NO328772B1 - Nye kinuklidinderivater fremgangsmate for fremstilling derav og medisinske sammensetninger inneholdende det samme - Google Patents

Nye kinuklidinderivater fremgangsmate for fremstilling derav og medisinske sammensetninger inneholdende det samme Download PDF

Info

Publication number: NO328772B1
Authority: NO; Norway
Prior art keywords: hydroxy; octane; azoniabicyclo; thien; trifluoroacetate
Prior art date: 2000-12-28

Application number

NO20033002A

Other languages

English (en)

Norwegian (no)

Other versions

NO20033002D0 (no

NO20033002L (no

Inventor

Maria Dolors Fernandez Forner

Maria Antonia Buil Albero

Maria Prat Quinones

Original Assignee

Almirall Lab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-12-28

Filing date

2003-06-30

Publication date

2010-05-10

2003-06-30 Application filed by Almirall Lab filed Critical Almirall Lab

2003-06-30 Publication of NO20033002D0 publication Critical patent/NO20033002D0/no

2003-06-30 Publication of NO20033002L publication Critical patent/NO20033002L/no

2010-05-10 Publication of NO328772B1 publication Critical patent/NO328772B1/no

Links

238000000034 method Methods 0.000 title claims description 87
238000002360 preparation method Methods 0.000 title claims description 34
239000000203 mixture Substances 0.000 title description 71
150000008584 quinuclidines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 195
-1 naphthalenyl- Chemical group 0.000 claims description 165
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000008194 pharmaceutical composition Substances 0.000 claims description 13
238000011282 treatment Methods 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 10
208000023504 respiratory system disease Diseases 0.000 claims description 10
125000001544 thienyl group Chemical group 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
150000001450 anions Chemical class 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
208000018522 Gastrointestinal disease Diseases 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
208000014001 urinary system disease Diseases 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 5
125000002723 alicyclic group Chemical group 0.000 claims description 5
239000005557 antagonist Substances 0.000 claims description 5
239000000043 antiallergic agent Substances 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
150000003431 steroids Chemical class 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
208000012931 Urologic disease Diseases 0.000 claims description 4
VONPJFCZRXYEDP-DIGIMVBOSA-M [(3r)-1-(3-naphthalen-1-yloxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C4=CC=CC=C4C=CC=3)C2)C=2SC=CC=2)CCCC1 VONPJFCZRXYEDP-DIGIMVBOSA-M 0.000 claims description 4
VNDDTXJENUQNEZ-HIJBICPQSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-thiophen-2-ylpent-4-enoate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(CC=C)(O)C=3SC=CC=3)[N+]21CCCOC1=CC=CC=C1 VNDDTXJENUQNEZ-HIJBICPQSA-M 0.000 claims description 4
XANWAYQCMJFLQY-QFBILLFUSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate Chemical compound C1([C@](O)(C(=O)O[C@@H]2C3CCN(CC3)C2)C=2OC=CC=2)CCCCC1 XANWAYQCMJFLQY-QFBILLFUSA-N 0.000 claims description 4
CFYRLPTXUIBRFO-MAUKXSAKSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate Chemical compound C1([C@](O)(C(=O)O[C@@H]2C3CCN(CC3)C2)C=2OC=CC=2)CCCC1 CFYRLPTXUIBRFO-MAUKXSAKSA-N 0.000 claims description 4
XANWAYQCMJFLQY-LPHOPBHVSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate Chemical compound C1([C@@](O)(C(=O)O[C@@H]2C3CCN(CC3)C2)C=2OC=CC=2)CCCCC1 XANWAYQCMJFLQY-LPHOPBHVSA-N 0.000 claims description 4
CFYRLPTXUIBRFO-YJBOKZPZSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate Chemical compound C1([C@@](O)(C(=O)O[C@@H]2C3CCN(CC3)C2)C=2OC=CC=2)CCCC1 CFYRLPTXUIBRFO-YJBOKZPZSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
