DK2570128T3 - Antagonists to muskarinerg acetylcholine. - Google Patents
Antagonists to muskarinerg acetylcholine. Download PDFInfo
- Publication number
- DK2570128T3 DK2570128T3 DK12170402.7T DK12170402T DK2570128T3 DK 2570128 T3 DK2570128 T3 DK 2570128T3 DK 12170402 T DK12170402 T DK 12170402T DK 2570128 T3 DK2570128 T3 DK 2570128T3
- Authority
- DK
- Denmark
- Prior art keywords
- methyl
- hydroxy
- azoniabicyclo
- octane bromide
- oxy
- Prior art date
Links
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 title claims description 10
- 229960004373 acetylcholine Drugs 0.000 title claims description 9
- 239000005557 antagonist Substances 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 93
- -1 2 - {[(3-fluorophenyl) methyl] oxy} ethyl Chemical group 0.000 claims description 48
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 46
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 44
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 22
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000004305 biphenyl Substances 0.000 claims description 14
- 235000010290 biphenyl Nutrition 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 102000005962 receptors Human genes 0.000 claims description 7
- 108020003175 receptors Proteins 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 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 description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 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 description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- BIJYAIPLEKXBGU-UHFFFAOYSA-N 2-[3-[4-[hydroxy(diphenyl)methyl]-1-azoniabicyclo[2.2.2]octan-1-yl]propoxy]phenol;bromide Chemical compound [Br-].OC1=CC=CC=C1OCCC[N+]1(CC2)CCC2(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 BIJYAIPLEKXBGU-UHFFFAOYSA-N 0.000 claims description 2
- 206010061876 Obstruction Diseases 0.000 claims description 2
- GXSUPSQXDPKCBP-UHFFFAOYSA-M [1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 GXSUPSQXDPKCBP-UHFFFAOYSA-M 0.000 claims description 2
- DHRPQUDMYBRWKJ-UHFFFAOYSA-M [1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]-dithiophen-2-ylmethanol;bromide Chemical compound [Br-].C=1C=CSC=1C(C12CC[N+](CCOC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CS1 DHRPQUDMYBRWKJ-UHFFFAOYSA-M 0.000 claims description 2
- RCJDDQUDTGKEGA-UHFFFAOYSA-M [1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-4-yl]-di(thiophen-3-yl)methanol;bromide Chemical compound [Br-].C1=CSC=C1C(C12CC[N+](CCCOC=3C=CC=CC=3)(CC1)CC2)(O)C=1C=CSC=1 RCJDDQUDTGKEGA-UHFFFAOYSA-M 0.000 claims description 2
- MVYUVZORWYSLPK-UHFFFAOYSA-M [1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 MVYUVZORWYSLPK-UHFFFAOYSA-M 0.000 claims description 2
- AZFBLKOSLDSFLF-UHFFFAOYSA-M [1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-4-yl]-dithiophen-2-ylmethanol;bromide Chemical compound [Br-].C=1C=CSC=1C(C12CC[N+](CCCOC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CS1 AZFBLKOSLDSFLF-UHFFFAOYSA-M 0.000 claims description 2
- 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 description 2
- NBNRDFMHLAKVME-UHFFFAOYSA-M [1-[3-(2-fluorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C(=CC=CC=3)F)(CC1)CC2)(O)C1=CC=CC=C1 NBNRDFMHLAKVME-UHFFFAOYSA-M 0.000 claims description 2
- OKBSOVWMXJPOJU-UHFFFAOYSA-M [1-[3-(2-methylphenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].CC1=CC=CC=C1OCCC[N+]1(CC2)CCC2(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 OKBSOVWMXJPOJU-UHFFFAOYSA-M 0.000 claims description 2
- XIDWOLDYKKJTMX-UHFFFAOYSA-M [1-[3-(3-nitrophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=C(C=CC=3)[N+]([O-])=O)(CC1)CC2)(O)C1=CC=CC=C1 XIDWOLDYKKJTMX-UHFFFAOYSA-M 0.000 claims description 2
- ZMIFYLXDBQOKGF-UHFFFAOYSA-M [1-[3-(4-fluorophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=CC(F)=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 ZMIFYLXDBQOKGF-UHFFFAOYSA-M 0.000 claims description 2
- XQVCZCXPHZGYBQ-UHFFFAOYSA-M [1-[3-(4-nitrophenoxy)propyl]-1-azoniabicyclo[2.2.2]octan-4-yl]-diphenylmethanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOC=3C=CC(=CC=3)[N+]([O-])=O)(CC1)CC2)(O)C1=CC=CC=C1 XQVCZCXPHZGYBQ-UHFFFAOYSA-M 0.000 claims description 2
- FTFQOHPIVJFSFN-UHFFFAOYSA-M bis(3-fluorophenyl)-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=CC(F)=CC=1C(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC(F)=C1 FTFQOHPIVJFSFN-UHFFFAOYSA-M 0.000 claims description 2
- LHOPKDSVDNZVFB-UHFFFAOYSA-M bis(4-fluorophenyl)-[1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=C(F)C=CC=1C(C12CC[N+](CCCOC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=C(F)C=C1 LHOPKDSVDNZVFB-UHFFFAOYSA-M 0.000 claims description 2
