JP2005514330A - アルツハイマー病治療のための置換アミン - Google Patents
アルツハイマー病治療のための置換アミン Download PDFInfo
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- JP2005514330A JP2005514330A JP2003530659A JP2003530659A JP2005514330A JP 2005514330 A JP2005514330 A JP 2005514330A JP 2003530659 A JP2003530659 A JP 2003530659A JP 2003530659 A JP2003530659 A JP 2003530659A JP 2005514330 A JP2005514330 A JP 2005514330A
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- JP
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- Prior art keywords
- alkyl
- butyl
- difluorobenzyl
- optionally substituted
- hydroxy
- Prior art date
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- Pending
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- 208000024827 Alzheimer disease Diseases 0.000 title claims abstract description 83
- 238000011282 treatment Methods 0.000 title claims description 39
- 150000001412 amines Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 307
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 63
- 201000010099 disease Diseases 0.000 claims abstract description 57
- 238000004519 manufacturing process Methods 0.000 claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- -1 substituted Chemical class 0.000 claims description 154
- 229910052736 halogen Inorganic materials 0.000 claims description 128
- 150000002367 halogens Chemical class 0.000 claims description 128
- 238000000034 method Methods 0.000 claims description 110
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 67
- 206010012289 Dementia Diseases 0.000 claims description 61
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 34
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
- 208000010877 cognitive disease Diseases 0.000 claims description 24
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 24
- 230000003412 degenerative effect Effects 0.000 claims description 22
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 201000010374 Down Syndrome Diseases 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 210000004558 lewy body Anatomy 0.000 claims description 13
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 12
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 12
- 230000007850 degeneration Effects 0.000 claims description 12
- 208000018737 Parkinson disease Diseases 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 11
- 230000002792 vascular Effects 0.000 claims description 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 10
- BHACQVFKSPPDLM-UHFFFAOYSA-N 3-n,3-n-dipropylbenzene-1,3,5-tricarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C(N)=O)=CC(C(N)=O)=C1 BHACQVFKSPPDLM-UHFFFAOYSA-N 0.000 claims description 10
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 10
- 230000001054 cortical effect Effects 0.000 claims description 10
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 9
- 206010044688 Trisomy 21 Diseases 0.000 claims description 9
- 210000004227 basal ganglia Anatomy 0.000 claims description 9
- 230000000750 progressive effect Effects 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 206010033799 Paralysis Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 150000003857 carboxamides Chemical class 0.000 claims description 7
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 5
- 241000257303 Hymenoptera Species 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 4
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- JSNGFLHVODTXRS-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(6-oxopiperidin-2-yl)pentan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzoxazine-6-carboxamide Chemical compound CCCCN1CCOC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC1NC(=O)CCC1)C=C2C1=NC=CO1 JSNGFLHVODTXRS-UHFFFAOYSA-N 0.000 claims description 3
