JP2006516251A5 - - Google Patents
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- Publication number
- JP2006516251A5 JP2006516251A5 JP2004563903A JP2004563903A JP2006516251A5 JP 2006516251 A5 JP2006516251 A5 JP 2006516251A5 JP 2004563903 A JP2004563903 A JP 2004563903A JP 2004563903 A JP2004563903 A JP 2004563903A JP 2006516251 A5 JP2006516251 A5 JP 2006516251A5
- Authority
- JP
- Japan
- Prior art keywords
- propoxy
- indanyl
- acetic acid
- thiazol
- optionally
- 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.)
- Granted
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- 229910052717 sulfur Inorganic materials 0.000 claims 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 17
- 125000002837 carbocyclic group Chemical group 0.000 claims 14
- 206010012601 diabetes mellitus Diseases 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 8
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 239000008103 glucose Substances 0.000 claims 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- NRMLKMKBUYOILR-QFIPXVFZSA-N 2-[(1s)-5-[3-[[2-(4-ethoxyphenyl)-5-methylpyrimidin-4-yl]methylamino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC(OCC)=CC=C1C1=NC=C(C)C(CNCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=N1 NRMLKMKBUYOILR-QFIPXVFZSA-N 0.000 claims 2
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 229940122199 Insulin secretagogue Drugs 0.000 claims 2
- 229940122355 Insulin sensitizer Drugs 0.000 claims 2
- 229940126033 PPAR agonist Drugs 0.000 claims 2
- 229940100389 Sulfonylurea Drugs 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 2
- 239000002220 antihypertensive agent Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 229920000080 bile acid sequestrant Polymers 0.000 claims 2
- 229940096699 bile acid sequestrants Drugs 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000029142 excretion Effects 0.000 claims 2
- 229940125753 fibrate Drugs 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- BNYHRGTXRPWASY-UHFFFAOYSA-N nonylsulfonylurea Chemical compound CCCCCCCCCS(=O)(=O)NC(N)=O BNYHRGTXRPWASY-UHFFFAOYSA-N 0.000 claims 2
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 2
- 239000008177 pharmaceutical agent Substances 0.000 claims 2
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 2
- 230000000580 secretagogue effect Effects 0.000 claims 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- JIBRBEPRUAKTNJ-AHWVRZQESA-N (2s)-2-[(1s)-5-[2-[6-(4-ethylphenyl)pyridin-2-yl]ethoxy]-2,3-dihydro-1h-inden-1-yl]butanoic acid Chemical compound C([C@H](C1=CC=2)[C@H](CC)C(O)=O)CC1=CC=2OCCC(N=1)=CC=CC=1C1=CC=C(CC)C=C1 JIBRBEPRUAKTNJ-AHWVRZQESA-N 0.000 claims 1
- TTXZAMXYYZRBGI-CUXXENAFSA-N 2-[(1r)-5-[3-[2-propyl-4-(3,5,6,7-tetrahydro-2h-pyrano[2,3-d][1,3]thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C(S1)NC2=C1CCCO2 TTXZAMXYYZRBGI-CUXXENAFSA-N 0.000 claims 1
- WYZVWTYQKOZQQS-NRFANRHFSA-N 2-[(1s)-5-[2-[6-(4-acetylphenyl)pyridin-2-yl]ethoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CC(CCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=N1 WYZVWTYQKOZQQS-NRFANRHFSA-N 0.000 claims 1
- IAOGDTFZZMHYHP-QFIPXVFZSA-N 2-[(1s)-5-[3-(4-phenoxy-2-propylphenoxy)propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1OC1=CC=CC=C1 IAOGDTFZZMHYHP-QFIPXVFZSA-N 0.000 claims 1
- GYLMBHYEEPSETC-KRWDZBQOSA-N 2-[(1s)-5-[3-[(3,7-dimethyl-1,2-benzoxazol-6-yl)oxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)CCC2=CC(OCCCOC=2C(C)=C3ON=C(C3=CC=2)C)=C1 GYLMBHYEEPSETC-KRWDZBQOSA-N 0.000 claims 1
