JP3981357B2 - 第4級アンモニウム化合物および抗ムスカリン剤としてのそれらの使用 - Google Patents
第4級アンモニウム化合物および抗ムスカリン剤としてのそれらの使用 Download PDFInfo
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- JP3981357B2 JP3981357B2 JP2003538115A JP2003538115A JP3981357B2 JP 3981357 B2 JP3981357 B2 JP 3981357B2 JP 2003538115 A JP2003538115 A JP 2003538115A JP 2003538115 A JP2003538115 A JP 2003538115A JP 3981357 B2 JP3981357 B2 JP 3981357B2
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- Prior art keywords
- quaternary ammonium
- compound according
- ammonium compound
- methylphenyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000003856 quaternary ammonium compounds Chemical class 0.000 title claims description 41
- 239000003149 muscarinic antagonist Substances 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- -1 compound (3R)-3-[2-hydroxy-5-(trifluoromethyl)phenyl]-N,N-diisopropyl-N-methyl-3-phenylpropan-1-aminium bromide Chemical class 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 208000006673 asthma Diseases 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 14
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 206010039101 Rhinorrhoea Diseases 0.000 claims description 13
- 201000009240 nasopharyngitis Diseases 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 208000010753 nasal discharge Diseases 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- RNTMLDNKBNBHNB-ZMBIFBSDSA-N [(3r)-3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-methyl-di(propan-2-yl)azanium;iodide Chemical compound [I-].C1([C@@H](CC[N+](C)(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 RNTMLDNKBNBHNB-ZMBIFBSDSA-N 0.000 claims description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 201000010105 allergic rhinitis Diseases 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- ISCNVPQNWZCJPY-ZMBIFBSDSA-N [(3r)-3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-methyl-di(propan-2-yl)azanium;bromide Chemical compound [Br-].C1([C@@H](CC[N+](C)(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 ISCNVPQNWZCJPY-ZMBIFBSDSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- HEZUKONMXSDPAM-GJFSDDNBSA-M [(3r)-3-(2-butanoyloxy-5-methylphenyl)-3-phenylpropyl]-methyl-di(propan-2-yl)azanium;iodide Chemical compound [I-].CCCC(=O)OC1=CC=C(C)C=C1[C@H](CC[N+](C)(C(C)C)C(C)C)C1=CC=CC=C1 HEZUKONMXSDPAM-GJFSDDNBSA-M 0.000 claims description 4
- XCJAYQXUPYJVJF-ZMBIFBSDSA-N [(3r)-3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-methyl-di(propan-2-yl)azanium;chloride Chemical compound [Cl-].C1([C@@H](CC[N+](C)(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 XCJAYQXUPYJVJF-ZMBIFBSDSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- PESFBMQBUBQIHZ-OAQYLSRUSA-N 4-methyl-2-[(1r)-3-[methyl-di(propan-2-yl)azaniumyl]-1-phenylpropyl]phenolate Chemical compound C1([C@@H](CC[N+](C)(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)[O-])=CC=CC=C1 PESFBMQBUBQIHZ-OAQYLSRUSA-N 0.000 claims description 2
- GLTLBMUDTQBVJJ-UHFFFAOYSA-N 4-methyl-2-[3-(1-methylpiperidin-1-ium-1-yl)-1-phenylpropyl]phenol;iodide Chemical compound [I-].CC1=CC=C(O)C(C(CC[N+]2(C)CCCCC2)C=2C=CC=CC=2)=C1 GLTLBMUDTQBVJJ-UHFFFAOYSA-N 0.000 claims description 2
- GFJJOVYVZWLZBJ-UHFFFAOYSA-N 4-methyl-2-[3-(1-methylpyrrolidin-1-ium-1-yl)-1-phenylpropyl]phenol;iodide Chemical compound [I-].CC1=CC=C(O)C(C(CC[N+]2(C)CCCC2)C=2C=CC=CC=2)=C1 GFJJOVYVZWLZBJ-UHFFFAOYSA-N 0.000 claims description 2
- ZDOOPTLDCVMMMJ-GNAFDRTKSA-N [(3r)-3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-di(propan-2-yl)-propylazanium;iodide Chemical compound [I-].C1([C@@H](CC[N+](CCC)(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 ZDOOPTLDCVMMMJ-GNAFDRTKSA-N 0.000 claims description 2
