêutica, método para prevenir e/ou tratar doença, e, uso do derivado de carbinol ou sal do mesmo, ou seu solvato |
| FR2938537B1 (fr) | 2008-11-14 | 2012-10-26 | Sanofi Aventis | Derives de carbamates d'alkyl-heterocycles, leur preparation et leur application en therapeutique. |
| AU2010243044C1 (en) * | 2009-04-29 | 2016-08-25 | Kowa Company, Ltd. | Carbinol compound having heterocyclic linker |
| RS54112B1 (en) | 2010-10-01 | 2015-12-31 | Taisho Pharmaceutical Co. Ltd | DERIVAT 1,2,4-TRIAZOLONA |
| DE102011055815A1 (de) | 2011-11-29 | 2013-05-29 | Aicuris Gmbh & Co. Kg | Carboxamid-substituierte Heteroaryl-Pyrazole und ihre Verwendung |
| RU2654484C1 (ru) | 2012-05-11 | 2018-05-21 | Ресет Терапьютикс, Инк. | Карбазолсодержащие сульфонамиды в качестве модуляторов криптохрома |
| DE102012016908A1 (de) | 2012-08-17 | 2014-02-20 | Aicuris Gmbh & Co. Kg | Tris-(Hetero)Aryl-Pyrazole und ihre Verwendung |
| AU2014232383B2 (en) | 2013-03-15 | 2019-01-17 | Epigen Biosciences, Inc. | Heterocyclic compounds useful in the treatment of disease |
| CN103910659B (zh) * | 2013-11-04 | 2016-05-11 | 迈克斯(如东)化工有限公司 | 2-硝基-4-甲磺酰基苯甲酸的精制方法及其中间体 |
| EP3080099B1 (en) | 2013-12-13 | 2018-04-11 | F.Hoffmann-La Roche Ag | Inhibitors of bruton's tyrosine kinase |
| US10669296B2 (en) | 2014-01-10 | 2020-06-02 | Rgenix, Inc. | LXR agonists and uses thereof |
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| WO2017023916A1 (en) * | 2015-08-05 | 2017-02-09 | Georgetown University | Small molecule androgen receptor inhibitors and methods of use thereof |
| CN109069461A (zh) | 2016-01-11 | 2018-12-21 | 洛克菲勒大学 | 与髓源性抑制细胞相关的病症的治疗方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003090732A1 (en) * | 2002-04-23 | 2003-11-06 | Chugai Seiyaku Kabushiki Kaisha | Lxr modulators for the treatment of cardiovascular diseases |
| WO2003090746A1 (en) * | 2002-04-23 | 2003-11-06 | Chugai Seiyaku Kabushiki Kaisha | 1,3-thiazoles as lxr modulators in the treatment of cardiovascular diseases |
| BR0311282A (pt) * | 2002-05-24 | 2005-04-19 | Pharmacia Corp | Moduladores sulfona de receptor-x do fìgado |
| TWI329111B (en) * | 2002-05-24 | 2010-08-21 | X Ceptor Therapeutics Inc | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| AU2003256655A1 (en) * | 2002-07-25 | 2004-02-16 | Merck And Co., Inc. | Therapeutic compounds for treating dyslipidemic conditions |
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2005
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- 2005-03-17 SI SI200530469T patent/SI1732892T1/sl unknown
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- 2005-03-17 BR BRPI0509275-2A patent/BRPI0509275A/pt not_active IP Right Cessation
- 2005-03-17 MX MXPA06010815A patent/MXPA06010815A/es active IP Right Grant
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- 2005-03-17 AU AU2005225524A patent/AU2005225524B2/en not_active Ceased
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