JP2668168B2 - Phenoxy derivatives - Google Patents
Phenoxy derivativesInfo
- Publication number
- JP2668168B2 JP2668168B2 JP2421191A JP2421191A JP2668168B2 JP 2668168 B2 JP2668168 B2 JP 2668168B2 JP 2421191 A JP2421191 A JP 2421191A JP 2421191 A JP2421191 A JP 2421191A JP 2668168 B2 JP2668168 B2 JP 2668168B2
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- Prior art keywords
- cis
- phenoxy
- pyrimidone
- group
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Description
【0001】[0001]
【産業上の利用分野】本発明は胃酸分泌抑制作用を有す
るピリミドン誘導体を製造するためのフェノキシ誘導体
に関する。The present invention relates to a phenoxy derivative for producing a pyrimidone derivative having a gastric acid secretion inhibitory action.
【0002】[0002]
【従来の技術】ヒスタミンH2 受容体拮抗作用に基づき
優れた胃酸分泌抑制作用を有する消化性潰瘍剤として、
例えばシメチジン、ラニチジン、ファモチジン、ロキサ
チジンが臨床に供されているが、治癒後に薬剤の投与を
中止すると消化性潰瘍が再発することが問題となってい
た。この様な副作用(リバウンド現象)を減じるため
に、胃酸分泌抑制作用と消化管粘膜防御作用を併せ持っ
た消化性潰瘍治療剤として以下の構造を有するピリミド
ン誘導体が知られている(特開平1−149774号公
報、特願平1−125067号)。 2. Description of the Related Art As a peptic ulcer agent having an excellent gastric acid secretion inhibitory action based on histamine H 2 receptor antagonism,
For example, cimetidine, ranitidine, famotidine, and roxatidine have been clinically used. However, if administration of the drug is stopped after healing, peptic ulcer recurs. In order to reduce such side effects (rebound phenomenon), a pyrimidone derivative having the following structure is known as a therapeutic agent for peptic ulcer having both a gastric acid secretion inhibitory action and a gastrointestinal mucosa protective action (JP-A-1-149774). No., Japanese Patent Application No. 1-125067).
【0003】[0003]
【化2】 Embedded image
【0004】[0004]
【発明が解決しようとする課題】本発明は、上記のピリ
ミドン誘導体を効率的に製造するための新規製造中間体
を提供するものである。The present invention provides a novel intermediate for efficiently producing the above pyrimidone derivative.
【0005】[0005]
【課題を解決するための手段】本発明者は上記の課題を
解決すべく鋭意努力した結果、新規製造中間体として下
記の一般式(I)で表される化合物Means for Solving the Problems The present inventors have made intensive efforts to solve the above-mentioned problems, and as a result, a compound represented by the following general formula (I) as a novel intermediate for production:
【0006】[0006]
【化3】 Embedded image
【0007】を選択し、本発明を完成するに至った。本
発明の式(I)で示される化合物は、下記の式(II)で
示される化合物The present invention has been completed by selecting The compound represented by the formula (I) of the present invention is a compound represented by the following formula (II)
【0008】[0008]
【化4】 Embedded image
【0009】(式中、Xはニトロアミノ基、メチルチオ
基、メトキシ基、若しくはハロゲン原子を示す)と反応
させて下記の一般式(III)で表される化合物(Wherein, X represents a nitroamino group, a methylthio group, a methoxy group, or a halogen atom) to react with a compound represented by the following general formula (III):
【0010】[0010]
【化5】 Embedded image
【0011】(式中、Yは前記定義の通りである)を
得、その後に例えばピペリジン等の2級アミンと還元的
に縮合させることにより消化性潰瘍治療剤として有用な
前記のピリミドン誘導体に変換することができる。本発
明の一般式(I)で表される化合物において、低級アル
キル基は直鎖であっても分枝していてもよく、アルキル
基として例えばメチル基、エチル基、n−プロピル基、
イソプロピル基、n−ブチル基、イソブチル基、n−ペ
ンチル基、n−ヘキシル基等を挙げることができ、好ま
しくはエチル基である。nは1が好ましい。Wherein Y is as defined above, followed by reductive condensation with a secondary amine such as piperidine to convert to the pyrimidone derivative useful as a therapeutic agent for peptic ulcer. can do. In the compound represented by the general formula (I) of the present invention, the lower alkyl group may be linear or branched, and as the alkyl group, for example, a methyl group, an ethyl group, an n-propyl group,
Examples thereof include an isopropyl group, an n-butyl group, an isobutyl group, an n-pentyl group, and an n-hexyl group, and an ethyl group is preferable. n is preferably 1.
