ZA200105835B - Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands. - Google Patents

Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands. Download PDF

Info

Publication number: ZA200105835B
Authority: ZA; South Africa
Prior art keywords: diazabicyclo; pyridinyl; chloro; octane; heptane
Prior art date: 1999-01-29

Application number

ZA200105835A

Other languages

English (en)

Inventor

William H Bunnelle

Jerome F Daanen

Michael D Meyer

Michael R Schrimpf

Richard B Toupence

Daniela Barlocco Cristina

Michael J Dart

Keith B Ryther

Kevin B Sippy

Original Assignee

Abbott Lab

Priority date (The priority date 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 date listed.)

1999-01-29

Filing date

2001-07-16

Publication date

2002-10-16

2001-07-16 Application filed by Abbott Lab filed Critical Abbott Lab

2002-10-16 Publication of ZA200105835B publication Critical patent/ZA200105835B/en

Links

102000019315 Nicotinic acetylcholine receptors Human genes 0.000 title description 6
108050006807 Nicotinic acetylcholine receptors Proteins 0.000 title description 6
239000003446 ligand Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 74
IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 60
239000000126 substance Substances 0.000 claims description 20
238000000034 method Methods 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
208000035475 disorder Diseases 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
230000003957 neurotransmitter release Effects 0.000 claims description 6
-1 nitro, 5-tetrazolyl Chemical group 0.000 claims description 6
AVGHIQUXSVAJBC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.1]heptane Chemical compound C1C2CCN1NC2 AVGHIQUXSVAJBC-UHFFFAOYSA-N 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004103 aminoalkyl group Chemical group 0.000 claims description 4
125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
206010012289 Dementia Diseases 0.000 claims description 3
208000018737 Parkinson disease Diseases 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
USXYDBGSWSSTGE-OCAPTIKFSA-N (1s,5r)-3-(6-chloropyridazin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=NC(Cl)=CC=C1N1C[C@H](N2)CC[C@H]2C1 USXYDBGSWSSTGE-OCAPTIKFSA-N 0.000 claims description 2
BQVKPWLMKZFHIT-UHFFFAOYSA-N 2-(6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(Cl)=CC=C1N1C(CN2)CC2C1 BQVKPWLMKZFHIT-UHFFFAOYSA-N 0.000 claims description 2
ZKTZNDDSSBHWTJ-UHFFFAOYSA-N 3-(6-chloropyrazin-2-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound ClC1=CN=CC(N2CC3CCC(N3)C2)=N1 ZKTZNDDSSBHWTJ-UHFFFAOYSA-N 0.000 claims description 2
YOWRIWKBABNICR-UHFFFAOYSA-N 8-(6-chloropyridazin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=NC(Cl)=CC=C1N1C2CCC1CNC2 YOWRIWKBABNICR-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000004967 formylalkyl group Chemical group 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000005358 mercaptoalkyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 18
239000000203 mixture Substances 0.000 claims 12
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 8
BOMUADPKDXMXIH-UHFFFAOYSA-M 1,3-bis(1-methylquinolin-1-ium-6-yl)urea;methyl sulfate Chemical compound COS([O-])(=O)=O.COS([O-])(=O)=O.C[N+]1=CC=CC2=CC(NC(=O)NC=3C=C4C=CC=[N+](C4=CC=3)C)=CC=C21 BOMUADPKDXMXIH-UHFFFAOYSA-M 0.000 claims 2
208000030507 AIDS Diseases 0.000 claims 2
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208000011231 Crohn disease Diseases 0.000 claims 2
208000030814 Eating disease Diseases 0.000 claims 2
208000010228 Erectile Dysfunction Diseases 0.000 claims 2
208000019454 Feeding and Eating disease Diseases 0.000 claims 2
206010061218 Inflammation Diseases 0.000 claims 2
