JP2005529975A5 - - Google Patents
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- JP2005529975A5 JP2005529975A5 JP2004515700A JP2004515700A JP2005529975A5 JP 2005529975 A5 JP2005529975 A5 JP 2005529975A5 JP 2004515700 A JP2004515700 A JP 2004515700A JP 2004515700 A JP2004515700 A JP 2004515700A JP 2005529975 A5 JP2005529975 A5 JP 2005529975A5
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- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- group
- phenyl
- independently
- 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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- 125000003118 aryl group Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- -1 trifluoromethylphenyl Chemical group 0.000 claims description 27
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- RUSPQRHGHITWEO-IBGZPJMESA-N (2s)-3-[4-[2-[2-[(2,6-dichlorophenyl)methylsulfanyl]ethylamino]-2-oxoethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NCCSCC1=C(Cl)C=CC=C1Cl RUSPQRHGHITWEO-IBGZPJMESA-N 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000005002 aryl methyl group Chemical group 0.000 claims 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical group C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 claims 2
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000005841 biaryl group Chemical group 0.000 claims 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- 150000003536 tetrazoles Chemical class 0.000 claims 2
- 125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
- 241000124008 Mammalia Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000006331 halo benzoyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000006277 halobenzyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NEJJCKFYYBEQRQ-LBPRGKRZSA-N ethyl (2s)-2-ethoxy-3-(4-hydroxyphenyl)propanoate Chemical compound CCOC(=O)[C@@H](OCC)CC1=CC=C(O)C=C1 NEJJCKFYYBEQRQ-LBPRGKRZSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NHLZFLNKLYWCTP-NRFANRHFSA-N (2s)-3-[4-[2-[benzyl-(3-ethoxy-3-oxopropyl)amino]-2-oxoethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C=1C=C(C[C@H](OC)C(O)=O)C=CC=1OCC(=O)N(CCC(=O)OCC)CC1=CC=CC=C1 NHLZFLNKLYWCTP-NRFANRHFSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LGWJZUHWCFYDGR-GGYWPGCISA-N (2s)-2-methoxy-3-[4-[2-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]-2-oxoethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NC(C(=O)OC)CC1=CC=CC=C1 LGWJZUHWCFYDGR-GGYWPGCISA-N 0.000 description 2
- CMQBESBIPOGASP-FQEVSTJZSA-N (2s)-2-methoxy-3-[4-[2-[3-(n-methylanilino)propylamino]-2-oxoethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NCCCN(C)C1=CC=CC=C1 CMQBESBIPOGASP-FQEVSTJZSA-N 0.000 description 2
- RRFYAKLUYFDDQO-ZDUSSCGKSA-N (2s)-3-[4-[2-[(5-tert-butyl-1,3,4-thiadiazol-2-yl)amino]-2-oxoethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NC1=NN=C(C(C)(C)C)S1 RRFYAKLUYFDDQO-ZDUSSCGKSA-N 0.000 description 2
- BYDFFKSDEOOVMU-QODXOHEASA-N (2s)-3-[4-[2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]-2-oxoethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)N1CCN(C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)CC1 BYDFFKSDEOOVMU-QODXOHEASA-N 0.000 description 2
