CA2551486A1 - Derives polycycliques de quinuclidine substitues par un bicycloheterocycle condense - Google Patents

Derives polycycliques de quinuclidine substitues par un bicycloheterocycle condense Download PDF

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Publication number: CA2551486A1
Authority: CA; Canada
Prior art keywords: group; yloxy; formula; mmol; aza
Prior art date: 2003-12-22
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.): Abandoned

Application number

CA002551486A

Other languages

English (en)

Inventor

Jianguo Ji

Tao Li

Kathleen H. Mortell

Michael R. Schrimpf

Diana L. Nersesian

Liping Pan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Abbott Laboratories

Original Assignee

Individual

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.)

2003-12-22

Filing date

2004-12-10

Publication date

2006-06-22

2004-12-10 Application filed by Individual filed Critical Individual

2006-06-22 Publication of CA2551486A1 publication Critical patent/CA2551486A1/fr

Status Abandoned legal-status Critical Current

Links

150000008584 quinuclidines Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 322
238000000034 method Methods 0.000 claims abstract description 67
125000003118 aryl group Chemical group 0.000 claims abstract description 40
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims description 64
102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 31
108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 28
230000000694 effects Effects 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 16
208000024827 Alzheimer disease Diseases 0.000 claims description 15
208000035475 disorder Diseases 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
150000001408 amides Chemical class 0.000 claims description 13
206010012289 Dementia Diseases 0.000 claims description 12
239000000651 prodrug Substances 0.000 claims description 11
229940002612 prodrug Drugs 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
208000002193 Pain Diseases 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
201000000980 schizophrenia Diseases 0.000 claims description 9
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 8
208000010877 cognitive disease Diseases 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
210000003169 central nervous system Anatomy 0.000 claims description 6
239000003693 atypical antipsychotic agent Substances 0.000 claims description 5
229940127236 atypical antipsychotics Drugs 0.000 claims description 5
230000004770 neurodegeneration Effects 0.000 claims description 5
208000030507 AIDS Diseases 0.000 claims description 4
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
201000010374 Down Syndrome Diseases 0.000 claims description 4
201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
206010039966 Senile dementia Diseases 0.000 claims description 4
206010044688 Trisomy 21 Diseases 0.000 claims description 4
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