150000001721 carbon Chemical class 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
SITDUJBTVBVJBA-NRFANRHFSA-N 1-azabicyclo[2.2.2]octan-4-yl (2r)-2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound C1([C@](O)(C(=O)OC23CCN(CC2)CC3)C=2C=CC=CC=2)CCCCC1 SITDUJBTVBVJBA-NRFANRHFSA-N 0.000 claims description 3
UAOIHPKVFPCLQU-FLZDTMBISA-M 2,2,2-trifluoroacetate;[(3r)-1-[3-[3-(trifluoromethyl)phenoxy]propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=C(C=CC=3)C(F)(F)F)C2)C=2SC=CC=2)CCCC1 UAOIHPKVFPCLQU-FLZDTMBISA-M 0.000 claims description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
ZDDHJSDGQKUTBN-HFYVASOVSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCOC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 ZDDHJSDGQKUTBN-HFYVASOVSA-M 0.000 claims description 3
HDHXECMEKVQENC-CFRCACJDSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCOC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 HDHXECMEKVQENC-CFRCACJDSA-M 0.000 claims description 3
YVTAVOFVQBNKGB-OXKVUICPSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-thiophen-2-ylpent-4-enoate;bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(CC=C)(O)C=3SC=CC=3)[N+]21CCOC1=CC=CC=C1 YVTAVOFVQBNKGB-OXKVUICPSA-M 0.000 claims description 3
VWKFXNJSBPSTCA-ZNUJAHEQSA-M [(3r)-1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCOCC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 VWKFXNJSBPSTCA-ZNUJAHEQSA-M 0.000 claims description 3
HZYXTVAOZNDNKZ-SVUMUAINSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2OC=CC=2)CCCCC1 HZYXTVAOZNDNKZ-SVUMUAINSA-M 0.000 claims description 3
INGCNBPIVXLXBP-RKFIKRHTSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclohexyl-2-hydroxy-2-phenylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2C=CC=CC=2)CCCCC1 INGCNBPIVXLXBP-RKFIKRHTSA-M 0.000 claims description 3
YVMUFOGUGYILBO-RRVPVRNKSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCCC1 YVMUFOGUGYILBO-RRVPVRNKSA-M 0.000 claims description 3
POXBCZIGBSYATB-GHFJOUEHSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2OC=CC=2)CCCC1 POXBCZIGBSYATB-GHFJOUEHSA-M 0.000 claims description 3
GXCFPRBHASPTQQ-XXPJZDDYSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-phenylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2C=CC=CC=2)CCCC1 GXCFPRBHASPTQQ-XXPJZDDYSA-M 0.000 claims description 3
QYOYLHDCZNMWNQ-XIVHMJBLSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 QYOYLHDCZNMWNQ-XIVHMJBLSA-M 0.000 claims description 3
GXCFPRBHASPTQQ-BTNNGFKNSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-phenylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2C=CC=CC=2)CCCC1 GXCFPRBHASPTQQ-BTNNGFKNSA-M 0.000 claims description 3
QYOYLHDCZNMWNQ-GHFJOUEHSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 QYOYLHDCZNMWNQ-GHFJOUEHSA-M 0.000 claims description 3
LWHLMQSNHOVNNE-NFMWMIBESA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2,3-diphenylpropanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)C(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCOC1=CC=CC=C1 LWHLMQSNHOVNNE-NFMWMIBESA-M 0.000 claims description 3
AWBZUDUZPSVGFK-ZTYMJOMLSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-thiophen-2-ylheptanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)C(O)(CCCCC)C=3SC=CC=3)[N+]21CCCOC1=CC=CC=C1 AWBZUDUZPSVGFK-ZTYMJOMLSA-M 0.000 claims description 3
CUUSTSDTFJAKHH-HIJBICPQSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-thiophen-2-ylpent-3-ynoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)C(O)(C#CC)C=3SC=CC=3)[N+]21CCCOC1=CC=CC=C1 CUUSTSDTFJAKHH-HIJBICPQSA-M 0.000 claims description 3
ZLMCGNPEKQCDML-AZFRURLMSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-3-phenyl-2-thiophen-2-ylpropanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O([C@@H]1C2CC[N+](CC2)(CCCOC=2C=CC=CC=2)C1)C(=O)C(C=1SC=CC=1)(O)CC1=CC=CC=C1 ZLMCGNPEKQCDML-AZFRURLMSA-M 0.000 claims description 3