- RUCDMFWKPPFRIZ-YSYXNDDBSA-N (2s)-3-[4-[2-[butyl(1-phenylethyl)amino]-2-oxoethoxy]phenyl]-2-methoxypropanoic acid Chemical compound C=1C=C(C[C@H](OC)C(O)=O)C=CC=1OCC(=O)N(CCCC)C(C)C1=CC=CC=C1 RUCDMFWKPPFRIZ-YSYXNDDBSA-N 0.000 description 2
- YMEZPZLMWZNGJG-UHFFFAOYSA-N 2-ethoxy-3-[4-[1-[2-(4-ethylphenyl)ethylamino]-1-oxopropan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OC(C)C(=O)NCCC1=CC=C(CC)C=C1 YMEZPZLMWZNGJG-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GQHGXHIEPRBWEO-MGPUTAFESA-N (2r)-3-[4-[(2s)-1-[2-(3-chlorophenyl)ethylamino]-1-oxopropan-2-yl]oxyphenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(C[C@@H](OCC)C(O)=O)=CC=C1O[C@@H](C)C(=O)NCCC1=CC=CC(Cl)=C1 GQHGXHIEPRBWEO-MGPUTAFESA-N 0.000 description 1
- GIDMFDDLYPPKAD-SMDDNHRTSA-N (2s)-2-[4-[(2r)-2,3-diethoxy-3-oxopropyl]phenoxy]propanoic acid Chemical compound CCOC(=O)[C@H](OCC)CC1=CC=C(O[C@@H](C)C(O)=O)C=C1 GIDMFDDLYPPKAD-SMDDNHRTSA-N 0.000 description 1
- GIDMFDDLYPPKAD-FZMZJTMJSA-N (2s)-2-[4-[(2s)-2,3-diethoxy-3-oxopropyl]phenoxy]propanoic acid Chemical compound CCOC(=O)[C@@H](OCC)CC1=CC=C(O[C@@H](C)C(O)=O)C=C1 GIDMFDDLYPPKAD-FZMZJTMJSA-N 0.000 description 1
- FKTHZBOIAZZAIE-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[1-(heptylamino)-2-methyl-1-oxopropan-2-yl]oxyphenyl]propanoic acid Chemical compound CCCCCCCNC(=O)C(C)(C)OC1=CC=C(C[C@H](OCC)C(O)=O)C=C1 FKTHZBOIAZZAIE-IBGZPJMESA-N 0.000 description 1
- DFVZVUPASJGJQG-QFIPXVFZSA-N (2s)-2-ethoxy-3-[4-[1-[2-(2-ethoxyphenyl)ethylamino]-2-methyl-1-oxopropan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCCC1=CC=CC=C1OCC DFVZVUPASJGJQG-QFIPXVFZSA-N 0.000 description 1
- HZZULILNTPZNRI-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[1-[2-(2-fluorophenyl)ethylamino]-2-methyl-1-oxopropan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCCC1=CC=CC=C1F HZZULILNTPZNRI-FQEVSTJZSA-N 0.000 description 1
- MBQIFHYCRDUOGT-QFIPXVFZSA-N (2s)-2-ethoxy-3-[4-[1-[2-(4-ethylphenyl)ethylamino]-2-methyl-1-oxopropan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCCC1=CC=C(CC)C=C1 MBQIFHYCRDUOGT-QFIPXVFZSA-N 0.000 description 1
- WGQNJVQXWDESPK-IBGZPJMESA-N (2s)-2-ethoxy-3-[4-[1-[[3-fluoro-5-(trifluoromethyl)phenyl]methylamino]-2-methyl-1-oxopropan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCC1=CC(F)=CC(C(F)(F)F)=C1 WGQNJVQXWDESPK-IBGZPJMESA-N 0.000 description 1
- BTPIKSAVBIOBHV-VWLOTQADSA-N (2s)-2-ethoxy-3-[4-[2-methyl-1-oxo-1-[(3-phenylphenyl)methylamino]propan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCC1=CC=CC(C=2C=CC=CC=2)=C1 BTPIKSAVBIOBHV-VWLOTQADSA-N 0.000 description 1
- KVSVDIMAQSFFNP-FQEVSTJZSA-N (2s)-2-ethoxy-3-[4-[2-methyl-1-oxo-1-[2-[3-(trifluoromethyl)phenyl]ethylamino]propan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCCC1=CC=CC(C(F)(F)F)=C1 KVSVDIMAQSFFNP-FQEVSTJZSA-N 0.000 description 1
- QRZGXSTWYLBVPY-DEOSSOPVSA-N (2s)-2-methoxy-3-[3-[2-methyl-1-oxo-1-[(3-phenylphenyl)methylamino]propan-2-yl]oxyphenyl]propanoic acid Chemical compound CO[C@H](C(O)=O)CC1=CC=CC(OC(C)(C)C(=O)NCC=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 QRZGXSTWYLBVPY-DEOSSOPVSA-N 0.000 description 1
