CA2545823A1 - 4-oxo-4,5-dihydro-furan-2-carboxylic and acid derivatives and methods of treatment of metabolic-related disorders thereof - Google Patents
4-oxo-4,5-dihydro-furan-2-carboxylic and acid derivatives and methods of treatment of metabolic-related disorders thereof Download PDFInfo
- Publication number
- CA2545823A1 CA2545823A1 CA002545823A CA2545823A CA2545823A1 CA 2545823 A1 CA2545823 A1 CA 2545823A1 CA 002545823 A CA002545823 A CA 002545823A CA 2545823 A CA2545823 A CA 2545823A CA 2545823 A1 CA2545823 A1 CA 2545823A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- phenyl
- oxo
- dihydro
- furan
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 95
- 238000011282 treatment Methods 0.000 title claims description 56
- 230000002503 metabolic effect Effects 0.000 title claims description 47
- 239000002253 acid Chemical class 0.000 title description 30
- BMZBEWUYETVZAG-UHFFFAOYSA-N 4-oxofuran-2-carboxylic acid Chemical class OC(=O)C1=CC(=O)CO1 BMZBEWUYETVZAG-UHFFFAOYSA-N 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims description 307
- -1 C1-6 alkykarboxamide Chemical group 0.000 claims description 199
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 95
- 125000001072 heteroaryl group Chemical group 0.000 claims description 74
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 57
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 125000001188 haloalkyl group Chemical group 0.000 claims description 37
- 241000282414 Homo sapiens Species 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 33
- 241001465754 Metazoa Species 0.000 claims description 32
- 125000004423 acyloxy group Chemical group 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 239000003112 inhibitor Substances 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 201000001320 Atherosclerosis Diseases 0.000 claims description 30
- 201000010099 disease Diseases 0.000 claims description 30
- 206010022489 Insulin Resistance Diseases 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- LDRXFNRHMPVZBO-UHFFFAOYSA-N 5-(cyclopenten-1-yl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1CCCC=1C1(C)OC(C(O)=O)=CC1=O LDRXFNRHMPVZBO-UHFFFAOYSA-N 0.000 claims description 26
- 239000000556 agonist Substances 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000003107 substituted aryl group Chemical group 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 19
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 19
- 208000029078 coronary artery disease Diseases 0.000 claims description 18
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 18
- 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 17
- 239000003937 drug carrier Substances 0.000 claims description 17
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 16
- 238000003786 synthesis reaction Methods 0.000 claims description 16
- 238000002560 therapeutic procedure Methods 0.000 claims description 16
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 12
- 229940123208 Biguanide Drugs 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 10
- 239000003623 enhancer Substances 0.000 claims description 10
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 235000020824 obesity Nutrition 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- 239000005541 ACE inhibitor Substances 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 9
- 208000006011 Stroke Diseases 0.000 claims description 9
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 9
- 208000019622 heart disease Diseases 0.000 claims description 9
- 229940031439 squalene Drugs 0.000 claims description 9
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 9
- 208000011580 syndromic disease Diseases 0.000 claims description 9
