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WO2007145203A1 - 2-amino-1-(4-fluorophenyl) éthanol optiquement actif - Google Patents

2-amino-1-(4-fluorophenyl) éthanol optiquement actif Download PDF

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Publication number
WO2007145203A1
WO2007145203A1 PCT/JP2007/061799 JP2007061799W WO2007145203A1 WO 2007145203 A1 WO2007145203 A1 WO 2007145203A1 JP 2007061799 W JP2007061799 W JP 2007061799W WO 2007145203 A1 WO2007145203 A1 WO 2007145203A1
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group
configuration
general formula
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atom
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PCT/JP2007/061799
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English (en)
Japanese (ja)
Inventor
Takeshi Tachinami
Yoshinori Matsumoto
Takahiro Isobe
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Daiichi Fine Chemical Co., Ltd.
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Publication of WO2007145203A1 publication Critical patent/WO2007145203A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • the present invention relates to an optically active 2-amino-1-mono (4-fluorophenyl) ethanol and a derivative thereof useful as an intermediate for producing a pharmaceutical, and a method for producing them.
  • pyrimidone derivatives are known as drugs that enable fundamental prevention and Z or treatment for neurodegenerative diseases such as Alzheimer's disease (International Publication WO03Z27 080), and the pyrimidone ring is modified with substituted morpholine.
  • Proposed composites have been proposed.
  • Compound No. B031 described on page 40 of the above-mentioned International Publication is a compound having an optically active morpholinyl group modified with a 4 fluorophenol group.
  • the above publication does not specifically disclose a method for producing the optically active morpholinyl group modified with the 4 fluorophenyl group.
  • optically active 2-amino-1- (4-fluorophenyl) ethanol can be produced as a starting material.
  • optically active 2-amino-1-mono (4-fluorophenol) ethanol and derivatives thereof are expected to be useful as intermediates for the production of pharmaceuticals.
  • the above compounds in which (4 fluorophenyl) ethanol and amino groups are protected, and 2-amino-1- (4 fluorophenyl) ethanol and its derivatives useful as raw materials for production thereof are not known.
  • compounds having a halogen atom on the benzene ring of those compounds are also known.
  • Non-Patent Document 1 Tetrahedron Lett., 30, 367 (1989)
  • Non-Patent Document 2 J. Chem. Soc. PerkinTrans 1, 1759-1762 (1992)
  • Non-Patent Document 3 Synthesis, (7), 575- 578 (1990)
  • Non-Patent Document 4 Indian J. Chem. Sect. B, 31B (12), 821-823 (1992)
  • Non-Patent Document 5 Journal of the Chemical Society of Japan, (5), 910-913 (1985)
  • Non-Patent Document 6 J. Org. Chem., 50, 3237-3239 (1985)
  • Patent Document 1 Japanese Patent Laid-Open No. 61-85197
  • Patent Document 2 JP-A-5-170780
  • Patent Document 3 International Publication WO 01/073100
  • Patent Document 4 Japanese Patent Laid-Open No. 2001-46076
  • Patent Document 5 European Patent Application Publication No. 294995
  • An object of the present invention is to provide optically active 2-amino-1-ethanol (4-fluorophenyl) ethanol and its derivatives, which are useful as intermediates for the production of pharmaceuticals, and methods for producing them.
  • R 11 represents a protecting group for an amino group
  • R 11 represents a protecting group for an amino group
  • a salt thereof is asymmetrically hydrogenated in the presence of an asymmetric catalyst.
  • the asymmetric catalyst is represented by the following general formula (III):
  • R 21 is a hydrogen atom, —COOR, —COOR ”, or —CONHR ′′ ′ (R ,: R ′′, and R ′′ ′ are each independently an optionally substituted carbon number. 1 to 10 linear or branched alkyl groups, an aralkyl group which may have a substituent, or an aryl group which may have a substituent), R 22 and R 23 may independently have a substituent! / ⁇ may represent an aryl group, and R 24 and R 25 may each independently have a substituent! / ⁇ may be a cycloalkyl group.