- IDZQSGYIZVYJHD-UHFFFAOYSA-N 4-butyl-n-[2-(3,5-difluorophenyl)ethyl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzoxazine-6-carboxamide Chemical compound CCCCN1CCOC2=C1C=C(C(=O)NCCC=1C=C(F)C=C(F)C=1)C=C2C1=NC=CO1 IDZQSGYIZVYJHD-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 2
- IHDYGLQPUPOOQF-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-1,2,4-triazol-5-yl)pentan-2-yl]indole-6-carboxamide Chemical compound C1=C2N(CCCC)C=CC2=CC=C1C(=O)NC(C(O)CCC=1NN=CN=1)CC1=CC(F)=CC(F)=C1 IHDYGLQPUPOOQF-UHFFFAOYSA-N 0.000 claims description 2
- SFXJLXCQVDVPMQ-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-indol-2-yl)pentan-2-yl]-5-(1,3-oxazol-2-yl)-3,4-dihydro-2h-quinoline-7-carboxamide Chemical compound CCCCN1CCCC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NC3=CC=CC=C3C=1)C=C2C1=NC=CO1 SFXJLXCQVDVPMQ-UHFFFAOYSA-N 0.000 claims description 2
- DCCIFJLXPUVSTK-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrazol-5-yl)pentan-2-yl]-5-(1,3-oxazol-2-yl)-3,4-dihydro-2h-quinoline-7-carboxamide Chemical compound CCCCN1CCCC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NN=CC=1)C=C2C1=NC=CO1 DCCIFJLXPUVSTK-UHFFFAOYSA-N 0.000 claims description 2
- WUSLPRMRFGUDMP-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrazol-5-yl)pentan-2-yl]indole-6-carboxamide Chemical compound C1=C2N(CCCC)C=CC2=CC=C1C(=O)NC(C(O)CCC=1NN=CC=1)CC1=CC(F)=CC(F)=C1 WUSLPRMRFGUDMP-UHFFFAOYSA-N 0.000 claims description 2
- CBZUAAHUVIPSKY-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrrol-2-yl)pentan-2-yl]-5-(1,3-oxazol-2-yl)-3,4-dihydro-2h-quinoline-7-carboxamide Chemical compound CCCCN1CCCC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NC=CC=1)C=C2C1=NC=CO1 CBZUAAHUVIPSKY-UHFFFAOYSA-N 0.000 claims description 2
- PJEOKKZDRSEKFU-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrrol-2-yl)pentan-2-yl]indole-6-carboxamide Chemical compound C1=C2N(CCCC)C=CC2=CC=C1C(=O)NC(C(O)CCC=1NC=CC=1)CC1=CC(F)=CC(F)=C1 PJEOKKZDRSEKFU-UHFFFAOYSA-N 0.000 claims description 2
- WUOSNJNGPXVMCH-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(2h-triazol-4-yl)pentan-2-yl]-5-(1,3-oxazol-2-yl)-3,4-dihydro-2h-quinoline-7-carboxamide Chemical compound CCCCN1CCCC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NN=NC=1)C=C2C1=NC=CO1 WUOSNJNGPXVMCH-UHFFFAOYSA-N 0.000 claims description 2
- XQZDLOHEQKVFDU-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(2h-triazol-4-yl)pentan-2-yl]indole-6-carboxamide Chemical compound C1=C2N(CCCC)C=CC2=CC=C1C(=O)NC(C(O)CCC=1NN=NC=1)CC1=CC(F)=CC(F)=C1 XQZDLOHEQKVFDU-UHFFFAOYSA-N 0.000 claims description 2
- RPKPQXPESCGNCV-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(5-oxopyrrolidin-2-yl)pentan-2-yl]-5-(1,3-oxazol-2-yl)-3,4-dihydro-2h-quinoline-7-carboxamide Chemical compound CCCCN1CCCC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC1NC(=O)CC1)C=C2C1=NC=CO1 RPKPQXPESCGNCV-UHFFFAOYSA-N 0.000 claims description 2
- WDHCPNAREXWPPA-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(5-oxopyrrolidin-2-yl)pentan-2-yl]indole-6-carboxamide Chemical compound C1=C2N(CCCC)C=CC2=CC=C1C(=O)NC(C(O)CCC1NC(=O)CC1)CC1=CC(F)=CC(F)=C1 WDHCPNAREXWPPA-UHFFFAOYSA-N 0.000 claims description 2
- HZQGLTSJPSXKIC-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(6-oxopiperidin-2-yl)pentan-2-yl]-5-(1,3-oxazol-2-yl)-3,4-dihydro-2h-quinoline-7-carboxamide Chemical compound CCCCN1CCCC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC1NC(=O)CCC1)C=C2C1=NC=CO1 HZQGLTSJPSXKIC-UHFFFAOYSA-N 0.000 claims description 2
