HRP20100693T1 - Derivati kinuklidina i njihova uporaba kao antagonista muskarinskih m3 receptora - Google Patents

Derivati kinuklidina i njihova uporaba kao antagonista muskarinskih m3 receptora Download PDF

Info

Publication number: HRP20100693T1
Authority: HR; Croatia
Prior art keywords: azonia; bicyclo; hydroxy; octane bromide; acetoxy
Prior art date: 2004-11-02

Application number

HR20100693T

Other languages

English (en)

Croatian (hr)

Inventor

John Press Neil

Paul Collingwood Stephen

Baettig Urs

Cox Brian

Devidasrao Garad Sudhakar

Kim Hyungchul

Papoutsakis Dimitris

James Watson Simon

Original Assignee

Novartis Ag

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.)

2004-11-02

Filing date

2010-12-14

Publication date

2011-01-31

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=33515948&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HRP20100693(T1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2010-12-14 Application filed by Novartis Ag filed Critical Novartis Ag

2011-01-31 Publication of HRP20100693T1 publication Critical patent/HRP20100693T1/hr

Links

229940122694 Muscarinic M3 receptor antagonist Drugs 0.000 title 1
239000003681 muscarinic M3 receptor antagonist Substances 0.000 title 1
150000008584 quinuclidines Chemical class 0.000 title 1
-1 9H-fluoren-9-yl Chemical group 0.000 claims abstract 27
150000001875 compounds Chemical class 0.000 claims abstract 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 22
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 16
239000001257 hydrogen Substances 0.000 claims abstract 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 10
125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims abstract 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 8
125000005842 heteroatom Chemical group 0.000 claims abstract 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 8
239000001301 oxygen Chemical group 0.000 claims abstract 8
229910052760 oxygen Inorganic materials 0.000 claims abstract 8
229910052717 sulfur Chemical group 0.000 claims abstract 8
239000011593 sulfur Chemical group 0.000 claims abstract 8
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 7
125000005843 halogen group Chemical group 0.000 claims abstract 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
150000003839 salts Chemical class 0.000 claims abstract 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 2
PTHNRUQVXLGKKT-WTHDWRSPSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3SC=CC=3)C=3SC=CC=3)[N+]21CC(=O)NC=1C=CON=1 PTHNRUQVXLGKKT-WTHDWRSPSA-N 0.000 claims abstract 2
KVYFPKJRJWDXCT-LWOCSEGBSA-O [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3SC=CC=3)C=3SC=CC=3)[N+]21CC(=O)NC1=CN=CC=N1 KVYFPKJRJWDXCT-LWOCSEGBSA-O 0.000 claims abstract 2
ZPFCXHFVCOFWOZ-XTBFPHCZSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3SC=CC=3)C=3SC=CC=3)[N+]21CC(=O)NC1=CC=NC=N1 ZPFCXHFVCOFWOZ-XTBFPHCZSA-N 0.000 claims abstract 2
239000012907 medicinal substance Substances 0.000 claims 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 4
230000003110 anti-inflammatory effect Effects 0.000 claims 3
229940124630 bronchodilator Drugs 0.000 claims 3
239000008194 pharmaceutical composition Substances 0.000 claims 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 2
PWSXXTLDLCIUGO-UTEXUTGQSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCC1 PWSXXTLDLCIUGO-UTEXUTGQSA-N 0.000 claims 2
NVQBJTIINOFPEC-OFIQDHIESA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyfluorene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C4=CC=CC=C43)[N+]21CC(=O)NC1=NC=NC=N1 NVQBJTIINOFPEC-OFIQDHIESA-N 0.000 claims 2
DQWQUUWAYXIMGT-ZVPZRTFFSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 DQWQUUWAYXIMGT-ZVPZRTFFSA-N 0.000 claims 2
CFMGCNDIOKQGHM-AYFIPJBYSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 CFMGCNDIOKQGHM-AYFIPJBYSA-N 0.000 claims 2
SLCAXYRZANJZTL-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyfluorene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C4=CC=CC=C43)[N+]21CC(=O)NC1=CN=CC=N1 SLCAXYRZANJZTL-SGFHCSRJSA-N 0.000 claims 2
239000000048 adrenergic agonist Substances 0.000 claims 2
230000000954 anitussive effect Effects 0.000 claims 2
230000001387 anti-histamine Effects 0.000 claims 2
239000000739 antihistaminic agent Substances 0.000 claims 2
229940124584 antitussives Drugs 0.000 claims 2
102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 claims 2
108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 claims 2
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims 2
125000002541 furyl group Chemical group 0.000 claims 2
239000003862 glucocorticoid Substances 0.000 claims 2
230000002757 inflammatory effect Effects 0.000 claims 2
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 2
125000000842 isoxazolyl group Chemical group 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 2
125000001544 thienyl group Chemical group 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
206010027654 Allergic conditions Diseases 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims 1
LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 claims 1
102000007202 Muscarinic M3 Receptor Human genes 0.000 claims 1
108010008405 Muscarinic M3 Receptor Proteins 0.000 claims 1
229910019142 PO4 Inorganic materials 0.000 claims 1
MXTHDVYBJMKRAW-TWBGCDCQSA-N [(2r)-2-methyl-1-[(5-methyl-1,2-oxazol-3-yl)carbamoyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-diphenylacetate;bromide Chemical compound [Br-].C1([C@H]([N+]2(CCC1CC2)C(=O)NC1=NOC(C)=C1)C)OC(=O)C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 MXTHDVYBJMKRAW-TWBGCDCQSA-N 0.000 claims 1
LBHUBPVFRVTKRE-NJSXXHIRSA-N [(3R)-1-[2-amino-1-(1,2-oxazol-3-yl)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate phosphate Chemical compound [O-]P([O-])([O-])=O.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCC3)C=3C=CC=CC=3)CC[N+]12C(C(=O)N)C=1C=CON=1.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCC3)C=3C=CC=CC=3)CC[N+]12C(C(=O)N)C=1C=CON=1.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCC3)C=3C=CC=CC=3)CC[N+]12C(C(=O)N)C=1C=CON=1 LBHUBPVFRVTKRE-NJSXXHIRSA-N 0.000 claims 1
