JPH115786A - Novel aminohydroxypropylpiperazine derivative - Google Patents

Novel aminohydroxypropylpiperazine derivative

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Publication number
JPH115786A
JPH115786A JP9173239A JP17323997A JPH115786A JP H115786 A JPH115786 A JP H115786A JP 9173239 A JP9173239 A JP 9173239A JP 17323997 A JP17323997 A JP 17323997A JP H115786 A JPH115786 A JP H115786A
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JP
Japan
Prior art keywords
group
piperazine
compound
hydroxy
phenyl
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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.)
Pending
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JP9173239A
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Japanese (ja)
Inventor
Yoko Kawakatsu
Makoto Kimura
Takayuki Namiki
Koji Yamada
Masayuki Yanagi
隆之 並木
浩次 山田
庸行 川勝
誠 木村
正行 柳
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Pola Chem Ind Inc
ポーラ化成工業株式会社
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Application filed by Pola Chem Ind Inc, ポーラ化成工業株式会社 filed Critical Pola Chem Ind Inc
Priority to JP9173239A priority Critical patent/JPH115786A/en
Publication of JPH115786A publication Critical patent/JPH115786A/en
Application status is Pending legal-status Critical

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    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of products other than chlorine, adipic acid, caprolactam, or chlorodifluoromethane, e.g. bulk or fine chemicals or pharmaceuticals
    • Y02P20/55Synthetic design, e.g. reducing the use of auxiliary or protecting groups

Abstract

PROBLEM TO BE SOLVED: To obtain a novel aminohydroxypropylpiperazine or its salt that is useful as a starting substance for a variety of pharmaceuticals. SOLUTION: This novel compound is an aminohydroxypropylpiperazine derivative of formula I (R1 is H, a protecting group; R2 and R3 are each H, a 1-4C alkyl, an aromatic group that may have substituents) or its salt, typically (S)-1-(2-hydroxy-3-phenylamino-propyl)-4-triphenylmethylpiperazine of formula II. A compound of formula I, for example, the compound of formula II is prepared by allowing (S)-N-(3-chloro-2-hydroxypropyl)aniline of formula III to react with 1-triphenylmethylpiperazine of formula IV in the presence of potassium carbonate and potassium iodide.

Description

【発明の詳細な説明】 DETAILED DESCRIPTION OF THE INVENTION

【0001】 [0001]

【発明の属する技術分野】本発明は各種医薬品原薬の原料として有用な、アミノヒドロキシプロピルピペラジン誘導体又はそれらの塩に関する。 The present invention relates to useful as a raw material for various pharmaceutical ingredients, about amino hydroxypropyl piperazine derivative or a salt thereof.

【0002】 [0002]

【従来の技術】アミノヒドロキシプロピルピペラジン構造は、医薬の分野では薬効を発現させるに有益な部分構造であり、例えば、ピペラジンのもう一方の窒素原子上の水素原子が4,4−ビス(4−フルオロフェニル)ブチル基やビス(4−フルオロフェニル)メチル基に置換した化合物は、ドーパミン再取込阻害作用やカルシウム拮抗作用等を有することが知られているし、ジベンゾスベラニル基やジフェニルアセチル基で置換された化合物は、多剤耐性癌に対して耐性を低下させ、薬剤に対する感受性を回復せしめる作用を有することが知られている。 BACKGROUND OF THE INVENTION Amino-hydroxypropyl piperazine structure, in the field of medicine are valuable partial structure to express drug efficacy, for example, a hydrogen atom on the other nitrogen atom of the piperazine 4,4-bis (4- fluorophenyl) butyl group or a bis (4-fluorophenyl) compound substituted on methyl group, to have been known to have dopamine reuptake inhibitory action and calcium antagonism and the like, dibenzosuberone Bella sulfonyl group and diphenylacetyl compounds substituted with groups resistance lowers the relative multidrug resistant cancer, are known to have an effect allowed to restore sensitivity to the drug. 更に、この様な薬理的に有用なアミノヒドロキシプロピルピペラジン構造に於いては、水酸基の結合した炭素原子が不斉炭素となり、光学異性体を生じ光学異性体によってその薬効が大きく異なる場合があることも既に知られていることである。 Further, In such pharmacologically useful amino hydroxypropyl piperazine structures, the carbon atoms bonded to the hydroxyl group becomes asymmetric carbon, it is when the efficacy by the optical isomers results in optical isomers are significantly different it is also what is already known.