- NUTUSSDZMGFKKF-SFHVURJKSA-N 2-[(1s)-5-[3-[(3-methyl-7-propyl-1,2-benzoxazol-6-yl)oxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)CCC2=CC(OCCCOC2=C(C=3ON=C(C)C=3C=C2)CCC)=C1 NUTUSSDZMGFKKF-SFHVURJKSA-N 0.000 claims 1
- KHWSFWPKNKLKPX-FQEVSTJZSA-N 2-[(1s)-5-[3-[2-ethoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OCC)=C1 KHWSFWPKNKLKPX-FQEVSTJZSA-N 0.000 claims 1
- HGRRXAJCQVQKSP-HSYKDVHTSA-N 2-[(1s)-5-[3-[2-methoxy-4-(3,5,6,7-tetrahydro-2h-pyrano[2,3-d][1,3]thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=CC=1C(S1)NC2=C1CCCO2 HGRRXAJCQVQKSP-HSYKDVHTSA-N 0.000 claims 1
- NPZMDWHUIIGJNS-IBGZPJMESA-N 2-[(1s)-5-[3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=C1 NPZMDWHUIIGJNS-IBGZPJMESA-N 0.000 claims 1
- BLJVVKCIOACNOQ-IBGZPJMESA-N 2-[(1s)-5-[3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(O2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=C1 BLJVVKCIOACNOQ-IBGZPJMESA-N 0.000 claims 1
- YUWKOSPDHRFEEF-KRWDZBQOSA-N 2-[(1s)-5-[3-[2-methoxy-4-(4-methoxy-1,3-thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound COC1=CSC(C=2C=C(OC)C(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 YUWKOSPDHRFEEF-KRWDZBQOSA-N 0.000 claims 1
- BRUFULPAONKCPM-INIZCTEOSA-N 2-[(1s)-5-[3-[2-methyl-4-[3-(trifluoromethyl)-1,2,4-thiadiazol-5-yl]phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(C)=CC=1C1=NC(C(F)(F)F)=NS1 BRUFULPAONKCPM-INIZCTEOSA-N 0.000 claims 1
- SLUNRBMNJCMKOE-NRFANRHFSA-N 2-[(1s)-5-[3-[2-propoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OCCC)=C1 SLUNRBMNJCMKOE-NRFANRHFSA-N 0.000 claims 1
- VCBBROSSYZDABH-IBGZPJMESA-N 2-[(1s)-5-[3-[2-propyl-4-(1,3-thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC=CS1 VCBBROSSYZDABH-IBGZPJMESA-N 0.000 claims 1
- TTXZAMXYYZRBGI-OORIHMLWSA-N 2-[(1s)-5-[3-[2-propyl-4-(3,5,6,7-tetrahydro-2h-pyrano[2,3-d][1,3]thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C(S1)NC2=C1CCCO2 TTXZAMXYYZRBGI-OORIHMLWSA-N 0.000 claims 1
- IAFVOFFJCUHEHP-NRFANRHFSA-N 2-[(1s)-5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=C1 IAFVOFFJCUHEHP-NRFANRHFSA-N 0.000 claims 1
- DPXRRYRDBWDWRM-NRFANRHFSA-N 2-[(1s)-5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(O2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=C1 DPXRRYRDBWDWRM-NRFANRHFSA-N 0.000 claims 1
- UJRNVHVWFAPHHZ-KRWDZBQOSA-N 2-[(1s)-5-[3-[2-propyl-4-(trifluoromethyl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCCC1=CC(C(F)(F)F)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 UJRNVHVWFAPHHZ-KRWDZBQOSA-N 0.000 claims 1
- HEGJINSQHTYDEX-SFHVURJKSA-N 2-[(1s)-5-[3-[2-propyl-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(C(F)(F)F)=CS1 HEGJINSQHTYDEX-SFHVURJKSA-N 0.000 claims 1
- UBZORZBZKNRJFC-IBGZPJMESA-N 2-[(1s)-5-[3-[4-(1,3-benzothiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC=C2SC(C=3C=C(C(=CC=3)OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)OC)=NC2=C1 UBZORZBZKNRJFC-IBGZPJMESA-N 0.000 claims 1
- NTVBAWSNQRKVKF-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C(C=C1)=CC=C1OCCCOC1=CC=C2[C@H](CC(=O)O)CCC2=C1 NTVBAWSNQRKVKF-FQEVSTJZSA-N 0.000 claims 1
- ZZKJSMBFWZMRRS-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(O2)=C1N=C2C(C=C1)=CC=C1OCCCOC1=CC=C2[C@H](CC(=O)O)CCC2=C1 ZZKJSMBFWZMRRS-FQEVSTJZSA-N 0.000 claims 1
- ZBFIQWUEGZKBFS-IBGZPJMESA-N 2-[(1s)-5-[3-[4-(4,5-dimethyl-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=CC=1C1=NC(C)=C(C)S1 ZBFIQWUEGZKBFS-IBGZPJMESA-N 0.000 claims 1
