RU2014138894A - Производные фенилалкановой кислоты в качестве агонистов gpr - Google Patents
Производные фенилалкановой кислоты в качестве агонистов gpr Download PDFInfo
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- RU2014138894A RU2014138894A RU2014138894A RU2014138894A RU2014138894A RU 2014138894 A RU2014138894 A RU 2014138894A RU 2014138894 A RU2014138894 A RU 2014138894A RU 2014138894 A RU2014138894 A RU 2014138894A RU 2014138894 A RU2014138894 A RU 2014138894A
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- Prior art keywords
- alkyl
- halogen
- methoxy
- oxetan
- phenyl
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- 239000002253 acid Substances 0.000 title 1
- 239000000556 agonist Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims abstract 211
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 120
- 239000001257 hydrogen Substances 0.000 claims abstract 120
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 115
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 108
- 150000002367 halogens Chemical class 0.000 claims abstract 104
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 87
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 54
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 50
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract 21
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 16
- 125000003118 aryl group Chemical group 0.000 claims abstract 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 276
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 91
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 59
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 51
- -1 chloro, bromo, iodo Chemical group 0.000 claims 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 20
- 230000000155 isotopic effect Effects 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 15
- 150000001204 N-oxides Chemical class 0.000 claims 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 14
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims 14
- 239000000651 prodrug Substances 0.000 claims 14
- 229940002612 prodrug Drugs 0.000 claims 14
- 125000001153 fluoro group Chemical group F* 0.000 claims 12
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 8
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims 7
- 102100026148 Free fatty acid receptor 1 Human genes 0.000 claims 6
- 101000912510 Homo sapiens Free fatty acid receptor 1 Proteins 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 230000001404 mediated effect Effects 0.000 claims 6
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 239000010802 sludge Substances 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 3
- 208000002705 Glucose Intolerance Diseases 0.000 claims 3
- 206010022489 Insulin Resistance Diseases 0.000 claims 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 3
- 230000007850 degeneration Effects 0.000 claims 3
- 201000001421 hyperglycemia Diseases 0.000 claims 3
- 201000009104 prediabetes syndrome Diseases 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- JDTHKUJBMUJGCR-UHFFFAOYSA-N 2-[1-acetyl-3-[4-[[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]phenyl]azetidin-3-yl]acetic acid Chemical compound C1N(C(=O)C)CC1(CC(O)=O)C(C=C1)=CC=C1OCC1=CC=CC(C=2C(=CC(OCCCS(C)(=O)=O)=CC=2C)C)=C1 JDTHKUJBMUJGCR-UHFFFAOYSA-N 0.000 claims 1