NDKPGOIGMAPCKZ-ADFHNETRSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 11-hydroxydibenzo[1,2-a:1',2'-e][7]annulene-11-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C=CC4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 NDKPGOIGMAPCKZ-ADFHNETRSA-N 0.000 claims 1
CZDAJDIMEGEBST-UXJVTRAKSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C3=COC=C3)[N+]21C(=O)NC1=CC=CN=N1 CZDAJDIMEGEBST-UXJVTRAKSA-N 0.000 claims 1
PPDAIKJPFBAEPV-BDVUIUMHSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C=3C=CC=CC=3)[N+]21C(=O)NC1=CC=CN=N1 PPDAIKJPFBAEPV-BDVUIUMHSA-N 0.000 claims 1
WOZUKJBPTBJMRI-AYFIPJBYSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C=1OC=CC=1)(O)C1CCCCC1 WOZUKJBPTBJMRI-AYFIPJBYSA-N 0.000 claims 1
ASIIWQLNQRMJJF-BDVUIUMHSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C1=COC=C1)(O)C1CCCCC1 ASIIWQLNQRMJJF-BDVUIUMHSA-N 0.000 claims 1
MDRKZBWOEKSIQL-ZVPZRTFFSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 MDRKZBWOEKSIQL-ZVPZRTFFSA-N 0.000 claims 1
HKJJONBLZRQIOO-AYFIPJBYSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 HKJJONBLZRQIOO-AYFIPJBYSA-N 0.000 claims 1
HOYHGTSNECKWMY-BDVUIUMHSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C1=CSC=C1)(O)C1CCCCC1 HOYHGTSNECKWMY-BDVUIUMHSA-N 0.000 claims 1
SZIQGRZMRQJLJF-PKPSOOLGSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C=1OC=CC=1)(O)C1CCCC1 SZIQGRZMRQJLJF-PKPSOOLGSA-N 0.000 claims 1
KGSIOSOOXZMXFH-SFZOXUKMSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C1=COC=C1)(O)C1CCCC1 KGSIOSOOXZMXFH-SFZOXUKMSA-N 0.000 claims 1
GAZDVSXUYQWHSZ-QVOXVMGDSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 GAZDVSXUYQWHSZ-QVOXVMGDSA-N 0.000 claims 1
DZCKMHXNWKSWTB-PKPSOOLGSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)C(=O)NC=1N=NC=CC=1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 DZCKMHXNWKSWTB-PKPSOOLGSA-N 0.000 claims 1
YVFLUJNRTOMJLQ-UXJVTRAKSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C3=CSC=C3)[N+]21C(=O)NC1=CC=CN=N1 YVFLUJNRTOMJLQ-UXJVTRAKSA-N 0.000 claims 1
UESPJDKHOUCQCC-BDVUIUMHSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C=3C=CC=CC=3)[N+]21C(=O)NC1=CC=CN=N1 UESPJDKHOUCQCC-BDVUIUMHSA-N 0.000 claims 1
CHLFOCRTPQDCQG-SGFHCSRJSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3C4=CC=CC=C4CC4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 CHLFOCRTPQDCQG-SGFHCSRJSA-N 0.000 claims 1
GKTUUSSQPLEKSD-SGFHCSRJSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4CC4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 GKTUUSSQPLEKSD-SGFHCSRJSA-N 0.000 claims 1
ZDNIVRNFHOJTJA-PMLWWUNYSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyfluorene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 ZDNIVRNFHOJTJA-PMLWWUNYSA-N 0.000 claims 1
IVYCCLOHYSTYRR-PMLWWUNYSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyxanthene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4OC4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 IVYCCLOHYSTYRR-PMLWWUNYSA-N 0.000 claims 1
WASPVIDRFWKIFH-PMLWWUNYSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3C4=CC=CC=C4C4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 WASPVIDRFWKIFH-PMLWWUNYSA-N 0.000 claims 1
IINGMDFVUYFQHG-PMLWWUNYSA-N [(3r)-1-(pyridazin-3-ylcarbamoyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)[N+]21C(=O)NC1=CC=CN=N1 IINGMDFVUYFQHG-PMLWWUNYSA-N 0.000 claims 1
XTOAYDTZDJBLAL-RSYCBKOKSA-N [(3r)-1-[1-(1,2-oxazol-3-ylamino)-1-oxopropan-2-yl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-diphenylacetate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C(O)(C=3C=CC=CC=3)C=3C=CC=CC=3)CC[N+]12C(C)C(=O)NC=1C=CON=1 XTOAYDTZDJBLAL-RSYCBKOKSA-N 0.000 claims 1
JCPYBEFKFGQQBW-DMWRAEOSSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 11-hydroxydibenzo[1,2-a:1',2'-e][7]annulene-11-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C=CC4=CC=CC=C43)[N+]21CC(=O)NC=1C=CON=1 JCPYBEFKFGQQBW-DMWRAEOSSA-N 0.000 claims 1
LYEUZKSCFWFFMP-OFIQDHIESA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(2-chlorophenyl)-2-hydroxyacetate;bromide Chemical group [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3C(=CC=CC=3)Cl)C=3C(=CC=CC=3)Cl)[N+]21CC(=O)NC=1C=CON=1 LYEUZKSCFWFFMP-OFIQDHIESA-N 0.000 claims 1
JXEBVFQBPQIYOH-FKYYSRDKSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C3=COC=C3)[N+]21CC(=O)NC=1C=CON=1 JXEBVFQBPQIYOH-FKYYSRDKSA-N 0.000 claims 1
HZGHGUPFITZHEX-GXVQUIFISA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-diphenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(C1)CC(=O)NC1=NOC=C1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 HZGHGUPFITZHEX-GXVQUIFISA-N 0.000 claims 1
QNGBQXNPFDMABV-WULMZJJMSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-diphenylpropanoate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(C)(C=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 QNGBQXNPFDMABV-WULMZJJMSA-N 0.000 claims 1
HLXFHYCWWFUOSC-IULAOUEKSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(2-chlorophenyl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3C=CC=CC=3)C=3C(=CC=CC=3)Cl)[N+]21CC(=O)NC=1C=CON=1 HLXFHYCWWFUOSC-IULAOUEKSA-N 0.000 claims 1
DOFPJTZAWLYUGW-FIQQBEOASA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 DOFPJTZAWLYUGW-FIQQBEOASA-N 0.000 claims 1
QURMEKJIUAZANR-FVRMQZBVSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclobutyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCC1 QURMEKJIUAZANR-FVRMQZBVSA-N 0.000 claims 1
JKNHJSSAZYNMIW-FIQQBEOASA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C1=COC=C1)(O)C1CCCCC1 JKNHJSSAZYNMIW-FIQQBEOASA-N 0.000 claims 1
JBYALQATTNNXLM-ROILBPFPSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 JBYALQATTNNXLM-ROILBPFPSA-N 0.000 claims 1
UYDZCDBOKNTCDY-NSLDKZMESA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 UYDZCDBOKNTCDY-NSLDKZMESA-N 0.000 claims 1
MUNWNMDXVFWWSJ-FIQQBEOASA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCCC1 MUNWNMDXVFWWSJ-FIQQBEOASA-N 0.000 claims 1
BQJVDKLIOBNQRU-JMYPFRHISA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C1=COC=C1)(O)C1CCCC1 BQJVDKLIOBNQRU-JMYPFRHISA-N 0.000 claims 1
IPYXMSOXADDKER-SUSCGCCGSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 IPYXMSOXADDKER-SUSCGCCGSA-N 0.000 claims 1
