JP2004532868A5 - - Google Patents
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- JP2004532868A5 JP2004532868A5 JP2002592925A JP2002592925A JP2004532868A5 JP 2004532868 A5 JP2004532868 A5 JP 2004532868A5 JP 2002592925 A JP2002592925 A JP 2002592925A JP 2002592925 A JP2002592925 A JP 2002592925A JP 2004532868 A5 JP2004532868 A5 JP 2004532868A5
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- JP
- Japan
- Prior art keywords
- alkyl
- group
- aryl
- independently
- coor
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 453
- 125000003118 aryl group Chemical group 0.000 claims 180
- 125000003545 alkoxy group Chemical group 0.000 claims 75
- 125000001424 substituent group Chemical group 0.000 claims 73
- 229910052739 hydrogen Inorganic materials 0.000 claims 72
- -1 R 7 -Benzyl Chemical group 0.000 claims 65
- 239000001257 hydrogen Substances 0.000 claims 64
- 125000003107 substituted aryl group Chemical group 0.000 claims 64
- 239000000203 mixture Substances 0.000 claims 50
- 125000001072 heteroaryl group Chemical group 0.000 claims 48
- 125000002947 alkylene group Chemical group 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 40
- 125000005843 halogen group Chemical group 0.000 claims 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 32
- 150000002431 hydrogen Chemical class 0.000 claims 32
- 238000006467 substitution reaction Methods 0.000 claims 32
- 150000003839 salts Chemical class 0.000 claims 30
- 239000012453 solvate Substances 0.000 claims 30
- 229910052736 halogen Inorganic materials 0.000 claims 29
- 150000002367 halogens Chemical class 0.000 claims 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 24
- 125000004432 carbon atom Chemical group C* 0.000 claims 20
- 125000003003 spiro group Chemical group 0.000 claims 20
- 229910052799 carbon Inorganic materials 0.000 claims 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000002541 furyl group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 125000002883 imidazolyl group Chemical group 0.000 claims 16
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 16
- 125000002757 morpholinyl group Chemical group 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 125000003386 piperidinyl group Chemical group 0.000 claims 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims 16
- 125000004076 pyridyl group Chemical group 0.000 claims 16
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 16
- 125000000168 pyrrolyl group Chemical group 0.000 claims 16
- 125000000335 thiazolyl group Chemical group 0.000 claims 16
- 125000001544 thienyl group Chemical group 0.000 claims 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 125000004450 alkenylene group Chemical group 0.000 claims 12
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims 12
- 125000001624 naphthyl group Chemical group 0.000 claims 12
- 125000002971 oxazolyl group Chemical group 0.000 claims 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 12
- 208000024827 Alzheimer disease Diseases 0.000 claims 9
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 9
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 9
- 125000002993 cycloalkylene group Chemical group 0.000 claims 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 150000001413 amino acids Chemical class 0.000 claims 8
- 125000004104 aryloxy group Chemical group 0.000 claims 8
- 150000001540 azides Chemical class 0.000 claims 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 8
- 125000005879 dioxolanyl group Chemical group 0.000 claims 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 7
- 239000008280 blood Substances 0.000 claims 6
- 210000004369 blood Anatomy 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 108010064539 amyloid beta-protein (1-42) Proteins 0.000 claims 5
- 210000004556 brain Anatomy 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims 4
- 108010025628 Apolipoproteins E Proteins 0.000 claims 4
- 102000013918 Apolipoproteins E Human genes 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 102000001708 Protein Isoforms Human genes 0.000 claims 4
- 108010029485 Protein Isoforms Proteins 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 4
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims 4
- 125000000676 alkoxyimino group Chemical group 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000005336 allyloxy group Chemical group 0.000 claims 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 4
- 125000002047 benzodioxolyl group Chemical class O1OC(C2=C1C=CC=C2)* 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims 4
- 230000001105 regulatory effect Effects 0.000 claims 4
- 125000004306 triazinyl group Chemical group 0.000 claims 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 239000000018 receptor agonist Substances 0.000 claims 3
