JPS6038398B2 - Thiazinoimidazole derivative and method for producing the same - Google Patents
Thiazinoimidazole derivative and method for producing the sameInfo
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- JPS6038398B2 JPS6038398B2 JP2835580A JP2835580A JPS6038398B2 JP S6038398 B2 JPS6038398 B2 JP S6038398B2 JP 2835580 A JP2835580 A JP 2835580A JP 2835580 A JP2835580 A JP 2835580A JP S6038398 B2 JPS6038398 B2 JP S6038398B2
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Description
【発明の詳細な説明】
本発明は新規なチァジノィミダゾール誘導体、更に詳細
には、次の一般式（１）、（式中、Ａは炭素原子又は窒
素原子を示し、Ｒ，及びＲ２は水素原子又はアルキル基
を示す。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel thiazinimidazole derivatives, more specifically, the following general formula (1), (wherein A represents a carbon atom or a nitrogen atom, R, and R2 represents a hydrogen atom or an alkyl group.
但し、Ｒ，及びＲ２が共に水素原子ではないものとする
）で表わされるチアジノィミダゾール誘導体及びその酸
付加塩、並びにその製造法に関する。従来、ィミダゾー
ル誘導体について多くの研究がなされており、就中前記
一般式（１）中、Ｒ，．Ｒ２が共に水素原子でＡが炭素
原子で表される化合分が解熱及び消炎作用を有すること
が報告されている（袴関昭５０−３６４９６号）。The present invention relates to a thiazinimidazole derivative represented by (provided that both R and R2 are not hydrogen atoms), an acid addition salt thereof, and a method for producing the same. Conventionally, many studies have been conducted on imidazole derivatives, in particular, in the general formula (1), R, . It has been reported that a compound in which R2 is both a hydrogen atom and A is a carbon atom has antipyretic and antiinflammatory effects (Hakamaseki No. 50-36496).
本発明者は、チァジノィミダゾール誘導体について種々
研究を重ねていたところ、前詩ｙｌ万式で表わされる新
規化合物が循環器系に対する諸作用、すなわち冠血管拡
張作用、末梢血管拡張作用、緩徐な降圧作用を有するこ
とを見出し、本発明を完成した。The present inventor has conducted various studies on thiazinimidazole derivatives, and discovered that a new compound represented by the above formula has various effects on the circulatory system, namely coronary vasodilatory effect, peripheral vasodilatory effect, and slow vasodilatory effect. The present invention was completed based on the discovery that it has a significant antihypertensive effect.
従って、本発明は循環器系薬剤として有用な新規チアジ
ノィミダゾール誘導体〜１）を提供するものである。Therefore, the present invention provides novel thiazinimidazole derivatives ~1) useful as cardiovascular drugs.
更にまた、本発明はチアジノィミダゾール誘導付ｄｌ）
の新規な製造法を提供するものである。本発明のチアジ
ノイミダゾール誘導体は、Ｒ，，Ｒ２及びＡの種類によ
って次式（ｌａ）〜（ｌｄ）の化合物に大別できる。Furthermore, the present invention provides thiazinimidazole-induced dl)
The present invention provides a new method for manufacturing. The thiazinoimidazole derivatives of the present invention can be roughly classified into compounds of the following formulas (la) to (ld) depending on the types of R, , R2 and A.
（式中、Ｒ，及びＲ２はアルキル基を示す）本発明化合
物（１）は、例えば次の反応式に従って、２−メルカプ
ト−ＩＨーイミダゾ化合物（０）に１，３ージハロゲノ
プロパン譲導体（ｍ）を反応せしめることにより製造さ
れる。The compound (1) of the present invention (wherein R and R2 represent an alkyl group) can be prepared by converting a 2-mercapto-IH-imidazo compound (0) into a 1,3-dihalogenopropane derivative ( It is produced by reacting m).
（式中、Ｘ及びＹはハロゲン原子を示し、Ｒ，，Ｒ２及
びＡは前記と同じものを示す）本方法を実施するには、
（０万犬中Ａが炭素原子で表わされる２−メルカブトー
ＩＨ−ィミダゾ〔４，５一ｂ〕ピリジン又はＡが窒素原
子で表わされる８ーメルカプトプリンと１，３ージハロ
ゲノプロパン議導体（ｍ）とを反応に不活性な溶媒中塩
基の存在下反応させる。(In the formula, X and Y represent halogen atoms, and R,, R2 and A represent the same as above.) To carry out this method,
(2-mercabuto IH-imidazo[4,51b]pyridine in which A is a carbon atom or 8-mercaptopurine and 1,3-dihalogenopropane conductor (m ) in the presence of a base in an inert solvent.