  • carbon atoms marked with * 2 and * 3 are both S-configuration carbon atoms or R-configuration carbon atoms
  • a rhodium complex having a pyrrolidine bisphosphine compound as a ligand. How is
  • the method as described above wherein R 11 is a benzyl group, R 1 is a hydrogen atom or a benzyl group, n is 0, and a carbon atom attached with is S configuration; an R 11 Gabe Njiru group, a n is the compound represented by formula (II) is 0, R 1 is benzyl group, n is 0, the carbon atom marked with is S configuration
  • a compound represented by the general formula (I) is produced, and then the compound is subjected to catalytic reduction so that R 1 is a hydrogen atom, n is 0,
  • the above method is provided, which comprises the step of producing a compound represented by the general formula (I) in which the carbon atom marked with is S configuration.
  • the pyrrolidine bisphosphine compound represented by the above general formula (III) is (2S, 4S) -N-methylaminocarbo-luo 4 dicyclohexylphosphino 2 diphene.
  • Another aspect of the invention is that, according to the present invention, the above general formula (I) (wherein (R) represents n identical or different halogen atoms present at substitutable positions on the benzene ring).
  • N represents an integer of 0 to 4
  • R 1 represents a hydrogen atom or an amino-protecting group
  • a carbon atom attached with is a carbon atom having any configuration of S configuration or R configuration
  • a salt thereof is provided.
  • n is 0,
  • R 1 is hydrogen atom or a base Njiru group, the compound is carbon atom marked with * 1 is S or its Of salt is provided.
  • the method of the present invention provides optically active 2 amino-1-mono (4-fluorophenyl) ethanol and its derivatives, which are useful as intermediates for the production of pharmaceuticals, and efficient production methods thereof.
  • the substitution position of one fluorine atom shown on the benzene ring is not particularly limited, but is preferably 4-position (para-position to the ethanone group or ethanol group). ).
  • (R) represents n (n is 0 to 4) halogen atoms present at substitutable positions on the benzene ring.
  • the type of the hydrogen atom or the rogen atom is not particularly limited, and may be any of a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, preferably a fluorine atom or a chlorine atom, more preferably a fluorine atom. .
  • n is a force indicating an integer of 0 to 4, preferably 0 to 2, and more preferably 0 or 1, more preferably 0.
  • n there is only one fluorine atom on the benzene ring.
  • the type of protecting group for the amino group represented by R 1 or R 11 is not particularly limited, and is not eliminated during the reduction of the oxo group of the compound represented by the general formula (II). Any material can be used as long as it can be easily detached later.
  • introduction methods, and elimination methods for example, “Protective Groups in Organic 3 ⁇ 4yntheses” (Brother 3rd Edition, Theodora W. Green, John Wiley & Sons, Inc., 1999), "Handbook of Reagents for Organic Synthesis” (4 liters, John Wiley & Sons , Inc., 1999), etc.
  • a protecting group for an amino group a substituted group can be used as a protecting group for an amino group.
  • a carbon atom marked with * 1 represents a carbon atom having any configuration in either the S configuration or the R configuration, and preferably the S configuration. .
  • R 21 represents a hydrogen atom, COR ′, one COOR ′′, or —CONHR ′′ ′
  • R ′, R ′′, and R ′′ ′ are each independently A linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, an aralkyl group which may have a substituent, or a substituent.
  • a good aryl group is shown.
  • alkyl group examples include methyl group, ethyl group, n propyl group, isopropyl group, n-butyl group, s butyl group, t butyl group, n pentyl group, isopentyl group, s pentyl group, t pentyl group, neopentyl group.
  • alkyl part of a substituent having an alkyl part for example, an aralkyl group or an alkoxy group.
  • aralkyl group examples include benzyl group, 1-phenylethyl group, 2-phenylethyl group, and the like.
  • the aryl group may be either a monocyclic or polycyclic aryl group, and examples thereof include a phenyl group and a naphthyl group.
  • the alkyl group, the aralkyl group, or the aryl group represented by R ', R ", and R" have a substituent
  • the type, number, and substitution position of the substituent are not particularly limited.
  • the substituent include a halogen atom (which may be any of a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom), an alkyl group, an alkoxy group, a hydroxyl group, an aryl group, or an alkoxy group. Forces that are not limited to these.
  • R 21 is preferably CON HR "', and R"' is preferably a methyl group or a phenyl group.
  • R 22 and R 23 each independently represents an aryl group which may have a substituent.
  • the aryl group include a phenyl group and a naphthyl group.
  • the type, number, and substitution position of the substituent are not particularly limited.
  • the substituent include a halogen atom (which may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom), an alkyl group, an alkoxy group, a hydroxyl group, an aryl group, or an alkoxycarbonyl group. Power It is not limited to these.
