WO2000056718A1 - Composes a base d'imidazole - Google Patents

Composes a base d'imidazole Download PDF

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Publication number
WO2000056718A1
WO2000056718A1 PCT/JP2000/001738 JP0001738W WO0056718A1 WO 2000056718 A1 WO2000056718 A1 WO 2000056718A1 JP 0001738 W JP0001738 W JP 0001738W WO 0056718 A1 WO0056718 A1 WO 0056718A1
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WO
WIPO (PCT)
Prior art keywords
group
acceptable salt
compound
diseases
receptor
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Ceased
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PCT/JP2000/001738
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English (en)
Japanese (ja)
Inventor
Nobuyuki Yasuda
Jun-Ichi Endoh
Masataka Miura
Hideyuki Aizawa
Norio Ohno
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tanabe Pharma Corp
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Mitsubishi Tokyo Pharmaceuticals Inc
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Filing date
Publication date
Application filed by Mitsubishi Tokyo Pharmaceuticals Inc filed Critical Mitsubishi Tokyo Pharmaceuticals Inc
Priority to AU33247/00A priority Critical patent/AU3324700A/en
Publication of WO2000056718A1 publication Critical patent/WO2000056718A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
    • 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
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A61P11/06—Antiasthmatics
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to a novel imidazole compound useful as a pharmaceutical, and more specifically, a novel imidazole compound which is a selective musculin receptor antagonist, a pharmacologically acceptable salt thereof, and a novel imidazole compound.
  • the present invention relates to a pharmaceutical composition containing the same and a musculin phosphorus M 0 receptor antagonist containing the same as an active ingredient.
  • Mus force phosphate receptor least three sub evening I flop the body Ari, receptors in the brain, Micromax 2 receptors in the heart, Micromax 3 receptors is known to be present in smooth muscle and glandular tissue Teshiru Pharmaceuticals having a muscarinic receptor antagonistic action exhibit an analgesic action, an analgesic action, and an antisecretory action, and are therefore used as a therapeutic drug for dysfunction of the intestine or bladder.
  • Atto port pins as a medicament having ⁇ Sukarin receptor antagonism, scopolamine, Okishipuchinin, Nioii ⁇ Purono Nterin, forces that Ipurato port Piu ⁇ rather, these muscarinic receptors, Micromax Ri and Micromax 3 receptors relative to It is known that they have almost the same affinity, and because they antagonize acetylcholine in a non-selective manner, side effects cannot be avoided. Therefore, a drug having a highly selective muscarinic receptor antagonistic action, particularly a drug which does not exhibit side effects on the heart involving the ⁇ 2 receptor has been desired.
  • 3-substituted pyrrolidine derivatives as compounds that selectively antagonize the muscular force 1 ⁇ receptor (Japanese Patent Application Laid-Open No. Hei 2-282, Japanese Patent Application Laid-Open No. Hei 4-2505927, Japanese Patent Laid-open No. Hei 7- No. 1 496 40), 3-substituted piperidine derivative (Japanese Patent Application Laid-Open No. 4-5000521 No. 1), carbamate derivative (W095 / 0663) ), diphenyl acetic acid derivative 3 ⁇ 4
  • Japanese Patent Application Laid-Open No. 7-215943 discloses an imidazole derivative having a strong antagonism, having an ill length of 14 ⁇ higher than that of the muscarinic receptor of the heart and of the muscarinic receptor of flat it®J. Is through an imidazole ring, substituted methyl and an alkylene group having 1 to 6 carbon atoms.
  • R 2 represents a cyano group, a hydroxyl group, a carboxyl group, a C ⁇ NR 7 R 8 group (wherein, R 7 , R Are the same or different and each represent a hydrogen atom or a lower alkyl group, or R 7 and R 8 may form a ring with an alkylene chain which may contain a heteroatom) or a COORQ group (formula Wherein R 0 represents a lower alkyl group), R 3 represents a hydrogen atom or a lower alkyl group, and R, R 5 and R 6 are the same or different and have a hydrogen atom and a substituent; T, a carbon atom representing a lower alkynole group or a cycloalkyl group, or a condensed ring with a benzene ring at R 5 and R 6 , and m represents an integer of 1 to 6]