BPEAOMGOAQZPDO-RAHNUCHMSA-M [(3r)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-4-phenyl-2-thiophen-2-ylbutanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O([C@@H]1C2CC[N+](CC2)(CCCOC=2C=CC=CC=2)C1)C(=O)C(C=1SC=CC=1)(O)CCC1=CC=CC=C1 BPEAOMGOAQZPDO-RAHNUCHMSA-M 0.000 claims description 3
ABZDAOWCLOEUDX-OKQXLFDGSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)C=2OC=CC=2)CCCCC1 ABZDAOWCLOEUDX-OKQXLFDGSA-M 0.000 claims description 3
CAPCZKHAJFFYSS-ZNUJAHEQSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)C=2OC=CC=2)CCCC1 CAPCZKHAJFFYSS-ZNUJAHEQSA-M 0.000 claims description 3
QFMVHYBPTSPZEF-FNWJFSHTSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 QFMVHYBPTSPZEF-FNWJFSHTSA-M 0.000 claims description 3
ABZDAOWCLOEUDX-ZHRJVOQKSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)C=2OC=CC=2)CCCCC1 ABZDAOWCLOEUDX-ZHRJVOQKSA-M 0.000 claims description 3
CAPCZKHAJFFYSS-FNWJFSHTSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)C=2OC=CC=2)CCCC1 CAPCZKHAJFFYSS-FNWJFSHTSA-M 0.000 claims description 3
QFMVHYBPTSPZEF-ZNUJAHEQSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 QFMVHYBPTSPZEF-ZNUJAHEQSA-M 0.000 claims description 3
AMAYDTSCJLKTQX-XXPJZDDYSA-M [(3r)-1-(3-phenylsulfanylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-phenylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCSC=3C=CC=CC=3)C2)C=2C=CC=CC=2)CCCC1 AMAYDTSCJLKTQX-XXPJZDDYSA-M 0.000 claims description 3
AMAYDTSCJLKTQX-BTNNGFKNSA-M [(3r)-1-(3-phenylsulfanylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-phenylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCSC=3C=CC=CC=3)C2)C=2C=CC=CC=2)CCCC1 AMAYDTSCJLKTQX-BTNNGFKNSA-M 0.000 claims description 3
VNRPVLMOXOJOKC-GHFJOUEHSA-M [(3r)-1-(3-phenylsulfanylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCSC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 VNRPVLMOXOJOKC-GHFJOUEHSA-M 0.000 claims description 3
QEVJTYLETFJRJK-OKFKHHGASA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3SC=CC=3)C2)C=2OC=CC=2)CCCC1 QEVJTYLETFJRJK-OKFKHHGASA-M 0.000 claims description 3
LFVDKLDNAFDAOQ-HFYVASOVSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3SC=CC=3)C2)C=2OC=CC=2)CCCCC1 LFVDKLDNAFDAOQ-HFYVASOVSA-M 0.000 claims description 3
UQUOPHMNADCCOB-OOSBWHIZSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclohexyl-2-hydroxy-2-phenylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3SC=CC=3)C2)C=2C=CC=CC=2)CCCCC1 UQUOPHMNADCCOB-OOSBWHIZSA-M 0.000 claims description 3
QEVJTYLETFJRJK-GACOWHTFSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-(furan-2-yl)-2-hydroxyacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3SC=CC=3)C2)C=2OC=CC=2)CCCC1 QEVJTYLETFJRJK-GACOWHTFSA-M 0.000 claims description 3
REGOUNFINUSWED-BNFNRWAISA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2,3-diphenylpropanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)C(CC=3C=CC=CC=3)C=3C=CC=CC=3)[N+]21CCCC1=CC=CS1 REGOUNFINUSWED-BNFNRWAISA-M 0.000 claims description 3
FOZTVPUYOVZWKM-LVWLLOTASA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-thiophen-2-ylbut-3-enoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)C(C=C)(O)C=3SC=CC=3)[N+]21CCCC1=CC=CS1 FOZTVPUYOVZWKM-LVWLLOTASA-M 0.000 claims description 3
ARCWEZHQRFNWSG-HIJBICPQSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-thiophen-2-ylheptanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)C(O)(CCCCC)C=3SC=CC=3)[N+]21CCCC1=CC=CS1 ARCWEZHQRFNWSG-HIJBICPQSA-M 0.000 claims description 3
LIUWGFJHRKBPPJ-RPEPZVHPSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-thiophen-2-ylpent-3-ynoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)C(O)(C#CC)C=3SC=CC=3)[N+]21CCCC1=CC=CS1 LIUWGFJHRKBPPJ-RPEPZVHPSA-M 0.000 claims description 3