206010026749 Mania Diseases 0.000 claims 2
208000019695 Migraine disease Diseases 0.000 claims 2
206010036618 Premenstrual syndrome Diseases 0.000 claims 2
208000034189 Sclerosis Diseases 0.000 claims 2
208000000323 Tourette Syndrome Diseases 0.000 claims 2
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206010046543 Urinary incontinence Diseases 0.000 claims 2
208000022531 anorexia Diseases 0.000 claims 2
230000036506 anxiety Effects 0.000 claims 2
206010061428 decreased appetite Diseases 0.000 claims 2
235000014632 disordered eating Nutrition 0.000 claims 2
206010015037 epilepsy Diseases 0.000 claims 2
201000001881 impotence Diseases 0.000 claims 2
230000002757 inflammatory effect Effects 0.000 claims 2
230000004054 inflammatory process Effects 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
230000007074 memory dysfunction Effects 0.000 claims 2
230000004770 neurodegeneration Effects 0.000 claims 2
230000004112 neuroprotection Effects 0.000 claims 2
201000000980 schizophrenia Diseases 0.000 claims 2
208000019116 sleep disease Diseases 0.000 claims 2
230000005586 smoking cessation Effects 0.000 claims 2
201000009032 substance abuse Diseases 0.000 claims 2
231100000736 substance abuse Toxicity 0.000 claims 2
208000011117 substance-related disease Diseases 0.000 claims 2
208000011580 syndromic disease Diseases 0.000 claims 2
VWVWGINOEMBUOB-HTQZYQBOSA-N (1r,4r)-2-(5,6-dichloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(Cl)=C1 VWVWGINOEMBUOB-HTQZYQBOSA-N 0.000 claims 1
HSOLSMYRWLJLEZ-PSASIEDQSA-N (1r,4r)-2-(5-bromopyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=CC(Br)=C1 HSOLSMYRWLJLEZ-PSASIEDQSA-N 0.000 claims 1
XXQBILVDTXLLLR-NXEZZACHSA-N (1r,4r)-2-(5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=CC(OC)=C1 XXQBILVDTXLLLR-NXEZZACHSA-N 0.000 claims 1
PJCWGAPXCCOGKP-HUUCEWRRSA-N (1r,4r)-2-(5-phenylmethoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C(C=1)=CN=CC=1OCC1=CC=CC=C1 PJCWGAPXCCOGKP-HUUCEWRRSA-N 0.000 claims 1
MYGNZAWJQQWAFE-GHMZBOCLSA-N (1r,4r)-2-(6-chloro-5-ethynylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(C#C)=C1 MYGNZAWJQQWAFE-GHMZBOCLSA-N 0.000 claims 1
LPMRSAKXONQJPJ-HTQZYQBOSA-N (1r,4r)-2-(6-chloro-5-methylpyridazin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC(C)=C(Cl)N=N1 LPMRSAKXONQJPJ-HTQZYQBOSA-N 0.000 claims 1
CGIVAYCVSYBNBO-RKDXNWHRSA-N (1r,4r)-2-(6-chloro-5-methylpyridazin-3-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C)[H])N2C1=CC(C)=C(Cl)N=N1 CGIVAYCVSYBNBO-RKDXNWHRSA-N 0.000 claims 1
KDAZWLLKSUFNTG-NXEZZACHSA-N (1r,4r)-2-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(C)=C1 KDAZWLLKSUFNTG-NXEZZACHSA-N 0.000 claims 1
WKMLUGOFDWMYKZ-HTQZYQBOSA-N (1r,4r)-2-(6-chloropyridazin-3-yl)-5-methyl-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(N(C[C@@]2([H])C1)C)[H])N2C1=CC=C(Cl)N=N1 WKMLUGOFDWMYKZ-HTQZYQBOSA-N 0.000 claims 1
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CBTCGPHDIOYTJM-PSASIEDQSA-N (1r,4r)-2-(6-fluoro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(F)C(C)=C1 CBTCGPHDIOYTJM-PSASIEDQSA-N 0.000 claims 1
YDTZQKVJVYSCBP-NXEZZACHSA-N (1r,4r)-2-(6-fluoro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(F)C(C)=C1 YDTZQKVJVYSCBP-NXEZZACHSA-N 0.000 claims 1
RKBKKRAXHYTUND-RKDXNWHRSA-N (1r,4r)-2-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CC=C(F)N=C1 RKBKKRAXHYTUND-RKDXNWHRSA-N 0.000 claims 1
MDWOWXOFKFFTAB-MWLCHTKSSA-N (1r,4r)-2-(6-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC=C(C)N=C1 MDWOWXOFKFFTAB-MWLCHTKSSA-N 0.000 claims 1
IKJZJZXKGKENDY-MWLCHTKSSA-N (1r,4r)-2-pyridin-3-yl-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CC=CN=C1 IKJZJZXKGKENDY-MWLCHTKSSA-N 0.000 claims 1