溶媒としては、メタノール、エタノール、ブロパノール
、ィソプロパノールの如きアルコール類が好ましく、塩
基としては水酸化ナトリウム、水酸化カリウム、炭素水
素ナトリウム、炭酸ナトリウム、炭酸カリウム等のアル
カリ金属あるいはアルカリ士類金属の水酸化物又は炭酸
塩が好ましい。As the solvent, alcohols such as methanol, ethanol, propanol, and isopropanol are preferable, and as the base, alkali metals or alkali metals such as sodium hydroxide, potassium hydroxide, sodium bicarbonate, sodium carbonate, and potassium carbonate are preferable. Hydroxides or carbonates are preferred.
反応は数時間ないしは十数時間還流を行うことによって
なし得る。更に収率を上げるためには、例えばョウ化カ
リウム、ョウ化ナトリウム等のヨウ素化合物を加えるこ
ともできる。The reaction can be carried out by refluxing for several hours to more than ten hours. In order to further increase the yield, iodine compounds such as potassium iodide and sodium iodide can be added.
このようにするとき、本発明化合物ＸＩ）は、その異性
体である次式（Ｗ）、（式中、Ｒ，，Ｒ２及びＡは前記
した意味を有する）で表わされる化合物との混合物とし
て得られる。In this case, the compound XI) of the present invention can be obtained as a mixture with its isomer, a compound represented by the following formula (W), in which R, , R2 and A have the meanings given above. It will be done.
しかし、両者は例えばカラムクロマトグラフィーによっ
て、すなわちその混合物をシリカゲル等を用いるカラム
クロマトグラフイーに付し、クロロホルム、クロロホル
ム：メタノール（１０：１）の混液の順に流出させると
クロロホルム流出部より（Ｎ）が、クロロホルム：メタ
ノール（１０：１）の濠液流出部より（１）が流出し、
各々の異性体を単機精製することができる。更に斯くし
て得られた本発明のチアジノィミダゾール誘導体は、必
要に応じて、常法により塩酸塩、臭化水素酸塩、過塩素
酸塩などの無機塩またはフマール酸塩、コハク酸塩、酒
石酸塩、マレィン酸塩、シュウ酸塩などの有機酸塩とす
ることができる。However, if the mixture is subjected to column chromatography using silica gel or the like, and chloroform and a mixture of chloroform:methanol (10:1) are flowed out in this order, (N) is produced from the chloroform outflow part. However, (1) flows out from the outflow part of the moat liquid of chloroform:methanol (10:1),
Each isomer can be purified in a single machine. Furthermore, the thiazinimidazole derivative of the present invention thus obtained can be treated with inorganic salts such as hydrochloride, hydrobromide, perchlorate, fumarate, succinic acid, etc. by a conventional method, if necessary. It can be a salt, an organic acid salt such as a tartrate, a maleate, an oxalate, etc.
斯くの如くして得られる本発明化合物の循環器に対する
作用を試験した結果は次のとおりである。The results of testing the effect of the compound of the present invention thus obtained on the circulatory system are as follows.
血管拡張作用及び降圧作用
体重１５〜２５ｋ９の雌雄成雑犬をペントバルビタール
ナトリウム（３０の９／ｋ９ｉｖ）で麻酔した後、人工
呼吸下に右大腿動脈に矩形波電磁流量計のフロープロー
ブを装着し、血流量を測定した。Vasodilator and antihypertensive effects After anesthetizing male and female adult mongrel dogs weighing 15 to 25k9 with sodium pentobarbital (309/k9iv), a flow probe of a square wave electromagnetic flowmeter was attached to the right femoral artery under artificial respiration. , blood flow was measured.
血圧は左大腿動脈内に挿入したポリエチレンカニューレ
から圧トランスデューサーを介し測定した。同時に心拍
数を測定した。この結果、本発明化合物には明らかな血
流量増加作用が認められた。Blood pressure was measured via a pressure transducer through a polyethylene cannula inserted into the left femoral artery. At the same time, heart rate was measured. As a result, the compound of the present invention was found to have a clear blood flow increasing effect.
次に本発明の実施例を挙げて説明する。Next, examples of the present invention will be described.