【0003】この様な観点から、アミノヒドロキシプロピルピペラジン構造を有する医薬品の立体構造を保持した種々の合成法が考案されてきた。 [0003] From such a viewpoint, various synthetic methods which holds the three-dimensional structure of a pharmaceutical having an amino hydroxypropyl piperazine structures have been devised. 例えば、予め置換アミノヒドロキシプロピル基以外の部分を構築しておき、 For example, advance to build a portion other than the pre-substituted amino hydroxypropyl group,
これに光学活性な2,3−エポキシプロピルハライド又はグリシジルトシレートを反応させ続いて置換アミン体をを反応させる方法や、光学活性な置換アミノプロペンオキシド類を開環付加させる方法などが開発され、光学純度の高い化合物が得られるようになった。 And a method of reacting it in optically active 2,3-epoxypropyl halide or glycidyl tosylate of and subsequently reacted substituted amine compound, a method for ring-opening addition of an optically active substituted amino propene oxides have been developed, but also higher optical purity compound. しかしながら、時としてこの様な反応に於いては一部ラセミ化が起こる場合があり、その様な場合には精製などを行って光学純度を向上させなければならないことがあった。 However, sometimes In such reactions may cause some racemization takes place, there may have to be to improve the optical purity performing such purification if such. 即ち、立体保持に優れた、アミノヒドロキシプロピルピペラジン構造を有する化合物の合成の手段が望まれていた。 That is, excellent solid retention, combining means a compound having an amino hydroxypropyl piperazine structure has been desired.

【0004】 [0004]

【発明が解決しようとする課題】本発明はかかる状況下為されたものであり、立体保持に優れたアミノヒドロキシプロピルピペラジン構造を有する化合物の合成に有用な中間体を提供することを課題とする。 [SUMMARY OF THE INVENTION The present invention has been made under such circumstances, and an object thereof is to provide intermediates useful for the synthesis of compounds having excellent amino hydroxypropyl piperazine structure retention of the configuration .

【0005】 [0005]

【課題の解決手段】本発明者等はこの様な状況に鑑みて、立体保持に優れたアミノヒドロキシプロピルピペラジン構造を有する化合物の合成に有用な中間体を求めて鋭意研究を重ねた結果、下記一般式(I)に示される化合物又はそれらの塩がその様な性質を有していることを見いだし発明を完成させるに至った。 BACKGROUND solutions to problems the present inventors in view of such circumstances, the results of extensive research in search of intermediates useful in the synthesis of compounds having excellent amino hydroxypropyl piperazine structures stereo holding, following generally the compounds shown in formula (I) or salt thereof and completed the invention found to have such properties. 以下、本発明について発明の実施の形態を中心に詳細に説明する。 Hereinafter, the present invention will be described in detail focusing on embodiments of the invention will.

【0006】 [0006]

【化2】 ## STR2 ## 一般式(I) (但し式中R1は水素原子又は保護基を表し、R2、R General formula (I) (where Shikichu R1 represents a hydrogen atom or a protecting group, R2, R
3はそれぞれ独立に水素原子、炭素数1〜4のアルキル基又は置換基を有していても良い芳香族基を表す。 3 are each independently a hydrogen atom, an alkyl group or which may have a substituent aromatic group having 1 to 4 carbon atoms. )

【0007】 [0007]

