JPS5840551B2 - Propanol derivatives and their production method - Google Patents
Propanol derivatives and their production methodInfo
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- JPS5840551B2 JPS5840551B2 JP51094177A JP9417776A JPS5840551B2 JP S5840551 B2 JPS5840551 B2 JP S5840551B2 JP 51094177 A JP51094177 A JP 51094177A JP 9417776 A JP9417776 A JP 9417776A JP S5840551 B2 JPS5840551 B2 JP S5840551B2
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Description
【発明の詳細な説明】
本発明は一般式
（但し、Ｋは低級脂肪族アシル基を表わし、Ｒ２は低級
アルコキシ基を表わし、Ｒ３はフェニル基、トリフルオ
ロメチルフェニル基、トリル基もしくはハロゲノフェニ
ル基を表わす。Detailed Description of the Invention The present invention is based on the general formula (where K represents a lower aliphatic acyl group, R2 represents a lower alkoxy group, and R3 represents a phenyl group, trifluoromethylphenyl group, tolyl group or halogenophenyl group). represents.
）テ示されるプロパツール誘導体及びその製法に関する
。) The present invention relates to a propatool derivative and a method for producing the same.
本発明の化合物「Ｉ〕はいずれも新規化合物であり、中
枢抑制作用を有し、トランキライザー鎮静剤、鎮吐剤と
して有用な医薬化合物である。Compounds "I" of the present invention are all new compounds, have a central depressant effect, and are pharmaceutical compounds useful as tranquilizer sedatives and antiemetics.
前記一般式ＣＩ）で示される本発明の化合物としては例
えば、記号Ｒ１で示される基がたとえば、ホルミル基、
アセチル基、プロパノイル基、分枝することもあるブチ
リル基、バレリル基の如き低級脂肪族アシル基であり、
記号Ｒ２で示される基がメトキシ基、エトキシ基等の低
級アルコキシ基である化合物が挙げられる。As for the compound of the present invention represented by the general formula CI), the group represented by the symbol R1 is, for example, a formyl group,
Lower aliphatic acyl groups such as acetyl group, propanoyl group, butyryl group which may be branched, and valeryl group,
Examples include compounds in which the group represented by the symbol R2 is a lower alkoxy group such as a methoxy group or an ethoxy group.
本発明の化合物［Ｉ）は一般式
（但し、Ｒ１及びＲ２は前記と同一意味を有する）で示
されるオキシラン誘導体ＣＩＤと一般式 ＊（但し、
Ｒ３は前記と同一意味を有する）で示される化合物［Ｉ
ＩＩ）とを反応させて実施することにより製することが
できる。Compound [I] of the present invention is an oxirane derivative CID represented by the general formula (wherein R1 and R2 have the same meanings as above) and the general formula * (however,
R3 has the same meaning as above) [I
It can be produced by reacting with II).
本反応は化合物ＣｌＩＤを試薬兼溶媒として使用して実
施することもでき、また１、適当な溶媒中で実施するこ
ともできる。This reaction can be carried out using the compound ClID as both a reagent and a solvent, or 1. It can also be carried out in an appropriate solvent.
反応はかくはん下室温乃至約１００℃位にて実施するの
が好ましく、高収率にて化合物〔■〕を得ることができ
る。The reaction is preferably carried out at room temperature to about 100° C. with stirring, and the compound [■] can be obtained in high yield.
尚、原料化合物〔■〕は例えば下記反応式で示される方
法により製することができる。Note that the starting compound [■] can be produced, for example, by the method shown in the following reaction formula.
（但し、Ｘはハロゲン原子を表わし、Ｒ１及びＲ２は前
記と同一意味を有する）
本発明の化合物〔■〕は遊離塩基のままで医薬として使
用することもでき、また医療上許容し得る適当な酸付加
塩に変えて使用することもできる。(wherein, It can also be used in place of an acid addition salt.