- GKLSUUFHQRWSPW-UHFFFAOYSA-N 2-[3-[3-fluoro-4-[(3-phenylphenyl)methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=CC=CC=2)C(F)=CC=1C1(CC(=O)O)COC1 GKLSUUFHQRWSPW-UHFFFAOYSA-N 0.000 claims 1
- FXKNDNLEODHULM-UHFFFAOYSA-N 2-[3-[3-fluoro-4-[(4-phenylphenyl)methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=CC(=CC=2)C=2C=CC=CC=2)C(F)=CC=1C1(CC(=O)O)COC1 FXKNDNLEODHULM-UHFFFAOYSA-N 0.000 claims 1
- NYCOWYGTENMXIZ-UHFFFAOYSA-N 2-[3-[3-fluoro-4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1COC(C(=C1)F)=CC=C1C1(CC(O)=O)COC1 NYCOWYGTENMXIZ-UHFFFAOYSA-N 0.000 claims 1
- AQVLCLFJYVQFPQ-UHFFFAOYSA-N 2-[3-[3-fluoro-4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C(F)=CC=1C1(CC(=O)O)COC1 AQVLCLFJYVQFPQ-UHFFFAOYSA-N 0.000 claims 1
- PTRMDDBICBJTDE-UHFFFAOYSA-N 2-[3-[4-[(3-fluorophenyl)methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C=CC=1C1(CC(=O)O)COC1 PTRMDDBICBJTDE-UHFFFAOYSA-N 0.000 claims 1
- DERYYBGEDFXPPA-UHFFFAOYSA-N 2-[3-[4-[(4-phenylphenyl)methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=CC(=CC=2)C=2C=CC=CC=2)C=CC=1C1(CC(=O)O)COC1 DERYYBGEDFXPPA-UHFFFAOYSA-N 0.000 claims 1
- ZTMIRMPETJSUCS-UHFFFAOYSA-N 2-[3-[4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1COC(C=C1)=CC=C1C1(CC(O)=O)COC1 ZTMIRMPETJSUCS-UHFFFAOYSA-N 0.000 claims 1
- YFNOCZUXRGEHCC-UHFFFAOYSA-N 2-[3-[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1COC(C=C1)=CC=C1C1(CC(O)=O)COC1 YFNOCZUXRGEHCC-UHFFFAOYSA-N 0.000 claims 1
- HNOKMOGUFIEMHN-UHFFFAOYSA-N 2-[3-[4-[[2-fluoro-3-(trifluoromethyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C(=C(C=CC=2)C(F)(F)F)F)C=CC=1C1(CC(=O)O)COC1 HNOKMOGUFIEMHN-UHFFFAOYSA-N 0.000 claims 1
- HRMQZIGYTJPABR-UHFFFAOYSA-N 2-[3-[4-[[2-fluoro-5-(trifluoromethoxy)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C(=CC=C(OC(F)(F)F)C=2)F)C=CC=1C1(CC(=O)O)COC1 HRMQZIGYTJPABR-UHFFFAOYSA-N 0.000 claims 1
- NRZQCSBCYGBYRA-UHFFFAOYSA-N 2-[3-[4-[[2-methoxy-5-(trifluoromethyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound COC1=CC=C(C(F)(F)F)C=C1COC1=CC=C(C2(CC(O)=O)COC2)C=C1 NRZQCSBCYGBYRA-UHFFFAOYSA-N 0.000 claims 1
- MYPIUMJFWOEURR-UHFFFAOYSA-N 2-[3-[4-[[2-methyl-5-(trifluoromethyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC1=CC=C(C(F)(F)F)C=C1COC1=CC=C(C2(CC(O)=O)COC2)C=C1 MYPIUMJFWOEURR-UHFFFAOYSA-N 0.000 claims 1
- KMIKDGOIESGKHC-UHFFFAOYSA-N 2-[3-[4-[[3-(2-morpholin-4-ylpyrimidin-5-yl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=NC(=NC=2)N2CCOCC2)C=CC=1C1(CC(=O)O)COC1 KMIKDGOIESGKHC-UHFFFAOYSA-N 0.000 claims 1
- JPDGJRIATDOMFF-UHFFFAOYSA-N 2-[3-[4-[[3-(4-butylsulfanylphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C1=CC(SCCCC)=CC=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 JPDGJRIATDOMFF-UHFFFAOYSA-N 0.000 claims 1
- UOQUPLATVGNJKN-UHFFFAOYSA-N 2-[3-[4-[[3-(4-cyclopentyloxy-2,6-dimethylphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(C)=CC=1OC1CCCC1 UOQUPLATVGNJKN-UHFFFAOYSA-N 0.000 claims 1
- OLBVFKTUYSDYCS-UHFFFAOYSA-N 2-[3-[4-[[3-(4-methylsulfanylphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C1=CC(SC)=CC=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 OLBVFKTUYSDYCS-UHFFFAOYSA-N 0.000 claims 1
