JP5531370B2 - プロスタグランジンd2受容体のアンタゴニスト - Google Patents
プロスタグランジンd2受容体のアンタゴニスト Download PDFInfo
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- JP5531370B2 JP5531370B2 JP2011516892A JP2011516892A JP5531370B2 JP 5531370 B2 JP5531370 B2 JP 5531370B2 JP 2011516892 A JP2011516892 A JP 2011516892A JP 2011516892 A JP2011516892 A JP 2011516892A JP 5531370 B2 JP5531370 B2 JP 5531370B2
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- Prior art keywords
- phenyl
- compound
- phenoxy
- acetic acid
- methoxy
- 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.)
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- 229940122913 Prostaglandin D2 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 247
- -1 2,2-dimethyl-propionylamino Chemical group 0.000 claims description 107
- 238000000034 method Methods 0.000 claims description 81
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 241000124008 Mammalia Species 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 44
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- 201000010099 disease Diseases 0.000 claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- 208000006673 asthma Diseases 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 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 description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 208000026935 allergic disease Diseases 0.000 claims description 6
- 239000003889 eye drop Substances 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 5
- WPOBVOJTGDGNMT-UHFFFAOYSA-N 2-[3-[2-(tert-butylsulfanylmethyl)-4-(2,2-dimethylpropanoylamino)phenoxy]-4-hydroxyphenyl]acetic acid Chemical compound CC(C)(C)SCC1=CC(NC(=O)C(C)(C)C)=CC=C1OC1=CC(CC(O)=O)=CC=C1O WPOBVOJTGDGNMT-UHFFFAOYSA-N 0.000 claims description 5
- QLCDZGGZPBEMNS-UHFFFAOYSA-N 2-[3-[4-[(4-chlorobenzoyl)amino]-2-[(4-chlorophenyl)sulfanylmethyl]phenoxy]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC(C(=C1)CSC=2C=CC(Cl)=CC=2)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 QLCDZGGZPBEMNS-UHFFFAOYSA-N 0.000 claims description 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
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- USWBKHALWGFONL-UHFFFAOYSA-N 2-[3-[4-(benzylcarbamoylamino)-2-[(4-chlorophenyl)sulfanylmethyl]phenoxy]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC(C(=C1)CSC=2C=CC(Cl)=CC=2)=CC=C1NC(=O)NCC1=CC=CC=C1 USWBKHALWGFONL-UHFFFAOYSA-N 0.000 claims description 4
- XIIYXRCKQZCTGN-UHFFFAOYSA-N 2-[3-[4-[(4-chlorobenzoyl)amino]-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC(C(=C1)CSCC(F)(F)F)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 XIIYXRCKQZCTGN-UHFFFAOYSA-N 0.000 claims description 4
- KKZKCOTVDVAABH-UHFFFAOYSA-N 2-[4-chloro-3-[4-(2,2-dimethylpropanoylamino)-2-(propan-2-ylsulfanylmethyl)phenoxy]phenyl]acetic acid Chemical compound CC(C)SCC1=CC(NC(=O)C(C)(C)C)=CC=C1OC1=CC(CC(O)=O)=CC=C1Cl KKZKCOTVDVAABH-UHFFFAOYSA-N 0.000 claims description 4
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- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 239000003826 tablet Substances 0.000 claims description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims description 3
- XSQWVIPFQQAXFK-UHFFFAOYSA-N 2-[3-[2-(tert-butylsulfanylmethyl)-4-(2,2-dimethylpropanoylamino)phenoxy]-5-chlorophenyl]acetic acid Chemical compound CC(C)(C)SCC1=CC(NC(=O)C(C)(C)C)=CC=C1OC1=CC(Cl)=CC(CC(O)=O)=C1 XSQWVIPFQQAXFK-UHFFFAOYSA-N 0.000 claims description 3