  • R 22 and R 23 are preferably both phenyl groups.
  • R 24 and R 25 each independently have a substituent and may represent a cycloalkyl group.
  • the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • the type, number, and substitution position of the substituent are not particularly limited.
  • substituents examples include a halogen atom (which may be a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom), an alkyl group, an alkoxy group, a hydroxyl group, an aryl group, or an alkoxycarbonyl group. Power It is not limited to these.
  • R 24 and R 25 are preferably both cyclohexyl groups.
  • Examples of the pyrrolidine bisphosphine compound include (2S, 4S) -N-methylaminocarbol 4 dicyclohexylphosphino 2 diphenolphosphinomethylpyrrolidine, (2S, 4S) -N-phenolaminocarbo-ru 4 Dicyclohexylphosphino2 2 diphenylphosphinomethylpyrrolidine, (2S, 4S) —N—t Butyloxycarboxyl 4 Dicyclohexylphosphino2 2 diphenylphosphinomethylpyrrolidine, (2S , 4S) — N— t Butylaminocarbol 4 dicyclohexylphosphino 2 diphenylphosphinomethylpyrrolidine, (2S, 4S) —N—t butylcarbolulu 4-dicyclohexylphosphino 2 diphenylphosphine Inomethylpyrrolidine, (2S, 4S) —N-phenoxy
  • Particularly preferred pyridolysine bisphosphine compounds include (2S, 4S) -N-methylaminocarbo-luo 4-dicyclohexylphosphino 2-diphenylphosphinomethylpyrrolidine (hereinafter referred to as “(S, S ) —MCCPM ”), (2S, 4S) —N—Phenolaminocarbolulu 4 Dicix Oral hexylphosphino 2-diphenylphosphinomethylpyrrolidine (hereinafter“ (S, S) -P CCPM Etc.)).
  • a compound represented by the general formula (II) or a compound thereof used as a raw material is used.
  • the salt of can be easily prepared, for example, by brominating the corresponding substituted acetophenone compound and then reacting the resulting prom compound with an amino compound such as benzylamine.
  • the method for producing the compound represented by (II) is not limited to the above method.
  • the salt of the compound represented by the general formula (II) is not particularly limited as long as it is an acid addition salt that does not inhibit the asymmetric hydrogenation reaction. For example, either an inorganic acid addition salt or an organic acid addition salt can be used.
  • Examples of the inorganic acid addition salt include hydrochloride, bromate, sulfate, nitrate, perchlorate, or phosphate.
  • Examples of the organic acid addition salt include acetate, trifluoroacetate. Oxalate, p-toluenesulfonate, p-toluenesulfonate monohydrate, trifluoromethanesulfonate, or camphorsulfonate. Of these, hydrochloride is particularly preferable.
  • the salts exemplified above can be used as the salt of the compound of the general formula (I), and hydrochloride is particularly preferable.
  • the asymmetric catalyst used in the method of the present invention is a rhodium complex having an optically active pyrrolidine bisphosphine compound represented by the general formula (III) as a ligand.
  • This rhodium complex can be easily prepared by reacting a pyrrolidine bisphosphine compound represented by the general formula (III) with a rhodium compound, preferably a monovalent rhodium compound.
  • the kind of rhodium compound is not particularly limited, and examples thereof include rhodium compounds having ligands such as ethylene, 1,5-cyclotagen, and 2,5-norbornagen as ligands. More specifically, for example, (acetylylacetonato) (7?
  • the asymmetric catalyst can be prepared by mixing a pyrrolidine bisphosphine compound and a rhodium compound in a solvent. In general, it can be prepared at the time of use in a reaction system in which an asymmetric hydrogenation reaction is carried out. Between the rhodium compound and the pyrrolidine bisphosphine compound. The ratio is not particularly limited. For example, the amount of the pyrrolidine bisphosphine compound is 0.5 to 10 mol, preferably 1 to 5 mol, relative to 1 mol of the rhodium compound.
  • the amount of the asymmetric catalyst in the asymmetric hydrogenation reaction is not particularly limited, but is generally a catalytic amount, for example, 1 mol of the compound represented by the general formula (II) or a salt thereof.
  • the asymmetric catalyst can be used at a ratio of about 1Z2,000 to 1Z100,000 moles, preferably about 1Z5,000 to 1Z50,000 moles.