【発明の実施の形態】本発明の化合物は上記一般式(I)に表される化合物からなる。 The compounds of the present invention DETAILED DESCRIPTION OF THE INVENTION comprises a compound represented by the general formula (I). ここでR1に表される基の内、保護基としては、アミノヒドロキシプロピル基を導入する反応においては安定であって、酸などで容易に脱離しうるものが好ましく、例えばこの様な基としてはトリフェニルメチル基、パラトルエンスルホニル基、ジベンゾスベラニル基等が例示でき、これらの内ではトリフェニルメチル基が特に好ましい。 Wherein among the groups represented in R1, the protecting group, are stable in the reaction of introducing an amino hydroxypropyl group are preferably those capable readily desorbed by an acid, for example, as such groups triphenylmethyl group, p-toluenesulfonyl group, can be exemplified the dibenzosuberone Bella sulfonyl group, and particularly preferably a triphenylmethyl group of these. これらは対応するクロリドを過剰のピペラジンに作用させることによって容易に得ることが出来る。 These can be easily obtained by the action of the corresponding chloride with excess piperazine. 即ち、片方の窒素原子に保護基を導入したピペラジンをこの様に作成し、このものに置換アミノハロゲン化ヒドロキシプロパンをアルカリ存在下縮合させれば、一般式(I)に表される化合物の内、R1が保護基である化合物を得ることが出来る。 That is, create a piperazine of introducing protecting groups to the nitrogen atom of one in this manner, if the intended substituted amino halogenated hydroxy propane a engaged alkali presence contraction, among compounds represented by the general formula (I) , to give compound R1 is a protecting group.
ここで置換アミノ基としては置換基を有していても良いフェニルアミノ基が好適に例示できる。 Here is a phenyl amino group which may have a substituent can be suitably exemplified as a substituted amino group. 勿論のこりのアミノ基の窒素原子上の水素原子を置換基で置換することも可能であり、このものも本発明の化合物である。 Of course it is also possible to replace the hydrogen atoms on the nitrogen atom of the amino group of the remaining substituents, also a compound of the present invention this compound. かかる置換基を有していても良いフェニル基以外のアミノ基の置換基としてはアルキル基が例示でき、炭素数は1〜 Have such a substituent may be exemplified an alkyl group as a substituent of an amino group other than a phenyl group which may a carbon number of 1 to
4が好ましい。 4 is preferred. 置換基を有していても良いフェニル基の置換基としては、例えば炭素数1〜4のアルコキシル基、炭素数1〜4のアルキル基、水酸基、カルボキシル基、炭素数1〜4のアルキルオキシカルボニル基、ハロゲン原子等が例示できる。 Examples of the substituent of which may have a substituent phenyl group, for example, an alkoxyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a hydroxyl group, a carboxyl group, an alkyloxycarbonyl having 1 to 4 carbon atoms group and a halogen atom can be exemplified. 置換基の数は0〜3が好ましく、0〜2が更に好ましい。 The number of the substituents is preferably 0-3, more preferably 0-2. ここで導入する置換アミノヒドロキシプロピル基は光学活性体であることが本発明では好ましい。 It is preferred in the present invention wherein the substituted amino hydroxypropyl group to be introduced is an optically active substance. これはこの様に製造される本発明の一般式(I)の化合物において、置換アミノハロゲン化ヒドロキシプロパンの立体が良く保持されて導入されるからである。 Which in the compound of general formula (I) of the present invention produced in this way is because stereoscopic substituted amino halogenated hydroxy propane is introduced is maintained well. 例えば、ラセミ体を導入すればそのまま立体が保持されてラセミ体が得られ、光学活性体を導入すれば、この光学活性が極めて良く保持されるためである。 For example, if introduced racemic it is held solid racemates can be obtained, if introduced optically active substance, it is because the optical activity is very well maintained.
かくして得られた、R1に保護基を有する一般式(I) Thus obtained of the general formula with a protecting group in R1 (I)
の化合物は例えば塩酸などの酸を作用させることにより、保護基を自由に外すことが出来る。 The compounds by the action of for example an acid such as hydrochloric acid can remove the protecting group freely. 塩としては通常医薬で用いられているものであれば何れも使用が可能であり、例えば、硫酸、塩酸、燐酸、硝酸、炭酸、マレイン酸、フマル酸、シュウ酸、クエン酸、メタンスルホン酸、パラトルエンスルホン酸、ベンゼンスルホン酸等が例示できる。 It can be used any as long as it is normally used in medicine as a salt, for example, sulfuric, hydrochloric, phosphoric, nitric, carbonic, maleic acid, fumaric acid, oxalic acid, citric acid, methanesulfonic acid, p-toluenesulfonic acid, benzenesulfonic acid can be exemplified. これら一般式(I)に表される化合物及びこれらの塩は何れも文献未記載の新規化合物である。 Compounds represented in the general formulas (I) and the salts thereof each a novel compound not disclosed in any literature. 本発明の化合物としては例えば、(S)−1−(2−ヒドロキシ−3−フェニルアミノプロピル)−4−トリフェニルメチルピペラジン、(R)−1−(2−ヒドロキシ−3−フェニルアミノプロピル)−4−トリフェニルメチルピペラジン、(S)−1−(2−ヒドロキシ−3− The compound of the present invention for example, (S) -1- (2- hydroxy-3-phenyl-aminopropyl) -4-triphenylmethyl piperazine, (R) -1- (2- hydroxy-3-phenyl-aminopropyl) 4-triphenylmethyl piperazine, (S) -1- (2- hydroxy-3-
フェニルアミノプロピル)ピペラジン、(R)−1− Phenyl aminopropyl) piperazine, (R)-1-
(2−ヒドロキシ−3−フェニルアミノプロピル)ピペラジンが挙げられる。 (2-hydroxy-3-phenyl-aminopropyl) piperazine.