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 8
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 8
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 229940125753 fibrate Drugs 0.000 claims description 7
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 6
- 150000003857 carboxamides Chemical class 0.000 claims description 6
- 230000015556 catabolic process Effects 0.000 claims description 6
- 230000003914 insulin secretion Effects 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 5
- VMKNMLFSCDCNTE-UHFFFAOYSA-N 5-(3-bromophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=CC(Br)=CC=1C1(C)OC(C(O)=O)=CC1=O VMKNMLFSCDCNTE-UHFFFAOYSA-N 0.000 claims description 5
- PXRNPXRNTIDHKJ-UHFFFAOYSA-N 5-methyl-5-(5-methylthiophen-2-yl)-4-oxofuran-2-carboxylic acid Chemical compound S1C(C)=CC=C1C1(C)C(=O)C=C(C(O)=O)O1 PXRNPXRNTIDHKJ-UHFFFAOYSA-N 0.000 claims description 5
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 5
- 239000003288 aldose reductase inhibitor Substances 0.000 claims description 5
- 239000004031 partial agonist Substances 0.000 claims description 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 4
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- YHFHOBUUFHAIJY-UHFFFAOYSA-N 5-(4-bromothiophen-2-yl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C(Br)=CSC=1C1(C)OC(C(O)=O)=CC1=O YHFHOBUUFHAIJY-UHFFFAOYSA-N 0.000 claims description 4
- OIUBTTBLZOOEFX-UHFFFAOYSA-N 5-(5-chlorothiophen-2-yl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=C(Cl)SC=1C1(C)OC(C(O)=O)=CC1=O OIUBTTBLZOOEFX-UHFFFAOYSA-N 0.000 claims description 4
- WZSGORNHMKJGII-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1CCCCC=1C1(C)OC(C(O)=O)=CC1=O WZSGORNHMKJGII-UHFFFAOYSA-N 0.000 claims description 4
- 229940118148 Aldose reductase inhibitor Drugs 0.000 claims description 4
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 4
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 4
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 4
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
- AAYKCDKHWYBBAC-UHFFFAOYSA-N methyl 5-(cyclohexen-1-yl)-5-methyl-4-oxofuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CCCCC1 AAYKCDKHWYBBAC-UHFFFAOYSA-N 0.000 claims description 4
- GSJDSFMRZXYCRX-UHFFFAOYSA-N methyl 5-methyl-5-(5-methylthiophen-2-yl)-4-oxofuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CC=C(C)S1 GSJDSFMRZXYCRX-UHFFFAOYSA-N 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- ALXBEPHGSHCMBN-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C(F)=CC(F)=CC=1C1(C)OC(C(O)=O)=CC1=O ALXBEPHGSHCMBN-UHFFFAOYSA-N 0.000 claims description 3
- DCWNQFBOTWDFNR-UHFFFAOYSA-N 5-(3-chlorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C1(C)OC(C(O)=O)=CC1=O DCWNQFBOTWDFNR-UHFFFAOYSA-N 0.000 claims description 3
- HUOYXUKHQBGESB-UHFFFAOYSA-N 5-(3-ethylphenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound CCC1=CC=CC(C2(C)C(C=C(O2)C(O)=O)=O)=C1 HUOYXUKHQBGESB-UHFFFAOYSA-N 0.000 claims description 3
- BLOJHYLVLSDXLQ-UHFFFAOYSA-N 5-(3-fluorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=CC(F)=CC=1C1(C)OC(C(O)=O)=CC1=O BLOJHYLVLSDXLQ-UHFFFAOYSA-N 0.000 claims description 3
- QJKQNKXFEZQYQP-UHFFFAOYSA-N 5-(3-iodophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=CC(I)=CC=1C1(C)OC(C(O)=O)=CC1=O QJKQNKXFEZQYQP-UHFFFAOYSA-N 0.000 claims description 3
- YFPAONQFZGAYEZ-UHFFFAOYSA-N 5-(4-bromo-5-methylthiophen-2-yl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound BrC1=C(C)SC(C2(C)C(C=C(O2)C(O)=O)=O)=C1 YFPAONQFZGAYEZ-UHFFFAOYSA-N 0.000 claims description 3
