HRP20161385T1 - Antagonisti muskarinskog acetilkolinskog receptora - Google Patents
Antagonisti muskarinskog acetilkolinskog receptora Download PDFInfo
- Publication number
- HRP20161385T1 HRP20161385T1 HRP20161385TT HRP20161385T HRP20161385T1 HR P20161385 T1 HRP20161385 T1 HR P20161385T1 HR P20161385T T HRP20161385T T HR P20161385TT HR P20161385 T HRP20161385 T HR P20161385T HR P20161385 T1 HRP20161385 T1 HR P20161385T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- hydroxy
- azoniabicyclo
- oxy
- octane bromide
- Prior art date
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- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 title claims 3
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 title claims 3
- 229940121683 Acetylcholine receptor antagonist Drugs 0.000 title 1
- -1 bromide 1-(2-{[(4-chlorophenyl)methyl]oxy}ethyl)-4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octane bromide Chemical compound 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- VLBDNNHJSKOGCJ-UHFFFAOYSA-M [1-[2-[(3-fluorophenyl)methoxy]ethyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=C(F)C=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 VLBDNNHJSKOGCJ-UHFFFAOYSA-M 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- JGZCAKYICCHTOV-UHFFFAOYSA-M bis(3-methylphenyl)-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide Chemical compound [Br-].CC1=CC=CC(C(O)(C=2C=C(C)C=CC=2)C23CC[N+](CCOCC=4C=CC=CC=4)(CC2)CC3)=C1 JGZCAKYICCHTOV-UHFFFAOYSA-M 0.000 claims 2
- POQXKEIISDGWLM-UHFFFAOYSA-M bis(4-fluorophenyl)-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=C(F)C=CC=1C(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=C(F)C=C1 POQXKEIISDGWLM-UHFFFAOYSA-M 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- UYHCLLDIQQNVPF-UHFFFAOYSA-M 2-[4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octan-1-yl]ethyl benzoate;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOC(=O)C=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 UYHCLLDIQQNVPF-UHFFFAOYSA-M 0.000 claims 1
- CMMCMQWMHZZQHV-UHFFFAOYSA-M 4-[3-[4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octan-1-yl]propoxy]benzonitrile;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=CC(=CC=3)C#N)(CC1)CC2)(O)C1=CC=CC=C1 CMMCMQWMHZZQHV-UHFFFAOYSA-M 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 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
- VURJNZIPUIEUGJ-UHFFFAOYSA-L CC1=CC=CC(C(C2(CC3)CC[N+]3(CCCOC3=CC=CC=C3)CC2)(C2=CC(C)=CC=C2)O)=C1.OC(C1(CC2)CC[N+]2(CCOC2=CC=CC=C2)CC1)(C1=CC=CC=C1)C1=CC=CC=C1.[Br-].[Br-].Br Chemical compound CC1=CC=CC(C(C2(CC3)CC[N+]3(CCCOC3=CC=CC=C3)CC2)(C2=CC(C)=CC=C2)O)=C1.OC(C1(CC2)CC[N+]2(CCOC2=CC=CC=C2)CC1)(C1=CC=CC=C1)C1=CC=CC=C1.[Br-].[Br-].Br VURJNZIPUIEUGJ-UHFFFAOYSA-L 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 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
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- COPKCSVWCOELAC-UHFFFAOYSA-M [1-(4-phenoxybutyl)-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCCOC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 COPKCSVWCOELAC-UHFFFAOYSA-M 0.000 claims 1
- NEYGAMRQICXESO-UHFFFAOYSA-M [1-[2-[(4-bromophenyl)methoxy]ethyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=CC(Br)=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 NEYGAMRQICXESO-UHFFFAOYSA-M 0.000 claims 1
- FPAAYJHLZCHQFL-UHFFFAOYSA-M [1-[2-[(4-chlorophenyl)methoxy]ethyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=CC(Cl)=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 FPAAYJHLZCHQFL-UHFFFAOYSA-M 0.000 claims 1
- QYCWFUYPCMJQHQ-UHFFFAOYSA-M [1-[2-[(4-fluorophenyl)methoxy]ethyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=CC(F)=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 QYCWFUYPCMJQHQ-UHFFFAOYSA-M 0.000 claims 1
- COGWXDUNGZOYBW-UHFFFAOYSA-M [1-[2-[(4-tert-butylphenyl)methoxy]ethyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C1=CC(C(C)(C)C)=CC=C1COCC[N+]1(CC2)CCC2(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 COGWXDUNGZOYBW-UHFFFAOYSA-M 0.000 claims 1
- UHPAGLHUFDGWRP-UHFFFAOYSA-M [1-[3-(2-methoxyphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].COC1=CC=CC=C1OCCC[N+]1(CC2)CCC2(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 UHPAGLHUFDGWRP-UHFFFAOYSA-M 0.000 claims 1
- GWWJICWVFUPBOS-UHFFFAOYSA-L [Br-].FC1=C(C=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O.[Br-].OC(C21CC[N+](CC2)(CC1)CCCOC1=CC=C(C=C1)[N+](=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Br-].FC1=C(C=CC=C1)OCCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O.[Br-].OC(C21CC[N+](CC2)(CC1)CCCOC1=CC=C(C=C1)[N+](=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1 GWWJICWVFUPBOS-UHFFFAOYSA-L 0.000 claims 1