- DAOYMMUOBYZBTI-VZYDHVRKSA-M [(3r)-3-(2-methoxy-5-methylphenyl)-3-phenylpropyl]-methyl-di(propan-2-yl)azanium;iodide Chemical compound [I-].COC1=CC=C(C)C=C1[C@H](CC[N+](C)(C(C)C)C(C)C)C1=CC=CC=C1 DAOYMMUOBYZBTI-VZYDHVRKSA-M 0.000 claims description 2
- HSNLBDOFLICSJT-HZPIKELBSA-N benzyl-[(3r)-3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-di(propan-2-yl)azanium;iodide Chemical compound [I-].C1([C@@H](CC[N+](C(C)C)(CC=2C=CC=CC=2)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 HSNLBDOFLICSJT-HZPIKELBSA-N 0.000 claims description 2
- MEQQKLUUMXRNNJ-VZYDHVRKSA-N ethyl-[(3r)-3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-di(propan-2-yl)azanium;iodide Chemical compound [I-].C1([C@@H](CC[N+](CC)(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 MEQQKLUUMXRNNJ-VZYDHVRKSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- SAHYUXAUEOHSTF-UHFFFAOYSA-N 2-[3-(1-ethylpyrrolidin-1-ium-1-yl)-1-phenylpropyl]-4-methylphenol;iodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C(=CC=C(C)C=1)O)CC[N+]1(CC)CCCC1 SAHYUXAUEOHSTF-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract description 6
- 229940102396 methyl bromide Drugs 0.000 abstract description 3
- FIZRZYUJJOUDHY-LJQANCHMSA-N 2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(trifluoromethyl)phenol Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C=2)C(F)(F)F)O)=CC=CC=C1 FIZRZYUJJOUDHY-LJQANCHMSA-N 0.000 abstract 1
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- 238000011282 treatment Methods 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000000443 aerosol Substances 0.000 description 29
- OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 229960004045 tolterodine Drugs 0.000 description 23
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 23
- 238000000034 method Methods 0.000 description 22
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- 125000004432 carbon atom Chemical group C* 0.000 description 19
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 18
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- 230000000694 effects Effects 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
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- OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 description 6
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- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/66—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with quaternised amino groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Pyridine Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (4)
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| US34893001P | 2001-10-26 | 2001-10-26 | |
| US36197902P | 2002-03-06 | 2002-03-06 | |
| US39152102P | 2002-06-25 | 2002-06-25 | |
| PCT/US2002/034529 WO2003035599A1 (en) | 2001-10-26 | 2002-10-25 | Quarternary ammonium compounds and their use as antimuscarinic agents |
Publications (3)
| Publication Number | Publication Date |
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| JP2005524605A JP2005524605A (ja) | 2005-08-18 |
| JP2005524605A5 JP2005524605A5 (https=) | 2006-01-19 |
| JP3981357B2 true JP3981357B2 (ja) | 2007-09-26 |
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| EP (1) | EP1461306B1 (https=) |
| JP (1) | JP3981357B2 (https=) |
| AT (1) | ATE418534T1 (https=) |
| BR (1) | BR0206207A (https=) |
| CA (1) | CA2464223C (https=) |
| CY (1) | CY1109898T1 (https=) |
| DE (1) | DE60230546D1 (https=) |