210000004204 blood vessel Anatomy 0.000 claims description 4
208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
210000004558 lewy body Anatomy 0.000 claims description 4
208000027061 mild cognitive impairment Diseases 0.000 claims description 4
208000000094 Chronic Pain Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
206010065390 Inflammatory pain Diseases 0.000 claims description 3
208000004550 Postoperative Pain Diseases 0.000 claims description 3
208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
206010053648 Vascular occlusion Diseases 0.000 claims description 3
208000005298 acute pain Diseases 0.000 claims description 3
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
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208000021722 neuropathic pain Diseases 0.000 claims description 3
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208000021331 vascular occlusion disease Diseases 0.000 claims description 3
230000029663 wound healing Effects 0.000 claims description 3
IYQKLJISQKXUEU-NRFANRHFSA-N 1-[5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1h-indol-3-yl]-n,n-dimethylmethanamine Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C2NC=C(CN(C)C)C2=C1 IYQKLJISQKXUEU-NRFANRHFSA-N 0.000 claims description 2
QGGUZNMEZCYFGG-UHFFFAOYSA-N 2-[4-(1-azabicyclo[2.2.2]octan-3-yloxy)phenyl]-1h-indole Chemical compound C1=CC=C2NC(C3=CC=C(C=C3)OC3C4CCN(C3)CC4)=CC2=C1 QGGUZNMEZCYFGG-UHFFFAOYSA-N 0.000 claims description 2
ILDQLEZWIYUAFF-UHFFFAOYSA-N 3-[4-(1-azabicyclo[2.2.2]octan-3-yloxy)phenyl]-1h-indole Chemical compound C1=CC=C2C(C3=CC=C(C=C3)OC3C4CCN(C3)CC4)=CNC2=C1 ILDQLEZWIYUAFF-UHFFFAOYSA-N 0.000 claims description 2
AGQZHWHGJXEHAU-UHFFFAOYSA-N 3-[6-(1-azabicyclo[2.2.2]octan-3-yloxy)pyridazin-3-yl]-1h-indole Chemical compound C1=CC=C2C(C3=CC=C(N=N3)OC3C4CCN(C3)CC4)=CNC2=C1 AGQZHWHGJXEHAU-UHFFFAOYSA-N 0.000 claims description 2
AGQZHWHGJXEHAU-SFHVURJKSA-N 3-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1h-indole Chemical compound C1=CC=C2C(C3=CC=C(N=N3)O[C@@H]3C4CCN(C3)CC4)=CNC2=C1 AGQZHWHGJXEHAU-SFHVURJKSA-N 0.000 claims description 2
UXEQQXQWJSFLPE-QFIPXVFZSA-N 3-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-9h-carbazole Chemical compound C1=CC=C2C3=CC(C4=CC=C(N=N4)O[C@@H]4C5CCN(C4)CC5)=CC=C3NC2=C1 UXEQQXQWJSFLPE-QFIPXVFZSA-N 0.000 claims description 2
AGQZHWHGJXEHAU-GOSISDBHSA-N 3-[6-[[(3s)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1h-indole Chemical compound C1=CC=C2C(C3=CC=C(N=N3)O[C@H]3C4CCN(C3)CC4)=CNC2=C1 AGQZHWHGJXEHAU-GOSISDBHSA-N 0.000 claims description 2
MXYDEQXRKKUFTL-SFHVURJKSA-N 4-[2-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-1h-indole Chemical compound O([C@@H]1C2CCN(C1)CC2)C(N=C1)=NC=C1C1=CC=CC2=C1C=CN2 MXYDEQXRKKUFTL-SFHVURJKSA-N 0.000 claims description 2
JVFHKRDZWLICSZ-XJCQOYGMSA-N 4-[2-[[(3r)-1-oxido-1-azoniabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-1h-indole Chemical compound O([C@@H]1C2CC[N+](CC2)(C1)[O-])C(N=C1)=NC=C1C1=CC=CC2=C1C=CN2 JVFHKRDZWLICSZ-XJCQOYGMSA-N 0.000 claims description 2
