WO2010059602A2 - Inhibitors of diacylglycerol acyltransferase - Google Patents
Inhibitors of diacylglycerol acyltransferase Download PDFInfo
- Publication number
- WO2010059602A2 WO2010059602A2 PCT/US2009/064738 US2009064738W WO2010059602A2 WO 2010059602 A2 WO2010059602 A2 WO 2010059602A2 US 2009064738 W US2009064738 W US 2009064738W WO 2010059602 A2 WO2010059602 A2 WO 2010059602A2
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- WIPO (PCT)
- Prior art keywords
- compound
- alkyl
- aryl
- group
- cycloalkyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title abstract description 17
- 108010001348 Diacylglycerol O-acyltransferase Proteins 0.000 title abstract description 7
- 102000002148 Diacylglycerol O-acyltransferase Human genes 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 403
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 208000008589 Obesity Diseases 0.000 claims abstract description 13
- 235000020824 obesity Nutrition 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
- 208000002249 Diabetes Complications Diseases 0.000 claims abstract description 5
- 206010012655 Diabetic complications Diseases 0.000 claims abstract description 5
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 5
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 5
- 208000035475 disorder Diseases 0.000 claims abstract description 5
- 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 4
- 206010056997 Impaired fasting glucose Diseases 0.000 claims abstract description 4
- 201000009104 prediabetes syndrome Diseases 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 273
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 125000000623 heterocyclic group Chemical group 0.000 claims description 87
- -1 cycloalkenylalkyl Chemical group 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 125000001072 heteroaryl group Chemical group 0.000 claims description 53
- 239000003814 drug Substances 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 229940124597 therapeutic agent Drugs 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 229940125708 antidiabetic agent Drugs 0.000 claims description 8
- 239000003472 antidiabetic agent Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000000883 anti-obesity agent Substances 0.000 claims description 6
- 229940125710 antiobesity agent Drugs 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 102100036869 Diacylglycerol O-acyltransferase 1 Human genes 0.000 abstract description 23
- 108050004099 Diacylglycerol O-acyltransferase 1 Proteins 0.000 abstract description 15
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 208
- 239000000543 intermediate Substances 0.000 description 195
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 179
- 239000007858 starting material Substances 0.000 description 109
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 86
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 71
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000011541 reaction mixture Substances 0.000 description 65
- 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 59
- 239000000203 mixture Substances 0.000 description 54
- 125000004193 piperazinyl group Chemical group 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 125000003386 piperidinyl group Chemical group 0.000 description 42
- 239000007787 solid Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 229940125904 compound 1 Drugs 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 32
- 235000019439 ethyl acetate Nutrition 0.000 description 32
- 229940125396 insulin Drugs 0.000 description 30
- 102000004877 Insulin Human genes 0.000 description 29
- 108090001061 Insulin Proteins 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 28
- 239000000047 product Substances 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 25
- 239000012453 solvate Substances 0.000 description 25
