JP2008507538A5 - - Google Patents
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- JP2008507538A5 JP2008507538A5 JP2007522711A JP2007522711A JP2008507538A5 JP 2008507538 A5 JP2008507538 A5 JP 2008507538A5 JP 2007522711 A JP2007522711 A JP 2007522711A JP 2007522711 A JP2007522711 A JP 2007522711A JP 2008507538 A5 JP2008507538 A5 JP 2008507538A5
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- JP
- Japan
- Prior art keywords
- alkyl
- compound
- composition
- substituted
- effective amount
- Prior art date
- 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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- 150000001875 compounds Chemical class 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 239000000203 mixture Substances 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 12
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 206010012289 Dementia Diseases 0.000 claims 7
- -1 heterocyclylene Chemical group 0.000 claims 7
- 230000004770 neurodegeneration Effects 0.000 claims 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000000732 arylene group Chemical group 0.000 claims 4
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 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 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 2
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims 1
- 102100033639 Acetylcholinesterase Human genes 0.000 claims 1
- 108010022752 Acetylcholinesterase Proteins 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims 1
- 230000007351 Aβ plaque formation Effects 0.000 claims 1
- 108010053652 Butyrylcholinesterase Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 102100032404 Cholinesterase Human genes 0.000 claims 1
- 229940125373 Gamma-Secretase Inhibitor Drugs 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims 1
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 claims 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 claims 1
- RVOLLAQWKVFTGE-UHFFFAOYSA-N Pyridostigmine Chemical compound CN(C)C(=O)OC1=CC=C[N+](C)=C1 RVOLLAQWKVFTGE-UHFFFAOYSA-N 0.000 claims 1
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims 1
- 229940022698 acetylcholinesterase Drugs 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 1
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 229960005370 atorvastatin Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229960000590 celecoxib Drugs 0.000 claims 1
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- 229960001259 diclofenac Drugs 0.000 claims 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 claims 1
- 229960000616 diflunisal Drugs 0.000 claims 1
- 229960003530 donepezil Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229960005293 etodolac Drugs 0.000 claims 1
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229960002390 flurbiprofen Drugs 0.000 claims 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims 1
- 229960003765 fluvastatin Drugs 0.000 claims 1
- 229960003980 galantamine Drugs 0.000 claims 1
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims 1
- 239000003540 gamma secretase inhibitor Substances 0.000 claims 1
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 1
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 125000005368 heteroarylthio group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 229960001680 ibuprofen Drugs 0.000 claims 1