  • the asymmetric hydrogenation reaction can be performed in a solvent.
  • the type of the solvent is not particularly limited, and any solvent can be used as long as it is an inert solvent.
  • a mixture of two or more solvents can also be used.
  • alcohols such as methanol, ethanol, and isopropyl alcohol, mixed solvents of organic solvents and alcohols such as toluene, tetrahydrofuran, acetone, methyl isobutyl ketone, and chloroform, or mixed solvents of water and alcohols Etc.
  • the amount of the solvent to be used is not particularly limited, but is about 3 to 50 parts by mass, preferably about 5 to 15 parts by mass with respect to the mass of the compound represented by the general formula (II).
  • the hydrogen pressure in the asymmetric hydrogenation reaction is not particularly limited. For example, it may be in the range of about 0.1 to 15 MPa, 0.5 to L0 MPa, and more preferably 0.5 to 5 MPa.
  • the temperature of the asymmetric hydrogenation reaction is not particularly limited, but is, for example, 0 to 150 ° C, preferably 20 to 80 ° C, particularly preferably about 40 to 60 ° C, and the reaction time is about 1 to 100 hours. It is.
  • the compound represented by the general formula (I) is separated and purified by a usual separation and purification means such as filtration, concentration, crystallization, recrystallization or a combination thereof. It can be done.
  • the compound represented by R 1 is an amino protecting group.
  • R 1 is a hydrogen atom in the general formula (I)
  • “Protective Groups in Organic Syntheses” (Third Edition, T heodora W. Green et al., John Wiley & Sons, Inc.) ., 1999).
  • the deprotection can generally be easily performed by performing catalytic hydrogenation.
  • a catalyst used for debenzylation a catalyst capable of hydrogenolysis of a benzyl group, such as a palladium-carbon catalyst or a palladium hydroxide catalyst, can be used.
  • the catalyst is not limited to these catalysts. Absent. Palladium amount of Norajiumu catalyst 30 wt 0/0 approximately, preferably 5 to 2 about 0 wt%. The amount of the catalyst used is about 0.1 to 10 parts by weight, preferably about 0.5 to 5 parts by weight per 1 part by weight of the compound having a protecting group or a salt thereof.
  • Catalytic hydrogenation for debenzylation can be carried out in a solvent.
  • the solvent any solvent can be used as long as it does not inhibit the progress of the reaction, but alcohols are particularly preferable. Examples of alcohols include methanol, ethanol, propanol, and isopropyl alcohol.
  • the solvents may be used alone or in combination of two or more.
  • the amount of the solvent used is not particularly limited, but is about 1 to 50 parts by weight, preferably about 3 to 10 parts by weight, per 1 part by weight of the compound having a protecting group or a salt thereof.
  • the hydrogen pressure in catalytic hydrogenation is, for example, about 1 to 15 MPa, and preferably about 1 to: LOPa.
  • the catalytic hydrogenation is generally carried out at a temperature not higher than the boiling point of the solvent, for example, about 15 to 50 ° C. for 1 to 150 hours.
  • the product from which the protecting group for the amino group has been removed can be separated and purified by separation / purification means such as filtration, concentration, crystallization, recrystallization, or a combination of these.
  • separation / purification means such as filtration, concentration, crystallization, recrystallization, or a combination of these.
  • the optical purity of the compound represented by the general formula (I) or a salt thereof obtained by the above production method can be easily measured by, for example, an HPLC method using a chiral column.
  • Example 12 2 Benzylamino-1 mono (3 bromo-4 fluorophenyl) ethanone hydrochloride
  • the reaction was carried out in the same manner as in Example 1 except that 15.2 g of 3 bromo-4 fluoroacetophenone was used as the raw material.
  • 9-olg yield 36%) was obtained in the form of gray-white crystals of 2-benzylamino-11- (3-bromo-4-1-fluoro) ethanone hydrochloride.
  • optically active 2 amino-1-mono (4-fluorophenyl) ethanol and its derivatives which are useful as intermediates for producing pharmaceuticals, and their efficient production methods are provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de production d'un composé utile en tant qu'intermédiaire de production d'une substance pharmaceutique, représenté par la formule générale suivante (I): (I) ((R)n représente les mêmes ou différents atomes d'halogène au nombre de (n) présents dans une position substituable du cycle benzène; n représente un nombre entier de 0 à 4; R1 représente un atome d'hydrogène ou un groupe protecteur pour un groupe amino; l'atome de carbone marqué par *1 est un atome de carbone doté soit de la configuration S soit de la configuration R), comprenant l'étape consistant à soumettre un composé oxo correspondant à une hydrogénation asymétrique en utilisant un catalyseur asymétrique, un complexe de rhodium ayant un composé pyrrolidinebisphosphine en tant que ligand.
