JP2005514330A5 - - Google Patents
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- JP2005514330A5 JP2005514330A5 JP2003530659A JP2003530659A JP2005514330A5 JP 2005514330 A5 JP2005514330 A5 JP 2005514330A5 JP 2003530659 A JP2003530659 A JP 2003530659A JP 2003530659 A JP2003530659 A JP 2003530659A JP 2005514330 A5 JP2005514330 A5 JP 2005514330A5
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- JP
- Japan
- Prior art keywords
- alkyl
- butyl
- difluorobenzyl
- optionally substituted
- hydroxy
- 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.)
- Pending
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- 229910052736 halogen Inorganic materials 0.000 claims 62
- 150000002367 halogens Chemical class 0.000 claims 62
- 125000000217 alkyl group Chemical group 0.000 claims 59
- 125000004663 dialkyl amino group Chemical group 0.000 claims 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 36
- 125000000623 heterocyclic group Chemical group 0.000 claims 30
- 125000001072 heteroaryl group Chemical group 0.000 claims 25
- 206010012289 Dementia Diseases 0.000 claims 22
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- -1 substituted Chemical class 0.000 claims 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims 10
- 208000024827 Alzheimer disease Diseases 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 230000003412 degenerative effect Effects 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 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 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 6
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 6
- 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 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 4
- 201000010374 Down Syndrome Diseases 0.000 claims 4
- 241000257303 Hymenoptera Species 0.000 claims 4
- 206010044688 Trisomy 21 Diseases 0.000 claims 4
- 210000004227 basal ganglia Anatomy 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 230000001054 cortical effect Effects 0.000 claims 4
- 230000007850 degeneration Effects 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 210000004558 lewy body Anatomy 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 230000002792 vascular Effects 0.000 claims 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 2
- 206010033799 Paralysis Diseases 0.000 claims 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 2
- 208000036536 dutch type ABeta amyloidosis Diseases 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 2
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000000750 progressive effect Effects 0.000 claims 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 2
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- KIKGANUEXHTONT-UHFFFAOYSA-N 1-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxypropan-2-yl]-5-(1,3-oxazol-2-yl)-3,4-dihydro-2h-quinoline-7-carboxamide Chemical compound CCCCN1CCCC2=C1C=C(C(=O)NC(CO)CC=1C=C(F)C=C(F)C=1)C=C2C1=NC=CO1 KIKGANUEXHTONT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- HFXYFEKNOJYCRC-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-1h-quinoxaline-6-carboxamide Chemical compound CCCCN1CCNC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC=1NN=CC=1)C=C2C1=NC=CO1 HFXYFEKNOJYCRC-UHFFFAOYSA-N 0.000 claims 1
- QKHGYICHUUVYGS-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrrol-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=1NC=CC=1)C=C2C1=NC=CO1 QKHGYICHUUVYGS-UHFFFAOYSA-N 0.000 claims 1
- YSCCZYIQLYWITG-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrrol-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=1NC=CC=1)C=C2C1=NC=CO1 YSCCZYIQLYWITG-UHFFFAOYSA-N 0.000 claims 1
- BNQYKUYVKHNHEH-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(1h-pyrrol-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=1NC=CC=1)C=C2C1=NC=CO1 BNQYKUYVKHNHEH-UHFFFAOYSA-N 0.000 claims 1