- OQGRFQCUGLKSAV-JTQLQIEISA-N n-[(3s)-2,6-dioxopiperidin-3-yl]-2-phenylacetamide Chemical compound N([C@@H]1C(NC(=O)CC1)=O)C(=O)CC1=CC=CC=C1 OQGRFQCUGLKSAV-JTQLQIEISA-N 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- MXNFUCNDPLBTMF-UHFFFAOYSA-N 1,3-oxazole-5-carboxamide Chemical compound NC(=O)C1=CN=CO1 MXNFUCNDPLBTMF-UHFFFAOYSA-N 0.000 description 20
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- 239000000651 prodrug Substances 0.000 description 20
- 229940002612 prodrug Drugs 0.000 description 20
- 239000000284 extract Substances 0.000 description 19
- 238000000746 purification Methods 0.000 description 19
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- FUEDHJBAZMUIQZ-UHFFFAOYSA-N 2-(trifluoromethyl)-1,3-oxazole-5-carboxamide Chemical compound NC(=O)C1=CN=C(C(F)(F)F)O1 FUEDHJBAZMUIQZ-UHFFFAOYSA-N 0.000 description 17
- 229910052740 iodine Inorganic materials 0.000 description 17
- 125000004122 cyclic group Chemical group 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 16
- 125000006413 ring segment Chemical group 0.000 description 16
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000013543 active substance Substances 0.000 description 15
- 125000002757 morpholinyl group Chemical group 0.000 description 15
- 229910052705 radium Inorganic materials 0.000 description 14
- 238000011282 treatment Methods 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- GSDNXGCHNWNELS-UHFFFAOYSA-N 2-piperidin-1-yl-4-(trifluoromethyl)-1,3-oxazole-5-carboxylic acid Chemical compound FC(F)(F)C1=C(C(=O)O)OC(N2CCCCC2)=N1 GSDNXGCHNWNELS-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- CNQYPGDMCBJWCI-UHFFFAOYSA-N ethyl 2-bromo-4-(trifluoromethyl)-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)C=1OC(Br)=NC=1C(F)(F)F CNQYPGDMCBJWCI-UHFFFAOYSA-N 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000008055 phosphate buffer solution Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CPNROAXMTJYXGE-UHFFFAOYSA-N 2-bromo-n-[6-(4-phenylpiperidin-1-yl)pyridin-3-yl]-4-(trifluoromethyl)-1,3-oxazole-5-carboxamide Chemical compound N1=C(Br)OC(C(=O)NC=2C=NC(=CC=2)N2CCC(CC2)C=2C=CC=CC=2)=C1C(F)(F)F CPNROAXMTJYXGE-UHFFFAOYSA-N 0.000 description 9
- 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 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 0 **c1cnc(*)[s]1 Chemical compound **c1cnc(*)[s]1 0.000 description 8
- RNDUCHISVYHVPG-UHFFFAOYSA-N 2-cyclohexylsulfanyl-4-(trifluoromethyl)-1,3-oxazole-5-carboxylic acid Chemical compound FC(F)(F)C1=C(C(=O)O)OC(SC2CCCCC2)=N1 RNDUCHISVYHVPG-UHFFFAOYSA-N 0.000 description 8
- GNQRFYRFHGAFNA-UHFFFAOYSA-N 4-(5-aminopyridin-2-yl)-1-benzylpiperazin-2-one Chemical compound N1=CC(N)=CC=C1N1CC(=O)N(CC=2C=CC=CC=2)CC1 GNQRFYRFHGAFNA-UHFFFAOYSA-N 0.000 description 8
- 101000927974 Homo sapiens Diacylglycerol O-acyltransferase 1 Proteins 0.000 description 8
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- MTGYRJWJAVBTAW-UHFFFAOYSA-N cyclopentyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate Chemical compound N1=CC(N)=CC=C1N1CCN(C(=O)OC2CCCC2)CC1 MTGYRJWJAVBTAW-UHFFFAOYSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- UELRBMZOMHKBJD-UHFFFAOYSA-N n-(2-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=CC=C1NC(=O)C=C UELRBMZOMHKBJD-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
- DSGKXGDSENGAHB-UHFFFAOYSA-N 1-(5-aminopyridin-2-yl)-4-phenylpiperidin-4-ol Chemical compound N1=CC(N)=CC=C1N1CCC(O)(C=2C=CC=CC=2)CC1 DSGKXGDSENGAHB-UHFFFAOYSA-N 0.000 description 7
- YEPRCPIKTUGVHG-UHFFFAOYSA-N 1-(5-nitropyridin-2-yl)piperazine Chemical compound N1=CC([N+](=O)[O-])=CC=C1N1CCNCC1 YEPRCPIKTUGVHG-UHFFFAOYSA-N 0.000 description 7
- XHSHWFWMMVVRNS-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)-4-(trifluoromethyl)-1,3-oxazole-5-carboxylic acid Chemical compound FC(F)(F)C1=C(C(=O)O)OC(N2C(CCC2)=O)=N1 XHSHWFWMMVVRNS-UHFFFAOYSA-N 0.000 description 7
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 7
