CA2692713A1 - Heterocyclic modulators of pkb - Google Patents
Heterocyclic modulators of pkb Download PDFInfo
- Publication number
- CA2692713A1 CA2692713A1 CA 2692713 CA2692713A CA2692713A1 CA 2692713 A1 CA2692713 A1 CA 2692713A1 CA 2692713 CA2692713 CA 2692713 CA 2692713 A CA2692713 A CA 2692713A CA 2692713 A1 CA2692713 A1 CA 2692713A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- compound
- formula
- aryl
- mmol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 350
- 239000000203 mixture Substances 0.000 claims abstract description 197
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 83
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 60
- 201000010099 disease Diseases 0.000 claims abstract description 47
- 201000011510 cancer Diseases 0.000 claims abstract description 45
- 230000001404 mediated effect Effects 0.000 claims abstract description 24
- 230000010261 cell growth Effects 0.000 claims abstract description 15
- 230000002159 abnormal effect Effects 0.000 claims abstract description 13
- 206010061218 Inflammation Diseases 0.000 claims abstract description 10
- 230000004054 inflammatory process Effects 0.000 claims abstract description 10
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 9
- -1 -OR11 Chemical group 0.000 claims description 253
- 125000003118 aryl group Chemical group 0.000 claims description 105
- 238000000034 method Methods 0.000 claims description 48
- 239000003814 drug Substances 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 208000035475 disorder Diseases 0.000 claims description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 229940124597 therapeutic agent Drugs 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 19
- 108091000080 Phosphotransferase Proteins 0.000 claims description 19
- 102000020233 phosphotransferase Human genes 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000006413 ring segment Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 7
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 230000035755 proliferation Effects 0.000 claims description 6
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 5
- 208000016097 disease of metabolism Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 5
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 5
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 102000001267 GSK3 Human genes 0.000 claims description 4
- 108060006662 GSK3 Proteins 0.000 claims description 4
- 101001064870 Homo sapiens Lon protease homolog, mitochondrial Proteins 0.000 claims description 4
- 101000669921 Homo sapiens Rho-associated protein kinase 2 Proteins 0.000 claims description 4
- 101000595531 Homo sapiens Serine/threonine-protein kinase pim-1 Proteins 0.000 claims description 4
- 101001001648 Homo sapiens Serine/threonine-protein kinase pim-2 Proteins 0.000 claims description 4
- 102100039314 Rho-associated protein kinase 2 Human genes 0.000 claims description 4
- 102100036077 Serine/threonine-protein kinase pim-1 Human genes 0.000 claims description 4
- 102100036120 Serine/threonine-protein kinase pim-2 Human genes 0.000 claims description 4
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- NFVJNJQRWPQVOA-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-ethyl-5-ethylsulfanyl-1,2,4-triazol-3-yl)piperidin-1-yl]acetamide Chemical compound CCN1C(SCC)=NN=C1C1CN(CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)CCC1 NFVJNJQRWPQVOA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
- 102100035427 Forkhead box protein O1 Human genes 0.000 claims description 3
- 101000877727 Homo sapiens Forkhead box protein O1 Proteins 0.000 claims description 3
- 108010001127 Insulin Receptor Proteins 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 claims description 2
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 102000003746 Insulin Receptor Human genes 0.000 claims 1
- 108091008611 Protein Kinase B Proteins 0.000 abstract description 56
- 230000001225 therapeutic effect Effects 0.000 abstract description 9
- 102000005765 Proto-Oncogene Proteins c-akt Human genes 0.000 abstract description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 247
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 166
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 121
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 97
- 239000007787 solid Substances 0.000 description 97
- 239000000047 product Substances 0.000 description 92
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 87
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 82
- 235000019439 ethyl acetate Nutrition 0.000 description 79
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 74
- 239000000243 solution Substances 0.000 description 73
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 71
- 238000005481 NMR spectroscopy Methods 0.000 description 70
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
- 229910001868 water Inorganic materials 0.000 description 60
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 57
