JP2007502806A5 - - Google Patents
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- Publication number
- JP2007502806A5 JP2007502806A5 JP2006523683A JP2006523683A JP2007502806A5 JP 2007502806 A5 JP2007502806 A5 JP 2007502806A5 JP 2006523683 A JP2006523683 A JP 2006523683A JP 2006523683 A JP2006523683 A JP 2006523683A JP 2007502806 A5 JP2007502806 A5 JP 2007502806A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- phenoxy
- phenyl
- acetic acid
- methylsulfonyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims 23
- 150000002431 hydrogen Chemical group 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- XPOUWICLOLTBKH-SNVBAGLBSA-N (2r)-2-[4-chloro-2-(4-methylsulfonylphenyl)sulfanylphenoxy]propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1SC1=CC=C(S(C)(=O)=O)C=C1 XPOUWICLOLTBKH-SNVBAGLBSA-N 0.000 claims 2
- TWMPQJAZWVLYFX-JTQLQIEISA-N (2s)-2-[2-(2-chloro-4-ethylsulfonylanilino)-4-fluorophenoxy]propanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1NC1=CC(F)=CC=C1O[C@@H](C)C(O)=O TWMPQJAZWVLYFX-JTQLQIEISA-N 0.000 claims 2
- OLDKDUZYBDYVHL-JTQLQIEISA-N (2s)-2-[2-(2-chloro-4-ethylsulfonylphenyl)sulfanyl-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1SC1=CC(C(F)(F)F)=CC=C1O[C@@H](C)C(O)=O OLDKDUZYBDYVHL-JTQLQIEISA-N 0.000 claims 2
- ZMOGYSHKDHKEPG-VIFPVBQESA-N (2s)-2-[2-(2-chloro-4-methylsulfonylanilino)-4-fluorophenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(F)C=C1NC1=CC=C(S(C)(=O)=O)C=C1Cl ZMOGYSHKDHKEPG-VIFPVBQESA-N 0.000 claims 2
- MYZVCTMXVBBSHQ-VIFPVBQESA-N (2s)-2-[2-(2-chloro-4-methylsulfonylphenyl)sulfanyl-4-(trifluoromethyl)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(C(F)(F)F)C=C1SC1=CC=C(S(C)(=O)=O)C=C1Cl MYZVCTMXVBBSHQ-VIFPVBQESA-N 0.000 claims 2
- QPLXURBDLUNNDK-JTQLQIEISA-N (2s)-2-[4-chloro-2-(2-chloro-4-ethylsulfonylanilino)phenoxy]propanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1NC1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O QPLXURBDLUNNDK-JTQLQIEISA-N 0.000 claims 2
- DCNNIFYZFCCXNZ-JTQLQIEISA-N (2s)-2-[4-chloro-2-(2-chloro-4-ethylsulfonylphenoxy)phenoxy]propanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1OC1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O DCNNIFYZFCCXNZ-JTQLQIEISA-N 0.000 claims 2
- HSLXQEAIKORKBC-JTQLQIEISA-N (2s)-2-[4-chloro-2-(2-chloro-4-ethylsulfonylphenyl)sulfanylphenoxy]propanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1SC1=CC(Cl)=CC=C1O[C@@H](C)C(O)=O HSLXQEAIKORKBC-JTQLQIEISA-N 0.000 claims 2
- IRHGWEOJANIAAG-VIFPVBQESA-N (2s)-2-[4-chloro-2-(2-chloro-4-methylsulfonylanilino)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1NC1=CC=C(S(C)(=O)=O)C=C1Cl IRHGWEOJANIAAG-VIFPVBQESA-N 0.000 claims 2
- QMDOBCGDJDENNL-VIFPVBQESA-N (2s)-2-[4-chloro-2-(2-chloro-4-methylsulfonylphenoxy)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1OC1=CC=C(S(C)(=O)=O)C=C1Cl QMDOBCGDJDENNL-VIFPVBQESA-N 0.000 claims 2
- BRFJGHZSNKHMLO-VIFPVBQESA-N (2s)-2-[4-chloro-2-(2-chloro-4-methylsulfonylphenyl)sulfanylphenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1SC1=CC=C(S(C)(=O)=O)C=C1Cl BRFJGHZSNKHMLO-VIFPVBQESA-N 0.000 claims 2
- RARNYMRRZAWUGS-JTQLQIEISA-N (2s)-2-[4-chloro-2-(4-methylsulfonylphenoxy)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1OC1=CC=C(S(C)(=O)=O)C=C1 RARNYMRRZAWUGS-JTQLQIEISA-N 0.000 claims 2