- WBHSEPLZVRMKHW-UHFFFAOYSA-N 2-[3-[2-(tert-butylsulfanylmethyl)-4-[(4-chlorobenzoyl)amino]phenoxy]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC(C(=C1)CSC(C)(C)C)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 WBHSEPLZVRMKHW-UHFFFAOYSA-N 0.000 claims description 3
- YDWVQQVDHDSJCX-UHFFFAOYSA-N 2-[3-[4-(2,2-dimethylpropanoylamino)-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC1=CC=C(NC(=O)C(C)(C)C)C=C1CSCC(F)(F)F YDWVQQVDHDSJCX-UHFFFAOYSA-N 0.000 claims description 3
- BSHRRPOEESYZAW-UHFFFAOYSA-N 2-[3-[4-(benzylcarbamoylamino)-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC(C(=C1)CSCC(F)(F)F)=CC=C1NC(=O)NCC1=CC=CC=C1 BSHRRPOEESYZAW-UHFFFAOYSA-N 0.000 claims description 3
- UZYVJBSFPATPAU-UHFFFAOYSA-N 2-[3-[4-[(4-chlorobenzoyl)amino]-2-(phenylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC(C(=C1)CSC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 UZYVJBSFPATPAU-UHFFFAOYSA-N 0.000 claims description 3
- GGRIZSRTFNFCDH-UHFFFAOYSA-N 2-[3-[4-[(4-chlorobenzoyl)amino]-2-(propan-2-ylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC(C(=C1)CSC(C)C)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 GGRIZSRTFNFCDH-UHFFFAOYSA-N 0.000 claims description 3
- OIZFSHNYUBVULW-UHFFFAOYSA-N 2-[4-(difluoromethoxy)-3-[4-(2,2-dimethylpropanoylamino)-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]phenyl]acetic acid Chemical compound FC(F)(F)CSCC1=CC(NC(=O)C(C)(C)C)=CC=C1OC1=CC(CC(O)=O)=CC=C1OC(F)F OIZFSHNYUBVULW-UHFFFAOYSA-N 0.000 claims description 3
- KOZPHQIQTTYSBP-UHFFFAOYSA-N 2-[4-methoxy-3-[4-(2-oxo-1,3-oxazolidin-3-yl)-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]phenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC1=CC=C(N2C(OCC2)=O)C=C1CSCC(F)(F)F KOZPHQIQTTYSBP-UHFFFAOYSA-N 0.000 claims description 3
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 claims description 3
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 3
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 3
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- 229940127113 compound 57 Drugs 0.000 claims description 3
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- 229940097496 nasal spray Drugs 0.000 claims description 3
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- 238000011200 topical administration Methods 0.000 claims description 3
- 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
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 2
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- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims description 2
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- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 claims description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims description 2
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- WNZGRYMQPNDSGY-UHFFFAOYSA-N ethyl 2-[3-[2-(tert-butylsulfanylmethyl)-4-[(4-chlorobenzoyl)amino]phenoxy]-4-chlorophenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(Cl)C(OC=2C(=CC(NC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CSC(C)(C)C)=C1 WNZGRYMQPNDSGY-UHFFFAOYSA-N 0.000 description 1
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- SVGOEGKETLHWPB-UHFFFAOYSA-N ethyl 2-[3-[2-(tert-butylsulfanylmethyl)-4-[(4-fluorobenzoyl)amino]phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(NC(=O)C=3C=CC(F)=CC=3)=CC=2)CSC(C)(C)C)=C1 SVGOEGKETLHWPB-UHFFFAOYSA-N 0.000 description 1