HBMAFIWQQZYQDP-HTQZYQBOSA-N (1r,5r)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(Cl)C(Cl)=C1 HBMAFIWQQZYQDP-HTQZYQBOSA-N 0.000 claims 1
NLBYJBDHHSULMA-MWLCHTKSSA-N (1r,5r)-3-(6-chloro-5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(Cl)C(C#C)=C1 NLBYJBDHHSULMA-MWLCHTKSSA-N 0.000 claims 1
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YMDKFHPQWHQEFT-NXEZZACHSA-N (1r,5r)-3-(6-fluoro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1([H])NC[C@@](C1)(C1)[H])N1C1=CN=C(F)C(C)=C1 YMDKFHPQWHQEFT-NXEZZACHSA-N 0.000 claims 1
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BDDBIULBMALEAN-HTQZYQBOSA-N (1r,5r)-6-(5-bromo-6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(Cl)C(Br)=C1 BDDBIULBMALEAN-HTQZYQBOSA-N 0.000 claims 1
PVRLCIPGIOMSTL-MWLCHTKSSA-N (1r,5r)-6-(5-ethynyl-6-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(F)C(C#C)=C1 PVRLCIPGIOMSTL-MWLCHTKSSA-N 0.000 claims 1
HVFAVMAEHDLGFX-NXEZZACHSA-N (1r,5r)-6-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=CC(OC)=C1 HVFAVMAEHDLGFX-NXEZZACHSA-N 0.000 claims 1
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FTGNYUNGLWDAOD-PSASIEDQSA-N (1r,5r)-6-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CC=C(Cl)N=C1 FTGNYUNGLWDAOD-PSASIEDQSA-N 0.000 claims 1
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GJVAKOWYUPGMPN-PWSUYJOCSA-N (1r,5s)-4-(6-chloro-5-ethynylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(Cl)C(C#C)=C1 GJVAKOWYUPGMPN-PWSUYJOCSA-N 0.000 claims 1
HOFIEMCFOWCLAI-KOLCDFICSA-N (1r,5s)-4-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(Cl)C(C)=C1 HOFIEMCFOWCLAI-KOLCDFICSA-N 0.000 claims 1
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UBKMVKPQYKJIRD-MNOVXSKESA-N (1r,6s)-4-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@@]1(CC[C@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(C)=C1 UBKMVKPQYKJIRD-MNOVXSKESA-N 0.000 claims 1
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GCYULHICELESPR-MNOVXSKESA-N (1r,6s)-9-(5-methoxypyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=CC(OC)=C1 GCYULHICELESPR-MNOVXSKESA-N 0.000 claims 1
ASYILFSEFBVAHP-MNOVXSKESA-N (1r,6s)-9-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@@]2([H])CC[C@@]1(CCNC2)[H])C1=CN=C(Cl)C(C)=C1 ASYILFSEFBVAHP-MNOVXSKESA-N 0.000 claims 1
IBCNMAGSFIKYFO-YUMQZZPRSA-N (1s,4s)-2-(5-bromo-6-chloropyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(Cl)C(Br)=C1 IBCNMAGSFIKYFO-YUMQZZPRSA-N 0.000 claims 1
XXQBILVDTXLLLR-UWVGGRQHSA-N (1s,4s)-2-(5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=CC(OC)=C1 XXQBILVDTXLLLR-UWVGGRQHSA-N 0.000 claims 1
XTBFEBHZTXDLNN-YUMQZZPRSA-N (1s,4s)-2-(6-chloro-5-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2C1=CN=C(Cl)C(OC)=C1 XTBFEBHZTXDLNN-YUMQZZPRSA-N 0.000 claims 1
KDAZWLLKSUFNTG-UWVGGRQHSA-N (1s,4s)-2-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CN=C(Cl)C(C)=C1 KDAZWLLKSUFNTG-UWVGGRQHSA-N 0.000 claims 1
IKJZJZXKGKENDY-ONGXEEELSA-N (1s,4s)-2-pyridin-3-yl-2,5-diazabicyclo[2.2.2]octane Chemical compound N1([C@@]2([H])CC[C@](NC2)(C1)[H])C1=CC=CN=C1 IKJZJZXKGKENDY-ONGXEEELSA-N 0.000 claims 1
VSNFTKFKMDNYIB-VHSXEESVSA-N (1s,5r)-4-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=CC(OC)=C1 VSNFTKFKMDNYIB-VHSXEESVSA-N 0.000 claims 1
AFMGMCFRGXNXME-WCBMZHEXSA-N (1s,5r)-4-(6-fluoropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CC=C(F)N=C1 AFMGMCFRGXNXME-WCBMZHEXSA-N 0.000 claims 1
WMYOQZRIEFMPDD-SFYZADRCSA-N (1s,5r)-7-(5-bromo-6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(Br)=C1 WMYOQZRIEFMPDD-SFYZADRCSA-N 0.000 claims 1
MXMWDEJGOFAQIF-ZJUUUORDSA-N (1s,5r)-7-(5-methoxypyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=CC(OC)=C1 MXMWDEJGOFAQIF-ZJUUUORDSA-N 0.000 claims 1