- BRBMTIKZRMBHLS-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(6-oxopiperidin-2-yl)pentan-2-yl]indole-6-carboxamide Chemical compound C1=C2N(CCCC)C=CC2=CC=C1C(=O)NC(C(O)CCC1NC(=O)CCC1)CC1=CC(F)=CC(F)=C1 BRBMTIKZRMBHLS-UHFFFAOYSA-N 0.000 claims description 2
- PCMLQPLBUSSQCO-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxypropan-2-yl]indole-6-carboxamide Chemical compound C1=C2N(CCCC)C=CC2=CC=C1C(=O)NC(CO)CC1=CC(F)=CC(F)=C1 PCMLQPLBUSSQCO-UHFFFAOYSA-N 0.000 claims description 2
- UKFITBRXJWZDIF-UHFFFAOYSA-N 1-butyl-n-[2-(3,5-difluorophenyl)ethyl]-5-(1,3-oxazol-2-yl)-3,4-dihydro-2h-quinoline-7-carboxamide Chemical compound CCCCN1CCCC2=C1C=C(C(=O)NCCC=1C=C(F)C=C(F)C=1)C=C2C1=NC=CO1 UKFITBRXJWZDIF-UHFFFAOYSA-N 0.000 claims description 2
- IHXWKLHECBKJEV-UHFFFAOYSA-N 1-butyl-n-[2-(3,5-difluorophenyl)ethyl]indole-6-carboxamide Chemical compound C1=C2N(CCCC)C=CC2=CC=C1C(=O)NCCC1=CC(F)=CC(F)=C1 IHXWKLHECBKJEV-UHFFFAOYSA-N 0.000 claims description 2
- JISSPBPUVKICME-QFIPXVFZSA-N 1-n-[(2s)-1-(3,5-difluorophenyl)-3-hydroxypropan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)N[C@H](CO)CC=2C=C(F)C=C(F)C=2)=C1 JISSPBPUVKICME-QFIPXVFZSA-N 0.000 claims description 2
- IRHDCWYPZODAGK-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-1,2,4-triazol-5-yl)pentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)CCC=2NN=CN=2)=C1 IRHDCWYPZODAGK-UHFFFAOYSA-N 0.000 claims description 2
- XUXAJQGPGCMOEK-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-indol-2-yl)pentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)CCC=2NC3=CC=CC=C3C=2)=C1 XUXAJQGPGCMOEK-UHFFFAOYSA-N 0.000 claims description 2
- BZKLEGILCVCVRW-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrazol-5-yl)pentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)CCC=2NN=CC=2)=C1 BZKLEGILCVCVRW-UHFFFAOYSA-N 0.000 claims description 2
- PXVDKHFQHQUBCI-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrrol-2-yl)pentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)CCC=2NC=CC=2)=C1 PXVDKHFQHQUBCI-UHFFFAOYSA-N 0.000 claims description 2
- QJWFUZFAVOWDGV-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(2h-triazol-4-yl)pentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)CCC=2NN=NC=2)=C1 QJWFUZFAVOWDGV-UHFFFAOYSA-N 0.000 claims description 2
- CZAIKKJMEMJBHM-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(5-oxopyrrolidin-2-yl)pentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)CCC2NC(=O)CC2)=C1 CZAIKKJMEMJBHM-UHFFFAOYSA-N 0.000 claims description 2
- FGCRREWITXOSDP-UHFFFAOYSA-N 1-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(6-oxopiperidin-2-yl)pentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)CCC2NC(=O)CCC2)=C1 FGCRREWITXOSDP-UHFFFAOYSA-N 0.000 claims description 2
- YCMYEVYIGMWBBM-UHFFFAOYSA-N 1-n-[5-(1h-benzimidazol-2-yl)-1-(3,5-difluorophenyl)-3-hydroxypentan-2-yl]-5-methyl-3-n,3-n-dipropylbenzene-1,3-dicarboxamide Chemical compound CCCN(CCC)C(=O)C1=CC(C)=CC(C(=O)NC(CC=2C=C(F)C=C(F)C=2)C(O)CCC=2NC3=CC=CC=C3N=2)=C1 YCMYEVYIGMWBBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
- NUQGGGIDFQWIFU-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-1,2,4-triazol-5-yl)pentan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzothiazine-6-carboxamide Chemical compound CCCCN1CCSC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NN=CN=1)C=C2C1=NC=CO1 NUQGGGIDFQWIFU-UHFFFAOYSA-N 0.000 claims description 2
- OVJPUYVERNVDBJ-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-1,2,4-triazol-5-yl)pentan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzoxazine-6-carboxamide Chemical compound CCCCN1CCOC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NN=CN=1)C=C2C1=NC=CO1 OVJPUYVERNVDBJ-UHFFFAOYSA-N 0.000 claims description 2