- RGTOQHDMEWJBSV-UHFFFAOYSA-N ethyl 2-[3-[2-(tert-butylsulfanylmethyl)-4-[(6-methoxypyridin-3-yl)carbamoyl]phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(=CC=2)C(=O)NC=2C=NC(OC)=CC=2)CSC(C)(C)C)=C1 RGTOQHDMEWJBSV-UHFFFAOYSA-N 0.000 description 1
- UWISNUMCVHVXGQ-UHFFFAOYSA-N ethyl 2-[3-[2-(tert-butylsulfanylmethyl)-4-[[1-(4-fluorophenyl)-2-methylpropan-2-yl]carbamoyl]phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(=CC=2)C(=O)NC(C)(C)CC=2C=CC(F)=CC=2)CSC(C)(C)C)=C1 UWISNUMCVHVXGQ-UHFFFAOYSA-N 0.000 description 1
- MRFBEWDWMSJAKJ-UHFFFAOYSA-N ethyl 2-[3-[2-(tert-butylsulfanylmethyl)-4-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(NS(=O)(=O)C=3C4=CC=CC(=C4C=CC=3)N(C)C)=CC=2)CSC(C)(C)C)=C1 MRFBEWDWMSJAKJ-UHFFFAOYSA-N 0.000 description 1
- NMXOZSBUSMANKN-UHFFFAOYSA-N ethyl 2-[3-[2-(tert-butylsulfanylmethyl)-4-[methyl(propan-2-yl)carbamoyl]phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(=CC=2)C(=O)N(C)C(C)C)CSC(C)(C)C)=C1 NMXOZSBUSMANKN-UHFFFAOYSA-N 0.000 description 1
- FVJGXSXUOCBNDC-UHFFFAOYSA-N ethyl 2-[3-[2-(tert-butylsulfanylmethyl)-4-nitrophenoxy]-4-chlorophenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(Cl)C(OC=2C(=CC(=CC=2)[N+]([O-])=O)CSC(C)(C)C)=C1 FVJGXSXUOCBNDC-UHFFFAOYSA-N 0.000 description 1
- HRZCQQKFWYPABC-UHFFFAOYSA-N ethyl 2-[3-[2-[(4-chlorophenyl)sulfanylmethyl]-4-(2,2-dimethylpropanoylamino)phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(NC(=O)C(C)(C)C)=CC=2)CSC=2C=CC(Cl)=CC=2)=C1 HRZCQQKFWYPABC-UHFFFAOYSA-N 0.000 description 1
- VFMLSFLJNQBIDW-UHFFFAOYSA-N ethyl 2-[3-[4-(2,2-dimethylpropanoylamino)-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(NC(=O)C(C)(C)C)=CC=2)CSCC(F)(F)F)=C1 VFMLSFLJNQBIDW-UHFFFAOYSA-N 0.000 description 1
- WUNHTUSOOIXTLG-UHFFFAOYSA-N ethyl 2-[3-[4-(2,2-dimethylpropanoylamino)-2-(propan-2-ylsulfanylmethyl)phenoxy]-5-(trifluoromethyl)phenyl]acetate Chemical compound FC(F)(F)C1=CC(CC(=O)OCC)=CC(OC=2C(=CC(NC(=O)C(C)(C)C)=CC=2)CSC(C)C)=C1 WUNHTUSOOIXTLG-UHFFFAOYSA-N 0.000 description 1
- BETUATDIWUKNQB-UHFFFAOYSA-N ethyl 2-[3-[4-(2-chloroethoxycarbonylamino)-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(NC(=O)OCCCl)=CC=2)CSCC(F)(F)F)=C1 BETUATDIWUKNQB-UHFFFAOYSA-N 0.000 description 1
- VPWOCRVDASKMKK-UHFFFAOYSA-N ethyl 2-[3-[4-(2-chloroethylcarbamoylamino)-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(NC(=O)NCCCl)=CC=2)CSCC(F)(F)F)=C1 VPWOCRVDASKMKK-UHFFFAOYSA-N 0.000 description 1
- VVUVPHKUEHFNEW-UHFFFAOYSA-N ethyl 2-[3-[4-(3,3-dimethylbutanoylamino)-2-(2,2,2-trifluoroethylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(NC(=O)CC(C)(C)C)=CC=2)CSCC(F)(F)F)=C1 VVUVPHKUEHFNEW-UHFFFAOYSA-N 0.000 description 1
- UYXGAFIPFYMYJS-UHFFFAOYSA-N ethyl 2-[3-[4-(benzylcarbamoylamino)-2-(tert-butylsulfanylmethyl)phenoxy]-4-methoxyphenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(OC)C(OC=2C(=CC(NC(=O)NCC=3C=CC=CC=3)=CC=2)CSC(C)(C)C)=C1 UYXGAFIPFYMYJS-UHFFFAOYSA-N 0.000 description 1
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- C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
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- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
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- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D263/18—Oxygen atoms
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- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013516475A (ja) * | 2010-01-06 | 2013-05-13 | アミラ ファーマシューティカルズ,インク. | Dp2アンタゴニストおよびその使用 |
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