LEJILTNCTMWMAF-MNOVXSKESA-N (1s,5r)-7-(6-chloro-5-ethynylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C#C)=C1 LEJILTNCTMWMAF-MNOVXSKESA-N 0.000 claims 1
TVSYLDOEQMXDNJ-ZJUUUORDSA-N (1s,5r)-7-(6-chloro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C)=C1 TVSYLDOEQMXDNJ-ZJUUUORDSA-N 0.000 claims 1
DOLPRZLBJYAFEQ-ZJUUUORDSA-N (1s,5r)-7-(6-fluoro-5-methylpyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CN=C(F)C(C)=C1 DOLPRZLBJYAFEQ-ZJUUUORDSA-N 0.000 claims 1
LODFTIXAWYPTQJ-BDAKNGLRSA-N (1s,5r)-7-(6-fluoropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@]2([H])CCN1)[H])N2C1=CC=C(F)N=C1 LODFTIXAWYPTQJ-BDAKNGLRSA-N 0.000 claims 1
UYYPHVFFQXEJKF-YUMQZZPRSA-N (1s,5s)-3-(5-bromo-6-chloropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=C(Cl)C(Br)=C1 UYYPHVFFQXEJKF-YUMQZZPRSA-N 0.000 claims 1
UVORMACRUDDZOI-UWVGGRQHSA-N (1s,5s)-3-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=CC(OC)=C1 UVORMACRUDDZOI-UWVGGRQHSA-N 0.000 claims 1
NSZNGOJYQHWDIQ-UWVGGRQHSA-N (1s,5s)-3-(6-chloro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=C(Cl)C(C)=C1 NSZNGOJYQHWDIQ-UWVGGRQHSA-N 0.000 claims 1
HVFAVMAEHDLGFX-UWVGGRQHSA-N (1s,5s)-6-(5-methoxypyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CN=CC(OC)=C1 HVFAVMAEHDLGFX-UWVGGRQHSA-N 0.000 claims 1
ZLFPSGCWGZRCNZ-ONGXEEELSA-N (1s,5s)-6-(6-chloro-5-ethynylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CN=C(Cl)C(C#C)=C1 ZLFPSGCWGZRCNZ-ONGXEEELSA-N 0.000 claims 1
MOALZDBEPGDEKO-ONGXEEELSA-N (1s,5s)-6-(6-fluoro-5-methylpyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CN=C(F)C(C)=C1 MOALZDBEPGDEKO-ONGXEEELSA-N 0.000 claims 1
RCUIVEFKYGBCPS-WPRPVWTQSA-N (1s,5s)-6-(6-fluoropyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CC=C(F)N=C1 RCUIVEFKYGBCPS-WPRPVWTQSA-N 0.000 claims 1
ZLHFGGWPDZHAJF-ONGXEEELSA-N (1s,5s)-6-pyridin-3-yl-3,6-diazabicyclo[3.2.1]octane Chemical compound C([C@]1(C[C@@]2([H])CNC1)[H])N2C1=CC=CN=C1 ZLHFGGWPDZHAJF-ONGXEEELSA-N 0.000 claims 1
GEWXCNBZLXRDAX-DTWKUNHWSA-N (1s,6r)-4-(5-bromo-6-chloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(Br)=C1 GEWXCNBZLXRDAX-DTWKUNHWSA-N 0.000 claims 1
HEAXNRWRTMPNJF-NWDGAFQWSA-N (1s,6r)-4-(5-ethynyl-6-fluoropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(F)C(C#C)=C1 HEAXNRWRTMPNJF-NWDGAFQWSA-N 0.000 claims 1
XGLUSGAITGFVAL-WDEREUQCSA-N (1s,6r)-4-(5-methoxypyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=CC(OC)=C1 XGLUSGAITGFVAL-WDEREUQCSA-N 0.000 claims 1
ZNBQVWOSKWWGGL-NWDGAFQWSA-N (1s,6r)-4-(6-chloro-5-ethynylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(C#C)=C1 ZNBQVWOSKWWGGL-NWDGAFQWSA-N 0.000 claims 1
UBKMVKPQYKJIRD-WDEREUQCSA-N (1s,6r)-4-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound C([C@]1(CC[C@@](CC2)(N1)[H])[H])N2C1=CN=C(Cl)C(C)=C1 UBKMVKPQYKJIRD-WDEREUQCSA-N 0.000 claims 1
RWOLEIVLXVKUNS-DTWKUNHWSA-N (1s,6r)-9-(5,6-dichloropyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@]2([H])CC[C@]1(CCNC2)[H])C1=CN=C(Cl)C(Cl)=C1 RWOLEIVLXVKUNS-DTWKUNHWSA-N 0.000 claims 1
ASYILFSEFBVAHP-WDEREUQCSA-N (1s,6r)-9-(6-chloro-5-methylpyridin-3-yl)-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@]2([H])CC[C@]1(CCNC2)[H])C1=CN=C(Cl)C(C)=C1 ASYILFSEFBVAHP-WDEREUQCSA-N 0.000 claims 1
UHVDNONGKVDHEZ-CMPLNLGQSA-N (1s,6r)-9-pyridin-3-yl-4,9-diazabicyclo[4.2.1]nonane Chemical compound N1([C@]2([H])CC[C@]1(CCNC2)[H])C1=CC=CN=C1 UHVDNONGKVDHEZ-CMPLNLGQSA-N 0.000 claims 1
BYYIXAPRYVEOEB-RKDXNWHRSA-N 1-chloro-4-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]phthalazine Chemical compound C1=CC=C2C(N3C[C@@]4(NC[C@@]3([H])C4)[H])=NN=C(Cl)C2=C1 BYYIXAPRYVEOEB-RKDXNWHRSA-N 0.000 claims 1
BYYIXAPRYVEOEB-IUCAKERBSA-N 1-chloro-4-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]phthalazine Chemical compound C1=CC=C2C(N3C[C@]4(NC[C@]3([H])C4)[H])=NN=C(Cl)C2=C1 BYYIXAPRYVEOEB-IUCAKERBSA-N 0.000 claims 1