NLYRWVYFBQLDNN-UHFFFAOYSA-N 4-[4-(1-azabicyclo[2.2.2]octan-3-yloxy)phenyl]-1h-indole Chemical compound C1CN(C2)CCC1C2OC(C=C1)=CC=C1C1=CC=CC2=C1C=CN2 NLYRWVYFBQLDNN-UHFFFAOYSA-N 0.000 claims description 2
GHFNBRCTKJMLHZ-UHFFFAOYSA-N 4-[6-(1-azabicyclo[2.2.2]octan-3-yloxy)pyridazin-3-yl]-1h-indole Chemical compound C1CN(C2)CCC1C2OC(N=N1)=CC=C1C1=CC=CC2=C1C=CN2 GHFNBRCTKJMLHZ-UHFFFAOYSA-N 0.000 claims description 2
UOBMVUNFDOOGIA-KRWDZBQOSA-N 5-[2-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-1,3-benzoxazole Chemical compound C1=C2OC=NC2=CC(C2=CN=C(N=C2)O[C@@H]2C3CCN(C2)CC3)=C1 UOBMVUNFDOOGIA-KRWDZBQOSA-N 0.000 claims description 2
GTSOUQUYFXGNJP-SFHVURJKSA-N 5-[2-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CN=C(N=C2)O[C@@H]2C3CCN(C2)CC3)=C1 GTSOUQUYFXGNJP-SFHVURJKSA-N 0.000 claims description 2
BVZJRDALCRCJQU-QFIPXVFZSA-N 5-[2-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-2-phenyl-1,3-benzoxazole Chemical compound O([C@@H]1C2CCN(C1)CC2)C(N=C1)=NC=C1C(C=C1N=2)=CC=C1OC=2C1=CC=CC=C1 BVZJRDALCRCJQU-QFIPXVFZSA-N 0.000 claims description 2
HFEZNZAPCVCKMP-INIZCTEOSA-N 5-[2-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1N(CC2)CCC2[C@H]1OC(N=C1)=NC=C1C1=CC=C(OC(=O)N2)C2=C1 HFEZNZAPCVCKMP-INIZCTEOSA-N 0.000 claims description 2
GTSOUQUYFXGNJP-GOSISDBHSA-N 5-[2-[[(3s)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CN=C(N=C2)O[C@H]2C3CCN(C2)CC3)=C1 GTSOUQUYFXGNJP-GOSISDBHSA-N 0.000 claims description 2
YULBEJGLTXDNOV-UHFFFAOYSA-N 5-[4-(1-azabicyclo[2.2.2]octan-3-yloxy)phenyl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CC=C(C=C2)OC2C3CCN(C2)CC3)=C1 YULBEJGLTXDNOV-UHFFFAOYSA-N 0.000 claims description 2
FXRKSLCORBVZAL-UHFFFAOYSA-N 5-[4-(1-azabicyclo[2.2.2]octan-3-yloxy)phenyl]-3-methyl-2h-indazole Chemical compound C1N(CC2)CCC2C1OC(C=C1)=CC=C1C1=CC=C2NN=C(C)C2=C1 FXRKSLCORBVZAL-UHFFFAOYSA-N 0.000 claims description 2
YULBEJGLTXDNOV-NRFANRHFSA-N 5-[4-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]phenyl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CC=C(C=C2)O[C@@H]2C3CCN(C2)CC3)=C1 YULBEJGLTXDNOV-NRFANRHFSA-N 0.000 claims description 2
LUKNJAQKVPBDSC-UHFFFAOYSA-N 5-[6-(1-azabicyclo[2.2.2]octan-3-yloxy)pyridazin-3-yl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CC=C(N=N2)OC2C3CCN(C2)CC3)=C1 LUKNJAQKVPBDSC-UHFFFAOYSA-N 0.000 claims description 2
ACLCJNOKGJPMLH-INIZCTEOSA-N 5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1,3-dihydrobenzimidazol-2-one Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C2NC(=O)NC2=C1 ACLCJNOKGJPMLH-INIZCTEOSA-N 0.000 claims description 2
UFGNPNHROKRPMA-KRWDZBQOSA-N 5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1,3-dihydroindol-2-one Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C(NC(=O)C2)C2=C1 UFGNPNHROKRPMA-KRWDZBQOSA-N 0.000 claims description 2
