[go: up one dir, main page]

WO2001016118A1 - Procedes pour la preparation de composes d'oxazolidinone optiquement actifs - Google Patents

Procedes pour la preparation de composes d'oxazolidinone optiquement actifs Download PDF

Info

Publication number
WO2001016118A1
WO2001016118A1 PCT/JP2000/005829 JP0005829W WO0116118A1 WO 2001016118 A1 WO2001016118 A1 WO 2001016118A1 JP 0005829 W JP0005829 W JP 0005829W WO 0116118 A1 WO0116118 A1 WO 0116118A1
Authority
WO
WIPO (PCT)
Prior art keywords
optically active
formula
producing
group
compound
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.)
Ceased
Application number
PCT/JP2000/005829
Other languages
English (en)
Japanese (ja)
Inventor
Hisao Ikeda
Toshiaki Takeyama
Motohiko Hidaka
Kazutaka Arai
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.)
Nissan Chemical Corp
Original Assignee
Nissan Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Publication of WO2001016118A1 publication Critical patent/WO2001016118A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2

Definitions

  • the present invention provides an optically active oxazolidinone compound, which is useful as an intermediate for the production of / 9-blockers, oxazolidinone antibacterial agents, etc., from an optically active tris- (2,3-epoxyalkyl) -isocyanurate compound. How to do it. Background art
  • Tetrahedron, vol. 43, No. 11, page 2505 (1989) describes a method for synthesizing optically active oxazolidinone compounds, but the process is long and not necessarily effective. It cannot be said that it is a simple manufacturing method.
  • Tetrahedron, Vol. 54, No. 14, pp. 3465 states that N- (2,3-epoxypropyl) carbamate and racemic oxazolidino from amines.
  • the method for producing styrene is described in Tetrahedron Letters, No. 12, p. 809 (1971), as a racemic material from phenyldaricidyl ether and isocyanate.
  • a method for producing oxazolidinone is described, but no description is given for an optically active substance.
  • US Pat. No. 3,446,814 discloses a racemic trisux (2,3- A method for producing oxazolidinone from monoisocyanurate and phenols has been described. So far, optically active oxazolidinone has been produced from optically active tris- (2,3-epoxypropyl) isocyanurate. There is no known method.
  • An object of the present invention is to provide a method for easily producing an optically active oxazolidinone compound, which is useful as an intermediate for producing an i-blocker or an oxazolidinone antibacterial agent.
  • the oxazolidinone compound of the present invention can be easily converted to the above-mentioned production intermediate aminopropanol derivative by hydrolysis.
  • -Broc is a wide-ranging therapeutic drug from the treatment of angina and arrhythmias, to hypertension, thyroid dysfunction, pheochromocytoma, cardiovascular disease, neuropsychiatry and anesthesia. Has been used as In addition, the oxazolidinone antibacterial agent Linez 0
  • 11d (trade name: Zyvox) is known to have high efficacy against microbial infections caused by noncomycin-resistant staphylococci, streptococci, anaerobic bacteria and tuberculosis bacteria.
  • the present inventors have conducted various studies to solve the above problems, and as a result, have found that an optically active tris (2,3-epoxyalkyl) monoisocyanurate compound and phenols, thiophenols, and anilines can be used in the presence of a base.
  • the present inventors have found that an optically active oxazolidinone compound useful as an intermediate for the production of ⁇ -blocker and oxazolidinone-based antibacterial agents and the like can be easily produced by reacting the compound with the compound (1), thereby completing the present invention.
  • Tris- (2,3-epoxyalkyl) monoisocyanurate used as a raw material in the present invention has a relatively small number of asymmetric centers, three in a molecule, and has relatively high purity due to good crystallinity. It is easy to react with phenols, thiophenols, and anilines, and has a mild and mild optically available characteristic. High purity oxazolidinone compound can be obtained under the conditions, disclosure of the invention
  • Equation (1) which is obtained by reacting an optically active tris- (2,3-epoxyalkyl) -isocyanurate represented by the formula (2) with a compound represented by the formula (2) R′XH,
  • * represents an asymmetric carbon
  • X represents 0, NR 3 , PR 3 , and S
  • R ′ represents at least one atom selected from the group consisting of 0, S, N, and F.
  • R ', R 2 and R 3 may be the same or different, respectively, to obtain a tris- (2,3-epoxyalkyl) -isocyanurate adduct represented by the formula: Process, and
  • the method for producing an optically active oxazolidinone compound according to the second aspect wherein a Lewis acid, an inorganic salt, an inorganic oxide, or an ionic salt is added as a catalyst to the step (A),
  • any one of the first to fifth aspects in which X is an oxygen atom is an oxygen atom