このような酸付加塩としては例えば塩酸、リン酸、硝酸
、硫酸の如き無機酸との塩、あるいは酢酸、乳酸、クエ
ン酸、酒石酸、フマール酸、マレイン酸、グリシン、ア
スパラギン酸、メタンスルホン酸、安息香酸などの有機
酸との塩などがある。Examples of such acid addition salts include salts with inorganic acids such as hydrochloric acid, phosphoric acid, nitric acid, and sulfuric acid, or acetic acid, lactic acid, citric acid, tartaric acid, fumaric acid, maleic acid, glycine, aspartic acid, methanesulfonic acid, These include salts with organic acids such as benzoic acid.
投与方法としては例えば散剤、錠剤、カプセル剤、溶液
剤、乳剤もしくはげん濁剤等適宜の剤型とし、経口的に
、もしくは非経口的に投与する。The administration method is, for example, in an appropriate dosage form such as a powder, tablet, capsule, solution, emulsion, or suspension, and the drug is administered orally or parenterally.
本発明化合物ＣＩ）の毒性（最大耐量）及び中枢抑制作
用を例示すれば下記の如（である。Examples of the toxicity (maximum tolerated dose) and central depressant effect of the compound CI of the present invention are as follows.
実験例
１群５匹の雄マウスに後記検体を腹腔内投与し、以下の
作用を検討した。Experimental Example The specimen described below was intraperitoneally administered to 5 male mice in Group 1, and the following effects were investigated.
その結果は表１に示す通りであった。The results were as shown in Table 1.
（１）最大耐量 検体投与４８時間後の死亡例の有無より求めた。(1) Maximum tolerance This was determined based on the presence or absence of death 48 hours after administration of the sample.
（２）自発運動抑制作用
検体投与３０分後に、５分間アニメソクスで運動量を測
定し、対照群の１／２以下に抑制された場合を有効と判
定してＥＤ５ｏ値を求めた。(2) Locomotor activity suppression effect 30 minutes after administration of the sample, the amount of locomotor activity was measured using Anime Sox for 5 minutes, and when the locomotor activity was suppressed to 1/2 or less of the control group, it was determined to be effective, and the ED5o value was determined.
（３Ｊ 麻酔増強作用
検体投与３０分後に、メチルへキサビタール・ナトリウ
ム（１００■／ｋｙ）を腹腔内投与した時の正向反射消
失時間が対照群の２倍以上延長した場合有効量と判定し
てＥＤ、ｏ値を求めた。(3J Anesthesia-enhancing effect If methylhexavital sodium (100 μ/ky) is intraperitoneally administered 30 minutes after administration of the sample, the righting reflex loss time is more than twice that of the control group, and the dose is determined to be an effective dose. ED and o values were determined.
（４）抗アポモルヒネ作用
検体投与３０分後に、塩酸アポモルヒネ
（２，５１ｎ９／ｋｇ）を皮下投与した時のケージよじ
登り反応の抑制を指標としてＥＤ、ｏ値を求めた。(4) Anti-apomorphine effect 30 minutes after administration of the sample, ED and o values were determined using the inhibition of cage climbing reaction as an index when apomorphine hydrochloride (2,51n9/kg) was subcutaneously administered.
実施例 １
３−（４−アセタミド−２−メトキシフェノキシ）−１
・２−エポキシプロパン１．Ｏｆをエタノール４０ｍ１
３にとかし、これに４−フェニルピペラジン７５０■を
加え、室温で１８時間かくはんする。Example 1 3-(4-acetamido-2-methoxyphenoxy)-1
・2-Epoxypropane 1. Of ethanol 40ml
3, add 750 ml of 4-phenylpiperazine, and stir at room temperature for 18 hours.