YMHRCMHOJRCQPZ-RPEPZVHPSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2-thiophen-2-ylpent-4-enoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C([C@@H](C(CC1)CC2)OC(=O)C(CC=C)(O)C=3SC=CC=3)[N+]21CCCC1=CC=CS1 YMHRCMHOJRCQPZ-RPEPZVHPSA-M 0.000 claims description 3
IXCSUZHNBOOMCF-ZTYMJOMLSA-M [(3r)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] 2-hydroxy-3-phenyl-2-thiophen-2-ylpropanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O([C@@H]1C2CC[N+](CC2)(CCCC=2SC=CC=2)C1)C(=O)C(C=1SC=CC=1)(O)CC1=CC=CC=C1 IXCSUZHNBOOMCF-ZTYMJOMLSA-M 0.000 claims description 3
PKNHWSCPTDXWKC-SVUMUAINSA-M [(3r)-1-(4-oxo-4-phenylbutyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC(=O)C=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 PKNHWSCPTDXWKC-SVUMUAINSA-M 0.000 claims description 3
FIRKIFPQHOMYIP-BPNBWRBTSA-M [(3r)-1-(4-oxo-4-thiophen-2-ylbutyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC(=O)C=3SC=CC=3)C2)C=2SC=CC=2)CCCC1 FIRKIFPQHOMYIP-BPNBWRBTSA-M 0.000 claims description 3
BZXRCPISSXBKKE-ZKMFZOPASA-M [(3r)-1-[3-(2,4-difluorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C(=CC(F)=CC=3)F)C2)C=2SC=CC=2)CCCC1 BZXRCPISSXBKKE-ZKMFZOPASA-M 0.000 claims description 3
NVNOQMCJQGQLIE-OCXUGVEJSA-N [(3r)-1-[3-(2-carbamoylphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.NC(=O)C1=CC=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)[C@@](O)(C3CCCC3)C=3SC=CC=3)CCC2CC1 NVNOQMCJQGQLIE-OCXUGVEJSA-N 0.000 claims description 3
XFANAXZQCFPKIU-AUMKFSQYSA-M [(3r)-1-[3-(2-chlorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C(=CC=CC=3)Cl)C2)C=2SC=CC=2)CCCC1 XFANAXZQCFPKIU-AUMKFSQYSA-M 0.000 claims description 3
SJSFJEUCDJYMBE-SVUMUAINSA-M [(3r)-1-[3-(2-methylphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC1=CC=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)[C@@](O)(C3CCCC3)C=3SC=CC=3)CCC2CC1 SJSFJEUCDJYMBE-SVUMUAINSA-M 0.000 claims description 3
ZKRWCSCWRWFRJE-SLMXWSJOSA-M [(3r)-1-[3-(3-cyanophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2r)-2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=C(C=CC=3)C#N)C2)C=2SC=CC=2)CCCCC1 ZKRWCSCWRWFRJE-SLMXWSJOSA-M 0.000 claims description 3
ZKRWCSCWRWFRJE-HJMJYENQSA-M [(3r)-1-[3-(3-cyanophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclohexyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=C(C=CC=3)C#N)C2)C=2SC=CC=2)CCCCC1 ZKRWCSCWRWFRJE-HJMJYENQSA-M 0.000 claims description 3
SCXNOHWCMHAFGN-MPYKNGODSA-M [(3r)-1-[3-(4-methoxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(OC)=CC=C1OCCC[N+]1(C[C@@H]2OC(=O)[C@@](O)(C3CCCC3)C=3SC=CC=3)CCC2CC1 SCXNOHWCMHAFGN-MPYKNGODSA-M 0.000 claims description 3
MRITUWHKIYEGFR-AUMKFSQYSA-M [(3r)-1-[3-(4-nitrophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC(=CC=3)[N+]([O-])=O)C2)C=2SC=CC=2)CCCC1 MRITUWHKIYEGFR-AUMKFSQYSA-M 0.000 claims description 3
KFLKWZUZMBYCFZ-ZZMDWBSISA-M [(3r)-1-[3-(4-phenylphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=CC(=CC=3)C=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 KFLKWZUZMBYCFZ-ZZMDWBSISA-M 0.000 claims description 3
HNSUKQBUPMWPFN-DIGIMVBOSA-M [(3r)-1-[3-(5,6,7,8-tetrahydronaphthalen-2-yloxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCOC=3C=C4CCCCC4=CC=3)C2)C=2SC=CC=2)CCCC1 HNSUKQBUPMWPFN-DIGIMVBOSA-M 0.000 claims description 3
WROMLIUYHQSKCT-RLPLPQPYSA-M [(3r)-1-[3-(n-methylanilino)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(C2)CCCN(C)C=2C=CC=CC=2)C=2SC=CC=2)CCCC1 WROMLIUYHQSKCT-RLPLPQPYSA-M 0.000 claims description 3
PZGGZOMINHWEBL-FPECWBOSSA-M [(3r)-1-[3-[3-(dimethylamino)phenoxy]propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CN(C)C1=CC=CC(OCCC[N+]23CCC(CC2)[C@H](C3)OC(=O)[C@@](O)(C2CCCC2)C=2SC=CC=2)=C1 PZGGZOMINHWEBL-FPECWBOSSA-M 0.000 claims description 3
MXBOIYDISGWKMQ-AKAAHHDGSA-M [(3r)-1-[4-(4-fluorophenyl)-4-oxobutyl]-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC(=O)C=3C=CC(F)=CC=3)C2)C=2SC=CC=2)CCCC1 MXBOIYDISGWKMQ-AKAAHHDGSA-M 0.000 claims description 3
