JP2005533799A5 - - Google Patents
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- JP2005533799A5 JP2005533799A5 JP2004514785A JP2004514785A JP2005533799A5 JP 2005533799 A5 JP2005533799 A5 JP 2005533799A5 JP 2004514785 A JP2004514785 A JP 2004514785A JP 2004514785 A JP2004514785 A JP 2004514785A JP 2005533799 A5 JP2005533799 A5 JP 2005533799A5
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- JP
- Japan
- Prior art keywords
- ylmethyl
- azoniabicyclo
- optionally substituted
- group
- compound
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 51
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 208000023504 respiratory system disease Diseases 0.000 claims description 6
- 208000014001 urinary system disease Diseases 0.000 claims description 6
- 230000008485 antagonism Effects 0.000 claims description 5
- 230000000241 respiratory effect Effects 0.000 claims description 5
- 230000002485 urinary effect Effects 0.000 claims description 5
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 4
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 4
- 230000001668 ameliorated effect Effects 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 102000007202 Muscarinic M3 Receptor Human genes 0.000 claims description 3
- 108010008405 Muscarinic M3 Receptor Proteins 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 2
- -1 furan-2-ylmethyl Chemical group 0.000 claims 84
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000004122 cyclic group Chemical group 0.000 claims 13
- PEITVFVWIKGNCJ-FERBBOLQSA-N [(3R)-1-azabicyclo[2.2.2]octan-3-yl] N-[(4-bromo-5-methylthiophen-2-yl)methyl]-N-[(3-methylthiophen-2-yl)methyl]carbamate (4,5-dimethylfuran-2-yl)methyl-[(5-methylfuran-2-yl)methyl]carbamic acid Chemical compound CC=1C=C(OC1C)CN(C(O)=O)CC=1OC(=CC1)C.N12C[C@@H](C(CC1)CC2)OC(N(CC=2SC=CC2C)CC=2SC(=C(C2)Br)C)=O PEITVFVWIKGNCJ-FERBBOLQSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 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 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 208000010643 digestive system disease Diseases 0.000 claims 3
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 230000001575 pathological effect Effects 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 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 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- UWFYPZAJXOAIHQ-UHFFFAOYSA-N (5-ethylthiophen-2-yl)methyl-[(3-methylthiophen-2-yl)methyl]carbamic acid Chemical compound S1C(CC)=CC=C1CN(C(O)=O)CC1=C(C)C=CS1 UWFYPZAJXOAIHQ-UHFFFAOYSA-N 0.000 claims 1
- CRDNCFIFWUFJEI-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n,n-diphenylcarbamate;1-azabicyclo[2.2.2]octan-3-yl n-ethyl-n-phenylcarbamate Chemical compound C1N(CC2)CCC2C1OC(=O)N(CC)C1=CC=CC=C1.C1N(CC2)CCC2C1OC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 CRDNCFIFWUFJEI-UHFFFAOYSA-N 0.000 claims 1
- LYHPZBKXSHVBDW-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane;hydroiodide Chemical compound [I-].C1CC2CC[NH+]1CC2 LYHPZBKXSHVBDW-UHFFFAOYSA-N 0.000 claims 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- TVSLNRQODQRVJZ-UHFFFAOYSA-N 2-(3,4,5-trifluorophenyl)acetonitrile Chemical group FC1=CC(CC#N)=CC(F)=C1F TVSLNRQODQRVJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 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 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- SJJRRCRUTRRCPJ-IGEPXSOLSA-N O([C@@H]1C2CCN(CC2)C1)C(=O)N(CCCC)C1=CC(F)=CC=C1F.C1=CSC(CN(CCC=2C=CC(F)=CC=2)C(=O)O[C@@H]2C3CCN(CC3)C2)=C1C Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)N(CCCC)C1=CC(F)=CC=C1F.C1=CSC(CN(CCC=2C=CC(F)=CC=2)C(=O)O[C@@H]2C3CCN(CC3)C2)=C1C