ES2360936T3 - Indoles sustituidos. - Google Patents
Indoles sustituidos. Download PDFInfo
- Publication number
- ES2360936T3 ES2360936T3 ES03725970T ES03725970T ES2360936T3 ES 2360936 T3 ES2360936 T3 ES 2360936T3 ES 03725970 T ES03725970 T ES 03725970T ES 03725970 T ES03725970 T ES 03725970T ES 2360936 T3 ES2360936 T3 ES 2360936T3
- Authority
- ES
- Spain
- Prior art keywords
- indole
- thio
- acetic acid
- dimethyl
- chlorophenyl
- 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.)
- Expired - Lifetime
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- 150000002475 indoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 187
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 28
- 125000001424 substituent group Chemical group 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- -1 C (O) R 9 Chemical group 0.000 claims abstract description 25
- 150000002367 halogens Chemical class 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 125000005843 halogen group Chemical group 0.000 claims abstract description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000004429 atom Chemical group 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 229910052731 fluorine Chemical group 0.000 claims abstract description 6
- 239000011737 fluorine Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 36
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- QVKASBDGAJXNIP-UHFFFAOYSA-N 1-(carboxymethyl)-3-(4-chlorophenyl)sulfanyl-2-methylindole-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 QVKASBDGAJXNIP-UHFFFAOYSA-N 0.000 claims description 4
- KQHIXPPVIKOOLR-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(4-methylsulfonylphenyl)sulfanylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(S(C)(=O)=O)C=C1 KQHIXPPVIKOOLR-UHFFFAOYSA-N 0.000 claims description 4
- LMABGPMMAGWWSK-UHFFFAOYSA-N 2-[2-methyl-3-(4-methylphenyl)sulfanyl-6-methylsulfonylindol-1-yl]acetic acid Chemical compound C12=CC=C(S(C)(=O)=O)C=C2N(CC(O)=O)C(C)=C1SC1=CC=C(C)C=C1 LMABGPMMAGWWSK-UHFFFAOYSA-N 0.000 claims description 4
- AVHRUHCKFKOSQN-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-(diethylsulfamoyl)-7-methoxy-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)N(CC)CC)=CC=C(OC)C=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 AVHRUHCKFKOSQN-UHFFFAOYSA-N 0.000 claims description 4
- XVHLCZJOPLXFKT-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-cyano-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=C(C#N)C(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 XVHLCZJOPLXFKT-UHFFFAOYSA-N 0.000 claims description 4
- QASSNBHSEOYFCR-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-5-methoxycarbonyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(C(=O)OC)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 QASSNBHSEOYFCR-UHFFFAOYSA-N 0.000 claims description 4
- ZJADDXNBGVBYTJ-UHFFFAOYSA-N 2-[4-amino-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=C(N)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 ZJADDXNBGVBYTJ-UHFFFAOYSA-N 0.000 claims description 4
- JGEHMBWPERYPAN-UHFFFAOYSA-N 2-[4-bromo-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=C(Br)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 JGEHMBWPERYPAN-UHFFFAOYSA-N 0.000 claims description 4
- IFDGTQCELPQPPK-UHFFFAOYSA-N 2-[5-bromo-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(Br)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 IFDGTQCELPQPPK-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000002825 nitriles Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- IEWVQISRDPDETE-UHFFFAOYSA-N 2-(2,5-dimethyl-3-quinolin-8-ylsulfanylindol-1-yl)acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC2=CC=CN=C12 IEWVQISRDPDETE-UHFFFAOYSA-N 0.000 claims description 3