PFNWPHKQGJNTSN-UTEXUTGQSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 PFNWPHKQGJNTSN-UTEXUTGQSA-N 0.000 claims 1
GUOWKYWHJRLGRT-VTTAHNPLSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopropyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC2=NOC=C2)C1)C(=O)C(C=1SC=CC=1)(O)C1CC1 GUOWKYWHJRLGRT-VTTAHNPLSA-N 0.000 claims 1
GUHYQPHICDOZIV-DMWRAEOSSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-ethylsulfanyl-2,2-diphenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(SCC)(C=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 GUHYQPHICDOZIV-DMWRAEOSSA-N 0.000 claims 1
XFDIKUJEOXYVQO-PKLCTQDOSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-bis(3-methoxyphenyl)acetate;bromide Chemical compound [Br-].COC1=CC=CC(C(O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=C(OC)C=CC=2)=C1 XFDIKUJEOXYVQO-PKLCTQDOSA-N 0.000 claims 1
JASBHIMHORBWBD-PKLCTQDOSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-bis(4-methoxyphenyl)acetate;bromide Chemical compound [Br-].C1=CC(OC)=CC=C1C(O)(C=1C=CC(OC)=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 JASBHIMHORBWBD-PKLCTQDOSA-N 0.000 claims 1
LMVPTKHKZQNMTP-DMWRAEOSSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-bis(4-methylphenyl)acetate;bromide Chemical compound [Br-].C1=CC(C)=CC=C1C(O)(C=1C=CC(C)=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 LMVPTKHKZQNMTP-DMWRAEOSSA-N 0.000 claims 1
KQZGFLAOVMRBJE-FKYYSRDKSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C3=CSC=C3)[N+]21CC(=O)NC=1C=CON=1 KQZGFLAOVMRBJE-FKYYSRDKSA-N 0.000 claims 1
KNRAZWQROOQZCD-HIPLPVRDSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-(2-methoxyphenyl)-2-phenylacetate;bromide Chemical compound [Br-].COC1=CC=CC=C1C(O)(C=1C=CC=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 KNRAZWQROOQZCD-HIPLPVRDSA-N 0.000 claims 1
SQKMLNPPWDJIOV-KNNDMWINSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-(2-methylphenyl)-2-phenylacetate;bromide Chemical compound [Br-].CC1=CC=CC=C1C(O)(C=1C=CC=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 SQKMLNPPWDJIOV-KNNDMWINSA-N 0.000 claims 1
UKIGHUJEPXNYAZ-HIPLPVRDSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-(4-methoxyphenyl)-2-phenylacetate;bromide Chemical compound [Br-].C1=CC(OC)=CC=C1C(O)(C=1C=CC=CC=1)C(=O)O[C@@H]1C(CC2)CC[N+]2(CC(=O)NC2=NOC=C2)C1 UKIGHUJEPXNYAZ-HIPLPVRDSA-N 0.000 claims 1
VTBLMPHPICFVKP-FIQQBEOASA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 VTBLMPHPICFVKP-FIQQBEOASA-N 0.000 claims 1
QJIBWXVASULUCW-WULMZJJMSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-methoxy-2,2-diphenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(OC)(C=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CC(=O)NC=1C=CON=1 QJIBWXVASULUCW-WULMZJJMSA-N 0.000 claims 1
DAKBDLXZFNNQTD-RTDUGLMJSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4CC4=CC=CC=C43)CC[N+]12CC(=O)NC=1C=CON=1 DAKBDLXZFNNQTD-RTDUGLMJSA-N 0.000 claims 1
IDKPHFMVEHJQHS-RTDUGLMJSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4CC4=CC=CC=C43)[N+]21CC(=O)NC=1C=CON=1 IDKPHFMVEHJQHS-RTDUGLMJSA-N 0.000 claims 1
BZWAIILYUZPDDF-YUXMWEGSSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4C4=CC=CC=C43)CC[N+]12CC(=O)NC=1C=CON=1 BZWAIILYUZPDDF-YUXMWEGSSA-N 0.000 claims 1
ZLXHOBGHKNOVHH-YUXMWEGSSA-N [(3r)-1-[2-(1,2-oxazol-3-ylamino)-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)CC[N+]12CC(=O)NC=1C=CON=1 ZLXHOBGHKNOVHH-YUXMWEGSSA-N 0.000 claims 1
YPNWAUAZEBXEDV-DXLVBJHUSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=COC=C2)C2=COC=C2)=N1 YPNWAUAZEBXEDV-DXLVBJHUSA-N 0.000 claims 1
YSLCOKGCOCSEPO-WQKGMRGTSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(2-chlorophenyl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)=N1 YSLCOKGCOCSEPO-WQKGMRGTSA-N 0.000 claims 1
ILKKYAURZDXSSS-OANMHNKXSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=COC=C2)C=2C=CC=CC=2)=N1 ILKKYAURZDXSSS-OANMHNKXSA-N 0.000 claims 1
UTLGONQMBRVFOI-PBYMMPLCSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclobutyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCC2)C=2SC=CC=2)=N1 UTLGONQMBRVFOI-PBYMMPLCSA-N 0.000 claims 1
LTWYADDGFGLFLX-OANMHNKXSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCCCC2)C2=CSC=C2)=N1 LTWYADDGFGLFLX-OANMHNKXSA-N 0.000 claims 1
ACHOBFNJGCSMLX-HLESCNFNSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCCC2)C2=COC=C2)=N1 ACHOBFNJGCSMLX-HLESCNFNSA-N 0.000 claims 1
PSIHJGFSCZDQJM-HLESCNFNSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCCC2)C2=CSC=C2)=N1 PSIHJGFSCZDQJM-HLESCNFNSA-N 0.000 claims 1
QVPAEXCVBGXRLP-DXLVBJHUSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=CSC=C2)C2=CSC=C2)=N1 QVPAEXCVBGXRLP-DXLVBJHUSA-N 0.000 claims 1
RCVVTPNGORUHNV-OANMHNKXSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=CSC=C2)C=2C=CC=CC=2)=N1 RCVVTPNGORUHNV-OANMHNKXSA-N 0.000 claims 1
JNSNUESJPBPJFB-XCEOWTAJSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3CC3=CC=CC=C32)=N1 JNSNUESJPBPJFB-XCEOWTAJSA-N 0.000 claims 1
JYGVFVNWVFASAH-XCEOWTAJSA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(O)C3=CC=CC=C3CC3=CC=CC=C32)=N1 JYGVFVNWVFASAH-XCEOWTAJSA-N 0.000 claims 1
BFZONOOZVKTCME-CJYZSSDISA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyxanthene-9-carboxylate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(O)C3=CC=CC=C3OC3=CC=CC=C32)=N1 BFZONOOZVKTCME-CJYZSSDISA-N 0.000 claims 1
XAPIRXONNQLWIT-CJYZSSDISA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3C3=CC=CC=C32)=N1 XAPIRXONNQLWIT-CJYZSSDISA-N 0.000 claims 1
DEDIGANFAOGJEA-CJYZSSDISA-N [(3r)-1-[2-[(5-ethyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].O1C(CC)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 DEDIGANFAOGJEA-CJYZSSDISA-N 0.000 claims 1
HXEXVYRMUSSNCH-ZJKFLMFHSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 11-hydroxydibenzo[1,2-a:1',2'-e][7]annulene-11-carboxylate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(O)C3=CC=CC=C3C=CC3=CC=CC=C32)=N1 HXEXVYRMUSSNCH-ZJKFLMFHSA-N 0.000 claims 1
UJEGNJDPSAYEKZ-FKBRAVIBSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=COC=C2)C2=COC=C2)=N1 UJEGNJDPSAYEKZ-FKBRAVIBSA-N 0.000 claims 1