【0012】本発明の式(I)で表される化合物は、以
下に示すスキームにより公知物質から製造することがで
きる(スキーム中、Yは上記の定義の通りであり、1及
び2の化合物は特開昭57−165348号公報に記載
されている)。The compound represented by the formula (I) of the present invention can be produced from a known substance by the following scheme (where Y is as defined above, and the compounds of 1 and 2 are JP-A-57-165348).
【0013】[0013]
【化6】 Embedded image
【0014】[0014]
【発明の効果】本発明により、優れた消化性潰瘍治療剤
であるピリミドン誘導体の新規製造中間体が提供され
た。本方法により該ピミドン誘導体が安価で効率的に製
造することができる。According to the present invention, a novel intermediate for producing a pyrimidone derivative, which is an excellent therapeutic agent for peptic ulcer, is provided. By this method, the pimidone derivative can be produced inexpensively and efficiently.
【0015】[0015]
【実施例】以下に本発明の製造方法を参考例及び実施例
によりさらに具体的に説明するが、本発明はこれらに限
定されることはない。 実施例14−〔3−(1,3−ジオキソラン−2−イル)フェノ
キシ〕−cis −2−ブテニルアミン A) N−〔4−〔3−(1,3−ジオキソラン−2−イ
ル)フェノキシ〕−cis −2−ブテニル〕フタルイミド 3−(1,3−ジオキソラン−2−イル)フェノール
(33.2g,0.2モル)をDMSO(200ml)に溶解
し、冷却下60%油性水素化ナトリウム(8.0g,0.2
モル)を少量ずつ加えた。更に50℃で30分間撹拌後
冷却下に4−クロル−cis −2−ブテニルフタルイミド
(49.6g,0.21モル)を加えて、室温下2時間撹拌
した。反応終了後に1500mlの水に注加して、分離し
た油状物を酢酸エチルエステル(250ml)で3回注出
した。合わせた有機層を飽和食塩水で洗浄、乾燥後溶媒
を留去し、題記の化合物62.1(85%)gを得た。EXAMPLES Hereinafter, the production method of the present invention will be described more specifically with reference examples and examples, but the present invention is not limited to these examples. Example 1 4- [3- (1,3-dioxolan-2-yl) pheno
Xy] -cis-2-butenylamine A) N- [4- [3- (1,3-dioxolan-2-i
Phenoxy] -cis-2-butenyl] phthalimide 3- (1,3-dioxolan-2-yl) phenol (33.2 g, 0.2 mol) was dissolved in DMSO (200 ml) and cooled to 60% oil. Sodium hydride (8.0 g, 0.2
Mol) was added in small portions. After further stirring at 50 ° C. for 30 minutes, 4-chloro-cis-2-butenylphthalimide (49.6 g, 0.21 mol) was added under cooling, and the mixture was stirred at room temperature for 2 hours. After the completion of the reaction, the mixture was poured into 1500 ml of water, and the separated oil was extracted three times with ethyl acetate (250 ml). The combined organic layer was washed with saturated saline and dried, and then the solvent was distilled off, thereby obtaining 62.1 g (85%) of the title compound.