- IJSKQXSIBXDXGF-UHFFFAOYSA-N 2-[3-[4-[[3-(4-propan-2-ylsulfanylphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C1=CC(SC(C)C)=CC=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 IJSKQXSIBXDXGF-UHFFFAOYSA-N 0.000 claims 1
- ORDMHKJAPOYBBF-UHFFFAOYSA-N 2-[3-[4-[[3-(5-methoxypyridin-3-yl)phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound COC1=CN=CC(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)=C1 ORDMHKJAPOYBBF-UHFFFAOYSA-N 0.000 claims 1
- KKROWBLUSZZBAL-UHFFFAOYSA-N 2-[3-[4-[[3-[2,6-dimethyl-4-(3-methylbutoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC1=CC(OCCC(C)C)=CC(C)=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 KKROWBLUSZZBAL-UHFFFAOYSA-N 0.000 claims 1
- VJNGDIYTJWAWGI-UHFFFAOYSA-N 2-[3-[4-[[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]-3-fluorophenyl]oxetan-3-yl]acetic acid Chemical compound CC1=CC(OCCCS(C)(=O)=O)=CC(C)=C1C1=CC=CC(COC=2C(=CC(=CC=2)C2(CC(O)=O)COC2)F)=C1 VJNGDIYTJWAWGI-UHFFFAOYSA-N 0.000 claims 1
- IMUJKRYLHJVNOY-UHFFFAOYSA-N 2-[3-[4-[[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]phenyl]-1-methylsulfonylazetidin-3-yl]acetic acid Chemical compound CC1=CC(OCCCS(C)(=O)=O)=CC(C)=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)CN(C2)S(C)(=O)=O)=C1 IMUJKRYLHJVNOY-UHFFFAOYSA-N 0.000 claims 1
- HFPZOBZRBCFVBX-UHFFFAOYSA-N 2-[3-[4-[[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC1=CC(OCCCS(C)(=O)=O)=CC(C)=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 HFPZOBZRBCFVBX-UHFFFAOYSA-N 0.000 claims 1
- ZSBPMSQBLHLFLQ-UHFFFAOYSA-N 2-[3-[4-[[3-[2,6-dimethyl-4-(oxan-4-ylmethoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(C)=CC=1OCC1CCOCC1 ZSBPMSQBLHLFLQ-UHFFFAOYSA-N 0.000 claims 1
- ZCNPMGFWDFJWLP-UHFFFAOYSA-N 2-[3-[4-[[3-[2,6-dimethyl-4-(oxolan-2-ylmethoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(C)=CC=1OCC1CCCO1 ZCNPMGFWDFJWLP-UHFFFAOYSA-N 0.000 claims 1
- ZLOLRZZJXXLDAM-UHFFFAOYSA-N 2-[3-[4-[[3-[2,6-dimethyl-4-(oxolan-3-ylmethoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(C)=CC=1OCC1CCOC1 ZLOLRZZJXXLDAM-UHFFFAOYSA-N 0.000 claims 1
- GRJBJYMERUQKRP-UHFFFAOYSA-N 2-[3-[4-[[3-[2,6-dimethyl-4-[(3-methyloxetan-3-yl)methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(C)=CC=1OCC1(C)COC1 GRJBJYMERUQKRP-UHFFFAOYSA-N 0.000 claims 1
- ZLOLRZZJXXLDAM-XMMPIXPASA-N 2-[3-[4-[[3-[2,6-dimethyl-4-[[(3r)-oxolan-3-yl]methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(C)=CC=1OC[C@@H]1CCOC1 ZLOLRZZJXXLDAM-XMMPIXPASA-N 0.000 claims 1
- HWVDJYYKCVTJQP-UHFFFAOYSA-N 2-[3-[4-[[3-[2-chloro-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound ClC1=CC(OCCCS(=O)(=O)C)=CC=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 HWVDJYYKCVTJQP-UHFFFAOYSA-N 0.000 claims 1
- QQCOGHHCLKAWMN-UHFFFAOYSA-N 2-[3-[4-[[3-[2-chloro-4-(oxan-4-ylmethoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3CCOCC3)=CC=2)Cl)C=CC=1C1(CC(=O)O)COC1 QQCOGHHCLKAWMN-UHFFFAOYSA-N 0.000 claims 1
- NTEBDOAQMGCQJB-UHFFFAOYSA-N 2-[3-[4-[[3-[2-chloro-4-[(1,1-dioxothian-4-yl)methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3CCS(=O)(=O)CC3)=CC=2)Cl)C=CC=1C1(CC(=O)O)COC1 NTEBDOAQMGCQJB-UHFFFAOYSA-N 0.000 claims 1
- HQVIIGHAPGNDJW-UHFFFAOYSA-N 2-[3-[4-[[3-[2-chloro-4-[(1,1-dioxothiolan-3-yl)methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3CS(=O)(=O)CC3)=CC=2)Cl)C=CC=1C1(CC(=O)O)COC1 HQVIIGHAPGNDJW-UHFFFAOYSA-N 0.000 claims 1
