JP2005538955A5 - - Google Patents
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- Publication number
- JP2005538955A5 JP2005538955A5 JP2004509654A JP2004509654A JP2005538955A5 JP 2005538955 A5 JP2005538955 A5 JP 2005538955A5 JP 2004509654 A JP2004509654 A JP 2004509654A JP 2004509654 A JP2004509654 A JP 2004509654A JP 2005538955 A5 JP2005538955 A5 JP 2005538955A5
- Authority
- JP
- Japan
- Prior art keywords
- indole
- acetic acid
- thio
- 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.)
- Granted
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- 125000003118 aryl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- -1 R 14 Chemical compound 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229910052731 fluorine Chemical group 0.000 claims 2
- 239000011737 fluorine Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- YLARYOPAOYGKNQ-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(1h-1,2,4-triazol-5-ylsulfanyl)indol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1SC=1N=CNN=1 YLARYOPAOYGKNQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- CVSLEUOVFJECNE-UHFFFAOYSA-N 2-[2,5-dimethyl-3-[(4-methyl-1,3-oxazol-2-yl)sulfanyl]indol-1-yl]acetic acid Chemical compound CC1=COC(SC=2C3=CC(C)=CC=C3N(CC(O)=O)C=2C)=N1 CVSLEUOVFJECNE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- VMBCXGGWSXMICG-UHFFFAOYSA-N 2-[3-(3-ethylphenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound CCC1=CC=CC(SC=2C3=CC(C)=CC=C3N(CC(O)=O)C=2C)=C1 VMBCXGGWSXMICG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WSYQDNBBRMZSBJ-UHFFFAOYSA-N 2-[3-(3-methoxyphenyl)sulfanyl-2,5-dimethylindol-1-yl]acetic acid Chemical compound COC1=CC=CC(SC=2C3=CC(C)=CC=C3N(CC(O)=O)C=2C)=C1 WSYQDNBBRMZSBJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- SKJAIFGOCYTZIP-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-phenylindol-1-yl]acetic acid Chemical compound C12=C(C=3C=CC=CC=3)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 SKJAIFGOCYTZIP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- JNPAVQUADRRDBK-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-ethylsulfonyl-7-methoxy-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)CC)=CC=C(OC)C=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 JNPAVQUADRRDBK-UHFFFAOYSA-N 0.000 claims 1
- RYPMOVMEQIGMGP-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-4-iodo-2-methylindol-1-yl]acetic acid Chemical compound C12=C(I)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 RYPMOVMEQIGMGP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- QKTSFQHDUXJUPC-UHFFFAOYSA-N 2-[5-fluoro-3-(2-methoxyphenyl)sulfanyl-2,4-dimethylindol-1-yl]acetic acid Chemical compound COC1=CC=CC=C1SC1=C(C)N(CC(O)=O)C2=CC=C(F)C(C)=C12 QKTSFQHDUXJUPC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 claims 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| PCT/SE2003/000856 WO2003101961A1 (en) | 2002-05-30 | 2003-05-27 | Novel substituted indoles |
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- 2003-05-27 PL PL03375111A patent/PL375111A1/xx not_active Application Discontinuation
- 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 US US10/516,557 patent/US7166607B2/en not_active Expired - Fee Related
- 2003-05-27 AT AT03725970T patent/ATE501118T1/de not_active IP Right Cessation
- 2003-05-27 EP EP03725970A patent/EP1513812B1/en not_active Expired - Lifetime
- 2003-05-27 UA UA20041109794A patent/UA79464C2/uk unknown
- 2003-05-27 AU AU2003228201A patent/AU2003228201A1/en not_active Abandoned
- 2003-05-27 JP JP2004509654A patent/JP4485354B2/ja not_active Expired - Fee Related
- 2003-05-27 KR KR10-2004-7019452A patent/KR20050010507A/ko not_active Ceased
- 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
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