JPH0559113B2 - - Google Patents
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- JPH0559113B2 JPH0559113B2 JP5845783A JP5845783A JPH0559113B2 JP H0559113 B2 JPH0559113 B2 JP H0559113B2 JP 5845783 A JP5845783 A JP 5845783A JP 5845783 A JP5845783 A JP 5845783A JP H0559113 B2 JPH0559113 B2 JP H0559113B2
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- group
- halogen atom
- benzothiazin
- substituted
- formula
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- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
【発明の詳細な説明】
本発明は新規なベンゾチアジン誘導体である式
（式中、R1は低級アルキル基、低級アルコキ
シアルキル基、水酸基もしくはハロゲン原子で置
換された低級アルキル基、又は低級ジアルキルア
ミノアルキル基、R2は水素原子、ハロゲン原子
又は低級アルコキシ基、R3はハロゲン原子、R4
は水素原子、R5は水酸基、アシルオキシ基又は
低級アルコキシ基を表す）で示される２，２−ジ
置換−４−置換−2H−１，４−ベンゾチアジン
−３（4H）−オン又はその酸付加塩及びその製造
方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel benzothiazine derivatives of the formula (In the formula, R 1 is a lower alkyl group, a lower alkoxyalkyl group, a lower alkyl group substituted with a hydroxyl group or a halogen atom, or a lower dialkylaminoalkyl group, R 2 is a hydrogen atom, a halogen atom, or a lower alkoxy group, R 3 is a halogen atom, R 4
2,2-disubstituted-4-substituted-2H-1,4-benzothiazin-3(4H)-one or its acid addition, represented by hydrogen atom, R 5 represents a hydroxyl group, acyloxy group or lower alkoxy group) Related to salt and its manufacturing method.
本発明新規化合物（）は中枢神経系調節作
用、鎮痛作用、解熱作用、消炎作用あるいは抗菌
作用などの薬理作用を示し、医薬として有用なも
のである。これらは経口または非経口的に錠剤、
カプセル、顆粒、シロツプ剤、注射剤またはそれ
らの類似物で形で必要により生理学的に許容され
る塩の形で通常１日10mg〜２ｇの用量で用いられ
る。 The novel compound () of the present invention exhibits pharmacological actions such as central nervous system regulating action, analgesic action, antipyretic action, anti-inflammatory action, and antibacterial action, and is useful as a medicine. These can be taken orally or parenterally as tablets,
It is usually used in the form of capsules, granules, syrups, injections or similar products, and if necessary in the form of physiologically acceptable salts, at a daily dose of 10 mg to 2 g.
次に本発明新規化合物（）の代表的な製造法
の１例を示す。 Next, one example of a typical method for producing the novel compound () of the present invention will be shown.
TMS−Ｘ：トリメチルハロゲノシラン
（式中、Ｘはハロゲン原子を表し、R1及びR2
は前記と同義）。 TMS-X: Trimethylhalogenosilane (wherein, X represents a halogen atom, R 1 and R 2
is the same as above).
すなわち、２−フエニルメチリデン〔または２
−（４−置換フエニルメチリデン）〕−４−置換−
2H−１，４−ベンゾチアジン−３（4H）−オン
（）に、塩化メチレン、クロロホルム、テトラ
ヒドロフランなどの溶媒中、たとえば30％過酸化
水素水のような形で過酸化水素と水およびトリメ
チルハロゲノシランを室温以下の温度で数時間作
用させると式（）の化合物である２−（α−ハ
ロゲノベンジル）〔または２−（４−置換−α−ハ
ロゲノベンジル）〕−２−ヒドロキシ−４−置換−
2H−１，４−ベンゾチアゾン−３（4H）−オン
（−５）を得る。反応後の処理および精製は通
常の方法、たとえば抽出、再結晶、カラムクロマ
トグラフイー、活性炭処理などによつて行われ
る。本発明に用いる原料（）は公知物質で、オ
ルトアミノチオフエノールから容易に合成するこ
とができる〔John Krapcho and Chester F.
Turk，J.Med.Chem.，16，776（1973）〕。 That is, 2-phenylmethylidene [or 2
-(4-substituted phenylmethylidene)]-4-substituted-
2H-1,4-benzothiazin-3(4H)-one () in a solvent such as methylene chloride, chloroform, tetrahydrofuran, etc., in a form such as 30% hydrogen peroxide, hydrogen peroxide, water and trimethylhalogenosilane. is reacted for several hours at a temperature below room temperature to form a compound of formula (2-(α-halogenobenzyl) [or 2-(4-substituted-α-halogenobenzyl)]-2-hydroxy-4-substituted-
2H-1,4-benzothiazon-3(4H)-one (-5) is obtained. Post-reaction treatment and purification are carried out by conventional methods, such as extraction, recrystallization, column chromatography, and activated carbon treatment. The raw material () used in the present invention is a known substance and can be easily synthesized from orthoaminothiophenol [John Krapcho and Chester F.