- UPJZWWWATGTOBC-XLDIYJRPSA-N (2s)-2-methoxy-3-[4-[2-(1-naphthalen-1-ylethylamino)-2-oxoethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NC(C)C1=CC=CC2=CC=CC=C12 UPJZWWWATGTOBC-XLDIYJRPSA-N 0.000 description 1
- YVIYAERGBLREAJ-HNNXBMFYSA-N (2s)-2-methoxy-3-[4-[2-(3-methylbutylamino)-2-oxoethoxy]phenyl]propanoic acid Chemical compound CO[C@H](C(O)=O)CC1=CC=C(OCC(=O)NCCC(C)C)C=C1 YVIYAERGBLREAJ-HNNXBMFYSA-N 0.000 description 1
- UIGCCCQYJOBHRJ-VYIIXAMBSA-N (2s)-2-methoxy-3-[4-[2-(4-methylpentan-2-ylamino)-2-oxoethoxy]phenyl]propanoic acid Chemical compound CO[C@H](C(O)=O)CC1=CC=C(OCC(=O)NC(C)CC(C)C)C=C1 UIGCCCQYJOBHRJ-VYIIXAMBSA-N 0.000 description 1
- SVXZYZHUUQXPKI-NRFANRHFSA-N (2s)-2-methoxy-3-[4-[2-(naphthalen-1-ylmethylamino)-2-oxoethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NCC1=CC=CC2=CC=CC=C12 SVXZYZHUUQXPKI-NRFANRHFSA-N 0.000 description 1
- HSHUCYOVPMLWTN-NRFANRHFSA-N (2s)-2-methoxy-3-[4-[2-[4-(4-methylphenyl)piperazin-1-yl]-2-oxoethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)N1CCN(C=2C=CC(C)=CC=2)CC1 HSHUCYOVPMLWTN-NRFANRHFSA-N 0.000 description 1
- WYBCQSSTYSFDCI-FUBQLUNQSA-N (2s)-2-methoxy-3-[4-[2-[methyl(1-phenylethyl)amino]-2-oxoethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)N(C)C(C)C1=CC=CC=C1 WYBCQSSTYSFDCI-FUBQLUNQSA-N 0.000 description 1
- SYQNHOCOOCALKF-QFIPXVFZSA-N (2s)-2-methoxy-3-[4-[2-[methyl(naphthalen-1-ylmethyl)amino]-2-oxoethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)N(C)CC1=CC=CC2=CC=CC=C12 SYQNHOCOOCALKF-QFIPXVFZSA-N 0.000 description 1
- BEEBGXKSMANYFX-DEOSSOPVSA-N (2s)-2-methoxy-3-[4-[2-methyl-1-oxo-1-[(3-phenylphenyl)methylamino]propan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCC1=CC=CC(C=2C=CC=CC=2)=C1 BEEBGXKSMANYFX-DEOSSOPVSA-N 0.000 description 1
- ZOGUTDIFRPDUPU-VWLOTQADSA-N (2s)-2-methoxy-3-[4-[2-methyl-1-oxo-1-[2-(4-phenoxyphenyl)ethylamino]propan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCCC(C=C1)=CC=C1OC1=CC=CC=C1 ZOGUTDIFRPDUPU-VWLOTQADSA-N 0.000 description 1
- VFHZHHHYXVSDJG-SFHVURJKSA-N (2s)-2-methoxy-3-[4-[2-methyl-1-oxo-1-[[3-(trifluoromethyl)phenyl]methylamino]propan-2-yl]oxyphenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OC(C)(C)C(=O)NCC1=CC=CC(C(F)(F)F)=C1 VFHZHHHYXVSDJG-SFHVURJKSA-N 0.000 description 1
- PCOOKOXRAOGYDJ-IBYPIGCZSA-N (2s)-2-methoxy-3-[4-[2-oxo-2-(1-phenylethylamino)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NC(C)C1=CC=CC=C1 PCOOKOXRAOGYDJ-IBYPIGCZSA-N 0.000 description 1
- XBTYCYSJEFNVOI-KRWDZBQOSA-N (2s)-2-methoxy-3-[4-[2-oxo-2-(2-pyridin-2-ylethylamino)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NCCC1=CC=CC=N1 XBTYCYSJEFNVOI-KRWDZBQOSA-N 0.000 description 1
- DCNHPLOOTBQRAJ-FZCLLLDFSA-N (2s)-2-methoxy-3-[4-[2-oxo-2-(4-phenylbutan-2-ylamino)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NC(C)CCC1=CC=CC=C1 DCNHPLOOTBQRAJ-FZCLLLDFSA-N 0.000 description 1
- BFYBHPYBJJMVEL-CVRLYYSRSA-N (2s)-2-methoxy-3-[4-[2-oxo-2-(pentan-2-ylamino)ethoxy]phenyl]propanoic acid Chemical compound CCCC(C)NC(=O)COC1=CC=C(C[C@H](OC)C(O)=O)C=C1 BFYBHPYBJJMVEL-CVRLYYSRSA-N 0.000 description 1
