TW200843765A - 2-aminopyridine analogs as glucokinase activators - Google Patents
2-aminopyridine analogs as glucokinase activators Download PDFInfo
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- TW200843765A TW200843765A TW097110307A TW97110307A TW200843765A TW 200843765 A TW200843765 A TW 200843765A TW 097110307 A TW097110307 A TW 097110307A TW 97110307 A TW97110307 A TW 97110307A TW 200843765 A TW200843765 A TW 200843765A
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- 108010021582 Glucokinase Proteins 0.000 title claims abstract description 25
- 102000030595 Glucokinase Human genes 0.000 title claims abstract description 20
- 150000003930 2-aminopyridines Chemical class 0.000 title description 6
- 239000012190 activator Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 319
- 238000000034 method Methods 0.000 claims abstract description 122
- 230000000694 effects Effects 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 203
- -1 compound oxime Chemical class 0.000 claims description 196
- 238000006243 chemical reaction Methods 0.000 claims description 160
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 96
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000004429 atom Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 22
- 150000003512 tertiary amines Chemical class 0.000 claims description 21
- 150000002923 oximes Chemical class 0.000 claims description 20
- 238000012360 testing method Methods 0.000 claims description 20
- 229910052740 iodine Inorganic materials 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000000565 sulfonamide group Chemical group 0.000 claims description 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 5
- 230000007017 scission Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- JCFWQBLQYTZMOF-UHFFFAOYSA-N [Cl-].C[NH2+]C.S Chemical compound [Cl-].C[NH2+]C.S JCFWQBLQYTZMOF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 2
- PXFIAYNRKNWKLV-UHFFFAOYSA-N 2-(dimethylamino)acetonitrile;hydrochloride Chemical compound Cl.CN(C)CC#N PXFIAYNRKNWKLV-UHFFFAOYSA-N 0.000 claims 1
- DTSCZKIBPYQEND-UHFFFAOYSA-L CN(C)[Ru](Cl)Cl Chemical compound CN(C)[Ru](Cl)Cl DTSCZKIBPYQEND-UHFFFAOYSA-L 0.000 claims 1
- XRJWYPZEAXAVPF-UHFFFAOYSA-N S.SNS Chemical compound S.SNS XRJWYPZEAXAVPF-UHFFFAOYSA-N 0.000 claims 1
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 abstract description 11
- 230000001404 mediated effect Effects 0.000 abstract description 5
- 206010011953 Decreased activity Diseases 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 230000002950 deficient Effects 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 208000037765 diseases and disorders Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 267
- 235000019439 ethyl acetate Nutrition 0.000 description 128
- 206010057190 Respiratory tract infections Diseases 0.000 description 90
- 239000000243 solution Substances 0.000 description 90
- 239000000203 mixture Substances 0.000 description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 86
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 81
- 239000007787 solid Substances 0.000 description 81
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 79
- 238000002360 preparation method Methods 0.000 description 78
- 239000002585 base Substances 0.000 description 77
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 73
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 63
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
- 238000005481 NMR spectroscopy Methods 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
- 238000005160 1H NMR spectroscopy Methods 0.000 description 37
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 36
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 33
- 239000012044 organic layer Substances 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
- 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 27
- 239000008103 glucose Substances 0.000 description 27
- 229910052938 sodium sulfate Inorganic materials 0.000 description 27
- 235000011152 sodium sulphate Nutrition 0.000 description 27
- 101150041968 CDC13 gene Proteins 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
- 239000000460 chlorine Substances 0.000 description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 238000001819 mass spectrum Methods 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 229910000104 sodium hydride Inorganic materials 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- ZVDDJPSHRNMSKV-UHFFFAOYSA-N acetaldehyde;hydrochloride Chemical compound Cl.CC=O ZVDDJPSHRNMSKV-UHFFFAOYSA-N 0.000 description 17
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 17
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
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- 125000004076 pyridyl group Chemical group 0.000 description 16
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- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000004949 mass spectrometry Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 15
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
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- 239000001257 hydrogen Substances 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 12
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- 150000001412 amines Chemical class 0.000 description 11
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- DUCOISOCHCDKOU-UHFFFAOYSA-N Cl.Cl.C(C)C(=O)CC Chemical compound Cl.Cl.C(C)C(=O)CC DUCOISOCHCDKOU-UHFFFAOYSA-N 0.000 description 9