実施例 １
３，４−ジヒドロ−４一ｎ−プロピル−２Ｈ−（１，３
）ーチアジノ〔３，２一ａ〕ピリド〔２，３−ｄ〕イミ
ダゾール：２−メルカプトーＩＨ−イミダゾ〔４，５−
ｂ〕ピリジン１．２０夕（７．９５ミリモル）をエタノ
ール５０の‘に懸濁させ、これに１，３ージブロモヘキ
サン２．００夕（８．２ミリモル）、ョウ化カリウム２
．６夕（１５７ミリモル）及び炭酸水素ナトリウム１．
３夕（１６．１ミリモル）を加えて７．虫篭間還流した
。Example 1 3,4-dihydro-4-n-propyl-2H-(1,3
)-thiazino[3,21a]pyrido[2,3-d]imidazole: 2-mercaptoIH-imidazo[4,5-
b] 1.20 mmol (7.95 mmol) of pyridine was suspended in 50 mmol of ethanol, and 2.00 mmol (8.2 mmol) of 1,3-dibromohexane and 2 mmol of potassium iodide were suspended in 50 mmol of ethanol.
．． 6 ml (157 mmol) and sodium bicarbonate 1.
7. Add 3 mol (16.1 mmol). The insect cage was refluxed.
冷後反応液を炉過し炉液を減圧濃縮した。残留物に１０
％水酸化ナトリウム水溶液５０の‘を加えクロロホルム
で抽出し、クロロホルム層を水洗した。無水硫酸ナトリ
ウムで乾燥後クロロホルムを減圧留去し、残澄をシリカ
ゲルカラムクロマトグラフイーに付し、まず、クロロホ
ルム５００の‘を流し流出部を除いた後、クロロホルム
：メタノール（１０：１）の混液５００の‘を流し流出
部を集め濃縮し淡黄色結晶（融点１２２〜４℃）の目的
物４８０奴ｏ（収率２６％）を得た。元素分析値：Ｃ，
２日，がぶ（２３３．３２）としてＣ 日 Ｎ Ｓ理論
値（％） ６１．７７ ６．４８ １８．０１
１３７４実測値（％） ６１．８２ ６．５６
１７．払 １４．雌ＮＭＲスペクトル：６ｐｐｍ（ＣＤ
Ｃ１４）７・３５（ｄｄ，Ｃ６−Ｈ）、７・〇。After cooling, the reaction liquid was filtered through a furnace, and the furnace liquid was concentrated under reduced pressure. 10 for residue
A 50% aqueous solution of sodium hydroxide was added and extracted with chloroform, and the chloroform layer was washed with water. After drying over anhydrous sodium sulfate, chloroform was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography. First, 500% of chloroform was poured in to remove the outflow, and then a mixture of chloroform and methanol (10:1) was added. 500° C. was poured, and the outflow was collected and concentrated to obtain 480 μg of the desired product (yield: 26%) as light yellow crystals (melting point: 122-4° C.). Elemental analysis value: C,
2nd, Gabu (233.32) C day NS theoretical value (%) 61.77 6.48 18.01
1374 Actual value (%) 61.82 6.56
17. Payment 14. Female NMR spectrum: 6ppm (CD
C14) 7.35 (dd, C6-H), 7.0.
（ｄｄ● Ｃ？−Ｈ）、８２８（ｄｄ，Ｃ８一Ｈ）、４
．５０（ｍ，Ｃ４一Ｈ）、２．滋（ｍ，Ｃ３−比）、３
１２（ｍ，Ｃ２−日２）、０．班（ｔ，ＣＨ３Ｃ比ＣＨ
２一）、１．７１（ｍ，Ｃ比ＣＨ２ＣＨ２一）実施例
３
３，４ージヒドロー４−ｎ−ベンチルー２Ｈ−（１，３
）ーチアジノ〔３，２一ａ〕ピリミジノ〔４，５−ｄ〕
イミダゾール：８ーメルカプトプリン１．５２夕（１０
．０ミリモル）をエタノール７０叫に懸濁させ、これに
１，３ージプロモオクタン２．９５夕（１０．８５ミリ
モル）、ョウ化カリウム３．４０夕（２０．５ミリモル
）及び炭酸水素ナトリウム１．８７夕（２２．３ミリモ
ル）を加え１母時間還流した。(dd● C?-H), 828 (dd, C8-H), 4
．． 50 (m, C4-H), 2. Shigeru (m, C3-ratio), 3
12 (m, C2-day 2), 0. Group (t, CH3C ratio CH
21), 1.71 (m, C ratio CH2CH2) Example
3 3,4-dihydro 4-n-benzene 2H-(1,3
) - Thiazino [3,21a] Pyrimidino [4,5-d]
Imidazole: 8-mercaptopurine 1.52 min (10
．． 0 mmol) was suspended in 70 mmol of ethanol, and to this were added 2.95 mmol of 1,3-dipromooctane (10.85 mmol), 3.40 mmol of potassium iodide (20.5 mmol), and sodium bicarbonate. 1.87 mmol (22.3 mmol) was added and the mixture was refluxed for 1 hour.