エタノールを留去し、残香を酢酸エチル・メタノール混
液より再結晶すれば、■−（４−アセタミド−２−メト
キシフェノキシ）−３−（４−フェニルピペラジノ）−
２−プロパツールを無色針状晶として１．５５ Ｐ得た
。If the ethanol is distilled off and the residual aroma is recrystallized from a mixture of ethyl acetate and methanol, ■-(4-acetamido-2-methoxyphenoxy)-3-(4-phenylpiperazino)-
1.55 P of 2-propertool was obtained as colorless needle crystals.
Ｍ、ｐ、１５４．５℃〜１５６℃収率９２．５％
ｕｊｏｌ
ＩＲν （ｃｒｒＬ ’）：３２５０．１６５０、
ａＸ
１１４０．１００Ｏ
ＮＭＲｌｏｏＯＮ ｄａ ）δ： ７．４−６．６
（ｍ１８Ｈ１芳香族水素）４．８０（ｂｒ、ＩＨｌｏ
Ｈ）、３．９２ （ｂｒ、 ｓ 、、 ３ Ｈ，−０−
ＣＨ，−ＣＨ−０Ｈ）、３．７５ （５１３Ｈ，ＯＣＨ
３） ２．０３（ｓ。M, p, 154.5°C to 156°C Yield 92.5% ujol IRν (crrL'): 3250.1650,
aX 1140.100O NMRlooON da) δ: 7.4-6.6
(m18H1 aromatic hydrogen) 4.80 (br, IHlo
H), 3.92 (br, s,, 3 H, -0-
CH, -CH-0H), 3.75 (513H, OCH
3) 2.03 (s.
３Ｈ，−ＣＯ−ＣＨ３）
Ｍａｓｓ ｍ／ ｅ ： ３９９ （Ｍ＋）本品の塩酸
塩：Ｍ、ｐ、２４２℃〜２４４℃（分解）本品のメタン
スルホン酸塩：Ｍ、ｐ、１９１℃〜１９３℃
実施例 ２
３−（４−アセタミド−２−メトキシフェノキシ）−１
・２−エポキシプロパン８００１ｎ９のエタノール４０
ｍ１ｌ溶液に、４−（２−フルオロフェニル）ピペラジ
ン６７０■を加え、４時間加熱還流させる。3H, -CO-CH3) Mass m/e: 399 (M+) Hydrochloride of this product: M, p, 242°C to 244°C (decomposition) Methanesulfonate of this product: M, p, 191°C to 193 °C Example 2 3-(4-acetamido-2-methoxyphenoxy)-1
・2-epoxypropane 8001n9 ethanol 40
670 μl of 4-(2-fluorophenyl)piperazine was added to the ml solution and heated under reflux for 4 hours.
減圧下にエタノールを留去し、残香をイソプロパノ−ル
ーインプロピルエーテル混液より再結晶すれば、■−（
４−アセタミド−２−メトキシフェノキシ）−３−（４
−（２−フルオロフェニル）ピペラジノコ−２−グロパ
ノールを無色粒状晶として７７０■得た。If the ethanol is distilled off under reduced pressure and the residual aroma is recrystallized from a mixture of isopropanol and propyl ether, ■-(
4-acetamido-2-methoxyphenoxy)-3-(4
-(2-Fluorophenyl)piperazinoco-2-glopanol was obtained as colorless granular crystals in an amount of 770 μl.
Ｍ、ｐ、１４３．５℃〜１４４．５℃
さらに、再結晶母液を濃縮乾固後、残香をシリカゲルカ
ラムクロマト（溶媒：メタノールを２％含有するクロロ
ホルム）で分離精製し、得られる結晶５５０ｒｎ９を前
記同様再結晶してＭ、 ｐ、１４２．５℃〜１４３．５
℃の粒状晶を４６０■得た。M, p, 143.5°C to 144.5°C Furthermore, after concentrating the recrystallized mother liquor to dryness, the residual aroma was separated and purified using silica gel column chromatography (solvent: chloroform containing 2% methanol), and the resulting crystal 550rn9 was Recrystallize as above to obtain M, p, 142.5°C to 143.5
460 °C of granular crystals were obtained.
計１．２３１収率８７．４％
ｕｊｏｌ
ＩＲｖ （ｃＩＩｌ ”）： ３２７５．１６５
５、ａＸ
１６０５．１１４５、ｉｏｏ。Total 1.231 Yield 87.4% ujol IRv (cIIl''): 3275.165
5, aX 1605.1145, ioo.
