JP2010513272A5 - - Google Patents
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- JP2010513272A5 JP2010513272A5 JP2009541322A JP2009541322A JP2010513272A5 JP 2010513272 A5 JP2010513272 A5 JP 2010513272A5 JP 2009541322 A JP2009541322 A JP 2009541322A JP 2009541322 A JP2009541322 A JP 2009541322A JP 2010513272 A5 JP2010513272 A5 JP 2010513272A5
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- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- halo
- group
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000000217 alkyl group Chemical group 0.000 claims 93
- 125000005843 halogen group Chemical group 0.000 claims 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 52
- 125000001153 fluoro group Chemical group F* 0.000 claims 40
- 239000000460 chlorine Substances 0.000 claims 22
- 229910052801 chlorine Inorganic materials 0.000 claims 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 229910052731 fluorine Inorganic materials 0.000 claims 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 11
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 9
- -1 benzopyrazinyl Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 150000003852 triazoles Chemical class 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 239000003112 inhibitor Substances 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
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 239000000556 agonist Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 2
- 102100039994 Gastric inhibitory polypeptide Human genes 0.000 claims 2
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 claims 2
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- 102000023984 PPAR alpha Human genes 0.000 claims 2
- 102000002808 Pituitary adenylate cyclase-activating polypeptide Human genes 0.000 claims 2
- 108010004684 Pituitary adenylate cyclase-activating polypeptide Proteins 0.000 claims 2
- 102100040918 Pro-glucagon Human genes 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 claims 2
- YERQPNCASYFOJZ-UHFFFAOYSA-N tert-butyl 4-[1-(4-methylsulfonylphenyl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)S(C)(=O)=O)CC1 YERQPNCASYFOJZ-UHFFFAOYSA-N 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- OUKJUVIGOPVKKG-UHFFFAOYSA-N 2-methylpropyl 4-[1-(4-methylsulfonylphenyl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC(C)C)CCC1C1CCN(C=2C=CC(=CC=2)S(C)(=O)=O)CC1 OUKJUVIGOPVKKG-UHFFFAOYSA-N 0.000 claims 1
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 claims 1
- YONFPTNGNZYQCW-UHFFFAOYSA-N 4-[4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]piperidin-1-yl]benzoic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)C(O)=O)CC1 YONFPTNGNZYQCW-UHFFFAOYSA-N 0.000 claims 1
- CBPFCGBLSOBBBG-UHFFFAOYSA-N 4-methyl-1-[4-[1-(4-methylsulfonylphenyl)piperidin-4-yl]piperidin-1-yl]pentane-1,2-dione Chemical compound C1CN(C(=O)C(=O)CC(C)C)CCC1C1CCN(C=2C=CC(=CC=2)S(C)(=O)=O)CC1 CBPFCGBLSOBBBG-UHFFFAOYSA-N 0.000 claims 1
- HRMQJFSNGDUFSY-UHFFFAOYSA-N 5-fluoro-2-methyl-4-[4-(1-pyrimidin-2-ylpiperidin-4-yl)piperidin-1-yl]pyrimidine Chemical compound CC1=NC=C(F)C(N2CCC(CC2)C2CCN(CC2)C=2N=CC=CN=2)=N1 HRMQJFSNGDUFSY-UHFFFAOYSA-N 0.000 claims 1
