RU2408589C2 - Соединения и композиции в качестве модуляторов ppar-рецепторов, активируемых пролифератором пероксисом - Google Patents
Соединения и композиции в качестве модуляторов ppar-рецепторов, активируемых пролифератором пероксисом Download PDFInfo
- Publication number
- RU2408589C2 RU2408589C2 RU2006144124/04A RU2006144124A RU2408589C2 RU 2408589 C2 RU2408589 C2 RU 2408589C2 RU 2006144124/04 A RU2006144124/04 A RU 2006144124/04A RU 2006144124 A RU2006144124 A RU 2006144124A RU 2408589 C2 RU2408589 C2 RU 2408589C2
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- acetic acid
- dichlorophenoxy
- ethylcarbamoyl
- isoxazol
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 15
- 239000000203 mixture Substances 0.000 title 1
- 239000003614 peroxisome proliferator Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 14
- 150000002367 halogens Chemical class 0.000 claims abstract 13
- -1 2-(2-nitro-4-trifluoromethylphenoxy)ethyl Chemical group 0.000 claims abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000002541 furyl group Chemical group 0.000 claims abstract 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims abstract 2
- IBBWEQWWSGGCBV-UHFFFAOYSA-N 3-(2,6-dichlorophenyl)-5-methyl-4-[2-[2-nitro-4-(trifluoromethyl)phenoxy]ethoxymethyl]-1,2-oxazole Chemical compound CC=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1COCCOC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O IBBWEQWWSGGCBV-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 102000005962 receptors Human genes 0.000 claims abstract 2
- 108020003175 receptors Proteins 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- CCDXWBJYZOEJJQ-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(2-methoxyphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound COC1=CC=CC=C1C1=C(C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)C(C=2C=C(CC(O)=O)C=CC=2)=NO1 CCDXWBJYZOEJJQ-UHFFFAOYSA-N 0.000 claims 1
- MAJGTGCBCFNXIJ-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(2-methylphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC1=CC=CC=C1C1=C(C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)C(C=2C=C(CC(O)=O)C=CC=2)=NO1 MAJGTGCBCFNXIJ-UHFFFAOYSA-N 0.000 claims 1
- FDJSINAEIWHOSF-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(3-methoxyphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound COC1=CC=CC(C2=C(C(=NO2)C=2C=C(CC(O)=O)C=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 FDJSINAEIWHOSF-UHFFFAOYSA-N 0.000 claims 1
- VSTUAPSSZABUPX-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(3-methylphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC1=CC=CC(C2=C(C(=NO2)C=2C=C(CC(O)=O)C=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 VSTUAPSSZABUPX-UHFFFAOYSA-N 0.000 claims 1
- FKVOGNAYDXYJHR-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(4-fluorophenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=CC(F)=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 FKVOGNAYDXYJHR-UHFFFAOYSA-N 0.000 claims 1
- GNANUCRWKHRWEN-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(4-methoxyphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)C(C=2C=C(CC(O)=O)C=CC=2)=NO1 GNANUCRWKHRWEN-UHFFFAOYSA-N 0.000 claims 1
- FXOLAKBYJJBRAM-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(4-methylphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1C1=C(C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)C(C=2C=C(CC(O)=O)C=CC=2)=NO1 FXOLAKBYJJBRAM-UHFFFAOYSA-N 0.000 claims 1
- SYGFYQKRQWNHHI-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(4-nitrophenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=CC(=CC=2)[N+]([O-])=O)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 SYGFYQKRQWNHHI-UHFFFAOYSA-N 0.000 claims 1