ＮＭＲ（ＣＤＣ１３）δ： ７．９５ （ｂｒｌｌ Ｈ
，ＮＨ）、７．５−６．７（ｍ、７Ｈ１芳香族水素）４
．０４ （ｂｒ、 ｓ、 ３Ｈ１−ＯＣＨ２−ＣＨ−Ｏ
Ｈ）、３．８１ （ｓ、 ３Ｈ１−０ＣＨ３）、３．７
（ｂｒ。NMR (CDC13) δ: 7.95 (brll H
, NH), 7.5-6.7 (m, 7H1 aromatic hydrogen) 4
．． 04 (br, s, 3H1-OCH2-CH-O
H), 3.81 (s, 3H1-0CH3), 3.7
(br.
ＬＨ，０Ｈ）２．１４（ｓ、３Ｈ，−ＣＯ−ＣＨ３）Ｍ
ａｓｓ ｍ／ ｅ ； ４１７ （Ｍ＋）実施例 ３〜
１６
実施例１乃至実施例２と同様にして、それぞれ対応する
原料化合物より、下記化合物を得た。LH,0H)2.14(s,3H,-CO-CH3)M
ass m/e; 417 (M+) Example 3~
16 In the same manner as in Examples 1 and 2, the following compounds were obtained from the corresponding raw material compounds.
（３Ｊ１−（４−アセタミド−２−メトキシフェノキシ
）−３−（４−（３−）リフルオロメチルフェニル）ピ
ペラジノコ−２−プロパツールＭ、ｐ、１２５℃〜１２
７℃針状晶（酢酸エチルから再結晶、以下、溶媒名のみ
記載）収率７３％
（４） １−（４−アセタミド−２−メトキシフェノ
キシ）−３−［ｌ４−（ｐ・トリル）ピペラジノコ−２
−プロパツールＭ、ｐ、１７２．５℃〜１７３．５℃針
状晶（メタノール）収率９１．１％
（５）１−（４−アセタミド−２−メトキシフェノキシ
）−３−Ｃ４−（ｍ・トリル）ピペラジノコ−２−グロ
パノールＭ、ｐ、 １２４．５℃〜１２６．５℃針状晶
（酢酸エチル）収率８８．２％
（６）１−（４−アセタミド−２−メトキシフェノキシ
）−３−Ｃ４−（ｏ・トリル）ピペラジノコ−２−グロ
パノールＩＬ ｐ、 １２６．５℃〜１２８℃プリズム
晶（イングロビルエーテル・イソプロパツール）収率８
７．５％
（’７１ １−（４−７セタミドー２−メトキシフェノ
キシ）−３−Ｃ４−（４−クロロフェニル）ピペラジノ
コ−２−プロパツールＭ、ｐ、１７７℃〜１７８．５℃
針状晶（メタノール）収率９２．３％
（８） １−（４−アセタミド−２−メトキシフェノ
キシ）−３−（４−（３−クロロフェニル）ピペラジノ
コ−２−プロパツールＭ、ｐ、１４１’Ｃ〜１４３．５
℃針状晶（エタノール）収率８８．２％
（９）ｌ−（４−アセタミド−２−メトキシフェノキシ
）−３−（４−（２−クロロフェニル）ピペラジノコ−
２−プロパツールＭ、Ｐ、１３７．５℃〜１４０℃プリ
ズム晶（酢酸エチル）収率９６．４％
（１０） １−（４−アセタミド−２−メトキシフェ
ノキシ）−３−［４−（４−フルオロフェニル）ピペラ
ジノツー２−プロパツールＭ、 ｐ 、 １７５．５℃
〜１７６．５℃針状晶（エタノール）収率８７．４％
（１１） １−（４−アセタミド−２−メトキシフェ
ノキシ）−３−Ｃ４−（３−フルオロフェニル）ピペラ
ジノツー２−プロパツールＭ、 ｐ、１４４．５℃〜１
４６℃針状晶（エタノール）収率９３．８％
塩酸塩：Ｍ、ｐ、２２４℃〜２２６℃(3J1-(4-acetamido-2-methoxyphenoxy)-3-(4-(3-)lifluoromethylphenyl)piperazinoco-2-propatol M, p, 125°C ~ 12
7°C needle-like crystals (recrystallized from ethyl acetate, only the solvent name is listed below) Yield 73% (4) 1-(4-acetamido-2-methoxyphenoxy)-3-[l4-(p-tolyl)piperazinoco -2
-Propatool M, p, 172.5℃~173.5℃ Needle crystals (methanol) yield 91.1% (5) 1-(4-acetamido-2-methoxyphenoxy)-3-C4-(m・Tolyl) piperazinoco-2-glopanol M, p, 124.5°C to 126.5°C Needle crystals (ethyl acetate) Yield 88.2% (6) 1-(4-acetamido-2-methoxyphenoxy)- 3-C4-(o-tolyl)piperazinoco-2-glopanol IL p, 126.5°C to 128°C Prism crystal (Inglovir ether isopropanol) Yield 8
7.5% ('71 1-(4-7 cetamide-2-methoxyphenoxy)-3-C4-(4-chlorophenyl)piperazinoco-2-propatol M, p, 177°C to 178.5°C
Needle crystals (methanol) yield 92.3% (8) 1-(4-acetamido-2-methoxyphenoxy)-3-(4-(3-chlorophenyl)piperazinoco-2-propatol M, p, 141' C~143.5
°C needle crystals (ethanol) yield 88.2% (9) l-(4-acetamido-2-methoxyphenoxy)-3-(4-(2-chlorophenyl)piperazinoco-