FRVGBUBUZLXEJI-UHFFFAOYSA-N 2-(6-chloro-5-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound N1=C(Cl)C(C)=CC(N2C3CC(NC3)C2)=C1 FRVGBUBUZLXEJI-UHFFFAOYSA-N 0.000 claims 1
ONPXTLLWQNBLPG-UHFFFAOYSA-N 2-(6-fluoropyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(F)=CC=C1N1C(CN2)CC2C1 ONPXTLLWQNBLPG-UHFFFAOYSA-N 0.000 claims 1
HNRIHCBMMRMJDG-UHFFFAOYSA-N 2-(6-methoxypyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(OC)=CC=C1N1C(CN2)CC2C1 HNRIHCBMMRMJDG-UHFFFAOYSA-N 0.000 claims 1
MDWOWXOFKFFTAB-UHFFFAOYSA-N 2-(6-methylpyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane Chemical compound C1=NC(C)=CC=C1N1C(CN2)CC2C1 MDWOWXOFKFFTAB-UHFFFAOYSA-N 0.000 claims 1
LVEDPTDGTCVLOE-UHFFFAOYSA-N 2-chloro-5-(3,7-diazabicyclo[3.3.1]nonan-3-yl)pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Cl)=NC=C1N1CC(C2)CNCC2C1 LVEDPTDGTCVLOE-UHFFFAOYSA-N 0.000 claims 1
QTGGWVSXJFOQQA-UHFFFAOYSA-N 2-chloro-5-(3,8-diazabicyclo[3.2.1]octan-3-yl)pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Cl)=NC=C1N1CC(N2)CCC2C1 QTGGWVSXJFOQQA-UHFFFAOYSA-N 0.000 claims 1
NRFYACWYEJZMRE-PSASIEDQSA-N 2-chloro-5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(Cl)C(C#N)=C1 NRFYACWYEJZMRE-PSASIEDQSA-N 0.000 claims 1
YWXHDGVOLPDNSV-NXEZZACHSA-N 2-chloro-5-[(1r,4r)-2,5-diazabicyclo[2.2.2]octan-2-yl]pyridine-3-carbonitrile Chemical compound N1([C@]2([H])CC[C@@](NC2)(C1)[H])C1=CN=C(Cl)C(C#N)=C1 YWXHDGVOLPDNSV-NXEZZACHSA-N 0.000 claims 1
ORTIGJSCTJQDMP-PSASIEDQSA-N 2-chloro-5-[(1r,5r)-3,6-diazabicyclo[3.2.1]octan-6-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1(C[C@]2([H])CNC1)[H])N2C1=CN=C(Cl)C(C#N)=C1 ORTIGJSCTJQDMP-PSASIEDQSA-N 0.000 claims 1
FEVLGLCNQGLREU-KOLCDFICSA-N 2-chloro-5-[(1r,5s)-4,7-diazabicyclo[3.2.1]octan-4-yl]pyridine-3-carbonitrile Chemical compound N1([C@@]2([H])C[C@](NC2)(CC1)[H])C1=CN=C(Cl)C(C#N)=C1 FEVLGLCNQGLREU-KOLCDFICSA-N 0.000 claims 1
CUVZIAWUWKJYRZ-VHSXEESVSA-N 2-chloro-5-[(1r,5s)-4,7-diazabicyclo[3.2.1]octan-7-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1(C[C@@]2([H])CCN1)[H])N2C1=CN=C(Cl)C(C#N)=C1 CUVZIAWUWKJYRZ-VHSXEESVSA-N 0.000 claims 1
FEVLGLCNQGLREU-GXSJLCMTSA-N 2-chloro-5-[(1s,5r)-4,7-diazabicyclo[3.2.1]octan-4-yl]pyridine-3-carbonitrile Chemical compound N1([C@]2([H])C[C@@](NC2)(CC1)[H])C1=CN=C(Cl)C(C#N)=C1 FEVLGLCNQGLREU-GXSJLCMTSA-N 0.000 claims 1
FBYJNKLXXDUKPJ-WPRPVWTQSA-N 2-chloro-5-[(1s,5s)-3,6-diazabicyclo[3.2.1]octan-3-yl]pyridine-3-carbonitrile Chemical compound C([C@@]1([H])NC[C@](C1)(C1)[H])N1C1=CN=C(Cl)C(C#N)=C1 FBYJNKLXXDUKPJ-WPRPVWTQSA-N 0.000 claims 1
GTFIBWYZLKFYGQ-UHFFFAOYSA-N 3-(5,6-dichloropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=C(Cl)C(Cl)=CC(N2CC3CCC(N3)C2)=C1 GTFIBWYZLKFYGQ-UHFFFAOYSA-N 0.000 claims 1
XSENXYRHJRRCCP-UHFFFAOYSA-N 3-(5-bromo-6-chloropyridin-3-yl)-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1=C(Br)C(Cl)=NC=C1N1CC(C2)CNCC2C1 XSENXYRHJRRCCP-UHFFFAOYSA-N 0.000 claims 1
XKHAMSWZBIFYEF-UHFFFAOYSA-N 3-(5-bromo-6-chloropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=C(Br)C(Cl)=NC=C1N1CC(N2)CCC2C1 XKHAMSWZBIFYEF-UHFFFAOYSA-N 0.000 claims 1
KKXRWJXNPLBROS-UHFFFAOYSA-N 3-(5-ethynyl-6-fluoropyridin-3-yl)-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1=C(C#C)C(F)=NC=C1N1CC(C2)CNCC2C1 KKXRWJXNPLBROS-UHFFFAOYSA-N 0.000 claims 1
AYECEKGNILHLRL-UHFFFAOYSA-N 3-(5-ethynyl-6-fluoropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=C(C#C)C(F)=NC=C1N1CC(N2)CCC2C1 AYECEKGNILHLRL-UHFFFAOYSA-N 0.000 claims 1
BNPCEETXPUKHLC-UHFFFAOYSA-N 3-(6-chloro-5-ethynylpyridin-3-yl)-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1=C(C#C)C(Cl)=NC=C1N1CC(C2)CNCC2C1 BNPCEETXPUKHLC-UHFFFAOYSA-N 0.000 claims 1