- NKYZEWBVEFZKMR-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-indol-2-yl)pentan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzothiazine-6-carboxamide Chemical compound CCCCN1CCSC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NC3=CC=CC=C3C=1)C=C2C1=NC=CO1 NKYZEWBVEFZKMR-UHFFFAOYSA-N 0.000 claims description 2
- YMWSLHJVFVZFLE-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-indol-2-yl)pentan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzoxazine-6-carboxamide Chemical compound CCCCN1CCOC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NC3=CC=CC=C3C=1)C=C2C1=NC=CO1 YMWSLHJVFVZFLE-UHFFFAOYSA-N 0.000 claims description 2
- NNDNYXNFAVYVMX-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-indol-2-yl)pentan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1h-quinoxaline-6-carboxamide Chemical compound CCCCN1CCNC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NC3=CC=CC=C3C=1)C=C2C1=NC=CO1 NNDNYXNFAVYVMX-UHFFFAOYSA-N 0.000 claims description 2
- IUKWKSGABPZERY-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrazol-5-yl)pentan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzothiazine-6-carboxamide Chemical compound CCCCN1CCSC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NN=CC=1)C=C2C1=NC=CO1 IUKWKSGABPZERY-UHFFFAOYSA-N 0.000 claims description 2
- YNHWVRIOWYBQBZ-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrazol-5-yl)pentan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzoxazine-6-carboxamide Chemical compound CCCCN1CCOC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NN=CC=1)C=C2C1=NC=CO1 YNHWVRIOWYBQBZ-UHFFFAOYSA-N 0.000 claims description 2
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 229960001603 tamoxifen Drugs 0.000 description 1
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- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 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 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 229960001722 verapamil Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
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- 229940046009 vitamin E Drugs 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32440701P | 2001-09-24 | 2001-09-24 | |
| PCT/US2002/030231 WO2003027068A2 (en) | 2001-09-24 | 2002-09-24 | Substituted amines for the treatment of neurological disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005514330A true JP2005514330A (ja) | 2005-05-19 |
| JP2005514330A5 JP2005514330A5 (enExample) | 2006-01-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2003530659A Pending JP2005514330A (ja) | 2001-09-24 | 2002-09-24 | アルツハイマー病治療のための置換アミン |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20060100196A1 (enExample) |
| EP (1) | EP1430032A2 (enExample) |
| JP (1) | JP2005514330A (enExample) |
| AU (1) | AU2002356525A1 (enExample) |
| BR (1) | BR0212787A (enExample) |
| CA (1) | CA2461603A1 (enExample) |
| MX (1) | MXPA04002785A (enExample) |
| WO (1) | WO2003027068A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016010092A1 (ja) * | 2014-07-16 | 2016-01-21 | 国立研究開発法人科学技術振興機構 | ベンゾチアゾール化合物及びこれを含有する医薬 |
| JP2018536641A (ja) * | 2015-10-23 | 2018-12-13 | ヴィフォール (インターナショナル) アクチェンゲゼルシャフトVifor (International) AG | 新規なフェロポーチン阻害剤 |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003077847A2 (en) | 2002-03-12 | 2003-09-25 | Merck & Co., Inc. | Substituted amides |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| US7521481B2 (en) | 2003-02-27 | 2009-04-21 | Mclaurin Joanne | Methods of preventing, treating and diagnosing disorders of protein aggregation |
