OA12812A - (4-phenyl) Piperidin-3-yl-phenylcarboxylate derovatoves and related compounds as beta-secretase inhibitors for the treatment of Alzheimer's Disease. - Google Patents

Info

Publication number

OA12812A

OA12812A OA1200400289A OA1200400289A OA12812A OA 12812 A OA12812 A OA 12812A OA 1200400289 A OA1200400289 A OA 1200400289A OA 1200400289 A OA1200400289 A OA 1200400289A OA 12812 A OA12812 A OA 12812A

Authority

OA

OAPI

Prior art keywords

alkyl

alkoxy

heteroaryl

aryl

optionally substituted

Prior art date

2001-11-19

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 236
• 208000024827 Alzheimer disease Diseases 0.000 title claims abstract description 55
• 238000011282 treatment Methods 0.000 title claims abstract description 26
• 239000002439 beta secretase inhibitor Substances 0.000 title description 2
• XLBBQFVOBCYVAO-UHFFFAOYSA-N piperidin-3-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCCNC1 XLBBQFVOBCYVAO-UHFFFAOYSA-N 0.000 title description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 525
• -1 indenyl,dihydronaphthyl Chemical group 0.000 claims description 283
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 99
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 98
• 125000003545 alkoxy group Chemical group 0.000 claims description 97
• 125000001424 substituent group Chemical group 0.000 claims description 81
• 238000000034 method Methods 0.000 claims description 65
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 61
• 201000010099 disease Diseases 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 206010012289 Dementia Diseases 0.000 claims description 31
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 27
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
• 150000002148 esters Chemical class 0.000 claims description 26
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• 208000010877 cognitive disease Diseases 0.000 claims description 25
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 25
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• 239000000460 chlorine Substances 0.000 claims description 18
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 16
• 238000004519 manufacturing process Methods 0.000 claims description 16
• 239000004576 sand Substances 0.000 claims description 16
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
• 208000032843 Hemorrhage Diseases 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 12
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 12
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 11
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 11
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 125000004193 piperazinyl group Chemical group 0.000 claims description 11
• 125000003386 piperidinyl group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• 201000010374 Down Syndrome Diseases 0.000 claims description 10
• 206010044688 Trisomy 21 Diseases 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 9
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
• 210000004558 lewy body Anatomy 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 230000001054 cortical effect Effects 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 7
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 230000007850 degeneration Effects 0.000 claims description 6
• 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 229910014585 C2-Ce Inorganic materials 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 5
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000005992 dihydrobenzisothiazinyl group Chemical group 0.000 claims description 5
• 125000005993 dihydrobenzisoxazinyl group Chemical group 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000005994 isobenzotetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000005995 isobenzotetrahydrothienyl group Chemical group 0.000 claims description 5
• 125000005990 isobenzothienyl group Chemical group 0.000 claims description 5
• 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 5
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 5
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 5
• 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 5
• 125000004306 triazinyl group Chemical group 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000004594 isoindolinyl group Chemical group C1(NCC2=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
• 125000006413 ring segment Chemical group 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 claims description 3