- ATHKTKOJWHIDPR-UHFFFAOYSA-N 2-[3-[4-[[3-[2-chloro-4-[(3-methyloxetan-3-yl)methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(Cl)=CC=1OCC1(C)COC1 ATHKTKOJWHIDPR-UHFFFAOYSA-N 0.000 claims 1
- FIQOSXVWSMGGNR-UHFFFAOYSA-N 2-[3-[4-[[3-[2-chloro-4-[[3-(hydroxymethyl)oxetan-3-yl]methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(Cl)=CC=1OCC1(CO)COC1 FIQOSXVWSMGGNR-UHFFFAOYSA-N 0.000 claims 1
- VKAPQEUNQXRCDK-UHFFFAOYSA-N 2-[3-[4-[[3-[2-methyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC1=CC(OCCCS(C)(=O)=O)=CC=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 VKAPQEUNQXRCDK-UHFFFAOYSA-N 0.000 claims 1
- FBLPCXZJXAXQHW-UHFFFAOYSA-N 2-[3-[4-[[3-[3,5-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC1=C(OCCCS(C)(=O)=O)C(C)=CC(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)=C1 FBLPCXZJXAXQHW-UHFFFAOYSA-N 0.000 claims 1
- IASNLCQWUMMANK-UHFFFAOYSA-N 2-[3-[4-[[3-[3-methoxy-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C1=C(OCCCS(C)(=O)=O)C(OC)=CC(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)=C1 IASNLCQWUMMANK-UHFFFAOYSA-N 0.000 claims 1
- BTKABEKHQWAKHH-UHFFFAOYSA-N 2-[3-[4-[[3-[4-(1,1-dioxothian-4-yl)oxy-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(C)=CC=1OC1CCS(=O)(=O)CC1 BTKABEKHQWAKHH-UHFFFAOYSA-N 0.000 claims 1
- IYNIYXKPGASVCF-UHFFFAOYSA-N 2-[3-[4-[[3-[4-(1,3-difluoropropan-2-yloxy)-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC1=CC(OC(CF)CF)=CC(C)=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 IYNIYXKPGASVCF-UHFFFAOYSA-N 0.000 claims 1
- SBRIRROHTQSSQH-UHFFFAOYSA-N 2-[3-[4-[[3-[4-(2,2-dimethylpropoxy)-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC1=CC(OCC(C)(C)C)=CC(C)=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 SBRIRROHTQSSQH-UHFFFAOYSA-N 0.000 claims 1
- FNHOYXFWTIFGKL-UHFFFAOYSA-N 2-[3-[4-[[3-[4-(2-methoxyethoxy)-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound CC1=CC(OCCOC)=CC(C)=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(O)=O)COC2)=C1 FNHOYXFWTIFGKL-UHFFFAOYSA-N 0.000 claims 1
- OPMYBLLCHWDSIO-UHFFFAOYSA-N 2-[3-[4-[[3-[4-(cyclobutylmethoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=CC(OCC3CCC3)=CC=2)C=CC=1C1(CC(=O)O)COC1 OPMYBLLCHWDSIO-UHFFFAOYSA-N 0.000 claims 1
- XJHGBFNUIDOODI-UHFFFAOYSA-N 2-[3-[4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C=CC=1C1(CC(=O)O)COC1 XJHGBFNUIDOODI-UHFFFAOYSA-N 0.000 claims 1
- PCWMWGFUMCOSCX-UHFFFAOYSA-N 2-[3-[4-[[3-[4-[(1,1-dioxothian-4-yl)methoxy]-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetic acid Chemical compound C=1C(C)=C(C=2C=C(COC=3C=CC(=CC=3)C3(CC(O)=O)COC3)C=CC=2)C(C)=CC=1OCC1CCS(=O)(=O)CC1 PCWMWGFUMCOSCX-UHFFFAOYSA-N 0.000 claims 1
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- MQBMPSMXBSVUPJ-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-(4-butylsulfanylphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C1=CC(SCCCC)=CC=C1C1=CC=CC(COC=2C=CC(=CC=2)C2(CC(=O)OCC)COC2)=C1 MQBMPSMXBSVUPJ-UHFFFAOYSA-N 0.000 claims 1
- HYIGSLPCSWYXQS-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-(4-cyclopentyloxy-2,6-dimethylphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OC3CCCC3)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 HYIGSLPCSWYXQS-UHFFFAOYSA-N 0.000 claims 1