- UESBCCUAXFBWRL-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(2-methylphenyl)sulfanylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1C UESBCCUAXFBWRL-UHFFFAOYSA-N 0.000 claims description 3
- ACXRWARMPADHBY-UHFFFAOYSA-N 2-[2,5-dimethyl-3-[(4-methyl-1,2,4-triazol-3-yl)sulfanyl]indol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=NN=CN1C ACXRWARMPADHBY-UHFFFAOYSA-N 0.000 claims description 3
- IPQPQZVZYOJUFM-UHFFFAOYSA-N 2-[3-(2,5-dichlorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC(Cl)=CC=C1Cl IPQPQZVZYOJUFM-UHFFFAOYSA-N 0.000 claims description 3
- MMCIWYZRJZIDLX-UHFFFAOYSA-N 2-[3-(2,6-dichlorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=C(Cl)C=CC=C1Cl MMCIWYZRJZIDLX-UHFFFAOYSA-N 0.000 claims description 3
- WOBKSMZKNXYFQV-UHFFFAOYSA-N 2-[3-(2-chloro-4-fluorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(F)C=C1Cl WOBKSMZKNXYFQV-UHFFFAOYSA-N 0.000 claims description 3
- PDGCGEBBDZEECC-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)sulfanyl-2,5-dimethyl-4-methylsulfonylindol-1-yl]acetic acid Chemical compound C12=C(S(C)(=O)=O)C(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1Cl PDGCGEBBDZEECC-UHFFFAOYSA-N 0.000 claims description 3
- SHWWFGVUTSBGRN-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1Cl SHWWFGVUTSBGRN-UHFFFAOYSA-N 0.000 claims description 3
- IABFDAOJHRHPDZ-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)sulfanyl-5-fluoro-2,4-dimethylindol-1-yl]acetic acid Chemical compound C12=C(C)C(F)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1Cl IABFDAOJHRHPDZ-UHFFFAOYSA-N 0.000 claims description 3
- DNVTZHZYMQVJTK-UHFFFAOYSA-N 2-[3-(2-methoxyphenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound COC1=CC=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=C(C)C=C12 DNVTZHZYMQVJTK-UHFFFAOYSA-N 0.000 claims description 3
- XLQGPVWRWOQMCL-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)sulfanyl-2,5-dimethyl-4-methylsulfonylindol-1-yl]acetic acid Chemical compound C12=C(S(C)(=O)=O)C(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC(Cl)=C1 XLQGPVWRWOQMCL-UHFFFAOYSA-N 0.000 claims description 3
- JJIHCZIBBZVFSD-UHFFFAOYSA-N 2-[3-(3-fluorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC(F)=C1 JJIHCZIBBZVFSD-UHFFFAOYSA-N 0.000 claims description 3
- SENGIEDFWADTAQ-UHFFFAOYSA-N 2-[3-(4-chloro-2-methylphenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1C SENGIEDFWADTAQ-UHFFFAOYSA-N 0.000 claims description 3
- BVKCMKBKPMUHOY-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 BVKCMKBKPMUHOY-UHFFFAOYSA-N 0.000 claims description 3
- YMPSPYMGGVRUEK-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]indol-1-yl]acetic acid Chemical compound C12=C(N3CCN(CC3)C(=O)OC(C)(C)C)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 YMPSPYMGGVRUEK-UHFFFAOYSA-N 0.000 claims description 3
- WYGCNVZZMIJVNO-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-piperazin-1-ylindol-1-yl]acetic acid Chemical compound C12=C(N3CCNCC3)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 WYGCNVZZMIJVNO-UHFFFAOYSA-N 0.000 claims description 3
- SYOJEOWVUQELIW-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-5-methylsulfonylindol-1-yl]acetic acid Chemical compound C12=CC(S(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 SYOJEOWVUQELIW-UHFFFAOYSA-N 0.000 claims description 3