QYOYLHDCZNMWNQ-FZUQKSRQSA-M [(3s)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;bromide Chemical compound [Br-].C1([C@](O)(C(=O)O[C@H]2C3CC[N+](CC3)(CCCOC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 QYOYLHDCZNMWNQ-FZUQKSRQSA-M 0.000 claims description 3
QFMVHYBPTSPZEF-NPHISCKGSA-M [(3s)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)C=2SC=CC=2)CCCC1 QFMVHYBPTSPZEF-NPHISCKGSA-M 0.000 claims description 3
SGSJVILQDFLXOS-WMCDIOBSSA-M [(3s)-1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] (2s)-2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)O[C@H]2C3CC[N+](CC3)(CCCC=3SC=CC=3)C2)C=2SC=CC=2)CCCC1 SGSJVILQDFLXOS-WMCDIOBSSA-M 0.000 claims description 3
KSZJAGSTGBVXJA-HHLMVONJSA-M [1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-4-yl] (2r)-2-cyclohexyl-2-hydroxy-2-phenylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)OC23CC[N+](CCCOC=4C=CC=CC=4)(CC2)CC3)C=2C=CC=CC=2)CCCCC1 KSZJAGSTGBVXJA-HHLMVONJSA-M 0.000 claims description 3
ODACIKLNNRLIGR-GNJBESRBSA-M [1-(3-thiophen-2-ylpropyl)-1-azoniabicyclo[2.2.2]octan-4-yl] (2r)-2-cyclohexyl-2-hydroxy-2-phenylacetate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1([C@](O)(C(=O)OC23CC[N+](CCCC=4SC=CC=4)(CC2)CC3)C=2C=CC=CC=2)CCCCC1 ODACIKLNNRLIGR-GNJBESRBSA-M 0.000 claims description 3
ZURKACODPCBURY-HNMNPFRUSA-M [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCC3)C=3C=CC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCC3)C=3C=CC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 ZURKACODPCBURY-HNMNPFRUSA-M 0.000 claims description 3
ZKOXNGMNRJZWKM-ZBNAEMFTSA-M [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCC3)C=3OC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCC3)C=3OC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 ZKOXNGMNRJZWKM-ZBNAEMFTSA-M 0.000 claims description 3
XSFUYXSSZFJACO-UYGDYMDRSA-M [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCCC3)C=3C=CC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCCC3)C=3C=CC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 XSFUYXSSZFJACO-UYGDYMDRSA-M 0.000 claims description 3
CCFMWZNNIHXPCU-PSCACLNXSA-M [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCCC3)C=3OC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCCC3)C=3OC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 CCFMWZNNIHXPCU-PSCACLNXSA-M 0.000 claims description 3
MXYMBPWBOWJSKW-PSCACLNXSA-M [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCCC3)C=3SC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@@](O)(C3CCCCC3)C=3SC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 MXYMBPWBOWJSKW-PSCACLNXSA-M 0.000 claims description 3
ZURKACODPCBURY-NVAQPETASA-M [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@](O)(C3CCCC3)C=3C=CC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@](O)(C3CCCC3)C=3C=CC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 ZURKACODPCBURY-NVAQPETASA-M 0.000 claims description 3
ZKOXNGMNRJZWKM-QCGIIVEOSA-M [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@](O)(C3CCCC3)C=3OC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@](O)(C3CCCC3)C=3OC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 ZKOXNGMNRJZWKM-QCGIIVEOSA-M 0.000 claims description 3
PWPISBDOVOTNCR-QCGIIVEOSA-M [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@](O)(C3CCCC3)C=3SC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 Chemical compound [O-]C(=O)C(F)(F)F.C1CC([C@H](C2)OC(=O)[C@](O)(C3CCCC3)C=3SC=CC=3)CC[N+]12C(C)C1=CC=CC=C1 PWPISBDOVOTNCR-QCGIIVEOSA-M 0.000 claims description 3
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JYFMJPJLHTVHMG-BBQAJUCSSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] 2-benzyl-3-hydroxy-2-phenylpropanoate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1C=CC=CC=1)(CO)CC1=CC=CC=C1 JYFMJPJLHTVHMG-BBQAJUCSSA-N 0.000 description 1
