ES2388967T3 - Agonistas [6,6]- y [6,7]-bicíclicos del receptor GPR119 acoplado a la proteína G - Google Patents
Agonistas [6,6]- y [6,7]-bicíclicos del receptor GPR119 acoplado a la proteína G Download PDFInfo
- Publication number
- ES2388967T3 ES2388967T3 ES08747129T ES08747129T ES2388967T3 ES 2388967 T3 ES2388967 T3 ES 2388967T3 ES 08747129 T ES08747129 T ES 08747129T ES 08747129 T ES08747129 T ES 08747129T ES 2388967 T3 ES2388967 T3 ES 2388967T3
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- ES
- Spain
- Prior art keywords
- aryl
- alkyl
- heteroaryl
- cycloalkyl
- nr9r9
- Prior art date
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- 101000996752 Homo sapiens Glucose-dependent insulinotropic receptor Proteins 0.000 title description 30
- 102100033839 Glucose-dependent insulinotropic receptor Human genes 0.000 title description 29
- 239000000556 agonist Substances 0.000 title description 18
- 108091006027 G proteins Proteins 0.000 title description 10
- 102000030782 GTP binding Human genes 0.000 title description 10
- 108091000058 GTP-Binding Proteins 0.000 title description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 198
- 150000001875 compounds Chemical class 0.000 claims abstract description 191
- 125000003118 aryl group Chemical group 0.000 claims abstract description 143
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 135
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 94
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 93
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 75
- 239000001257 hydrogen Substances 0.000 claims abstract description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 66
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 65
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 49
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 48
- 125000001424 substituent group Chemical group 0.000 claims abstract description 44
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 42
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 33
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 30
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 17
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 4
- -1 aryl-arylalkyl Chemical group 0.000 claims description 236
- 238000000034 method Methods 0.000 claims description 158
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 119
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 76
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 75
- 125000005843 halogen group Chemical group 0.000 claims description 70
- 238000011282 treatment Methods 0.000 claims description 57
- 206010012601 diabetes mellitus Diseases 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 27
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- 230000002265 prevention Effects 0.000 claims description 19
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- 125000004076 pyridyl group Chemical group 0.000 claims description 13
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- 125000004429 atom Chemical group 0.000 claims description 11
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 10
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- 201000001421 hyperglycemia Diseases 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000003877 glucagon like peptide 1 receptor agonist Substances 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 208000028698 Cognitive impairment Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical group C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- 229940089838 Glucagon-like peptide 1 receptor agonist Drugs 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 24
- 239000013543 active substance Substances 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 1
- 125000005325 aryloxy aryl group Chemical group 0.000 claims 1
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 266
- 238000005160 1H NMR spectroscopy Methods 0.000 description 133
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 105
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 80
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 56
- 239000011541 reaction mixture Substances 0.000 description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
- 235000019439 ethyl acetate Nutrition 0.000 description 52
- 239000000203 mixture Substances 0.000 description 42
- UGUIBNHHDIEZJI-UHFFFAOYSA-N 2-fluoro-4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C(F)=C1 UGUIBNHHDIEZJI-UHFFFAOYSA-N 0.000 description 40
