JP2009504768A5 - - Google Patents
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- Publication number
- JP2009504768A5 JP2009504768A5 JP2008527135A JP2008527135A JP2009504768A5 JP 2009504768 A5 JP2009504768 A5 JP 2009504768A5 JP 2008527135 A JP2008527135 A JP 2008527135A JP 2008527135 A JP2008527135 A JP 2008527135A JP 2009504768 A5 JP2009504768 A5 JP 2009504768A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- azoniabicyclo
- diphenyl
- hydroxy
- heptane bromide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 claims description 10
- -1 trifluoroacetate ion Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims 3
- 229960004373 acetylcholine Drugs 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229940112141 dry powder inhaler Drugs 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- PDJGIOVYWCVUTC-UHFFFAOYSA-M (1-ethyl-1-azoniabicyclo[2.2.1]heptan-4-yl)-diphenylmethanol;bromide Chemical compound [Br-].C1C[N+](CC)(C2)CCC12C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 PDJGIOVYWCVUTC-UHFFFAOYSA-M 0.000 claims 1
- BPURUAIDMARGPI-UHFFFAOYSA-M (1-hex-5-enyl-1-azoniabicyclo[2.2.1]heptan-4-yl)-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCCC=C)(CC1)C2)(O)C1=CC=CC=C1 BPURUAIDMARGPI-UHFFFAOYSA-M 0.000 claims 1
- BUQWNAIAQSJBGF-UHFFFAOYSA-M (1-hexyl-1-azoniabicyclo[2.2.1]heptan-4-yl)-diphenylmethanol;bromide Chemical compound [Br-].C1C[N+](CCCCCC)(C2)CCC12C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 BUQWNAIAQSJBGF-UHFFFAOYSA-M 0.000 claims 1
- QTOYIMYSNVABAB-UHFFFAOYSA-M (1-nonyl-1-azoniabicyclo[2.2.1]heptan-4-yl)-diphenylmethanol;bromide Chemical compound [Br-].C1C[N+](CCCCCCCCC)(C2)CCC12C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 QTOYIMYSNVABAB-UHFFFAOYSA-M 0.000 claims 1
- KDPYXAKZNYGSFT-UHFFFAOYSA-M 2,2-diphenyl-2-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]acetonitrile;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)C2)(C#N)C1=CC=CC=C1 KDPYXAKZNYGSFT-UHFFFAOYSA-M 0.000 claims 1
- IXIBREPTIQOQGP-UHFFFAOYSA-M 2,2-diphenyl-2-[1-(3-phenylpropyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]acetonitrile;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCC=3C=CC=CC=3)(CC1)C2)(C#N)C1=CC=CC=C1 IXIBREPTIQOQGP-UHFFFAOYSA-M 0.000 claims 1
- ZUFGHLIVMMFQLU-UHFFFAOYSA-M 2-(1-benzyl-1-azoniabicyclo[2.2.1]heptan-4-yl)-2,2-diphenylacetonitrile;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CC=3C=CC=CC=3)(CC1)C2)(C#N)C1=CC=CC=C1 ZUFGHLIVMMFQLU-UHFFFAOYSA-M 0.000 claims 1
- OETZWJYIMJQDRQ-UHFFFAOYSA-M 2-(1-ethyl-1-azoniabicyclo[2.2.1]heptan-4-yl)-2,2-diphenylacetonitrile;bromide Chemical compound [Br-].C1C[N+](CC)(C2)CCC12C(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 OETZWJYIMJQDRQ-UHFFFAOYSA-M 0.000 claims 1
- SEDAKDQHHDXQQE-UHFFFAOYSA-M 2-(1-hexyl-1-azoniabicyclo[2.2.1]heptan-4-yl)-2,2-diphenylacetonitrile;bromide Chemical compound [Br-].C1C[N+](CCCCCC)(C2)CCC12C(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 SEDAKDQHHDXQQE-UHFFFAOYSA-M 0.000 claims 1
- ANIPEIJJIGNLCU-UHFFFAOYSA-M 2-[1-(2-hydroxyethyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-2,2-diphenylacetonitrile;bromide Chemical compound [Br-].C1C[N+](CCO)(C2)CCC12C(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 ANIPEIJJIGNLCU-UHFFFAOYSA-M 0.000 claims 1
- YENBEILOHOLUOO-UHFFFAOYSA-M 2-[1-(3-methoxypropyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-2,2-diphenylacetonitrile;bromide Chemical compound [Br-].C1C[N+](CCCOC)(C2)CCC12C(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 YENBEILOHOLUOO-UHFFFAOYSA-M 0.000 claims 1
- FPVHGDXLYQQKRZ-UHFFFAOYSA-M 2-[1-(cyclohexylmethyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-2,2-diphenylacetonitrile;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CC3CCCCC3)(CC1)C2)(C#N)C1=CC=CC=C1 FPVHGDXLYQQKRZ-UHFFFAOYSA-M 0.000 claims 1