WTQSSEGZNBJVOB-VYIGTOTHSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(2-chlorophenyl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)=N1 WTQSSEGZNBJVOB-VYIGTOTHSA-N 0.000 claims 1
JOMHYNAWONELCA-SUSCGCCGSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=COC=C2)C=2C=CC=CC=2)=N1 JOMHYNAWONELCA-SUSCGCCGSA-N 0.000 claims 1
RJKIEYOHIQSNMU-UTEXUTGQSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclobutyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCC2)C=2SC=CC=2)=N1 RJKIEYOHIQSNMU-UTEXUTGQSA-N 0.000 claims 1
VFEGPHAWGSNMOD-SUSCGCCGSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCCCC2)C2=COC=C2)=N1 VFEGPHAWGSNMOD-SUSCGCCGSA-N 0.000 claims 1
YNFBYINXTBJLAC-SUSCGCCGSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCCCC2)C2=CSC=C2)=N1 YNFBYINXTBJLAC-SUSCGCCGSA-N 0.000 claims 1
WIQJVHQRIJIIIT-NSLDKZMESA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCCC2)C=2OC=CC=2)=N1 WIQJVHQRIJIIIT-NSLDKZMESA-N 0.000 claims 1
DRJQIJVVNXCFIL-FIQQBEOASA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CCCC2)C2=COC=C2)=N1 DRJQIJVVNXCFIL-FIQQBEOASA-N 0.000 claims 1
RLIHYEQLMBPUPE-FVRMQZBVSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopropyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2CC2)C=2SC=CC=2)=N1 RLIHYEQLMBPUPE-FVRMQZBVSA-N 0.000 claims 1
YBQUOFVNBMCGCF-FKBRAVIBSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=CSC=C2)C2=CSC=C2)=N1 YBQUOFVNBMCGCF-FKBRAVIBSA-N 0.000 claims 1
GHWDLGZAQGDKCA-SUSCGCCGSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C(O)(C2=CSC=C2)C=2C=CC=CC=2)=N1 GHWDLGZAQGDKCA-SUSCGCCGSA-N 0.000 claims 1
BAJKRLDRJMTAPQ-PKLCTQDOSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3CC3=CC=CC=C32)=N1 BAJKRLDRJMTAPQ-PKLCTQDOSA-N 0.000 claims 1
HSRJLUDXMMAKFW-PKLCTQDOSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(O)C3=CC=CC=C3CC3=CC=CC=C32)=N1 HSRJLUDXMMAKFW-PKLCTQDOSA-N 0.000 claims 1
ORONXPJTLSUYAG-RTDUGLMJSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyxanthene-9-carboxylate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2(O)C3=CC=CC=C3OC3=CC=CC=C32)=N1 ORONXPJTLSUYAG-RTDUGLMJSA-N 0.000 claims 1
USIMCYSRHQZCOQ-RTDUGLMJSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3C3=CC=CC=C32)=N1 USIMCYSRHQZCOQ-RTDUGLMJSA-N 0.000 claims 1
DKCODRXMQIFZBL-RTDUGLMJSA-N [(3r)-1-[2-[(5-methyl-1,2-oxazol-3-yl)amino]-2-oxoethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].O1C(C)=CC(NC(=O)C[N+]23CCC(CC2)[C@H](C3)OC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 DKCODRXMQIFZBL-RTDUGLMJSA-N 0.000 claims 1
RKGNQYRWOANOMP-FKEZYDJSSA-N [(3r)-1-[2-amino-2-oxo-1-(1,3,5-triazin-2-yl)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 11-hydroxydibenzo[1,2-a:1',2'-e][7]annulene-11-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3(O)C4=CC=CC=C4C=CC4=CC=CC=C43)CC[N+]12C(C(=O)N)C1=NC=NC=N1 RKGNQYRWOANOMP-FKEZYDJSSA-N 0.000 claims 1
FWBDUQHLLIWQPZ-NSOJYXMXSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C3=COC=C3)[N+]21CC(=O)NC1=NC=NC=N1 FWBDUQHLLIWQPZ-NSOJYXMXSA-N 0.000 claims 1
GGSBTIUOMADSDN-YSAQQSICSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=NC=NC=N1 GGSBTIUOMADSDN-YSAQQSICSA-N 0.000 claims 1
XBHHWDUIBLQRJI-NOWPHXOYSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCCC1 XBHHWDUIBLQRJI-NOWPHXOYSA-N 0.000 claims 1
NWBVZKXXTJBIMK-YSAQQSICSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C1=COC=C1)(O)C1CCCCC1 NWBVZKXXTJBIMK-YSAQQSICSA-N 0.000 claims 1
ILVLVFWRALKHCJ-DFUUOGHFSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 ILVLVFWRALKHCJ-DFUUOGHFSA-N 0.000 claims 1
OBLKUAOGTWYWDH-NOWPHXOYSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 OBLKUAOGTWYWDH-NOWPHXOYSA-N 0.000 claims 1
PYCJKYAGHQMPCB-YSAQQSICSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCCC1 PYCJKYAGHQMPCB-YSAQQSICSA-N 0.000 claims 1
XEFQMFZTUHWAAO-KMIFLNSOSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCC1 XEFQMFZTUHWAAO-KMIFLNSOSA-N 0.000 claims 1
CHEJEFSNPMQJRZ-YHRORWFSSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 CHEJEFSNPMQJRZ-YHRORWFSSA-N 0.000 claims 1
NUSSSVNHXDWJET-KMIFLNSOSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 NUSSSVNHXDWJET-KMIFLNSOSA-N 0.000 claims 1
RSRZRXSREIBLKA-UXHKZPOWSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CN=2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCC1 RSRZRXSREIBLKA-UXHKZPOWSA-N 0.000 claims 1
NYNBJOURLGSFHV-NSOJYXMXSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C3=CSC=C3)[N+]21CC(=O)NC1=NC=NC=N1 NYNBJOURLGSFHV-NSOJYXMXSA-N 0.000 claims 1
NEWXOMFLRSEFQU-YSAQQSICSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=NC=NC=N1 NEWXOMFLRSEFQU-YSAQQSICSA-N 0.000 claims 1
DEODHGSTQZRJAR-OASTYHRRSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4CC4=CC=CC=C43)CC[N+]12CC(=O)NC1=NC=NC=N1 DEODHGSTQZRJAR-OASTYHRRSA-N 0.000 claims 1
HBDHQNASIFJDMR-OASTYHRRSA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4CC4=CC=CC=C43)[N+]21CC(=O)NC1=NC=NC=N1 HBDHQNASIFJDMR-OASTYHRRSA-N 0.000 claims 1
SSEUVGQKRYVPBR-OFIQDHIESA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyxanthene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4OC4=CC=CC=C43)[N+]21CC(=O)NC1=NC=NC=N1 SSEUVGQKRYVPBR-OFIQDHIESA-N 0.000 claims 1
QNJOKWDGICCMGR-OFIQDHIESA-N [(3r)-1-[2-oxo-2-(1,3,5-triazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)CC[N+]12CC(=O)NC1=NC=NC=N1 QNJOKWDGICCMGR-OFIQDHIESA-N 0.000 claims 1
XTQWLMJWVILPLV-WHPWLWEVSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C3=COC=C3)[N+]21CC(=O)NC1=CN=CC=N1 XTQWLMJWVILPLV-WHPWLWEVSA-N 0.000 claims 1
WFHLUCIMTYUEBR-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=CN=CC=N1 WFHLUCIMTYUEBR-QVOXVMGDSA-N 0.000 claims 1
GZNVXBRNMFONBM-YGXSZZIWSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCCC1 GZNVXBRNMFONBM-YGXSZZIWSA-N 0.000 claims 1
VTFGHQOKBDCJRA-WNCQOFSISA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 VTFGHQOKBDCJRA-WNCQOFSISA-N 0.000 claims 1
GDIDDJZPLUFRLC-YGXSZZIWSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 GDIDDJZPLUFRLC-YGXSZZIWSA-N 0.000 claims 1
YYFZLFYVXCVDIT-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCCC1 YYFZLFYVXCVDIT-QVOXVMGDSA-N 0.000 claims 1
HLKWSDNOBXLJTF-BDVUIUMHSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=NC=2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCC1 HLKWSDNOBXLJTF-BDVUIUMHSA-N 0.000 claims 1