- AEEITRBWTGFCQT-UHFFFAOYSA-N 2-bromo-4-(trifluoromethyl)-1,3-oxazole-5-carbonyl chloride Chemical compound FC(F)(F)C=1N=C(Br)OC=1C(Cl)=O AEEITRBWTGFCQT-UHFFFAOYSA-N 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- KJXCUVXXNXPFCC-UHFFFAOYSA-N 6-(4-phenylpiperidin-1-yl)pyridin-3-amine Chemical compound N1=CC(N)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 KJXCUVXXNXPFCC-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229940127007 Compound 39 Drugs 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 229940100389 Sulfonylurea Drugs 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 238000002648 combination therapy Methods 0.000 description 7
- MZZWBPKSIOWCJA-UHFFFAOYSA-N cyclopentyl 4-[5-[[2-bromo-4-(trifluoromethyl)-1,3-oxazole-5-carbonyl]amino]pyridin-2-yl]piperazine-1-carboxylate Chemical compound N1=C(Br)OC(C(=O)NC=2C=NC(=CC=2)N2CCN(CC2)C(=O)OC2CCCC2)=C1C(F)(F)F MZZWBPKSIOWCJA-UHFFFAOYSA-N 0.000 description 7
- MWTKTJSKHCDMOW-UHFFFAOYSA-N ethyl 2-amino-4-(trifluoromethyl)-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)C=1OC(N)=NC=1C(F)(F)F MWTKTJSKHCDMOW-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 230000000670 limiting effect Effects 0.000 description 7
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 235000000346 sugar Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 6
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 6
- CATDAABUMRVZPW-UHFFFAOYSA-N 1-benzyl-4-(5-nitropyridin-2-yl)piperazin-2-one Chemical compound N1=CC([N+](=O)[O-])=CC=C1N1CC(=O)N(CC=2C=CC=CC=2)CC1 CATDAABUMRVZPW-UHFFFAOYSA-N 0.000 description 6
- CNXYDFQAYBCJLV-UHFFFAOYSA-N 3-(2-fluoroanilino)-4-[4-(5-nitropyridin-2-yl)piperazin-1-yl]cyclobut-3-ene-1,2-dione Chemical compound N1=CC([N+](=O)[O-])=CC=C1N1CCN(C=2C(C(=O)C=2NC=2C(=CC=CC=2)F)=O)CC1 CNXYDFQAYBCJLV-UHFFFAOYSA-N 0.000 description 6
- MDTKXYHASLYJOH-UHFFFAOYSA-N 3-ethoxy-4-[4-(5-nitropyridin-2-yl)piperazin-1-yl]cyclobut-3-ene-1,2-dione Chemical compound O=C1C(=O)C(OCC)=C1N1CCN(C=2N=CC(=CC=2)[N+]([O-])=O)CC1 MDTKXYHASLYJOH-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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/02—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 containing two hetero rings
- C07D417/12—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 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D417/14—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 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
-
- 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
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Abstract
Description
Claims
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MX2011005234A MX2011005234A (en) | 2008-11-19 | 2009-11-17 | Inhibitors of diacylglycerol acyltransferase. |
JP2011536587A JP2012509274A (en) | 2008-11-19 | 2009-11-17 | Diacylglycerol acyltransferase inhibitors |
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EP09752998.6A EP2367598B1 (en) | 2008-11-19 | 2009-11-17 | Inhibitors of diacylglycerol acyltransferase |
AU2009316786A AU2009316786A1 (en) | 2008-11-19 | 2009-11-17 | Inhibitors of diacylglycerol acyltransferase |
CN2009801549757A CN102281919A (en) | 2008-11-19 | 2009-11-17 | Inhibitors of diacylglycerol acyltransferase |
US13/129,843 US8716312B2 (en) | 2008-11-19 | 2009-11-17 | Inhibitors of diacylglycerol acyltransferase |
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JP (1) | JP2012509274A (en) |
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AR (1) | AR074130A1 (en) |
AU (1) | AU2009316786A1 (en) |
CA (1) | CA2743609A1 (en) |
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Also Published As
Publication number | Publication date |
---|---|
AR074130A1 (en) | 2010-12-22 |
US20110224137A1 (en) | 2011-09-15 |
JP2012509274A (en) | 2012-04-19 |
WO2010059602A3 (en) | 2010-07-15 |
CA2743609A1 (en) | 2010-05-27 |
US8716312B2 (en) | 2014-05-06 |
CN102281919A (en) | 2011-12-14 |
TW201031657A (en) | 2010-09-01 |
EP2367598B1 (en) | 2014-04-09 |
AU2009316786A1 (en) | 2010-05-27 |
MX2011005234A (en) | 2011-06-01 |
EP2367598A2 (en) | 2011-09-28 |
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