- WJDLYZAOTHNUJX-UHFFFAOYSA-N 5-(5-bromothiophen-3-yl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1SC(Br)=CC=1C1(C)OC(C(O)=O)=CC1=O WJDLYZAOTHNUJX-UHFFFAOYSA-N 0.000 claims description 3
- JPZPZVVRVYTIHX-UHFFFAOYSA-N 5-(5-chlorothiophen-3-yl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1SC(Cl)=CC=1C1(C)OC(C(O)=O)=CC1=O JPZPZVVRVYTIHX-UHFFFAOYSA-N 0.000 claims description 3
- SZAVHIWMBRHRGF-UHFFFAOYSA-N 5-methyl-4-oxo-5-thiophen-2-ylfuran-2-carboxylic acid Chemical compound C=1C=CSC=1C1(C)OC(C(O)=O)=CC1=O SZAVHIWMBRHRGF-UHFFFAOYSA-N 0.000 claims description 3
- GRUPRIDVEUNNIP-UHFFFAOYSA-N 5-methyl-4-oxo-5-thiophen-3-ylfuran-2-carboxylic acid Chemical compound C1=CSC=C1C1(C)OC(C(O)=O)=CC1=O GRUPRIDVEUNNIP-UHFFFAOYSA-N 0.000 claims description 3
- UOXNSDQVISINNS-UHFFFAOYSA-N 5-methyl-5-(3-methylphenyl)-4-oxofuran-2-carboxylic acid Chemical compound CC1=CC=CC(C2(C)C(C=C(O2)C(O)=O)=O)=C1 UOXNSDQVISINNS-UHFFFAOYSA-N 0.000 claims description 3
- YPMMNDVOYQLHIX-UHFFFAOYSA-N methyl 5-(3-bromophenyl)-5-methyl-4-oxofuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CC=CC(Br)=C1 YPMMNDVOYQLHIX-UHFFFAOYSA-N 0.000 claims description 3
- SFKSKFHIKWBWME-UHFFFAOYSA-N methyl 5-(5-chlorothiophen-3-yl)-5-methyl-4-oxofuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CSC(Cl)=C1 SFKSKFHIKWBWME-UHFFFAOYSA-N 0.000 claims description 3
- ZRNYKLLJEIBOST-UHFFFAOYSA-N methyl 5-methyl-4-oxo-5-(3-phenylphenyl)furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CC=CC(C=2C=CC=CC=2)=C1 ZRNYKLLJEIBOST-UHFFFAOYSA-N 0.000 claims description 3
- SUUNVIHQZOEGPA-UHFFFAOYSA-N methyl 5-methyl-4-oxo-5-(3-thiophen-2-ylphenyl)furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CC=CC(C=2SC=CC=2)=C1 SUUNVIHQZOEGPA-UHFFFAOYSA-N 0.000 claims description 3
- YFVYMZBCJBUWNH-UHFFFAOYSA-N methyl 5-methyl-4-oxo-5-thiophen-3-ylfuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CSC=C1 YFVYMZBCJBUWNH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- SUHZZFNDVLWPTL-UHFFFAOYSA-N 5-ethyl-4-oxo-5-phenylfuran-2-carboxylic acid Chemical compound C=1C=CC=CC=1C1(CC)OC(C(O)=O)=CC1=O SUHZZFNDVLWPTL-UHFFFAOYSA-N 0.000 claims description 2
- GIOPESNBNCSBLX-UHFFFAOYSA-N 5-methyl-4-oxo-5-[3-(trifluoromethyl)phenyl]furan-2-carboxylic acid Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(C)OC(C(O)=O)=CC1=O GIOPESNBNCSBLX-UHFFFAOYSA-N 0.000 claims description 2
- ZTLLDBJMDZIAQP-UHFFFAOYSA-N methyl 5-(5-bromothiophen-3-yl)-5-methyl-4-oxofuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CSC(Br)=C1 ZTLLDBJMDZIAQP-UHFFFAOYSA-N 0.000 claims description 2
- DGTZAUKZDBYWNN-UHFFFAOYSA-N methyl 5-methyl-4-oxo-5-thiophen-2-ylfuran-2-carboxylate Chemical compound O1C(C(=O)OC)=CC(=O)C1(C)C1=CC=CS1 DGTZAUKZDBYWNN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 5
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- TVRUYIIGGOWPAG-UHFFFAOYSA-N 4-oxo-5-phenyl-5-(trifluoromethyl)furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC(=O)C1(C(F)(F)F)C1=CC=CC=C1 TVRUYIIGGOWPAG-UHFFFAOYSA-N 0.000 claims 1
- AZQHSNYXCFYODD-UHFFFAOYSA-N 5-(2,4-difluorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=C(F)C=C(F)C=1C1(C)OC(C(O)=O)=CC1=O AZQHSNYXCFYODD-UHFFFAOYSA-N 0.000 claims 1
- NLWVUJBQWNYFGM-UHFFFAOYSA-N 5-(2,5-dichlorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C(Cl)=CC=C(Cl)C=1C1(C)OC(C(O)=O)=CC1=O NLWVUJBQWNYFGM-UHFFFAOYSA-N 0.000 claims 1
- NINDTCSJSZFQTN-UHFFFAOYSA-N 5-(2,6-difluorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound FC=1C=CC=C(F)C=1C1(C)OC(C(O)=O)=CC1=O NINDTCSJSZFQTN-UHFFFAOYSA-N 0.000 claims 1
- VUJKPKCBMUEMHQ-UHFFFAOYSA-N 5-(2-fluorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=CC=C(F)C=1C1(C)OC(C(O)=O)=CC1=O VUJKPKCBMUEMHQ-UHFFFAOYSA-N 0.000 claims 1