  • Compound (I) has a pyrrolidine skeleton, a piperidine skeleton, or a cycloalkane skeleton in its structure, and obviously has a different structure.
  • the compound (III) described in Example 11 of this publication has a different structure.
  • the present invention is to provide a compound having a strong antagonism which is higher in the scale of the musk-phosphorus receptor than that of the heart.
  • the present inventors have focused on imidazole compounds and conducted intensive studies.
  • Y is a hydrogen atom, a cyano group or a canolebamoinole group, preferably a rubamoyl group.
  • Z is a CH group or a nitrogen atom, preferably a CH group.
  • One A—B— is one CH.
  • a CH 2 — group or —CH CH— group, preferably one CH 2 —CH.
  • —It is a group.
  • m is 1 or 2, and preferably 1.
  • n is 0 or 1, and is preferably 0.
  • the “chemically acceptable salts” include inorganic salts such as hydrochloric acid, nitric acid and sulfuric acid, organic acid salts such as acetic acid, citric acid, fumaric acid and alcohol, methanesulfonic acid, p — Sulfonic acids such as toluenesulfonic acid, etc., and aminic acid power such as alanine, leucine, guanolemic acid, and gluminamine.
  • optical isomers may be present, and those optical isomers and mixtures thereof may be L-shift.
  • the compound (I) of the present invention or a pharmaceutically acceptable salt thereof may be isolated as a hydrate or a solvent. These are also included in the present invention.
  • chronic obstruction 'respiratory diseases such as sickness disease, asthma, fibrosis and rhinitis
  • hypersensitivity' Used as a preventive or therapeutic agent for gastrointestinal diseases such as spastic inflammation and diverticulitis
  • central illness such as nausea and vomiting, sickness, and menure's disease caused by drug administration
  • urinary diseases such as urinary incontinence and pollakisuria be able to.
  • a solvent such as acetone nitrine, acetone, ethyl methyl ketone, etc.
  • the mixture can be obtained as a salt of compound (I) or compound (I) by ordinary operations such as extraction and purification.
  • any group may be used as long as it functions as a leaving group in a normal chemical reaction.
  • a sulfonyloxy group for example, p-toluenesulfonyloxy group, benzenesulfonyloxy group, methyl sulfonyloxy group, trifluoromethanesulfonyloxy group, etc.
  • a halogen atom for example, chlorine, Bromine, iodine
  • Y, Z, m and n are the same as above.
  • a solvent such as tetrahydrofuran, ether, chloroform, dichloromethane, or the like
  • a base such as triethylamine, 4-dimethylaminopyridine, sodium carbonate, or carbonated lithium, and p-toluenesulfonyl chloride or medium.
  • the compound can be obtained by reacting with a force for forming a sulfonyl chloride or the like, or by reacting with triphenylphosphine in carbon tetrachloride or carbon tetrabromide.
  • a salt thereof in a solvent such as acetonitrile, tetrahydrofuran, ether, chloroform, dichloromethane, etc.
  • a base such as triethylamine, 4-dimethinoleaminopyridine, sodium carbonate, carbonic acid lime is added, and the mixture can be stirred under a solution.
  • the pharmacologically acceptable salts of (I) include, for example, carboxylic acid salts such as hydrochloric acid, nitric acid, and sulfuric acid; organic acid salts such as acetic acid, citric acid, and fumaric acid; methanesulfonic acid; Sulfonic acid ⁇ X such as tosylic acid can be situated by the action of an amino acid such as alanine, leucine, glutamic acid or glutamine in a conventional manner.
  • P-Toluenesulfonic acid 3 [(1-cyano-1,1-diphenyl) methyl] cyclopentylester (16.7 g: 38.8 mmol) obtained from Production Example 3, 2-methyl-1,4—
  • a solution of dihydroimidazole (16.3 g: 193.8 mmol) in acetonitrile (150 ml) was stirred with heating under reflux for 7 hours.
  • the reaction solution was concentrated under reduced pressure, water was added, and the mixture was extracted with black hole form, and then washed twice with water. After drying with anhydrous sodium sulfate, the solvent is distilled off under reduced pressure.