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| ES (1) | ES2315425T3 (https=) |
| MX (1) | MXPA04003865A (https=) |
| MY (1) | MY130316A (https=) |
| NO (1) | NO20032938L (https=) |
| PT (1) | PT1461306E (https=) |
| SG (1) | SG168451A1 (https=) |
| WO (1) | WO2003035599A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0957073A1 (en) | 1998-05-12 | 1999-11-17 | Schwarz Pharma Ag | Novel derivatives of 3,3-diphenylpropylamines |
| DE60230546D1 (de) * | 2001-10-26 | 2009-02-05 | Pharmacia & Upjohn Co Llc | Quaternäre ammoniumverbindungen und deren verwendung als antimuscarinische wirkstoffe |
| US7754242B2 (en) * | 2002-03-20 | 2010-07-13 | Alkermes, Inc. | Inhalable sustained therapeutic formulations |
| AU2003231777C1 (en) * | 2002-04-29 | 2009-10-29 | Supernus Pharmaceuticals, Inc. | Pharmaceutical formulations with improved bioavailability |
| DE10315917A1 (de) * | 2003-04-08 | 2004-11-18 | Schwarz Pharma Ag | Hochreine Basen von 3,3-Diphenylpropylaminmonoestern |
| JP2006523676A (ja) * | 2003-04-15 | 2006-10-19 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 第四級アンモニウム化合物と、その抗ムスカリン性剤としての使用 |
| WO2004091597A2 (en) * | 2003-04-15 | 2004-10-28 | Pharmacia & Upjohn Company Llc | Method of treating irritable bowel syndrome (ibs) |
| JP2006523674A (ja) * | 2003-04-18 | 2006-10-19 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 慢性閉塞性肺疾患(copd)のための組合せ治療法 |
| WO2004096751A1 (en) * | 2003-04-25 | 2004-11-11 | Pharmacia & Upjohn Company Llc | Halogen substituted 3,3-diphenylpropylamines (tolterodine) having antimuscarinic activity |
| DK2210605T3 (en) * | 2003-11-04 | 2017-05-22 | Tcd Royalty Sub Llc | Daily single dose doses of trospium. |
| US8709476B2 (en) | 2003-11-04 | 2014-04-29 | Supernus Pharmaceuticals, Inc. | Compositions of quaternary ammonium compounds containing bioavailability enhancers |
| ES2235648B1 (es) * | 2003-12-22 | 2006-11-01 | Ragactives, S.L. | Procedimiento para la obtencion de tolterodina. |
| EP1701932B1 (en) * | 2003-12-24 | 2012-07-18 | Cipla Ltd. | Tolterodine, compositions and uses thereof, and preparation of the same |
| JP2007530451A (ja) * | 2004-03-11 | 2007-11-01 | 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 |
| EP1838659B1 (en) * | 2004-12-24 | 2015-07-15 | LEK Pharmaceuticals d.d. | Process for preparation of n,n-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine |
| US20110135580A1 (en) * | 2006-05-24 | 2011-06-09 | Boehringer Ingelheim International Gmbh | Novel Medicament Combinations for the Treatment of Respiratory Diseases |
| EP1908502A1 (en) * | 2006-10-02 | 2008-04-09 | Koninklijke Philips Electronics N.V. | Interactive modular tile system |
| US7731604B2 (en) * | 2006-10-31 | 2010-06-08 | Taylor Made Golf Company, Inc. | Golf club iron head |
| US20100112061A1 (en) * | 2006-12-13 | 2010-05-06 | William Baker | Monophosphates as Mutual Prodrugs of Muscarinic Receptor Antagonists and Beta-Agonists for the Treatment of COPD And Chronic Bronchitis |
| ES2554646T3 (es) * | 2007-02-23 | 2015-12-22 | Theravance Biopharma R&D Ip, Llc | Compuestos de difenilmetilo de amonio cuaternario, de utilidad como antagonistas de receptores muscarínicos |
| CA2682032A1 (en) | 2007-04-24 | 2008-11-06 | Theravance, Inc. | Quaternary ammonium compounds useful as muscarinic receptor antagonists |
| US20090246146A1 (en) * | 2008-01-25 | 2009-10-01 | Botond Banfi | Halides in the treatment of pathogenic infection |
| US20090318396A1 (en) * | 2008-06-10 | 2009-12-24 | Gilead Sciences, Inc. | Corticosteroid linked beta-agonist compounds for use in therapy |