QLMOJOJZOMDMNW-WHPWLWEVSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C3=CSC=C3)[N+]21CC(=O)NC1=CN=CC=N1 QLMOJOJZOMDMNW-WHPWLWEVSA-N 0.000 claims 1
MEWVUKMLGXIVMX-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=CN=CC=N1 MEWVUKMLGXIVMX-QVOXVMGDSA-N 0.000 claims 1
ZCIMJCILQZIZTC-LNORMHFUSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4CC4=CC=CC=C43)CC[N+]12CC(=O)NC1=CN=CC=N1 ZCIMJCILQZIZTC-LNORMHFUSA-N 0.000 claims 1
LJNYWXYTSQSFRH-LNORMHFUSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4CC4=CC=CC=C43)[N+]21CC(=O)NC1=CN=CC=N1 LJNYWXYTSQSFRH-LNORMHFUSA-N 0.000 claims 1
KELKXMKWBZVARH-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyxanthene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4OC4=CC=CC=C43)[N+]21CC(=O)NC1=CN=CC=N1 KELKXMKWBZVARH-SGFHCSRJSA-N 0.000 claims 1
WUJYVHUCCLKWKW-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4C4=CC=CC=C43)CC[N+]12CC(=O)NC1=CN=CC=N1 WUJYVHUCCLKWKW-SGFHCSRJSA-N 0.000 claims 1
BXAQTQSNHWPVFY-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrazin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)CC[N+]12CC(=O)NC1=CN=CC=N1 BXAQTQSNHWPVFY-SGFHCSRJSA-N 0.000 claims 1
PDGAHRBJCQCRPZ-XLKOHVDKSA-N [(3r)-1-[2-oxo-2-(pyridin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 11-hydroxydibenzo[1,2-a:1',2'-e][7]annulene-11-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C=CC4=CC=CC=C43)[N+]21CC(=O)NC1=CC=CC=N1 PDGAHRBJCQCRPZ-XLKOHVDKSA-N 0.000 claims 1
DZIZKRWZUCSZLP-ROILBPFPSA-N [(3r)-1-[2-oxo-2-(pyridin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=CC=CC=N1 DZIZKRWZUCSZLP-ROILBPFPSA-N 0.000 claims 1
DLBQMPBEOZQBAY-NVJOYBRVSA-N [(3r)-1-[2-oxo-2-(pyridin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4CC4=CC=CC=C43)[N+]21CC(=O)NC1=CC=CC=N1 DLBQMPBEOZQBAY-NVJOYBRVSA-N 0.000 claims 1
IMZUFXGEXYQVPC-WHPWLWEVSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C3=COC=C3)[N+]21CC(=O)NC1=NC=CC=N1 IMZUFXGEXYQVPC-WHPWLWEVSA-N 0.000 claims 1
CDBOJSYPKSLCAQ-YGXSZZIWSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCCC1 CDBOJSYPKSLCAQ-YGXSZZIWSA-N 0.000 claims 1
HWBRWDLMEZLCFM-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C1=COC=C1)(O)C1CCCCC1 HWBRWDLMEZLCFM-QVOXVMGDSA-N 0.000 claims 1
PEFOWOYEHBJITF-WNCQOFSISA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 PEFOWOYEHBJITF-WNCQOFSISA-N 0.000 claims 1
PTXMAWMLZHIOEP-YGXSZZIWSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 PTXMAWMLZHIOEP-YGXSZZIWSA-N 0.000 claims 1
HMGQOEGPGTXZLJ-AYFIPJBYSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCC1 HMGQOEGPGTXZLJ-AYFIPJBYSA-N 0.000 claims 1
PUTZVIMHMIDAJN-BDVUIUMHSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C1=COC=C1)(O)C1CCCC1 PUTZVIMHMIDAJN-BDVUIUMHSA-N 0.000 claims 1
UHNAGLQQLRRVGH-ZVPZRTFFSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 UHNAGLQQLRRVGH-ZVPZRTFFSA-N 0.000 claims 1
LQSPCDHPVNKHMN-AYFIPJBYSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 LQSPCDHPVNKHMN-AYFIPJBYSA-N 0.000 claims 1
HUIUSUAROAOBLQ-BDVUIUMHSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CC=CN=2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCC1 HUIUSUAROAOBLQ-BDVUIUMHSA-N 0.000 claims 1
VNHVFUQTCCGRTQ-WHPWLWEVSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C3=CSC=C3)[N+]21CC(=O)NC1=NC=CC=N1 VNHVFUQTCCGRTQ-WHPWLWEVSA-N 0.000 claims 1
DIWDICYHMOAPRL-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=NC=CC=N1 DIWDICYHMOAPRL-QVOXVMGDSA-N 0.000 claims 1
YZPBSTOKTIAJRI-LNORMHFUSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4CC4=CC=CC=C43)CC[N+]12CC(=O)NC1=NC=CC=N1 YZPBSTOKTIAJRI-LNORMHFUSA-N 0.000 claims 1
HLASKHSYFAXUIS-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyfluorene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C4=CC=CC=C43)[N+]21CC(=O)NC1=NC=CC=N1 HLASKHSYFAXUIS-SGFHCSRJSA-N 0.000 claims 1
HUEDRJVKOUXUAU-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)CC[N+]12CC(=O)NC1=NC=CC=N1 HUEDRJVKOUXUAU-SGFHCSRJSA-N 0.000 claims 1
XRUYSILIWCNGBE-WHPWLWEVSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C3=COC=C3)[N+]21CC(=O)NC1=CC=NC=N1 XRUYSILIWCNGBE-WHPWLWEVSA-N 0.000 claims 1
OEYHQTXLMJHSOB-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=CC=NC=N1 OEYHQTXLMJHSOB-QVOXVMGDSA-N 0.000 claims 1
NJFVAMNYKFYERH-YGXSZZIWSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCCC1 NJFVAMNYKFYERH-YGXSZZIWSA-N 0.000 claims 1
VBIYLYUWXZELLQ-WNCQOFSISA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 VBIYLYUWXZELLQ-WNCQOFSISA-N 0.000 claims 1
HYHOFJXUEWBJOB-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCCC1 HYHOFJXUEWBJOB-QVOXVMGDSA-N 0.000 claims 1
PUOMOFCXVAAXCE-AYFIPJBYSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCC1 PUOMOFCXVAAXCE-AYFIPJBYSA-N 0.000 claims 1
FUGGBRBLEUYEIP-BDVUIUMHSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C1=COC=C1)(O)C1CCCC1 FUGGBRBLEUYEIP-BDVUIUMHSA-N 0.000 claims 1
QGJDAWHXJGNHNS-ZVPZRTFFSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 QGJDAWHXJGNHNS-ZVPZRTFFSA-N 0.000 claims 1
NINFWSUPOJXCOM-AYFIPJBYSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 NINFWSUPOJXCOM-AYFIPJBYSA-N 0.000 claims 1
WRRCJHMXWXUJAD-BDVUIUMHSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2N=CN=CC=2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCC1 WRRCJHMXWXUJAD-BDVUIUMHSA-N 0.000 claims 1
DFGHFDKLUVABAW-WHPWLWEVSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C3=CSC=C3)[N+]21CC(=O)NC1=CC=NC=N1 DFGHFDKLUVABAW-WHPWLWEVSA-N 0.000 claims 1
DDJBAJDWPDCKNP-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=CC=NC=N1 DDJBAJDWPDCKNP-QVOXVMGDSA-N 0.000 claims 1
KELOTVXGBURWDT-LNORMHFUSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9,10-dihydroanthracene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4CC4=CC=CC=C43)CC[N+]12CC(=O)NC1=CC=NC=N1 KELOTVXGBURWDT-LNORMHFUSA-N 0.000 claims 1
BASRJFATTNGULG-LNORMHFUSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4CC4=CC=CC=C43)[N+]21CC(=O)NC1=CC=NC=N1 BASRJFATTNGULG-LNORMHFUSA-N 0.000 claims 1
GBFGPOWJLPODQG-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyfluorene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C4=CC=CC=C43)[N+]21CC(=O)NC1=CC=NC=N1 GBFGPOWJLPODQG-SGFHCSRJSA-N 0.000 claims 1
