MXPA02012560A - Compuestos para tratar la enfermedad de alzheimer. - Google Patents
Compuestos para tratar la enfermedad de alzheimer.Info
- Publication number
- MXPA02012560A MXPA02012560A MXPA02012560A MXPA02012560A MXPA02012560A MX PA02012560 A MXPA02012560 A MX PA02012560A MX PA02012560 A MXPA02012560 A MX PA02012560A MX PA02012560 A MXPA02012560 A MX PA02012560A MX PA02012560 A MXPA02012560 A MX PA02012560A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- defined above
- group
- optionally substituted
- heteroaryl
- Prior art date
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 33
- 201000010099 disease Diseases 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 title claims description 50
- 150000001412 amines Chemical class 0.000 claims abstract description 69
- -1 dihydronaphtalyl Chemical group 0.000 claims description 758
- 125000000217 alkyl group Chemical group 0.000 claims description 628
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 513
- 125000001424 substituent group Chemical group 0.000 claims description 441
- 125000001246 bromo group Chemical group Br* 0.000 claims description 382
- 125000003545 alkoxy group Chemical group 0.000 claims description 334
- 229910052799 carbon Inorganic materials 0.000 claims description 265
- 229910052739 hydrogen Inorganic materials 0.000 claims description 221
- 125000000623 heterocyclic group Chemical group 0.000 claims description 204
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 186
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 160
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 141
- 125000003342 alkenyl group Chemical group 0.000 claims description 102
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 96
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 93
- 125000000304 alkynyl group Chemical group 0.000 claims description 88
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 84
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 81
- 108010052300 RA X peptide Proteins 0.000 claims description 79
- HPQVYPRTUSUIMA-UHFFFAOYSA-N Rubia akane RA-X Natural products C1=CC(OC)=CC=C1CC(N(C)C(=O)C(CCC(O)=O)NC(=O)C(C)NC(=O)C(N(C1=O)C)C2)C(=O)NC(C)C(=O)N(C)C1CC(C=C1)=CC=C1OC1=CC2=CC=C1OC HPQVYPRTUSUIMA-UHFFFAOYSA-N 0.000 claims description 79
- BNAKNBRLTYXQLE-VTENTOHYSA-N (2s)-n-[(e,2s,4s,7s)-7-[[(2r)-2-aminopropanoyl]amino]-4-formyl-5-(3-hydroxy-4-methoxyphenyl)-2-[[(z)-3-(4-methoxyphenyl)-2-(methylamino)prop-2-enoyl]amino]-3,6,10-trioxodec-8-en-4-yl]-3-(4-hydroxyphenyl)-n-methyl-2-(methylamino)propanamide Chemical compound C([C@H](NC)C(=O)N(C)[C@](C=O)(C(C(=O)[C@@H](NC(=O)[C@@H](C)N)\C=C\C=O)C=1C=C(O)C(OC)=CC=1)C(=O)[C@H](C)NC(=O)C(\NC)=C\C=1C=CC(OC)=CC=1)C1=CC=C(O)C=C1 BNAKNBRLTYXQLE-VTENTOHYSA-N 0.000 claims description 78
- 238000011282 treatment Methods 0.000 claims description 73
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 60
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 46
- 208000024827 Alzheimer disease Diseases 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 37
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 36
- 125000002971 oxazolyl group Chemical group 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 125000002541 furyl group Chemical group 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 35
- 125000000335 thiazolyl group Chemical group 0.000 claims description 35
- 125000001544 thienyl group Chemical group 0.000 claims description 35
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 35
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 34
- 125000004076 pyridyl group Chemical group 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000003386 piperidinyl group Chemical group 0.000 claims description 28
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 27
- 125000002757 morpholinyl group Chemical group 0.000 claims description 27
- 125000004193 piperazinyl group Chemical group 0.000 claims description 27
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 27
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 27
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 26
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 150000001721 carbon Chemical group 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 23
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 claims description 22
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 claims description 22
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 21
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 21
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000002883 imidazolyl group Chemical group 0.000 claims description 20
- 125000001041 indolyl group Chemical group 0.000 claims description 20
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 20
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 20
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 19
- 125000001425 triazolyl group Chemical group 0.000 claims description 19
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 18
- 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 18
- 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 18
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 18
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 18
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 18
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 18
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 18
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 18
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 18
- 125000004617 chromonyl group Chemical group O1C(=CC(C2=CC=CC=C12)=O)* 0.000 claims description 18
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 18
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 claims description 18
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 18
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 18
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 18
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 18
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 18
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 18
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 18
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 18
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 18
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 18
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 18
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 18
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 18
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 18
- 125000004306 triazinyl group Chemical group 0.000 claims description 18
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 18
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 17
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 16
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims description 16
- 125000005995 isobenzotetrahydrothienyl group Chemical group 0.000 claims description 16
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 16
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 16
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 16