【0016】NMR (δ, CDCl3): 3.95〜4.2(4H, m)、
4.3〜4.5(2H, d)、 4.8〜4.9(2H, d)、 5.5〜6.2(3H,
m)、 6.8〜7.3(4H, m)、 7.6〜7.9(4H, m)。 B) 4−〔3−(1,3−ジオキソラン−2−イル)フ
ェノキシ〕−cis −2−ブテニルアミン 実施例1のA)で得たN−〔4−〔3−(1,3−ジオキ
ソラン−2−イル)フェノキシ〕−cis −2−ブテニ
ル〕フタルイミド(62g,0.17モル)をエタノール
(1000ml)に溶解し、ヒドラジン・ヒドラート(3
2ml)を加えて室温下18時間撹拌した。反応終了後析
出した結晶を吸引ろ過、結晶をエタノールで洗浄した。
ろ液と洗液を合わせ減圧に濃縮し、残渣をシリカゲル・
カラムクロマトを用いて精製し淡黄色油状物として題記
の化合物35.1g(88%)を得た。NMR (δ, CDCl 3 ): 3.95 to 4.2 (4H, m),
4.3 to 4.5 (2H, d), 4.8 to 4.9 (2H, d), 5.5 to 6.2 (3H, d)
m), 6.8-7.3 (4H, m), 7.6-7.9 (4H, m). B) 4- [3- (1,3-dioxolan-2-yl) fur
[ Enoxy] -cis-2-butenylamine N- [4- [3- (1,3-dioxolan-2-yl) phenoxy] -cis-2-butenyl] phthalimide obtained in A) of Example 1 (62 g, 0 0.17 mol) was dissolved in ethanol (1000 ml) and hydrazine hydrate (3
2 ml) and stirred at room temperature for 18 hours. After completion of the reaction, the precipitated crystals were suction filtered, and the crystals were washed with ethanol.
The filtrate and washings are combined and concentrated under reduced pressure.
Purification using column chromatography gave 35.1 g (88%) of the title compound as a pale yellow oil.
【0017】NMR (δ, CDCl3): 3.3〜3.5(2H, d)、
3.9〜4.2(4H, m)、 4.5〜4.8(2H, d)、 5.6〜5.9(3H,
m)、6.8〜7.4(4H, m)。 実施例24−(3−ジエトキシメチルフェノキシ)−cis −2−
ブテニルアミン A) N−〔4−(3−ジエトキシフェノ
キシ)−cis −2−ブテニル〕フタルイミド 実施例1のA)の3−(1,3−ジオキソラン−2−イ
ル)フェノールを3−ジエトキシメチルフェノールに替
える以外は同様に操作して題記の化合物を淡黄色油状物
として得た。NMR (δ, CDCl 3 ): 3.3 to 3.5 (2H, d),
3.9-4.2 (4H, m), 4.5-4.8 (2H, d), 5.6-5.9 (3H,
m), 6.8-7.4 (4H, m). Example 2 4- (3-diethoxymethylphenoxy) -cis-2-
Butenylamine A) N- [4- (3-diethoxypheno
[Xy) -cis-2-butenyl] phthalimide The title compound was prepared in the same manner as in Example 1 A) except that 3- (1,3-dioxolan-2-yl) phenol in Example A) was replaced with 3-diethoxymethylphenol. Was obtained as a pale yellow oil.
【0018】NMR (δ, CDCl3): 1.05〜1.3(6H, t)、
3.35〜3.7(4H, q)、 4.3〜4.5(2H, d)、 4.7〜4.9(2H,
d)、 5.4(1H, s) 、 5.5〜6.0(2H, m)、 6.8〜7.4(4H,
m)、7.5 〜7.9(4H, m)。 B) 4−(3−ジエトキシメチル)フェノキシ−cis −
2−ブテニルアミン 実施例2のA)の原料を用いて参考例1のB)と同様に操作
して題記の化合物を得た。NMR (δ, CDCl 3 ): 1.05 to 1.3 (6H, t),
3.35 to 3.7 (4H, q), 4.3 to 4.5 (2H, d), 4.7 to 4.9 (2H,
d), 5.4 (1H, s), 5.5-6.0 (2H, m), 6.8-7.4 (4H,
m), 7.5-7.9 (4H, m). B) 4- (3-Diethoxymethyl) phenoxy-cis-
2-Butenylamine The title compound was obtained in the same manner as in B) of Reference Example 1 using the starting material A) of Example 2.