- XPOUWICLOLTBKH-JTQLQIEISA-N (2s)-2-[4-chloro-2-(4-methylsulfonylphenyl)sulfanylphenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1SC1=CC=C(S(C)(=O)=O)C=C1 XPOUWICLOLTBKH-JTQLQIEISA-N 0.000 claims 2
- TYEGCPIOTUQBFB-VIFPVBQESA-N (2s)-2-[4-chloro-2-(4-nitrophenoxy)phenoxy]propanoic acid Chemical compound OC(=O)[C@H](C)OC1=CC=C(Cl)C=C1OC1=CC=C([N+]([O-])=O)C=C1 TYEGCPIOTUQBFB-VIFPVBQESA-N 0.000 claims 2
- ASFUMSRMZLIYEI-UHFFFAOYSA-N 2-(4-chloro-2-pyrimidin-5-yloxyphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1OC1=CN=CN=C1 ASFUMSRMZLIYEI-UHFFFAOYSA-N 0.000 claims 2
- IGGJVDVYSKYZKT-UHFFFAOYSA-N 2-(4-chloro-2-quinolin-3-yloxyphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1OC1=CN=C(C=CC=C2)C2=C1 IGGJVDVYSKYZKT-UHFFFAOYSA-N 0.000 claims 2
- LVIQCCBIKCDGNC-UHFFFAOYSA-N 2-(4-chloro-2-quinolin-8-ylsulfanylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1SC1=CC=CC2=CC=CN=C12 LVIQCCBIKCDGNC-UHFFFAOYSA-N 0.000 claims 2
- PVSMIEQMXVXBSP-UHFFFAOYSA-N 2-[2-(2-chloro-4-ethylsulfonylanilino)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1NC1=CC(C(F)(F)F)=CC=C1OCC(O)=O PVSMIEQMXVXBSP-UHFFFAOYSA-N 0.000 claims 2
- CIOFTFQCOATEJS-UHFFFAOYSA-N 2-[2-(2-chloro-4-ethylsulfonylanilino)-4-fluorophenoxy]-2-methylpropanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1NC1=CC(F)=CC=C1OC(C)(C)C(O)=O CIOFTFQCOATEJS-UHFFFAOYSA-N 0.000 claims 2
- KAGQFTKJGKFBGK-UHFFFAOYSA-N 2-[2-(2-chloro-4-ethylsulfonylanilino)-4-fluorophenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1NC1=CC(F)=CC=C1OCC(O)=O KAGQFTKJGKFBGK-UHFFFAOYSA-N 0.000 claims 2
- JSOMLHMTXRHZQC-UHFFFAOYSA-N 2-[2-(2-chloro-4-ethylsulfonylphenoxy)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1OC1=CC(C(F)(F)F)=CC=C1OCC(O)=O JSOMLHMTXRHZQC-UHFFFAOYSA-N 0.000 claims 2
- MBBBUWIKGWSTAO-UHFFFAOYSA-N 2-[2-(2-chloro-4-ethylsulfonylphenoxy)-4-fluorophenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1OC1=CC(F)=CC=C1OCC(O)=O MBBBUWIKGWSTAO-UHFFFAOYSA-N 0.000 claims 2
- GFPSZCWTXRMYBY-UHFFFAOYSA-N 2-[2-(2-chloro-4-ethylsulfonylphenyl)sulfanyl-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1SC1=CC(C(F)(F)F)=CC=C1OCC(O)=O GFPSZCWTXRMYBY-UHFFFAOYSA-N 0.000 claims 2
- UGMFVRAEYTYCPF-UHFFFAOYSA-N 2-[2-(2-chloro-4-ethylsulfonylphenyl)sulfanyl-4-fluorophenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1SC1=CC(F)=CC=C1OCC(O)=O UGMFVRAEYTYCPF-UHFFFAOYSA-N 0.000 claims 2
- NUCZOSYRWLTSCW-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylanilino)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1NC1=CC(C(F)(F)F)=CC=C1OCC(O)=O NUCZOSYRWLTSCW-UHFFFAOYSA-N 0.000 claims 2
- MCMSVHAYHSAWLW-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylanilino)-4-fluorophenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1NC1=CC(F)=CC=C1OCC(O)=O MCMSVHAYHSAWLW-UHFFFAOYSA-N 0.000 claims 2
- YVWIJOUCWQAOKM-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylphenoxy)-4,5-difluorophenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1OC1=CC(F)=C(F)C=C1OCC(O)=O YVWIJOUCWQAOKM-UHFFFAOYSA-N 0.000 claims 2
- SWWTWGYWXKBZMM-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylphenoxy)-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1OC1=CC(C(F)(F)F)=CC=C1OCC(O)=O SWWTWGYWXKBZMM-UHFFFAOYSA-N 0.000 claims 2
- HABMSFJEZJYHMJ-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylphenoxy)-4-(trifluoromethyl)phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=C(C(F)(F)F)C=C1OC1=CC=C(S(C)(=O)=O)C=C1Cl HABMSFJEZJYHMJ-UHFFFAOYSA-N 0.000 claims 2