- YHAAUXAGUYRMQS-UHFFFAOYSA-N 5-fluoro-4-[4-[1-(5-fluoropyrimidin-2-yl)piperidin-4-yl]piperidin-1-yl]-2-methylpyrimidine Chemical compound CC1=NC=C(F)C(N2CCC(CC2)C2CCN(CC2)C=2N=CC(F)=CN=2)=N1 YHAAUXAGUYRMQS-UHFFFAOYSA-N 0.000 claims 1
- IGPOYFLMHPMDHS-UHFFFAOYSA-N 6-[4-(1-pyrimidin-2-ylpiperidin-4-yl)piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound C1=NC(C#N)=CC(N2CCC(CC2)C2CCN(CC2)C=2N=CC=CN=2)=N1 IGPOYFLMHPMDHS-UHFFFAOYSA-N 0.000 claims 1
- SMZJLTZXLFJERT-UHFFFAOYSA-N 6-[4-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound N1=CC(Cl)=CN=C1N1CCC(C2CCN(CC2)C=2N=CN=C(C=2)C#N)CC1 SMZJLTZXLFJERT-UHFFFAOYSA-N 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002083 C09CA01 - Losartan Substances 0.000 claims 1
- 239000002080 C09CA02 - Eprosartan Substances 0.000 claims 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 claims 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 claims 1
- 239000002081 C09CA05 - Tasosartan Substances 0.000 claims 1
- 239000002053 C09CA06 - Candesartan Substances 0.000 claims 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 claims 1
- 108010061435 Enalapril Proteins 0.000 claims 1
- 229940122904 Glucagon receptor antagonist Drugs 0.000 claims 1
- 229940089838 Glucagon-like peptide 1 receptor agonist Drugs 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 229940122199 Insulin secretagogue Drugs 0.000 claims 1
- 229940122355 Insulin sensitizer Drugs 0.000 claims 1
- 108010007859 Lisinopril Proteins 0.000 claims 1
- 229940126033 PPAR agonist Drugs 0.000 claims 1
- 229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 claims 1
- 102000014743 Pituitary Adenylate Cyclase-Activating Polypeptide Receptors Human genes 0.000 claims 1
- 108010064032 Pituitary Adenylate Cyclase-Activating Polypeptide Receptors Proteins 0.000 claims 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 claims 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000002404 acyltransferase inhibitor Substances 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 239000003529 anticholesteremic agent Substances 0.000 claims 1
- 229940127226 anticholesterol agent Drugs 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229960000932 candesartan Drugs 0.000 claims 1
- SGZAIDDFHDDFJU-UHFFFAOYSA-N candesartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SGZAIDDFHDDFJU-UHFFFAOYSA-N 0.000 claims 1
- 229960000830 captopril Drugs 0.000 claims 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims 1
- 230000001906 cholesterol absorption Effects 0.000 claims 1
- 229960005025 cilazapril Drugs 0.000 claims 1
- HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 claims 1
- 229950006523 cilexetil Drugs 0.000 claims 1
- VTDCYOLLYVAJSY-UHFFFAOYSA-N cyclohexyl propan-2-yl carbonate Chemical compound CC(C)OC(=O)OC1CCCCC1 VTDCYOLLYVAJSY-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940125542 dual agonist Drugs 0.000 claims 1
- 229960000873 enalapril Drugs 0.000 claims 1
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 claims 1
- 229960004563 eprosartan Drugs 0.000 claims 1
- OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 claims 1
- 229960002490 fosinopril Drugs 0.000 claims 1
- 108010036598 gastric inhibitory polypeptide receptor Proteins 0.000 claims 1
- 239000003877 glucagon like peptide 1 receptor agonist Substances 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 229940121380 ileal bile acid transporter inhibitor Drugs 0.000 claims 1