SJJRRCRUTRRCPJ-IGEPXSOLSA-N 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- UTYGHIGCVWXKLZ-FYZYNONXSA-N [(3R)-1-azabicyclo[2.2.2]octan-3-yl] N-(4-fluoro-2-methylphenyl)-N-[(3-methylthiophen-2-yl)methyl]carbamate (3-fluoro-4-methoxyphenyl)-(thiophen-3-ylmethyl)carbamic acid Chemical compound C1=C(F)C(OC)=CC=C1N(C(O)=O)CC1=CSC=C1.C1=CSC(CN(C(=O)O[C@@H]2C3CCN(CC3)C2)C=2C(=CC(F)=CC=2)C)=C1C UTYGHIGCVWXKLZ-FYZYNONXSA-N 0.000 claims 1
- TZSALUUQCIDZIQ-BQAIUKQQSA-N [(3R)-1-azabicyclo[2.2.2]octan-3-yl] N-[2-(3,4-dimethoxyphenyl)ethyl]-N-[(5-methylfuran-2-yl)methyl]carbamate (5-bromothiophen-2-yl)methyl-(2,4,5-trifluorophenyl)carbamic acid Chemical compound C=1C(F)=C(F)C=C(F)C=1N(C(=O)O)CC1=CC=C(Br)S1.C1=C(OC)C(OC)=CC=C1CCN(C(=O)O[C@@H]1C2CCN(CC2)C1)CC1=CC=C(C)O1 TZSALUUQCIDZIQ-BQAIUKQQSA-N 0.000 claims 1
- CAKRLTNLKHYGIV-DFXIHDQSSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-fluorophenyl)-n-[(3,4,5-trifluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].FC1=CC=CC(N(CC=2C=C(F)C(F)=C(F)C=2)C(=O)O[C@@H]2C3CC[N+](CC3)(CCOC=3C=CC=CC=3)C2)=C1 CAKRLTNLKHYGIV-DFXIHDQSSA-M 0.000 claims 1
- QBNZACLTBQTGJP-VRCWUQCGSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-fluorophenyl)-n-[(3-fluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].FC1=CC=CC(CN(C(=O)O[C@@H]2C3CC[N+](CC3)(CCOC=3C=CC=CC=3)C2)C=2C=C(F)C=CC=2)=C1 QBNZACLTBQTGJP-VRCWUQCGSA-M 0.000 claims 1
- QNJLKXCSRKQDKU-JQXPCOHGSA-M [(3r)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-methylphenyl)-n-[(2,4,5-trifluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].CC1=CC=CC(N(CC=2C(=CC(F)=C(F)C=2)F)C(=O)O[C@@H]2C3CC[N+](CC3)(CCOC=3C=CC=CC=3)C2)=C1 QNJLKXCSRKQDKU-JQXPCOHGSA-M 0.000 claims 1
- IJROGYSFHCIWAC-PVQGFKEISA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-fluorophenyl)-n-[(3,4,5-trifluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].FC1=CC=CC(N(CC=2C=C(F)C(F)=C(F)C=2)C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)=C1 IJROGYSFHCIWAC-PVQGFKEISA-M 0.000 claims 1
- FZXAKJUEACVCHO-OCCBKRFISA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-fluorophenyl)-n-[(3-fluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].FC1=CC=CC(CN(C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)C=2C=C(F)C=CC=2)=C1 FZXAKJUEACVCHO-OCCBKRFISA-M 0.000 claims 1
- QKWOYWROMVNAEX-QKIIOBKNSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-(3-methylphenyl)-n-[(2,4,5-trifluorophenyl)methyl]carbamate;bromide Chemical compound [Br-].CC1=CC=CC(N(CC=2C(=CC(F)=C(F)C=2)F)C(=O)O[C@@H]2C3CC[N+](CC3)(CCCC=3C=CC=CC=3)C2)=C1 QKWOYWROMVNAEX-QKIIOBKNSA-M 0.000 claims 1
- WAWYUYIDNWSAPS-PNYZXNCNSA-M [(3r)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octan-3-yl] n-[(5-ethylthiophen-2-yl)methyl]-n-[(3-methylthiophen-2-yl)methyl]carbamate;bromide Chemical compound [Br-].S1C(CC)=CC=C1CN(C(=O)O[C@@H]1C2CC[N+](CC2)(CCCC=2C=CC=CC=2)C1)CC1=C(C)C=CS1 WAWYUYIDNWSAPS-PNYZXNCNSA-M 0.000 claims 1
- WIFYAJXTBJHEAS-NSTLWARWSA-N [(3r)-1-[3-(3-hydroxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-3-yl] n-[(4,5-dimethylfuran-2-yl)methyl]-n-[(5-methylfuran-2-yl)methyl]carbamate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O1C(C)=CC=C1CN(C(=O)O[C@@H]1C2CC[N+](CC2)(CCCOC=2C=C(O)C=CC=2)C1)CC1=CC(C)=C(C)O1 WIFYAJXTBJHEAS-NSTLWARWSA-N 0.000 claims 1
- WWXBHTZSYYGCSG-UHFFFAOYSA-N [4-(carbamoylamino)phenyl]arsonic acid Chemical compound NC(=O)NC1=CC=C([As](O)(O)=O)C=C1 WWXBHTZSYYGCSG-UHFFFAOYSA-N 0.000 claims 1