- 229940044601 receptor agonist Drugs 0.000 claims 3
- 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 claims 2
- 102100037808 Mitogen-activated protein kinase 8 Human genes 0.000 claims 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 239000003963 antioxidant agent Substances 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 230000017531 blood circulation Effects 0.000 claims 2
- 208000006752 brain edema Diseases 0.000 claims 2
- 210000005013 brain tissue Anatomy 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003149 muscarinic antagonist Substances 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229960002855 simvastatin Drugs 0.000 claims 2
- 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 2
- 208000024891 symptom Diseases 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
- 101710175516 14 kDa zinc-binding protein Proteins 0.000 claims 1
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003140 4 aminobutyric acid A receptor blocking agent Substances 0.000 claims 1
- 239000003412 4 aminobutyric acid B receptor blocking agent Substances 0.000 claims 1
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 claims 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 claims 1
- 102000003678 AMPA Receptors Human genes 0.000 claims 1
- 108090000078 AMPA Receptors Proteins 0.000 claims 1
- 229940121975 Acetylcholine release stimulant Drugs 0.000 claims 1
- 229940123324 Acyltransferase inhibitor Drugs 0.000 claims 1
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 claims 1
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 claims 1
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 claims 1
- 108010060159 Apolipoprotein E4 Proteins 0.000 claims 1
- 229940088872 Apoptosis inhibitor Drugs 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
- 102000017926 CHRM2 Human genes 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- 229940121926 Calpain inhibitor Drugs 0.000 claims 1
- 102100035037 Calpastatin Human genes 0.000 claims 1
- 229940123169 Caspase inhibitor Drugs 0.000 claims 1
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229940122010 Corticotropin releasing factor antagonist Drugs 0.000 claims 1
- 102100032165 Corticotropin-releasing factor-binding protein Human genes 0.000 claims 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 229940123457 Free radical scavenger Drugs 0.000 claims 1
- 229940090502 GABA A receptor antagonist Drugs 0.000 claims 1
- 229940119207 GABA B receptor antagonist Drugs 0.000 claims 1
- 239000003691 GABA modulator Substances 0.000 claims 1
- 102400001370 Galanin Human genes 0.000 claims 1
- 101800002068 Galanin Proteins 0.000 claims 1
- 229940125373 Gamma-Secretase Inhibitor Drugs 0.000 claims 1
- 229940124108 Growth factor receptor agonist Drugs 0.000 claims 1
- 229940122236 Histamine receptor antagonist Drugs 0.000 claims 1
- 229940123486 Hormone receptor agonist Drugs 0.000 claims 1
- 102000009032 Imidazoline Receptors Human genes 0.000 claims 1
- 108010049134 Imidazoline Receptors Proteins 0.000 claims 1
- 238000008214 LDL Cholesterol Methods 0.000 claims 1
- 102000011965 Lipoprotein Receptors Human genes 0.000 claims 1
- 108010061306 Lipoprotein Receptors Proteins 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
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 claims 1
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- 239000012661 PARP inhibitor Substances 0.000 claims 1
- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 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
- 108010036933 Presenilin-1 Proteins 0.000 claims 1
- 102100022033 Presenilin-1 Human genes 0.000 claims 1
- 108010036908 Presenilin-2 Proteins 0.000 claims 1
- 102100022036 Presenilin-2 Human genes 0.000 claims 1
- 229940122210 Prolyl endopeptidase inhibitor Drugs 0.000 claims 1
- 229940123924 Protein kinase C inhibitor Drugs 0.000 claims 1
- 102000016983 Releasing hormones receptors Human genes 0.000 claims 1
- 108070000025 Releasing hormones receptors Proteins 0.000 claims 1
- 102000007451 Steroid Receptors Human genes 0.000 claims 1
- 108010085012 Steroid Receptors Proteins 0.000 claims 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 claims 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 claims 1
- 229940123186 Superoxide dismutase stimulant Drugs 0.000 claims 1
- 102000011923 Thyrotropin Human genes 0.000 claims 1
- 108010061174 Thyrotropin Proteins 0.000 claims 1
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 claims 1
- 102000012088 Vasoactive Intestinal Peptide Receptors Human genes 0.000 claims 1
- 108010075974 Vasoactive Intestinal Peptide Receptors Proteins 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 239000002404 acyltransferase inhibitor Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