  • the white powder was collected by filtration, and 2.77 g of the compound (30% yield: 76.7% e e) obtained. After dissolving the powder in ethanol (180 ml) under heating and refluxing, it is left at room temperature, and the resulting white powder is collected by filtration, and 1.66 g of the chloride is obtained (13% yield). : 95.0% ee). The same operation was repeated using ethanol (100 ml) to obtain 1.08 g of a tfe crystalline powder (yield 8%: 99.9% ee). The optics were determined by high performance liquid chromatography under the same conditions as in Example 2.
  • Example 6 2- [3- (2-methyl-1,4,5-dihydromidazole-11-yl) cyclopentyl] 1,2,2-diphenylacetonitrile obtained from Example 1 (0. From 26 g: 0.76 mmo 1), 0.07 g (yield: 26%) of an oxide was obtained as amorphous ⁇ .
  • Example 6 2- [3- (2-methylimidazole-11-yl) -cyclopentyl] -2,2-diphenylacetonitrile obtained from Example 9 (0.21 g: 0.6 mmo 1 ), 0.1 g (46% yield) of the nitride was obtained as ⁇ amorphization ⁇ .
  • Example 11 According to 1, p-toluenesulfonic acid 3-[(1-cyano 1,1-diphenyl) methyl] cyclopentyl ester (0.65 g: l. 51 mm 01) obtained from Production Example 5, 2 —Methylimidazole (0.19 g: 2.26 mmol) and 7j sodium iodide (0.05 g: 2.26 mmol) react 3 ⁇ 4S ⁇ to a pale brown amorphous 0.35 g (yield 67%) was obtained as the compound ⁇ /.
  • Example 6 «2— [3- (2-methylimidazo-1-one) -1-pentyl) cyclopentyl] obtained from Example 14—2,2-diphenylacetonitrinole (0.2 g : 0.6 mmo 1): 0.12 g (yield 57%) was obtained as:
  • Example 16 2— [3- (2-Methylimidazole-1-yl) cyclopentinole] —2,2-diphenylacetonitrile
  • 2- (3-chlorocyclopentyl) -1,2,2-diphenylacetonitrinole obtained from Production Example 4 (0.44 g: l.5mmo 1), 2-methylimidazo (0.19 g: 2.26 mmo 1) and sodium hydride (0.05 g: 2.26 mmo 1) to react with 0.17 g (yield 32 %)
  • 2- (3-chlorocyclopentyl) -1,2,2-diphenylacetonitrinole obtained from Production Example 4 (0.44 g: l.5mmo 1), 2-methylimidazo (0.19 g: 2.26 mmo 1) and sodium hydride (0.05 g: 2.26 mmo 1)
  • Example 6 2- [3- (2-methylimidazole-1-yl) cyclopentyl] —2,2-diphenylacetonitrinole obtained from Example 16 (0.17 g: From 0.49 mmo 1), 0.14 g (yield 77%) of an oxide was obtained as »amorphized ⁇ 3 ⁇ 4.
  • Example 6 (-)-1- [3- (2-methylimidazo-1-yl 1-cyclopentyl) cyclopentyl] _2,2-diphenylacetonitrile obtained from Example 20 (1.3 g: 3 81 mm 0 1), 1.03 g (yield: 75%) of 3 ⁇ 4 was converted to fe amorphization!.
  • Example 11 1-[(1-chloro-1,1,1-diphenyl) methyl] pyrrolidine-3-yl methanesulfonate (0.36 g: lmmol), 2-methylimidazole ( 0.17 g: 2mmo 1) and sodium hydride (0.05 g: 2mmo 1) were reacted with 0.17 g (yield 48%) of the fluorinated ⁇ 7 compound as pale yellow oily ⁇ . )Obtained.
  • reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solvent: toluene] to obtain an oil. Isopropyl ether was added to the oil to crystallize it, and 16.7 g (70% yield) of the compound was obtained as white crystalline powder.
  • the occipital region of a male Hartley guinea pig was beaten, »slaughtered, and the trachea was removed while removing connective tissue. Thereafter, the esophagus and the remaining connective tissue were excised, cut at intervals of two tracheal cartilages, and used as specimens.
  • the specimen was incubated at 37 ° C and suspended in a 5 m 1 Magnus bath filled with Krepus carbonate buffer containing indomethacin (1 ⁇ M) through 95% O 2 — 5% CO at a static tension of 1 g. Later, a stabilization period of 60 minutes was allowed.
  • the suspension was suspended at a static tension of 1 g in a 10-ml 1-magnus bath filled with Krebs carbonate buffer solution, followed by a 60-minute stabilization period.
  • the contractile response by carbachol was measured isotonic with Oyakehi 3 than use ,, 10 8 M cumulative method.
  • the sample was washed immediately after the measurement, and a 45-minute stabilization period was allowed until the next contraction.
  • the time point at which EC5 () of the contractile response by carbachol was strongly stabilized was used as a control.
  • Test ⁇ / was also applied 15 minutes prior to carbachol application.
  • the affinity (pA 9 ) of the test substance was determined in the same manner as in the case of the trachea. Table 1 shows the results.