以下実施例１と同様に処理し無色結晶（融点１０７〜９
℃）の目的物９００のｃ（収率３４．４％）を得た。Thereafter, the treatment was carried out in the same manner as in Example 1, and colorless crystals (melting point 107-9
The desired product 900°C (yield 34.4%) was obtained.
元素分析値：Ｃ，３日，８Ｎ４Ｓ（２６２．３７）とし
てＣ 日 Ｎ Ｓ理論値（％） ５９．５１ ６．
９１ ２１．３６ １２．２０実測値（％） ５９
．８１ ７．０５ ２１．Ｍ １２．１０ＮＭＲス
ペクトル：６ｐｐｍ（ＣＤＣ１３）８．６９（ｓ，Ｃ６
−Ｈ）、８．斑（ｓ，Ｃ８一Ｈ）、４．７８（ｍ，Ｃ４
−Ｈ）、２．６０（ｍ，Ｃ３一日２）、３．２８（Ｃ２
一比）、０．９０（ｔ，ＣＨ３ −）、１，４０（ｂ・
，ｓ，一Ｃ３ＨＢ −）、１．班（ｍ，一ＣＨ２−）実
施例 ３
３，４−ジヒドロー３一ｎーブチルー２Ｈ−（１，３）
−チアジノ〔３，２−ａ〕ピリド〔２，３一ｄ〕イミダ
ゾール：２−メルカプト−ＩＨ−イミダゾ〔４，５−ｂ
〕ピリジン１．５１夕（１０ミリモル）をエタノール６
０の‘に懸濁させ、これに１ーブロモー２−フロモメチ
ルヘキサン２．８４夕（１１ミリモル）、ヨウ化カリウ
ム３．３２夕（松．３ミリモル）及び炭酸水素ナトリウ
ム１．８７夕（２０ミリモル）を加えて８時間還流した
。Elemental analysis value: C, 3 days, 8N4S (262.37) C day N S theoretical value (%) 59.51 6.
91 21.36 12.20 Actual value (%) 59
．． 81 7.05 21. M 12.10 NMR spectrum: 6 ppm (CDC13) 8.69 (s, C6
-H), 8. Spot (s, C8-H), 4.78 (m, C4
-H), 2.60 (m, C3 2 days), 3.28 (C2
1 ratio), 0.90 (t, CH3 −), 1,40 (b・
, s, -C3HB-), 1. Group (m,1CH2-) Example 3 3,4-dihydro31n-butyl-2H-(1,3)
-thiazino[3,2-a]pyrido[2,31d]imidazole: 2-mercapto-IH-imidazo[4,5-b
] 1.51 liters (10 mmol) of pyridine to 6 ml of ethanol
To this were added 2.84 mmol (11 mmol) of 1-bromo-2-furomomethylhexane, 3.32 mmol potassium iodide (3 mmol) and 1.87 mmole (20 mmol) of sodium bicarbonate. mmol) and refluxed for 8 hours.
以下実施例１と同様に処理して無色結晶（融点８５〜７
℃）の目的物偽０雌（収率２５．５％）を得た。Thereafter, the same treatment as in Example 1 was carried out to obtain colorless crystals (melting point 85-7).
The target pseudo-0 female (yield: 25.5%) was obtained.