- 229960000905 indomethacin Drugs 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims 1
- 229960000991 ketoprofen Drugs 0.000 claims 1
- 229960004752 ketorolac Drugs 0.000 claims 1
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims 1
- 229960004844 lovastatin Drugs 0.000 claims 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical group C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims 1
- 229960004640 memantine Drugs 0.000 claims 1
- 229960004270 nabumetone Drugs 0.000 claims 1
- 229960002009 naproxen Drugs 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 229960002362 neostigmine Drugs 0.000 claims 1
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 claims 1
- 229960002739 oxaprozin Drugs 0.000 claims 1
- 229960002702 piroxicam Drugs 0.000 claims 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims 1
- 229960002965 pravastatin Drugs 0.000 claims 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229960002290 pyridostigmine Drugs 0.000 claims 1
- 229960004136 rivastigmine Drugs 0.000 claims 1
- 229960000371 rofecoxib Drugs 0.000 claims 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims 1
- 229960000672 rosuvastatin Drugs 0.000 claims 1
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims 1
- 229960002855 simvastatin Drugs 0.000 claims 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 claims 1
- 229960000894 sulindac Drugs 0.000 claims 1
- 229960001685 tacrine Drugs 0.000 claims 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical group C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims 1
- 0 ***CC(C(*)O)NC(*)=O Chemical compound ***CC(C(*)O)NC(*)=O 0.000 description 14
- QMXPTUUFGSTIKK-UHFFFAOYSA-N CCC(CC1)NC1=O Chemical compound CCC(CC1)NC1=O QMXPTUUFGSTIKK-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N CCc1ccccc1 Chemical compound CCc1ccccc1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 3
- ALMHSXDYCFOZQD-UHFFFAOYSA-N CC(Nc1cccc(C)c1)=O Chemical compound CC(Nc1cccc(C)c1)=O ALMHSXDYCFOZQD-UHFFFAOYSA-N 0.000 description 2
- KAMADDWOIUPNMK-UHFFFAOYSA-N CCCN(CCO1)C1=O Chemical compound CCCN(CCO1)C1=O KAMADDWOIUPNMK-UHFFFAOYSA-N 0.000 description 2
- JAWZAONCXMJLFT-UHFFFAOYSA-N CCCc1ccncc1 Chemical compound CCCc1ccncc1 JAWZAONCXMJLFT-UHFFFAOYSA-N 0.000 description 2
- MLAXEZHEGARMPE-UHFFFAOYSA-N CCCc1cnccc1 Chemical compound CCCc1cnccc1 MLAXEZHEGARMPE-UHFFFAOYSA-N 0.000 description 2
- GPOFSFLJOIAMSA-UHFFFAOYSA-N CCc(cc1)ccc1Cl Chemical compound CCc(cc1)ccc1Cl GPOFSFLJOIAMSA-UHFFFAOYSA-N 0.000 description 2
- BLDNWXVISIXWKZ-UHFFFAOYSA-N CCc(cc1)ccc1F Chemical compound CCc(cc1)ccc1F BLDNWXVISIXWKZ-UHFFFAOYSA-N 0.000 description 2
- WOSJQXCRYIYFKT-UHFFFAOYSA-N CCc(cn1)ccc1OC Chemical compound CCc(cn1)ccc1OC WOSJQXCRYIYFKT-UHFFFAOYSA-N 0.000 description 2
- ULVNWAWZNVCNRB-UHFFFAOYSA-N CCc1ccc(C(F)(F)F)[o]1 Chemical compound CCc1ccc(C(F)(F)F)[o]1 ULVNWAWZNVCNRB-UHFFFAOYSA-N 0.000 description 2
- ZLCSFXXPPANWQY-UHFFFAOYSA-N CCc1cccc(C)c1 Chemical compound CCc1cccc(C)c1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 2
- DWLZULQNIPIABE-UHFFFAOYSA-N CCc1cccc(OC)c1 Chemical compound CCc1cccc(OC)c1 DWLZULQNIPIABE-UHFFFAOYSA-N 0.000 description 2
- MFEIKQPHQINPRI-UHFFFAOYSA-N CCc1cccnc1 Chemical compound CCc1cccnc1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 description 2