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- VCYJBWFTJPESMN-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-(4-hydroxyphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=CC(O)=CC=2)C=CC=1C1(CC(=O)OCC)COC1 VCYJBWFTJPESMN-UHFFFAOYSA-N 0.000 claims 1
- AMADJLJJMWISLV-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-(4-methylsulfanylphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=CC(SC)=CC=2)C=CC=1C1(CC(=O)OCC)COC1 AMADJLJJMWISLV-UHFFFAOYSA-N 0.000 claims 1
- CQUKSMIJRNPKJE-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-(4-propan-2-ylsulfanylphenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=CC(SC(C)C)=CC=2)C=CC=1C1(CC(=O)OCC)COC1 CQUKSMIJRNPKJE-UHFFFAOYSA-N 0.000 claims 1
- LRSFUZRZCDZOIK-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2,6-dimethyl-4-(3-methylbutoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCCC(C)C)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 LRSFUZRZCDZOIK-UHFFFAOYSA-N 0.000 claims 1
- RRPKUPKOWYOYRD-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]-3-fluorophenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCCCS(C)(=O)=O)=CC=2C)C)C(F)=CC=1C1(CC(=O)OCC)COC1 RRPKUPKOWYOYRD-UHFFFAOYSA-N 0.000 claims 1
- YXNDNHIBPFJWSZ-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]phenyl]-1-methylsulfonylazetidin-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCCCS(C)(=O)=O)=CC=2C)C)C=CC=1C1(CC(=O)OCC)CN(S(C)(=O)=O)C1 YXNDNHIBPFJWSZ-UHFFFAOYSA-N 0.000 claims 1
- PUFLJBAMMBIXBH-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2,6-dimethyl-4-(oxan-4-ylmethoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3CCOCC3)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 PUFLJBAMMBIXBH-UHFFFAOYSA-N 0.000 claims 1
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- IOKWGRKMMISBSQ-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2,6-dimethyl-4-(oxolan-3-ylmethoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3COCC3)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 IOKWGRKMMISBSQ-UHFFFAOYSA-N 0.000 claims 1
- OFEQWMIWKNZNDE-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2,6-dimethyl-4-[(3-methyloxetan-3-yl)methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3(C)COC3)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 OFEQWMIWKNZNDE-UHFFFAOYSA-N 0.000 claims 1
- IOKWGRKMMISBSQ-AREMUKBSSA-N ethyl 2-[3-[4-[[3-[2,6-dimethyl-4-[[(3r)-oxolan-3-yl]methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OC[C@H]3COCC3)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 IOKWGRKMMISBSQ-AREMUKBSSA-N 0.000 claims 1
- VZYDLBHTHHWDDD-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2-chloro-4-(oxan-4-ylmethoxy)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3CCOCC3)=CC=2)Cl)C=CC=1C1(CC(=O)OCC)COC1 VZYDLBHTHHWDDD-UHFFFAOYSA-N 0.000 claims 1
- MERKRJYSSUFRSD-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2-chloro-4-[(1,1-dioxothiolan-3-yl)methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3CS(=O)(=O)CC3)=CC=2)Cl)C=CC=1C1(CC(=O)OCC)COC1 MERKRJYSSUFRSD-UHFFFAOYSA-N 0.000 claims 1
- XJTQZANFNDROGP-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2-chloro-4-[(3-methyloxetan-3-yl)methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3(C)COC3)=CC=2)Cl)C=CC=1C1(CC(=O)OCC)COC1 XJTQZANFNDROGP-UHFFFAOYSA-N 0.000 claims 1
- AVUCXKSJWNQTCW-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[2-chloro-4-[[3-(hydroxymethyl)oxetan-3-yl]methoxy]phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3(CO)COC3)=CC=2)Cl)C=CC=1C1(CC(=O)OCC)COC1 AVUCXKSJWNQTCW-UHFFFAOYSA-N 0.000 claims 1