2-Propatol M, P, 137.5°C to 140°C Prism crystal (ethyl acetate) Yield 96.4% (10) 1-(4-acetamido-2-methoxyphenoxy)-3-[4-(4 -fluorophenyl)piperazino2-propatool M, p, 175.5°C
~176.5°C needle crystals (ethanol) yield 87.4% (11) 1-(4-acetamido-2-methoxyphenoxy)-3-C4-(3-fluorophenyl)piperazino-2-propatol M, p, 144.5°C ~ 1
46°C needle crystals (ethanol) yield 93.8% Hydrochloride: M, p, 224°C to 226°C
Claims (1)
級アルコキシ基を表わし、Ｒ３はフェニル基、トリフル
オロメチルフェニル基、トリル基もしくはハロゲノフェ
ニル基を表わす。 ）＊＊ テ示すｔ’Ｌ ルア’ロバノール誘導体もしく
はその薬理的に許容しうる酸付加塩。 ２一般式ＣＩ、）で示される化合物が である特許請求の範囲第１項記載の化合物。 である特許請求の範囲第１項又は第２項記載の化合物。 一般式（１）で示される化合物が ４１’−（４−アセタミド−２−メトキシフェノキシ）
−３−（４−フェニルピペラジノ）−２−プロパツール
もしくはその薬理的に許容し５る酸付加塩である特許請
求の範囲第３項記載の化合物。 ５ｌ−（４−アセタミド−２−メトキシフェノキシ）−
３−（４−（ｍ・トリル）ピペラジノコ２−プロパツー
ルもしくはその薬理的に許容しうる酸付加塩である特許
請求の範囲第３項記載の化合物。 ６１−（４−アセタミド−２−メトキシフェノキシ）−
３−（４−（２−フルオロフェニル）ピペラジノコ−２
−プロパツールもしくはその薬理的に許容しうる酸付加
塩である特許請求の範囲第３項記載の化合物。 ７ｌ−（４−アセタミド−２−メトキシフェノキシ）−
３−（４−（３−フルオロフェニル）ピペラジノコ−２
−プロパツールもしくはその薬理的に許容し５る酸付加
塩である特許請求の範囲第３項記載の化合物。 ｆ３１−（４−アセタミド−２−メトキシフェノキシ）
−３−（４−（２−クロロフェニル）ピペラジノコ−２
−プロパツールもしくはその薬理的に許容しうる酸付加
塩である特許請求の範囲第３項記載の化合物。 ９ｌ−（４−アセタミド−２−メトキシフェノキシ）−
３−（４−（３−クロロフェニル）ピペ＊＊ラジノ〕−
２−グロパノールもしくはその薬理的に許容しうる酸付
加塩である特許請求の範囲第３項記載の化合物。 １〇 一般式 （但し、Ｒ′は低級脂肪族アシル基を表わし、は低級ア
ルコキシ基を表わす。 ）で示されるオキシラン誘導体と一般式 （但し Ｒ３はフェニル基、トリフルオロメチルフェニ
ル基、トリル基もしくはハロゲノフェニル基を表わす。 ）で示される化合物とを反応させ、次いで所望により生
成物をその薬理的に許容しうる酸付加塩とすることを特
徴とする一般式 （但し、Ｒ１、Ｒ２及びＲ３は前記と同一意味を有する
。 ）で示されるプロパツール誘導体もしくはその薬理※※
的に許容しうる酸付加塩の製法。[Claims] 1 General formula (wherein R' represents a lower aliphatic acyl group, R2 represents a lower alkoxy group, and R3 represents a phenyl group, trifluoromethylphenyl group, tolyl group or halogenophenyl group) )** t'L Lua'lovanol derivative or a pharmacologically acceptable acid addition salt thereof. 2. The compound according to claim 1, wherein the compound is represented by the general formula CI,). The compound according to claim 1 or 2, which is The compound represented by general formula (1) is 41'-(4-acetamido-2-methoxyphenoxy)
3. The compound according to claim 3, which is -3-(4-phenylpiperazino)-2-propatol or a pharmacologically acceptable acid addition salt thereof. 5l-(4-acetamido-2-methoxyphenoxy)-
The compound according to claim 3, which is 3-(4-(m-tolyl)piperazinoco-2-propatol or a pharmacologically acceptable acid addition salt thereof. )−
3-(4-(2-fluorophenyl)piperazinoco-2
- The compound according to claim 3, which is propatool or a pharmacologically acceptable acid addition salt thereof. 7l-(4-acetamido-2-methoxyphenoxy)-