OCUUBBDATKSJCC-IBGZPJMESA-N 5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1-methylindole Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C2N(C)C=CC2=C1 OCUUBBDATKSJCC-IBGZPJMESA-N 0.000 claims description 2
LUKNJAQKVPBDSC-SFHVURJKSA-N 5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CC=C(N=N2)O[C@@H]2C3CCN(C2)CC3)=C1 LUKNJAQKVPBDSC-SFHVURJKSA-N 0.000 claims description 2
XZVULKFJGAJNOG-IBGZPJMESA-N 5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-3-methyl-1h-indole Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C2NC=C(C)C2=C1 XZVULKFJGAJNOG-IBGZPJMESA-N 0.000 claims description 2
JQQQPXXRUGNREH-SFHVURJKSA-N 5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-3-methyl-2h-indazole Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C2NN=C(C)C2=C1 JQQQPXXRUGNREH-SFHVURJKSA-N 0.000 claims description 2
NSPBIYQIBBJULY-IBGZPJMESA-N 5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridin-3-yl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CC=C(N=C2)O[C@@H]2C3CCN(C2)CC3)=C1 NSPBIYQIBBJULY-IBGZPJMESA-N 0.000 claims description 2
WYRNXLDJVZZQOW-XJCQOYGMSA-N 5-[6-[[(3r)-1-oxido-1-azoniabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CC=C(N=N2)O[C@@H]2C3CC[N+](CC3)(C2)[O-])=C1 WYRNXLDJVZZQOW-XJCQOYGMSA-N 0.000 claims description 2
LUKNJAQKVPBDSC-GOSISDBHSA-N 5-[6-[[(3s)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1h-indole Chemical compound C1=C2NC=CC2=CC(C2=CC=C(N=N2)O[C@H]2C3CCN(C2)CC3)=C1 LUKNJAQKVPBDSC-GOSISDBHSA-N 0.000 claims description 2
CQLRRWLSSBLWCT-UHFFFAOYSA-N 6-[4-(1-azabicyclo[2.2.2]octan-3-yloxy)phenyl]-1,3-benzothiazol-2-amine Chemical compound C1N(CC2)CCC2C1OC(C=C1)=CC=C1C1=CC=C2N=C(N)SC2=C1 CQLRRWLSSBLWCT-UHFFFAOYSA-N 0.000 claims description 2
QOIFHUCHKRDTMO-UHFFFAOYSA-N 6-[4-(1-azabicyclo[2.2.2]octan-3-yloxy)phenyl]-1h-indole Chemical compound C1=C2C=CNC2=CC(C2=CC=C(C=C2)OC2C3CCN(C2)CC3)=C1 QOIFHUCHKRDTMO-UHFFFAOYSA-N 0.000 claims description 2
CQLRRWLSSBLWCT-SFHVURJKSA-N 6-[4-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]phenyl]-1,3-benzothiazol-2-amine Chemical compound C1N(CC2)CCC2[C@H]1OC(C=C1)=CC=C1C1=CC=C2N=C(N)SC2=C1 CQLRRWLSSBLWCT-SFHVURJKSA-N 0.000 claims description 2
BVKMGWVIBHOSIG-KRWDZBQOSA-N 6-[4-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]phenyl]-4-bromo-1,3-benzothiazol-2-amine Chemical compound C1N(CC2)CCC2[C@H]1OC(C=C1)=CC=C1C1=CC(Br)=C2N=C(N)SC2=C1 BVKMGWVIBHOSIG-KRWDZBQOSA-N 0.000 claims description 2
VCVSVFQKULDZAO-HNNXBMFYSA-N 6-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1,3-benzothiazol-2-amine Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C2N=C(N)SC2=C1 VCVSVFQKULDZAO-HNNXBMFYSA-N 0.000 claims description 2
MSGNEVBGFWYKGM-KRWDZBQOSA-N 6-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-1h-benzimidazole Chemical compound C1=C2NC=NC2=CC(C2=CC=C(N=N2)O[C@@H]2C3CCN(C2)CC3)=C1 MSGNEVBGFWYKGM-KRWDZBQOSA-N 0.000 claims description 2
UCMSCKUCBHWGGD-KRWDZBQOSA-N [2-amino-6-[4-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]phenyl]-1,3-benzothiazol-4-yl] thiocyanate Chemical compound C1N(CC2)CCC2[C@H]1OC(C=C1)=CC=C1C1=CC(SC#N)=C2N=C(N)SC2=C1 UCMSCKUCBHWGGD-KRWDZBQOSA-N 0.000 claims description 2
