SK82398A3 - 4-substituted piperidine analogs and their use as subtype selective nmda receptor antagonists - Google Patents
4-substituted piperidine analogs and their use as subtype selective nmda receptor antagonists Download PDFInfo
- Publication number
- SK82398A3 SK82398A3 SK823-98A SK82398A SK82398A3 SK 82398 A3 SK82398 A3 SK 82398A3 SK 82398 A SK82398 A SK 82398A SK 82398 A3 SK82398 A3 SK 82398A3
- Authority
- SK
- Slovakia
- Prior art keywords
- benzyl
- butynyl
- piperidine
- hydroxy
- ynyl
- Prior art date
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- -1 4-substituted piperidine Chemical class 0.000 title claims abstract description 90
- 229940127523 NMDA Receptor Antagonists Drugs 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 50
- 208000006011 Stroke Diseases 0.000 claims abstract description 12
- 208000002193 Pain Diseases 0.000 claims abstract description 11
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 10
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 10
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 9
- 230000036506 anxiety Effects 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 7
- 206010008118 cerebral infarction Diseases 0.000 claims abstract description 7
- 201000006474 Brain Ischemia Diseases 0.000 claims abstract description 6
- 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 6
- 206010011878 Deafness Diseases 0.000 claims abstract description 6
- 208000013016 Hypoglycemia Diseases 0.000 claims abstract description 6
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims abstract description 6
- 230000010370 hearing loss Effects 0.000 claims abstract description 6
- 231100000888 hearing loss Toxicity 0.000 claims abstract description 6
- 208000016354 hearing loss disease Diseases 0.000 claims abstract description 6
- 206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 claims abstract description 5
- 208000001763 cytomegalovirus retinitis Diseases 0.000 claims abstract description 5
- 230000002218 hypoglycaemic effect Effects 0.000 claims abstract description 5
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 4
- 208000001738 Nervous System Trauma Diseases 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 152
- 125000000217 alkyl group Chemical group 0.000 claims description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 67
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 58
- 125000003545 alkoxy group Chemical group 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 46
- 150000002431 hydrogen Chemical group 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 35
- 238000011282 treatment Methods 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 150000002367 halogens Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 125000003282 alkyl amino group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 21
- 241001465754 Metazoa Species 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 11
- CZBDUSALKFUNTF-UHFFFAOYSA-N 1-but-3-ynyl-4-[(4-chlorophenyl)methyl]piperidine Chemical compound C1=CC(Cl)=CC=C1CC1CCN(CCC#C)CC1 CZBDUSALKFUNTF-UHFFFAOYSA-N 0.000 claims description 9