- ZHMBONPBHCQABZ-UHFFFAOYSA-M 2-[1-[2-(1h-indol-2-yl)ethyl]-1-azoniabicyclo[2.2.1]heptan-4-yl]-2,2-diphenylacetonitrile;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCC=3NC4=CC=CC=C4C=3)(CC1)C2)(C#N)C1=CC=CC=C1 ZHMBONPBHCQABZ-UHFFFAOYSA-M 0.000 claims 1
- MXMVOGBLQLSFLG-UHFFFAOYSA-N 2-[3-[4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.1]heptan-1-yl]propoxy]phenol;bromide Chemical compound [Br-].OC1=CC=CC=C1OCCC[N+]1(C2)CCC2(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 MXMVOGBLQLSFLG-UHFFFAOYSA-N 0.000 claims 1
- OQDYATWZZXSYBS-UHFFFAOYSA-M 2-[4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.1]heptan-1-yl]ethyl benzoate;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOC(=O)C=3C=CC=CC=3)(CC1)C2)(O)C1=CC=CC=C1 OQDYATWZZXSYBS-UHFFFAOYSA-M 0.000 claims 1
- PFVDQAVJJJSHDR-UHFFFAOYSA-M 4-[4-[cyano(diphenyl)methyl]-1-azoniabicyclo[2.2.1]heptan-1-yl]butanenitrile;bromide Chemical compound [Br-].C1C[N+](CCCC#N)(C2)CCC12C(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 PFVDQAVJJJSHDR-UHFFFAOYSA-M 0.000 claims 1
- FVWNDVASSKEXHZ-UHFFFAOYSA-M 6-[4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.1]heptan-1-yl]hexan-1-ol;bromide Chemical compound [Br-].C1C[N+](CCCCCCO)(C2)CCC12C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 FVWNDVASSKEXHZ-UHFFFAOYSA-M 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 206010061876 Obstruction Diseases 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- YBLDQQDCSJWQIC-UHFFFAOYSA-M [1-(2-methoxyethyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C1C[N+](CCOC)(C2)CCC12C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 YBLDQQDCSJWQIC-UHFFFAOYSA-M 0.000 claims 1
- OTSMGVLZNNGFKG-UHFFFAOYSA-M [1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOC=3C=CC=CC=3)(CC1)C2)(O)C1=CC=CC=C1 OTSMGVLZNNGFKG-UHFFFAOYSA-M 0.000 claims 1
- KMRVAHIHUIKLNB-UHFFFAOYSA-M [1-(3-naphthalen-2-yloxypropyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=C4C=CC=CC4=CC=3)(CC1)C2)(O)C1=CC=CC=C1 KMRVAHIHUIKLNB-UHFFFAOYSA-M 0.000 claims 1
- BXQZGQXBRYYDAC-UHFFFAOYSA-M [1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=CC=CC=3)(CC1)C2)(O)C1=CC=CC=C1 BXQZGQXBRYYDAC-UHFFFAOYSA-M 0.000 claims 1
- JACIGCRJLAQOAG-UHFFFAOYSA-M [1-(4-phenoxybutyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCCOC=3C=CC=CC=3)(CC1)C2)(O)C1=CC=CC=C1 JACIGCRJLAQOAG-UHFFFAOYSA-M 0.000 claims 1
- URCMEQZIXFRGBA-UHFFFAOYSA-M [1-(cyclohexylmethyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CC3CCCCC3)(CC1)C2)(O)C1=CC=CC=C1 URCMEQZIXFRGBA-UHFFFAOYSA-M 0.000 claims 1
- UOQCSFHGPNSHSG-UHFFFAOYSA-M [1-[(3-methoxyphenyl)methyl]-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].COC1=CC=CC(C[N+]23CCC(CC2)(C3)C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 UOQCSFHGPNSHSG-UHFFFAOYSA-M 0.000 claims 1
- QNHNXNPIPCSLBP-UHFFFAOYSA-M [1-[2-[(3-methoxyphenyl)methoxy]ethyl]-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].COC1=CC=CC(COCC[N+]23CCC(CC2)(C3)C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 QNHNXNPIPCSLBP-UHFFFAOYSA-M 0.000 claims 1
- AXBOBELJLQOWPL-UHFFFAOYSA-M [1-[3-(3-chlorophenoxy)propyl]-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=C(Cl)C=CC=3)(CC1)C2)(O)C1=CC=CC=C1 AXBOBELJLQOWPL-UHFFFAOYSA-M 0.000 claims 1
- NGTQNKCGHRSIPQ-UHFFFAOYSA-M [1-[3-(4-bromophenoxy)propyl]-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=CC(Br)=CC=3)(CC1)C2)(O)C1=CC=CC=C1 NGTQNKCGHRSIPQ-UHFFFAOYSA-M 0.000 claims 1
- AWFAZKNPXWIEBQ-UHFFFAOYSA-M [1-[3-(4-nitrophenoxy)propyl]-1-azoniabicyclo[2.2.1]heptan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=CC(=CC=3)[N+]([O-])=O)(CC1)C2)(O)C1=CC=CC=C1 AWFAZKNPXWIEBQ-UHFFFAOYSA-M 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- SUVOQQBXZFXBFI-UHFFFAOYSA-M diphenyl-[1-(2-phenylethyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCC=3C=CC=CC=3)(CC1)C2)(O)C1=CC=CC=C1 SUVOQQBXZFXBFI-UHFFFAOYSA-M 0.000 claims 1
- VEXJMDRECRGFAV-UHFFFAOYSA-M diphenyl-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)C2)(O)C1=CC=CC=C1 VEXJMDRECRGFAV-UHFFFAOYSA-M 0.000 claims 1