【0019】NMR (δ, CDCl3): 1.05〜1.4(6H, t)、
1.5(2H, s)、 3.3〜3.8(6H, m)、 4.5〜4.7(2H, s)、
5.4(1H, s) 、 5.6〜5.8(2H, t)、 6.7〜7.4(4H, m)。 参考例15,6−ジメチル−2−〔〔4−(3−ジエトキシメチ
ル)フェノキシ〕−cis −2−ブテニルアミノ〕−4−
(1H)−ピリミドン 実施例2のB)の4−(3−ジエトキシメチル)フェノキ
シ−cis −2−ブテニルアミン(3.5g,0.0132モル)
及び5,6−ジメチル−2−メチルチオ−4−(1H)
−ピリミドン(薬学雑誌1976年、96巻、No. 3、
384頁に記載の方法で製造した。)(2.5g、0.0147
モル)をトルエン(100ml)に溶解し、撹拌下に48
時間還流した。NMR (δ, CDCl 3 ): 1.05 to 1.4 (6H, t),
1.5 (2H, s), 3.3-3.8 (6H, m), 4.5-4.7 (2H, s),
5.4 (1H, s), 5.6-5.8 (2H, t), 6.7-7.4 (4H, m). Reference Example 1 5,6-dimethyl-2-[[4- (3-diethoxymethyi
) Phenoxy] -cis-2-butenylamino] -4-
(1H) -Pyrimidone 4- (3-diethoxymethyl) phenoxy-cis-2-butenylamine of Example 2B) (3.5 g, 0.0132 mol)
And 5,6-dimethyl-2-methylthio-4- (1H)
-Pyrimidone (Pharmaceutical Journal, 1976, Volume 96, No. 3,
It was prepared by the method described on page 384. ) (2.5 g, 0.0147)
Mol) was dissolved in toluene (100 ml) and stirred for 48 hours.
Refluxed for hours.
【0020】反応終了後、減圧下に溶媒を留去し、残渣
の油状物をカラムクロマトグラフィーにて精製して題記
の化合物1.38g(27.0%)を淡黄色油状物として得
た。NMR (δ, CDCl3): 1.1〜1.4(6H, t)、 1.9(3H,
s) 、2.15(3H, s) 、 3.3〜3.8(4H, m)、 3.9〜4.2(2H,
m)、 4.6〜4.8(2H, d)、 5.5〜6.0(3H, m)、 6.4〜6.8
(1H, b)、 6.7〜7.4(4H, m)。 参考例25,6−ジメチル−2−〔4−〔3−(1−ピペリジノ
メチル)フェノキシ〕−cis −2−ブテニルアミノ〕−
4−(1H)−ピリミドン 参考例1で製造した5,6−ジメチル−2−〔〔4−
(3−ジエトキシメチル)フェノキシ〕−cis −2−ブ
テニルアミノ〕−4−(1H)−ピリミドン(2.0g)
をトルエン(80ml)に溶解し、ピペリジン(1.5g)
及び蟻酸(8ml)を加えて撹拌下に12時間還流し、そ
の間に分離する水を反応容器から除去した。反応終了
後、10%炭酸カリウム水溶液を加えてアルカリ性と
し、有機層を水洗、乾燥後、減圧下に溶媒を留去した。
残渣をカラムクロマトグラフィーに付して精製して題記
の化合物1.51g(76.5%)を淡黄色油状物として得
た。After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 1.38 g (27.0%) of the title compound as a pale yellow oil. NMR (δ, CDCl 3 ): 1.1-1.4 (6H, t), 1.9 (3H,
s), 2.15 (3H, s), 3.3-3.8 (4H, m), 3.9-4.2 (2H,
m), 4.6-4.8 (2H, d), 5.5-6.0 (3H, m), 6.4-6.8
(1H, b), 6.7-7.4 (4H, m). Reference Example 2 5,6-dimethyl-2- [4- [3- (1-piperidino
Methyl) phenoxy] -cis-2-butenylamino]-
4- (1H) -pyrimidone 5,6-dimethyl-2-[[4-
(3-Diethoxymethyl) phenoxy] -cis-2-butenylamino] -4- (1H) -pyrimidone (2.0 g)
Dissolved in toluene (80 ml) and piperidine (1.5 g)
And formic acid (8 ml) were added and the mixture was refluxed for 12 hours with stirring, during which time the separated water was removed from the reaction vessel. After completion of the reaction, a 10% aqueous potassium carbonate solution was added to make the mixture alkaline, and the organic layer was washed with water and dried, and the solvent was distilled off under reduced pressure.