VPSQEXUYUGDHSR-SGFHCSRJSA-N [(3r)-1-[2-oxo-2-(pyrimidin-4-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)CC[N+]12CC(=O)NC1=CC=NC=N1 VPSQEXUYUGDHSR-SGFHCSRJSA-N 0.000 claims 1
DGNMUQUXQWLGQN-WWAPZXQFSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 11-hydroxydibenzo[1,2-a:1',2'-e][7]annulene-11-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C=CC4=CC=CC=C43)[N+]21CC(=O)NC1=CN=CN=C1 DGNMUQUXQWLGQN-WWAPZXQFSA-N 0.000 claims 1
QSQDXNCTHMRZPS-DXLVBJHUSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2,2-bis(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C3=COC=C3)[N+]21CC(=O)NC1=CN=CN=C1 QSQDXNCTHMRZPS-DXLVBJHUSA-N 0.000 claims 1
CXNXVWKVLHDHJZ-AVRGKSJGSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-(furan-3-yl)-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=COC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=CN=CN=C1 CXNXVWKVLHDHJZ-AVRGKSJGSA-N 0.000 claims 1
IBFHCPMNGCRVGP-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCCC1 IBFHCPMNGCRVGP-QVOXVMGDSA-N 0.000 claims 1
XRHXDEOWHHDRGS-AVRGKSJGSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C1=COC=C1)(O)C1CCCCC1 XRHXDEOWHHDRGS-AVRGKSJGSA-N 0.000 claims 1
SJLLTBPMESHADM-CXEAGMIJSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 SJLLTBPMESHADM-CXEAGMIJSA-N 0.000 claims 1
YIHPGYTUXLBQJB-QVOXVMGDSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCCC1 YIHPGYTUXLBQJB-QVOXVMGDSA-N 0.000 claims 1
BRILMVBXECABEL-AVRGKSJGSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C1=CSC=C1)(O)C1CCCCC1 BRILMVBXECABEL-AVRGKSJGSA-N 0.000 claims 1
CBCSMHWZCBFINO-BDVUIUMHSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCC1 CBCSMHWZCBFINO-BDVUIUMHSA-N 0.000 claims 1
UYFKNXVQKKUIIT-FGXDWOATSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-(furan-3-yl)-2-hydroxyacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C1=COC=C1)(O)C1CCCC1 UYFKNXVQKKUIIT-FGXDWOATSA-N 0.000 claims 1
RVZBZXKTDZTEDW-AFHFFQAUSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 RVZBZXKTDZTEDW-AFHFFQAUSA-N 0.000 claims 1
DUYCENKMMAZWNR-BDVUIUMHSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C=NC=NC=2)C1)C(=O)C(C=1SC=CC=1)(O)C1CCCC1 DUYCENKMMAZWNR-BDVUIUMHSA-N 0.000 claims 1
DMFLXIOETUDIRP-DXLVBJHUSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-di(thiophen-3-yl)acetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C3=CSC=C3)[N+]21CC(=O)NC1=CN=CN=C1 DMFLXIOETUDIRP-DXLVBJHUSA-N 0.000 claims 1
DQHCQNAXJMUYBD-AVRGKSJGSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-phenyl-2-thiophen-3-ylacetate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C3=CSC=C3)C=3C=CC=CC=3)[N+]21CC(=O)NC1=CN=CN=C1 DQHCQNAXJMUYBD-AVRGKSJGSA-N 0.000 claims 1
BYBFJHNMVLBVBU-XCEOWTAJSA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxy-10h-anthracene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4CC4=CC=CC=C43)[N+]21CC(=O)NC1=CN=CN=C1 BYBFJHNMVLBVBU-XCEOWTAJSA-N 0.000 claims 1
XPXSBGICJHODQB-CJYZSSDISA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyfluorene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4C4=CC=CC=C43)[N+]21CC(=O)NC1=CN=CN=C1 XPXSBGICJHODQB-CJYZSSDISA-N 0.000 claims 1
LOGKHQPVIHNRQC-CJYZSSDISA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9-hydroxyxanthene-9-carboxylate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C3(O)C4=CC=CC=C4OC4=CC=CC=C43)[N+]21CC(=O)NC1=CN=CN=C1 LOGKHQPVIHNRQC-CJYZSSDISA-N 0.000 claims 1
SZUGBQXPVVBDJC-CJYZSSDISA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-fluorene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4C4=CC=CC=C43)CC[N+]12CC(=O)NC1=CN=CN=C1 SZUGBQXPVVBDJC-CJYZSSDISA-N 0.000 claims 1
HBHKKIXTJCXTEU-CJYZSSDISA-N [(3r)-1-[2-oxo-2-(pyrimidin-5-ylamino)ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 9h-xanthene-9-carboxylate;bromide Chemical compound [Br-].C1CC([C@H](C2)OC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)CC[N+]12CC(=O)NC1=CN=CN=C1 HBHKKIXTJCXTEU-CJYZSSDISA-N 0.000 claims 1
KVRBYPPMUIHVSM-NXCMLHJESA-N [(3r)-1-[2-oxo-2-[(4-phenyl-1,2-oxazol-3-yl)amino]ethyl]-1-azoniabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate;bromide Chemical compound [Br-].O([C@@H]1C2CC[N+](CC2)(CC(=O)NC=2C(=CON=2)C=2C=CC=CC=2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 KVRBYPPMUIHVSM-NXCMLHJESA-N 0.000 claims 1
KWOSOGIXVROBEO-RSYBFYOOSA-N [O-]P([O-])([O-])=O.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1 Chemical compound [O-]P([O-])([O-])=O.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2C=CC=CC=2)CCCCC1 KWOSOGIXVROBEO-RSYBFYOOSA-N 0.000 claims 1
PWFMLWUCJBKRTI-IVPFZVFJSA-N [O-]P([O-])([O-])=O.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2SC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2SC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2SC=CC=2)CCCCC1 Chemical compound [O-]P([O-])([O-])=O.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2SC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2SC=CC=2)CCCCC1.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CC(=O)NC3=NOC=C3)C2)C=2SC=CC=2)CCCCC1 PWFMLWUCJBKRTI-IVPFZVFJSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
229960004436 budesonide Drugs 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
229960003728 ciclesonide Drugs 0.000 claims 1
239000000850 decongestant Substances 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229960000289 fluticasone propionate Drugs 0.000 claims 1
WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 claims 1
239000011630 iodine Chemical group 0.000 claims 1
229910052740 iodine Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
238000000034 method Methods 0.000 claims 1
229960002744 mometasone furoate Drugs 0.000 claims 1
WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 claims 1
230000000414 obstructive effect Effects 0.000 claims 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
210000002345 respiratory system Anatomy 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 abstract 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 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
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