| WO2010010464A2 (en) * | 2008-07-21 | 2010-01-28 | Actavis Group Ptc Ehf | Fesoterodine substantially free of dehydroxy impurity |
| JP5801997B2 (ja) | 2009-07-07 | 2015-10-28 | ファイザー・リミテッドPfizer Limited | 薬品の組合せを吸入するための投薬ユニット、投薬ユニットのパック、および吸入器 |
| CN110372571B (zh) * | 2018-04-12 | 2022-11-15 | 中国科学院大连化学物理研究所 | 一种2-(2,2-二芳基乙基)-环胺衍生物或盐及合成和应用与组合物 |
| CN110845357B (zh) * | 2019-11-22 | 2022-09-30 | 华东理工大学 | 季铵盐型酰肼化合物及由其制备的季铵盐型腙类化合物与应用 |
| CN116033893A (zh) | 2020-06-26 | 2023-04-28 | 迈兰制药英国有限公司 | 包含5-[3-(3-羟基苯氧基)氮杂环丁烷-1-基]-5-甲基-2,2-二苯基己酰胺的制剂 |
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| US2592191A (en) * | 1949-09-16 | 1952-04-08 | Sterling Drug Inc | Quaternary ammonium salts of nu-(3, 3-diphenylpropyl) pyrrolidine |
| NL267508A (https=) | 1960-07-26 | |||
| NL6717123A (https=) | 1966-12-29 | 1968-07-01 | ||
| US3505337A (en) | 1967-12-22 | 1970-04-07 | Boehringer Sohn Ingelheim | N - hydrocarbyl-substituted noratropinium,haloalkylates and o-acyl derivatives thereof |
| US5382600A (en) | 1988-01-22 | 1995-01-17 | Pharmacia Aktiebolag | 3,3-diphenylpropylamines and pharmaceutical compositions thereof |
| IL91377A (en) | 1988-09-14 | 1996-09-12 | Nippon Shinyaku Co Ltd | Derivatives of botinylamine glycolate |
| GB8906166D0 (en) | 1989-03-17 | 1989-05-04 | Pfizer Ltd | Therapeutic agents |
| 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 |
| SE9203318D0 (sv) | 1992-11-06 | 1992-11-06 | Kabi Pharmacia Ab | Novel 3,3-diphenylpropylamines, their use and preparation |
| US5492933A (en) | 1993-10-08 | 1996-02-20 | Sepracor, Inc. | Methods and compositions for treating urinary incontinence and other disorders using optically pure R-terodiline and hydroxylated derivatives thereof |
| AU7971394A (en) | 1993-10-08 | 1995-05-04 | Sepracor, Inc. | Method for treating urinary incontinence using optically pure s-terodiline |
| KR20000057548A (ko) | 1996-12-13 | 2000-09-25 | 알프레드 엘. 미첼슨 | 광학적 전송물질 및 결합재 |
| SE9701144D0 (sv) * | 1997-03-27 | 1997-03-27 | Pharmacia & Upjohn Ab | Novel compounds, their use and preparation |
| PE20020547A1 (es) * | 2000-10-24 | 2002-06-12 | Upjohn Co | Uso de la tolterodina en tratamientos del asma |
| WO2002035245A1 (en) | 2000-10-26 | 2002-05-02 | Koninklijke Philips Electronics N.V. | Electronic device |
| DE60230546D1 (de) * | 2001-10-26 | 2009-02-05 | Pharmacia & Upjohn Co Llc | Quaternäre ammoniumverbindungen und deren verwendung als antimuscarinische wirkstoffe |
| JP2006523676A (ja) * | 2003-04-15 | 2006-10-19 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 第四級アンモニウム化合物と、その抗ムスカリン性剤としての使用 |
| WO2004096751A1 (en) * | 2003-04-25 | 2004-11-11 | Pharmacia & Upjohn Company Llc | Halogen substituted 3,3-diphenylpropylamines (tolterodine) having antimuscarinic activity |
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| EP1461306B1 (en) | 2008-12-24 |
| CA2464223C (en) | 2009-05-26 |
| NO20032938D0 (no) | 2003-06-26 |
| NO20032938L (no) | 2003-08-25 |
| ES2315425T3 (es) | 2009-04-01 |
| PT1461306E (pt) | 2009-04-01 |
| CA2464223A1 (en) | 2003-05-01 |
| ATE418534T1 (de) | 2009-01-15 |
| MXPA04003865A (es) | 2004-07-08 |
| US7439397B2 (en) | 2008-10-21 |
| JP2005524605A (ja) | 2005-08-18 |
| BR0206207A (pt) | 2003-12-23 |
| DK1461306T3 (da) | 2009-03-09 |
| MY130316A (en) | 2007-06-29 |
| CY1109898T1 (el) | 2014-09-10 |
| US20030158176A1 (en) | 2003-08-21 |
| US20050148672A1 (en) | 2005-07-07 |
| US6890920B2 (en) | 2005-05-10 |
| SG168451A1 (en) | 2011-02-28 |
| DE60230546D1 (de) | 2009-02-05 |
| EP1461306A1 (en) | 2004-09-29 |
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