TXSUUUHHYAMRKK-UHFFFAOYSA-N 3-(6-chloro-5-ethynylpyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=C(C#C)C(Cl)=NC=C1N1CC(N2)CCC2C1 TXSUUUHHYAMRKK-UHFFFAOYSA-N 0.000 claims 1
BXQVWZDNOZKPLA-UHFFFAOYSA-N 3-(6-chloropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=NC(Cl)=CC=C1N1CC(N2)CCC2C1 BXQVWZDNOZKPLA-UHFFFAOYSA-N 0.000 claims 1
RPBHQOWASYRAGS-UHFFFAOYSA-N 3-(6-fluoro-5-methylpyridin-3-yl)-3,7-diazabicyclo[3.3.1]nonane Chemical compound N1=C(F)C(C)=CC(N2CC3CNCC(C3)C2)=C1 RPBHQOWASYRAGS-UHFFFAOYSA-N 0.000 claims 1
CVLNMKCUYYJTQN-UHFFFAOYSA-N 3-(6-fluoro-5-methylpyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound N1=C(F)C(C)=CC(N2CC3CCC(N3)C2)=C1 CVLNMKCUYYJTQN-UHFFFAOYSA-N 0.000 claims 1
BLYYOMPZEPOXIT-UHFFFAOYSA-N 3-(6-fluoropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=NC(F)=CC=C1N1CC(N2)CCC2C1 BLYYOMPZEPOXIT-UHFFFAOYSA-N 0.000 claims 1
KVCPNCMGNJWKCS-UHFFFAOYSA-N 3-(6-nitropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octane Chemical compound C1=NC([N+](=O)[O-])=CC=C1N1CC(N2)CCC2C1 KVCPNCMGNJWKCS-UHFFFAOYSA-N 0.000 claims 1
VMNQBOWUPKNWAS-DGCLKSJQSA-N 3-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]quinoline Chemical compound C1=CC=CC2=CC(N3C[C@@]4(NC[C@@]3([H])C4)[H])=CN=C21 VMNQBOWUPKNWAS-DGCLKSJQSA-N 0.000 claims 1
QGPJNUIJAGMDMT-UHFFFAOYSA-N 3-pyridin-3-yl-3,7-diazabicyclo[3.3.1]nonane Chemical compound C1NCC(C2)CC1CN2C1=CC=CN=C1 QGPJNUIJAGMDMT-UHFFFAOYSA-N 0.000 claims 1
GFPKENYJHPZLJI-UHFFFAOYSA-N 3-pyridin-3-yl-3,8-diazabicyclo[3.2.1]octane Chemical compound C1C(N2)CCC2CN1C1=CC=CN=C1 GFPKENYJHPZLJI-UHFFFAOYSA-N 0.000 claims 1
JYFFKBVSSSXOBJ-UHFFFAOYSA-N 4-(6-chloropyridin-3-yl)-4,7-diazabicyclo[3.2.1]octane Chemical compound C1=NC(Cl)=CC=C1N1C(CN2)CC2CC1 JYFFKBVSSSXOBJ-UHFFFAOYSA-N 0.000 claims 1
RXMPTHLJGKSEAG-UHFFFAOYSA-N 4-pyridin-3-yl-4,7-diazabicyclo[3.2.1]octane Chemical compound C1NC(CC2)CC1N2C1=CC=CN=C1 RXMPTHLJGKSEAG-UHFFFAOYSA-N 0.000 claims 1
IMAFPMMJFGWHQM-UHFFFAOYSA-N 4-pyridin-3-yl-4,9-diazabicyclo[4.2.1]nonane Chemical compound C1CC(N2)CCC2CN1C1=CC=CN=C1 IMAFPMMJFGWHQM-UHFFFAOYSA-N 0.000 claims 1
CJRLDFQDWXLGLH-UHFFFAOYSA-N 5-(2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C3CC(NC3)C2)=C1 CJRLDFQDWXLGLH-UHFFFAOYSA-N 0.000 claims 1
IYNBYHMSSSABOB-UHFFFAOYSA-N 5-(2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(N2C3CC(NC3)C2)=C1 IYNBYHMSSSABOB-UHFFFAOYSA-N 0.000 claims 1
ZHJMFUVNZRJUNC-UHFFFAOYSA-N 5-(3,7-diazabicyclo[3.3.1]nonan-3-yl)-2-fluoropyridine-3-carbonitrile Chemical compound C1=C(C#N)C(F)=NC=C1N1CC(C2)CNCC2C1 ZHJMFUVNZRJUNC-UHFFFAOYSA-N 0.000 claims 1
XIEKCSAAGQQQEN-UHFFFAOYSA-N 5-(3,8-diazabicyclo[3.2.1]octan-3-yl)-2-fluoropyridine-3-carbonitrile Chemical compound C1=C(C#N)C(F)=NC=C1N1CC(N2)CCC2C1 XIEKCSAAGQQQEN-UHFFFAOYSA-N 0.000 claims 1
PZYQHIBWPHJONC-RNFRBKRXSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-fluoropyridine-3-carboxamide Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(F)C(C(N)=O)=C1 PZYQHIBWPHJONC-RNFRBKRXSA-N 0.000 claims 1
DKGVDEQTBDIKJT-RNFRBKRXSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-fluoropyridine-3-sulfonamide Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=C(F)C(S(N)(=O)=O)=C1 DKGVDEQTBDIKJT-RNFRBKRXSA-N 0.000 claims 1
QASONRSLKVKRRW-VXNVDRBHSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridin-2-amine Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CC=C(N)N=C1 QASONRSLKVKRRW-VXNVDRBHSA-N 0.000 claims 1
NMHTXPVGXBELTF-PSASIEDQSA-N 5-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]pyridine-3-carboxylic acid Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C1=CN=CC(C(O)=O)=C1 NMHTXPVGXBELTF-PSASIEDQSA-N 0.000 claims 1
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Classifications