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FOCQNTNWTGIHSZ-UHFFFAOYSA-N n-[4-(3-methyl-2h-indazol-5-yl)phenyl]-1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1N(CC2)CCC2C1NC(C=C1)=CC=C1C1=CC=C2NN=C(C)C2=C1 FOCQNTNWTGIHSZ-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
AISLHDKYJVYDRH-SFHVURJKSA-N 5-[2-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-2-ethyl-1,3-benzoxazole Chemical compound C1N(CC2)CCC2[C@H]1OC(N=C1)=NC=C1C1=CC=C(OC(CC)=N2)C2=C1 AISLHDKYJVYDRH-SFHVURJKSA-N 0.000 claims 1
AFDHPNZUBQZHGV-SFHVURJKSA-N 5-[2-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyrimidin-5-yl]-2-methyl-1,3-benzoxazole Chemical compound C1N(CC2)CCC2[C@H]1OC(N=C1)=NC=C1C1=CC=C(OC(C)=N2)C2=C1 AFDHPNZUBQZHGV-SFHVURJKSA-N 0.000 claims 1
PQNZDACRFIZDAW-SFHVURJKSA-N 5-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]oxy]pyridazin-3-yl]-3-bromo-1h-indole Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C2NC=C(Br)C2=C1 PQNZDACRFIZDAW-SFHVURJKSA-N 0.000 claims 1
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125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000002336 repolarization Effects 0.000 description 1
239000003340 retarding agent Substances 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
229960001534 risperidone Drugs 0.000 description 1
RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000000698 schizophrenic effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
230000009151 sensory gating Effects 0.000 description 1
230000031893 sensory processing Effects 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
XWNXEWLCHSLQOI-UHFFFAOYSA-K trisodium;triacetate Chemical compound [Na+].[Na+].[Na+].CC([O-])=O.CC([O-])=O.CC([O-])=O XWNXEWLCHSLQOI-UHFFFAOYSA-K 0.000 description 1
238000001665 trituration Methods 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 0.000 description 1
229960000607 ziprasidone Drugs 0.000 description 1
MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
HDOZVRUNCMBHFH-UHFFFAOYSA-N zotepine Chemical compound CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12 HDOZVRUNCMBHFH-UHFFFAOYSA-N 0.000 description 1
229960004496 zotepine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Psychiatry (AREA)
Reproductive Health (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Rheumatology (AREA)
Psychology (AREA)
Urology & Nephrology (AREA)
Hospice & Palliative Care (AREA)
Dermatology (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Vascular Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA002551486A 2003-12-22 2004-12-10 Derives polycycliques de quinuclidine substitues par un bicycloheterocycle condense Abandoned CA2551486A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US10/744,208		2003-12-22
PCT/US2004/041471 WO2006065233A1 (fr)	2004-12-10	2004-12-10	Dérivés polycycliques de quinuclidine substitués par un bicyclohétérocycle condensé