- SKSJHAHDMQHSQS-UHFFFAOYSA-L [Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2.[Br-].FC=2C=C(C=CC2)C(C21CC[N+](CC2)(CC1)CCCOC1=CC=CC=C1)(O)C1=CC(=CC=C1)F Chemical compound [Br-].OC(C12CC[N+](CC1)(CC2)CCOC2=CC=CC=C2)(C=2SC=CC2)C=2SC=CC2.[Br-].FC=2C=C(C=CC2)C(C21CC[N+](CC2)(CC1)CCCOC1=CC=CC=C1)(O)C1=CC(=CC=C1)F SKSJHAHDMQHSQS-UHFFFAOYSA-L 0.000 claims 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims 1
- 229960004373 acetylcholine Drugs 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- FQGXKIQQELWWLZ-UHFFFAOYSA-M bis(3-methoxyphenyl)-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide Chemical compound [Br-].COC1=CC=CC(C(O)(C=2C=C(OC)C=CC=2)C23CC[N+](CCOCC=4C=CC=CC=4)(CC2)CC3)=C1 FQGXKIQQELWWLZ-UHFFFAOYSA-M 0.000 claims 1
- GYBJLQNXDYKARM-UHFFFAOYSA-M bis(4-methoxyphenyl)-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide Chemical compound [Br-].C1=CC(OC)=CC=C1C(O)(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)CC2)C1=CC=C(OC)C=C1 GYBJLQNXDYKARM-UHFFFAOYSA-M 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-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
- 229940071648 metered dose inhaler Drugs 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/452—Piperidinium derivatives
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
Claims (10)
1. Spoj formule (I), kao što je prikazano niže:
[image]
,
naznačen time što
R1 je
[image]
;
R2 i R3 se neovisno bira iz skupine koju čine:
[image]
F, G, H, K i L se neovisno bira iz skupine koju čine vodik, halogen, C1-4 alkil, halogenom supstituirani C1-4 alkil, hidroksi supstituirani C1-4 alkil i C1-4 alkoksi;
R4 i R5 se neovisno bira iz skupine koju čine vodik, halogen, C1-4 alkil, aril, C1-4 alkil aril, cijano, nitro, (CR7R7)pORb, (CR7R7)pNRbRb, ili R4 i R5 zajedno mogu tvoriti 5 do 6-eročlani zasićeni ili nezasićeni prsten;
m je cijeli broj s vrijednošću od 1 do 5;
p je 0, 1 ili 2;
t je 0, 1 ili 2;
R6 se bira iz skupine koju čine vodik i C1-4 alkil;
Rb se bira iz skupine koju čine vodik, C1-4 alkil i aril C1-4 alkil;
R7 se bira iz skupine koju čine vodik i C1-4 alkil;
X- je fiziološki prihvatljiv anion kojeg se bira iz skupine koju čine klorid, bromid, jodid, hidroksid, sulfat, nitrat, fosfat, acetat, trifluoracetat, fumarat, citrat, tartarat, oksalat, sukcinat, mandelat, metansulfonat i p-toluensulfonat.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine:
1-(2-{[(3-fluorfenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-(2-{[[(4-bromfenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-(2-{[(4-klorfenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[bis(4-fluorfenil)(hidroksi)metil]-1-{2-[(fenilmetil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-{hidroksi[bis(3-metilfenil)]metil}-1-{2-[(fenilmetil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
1-(2-{[(4-fluorfenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-{3-[(3-fluorfenil)oksi]propil}-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-{hidroksi[bis(4-metilfenil)]metil}-1-{2-[(fenilmetil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-[bis(3-fluorfenil)(hidroksi)metil]-1-{2-[(fenilmetil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
1-{3-[(3-klorfenil)oksi]propil}-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(di-2-tienil)metil]-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-(2-{[(4-cijanofenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-{3-[(4-bromfenil)oksi]propil}-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[bis(4-fluorfenil)(hidroksi)metil]-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-{3-[(4-fluorfenil)oksi]propil}-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-{2-[(1-metil-1-feniletil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(di-3-tienil)metil]-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-[2-(feniloksi)etil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-{hidroksi[bis(3-metilfenil)]metil}-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-{hidroksi[bis(4-metilfenil)]metil}-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-(3-{[4-(metiloksi)fenil]oksi}propil)-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-[2-({[3-(metiloksi)fenil]metil}oksi)etil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[bis(3-fluorfenil)(hidroksi)metil]-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(di-2-tienil)metil]-1-[2-(feniloksi)etil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-(hidroksi{bis[3-(metiloksi)fenil]}metil)-1-{2-[(fenilmetil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-{3-[(4-nitrofenil)oksi]propil}-1-azoniabiciklo[2.2.2]oktan-bromid