- DXNQLZJOTVNBOZ-UHFFFAOYSA-N [O]C(=O)Nc1ccccc1 Chemical group [O]C(=O)Nc1ccccc1 DXNQLZJOTVNBOZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 239000000043 antiallergic agent Substances 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 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 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RWOANIBIINMNEZ-SUVRUAAESA-M ethyl 5-[(3r)-3-[2-(3,4-dimethoxyphenyl)ethyl-[(5-methylfuran-2-yl)methyl]carbamoyl]oxy-1-azoniabicyclo[2.2.2]octan-1-yl]pentanoate;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.O([C@@H]1C2CC[N+](CC2)(C1)CCCCC(=O)OCC)C(=O)N(CC=1OC(C)=CC=1)CCC1=CC=C(OC)C(OC)=C1 RWOANIBIINMNEZ-SUVRUAAESA-M 0.000 claims 1
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims 1
- BDDIUTHMWNWMRJ-UHFFFAOYSA-N octane;hydrobromide Chemical compound Br.CCCCCCCC BDDIUTHMWNWMRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 5
- 206010036018 Pollakiuria Diseases 0.000 description 4
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 3
- 206010048994 Bladder spasm Diseases 0.000 description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- 206010063057 Cystitis noninfective Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 description 3
- 206010029279 Neurogenic bladder Diseases 0.000 description 3
- 206010046543 Urinary incontinence Diseases 0.000 description 3
- 206010006451 bronchitis Diseases 0.000 description 3
- 201000003139 chronic cystitis Diseases 0.000 description 3
- 206010009887 colitis Diseases 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 208000007784 diverticulitis Diseases 0.000 description 3
- 208000002551 irritable bowel syndrome Diseases 0.000 description 3
- 206010039083 rhinitis Diseases 0.000 description 3
- 230000001148 spastic effect Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 210000003932 urinary bladder Anatomy 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010066091 Bronchial Hyperreactivity Diseases 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 208000008967 Enuresis Diseases 0.000 description 2
- 206010020853 Hypertonic bladder Diseases 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- 206010040741 Sinus bradycardia Diseases 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 230000036427 bronchial hyperreactivity Effects 0.000 description 2
- 239000007941 film coated tablet Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 208000005346 nocturnal enuresis Diseases 0.000 description 2
- 208000022934 urinary frequency Diseases 0.000 description 2
- 230000036318 urination frequency Effects 0.000 description 2
- 210000001186 vagus nerve Anatomy 0.000 description 2
- NLAVHUUABUFSIG-UHFFFAOYSA-N 3,4,5-trifluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1F NLAVHUUABUFSIG-UHFFFAOYSA-N 0.000 description 1
- SMJWCIJUYKXZHU-UHFFFAOYSA-N 3-fluoro-n-[(3,4,5-trifluorophenyl)methyl]aniline Chemical compound FC1=CC=CC(NCC=2C=C(F)C(F)=C(F)C=2)=C1 SMJWCIJUYKXZHU-UHFFFAOYSA-N 0.000 description 1
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| PCT/EP2003/006472 WO2004000840A2 (en) | 2002-06-21 | 2003-06-18 | Quinuclidine derivatives and pharmaceutical compositions containing the same |
Publications (2)
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| JP2005533799A JP2005533799A (ja) | 2005-11-10 |
| JP2005533799A5 true JP2005533799A5 (https=) | 2006-07-06 |
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| JP4445704B2 (ja) | 2000-12-22 | 2010-04-07 | アルミラル・ソシエダッド・アノニマ | キヌクリジンカルバメート誘導体およびｍ３アンダゴニストとしてのそれらの使用 |
| 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. |
