JPS603061B2 - Method for producing 5-(α-substituted aminoalkanoyl)carbostyryl derivative - Google Patents
Method for producing 5-(α-substituted aminoalkanoyl)carbostyryl derivativeInfo
- Publication number
- JPS603061B2 JPS603061B2 JP50072172A JP7217275A JPS603061B2 JP S603061 B2 JPS603061 B2 JP S603061B2 JP 50072172 A JP50072172 A JP 50072172A JP 7217275 A JP7217275 A JP 7217275A JP S603061 B2 JPS603061 B2 JP S603061B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- carbon atoms
- lower alkyl
- represented
- 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.)
- Expired
Links
- 125000005606 carbostyryl group Chemical group 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- -1 for example Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は新規なる５−（ａ−置換ァミノァルカノィル）
カルボスチリル誘導体の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel 5-(a-substituted aminoalkanoyl)
This invention relates to a method for producing carbostyril derivatives.
本発明で得られる５‐‐（ａ−置換アミノアルカノィル
）カルボスチリル議導体は一般式〔式中Ｒ，及びＲ３は
水素原子又は炭素数１〜２個の低級ァルキル基を示し、
Ｒ２は炭素数１〜２個の低級アルキル基又は一般式（式
中ｎは１〜４の整
数）で表わされるアラルキル基を示す。The 5--(a-substituted aminoalkanoyl)carbostyryl derivative obtained in the present invention has the general formula [wherein R and R3 represent a hydrogen atom or a lower alkyl group having 1 to 2 carbon atoms,
R2 represents a lower alkyl group having 1 to 2 carbon atoms or an aralkyl group represented by the general formula (wherein n is an integer of 1 to 4).
またＲ４は水素原子、炭素数１〜４個の低級アルキル基
又は一般式（式中ｎ‘ま上記
に同じ）で表わされるアラルキル基を示す。Further, R4 represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or an aralkyl group represented by the general formula (in the formula, n' is the same as above).
但し、Ｒ，及びＲ２が炭素数１〜２個の低級アルキル基
を示し、且つＲ３が水素原子を示す場合には、Ｒ４は炭
素数１〜４個の低級アルキル基であってはならない。で
表わされる化合物である。本発明２に於いては更に上記
化合物の酸付加塩を包含する。本発明の上記化合物及び
その酸付加塩は新規化合物であって、Ｂ−アドレナリン
作動薬として有用である。本発明に係る５−（ａ−置換
アミノァルカノィ３ル）カルボスチリル議導体は−般式
〔式中Ｒ，，Ｒ２，Ｒ３は上記に同じであり、×はハロ
ゲン原子を示す。However, when R and R2 represent a lower alkyl group having 1 to 2 carbon atoms, and R3 represents a hydrogen atom, R4 must not be a lower alkyl group having 1 to 4 carbon atoms. It is a compound represented by Invention 2 further includes acid addition salts of the above compounds. The above compounds of the present invention and their acid addition salts are novel compounds and are useful as B-adrenergic agonists. The 5-(a-substituted aminoalkanoyl)carbostyryl conductor according to the present invention has the general formula [wherein R, , R2, and R3 are the same as above, and x represents a halogen atom.
〕で表わされる５一（ａ−ハロアルカノィル）カルポス
チリル譲導体と一般式Ｒ４Ｎ仏
（０）〔式中Ｒ４は上記に同じ。] 5-(a-haloalkanoyl) carpostyryl transfer derivative and the general formula R4N Buddha
(0) [In the formula, R4 is the same as above.
〕で表わされるアミンとを反応させることにより製造さ
れる。] is produced by reacting with an amine represented by:
本発明の出発物質である一般式（１）で表わされる５−
（ａーハロアルカ／イル）カルボスチリル譲導体は新規
化合物である。5- represented by general formula (1) which is the starting material of the present invention
(a-haloalka/yl)carbostyryl derivatives are new compounds.
該化合物は例えば一般式〔式中Ｒ，及びＲ２は上記に同
じ。The compound has, for example, the general formula [wherein R and R2 are the same as above].
〕で表わされるカルボスチリル譲導体と一般式〔式中Ｒ
３及びＸは上記に同じであり、Ｘ′はハロゲン原子を示
す。] and the general formula [wherein R
3 and X are the same as above, and X' represents a halogen atom.
〕で表わされるａ−ハロアルカン酸ハラィドとを反応さ
せることにより得られる。It is obtained by reacting with an a-haloalkanoic acid halide represented by the following formula.