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000007787 solid Substances 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
- 239000002904 solvent Substances 0.000 description 38
- 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 description 37
- 239000002585 base Substances 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 29
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 238000003818 flash chromatography Methods 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 21
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- 235000019341 magnesium sulphate Nutrition 0.000 description 20
- 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 description 19
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91594407P | 2007-05-04 | 2007-05-04 | |
| US915944P | 2007-05-04 | ||
| PCT/US2008/061928 WO2008137435A1 (en) | 2007-05-04 | 2008-04-30 | [6,6] and [6,7]-bicyclic gpr119 g protein-coupled receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2388967T3 true ES2388967T3 (es) | 2012-10-22 |
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| Application Number | Title | Priority Date | Filing Date |
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| ES08747129T Active ES2388967T3 (es) | 2007-05-04 | 2008-04-30 | Agonistas [6,6]- y [6,7]-bicíclicos del receptor GPR119 acoplado a la proteína G |
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| Country | Link |
|---|---|
| US (4) | US7910583B2 (enExample) |
| EP (1) | EP2144902B1 (enExample) |
| JP (1) | JP2010526145A (enExample) |
| CN (1) | CN101668756A (enExample) |
| AR (1) | AR066437A1 (enExample) |
| CL (1) | CL2008001271A1 (enExample) |
| ES (1) | ES2388967T3 (enExample) |
| PE (1) | PE20090222A1 (enExample) |
| TW (1) | TW200848055A (enExample) |
| WO (1) | WO2008137435A1 (enExample) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| BRPI0711558A2 (pt) | 2006-05-04 | 2011-11-08 | Boeringer Ingelheim Internat Gmbh | polimorfos |
| PL2170864T3 (pl) * | 2007-07-17 | 2012-02-29 | Bristol Myers Squibb Co | Agoniści receptora gpr119 sprężonego z białkiem g - pirydon |
| PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| US8188098B2 (en) | 2008-05-19 | 2012-05-29 | Hoffmann-La Roche Inc. | GPR119 receptor agonists |
| MX2011000664A (es) | 2008-07-16 | 2011-02-24 | Schering Corp | Derivados biciclicos heterociclicos y uso de los mismos como moduladores de gpr119. |
| TW201006821A (en) * | 2008-07-16 | 2010-02-16 | Bristol Myers Squibb Co | Pyridone and pyridazone analogues as GPR119 modulators |
| JP2011528368A (ja) * | 2008-07-16 | 2011-11-17 | シェーリング コーポレイション | 二環式ヘテロ環誘導体およびｇｐｃｒモジュレーターとしてのその使用 |
| JP2011528369A (ja) * | 2008-07-16 | 2011-11-17 | シェーリング コーポレイション | 二環式ヘテロ環誘導体およびそれらの使用方法 |
| BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| WO2010075273A1 (en) * | 2008-12-23 | 2010-07-01 | Schering Corporation | Bicyclic heterocycle derivatives and methods of use thereof |
| EP2382216A1 (en) | 2008-12-23 | 2011-11-02 | Boehringer Ingelheim International GmbH | Salt forms of organic compound |
| EP2390254A1 (en) * | 2009-01-22 | 2011-11-30 | Mitsubishi Tanabe Pharma Corporation | NOVEL PYRROLOÝ2,3-d¨PYRIMIDINE COMPOUND |
| WO2010088518A2 (en) * | 2009-01-31 | 2010-08-05 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| JP5657518B2 (ja) | 2009-02-18 | 2015-01-21 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| EP2414348B1 (en) | 2009-04-03 | 2013-11-20 | Merck Sharp & Dohme Corp. | Bicyclic piperidine and piperazine derivatives as gpcr modulators for the treatment of obesity, diabetes and other metabolic disorders |
| US8293729B2 (en) | 2009-06-24 | 2012-10-23 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical composition and methods relating thereto |
| US8481731B2 (en) | 2009-06-24 | 2013-07-09 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical composition and methods relating thereto |
| EA034869B1 (ru) | 2009-11-27 | 2020-03-31 | Бёрингер Ингельхайм Интернациональ Гмбх | Лечение генотипированных пациентов с диабетом ингибиторами дпп-4, такими как линаглиптин |
| 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 |
| US8415367B2 (en) | 2010-04-08 | 2013-04-09 | Bristol-Myers Squibb Company | Pyrimidinylpiperidinyloxypyridinone analogues as GPR119 modulators |
| MX341025B (es) | 2010-05-05 | 2016-08-04 | Boehringer Ingelheim Int Gmbh * | Terapia de combinacion. |
| EP2566862B1 (en) | 2010-05-06 | 2015-09-16 | Bristol-Myers Squibb Company | Benzofuranyl analogues as gpr119 modulators |