HR20100693T 2004-11-02 2010-12-14 Derivati kinuklidina i njihova uporaba kao antagonista muskarinskih m3 receptora HRP20100693T1 (hr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0424284.8A GB0424284D0 (en)	2004-11-02	2004-11-02	Organic compounds
PCT/EP2005/011662 WO2006048225A1 (fr)	2004-11-02	2005-10-31	Derives de la quinuclidine et leur utilisation en tant qu'antagonistes du recepteur m3 muscarinique

Publications (1)

Publication Number	Publication Date
HRP20100693T1 true HRP20100693T1 (hr)	2011-01-31

Family

ID=33515948

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HR20100693T HRP20100693T1 (hr)	2004-11-02	2010-12-14	Derivati kinuklidina i njihova uporaba kao antagonista muskarinskih m3 receptora

Country Status (33)

Country	Link
US (2)	US7723356B2 (fr)
EP (2)	EP1811999B1 (fr)
JP (1)	JP4950896B2 (fr)
KR (1)	KR101252307B1 (fr)
CN (1)	CN101056634B (fr)
AR (1)	AR054090A1 (fr)
AT (1)	ATE481099T1 (fr)
AU (1)	AU2005300710B2 (fr)
BR (1)	BRPI0517945A (fr)
CA (1)	CA2583237C (fr)
CY (1)	CY1110952T1 (fr)
DE (1)	DE602005023639D1 (fr)
DK (1)	DK1811999T3 (fr)
EC (1)	ECSP077424A (fr)
ES (1)	ES2353142T3 (fr)
GB (1)	GB0424284D0 (fr)
HR (1)	HRP20100693T1 (fr)
IL (1)	IL182695A0 (fr)
JO (1)	JO2613B1 (fr)
MA (1)	MA29080B1 (fr)
MX (1)	MX2007005189A (fr)
MY (1)	MY145207A (fr)
NO (1)	NO20072371L (fr)
NZ (1)	NZ554302A (fr)
PE (1)	PE20060609A1 (fr)
PL (1)	PL1811999T3 (fr)
PT (1)	PT1811999E (fr)
RU (1)	RU2399620C2 (fr)
SI (1)	SI1811999T1 (fr)
TN (1)	TNSN07164A1 (fr)
TW (1)	TW200628154A (fr)
WO (1)	WO2006048225A1 (fr)
ZA (1)	ZA200702772B (fr)