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 239000000741 silica gel Substances 0.000 description 50
- 229910002027 silica gel Inorganic materials 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 49
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 47
- 239000011541 reaction mixture Substances 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 41
- 230000002829 reductive effect Effects 0.000 description 40
- 239000002904 solvent Substances 0.000 description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
- 238000001819 mass spectrum Methods 0.000 description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- 229910052938 sodium sulfate Inorganic materials 0.000 description 29
- 235000011152 sodium sulphate Nutrition 0.000 description 29
- 239000003795 chemical substances by application Substances 0.000 description 28
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 235000019341 magnesium sulphate Nutrition 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- 238000003818 flash chromatography Methods 0.000 description 26
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 25
- 239000012267 brine Substances 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- 230000027455 binding Effects 0.000 description 21
- 238000011282 treatment Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 125000003342 alkenyl group Chemical group 0.000 description 19
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- 239000002246 antineoplastic agent Substances 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- NASHXMFMSHZCQF-LBPRGKRZSA-N tert-butyl (4s)-2,2-dioxo-4-[[4-(trifluoromethyl)phenyl]methyl]oxathiazolidine-3-carboxylate Chemical compound C1OS(=O)(=O)N(C(=O)OC(C)(C)C)[C@H]1CC1=CC=C(C(F)(F)F)C=C1 NASHXMFMSHZCQF-LBPRGKRZSA-N 0.000 description 18
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 17
- 238000000746 purification Methods 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
- SMVCCWNHCHCWAZ-NSHDSACASA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-(trifluoromethyl)phenyl]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=C(C(F)(F)F)C=C1 SMVCCWNHCHCWAZ-NSHDSACASA-N 0.000 description 14
- 101150041968 CDC13 gene Proteins 0.000 description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- 239000000427 antigen Substances 0.000 description 14
- 102000036639 antigens Human genes 0.000 description 14
- 108091007433 antigens Proteins 0.000 description 14
- 229940034982 antineoplastic agent Drugs 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 239000007832 Na2SO4 Substances 0.000 description 13
- 229910000024 caesium carbonate Inorganic materials 0.000 description 13
- 239000002552 dosage form Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000003112 inhibitor Substances 0.000 description 13
- 229940002612 prodrug Drugs 0.000 description 13
- 239000000651 prodrug Substances 0.000 description 13
- WUZQTGRXFSRYQS-LBPRGKRZSA-N tert-butyl (4s)-4-[(4-chlorophenyl)methyl]-2,2-dioxooxathiazolidine-3-carboxylate Chemical compound C1OS(=O)(=O)N(C(=O)OC(C)(C)C)[C@H]1CC1=CC=C(Cl)C=C1 WUZQTGRXFSRYQS-LBPRGKRZSA-N 0.000 description 13
- 239000000546 pharmaceutical excipient Substances 0.000 description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 235000017550 sodium carbonate Nutrition 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 235000019270 ammonium chloride Nutrition 0.000 description 10
- 239000012455 biphasic mixture Substances 0.000 description 10
- 125000001188 haloalkyl group Chemical group 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 239000012279 sodium borohydride Substances 0.000 description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 description 10
- FVPYRAPXXNARAH-NSHDSACASA-N (3s)-3-[(4-chlorophenyl)methyl]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid Chemical compound CC(C)(C)OC(=O)[C@H](CC(O)=O)CC1=CC=C(Cl)C=C1 FVPYRAPXXNARAH-NSHDSACASA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 239000004037 angiogenesis inhibitor Substances 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
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- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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-
2008
- 2008-07-16 US US12/218,754 patent/US7897619B2/en not_active Expired - Fee Related
- 2008-07-16 EP EP08794537A patent/EP2173728A2/en not_active Withdrawn
- 2008-07-16 JP JP2010517014A patent/JP2010533715A/ja not_active Withdrawn
- 2008-07-16 WO PCT/US2008/008723 patent/WO2009011880A2/en not_active Ceased
- 2008-07-16 CA CA 2692713 patent/CA2692713A1/en not_active Abandoned
- 2008-07-16 AU AU2008276521A patent/AU2008276521B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008276521B2 (en) | 2011-11-03 |
| WO2009011880A2 (en) | 2009-01-22 |
| JP2010533715A (ja) | 2010-10-28 |
| US20090275592A1 (en) | 2009-11-05 |
| EP2173728A2 (en) | 2010-04-14 |
| US7897619B2 (en) | 2011-03-01 |
| WO2009011880A3 (en) | 2009-04-02 |
| AU2008276521A1 (en) | 2009-01-22 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140514 |