- CUTONGFQGBPDDB-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(furan-2-yl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(C=3OC=CC=3)ON=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 CUTONGFQGBPDDB-UHFFFAOYSA-N 0.000 claims 1
- QFWZZPBMVBLFQI-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(furan-3-yl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(C3=COC=C3)ON=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 QFWZZPBMVBLFQI-UHFFFAOYSA-N 0.000 claims 1
- GWFOXDGIUIFNTJ-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-[2-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C(=CC=CC=2)C(F)(F)F)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 GWFOXDGIUIFNTJ-UHFFFAOYSA-N 0.000 claims 1
- OJQNWAUOGCOWMX-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-[3-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=C(C=CC=2)C(F)(F)F)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 OJQNWAUOGCOWMX-UHFFFAOYSA-N 0.000 claims 1
- YYHLPMOINRCEAK-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-[4-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=CC(=CC=2)C(F)(F)F)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 YYHLPMOINRCEAK-UHFFFAOYSA-N 0.000 claims 1
- VNRXJIKFEPCNQD-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-ethyl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CCC=1ON=C(C=2C=C(CC(O)=O)C=CC=2)C=1C(=O)NCCOC1=CC=C(Cl)C=C1Cl VNRXJIKFEPCNQD-UHFFFAOYSA-N 0.000 claims 1
- CEBCGESREWBUNL-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-methyl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC=1ON=C(C=2C=C(CC(O)=O)C=CC=2)C=1C(=O)NCCOC1=CC=C(Cl)C=C1Cl CEBCGESREWBUNL-UHFFFAOYSA-N 0.000 claims 1
- HINPKGVWVQYESB-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-phenyl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=CC=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 HINPKGVWVQYESB-UHFFFAOYSA-N 0.000 claims 1
- VGDVHUHMEGINCY-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-propan-2-yl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC(C)C=1ON=C(C=2C=C(CC(O)=O)C=CC=2)C=1C(=O)NCCOC1=CC=C(Cl)C=C1Cl VGDVHUHMEGINCY-UHFFFAOYSA-N 0.000 claims 1
- OSLPDQVNYLFKEI-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-propyl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CCCC=1ON=C(C=2C=C(CC(O)=O)C=CC=2)C=1C(=O)NCCOC1=CC=C(Cl)C=C1Cl OSLPDQVNYLFKEI-UHFFFAOYSA-N 0.000 claims 1
- GREUJJGCEBEWOM-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-pyridin-2-yl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2N=CC=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 GREUJJGCEBEWOM-UHFFFAOYSA-N 0.000 claims 1
- SAGLIYWQRRYNEF-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-pyridin-3-yl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=NC=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 SAGLIYWQRRYNEF-UHFFFAOYSA-N 0.000 claims 1
- NWPWVYUZXHEEKG-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-pyridin-4-yl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=CN=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 NWPWVYUZXHEEKG-UHFFFAOYSA-N 0.000 claims 1
- UIVUKJFRZDCUDN-UHFFFAOYSA-N 2-[3-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-thiophen-2-yl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(C=3SC=CC=3)ON=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 UIVUKJFRZDCUDN-UHFFFAOYSA-N 0.000 claims 1
- JYAAMGHQVBAUOL-UHFFFAOYSA-N 2-[3-[5-(2-chlorophenyl)-4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C(=CC=CC=2)Cl)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 JYAAMGHQVBAUOL-UHFFFAOYSA-N 0.000 claims 1
