ES2392848T4 - Antagonistas de los receptores muscarínicos de la acetilcolina - Google Patents
Antagonistas de los receptores muscarínicos de la acetilcolina Download PDFInfo
- Publication number
- ES2392848T4 ES2392848T4 ES05746609.6T ES05746609T ES2392848T4 ES 2392848 T4 ES2392848 T4 ES 2392848T4 ES 05746609 T ES05746609 T ES 05746609T ES 2392848 T4 ES2392848 T4 ES 2392848T4
- Authority
- ES
- Spain
- Prior art keywords
- compound
- alkyl
- group
- machr
- ethyl
- 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.)
- Expired - Lifetime
Links
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 title claims description 37
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 title claims description 37
- 229940121683 Acetylcholine receptor antagonist Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000003814 drug Substances 0.000 claims description 29
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229960004373 acetylcholine Drugs 0.000 claims description 7
- 229940112141 dry powder inhaler Drugs 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 102000005962 receptors Human genes 0.000 claims description 6
- 108020003175 receptors Proteins 0.000 claims description 6
- PEJHHXHHNGORMP-UHFFFAOYSA-M Umeclidinium bromide Chemical compound [Br-].C=1C=CC=CC=1C(C12CC[N+](CCOCC=3C=CC=CC=3)(CC1)CC2)(O)C1=CC=CC=C1 PEJHHXHHNGORMP-UHFFFAOYSA-M 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 206010061876 Obstruction Diseases 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
- 201000010105 allergic rhinitis Diseases 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
- 230000000241 respiratory effect Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- BDDIUTHMWNWMRJ-UHFFFAOYSA-N octane;hydrobromide Chemical compound Br.CCCCCCCC BDDIUTHMWNWMRJ-UHFFFAOYSA-N 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 16
- 239000001257 hydrogen Substances 0.000 description 15
- 239000002245 particle Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- 210000004072 lung Anatomy 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000002367 halogens Chemical group 0.000 description 11
- -1 tertiary alcohol derivatives of 8-azoniabicyclo [3.2.1] octanes Chemical class 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 210000001519 tissue Anatomy 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000000443 aerosol Substances 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 8
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000009471 action Effects 0.000 description 7
- 239000008101 lactose Substances 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000001078 anti-cholinergic effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 210000002460 smooth muscle Anatomy 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 231100000673 dose–response relationship Toxicity 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 229940071648 metered dose inhaler Drugs 0.000 description 5
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 5
- 229960002329 methacholine Drugs 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 210000003437 trachea Anatomy 0.000 description 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- VUUAKOZGGDHCRP-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-4-yl(diphenyl)methanol Chemical compound C=1C=CC=CC=1C(C12CCN(CC1)CC2)(O)C1=CC=CC=C1 VUUAKOZGGDHCRP-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 4
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- 229940039009 isoproterenol Drugs 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
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- 229910052717 sulfur Inorganic materials 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
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- 239000002775 capsule Substances 0.000 description 3
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- 239000012043 crude product Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 210000005037 parasympathetic nerve Anatomy 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
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- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
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- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
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- 230000004962 physiological condition Effects 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
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- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000013630 prepared media Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 238000003653 radioligand binding assay Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect 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