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- 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
- C07D401/08—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 alicyclic rings
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- C07D417/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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ZA200105835A 1999-01-29 2001-07-16 Diazabicyclic derivatives as nicotinic acetylcholine receptor ligands. ZA200105835B (en)

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US23983899A	1999-01-29	1999-01-29

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EP (2)	EP1359152B1 (es)
JP (1)	JP4676062B2 (es)
KR (1)	KR20010101725A (es)
CN (2)	CN1636996A (es)
AR (1)	AR034538A1 (es)
AT (2)	ATE394401T1 (es)
AU (1)	AU773795B2 (es)
BG (1)	BG105836A (es)
BR (1)	BR0007664A (es)
CA (1)	CA2361525C (es)
CO (1)	CO5150231A1 (es)
CZ (1)	CZ20012716A3 (es)
DE (2)	DE60006213T2 (es)
DK (1)	DK1147112T3 (es)
ES (2)	ES2305373T3 (es)
HK (1)	HK1043116B (es)
HU (1)	HUP0200332A3 (es)
IL (1)	IL144340A0 (es)
NO (1)	NO20013731L (es)
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SK (1)	SK10692001A3 (es)
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TW (1)	TW200300021A (es)
WO (1)	WO2000044755A1 (es)
ZA (1)	ZA200105835B (es)