• RMDRPJICNOYAKA-UHFFFAOYSA-N 4-(furan-3-yl)-3-phenylmethoxypiperidine Chemical compound C=1C=CC=CC=1COC1CNCCC1C=1C=COC=1 RMDRPJICNOYAKA-UHFFFAOYSA-N 0.000 claims description 3
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 claims description 3
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000003151 isocoumarinyl group Chemical group C1(=O)OC(=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• HGIMBSWXDDCBSB-UHFFFAOYSA-N piperidin-3-yl benzoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)OC1CCCNC1 HGIMBSWXDDCBSB-UHFFFAOYSA-N 0.000 claims description 3
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
• 125000004620 quinolinyl-N-oxide group Chemical group 0.000 claims description 3
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• 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 claims description 2
• WEZPWYINNFMBFP-UHFFFAOYSA-N 3-(2-ethylbutoxy)-4-(furan-3-yl)piperidine Chemical compound CCC(CC)COC1CNCCC1C1=COC=C1 WEZPWYINNFMBFP-UHFFFAOYSA-N 0.000 claims description 2
• GURJTLNIHIJDTD-UHFFFAOYSA-N 3-benzyl-5-[(3,5-difluorophenyl)methoxy]piperidine;hydrochloride Chemical compound Cl.FC1=CC(F)=CC(COC2CC(CC=3C=CC=CC=3)CNC2)=C1 GURJTLNIHIJDTD-UHFFFAOYSA-N 0.000 claims description 2
• HNCBMNIJIFASAN-UHFFFAOYSA-N 4-(furan-3-yl)-3-[(3-methylphenyl)methoxy]piperidine Chemical compound CC1=CC=CC(COC2C(CCNC2)C2=COC=C2)=C1 HNCBMNIJIFASAN-UHFFFAOYSA-N 0.000 claims description 2
• 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
• PNLXQFOXOPGOGI-UHFFFAOYSA-N 4-tert-butylbenzoic acid;hydrochloride Chemical compound Cl.CC(C)(C)C1=CC=C(C(O)=O)C=C1 PNLXQFOXOPGOGI-UHFFFAOYSA-N 0.000 claims description 2
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• RRPFCEOETNGQTJ-PKTZIBPZSA-N [(3r,4r)-4-phenylpiperidin-3-yl] 4-phenylbenzoate Chemical compound C1([C@H]2CCNC[C@@H]2OC(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=CC=CC=C1 RRPFCEOETNGQTJ-PKTZIBPZSA-N 0.000 claims description 2
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims description 2
• 150000001721 carbon Chemical group 0.000 claims description 2
• 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• BGTWFLFIGDHQLW-UHFFFAOYSA-N naphthalene-1-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=C2C(C(=O)O)=CC=CC2=C1 BGTWFLFIGDHQLW-UHFFFAOYSA-N 0.000 claims description 2
• CCDHNWMQXILBED-UHFFFAOYSA-N tert-butyl 3-(2-ethylbutoxy)-4-(furan-3-yl)piperidine-1-carboxylate Chemical compound CCC(CC)COC1CN(C(=O)OC(C)(C)C)CCC1C1=COC=C1 CCDHNWMQXILBED-UHFFFAOYSA-N 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• 125000004001 thioalkyl group Chemical group 0.000 claims description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
• SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 2
• JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 claims 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• JCGGLXLQYKVCJQ-UHFFFAOYSA-N 2-methylbenzoic acid;hydrochloride Chemical compound Cl.CC1=CC=CC=C1C(O)=O JCGGLXLQYKVCJQ-UHFFFAOYSA-N 0.000 claims 1
• PFPVBWQNIZSRML-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.COC=1C=C(C(=O)O)C=CC1OC PFPVBWQNIZSRML-UHFFFAOYSA-N 0.000 claims 1
• QCYSDQPAJYSSNZ-UHFFFAOYSA-N 3-benzyl-5-[[4-(trifluoromethyl)phenyl]methoxy]piperidine;hydrochloride Chemical compound Cl.C1=CC(C(F)(F)F)=CC=C1COC1CC(CC=2C=CC=CC=2)CNC1 QCYSDQPAJYSSNZ-UHFFFAOYSA-N 0.000 claims 1
• HVNKNWVPVZWGDW-UHFFFAOYSA-N 4-nitrobenzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C([N+]([O-])=O)C=C1 HVNKNWVPVZWGDW-UHFFFAOYSA-N 0.000 claims 1
• GZVSWJNWQWALEB-UHFFFAOYSA-N C(C)(C)(C)OC(=O)N1C(CC(CC1)C1=COC=C1)OCC1=CC=CC=C1 Chemical compound C(C)(C)(C)OC(=O)N1C(CC(CC1)C1=COC=C1)OCC1=CC=CC=C1 GZVSWJNWQWALEB-UHFFFAOYSA-N 0.000 claims 1
• REZZCCSEWOWPQV-UHFFFAOYSA-N Cl.C(C1=CC=CC=C1)N1CCCC(C1)OCC1=CC(=CC=C1)OC Chemical compound Cl.C(C1=CC=CC=C1)N1CCCC(C1)OCC1=CC(=CC=C1)OC REZZCCSEWOWPQV-UHFFFAOYSA-N 0.000 claims 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
• 239000013256 coordination polymer Substances 0.000 claims 1
• 125000002946 cyanobenzyl group Chemical group 0.000 claims 1
• 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims 1
• 229910052698 phosphorus Inorganic materials 0.000 claims 1
• UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 claims 1
• 125000005289 uranyl group Chemical group 0.000 claims 1
• 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 abstract description 87
• 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 abstract description 87
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