- CFXRBEDIYVRMIQ-UHFFFAOYSA-M bis(4-methylphenyl)-[1-(2-phenylmethoxyethyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide Chemical compound [Br-].C1=CC(C)=CC=C1C(O)(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)CC2)C1=CC=C(C)C=C1 CFXRBEDIYVRMIQ-UHFFFAOYSA-M 0.000 claims description 2
- KEMWNQKRGGOVDG-UHFFFAOYSA-M diphenyl-[1-(3-phenylmethoxypropyl)-1-azoniabicyclo[2.2.2]octan-4-yl]methanol;bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCCOCC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 KEMWNQKRGGOVDG-UHFFFAOYSA-M 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
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- 125000006267 biphenyl group Chemical group 0.000 claims 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 3
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- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
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- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 150000008584 quinuclidines Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 238000003653 radioligand binding assay Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940046810 spiriva Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012385 systemic delivery Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000006068 taste-masking agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 230000007384 vagal nerve stimulation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 238000005406 washing Methods 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| 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 |
| EP05746609A EP1740177B1 (en) | 2004-04-27 | 2005-04-27 | Muscarinic acetylcholine receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2570128T3 true DK2570128T3 (en) | 2016-11-07 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK12170402.7T DK2570128T3 (en) | 2004-04-27 | 2005-04-27 | Antagonists to muskarinerg acetylcholine. |
| DK05746609.6T DK1740177T3 (da) | 2004-04-27 | 2005-04-27 | Antagonister til muskarinfølsomme acetylcholinreceptorer |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK05746609.6T DK1740177T3 (da) | 2004-04-27 | 2005-04-27 | Antagonister til muskarinfølsomme acetylcholinreceptorer |
Country Status (38)
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| TW200519108A (en) * | 2003-07-17 | 2005-06-16 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
| WO2005037224A2 (en) * | 2003-10-17 | 2005-04-28 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists |
| PE20050489A1 (es) * | 2003-11-04 | 2005-09-02 | Glaxo Group Ltd | Antagonistas de receptores de acetilcolina muscarinicos |
| US20090253908A1 (en) * | 2004-03-11 | 2009-10-08 | Glaxo Group Limited | Novel m3 muscarinic acetylchoine receptor antagonists |
| US7384946B2 (en) * | 2004-03-17 | 2008-06-10 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
| WO2005094251A2 (en) * | 2004-03-17 | 2005-10-13 | Glaxo Group Limited | M3muscarinic acetylcholine receptor antagonists |
| US20080194619A1 (en) * | 2004-04-05 | 2008-08-14 | Laurent Lecanu | Anti-Hiv Quinuclidine Compounds |
| MY144753A (en) | 2004-04-27 | 2011-10-31 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
| WO2005112644A2 (en) * | 2004-05-13 | 2005-12-01 | Glaxo Group Limited | Muscarinic acetylcholine receptor antagonists |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
| JP2008520579A (ja) * | 2004-11-15 | 2008-06-19 | グラクソ グループ リミテッド | 新規ｍ３ムスカリン性アセチルコリン受容体アンタゴニスト |
| US20080275079A1 (en) * | 2005-08-02 | 2008-11-06 | Glaxo Group Limited | M3 Muscarinic Acetylcholine Receptor Antagonists |
| JP2009504768A (ja) * | 2005-08-18 | 2009-02-05 | 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 |
| AU2007242851A1 (en) | 2006-04-20 | 2007-11-01 | Glaxo Group Limited | Novel compounds |
| GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| AU2007280214A1 (en) | 2006-08-01 | 2008-02-07 | Glaxo Group Limited | Pyrazolo[3,4-b]pyridine compounds, and their use as PDE4 inhibitors |
| PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
| PE20091553A1 (es) | 2008-02-06 | 2009-10-30 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
| PE20091563A1 (es) | 2008-02-06 | 2009-11-05 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
| AR070562A1 (es) | 2008-02-06 | 2010-04-21 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
| US8765743B2 (en) | 2008-06-05 | 2014-07-01 | Glaxosmithkline Intellectual Property Development Limited | Compounds |
| JP5502858B2 (ja) | 2008-06-05 | 2014-05-28 | グラクソ グループ リミテッド | Ｐｉ３キナーゼの阻害剤として有用な４−カルボキサミドインダゾール誘導体 |