- 208000018737 Parkinson disease Diseases 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- RFZQVGCGPXJANP-UHFFFAOYSA-N 3-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]aniline Chemical compound NC1=CC=CC(C#CCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 RFZQVGCGPXJANP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- PDBVBEUUEWBWHA-UHFFFAOYSA-N 1-[4-(3-aminophenyl)but-3-ynyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound NC1=CC=CC(C#CCCN2CCC(O)(CC2)C=2C=CC(Cl)=CC=2)=C1 PDBVBEUUEWBWHA-UHFFFAOYSA-N 0.000 claims description 6
- ISVKCDBNGIPSLZ-UHFFFAOYSA-N 1-[4-(4-aminophenyl)but-3-ynyl]-4-benzylpiperidin-4-ol Chemical compound C1=CC(N)=CC=C1C#CCCN1CCC(O)(CC=2C=CC=CC=2)CC1 ISVKCDBNGIPSLZ-UHFFFAOYSA-N 0.000 claims description 6
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 claims description 6
- VTDNMOIPAWUQFC-UHFFFAOYSA-N 4-[4-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]but-1-ynyl]aniline Chemical compound C1=CC(N)=CC=C1C#CCCN1CCC(CC=2C=CC(Cl)=CC=2)CC1 VTDNMOIPAWUQFC-UHFFFAOYSA-N 0.000 claims description 6
- YRFCOODQNSADOY-UHFFFAOYSA-N 4-[4-[4-[(4-methylphenyl)methyl]piperidin-1-yl]but-1-ynyl]phenol Chemical compound C1=CC(C)=CC=C1CC1CCN(CCC#CC=2C=CC(O)=CC=2)CC1 YRFCOODQNSADOY-UHFFFAOYSA-N 0.000 claims description 6
- WFNXZUROSQEVEL-UHFFFAOYSA-N 4-benzyl-1-[4-(3-methylphenyl)but-3-ynyl]piperidin-4-ol Chemical compound CC1=CC=CC(C#CCCN2CCC(O)(CC=3C=CC=CC=3)CC2)=C1 WFNXZUROSQEVEL-UHFFFAOYSA-N 0.000 claims description 6
- IPHNHHOINYUNHW-UHFFFAOYSA-N 4-benzyl-1-but-3-ynylpiperidine Chemical compound C1CN(CCC#C)CCC1CC1=CC=CC=C1 IPHNHHOINYUNHW-UHFFFAOYSA-N 0.000 claims description 6
- ILABISIOLQXNHJ-UHFFFAOYSA-N 5-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1C#CCCN(CC1)CCC1CC1=CC=CC=C1 ILABISIOLQXNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 206010046543 Urinary incontinence Diseases 0.000 claims description 6
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- SSGDKVACQQSLGX-UHFFFAOYSA-N 1-[4-(3-aminophenyl)but-3-ynyl]-4-(4-chlorophenyl)piperidin-2-amine Chemical compound NC=1C=C(C=CC=1)C#CCCN1C(CC(CC1)C1=CC=C(C=C1)Cl)N SSGDKVACQQSLGX-UHFFFAOYSA-N 0.000 claims description 5
- XQAQHAILWBQCJU-UHFFFAOYSA-N 1-[4-(4-aminophenyl)but-3-ynyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1=CC(N)=CC=C1C#CCCN1CCC(O)(C=2C=CC(Cl)=CC=2)CC1 XQAQHAILWBQCJU-UHFFFAOYSA-N 0.000 claims description 5
- KOOZXZDEBFUPRI-UHFFFAOYSA-N 1-but-3-ynyl-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCN(CCC#C)CC1 KOOZXZDEBFUPRI-UHFFFAOYSA-N 0.000 claims description 5
- ZITZUKAOCKEMQS-UHFFFAOYSA-N 3-[4-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]but-1-ynyl]aniline Chemical compound NC1=CC=CC(C#CCCN2CC=C(CC2)C=2C=CC(Cl)=CC=2)=C1 ZITZUKAOCKEMQS-UHFFFAOYSA-N 0.000 claims description 5
- COTXHBXDTNKBKW-UHFFFAOYSA-N 4-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 COTXHBXDTNKBKW-UHFFFAOYSA-N 0.000 claims description 5
- YFYRNQJYAUAGBK-UHFFFAOYSA-N 4-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]-n-butylbenzamide Chemical compound C1=CC(C(=O)NCCCC)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 YFYRNQJYAUAGBK-UHFFFAOYSA-N 0.000 claims description 5
- ZBDREQAUXIWPPQ-UHFFFAOYSA-N 4-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]aniline Chemical compound C1=CC(N)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 ZBDREQAUXIWPPQ-UHFFFAOYSA-N 0.000 claims description 5
