CN107243007A - 改善认知功能的方法和组合物 - Google Patents

Info

Publication number

CN107243007A

CN107243007A CN201710440380.4A CN201710440380A CN107243007A CN 107243007 A CN107243007 A CN 107243007A CN 201710440380 A CN201710440380 A CN 201710440380A CN 107243007 A CN107243007 A CN 107243007A

Authority

CN

China

Prior art keywords

oxo

methyl

hydrogen

alkyl

butanamide

Prior art date

2008-10-16

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.)

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• 239000000203 mixture Substances 0.000 title claims description 81
• 230000003920 cognitive function Effects 0.000 title abstract description 33
• 238000000034 method Methods 0.000 title description 71
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 72
• 229960004002 levetiracetam Drugs 0.000 claims abstract description 62
• 208000028698 Cognitive impairment Diseases 0.000 claims abstract description 48
• 208000027061 mild cognitive impairment Diseases 0.000 claims abstract description 21
• 230000007000 age related cognitive decline Effects 0.000 claims abstract description 17
• 206010027175 memory impairment Diseases 0.000 claims abstract description 8
• HPHUVLMMVZITSG-ZCFIWIBFSA-N levetiracetam Chemical compound CC[C@H](C(N)=O)N1CCCC1=O HPHUVLMMVZITSG-ZCFIWIBFSA-N 0.000 claims abstract 5
• 150000003839 salts Chemical class 0.000 claims description 72
• 239000003814 drug Substances 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 239000003112 inhibitor Substances 0.000 abstract description 70
• 238000011282 treatment Methods 0.000 abstract description 25
• MSYKRHVOOPPJKU-BDAKNGLRSA-N brivaracetam Chemical compound CCC[C@H]1CN([C@@H](CC)C(N)=O)C(=O)C1 MSYKRHVOOPPJKU-BDAKNGLRSA-N 0.000 abstract description 21
• 229960002161 brivaracetam Drugs 0.000 abstract description 18
• 101000584505 Homo sapiens Synaptic vesicle glycoprotein 2A Proteins 0.000 abstract description 5
• 102100030701 Synaptic vesicle glycoprotein 2A Human genes 0.000 abstract description 5
• 102000004874 Synaptophysin Human genes 0.000 abstract description 4
• 108090001076 Synaptophysin Proteins 0.000 abstract description 4
• -1 azido, carboxyl Chemical group 0.000 description 526
• 229910052739 hydrogen Inorganic materials 0.000 description 299
• 239000001257 hydrogen Substances 0.000 description 298
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 191
• 125000000217 alkyl group Chemical group 0.000 description 190
• 229910052736 halogen Inorganic materials 0.000 description 159
• 150000002367 halogens Chemical class 0.000 description 138
• 150000001875 compounds Chemical class 0.000 description 130
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 109
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 107
• 125000003118 aryl group Chemical group 0.000 description 98
• 241000700159 Rattus Species 0.000 description 88
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 74
• 125000000623 heterocyclic group Chemical group 0.000 description 69
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 68
• 125000001424 substituent group Chemical group 0.000 description 68
• 125000004093 cyano group Chemical group *C#N 0.000 description 65
• HPHUVLMMVZITSG-LURJTMIESA-N levetiracetam Chemical group CC[C@@H](C(N)=O)N1CCCC1=O HPHUVLMMVZITSG-LURJTMIESA-N 0.000 description 58
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 51
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 49
• 239000002585 base Substances 0.000 description 47
• 125000003545 alkoxy group Chemical group 0.000 description 46
• NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 43
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 43
• 125000002252 acyl group Chemical group 0.000 description 41
• 125000005843 halogen group Chemical group 0.000 description 37
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 37
• 125000004432 carbon atom Chemical group C* 0.000 description 36
• 150000002148 esters Chemical class 0.000 description 36
• 238000012549 training Methods 0.000 description 35
• 125000003342 alkenyl group Chemical group 0.000 description 34
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 32
• 125000003368 amide group Chemical group 0.000 description 31
• 125000004414 alkyl thio group Chemical group 0.000 description 29
• 125000000304 alkynyl group Chemical group 0.000 description 28
• 125000000753 cycloalkyl group Chemical group 0.000 description 26
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 25
• 239000000460 chlorine Substances 0.000 description 25
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 25
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• 229910052801 chlorine Inorganic materials 0.000 description 23
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 22
• 238000012360 testing method Methods 0.000 description 22
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 21