- SJWHILBZPGQBJE-UHFFFAOYSA-N CCc1ccnc(N)c1 Chemical compound CCc1ccnc(N)c1 SJWHILBZPGQBJE-UHFFFAOYSA-N 0.000 description 2
- VJXRKZJMGVSXPX-UHFFFAOYSA-N CCc1ccncc1 Chemical compound CCc1ccncc1 VJXRKZJMGVSXPX-UHFFFAOYSA-N 0.000 description 2
- BJZMHNBXROHGCM-UHFFFAOYSA-N CCc1ccncc1Br Chemical compound CCc1ccncc1Br BJZMHNBXROHGCM-UHFFFAOYSA-N 0.000 description 2
- APVBPNQCNREQQD-UHFFFAOYSA-N CCc1ccncc1CC Chemical compound CCc1ccncc1CC APVBPNQCNREQQD-UHFFFAOYSA-N 0.000 description 2
- XGHABZPSYISTKF-UHFFFAOYSA-N CCc1ccnnc1 Chemical compound CCc1ccnnc1 XGHABZPSYISTKF-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N Cc1cc(N)ccc1 Chemical compound Cc1cc(N)ccc1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N Cc1ccncc1 Chemical compound Cc1ccncc1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- BOULMKGNQBTPMU-AHWVRZQESA-N CC(C)CCOc1cc(F)cc(C[C@@H](C[C@@H]2NCCN(Cc3ccccc3)C2=O)NC(C)=O)c1 Chemical compound CC(C)CCOc1cc(F)cc(C[C@@H](C[C@@H]2NCCN(Cc3ccccc3)C2=O)NC(C)=O)c1 BOULMKGNQBTPMU-AHWVRZQESA-N 0.000 description 1
- XCWCIKYMVDFWLR-UHFFFAOYSA-N CC(C)S(c1cccc(C)c1)(=O)=O Chemical compound CC(C)S(c1cccc(C)c1)(=O)=O XCWCIKYMVDFWLR-UHFFFAOYSA-N 0.000 description 1
- GOFGZFDCXCHPAZ-HFKVKABFSA-N CC(CCOc1cc(F)cc(C[C@@H](C[C@@H]2NCCN(Cc3ccccc3)C2=O)NC(C)=O)c1)OC Chemical compound CC(CCOc1cc(F)cc(C[C@@H](C[C@@H]2NCCN(Cc3ccccc3)C2=O)NC(C)=O)c1)OC GOFGZFDCXCHPAZ-HFKVKABFSA-N 0.000 description 1
- SUYWPEXSOTVOFJ-UHFFFAOYSA-O CC(NC(CC1NCCN(Cc2ccccc2)C1=O)Cc1cc(OCC(C=C[NH3+])=CN)cc(F)c1)=O Chemical compound CC(NC(CC1NCCN(Cc2ccccc2)C1=O)Cc1cc(OCC(C=C[NH3+])=CN)cc(F)c1)=O SUYWPEXSOTVOFJ-UHFFFAOYSA-O 0.000 description 1
- LGPHOTSXLIEWJR-UOCXPQTGSA-N CC(N[C@H](CCNCCN(C)C(C[O]=C1)C1c1cc(C)ccc1)Cc1cc(F)cc(OCc2cccnc2)c1)=O Chemical compound CC(N[C@H](CCNCCN(C)C(C[O]=C1)C1c1cc(C)ccc1)Cc1cc(F)cc(OCc2cccnc2)c1)=O LGPHOTSXLIEWJR-UOCXPQTGSA-N 0.000 description 1
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| AU2008220785B2 (en) | 2007-03-01 | 2013-02-21 | Vivoryon Therapeutics N.V. | New use of glutaminyl cyclase inhibitors |
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| EP2227471A1 (en) * | 2007-12-11 | 2010-09-15 | Schering Corporation | Gamma secretase modulators |
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| RU2011123862A (ru) | 2008-11-13 | 2012-12-20 | Шеринг Корпорейшн | Модуляторы гамма-секретазы |
| US8759337B2 (en) | 2008-12-22 | 2014-06-24 | Merck Sharp & Dohme Corp. | Gamma secretase modulators |
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| EP2443118A1 (en) | 2009-06-16 | 2012-04-25 | Schering Corporation | Gamma secretase modulators |
| WO2010147969A2 (en) | 2009-06-16 | 2010-12-23 | Schering Corporation | Gamma secretase modulators |
| US20120245158A1 (en) | 2009-06-16 | 2012-09-27 | Xianhai Huang | Gamma secretase modulators |
| JP5934645B2 (ja) | 2009-09-11 | 2016-06-15 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのヘテロ環式誘導体 |
| US8563543B2 (en) | 2009-10-08 | 2013-10-22 | Merck Sharp & Dohme Corp. | Iminothiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| UA108363C2 (uk) | 2009-10-08 | 2015-04-27 | Похідні імінотіадіазиндіоксиду як інгібітори bace, композиція на їх основі і їх застосування | |