【0008】 [0008]

【実施例】以下に実施例を示して本発明について更に詳細に説明を加えるが、本発明がこれら実施例にのみ限定を受けないことは言うまでもない。 EXAMPLES While adding more detail described the present invention by the following examples, but the present invention is not subject to limited to these examples.

【0009】実施例1 下記反応式1に示す方法に従って(S)−1−(2−ヒドロキシ−3−フェニルアミノプロピル)−4−トリフェニルメチルピペラジンを合成した。 [0009] (S) -1- (2- hydroxy-3-phenyl-aminopropyl) was synthesized 4-triphenylmethyl-methylpiperazine according to the method shown in Example 1 the following reaction scheme 1. 即ち、(S)−N In other words, (S) -N
−(3−クロロ−2−ヒドロキシプロピル)アニリン2.4g(12.93mmol)、1−トリフェニルメチルピペラジン4.46g(13.58mmol)炭酸カリウム2.16g(15.63mmol)、粉砕したヨウ化カリウム1.08g(6.51mmol)に乾燥エタノール50mlを加え、窒素雰囲気下、室温で19 - (3-chloro-2-hydroxypropyl) aniline 2.4 g (12.93 mmol), 1-triphenylmethyl-methylpiperazine 4.46 g (13.58Mmol) potassium carbonate 2.16g (15.63mmol), ground iodide added dry ethanol 50ml potassium 1.08 g (6.51 mmol), under a nitrogen atmosphere, 19 at room temperature
1時間攪拌し、更に3時間攪拌しながら還流した。 Stirred for 1 hour and then refluxed with stirring for further 3 hours. その後、室温まで冷却し、0.5N−水酸化ナトリウム水溶液150ml、ベンゼン60mlの系に注ぎ、分液し、 After cooling to room temperature, 0.5N-aqueous sodium 150ml hydroxide, poured into a system of benzene 60 ml was separated,
有機層を分離し、水層は更にベンゼンで抽出した(30 The organic layer was separated and the aqueous layer was further extracted with benzene (30
ml×2)。 ml × 2). 全有機層は合わせて飽和食塩水50mlで洗い、硫酸ナトリウム乾燥後、減圧下濃縮した。 All organic layers are combined washed with brine 50 ml, after sodium sulfate dried, and concentrated under reduced pressure. 残渣をシリカゲルカラムクロマトグラフィーに付し、目的フラクションを濃縮後、ベンゼン40mlに溶解し、0.5 The residue was subjected to silica gel column chromatography, after concentration of the desired fractions was dissolved in benzene 40 ml, 0.5
N−水酸化ナトリウム水溶液80mlと共に振とうし有機層を分離、水層は更にベンゼンで抽出した(20ml Shi shaking with N- hydroxide aqueous sodium 80ml organic layer separated and the aqueous layer was further extracted with benzene (20ml