- KZAIHPRSXFXXNU-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4,5-dimethyl-1,3-thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound S1C(C)=C(C)N=C1C(C=C1)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 KZAIHPRSXFXXNU-FQEVSTJZSA-N 0.000 claims 1
- WMOAALINFRTEGC-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(4-ethoxy-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCOC1=CSC(C=2C=C(OC)C(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 WMOAALINFRTEGC-SFHVURJKSA-N 0.000 claims 1
- DTSZUNRPQWYGHX-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4-ethoxy-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(OCC)=CS1 DTSZUNRPQWYGHX-FQEVSTJZSA-N 0.000 claims 1
- UQFZTBWTJZBMDL-IBGZPJMESA-N 2-[(1s)-5-[3-[4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound S1C(C)=C(OCC)N=C1C(C=C1OC)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 UQFZTBWTJZBMDL-IBGZPJMESA-N 0.000 claims 1
- XFEBTJLTAZGGPY-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(OCC)=C(C)S1 XFEBTJLTAZGGPY-NRFANRHFSA-N 0.000 claims 1
- WLFRWUYWTYPAOJ-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(4-ethyl-1,3-oxazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCC1=COC(C=2C=C(OC)C(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 WLFRWUYWTYPAOJ-SFHVURJKSA-N 0.000 claims 1
- KKELJTWGLRARIG-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4-ethyl-1,3-oxazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(CC)=CO1 KKELJTWGLRARIG-FQEVSTJZSA-N 0.000 claims 1
- YVTAAESLMBHKDQ-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCC1=CSC(C=2C=C(OC)C(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 YVTAAESLMBHKDQ-SFHVURJKSA-N 0.000 claims 1
- WCDXSIMIKBDXKI-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(CC)=CS1 WCDXSIMIKBDXKI-FQEVSTJZSA-N 0.000 claims 1
- HBKNDUAKMHVGNM-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(4-methoxy-1,3-thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound COC1=CSC(C=2C=CC(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 HBKNDUAKMHVGNM-SFHVURJKSA-N 0.000 claims 1
- DABDLIFECGXQNC-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(4-propan-2-yloxy-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(OC(C)C)=CS1 DABDLIFECGXQNC-NRFANRHFSA-N 0.000 claims 1
- ZTQUDSFSSMPWPD-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(4-tert-butyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(C(C)(C)C)=CS1 ZTQUDSFSSMPWPD-NRFANRHFSA-N 0.000 claims 1
- QJKOTSRVMJGHRK-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(5,5-dimethyl-7-oxo-4,6-dihydro-1,3-benzothiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1C(C)(C)CC(=O)C(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=C1 QJKOTSRVMJGHRK-NRFANRHFSA-N 0.000 claims 1
- IELCDGLGXNKKIF-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(5,6-dihydro-4h-cyclopenta[d][1,3]thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)CCC2=CC(OCCCOC2=CC=C(C=C2OC)C=2SC=3CCCC=3N=2)=C1 IELCDGLGXNKKIF-SFHVURJKSA-N 0.000 claims 1
- FQTHEIJACHCXRP-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(5,6-dihydro-4h-cyclopenta[d][1,3]thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)CCC2=CC(OCCCOC2=CC=C(C=C2CCC)C=2SC=3CCCC=3N=2)=C1 FQTHEIJACHCXRP-FQEVSTJZSA-N 0.000 claims 1
- DCJCLUBXJKPDCS-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(5-acetyl-4-methyl-1,3-oxazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(C)=C(C(C)=O)O1 DCJCLUBXJKPDCS-NRFANRHFSA-N 0.000 claims 1
- IILOBIPXSQDFDA-IBGZPJMESA-N 2-[(1s)-5-[3-[4-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=CC=1C1=NC(C)=C(C(C)=O)S1 IILOBIPXSQDFDA-IBGZPJMESA-N 0.000 claims 1