  • X is a first aspect to optically active Okisazorijinon compound of placing serial to any one of the fifth aspect is NR 3,
  • the optics according to any one of the first to fifth aspects wherein X is 0 and R 1 is an optionally substituted aromatic ring or an optionally substituted heterocyclic ring.
  • the optics according to any one of the first to fifth aspects, wherein X is NH and R 1 is an optionally substituted aromatic ring or an optionally substituted heterocyclic ring.
  • a method for producing an optically active oxazolidinone compound according to any one of the first to fifth aspects wherein R 2 is hydrogen and X is an oxygen atom.
  • R 1 represents an organic group having 1 to 36 carbon atoms which may contain one or more atoms selected from the group consisting of 0, S, N and P.
  • Force 5 is not particularly restricted but includes organic group, preferably an alkyl group, an aliphatic hydrocarbon group, cycloalkyl group, optionally substituted aromatic hydrocarbon group, heterocyclic, alkoxycarbonylalkyl And the like.
  • R ′ is an organic group having 1 to 36 carbon atoms, including the atomic groups exemplified above, and is preferably an organic group having 1 to 18 carbon atoms.
  • R 2 and R 3 represent H or an organic group having 1 to 36 carbon atoms which may contain one or more atoms selected from the group consisting of 0, S, N and P.
  • the organic group is not particularly limited, but is preferably an aliphatic hydrocarbon group such as an alkyl group or a cycloalkyl group, an aromatic hydrocarbon group, a heterocyclic ring, an alkoxycarbonylalkyl group, or the like. It is. It is an organic group having 1 to 36 carbon atoms comprising the atomic groups exemplified above, and preferably an organic group having 1 to 18 carbon atoms.
  • the alkyl group includes a methyl group, an ethyl group, a propyl group and the like
  • the cycloalkyl group includes a cyclopropyl group, a cyclopentyl group and a cyclohexyl group.
  • aromatic hydrocarbon group examples include fuunyl and naphthyl.
  • Heterocycles include indole, benzothiophene, 1,2,5-thiadiazol, pyridine and the like.
  • alkoxycarbonylalkyl group examples include a methoxycarbonylmethyl group and an ethoxycarbonylethyl group.
  • the above-mentioned organic group includes a halogen, an alkyl group, a cycloalkyl group, an alkylamino group, an alkoxy group, an alkylthio group, a cyano group, a nitro group, an alkoxyl group, a hydroxyl group, and an amino group. And may have one or more substituents selected from the group consisting of the same or different substituents.
  • the preferred method for producing the optically active oxazolidinone compound represented by the formula (3) according to the present invention comprises, as the step (A), an optically active tris- (epoxyalkylene) -iso-isocyanurate represented by the formula (1):
  • the phenols and anilines represented by (2) are reacted to obtain an optically active tris (epoxyalkyl) -isocyanurate adduct represented by the formula (4).
  • the optically active tris- (2,3-epoxyalkyl) isocyanurate used as a raw material in the present invention easily reacts with the compound represented by the formula (2) R'XH, and has a high purity optical property under mild conditions.
  • Formula (1) which is a starting material of the present method, represents a compound of (2R, 2R,, 2R ") or (2S, 2S ', 2S").
  • 2R, 2R, 2R represents a compound of (2R, 2R,, 2R ") or (2S, 2S ', 2S").
  • optically active tris (2,3_epoxypropyl)
  • the isocyanurate is reacted with optically active epichlorohydrin on cyanolic acid, followed by the dropwise addition of an aqueous solution of NaOH while dehydrating and refluxing, whereby a dehydrochlorination reaction takes place, and the desired optically active tris (2) , 3-epoxypropyl)
  • One isocyanurate can be obtained.
  • optically active tris (2,3-epoxyalkyl) isocyanurate used as a raw material in the present invention include a hydrogen atom for R 2 and a lower alkyl group such as a methyl group or an ethyl group.
  • (2,3-epoxypropyl) monoisocyanurate and tris (2,3-epoxypropyl-12-methyl) isocyanurate can be exemplified.
  • R 2 is a hydrogen atom during the production process of the present application, that is, when tris- (2,3-epoxypropyl) -isocyanurate is used, the compound easily reacts with the compound represented by the formula (2) and is mild. It is most preferable because a high purity optically active oxazolidinone compound can be obtained under the conditions.
  • the optically active tris- (2,3-epoxyalkyl) monoisocyanurate used in the present invention is preferably of high purity due to the nature of its use.
  • the purity is preferably 0% or more, and more preferably 95% or more.
  • the optical purity of the raw material is important because it affects the optical purity of the target substance, and is preferably S0% e.e. or more, more preferably 90% e.e. or more.