XANWAYQCMJFLQY-UCFFOFKASA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-(furan-2-yl)-2-hydroxyacetate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1OC=CC=1)(O)C1CCCCC1 XANWAYQCMJFLQY-UCFFOFKASA-N 0.000 description 1
SWZDDEVSNRTITP-ZQRQZVKFSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] 2-cyclohexyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCCC1 SWZDDEVSNRTITP-ZQRQZVKFSA-N 0.000 description 1
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RFXCNPOWSCFJCD-LROBGIAVSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] 2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1C=CC=CC=1)(O)C1CCCC1 RFXCNPOWSCFJCD-LROBGIAVSA-N 0.000 description 1
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FUQUXNYXJYOMKW-YMXDCFFPSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] 2-hydroxy-4-phenyl-2-thiophen-2-ylbutanoate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1SC=CC=1)(O)CCC1=CC=CC=C1 FUQUXNYXJYOMKW-YMXDCFFPSA-N 0.000 description 1
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208000023819 chronic asthma Diseases 0.000 description 1
208000007451 chronic bronchitis Diseases 0.000 description 1
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239000008120 corn starch Substances 0.000 description 1
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HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
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XWCQLLDGXBLGMD-UHFFFAOYSA-M magnesium;pentane;bromide Chemical compound [Mg+2].[Br-].CCCC[CH2-] XWCQLLDGXBLGMD-UHFFFAOYSA-M 0.000 description 1
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BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
FGMUSNHTKNGVQD-UHFFFAOYSA-N methyl 2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical compound C=1C=CC=CC=1C(O)(C(=O)OC)C1CCCC1 FGMUSNHTKNGVQD-UHFFFAOYSA-N 0.000 description 1
CYOJLERNTVFORQ-UHFFFAOYSA-N methyl 2-cyclopentyl-2-hydroxy-2-thiophen-2-ylacetate Chemical compound C=1C=CSC=1C(O)(C(=O)OC)C1CCCC1 CYOJLERNTVFORQ-UHFFFAOYSA-N 0.000 description 1
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239000003149 muscarinic antagonist Substances 0.000 description 1
UANSQQFYKHHDJM-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=CC2=C1 UANSQQFYKHHDJM-KRWDZBQOSA-N 0.000 description 1
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208000005346 nocturnal enuresis Diseases 0.000 description 1
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
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125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229920000075 poly(4-vinylpyridine) Polymers 0.000 description 1
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239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
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239000000018 receptor agonist Substances 0.000 description 1
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CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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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
125000003944 tolyl group Chemical group 0.000 description 1
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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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
- 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)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO20033002A 2000-12-28 2003-06-30 Nye kinuklidinderivater fremgangsmate for fremstilling derav og medisinske sammensetninger inneholdende det samme NO328772B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES200003130		2000-12-28
PCT/EP2001/015168 WO2002053564A2 (en)	2000-12-28	2001-12-20	Quinuclidine derivatives and their use as m3 antagonists