- NFCWTNPYAANPJO-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=C(F)C(F)=CC=1C1(C)OC(C(O)=O)=CC1=O NFCWTNPYAANPJO-UHFFFAOYSA-N 0.000 claims 1
- RLXNZMWKPKPBFR-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C(Cl)=CC(Cl)=CC=1C1(C)OC(C(O)=O)=CC1=O RLXNZMWKPKPBFR-UHFFFAOYSA-N 0.000 claims 1
- RCCLJOBPQSVKOB-UHFFFAOYSA-N 5-(3-cyanophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=CC(C#N)=CC=1C1(C)OC(C(O)=O)=CC1=O RCCLJOBPQSVKOB-UHFFFAOYSA-N 0.000 claims 1
- AAJWNMBSTFQBSD-UHFFFAOYSA-N 5-(3-ethenylphenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=CC(C=C)=CC=1C1(C)OC(C(O)=O)=CC1=O AAJWNMBSTFQBSD-UHFFFAOYSA-N 0.000 claims 1
- KJRXFRPWDMVTLR-UHFFFAOYSA-N 5-(3-methoxyphenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound COC1=CC=CC(C2(C)C(C=C(O2)C(O)=O)=O)=C1 KJRXFRPWDMVTLR-UHFFFAOYSA-N 0.000 claims 1
- XZXUIFUBIDTNOU-UHFFFAOYSA-N 5-(4-fluorophenyl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C)OC(C(O)=O)=CC1=O XZXUIFUBIDTNOU-UHFFFAOYSA-N 0.000 claims 1
- HWWTURDCJBNZDY-UHFFFAOYSA-N 5-(furan-2-yl)-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C=1C=COC=1C1(C)OC(C(O)=O)=CC1=O HWWTURDCJBNZDY-UHFFFAOYSA-N 0.000 claims 1
- CRGARTVGZYPKJA-UHFFFAOYSA-N 5-cyclopentyl-5-methyl-4-oxofuran-2-carboxylic acid Chemical compound C1CCCC1C1(C)OC(C(O)=O)=CC1=O CRGARTVGZYPKJA-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/04—Anorexiants; Antiobesity agents
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- A61P3/06—Antihyperlipidemics
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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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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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/02—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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/02—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
- C07D409/10—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 carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Biomedical Technology (AREA)
- Neurology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52426903P | 2003-11-21 | 2003-11-21 | |
| US60/524,269 | 2003-11-21 | ||
| PCT/US2004/038920 WO2005051937A2 (en) | 2003-11-21 | 2004-11-18 | 4-oxo-4,5-dihydro-furan-2-carboxylic and acid derivatives and methods of treatment of metabolic-related disorders thereof |
Publications (1)
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| CA2545823A1 true CA2545823A1 (en) | 2005-06-09 |
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|---|---|---|---|
| CA002545823A Abandoned CA2545823A1 (en) | 2003-11-21 | 2004-11-18 | 4-oxo-4,5-dihydro-furan-2-carboxylic and acid derivatives and methods of treatment of metabolic-related disorders thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20070093545A1 (enExample) |
| EP (1) | EP1701947B1 (enExample) |
| JP (1) | JP2007512346A (enExample) |
| CN (1) | CN1882557A (enExample) |
| AT (1) | ATE440828T1 (enExample) |
| AU (1) | AU2004293415A1 (enExample) |
| CA (1) | CA2545823A1 (enExample) |
| DE (1) | DE602004022864D1 (enExample) |
| ES (1) | ES2331521T3 (enExample) |
| WO (1) | WO2005051937A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004083388A2 (en) | 2003-03-14 | 2004-09-30 | Bristol-Myers Squibb Company | Polynucleotide encoding a novel human g-protein coupled receptor variant of hm74, hgprbmy74 |
| EP1819684B1 (en) | 2004-12-03 | 2013-08-07 | Intervet International B.V. | Substituted piperazines as cb1 antagonists |
| KR100826108B1 (ko) | 2006-08-04 | 2008-04-29 | 한국화학연구원 | 퓨란-2-카복실산 유도체 및 그의 제조 방법 |
| WO2011044139A1 (en) * | 2009-10-05 | 2011-04-14 | Catabasis Pharmaceuticals, Inc. | Fatty acid acifran derivatives and their uses |