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- 102000004305 alpha Adrenergic Receptors Human genes 0.000 claims 1
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 claims 1
- 230000006933 amyloid-beta aggregation Effects 0.000 claims 1
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000000739 antihistaminic agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 239000000074 antisense oligonucleotide Substances 0.000 claims 1
- 238000012230 antisense oligonucleotides Methods 0.000 claims 1
- 239000000158 apoptosis inhibitor Substances 0.000 claims 1
- 229960005370 atorvastatin Drugs 0.000 claims 1
- VJBCNMFKFZIXHC-UHFFFAOYSA-N azanium;2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)quinoline-3-carboxylate Chemical compound N.N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O VJBCNMFKFZIXHC-UHFFFAOYSA-N 0.000 claims 1
- 239000000755 benzodiazepine receptor inverse stimulating agent Substances 0.000 claims 1
- ORZXYSPOAVJYRU-UHFFFAOYSA-N benzyl 2-(2-formylpyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate Chemical compound O=CC1CCCN1C(=O)C1N(C(=O)OCC=2C=CC=CC=2)CCC1 ORZXYSPOAVJYRU-UHFFFAOYSA-N 0.000 claims 1
- 239000002439 beta secretase inhibitor Substances 0.000 claims 1
- 229920000080 bile acid sequestrant Polymers 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
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- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 claims 1
- 230000003196 chaotropic effect Effects 0.000 claims 1
- 239000002738 chelating agent Substances 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
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- 239000002769 corticotropin releasing factor antagonist Substances 0.000 claims 1
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- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
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- 150000002194 fatty esters Chemical class 0.000 claims 1
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- 239000003102 growth factor Substances 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- 229960004844 lovastatin Drugs 0.000 claims 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical group 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
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| US5130333A (en) * | 1990-10-19 | 1992-07-14 | E. R. Squibb & Sons, Inc. | Method for treating type II diabetes employing a cholesterol lowering drug |
| JP2640986B2 (ja) * | 1990-11-08 | 1997-08-13 | 高砂香料工業株式会社 | (1′r,3s)―3―(1′―ヒドロキシエチル)―アゼチジン―2―オン又はその誘導体の製造法 |
| US5145684A (en) * | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| US5157025A (en) * | 1991-04-01 | 1992-10-20 | E. R. Squibb & Sons, Inc. | Method for lowering serum cholesterol employing a phosphorus containing ace inhibitor alone or in combination with a cholesterol lowering drug |
| US5162117A (en) * | 1991-11-22 | 1992-11-10 | Schering Corporation | Controlled release flutamide composition |
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| US5631365A (en) * | 1993-09-21 | 1997-05-20 | Schering Corporation | Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents |
| JP3144624B2 (ja) * | 1995-06-02 | 2001-03-12 | 杏林製薬株式会社 | N−ベンジルジオキソチアゾリジルベンズアミド誘導体及びその製造法 |
| EP0865429A1 (en) * | 1995-12-08 | 1998-09-23 | Smithkline Beecham Plc | Azetidinone compounds for the treatment of atherosclerosis |
| GB9600464D0 (en) * | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
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| US20030153541A1 (en) * | 1997-10-31 | 2003-08-14 | Robert Dudley | Novel anticholesterol compositions and method for using same |
| CA2311356C (en) * | 1998-01-28 | 2004-07-13 | Warner-Lambert Company | Method for treating alzheimer's disease |
-
2002
- 2002-05-22 PT PT02774113T patent/PT1392287E/pt unknown
- 2002-05-22 CA CA002447884A patent/CA2447884A1/en not_active Abandoned
- 2002-05-22 AU AU2002308778A patent/AU2002308778A1/en not_active Abandoned
- 2002-05-22 DE DE60216275T patent/DE60216275T2/de not_active Expired - Fee Related
- 2002-05-22 JP JP2002592925A patent/JP2004532868A/ja active Pending
- 2002-05-22 WO PCT/US2002/016306 patent/WO2002096415A2/en not_active Ceased
- 2002-05-22 AR ARP020101893A patent/AR038956A1/es unknown
- 2002-05-22 MX MXPA03010843A patent/MXPA03010843A/es active IP Right Grant
- 2002-05-22 EP EP02774113A patent/EP1392287B8/en not_active Expired - Lifetime
- 2002-05-22 ES ES02774113T patent/ES2275007T3/es not_active Expired - Lifetime
- 2002-05-22 DK DK02774113T patent/DK1392287T3/da active
- 2002-05-22 AT AT02774113T patent/ATE345792T1/de not_active IP Right Cessation
- 2002-05-22 US US10/154,106 patent/US20030013699A1/en not_active Abandoned
-
2007
- 2007-01-15 CY CY20071100048T patent/CY1105922T1/el unknown
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