Turk, J.Med.Chem., 16, 776 (1973)].
かくして得られた式（）の新規化合物は所望
により公知の方法で各種無機塩あるいは有機塩と
することができる。 The novel compound of formula () thus obtained can be converted into various inorganic or organic salts by known methods, if desired.
次に実施例を挙げて本発明を詳細に説明する。 Next, the present invention will be explained in detail with reference to Examples.
実施例 １
２−（４−メトキシフエニルメチリデン）−４−
（２−ヒドロキシエチル）−2H−１，４−ベンゾ
チアジン−３（4H）−オン2.0ｇを20mlのテトラヒ
ドロフランに溶解し、−20℃に冷却する。液温を
０℃以下に保ちつつ、60％過酸化水素水0.5ｇを
加える。トリメチルシリルクロライドの2.8mlを
10分間で滴下し同温で４時間撹拌した後、氷水20
mlに注ぎジエチルエーテル20mlで２回抽出する。
抽出液をよく水洗した後、無水硫酸ナトリウムで
乾燥する。減圧下溶媒を留去すると、２−（４−
メトキシ−α−クロルベンジル）−２−ヒドロキ
シ−４−（２−ヒドロキシエチル）−2H−１，４
−ベンゾチアジン−３（4H）−オン2.0ｇを油状物
として得る。Example 1 2-(4-methoxyphenylmethylidene)-4-
2.0 g of (2-hydroxyethyl)-2H-1,4-benzothiazin-3(4H)-one is dissolved in 20 ml of tetrahydrofuran and cooled to -20°C. Add 0.5g of 60% hydrogen peroxide while keeping the liquid temperature below 0℃. 2.8ml of trimethylsilyl chloride
Dropwise over 10 minutes and stirred at the same temperature for 4 hours, then soaked in ice water for 20 minutes.
ml and extracted twice with 20 ml of diethyl ether.
After thoroughly washing the extract with water, it is dried over anhydrous sodium sulfate. When the solvent was distilled off under reduced pressure, 2-(4-
Methoxy-α-chlorobenzyl)-2-hydroxy-4-(2-hydroxyethyl)-2H-1,4
2.0 g of -benzothiazin-3(4H)-one are obtained as an oil.
N.M.R.（CDCl3，ppm）3.80（ｍ，6H），4.36
（ｍ，2H），5.73，5.96（ｓ，1H），6.80−7.68（ｍ，
8H）．
I.R.（Neat，cm-1）3350，1670，1605，1580.
実施例 ２
２−（４−メトキシフエニルメチリデン）−４−
（２−クロロエチル）−2H−１，４−ベンゾチア
ジン−３（4H）−オン0.4ｇ及び60％過酸化水素水
0.1ｇをテトラヒドロフラン５mlに溶解し、−20℃
に冷却する。トリメチルシリルクロライド0.5ml
を10分間で滴下し同温度で４時間撹拌する。反応
終了後氷水20mlに注ぎ、ジエチルエーテル20mlで
２回抽出し抽出液をよく水洗して無水硫酸ナトリ
ウムで乾燥後減圧下溶媒を留去すると、２−（４
−メトキシ−α−クロロベンジル）−２−ヒドロ
キシ−４−（２−クロロエチル）−2H−１，４−
ベンゾチアジン−３（4H）−オン0.37ｇを得る。 NMR (CDCl 3 , ppm) 3.80 (m, 6H), 4.36
(m, 2H), 5.73, 5.96 (s, 1H), 6.80−7.68 (m,
8H). IR (Neat, cm -1 ) 3350, 1670, 1605, 1580. Example 2 2-(4-methoxyphenylmethylidene)-4-
(2-chloroethyl)-2H-1,4-benzothiazin-3(4H)-one 0.4g and 60% hydrogen peroxide solution
Dissolve 0.1g in 5ml of tetrahydrofuran and cool at -20℃.
Cool to Trimethylsilyl chloride 0.5ml
was added dropwise over 10 minutes and stirred at the same temperature for 4 hours. After the reaction was completed, it was poured into 20 ml of ice water, extracted twice with 20 ml of diethyl ether, the extract was thoroughly washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2-(4
-methoxy-α-chlorobenzyl)-2-hydroxy-4-(2-chloroethyl)-2H-1,4-
0.37 g of benzothiazin-3(4H)-one is obtained.
N.M.R.（CDCl3，ppm）3.68（ｍ，5H），4.37
（Tri，2H），5.70，5.97（ｓ，1H），6.70−7.70
（ｍ，8H）．
I.R.（Neat，cm-1）3325，1670，1610，1585.