- XUJUKBDYMUPHEK-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(C)=C(C(C)=O)S1 XUJUKBDYMUPHEK-NRFANRHFSA-N 0.000 claims 1
- LMHOCAPOMOVOTR-IBGZPJMESA-N 2-[(1s)-5-[3-[4-[4-(carboxymethyl)-1,3-thiazol-2-yl]-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(CC(O)=O)=CS1 LMHOCAPOMOVOTR-IBGZPJMESA-N 0.000 claims 1
- BOIFMTPHEQFLJE-NRFANRHFSA-N 2-[(1s)-5-[3-[4-[5-(dimethylcarbamoyl)-4-methyl-1,3-thiazol-2-yl]-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(C)=C(C(=O)N(C)C)S1 BOIFMTPHEQFLJE-NRFANRHFSA-N 0.000 claims 1
- INSJDULTKROYCO-SFHVURJKSA-N 2-[(1s)-5-[3-[5-(4,5-dimethyl-1,3-thiazol-2-yl)pyridin-2-yl]oxypropoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound S1C(C)=C(C)N=C1C(C=N1)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 INSJDULTKROYCO-SFHVURJKSA-N 0.000 claims 1
- NDSVGELSLGUYIY-KRWDZBQOSA-N 2-[(1s)-5-[3-[5-(4-ethyl-1,3-thiazol-2-yl)pyridin-2-yl]oxypropoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCC1=CSC(C=2C=NC(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 NDSVGELSLGUYIY-KRWDZBQOSA-N 0.000 claims 1
- VZQYLUXYBCRPJQ-SFHVURJKSA-N 2-[(1s)-5-[3-[5-(5-acetyl-4-methyl-1,3-thiazol-2-yl)pyridin-2-yl]oxypropoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CC1=C(C(=O)C)SC(C=2C=NC(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 VZQYLUXYBCRPJQ-SFHVURJKSA-N 0.000 claims 1
- QBXKXZJIAQWBEG-MHZLTWQESA-N 2-[(1s)-5-[3-[[2-(4-cyclohexylphenyl)-6-methylpyrimidin-4-yl]methylamino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound N=1C(C)=CC(CNCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=NC=1C(C=C1)=CC=C1C1CCCCC1 QBXKXZJIAQWBEG-MHZLTWQESA-N 0.000 claims 1
- SHQLOBYFHIDANF-QHCPKHFHSA-N 2-[(1s)-5-[3-[[2-(4-ethylphenyl)-5-methylpyrimidin-4-yl]methylamino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC(CC)=CC=C1C1=NC=C(C)C(CNCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=N1 SHQLOBYFHIDANF-QHCPKHFHSA-N 0.000 claims 1
- OLIWARCYLRSRSC-FQEVSTJZSA-N 2-[(1s)-5-[3-[[2-(4-fluorophenyl)-6-methylpyrimidin-4-yl]methylamino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound N=1C(C)=CC(CNCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=NC=1C1=CC=C(F)C=C1 OLIWARCYLRSRSC-FQEVSTJZSA-N 0.000 claims 1
- XAYFBMKODHRPRK-QHCPKHFHSA-N 2-[(1s)-5-[3-[[2-(4-tert-butylphenyl)-5-methylpyrimidin-4-yl]methylamino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound N1=C(CNCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(C)=CN=C1C1=CC=C(C(C)(C)C)C=C1 XAYFBMKODHRPRK-QHCPKHFHSA-N 0.000 claims 1
- GFQFGNOBZDTGGV-IBGZPJMESA-N 2-[(1s)-5-[3-[[5-fluoro-2-(4-methoxyphenyl)pyrimidin-4-yl]methylamino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NC=C(F)C(CNCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=N1 GFQFGNOBZDTGGV-IBGZPJMESA-N 0.000 claims 1
- WZGYQSLQJYNOER-QFIPXVFZSA-N 2-[(1s)-5-[3-[[5-fluoro-2-(4-propan-2-ylphenyl)pyrimidin-4-yl]methylamino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=NC=C(F)C(CNCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=N1 WZGYQSLQJYNOER-QFIPXVFZSA-N 0.000 claims 1
- VAXBUDASTPYURF-DEOSSOPVSA-N 2-[(1s)-5-[3-[methyl-[5-methyl-2-(4-propan-2-ylphenyl)pyrimidin-4-yl]amino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=NC=C(C)C(N(C)CCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=N1 VAXBUDASTPYURF-DEOSSOPVSA-N 0.000 claims 1
- FKPYJIJYMXBAFW-IBGZPJMESA-N 2-[4-[3-[[(1s)-1-(carboxymethyl)-2,3-dihydro-1h-inden-5-yl]oxy]propoxy]-3-propylphenyl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(C)=C(C(O)=O)S1 FKPYJIJYMXBAFW-IBGZPJMESA-N 0.000 claims 1