• 239000013543 active substance Substances 0.000 description 20
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
• 230000032683 aging Effects 0.000 description 19
• 229910052794 bromium Inorganic materials 0.000 description 19
• 229960000604 valproic acid Drugs 0.000 description 19
• 229910052731 fluorine Inorganic materials 0.000 description 18
• 125000002541 furyl group Chemical group 0.000 description 18
• 125000004076 pyridyl group Chemical group 0.000 description 18
• 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 17
• 241001465754 Metazoa Species 0.000 description 17
• 238000012347 Morris Water Maze Methods 0.000 description 17
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
• 230000014759 maintenance of location Effects 0.000 description 17
• 229910052760 oxygen Inorganic materials 0.000 description 17
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 17
• 230000015654 memory Effects 0.000 description 16
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 16
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
• 229940079593 drug Drugs 0.000 description 14
• 239000012453 solvate Substances 0.000 description 14
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 13
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 13
• 230000006399 behavior Effects 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• 125000003386 piperidinyl group Chemical group 0.000 description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
• 229920002554 vinyl polymer Polymers 0.000 description 13
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 12
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 12
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 12
• 125000000335 thiazolyl group Chemical group 0.000 description 12
• 125000001544 thienyl group Chemical group 0.000 description 12
• 125000003396 thiol group Chemical group [H]S* 0.000 description 12
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 11
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
• 239000011737 fluorine Substances 0.000 description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 11
• 229910052717 sulfur Inorganic materials 0.000 description 11
• 239000003981 vehicle Substances 0.000 description 11
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 10
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• 125000004104 aryloxy group Chemical group 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 10
• 125000002883 imidazolyl group Chemical group 0.000 description 10
• 230000001771 impaired effect Effects 0.000 description 10
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 10
• 108090000623 proteins and genes Proteins 0.000 description 10
• 125000000168 pyrrolyl group Chemical group 0.000 description 10
• 229940124530 sulfonamide Drugs 0.000 description 10
• 150000003456 sulfonamides Chemical class 0.000 description 10
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 9
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• 241000282412 Homo Species 0.000 description 9
• 125000003282 alkyl amino group Chemical group 0.000 description 9
• 230000003542 behavioural effect Effects 0.000 description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
• 125000002971 oxazolyl group Chemical group 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• 125000003831 tetrazolyl group Chemical group 0.000 description 9
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 9
• 125000001425 triazolyl group Chemical group 0.000 description 9
• YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 8
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 8
• ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 8
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 8
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 125000002837 carbocyclic group Chemical group 0.000 description 8
• 125000004122 cyclic group Chemical group 0.000 description 8
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• 235000013305 food Nutrition 0.000 description 8
• 230000013016 learning Effects 0.000 description 8
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 8
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
• 125000001624 naphthyl group Chemical group 0.000 description 8
• 239000001301 oxygen Substances 0.000 description 8
• 125000004193 piperazinyl group Chemical group 0.000 description 8
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 7
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• DHSHMTXXPHLFOX-UHFFFAOYSA-N 1-(imidazol-1-ylmethyl)-4-propylpyrrolidin-2-one Chemical compound O=C1CC(CCC)CN1CN1C=NC=C1 DHSHMTXXPHLFOX-UHFFFAOYSA-N 0.000 description 6
• HYZJCKYKOHLVJF-SFIIULIVSA-N 1H-benzimidazole Chemical group C1=CC=C2N[11CH]=NC2=C1 HYZJCKYKOHLVJF-SFIIULIVSA-N 0.000 description 6
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