- QPZCNPOQSRZYOA-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-5-phenylindol-1-yl]acetic acid Chemical compound C12=CC(C=3C=CC=CC=3)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 QPZCNPOQSRZYOA-UHFFFAOYSA-N 0.000 claims description 3
- KAGIMALSSHYKDX-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-(ethylamino)-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NCC)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 KAGIMALSSHYKDX-UHFFFAOYSA-N 0.000 claims description 3
- VAJPAWXFYKFUMH-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-5-fluoro-2,4-dimethylindol-1-yl]acetic acid Chemical compound C12=C(C)C(F)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 VAJPAWXFYKFUMH-UHFFFAOYSA-N 0.000 claims description 3
- AGIYYKVDVOPMKX-UHFFFAOYSA-N 2-[3-(4-cyanophenyl)sulfanyl-5-fluoro-2,4-dimethylindol-1-yl]acetic acid Chemical compound C12=C(C)C(F)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(C#N)C=C1 AGIYYKVDVOPMKX-UHFFFAOYSA-N 0.000 claims description 3
- HBLKTOAFLTUBEJ-UHFFFAOYSA-N 2-[3-(4-ethylphenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C1=CC(CC)=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=C(C)C=C12 HBLKTOAFLTUBEJ-UHFFFAOYSA-N 0.000 claims description 3
- VDGALQGVARKWPY-UHFFFAOYSA-N 2-[4-chloro-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=C(Cl)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 VDGALQGVARKWPY-UHFFFAOYSA-N 0.000 claims description 3
- XYCNWYSSGJBPJP-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 XYCNWYSSGJBPJP-UHFFFAOYSA-N 0.000 claims description 3
- UEPKUIFQQPXWRU-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)sulfanyl-6-cyano-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(Cl)=C(C#N)C=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 UEPKUIFQQPXWRU-UHFFFAOYSA-N 0.000 claims description 3
- IMLZSMXWFHNILV-UHFFFAOYSA-N 2-[5-fluoro-2,4-dimethyl-3-(2-propan-2-ylphenyl)sulfanylindol-1-yl]acetic acid Chemical compound CC(C)C1=CC=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=C(F)C(C)=C12 IMLZSMXWFHNILV-UHFFFAOYSA-N 0.000 claims description 3
- YSBNMIAQDHUQBL-UHFFFAOYSA-N 2-[6-chloro-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC=C(Cl)C=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 YSBNMIAQDHUQBL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- JYGXLHUYAAOBPT-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(1-methylimidazol-2-yl)sulfanylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=NC=CN1C JYGXLHUYAAOBPT-UHFFFAOYSA-N 0.000 claims description 2
- PFVHQFMUOPXZTH-UHFFFAOYSA-N 2-[2,5-dimethyl-4-methylsulfonyl-3-[(4-phenyl-1,3-thiazol-2-yl)sulfanyl]indol-1-yl]acetic acid Chemical compound C12=C(S(C)(=O)=O)C(C)=CC=C2N(CC(O)=O)C(C)=C1SC(SC=1)=NC=1C1=CC=CC=C1 PFVHQFMUOPXZTH-UHFFFAOYSA-N 0.000 claims description 2
- QQAVOUWHBSNMAR-UHFFFAOYSA-N 2-[3-(1h-imidazol-2-ylsulfanyl)-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=NC=CN1 QQAVOUWHBSNMAR-UHFFFAOYSA-N 0.000 claims description 2
- MVAKCYPWCNIEOC-UHFFFAOYSA-N 2-[3-(2-ethylphenyl)sulfanyl-5-fluoro-2,4-dimethylindol-1-yl]acetic acid Chemical compound CCC1=CC=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=C(F)C(C)=C12 MVAKCYPWCNIEOC-UHFFFAOYSA-N 0.000 claims description 2
- YKWFTIHLWPKRSJ-UHFFFAOYSA-N 2-[3-(2-fluorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1F YKWFTIHLWPKRSJ-UHFFFAOYSA-N 0.000 claims description 2
- YSADWAYQAQVVGD-UHFFFAOYSA-N 2-[3-(3-chloro-4-fluorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(F)C(Cl)=C1 YSADWAYQAQVVGD-UHFFFAOYSA-N 0.000 claims description 2
- FFCUWXVMSDAPAN-UHFFFAOYSA-N 2-[3-(3-chlorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC(Cl)=C1 FFCUWXVMSDAPAN-UHFFFAOYSA-N 0.000 claims description 2