実施例 ３
２−（４−メトキシフエニルメチリデン）−４−
（２−ブロモエチル）−2H−１，４−ベンゾチア
ジン−３（4H）−オン0.5ｇ及び60％過酸化水素水
0.1ｇをテトラヒドロフラン５mlに溶かし、−20℃
に保つ。トリメチルクロロシラン0.5mlを10分間
で滴下する。同温度で４時間撹拌後氷水20mlに注
ぎジエチルエーテル15mlで２回抽出する。ジエチ
ルエーテル層をよく水洗し無水硫酸ナトリウムで
乾燥後減圧下溶媒を留去すると、２−（４−メト
キシ−α−クロロベンジル）−２−ヒドロキシ−
４−（２−ブロモエチル）−2H−１，４−ベンゾ
チアジン−３（4H）−オン0.3ｇを得る。 NMR (CDCl 3 , ppm) 3.68 (m, 5H), 4.37
(Tri, 2H), 5.70, 5.97 (s, 1H), 6.70−7.70
(m, 8H). IR (Neat, cm -1 ) 3325, 1670, 1610, 1585. Example 3 2-(4-methoxyphenylmethylidene)-4-
(2-bromoethyl)-2H-1,4-benzothiazin-3(4H)-one 0.5g and 60% hydrogen peroxide solution
Dissolve 0.1g in 5ml of tetrahydrofuran and -20℃
Keep it. Add 0.5 ml of trimethylchlorosilane dropwise over 10 minutes. After stirring at the same temperature for 4 hours, the mixture was poured into 20 ml of ice water and extracted twice with 15 ml of diethyl ether. The diethyl ether layer was thoroughly washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2-(4-methoxy-α-chlorobenzyl)-2-hydroxy-
0.3 g of 4-(2-bromoethyl)-2H-1,4-benzothiazin-3(4H)-one is obtained.
N.M.R.（CDCl3，ppm）3.58（broad，2H），
3.76（ｓ，3H），4.34（ｍ，2H），5.71，5.97（ｓ，
1H），6.80−7.70（ｍ，8H）．
実施例 ４
２−フエニルメチリデン−４−メチル−2H−
１，４−ベンゾチアジン−３（4H）−オン１ｇと
30％過酸化水素水0.58mlとを10mlのテトラヒドロ
フランに溶かし、−20ないし−10℃に冷却し、こ
の溶液にトリメチルクロロシラン1.43mlを徐々に
15分間で滴下した後に４時間撹拌する。さらに室
温で２時間撹拌して反応は終了する。反応液を氷
水20mlに注ぎ、酢酸エチル10mlで２回抽出を行
う。抽出液を水洗し芒硝で乾燥後、溶媒を減圧下
で留去すると２−（α−クロロベンジル）−２−ヒ
ドロキシ−４−メチル−2H−１，４−ベンゾチ
アジン−３（4H）−オンの油状物0.96ｇを得る。 NMR (CDCl 3 , ppm) 3.58 (broad, 2H),
3.76 (s, 3H), 4.34 (m, 2H), 5.71, 5.97 (s,
1H), 6.80-7.70 (m, 8H). Example 4 2-phenylmethylidene-4-methyl-2H-
1 g of 1,4-benzothiazin-3(4H)-one and
Dissolve 0.58 ml of 30% hydrogen peroxide in 10 ml of tetrahydrofuran, cool to -20 to -10°C, and gradually add 1.43 ml of trimethylchlorosilane to this solution.
After dropping for 15 minutes, stir for 4 hours. The reaction was completed by further stirring at room temperature for 2 hours. Pour the reaction solution into 20 ml of ice water and extract twice with 10 ml of ethyl acetate. After washing the extract with water and drying with Glauber's salt, the solvent was distilled off under reduced pressure to obtain 2-(α-chlorobenzyl)-2-hydroxy-4-methyl-2H-1,4-benzothiazin-3(4H)-one. 0.96 g of oil is obtained.
