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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- C07—ORGANIC CHEMISTRY
- 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 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (10)
| 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 (65)
| 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 |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| SG174054A1 (en) | 2006-05-04 | 2011-09-29 | Boehringer Ingelheim Int | Polymorphs |
| HRP20110806T1 (hr) * | 2007-07-17 | 2011-11-30 | Bristol-Myers Squibb Company | Agonisti piridon gpr119 g protein-vezanih receptora |
| AR071175A1 (es) | 2008-04-03 | 2010-06-02 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un inhibidor de la dipeptidil-peptidasa-4 (dpp4) y un farmaco acompanante |
| US8188098B2 (en) | 2008-05-19 | 2012-05-29 | Hoffmann-La Roche Inc. | GPR119 receptor agonists |
| CA2730593A1 (en) * | 2008-07-16 | 2010-01-21 | Schering Corporation | Bicyclic heterocycle derivatives and use thereof as gpr119 modulators |
| US8815876B2 (en) | 2008-07-16 | 2014-08-26 | Merck Sharp & Dohme Corp. | Bicyclic heterocycle derivatives and methods of use thereof |
| TW201006821A (en) * | 2008-07-16 | 2010-02-16 | Bristol Myers Squibb Co | Pyridone and pyridazone analogues as GPR119 modulators |
| AU2009270983A1 (en) * | 2008-07-16 | 2010-01-21 | Schering Corporation | Bicyclic heterocycle derivatives and their use as GPCR modulators |
| KR20190016601A (ko) | 2008-08-06 | 2019-02-18 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
| 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 |
| EA022310B1 (ru) | 2008-12-23 | 2015-12-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Солевые формы органического соединения |
| WO2010075273A1 (en) * | 2008-12-23 | 2010-07-01 | Schering Corporation | Bicyclic heterocycle derivatives and methods of use thereof |
| US20120016119A1 (en) * | 2009-01-22 | 2012-01-19 | Yasunori Tsuboi | NOVEL PYRROLO(2,3-d)PYRIMIDINE COMPOUND |
| WO2010088518A2 (en) * | 2009-01-31 | 2010-08-05 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| EP2399914A4 (en) | 2009-02-18 | 2012-08-29 | Takeda Pharmaceutical | FUSED HETEROCYCLIC CORE COMPOUND |
| WO2010114957A1 (en) | 2009-04-03 | 2010-10-07 | Schering Corporation | 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 |
| BR112012012641A2 (pt) | 2009-11-27 | 2020-08-11 | Boehringer Ingelheim International Gmbh | TRATAMENTO DE PACIENTES DIABÉTICOS GENOTIPADOS COM INIBIDORES DE DPP-lVTAL COMO LINAGLIPTINA |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
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| CL2008001271A1 (es) | 2008-09-12 |
| EP2144902A1 (en) | 2010-01-20 |
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| US7910583B2 (en) | 2011-03-22 |
| US20080293690A1 (en) | 2008-11-27 |
| CN101668756A (zh) | 2010-03-10 |
| EP2144902B1 (en) | 2012-05-16 |
| TW200848055A (en) | 2008-12-16 |
| US8314095B2 (en) | 2012-11-20 |
| PE20090222A1 (es) | 2009-03-27 |
| US8513265B2 (en) | 2013-08-20 |
| AR066437A1 (es) | 2009-08-19 |
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