- 229960002198 irbesartan Drugs 0.000 claims 1
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 claims 1
- 229960002394 lisinopril Drugs 0.000 claims 1
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 claims 1
- 229960004773 losartan Drugs 0.000 claims 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 229960004738 nicotinyl alcohol Drugs 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 1
- 229960001455 quinapril Drugs 0.000 claims 1
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 claims 1
- 229960003401 ramipril Drugs 0.000 claims 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 claims 1
- 229940044601 receptor agonist Drugs 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 1
- 229960000651 tasosartan Drugs 0.000 claims 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 claims 1
- 229960005187 telmisartan Drugs 0.000 claims 1
- PPFBJVUEGARPHQ-UHFFFAOYSA-N tert-butyl 4-(1-pyrimidin-4-ylpiperidin-4-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=CN=CC=2)CC1 PPFBJVUEGARPHQ-UHFFFAOYSA-N 0.000 claims 1
- OCZPWTVYEVYGAU-UHFFFAOYSA-N tert-butyl 4-[1-(3-chloro-1,2,4-thiadiazol-5-yl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2SN=C(Cl)N=2)CC1 OCZPWTVYEVYGAU-UHFFFAOYSA-N 0.000 claims 1
- WQRJQIVAIVUPIZ-UHFFFAOYSA-N tert-butyl 4-[1-(4-carbamoylphenyl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)C(N)=O)CC1 WQRJQIVAIVUPIZ-UHFFFAOYSA-N 0.000 claims 1
- RFKUSFSXEGGYQA-UHFFFAOYSA-N tert-butyl 4-[1-(4-cyanophenyl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)C#N)CC1 RFKUSFSXEGGYQA-UHFFFAOYSA-N 0.000 claims 1
- JDQGBFFBIJVSEA-UHFFFAOYSA-N tert-butyl 4-[1-(4-methoxycarbonylphenyl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1N1CCC(C2CCN(CC2)C(=O)OC(C)(C)C)CC1 JDQGBFFBIJVSEA-UHFFFAOYSA-N 0.000 claims 1
- PQSOMXBPDSHUJE-UHFFFAOYSA-N tert-butyl 4-[1-(4-methylsulfanylphenyl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1=CC(SC)=CC=C1N1CCC(C2CCN(CC2)C(=O)OC(C)(C)C)CC1 PQSOMXBPDSHUJE-UHFFFAOYSA-N 0.000 claims 1
- WGIPWFWDEXLPAV-UHFFFAOYSA-N tert-butyl 4-[1-(4-methylsulfinylphenyl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1=CC(S(=O)C)=CC=C1N1CCC(C2CCN(CC2)C(=O)OC(C)(C)C)CC1 WGIPWFWDEXLPAV-UHFFFAOYSA-N 0.000 claims 1
- VUNYEFFEVPDCTL-UHFFFAOYSA-N tert-butyl 4-[1-(5-bromopyrazin-2-yl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=CC(Br)=NC=2)CC1 VUNYEFFEVPDCTL-UHFFFAOYSA-N 0.000 claims 1
- IHQVNLNQOCIRPT-UHFFFAOYSA-N tert-butyl 4-[1-(5-chloropyrazin-2-yl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=CC(Cl)=NC=2)CC1 IHQVNLNQOCIRPT-UHFFFAOYSA-N 0.000 claims 1
- MNYIVYPOMBLYDE-UHFFFAOYSA-N tert-butyl 4-[1-(5-fluoro-2-methoxypyrimidin-4-yl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound COC1=NC=C(F)C(N2CCC(CC2)C2CCN(CC2)C(=O)OC(C)(C)C)=N1 MNYIVYPOMBLYDE-UHFFFAOYSA-N 0.000 claims 1
- IUTKEXNDCBCKKW-UHFFFAOYSA-N tert-butyl 4-[1-(6-chloropyrazin-2-yl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=C(Cl)C=NC=2)CC1 IUTKEXNDCBCKKW-UHFFFAOYSA-N 0.000 claims 1
- UGVSURZVGPJZKR-UHFFFAOYSA-N tert-butyl 4-[1-(6-cyanopyrazin-2-yl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=C(C=NC=2)C#N)CC1 UGVSURZVGPJZKR-UHFFFAOYSA-N 0.000 claims 1