×2)。 × 2). 全有機層は合わせて飽和食塩水40mlで洗浄後硫酸ナトリウムで乾燥させ、減圧濃縮した。 All organic layers were dried after washing sodium sulfate and saturated brine 40ml combined and concentrated under reduced pressure. 残渣にエタノールを加え、結晶化させこれを濾取し、乾燥し(S)−1−(2−ヒドロキシ−3−フェニルアミノプロピル)−4−トリフェニルメチルピペラジン(化合物1)を4.04g(収率65.5%)得た。 Ethanol was added to the residue, which is filtered off and crystallized, dried with (S)-1-(2-hydroxy-3-phenyl-aminopropyl) -4-triphenylmethyl piperazine (Compound 1) 4.04 g ( yield 65.5%) was obtained. mp. mp. :198〜200℃ IR(KBr錠剤、cm -1 ):3402、1602、1 : 198~200 ℃ IR (KBr tablet, cm -1): 3402,1602,1
504、1448、1004、749、714、694 1 H−NMR(CDCl 3 )δ:2.35〜2.70(8 504,1448,1004,749,714,694 1 H-NMR (CDCl 3 ) δ: 2.35~2.70 (8
H,m)、2.70〜2.90(2H,m)、2.90 H, m), 2.70~2.90 (2H, m), 2.90
〜3.10(1H,m),3.13〜3.28(1H, ~3.10 (1H, m), 3.13~3.28 (1H,
m)、3.35(1H,brs)、3.82〜3.96 m), 3.35 (1H, brs), 3.82~3.96
(1H,m)、4.08(1H,brs)、6.60 (1H, m), 4.08 (1H, brs), 6.60
(2H,d,J=7.6Hz)、6.70(1H,t, (2H, d, J = 7.6Hz), 6.70 (1H, t,
J=7.4Hz)、7.16(5H,t,J=8.0H J = 7.4Hz), 7.16 (5H, t, J = 8.0H
z),7.21〜7.32(7H,m)、7.32〜 z), 7.21~7.32 (7H, m), 7.32~
7.60(5H,m) 7.60 (5H, m)

【0010】 [0010]

【化3】 ## STR3 ## 反応式1 Scheme 1

【0011】実施例2 下記反応式2に示す方法に従って(S)−1−(2−ヒドロキシ−3−フェニルアミノプリピル)ピペラジン・ [0011] (S) -1- (2- hydroxy-3-phenylamino pre pills) according to the method shown in Example 2 Reaction Scheme 2 below piperazine
3塩酸塩を合成した。 3 hydrochloride salt was synthesized. 即ち、(S)−1−(2−ヒドロキシ−3−フェニルアミノプロピル)−4−トリフェニルメチルピペラジン(化合物1)7g(14.66mm That, (S)-1-(2-hydroxy-3-phenyl-aminopropyl) -4-triphenylmethyl piperazine (Compound 1) 7g (14.66mm
ol)をテトラヒドロフラン146mlに溶解し、これを室温で攪拌しながら濃塩酸5.8mlを加え、更に4 The ol) was dissolved in tetrahydrofuran 146 ml, which while stirring concentrated hydrochloric acid 5.8ml was added at room temperature, 4
5分間攪拌した。 5 minutes and the mixture was stirred. その後反応液を減圧濃縮し、残渣にベンゼン100mlを加え再び減圧濃縮した。 Then the reaction solution was concentrated under reduced pressure, and concentrated again under reduced pressure benzene 100ml added to the residue. 残渣をジエチルエーテルで洗い、エタノール50ml、メタノール25mlを加え、更にジエチルエーテル250mlを加えて粉末とし、濾取しジエチルエーテルで洗い、乾燥させて、(S)−1−(2−ヒドロキシ−3−フェニルアミノプロピル)ピペラジン・3塩酸塩(化合物2)を5.00g(収率99%)得た。 The residue was washed with diethyl ether, ethanol 50 ml, of methanol 25ml was added, further to a powder by addition of diethyl ether 250 ml, washed with filtered and diethyl ether and dried, (S) -1- (2- hydroxy-3- phenyl aminopropyl) piperazine trihydrochloride (compound 2) was obtained 5.00 g (99% yield).