元素分析値：Ｃ，３日，？Ｎぶ（２４７．３５）として
Ｃ 日 Ｎ Ｓ理論値（％） ６３．１２ ６．９
３ １６．９９ １２．９６実測値（％） 筋．２
６ ７．０１ １０６２ １３１１ＮＭＲスペクト
ル：６ｐｐｍ（ＣＤＣ１３）７．３（ｄｄ，Ｃ６一Ｈ）
、６９（ｄｄ，Ｃ７一Ｈ）、８．３（ｄｄ，Ｃ８−Ｈ）
、４．１５（ｄｄ，Ｃ４−日２）、３．６５（ｄｄ，Ｃ
４−日２）、２．５−２．０（ｂ，Ｃ３−Ｈ）、３（ｍ
，Ｃ２一日２）、１．６−１．１（ｂ．−Ｃ３ＨＢ−）
、０．９（ｂ（ｔ），一ＣＨ３）
実施例 ４
３，４−ジヒドロ−３一ｎ−ベンチルー２Ｈ−（１，３
）−チアジノ〔３，２−ａ〕ピリミジ／〔４，５一ｄ〕
イミダゾール：８ーメルカプトプリン１．５２夕（１０
．０ミリモル）をエタノール７０の‘に懸濁させ、これ
に１−ブロモ−２−フロモメチルヘブタン２．９５夕（
１０．８５ミリモル）、ョウ化カリウム３．４０夕（２
０．５ミリモル）及び炭酸水酸ナトリウム１．８７夕（
２２．３ミリモル）を加え１曲時間還流した。Elemental analysis value: C, 3 days, ? C day N S theoretical value (%) 63.12 6.9 as N (247.35)
3 16.99 12.96 Actual value (%) Line. 2
6 7.01 1062 1311 NMR spectrum: 6 ppm (CDC13) 7.3 (dd, C6-H)
, 69 (dd, C7-H), 8.3 (dd, C8-H)
, 4.15 (dd, C4-day 2), 3.65 (dd, C
4-day 2), 2.5-2.0 (b, C3-H), 3 (m
, C2 day 2), 1.6-1.1 (b.-C3HB-)
,0.9(b(t),-CH3) Example 4 3,4-dihydro-3-n-benzene-2H-(1,3
)-thiazino[3,2-a]pyrimidi/[4,5-d]
Imidazole: 8-mercaptopurine 1.52 min (10
．． 0 mmol) was suspended in 70' of ethanol, and to this was added 2.95 mmol of 1-bromo-2-furomomethylhebutane (
10.85 mmol), potassium iodide 3.40 mmol (2
0.5 mmol) and 1.87 mmol of sodium carbonate hydroxide (
22.3 mmol) was added and refluxed for one hour.
以下実施例１と同様に処理し無色結晶（融点９１〜３℃
）の目的物５７０の９（収率２１．７％）を得た。Thereafter, the treatment was carried out in the same manner as in Example 1, and colorless crystals (melting point 91-3℃)
) The desired product 570:9 (yield 21.7%) was obtained.
元素分析値：Ｃ，３日，８Ｎ４Ｓ（２６２．３７）とし
てＣ 日 Ｎ Ｓ理論値（％） ５９．５１ ６．
９１ ２１．３６ １２．２０実測値（％） ５９
．桝 ７．１２ ２０．９６ １２．雌ＮＭＲスペ
クトル：６ｐｐｍ（ＣＤＣ１３）８．６５（ｓ，Ｃ６−
Ｈ）、８．９（ｓ，Ｃ８−Ｈ）、４．４（ｄｄ，Ｃ４−
Ｈ）、３．９（ｄｄ，Ｃ４一Ｈ）、２．７−２．１（ｂ
，Ｃ３−Ｈ）、３．２（ｍ，Ｃ２−Ｈ）、１．７−１‐
１（ｂ，一Ｃ４土虫 −）、０‐９（ｂ（ｔ），一Ｃ旦
３ ）実施例 ５〜１２
実施例１と同様にして第１表に示す化合物を製造した。Elemental analysis value: C, 3 days, 8N4S (262.37) C day N S theoretical value (%) 59.51 6.
91 21.36 12.20 Actual value (%) 59
．． Masu 7.12 20.96 12. Female NMR spectrum: 6 ppm (CDC13) 8.65 (s, C6-
H), 8.9 (s, C8-H), 4.4 (dd, C4-
H), 3.9 (dd, C4-H), 2.7-2.1 (b
, C3-H), 3.2(m, C2-H), 1.7-1-
1 (b, 1C4 earthworm-), 0-9 (b(t), 1Cdan3) Examples 5 to 12 The compounds shown in Table 1 were produced in the same manner as in Example 1.
第１表実施例 １３〜１９
実施例２と同様にして第２表に示す化合物を製＊造した
。Table 1 Examples 13 to 19 The compounds shown in Table 2 were produced in the same manner as in Example 2.
第２表 実施例 ２０〜２５ 実施例３と同様にして第３表に示す化合物を製造した。Table 2 Examples 20-25 The compounds shown in Table 3 were produced in the same manner as in Example 3.
第３表実施例 ２６〜３１ 実施例４と同様にして第４表に示す化合物を製造した。Table 3 Examples 26-31 The compounds shown in Table 4 were produced in the same manner as in Example 4.