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KR20080036632A (ko)	2005-08-08	2008-04-28	아젠터 디스커버리 리미티드	바이시클로[2.2.1]헵트-7-일아민 유도체 및 이들의 용도
US8329681B2 (en)	2005-08-11	2012-12-11	University Of Massachusetts	Methods and compositions for the efficient delivery of therapeutic agents to cells and animals
GB0601951D0 (en)	2006-01-31	2006-03-15	Novartis Ag	Organic compounds
EP1894568A1 (fr) *	2006-08-31	2008-03-05	Novartis AG	Composées pharmaceutiques destinées au traitement des maladies inflammatoires ou obstructives des bronches
UA97492C2 (ru) *	2006-11-14	2012-02-27	Астразенека Аб	Хиниклидиновые производные (гетеро) арилциклогептанкарбоксиловой кислоты как антагонисты мускаринового рецептора
TW200825084A (en) *	2006-11-14	2008-06-16	Astrazeneca Ab	New compounds 521
BRPI0721039A2 (pt) *	2006-12-19	2014-07-29	Astrazeneca Ab	" derivados de quinuclidinol como antagonistas de receptores muscarínicos ".
BRPI0816219B8 (pt)	2007-09-07	2021-05-25	Theravance Biopharma R&D Ip Llc	compostos contendo guanidina úteis como antagonistas de receptor muscarínico, composição farmacêutica e uso
US8017617B2 (en)	2007-12-14	2011-09-13	Theravance, Inc.	Amidine-containing compounds useful as muscarinic receptor antagonists
US8431578B2 (en)	2008-01-11	2013-04-30	Novartis Ag	Organic compounds
GB0808707D0 (en) *	2008-05-13	2008-06-18	Argenta Discovery Ltd	New compounds 275
WO2009139708A1 (fr) *	2008-05-13	2009-11-19	Astrazeneca Ab	PRODUIT PHARMACEUTIQUE COMPRENANT UN ANTAGONISTE DU RÉCEPTEUR MUSCARINIQUE ET UN AGONISTE DES β2-ADRÉNOCEPTEURS
GB0808708D0 (en) *	2008-05-13	2008-06-18	Astrazeneca Ab	New compounds 274
CN102089304A (zh)	2008-05-13	2011-06-08	阿斯利康(瑞典)有限公司	作为m3毒蕈碱性受体拮抗剂的奎宁环衍生物
US20090326004A1 (en) *	2008-06-03	2009-12-31	Ranbaxy Laboratories Limited	Muscarinic receptor antagonists
GB0811100D0 (en) *	2008-06-17	2008-07-23	Astrazeneca Ab	New combination
WO2009153536A1 (fr) *	2008-06-17	2009-12-23	Argenta Discovery Limited	Dérivés de 1-aza-bicyclo [2.2.2] octane utiles en tant qu’antagonistes des récepteurs muscariniques
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US20120022127A1 (en)	2009-04-09	2012-01-26	Thomas Allmendinger	Process for preparing pyrrolidinium salts
CN102947298B (zh) *	2010-06-22	2016-03-02	奇斯药制品公司	生物碱氨基酯衍生物及其药物组合物
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2005
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- 2005-10-24 MY MYPI20054966A patent/MY145207A/en unknown
- 2005-10-31 EP EP05798470A patent/EP1811999B1/fr active Active
- 2005-10-31 BR BRPI0517945-9A patent/BRPI0517945A/pt not_active IP Right Cessation
- 2005-10-31 AU AU2005300710A patent/AU2005300710B2/en not_active Ceased
- 2005-10-31 WO PCT/EP2005/011662 patent/WO2006048225A1/fr active Application Filing
- 2005-10-31 SI SI200531188T patent/SI1811999T1/sl unknown
- 2005-10-31 RU RU2007120454/04A patent/RU2399620C2/ru not_active IP Right Cessation
- 2005-10-31 PE PE2005001274A patent/PE20060609A1/es not_active Application Discontinuation
- 2005-10-31 DK DK05798470.0T patent/DK1811999T3/da active
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- 2005-10-31 EP EP10156591A patent/EP2206499A1/fr not_active Withdrawn
- 2005-10-31 KR KR1020077009938A patent/KR101252307B1/ko not_active IP Right Cessation
- 2005-10-31 DE DE602005023639T patent/DE602005023639D1/de active Active
- 2005-10-31 PT PT05798470T patent/PT1811999E/pt unknown
- 2005-10-31 AR ARP050104547A patent/AR054090A1/es not_active Application Discontinuation
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2007
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- 2007-04-19 IL IL182695A patent/IL182695A0/en unknown
- 2007-04-27 EC EC2007007424A patent/ECSP077424A/es unknown
- 2007-04-30 TN TNP2007000164A patent/TNSN07164A1/fr unknown
- 2007-05-08 NO NO20072371A patent/NO20072371L/no not_active Application Discontinuation
- 2007-05-30 MA MA29952A patent/MA29080B1/fr unknown
2010
- 2010-03-11 US US12/721,897 patent/US8084463B2/en not_active Expired - Fee Related
- 2010-11-25 CY CY20101101081T patent/CY1110952T1/el unknown
- 2010-12-14 HR HR20100693T patent/HRP20100693T1/hr unknown

Also Published As

Publication number	Publication date
DK1811999T3 (da)	2010-12-13
DE602005023639D1 (de)	2010-10-28
MY145207A (en)	2012-01-13
CA2583237A1 (fr)	2006-05-11
US20100168132A1 (en)	2010-07-01
NZ554302A (en)	2009-12-24
US20090048281A1 (en)	2009-02-19
TW200628154A (en)	2006-08-16
MX2007005189A (es)	2007-05-11
CY1110952T1 (el)	2015-06-11
US8084463B2 (en)	2011-12-27
KR20070073849A (ko)	2007-07-10
EP1811999B1 (fr)	2010-09-15
RU2399620C2 (ru)	2010-09-20
JP4950896B2 (ja)	2012-06-13
KR101252307B1 (ko)	2013-04-08
RU2007120454A (ru)	2008-12-10
US7723356B2 (en)	2010-05-25
ES2353142T3 (es)	2011-02-25
ATE481099T1 (de)	2010-10-15
SI1811999T1 (sl)	2011-01-31
PT1811999E (pt)	2010-10-29
CA2583237C (fr)	2013-01-22
IL182695A0 (en)	2007-09-20
PE20060609A1 (es)	2006-08-21
CN101056634A (zh)	2007-10-17
EP2206499A1 (fr)	2010-07-14
JP2008518890A (ja)	2008-06-05
EP1811999A1 (fr)	2007-08-01
ECSP077424A (es)	2007-05-30
JO2613B1 (ar)	2011-11-01
BRPI0517945A (pt)	2008-10-21
AR054090A1 (es)	2007-06-06
CN101056634B (zh)	2011-11-30
MA29080B1 (fr)	2007-12-03
AU2005300710B2 (en)	2009-05-14
ZA200702772B (en)	2008-08-27
PL1811999T3 (pl)	2011-03-31
WO2006048225A1 (fr)	2006-05-11
AU2005300710A1 (en)	2006-05-11
NO20072371L (no)	2007-07-12
GB0424284D0 (en)	2004-12-01
TNSN07164A1 (en)	2008-11-21

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