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 16
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 16
- 229910014585 C2-Ce Inorganic materials 0.000 claims description 15
- 125000005994 isobenzotetrahydrofuranyl group Chemical group 0.000 claims description 14
- 125000003151 isocoumarinyl group Chemical group C1(=O)OC(=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 claims description 14
- 206010012289 Dementia Diseases 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 13
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 12
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 101710201629 Ribulose bisphosphate carboxylase/oxygenase activase 2, chloroplastic Proteins 0.000 claims description 10
- 210000004556 brain Anatomy 0.000 claims description 10
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 10
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 10
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 9
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 9
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 9
- 125000005051 dihydropyrazinyl group Chemical group N1(CC=NC=C1)* 0.000 claims description 9
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims description 9
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 9
- 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 claims description 9
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
- 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 description 8
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 201000010374 Down Syndrome Diseases 0.000 claims description 6
- 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 description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 5
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 claims description 5
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 claims description 5
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 208000037259 Amyloid Plaque Diseases 0.000 claims description 3
- 241000282412 Homo Species 0.000 claims description 3
- 125000005992 dihydrobenzisothiazinyl group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000000750 progressive effect Effects 0.000 claims description 3
- ANOSMWHGNPTQJO-UHFFFAOYSA-N 1-indazol-1-yloxyindazole Chemical compound N1=CC2=CC=CC=C2N1ON1C2=CC=CC=C2C=N1 ANOSMWHGNPTQJO-UHFFFAOYSA-N 0.000 claims description 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 125000005993 dihydrobenzisoxazinyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 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 70
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 42
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 34
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 34
- 125000004103 aminoalkyl group Chemical group 0.000 claims 34
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 34
- 125000001188 haloalkyl group Chemical group 0.000 claims 34
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 28
- 150000001204 N-oxides Chemical class 0.000 claims 27
- 150000002431 hydrogen Chemical group 0.000 claims 26
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 18
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 18
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 17
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 17
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims 17
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 17
- 125000003282 alkyl amino group Chemical group 0.000 claims 17
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims 17
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims 17
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 17
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 17
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 17
- 125000004663 dialkyl amino group Chemical group 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 17
- 125000005429 oxyalkyl group Chemical group 0.000 claims 17
- 125000004001 thioalkyl group Chemical group 0.000 claims 17
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 16
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims 16
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 16
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 15
- 229910052760 oxygen Inorganic materials 0.000 claims 15
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 15
- 239000000470 constituent Substances 0.000 claims 12
- 230000001681 protective effect Effects 0.000 claims 11
- 238000006467 substitution reaction Methods 0.000 claims 11
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 9
- 125000006196 aroyl alkyl group Chemical group 0.000 claims 9
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 9
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 9
- 210000004027 cell Anatomy 0.000 claims 8
- 230000002401 inhibitory effect Effects 0.000 claims 8
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 6
- 230000003412 degenerative effect Effects 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 5
- 208000018282 ACys amyloidosis Diseases 0.000 claims 5
- 208000007487 Familial Cerebral Amyloid Angiopathy Diseases 0.000 claims 5
- 208000032849 Hereditary cerebral hemorrhage with amyloidosis Diseases 0.000 claims 5
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 4
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims 4
- OTTXCOAOKOEENK-UHFFFAOYSA-N 2,2-difluoroethenone Chemical group FC(F)=C=O OTTXCOAOKOEENK-UHFFFAOYSA-N 0.000 claims 4
- 208000028698 Cognitive impairment Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 3
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 claims 3
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 3
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 3
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 claims 3
- ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 claims 3
- 239000002895 emetic Substances 0.000 claims 3
- FGIVSGPRGVABAB-UHFFFAOYSA-N fluoren-9-ylmethyl hydrogen carbonate Chemical compound C1=CC=C2C(COC(=O)O)C3=CC=CC=C3C2=C1 FGIVSGPRGVABAB-UHFFFAOYSA-N 0.000 claims 3
- 210000004558 lewy body Anatomy 0.000 claims 3
- 230000035772 mutation Effects 0.000 claims 3
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Classifications
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- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
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- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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Applications Claiming Priority (2)
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| US21532300P | 2000-06-30 | 2000-06-30 | |
| PCT/US2001/020930 WO2002002506A2 (en) | 2000-06-30 | 2001-06-29 | Compounds to treat alzheimer's disease |
Publications (1)
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| MXPA02012560A true MXPA02012560A (es) | 2003-05-14 |
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| MXPA02012560A MXPA02012560A (es) | 2000-06-30 | 2001-06-29 | Compuestos para tratar la enfermedad de alzheimer. |
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