DK2346500T3 - Methods and compositions for improving cognitive function - Google Patents

Info

Publication number

DK2346500T3

DK2346500T3 DK09748527.0T DK09748527T DK2346500T3 DK 2346500 T3 DK2346500 T3 DK 2346500T3 DK 09748527 T DK09748527 T DK 09748527T DK 2346500 T3 DK2346500 T3 DK 2346500T3

Authority

DK

Denmark

Prior art keywords

oxo

methyl

hydrogen

alkyl

butanamide

Prior art date

2008-10-16

Links

• Espacenet
• Global Dossier
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• 239000000203 mixture Substances 0.000 title claims description 92
• 238000000034 method Methods 0.000 title description 70
• 230000003920 cognitive function Effects 0.000 title description 34
• 150000003839 salts Chemical class 0.000 claims description 73
• 208000010877 cognitive disease Diseases 0.000 claims description 66
• HPHUVLMMVZITSG-ZCFIWIBFSA-N levetiracetam Chemical compound CC[C@H](C(N)=O)N1CCCC1=O HPHUVLMMVZITSG-ZCFIWIBFSA-N 0.000 claims description 66
• 229960004002 levetiracetam Drugs 0.000 claims description 62
• 238000011282 treatment Methods 0.000 claims description 32
• 239000003814 drug Substances 0.000 claims description 23
• 230000007000 age related cognitive decline Effects 0.000 claims description 15
• 238000013265 extended release Methods 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims 1
• 230000007074 memory dysfunction Effects 0.000 claims 1
• -1 solubility Chemical class 0.000 description 551
• 229910052739 hydrogen Inorganic materials 0.000 description 297
• 239000001257 hydrogen Substances 0.000 description 296
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 236
• 125000000217 alkyl group Chemical group 0.000 description 184
• 229910052736 halogen Inorganic materials 0.000 description 176
• 150000002367 halogens Chemical class 0.000 description 141
• 150000001875 compounds Chemical class 0.000 description 120
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 112
• 125000003118 aryl group Chemical group 0.000 description 95
• 101710084141 Synaptic vesicle glycoprotein 2A Proteins 0.000 description 86
• 241000700159 Rattus Species 0.000 description 85
• 102100030701 Synaptic vesicle glycoprotein 2A Human genes 0.000 description 79
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 73
• 125000000623 heterocyclic group Chemical group 0.000 description 69
• 239000003112 inhibitor Substances 0.000 description 69
• 125000001424 substituent group Chemical group 0.000 description 66
• 125000004093 cyano group Chemical group *C#N 0.000 description 65
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 63
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 60
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 59
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 56
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 54
• 125000003545 alkoxy group Chemical group 0.000 description 49
• 208000028698 Cognitive impairment Diseases 0.000 description 45
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 45
• 125000005843 halogen group Chemical group 0.000 description 44
• 125000002252 acyl group Chemical group 0.000 description 41
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 37
• 125000003368 amide group Chemical group 0.000 description 36
• 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
• 239000003795 chemical substances by application Substances 0.000 description 34
• 125000003342 alkenyl group Chemical group 0.000 description 32
• 125000000753 cycloalkyl group Chemical group 0.000 description 32
• NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 29
• 125000000304 alkynyl group Chemical group 0.000 description 27
• 125000004414 alkyl thio group Chemical group 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 26
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 25
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 25
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• 238000012360 testing method Methods 0.000 description 24
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 23
• 125000001309 chloro group Chemical group Cl* 0.000 description 22
• MSYKRHVOOPPJKU-BDAKNGLRSA-N brivaracetam Chemical compound CCC[C@H]1CN([C@@H](CC)C(N)=O)C(=O)C1 MSYKRHVOOPPJKU-BDAKNGLRSA-N 0.000 description 20
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 19
• 125000002541 furyl group Chemical group 0.000 description 18
• 239000000523 sample Substances 0.000 description 18
• 125000003396 thiol group Chemical class [H]S* 0.000 description 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 17
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
• 230000014759 maintenance of location Effects 0.000 description 17
• 208000027061 mild cognitive impairment Diseases 0.000 description 17
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 17
• 125000004076 pyridyl group Chemical group 0.000 description 17
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 17
• 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 16
• 230000015654 memory Effects 0.000 description 16
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 15
• 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
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 15
• 229910052760 oxygen Inorganic materials 0.000 description 15
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
• AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 14
• 239000012453 solvate Substances 0.000 description 14
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 13
• 229910052731 fluorine Inorganic materials 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
• 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 12
• 230000032683 aging Effects 0.000 description 12