  • optically active tris- (2,3-epoxypropyl) -isocyanurate is purified by recrystallization using a solvent such as methanol. It is possible to
  • R 1 is a fuunyl group or a naphthyl group as an aromatic hydrocarbon group, and indole, benzothiophene, 3,4-dihydro-12 (1H) 1 as an organic group comprising a heterocyclic ring.
  • Those having a skeleton of quinolinone, pyridine or the like are preferred.
  • the steps (A) and (B) are diluted with a solvent and reacted under milder conditions.
  • the solvent only needs to be inert to the reaction.
  • aromatic hydrocarbons such as toluene and benzene
  • ethers such as dioxane, dimethyloxetane and tetrahydrofuran, methanol, ethanol, 2- Alcohols such as methoxyethanol and 2-ethoxyethanol
  • halogenated hydrocarbons such as dichloroethane and chloroform
  • ketones such as acetone and methyl ethyl ketone
  • nitriles such as acetonitrile
  • pyridine Tertiary amines such as triethylamine, amides such as N, N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide, nitrone compounds such as nitroethane and nitrobenzene, esters such as ethyl acetate, and water
  • the reaction can be carried out at a temperature between 178 and the boiling point of the solvent. Preferably, it is carried out between room temperature (20 ° C.) and the boiling point of the solvent.
  • these solvents can be used using a solvent in which the steps (A) and (B) are the same, or using different solvents.
  • the present invention provides a first method in which the steps (A) and (B) are performed continuously, and a step (B) in a preferred solvent after the adduct (4) is isolated and purified in the step (A).
  • the second method is mentioned.
  • Examples of the compound of the formula (2), which is one of the starting materials used in the process of the present invention, include phenol, naphthol, guaiacol (2-methoxyphenol), 2-cyclopentylphenol, aniline, and 3-fluoro-41-morpholinoa. Diphosphorus, 3-hydroxyl 4-morpholino 1, 2, 5-thiadiazol, chiopheno , Difuunilphosphite, and the like, but the present invention is not limited thereto.
  • the amount of the formula (2) used in the present invention is not particularly limited, but is preferably from 3 to 100 mol per 1 mol of tris (2,3-epoxyalkyl) -isocyanurate. More preferably, it is used in the range of 3 mol to 30 mol.
  • a catalyst can be used if necessary. It can use any catalyst that promotes the reaction of the epoxy compound.
  • examples of the acid catalyst include Lewis acids such as aluminum chloride, tin chloride, boron trifluoride, and 3 (trifluoromethanesulfonic acid) ittibidium.
  • inorganic salts such as sodium bromide, lithium bromide, and calcium chloride; inorganic oxides such as titanium oxide and silica; tetraethylammonium bromide; triphenylethylphosphonium bromide; Onion salt. .
  • the catalyst used in the step B for decomposing the optically active tris (epoxyalkyl) -isocyanurate adduct represented by the formula (4) a basic substance or an ionic salt is mentioned as a preferable catalyst.
  • a basic substance or an ionic salt is mentioned as a preferable catalyst.
  • Can be These can be used alone or in combination.
  • Examples of the basic substance include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; metal hydrides such as sodium hydride; and potassium t. -Metal alkoxides such as butoxide; organometallic amides such as lithium diisopropylamide; organic metal compounds such as n-butyllithium; pyridine; 4-dimethylaminopyridine, triethylamine, and methyl isopropylamide And an organic base such as dimethylbenzylamine.
  • an inorganic base such as sodium hydroxide or hydroxylating sphere, or an organic base such as dimethylpentylamine is used.
  • Examples of the honium salt used in the present invention include an ammonium salt, a phosphonium salt, an arsonium salt, a stibonium salt, an oxonium salt, a sulfonium salt, a selenonium salt, a stannonium salt, and a jordonium salt.
  • the use of a quaternary ammonium salt or a tertiary sulfonium salt is preferable because side reactions can be suppressed, and a quaternary ammonium salt can be reacted under mild conditions, and the yield and purity are relatively high. It is particularly preferable because a good product is obtained.
  • Preferred as the quaternary ammonium salt are, for example, halogenated tribenzylbenzylammonium, norogendanitriethylbenzylammonium, nordogenidanitrioctylmethylammonium, and nordogenidhitritribenzylbenzylammonium. And halogenated trimethylbenzylammonium, halogenated tetramethylammonium, halogenated tetraethylammonium, halogenated tetrabutylammonium, and the like. 1,8-diaza-1 8-benzylbicyclo
  • Preferable quaternary phosphonium salts include halogenated tetraalkylphosphonium, such as halogenated tetra-n-butylphosphonium and halogenated tetra-n-propylphosphonium, and halogenated tetramethylphosphonate.
  • Halogenated trialkyl benzylphosphonium such as benzylbenzylphosphoric acid, halogenated triphenylmethylphosphonium, halogenated triphenylmethylphosphonium, etc.