- OGVFMJNCHAWNNN-UHFFFAOYSA-N 4-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 OGVFMJNCHAWNNN-UHFFFAOYSA-N 0.000 claims description 5
- DQZBYMUDSJTGLY-UHFFFAOYSA-N 4-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]phenol Chemical compound C1=CC(O)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 DQZBYMUDSJTGLY-UHFFFAOYSA-N 0.000 claims description 5
- SFDSSPBJYBMRGW-UHFFFAOYSA-N 4-[4-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]but-1-ynyl]-2-fluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C#CCCN1CCC(CC=2C=CC(Cl)=CC=2)CC1 SFDSSPBJYBMRGW-UHFFFAOYSA-N 0.000 claims description 5
- TYZGRLKUJKJAPY-UHFFFAOYSA-N 4-benzyl-1-[4-(3-methylphenyl)but-3-ynyl]piperidine Chemical compound CC1=CC=CC(C#CCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 TYZGRLKUJKJAPY-UHFFFAOYSA-N 0.000 claims description 5
- VBQGLKVYZYVDKA-UHFFFAOYSA-N 4-benzyl-1-[4-(4-chlorophenyl)but-3-ynyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 VBQGLKVYZYVDKA-UHFFFAOYSA-N 0.000 claims description 5
- IPSPEWKFMKDKSD-UHFFFAOYSA-N 4-benzyl-1-[4-(4-fluorophenyl)but-3-ynyl]piperidine Chemical compound C1=CC(F)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 IPSPEWKFMKDKSD-UHFFFAOYSA-N 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- SLUSUHNSAJADBJ-UHFFFAOYSA-N 1-(4-phenylbut-3-ynyl)-4-[3-(trifluoromethyl)phenyl]piperidin-3-ol Chemical compound C1CC(C=2C=C(C=CC=2)C(F)(F)F)C(O)CN1CCC#CC1=CC=CC=C1 SLUSUHNSAJADBJ-UHFFFAOYSA-N 0.000 claims description 4
- NWBGTSNKOYVTRT-UHFFFAOYSA-N 1-[4-(3-aminophenyl)but-3-ynyl]-4-benzylpiperidin-3-ol Chemical compound NC1=CC=CC(C#CCCN2CC(O)C(CC=3C=CC=CC=3)CC2)=C1 NWBGTSNKOYVTRT-UHFFFAOYSA-N 0.000 claims description 4
- MDVYAYYFUIREDQ-UHFFFAOYSA-N 1-[5-(3-aminophenyl)pent-4-ynyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound NC1=CC=CC(C#CCCCN2CCC(O)(CC2)C=2C=CC(Cl)=CC=2)=C1 MDVYAYYFUIREDQ-UHFFFAOYSA-N 0.000 claims description 4
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 4
- MCILTFLACBDPGR-UHFFFAOYSA-N 3-[4-(4-phenoxypiperidin-1-yl)but-1-ynyl]aniline Chemical compound NC1=CC=CC(C#CCCN2CCC(CC2)OC=2C=CC=CC=2)=C1 MCILTFLACBDPGR-UHFFFAOYSA-N 0.000 claims description 4
- FCFNEHFCHRJYQM-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)but-3-ynyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCC#CC1=CC=C(F)C=C1 FCFNEHFCHRJYQM-UHFFFAOYSA-N 0.000 claims description 4
- KSAODGRRVYJNHC-UHFFFAOYSA-N 4-[3-(4-benzylpiperidin-1-yl)prop-1-ynyl]aniline Chemical compound C1=CC(N)=CC=C1C#CCN1CCC(CC=2C=CC=CC=2)CC1 KSAODGRRVYJNHC-UHFFFAOYSA-N 0.000 claims description 4
- RTNDIYAWRAEQKB-UHFFFAOYSA-N 4-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 RTNDIYAWRAEQKB-UHFFFAOYSA-N 0.000 claims description 4
- YPBXVUBCNUFOIU-UHFFFAOYSA-N 4-[4-[4-[(4-methylphenyl)methyl]piperidin-1-yl]but-1-ynyl]aniline Chemical compound C1=CC(C)=CC=C1CC1CCN(CCC#CC=2C=CC(N)=CC=2)CC1 YPBXVUBCNUFOIU-UHFFFAOYSA-N 0.000 claims description 4
- GUUKLWSWNFCKJI-UHFFFAOYSA-N 4-benzyl-1-(4-phenylbut-3-ynyl)piperidin-3-ol Chemical compound C1CC(CC=2C=CC=CC=2)C(O)CN1CCC#CC1=CC=CC=C1 GUUKLWSWNFCKJI-UHFFFAOYSA-N 0.000 claims description 4