Publications (1)

Publication Number	Publication Date
CA2551486A1 true CA2551486A1 (fr)	2006-06-22

Family

ID=34960429

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002551486A Abandoned CA2551486A1 (fr)	2003-12-22	2004-12-10	Derives polycycliques de quinuclidine substitues par un bicycloheterocycle condense

Country Status (6)

Country	Link
EP (1)	EP1824848A1 (fr)
JP (1)	JP2008523058A (fr)
CN (1)	CN1922176A (fr)
AU (1)	AU2004325725A1 (fr)
CA (1)	CA2551486A1 (fr)
WO (1)	WO2006065233A1 (fr)

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DE10164139A1 (de)	2001-12-27	2003-07-10	Bayer Ag	2-Heteroarylcarbonsäureamide
GB0220581D0 (en)	2002-09-04	2002-10-09	Novartis Ag	Organic Compound
US20050245531A1 (en) *	2003-12-22	2005-11-03	Abbott Laboratories	Fused bicycloheterocycle substituted quinuclidine derivatives
US7655657B2 (en)	2003-12-22	2010-02-02	Abbott Laboratories	Fused bicycloheterocycle substituted quinuclidine derivatives
US7160876B2 (en)	2003-12-22	2007-01-09	Abbott Laboratories	Fused bicycloheterocycle substituted quinuclidine derivatives
PE20060437A1 (es)	2004-06-18	2006-06-08	Novartis Ag	COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR
GB0415746D0 (en)	2004-07-14	2004-08-18	Novartis Ag	Organic compounds
GB0521508D0 (en)	2005-10-21	2005-11-30	Novartis Ag	Organic compounds
GB0525672D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
GB0525673D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
US8314119B2 (en) *	2006-11-06	2012-11-20	Abbvie Inc.	Azaadamantane derivatives and methods of use
DE102007058504A1 (de)	2007-12-05	2009-07-09	Acino Ag	Transdermales therapeutisches System mit einem Gehalt an einem Modulator für nikotinische Acetylcholinrezeptoren (nAChR)
KR20180011888A (ko)	2008-11-19	2018-02-02	포럼 파마슈티칼즈 인크.	(ｒ)-７-클로로-ｎ-(퀴누클리딘-３-일)벤조［ｂ］티오펜-２-카르복사미드 및 그 약학적으로 허용가능한 염을 이용한 인지 장애의 치료
JO3250B1 (ar)	2009-09-22	2018-09-16	Novartis Ag	إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7
AR081402A1 (es)	2010-05-17	2012-08-29	Envivo Pharmaceuticals Inc	Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il) benzo(b)tiofeno-2-carboxamida monohidrato
US20130225560A1 (en)	2010-07-26	2013-08-29	Envivo Pharmaceuticals, Inc.	Treatment of Cognitive Disorders with Certain Alpha-7 Nicotinic Acid Receptor Agonists in Combination with Acetylcholinesterase Inhibitors
CN103180321A (zh)	2010-09-23	2013-06-26	Abbvie公司	氮杂金刚烷衍生物的一水合物
KR20140003580A (ko)	2011-01-27	2014-01-09	노파르티스 아게	니코틴성 아세틸콜린 수용체 알파 7 활성화제의 용도
WO2012127393A1 (fr)	2011-03-18	2012-09-27	Novartis Ag	Combinaisons d'activateurs des récepteurs nicotiniques à l'acétylcholine alpha 7 et d'antagonistes des mglur5 destinées à être utilisées dans la dyskinésie induite par la dopamine dans la maladie de parkinson
KR20140027939A (ko)	2011-06-30	2014-03-07	도레이 카부시키가이샤	지양제
TWI589576B (zh)	2011-07-15	2017-07-01	諾華公司	氮雜－雙環二芳基醚之鹽類及製造彼等或其前驅物之方法
JP6162705B2 (ja)	2011-10-20	2017-07-12	ノバルティスアーゲー	アルファ７ニコチン性アセチルコリン受容体活性化剤による処置に対する応答性を予測するバイオマーカー
CA2872005A1 (fr)	2012-05-08	2013-11-14	Forum Pharmaceuticals, Inc.	Procedes de maintien, de traitement ou d'amelioration de la fonction cognitive
KR102043309B1 (ko)	2012-12-11	2019-11-11	노파르티스 아게	알파 7 니코틴성 아세틸콜린 수용체 활성화제 치료에 대한 반응성의 예측 바이오마커
EP2945633B1 (fr)	2013-01-15	2021-06-30	Novartis AG	Utilisation d'agonistes du recepteur nicotinique de l' acetylcholine alpha 7
BR112015016992A8 (pt)	2013-01-15	2018-01-23	Novartis Ag	uso de agonistas do receptor alfa 7 nicotínico de acetilcolina
WO2017027600A1 (fr) *	2015-08-12	2017-02-16	Forum Pharmaceuticals, Inc.	Composés d'aminobenzisoxazole à substitution géminale utilisés en tant qu'agonistes de récepteurs de l'acétylcholine α7-nicotinique