- AVUICKWYCZKZGG-UHFFFAOYSA-N 2-[3-[5-(3-chlorophenyl)-4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=C(Cl)C=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 AVUICKWYCZKZGG-UHFFFAOYSA-N 0.000 claims 1
- PWEWVTRKGCYELK-UHFFFAOYSA-N 2-[3-[5-(4-chlorophenyl)-4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C=2C(=C(ON=2)C=2C=CC(Cl)=CC=2)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 PWEWVTRKGCYELK-UHFFFAOYSA-N 0.000 claims 1
- FJSFNOBDYQHUOE-UHFFFAOYSA-N 2-[3-[5-tert-butyl-4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC(C)(C)C=1ON=C(C=2C=C(CC(O)=O)C=CC=2)C=1C(=O)NCCOC1=CC=C(Cl)C=C1Cl FJSFNOBDYQHUOE-UHFFFAOYSA-N 0.000 claims 1
- HLABUWNFXQNRKZ-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethoxymethyl]-5-phenyl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C=CC=CC=2)=C1COCCOC1=CC=C(Cl)C=C1Cl HLABUWNFXQNRKZ-UHFFFAOYSA-N 0.000 claims 1
- PBKVGQXEGAUCCA-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(2-methoxyphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound COC1=CC=CC=C1C1=C(C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)C(C=2C(=CC(CC(O)=O)=CC=2)Cl)=NO1 PBKVGQXEGAUCCA-UHFFFAOYSA-N 0.000 claims 1
- JNSSABCYJVAZSA-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(3-methoxyphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound COC1=CC=CC(C2=C(C(=NO2)C=2C(=CC(CC(O)=O)=CC=2)Cl)C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)=C1 JNSSABCYJVAZSA-UHFFFAOYSA-N 0.000 claims 1
- XJMBJPHDKOWSEK-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(4-fluorophenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C=CC(F)=CC=2)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl XJMBJPHDKOWSEK-UHFFFAOYSA-N 0.000 claims 1
- GKKHQLSXRHQCEK-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(4-methoxyphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)C(C=2C(=CC(CC(O)=O)=CC=2)Cl)=NO1 GKKHQLSXRHQCEK-UHFFFAOYSA-N 0.000 claims 1
- FULUAKDKKSQSIC-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(4-methylphenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1C1=C(C(=O)NCCOC=2C(=CC(Cl)=CC=2)Cl)C(C=2C(=CC(CC(O)=O)=CC=2)Cl)=NO1 FULUAKDKKSQSIC-UHFFFAOYSA-N 0.000 claims 1
- PEANYKWUIHETQC-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(4-nitrophenyl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C=CC(=CC=2)[N+]([O-])=O)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl PEANYKWUIHETQC-UHFFFAOYSA-N 0.000 claims 1
- GIVLJFANLOYRFJ-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(furan-2-yl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2OC=CC=2)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl GIVLJFANLOYRFJ-UHFFFAOYSA-N 0.000 claims 1
- PKVOAAKXDBFFIZ-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-(furan-3-yl)-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C2=COC=C2)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl PKVOAAKXDBFFIZ-UHFFFAOYSA-N 0.000 claims 1
- KJLHYMLNCQJDQK-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-[2-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C(=CC=CC=2)C(F)(F)F)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl KJLHYMLNCQJDQK-UHFFFAOYSA-N 0.000 claims 1
- ZOHNPCHOEOYHRN-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-[3-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C=C(C=CC=2)C(F)(F)F)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl ZOHNPCHOEOYHRN-UHFFFAOYSA-N 0.000 claims 1
- DDNWVNNNFOVUEU-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-[4-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C=CC(=CC=2)C(F)(F)F)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl DDNWVNNNFOVUEU-UHFFFAOYSA-N 0.000 claims 1