- JKHKJUWIHNVFFI-UHFFFAOYSA-N 4-benzyl-1-(4-phenylbut-3-ynyl)piperidine Chemical compound C=1C=CC=CC=1C#CCCN(CC1)CCC1CC1=CC=CC=C1 JKHKJUWIHNVFFI-UHFFFAOYSA-N 0.000 claims description 4
- XOWUZGPOBDUMHM-UHFFFAOYSA-N 4-benzyl-1-[4-(2,3-dichlorophenyl)but-3-ynyl]piperidine Chemical compound ClC1=CC=CC(C#CCCN2CCC(CC=3C=CC=CC=3)CC2)=C1Cl XOWUZGPOBDUMHM-UHFFFAOYSA-N 0.000 claims description 4
- LXOPXXXIPXJRRO-UHFFFAOYSA-N 4-benzyl-1-[4-(3,4-dichlorophenyl)but-3-ynyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 LXOPXXXIPXJRRO-UHFFFAOYSA-N 0.000 claims description 4
- ONYQRRJQXHSZDR-UHFFFAOYSA-N 4-benzyl-1-[4-(3,4-dimethylphenyl)but-3-ynyl]piperidine Chemical compound C1=C(C)C(C)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 ONYQRRJQXHSZDR-UHFFFAOYSA-N 0.000 claims description 4
- VVYCKPKSEYDOAF-UHFFFAOYSA-N 4-benzyl-1-[4-(4-methoxyphenyl)but-3-ynyl]piperidine Chemical compound C1=CC(OC)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 VVYCKPKSEYDOAF-UHFFFAOYSA-N 0.000 claims description 4
- WOXWQFUUNSRFNC-UHFFFAOYSA-N 4-phenoxy-1-(4-phenylbut-3-ynyl)piperidine Chemical compound C=1C=CC=CC=1C#CCCN(CC1)CCC1OC1=CC=CC=C1 WOXWQFUUNSRFNC-UHFFFAOYSA-N 0.000 claims description 4
- YXLSRUXXMCDOSW-UHFFFAOYSA-N 4-phenyl-1-(4-phenylbut-3-ynyl)piperidin-2-amine Chemical compound C1(=CC=CC=C1)C#CCCN1C(CC(CC1)C1=CC=CC=C1)N YXLSRUXXMCDOSW-UHFFFAOYSA-N 0.000 claims description 4
- VSRIYVIORLQEQY-UHFFFAOYSA-N 4-phenyl-1-(4-phenylbut-3-ynyl)piperidine Chemical compound C=1C=CC=CC=1C#CCCN(CC1)CCC1C1=CC=CC=C1 VSRIYVIORLQEQY-UHFFFAOYSA-N 0.000 claims description 4
- JTHIYPHEWHYVLG-UHFFFAOYSA-N 5-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]-1h-indazole Chemical compound C=1C=C2NN=CC2=CC=1C#CCCN(CC1)CCC1CC1=CC=CC=C1 JTHIYPHEWHYVLG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 claims description 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- XUIIEFRDBMIDAY-UHFFFAOYSA-N n-[4-[3-(4-benzylpiperidin-1-yl)prop-1-ynyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C#CCN1CCC(CC=2C=CC=CC=2)CC1 XUIIEFRDBMIDAY-UHFFFAOYSA-N 0.000 claims description 4
- XRVOIGOCEXMZCZ-UHFFFAOYSA-N n-[4-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 XRVOIGOCEXMZCZ-UHFFFAOYSA-N 0.000 claims description 4
- AOLADAASUPWOIE-UHFFFAOYSA-N n-[4-[4-(4-phenylsulfanylpiperidin-1-yl)but-1-ynyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C#CCCN1CCC(SC=2C=CC=CC=2)CC1 AOLADAASUPWOIE-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- ZGHBDTLGGUJOEZ-UHFFFAOYSA-N 1-[4-(3-aminophenyl)but-3-ynyl]-4-phenylpiperidin-2-amine Chemical compound NC=1C=C(C=CC=1)C#CCCN1C(CC(CC1)C1=CC=CC=C1)N ZGHBDTLGGUJOEZ-UHFFFAOYSA-N 0.000 claims description 3
- GYXQIQUDONKGID-UHFFFAOYSA-N 1-[4-(4-aminophenyl)but-3-ynyl]-4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CCC#CC=2C=CC(N)=CC=2)CC1 GYXQIQUDONKGID-UHFFFAOYSA-N 0.000 claims description 3
- YFALZLZSGFNKFB-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)but-3-ynyl]-4-[[3-(trifluoromethyl)phenyl]methyl]piperidin-3-ol Chemical compound C1CC(CC=2C=C(C=CC=2)C(F)(F)F)C(O)CN1CCC#CC1=CC=C(F)C=C1 YFALZLZSGFNKFB-UHFFFAOYSA-N 0.000 claims description 3
- XQXBTRPARQNLEB-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)but-3-ynyl]-4-[[3-(trifluoromethyl)phenyl]methyl]piperidine Chemical compound C1=CC(F)=CC=C1C#CCCN1CCC(CC=2C=C(C=CC=2)C(F)(F)F)CC1 XQXBTRPARQNLEB-UHFFFAOYSA-N 0.000 claims description 3