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- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000000707 wrist Anatomy 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Ophthalmology & Optometry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91971907P | 2007-03-23 | 2007-03-23 | |
| PCT/US2007/007444 WO2007117381A2 (en) | 2006-03-24 | 2007-03-23 | 2 -aminopyridine analogs as glucokinase activators |
| US97426007P | 2007-09-21 | 2007-09-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200843765A true TW200843765A (en) | 2008-11-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097110307A TW200843765A (en) | 2007-03-23 | 2008-03-21 | 2-aminopyridine analogs as glucokinase activators |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8362037B2 (enExample) |
| EP (1) | EP2173745A2 (enExample) |
| JP (1) | JP5450108B2 (enExample) |
| CN (1) | CN101679405A (enExample) |
| CA (1) | CA2681695A1 (enExample) |
| TW (1) | TW200843765A (enExample) |
| WO (1) | WO2008118718A2 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US8431713B2 (en) * | 2007-01-24 | 2013-04-30 | Array Biopharma, Inc. | 2-aminopyridine derivatives as glucokinase activators |
| UA101166C2 (ru) | 2007-09-21 | 2013-03-11 | Аррей Биофарма Инк. | Производные пиридин-2-иламино-1,2,4-тиадиазола как активаторы глюкокиназы для лечения сахарного диабета |
| EA201000561A1 (ru) * | 2007-10-09 | 2010-10-29 | Мерк Патент Гмбх | Производные пиридина, пригодные в качестве активаторов глюкокиназы |
| JP5529044B2 (ja) * | 2008-01-25 | 2014-06-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺菌性複素環化合物 |
| AR077821A1 (es) * | 2009-08-11 | 2011-09-28 | Sanofi Aventis Us Llc | Procedimiento para preparar hidrocloruro de 4-metil-3-tienilamina |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2553086B1 (en) | 2010-03-31 | 2017-04-19 | The Scripps Research Institute | Reprogramming cells |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| 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 |
| 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 |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| JPWO2012121314A1 (ja) | 2011-03-09 | 2014-07-17 | 第一三共株式会社 | ジピリジルアミン誘導体 |
| 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 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US9296735B2 (en) | 2012-05-18 | 2016-03-29 | Amgen Inc. | Method for the preparation of thiadiazoles |
| US9663536B2 (en) | 2013-03-13 | 2017-05-30 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| US9580431B2 (en) | 2013-03-13 | 2017-02-28 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| CN105829296A (zh) | 2013-12-18 | 2016-08-03 | 巴斯夫欧洲公司 | 带有亚胺衍生的取代基的唑类化合物 |
| AU2015237253B2 (en) | 2014-03-28 | 2019-11-14 | Azevan Pharmaceuticals, Inc. | Compositions and methods for treating neurodegenerative diseases |
| CN106349159B (zh) * | 2016-08-29 | 2019-03-22 | 山东省联合农药工业有限公司 | 一种3-氯-2-氰基-5-三氟甲基吡啶的制备方法 |
| CN107286087B (zh) * | 2017-04-16 | 2020-01-07 | 内蒙古佳瑞米精细化工有限公司 | 一种2-氰基-3-氯-5-三氟甲基吡啶的合成方法 |
| MY208313A (en) | 2017-09-15 | 2025-04-30 | Azevan Pharmaceuticals Inc | Compositions and methods for treating brain injury |
| EP3703675A4 (en) | 2017-10-30 | 2021-06-16 | Neuropore Therapies, Inc. | SUBSTITUTED PHENYLSULFONYLPHÉNYLTRIAZOLETHIONES AND ASSOCIATED USES |
| EP3846793B1 (en) | 2018-09-07 | 2024-01-24 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| JP7648027B2 (ja) | 2019-12-19 | 2025-03-18 | クリア、スペイン、エセ、ア、ウ | ウパダシチニブの調製のための方法及び中間体 |
| MX2022010944A (es) | 2020-03-03 | 2022-11-09 | Pic Therapeutics Inc | Inhibidores del factor de iniciacion de traduccion eucariotica 4e (eif4e) y sus usos. |
| TW202315621A (zh) | 2021-08-25 | 2023-04-16 | 美商皮克醫療公司 | Ｅｉｆ４ｅ抑制劑及其用途 |
| JP2024532276A (ja) | 2021-08-25 | 2024-09-05 | ピク セラピューティクス， インコーポレイテッド | ｅＩＦ４Ｅ阻害剤及びその使用 |
| US20250340570A1 (en) | 2022-04-27 | 2025-11-06 | Skyhawk Therapeutics, Inc. | Compositions useful for modulating splicing |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3703435A1 (de) * | 1987-02-05 | 1988-08-18 | Thomae Gmbh Dr K | Neue thiazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US5260311A (en) * | 1989-02-22 | 1993-11-09 | Novo Nordisk A/S | Piperidine compounds and their use |
| US7629362B2 (en) * | 2003-02-13 | 2009-12-08 | Banyu Pharmaceutical Co., Ltd. | 2-pyridine carboxamide derivatives |
| AR049418A1 (es) * | 2004-02-27 | 2006-08-02 | Bayer Pharmaceuticals Corp | Derivados de heteroarilaminopirazol y composiciones farmaceuticas para el tratamiento de la diabetes. |
| AU2005223610B2 (en) | 2004-03-23 | 2008-05-29 | Banyu Pharmaceutical Co., Ltd. | Substituted quinazoline or pyridopyrimidine derivative |
| ATE521608T1 (de) * | 2005-11-01 | 2011-09-15 | Array Biopharma Inc | Glucokinaseaktivatoren |
| ES2378704T3 (es) * | 2006-01-27 | 2012-04-17 | Array Biopharma, Inc. | Activadores de la glucocinasa |
| EP2543667B1 (en) * | 2006-03-24 | 2015-01-28 | Array Biopharma, Inc. | A method of preparing 2-aminopyridine analogs as glucokinase activators |
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- 2008-03-19 JP JP2009554721A patent/JP5450108B2/ja not_active Expired - Fee Related
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- 2008-03-21 TW TW097110307A patent/TW200843765A/zh unknown
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| JP2010527911A (ja) | 2010-08-19 |
| WO2008118718A3 (en) | 2008-11-13 |
| JP5450108B2 (ja) | 2014-03-26 |
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| WO2008118718A2 (en) | 2008-10-02 |
| CA2681695A1 (en) | 2008-10-02 |
| EP2173745A2 (en) | 2010-04-14 |
| US20100105659A1 (en) | 2010-04-29 |
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