- GSLHJLJWFXZJGP-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[4-(1,1-dioxothian-4-yl)oxy-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OC3CCS(=O)(=O)CC3)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 GSLHJLJWFXZJGP-UHFFFAOYSA-N 0.000 claims 1
- VOLQSCPSVZBPPP-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[4-(1,3-difluoropropan-2-yloxy)-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OC(CF)CF)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 VOLQSCPSVZBPPP-UHFFFAOYSA-N 0.000 claims 1
- FIKBEAZCHZBJRN-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[4-(2,2-dimethylpropoxy)-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC(C)(C)C)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 FIKBEAZCHZBJRN-UHFFFAOYSA-N 0.000 claims 1
- QDPKDSYPFUVSMO-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C=CC(=CC=2)C(F)(F)F)C=CC=1C1(CC(=O)OCC)COC1 QDPKDSYPFUVSMO-UHFFFAOYSA-N 0.000 claims 1
- XADNVAIRVXZOIS-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-[4-[(1,1-dioxothian-4-yl)methoxy]-2,6-dimethylphenyl]phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C=CC=2)C=2C(=CC(OCC3CCS(=O)(=O)CC3)=CC=2C)C)C=CC=1C1(CC(=O)OCC)COC1 XADNVAIRVXZOIS-UHFFFAOYSA-N 0.000 claims 1
- BHYARSVBDQKPCE-UHFFFAOYSA-N ethyl 2-[3-[4-[[3-fluoro-5-(trifluoromethoxy)phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(OC(F)(F)F)C=C(F)C=2)C=CC=1C1(CC(=O)OCC)COC1 BHYARSVBDQKPCE-UHFFFAOYSA-N 0.000 claims 1
- IFQCPNLEDXQYQU-UHFFFAOYSA-N ethyl 2-[3-[4-[[4-(2-cyanophenyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=CC(=CC=2)C=2C(=CC=CC=2)C#N)C=CC=1C1(CC(=O)OCC)COC1 IFQCPNLEDXQYQU-UHFFFAOYSA-N 0.000 claims 1
- JOUOSIWSYHAREP-UHFFFAOYSA-N ethyl 2-[3-[4-[[4-methoxy-3-(trifluoromethyl)phenyl]methoxy]phenyl]oxetan-3-yl]acetate Chemical compound C=1C=C(OCC=2C=C(C(OC)=CC=2)C(F)(F)F)C=CC=1C1(CC(=O)OCC)COC1 JOUOSIWSYHAREP-UHFFFAOYSA-N 0.000 claims 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 230000002218 hypoglycaemic effect Effects 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
- OVSQVDMCBVZWGM-DTGCRPNFSA-N quercetin 3-O-beta-D-galactopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-DTGCRPNFSA-N 0.000 claims 1
- BBFYUPYFXSSMNV-UHFFFAOYSA-N quercetin-7-o-galactoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=CC=3)OC2=C1 BBFYUPYFXSSMNV-UHFFFAOYSA-N 0.000 claims 1
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- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
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Classifications
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- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
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- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no 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 the ring atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Dermatology (AREA)
- Reproductive Health (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| US201261736622P | 2012-12-13 | 2012-12-13 | |
| US61/736,622 | 2012-12-13 | ||
| PCT/IB2013/051555 WO2013128378A1 (en) | 2012-02-28 | 2013-02-27 | Phenyl alkanoic acid derivatives as gpr agonists |