- ZNAQLMKOHTYVPZ-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-methyl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC=1ON=C(C=2C(=CC(CC(O)=O)=CC=2)Cl)C=1C(=O)NCCOC1=CC=C(Cl)C=C1Cl ZNAQLMKOHTYVPZ-UHFFFAOYSA-N 0.000 claims 1
- SUEZNXXKBMUSQM-UHFFFAOYSA-N 2-[3-chloro-4-[4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-5-phenyl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C=CC=CC=2)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl SUEZNXXKBMUSQM-UHFFFAOYSA-N 0.000 claims 1
- VINJHESJAFNNRA-UHFFFAOYSA-N 2-[3-chloro-4-[4-[4-(2,4-dichlorophenoxy)butanoyl]-5-phenyl-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C=CC=CC=2)=C1C(=O)CCCOC1=CC=C(Cl)C=C1Cl VINJHESJAFNNRA-UHFFFAOYSA-N 0.000 claims 1
- WWYISGKKEXZEAN-UHFFFAOYSA-N 2-[3-chloro-4-[5-(2-chlorophenyl)-4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C(=CC=CC=2)Cl)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl WWYISGKKEXZEAN-UHFFFAOYSA-N 0.000 claims 1
- XUSZJUSCVLMJMD-UHFFFAOYSA-N 2-[3-chloro-4-[5-(4-chlorophenyl)-4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C=2C=CC(Cl)=CC=2)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl XUSZJUSCVLMJMD-UHFFFAOYSA-N 0.000 claims 1
- GSIWZVSUBWAXOJ-UHFFFAOYSA-N 2-[3-chloro-4-[5-cyclopropyl-4-[2-(2,4-dichlorophenoxy)ethylcarbamoyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=NOC(C2CC2)=C1C(=O)NCCOC1=CC=C(Cl)C=C1Cl GSIWZVSUBWAXOJ-UHFFFAOYSA-N 0.000 claims 1
- AYOXOSLQDVPREQ-UHFFFAOYSA-N 2-[3-chloro-4-[5-methyl-4-[2-[2-nitro-4-(trifluoromethyl)phenoxy]ethoxymethyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC=1ON=C(C=2C(=CC(CC(O)=O)=CC=2)Cl)C=1COCCOC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O AYOXOSLQDVPREQ-UHFFFAOYSA-N 0.000 claims 1
- HHKOUWVTKOVZSW-UHFFFAOYSA-N 2-[3-chloro-4-[5-methyl-4-[2-[2-nitro-4-(trifluoromethyl)phenoxy]ethylcarbamoyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC=1ON=C(C=2C(=CC(CC(O)=O)=CC=2)Cl)C=1C(=O)NCCOC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O HHKOUWVTKOVZSW-UHFFFAOYSA-N 0.000 claims 1
- LQWZGIWJGJVXRJ-UHFFFAOYSA-N 2-[3-chloro-4-[5-methyl-4-[[2-nitro-4-(trifluoromethyl)phenoxy]methyl]-1,2-oxazol-3-yl]phenyl]acetic acid Chemical compound CC=1ON=C(C=2C(=CC(CC(O)=O)=CC=2)Cl)C=1COC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O LQWZGIWJGJVXRJ-UHFFFAOYSA-N 0.000 claims 1
- GYIROJSAFURELI-UHFFFAOYSA-N 2-[4-[4-[2-[2,4-bis(trifluoromethyl)phenoxy]ethylcarbamoyl]-5-methyl-1,2-oxazol-3-yl]-3-chlorophenyl]acetic acid Chemical compound CC=1ON=C(C=2C(=CC(CC(O)=O)=CC=2)Cl)C=1C(=O)NCCOC1=CC=C(C(F)(F)F)C=C1C(F)(F)F GYIROJSAFURELI-UHFFFAOYSA-N 0.000 claims 1
- 108010015181 PPAR delta Proteins 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 abstract 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
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- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
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- Immunology (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
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| US57100304P | 2004-05-14 | 2004-05-14 | |
| US60/571,003 | 2004-05-14 |
Publications (2)
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| RU2006144124A RU2006144124A (ru) | 2008-06-20 |
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| EP (1) | EP1745027A4 (enExample) |
| JP (1) | JP2007537286A (enExample) |
| KR (1) | KR20070034993A (enExample) |
| CN (1) | CN1984894A (enExample) |
| AR (1) | AR048789A1 (enExample) |
| AU (2) | AU2005245411B2 (enExample) |
| BR (1) | BRPI0511099A (enExample) |
| CA (1) | CA2564429A1 (enExample) |
| MX (1) | MXPA06013196A (enExample) |
| PE (1) | PE20060357A1 (enExample) |
| RU (1) | RU2408589C2 (enExample) |
| TW (1) | TW200602330A (enExample) |
| WO (1) | WO2005113519A1 (enExample) |
