JP2013506695A - リゾホスファチジン酸受容体アンタゴニストとしての化合物 - Google Patents
リゾホスファチジン酸受容体アンタゴニストとしての化合物 Download PDFInfo
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- JP2013506695A JP2013506695A JP2012532368A JP2012532368A JP2013506695A JP 2013506695 A JP2013506695 A JP 2013506695A JP 2012532368 A JP2012532368 A JP 2012532368A JP 2012532368 A JP2012532368 A JP 2012532368A JP 2013506695 A JP2013506695 A JP 2013506695A
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- Prior art keywords
- methyl
- isoxazol
- phenyl
- compound
- biphenyl
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- CXIZYLQCASDUKL-UHFFFAOYSA-N 1-[4-[4-[4-(1-hydroxy-4-phenylbutyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]-n-(4-methylphenyl)sulfonylcyclopropane-1-carboxamide Chemical compound CC1=NOC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C2(CC2)C(=O)NS(=O)(=O)C=2C=CC(C)=CC=2)=C1C(O)CCCC1=CC=CC=C1 CXIZYLQCASDUKL-UHFFFAOYSA-N 0.000 claims description 5
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- MOPKQIHRUWWSKC-UHFFFAOYSA-N 1-[4-[4-[3-methyl-4-(1-phenylpropan-2-yloxymethyl)-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound CC1=NOC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C2(CC2)C(O)=O)=C1COC(C)CC1=CC=CC=C1 MOPKQIHRUWWSKC-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
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- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 2
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- KOPWWIQRTOAISS-UHFFFAOYSA-N ethyl 1-[4-[4-(4-formyl-3-methyl-1,2-oxazol-5-yl)phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C=O)C=CC=1C1(C(=O)OCC)CC1 KOPWWIQRTOAISS-UHFFFAOYSA-N 0.000 description 1
- UMORZQOTFLLUSM-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-(1-phenylpentan-3-ylamino)-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)NC(CC)CCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 UMORZQOTFLLUSM-UHFFFAOYSA-N 0.000 description 1
- KZLXLTBTCSQVIT-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-(2-phenylethylsulfanylmethyl)-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CSCCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 KZLXLTBTCSQVIT-UHFFFAOYSA-N 0.000 description 1
- OFPRQDWIMSKMCI-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-(2-phenylmethoxyethyl)-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CCOCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 OFPRQDWIMSKMCI-UHFFFAOYSA-N 0.000 description 1
- KUUULBJIXCMUHO-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-(3-phenylpropanoyl)-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(=O)CCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 KUUULBJIXCMUHO-UHFFFAOYSA-N 0.000 description 1
- WQMDQFDUFKECPP-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-(3-phenylpropylamino)-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)NCCCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 WQMDQFDUFKECPP-UHFFFAOYSA-N 0.000 description 1
- UNIQOYYFHJEBGL-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-(4-phenylbutanoyl)-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(=O)CCCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 UNIQOYYFHJEBGL-UHFFFAOYSA-N 0.000 description 1
- NYZCSBPOJRUETR-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-[(2-phenylethylamino)methyl]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CNCCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 NYZCSBPOJRUETR-UHFFFAOYSA-N 0.000 description 1
- IZRZROSZZFAARA-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-[(2-phenylpropylamino)methyl]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CNCC(C)C=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 IZRZROSZZFAARA-UHFFFAOYSA-N 0.000 description 1
- UUDZMOJAEBBCBO-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-[(4-methyl-4-phenylpentan-2-yl)amino]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)NC(C)CC(C)(C)C=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 UUDZMOJAEBBCBO-UHFFFAOYSA-N 0.000 description 1
- SVDYZZQQQAVCCQ-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-[3-[3-(trifluoromethyl)phenyl]propanoyl]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(=O)CCC=2C=C(C=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 SVDYZZQQQAVCCQ-UHFFFAOYSA-N 0.000 description 1