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| RU2014138894A true RU2014138894A (ru) | 2016-04-20 |
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| MX347855B (es) | 2011-09-16 | 2017-05-16 | Sanofi Sa | Derivados de anilina, su preparación y su aplicación terapéutica. |
| WO2015028960A1 (en) * | 2013-08-28 | 2015-03-05 | Piramal Enterprises Limited | Substituted heterocyclic derivatives as gpr agonists and uses thereof |
| EA201690888A1 (ru) | 2013-11-14 | 2016-10-31 | Кадила Хелзкэр Лимитед | Новые гетероциклические соединения |
| WO2015084692A1 (en) | 2013-12-04 | 2015-06-11 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| EP3102198B1 (en) | 2014-02-06 | 2020-08-26 | Merck Sharp & Dohme Corp. | Antidiabetic compounds |
| DK3107901T3 (da) | 2014-02-19 | 2020-06-22 | Piramal Entpr Ltd | Forbindelser til brug som gpr120 agonister |
| CA2955919A1 (en) * | 2014-07-25 | 2016-01-28 | Piramal Enterprises Limited | Substituted phenyl alkanoic acid compounds as gpr120 agonists and uses thereof |
| EP3177287B1 (en) | 2014-08-08 | 2022-02-23 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| US10100042B2 (en) | 2014-08-08 | 2018-10-16 | Merck Sharp & Dohme Corp. | [5,6]—fused bicyclic antidiabetic compounds |
| WO2016019587A1 (en) | 2014-08-08 | 2016-02-11 | Merck Sharp & Dohme Corp. | [7, 6]-fused bicyclic antidiabetic compounds |
| WO2016022448A1 (en) | 2014-08-08 | 2016-02-11 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| KR101641023B1 (ko) | 2014-08-27 | 2016-07-20 | 씨제이헬스케어 주식회사 | 신규한 아미노-페닐-설포닐-아세테이트 유도체 및 이의 용도 |
| WO2016032120A1 (ko) * | 2014-08-27 | 2016-03-03 | 씨제이헬스케어 주식회사 | 신규한 아미노-페닐-설포닐-아세테이트 유도체 및 이의 용도 |
| AU2015313829B2 (en) | 2014-09-11 | 2020-07-23 | Piramal Enterprises Limited | Fused heterocyclic compounds as GPR120 agonists |
| DK3737470T5 (da) | 2018-01-08 | 2024-05-27 | Celon Pharma Sa | 3-phenyl-4-hexynsyrederivater som gpr40-agonister |
| MY196582A (en) | 2018-02-13 | 2023-04-19 | Gilead Sciences Inc | PD-1/PD-L1 Inhibitors |
| WO2019204609A1 (en) | 2018-04-19 | 2019-10-24 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| PT3820572T (pt) | 2018-07-13 | 2023-11-10 | Gilead Sciences Inc | Inibidores pd-1/pd-l1 |
| EP3870566A1 (en) | 2018-10-24 | 2021-09-01 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| KR20220150270A (ko) | 2019-10-07 | 2022-11-10 | 칼리오페, 인크. | Gpr119 효능제 |
| JP7745559B2 (ja) | 2020-02-28 | 2025-09-29 | キャリーオペ，インク． | Ｇｐｒ４０アゴニスト |
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| WO2024211164A2 (en) * | 2023-04-03 | 2024-10-10 | Trustees Of Dartmouth College | Fatty acid mimetics as modulators of gpr40 and/or gpr120 |
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| US5883106A (en) * | 1994-10-18 | 1999-03-16 | Pfizer Inc. | 5-lipoxygenase inhibitors |
| JP3400392B2 (ja) * | 1994-10-18 | 2003-04-28 | ファイザー製薬株式会社 | ５−リポキシゲナーゼ阻害剤及び新規医薬組成物 |
| SK281577B6 (sk) * | 1994-10-18 | 2001-05-10 | Pfizer Inc. | Heterocyklické zlúčeniny a farmaceutický prostriedok na ich báze |
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| WO2004012663A2 (en) * | 2002-08-01 | 2004-02-12 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or tnf-alpha converting enzyme |
| US20070054902A1 (en) * | 2003-12-02 | 2007-03-08 | Shionogi & Co., Ltd. | Isoxazole derivatives as peroxisome proliferator-activated receptors agonists |