この反応はフリーデル・クラフッ反応と呼ばれるもので
あり、一般にルイス酸の存在下行なわれる。ここに使用
されるルイス酸としては例えば無水塩化アルミニウム、
塩化チタン等が挙げられる。之等ルイス酸の使用量は適
宜選択すれば良いが、通常一般式（１）′で表わされる
カルボスチリル誘導体に対し１〜５倍モル（好ましくは
２〜４倍モル）用いられる。また一般式（１）′で表わ
されるカルボスチリル誘導体と一般式（０）′で表わさ
れるａ−ハロアルカン酸ハライドとの使用割合も適宜選
択すればよいが、通常前者に対し、後者を等倍モル〜大
過乗り（好ましくは１．５〜５倍モル）を用いればよい
。この反応は無溶媒又は溶媒中のいずれでも行なうこと
ができる。溶媒としては通常例えばニトロベンゼン、メ
チレンクロライド、エチレンクロラィド等が使用される
。この反応に於ける反応温度は特に限定されないが一般
に室温〜１２０℃（好ましくは５０〜８０℃）で有利に
進行する。上記反応により本発明の上記出発物質を容易
に得ることができる。上記一般式（１）で表わされる５
−（ａーハロアルカノィル）カルボスチリル誘導体に於
いて、Ｒ，，Ｒ２及びＲ３で示される炭素数１〜２個の
低級アルキル基としてはメチル及びエチル基が挙げられ
る。This reaction is called the Friedel-Krach reaction, and is generally carried out in the presence of a Lewis acid. Examples of the Lewis acid used here include anhydrous aluminum chloride,
Examples include titanium chloride. The amount of Lewis acid to be used may be selected as appropriate, but it is usually used in an amount of 1 to 5 times the mole (preferably 2 to 4 times) of the carbostyril derivative represented by the general formula (1)'. Furthermore, the ratio of the carbostyril derivative represented by the general formula (1)' and the a-haloalkanoic acid halide represented by the general formula (0)' may be selected as appropriate, but usually the latter is used in equal molar proportions to the former. - A large overload (preferably 1.5 to 5 times the mole) may be used. This reaction can be carried out without a solvent or in a solvent. As the solvent, for example, nitrobenzene, methylene chloride, ethylene chloride, etc. are usually used. The reaction temperature in this reaction is not particularly limited, but it generally proceeds advantageously at room temperature to 120°C (preferably 50 to 80°C). The above-mentioned starting material of the present invention can be easily obtained by the above-mentioned reaction. 5 represented by the above general formula (1)
In the -(a-haloalkanoyl)carbostyryl derivative, examples of the lower alkyl group having 1 to 2 carbon atoms represented by R, , R2 and R3 include methyl and ethyl groups.
Ｒ２で表わされるアラルキル基として例えばペンジル及
びフェネル基等が挙げられる。またＸで示されるハロゲ
ン原子としては例えば塩素、臭素及び沃素原子等が挙げ
られる。 タ本発明の他方の出発物質である
一般式（０）で表わされるアミンとしては具体的には例
えばアンモニアの他〆チルアミン、エチルアミン、プロ
ピルアミン、イソブロピルアミン、ブチルアミン、ｓｅ
ｃーブチルアミン、企てｔーブチルアミン等の脂の肪族
アミン、ベンジルアミン、フェネルアミン、フェニルプ
ロピルアミン等の芳香族アミンが挙げられる。本発明に
於いて一般式（１）で表わされる５一（ａーハロアルカ
ノイル）カルボスチリル誘導体Ｊと一般式（０）で表わ
されるアミンとの反応は、上記原料アミン自体溶媒とし
て作用するため無溶媒で行なってもよく、又適当な溶媒
中で行なってもよい。Examples of the aralkyl group represented by R2 include penzyl and phenel groups. Examples of the halogen atom represented by X include chlorine, bromine, and iodine atoms. Examples of the amine represented by the general formula (0), which is the other starting material of the present invention, include ammonia, ethylamine, ethylamine, propylamine, isopropylamine, butylamine, se
Examples include fatty aliphatic amines such as c-butylamine and t-butylamine, and aromatic amines such as benzylamine, phenelamine, and phenylpropylamine. In the present invention, the reaction between the 5-(a-haloalkanoyl)carbostyryl derivative J represented by the general formula (1) and the amine represented by the general formula (0) is unnecessary because the raw material amine itself acts as a solvent. It may be carried out in a solvent or in a suitable solvent.