- NKYAYPFWGYJSBF-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-nitroindol-1-yl]acetic acid Chemical compound C12=C([N+]([O-])=O)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 NKYAYPFWGYJSBF-UHFFFAOYSA-N 0.000 claims description 2
- ABYZCRCJKRGHGN-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-5-cyano-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(C#N)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 ABYZCRCJKRGHGN-UHFFFAOYSA-N 0.000 claims description 2
- GXKGJTHEVRGSPC-UHFFFAOYSA-N 2-[3-(4-cyanophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(C#N)C=C1 GXKGJTHEVRGSPC-UHFFFAOYSA-N 0.000 claims description 2
- RQWCBKNTMPVMLL-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(F)C=C1 RQWCBKNTMPVMLL-UHFFFAOYSA-N 0.000 claims description 2
- RDWNQKGVOHYXCK-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=C(C)C=C12 RDWNQKGVOHYXCK-UHFFFAOYSA-N 0.000 claims description 2
- LOIQYRPACDIWFV-UHFFFAOYSA-N 2-[5-fluoro-2,4-dimethyl-3-[2-(trifluoromethyl)phenyl]sulfanylindol-1-yl]acetic acid Chemical compound C12=C(C)C(F)=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=CC=C1C(F)(F)F LOIQYRPACDIWFV-UHFFFAOYSA-N 0.000 claims description 2
- UDYKRMHOQKAQNZ-UHFFFAOYSA-N 2-[7-chloro-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C12=CC=CC(Cl)=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 UDYKRMHOQKAQNZ-UHFFFAOYSA-N 0.000 claims description 2
- 101100533888 Hypocrea jecorina (strain QM6a) sor4 gene Proteins 0.000 claims description 2
- 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims description 2
- KFDLHDGFDLHFRW-UHFFFAOYSA-N [O-][N+](Br)=O Chemical group [O-][N+](Br)=O KFDLHDGFDLHFRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- TYAGDQIMEKEYLD-UHFFFAOYSA-N 2-[(2,5-dimethyl-1h-indol-3-yl)sulfanyl]-4-methyl-1,3-oxazole;2-indol-1-ylacetic acid Chemical compound C1=CC=C2N(CC(=O)O)C=CC2=C1.CC1=COC(SC=2C3=CC(C)=CC=C3NC=2C)=N1 TYAGDQIMEKEYLD-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 91
- 239000000243 solution Substances 0.000 description 90
- 239000000047 product Substances 0.000 description 88
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- C07D209/04—Indoles; Hydrogenated indoles
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- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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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- 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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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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| AR017256A1 (es) | 1997-08-21 | 2001-09-05 | American Home Prod | Compuestos de indol sustituidos, metodo para la sintesis en fase solida de los mismos, conjuntos de combinacion para ser empleados en dicho metodo, uso delos compuestos para preparar un medicamento y composiciones farmaceuticas que los comprenden |
| DE69814012T2 (de) | 1997-12-19 | 2004-04-01 | Eli Lilly And Co., Indianapolis | Hypoglykàmische imidazoline derivate |
| AU5886500A (en) | 1999-06-23 | 2001-01-09 | Sepracor, Inc. | Indolyl-benzimidazole antibacterials, and methods of use thereof |
| AU7962200A (en) | 1999-10-29 | 2001-05-14 | Wakunaga Pharmaceutical Co., Ltd | Novel indole derivatives and drugs containing the same as the active ingredient |
| OA12514A (en) | 1999-12-24 | 2006-05-29 | Aventis Pharma Ltd | Azaindoles. |
| NZ522074A (en) | 2000-05-31 | 2004-06-25 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| US6878522B2 (en) | 2000-07-07 | 2005-04-12 | Baiyong Li | Methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2 |