  • Examples of the halogen used as a counter ion of the onium salt in the present invention include chloride ion (C 1 ⁇ ), bromide ion (Br—), and iodine ion (I—). it can.
  • the quaternary ammonium salt can be converted to a hydroxyl group (OH—) by converting it with a hydroxyl group such as NaOH to form a base. Yes, and this can also be used as a preference.
  • step (A) and step (B) are performed consecutively, the compound of formula (1), the compound of formula (2) and the catalyst used in step (B) are added simultaneously to the solvent and reacted. Can be.
  • an optically active tris- (2,3-epoxyalkyl) monoisocyanurate of the formula (1) and a hydroxyl group-containing compound in which X is an oxygen atom in the compound of the formula (2) are included.
  • an optically active oxazolidinone compound in which X is an oxygen atom can be produced also in the formula (3).
  • optically active tris- (2,3-epoxyalkyl) -isocyanurate of the formula (1) and an amine-based compound of the formula (2) wherein X is NR 3 (particularly NH) are used.
  • the reaction is carried out in the presence of a base or an onium salt to produce an optically active oxazolidinone compound in which X is NR 3 (particularly NH) in formula (3).
  • an optically active tris- (2,3-epoxyalkyl) -isocyanurate of the formula (1) an optically active tris- (2,3-epoxypropyl) -isocyanurate in which R 2 is a hydrogen atom, and the formula (2)
  • R 2 is a hydrogen atom
  • the formula (3) a compound having a hydroxyl group or an amino group, wherein X is an oxygen atom or NH, is reacted in the presence of a base or onium salt.
  • a zolidinone compound can be produced.
  • the optically active tris (2,3-epoxypropyl) monoisocyanurate in the formula (1) is used in a solvent in the presence of a phenol or aniline of the formula (2) and a base or an oxime.
  • a salt By reacting in the presence of a salt, an optically active oxazolidinone compound of the formula (3) can be synthesized.
  • step (C) of hydrolyzing the tris (2,3-epoxyalkyl) -isocyanurate adduct of the formula (4) obtained in the step (B) is carried out, and the step of the formula (5) is carried out. Is obtained.
  • the step (C) of hydrolyzing the optically active oxazolidinone compound represented by the formula (3) is carried out to obtain the optically active amino alcohol represented by the formula (5).
  • the catalyst used in the steps (C) and (C,) include a basic substance and an acidic substance.
  • the basic substance include inorganic bases such as sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium carbonate, sodium methoxide, sodium methoxide, and potassium.
  • Metal alkoxides such as t-butoxide, and organic bases such as pyridine, 4-dimethylaminopyridine, triethylamine, getyl isopropylamine, and dimethylpendiamine can be used.
  • an inorganic base such as sodium hydroxide and potassium hydroxide is used.
  • the acidic substance include inorganic acids such as hydrochloric acid, hydrobromic acid, hydrofluoric acid, sulfuric acid, and nitric acid, organic acids such as formic acid, acetic acid, methanesulfonic acid, trifluoroacetic acid, and trifluoromethanesulfonic acid, naphthion, and amberlyst.
  • Cation exchange resin can be used.
  • Powdered potassium hydroxide 140 mg, (2R, 2R ', 2R ")-tris- (2,3-epoxypropyl) -isocyanurate (optical purity 99% e.e. or more) 6.1 50 ml of benzene with monochrome mouth was added to 8 g and 9.0 g of ⁇ -naphthol, and the mixture was heated and refluxed with stirring, allowed to react for 2 hours, allowed to cool to room temperature, and the resulting crystals were collected by filtration. After washing with water, drying was performed to obtain 13.38 g (melting point: 157.6 to 158.0, yield: 88%) of the title compound as white crystals.
  • an optically active oxazolidinone compound which is useful as an intermediate for the production of /?-Blockers, etc., can be easily converted from an optically active tris- (epoxyalkyl) -iso cyanurate compound as a raw material.
  • a method of manufacturing can be provided.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Cette invention se rapporte à un procédé servant à préparer des composés d'oxazolidinone optiquement actifs utiles comme intermédiaires dans la préparation de bêta-bloquants à partir de composés d'isocyanurate tris(2,3-époxyalkyle) optiquement actifs. Cette invention se rapporte spécifiquement à un procédé consistant à faire réagir un isocyanurate tris(2,3-époxyalkyle) optiquement actif, représenté par la formule générale (1) avec un composé représenté par la formule générale R1XH (2), et à obtenir ainsi un composé d'oxazolidinone optiquement actif représenté par la formule générale (3).
PCT/JP2000/005829 1999-08-30 2000-08-29 Procedes pour la preparation de composes d'oxazolidinone optiquement actifs Ceased WO2001016118A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP24330999 1999-08-30
JP11/243309 1999-08-30

