CA2474874C - Anticholinergic agents, method for producing the same and use thereof as medicaments - Google Patents
Anticholinergic agents, method for producing the same and use thereof as medicaments Download PDFInfo
- Publication number
- CA2474874C CA2474874C CA2474874A CA2474874A CA2474874C CA 2474874 C CA2474874 C CA 2474874C CA 2474874 A CA2474874 A CA 2474874A CA 2474874 A CA2474874 A CA 2474874A CA 2474874 C CA2474874 C CA 2474874C
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- denote
- different
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- methyl
- hydroxy
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- 239000000812 cholinergic antagonist Substances 0.000 title abstract description 5
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title description 2
- 239000003814 drug Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000001257 hydrogen Substances 0.000 claims abstract description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 55
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 35
- -1 substituted Chemical class 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 24
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- 150000001450 anions Chemical class 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 109
- 150000003839 salts Chemical class 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 36
- 239000013543 active substance Substances 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229940043355 kinase inhibitor Drugs 0.000 claims description 11
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 239000000808 adrenergic beta-agonist Substances 0.000 claims description 9
- 230000003454 betamimetic effect Effects 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
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- 229960001334 corticosteroids Drugs 0.000 claims description 6
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 6
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 6
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000043 antiallergic agent Substances 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
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- 206010040741 Sinus bradycardia Diseases 0.000 claims description 3
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- 230000033764 rhythmic process Effects 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 3
- 210000001635 urinary tract Anatomy 0.000 claims description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- 230000003266 anti-allergic effect Effects 0.000 claims description 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000013312 porous aromatic framework Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 206010062225 Urinary tract pain Diseases 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 230000001078 anti-cholinergic effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 125000002947 alkylene group Chemical group 0.000 abstract description 3
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000013078 crystal Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
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- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 15
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
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- SBXDXDHBBHYRGU-HXUWFJFHSA-N n-[7-(cyclopropylmethoxy)-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]-4-morpholin-4-ylbut-2-enamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C1=CC=2NC(=O)C=CCN3CCOCC3)=NC=NC1=CC=2OCC1CC1 SBXDXDHBBHYRGU-HXUWFJFHSA-N 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 150000008163 sugars Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HNDGEYCCZGRMTN-UHFFFAOYSA-N thieno[3,2-f:4,5-f]bis[1]benzothiophene Chemical compound S1C2=CC=3SC=CC=3C=C2C2=C1C=C(SC=C1)C1=C2 HNDGEYCCZGRMTN-UHFFFAOYSA-N 0.000 description 1
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- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 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
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10203749A DE10203749A1 (de) | 2002-01-31 | 2002-01-31 | Neue Anticholinergika, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