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 3
- UAZSCOFMJCDPOP-UHFFFAOYSA-N 2-[4-(4-phenylpiperidin-1-yl)but-1-ynyl]aniline Chemical compound NC1=CC=CC=C1C#CCCN1CCC(C=2C=CC=CC=2)CC1 UAZSCOFMJCDPOP-UHFFFAOYSA-N 0.000 claims description 3
- YFDLLNIGMTVMON-UHFFFAOYSA-N 4-[3-(4-benzylpiperidin-1-yl)prop-1-ynyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C#CCN1CCC(CC=2C=CC=CC=2)CC1 YFDLLNIGMTVMON-UHFFFAOYSA-N 0.000 claims description 3
- SYYKYYJFGJHYGB-UHFFFAOYSA-N 4-[4-(4-benzylpiperidin-1-yl)but-1-ynyl]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 SYYKYYJFGJHYGB-UHFFFAOYSA-N 0.000 claims description 3
- VBQOHGITPGAJDD-UHFFFAOYSA-N 4-[4-[4-(4-chlorophenoxy)piperidin-1-yl]but-1-ynyl]aniline Chemical compound C1=CC(N)=CC=C1C#CCCN1CCC(OC=2C=CC(Cl)=CC=2)CC1 VBQOHGITPGAJDD-UHFFFAOYSA-N 0.000 claims description 3
- QZCFWXKDDJAIKH-UHFFFAOYSA-N 4-benzyl-1-[4-(3-chlorophenyl)but-3-ynyl]piperidine Chemical compound ClC1=CC=CC(C#CCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 QZCFWXKDDJAIKH-UHFFFAOYSA-N 0.000 claims description 3
- XBGIMQCGDSYYIA-UHFFFAOYSA-N 4-benzyl-1-[4-(4-methylphenyl)but-3-ynyl]piperidine Chemical compound C1=CC(C)=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 XBGIMQCGDSYYIA-UHFFFAOYSA-N 0.000 claims description 3
- WKOIWFDPOLFHOG-UHFFFAOYSA-N 4-benzyl-1-[4-(4-nitrophenyl)but-3-ynyl]piperidine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C#CCCN1CCC(CC=2C=CC=CC=2)CC1 WKOIWFDPOLFHOG-UHFFFAOYSA-N 0.000 claims description 3
- JNMBUZAZEDOCAV-UHFFFAOYSA-N 4-benzyl-1-but-3-ynylpiperidin-4-ol Chemical compound C=1C=CC=CC=1CC1(O)CCN(CCC#C)CC1 JNMBUZAZEDOCAV-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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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- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/54—Sulfur atoms
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Engineering & Computer Science (AREA)
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- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US919295P | 1995-12-22 | 1995-12-22 | |
PCT/US1996/020766 WO1997023214A1 (fr) | 1995-12-22 | 1996-12-20 | Analogues de piperidine a substitution en position 4 et utilisation de ces derniers en tant qu'antagonistes selectivement actifs contre les sous-types du recepteurs de nmda |
Publications (1)
Publication Number | Publication Date |
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SK82398A3 true SK82398A3 (en) | 1999-03-12 |
Family
ID=21736135
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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SK823-98A SK82398A3 (en) | 1995-12-22 | 1996-12-20 | 4-substituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
Country Status (22)
Country | Link |
---|---|
US (4) | US6130234A (fr) |
EP (1) | EP0869791B1 (fr) |
JP (1) | JP2000502352A (fr) |
AT (1) | ATE239473T1 (fr) |
AU (1) | AU719430B2 (fr) |
BG (1) | BG63424B1 (fr) |
BR (1) | BR9612153A (fr) |
CA (1) | CA2240038A1 (fr) |
CZ (1) | CZ177898A3 (fr) |
DE (1) | DE69628035T2 (fr) |
DK (1) | DK0869791T3 (fr) |
EA (1) | EA001133B1 (fr) |
ES (1) | ES2196196T3 (fr) |