  • the occipital region of a male guinea pig was beaten, exsanguinated and sacrificed, and the ileum was removed while immediately removing the mesentery. After thoroughly washing the contents of the ileum, insert a 57-mm-diameter glass rod into the lumen, cut the longitudinal muscle only along the intestinal membrane attachment with a force razor, and swab the swab with the longitudinal muscle. At the boundary of the muscle, the longitudinal muscle was peeled off while making sure that the paper weave was slightly thin, and used as a specimen.
  • the specimens were incubated at 37 ° C for a 95% 0 2 - After suspended in 5% C 0 static 9 in 10ml organ bath filled with click Repusu carbonate ⁇ liquid through il ⁇ S force 1 g, 6 0 min After a stable period.
  • the contractile response by lightly call was measured isotonic with Oyakehi 3 than use L 10- 9 M accumulation method. After the measurement, the sample was washed quickly and quickly, and allowed a 45-minute stabilization period until the next contraction reaction. It was used as a control point when by lightly call was EC 5 force stable of contraction.
  • the test compound was applied 15 minutes before the application of carbachol, and the affinity (pA 2 ) of the test compound was determined in the same manner as for the trachea. Table 1 shows the results.
  • the occipital region of the Hartley-type guinea pig was beaten, exsanguinated and sacrificed. Immediately after the cardiopulmonary extirpation, the lungs, combined paper tissue, etc. were excised in the order of the ventricles, cut into the left atrium and the right atrium, and used as a specimen. The specimens were incubated at 32 ° C, to 10 m 1 organ bus meets with Krebs carbonate buffer through 95% 0 95% C_ ⁇ 2, it was suspended in resting tension 0. 5 g. Thereafter, contraction due to field electric stimulation (4 Hz, 2 ms ec, 1. ⁇ x threshold 'EE) was measured.
  • Wistar male rats (230-290 g) were anesthetized with urethane (1.2 g / kg, ip), and the right thigh was incised. did.
  • a solvent was administered as a test compound or a control group through this force adjusting device.
  • Five minutes later, 100 g / kg of oxotremorine was administered intravenously to induce salivation.
  • Salivary secretion was measured using a cotton ball for 10 minutes immediately after the administration of oxotremorine. Calculated percent inhibition on the secretion amount of saliva in the control group, the dose of secreted saliva amount of the control group 5 0% inhibition of the test I spoon compound was ID 5 0 value.
  • Table 2 shows the results.
  • Table 2 Musculin receptor antagonistic activity (invi vo: intravenous administration of test compound)
  • the disease present invention I spoon was involved muscarinic M 3 receptors, in particular, ⁇ occlusion City disease, asthma, respiratory diseases such as lung fiber beauty rhinitis; hypersensitivity syndrome, spastic colitis, diverticulitis, etc. It is useful as a preventive or return IJ for central illness such as digestive tract diseases caused by drug administration, nausea and vomiting, vomiting, and Meniere's disease; urinary incontinence and frequent urination such as pollakiuria.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pulmonology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Otolaryngology (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des composés représentés par la formule générale (I) ou leurs sels acceptables du point de vue pharmacologique. Dans la formule (I) selon l'invention, Y représente un hydrogène, un cyano ou un carbamoyle; Z représente CH ou un azote; -A-B- représente -CH2-CH2- ou -CH=CH-; m désigne 1 ou 2; et n désigne 0 ou 1. Parce qu'ils présentent un antagonisme extrêmement puissant et sélectif au récepteur M3 de muscarine, ces composés s'utilisent comme préventifs ou remèdes contre des maladies dans lesquelles intervient le récepteur M3 de muscarine. En outre, ces composés permettent de produire des médicaments sûrs entraînant à peine la soif, qui est un effet secondaire des antagonistes du récepteur M3 de muscarine.
PCT/JP2000/001738 1999-03-24 2000-03-22 Composes a base d'imidazole Ceased WO2000056718A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU33247/00A AU3324700A (en) 1999-03-24 2000-03-22 Imidazole compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP08034999A JP2003286266A (ja) 1999-03-24 1999-03-24 イミダゾール化合物
JP11/80349 1999-03-24