- XRUXVYZGNDCMKV-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(2h-triazol-4-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=NC=1)C=C2C1=NC=CO1 XRUXVYZGNDCMKV-UHFFFAOYSA-N 0.000 claims 1
- LSRXGNNAUBZPAE-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(2h-triazol-4-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=NC=1)C=C2C1=NC=CO1 LSRXGNNAUBZPAE-UHFFFAOYSA-N 0.000 claims 1
- VTDUFWWEUCKCBF-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(2h-triazol-4-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=1NN=NC=1)C=C2C1=NC=CO1 VTDUFWWEUCKCBF-UHFFFAOYSA-N 0.000 claims 1
- GTMKLWQBKOTLHV-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(5-oxopyrrolidin-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)CCC1NC(=O)CC1)C=C2C1=NC=CO1 GTMKLWQBKOTLHV-UHFFFAOYSA-N 0.000 claims 1
- GNJWTCDBLPZBSM-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(5-oxopyrrolidin-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)CC1)C=C2C1=NC=CO1 GNJWTCDBLPZBSM-UHFFFAOYSA-N 0.000 claims 1
- QPEVICIBZKGDFL-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxy-5-(5-oxopyrrolidin-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)CCC1NC(=O)CC1)C=C2C1=NC=CO1 QPEVICIBZKGDFL-UHFFFAOYSA-N 0.000 claims 1
- VGCSKCKTGUNVKO-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-benzothiazine-6-carboxamide Chemical compound CCCCN1CCSC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC1NC(=O)CCC1)C=C2C1=NC=CO1 VGCSKCKTGUNVKO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PRCFBPVZVDCOHK-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-1h-quinoxaline-6-carboxamide Chemical compound CCCCN1CCNC2=C1C=C(C(=O)NC(CC=1C=C(F)C=C(F)C=1)C(O)CCC1NC(=O)CCC1)C=C2C1=NC=CO1 PRCFBPVZVDCOHK-UHFFFAOYSA-N 0.000 claims 1
- WJRBJNQQTFGYSW-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxypropan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzothiazine-6-carboxamide Chemical compound CCCCN1CCSC2=C1C=C(C(=O)NC(CO)CC=1C=C(F)C=C(F)C=1)C=C2C1=NC=CO1 WJRBJNQQTFGYSW-UHFFFAOYSA-N 0.000 claims 1
- AWKYLEDPGJKVBZ-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxypropan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzoxazine-6-carboxamide Chemical compound CCCCN1CCOC2=C1C=C(C(=O)NC(CO)CC=1C=C(F)C=C(F)C=1)C=C2C1=NC=CO1 AWKYLEDPGJKVBZ-UHFFFAOYSA-N 0.000 claims 1
- MAFSYLQABRNGGZ-UHFFFAOYSA-N 4-butyl-n-[1-(3,5-difluorophenyl)-3-hydroxypropan-2-yl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1h-quinoxaline-6-carboxamide Chemical compound CCCCN1CCNC2=C1C=C(C(=O)NC(CO)CC=1C=C(F)C=C(F)C=1)C=C2C1=NC=CO1 MAFSYLQABRNGGZ-UHFFFAOYSA-N 0.000 claims 1
- IRJCDTSTOAETIP-UHFFFAOYSA-N 4-butyl-n-[2-(3,5-difluorophenyl)ethyl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1,4-benzothiazine-6-carboxamide Chemical compound CCCCN1CCSC2=C1C=C(C(=O)NCCC=1C=C(F)C=C(F)C=1)C=C2C1=NC=CO1 IRJCDTSTOAETIP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FGVMSEHSENMHHK-UHFFFAOYSA-N 4-butyl-n-[2-(3,5-difluorophenyl)ethyl]-8-(1,3-oxazol-2-yl)-2,3-dihydro-1h-quinoxaline-6-carboxamide Chemical compound CCCCN1CCNC2=C1C=C(C(=O)NCCC=1C=C(F)C=C(F)C=1)C=C2C1=NC=CO1 FGVMSEHSENMHHK-UHFFFAOYSA-N 0.000 claims 1
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- JEMNNNQAPVQJSZ-UHFFFAOYSA-N n-[5-(1h-benzimidazol-2-yl)-1-(3,5-difluorophenyl)-3-hydroxypentan-2-yl]-1-butyl-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=C3N=1)C=C2C1=NC=CO1 JEMNNNQAPVQJSZ-UHFFFAOYSA-N 0.000 claims 1
- XDMZDMWZYKEEIR-UHFFFAOYSA-N n-[5-(1h-benzimidazol-2-yl)-1-(3,5-difluorophenyl)-3-hydroxypentan-2-yl]-4-butyl-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=C3N=1)C=C2C1=NC=CO1 XDMZDMWZYKEEIR-UHFFFAOYSA-N 0.000 claims 1