- RLDHAABFWXUBDC-SFHVURJKSA-N 2-[4-[3-[[(1s)-1-(carboxymethyl)-2,3-dihydro-1h-inden-5-yl]oxy]propoxy]phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C(C=C1)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 RLDHAABFWXUBDC-SFHVURJKSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 102000018997 Growth Hormone Human genes 0.000 claims 1
- 108010051696 Growth Hormone Proteins 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 239000000883 anti-obesity agent Substances 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 claims 1
- 229940127088 antihypertensive drug Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 208000004104 gestational diabetes Diseases 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- 239000000122 growth hormone Substances 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 1
- 208000021822 hypotensive Diseases 0.000 claims 1
- 230000001077 hypotensive effect Effects 0.000 claims 1
- 230000003914 insulin secretion Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 208000028591 pheochromocytoma Diseases 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (3)
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| US43531002P | 2002-12-20 | 2002-12-20 | |
| US60/435,310 | 2002-12-20 | ||
| PCT/US2003/040842 WO2004058174A2 (en) | 2002-12-20 | 2003-12-19 | Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation |
Publications (3)
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| JP2006516251A JP2006516251A (ja) | 2006-06-29 |
| JP2006516251A5 true JP2006516251A5 (enExample) | 2007-02-15 |
| JP4974463B2 JP4974463B2 (ja) | 2012-07-11 |
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| JP2004563903A Expired - Fee Related JP4974463B2 (ja) | 2002-12-20 | 2003-12-19 | インダン酢酸誘導体ならびに製薬学的薬剤としてのそれらの使用、中間体及び製造方法 |
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| US (2) | US7714004B2 (enExample) |
| EP (1) | EP1578715B1 (enExample) |
| JP (1) | JP4974463B2 (enExample) |
| AU (1) | AU2003299790A1 (enExample) |
| CA (1) | CA2510793A1 (enExample) |
| DE (1) | DE60336264D1 (enExample) |
| WO (1) | WO2004058174A2 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101078098B1 (ko) | 2003-01-14 | 2011-10-28 | 아레나 파마슈티칼스, 인크. | 대사 조절제로서의 １,２,３-삼치환된 아릴 및 헤테로아릴유도체, 및 당뇨병 및 고혈당증을 비롯한 이에 관련된장애의 예방 및 치료 |
| DE602004002394T2 (de) * | 2003-04-17 | 2007-09-13 | Kalypsys, Inc., San Diego | (3-{3-'(2,4-bis-trifluormethyl-benzyl)-(5-ethyl-pyrimidin-2-yl)-amino]-propoxy}-phenyl)-essigsäure und verwandte verbindungen als modulatoren von ppars und verfahren zur behandlung von stoffwechselstörungen |
| EP1630152A4 (en) * | 2003-05-30 | 2009-09-23 | Takeda Pharmaceutical | CONDENSED CYCLIC COMPOUND |
| JP4805552B2 (ja) * | 2003-05-30 | 2011-11-02 | 武田薬品工業株式会社 | 縮合環化合物 |
| AR045697A1 (es) | 2003-07-14 | 2005-11-09 | Arena Pharm Inc | Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos relacionados con el mismo |
| KR20060109925A (ko) * | 2003-10-31 | 2006-10-23 | 얀센 파마슈티카 엔.브이. | 퍼옥시좀 증식체-활성화된 수용체(ｐｐａｒ) 이중작용제로서 유용한 페녹시아세트산 유도체 |
| CA2545048A1 (en) * | 2003-11-20 | 2005-06-02 | Warner-Lambert Company Llc | Androgen receptor modulators |
| US7622491B2 (en) * | 2004-08-13 | 2009-11-24 | Metabolex Inc. | Modulators of PPAR and methods of their preparation |
| MY148521A (en) | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| US20100130737A1 (en) * | 2005-02-18 | 2010-05-27 | Takeda Pharmaceutical Company Limited | Regulating Agent of GPR34 Receptor Function |