- RKQNPIDWSJSRNW-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-[4-[3-(trifluoromethyl)phenyl]butan-2-ylamino]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)NC(C)CCC=2C=C(C=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 RKQNPIDWSJSRNW-UHFFFAOYSA-N 0.000 description 1
- UHVUFLDKAHQKBL-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-[[2-methyl-3-(4-propan-2-ylphenyl)propyl]amino]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)NCC(C)CC=2C=CC(=CC=2)C(C)C)C=CC=1C1(C(=O)OCC)CC1 UHVUFLDKAHQKBL-UHFFFAOYSA-N 0.000 description 1
- IZRZROSZZFAARA-QFIPXVFZSA-N ethyl 1-[4-[4-[3-methyl-4-[[[(2r)-2-phenylpropyl]amino]methyl]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CNC[C@H](C)C=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 IZRZROSZZFAARA-QFIPXVFZSA-N 0.000 description 1
- JQUNORLKLMZDEE-UHFFFAOYSA-N ethyl 1-[4-[4-[3-methyl-4-[[methyl(2-phenylethyl)amino]methyl]-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CN(C)CCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 JQUNORLKLMZDEE-UHFFFAOYSA-N 0.000 description 1
- KCBBFUDYDJYODW-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(1,1-difluoro-4-phenylbutyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical class C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(F)(F)CCCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 KCBBFUDYDJYODW-UHFFFAOYSA-N 0.000 description 1
- SKRBJGXYPCQCDZ-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(1-hydroxy-2,2-dimethyl-4-phenylbutyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C(C)(C)CCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 SKRBJGXYPCQCDZ-UHFFFAOYSA-N 0.000 description 1
- ULGHLLNFJWCCJS-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(1-hydroxy-2,2-dimethylbut-3-enyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C(C)(C)C=C)C=CC=1C1(C(=O)OCC)CC1 ULGHLLNFJWCCJS-UHFFFAOYSA-N 0.000 description 1
- QKCWHQGPSKHOJM-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(1-hydroxy-3,3-dimethyl-4-phenylbutyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)CC(C)(C)CC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 QKCWHQGPSKHOJM-UHFFFAOYSA-N 0.000 description 1
- LJOANVWTORBYPV-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(1-hydroxyprop-2-enyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C=C)C=CC=1C1(C(=O)OCC)CC1 LJOANVWTORBYPV-UHFFFAOYSA-N 0.000 description 1
- LGGLOZWPHKIMNS-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(2,2-difluoro-1-hydroxybut-3-enyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C(F)(F)C=C)C=CC=1C1(C(=O)OCC)CC1 LGGLOZWPHKIMNS-UHFFFAOYSA-N 0.000 description 1
- VRZPXYCYQKNNMJ-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(2,2-difluoro-4-phenylbutyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CC(F)(F)CCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 VRZPXYCYQKNNMJ-UHFFFAOYSA-N 0.000 description 1
- POWNXJRZPJDPSK-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(2-benzylsulfanyl-1-hydroxyethyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)CSCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 POWNXJRZPJDPSK-UHFFFAOYSA-N 0.000 description 1
- NICGODIPFLIEMT-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(2-benzylsulfanylethyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CCSCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 NICGODIPFLIEMT-UHFFFAOYSA-N 0.000 description 1
- GFEOVRUUUSFJIP-UHFFFAOYSA-N ethyl 1-[4-[4-[4-(3-hydroxy-4-phenylbutyl)-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)CCC(O)CC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 GFEOVRUUUSFJIP-UHFFFAOYSA-N 0.000 description 1
- DSRBKOWVBPIFNZ-SKCUWOTOSA-N ethyl 1-[4-[4-[4-[(1s)-1-hydroxy-2-[(1r)-1-phenylethoxy]ethyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)[C@H](O)CO[C@H](C)C=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 DSRBKOWVBPIFNZ-SKCUWOTOSA-N 0.000 description 1
- HXHDPBPUKGBJJN-HHHXNRCGSA-N ethyl 1-[4-[4-[4-[(1s)-1-hydroxy-2-phenylmethoxyethyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)[C@H](O)COCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 HXHDPBPUKGBJJN-HHHXNRCGSA-N 0.000 description 1