| KR20070004769A (ko) * | 2004-02-27 | 2007-01-09 | 암젠 인코포레이션 | 대사 장애의 치료에 사용되는 화합물, 약제학적 조성물 및그 사용방법 |
| US8076338B2 (en) | 2004-04-23 | 2011-12-13 | Exelixis, Inc. | Kinase modulators and methods of use |
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| WO2007137008A2 (en) * | 2006-05-18 | 2007-11-29 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
| EP2431367A3 (en) | 2006-06-27 | 2012-07-04 | Takeda Pharmaceutical Company Limited | Fused cyclic compounds as GPR40 receptor modulators |
| TW200838526A (en) * | 2006-12-01 | 2008-10-01 | Astellas Pharma Inc | Carboxylic acid derivatives |
| MX2010003876A (es) * | 2007-10-10 | 2010-12-02 | Amgen Inc | Moduladores de gpr40 bifenilo- sustituidos. |
| JP2011507909A (ja) * | 2007-12-20 | 2011-03-10 | エンビボ ファーマシューティカルズ インコーポレイテッド | 四置換ベンゼン |
| EP2260017A1 (en) | 2008-03-06 | 2010-12-15 | Amgen, Inc | Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders |
| AU2009303475B2 (en) | 2008-10-15 | 2012-09-13 | Amgen Inc. | Spirocyclic GPR40 modulators |
| NZ592603A (en) * | 2008-10-21 | 2013-02-22 | Metabolex Inc | Aryl gpr120 receptor agonists and uses thereof |
| EA022271B1 (ru) * | 2008-11-14 | 2015-12-30 | Байер Интеллектуэль Проперти Гмбх | Гетероциклические замещенные соединения арила в качестве ингибиторов hif |
| KR20120022801A (ko) | 2009-04-22 | 2012-03-12 | 아스텔라스세이야쿠 가부시키가이샤 | 카르복실산 화합물 |
| WO2010138901A1 (en) * | 2009-05-29 | 2010-12-02 | Biogen Idec Ma Inc | Carboxylic acid-containing compounds, derivatives thereof, and related methods of use |
| BR112012001164A2 (pt) * | 2009-07-17 | 2016-03-01 | Shire Llc | aminoácido de carbamato e pró-fármacos de peptídeo de opioides e usos dos mesmos |
| DE102009046115A1 (de) * | 2009-10-28 | 2011-09-08 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 3-Phenylpropansäuren und ihre Verwendung |
| MX2013000803A (es) | 2010-07-23 | 2013-10-28 | Conexios Life Sciences Pvt Ltd | Agonistas del gpr40. |
| JP6097998B2 (ja) * | 2010-12-16 | 2017-03-22 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロイコトリエン生成のビアリールアミドインヒビター |
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- 2013-02-27 CA CA2866210A patent/CA2866210A1/en not_active Abandoned
- 2013-02-27 JP JP2014559335A patent/JP2015508809A/ja active Pending
- 2013-02-27 EP EP13719305.8A patent/EP2820005A1/en not_active Withdrawn
- 2013-02-27 IN IN1839MUN2014 patent/IN2014MN01839A/en unknown
- 2013-02-27 US US14/381,696 patent/US20150072969A1/en not_active Abandoned
- 2013-02-28 AR ARP130100630A patent/AR090191A1/es unknown
-
2014
- 2014-08-21 IL IL234254A patent/IL234254A/en not_active IP Right Cessation
- 2014-09-26 ZA ZA2014/07034A patent/ZA201407034B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201407034B (en) | 2017-08-30 |
| IL234254A (en) | 2017-03-30 |
| TW201341356A (zh) | 2013-10-16 |
| CA2866210A1 (en) | 2013-09-06 |
| JP2015508809A (ja) | 2015-03-23 |
| WO2013128378A1 (en) | 2013-09-06 |
| KR20140138243A (ko) | 2014-12-03 |
| US20150072969A1 (en) | 2015-03-12 |
| EP2820005A1 (en) | 2015-01-07 |
| MX2014010272A (es) | 2015-08-14 |
| NZ631569A (en) | 2016-10-28 |
| AU2013227266A1 (en) | 2014-10-02 |
| IN2014MN01839A (enExample) | 2015-07-03 |
| AR090191A1 (es) | 2014-10-29 |
| CN104144920A (zh) | 2014-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20170417 |