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YU84791A (sh) *	1990-05-19	1994-06-10	Boehringer Ingelheim Kg.	Biciklicni 1-aza-cikloalkalni
CA2105655A1 (fr) *	1991-03-08	1992-09-09	Kent Neuenschwander	Inhibiteurs de la squalene synthetase, a base de composes polyaromatiques renfermant une amine tertiaire
AU7394394A (en) *	1992-10-13	1995-12-05	Rhone-Poulenc Rorer Pharmaceuticals Inc.	3-hydroxyquinuclidin-3-ylphenylquinolines as squalene synthase inhibitors
HN1998000118A (es) *	1997-08-27	1999-02-09	Pfizer Prod Inc	2 - aminopiridinas que contienen sustituyentes de anillos condensados.
PL348107A1 (en) *	1998-10-16	2002-05-06	Janssen Pharmaceutica Nv	Therapy for improving cognition
AU2003250322B2 (en) *	2002-08-14	2010-01-21	Neurosearch A/S	Novel quinuclidine derivatives and their use
GB0220581D0 (en) *	2002-09-04	2002-10-09	Novartis Ag	Organic Compound

2004
- 2004-12-10 EP EP04813737A patent/EP1824848A1/fr not_active Withdrawn
- 2004-12-10 CA CA002551486A patent/CA2551486A1/fr not_active Abandoned
- 2004-12-10 CN CNA2004800419490A patent/CN1922176A/zh active Pending
- 2004-12-10 AU AU2004325725A patent/AU2004325725A1/en not_active Abandoned
- 2004-12-10 JP JP2007545431A patent/JP2008523058A/ja not_active Ceased
- 2004-12-10 WO PCT/US2004/041471 patent/WO2006065233A1/fr not_active Ceased

Also Published As

Publication number	Publication date
EP1824848A1 (fr)	2007-08-29
AU2004325725A1 (en)	2006-06-22
WO2006065233A1 (fr)	2006-06-22
CN1922176A (zh)	2007-02-28
JP2008523058A (ja)	2008-07-03

Legal Events

Date	Code	Title	Description
2009-09-04	EEER	Examination request
2012-09-24	FZDE	Dead
2012-12-17	FZDE	Dead	Effective date: 20120924

Publication	Publication Date	Title
US7655657B2 (en)	2010-02-02	Fused bicycloheterocycle substituted quinuclidine derivatives
US20050245531A1 (en)	2005-11-03	Fused bicycloheterocycle substituted quinuclidine derivatives
CA2551486A1 (fr)	2006-06-22	Derives polycycliques de quinuclidine substitues par un bicycloheterocycle condense
US7309699B2 (en)	2007-12-18	3-Quinuclidinyl amino-substituted biaryl derivatives
US7674794B2 (en)	2010-03-09	Fused bicycloheterocycle substituted quinuclidine derivatives
RU2437884C2 (ru)	2011-12-27	Азабициклические алкановые производные, замещенные конденсированным бициклогетероциклом
JP5693229B2 (ja)	2015-04-01	ニコチンアセチルコリン受容体活性モジュレータとしてのビアリール置換アザ二環式アルカン誘導体
US20050137204A1 (en)	2005-06-23	Fused bicycloheterocycle substituted quinuclidine derivatives
US20050137203A1 (en)	2005-06-23	3-quinuclidinyl amino-substituted biaryl derivatives
US20070060588A1 (en)	2007-03-15	Fused bicycloheterocycle substituted quinuclidine derivatives
US7045530B2 (en)	2006-05-16	Spirocyclic quinuclidinic ether derivatives
NZ548231A (en)	2010-06-25	Fused bicycloheterocycle substituted quinuclidine derivatives
US20050137217A1 (en)	2005-06-23	Spirocyclic quinuclidinic ether derivatives
MXPA06007189A (en)	2006-12-13	Fused bicycloheterocycle substituted quinuclidine derivatives
KR20070085053A (ko)	2007-08-27	융합된 바이사이클로헤테로사이클 치환된 퀴누클리딘유도체