- DKYRCNGCAWIMMJ-DEOSSOPVSA-N (2s)-2-methoxy-3-[4-[2-oxo-2-[2-(4-phenoxyphenyl)ethylamino]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)NCCC(C=C1)=CC=C1OC1=CC=CC=C1 DKYRCNGCAWIMMJ-DEOSSOPVSA-N 0.000 description 1
- NCVJBVDWOWTSQQ-FQEVSTJZSA-N (2s)-2-methoxy-3-[4-[2-oxo-2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OC)C(O)=O)=CC=C1OCC(=O)N1CCN(C=2C=CC(=CC=2)C(F)(F)F)CC1 NCVJBVDWOWTSQQ-FQEVSTJZSA-N 0.000 description 1
- ZHDBPJIHUCUJLN-SFHVURJKSA-N (2s)-3-[3-[1-(heptylamino)-2-methyl-1-oxopropan-2-yl]oxyphenyl]-2-methoxypropanoic acid Chemical compound CCCCCCCNC(=O)C(C)(C)OC1=CC=CC(C[C@H](OC)C(O)=O)=C1 ZHDBPJIHUCUJLN-SFHVURJKSA-N 0.000 description 1
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39010202P | 2002-06-19 | 2002-06-19 | |
| PCT/US2003/016207 WO2004000789A1 (en) | 2002-06-19 | 2003-06-11 | Amide linker peroxisome proliferator activated receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005529975A JP2005529975A (ja) | 2005-10-06 |
| JP2005529975A5 true JP2005529975A5 (cg-RX-API-DMAC7.html) | 2006-07-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2004515700A Pending JP2005529975A (ja) | 2002-06-19 | 2003-06-11 | アミドリンカーペルオキシソーム増殖因子活性化受容体調節因子 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7220880B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1517882A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2005529975A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1662487A (cg-RX-API-DMAC7.html) |
| AR (1) | AR039684A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003241579B9 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0311834A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2488972A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA04013000A (cg-RX-API-DMAC7.html) |
| PE (1) | PE20040580A1 (cg-RX-API-DMAC7.html) |
| TW (1) | TW200406371A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2004000789A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0229931D0 (en) * | 2002-12-21 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| SE0104334D0 (sv) * | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0314079D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| JP2007516267A (ja) * | 2003-12-15 | 2007-06-21 | イーライ リリー アンド カンパニー | 選択的ペルオキシソーム増殖因子活性化受容体モジュレータ |
| GB0405033D0 (en) * | 2004-03-05 | 2004-04-07 | Karobio Ab | Novel pharmaceutical compositions |
| US8071624B2 (en) | 2004-06-24 | 2011-12-06 | Incyte Corporation | N-substituted piperidines and their use as pharmaceuticals |
| CA2584502A1 (en) * | 2004-06-24 | 2006-01-05 | Incyte Corporation | 2-methylpropanamides and their use as pharmaceuticals |
| GT200500375A (es) * | 2004-12-20 | 2006-11-28 | Derivados de piperidina y su uso como agentes antiinflamatorios | |
| EP1893583B1 (en) | 2005-05-31 | 2012-04-04 | Pfizer Inc. | Substituted aryloxy-n-bicyclomethyl acetamide compounds as vr1 antagonists |
| US8097610B2 (en) * | 2005-08-26 | 2012-01-17 | Shionogi & Co., Ltd. | Derivative having PPAR agonistic activity |
| JP2008239616A (ja) * | 2007-02-28 | 2008-10-09 | Iyaku Bunshi Sekkei Kenkyusho:Kk | Ｈｄｌ上昇剤 |