The residue was purified by column chromatography to give 1.51 g (76.5%) of the title compound as a pale yellow oil.
【0021】NMR (δ, CDCl3): 1.2〜1.7(6H, m)、
1.85(3H, s)、2.1(3H, s)、 2.2〜2.5(4H, m)、 3.4(2
H, s) 、 3.9〜4.2(2H, m)、 4.5〜4.8(2H, d)、 5.5〜
6.0(2H, m)、 4.6〜7.3(4H, m)。 参考例35,6−ジメチル−2−〔4−〔3−(1,3−ジオキ
ソラン−2−イル)フェノキシ〕−cis −2−ブテニル
アミノ〕−4−(1H)−ピリミドン 実施例1のB)の方法で製造した4−〔3−(1,3−ジ
オキソラン−2−イル)フェノキシ〕−cis −2−ブテ
ニルアミン(2.35g,0.01モル)及び5,6−ジメ
チル−2−ニトロアミン−4−(1H)−ピリミドン
(特開昭60−228465号の参考例に記載の方法を
利用して製造した。)(1.84g,0.01モル)をピリ
ジン(50ml)に溶解し、撹拌下に15時間還流した。
反応終了後、減圧下に溶媒を留去し、残渣をシリカゲル
カラムクロマトグラフィーにて精製した。題記の化合物
を褐色油状物として得た。収量2.21g(62%)。NMR (δ, CDCl 3 ): 1.2 to 1.7 (6H, m),
1.85 (3H, s), 2.1 (3H, s), 2.2 to 2.5 (4H, m), 3.4 (2
H, s), 3.9-4.2 (2H, m), 4.5-4.8 (2H, d), 5.5-
6.0 (2H, m), 4.6 ~ 7.3 (4H, m). Reference Example 3 5,6-Dimethyl-2- [4- [3- (1,3-dioki
Solan-2-yl) phenoxy] -cis-2-butenyl
Amino] -4- (1H) -pyrimidone 4- [3- (1,3-dioxolan-2-yl) phenoxy] -cis-2-butenylamine prepared by the method of B) of Example 1 (2.35 g, 0.01 mol) and 5,6-dimethyl-2-nitroamine-4- (1H) -pyrimidone (prepared using the method described in Reference Example of JP-A-60-228465) (1.84 g). , 0.01 mol) was dissolved in pyridine (50 ml) and refluxed with stirring for 15 hours.
After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography. The title compound was obtained as a brown oil. Yield 2.21 g (62%).