| CA2473803A1 (en) | 2002-02-01 | 2003-08-07 | Robert Greenhouse | Substituted indoles as alpha-1 agonists |
| EP2423190A1 (en) | 2002-05-16 | 2012-02-29 | Shionogi&Co., Ltd. | Compounds Exhibiting PGD 2 Receptor Antagonism |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| TW200307542A (en) | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| SE0301569D0 (sv) | 2003-05-27 | 2003-05-27 | Astrazeneca Ab | Novel compounds |
| SE0302232D0 (sv) | 2003-08-18 | 2003-08-18 | Astrazeneca Ab | Novel Compounds |
| SE0303180D0 (sv) | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
-
2002
- 2002-05-30 SE SE0201635A patent/SE0201635D0/xx unknown
-
2003
- 2003-05-26 TW TW092114174A patent/TW200407305A/zh unknown
- 2003-05-27 WO PCT/SE2003/000856 patent/WO2003101961A1/en not_active Ceased
- 2003-05-27 BR BR0311494-5A patent/BR0311494A/pt not_active IP Right Cessation
- 2003-05-27 ES ES03725970T patent/ES2360936T3/es not_active Expired - Lifetime
- 2003-05-27 AU AU2003228201A patent/AU2003228201A1/en not_active Abandoned
- 2003-05-27 KR KR10-2004-7019452A patent/KR20050010507A/ko not_active Ceased
- 2003-05-27 NZ NZ536883A patent/NZ536883A/en unknown
- 2003-05-27 EP EP03725970A patent/EP1513812B1/en not_active Expired - Lifetime
- 2003-05-27 UA UA20041109794A patent/UA79464C2/uk unknown
- 2003-05-27 CN CNB038183447A patent/CN100404505C/zh not_active Expired - Fee Related
- 2003-05-27 CA CA002487675A patent/CA2487675A1/en not_active Abandoned
- 2003-05-27 US US10/516,557 patent/US7166607B2/en not_active Expired - Fee Related
- 2003-05-27 MX MXPA04011876A patent/MXPA04011876A/es active IP Right Grant
- 2003-05-27 JP JP2004509654A patent/JP4485354B2/ja not_active Expired - Fee Related
- 2003-05-27 DE DE60336314T patent/DE60336314D1/de not_active Expired - Lifetime
- 2003-05-27 RU RU2004135064/04A patent/RU2288914C2/ru not_active IP Right Cessation
- 2003-05-27 PL PL03375111A patent/PL375111A1/xx not_active Application Discontinuation
- 2003-05-27 AT AT03725970T patent/ATE501118T1/de not_active IP Right Cessation
- 2003-05-28 MY MYPI20031973A patent/MY133624A/en unknown
- 2003-05-30 AR ARP030101932A patent/AR039934A1/es not_active Application Discontinuation
-
2004
- 2004-11-29 CO CO04120052A patent/CO5631431A2/es not_active Application Discontinuation
- 2004-11-29 ZA ZA200409641A patent/ZA200409641B/xx unknown
- 2004-12-21 IS IS7607A patent/IS7607A/is unknown
- 2004-12-22 NO NO20045589A patent/NO20045589L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20050165055A1 (en) | 2005-07-28 |
| SE0201635D0 (sv) | 2002-05-30 |
| CN1671659A (zh) | 2005-09-21 |
| AR039934A1 (es) | 2005-03-09 |
| TW200407305A (en) | 2004-05-16 |
| CA2487675A1 (en) | 2003-12-11 |
| CN100404505C (zh) | 2008-07-23 |
| KR20050010507A (ko) | 2005-01-27 |
| PL375111A1 (en) | 2005-11-28 |
| IS7607A (is) | 2004-12-21 |
| AU2003228201A1 (en) | 2003-12-19 |
| MY133624A (en) | 2007-11-30 |
| NZ536883A (en) | 2006-08-31 |
| RU2004135064A (ru) | 2005-08-10 |
| US7166607B2 (en) | 2007-01-23 |
| NO20045589L (no) | 2005-02-02 |
| BR0311494A (pt) | 2005-03-29 |
| WO2003101961A1 (en) | 2003-12-11 |
| EP1513812A1 (en) | 2005-03-16 |
| ZA200409641B (en) | 2006-02-22 |
| UA79464C2 (en) | 2007-06-25 |
| ATE501118T1 (de) | 2011-03-15 |
| EP1513812B1 (en) | 2011-03-09 |
| CO5631431A2 (es) | 2006-04-28 |
| JP4485354B2 (ja) | 2010-06-23 |
| MXPA04011876A (es) | 2005-03-31 |
| RU2288914C2 (ru) | 2006-12-10 |
| JP2005538955A (ja) | 2005-12-22 |
| DE60336314D1 (de) | 2011-04-21 |
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