この際使用される溶媒としては、反応に関与しないもの
であれば特に限定されないが、通２常例えばメタノール
、エタノール、ィソプロバノール等の低級アルコール類
、水等が好適に使用される。一般式（１）で表わされる
５一（ａーハロアルカノィル）カルポスチリル誘導体と
一般式（Ｕ）２で表わされるアミンとの使用割合は適宜
選択すれば良いが、通常無溶媒で反応を行なう場合には
前ｉ者に対し後者を大過剰荊・、又溶媒中で行なう場合
には前者に対し後者を等モル〜３倍モル程度用いるのが
好ましい。The solvent used at this time is not particularly limited as long as it does not participate in the reaction, but lower alcohols such as methanol, ethanol, isoprobanol, water, etc. are usually preferably used. The ratio of the 5-(a-haloalkanoyl)carpostyryl derivative represented by the general formula (1) and the amine represented by the general formula (U)2 may be selected as appropriate, but the reaction is usually carried out without a solvent. In this case, it is preferable to use a large excess of the latter with respect to the former, and when carrying out the reaction in a solvent, it is preferable to use the latter in an equimolar to about 3 times the molar amount of the former.
３本反応に於ける反応温度は
特に限定されないが、一般に室温乃至還流温度附近（好
ましくは４０〜６ぴ０）で有利に進行し、原料の種類、
使用量等により適宜選択される。本反応により得られる
５一（ａ−鷹換アミノア３ルカノイル）カルボスチリル
誘導体は塩酸、硫酸、フツ化水素酸、臭化水素酸等の無
機酸、シュウ酸、マレィン酸等の有機酸と反応させ、生
理的に許容される酸付加塩として単離することができる
。The reaction temperature in the three-step reaction is not particularly limited, but it generally proceeds advantageously at room temperature to around reflux temperature (preferably 40 to 60 mm), and depends on the type of raw materials,
It is selected appropriately depending on the usage amount, etc. The 5-(a-converted aminoalkanoyl)carbostyryl derivative obtained by this reaction is reacted with an inorganic acid such as hydrochloric acid, sulfuric acid, hydrofluoric acid, or hydrobromic acid, or an organic acid such as oxalic acid or maleic acid. , can be isolated as a physiologically acceptable acid addition salt.
４本発明の出発
物質である一般式（１）で表わされる５−（ａーハロア
ルカノイル）カルボスチリル誘導体を得るための適当な
方法を下記参考例に示し、引き続き実施例を示す。参考
例 １
８ーメトキシカルボスチリル４０夕にニトロベンゼン３
０の【、クロロアセチルクロライド７０のＺを加えて全
液を氷水で冷却しながらこれに塩化アルミニウム２３０
夕を徐々に加えて、６０℃で４時間瀦梓反応させる。4 An appropriate method for obtaining the 5-(a-haloalkanoyl)carbostyryl derivative represented by the general formula (1), which is the starting material of the present invention, is shown in the following Reference Examples, followed by Examples. Reference example 1 8-methoxycarbostyryl 40 nitrobenzene 3
Add 70% Z of chloroacetyl chloride and add 230% aluminum chloride to the whole solution while cooling it with ice water.
Gradually add water and allow to react at 60°C for 4 hours.
反応後全反応液を１その氷水中に注力０して得られる析
出物を炉取し、エーテルで洗浄し、メタノールから再結
晶して５ークロロアセチル−８ーメトキシカルボスチリ
ル３１夕を得る。参考例 ２参考例１と同様にして、５
一（ａーブロモプチリル）一８ーメトキシカルボスチリ
ルを得る。After the reaction, the entire reaction solution was concentrated in ice water, and the resulting precipitate was collected in a furnace, washed with ether, and recrystallized from methanol to obtain 5-chloroacetyl-8-methoxycarbostyryl. Reference example 2 In the same way as reference example 1, 5
1-(a-bromoptyryl)-18-methoxycarbostyryl is obtained.
ｍ．ｐ．１６９〜１７０℃（メタノールより再結晶）。
実施例 １５一（ａ−プロモブチリル）−８ーメトキシ
カルボスチリル２夕をペンジルアミン４の【に徐々に加
え、室温で４時間縄拝する。m. p. 169-170°C (recrystallized from methanol).
Example 15 -(a-Promobutyryl)-8-methoxycarbostyryl was gradually added to pendylamine (4) and allowed to stand at room temperature for 4 hours.