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 239000000523 sample Substances 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
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- 230000004936 stimulating effect Effects 0.000 description 1
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- 125000003107 substituted aryl 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
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- 238000013268 sustained release Methods 0.000 description 1
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- 230000005062 synaptic transmission Effects 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- 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
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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)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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 | |
| US565623P | 2004-04-27 | ||
| PCT/US2005/014386 WO2005104745A2 (en) | 2004-04-27 | 2005-04-27 | Muscarinic acetylcholine receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2392848T3 ES2392848T3 (es) | 2012-12-14 |
| ES2392848T4 true ES2392848T4 (es) | 2014-10-01 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05746609.6T Expired - Lifetime ES2392848T4 (es) | 2004-04-27 | 2005-04-27 | Antagonistas de los receptores muscarínicos de la acetilcolina |
| ES12170402.7T Expired - Lifetime ES2600405T3 (es) | 2004-04-27 | 2005-04-27 | Antagonistas de receptores muscarínicos de la acetilcolina |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12170402.7T Expired - Lifetime ES2600405T3 (es) | 2004-04-27 | 2005-04-27 | Antagonistas de receptores muscarínicos de la acetilcolina |
Country Status (38)
Families Citing this family (78)
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| AR045914A1 (es) * | 2003-07-17 | 2005-11-16 | Glaxo Group Ltd | Compuesto alcoholico terciario del 8-azoniabiciclo [3.2.1] octano, composicion farmaceutica que lo comprende y su uso para preparar esta ultima |
| AR046114A1 (es) * | 2003-10-17 | 2005-11-23 | Glaxo Group Ltd | Compuesto de 8- azoniabiciclo (3.2.1) octano, composicion farmaceutica para el tratamiento de enfermedades mediadas por receptores de acetilcolina muscarinicos y uso del compuesto para preparar dicha composicion |
| TW200524577A (en) * | 2003-11-04 | 2005-08-01 | Glaxo Group Ltd | Muscarinic acetylcholine receptor antagonists |
| US20090253908A1 (en) * | 2004-03-11 | 2009-10-08 | Glaxo Group Limited | Novel m3 muscarinic acetylchoine receptor antagonists |
| EP1725564A4 (en) * | 2004-03-17 | 2007-09-12 | Glaxo Group Ltd | ANTAGONISTS OF THE M3 MUSCARIN ACETYL CHOLIN RECEPTOR |
| US20070185148A1 (en) * | 2004-03-17 | 2007-08-09 | Glaxo Group Limited | M3 muscarinic acetylchoine receptor antagonists |
| ATE405263T1 (de) * | 2004-04-05 | 2008-09-15 | Samaritan Pharmaceuticals Inc | Anti-hiv-chinuklidinverbindungen |
| AR050902A1 (es) * | 2004-04-27 | 2006-12-06 | Glaxo Group Ltd | Compuesto de quinuclidina, composicion farmaceutica que lo comprende y su usopara preparar dicha composicion |
| US7598267B2 (en) * | 2004-05-13 | 2009-10-06 | 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 |
| EP1937267A4 (en) * | 2005-08-02 | 2009-08-26 | Glaxo Group Ltd | M3-MUSCARIN ACETYLCHOLIN RECEPTOR ANTAGONISTS |
| EP1937068A4 (en) * | 2005-08-18 | 2010-08-04 | Glaxo Group Ltd | ANTAGONISTS OF ACETYLCHOLINE MUSCARINIC RECEPTORS |
| EA200801997A1 (ru) | 2006-04-20 | 2009-04-28 | Глаксо Груп Лимитед | Новые соединения |
| GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| PL2046787T3 (pl) | 2006-08-01 | 2011-10-31 | Glaxo Group Ltd | Związki pirazolo[3,4-b]pirydynowe i ich zastosowanie jako inhibitory PDE4 |
| AR065804A1 (es) | 2007-03-23 | 2009-07-01 | Smithkline Beecham Corp | Compuesto de indol carboxamida, composicion farmaceutica que lo comprende y uso de dicho compuesto para preparar un medicamento |
| AR070563A1 (es) | 2008-02-06 | 2010-04-21 | Glaxo Group Ltd | Compuesto de un biciclo condensado pirazol-piridin-amina, composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para el tratamiento de enfermedades respiratorias. |
| TW200946526A (en) | 2008-02-06 | 2009-11-16 | Glaxo Group Ltd | Dual pharmacophores-PDE4-muscarinic antagonistics |
| AR070562A1 (es) | 2008-02-06 | 2010-04-21 | Glaxo Group Ltd | Farmacoforos duales - antagonistas muscarinicos de pde4 |
| ATE552255T1 (de) | 2008-06-05 | 2012-04-15 | Glaxo Group Ltd | 4-aminoindazole |