| EP1866293A1 (en) * | 2005-03-31 | 2007-12-19 | UCB Pharma, S.A. | Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses |
| US7816536B2 (en) * | 2005-06-10 | 2010-10-19 | The Research Foundation Of State University Of New York | 4-substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazoles, benzoxazoles, and benzothiazoles and methods for making same |
| JP4999923B2 (ja) | 2006-06-13 | 2012-08-15 | 中国科学院上海薬物研究所 | 複素環非ヌクレオシド系化合物、抗ウィルス医薬組成物、及びウィルス性疾病治療薬物 |
| TW200936130A (en) * | 2008-02-26 | 2009-09-01 | Lundbeck & Co As H | Uses of indane compounds |
| WO2010085525A1 (en) | 2009-01-23 | 2010-07-29 | Schering Corporation | Bridged and fused heterocyclic antidiabetic compounds |
| CA2749891A1 (en) | 2009-01-23 | 2010-07-29 | Hubert B. Josien | Bridged and fused antidiabetic compounds |
| WO2010091176A1 (en) | 2009-02-05 | 2010-08-12 | Schering Corporation | Phthalazine-containing antidiabetic compounds |
| WO2010141696A1 (en) * | 2009-06-04 | 2010-12-09 | Dara Biosciences, Inc. | Methods of treating or preventing psoriasis, and/or alzheimer's disease using indane acetic acid derivatives |
| JP2012188352A (ja) * | 2009-07-13 | 2012-10-04 | Dainippon Sumitomo Pharma Co Ltd | ３−（４−置換アルキル−フェニル）−２−フランカルボン酸誘導体およびその薬学的に許容される塩 |
| SG188548A1 (en) | 2010-09-22 | 2013-04-30 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2012074980A2 (en) * | 2010-12-01 | 2012-06-07 | Dara Biosciences, Inc. | Methods of treating or preventing autoimmune disorders and liver disorders using indane acetic acid derivatives |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| HUE060476T2 (hu) | 2015-06-22 | 2023-03-28 | Arena Pharm Inc | (R)-2-(7-(4-ciklopentil-3-(trifluormetil)benziloxi)-1,2,3,4- tetrahidrociklopenta[B]indol-3-il)ecetsav kristályos L-arginin-sója S1P1 receptorral kapcsolatos rendellenességek esetén való alkalmazásra |
| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| US12156866B2 (en) | 2018-06-06 | 2024-12-03 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| RS66416B1 (sr) * | 2019-01-18 | 2025-02-28 | Astrazeneca Ab | 6'-[[(1s,3s)-3-[[5-(difluorometoksi)-2-pirimidinil]amino]ciklopentil]amino][1(2h),3'-bipiridin]-2-on kao inhibitor pcsk9 i metode njegove primene |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6197241A (ja) * | 1984-10-16 | 1986-05-15 | Yamanouchi Pharmaceut Co Ltd | 新規カルボン酸誘導体 |
| CA1314224C (en) * | 1987-07-07 | 1993-03-09 | Shinichiro Ashida | Antidiabetic agent |
| AR036237A1 (es) | 2001-07-27 | 2004-08-25 | Bayer Corp | Derivados del acido indan acetico, intermediarios, y metodo para su preparacion, composicion farmaceutica y el uso de dichos derivados para la manufactura de un medicamento |
| UA79755C2 (en) | 2002-04-16 | 2007-07-25 | Bayer Pharmaceuticals Corp | Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation |
-
2003
- 2003-12-19 CA CA002510793A patent/CA2510793A1/en not_active Abandoned
- 2003-12-19 JP JP2004563903A patent/JP4974463B2/ja not_active Expired - Fee Related
- 2003-12-19 DE DE60336264T patent/DE60336264D1/de not_active Expired - Lifetime
- 2003-12-19 AU AU2003299790A patent/AU2003299790A1/en not_active Abandoned
- 2003-12-19 EP EP03800063A patent/EP1578715B1/en not_active Expired - Lifetime
- 2003-12-19 US US10/537,630 patent/US7714004B2/en not_active Expired - Fee Related
- 2003-12-19 WO PCT/US2003/040842 patent/WO2004058174A2/en not_active Ceased
-
2010
- 2010-04-13 US US12/759,328 patent/US7906653B2/en not_active Expired - Fee Related
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