- OEHSOQBBWXZTSY-UHFFFAOYSA-N tert-butyl 4-[1-(6-methylsulfonylpyrimidin-4-yl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=CN=C(C=2)S(C)(=O)=O)CC1 OEHSOQBBWXZTSY-UHFFFAOYSA-N 0.000 claims 1
- OGQOIAWKPHIPJU-UHFFFAOYSA-N tert-butyl 4-[1-(6-phenylmethoxypyrimidin-4-yl)piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=CN=C(OCC=3C=CC=CC=3)C=2)CC1 OGQOIAWKPHIPJU-UHFFFAOYSA-N 0.000 claims 1
- CSHVQUUDLOXMNC-UHFFFAOYSA-N tert-butyl 4-[1-[2-(trifluoromethyl)pyrimidin-4-yl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=C(N=CC=2)C(F)(F)F)CC1 CSHVQUUDLOXMNC-UHFFFAOYSA-N 0.000 claims 1
- MIVJAHUWKWJUPB-UHFFFAOYSA-N tert-butyl 4-[1-[3-(dimethylamino)-1,2,4-thiadiazol-5-yl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound CN(C)C1=NSC(N2CCC(CC2)C2CCN(CC2)C(=O)OC(C)(C)C)=N1 MIVJAHUWKWJUPB-UHFFFAOYSA-N 0.000 claims 1
- ULHGRYYDJZNACS-UHFFFAOYSA-N tert-butyl 4-[1-[3-chloro-4-(1,3-thiazole-4-carbonylamino)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=C(Cl)C(NC(=O)C=3N=CSC=3)=CC=2)CC1 ULHGRYYDJZNACS-UHFFFAOYSA-N 0.000 claims 1
- FYSHHBLCJJMPRE-UHFFFAOYSA-N tert-butyl 4-[1-[4-(1,2,4-thiadiazol-5-ylcarbamoyl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)C(=O)NC=2SN=CN=2)CC1 FYSHHBLCJJMPRE-UHFFFAOYSA-N 0.000 claims 1
- OCIBPECTLYPZSF-UHFFFAOYSA-N tert-butyl 4-[1-[4-(1,2,4-triazol-1-yl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)N2N=CN=C2)CC1 OCIBPECTLYPZSF-UHFFFAOYSA-N 0.000 claims 1
- GZBNEPYALVYMCR-UHFFFAOYSA-N tert-butyl 4-[1-[4-(1,3-oxazol-2-yl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)C=2OC=CN=2)CC1 GZBNEPYALVYMCR-UHFFFAOYSA-N 0.000 claims 1
- MVFVBZJDIVTFJP-UHFFFAOYSA-N tert-butyl 4-[1-[4-(1,3-thiazol-2-yl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)C=2SC=CN=2)CC1 MVFVBZJDIVTFJP-UHFFFAOYSA-N 0.000 claims 1
- XUDZLEBGBXWFHS-UHFFFAOYSA-N tert-butyl 4-[1-[4-(1,3-thiazole-2-carbonylamino)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(NC(=O)C=3SC=CN=3)=CC=2)CC1 XUDZLEBGBXWFHS-UHFFFAOYSA-N 0.000 claims 1
- WNCHOIOJVDZJRA-UHFFFAOYSA-N tert-butyl 4-[1-[4-(1,3-thiazole-4-carbonylamino)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(NC(=O)C=3N=CSC=3)=CC=2)CC1 WNCHOIOJVDZJRA-UHFFFAOYSA-N 0.000 claims 1
- ITWIYDCRMLYAJX-UHFFFAOYSA-N tert-butyl 4-[1-[4-(2-amino-2-oxoethyl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(CC(N)=O)=CC=2)CC1 ITWIYDCRMLYAJX-UHFFFAOYSA-N 0.000 claims 1
- XTGLERXCHHHNDC-UHFFFAOYSA-N tert-butyl 4-[1-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)C=2OCCN=2)CC1 XTGLERXCHHHNDC-UHFFFAOYSA-N 0.000 claims 1
- ALJVEYZNSSJEEH-UHFFFAOYSA-N tert-butyl 4-[1-[4-(hydroxymethyl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(CO)=CC=2)CC1 ALJVEYZNSSJEEH-UHFFFAOYSA-N 0.000 claims 1
- LCFAVUNISIHQKR-UHFFFAOYSA-N tert-butyl 4-[1-[4-(methylsulfonylmethyl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(CS(C)(=O)=O)=CC=2)CC1 LCFAVUNISIHQKR-UHFFFAOYSA-N 0.000 claims 1
- RIGZOBFNMFLCMF-UHFFFAOYSA-N tert-butyl 4-[1-[4-(trifluoromethylsulfonyl)phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(=CC=2)S(=O)(=O)C(F)(F)F)CC1 RIGZOBFNMFLCMF-UHFFFAOYSA-N 0.000 claims 1
- MEDMEAXHXQPAMO-UHFFFAOYSA-N tert-butyl 4-[1-[4-[2-(1,3-thiazol-2-yl)ethyl]phenyl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2C=CC(CCC=3SC=CN=3)=CC=2)CC1 MEDMEAXHXQPAMO-UHFFFAOYSA-N 0.000 claims 1