| WO2010094643A1 (en) | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Quinoline derivatives and their uses for rhinitis and urticaria |
| ES2739352T3 (es) | 2009-02-26 | 2020-01-30 | Glaxo Group Ltd | Formulaciones farmacéuticas que comprenden 4-{(1R)-2-[(6-{2-[(2,6-diclorobencil)oxi]etoxi}hexil)amino]-1-hidroxietil}-2-(hidroximetil)fenol |
| WO2010102958A1 (en) | 2009-03-09 | 2010-09-16 | Glaxo Group Limited | 4-oxadiazol-2 -yl- indazoles as inhibitors of p13 kinases |
| JP2012520257A (ja) | 2009-03-10 | 2012-09-06 | グラクソ グループ リミテッド | Ｉｋｋ２阻害剤としてのインドール誘導体 |
| WO2010106016A1 (en) | 2009-03-17 | 2010-09-23 | Glaxo Group Limited | Pyrimidine derivatives used as itk inhibitors |
| JO3025B1 (ar) | 2009-04-30 | 2016-09-05 | Glaxo Group Ltd | الأندازولات المستبدلة بالأوكسازول كمثبطات كيناز pi3 |
| WO2011029896A1 (en) | 2009-09-11 | 2011-03-17 | Glaxo Group Limited | Methods of preparation of muscarinic acetylcholine receptor antagonists |
| GB0921075D0 (en) * | 2009-12-01 | 2010-01-13 | Glaxo Group Ltd | Novel combination of the therapeutic agents |
| EP2507223A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Benzpyrazole derivatives as inhibitors of p13 kinases |
| US20120238571A1 (en) | 2009-12-03 | 2012-09-20 | Glaxo Group Limited | Indazole derivatives as pi 3-kinase |
| WO2011067364A1 (en) | 2009-12-03 | 2011-06-09 | Glaxo Group Limited | Novel compounds |
| CA2788364C (en) * | 2010-01-28 | 2017-10-31 | Theron Pharmaceuticals, Inc. | 7-azoniabicyclo[2.2.1]heptane derivatives, methods of production, and pharmaceutical uses thereof |
| WO2011110575A1 (en) | 2010-03-11 | 2011-09-15 | Glaxo Group Limited | Derivatives of 2-[2-(benzo- or pyrido-) thiazolylamino]-6-aminopyridine, useful in the treatment of respiratoric, allergic or inflammatory diseases |
| JP2013529606A (ja) * | 2010-06-22 | 2013-07-22 | シエシー ファルマセウティチィ ソシエタ ペル アチオニ | 抗ムスカリン薬含有乾燥粉末配合物 |
| PT2614058E (pt) | 2010-09-08 | 2015-10-27 | Glaxosmithkline Ip Dev Ltd | Polimorfos e sais de n-[5-[4-(5-{[(2r,6s)-2,6-dimetil-4- morfolinil]metil}-1,3-oxazol-2-il)-1h-indazol-6-il]-2- (metiloxi)-3-piridinil]metanossulfonamida |
| WO2012035055A1 (en) | 2010-09-17 | 2012-03-22 | Glaxo Group Limited | Novel compounds |
| GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
| EP2717867A1 (en) | 2011-06-08 | 2014-04-16 | Glaxo Group Limited | Dry powder inhaler compositions comprising umeclidinium |
| CA2838030A1 (en) | 2011-06-08 | 2012-12-13 | Glaxo Group Limited | Combination comprising umeclidinium and a corticosteroid |
| CA2869849A1 (en) | 2012-04-13 | 2013-10-17 | Glaxosmithkline Intellectual Property Development Limited | Aggregate particles comprising nanoparticulate drug particles of umeclidinium bromide, vilanterol trifenatate and fluticasone furoate |
| RU2502743C1 (ru) * | 2012-08-03 | 2013-12-27 | Федеральное государственное бюджетное учреждение "Российский кардиологический научно-производственный комплекс" Министерства здравоохранения и социального развития РФ (ФГБУ "РКНПК" Минздравсоцразвития России) | Синтетический антиген, обладающий способностью связывать аутоантитела к мускариновому м2-рецептору |
| KR20150043465A (ko) * | 2012-08-15 | 2015-04-22 | 글락소 그룹 리미티드 | 화학 공정 |
| GB201222679D0 (en) * | 2012-12-17 | 2013-01-30 | Glaxo Group Ltd | Pharmaceutical combination products |
| CA2921621C (en) * | 2013-07-13 | 2018-08-28 | Beijing Fswelcome Technology Development Co., Ltd | Quinine compounds, and optical isomers, preparation method and medical use thereof |
| SG11201600045UA (en) * | 2013-07-30 | 2016-02-26 | Glaxosmithkline Ip Dev Ltd | Topical compositions for treatment of excessive sweating and methods of use thereof |
| US20160263109A1 (en) | 2013-10-17 | 2016-09-15 | Glaxosmithkline Intellectual Property Development Limited | P13k inhibitor for treatment of respiratory disease |
| KR20160062179A (ko) | 2013-10-17 | 2016-06-01 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | 호흡기 질병의 치료를 위한 ｐｉ３ｋ 억제제 |
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| US10987363B2 (en) | 2014-05-28 | 2021-04-27 | Glaxosmithkline Intellectual Property Development Limited | Fluticasone furoate in the treatment of COPD |
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| GB201706102D0 (en) | 2017-04-18 | 2017-05-31 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| IT201700058796A1 (it) * | 2017-05-30 | 2018-11-30 | Olon Spa | Procedimento per la preparazione di un nuovo intermedio di sintesi dell’umeclidinio. |
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| KR102651043B1 (ko) | 2017-10-30 | 2024-03-22 | 다케다 야쿠힌 고교 가부시키가이샤 | 지질-외피보유 바이러스의 불활성화를 위한 환경 친화적 세제 |
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