| CN102971311B (zh) | 2010-05-06 | 2015-07-08 | 百时美施贵宝公司 | 作为gpr119调节剂的二环杂芳基化合物 |
| TW201202230A (en) * | 2010-05-24 | 2012-01-16 | Mitsubishi Tanabe Pharma Corp | Novel quinazoline compound |
| 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 |
| PH12012502524A1 (en) | 2010-06-24 | 2014-02-10 | Boehringer Ingelheim Int | Diabetes therapy |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| 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 |
| CN103221410B (zh) | 2010-09-22 | 2017-09-15 | 艾尼纳制药公司 | Gpr119受体调节剂和对与其相关的障碍的治疗 |
| JP2013253019A (ja) * | 2010-09-28 | 2013-12-19 | Kowa Co | 新規なピペリジン誘導体及びこれを含有する医薬 |
| US9034883B2 (en) | 2010-11-15 | 2015-05-19 | Boehringer Ingelheim International Gmbh | Vasoprotective and cardioprotective antidiabetic therapy |
| UY33805A (es) * | 2010-12-17 | 2012-07-31 | Boehringer Ingelheim Int | ?Derivados de dihidrobenzofuranil-piperidinilo, aza-dihidrobenzofuranilpiperidinilo y diaza-dihidrobenzofuranil-piperidinilo, composiciones farmacéuticas que los contienen y usos de los mismos?. |
| KR20120079015A (ko) | 2011-01-03 | 2012-07-11 | 한미약품 주식회사 | Ｇ 단백질-커플링된 수용체의 조절을 위한 신규한 비사이클릭 화합물 |
| CN102617548A (zh) * | 2011-01-31 | 2012-08-01 | 北京赛林泰医药技术有限公司 | 作为gpr受体激动剂的双环杂芳基化合物及其组合物和应用 |
| KR101913619B1 (ko) | 2011-06-09 | 2018-12-28 | 리젠 파마슈티컬스 소시에떼 아노님 | Gpr-119의 조절제로서의 신규한 화합물 |
| EP3517539B1 (en) | 2011-07-15 | 2022-12-14 | Boehringer Ingelheim International GmbH | Substituted dimeric quinazoline derivative, its preparation and its use in pharmaceutical compositions for the treatment of type i and ii diabetes |
| 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 |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| JP6224084B2 (ja) | 2012-05-14 | 2017-11-01 | 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 | 糸球体上皮細胞関連障害及び／又はネフローゼ症候群の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体 |
| US20130303554A1 (en) | 2012-05-14 | 2013-11-14 | Boehringer Ingelheim International Gmbh | Use of a dpp-4 inhibitor in sirs and/or sepsis |
| US9174965B2 (en) | 2012-05-16 | 2015-11-03 | Bristol-Myers Squibb Company | Pyrimidinylpiperidinyloxypyridone analogues as GPR119 modulators |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| AU2013290100A1 (en) | 2012-07-11 | 2015-01-29 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| US9526728B2 (en) | 2014-02-28 | 2016-12-27 | Boehringer Ingelheim International Gmbh | Medical use of a DPP-4 inhibitor |
| EP3149879B1 (en) * | 2014-06-02 | 2018-05-23 | Marvell World Trade Ltd. | High efficiency orthogonal frequency division multiplexing (ofdm) physical layer (phy) |
| CN105218561B (zh) * | 2014-06-25 | 2018-10-30 | 上海艾力斯医药科技有限公司 | 稠合嘧啶环衍生物、其制备方法及应用 |
| CA3002540C (en) | 2015-01-06 | 2023-11-07 | Arena Pharmaceuticals, Inc. | Use of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid for treating conditions related to the s1p1 receptor |
| JP6838744B2 (ja) | 2015-06-22 | 2021-03-03 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｓ１Ｐ１レセプター関連障害における使用のための（Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸（化合物１）の結晶性Ｌ−アルギニン塩 |
| CN109310697A (zh) | 2016-06-10 | 2019-02-05 | 勃林格殷格翰国际有限公司 | 利格列汀和二甲双胍的组合 |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| JP7397011B2 (ja) | 2018-06-06 | 2023-12-12 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｓ１ｐ１受容体に関連する状態を治療する方法 |
| MX2022010548A (es) | 2020-02-28 | 2022-09-23 | Kallyope Inc | Agonistas de gpr40. |
| MX2022014505A (es) | 2020-05-19 | 2022-12-13 | Kallyope Inc | Activadores de la ampk. |
| CA3183575A1 (en) | 2020-06-26 | 2021-12-30 | Iyassu Sebhat | Ampk activators |
| WO2023178130A1 (en) * | 2022-03-16 | 2023-09-21 | Biotheryx, Inc. | Sos1 protein degraders, pharmaceutical compositions, and therapeutic applications |
| CN114969044B (zh) * | 2022-05-30 | 2024-10-11 | 北京火山引擎科技有限公司 | 一种基于数据湖的物化列创建方法以及数据查询方法 |
| CN115160340B (zh) * | 2022-06-07 | 2023-07-21 | 四川大学华西医院 | 一种具有ack1抑制活性的小分子化合物及其应用 |
| AU2025220986A1 (en) * | 2024-02-17 | 2026-08-13 | Padarn Therapeutics, Inc. | Inhibitors of cdk2 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3826643A (en) | 1967-08-07 | 1974-07-30 | American Cyanamid Co | Method of controlling undesirable plant species using 3-nitropyridines |
| US5776983A (en) | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5488064A (en) | 1994-05-02 | 1996-01-30 | Bristol-Myers Squibb Company | Benzo 1,3 dioxole derivatives |
| US5612359A (en) | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