| CN107382980B (zh) * | 2016-05-14 | 2020-05-15 | 湖南大学 | N-[(二氢苯并呋喃-7-氧基)烷基]-2-芳氧基酰胺衍生物 |
| EP3689324B1 (de) * | 2019-02-04 | 2024-11-20 | Symrise AG | Neue kühlstoffe und zubereitungen, die diese enthalten |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3889545T2 (de) | 1987-10-20 | 1994-10-13 | Otsuka Pharma Co Ltd | Phenylcarbonsäure-abkömmlinge. |
| US5122539A (en) | 1990-02-12 | 1992-06-16 | Center For Innovative Technology | Allosteric hemoglobin modifiers useful for decreasing oxygen affinity and preserving oxygen carrying capability of stored blood |
| GB9027023D0 (en) | 1990-12-12 | 1991-01-30 | Wellcome Found | Anti-atherosclerotic aryl compounds |
| CA2090283A1 (en) | 1992-02-28 | 1993-08-29 | Nobuyuki Hamanaka | Phenoxyacetic acid derivatives |
| JP3144624B2 (ja) | 1995-06-02 | 2001-03-12 | 杏林製薬株式会社 | Ｎ−ベンジルジオキソチアゾリジルベンズアミド誘導体及びその製造法 |
| AU721452B2 (en) | 1996-02-02 | 2000-07-06 | Merck & Co., Inc. | Antidiabetic agents |
| EP1019364B1 (en) | 1997-08-28 | 2004-06-09 | Biovitrum Ab | Inhibitors of protein tyrosine phosphatase |
| AU3958200A (en) * | 1999-04-20 | 2000-11-02 | Novo Nordisk A/S | New compounds, their preparation and use |
| US6417212B1 (en) | 1999-08-27 | 2002-07-09 | Eli Lilly & Company | Modulators of peroxisome proliferator activated receptors |
| PE20011010A1 (es) | 1999-12-02 | 2001-10-18 | Glaxo Group Ltd | Oxazoles y tiazoles sustituidos como agonista del receptor activado por el proliferador de peroxisomas humano |
| JP2001261612A (ja) * | 2000-03-22 | 2001-09-26 | Mitsui Chemicals Inc | カテコールプロピオン酸誘導体およびそれを有効成分として含有する核内レセプター作動薬 |
| EP1310494B1 (en) | 2000-08-11 | 2012-01-25 | Nippon Chemiphar Co., Ltd. | PPAR (delta) ACTIVATORS |
| UA82048C2 (uk) | 2000-11-10 | 2008-03-11 | Эли Лилли Энд Компани | Агоністи альфа-рецепторів, активованих проліфератором пероксисом |
| GB0113232D0 (en) | 2001-05-31 | 2001-07-25 | Glaxo Group Ltd | Chemical process |
| CN1582279A (zh) | 2001-11-30 | 2005-02-16 | 伊莱利利公司 | 过氧化物酶体激活的受体激动剂 |
| SE0104334D0 (sv) * | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| DE60327922D1 (de) | 2002-02-05 | 2009-07-23 | Lilly Co Eli | Harnstoff-linker verbindungen und ihre verwendung als ppar regulatoren |
-
2003
- 2003-06-11 JP JP2004515700A patent/JP2005529975A/ja active Pending
- 2003-06-11 CN CN038141736A patent/CN1662487A/zh active Pending
- 2003-06-11 CA CA002488972A patent/CA2488972A1/en not_active Abandoned
- 2003-06-11 WO PCT/US2003/016207 patent/WO2004000789A1/en not_active Ceased
- 2003-06-11 MX MXPA04013000A patent/MXPA04013000A/es active IP Right Grant
- 2003-06-11 US US10/517,581 patent/US7220880B2/en not_active Expired - Fee Related
- 2003-06-11 EP EP03731326A patent/EP1517882A1/en not_active Withdrawn
- 2003-06-11 AU AU2003241579A patent/AU2003241579B9/en not_active Ceased
- 2003-06-11 BR BR0311834-7A patent/BR0311834A/pt not_active IP Right Cessation
- 2003-06-16 TW TW092116259A patent/TW200406371A/zh unknown
- 2003-06-17 AR ARP030102136A patent/AR039684A1/es unknown
- 2003-06-18 PE PE2003000616A patent/PE20040580A1/es not_active Application Discontinuation
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