| AU2013290100A1 (en) | 2012-07-11 | 2015-01-29 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| CN109416406B (zh) * | 2016-07-05 | 2023-06-20 | 深圳帧观德芯科技有限公司 | 具有不同热膨胀系数的接合材料 |
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| US4169202A (en) * | 1978-06-05 | 1979-09-25 | American Home Products Corporation | Process for preparing 4,5-dihydro-4-oxofuran-2-carboxylic acid derivatives |
| US4244958A (en) * | 1979-05-10 | 1981-01-13 | American Home Products Corporation | Hypolipidemic derivatives of 4,5-dihydro-4-oxofuran-2-carboxylic acid |
| US6902902B2 (en) * | 2001-11-27 | 2005-06-07 | Arena Pharmaceuticals, Inc. | Human G protein-coupled receptors and modulators thereof for the treatment of metabolic-related disorders |
| AU2003282679A1 (en) | 2002-10-04 | 2004-05-04 | Arena Pharmaceuticals, Inc. | Hydroxypyrazoles for use against metabolic-related disorders |
| CN1720046A (zh) | 2002-10-10 | 2006-01-11 | 阿伦纳药品公司 | 作为抗脂解药用于治疗血脂异常等代谢相关疾病的5－取代的2h－吡唑－3－甲酸衍生物 |
| US20060122240A1 (en) * | 2002-11-05 | 2006-06-08 | Arena Pharmaceuticals, Inc. | Benzotriazoles and methods of prophylaxis or treatment of metabolic-related disorders thereof |
| US20070032537A1 (en) * | 2003-06-13 | 2007-02-08 | Arena Pharmaceuticals, Inc. | 5-Substituted 2h-pyrazole-3-carboxylic acid derivatives as agonists for the acid receptor rup25 for the treatment of dyslipidemia and related diseases |
| TWI258478B (en) * | 2003-10-31 | 2006-07-21 | Arena Pharm Inc | Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof |
| US20080139628A1 (en) * | 2004-11-05 | 2008-06-12 | Arena Pharmaceuticals, Inc. | Compositions For Treating Flushing And Lipid-Associated Disorders Comprising Niacin Receptor Partial Agonists |
| PE20060949A1 (es) * | 2004-12-23 | 2006-10-11 | Arena Pharm Inc | Derivados fusionados de pirazol como agonistas del receptor de niacina |
| AU2006214286A1 (en) | 2005-02-18 | 2006-08-24 | Arena Pharmaceuticals, Inc. | Methods and compositions for the treatment of lipid-associated disorders |
| EP1899304A1 (en) | 2005-05-23 | 2008-03-19 | Arena Pharmaceuticals, Inc. | 5-amino-1h-pyrazole-3-carboxylic acid derivatives as agonists for the g-protein coupled receptor (gpcr) rup38 for the treatment of metabolic-related disorders thereof |
| WO2007021744A1 (en) | 2005-08-10 | 2007-02-22 | Arena Pharmaceuticals, Inc. | Methods for determining probability of an adverse or favorable reaction to a niacin receptor agonist |
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- 2004-11-18 WO PCT/US2004/038920 patent/WO2005051937A2/en not_active Ceased
- 2004-11-18 CN CNA2004800340741A patent/CN1882557A/zh active Pending
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- 2004-11-18 EP EP04811612A patent/EP1701947B1/en not_active Expired - Lifetime
- 2004-11-18 DE DE602004022864T patent/DE602004022864D1/de not_active Expired - Lifetime
- 2004-11-18 US US10/578,732 patent/US20070093545A1/en not_active Abandoned
- 2004-11-18 JP JP2006541430A patent/JP2007512346A/ja active Pending
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2006
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| JP2007512346A (ja) | 2007-05-17 |
| ES2331521T3 (es) | 2010-01-07 |
| EP1701947A2 (en) | 2006-09-20 |
| WO2005051937A2 (en) | 2005-06-09 |
| US20070093545A1 (en) | 2007-04-26 |
| US7803837B2 (en) | 2010-09-28 |
| ATE440828T1 (de) | 2009-09-15 |
| CN1882557A (zh) | 2006-12-20 |
| AU2004293415A1 (en) | 2005-06-09 |
| DE602004022864D1 (de) | 2009-10-08 |
| EP1701947B1 (en) | 2009-08-26 |
| US20070161701A1 (en) | 2007-07-12 |
| WO2005051937A3 (en) | 2005-09-15 |
| WO2005051937A8 (en) | 2006-08-31 |
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