Publications (3)

Publication Number	Publication Date
NO20033002D0 NO20033002D0 (no)	2003-06-30
NO20033002L NO20033002L (no)	2003-06-30
NO328772B1 true NO328772B1 (no)	2010-05-10

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US (4)	US7122558B2 (et)
EP (1)	EP1353919B1 (et)
JP (1)	JP4295985B2 (et)
KR (1)	KR100869721B1 (et)
CN (1)	CN1250545C (et)
AR (1)	AR032072A1 (et)
AT (1)	ATE334128T1 (et)
AU (1)	AU2002238471B2 (et)
BG (1)	BG66162B1 (et)
BR (1)	BR0116624A (et)
CA (1)	CA2433128C (et)
CY (1)	CY1105719T1 (et)
CZ (1)	CZ301209B6 (et)
DE (1)	DE60121813T2 (et)
DK (1)	DK1353919T3 (et)
EC (1)	ECSP034672A (et)
EE (1)	EE05404B1 (et)
ES (1)	ES2266291T3 (et)
HK (1)	HK1055739A1 (et)
HU (1)	HUP0303524A3 (et)
IL (2)	IL156558A0 (et)
MX (1)	MXPA03005862A (et)
MY (1)	MY136067A (et)
NO (1)	NO328772B1 (et)
NZ (1)	NZ526674A (et)
PE (1)	PE20020721A1 (et)
PL (1)	PL363807A1 (et)
PT (1)	PT1353919E (et)
RU (1)	RU2282629C2 (et)
SI (1)	SI1353919T1 (et)
SK (1)	SK287414B6 (et)
UA (1)	UA75626C2 (et)
WO (1)	WO2002053564A2 (et)
ZA (1)	ZA200305008B (et)

Families Citing this family (92)

