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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| ATE486842T1 (de) | 2002-03-12 | 2010-11-15 | Merck Sharp & Dohme | Substituierte amide |
| 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 |
| 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 |
| US8367657B2 (en) | 2003-06-17 | 2013-02-05 | Arena Pharmaceuticals, Inc. | Processes for preparing 3-benzazepines |
| CN1863770B (zh) * | 2003-08-08 | 2011-05-25 | 先灵公司 | 具有杂环取代基的环胺base-1抑制剂 |
| JP2007517781A (ja) | 2003-12-19 | 2007-07-05 | 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用のフェニルアミドおよびピリジルアミド系β−セクレターゼ阻害薬 |
| 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 |
| EP2149562A1 (en) | 2004-12-21 | 2010-02-03 | Arena Pharmaceuticals, Inc. | method of preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate |
| MX2007012341A (es) | 2005-04-08 | 2008-02-12 | Comentis Inc | Compuestos que inhiben actividad beta-secretasa y metodos de uso de los mismos. |
| CA2609392A1 (en) * | 2005-05-24 | 2006-11-30 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| CA2646044A1 (en) | 2006-04-03 | 2007-10-25 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto |
| EP2099743B1 (en) | 2006-12-05 | 2014-08-27 | Arena Pharmaceuticals, Inc. | Processes for preparing (r)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates thereof |
| US8822727B2 (en) | 2008-03-04 | 2014-09-02 | 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 |
| WO2010148207A2 (en) | 2009-06-18 | 2010-12-23 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| WO2011153206A1 (en) | 2010-06-02 | 2011-12-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 5-ht2c receptor agonists |
| KR20180118801A (ko) | 2010-09-01 | 2018-10-31 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 체중 관리에 유용한 5-ｈｔ2ｃ 작동제의 변형-방출 투여 형태 |
| JP2013539470A (ja) | 2010-09-01 | 2013-10-24 | 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 | ロルカセリンと光学活性な酸との塩 |
| EA201390335A1 (ru) | 2010-09-01 | 2013-09-30 | Арена Фармасьютикалз, Инк. | Введение лоркасерина индивидуумам с почечной недостаточностью |
| KR20130101524A (ko) | 2010-09-01 | 2013-09-13 | 아레나 파마슈티칼스, 인크. | 5-ｈｔ2ｃ 아고니스트의 비-흡습성 염 |
| RU2674670C1 (ru) | 2012-10-09 | 2018-12-12 | Арена Фармасьютикалз, Инк. | Способ коррекции массы тела |
| US9624184B2 (en) * | 2013-04-04 | 2017-04-18 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| 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 |
| WO2017068089A2 (en) | 2015-10-23 | 2017-04-27 | Vifor (International) Ag | Novel ferroportin inhibitors |
| 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 |
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| CA1338012C (en) * | 1987-04-27 | 1996-01-30 | John Michael Mccall | Pharmaceutically active amines |
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| CN1100777C (zh) * | 1997-02-19 | 2003-02-05 | 伯莱克斯实验室公司 | 作为nos抑制剂的n－杂环衍生物 |
| AU771358B2 (en) * | 1997-11-21 | 2004-03-18 | Astrazeneca Ab | Metabotropic glutamate receptor antagonists for treating central nervous system diseases |
| GB9800750D0 (en) * | 1998-01-14 | 1998-03-11 | Lilly Co Eli | Pharmaceutical compound |
| DE60003899T2 (de) * | 1999-03-11 | 2004-05-27 | Neurogen Corp., Branford | Aryl-annellierte disubstituierte pyridine : nk3 rezeptor-liganden |
| CH1196397H1 (de) * | 1999-06-02 | 2007-05-31 | Nps Pharma Inc | Metabotrope Glutamatrezeptorantagonisten zur Behandlung von Krankheiten des zentralen Nervensystems. |
| WO2000078730A1 (en) * | 1999-06-23 | 2000-12-28 | Ajinomoto Co., Inc. | Novel dihydropyrimidine derivatives |
| ES2270867T3 (es) * | 1999-09-23 | 2007-04-16 | Astrazeneca Ab | Compuestos de quinazolina terapeuticos. |
| EP1268484A1 (en) * | 2000-03-17 | 2003-01-02 | Novo Nordisk A/S | Condensed imidazoles as histamine h3 receptor ligands |
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| WO2002032896A1 (en) * | 2000-10-16 | 2002-04-25 | Novo Nordisk A/S | Furazanyl-triazole derivates for the treatment of diseases |
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| NZ530782A (en) * | 2001-08-06 | 2005-11-25 | Pharmacia Italia S | Aminoisoxazole derivatives active as kinase inhibitors |
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| EP1506196B1 (en) * | 2001-11-01 | 2012-01-18 | Icagen, Inc. | Pyrazolopyrimidines as sodium channel inhibitors |
| EP1451156A4 (en) * | 2001-11-27 | 2005-05-25 | Merck & Co Inc | 4-AMINOCHINOLINVERBINDUNGEN |
| HUP0105406A3 (en) * | 2001-12-21 | 2003-12-29 | Sanofi Aventis | Imidazo[1,2-a]quinolin derivatives, process for their preparation, pharmaceutical compositions thereof and intermediates |
-
2002
- 2002-09-24 JP JP2003530659A patent/JP2005514330A/ja active Pending
- 2002-09-24 CA CA002461603A patent/CA2461603A1/en not_active Abandoned
- 2002-09-24 WO PCT/US2002/030231 patent/WO2003027068A2/en not_active Ceased
- 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 MX MXPA04002785A patent/MXPA04002785A/es not_active Application Discontinuation
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