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| EP1707202A1 (de) * | 2005-03-31 | 2006-10-04 | Speedel Experimenta AG | Organische Verbindungen |
| CA2614664A1 (en) * | 2005-07-14 | 2007-01-25 | Franco Folli | Daily dosage regimen for treating diabetes, obesity,metabolic syndrome and polycystic ovary syndrome |
| CA2625646A1 (en) * | 2005-10-25 | 2007-05-03 | Merck & Co., Inc. | Combination of a dipeptidyl peptidase-4 inhibitor and an anti-hypertensive agent for the treatment of diabetes and hypertension |
| DE102006014165A1 (de) * | 2006-03-24 | 2007-09-27 | Schebo Biotech Ag | Neue Isooxazol-Derivate und deren Verwendungen |
| TW200811164A (en) * | 2006-05-12 | 2008-03-01 | Jerini Ag | New heterocyclic compounds for the inhibition of integrins and use thereof |
| WO2008035359A2 (en) * | 2006-06-12 | 2008-03-27 | Cadila Healthcare Limited | Oximinophenoxyalkanoic acid and phenylalkanoic acid derivatives |
| US20080020014A1 (en) * | 2006-07-19 | 2008-01-24 | Paul Consigny | Implantable devices containing nuclear receptor ligands for the treatment of vascular and related disorders |
| US7943619B2 (en) * | 2007-12-04 | 2011-05-17 | Hoffmann-La Roche Inc. | Isoxazolo-pyridazine derivatives |
| EP2229383B1 (en) * | 2007-12-04 | 2017-01-18 | F. Hoffmann-La Roche AG | Isoxazolo-pyrazine derivatives |
| PT2767536E (pt) * | 2007-12-04 | 2015-11-17 | Hoffmann La Roche | Derivados de isoxazolo-piridina |
| US20110293520A1 (en) * | 2008-06-09 | 2011-12-01 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften E.V. | New drug for inhibiting aggregation of proteins involved in diseases linked to protein aggregation and/or neurodegenerative diseases |
| EP2545964A1 (en) | 2011-07-13 | 2013-01-16 | Phenex Pharmaceuticals AG | Novel FXR (NR1H4) binding and activity modulating compounds |
| US8604062B2 (en) | 2011-10-20 | 2013-12-10 | Hoffman-La Roche Inc. | Process for the preparation of isoxazolyl-methoxy nicotinic acids |
| US8785435B2 (en) | 2011-10-20 | 2014-07-22 | Hoffmann-La Roche Inc. | Solid forms |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
| CN105030771B (zh) * | 2015-04-10 | 2017-11-17 | 广州市爱菩新医药科技有限公司 | 连吡啶异恶唑类化合物作为法尼醇x受体激动剂的应用 |
| CN105622536B (zh) * | 2015-12-30 | 2018-06-29 | 商丘师范学院 | 一种三氟甲基化烯基异噁唑化合物及其制备方法和应用 |
| CN105622537A (zh) * | 2016-03-01 | 2016-06-01 | 青岛大学 | 一种3,4,5-三取代异恶唑类化合物的合成方法 |
| CA3252823A1 (en) | 2016-06-13 | 2025-02-25 | Gilead Sciences, Inc. | Fxr (nr1h4) modulating compounds |
| WO2017218337A1 (en) | 2016-06-13 | 2017-12-21 | Gilead Sciences, Inc. | Fxr (nr1h4) modulating compounds |
| SI3600309T1 (sl) | 2017-03-28 | 2022-10-28 | Gilead Sciences, Inc. | Terapevtske kombinacije za zdravljenje bolezni jeter |
| WO2020150136A1 (en) | 2019-01-15 | 2020-07-23 | Gilead Sciences, Inc. | Fxr (nr1h4) modulating compounds |
| US11524005B2 (en) | 2019-02-19 | 2022-12-13 | Gilead Sciences, Inc. | Solid forms of FXR agonists |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0573883A1 (de) * | 1992-06-12 | 1993-12-15 | Bayer Ag | Verwendung von 3-arylsubstituierten 5-Alkyl-isoxazol-4-carbonsäurederivaten zur Bekämpfung von Endoparasiten, neue 3-arylsubstituierte-5-Alkyl-isoxazol-4-carbonsäurederivate und Verfahren zu ihrer Herstellung |
| RU2165415C2 (ru) * | 1996-02-27 | 2001-04-20 | Санкио Компани Лимитед | Производные изоксазола и фармацевтическая композиция на их основе |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2088996A (en) * | 1935-11-22 | 1937-08-03 | Hoffmann La Roche | Double compounds of secondary amides of 3.5-dimethyl-isoxazole-4-carboxylic acid and process for the manufacture of same |
| DE1670249B2 (de) * | 1966-07-25 | 1974-07-18 | Bristol-Myers Co., East Syracuse, N.Y. (V.St.A.) | Verfahren zur Herstellung von 4-Isothiazolcarbonsäuren |