- POWNXJRZPJDPSK-HHHXNRCGSA-N ethyl 1-[4-[4-[4-[(1s)-2-benzylsulfanyl-1-hydroxyethyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)[C@H](O)CSCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 POWNXJRZPJDPSK-HHHXNRCGSA-N 0.000 description 1
- LUNAKDSHXGFMSB-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[(3-acetyloxy-4-phenylbutan-2-yl)amino]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)NC(C)C(CC=2C=CC=CC=2)OC(C)=O)C=CC=1C1(C(=O)OCC)CC1 LUNAKDSHXGFMSB-UHFFFAOYSA-N 0.000 description 1
- KDCDCTIRNIYRPT-FMQUCBEESA-N ethyl 1-[4-[4-[4-[(e)-1-hydroxy-2,2-dimethyl-4-phenylbut-3-enyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C(C)(C)\C=C\C=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 KDCDCTIRNIYRPT-FMQUCBEESA-N 0.000 description 1
- BMCDQIPIHGZDGT-ZHACJKMWSA-N ethyl 1-[4-[4-[4-[(e)-1-hydroxy-2-methyl-4-phenylbut-3-enyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C(C)\C=C\C=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 BMCDQIPIHGZDGT-ZHACJKMWSA-N 0.000 description 1
- KQZANGQWTICNBP-RMKNXTFCSA-N ethyl 1-[4-[4-[4-[(e)-1-hydroxy-4-(3-methylphenyl)but-3-enyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C\C=C\C=2C=C(C)C=CC=2)C=CC=1C1(C(=O)OCC)CC1 KQZANGQWTICNBP-RMKNXTFCSA-N 0.000 description 1
- CFAPLYJTJUZBKZ-FNORWQNLSA-N ethyl 1-[4-[4-[4-[(e)-1-hydroxy-4-[3-(trifluoromethyl)phenyl]but-3-enyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C\C=C\C=2C=C(C=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 CFAPLYJTJUZBKZ-FNORWQNLSA-N 0.000 description 1
- XSRNFHHNKSHZOF-JXMROGBWSA-N ethyl 1-[4-[4-[4-[(e)-1-hydroxy-4-phenylbut-3-enyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C\C=C\C=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 XSRNFHHNKSHZOF-JXMROGBWSA-N 0.000 description 1
- TVDNKDSOLJNHGG-WUKNDPDISA-N ethyl 1-[4-[4-[4-[(e)-2,2-difluoro-1-hydroxy-4-[4-(trifluoromethyl)phenyl]but-3-enyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C(F)(F)\C=C\C=2C=CC(=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 TVDNKDSOLJNHGG-WUKNDPDISA-N 0.000 description 1
- YJIXLARYCVLDGO-ISLYRVAYSA-N ethyl 1-[4-[4-[4-[(e)-2,2-difluoro-1-hydroxy-4-phenylbut-3-enyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C(F)(F)\C=C\C=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 YJIXLARYCVLDGO-ISLYRVAYSA-N 0.000 description 1
- XDIBJLRGJBSDNW-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[1-[tert-butyl(dimethyl)silyl]oxy-4-phenylbutyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(CCCC=2C=CC=CC=2)O[Si](C)(C)C(C)(C)C)C=CC=1C1(C(=O)OCC)CC1 XDIBJLRGJBSDNW-UHFFFAOYSA-N 0.000 description 1
- ZIQHAESITZKVOP-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[1-hydroxy-2-(2-phenylethoxy)ethyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)COCCC=2C=CC=CC=2)C=CC=1C1(C(=O)OCC)CC1 ZIQHAESITZKVOP-UHFFFAOYSA-N 0.000 description 1
- CADFZGCUESKKDJ-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[1-hydroxy-2-[[3-(trifluoromethyl)phenyl]methoxy]ethyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)COCC=2C=C(C=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 CADFZGCUESKKDJ-UHFFFAOYSA-N 0.000 description 1
- YCNDQEZMHHXMAG-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[1-hydroxy-2-[[3-(trifluoromethyl)phenyl]methylsulfanyl]ethyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)CSCC=2C=C(C=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 YCNDQEZMHHXMAG-UHFFFAOYSA-N 0.000 description 1
- ZZUPMQFZOOCOGM-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[1-hydroxy-4-(3-methylphenyl)butyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical class C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)CCCC=2C=C(C)C=CC=2)C=CC=1C1(C(=O)OCC)CC1 ZZUPMQFZOOCOGM-UHFFFAOYSA-N 0.000 description 1
- GDTSZYBEFGGAKE-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[1-hydroxy-4-[2-(trifluoromethyl)phenyl]butyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)CCCC=2C(=CC=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 GDTSZYBEFGGAKE-UHFFFAOYSA-N 0.000 description 1
- YARZEABLSXRRMY-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[1-hydroxy-4-[3-(trifluoromethyl)phenyl]butyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)CCCC=2C=C(C=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 YARZEABLSXRRMY-UHFFFAOYSA-N 0.000 description 1