- HTAFQIUGLLIWJE-UHFFFAOYSA-N tert-butyl 4-[1-[6-(1,2,4-triazol-1-yl)pyrimidin-4-yl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1CCN(C=2N=CN=C(C=2)N2N=CN=C2)CC1 HTAFQIUGLLIWJE-UHFFFAOYSA-N 0.000 claims 1
- ZFDMIBGFJJYIGT-UHFFFAOYSA-N tert-butyl 4-[1-[6-(methylamino)pyrimidin-4-yl]piperidin-4-yl]piperidine-1-carboxylate Chemical compound C1=NC(NC)=CC(N2CCC(CC2)C2CCN(CC2)C(=O)OC(C)(C)C)=N1 ZFDMIBGFJJYIGT-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 229960004699 valsartan Drugs 0.000 claims 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 claims 1
- 229960002769 zofenopril Drugs 0.000 claims 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 claims 1
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| US87490706P | 2006-12-14 | 2006-12-14 | |
| PCT/US2007/025225 WO2008076243A2 (en) | 2006-12-14 | 2007-12-10 | Acyl bipiperidinyl compounds, compositions containing such compounds and methods of treatment |
Publications (2)
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| JP2010513272A JP2010513272A (ja) | 2010-04-30 |
| JP2010513272A5 true JP2010513272A5 (OSRAM) | 2010-11-18 |
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| EP (1) | EP2112880A4 (OSRAM) |
| JP (1) | JP2010513272A (OSRAM) |
| AU (1) | AU2007334519A1 (OSRAM) |
| CA (1) | CA2672059A1 (OSRAM) |
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| HRP20050696B1 (en) | 2003-01-14 | 2008-10-31 | Arena Pharmaceuticals Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prpphylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| AR045047A1 (es) * | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| DOP2006000008A (es) * | 2005-01-10 | 2006-08-31 | Arena Pharm Inc | Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP2146210A1 (en) | 2008-04-07 | 2010-01-20 | Arena Pharmaceuticals, Inc. | Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditions modulated by PYY |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| JP2013522279A (ja) | 2010-03-18 | 2013-06-13 | 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 | 糖尿病及び関連状態の治療で用いるｇｐｒ１１９作動薬とｄｄｐ−ｉｖ阻害薬リナグリプチンの組合せ |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| MX2013003184A (es) | 2010-09-22 | 2013-06-07 | Arena Pharm Inc | Moduladores del receptor gpr119 y el tratamiento de transtornos relacionados con el mismo. |
| PL2625177T3 (pl) | 2010-10-08 | 2015-12-31 | Cadila Healthcare Ltd | Nowi agoniści GPR 119 |
| WO2012145361A1 (en) * | 2011-04-19 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| AU2012267556B9 (en) | 2011-06-09 | 2017-05-11 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of GPR-119 |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US11007175B2 (en) | 2015-01-06 | 2021-05-18 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| AU2016324598A1 (en) | 2015-09-17 | 2018-03-15 | Marvin J. Miller | Benzyl amine-containing heterocyclic compounds and compositions useful against mycobacterial infection |
| EP3373933B1 (en) * | 2015-11-12 | 2020-08-26 | Merck Sharp & Dohme Corp. | Bispiperidinyl derivatives as liver x receptor beta agonists, compositions, and their use |
| WO2018068296A1 (en) * | 2016-10-14 | 2018-04-19 | Merck Sharp & Dohme Corp. | PIPERIDINE DERIVATIVES AS LIVER X RECEPTOR β AGONISTS, COMPOSITIONS, AND THEIR USE |