| DE10203749.3 | 2002-01-31 | ||
| PCT/EP2003/000533 WO2003064418A1 (de) | 2002-01-31 | 2003-01-21 | Anticholinergika, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2474874A1 CA2474874A1 (en) | 2003-08-07 |
| CA2474874C true CA2474874C (en) | 2012-10-30 |
Family
ID=27588163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2474874A Expired - Fee Related CA2474874C (en) | 2002-01-31 | 2003-01-21 | Anticholinergic agents, method for producing the same and use thereof as medicaments |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1472250B1 (enExample) |
| JP (1) | JP4484521B2 (enExample) |
| KR (1) | KR100950870B1 (enExample) |
| CN (1) | CN1291986C (enExample) |
| AR (1) | AR038331A1 (enExample) |
| AU (1) | AU2003206760B8 (enExample) |
| BR (1) | BR0307299A (enExample) |
| CA (1) | CA2474874C (enExample) |
| CO (1) | CO5601000A2 (enExample) |
| DE (1) | DE10203749A1 (enExample) |
| IL (1) | IL162669A0 (enExample) |
| MX (1) | MXPA04007249A (enExample) |
| NZ (1) | NZ534927A (enExample) |
| PE (1) | PE20030964A1 (enExample) |
| PL (1) | PL211064B1 (enExample) |
| RU (1) | RU2325388C2 (enExample) |
| TW (1) | TWI260323B (enExample) |
| UY (1) | UY27629A1 (enExample) |
| WO (1) | WO2003064418A1 (enExample) |
| ZA (1) | ZA200404569B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004206846B2 (en) * | 2003-01-16 | 2009-05-28 | University Of Rochester | Quaternary antimuscarinic compounds for the treatment of bladder diseases |
| EP1651224B1 (en) * | 2003-07-31 | 2011-10-05 | Boehringer Ingelheim International GmbH | Medicaments for inhalation comprising an anticholinergic and a betamimetic |
| WO2005079794A1 (en) * | 2004-02-20 | 2005-09-01 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions based on anticholinergics and pegsunercept |
| US7507745B2 (en) | 2004-02-20 | 2009-03-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions based on fluorenecarboxylic acid esters and soluble TNF receptor fusion proteins |
| DE102004016179A1 (de) * | 2004-03-30 | 2005-10-20 | Boehringer Ingelheim Pharma | Verbindungen zur Behandlung von proliferativen Prozessen |
| ES2322148T3 (es) * | 2004-08-11 | 2009-06-17 | BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG | Medicamentos que contienen anticolinergicos para el tratamiento en las vias urinarias. |
| EP1785421A1 (en) * | 2004-08-30 | 2007-05-16 | Ono Pharmaceutical Co., Ltd. | Tropan compound |
| WO2006087316A1 (en) * | 2005-02-16 | 2006-08-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions comprising anticholinergics and etiprednol |
| EP1858554A2 (en) * | 2005-03-09 | 2007-11-28 | Boehringer Ingelheim International GmbH | New pharmaceutical compositions based on anticholinergics and pde 5-inhibitors |
| CA2609429A1 (en) * | 2005-05-31 | 2006-12-07 | Boehringer Ingelheim International Gmbh | Medicament containing a betamimetic in conjunction with an anticholinergic and a pde iv inhibitor |
| DE102005030733A1 (de) | 2005-07-01 | 2007-01-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkombinationen zur Behandlung von Atemwegserkrankungen enthaltend langwirksame Beta-2-Agonisten und wenigstens einen weiteren Wirkstoff |
| US7423146B2 (en) | 2005-11-09 | 2008-09-09 | Boehringer Ingelheim International Gmbh | Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones |
| JP2009091250A (ja) * | 2006-01-30 | 2009-04-30 | Ono Pharmaceut Co Ltd | トロパン化合物およびそれらを有効成分として含有する医薬組成物 |
| ES2360963T3 (es) | 2006-08-07 | 2011-06-10 | Boehringer Ingelheim International Gmbh | Combinaciones de fármacos para el tratamiento de enfermedades de las vías respiratorias. |
| UY30550A1 (es) | 2006-08-22 | 2008-03-31 | Boehringer Ingelheim Int | Nuevos beta-agonistas enantioméricamente puros, procedimientos para su preparacion y su uso como medicamentos |
| ES2569359T3 (es) | 2007-07-06 | 2016-05-10 | Vectura Delivery Devices Limited | Inhalador |
| US20100234411A1 (en) * | 2007-07-18 | 2010-09-16 | Boehringer Ingelheim Intermational Gmbh | New Combination for the Treatment of Respiratory Diseases |