【0022】NMR (δ, CDCl3): 1.9(3H, s) 、 2.2(3
H, s) 、 3.2〜3.8(4H,m)、 3.8〜4.1(2H, m)、 4.4〜
4.6(2H, d)、 5.6〜5.8(3H, m)、 6.4〜6.7(1H, b)、
6.7〜7.4(4H, m)。 参考例45,6−ジメチル−2−〔4−〔3−(1−ピペリジノ
メチル)フェノキシ〕−cis −2−ブテニルアミノ〕−
4−(1H)−ピリミドン・塩酸塩 参考例3で得た5,6−ジメチル−2−〔4−〔3−
(1,3−ジオキソラン−2−イル)フェノキシ〕−ci
s −2−ブテニルアミン〕−4−(1H)−ピリミドン
(3.6g,0.01モル)を使用し、参考例2と同様に操
作して得た淡黄色油状物にn−ブタノール溶媒中、当モ
ルの塩酸を反応させて題記の化合物1.0gを無色の結晶
として得た。NMR (δ, CDCl 3 ): 1.9 (3H, s), 2.2 (3
H, s), 3.2-3.8 (4H, m), 3.8-4.1 (2H, m), 4.4-
4.6 (2H, d), 5.6-5.8 (3H, m), 6.4-6.7 (1H, b),
6.7-7.4 (4H, m). Reference Example 4 5,6-Dimethyl-2- [4- [3- (1-piperidino
Methyl) phenoxy] -cis-2-butenylamino]-
4- (1H) -pyrimidone hydrochloride 5,6-dimethyl-2- [4- [3-
(1,3-Dioxolan-2-yl) phenoxy] -ci
s-2-butenylamine] -4- (1H) -pyrimidone (3.6 g, 0.01 mol) was treated in the same manner as in Reference Example 2 to give a pale yellow oil in n-butanol solvent. Equimolar hydrochloric acid was reacted to obtain 1.0 g of the title compound as colorless crystals.
【0023】融点:101〜2℃(d) NMR (δ, DMSO-d6): 0.9〜1.15(3H, d) 、 1.4〜2.0
(6H, m)、 2.1(3H, s) 、 2.6〜3.4(4H, m)、3.85〜4.2
(2H, m)、 4.25(2H, s)、 4.1〜4.9(2H, m)、 5.5〜5.9
(2H, m)、 6.7〜7.5(4H, m)。 参考例4で得られるピリミドン誘導体は消化性潰瘍治療
剤としての有用性が知られており(特開平1−1497
74号公報)、本発明の製造中間体の有用性が明らかで
ある。Melting point: 101 to 2 ° C. (d) NMR (δ, DMSO-d 6 ): 0.9 to 1.15 (3H, d), 1.4 to 2.0
(6H, m), 2.1 (3H, s), 2.6-3.4 (4H, m), 3.85-4.2
(2H, m), 4.25 (2H, s), 4.1-4.9 (2H, m), 5.5-5.9
(2H, m), 6.7-7.5 (4H, m). The pyrimidone derivative obtained in Reference Example 4 is known to be useful as a therapeutic agent for peptic ulcer (JP-A-1-14997).
74), and the usefulness of the production intermediate of the present invention is clear.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2421191A JP2668168B2 (en) | 1991-02-19 | 1991-02-19 | Phenoxy derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2421191A JP2668168B2 (en) | 1991-02-19 | 1991-02-19 | Phenoxy derivatives |
Related Parent Applications (1)
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JP20870490A Division JP2944165B2 (en) | 1990-08-07 | 1990-08-07 | Method for producing pyrimidone derivative |
Publications (2)
Publication Number | Publication Date |
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JPH04217646A JPH04217646A (en) | 1992-08-07 |
JP2668168B2 true JP2668168B2 (en) | 1997-10-27 |
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Application Number | Title | Priority Date | Filing Date |
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JP2421191A Expired - Lifetime JP2668168B2 (en) | 1991-02-19 | 1991-02-19 | Phenoxy derivatives |
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JP (1) | JP2668168B2 (en) |
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1991
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Publication number | Publication date |
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JPH04217646A (en) | 1992-08-07 |
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