| WO2018068297A1 (en) * | 2016-10-14 | 2018-04-19 | Merck Sharp & Dohme Corp. | N-ARYL AND N-HETEROARYL PIPERIDINE DERIVATIVES AS LIVER X RECEPTOR β AGONISTS, COMPOSITIONS, AND THEIR USE |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
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| US5242924A (en) | 1992-07-02 | 1993-09-07 | Sterling Winthrop Inc. | Tetrazolyl-(phenoxy and phenoxyalkyl)-piperidinylpyridazines as antiviral agents |
| US5364865A (en) * | 1992-12-30 | 1994-11-15 | Sterling Winthrop Inc. | Phenoxy- and phenoxyalkyl-piperidines as antiviral agents |
| AR012443A1 (es) * | 1997-04-16 | 2000-10-18 | Uriach & Cia Sa J | Nuevas carboxamidas como inhibidores de la agregacion plaquetaria, procedimiento para su preparacion, composiciones farmaceuticas que loscontienen y uso de los mismos en la manufactura de medicamentos |
| AR013693A1 (es) | 1997-10-23 | 2001-01-10 | Uriach & Cia Sa J | Nuevas piperidinas y piperazinas como inhibidores de la agregacion plaquetaria |
| KR20010102000A (ko) * | 1999-02-08 | 2001-11-15 | 윌리암스 로저 에이 | 술파마토 히드록삼산 메탈로프로테아제 억제제 |
| US6800646B1 (en) * | 1999-02-08 | 2004-10-05 | Pharmacia Corporation | Sulfamato hydroxamic acid metalloprotease inhibitor |
| US6498161B1 (en) * | 1999-04-06 | 2002-12-24 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
| AUPR213700A0 (en) | 2000-12-18 | 2001-01-25 | Biota Scientific Management Pty Ltd | Antiviral agents |
| AU2003225027A1 (en) * | 2002-04-16 | 2003-11-03 | Merck And Co., Inc. | Combination therapy using a ppar alpha/gamma agonist |
| HRP20050696B1 (en) | 2003-01-14 | 2008-10-31 | Arena Pharmaceuticals Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prpphylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| ES2316964T3 (es) | 2003-02-24 | 2009-04-16 | Arena Pharmaceuticals, Inc. | Fenil-y piridilpipereidinia-derivados como moduladores del metabolismo de la glucosa. |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| NZ547965A (en) | 2003-12-24 | 2009-12-24 | Prosidion Ltd | 1,2,4-Oxadiazole derivatives as GPCR receptor agonists |
| TW200610761A (en) * | 2004-04-23 | 2006-04-01 | Astrazeneca Ab | Chemical compounds |
| JP2008508314A (ja) | 2004-07-28 | 2008-03-21 | アイアールエム・リミテッド・ライアビリティ・カンパニー | ステロイドホルモン核内受容体のモジュレーターとしての化合物および組成物 |
| GB0419160D0 (en) * | 2004-08-27 | 2004-09-29 | Novartis Ag | Organic compounds |
| US8193359B2 (en) | 2004-12-24 | 2012-06-05 | Prosidion Limited | G-protein coupled receptor agonists |
| MX2007007553A (es) | 2004-12-24 | 2007-08-15 | Prosidion Ltd | Agonistas del receptor acoplado a proteina g (gpr116) y uso de los mismos para tratar obesidad y diabetes. |
| GB0428514D0 (en) | 2004-12-31 | 2005-02-09 | Prosidion Ltd | Compounds |
| DOP2006000008A (es) * | 2005-01-10 | 2006-08-31 | Arena Pharm Inc | Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1 |
-
2007
- 2007-12-10 EP EP07862712A patent/EP2112880A4/en not_active Withdrawn
- 2007-12-10 AU AU2007334519A patent/AU2007334519A1/en not_active Abandoned
- 2007-12-10 JP JP2009541322A patent/JP2010513272A/ja not_active Withdrawn
- 2007-12-10 WO PCT/US2007/025225 patent/WO2008076243A2/en not_active Ceased
- 2007-12-10 US US12/517,142 patent/US8399485B2/en not_active Expired - Fee Related
- 2007-12-10 CA CA002672059A patent/CA2672059A1/en not_active Abandoned
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