DK2922850T3 - Compounds and Methods for Their Use - Google Patents

Info

Publication number

DK2922850T3

DK2922850T3 DK13857585.7T DK13857585T DK2922850T3 DK 2922850 T3 DK2922850 T3 DK 2922850T3 DK 13857585 T DK13857585 T DK 13857585T DK 2922850 T3 DK2922850 T3 DK 2922850T3

Authority

DK

Denmark

Prior art keywords

compound

bis

diyl

alkyl

nmr

Prior art date

2012-11-22

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 346
• 238000000034 method Methods 0.000 title description 230
• -1 -OH Chemical group 0.000 claims description 245
• 229910052757 nitrogen Inorganic materials 0.000 claims description 179
• 125000000217 alkyl group Chemical group 0.000 claims description 123
• 230000014509 gene expression Effects 0.000 claims description 103
• 206010028980 Neoplasm Diseases 0.000 claims description 96
• 201000011510 cancer Diseases 0.000 claims description 70
• 108050007957 Cadherin Proteins 0.000 claims description 52
• 102000000905 Cadherin Human genes 0.000 claims description 51
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 47
• 108010065472 Vimentin Proteins 0.000 claims description 44
• 102000013127 Vimentin Human genes 0.000 claims description 43
• 210000005048 vimentin Anatomy 0.000 claims description 42
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 41
• 108010053763 Pyruvate Carboxylase Proteins 0.000 claims description 39
• 102100039895 Pyruvate carboxylase, mitochondrial Human genes 0.000 claims description 39
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 36
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
• 125000001072 heteroaryl group Chemical group 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 239000001257 hydrogen Substances 0.000 claims description 31
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 28
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 25
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 11
• 125000002619 bicyclic group Chemical group 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 5
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• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 5
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
• 208000006265 Renal cell carcinoma Diseases 0.000 claims description 3
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
• 229910052736 halogen Inorganic materials 0.000 claims description 3
• 150000002367 halogens Chemical class 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000003367 polycyclic group Chemical group 0.000 claims description 3
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• 208000034578 Multiple myelomas Diseases 0.000 claims description 2
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• 201000008968 osteosarcoma Diseases 0.000 claims description 2
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
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• 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 260
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 256
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• 239000000203 mixture Substances 0.000 description 94
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• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 87
• 239000000243 solution Substances 0.000 description 87
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• 239000000523 sample Substances 0.000 description 70
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
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• 150000007523 nucleic acids Chemical class 0.000 description 38
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• 108020004707 nucleic acids Proteins 0.000 description 36
• 102000039446 nucleic acids Human genes 0.000 description 36
• 235000019439 ethyl acetate Nutrition 0.000 description 34
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
• 238000006243 chemical reaction Methods 0.000 description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
• DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-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 30
• 239000012044 organic layer Substances 0.000 description 30
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• 229910052938 sodium sulfate Inorganic materials 0.000 description 25
• 235000011152 sodium sulphate Nutrition 0.000 description 25
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 24
• 125000005843 halogen group Chemical group 0.000 description 24
• 235000002639 sodium chloride Nutrition 0.000 description 24
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• 239000012267 brine Substances 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
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• 125000001188 haloalkyl group Chemical group 0.000 description 17
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• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 15
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• CDTYEYUKQITJGQ-UHFFFAOYSA-N 2-[6-(3-hydroxyazetidin-1-yl)pyridin-2-yl]acetamide Chemical compound OC1CN(C1)C1=CC=CC(=N1)CC(=O)N CDTYEYUKQITJGQ-UHFFFAOYSA-N 0.000 description 14
• UXVCEKRAZBZVSL-UHFFFAOYSA-N 2-pyridin-2-ylacetamide Chemical compound NC(=O)CC1=CC=CC=N1 UXVCEKRAZBZVSL-UHFFFAOYSA-N 0.000 description 14
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
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