反応液にエチルエーテル５０私を加えて不溶分を除去後
、該反応液を１／３倍に濃縮する。この濃縮液に石油エ
ーテル１２０の‘を加え、析出油状物を鏡斜により取り
出し、ィソブロパノール１０私に溶解する。次いで濃塩
酸を加えてｐＨＩ〜２とする。析出物を炉取し、エタノ
ールーアセトンより再結晶して融点１６２〜１６４℃（
分解点）の５一（ａーベンジルアミノブチリル）一８ー
メトキシカルボスチリル塩酸塩１．１夕を得る。実施例
２〜６
適当な出発物質を用い、上記と同様に反応させて得られ
る本発明の各化合物を下記第１表に示す。After adding 50 μl of ethyl ether to the reaction solution to remove insoluble matter, the reaction solution is concentrated to 1/3. 120 parts of petroleum ether is added to this concentrated solution, and the precipitated oily substance is taken out using a microscope and dissolved in 10 parts of isopropanol. Concentrated hydrochloric acid is then added to bring the pH to ~2. The precipitate was collected in a furnace and recrystallized from ethanol-acetone to a melting point of 162-164°C (
1.1 tons of 5-(a-benzylaminobutyryl)-18-methoxycarbostyril hydrochloride with a decomposition point) of Examples 2 to 6 Compounds of the present invention obtained by reacting in the same manner as above using appropriate starting materials are shown in Table 1 below.
第１表Table 1
Claims (1)
個の低級アルキル基を示し、Ｒ＿２は炭素数１〜２個の
低級アルキル基又は一般式▲数式、化学式、表等があり
ます▼ （式中ｎは１〜４の整数 を示す）で表わされるアラルキル基を示す。 またＸはハロゲン原子を示す。〕で表わされる５−（ａ
−ハロアルカノイル）カルボスチリル誘導体と一般式Ｒ
＿４ＮＨ＿２ 〔式中Ｒ＿４は水素原子、炭素数１〜４個の低級アル
キル基又は一般式▲数式、化学式、表等があります▼ （式中ｎは１〜４の整数を示す）で表わされるアラル
キル基を示す。 〕で表わされるアミンとを反応させることを特徴とする
一般式▲数式、化学式、表等があります▼ 〔式中Ｒ＿１，Ｒ＿２，Ｒ＿３及びＲ＿４は上記に同
じ。 但し、Ｒ＿１及びＲ＿２が炭素数１〜２個の低級アルキ
ル基を示し、且つＲ＿３が水素原子を示す場合には、Ｒ
＿４は炭素数１〜４個の低級アルキル基であってはなら
ない。〕で表わされる５−（ａ−置換アミノアルカノイ
ル）カルボスチリル誘導体の製造法。[Claims] 1 General formula ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_1 and R_3 are hydrogen atoms or have 1 to 2 carbon atoms]
R_2 is a lower alkyl group having 1 to 2 carbon atoms or an aralkyl group represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (in the formula, n represents an integer from 1 to 4) Indicates the group. Moreover, X represents a halogen atom. ] 5-(a
-haloalkanoyl)carbostyryl derivative and general formula R
_4NH_2 [In the formula, R_4 is a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or an aralkyl group represented by the general formula ▲ Numerical formula, chemical formula, table, etc. ▼ (in the formula, n represents an integer of 1 to 4) shows. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_1, R_2, R_3 and R_4 are the same as above. However, when R_1 and R_2 represent a lower alkyl group having 1 to 2 carbon atoms, and R_3 represents a hydrogen atom, R
_4 must not be a lower alkyl group having 1 to 4 carbon atoms. ] A method for producing a 5-(a-substituted aminoalkanoyl)carbostyryl derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50072172A JPS603061B2 (en) | 1975-06-13 | 1975-06-13 | Method for producing 5-(α-substituted aminoalkanoyl)carbostyryl derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50072172A JPS603061B2 (en) | 1975-06-13 | 1975-06-13 | Method for producing 5-(α-substituted aminoalkanoyl)carbostyryl derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51149283A JPS51149283A (en) | 1976-12-22 |
| JPS603061B2 true JPS603061B2 (en) | 1985-01-25 |
Family
ID=13481531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50072172A Expired JPS603061B2 (en) | 1975-06-13 | 1975-06-13 | Method for producing 5-(α-substituted aminoalkanoyl)carbostyryl derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS603061B2 (en) |
-
1975
- 1975-06-13 JP JP50072172A patent/JPS603061B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51149283A (en) | 1976-12-22 |
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