| US5491134A (en) | 1994-09-16 | 1996-02-13 | Bristol-Myers Squibb Company | Sulfonic, phosphonic or phosphiniic acid β3 agonist derivatives |
| US5541204A (en) | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| US5620997A (en) | 1995-05-31 | 1997-04-15 | Warner-Lambert Company | Isothiazolones |
| WO1997012613A1 (en) | 1995-10-05 | 1997-04-10 | Warner-Lambert Company | Method for treating and preventing inflammation and atherosclerosis |
| US5770615A (en) | 1996-04-04 | 1998-06-23 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US6566384B1 (en) | 1996-08-07 | 2003-05-20 | Darwin Discovery Ltd. | Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity |
| TW536540B (en) | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| UA57811C2 (uk) | 1997-11-21 | 2003-07-15 | Пфайзер Продактс Інк. | Фармацевтична композиція, що містить інгібітор альдозоредуктази та інгібітор глікогенфосфорилази (варіанти), комплект, який її включає, та способи лікування ссавців зі станом інсулінорезистентності |
| ID26984A (id) | 1998-07-06 | 2001-02-22 | Bristol Myers Squibb Co | Senyawa-senyawa sulfonamida sebagai antagonis reseptor angiotensin endotelin ganda |
| WO2000038683A1 (en) | 1998-12-23 | 2000-07-06 | Du Pont Pharmaceuticals Company | THROMBIN OR FACTOR Xa INHIBITORS |
| US6586418B2 (en) | 2000-06-29 | 2003-07-01 | Bristol-Myers Squibb Company | Thrombin or factor Xa inhibitors |
| EP1770159A1 (en) | 2000-12-01 | 2007-04-04 | Astellas Pharma Inc. | Process for manufacturing a pharmaceutical composition for treating diabetes |
| US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| US7998986B2 (en) | 2001-12-21 | 2011-08-16 | Exelixis Patent Company Llc | Modulators of LXR |
| RS20050532A (sr) | 2003-01-14 | 2007-12-31 | Arena Pharmaceuticals Inc., | Derivati 1,2,3-trisupstituisanog arila i heteroarila kao modulatori metabolizma za profilaksu i tretman poremećaja povezanih sa njim, kao što su dijebetes i hiperglikemija |
| DE602004017703D1 (de) | 2003-02-24 | 2008-12-24 | Arena Pharm Inc | Phenyl- und pyridylpiperidinderivate als modulatoren des glucose-metabolismus |
| SE0301010D0 (sv) | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| 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 |
| KR20060056944A (ko) | 2003-07-14 | 2006-05-25 | 아레나 파마슈티칼스, 인크. | 대사 조절제로서 융합된 아릴 및 헤테로아릴 유도체 및이에 관련된 장애의 예방 또는 치료 |
| US20070088163A1 (en) | 2003-09-12 | 2007-04-19 | Kemia, Inc. | Modulators of calcitonin and amylin activity |
| DK2060266T3 (da) | 2004-03-17 | 2011-11-14 | 7Tm Pharma As | Y4-selektiv receptoragonist PP2-36 til terapeutiske indgreb |
| MXPA06012683A (es) | 2004-05-03 | 2007-01-16 | Hoffmann La Roche | Derivados de indolilo como moduladores de receptor x del higado. |
| EA011671B1 (ru) | 2004-06-04 | 2009-04-28 | Арена Фармасьютикалз, Инк. | Замещенные производные арила и гетероарила в качестве модуляторов метаболизма и для профилактики и лечения связанных с ним расстройств |
| EP1838706A1 (en) | 2004-12-24 | 2007-10-03 | Prosidion Limited | G-protein coupled receptor agonists |
| 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 |
| CA2612187C (en) | 2005-06-23 | 2013-05-07 | Emory University | Stereoselective synthesis of amino acid analogs for tumor imaging |
| EP2152707B1 (en) | 2007-05-04 | 2012-06-20 | Bristol-Myers Squibb Company | [6,5]-bicyclic gpr119 g protein-coupled receptor agonists |
| PL2170864T3 (pl) | 2007-07-17 | 2012-02-29 | Bristol Myers Squibb Co | Agoniści receptora gpr119 sprężonego z białkiem g - pirydon |
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- 2008-04-30 CN CN200880014028A patent/CN101668756A/zh active Pending
- 2008-04-30 WO PCT/US2008/061928 patent/WO2008137435A1/en not_active Ceased
- 2008-04-30 JP JP2010507528A patent/JP2010526145A/ja not_active Withdrawn
- 2008-04-30 EP EP08747129A patent/EP2144902B1/en not_active Not-in-force
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| TW200848055A (en) | 2008-12-16 |
| US8076322B2 (en) | 2011-12-13 |
| US7910583B2 (en) | 2011-03-22 |
| US20120202790A1 (en) | 2012-08-09 |
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| JP2010526145A (ja) | 2010-07-29 |
| EP2144902B1 (en) | 2012-05-16 |
| US8314095B2 (en) | 2012-11-20 |
| US20130116237A1 (en) | 2013-05-09 |
| EP2144902A1 (en) | 2010-01-20 |
| WO2008137435A1 (en) | 2008-11-13 |
| AR066437A1 (es) | 2009-08-19 |
| CN101668756A (zh) | 2010-03-10 |
| US20110136783A1 (en) | 2011-06-09 |
| US8513265B2 (en) | 2013-08-20 |
| US20080293690A1 (en) | 2008-11-27 |
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