1-{3-[(2-fluorfenil)oksi]propil}-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-{3-[(3-nitrofenil)oksi]propil}-1-azoniabiciklo[2.2.2]oktan-bromid
1-[3-(4-bifenililoksi)propil]-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-{3-[(2-metilfenil)oksi]propil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-{3-[(fenilmetil)oksi]propil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-[4-(feniloksi)butil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-{3-[(2-hidroksifenil)oksi]propil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(di-3-tienil)metil]-1-[2-(feniloksi)etil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-(hidroksi{bis[4-(metiloksi)fenil]}metil)-1-{2-[(fenilmetil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
1-{3-[(4-cijanofenil)oksi]propil}-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-[2-({[4-(1,1-dimetiletil)fenil]metil}oksi)etil]-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-(hidroksi{bis[[4-(metiloksi)fenil]}metil)-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-{3-[(2-bromfenil)oksi]propil}-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-{4-[(fenilmetil)oksi]butil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-(hidroksi{bis[3-(metiloksi)fenil]}metil)-1-[3-(feniloksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-(3-{[3-(dietilamino)fenil]oksi}propil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-{2-[(2,4-dibromfenil)oksi]etil}-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[hidroksi(difenil)metil]-1-[3-({2-[(fenilmetil)oksi]fenil}oksi)propil]-1-azoniabiciklo[2.2.2]oktan-bromid, i
4-[hidroksi(difenil)metil]-1-(3-{[2-(metiloksi)fenil]oksi}propil)-1-azoniabiciklo[2.2.2]oktan-bromid.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine:
1-(2-{[(3-fluorfenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-(2-{[(4-bromfenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
1-(2-{[(4-klorfenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid
4-[bis(4-fluorfenil)(hidroksi)metil]-1-{2-[(fenilmetil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
4-{hidroksi[bis(3-metilfenil)]metil}-1-{2-[(fenilmetil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid
1-(2-{[(4-fluorfenil)metil]oksi}etil)-4-[hidroksi(difenil)metil]-1-azoniabiciklo[2.2.2]oktan-bromid; i
4-[hidroksi(difenil)metil]-1-{2-[(fenilcarbonil)oksi]etil}-1-azoniabiciklo[2.2.2]oktan-bromid.
4. Farmaceutski pripravak namijenjen liječenju bolesti posredovanih muskarinskim acetilkolinskim receptorm, naznačen time što sadrži spoj u skladu s patentnim zahtjevom 1, ili njegovu farmaceutski prihvatljivu sol, kao i farmaceutski prihvatljivu podlogu.
5. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 3, ili njegova farmaceutski prihvatljiva sol, namijenjen upotrebi u liječenju bolesti posredovane muskarinskim acetilkolinskim receptorm, naznačen time što se acetilkolin veže na navedeni receptor.
6. Spoj, ili njegova farmaceutski prihvatljiva sol, namijenjen upotrebi u skladu s patentnim zahtjevom 5, naznačen time što se bolest bira iz skupine koju čine kronična opstruktivna plućna bolest, kronični bronhitis, astma, kronična opstrukcija dišnih puteva, plućna fibroza, plućni emfizem i alergijski rinitis.
7. Spoj, ili njegova farmaceutski prihvatljiva sol, namijenjen upotrebi u skladu s patentnim zahtjevom 6, naznačen time što je bolest kronična opstruktivna plućna bolest.
8. Spoj, ili njegova farmaceutski prihvatljiva sol, namijenjen upotrebi u skladu s patentnim zahtjevom 6, naznačen time što je bolest astma.
9. Spoj, ili njegova farmaceutski prihvatljiva sol, namijenjen upotrebi u skladu s patentnim zahtjevom 5, naznačen time što se primjena provodi inhaliranjem na usta ili nos.
10. Spoj, ili njegova farmaceutski prihvatljiva sol, namijenjen upotrebi u skladu s patentnim zahtjevom 5, naznačen time što se primjena provodi putem dozatora za medikament koji se bira između inhalatora sa spremnikom suhog praha, višedoznog inhalatora sa suhim prahom ili inhalatora za odmjerene doze.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56562304P | 2004-04-27 | 2004-04-27 | |
| PCT/US2005/014386 WO2005104745A2 (en) | 2004-04-27 | 2005-04-27 | Muscarinic acetylcholine receptor antagonists |
| EP12170402.7A EP2570128B1 (en) | 2004-04-27 | 2005-04-27 | Muscarinic acetylcholine receptor antagonists |
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| HRP20120832TT HRP20120832T1 (hr) | 2004-04-27 | 2012-10-15 | Antagonisti muskarinskih acetilkolinskih receptora |
| HRP20161385TT HRP20161385T1 (hr) | 2004-04-27 | 2016-10-25 | Antagonisti muskarinskog acetilkolinskog receptora |
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