- UZAOATGNJCHHEW-UHFFFAOYSA-N n-[5-(1h-benzimidazol-2-yl)-1-(3,5-difluorophenyl)-3-hydroxypentan-2-yl]-4-butyl-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=C3N=1)C=C2C1=NC=CO1 UZAOATGNJCHHEW-UHFFFAOYSA-N 0.000 claims 1
- AQCYABAJBRLJTA-UHFFFAOYSA-N n-[5-(1h-benzimidazol-2-yl)-1-(3,5-difluorophenyl)-3-hydroxypentan-2-yl]-4-butyl-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=C3N=1)C=C2C1=NC=CO1 AQCYABAJBRLJTA-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 0 C*(C)c1cnn[n]1 Chemical compound C*(C)c1cnn[n]1 0.000 description 2
- YIDCITOHTLPMMZ-UHFFFAOYSA-N CC(C)(C)c1ccn[nH]1 Chemical compound CC(C)(C)c1ccn[nH]1 YIDCITOHTLPMMZ-UHFFFAOYSA-N 0.000 description 1
- XPMMAKUHNMSONL-YFKPBYRVSA-N C[C@@H](CCC1)NC1=O Chemical compound C[C@@H](CCC1)NC1=O XPMMAKUHNMSONL-YFKPBYRVSA-N 0.000 description 1
- PZKFSRWSQOQYNR-UHFFFAOYSA-N Cc1ncn[nH]1 Chemical compound Cc1ncn[nH]1 PZKFSRWSQOQYNR-UHFFFAOYSA-N 0.000 description 1
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| PCT/US2002/030231 WO2003027068A2 (en) | 2001-09-24 | 2002-09-24 | Substituted amines for the treatment of neurological disorders |
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| JP2005514330A JP2005514330A (ja) | 2005-05-19 |
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| CA (1) | CA2461603A1 (https=) |
| MX (1) | MXPA04002785A (https=) |
| WO (1) | WO2003027068A2 (https=) |
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| JP3813152B2 (ja) | 2002-03-12 | 2006-08-23 | メルク エンド カムパニー インコーポレーテッド | 置換アミド類 |
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| US7521481B2 (en) | 2003-02-27 | 2009-04-21 | Mclaurin Joanne | Methods of preventing, treating and diagnosing disorders of protein aggregation |
| PL2332921T3 (pl) | 2003-06-17 | 2016-08-31 | Arena Pharm Inc | Chlorowodorek 8-chloro-1-metylo-2,3,4,5-tetrahydro-1H-3-benzazepiny |
| CN1805938B (zh) | 2003-06-17 | 2010-06-16 | 艾尼纳制药公司 | 用于治疗5ht2c受体相关疾病的苯并氮杂卓衍生物 |
| AR045219A1 (es) * | 2003-08-08 | 2005-10-19 | Pharmacopeia Inc | Aminas ciclicas inhibidoras de base - 1 que poseen un sustiuyente heterociclico |
| US7550481B2 (en) | 2003-12-19 | 2009-06-23 | Merck & Co., Inc. | Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of Alzheimer's disease |
| JP2007533743A (ja) * | 2004-04-20 | 2007-11-22 | メルク エンド カムパニー インコーポレーテッド | アルツハイマー病治療のためのβ−セクレターゼ阻害薬として有用な１，３，５−置換フェニル誘導体化合物 |
| US7714021B2 (en) * | 2004-06-15 | 2010-05-11 | Merck & Co., Inc. | Pyrrolidin-3-yl compounds useful as beta-secretase inhibitors for the treatment of Alzheimer's disease |
| NZ555981A (en) | 2004-12-21 | 2011-01-28 | Arena Pharm Inc | Crystalline forms of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride |
| NZ562314A (en) | 2005-04-08 | 2010-02-26 | Comentis Inc | Compounds which inhibit beta-secretase activity and methods of use thereof |
| EP1891018B1 (en) * | 2005-05-24 | 2011-11-16 | Vertex Pharmaceuticals, Inc. | Modulators of atp-binding cassette transporters |
| EP2001852A2 (en) | 2006-04-03 | 2008-12-17 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto |
| CN101547892B (zh) | 2006-12-05 | 2014-08-20 | 艾尼纳制药公司 | 制备(r)-8-氯-1-甲基-2,3,4,5-四氢-1h-3-苯并氮杂卓的方法和其中间体 |
| EP2288585A1 (en) | 2008-03-04 | 2011-03-02 | 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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| US9045431B2 (en) | 2010-06-02 | 2015-06-02 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-HT2C receptor agonists |
| AU2011296015B2 (en) | 2010-09-01 | 2015-11-12 | Arena Pharmaceuticals, Inc. | Administration of lorcaserin to individuals with renal impairment |
| JP2013536859A (ja) | 2010-09-01 | 2013-09-26 | 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 | ５−ｈｔ２ｃアゴニストの非吸湿性塩 |
| JP6272695B2 (ja) | 2010-09-01 | 2018-01-31 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 体重管理のために有用な５−ｈｔ２ｃアゴニストの改変放出剤形 |
| KR20130138770A (ko) | 2010-09-01 | 2013-12-19 | 아레나 파마슈티칼스, 인크. | 광학적으로 활성 산을 갖는 로르카세린의 염 |