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NO20013731L (no)	2001-09-18
NO20013731D0 (no)	2001-07-30
HUP0200332A3 (en)	2002-09-30
AU773795B2 (en)	2004-06-03
AU2856900A (en)	2000-08-18
DE60006213T2 (de)	2004-07-29
DE60038823D1 (de)	2008-06-19
CZ20012716A3 (cs)	2001-11-14
NZ512884A (en)	2004-03-26
TW200300021A (en)	2003-05-01
HK1043116A1 (en)	2002-09-06
DK1147112T3 (da)	2004-02-23
EP1359152A2 (en)	2003-11-05
JP2002535409A (ja)	2002-10-22
JP4676062B2 (ja)	2011-04-27
ATE394401T1 (de)	2008-05-15
WO2000044755A1 (en)	2000-08-03
EP1359152B1 (en)	2008-05-07
BR0007664A (pt)	2002-05-07
HUP0200332A2 (en)	2002-06-29
EP1359152A3 (en)	2003-12-17
ATE253067T1 (de)	2003-11-15
CN1636996A (zh)	2005-07-13
AR034538A1 (es)	2004-03-03
KR20010101725A (ko)	2001-11-14
ES2209825T3 (es)	2004-07-01
SK10692001A3 (sk)	2002-01-07
CN1345320A (zh)	2002-04-17
BG105836A (en)	2002-03-29
ES2305373T3 (es)	2008-11-01
CO5150231A1 (es)	2002-04-29
PT1147112E (pt)	2004-03-31
HK1043116B (zh)	2004-10-15
IL144340A0 (en)	2002-05-23
CA2361525A1 (en)	2000-08-03
DE60006213D1 (de)	2003-12-04
EP1147112A1 (en)	2001-10-24
CA2361525C (en)	2009-12-08
TR200102162T2 (tr)	2001-12-21
EP1147112B1 (en)	2003-10-29

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