| US8163743B2 (en) | 2008-06-05 | 2012-04-24 | GlaxoGroupLimited | 4-carboxamide indazole derivatives useful as inhibitors of PI3-kinases |
| WO2010094643A1 (en) | 2009-02-17 | 2010-08-26 | Glaxo Group Limited | Quinoline derivatives and their uses for rhinitis and urticaria |
| EP4578502A3 (en) | 2009-02-26 | 2025-10-08 | Glaxo Group Limited | Pharmaceutical formulations comprising 4-{(1 r)-2-[(6-{2-[(2,6-dichlorobenzyl)oxy]ethoxy}hexyl)amino]-1-hydroxyethyl}-2-(hydroxymethyl)phenol |
| EP2406255B1 (en) | 2009-03-09 | 2015-04-29 | Glaxo Group Limited | 4-oxadiazol-2-yl-indazoles as inhibitors of pi3 kinases |
| EP2406249A1 (en) | 2009-03-10 | 2012-01-18 | Glaxo Group Limited | Indole derivatives as ikk2 inhibitors |
| US20120058984A1 (en) | 2009-03-17 | 2012-03-08 | Catherine Mary Alder | Pyrimidine derivatives used as itk inhibitors |
| JP5570589B2 (ja) | 2009-04-30 | 2014-08-13 | グラクソ グループ リミテッド | Ｐｉ３キナーゼ阻害剤としてのオキサゾール置換インダゾール |
| 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 |
| EP2507226A1 (en) | 2009-12-03 | 2012-10-10 | Glaxo Group Limited | Novel compounds |
| JP2013512879A (ja) | 2009-12-03 | 2013-04-18 | 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のベンズピラゾール誘導体 |
| WO2011067366A1 (en) | 2009-12-03 | 2011-06-09 | Glaxo Group Limited | Indazole derivatives as pi 3 - kinase inhibitors |
| JP5833026B2 (ja) * | 2010-01-28 | 2015-12-16 | セロン ファーマシューティカルズ， インコーポレイテッド | ７−アゾニアビシクロ［２．２．１］ヘプタン誘導体、その産生方法、および薬学的使用 |
| 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 |
| NZ604983A (en) * | 2010-06-22 | 2014-07-25 | Chiesi Farma Spa | Dry powder formulation comprising an antimuscarinic drug |
| WO2012032067A1 (en) | 2010-09-08 | 2012-03-15 | Glaxo Group Limited | Polymorphs and salts of n- [5- [4- (5- { [(2r,6s) -2, 6 - dimethyl - 4 -morpholinyl] methyl} - 1, 3 - oxazol - 2 - yl) - 1h- inda zol-6-yl] -2- (methyloxy) - 3 - pyridinyl] methanesulfonamide |
| 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 |
| PE20141048A1 (es) | 2011-06-08 | 2014-09-08 | Glaxo Group Ltd | Combinacion que comprende umeclidinio y un corticosteroide |
| WO2012168160A1 (en) | 2011-06-08 | 2012-12-13 | Glaxo Group Limited | Dry powder inhaler compositions comprising umeclidinium |
| US9763965B2 (en) | 2012-04-13 | 2017-09-19 | Glaxosmithkline Intellectual Property Development Limited | Aggregate particles |
| 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 |
| CN104619706B (zh) * | 2012-08-15 | 2017-06-20 | 葛兰素集团有限公司 | 化学方法 |
| GB201222679D0 (en) | 2012-12-17 | 2013-01-30 | Glaxo Group Ltd | Pharmaceutical combination products |
| TR201906532T4 (tr) * | 2013-07-13 | 2019-05-21 | Beijing Shuobai Pharmaceutical Co Ltd | Kinin bileşikleri ve optik izomerleri, hazırlanış yöntemleri ve tıbbi kullanımları. |
| BR112016001696A2 (pt) | 2013-07-30 | 2017-08-01 | Glaxosmithkline Ip Dev Ltd | composições tópicas para o tratamento de sudorese excessiva e métodos de uso destas |
| AU2014336250A1 (en) | 2013-10-17 | 2016-04-14 | Glaxosmithkline Intellectual Property Development Limited | PI3K inhibitor for treatment of respiratory disease |
| KR20160062178A (ko) | 2013-10-17 | 2016-06-01 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | 호흡기 질병의 치료를 위한 ｐｉ３ｋ 억제제 |
| EP3142694A2 (en) | 2014-05-12 | 2017-03-22 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pharmaceutical compositions comprising danirixin for treating infectious diseases |
| JP6758196B2 (ja) | 2014-05-28 | 2020-09-23 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | Ｃｏｐｄの治療におけるフルチカゾンフランカルボン酸エステル |
| US10023535B2 (en) | 2014-11-03 | 2018-07-17 | Olon S.P.A. | Method for the preparation of 1-(2-halogen-ethyl)-4 piperidine-carboxylic acid ethyl esters |
| KR101613245B1 (ko) | 2015-04-27 | 2016-04-18 | 주식회사 대웅제약 | 신규의 4-메톡시 피롤 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 |
| CN105461710A (zh) * | 2015-10-23 | 2016-04-06 | 安徽德信佳生物医药有限公司 | 一种芜地溴铵的制备方法 |
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| GB201602527D0 (en) | 2016-02-12 | 2016-03-30 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| CN107200734B (zh) * | 2016-03-18 | 2019-12-24 | 益方生物科技（上海）有限公司 | 奎宁环衍生物及其制备方法和用途 |
| EP3248970A1 (en) | 2016-05-27 | 2017-11-29 | Zentiva K.S. | Forms of umeclidinium bromide |
| JP2019524792A (ja) | 2016-08-08 | 2019-09-05 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 化合物 |
| PT109740B (pt) * | 2016-11-14 | 2020-07-30 | Hovione Farmaciencia Sa | Processo para a preparação de brometo de umeclidínio |
| WO2018163212A1 (en) * | 2017-03-08 | 2018-09-13 | Gbr Laboratories Pvt. Ltd | A process for the preparation of umeclidinium bromide and intermediates thereof |
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