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| EP2485590B1 (en) | 2009-10-08 | 2015-01-07 | Merck Sharp & Dohme Corp. | Pentafluorosulfur imino heterocyclic compounds as bace-1 inhibitors, compositions, and their use |
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| JP5688745B2 (ja) | 2010-03-10 | 2015-03-25 | プロビオドルグ エージー | グルタミニルシクラーゼ（ｑｃ、ｅｃ２．３．２．５）の複素環阻害剤 |
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| EP2694489B1 (en) | 2011-04-07 | 2017-09-06 | Merck Sharp & Dohme Corp. | C5-c6 oxacyclic-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| RU2014111055A (ru) | 2011-08-22 | 2015-09-27 | Мерк Шарп И Доум Корп. | 2-спирозамещенные иминотиазины и их моно- и диоксиды в качестве ингибиторов bace, композиции и их применение |
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| AU2013235422B2 (en) | 2012-03-19 | 2016-12-15 | Buck Institute For Research On Aging | APP specific BACE inhibitors (ASBIs) and uses thereof |
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| WO2003014075A2 (en) * | 2001-08-03 | 2003-02-20 | Schering Corporation | Novel gamma secretase inhibitors |
| HUP0401241A3 (en) | 2001-08-21 | 2008-03-28 | Merck Sharp & Dohme | Novel cyclohexyl sulphones, process for their preparation and pharmaceutical compositions containing them |
| US6673821B2 (en) * | 2001-10-22 | 2004-01-06 | Enanta Pharmaceuticals, Inc. | Nitrogen heterocycle inhibitors of aspartyl protease |
| TW200302717A (en) | 2002-02-06 | 2003-08-16 | Schering Corp | Novel gamma secretase inhibitors |
| WO2003094854A2 (en) * | 2002-05-07 | 2003-11-20 | Elan Pharmaceuticals, Inc. | Succinoyl aminopyrazoles and related compounds |
| WO2004004396A1 (en) | 2002-06-26 | 2004-01-08 | Nokia Corporation | Method and network element for optimisation of radio resource utilisation in a radio access network |
| CA2505098A1 (en) * | 2002-11-12 | 2004-05-27 | Merck & Co., Inc. | Phenylcarboxamide beta-secretase inhibitors for the treatment of alzheimer's disease |
| WO2005108358A2 (en) * | 2004-04-22 | 2005-11-17 | Eli Lilly And Company | Pyrrolidine derivatives useful as bace inhibitors |
| AU2006315817A1 (en) * | 2005-11-16 | 2007-05-24 | Merck & Co., Inc. | Imidazolidinone compounds useful as beta-secretase inhibitors for the treatment of Alzheimer's disease |
-
2005
- 2005-07-20 EP EP05773473A patent/EP1781625B1/en not_active Expired - Lifetime
- 2005-07-20 JP JP2007522711A patent/JP2008507538A/ja active Pending
- 2005-07-20 ES ES05773473T patent/ES2355733T3/es not_active Expired - Lifetime
- 2005-07-20 CN CNA2005800300344A patent/CN101014577A/zh active Pending
- 2005-07-20 AR ARP050103000A patent/AR049726A1/es not_active Application Discontinuation
- 2005-07-20 US US11/185,419 patent/US7803802B2/en active Active
- 2005-07-20 CA CA002574218A patent/CA2574218A1/en not_active Abandoned
- 2005-07-20 WO PCT/US2005/025780 patent/WO2006014762A1/en not_active Ceased
- 2005-07-20 AT AT05773473T patent/ATE491693T1/de not_active IP Right Cessation
- 2005-07-20 MX MX2007000760A patent/MX2007000760A/es active IP Right Grant
- 2005-07-20 DE DE602005025363T patent/DE602005025363D1/de not_active Expired - Lifetime
- 2005-07-21 TW TW094124686A patent/TW200621249A/zh unknown
-
2010
- 2010-08-23 US US12/861,347 patent/US8367712B2/en not_active Expired - Lifetime
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