| DK2332921T3 (en) | 2003-06-17 | 2016-05-09 | Arena Pharm Inc | 8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3benzazepine hydrochloride |
| JP4782003B2 (ja) | 2003-06-17 | 2011-09-28 | アリーナ ファーマシューティカルズ, インコーポレイテッド | 5ht2cレセプター関連疾患の処置に有用なベンズアゼピン誘導体 |
| CA2534672A1 (en) | 2003-08-08 | 2005-02-17 | Schering Corporation | Cyclic amine bace-1 inhibitors having a heterocyclic substituent |
| EP1697308B1 (en) | 2003-12-19 | 2014-03-19 | Merck Sharp & Dohme Corp. | Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of alzheimer's disease |
| US7847100B2 (en) * | 2004-04-20 | 2010-12-07 | Merck, Sharp & Dohme, Inc. | 1,3,5-substituted phenyl derivative compounds useful as beta-secretase inhibitors for the treatment of Alzheimer's disease |
| EP1758854B1 (en) * | 2004-06-15 | 2014-07-16 | Merck Sharp & Dohme Corp. | Pyrrolidin-3-yl compounds useful as beta-secretase inhibitors for the treatment of alzheimer's disease |
| RS50996B (sr) | 2004-12-21 | 2010-10-31 | Arena Pharmaceuticals Inc. | Kristalni oblici (r)-8-hloro-1-metil-2,3,4,5-tetrahidro-1h-benzazepin hlorhidrat |
| AU2006235344B2 (en) | 2005-04-08 | 2012-07-26 | Comentis, Inc. | Compounds which inhibit beta-secretase activity and methods of use thereof |
| JP5426878B2 (ja) * | 2005-05-24 | 2014-02-26 | バーテックス ファーマシューティカルズ インコーポレイテッド | Atp−結合カセットトランスポーターのモジュレーター |
| CN101466684B (zh) | 2006-04-03 | 2012-06-20 | 艾尼纳制药公司 | 8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的制备工艺和其相关中间体 |
| ES2522587T3 (es) | 2006-12-05 | 2014-11-17 | Arena Pharmaceuticals, Inc. | Procesos para preparar (R)-8-cloro-1-metil-2,3,4,5-tetrahidro-1H-3-benzacepina e intermedios de la misma |
| WO2009111004A1 (en) | 2008-03-04 | 2009-09-11 | Arena Pharmaceuticals, Inc. | Processes for the preparation of intermediates related to the 5-ht2c agonist (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine |
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2002
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- 2002-09-24 EP EP02799615A patent/EP1430032A2/en not_active Withdrawn
- 2002-09-24 US US10/490,682 patent/US20060100196A1/en not_active Abandoned
- 2002-09-24 AU AU2002356525A patent/AU2002356525A1/en not_active Abandoned
- 2002-09-24 WO PCT/US2002/030231 patent/WO2003027068A2/en not_active Ceased
- 2002-09-24 JP JP2003530659A patent/JP2005514330A/ja active Pending
- 2002-09-24 BR BR0212787-3A patent/BR0212787A/pt not_active IP Right Cessation
- 2002-09-24 CA CA002461603A patent/CA2461603A1/en not_active Abandoned
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016010092A1 (ja) * | 2014-07-16 | 2016-01-21 | 国立研究開発法人科学技術振興機構 | ベンゾチアゾール化合物及びこれを含有する医薬 |
| JPWO2016010092A1 (ja) * | 2014-07-16 | 2017-06-15 | 国立研究開発法人科学技術振興機構 | ベンゾチアゾール化合物及びこれを含有する医薬 |
| US9932333B2 (en) | 2014-07-16 | 2018-04-03 | Japan Science And Technology Agency | Benzothiazole compound and medicine containing same |
| JP2018536641A (ja) * | 2015-10-23 | 2018-12-13 | ヴィフォール (インターナショナル) アクチェンゲゼルシャフトVifor (International) AG | 新規なフェロポーチン阻害剤 |
| JP2020143136A (ja) * | 2015-10-23 | 2020-09-10 | ヴィフォール (インターナショナル) アクチェンゲゼルシャフトVifor (International) AG | 新規なフェロポーチン阻害剤 |
Also Published As
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| WO2003027068A3 (en) | 2004-04-08 |
| AU2002356525A1 (en) | 2003-04-07 |
| WO2003027068A2 (en) | 2003-04-03 |
| EP1430032A2 (en) | 2004-06-23 |
| MXPA04002785A (es) | 2004-07-29 |
| US20060100196A1 (en) | 2006-05-11 |
| CA2461603A1 (en) | 2003-04-03 |
| BR0212787A (pt) | 2005-01-25 |
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