EA030958B1 - Ингибиторы акк и их применение - Google Patents

Info

Publication number

EA030958B1

EA030958B1 EA201591961A EA201591961A EA030958B1 EA 030958 B1 EA030958 B1 EA 030958B1 EA 201591961 A EA201591961 A EA 201591961A EA 201591961 A EA201591961 A EA 201591961A EA 030958 B1 EA030958 B1 EA 030958B1

Authority

EA

Eurasian Patent Office

Prior art keywords

compound

compounds

inhibitors

present

mmol

Prior art date

2013-05-10

Links

• Espacenet
• Global Dossier
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• 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 title claims 23
• 150000001875 compounds Chemical class 0.000 claims abstract 355
• 239000000203 mixture Substances 0.000 claims abstract 176
• 238000000034 method Methods 0.000 claims abstract 80
• 239000003112 inhibitor Substances 0.000 claims abstract 68
• 108010018763 Biotin carboxylase Proteins 0.000 claims abstract 43
• 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims abstract 40
• 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims abstract 40
• -1 benzyl compound 9.13 Chemical compound 0.000 claims 145
• 239000000243 solution Substances 0.000 claims 89
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 77
• 230000015572 biosynthetic process Effects 0.000 claims 74
• 229910052757 nitrogen Inorganic materials 0.000 claims 68
• 239000013543 active substance Substances 0.000 claims 67
• 238000003786 synthesis reaction Methods 0.000 claims 65
• 238000006243 chemical reaction Methods 0.000 claims 62
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 62
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 61
• 229910052717 sulfur Chemical group 0.000 claims 61
• 239000011593 sulfur Chemical group 0.000 claims 61
• 125000005842 heteroatom Chemical group 0.000 claims 58
• 239000007787 solid Substances 0.000 claims 58
• 239000002904 solvent Substances 0.000 claims 58
• 210000004027 cell Anatomy 0.000 claims 57
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 55
• 229910052760 oxygen Inorganic materials 0.000 claims 55
• 239000001301 oxygen Chemical group 0.000 claims 55
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 51
• 229920006395 saturated elastomer Polymers 0.000 claims 50
• 235000002639 sodium chloride Nutrition 0.000 claims 49
• 235000014113 dietary fatty acids Nutrition 0.000 claims 47
• 239000000194 fatty acid Substances 0.000 claims 47
• 229930195729 fatty acid Natural products 0.000 claims 47
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 44
• 150000004665 fatty acids Chemical class 0.000 claims 44
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 42
• 238000011282 treatment Methods 0.000 claims 40
• 206010028980 Neoplasm Diseases 0.000 claims 39
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• 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 claims 38
• 150000003839 salts Chemical class 0.000 claims 38
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 37
• 125000000623 heterocyclic group Chemical group 0.000 claims 37
• 125000001931 aliphatic group Chemical group 0.000 claims 35
• 208000008589 Obesity Diseases 0.000 claims 34
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 34
• 229910052736 halogen Inorganic materials 0.000 claims 34
• 150000002367 halogens Chemical class 0.000 claims 34
• 230000000694 effects Effects 0.000 claims 33
• 235000020824 obesity Nutrition 0.000 claims 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 31
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 31
• 125000003118 aryl group Chemical group 0.000 claims 28
• 229910052739 hydrogen Inorganic materials 0.000 claims 28
• 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 claims 28
• 125000001424 substituent group Chemical group 0.000 claims 28
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 27
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• 239000001257 hydrogen Substances 0.000 claims 27
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• 125000002950 monocyclic group Chemical group 0.000 claims 24
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• 239000003153 chemical reaction reagent Substances 0.000 claims 22
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 21
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 17
• 239000003814 drug Substances 0.000 claims 17
• 239000012634 fragment Substances 0.000 claims 17
• 125000001072 heteroaryl group Chemical group 0.000 claims 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
• 239000000126 substance Substances 0.000 claims 17
• 241001465754 Metazoa Species 0.000 claims 16
• 125000000217 alkyl group Chemical group 0.000 claims 16
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• 235000019198 oils Nutrition 0.000 claims 16
• 230000003647 oxidation Effects 0.000 claims 16
• 238000007254 oxidation reaction Methods 0.000 claims 16
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 16
• 101100288236 Arabidopsis thaliana KRP4 gene Proteins 0.000 claims 15
• 101100433979 Bos taurus TNK2 gene Proteins 0.000 claims 15
• 241000700159 Rattus Species 0.000 claims 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 15
• 101100385394 Zea mays ACK2 gene Proteins 0.000 claims 15
• 235000005911 diet Nutrition 0.000 claims 15
• 230000037213 diet Effects 0.000 claims 15
• 150000002430 hydrocarbons Chemical group 0.000 claims 15
• 239000000843 powder Substances 0.000 claims 15
• 102000004877 Insulin Human genes 0.000 claims 14
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• 238000007792 addition Methods 0.000 claims 14
• 239000005557 antagonist Substances 0.000 claims 14
• 239000003054 catalyst Substances 0.000 claims 14
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• 235000019441 ethanol Nutrition 0.000 claims 14
• 239000000417 fungicide Substances 0.000 claims 14
• 229940125396 insulin Drugs 0.000 claims 14
• 210000004185 liver Anatomy 0.000 claims 14
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• 229910052799 carbon Inorganic materials 0.000 claims 13
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
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• 241000124008 Mammalia Species 0.000 claims 12
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• 150000002431 hydrogen Chemical group 0.000 claims 12
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• 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 claims 11
• 208000001145 Metabolic Syndrome Diseases 0.000 claims 11
• 235000011054 acetic acid Nutrition 0.000 claims 11
• 125000004429 atom Chemical group 0.000 claims 11
• 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 claims 11
• 230000037396 body weight Effects 0.000 claims 11
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• 108090000623 proteins and genes Proteins 0.000 claims 11
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 11
• 102100036409 Activated CDC42 kinase 1 Human genes 0.000 claims 10
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 10
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 10
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• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 10
• LTYOQGRJFJAKNA-KKIMTKSISA-N Malonyl CoA Natural products S(C(=O)CC(=O)O)CCNC(=O)CCNC(=O)[C@@H](O)C(CO[P@](=O)(O[P@](=O)(OC[C@H]1[C@@H](OP(=O)(O)O)[C@@H](O)[C@@H](n2c3ncnc(N)c3nc2)O1)O)O)(C)C LTYOQGRJFJAKNA-KKIMTKSISA-N 0.000 claims 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 10
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 10
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• NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims 10
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