• 229910052794 bromium Inorganic materials 0.000 description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 12
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 12
• 125000000335 thiazolyl group Chemical group 0.000 description 12
• 125000001544 thienyl group Chemical group 0.000 description 12
• 229940102566 valproate Drugs 0.000 description 12
• 229960000604 valproic acid Drugs 0.000 description 12
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 11
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 11
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 11
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 239000000460 chlorine 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
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
• 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 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 11
• 239000003981 vehicle Substances 0.000 description 11
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 10
• 241000282412 Homo Species 0.000 description 10
• 125000004104 aryloxy group Chemical group 0.000 description 10
• 125000002883 imidazolyl group Chemical group 0.000 description 10
• 125000003386 piperidinyl group Chemical group 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
• 125000003831 tetrazolyl group Chemical group 0.000 description 10
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
• MSTWYMAKOBGMBF-UHFFFAOYSA-N 1-(imidazol-1-ylmethyl)-4-phenylpyrrolidin-2-one Chemical compound O=C1CC(C=2C=CC=CC=2)CN1CN1C=CN=C1 MSTWYMAKOBGMBF-UHFFFAOYSA-N 0.000 description 9
• 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 description 9
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 9
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 9
• 206010012289 Dementia Diseases 0.000 description 9
• 125000003282 alkyl amino group Chemical group 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 9
• 206010027175 memory impairment Diseases 0.000 description 9
• 125000002971 oxazolyl group Chemical group 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• 229910052717 sulfur Inorganic materials 0.000 description 9
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 9
• 125000001425 triazolyl group Chemical group 0.000 description 9
• 229920002554 vinyl polymer Polymers 0.000 description 9
• HKNUWEVPOFSOKN-UHFFFAOYSA-N 4-(3-azido-2,4-difluorophenyl)-1-(imidazol-1-ylmethyl)pyrrolidin-2-one Chemical compound FC1=C(N=[N+]=[N-])C(F)=CC=C1C1CC(=O)N(CN2C=NC=C2)C1 HKNUWEVPOFSOKN-UHFFFAOYSA-N 0.000 description 8
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 8
• 239000004215 Carbon black (E152) Substances 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 125000002837 carbocyclic group Chemical group 0.000 description 8
• 229910052799 carbon Inorganic materials 0.000 description 8
• 125000004122 cyclic group Chemical group 0.000 description 8
• 235000013305 food Nutrition 0.000 description 8
• 229930195733 hydrocarbon Natural products 0.000 description 8
• 230000001771 impaired effect Effects 0.000 description 8
• 230000013016 learning Effects 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
• 125000004193 piperazinyl group Chemical group 0.000 description 8
• 239000000243 solution Substances 0.000 description 8
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 7
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 7
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 7
• 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 7
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 7
• 125000004423 acyloxy group Chemical group 0.000 description 7
• 125000005110 aryl thio group Chemical group 0.000 description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
• 230000003542 behavioural effect Effects 0.000 description 7
• 210000004027 cell Anatomy 0.000 description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
• 230000007423 decrease Effects 0.000 description 7
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• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 7
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
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• 108091032973 (ribonucleotides)n+m Proteins 0.000 description 6
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• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 6
• LWOVRKKVJJZLHR-UHFFFAOYSA-N 3-[[2-oxo-4-(3,4,5-trifluorophenyl)pyrrolidin-1-yl]methyl]imidazole-4-carbonitrile Chemical compound FC1=C(F)C(F)=CC(C2CC(=O)N(CN3C(=CN=C3)C#N)C2)=C1 LWOVRKKVJJZLHR-UHFFFAOYSA-N 0.000 description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
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• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
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• VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 6
• 125000005135 aryl sulfinyl group Chemical group 0.000 description 6
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• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 5
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• 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 4
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• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
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• 125000003725 azepanyl group Chemical group 0.000 description 4
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• 239000008280 blood Substances 0.000 description 4
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• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
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• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 4
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