- UEZBNKZOFMZIKN-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylphenoxy)-4-fluorophenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1OC1=CC(F)=CC=C1OCC(O)=O UEZBNKZOFMZIKN-UHFFFAOYSA-N 0.000 claims 2
- JTUSETDYFVBGCR-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylphenoxy)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1OC1=CC=CC=C1OCC(O)=O JTUSETDYFVBGCR-UHFFFAOYSA-N 0.000 claims 2
- YXRXXVSHKRJRJQ-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylphenyl)sulfanyl-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1SC1=CC(C(F)(F)F)=CC=C1OCC(O)=O YXRXXVSHKRJRJQ-UHFFFAOYSA-N 0.000 claims 2
- ZUWRUWDEYPSFBL-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylphenyl)sulfanyl-4-fluorophenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(F)C=C1SC1=CC=C(S(C)(=O)=O)C=C1Cl ZUWRUWDEYPSFBL-UHFFFAOYSA-N 0.000 claims 2
- VTNPFXJTTSYULZ-UHFFFAOYSA-N 2-[2-(2-chloro-4-methylsulfonylphenyl)sulfanyl-4-fluorophenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1SC1=CC(F)=CC=C1OCC(O)=O VTNPFXJTTSYULZ-UHFFFAOYSA-N 0.000 claims 2
- WTKOTNKDXKSMEB-UHFFFAOYSA-N 2-[2-[(4-ethylsulfonylphenyl)methyl]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1CC1=CC(C(F)(F)F)=CC=C1OCC(O)=O WTKOTNKDXKSMEB-UHFFFAOYSA-N 0.000 claims 2
- IEDDSVITIOMMBA-UHFFFAOYSA-N 2-[2-[2-chloro-4-(ethylsulfonylamino)phenoxy]-4-fluorophenoxy]acetic acid Chemical compound ClC1=CC(NS(=O)(=O)CC)=CC=C1OC1=CC(F)=CC=C1OCC(O)=O IEDDSVITIOMMBA-UHFFFAOYSA-N 0.000 claims 2
- RREYSGDVUFORPK-UHFFFAOYSA-N 2-[2-[4-(dimethylsulfamoyl)phenoxy]-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1OC1=CC(C(F)(F)F)=CC=C1OCC(O)=O RREYSGDVUFORPK-UHFFFAOYSA-N 0.000 claims 2
- CVCUSGPSZYITAD-UHFFFAOYSA-N 2-[2-[4-(dimethylsulfamoyl)phenyl]sulfanyl-4-(trifluoromethyl)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1SC1=CC(C(F)(F)F)=CC=C1OCC(O)=O CVCUSGPSZYITAD-UHFFFAOYSA-N 0.000 claims 2
- DMWNJFGNKHRMJL-UHFFFAOYSA-N 2-[4,5-dichloro-2-(2-chloro-4-methylsulfonylphenoxy)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1OC1=CC(Cl)=C(Cl)C=C1OCC(O)=O DMWNJFGNKHRMJL-UHFFFAOYSA-N 0.000 claims 2
- RVCFZMTUSAMOPJ-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-cyanophenyl)sulfanylphenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1SC1=CC=C(C#N)C=C1Cl RVCFZMTUSAMOPJ-UHFFFAOYSA-N 0.000 claims 2
- WPDQQKXECYFDHI-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-ethylsulfonylanilino)phenoxy]-2-methylpropanoic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1NC1=CC(Cl)=CC=C1OC(C)(C)C(O)=O WPDQQKXECYFDHI-UHFFFAOYSA-N 0.000 claims 2
- DQORQOAIMOXSAP-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-ethylsulfonylanilino)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1NC1=CC(Cl)=CC=C1OCC(O)=O DQORQOAIMOXSAP-UHFFFAOYSA-N 0.000 claims 2
- UBLYUSFUHDOYHN-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-ethylsulfonylphenoxy)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1OC1=CC(Cl)=CC=C1OCC(O)=O UBLYUSFUHDOYHN-UHFFFAOYSA-N 0.000 claims 2
- BOUMNJZRBSZUDN-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-ethylsulfonylphenyl)sulfanylphenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)CC)=CC=C1SC1=CC(Cl)=CC=C1OCC(O)=O BOUMNJZRBSZUDN-UHFFFAOYSA-N 0.000 claims 2