| US7056916B2 (en) | 2002-11-15 | 2006-06-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Medicaments for the treatment of chronic obstructive pulmonary disease |
| AU2005235419B2 (en) * | 2004-04-22 | 2010-11-04 | Boehringer Ingelheim International Gmbh | Pharmaceutical combinations containing benzoxazine for treating respiratory diseases |
| JP2008505118A (ja) * | 2004-06-30 | 2008-02-21 | グラクソ グループ リミテッド | ムスカリン性アセチルコリン受容体アンタゴニスト |
| ES2246170B1 (es) * | 2004-07-29 | 2007-04-01 | Almirall Prodesfarma, S.A. | Nuevo procedimiento para preparar derivados de carbamato de quinuclidinio. |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
| CN101208316B (zh) | 2005-08-15 | 2012-05-09 | 贝林格尔·英格海姆国际有限公司 | 制备β-模拟物的方法 |
| DE102006028286A1 (de) * | 2006-06-20 | 2007-12-27 | Wirsich, Konrad, Dipl.-Ing. (FH) | Drehmoment- und rutschfest verbundene aus zwei Teilen bestehende Schaltzahnräder |
| EP1882691A1 (en) * | 2006-07-26 | 2008-01-30 | CHIESI FARMACEUTICI S.p.A. | Quinuclidine derivatives as M3 antagonists |
| KR20090107567A (ko) * | 2007-02-09 | 2009-10-13 | 아스텔라스세이야쿠 가부시키가이샤 | 아자 가교환 화합물 |
| ES2554646T3 (es) * | 2007-02-23 | 2015-12-22 | Theravance Biopharma R&D Ip, Llc | Compuestos de difenilmetilo de amonio cuaternario, de utilidad como antagonistas de receptores muscarínicos |
| EP2065385A1 (en) | 2007-11-28 | 2009-06-03 | Laboratorios SALVAT, S.A. | Stable crystalline salt of (R)-3-fluorophenyl-3,4,5-trifluorobenzylcarbamic acid 1-azabiciyclo [2.2.2]oct-3-yl ester |
| EP2080507A1 (en) * | 2008-01-15 | 2009-07-22 | CHIESI FARMACEUTICI S.p.A. | Pharmaceutical formulations comprising an anticholinergic drug |
| US8742131B2 (en) * | 2010-01-28 | 2014-06-03 | Theron Pharmaceuticals, Inc. | 7-azoniabicyclo [2.2.1] heptane derivatives, methods of production, and pharmaceutical uses thereof |
| AU2012231275A1 (en) * | 2011-03-18 | 2013-10-17 | Genzyme Corporation | Glucosylceramide synthase inhibitors |
| EP2631674A1 (de) * | 2012-02-23 | 2013-08-28 | ELMOS Semiconductor AG | Verfahren und Sensorsystem zur Vermessung der Eigenschaften einer Übertragungsstrecke eines Messsystems zwischen Sender und Empfänger |
| MA37975B2 (fr) | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| EP3023424B1 (en) * | 2013-07-13 | 2019-02-27 | Beijing Shuobai Pharmaceutical Co., Ltd. | Quinine compounds, and optical isomers, preparation method and medical use thereof |
| US10570127B1 (en) | 2018-11-05 | 2020-02-25 | Renexxion, Llc | Material and methods for the treatment of gastro-intestinal disorders |
| CN114040762A (zh) | 2019-02-04 | 2022-02-11 | 建新公司 | 使用葡糖神经酰胺合酶(gcs)的抑制剂治疗纤毛疾病 |
| TW202142236A (zh) | 2020-02-03 | 2021-11-16 | 美商健臻公司 | 用於治療與溶體儲積症相關的神經症狀之方法 |
| US12527775B2 (en) | 2020-03-26 | 2026-01-20 | Shionogi & Co., Ltd. | Heteroaromatic derivatives having serotonin receptor binding activity |
| KR20230043024A (ko) | 2020-07-24 | 2023-03-30 | 젠자임 코포레이션 | 벤글루스타트를 포함하는 제약 조성물 |
| JP7741820B2 (ja) * | 2020-12-28 | 2025-09-18 | 塩野義製薬株式会社 | セロトニン受容体結合活性を有する環状アミン誘導体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US2762796A (en) | 1956-09-11 | Iminodibenzyl derivative | ||
| GB1219606A (en) | 1968-07-15 | 1971-01-20 | Rech S Et D Applic Scient Soge | Quinuclidinol derivatives and preparation thereof |
| GB1246606A (en) | 1969-04-28 | 1971-09-15 | Starogardzkie Zakl Farma | Dibenzo-azepine derivatives |
| GB8825505D0 (en) * | 1988-11-01 | 1988-12-07 | Pfizer Ltd | Therapeutic agents |
| GB8923590D0 (en) | 1989-10-19 | 1989-12-06 | Pfizer Ltd | Antimuscarinic bronchodilators |