IL (1) | IL125060A (fr) |
MX (1) | MX9805032A (fr) |
NO (1) | NO312028B1 (fr) |
NZ (1) | NZ325735A (fr) |
PL (1) | PL327413A1 (fr) |
PT (1) | PT869791E (fr) |
SK (1) | SK82398A3 (fr) |
WO (1) | WO1997023214A1 (fr) |
ZA (1) | ZA9610741B (fr) |
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-
1996
- 1996-12-19 ZA ZA9610741A patent/ZA9610741B/xx unknown
- 1996-12-20 SK SK823-98A patent/SK82398A3/sk unknown
- 1996-12-20 NZ NZ325735A patent/NZ325735A/en unknown
- 1996-12-20 CA CA002240038A patent/CA2240038A1/fr not_active Abandoned
- 1996-12-20 IL IL12506096A patent/IL125060A/xx not_active IP Right Cessation
- 1996-12-20 US US09/091,594 patent/US6130234A/en not_active Expired - Fee Related
- 1996-12-20 EP EP96944537A patent/EP0869791B1/fr not_active Expired - Lifetime
- 1996-12-20 EA EA199800591A patent/EA001133B1/ru not_active IP Right Cessation
- 1996-12-20 AT AT96944537T patent/ATE239473T1/de not_active IP Right Cessation
- 1996-12-20 JP JP09523881A patent/JP2000502352A/ja not_active Ceased
- 1996-12-20 DK DK96944537T patent/DK0869791T3/da active
- 1996-12-20 CZ CZ981778A patent/CZ177898A3/cs unknown
- 1996-12-20 WO PCT/US1996/020766 patent/WO1997023214A1/fr not_active Application Discontinuation
- 1996-12-20 ES ES96944537T patent/ES2196196T3/es not_active Expired - Lifetime
- 1996-12-20 DE DE69628035T patent/DE69628035T2/de not_active Expired - Fee Related
- 1996-12-20 PL PL96327413A patent/PL327413A1/xx unknown
- 1996-12-20 BR BR9612153-0A patent/BR9612153A/pt not_active Application Discontinuation
- 1996-12-20 AU AU14310/97A patent/AU719430B2/en not_active Ceased
- 1996-12-20 PT PT96944537T patent/PT869791E/pt unknown
-
1998
- 1998-06-19 BG BG102561A patent/BG63424B1/bg unknown
- 1998-06-19 MX MX9805032A patent/MX9805032A/es not_active IP Right Cessation
- 1998-06-19 NO NO19982869A patent/NO312028B1/no unknown
-
2000
- 2000-06-13 US US09/592,883 patent/US6448270B1/en not_active Expired - Fee Related
-
2002
- 2002-07-29 US US10/206,578 patent/US20030105133A1/en not_active Abandoned
- 2002-08-06 US US10/172,525 patent/US20030100018A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
ATE239473T1 (de) | 2003-05-15 |
EA199800591A1 (ru) | 1999-02-25 |
NO982869D0 (no) | 1998-06-19 |
MX9805032A (es) | 1998-11-30 |
DE69628035T2 (de) | 2004-02-12 |
WO1997023214A1 (fr) | 1997-07-03 |
DK0869791T3 (da) | 2003-06-10 |
US6130234A (en) | 2000-10-10 |
ES2196196T3 (es) | 2003-12-16 |
EA001133B1 (ru) | 2000-10-30 |
EP0869791A1 (fr) | 1998-10-14 |
PT869791E (pt) | 2003-08-29 |
US20030105133A1 (en) | 2003-06-05 |
AU719430B2 (en) | 2000-05-11 |
PL327413A1 (en) | 1998-12-07 |
IL125060A0 (en) | 1999-01-26 |
CA2240038A1 (fr) | 1997-07-03 |
NO982869L (no) | 1998-08-24 |
AU1431097A (en) | 1997-07-17 |
IL125060A (en) | 2003-07-31 |
NO312028B1 (no) | 2002-03-04 |
BG63424B1 (bg) | 2002-01-31 |
BR9612153A (pt) | 1999-12-28 |
US20030100018A1 (en) | 2003-05-29 |
US6448270B1 (en) | 2002-09-10 |
BG102561A (en) | 1999-04-30 |
JP2000502352A (ja) | 2000-02-29 |
ZA9610741B (en) | 1997-06-24 |
NZ325735A (en) | 2000-02-28 |
DE69628035D1 (de) | 2003-06-12 |
CZ177898A3 (cs) | 1998-12-16 |
EP0869791A4 (fr) | 1999-04-28 |
EP0869791B1 (fr) | 2003-05-07 |
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