- YBAXVESRANBHIA-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[1-hydroxy-4-[4-(trifluoromethyl)phenyl]butyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)CCCC=2C=CC(=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 YBAXVESRANBHIA-UHFFFAOYSA-N 0.000 description 1
- DSYTYVAAUNUAPP-UHFFFAOYSA-N ethyl 1-[4-[4-[4-[2,2-difluoro-1-hydroxy-4-[4-(trifluoromethyl)phenyl]butyl]-3-methyl-1,2-oxazol-5-yl]phenyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C2=C(C(C)=NO2)C(O)C(F)(F)CCC=2C=CC(=CC=2)C(F)(F)F)C=CC=1C1(C(=O)OCC)CC1 DSYTYVAAUNUAPP-UHFFFAOYSA-N 0.000 description 1
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2013506694A (ja) * | 2009-10-01 | 2013-02-28 | アミラ ファーマシューティカルス,インコーポレーテッド | リゾホスファチジン酸受容体アンタゴニストとしての化合物 |
JP2016515536A (ja) * | 2013-03-15 | 2016-05-30 | エピゲン バイオサイエンシズ, インコーポレイテッドEpigen Biosciences, Inc. | 疾患の治療に有用な複素環化合物 |
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WO2010068775A2 (en) | 2008-12-11 | 2010-06-17 | Amira Pharmaceuticals, Inc. | Alkyne antagonists of lysophosphatidic acid receptors |
GB2466121B (en) * | 2008-12-15 | 2010-12-08 | Amira Pharmaceuticals Inc | Antagonists of lysophosphatidic acid receptors |
GB2470833B (en) | 2009-06-03 | 2011-06-01 | Amira Pharmaceuticals Inc | Polycyclic antagonists of lysophosphatidic acid receptors |
JP2013501064A (ja) | 2009-08-04 | 2013-01-10 | アミラ ファーマシューティカルス,インコーポレーテッド | リゾホスファチジン酸受容体アンタゴニストとしての化合物 |
GB2474748B (en) | 2009-10-01 | 2011-10-12 | Amira Pharmaceuticals Inc | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
CA2820817A1 (en) | 2010-12-07 | 2012-06-14 | Amira Pharmaceuticals, Inc. | Lysophosphatidic acid receptor antagonists and uses thereof |
WO2012138797A1 (en) | 2011-04-05 | 2012-10-11 | Amira Pharmaceuticals, Inc. | 3- or 5 - bi phenyl - 4 - ylisoxazole - based compounds useful for the treatment of fibrosis, pain, cancer and respiratory, allergic, nervous system or cardiovascular disorders |
WO2013020622A1 (en) * | 2011-08-08 | 2013-02-14 | Merck Patent Gmbh | N-(benzimimdazol-2-yl)-cyclopropane carboxamides as lysophosphatidic acid antagonists |
HK1199259A1 (en) | 2011-08-15 | 2015-06-26 | Intermune, Inc. | Lysophosphatidic acid receptor antagonists |
WO2013070879A1 (en) * | 2011-11-10 | 2013-05-16 | Bristol-Myers Squibb Company | Methods for treating spinal cord injury with lpa receptor antagonists |
CN103987858A (zh) | 2011-11-22 | 2014-08-13 | 英特芒尼公司 | 诊断和治疗特发性肺纤维化的方法 |
JP2015505536A (ja) | 2012-01-20 | 2015-02-23 | アクセラ インク. | 疾患の処置のための置換された複素環化合物 |
RU2649398C2 (ru) | 2012-12-28 | 2018-04-03 | Убе Индастриз, Лтд. | Галогензамещенное гетероциклическое соединение |
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WO2001060819A1 (fr) * | 2000-02-18 | 2001-08-23 | Kirin Beer Kabushiki Kaisha | Nouveaux composes d'isoxazole et de thiazole et leur utilisation en tant que medicaments |
JP2003261545A (ja) * | 2001-12-28 | 2003-09-19 | Takeda Chem Ind Ltd | 神経栄養因子産生・分泌促進剤 |
JP2012512178A (ja) * | 2008-12-15 | 2012-05-31 | パンミラ ファーマシューティカルズ,エルエルシー. | リゾホスファチジン酸受容体のアンタゴニスト |
JP2013506694A (ja) * | 2009-10-01 | 2013-02-28 | アミラ ファーマシューティカルス,インコーポレーテッド | リゾホスファチジン酸受容体アンタゴニストとしての化合物 |
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CN102639515A (zh) | 2012-08-15 |
WO2011041694A2 (en) | 2011-04-07 |
EP2483252A4 (en) | 2013-04-03 |
TW201116278A (en) | 2011-05-16 |
UY32926A (es) | 2010-11-30 |
WO2011041729A3 (en) | 2011-08-04 |
JP2013506694A (ja) | 2013-02-28 |
US20150329502A1 (en) | 2015-11-19 |
US20120289522A1 (en) | 2012-11-15 |
CN102666504A (zh) | 2012-09-12 |
WO2011041729A2 (en) | 2011-04-07 |
TWI401082B (zh) | 2013-07-11 |
US9624182B2 (en) | 2017-04-18 |
EP2483252B1 (en) | 2017-03-08 |
US9090573B2 (en) | 2015-07-28 |
US8217066B2 (en) | 2012-07-10 |
EP2483252A2 (en) | 2012-08-08 |
EP2483253A4 (en) | 2013-04-03 |
GB201016314D0 (en) | 2010-11-10 |
EP2483253A2 (en) | 2012-08-08 |
GB2474120B (en) | 2011-12-21 |
IN2012DN02177A (en:Method) | 2015-08-21 |
WO2011041694A3 (en) | 2011-08-18 |
US20110082181A1 (en) | 2011-04-07 |
AR078497A1 (es) | 2011-11-09 |
IN2012DN02735A (en:Method) | 2015-09-11 |
CN102666504B (zh) | 2016-06-01 |
GB2474120A (en) | 2011-04-06 |
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