| EP2082768A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082771A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082767A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082772A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082766A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Blister Strip Coil Forming |
| EP2093219A1 (de) | 2008-02-22 | 2009-08-26 | Boehringer Ingelheim International Gmbh | Kristalline, enantiomerenreine Salzform eines Betamimetikums und dessen Verwendung als Arzneimittel |
| GB0918450D0 (en) | 2009-10-21 | 2009-12-09 | Innovata Ltd | Composition |
| RU2535027C2 (ru) * | 2012-08-10 | 2014-12-10 | Федеральное государственное бюджетное учреждение "Научно-исследовательский институт экспериментальной медицины" Северо-Западного отделения Российской академии медицинских наук (ФГБУ "НИИЭМ" СЗО РАМН) | Антидепрессивное средство |
| CN102964345B (zh) * | 2012-12-06 | 2016-07-13 | 四川理工学院 | 一种2―羟基―2,2―二苯基乙酸―3α―(8―氮杂双环[3,2,1])―3―辛酯的制备方法 |
| EP3380470A1 (en) | 2015-11-23 | 2018-10-03 | Syngenta Participations AG | Pesticidally active heterocyclic derivatives with sulphur and cyclopropyl containing substituents |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
| CA3127373A1 (en) | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce dux4 and downstream gene expression for the treatment of fshd |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3931041C2 (de) * | 1989-09-16 | 2000-04-06 | Boehringer Ingelheim Kg | Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| DE4108393A1 (de) * | 1991-03-15 | 1992-09-17 | Boehringer Ingelheim Kg | Neue ester bi- und tricyclischer aminoalkohole, ihre herstellung und ihre verwendung in arzneimitteln |
-
2002
- 2002-01-31 DE DE10203749A patent/DE10203749A1/de not_active Withdrawn
-
2003
- 2003-01-21 IL IL16266903A patent/IL162669A0/xx not_active IP Right Cessation
- 2003-01-21 MX MXPA04007249A patent/MXPA04007249A/es active IP Right Grant
- 2003-01-21 NZ NZ534927A patent/NZ534927A/en not_active IP Right Cessation
- 2003-01-21 PL PL369889A patent/PL211064B1/pl unknown
- 2003-01-21 RU RU2004126441/04A patent/RU2325388C2/ru not_active IP Right Cessation
- 2003-01-21 KR KR1020047011901A patent/KR100950870B1/ko not_active Expired - Fee Related
- 2003-01-21 CA CA2474874A patent/CA2474874C/en not_active Expired - Fee Related
- 2003-01-21 EP EP03704441.9A patent/EP1472250B1/de not_active Expired - Lifetime
- 2003-01-21 WO PCT/EP2003/000533 patent/WO2003064418A1/de not_active Ceased
- 2003-01-21 CN CNB038029995A patent/CN1291986C/zh not_active Expired - Fee Related
- 2003-01-21 AU AU2003206760A patent/AU2003206760B8/en not_active Ceased
- 2003-01-21 JP JP2003564041A patent/JP4484521B2/ja not_active Expired - Lifetime
- 2003-01-21 BR BR0307299-1A patent/BR0307299A/pt not_active IP Right Cessation
- 2003-01-29 UY UY27629A patent/UY27629A1/es not_active Application Discontinuation
- 2003-01-29 TW TW092101967A patent/TWI260323B/zh not_active IP Right Cessation
- 2003-01-29 AR ARP030100253A patent/AR038331A1/es active IP Right Grant
- 2003-01-29 PE PE2003000090A patent/PE20030964A1/es not_active Application Discontinuation
-
2004
- 2004-06-09 ZA ZA200404569A patent/ZA200404569B/en unknown
- 2004-08-06 CO CO04076776A patent/CO5601000A2/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| IL162669A0 (en) | 2005-11-20 |
| JP4484521B2 (ja) | 2010-06-16 |
| AR038331A1 (es) | 2005-01-12 |
| BR0307299A (pt) | 2004-12-21 |
| RU2004126441A (ru) | 2005-07-10 |
| PL211064B1 (pl) | 2012-04-30 |
| MXPA04007249A (es) | 2004-10-29 |
| TWI260323B (en) | 2006-08-21 |
| EP1472250B1 (de) | 2014-11-26 |
| PE20030964A1 (es) | 2003-12-24 |
| UY27629A1 (es) | 2003-08-29 |
| PL369889A1 (en) | 2005-05-02 |
| RU2325388C2 (ru) | 2008-05-27 |
| NZ534927A (en) | 2006-10-27 |
| KR100950870B1 (ko) | 2010-04-06 |
| HK1077818A1 (en) | 2006-02-24 |
| CN1291986C (zh) | 2006-12-27 |
| DE10203749A1 (de) | 2003-08-14 |
| KR20040081168A (ko) | 2004-09-20 |
| EP1472250A1 (de) | 2004-11-03 |
| ZA200404569B (en) | 2006-08-30 |
| CO5601000A2 (es) | 2006-01-31 |
| TW200404800A (en) | 2004-04-01 |
| AU2003206760B8 (en) | 2009-05-07 |
| WO2003064418A1 (de) | 2003-08-07 |
| JP2005525323A (ja) | 2005-08-25 |
| CA2474874A1 (en) | 2003-08-07 |
| AU2003206760B2 (en) | 2009-03-26 |
| CN1625556A (zh) | 2005-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160121 |