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WO2000056718A1 true WO2000056718A1 (fr) 2000-09-28

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005120067A (ja) * 2003-09-22 2005-05-12 Dai Ichi Seiyaku Co Ltd 光学活性シクロプロピルアミン誘導体およびその製造方法
WO2005056526A1 (fr) * 2003-12-12 2005-06-23 Daiichi Pharmaceutical Co., Ltd. Intermediaires destines a la production de derives de cyclopropylamine optiquement actifs et processus de production de ces intermediaires
WO2007013421A1 (fr) * 2005-07-25 2007-02-01 Mitsubishi Tanabe Pharma Corporation Nouveau composé hétérocyclique azoté
WO2007077510A2 (fr) 2005-12-30 2007-07-12 Ranbaxy Laboratories Limited Antagonistes des récepteurs muscariniques
EP2130830A1 (fr) 2008-06-03 2009-12-09 Ranbaxy Laboratories Limited Antagonistes de récepteur muscarinique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085184A1 (fr) * 2004-03-09 2005-09-15 Japan Science And Technology Agency Procédé de production de dérivés du cyclopentènenitrile

Citations (3)

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Publication number Priority date Publication date Assignee Title
JPH07291936A (ja) * 1994-03-01 1995-11-07 Kyorin Pharmaceut Co Ltd 新規イミダゾール誘導体及びその製造法
EP0733621A1 (fr) * 1993-12-10 1996-09-25 Kyorin Pharmaceutical Co., Ltd. Nouveau derive de l'imidazole et sa methode d'obtention
WO1999014200A1 (fr) * 1997-09-18 1999-03-25 Mitsubishi-Tokyo Pharmaceuticals, Inc. Composes d'imidazoline

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0733621A1 (fr) * 1993-12-10 1996-09-25 Kyorin Pharmaceutical Co., Ltd. Nouveau derive de l'imidazole et sa methode d'obtention
JPH07291936A (ja) * 1994-03-01 1995-11-07 Kyorin Pharmaceut Co Ltd 新規イミダゾール誘導体及びその製造法
WO1999014200A1 (fr) * 1997-09-18 1999-03-25 Mitsubishi-Tokyo Pharmaceuticals, Inc. Composes d'imidazoline

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
MIYACHI H. ET AL.: "Novel imidazole derivatives with subtype-selective antimuscarinic activity (1)", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, no. 14, 1998, pages 1807 - 1812, XP002933245 *
MIYACHI H. ET AL.: "Novel imidazole derivatives with subtype-selective antimuscarinic activity (2)", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, no. 16, 1998, pages 2163 - 2168, XP002933244 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005120067A (ja) * 2003-09-22 2005-05-12 Dai Ichi Seiyaku Co Ltd 光学活性シクロプロピルアミン誘導体およびその製造方法
WO2005056526A1 (fr) * 2003-12-12 2005-06-23 Daiichi Pharmaceutical Co., Ltd. Intermediaires destines a la production de derives de cyclopropylamine optiquement actifs et processus de production de ces intermediaires
US7569599B2 (en) 2003-12-12 2009-08-04 Daiichi Pharmaceutical Co., Ltd. Intermediates for the production of optically active cyclopropylamine derivatives and process for the production of the intermediates
US7994344B2 (en) 2003-12-12 2011-08-09 Daiichi Sankyo Company, Limited Intermediates for the production of optically active cyclopropylamine derivatives and process for the production of the intermediates
WO2007013421A1 (fr) * 2005-07-25 2007-02-01 Mitsubishi Tanabe Pharma Corporation Nouveau composé hétérocyclique azoté
WO2007077510A2 (fr) 2005-12-30 2007-07-12 Ranbaxy Laboratories Limited Antagonistes des récepteurs muscariniques
EP2130830A1 (fr) 2008-06-03 2009-12-09 Ranbaxy Laboratories Limited Antagonistes de récepteur muscarinique

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AU3324700A (en) 2000-10-09

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