Claims (1)
Ｒ＿２は水素原子又はアルキル基を示す。 但し、Ｒ＿１及びＲ＿２が共に水素原子ではないものと
する）で表わされるチアジノイミダゾール誘導体及びそ
の酸付加塩。２ 次の一般式（Iａ）▲数式、化学式、
表等があります▼ （式中、Ｒ′＿１はアルキル基を示す） で表わされる化合物である特許請求の範囲第１項記載の
チアジノイミダゾール誘導体及びその酸付加塩３ 次の
一般式（Iｂ）、 ▲数式、化学式、表等があります▼ （式中、Ｒ′＿２はアルキル基を示す） で表わされる特許請求の範囲第１項記載のチアジノイミ
ダゾール誘導体及びその酸付加塩。 ４ 次の一般式（Iｃ）、 ▲数式、化学式、表等があります▼ （式中、Ｒ′＿１は前記と同じものを示す）で表わされ
る特許請求の範囲第１項記載のチアジノイミダゾール誘
導体及びその酸付加塩。 ５ 次の一般式（Iｄ）、 ▲数式、化学式、表等があります▼ （式中、Ｒ′＿２は前記と同じものを示す）で表わされ
る特許請求の範囲第１項記載のチアジノイミダゾール誘
導体及びその酸付加塩。 ６ 一般式（II）、 ▲数式、化学式、表等があります▼ （式中、Ａは炭素原子又は窒素原子を示す）で表わされ
る２−メルカプト−１Ｈ−イミダゾ化合物に一般式（I
II）、▲数式、化学式、表等があります▼ （式中、Ｘ及びＹはハロゲン原子を、Ｒ＿１及びＲ＿２
は水素原子又はアルキル基を示す。 但し、Ｒ＿１及びＲ＿２が共に水素原子でないものとす
る）で表わされる１，３−ジハロゲノプロパン誘導体を
反応せしめることを特徴とする一般式（I）、▲数式、
化学式、表等があります▼（式中、Ａ、Ｒ＾１及びＲ＿
２は前記と同じものを示す）で表わされるチアジノイミ
ダゾール誘導体及びその酸付加塩の製造法。[Claims] 1 The following general formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼ (In the formula, A represents a carbon atom or a nitrogen atom, and R_1 and R_2 represent a hydrogen atom or an alkyl group. provided that both R_1 and R_2 are not hydrogen atoms) and acid addition salts thereof. 2 The following general formula (Ia) ▲ Numerical formula, chemical formula,
There are tables, etc.▼ (In the formula, R'_1 represents an alkyl group) Thiaziniimidazole derivative and acid addition salt thereof according to claim 1 3 The following general formula (Ib) , ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R'_2 represents an alkyl group.) The thiaziniimidazole derivative and its acid addition salt according to claim 1, which are represented by the following. 4 The thiaziniimidazole derivative according to claim 1, which is represented by the following general formula (Ic), ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (in the formula, R'_1 represents the same thing as above) and acid addition salts thereof. 5. The thiaziniimidazole derivative according to claim 1, which is represented by the following general formula (Id), ▲a mathematical formula, a chemical formula, a table, etc.▼ (in the formula, R'_2 represents the same thing as above) and acid addition salts thereof. 6 General formula (II), ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, A represents a carbon atom or a nitrogen atom)
II), ▲Mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X and Y are halogen atoms, R_1 and R_2
represents a hydrogen atom or an alkyl group. However, both R_1 and R_2 are not hydrogen atoms) General formula (I) characterized by reacting a 1,3-dihalogenopropane derivative represented by ▲ Formula,
There are chemical formulas, tables, etc. ▼ (In the formula, A, R^1 and R_
2 is the same as above) and its acid addition salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2835580A JPS6038398B2 (en) | 1980-03-06 | 1980-03-06 | Thiazinoimidazole derivative and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2835580A JPS6038398B2 (en) | 1980-03-06 | 1980-03-06 | Thiazinoimidazole derivative and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56123992A JPS56123992A (en) | 1981-09-29 |
| JPS6038398B2 true JPS6038398B2 (en) | 1985-08-31 |
Family
ID=12246294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2835580A Expired JPS6038398B2 (en) | 1980-03-06 | 1980-03-06 | Thiazinoimidazole derivative and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6038398B2 (en) |
-
1980
- 1980-03-06 JP JP2835580A patent/JPS6038398B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56123992A (en) | 1981-09-29 |
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