| JP2015534563A (ja) | 2012-10-09 | 2015-12-03 | 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 | 体重管理の方法 |
| JP6272833B2 (ja) * | 2013-04-04 | 2018-01-31 | 武田薬品工業株式会社 | 複素環化合物 |
| EP3170820B1 (en) * | 2014-07-16 | 2019-02-20 | Japan Science and Technology Agency | Benzothiazole compound and medicine containing same |
| UA123219C2 (uk) | 2015-10-23 | 2021-03-03 | Віфор (Інтернаціональ) Аґ | Інгібітори феропортину |
| JOP20180036A1 (ar) | 2017-04-18 | 2019-01-30 | Vifor Int Ag | أملاح لمثبطات فروبورتين جديدة |
| WO2023049953A1 (en) * | 2021-09-30 | 2023-04-06 | TroBio Therapeutics Pty Ltd | Substituted indole compounds and the use thereof |
| CN117229257B (zh) * | 2022-06-06 | 2026-01-30 | 中国药科大学 | 间氨磺酰苯甲酰胺类化合物及制法、药物组合物和应用 |
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| US2057145A (en) * | 1934-02-09 | 1936-10-13 | Firm Chem Fab Grunau Landshoff | Pharmaceutical preparation for stimulating the respiratory centre and increasing the circulation |
| US2971027A (en) * | 1956-08-30 | 1961-02-07 | California Research Corp | Diamides of terephthalic acid |
| US4562201A (en) * | 1982-07-26 | 1985-12-31 | American Hospital Supply Corporation | Aminomethyl benzanilides |
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| US5399565A (en) * | 1990-07-17 | 1995-03-21 | Eli Lilly And Company | Pyrazolidinone CCK and gastrin antagonists and pharmaceutical formulations therof |
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| GB9800750D0 (en) * | 1998-01-14 | 1998-03-11 | Lilly Co Eli | Pharmaceutical compound |
| CA2365401A1 (en) * | 1999-03-11 | 2000-10-05 | Neurogen Corporation | Aryl fused 2,4-disubstituted pyridines: nk3 receptor ligands |
| DK1196397T3 (da) * | 1999-06-02 | 2006-01-02 | Nps Pharma Inc | Metabotrope glutamatreceptorantagonister og anvendelse deraf til behandling af sygdomme i centralnervesystemet |
| WO2000078730A1 (en) * | 1999-06-23 | 2000-12-28 | Ajinomoto Co., Inc. | Novel dihydropyrimidine derivatives |
| AU7031500A (en) * | 1999-09-23 | 2001-04-24 | Astrazeneca Ab | Therapeutic quinazoline compounds |
| JP2003527395A (ja) * | 2000-03-17 | 2003-09-16 | ノボ ノルディスク アクティーゼルスカブ | ヒスタミンｈ３受容体リガンドとしての縮環イミダゾール |
| AUPQ969800A0 (en) * | 2000-08-28 | 2000-09-21 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazolopyridine compound and pharmaceutical use thereof |
| WO2002032896A1 (en) * | 2000-10-16 | 2002-04-25 | Novo Nordisk A/S | Furazanyl-triazole derivates for the treatment of diseases |
| HU227197B1 (en) * | 2000-10-24 | 2010-10-28 | Richter Gedeon Nyrt | Nmda receptor antagonist carboxylic acid amide derivatives and pharmaceutical compositions containing them |
| US6656971B2 (en) * | 2001-01-25 | 2003-12-02 | Guilford Pharmaceuticals Inc. | Trisubstituted carbocyclic cyclophilin binding compounds and their use |
| AU2002342607B2 (en) * | 2001-08-06 | 2006-10-19 | Pharmacia Italia S.P.A. | Aminoisoxazole derivatives active as kinase inhibitors |
| TWI231757B (en) * | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| CA2465326C (en) * | 2001-11-01 | 2011-03-29 | Icagen, Inc. | Pyrazolopyrimidines for decreasing ion flow through a voltage-dependent sodium channel |
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-
2002
- 2002-09-24 AU AU2002356525A patent/AU2002356525A1/en not_active Abandoned
- 2002-09-24 US US10/490,682 patent/US20060100196A1/en not_active Abandoned
- 2002-09-24 EP EP02799615A patent/EP1430032A2/en not_active Withdrawn
- 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
- 2002-09-24 MX MXPA04002785A patent/MXPA04002785A/es not_active Application Discontinuation
- 2002-09-24 WO PCT/US2002/030231 patent/WO2003027068A2/en not_active Ceased
- 2002-09-24 JP JP2003530659A patent/JP2005514330A/ja active Pending
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