| GB9201751D0 (en) | 1992-01-28 | 1992-03-11 | Smithkline Beecham Plc | Compounds |
| GB9202443D0 (en) | 1992-02-05 | 1992-03-18 | Fujisawa Pharmaceutical Co | A novel substituted-acetamide compound and a process for the preparation thereof |
| WO1995006635A1 (en) * | 1993-09-02 | 1995-03-09 | Yamanouchi Pharmaceutical Co., Ltd. | Carbamate derivative and medicine containing the same |
| WO1995021820A1 (en) * | 1994-02-10 | 1995-08-17 | Yamanouchi Pharmaceutical Co., Ltd. | Novel carbamate derivative and medicinal composition containing the same |
| NO2005012I1 (no) * | 1994-12-28 | 2005-06-06 | Debio Rech Pharma Sa | Triptorelin og farmasoytisk akseptable salter derav |
| ATE205490T1 (de) | 1995-10-13 | 2001-09-15 | Banyu Pharma Co Ltd | Substituierte heteroaromatische derivate |
| AUPN862996A0 (en) | 1996-03-13 | 1996-04-04 | Fujisawa Pharmaceutical Co., Ltd. | A novel substituted-acetamide compound |
| PE92198A1 (es) | 1996-08-01 | 1999-01-09 | Banyu Pharma Co Ltd | Derivados de 1,4-piperidina disustituida que contienen fluor |
| ES2165768B1 (es) * | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| CZ294251B6 (cs) | 2000-06-27 | 2004-11-10 | Laboratorios S. A. L. V. A. T., S. A. | Karbamáty a jejich použití pro výrobu farmaceutického prostředku |
| JP4445704B2 (ja) | 2000-12-22 | 2010-04-07 | アルミラル・ソシエダッド・アノニマ | キヌクリジンカルバメート誘導体およびｍ３アンダゴニストとしてのそれらの使用 |
| IL156558A0 (en) | 2000-12-28 | 2004-01-04 | Almirall Prodesfarma Ag | Novel quinuclidine derivatives and medicinal compositions containing the same |
| EP1461336B1 (en) | 2001-12-20 | 2013-05-22 | CHIESI FARMACEUTICI S.p.A. | 1-alkyl-1-azoniabicyclo (2.2.2) octane carbamate derivatives and their use as muscarinic receptor antagonists |
| 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. |
-
2002
- 2002-06-21 ES ES200201439A patent/ES2203327B1/es not_active Expired - Fee Related
-
2003
- 2003-06-16 UY UY27850A patent/UY27850A1/es not_active Application Discontinuation
- 2003-06-18 WO PCT/EP2003/006472 patent/WO2004000840A2/en not_active Ceased
- 2003-06-18 RU RU2005101409/04A patent/RU2321588C2/ru not_active IP Right Cessation
- 2003-06-18 US US10/518,496 patent/US7435742B2/en not_active Expired - Fee Related
- 2003-06-18 MX MXPA04012272A patent/MXPA04012272A/es not_active Application Discontinuation
- 2003-06-18 UA UAA200500504A patent/UA85541C2/ru unknown
- 2003-06-18 AU AU2003279384A patent/AU2003279384A1/en not_active Abandoned
- 2003-06-18 CA CA002490082A patent/CA2490082A1/en not_active Abandoned
- 2003-06-18 JP JP2004514785A patent/JP2005533799A/ja active Pending
- 2003-06-18 PE PE2003000615A patent/PE20040579A1/es not_active Application Discontinuation
- 2003-06-18 BR BR0312169-0A patent/BR0312169A/pt not_active IP Right Cessation
- 2003-06-18 NZ NZ537252A patent/NZ537252A/en unknown
- 2003-06-18 CN CNB038193272A patent/CN100363363C/zh not_active Expired - Fee Related
- 2003-06-18 EP EP03740284A patent/EP1515968A2/en not_active Withdrawn
- 2003-06-19 AR ARP030102175A patent/AR040275A1/es unknown
- 2003-06-20 TW TW092116832A patent/TW200401776A/zh unknown
-
2004
- 2004-12-10 EC EC2004005484A patent/ECSP045484A/es unknown
- 2004-12-15 IL IL16577504A patent/IL165775A0/xx unknown
- 2004-12-17 ZA ZA200410211A patent/ZA200410211B/xx unknown
-
2005
- 2005-01-13 NO NO20050217A patent/NO20050217L/no not_active Application Discontinuation
-
2008
- 2008-09-05 US US12/205,315 patent/US20090005412A1/en not_active Abandoned
- 2008-09-05 US US12/205,334 patent/US20090054480A1/en not_active Abandoned
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