【0012】 [0012]

【化4】 [Of 4] 反応式2 Scheme 2

【0013】実施例3 実施例1と同様に(R)−N−(3−クロロ−2−ヒドロキシプロピル)アニリン5.67g(30.54mm [0013] Similarly to Example 3 Example 1 (R) -N- (3- chloro-2-hydroxypropyl) aniline 5.67g (30.54mm
ol)、1−トリフェニルメチルピペラジン10.53 ol), 1-triphenylmethyl piperazine 10.53
g(32.06mmol)、炭酸カリウム5.10g g (32.06mmol), potassium carbonate 5.10g
(36.90mmol)、粉砕したヨウ化カリウム2. (36.90mmol), ground potassium iodide 2.
55g(15.36mmol)を処理し、(R)−1− Handles 55g (15.36mmol), (R) -1-
(2−ヒドロキシ−3−フェニルアミノプロピル)−4 (2-hydroxy-3-phenyl-aminopropyl) -4
−トリフェニルメチルピペラジン(化合物3)を10. - triphenylmethyl piperazine (Compound 3) 10.
64g(収率72.9%)得た。 To give 64 g (72.9% yield). 旋光度より本発明の化合物が立体保持性に優れていることが判る。 It can be seen that the compounds of the present invention than optical rotation is superior to the stereo retention. mp. mp. :196〜197.5℃ IR(KBr錠剤、cm -1 ):3402、1601、1 : 196~197.5 ℃ IR (KBr tablet, cm -1): 3402,1601,1
504、1448、1004、741、715、694 1 H−NMR(CDCl 3 )δ:2.35〜2.70(8 504,1448,1004,741,715,694 1 H-NMR (CDCl 3 ) δ: 2.35~2.70 (8
H,m)、2.70〜2.90(2H,m)、2.90 H, m), 2.70~2.90 (2H, m), 2.90
〜3.10(1H,m),3.13〜3.28(1H, ~3.10 (1H, m), 3.13~3.28 (1H,
m)、3.35(1H,brs)、3.82〜3.96 m), 3.35 (1H, brs), 3.82~3.96
(1H,m)、4.08(1H,brs)、6.60 (1H, m), 4.08 (1H, brs), 6.60
(2H,d,J=7.6Hz)、6.70(1H,t, (2H, d, J = 7.6Hz), 6.70 (1H, t,
J=7.4Hz)、7.16(5H,t,J=8.0H J = 7.4Hz), 7.16 (5H, t, J = 8.0H
z),7.21〜7.32(7H,m)、7.32〜 z), 7.21~7.32 (7H, m), 7.32~
7.60(5H,m) [α] 20 D :−9.7゜(C=1.0、CHCl 3 7.60 (5H, m) [α ] 20 D: -9.7 ° (C = 1.0, CHCl 3)

【0014】実施例4 実施例2と同様に、化合物3の7g(14.66mmo [0014] Similarly to Example 4 Example 2, Compound 3 of 7g (14.66mmo
l)を処理して、(R)−1−(2−ヒドロキシ−3− Processing the l), (R) -1- (2- hydroxy-3-
フェニルアミノプロピル)ピペラジン・3塩酸塩(化合物4)を5.00g(収率99%)得た。 Phenyl aminopropyl) piperazine trihydrochloride (compound 4) was obtained 5.00 g (99% yield).