| GB1203039A (en) * | 1967-02-15 | 1970-08-26 | Geigy Ag J R | Process for the production of nitrofuryl derivatives |
| US3466296A (en) | 1967-05-16 | 1969-09-09 | American Home Prod | Process for the preparation of alkyl 3,5-disubstituted-isoxazole-4-carboxylates |
| IT1228288B (it) * | 1989-01-09 | 1991-06-07 | Zambon Spa | Composti ad attivita' antiserotoninica |
| PL343313A1 (en) * | 1998-04-08 | 2001-08-13 | Lilly Co Eli | Methods for inhibiting mrp1 |
| EP1102755B1 (en) * | 1998-08-07 | 2006-01-04 | Chiron Corporation | Substituted isoxazole derivatives as estrogen receptor modulators |
| WO2001016116A1 (en) * | 1999-09-01 | 2001-03-08 | Chemrx Advanced Technologies, Inc. | Process for synthesizing isoxazolines and isoxazoles |
| CA2411813A1 (en) * | 2000-06-14 | 2001-12-20 | Eli Lilly And Company | Tricyclic compounds as mrp1-inhibitors |
| GB0119911D0 (en) * | 2001-08-15 | 2001-10-10 | Novartis Ag | Organic Compounds |
| US6875780B2 (en) | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| AU2003278814A1 (en) * | 2002-09-13 | 2004-04-30 | Georgetown University | Ligands for the peroxisome proliferator-activated receptor, and methods of use thereof |
| WO2005033103A1 (en) | 2003-09-12 | 2005-04-14 | Rigel Pharmaceuticals, Inc. | Quinoline compounds and their uses |
-
2005
- 2005-05-12 RU RU2006144124/04A patent/RU2408589C2/ru not_active IP Right Cessation
- 2005-05-12 KR KR1020067023769A patent/KR20070034993A/ko not_active Ceased
- 2005-05-12 EP EP05769154A patent/EP1745027A4/en not_active Withdrawn
- 2005-05-12 JP JP2007513366A patent/JP2007537286A/ja active Pending
- 2005-05-12 CA CA002564429A patent/CA2564429A1/en not_active Abandoned
- 2005-05-12 AU AU2005245411A patent/AU2005245411B2/en not_active Ceased
- 2005-05-12 CN CNA2005800196529A patent/CN1984894A/zh active Pending
- 2005-05-12 BR BRPI0511099-8A patent/BRPI0511099A/pt not_active IP Right Cessation
- 2005-05-12 US US11/596,596 patent/US7820705B2/en not_active Expired - Fee Related
- 2005-05-12 WO PCT/US2005/016672 patent/WO2005113519A1/en not_active Ceased
- 2005-05-12 MX MXPA06013196A patent/MXPA06013196A/es not_active Application Discontinuation
- 2005-05-13 AR ARP050101972A patent/AR048789A1/es unknown
- 2005-05-13 PE PE2005000536A patent/PE20060357A1/es not_active Application Discontinuation
- 2005-05-13 TW TW094115655A patent/TW200602330A/zh unknown
-
2009
- 2009-07-09 AU AU2009202781A patent/AU2009202781A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| EP0573883A1 (de) * | 1992-06-12 | 1993-12-15 | Bayer Ag | Verwendung von 3-arylsubstituierten 5-Alkyl-isoxazol-4-carbonsäurederivaten zur Bekämpfung von Endoparasiten, neue 3-arylsubstituierte-5-Alkyl-isoxazol-4-carbonsäurederivate und Verfahren zu ihrer Herstellung |
| RU2165415C2 (ru) * | 1996-02-27 | 2001-04-20 | Санкио Компани Лимитед | Производные изоксазола и фармацевтическая композиция на их основе |
Also Published As
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| MXPA06013196A (es) | 2007-02-14 |
| US7820705B2 (en) | 2010-10-26 |
| BRPI0511099A (pt) | 2007-12-26 |
| JP2007537286A (ja) | 2007-12-20 |
| AU2005245411B2 (en) | 2009-04-23 |
| AU2005245411A1 (en) | 2005-12-01 |
| TW200602330A (en) | 2006-01-16 |
| EP1745027A1 (en) | 2007-01-24 |
| US20080114044A1 (en) | 2008-05-15 |
| CN1984894A (zh) | 2007-06-20 |
| PE20060357A1 (es) | 2006-05-09 |
| AR048789A1 (es) | 2006-05-24 |
| AU2009202781A1 (en) | 2009-07-30 |
| KR20070034993A (ko) | 2007-03-29 |
| RU2006144124A (ru) | 2008-06-20 |
| CA2564429A1 (en) | 2005-12-01 |
| WO2005113519A1 (en) | 2005-12-01 |
| EP1745027A4 (en) | 2009-06-03 |
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