3-(4-(3-fluorophenyl)piperazinoco-2
- The compound according to claim 3, which is propatool or a pharmacologically acceptable acid addition salt thereof. f31-(4-acetamido-2-methoxyphenoxy)
-3-(4-(2-chlorophenyl)piperazinoco-2)
- The compound according to claim 3, which is propatool or a pharmacologically acceptable acid addition salt thereof. 9l-(4-acetamido-2-methoxyphenoxy)-
3-(4-(3-chlorophenyl)pipe**radino]-
4. The compound according to claim 3, which is 2-gropanol or a pharmacologically acceptable acid addition salt thereof. 10 Oxirane derivatives represented by the general formula (where R' represents a lower aliphatic acyl group and represents a lower alkoxy group) and the general formula (where R3 represents a phenyl group, trifluoromethylphenyl group, tolyl group, or (representing a halogenophenyl group), and then optionally converting the product into its pharmacologically acceptable acid addition salt (wherein R1, R2 and R3 are has the same meaning as above. ) or its pharmacology ※※
A process for producing legally acceptable acid addition salts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51094177A JPS5840551B2 (en) | 1976-08-06 | 1976-08-06 | Propanol derivatives and their production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51094177A JPS5840551B2 (en) | 1976-08-06 | 1976-08-06 | Propanol derivatives and their production method |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57191325A Division JPS596850B2 (en) | 1982-10-29 | 1982-10-29 | Propanol derivatives and their production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5321127A JPS5321127A (en) | 1978-02-27 |
| JPS5840551B2 true JPS5840551B2 (en) | 1983-09-06 |
Family
ID=14103050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51094177A Expired JPS5840551B2 (en) | 1976-08-06 | 1976-08-06 | Propanol derivatives and their production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5840551B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56115769A (en) * | 1980-02-18 | 1981-09-11 | Tanabe Seiyaku Co Ltd | Piperazine derivative and its preparation |
| DK0958280T3 (en) | 1997-10-31 | 2005-08-29 | Daiichi Suntory Pharma Co Ltd | Arylpiperidinopropanol and arylpiperazinopropanol derivatives and pharmaceutical agents containing them |
-
1976
- 1976-08-06 JP JP51094177A patent/JPS5840551B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5321127A (en) | 1978-02-27 |
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