- KNKZIOAABKESLW-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-methylsulfonylanilino)phenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1NC1=CC=C(S(C)(=O)=O)C=C1Cl KNKZIOAABKESLW-UHFFFAOYSA-N 0.000 claims 2
- MUYJHGJCOZNEEC-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-methylsulfonylanilino)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1NC1=CC(Cl)=CC=C1OCC(O)=O MUYJHGJCOZNEEC-UHFFFAOYSA-N 0.000 claims 2
- PIAAHYFALWUUPI-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-methylsulfonylphenoxy)phenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1OC1=CC=C(S(C)(=O)=O)C=C1Cl PIAAHYFALWUUPI-UHFFFAOYSA-N 0.000 claims 2
- LQCYYTFHZPEXAT-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-methylsulfonylphenoxy)phenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1OC1=CC(Cl)=CC=C1OCC(O)=O LQCYYTFHZPEXAT-UHFFFAOYSA-N 0.000 claims 2
- WHYIHUSSUFKTBZ-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-methylsulfonylphenyl)sulfanylphenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1SC1=CC=C(S(C)(=O)=O)C=C1Cl WHYIHUSSUFKTBZ-UHFFFAOYSA-N 0.000 claims 2
- QRQZNGXNIKSCPW-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-4-methylsulfonylphenyl)sulfanylphenoxy]acetic acid Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1SC1=CC(Cl)=CC=C1OCC(O)=O QRQZNGXNIKSCPW-UHFFFAOYSA-N 0.000 claims 2
- MWHCVLWDSWEWFL-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-n-ethyl-4-methylsulfonylanilino)phenoxy]acetic acid Chemical compound C=1C(Cl)=CC=C(OCC(O)=O)C=1N(CC)C1=CC=C(S(C)(=O)=O)C=C1Cl MWHCVLWDSWEWFL-UHFFFAOYSA-N 0.000 claims 2
- UUCMUZNLQKZMOG-UHFFFAOYSA-N 2-[4-chloro-2-(2-chloro-n-methyl-4-methylsulfonylanilino)phenoxy]acetic acid Chemical compound C=1C(Cl)=CC=C(OCC(O)=O)C=1N(C)C1=CC=C(S(C)(=O)=O)C=C1Cl UUCMUZNLQKZMOG-UHFFFAOYSA-N 0.000 claims 2
- HNUXVOMXQYGQQK-UHFFFAOYSA-N 2-[4-chloro-2-(2-methylsulfonylphenyl)sulfanylphenoxy]acetic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1SC1=CC(Cl)=CC=C1OCC(O)=O HNUXVOMXQYGQQK-UHFFFAOYSA-N 0.000 claims 2
- JIIYLKVZKUJYCH-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonyl-2-methylphenyl)sulfanylphenoxy]acetic acid Chemical compound CC1=CC(S(=O)(=O)CC)=CC=C1SC1=CC(Cl)=CC=C1OCC(O)=O JIIYLKVZKUJYCH-UHFFFAOYSA-N 0.000 claims 2
- IEACYKMVFGVBLH-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonylphenoxy)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1OC1=CC(Cl)=CC=C1OCC(O)=O IEACYKMVFGVBLH-UHFFFAOYSA-N 0.000 claims 2
- KYMFVCOUPCLCHE-UHFFFAOYSA-N 2-[4-chloro-2-(4-ethylsulfonylphenyl)sulfanylphenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1SC1=CC(Cl)=CC=C1OCC(O)=O KYMFVCOUPCLCHE-UHFFFAOYSA-N 0.000 claims 2
- YVBCTEDNWTUIHB-UHFFFAOYSA-N 2-[4-chloro-2-(4-methylsulfonylanilino)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=CC(Cl)=CC=C1OCC(O)=O YVBCTEDNWTUIHB-UHFFFAOYSA-N 0.000 claims 2
- OOUJECDNSYKLLO-UHFFFAOYSA-N 2-[4-chloro-2-(4-methylsulfonylphenoxy)phenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1=CC(Cl)=CC=C1OCC(O)=O OOUJECDNSYKLLO-UHFFFAOYSA-N 0.000 claims 2
- CKMHCINAXMIZBD-UHFFFAOYSA-N 2-[4-chloro-2-(4-methylsulfonylphenyl)sulfanylphenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1SC1=CC(Cl)=CC=C1OCC(O)=O CKMHCINAXMIZBD-UHFFFAOYSA-N 0.000 claims 2
- PVEGPGIMLMOMHO-UHFFFAOYSA-N 2-[4-chloro-2-(4-methylsulfonylphenyl)sulfinylphenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1S(=O)C1=CC(Cl)=CC=C1OCC(O)=O PVEGPGIMLMOMHO-UHFFFAOYSA-N 0.000 claims 2