PCT/JP2007/061799 2006-06-13 2007-06-12 2-amino-1-(4-fluorophenyl) éthanol optiquement actif WO2007145203A1 (fr)

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JP2006163293 2006-06-13
JP2006-163293 2006-06-13

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5350167A (en) * 1976-10-18 1978-05-08 Morton Norwich Products Inc 11***55*substituted**22oxazolyl*methlene*amino** 2*44imidalizinedione and its preparation
JPS572245A (en) * 1980-05-08 1982-01-07 Beecham Group Ltd Arylethanol amine derivatives, their manufacture and medicinal composition containing them
JPH0228110A (ja) * 1989-06-13 1990-01-30 Lab L Lafon Sa 抗抑うつ剤
JPH0570412A (ja) * 1991-09-13 1993-03-23 Fuji Yakuhin Kogyo Kk 光学活性なβ−アミノアルコールの製造方法
JP3068198B2 (ja) * 1995-05-12 2000-07-24 日清製粉株式会社 １，４−ベンゾジオキシン誘導体
JP2003507357A (ja) * 1999-08-14 2003-02-25 ベーリンガー インゲルハイム ファルマ コマンディトゲゼルシャフト アドレナリンの調製方法
JP2003201269A (ja) * 2001-10-31 2003-07-18 Kanto Chem Co Inc 光学活性アミノアルコールおよびその中間体の製造方法
JP2004115437A (ja) * 2002-09-26 2004-04-15 Iwaki Seiyaku Co Ltd Ｌ−フェニレフリンを製造する方法
JP2004534010A (ja) * 2001-03-28 2004-11-11 ブリストル−マイヤーズ　スクイブ　カンパニー 新規なチロシンキナーゼ阻害剤
JP2006503884A (ja) * 2002-10-24 2006-02-02 ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト （ｒ）−サルブタモールの調製方法
WO2007011065A2 (fr) * 2005-07-22 2007-01-25 Mitsubishi Tanabe Pharma Corporation Compose intermediaire utilise pour la synthese d'un agent pharmaceutique, procede de production de ce dernier

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5350167A (en) * 1976-10-18 1978-05-08 Morton Norwich Products Inc 11***55*substituted**22oxazolyl*methlene*amino** 2*44imidalizinedione and its preparation
JPS572245A (en) * 1980-05-08 1982-01-07 Beecham Group Ltd Arylethanol amine derivatives, their manufacture and medicinal composition containing them
JPH0228110A (ja) * 1989-06-13 1990-01-30 Lab L Lafon Sa 抗抑うつ剤
JPH0570412A (ja) * 1991-09-13 1993-03-23 Fuji Yakuhin Kogyo Kk 光学活性なβ−アミノアルコールの製造方法
JP3068198B2 (ja) * 1995-05-12 2000-07-24 日清製粉株式会社 １，４−ベンゾジオキシン誘導体
JP2003507357A (ja) * 1999-08-14 2003-02-25 ベーリンガー インゲルハイム ファルマ コマンディトゲゼルシャフト アドレナリンの調製方法
JP2004534010A (ja) * 2001-03-28 2004-11-11 ブリストル−マイヤーズ　スクイブ　カンパニー 新規なチロシンキナーゼ阻害剤
JP2003201269A (ja) * 2001-10-31 2003-07-18 Kanto Chem Co Inc 光学活性アミノアルコールおよびその中間体の製造方法
JP2004115437A (ja) * 2002-09-26 2004-04-15 Iwaki Seiyaku Co Ltd Ｌ−フェニレフリンを製造する方法
JP2006503884A (ja) * 2002-10-24 2006-02-02 ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト （ｒ）−サルブタモールの調製方法
WO2007011065A2 (fr) * 2005-07-22 2007-01-25 Mitsubishi Tanabe Pharma Corporation Compose intermediaire utilise pour la synthese d'un agent pharmaceutique, procede de production de ce dernier

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