Publications (1)

Publication Number Publication Date
WO2001016118A1 true WO2001016118A1 (fr) 2001-03-08

Family

ID=17101927

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2000/005829 Ceased WO2001016118A1 (fr) 1999-08-30 2000-08-29 Procedes pour la preparation de composes d'oxazolidinone optiquement actifs

Country Status (1)

Country Link
WO (1) WO2001016118A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10219670B2 (en) 2014-09-05 2019-03-05 Tennant Company Systems and methods for supplying treatment liquids having nanobubbles

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3446814A (en) * 1965-07-24 1969-05-27 Henkel & Cie Gmbh Process for the preparation of substituted oxazolidones
JPH0713338A (ja) * 1993-06-18 1995-01-17 Iwatsu Electric Co Ltd 製版機
WO1999045005A1 (fr) * 1998-03-02 1999-09-10 Nissan Chemical Industries, Ltd. Compose epoxy optiquement actif

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3446814A (en) * 1965-07-24 1969-05-27 Henkel & Cie Gmbh Process for the preparation of substituted oxazolidones
JPH0713338A (ja) * 1993-06-18 1995-01-17 Iwatsu Electric Co Ltd 製版機
WO1999045005A1 (fr) * 1998-03-02 1999-09-10 Nissan Chemical Industries, Ltd. Compose epoxy optiquement actif

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BOLOGNA, CARDILLO G. ET AL.: "An efficient synthesis of (R)-(+)- and (S)-(-)- propranolol from resolved 5-iodomethyloxazolidin-2-ones", TETRAHEDRON, vol. 43, no. 11, 1987, pages 2505 - 2512, XP002934221 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10219670B2 (en) 2014-09-05 2019-03-05 Tennant Company Systems and methods for supplying treatment liquids having nanobubbles

Similar Documents

Publication Publication Date Title
US6362334B1 (en) Phthalamide compounds
JP2004532210A (ja) アゼチジノン中間体化合物のエナンチオ選択性合成
JPH04500077A (ja) ペネムおよびカルバペネム製造のための中間体化合物の製造法
US5036090A (en) 3-Aryloxazolidinone derivatives, process for their preparation and their use in therapy
TW201028374A (en) Method of preparing ezetimibe and intermediates used therein
TW200838855A (en) Method for preparing 1-substituted-4-nitroimidazole compound
US5264443A (en) 3-aryl oxazolidinone compounds and therapeutic use thereof
WO2001016118A1 (fr) Procedes pour la preparation de composes d'oxazolidinone optiquement actifs
JP2001139564A (ja) 光学活性オキサゾリジノン化合物の製造法
US8178666B2 (en) 2-aminobenzoxazole process
JP3740886B2 (ja) オキサゾリジン−２−オン類の製造方法
WO2016158737A1 (fr) Procédé de production de 1-(4-hydroxyphényl)-4-(4-trifluorométhoxyphénoxy)pipéridine ou d'un sel dudit composé
US5235063A (en) Process of preparing by condensation certain
JPWO2002076958A1 (ja) ５−置換オキサゾール化合物および５−置換イミダゾール化合物の製造方法
JP4614026B2 (ja) Ｎ−置換−５−ヒドロキシ−テトラヒドロ−２−ピリミジノンの製造方法
JP2002179663A (ja) オキシラン化合物の製造方法
JP3002978B2 (ja) プロポキシニトロベンゼン類の製造法
JPH04270272A (ja) アミノアルキルモルホリン誘導体の製造法
JPH09278748A (ja) Ｎ−置換−β−ラクタム化合物の製造法
JPH06116240A (ja) 光学活性２−プロパノール誘導体の製造法
JPS607985B2 (ja) ヒダントイン類の製法
JP2002275167A (ja) ５−置換オキサゾール化合物の製造方法
JP2002145879A (ja) 光学活性トリス−（２，３−エポキシプロピル）−イソシアヌレートの製造方法
JP2002047229A (ja) 光学活性化合物の合成法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
122 Ep: pct application non-entry in european phase