- BEAWNVDIFYFJKR-UHFFFAOYSA-N 2-[4-chloro-2-(4-methylsulfonylphenyl)sulfonylphenoxy]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1S(=O)(=O)C1=CC(Cl)=CC=C1OCC(O)=O BEAWNVDIFYFJKR-UHFFFAOYSA-N 0.000 claims 2
- GHFLOZJXCILUDU-UHFFFAOYSA-N 2-[4-chloro-2-(5-chloropyridin-2-yl)sulfanylphenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1SC1=CC=C(Cl)C=N1 GHFLOZJXCILUDU-UHFFFAOYSA-N 0.000 claims 2
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| WO2007149312A2 (en) | 2006-06-16 | 2007-12-27 | The Trustees Of The University Of Pennsylvania | Methods and compositions for inhibiting or reducing hair loss, acne, rosacea, prostate cancer, and bph |
| GB0702456D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | New combination |
| SI2139881T1 (sl) | 2007-04-04 | 2012-05-31 | Pulmagen Therapeutics Asthma Ltd | Kinolini in njihova terapevtska raba |
| UA100983C2 (ru) * | 2007-07-05 | 2013-02-25 | Астразенека Аб | Бифенилоксипропановая кислота как модулятор crth2 и интермедиаты |
| ATE502920T1 (de) | 2007-12-14 | 2011-04-15 | Pulmagen Therapeutics Asthma Ltd | Indole und ihre therapeutische verwendung |
| WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
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| MX2011005120A (es) * | 2008-11-17 | 2011-05-30 | Hoffmann La Roche | Acidos naftilaceticos. |
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| EP2590944B1 (en) | 2010-07-05 | 2015-09-30 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
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| EP2526945A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | New CRTH2 Antagonists |
| EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
| EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| JP2015500326A (ja) | 2011-12-16 | 2015-01-05 | アトピックス テラピューティクス リミテッド | 好酸球性食道炎の治療のためのｃｒｔｈ２拮抗薬およびプロトンポンプ阻害薬の組み合わせ |
| EP2794563B1 (en) | 2011-12-21 | 2017-02-22 | Actelion Pharmaceuticals Ltd | Heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| JP6193968B2 (ja) | 2012-03-21 | 2017-09-06 | ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア | 発毛を調節するための組成物および方法 |
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| US20180021302A1 (en) | 2015-02-13 | 2018-01-25 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Ptgdr-1 and/or ptgdr-2 antagonists for preventing and/or treating systemic lupus erythematosus |
| PT3305768T (pt) * | 2015-05-27 | 2020-08-03 | Jiangsu Hengrui Medicine Co | Sal de sódio de um inibidor do transportador do ácido úrico e forma cristalina do mesmo |
| HK1256553A1 (zh) | 2015-07-30 | 2019-09-27 | The Trustees Of The University Of Pennsylvania | 用於检测pgd2对毛发生长抑制的易感性的人dp-2基因的单核苷酸多态性等位基因 |
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- 2004-08-15 SA SA4250253A patent/SA04250253B1/ar unknown
- 2004-08-16 TW TW093124572A patent/TWI347313B/zh not_active IP Right Cessation
- 2004-08-18 HR HR20090280T patent/HRP20090280T1/xx unknown
- 2004-08-18 US US10/569,065 patent/US8003703B2/en not_active Expired - Fee Related
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- 2004-08-18 ES ES04768111T patent/ES2322653T3/es not_active Expired - Lifetime
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- 2004-08-18 PL PL04768111T patent/PL1660431T3/pl unknown
- 2004-08-18 AU AU2004266485A patent/AU2004266485B2/en not_active Ceased
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