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Publication number	Priority date	Publication date	Assignee	Title
ES2165768B1 (es)	1999-07-14	2003-04-01	Almirall Prodesfarma Sa	Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen.
AU2002228015B2 (en)	2000-12-22	2007-08-23	Almirall, S.A.	Quinuclidine carbamate derivatives and their use as M3 antagonists
EP1353919B1 (en) *	2000-12-28	2006-07-26	Almirall Prodesfarma AG	Novel quinuclidine derivatives and medicinal compositions containing the same
GB0118373D0 (en) *	2001-07-27	2001-09-19	Glaxo Group Ltd	Novel therapeutic method
ES2203327B1 (es)	2002-06-21	2005-06-16	Almirall Prodesfarma, S.A.	Nuevos carbamatos de quinuclidina y composiciones farmaceuticas que los contienen.
ES2204295B1 (es)	2002-07-02	2005-08-01	Almirall Prodesfarma, S.A.	Nuevos derivados de quinuclidina-amida.
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AU2002238471B2 (en)	2007-06-28
PE20020721A1 (es)	2002-10-01
IL156558A0 (en)	2004-01-04
US20100234332A1 (en)	2010-09-16
RU2003123120A (ru)	2005-01-10
WO2002053564A2 (en)	2002-07-11
PT1353919E (pt)	2006-11-30
US7122558B2 (en)	2006-10-17
US20040072863A1 (en)	2004-04-15
BG66162B1 (bg)	2011-09-30
CA2433128A1 (en)	2002-07-11
US7893087B2 (en)	2011-02-22
EP1353919B1 (en)	2006-07-26
UA75626C2 (en)	2006-05-15
JP2004517123A (ja)	2004-06-10
HK1055739A1 (en)	2004-01-21
CN1487938A (zh)	2004-04-07
BR0116624A (pt)	2003-12-23
CY1105719T1 (el)	2010-12-22
CZ20031812A3 (en)	2004-05-12
NZ526674A (en)	2005-03-24
EE200300312A (et)	2003-10-15
PL363807A1 (en)	2004-11-29
ES2266291T3 (es)	2007-03-01
IL156558A (en)	2009-06-15
KR20030067726A (ko)	2003-08-14
MY136067A (en)	2008-08-29
SK7992003A3 (en)	2004-08-03
CA2433128C (en)	2010-05-25
WO2002053564A3 (en)	2002-10-31
EP1353919A2 (en)	2003-10-22
ATE334128T1 (de)	2006-08-15
NO20033002D0 (no)	2003-06-30
DE60121813D1 (de)	2006-09-07
AR032072A1 (es)	2003-10-22
RU2282629C2 (ru)	2006-08-27
US20070105897A1 (en)	2007-05-10
NO20033002L (no)	2003-06-30
EE05404B1 (et)	2011-04-15
JP4295985B2 (ja)	2009-07-15
CZ301209B6 (cs)	2009-12-09
SI1353919T1 (sl)	2006-12-31
HUP0303524A2 (hu)	2004-01-28
CN1250545C (zh)	2006-04-12
MXPA03005862A (es)	2005-09-08
HUP0303524A3 (en)	2008-03-28
BG107950A (bg)	2004-03-31
DE60121813T2 (de)	2007-09-20
ECSP034672A (es)	2003-08-29
US7879874B2 (en)	2011-02-01
DK1353919T3 (da)	2006-11-20
US20070129398A1 (en)	2007-06-07
SK287414B6 (sk)	2010-09-07
KR100869721B1 (ko)	2008-11-21
ZA200305008B (en)	2005-01-26

Publication	Publication Date	Title
NO328772B1 (no)	2010-05-10	Nye kinuklidinderivater fremgangsmate for fremstilling derav og medisinske sammensetninger inneholdende det samme
AU2002238471A1 (en)	2003-01-23	Quinuclidine derivatives and their use as M3 antagonists
AU2003242757B2 (en)	2009-01-08	New quinuclidine amide derivatives
EP1345937B1 (en)	2005-09-28	Quinuclidine carbamate derivatives and their use as m3 antagonists
US20090054480A1 (en)	2009-02-26	Novel quinuclidine carbamate derivatives and medicinal compositions containing the same
AU2002228015A1 (en)	2003-01-23	Quinuclidine carbamate derivatives and their use as M3 antagonists

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