- ONHJTLAXELJOER-UHFFFAOYSA-M diphenyl-[1-(3-phenylmethoxypropyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOCC=3C=CC=CC=3)(CC1)C2)(O)C1=CC=CC=C1 ONHJTLAXELJOER-UHFFFAOYSA-M 0.000 claims 1
- LRNNXNVGBVUJLH-UHFFFAOYSA-M diphenyl-[1-(4-phenylmethoxybutyl)-1-azoniabicyclo[2.2.1]heptan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCCOCC=3C=CC=CC=3)(CC1)C2)(O)C1=CC=CC=C1 LRNNXNVGBVUJLH-UHFFFAOYSA-M 0.000 claims 1
- PFCWMSURHUQAQA-UHFFFAOYSA-M diphenyl-[1-[[4-(trifluoromethoxy)phenyl]methyl]-1-azoniabicyclo[2.2.1]heptan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CC=3C=CC(OC(F)(F)F)=CC=3)(CC1)C2)(O)C1=CC=CC=C1 PFCWMSURHUQAQA-UHFFFAOYSA-M 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 229940071648 metered dose inhaler Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000010807 negative regulation of binding Effects 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 229940085991 phosphate ion Drugs 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70930105P | 2005-08-18 | 2005-08-18 | |
| PCT/US2006/032138 WO2007022351A2 (en) | 2005-08-18 | 2006-08-17 | Muscarinic acetylcholine receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009504768A JP2009504768A (ja) | 2009-02-05 |
| JP2009504768A5 true JP2009504768A5 (https=) | 2009-10-01 |
Family
ID=37758395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008527135A Pending JP2009504768A (ja) | 2005-08-18 | 2006-08-17 | ムスカリン性アセチルコリン受容体アンタゴニスト |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US7767691B2 (https=) |
| EP (1) | EP1937068A4 (https=) |
| JP (1) | JP2009504768A (https=) |
| WO (1) | WO2007022351A2 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20050250A1 (es) | 2003-07-17 | 2005-04-08 | Glaxo Group Ltd | Antagonistas de los receptores muscarinicos de la acetilcolina |
| WO2005037280A1 (en) | 2003-10-14 | 2005-04-28 | Glaxo Group Limited | Muscarinic acetycholine receptor antagonists |
| PE20050489A1 (es) | 2003-11-04 | 2005-09-02 | Glaxo Group Ltd | Antagonistas de receptores de acetilcolina muscarinicos |
| WO2005087236A1 (en) * | 2004-03-11 | 2005-09-22 | Glaxo Group Limited | Novel m3 muscarinic acetylcholine receptor antagonists |
| JP2007529513A (ja) | 2004-03-17 | 2007-10-25 | グラクソ グループ リミテッド | Ｍ３ムスカリン性アセチルコリン受容体アンタゴニスト |
| UY28871A1 (es) | 2004-04-27 | 2005-11-30 | Glaxo Group Ltd | Antagonistas del receptor de acetilcolina muscarinico |
| EP1747219A4 (en) * | 2004-05-13 | 2010-05-26 | Glaxo Group Ltd | Antagonists of muscarinic acetylcholine receptor |
| CA2675942C (en) | 2007-02-23 | 2016-04-12 | Theravance, Inc. | Quaternary ammonium diphenylmethyl compounds useful as muscarinic receptor antagonists |
| US8202891B2 (en) | 2007-04-24 | 2012-06-19 | Theravance, Inc. | Quaternary ammonium compounds useful as muscarinic receptor antagonists |
| PE20091553A1 (es) | 2008-02-06 | 2009-10-30 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
| UY31636A1 (es) | 2008-02-06 | 2009-08-03 | Farmacoforos duales-antagonistas muscarinicos de pde4 | |
| AR070562A1 (es) | 2008-02-06 | 2010-04-21 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
| WO2010094643A1 (en) | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Quinoline derivatives and their uses for rhinitis and urticaria |
| KR102794286B1 (ko) * | 2016-01-08 | 2025-04-09 | 테론 파마슈티칼즈, 인크. | 7-아조니아바이사이클로[2.2.1]헵탄 유도체의 건조 분말 흡입기 조성물 |
| AU2021266148A1 (en) | 2020-04-30 | 2023-01-05 | Idorsia Pharmaceuticals Ltd | Azetidin-3-ylmethanol derivatives as CCR6 receptor modulators |
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- 2006-08-17 WO PCT/US2006/032138 patent/WO2007022351A2/en not_active Ceased
- 2006-08-17 US US12/063,719 patent/US7767691B2/en not_active Expired - Fee Related
- 2006-08-17 EP EP06801732A patent/EP1937068A4/en not_active Withdrawn
- 2006-08-17 JP JP2008527135A patent/JP2009504768A/ja active Pending
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