【0015】 [0015]

【発明の効果】本発明によれば、立体保持に優れたアミノヒドロキシプロピルピペラジン構造を有する化合物の合成に有用な中間体を提供することができる。 According to the present invention, it is possible to provide useful intermediates in the synthesis of compounds having excellent amino hydroxypropyl piperazine structures stereo retention.

フロントページの続き (72)発明者 柳 正行 神奈川県横浜市戸塚区柏尾町560 ポーラ 化成工業株式会社戸塚研究所内 (72)発明者 山田 浩次 神奈川県横浜市戸塚区柏尾町560 ポーラ 化成工業株式会社戸塚研究所内 Of the front page Continued (72) inventor Masayuki Yanagi Kanagawa Prefecture, Totsuka-ku, Yokohama-shi Casio-cho, 560 Pola Chemical Industry Co., Ltd. Totsuka the laboratory (72) inventor Koji Yamada, Kanagawa Prefecture, Totsuka-ku, Yokohama-shi Casio-cho, 560 Pola Chemical Industry Co., Ltd. Totsuka the laboratory

Claims (4)

    【特許請求の範囲】 [The claims]
  1. 【請求項1】 次に示す一般式(I)で表されるアミノヒドロキシプロピルピペラジン誘導体又はそれらの塩。 1. A Amino hydroxypropyl piperazine derivative or salt thereof then represented by the general formula (I) shown. 【化1】 [Formula 1] 一般式(I) (但し式中R1は水素原子又は保護基を表し、R2、R General formula (I) (where Shikichu R1 represents a hydrogen atom or a protecting group, R2, R
    3はそれぞれ独立に水素原子、炭素数1〜4のアルキル基又は置換基を有していても良い芳香族基を表す。 3 are each independently a hydrogen atom, an alkyl group or which may have a substituent aromatic group having 1 to 4 carbon atoms. )
  2. 【請求項2】 保護基がトリフェニルメチル基であり、 Wherein the protecting group is a triphenylmethyl group,
    芳香族基がフェニル基である、請求項1に記載のアミノヒドロキシプロピルピペラジン誘導体又はそれらの塩。 Aromatic group is a phenyl group, an amino hydroxypropyl piperazine derivative or salt thereof according to claim 1.
  3. 【請求項3】 光学活性な化合物であることを特徴とする、請求項1又は2に記載のアミノヒドロキシプロピルピペラジン誘導体又はそれらの塩。 Characterized in that wherein an optically active compound, an amino hydroxypropyl piperazine derivative or salt thereof according to claim 1 or 2.
  4. 【請求項4】 一般式(I)に表される化合物が、 4. A compound represented by the general formula (I) is
    (S)−1−(2−ヒドロキシ−3−フェニルアミノプロピル)−4−トリフェニルメチルピペラジン、(R) (S) -1- (2- hydroxy-3-phenyl-aminopropyl) -4-triphenylmethyl piperazine, (R)
    −1−(2−ヒドロキシ−3−フェニルアミノプロピル)−4−トリフェニルメチルピペラジン、(S)−1 -1- (2-hydroxy-3-phenyl-aminopropyl) -4-triphenylmethyl piperazine, (S) -1
    −(2−ヒドロキシ−3−フェニルアミノプロピル)ピペラジン、(R)−1−(2−ヒドロキシ−3−フェニルアミノプロピル)ピペラジンの何れかである、請求項1〜3何れか一項に記載のアミノヒドロキシプロピルピペラジン誘導体又はそれらの塩。 - (2-hydroxy-3-phenyl-aminopropyl) piperazine, (R)-1-is either (2-hydroxy-3-phenyl-aminopropyl) piperazine, according to any one of claims 1 to 3 amino hydroxypropyl piperazine derivative or a salt thereof.
JP9173239A 1997-06-13 1997-06-13 Novel aminohydroxypropylpiperazine derivative Pending JPH115786A (en)

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