I.R.スペクトル：（Neat，cm-1）3300（broad，
weak），1670，1585
N.M.R.スペクトル：（CDCl3，ppm）3.40（ｓ，
1H），3.53（ｓ，3H），5.85(s)，6.05(s)，6.95−
7.80（ｍ，9H）．
元素分析値（％） C16H14NO2SClとして
理論値 Ｃ，60.09；Ｈ，4.41；Ｎ，4.38
実測値 Ｃ，59.87；Ｈ，4.38；Ｎ，4.26
実施例 ５
２−（４−クロロフエニルメチリデン）−４−メ
チル−2H−１，４−ベンゾチアジン−３（4H）−
オン１ｇと30％過酸化水素水0.51mlとをテトラヒ
ドロフラン10mlに溶かし−20ないし−10℃に保ち
つつ、トリメチルクロロシラン1.26mlを徐々に15
分間で滴下し４時間撹拌する。さらに室温で２時
間撹拌した後、これを氷水20mlに注ぎ、酢酸エチ
ル10mlで２回抽出を行う。抽出液を水洗し芒硝で
乾燥後、溶媒を減圧下に留去すると油状の２−
（４−クロロ−α−クロロベンジル）−２−ヒドロ
キシ−４−メチル−2H−１，４−ベンゾチアジ
ン−３（4H）−オン0.67ｇを得る。 IR spectrum: (Neat, cm -1 ) 3300 (broad,
weak), 1670, 1585 NMR spectrum: (CDCl 3 , ppm) 3.40 (s,
1H), 3.53(s, 3H), 5.85(s), 6.05(s), 6.95−
7.80 (m, 9H). Elemental analysis value (%) C 16 H 14 NO 2 As SCl Theoretical value C, 60.09; H, 4.41; N, 4.38 Actual value C, 59.87; H, 4.38; N, 4.26 Example 5 2-(4-chlorophenyl methylidene)-4-methyl-2H-1,4-benzothiazine-3(4H)-
Dissolve 1 g of silane and 0.51 ml of 30% hydrogen peroxide in 10 ml of tetrahydrofuran and gradually add 1.26 ml of trimethylchlorosilane to 150 ml while keeping the temperature at -20 to -10°C.
Add dropwise over minutes and stir for 4 hours. After further stirring at room temperature for 2 hours, the mixture was poured into 20 ml of ice water and extracted twice with 10 ml of ethyl acetate. After washing the extract with water and drying with Glauber's salt, the solvent was distilled off under reduced pressure to obtain an oily 2-
0.67 g of (4-chloro-α-chlorobenzyl)-2-hydroxy-4-methyl-2H-1,4-benzothiazin-3(4H)-one are obtained.
I.R.スペクトル：（Neat，cm-1），3350，1675，
1580.
N.M.R.スペクトル：（CDCl3，ppm）3.40（ｓ，
1H），3.50（ｓ，3H），6.05（ｓ，1H），6.96−7.80
（ｍ，8H）．
元素分析値（％） C16H13NO2SCl2として
理論値 Ｃ，54.23；Ｈ，3.70；N.3.95
実測値 Ｃ，54.34；Ｈ，4.00；Ｎ，3.88
実施例 ６
２−（４−メトキシフエニルメチリデン）−４−
メトキシメチル−2H−１，４−ベンゾチアジン
−３（4H）−オン10ｇをテトラヒドロフラン60ml
に溶かし、この溶液に60％過酸化水素水2.5mlを
加え、−10ないし−20℃に冷却してトリメチルク
ロロシラン13mlを徐々に10ないし20分間で滴下
後、同温度にて一晩放置、これを氷水200mlに注
ぎ、クロロホルム100mlで２回抽出する。抽出液
を芒硝で乾燥後、減圧下で溶媒を留去すると２−
（４−メトキシ−α−クロロベンジル）−２−ヒド
ロキシ−４−メトキシメチル−2H−１，４−ベ
ンゾチアジン−３（4H）−オンの油状物質11ｇを
得る。 IR spectrum: (Neat, cm -1 ), 3350, 1675,
1580. NMR spectrum: (CDCl 3 , ppm) 3.40 (s,
1H), 3.50 (s, 3H), 6.05 (s, 1H), 6.96-7.80
(m, 8H). Elemental analysis value (%) C 16 H 13 NO 2 SCl 2 Theoretical value C, 54.23; H, 3.70; N. 3.95 Actual value C, 54.34; H, 4.00; N, 3.88 Example 6 2-(4-methoxy phenylmethylidene)-4-
10g of methoxymethyl-2H-1,4-benzothiazin-3(4H)-one in 60ml of tetrahydrofuran
Add 2.5 ml of 60% hydrogen peroxide to this solution, cool it to -10 to -20°C, gradually add 13 ml of trimethylchlorosilane dropwise over 10 to 20 minutes, and leave it overnight at the same temperature. Pour into 200 ml of ice water and extract twice with 100 ml of chloroform. After drying the extract with Glauber's salt and distilling off the solvent under reduced pressure, 2-
11 g of an oily substance of (4-methoxy-α-chlorobenzyl)-2-hydroxy-4-methoxymethyl-2H-1,4-benzothiazin-3(4H)-one are obtained.
I.R.スペクトル：（Neat，cm-1）3300，1690，
1605，1580.
N.M.R.スペクトル：（CDCl3，ppm）3.44（ｓ，
1H），3.49（ｓ，3H），3.82（ｓ，3H），5.45
（quartet，2H），6.03（ｓ，1H），6.80−7.70（ｍ，
8H）．
元素分析値（％） C18H18NO4SClとして
理論値 Ｃ，56.91；Ｈ，4.77；Ｎ，3.68
実測値 Ｃ，57.03；Ｈ，4.79；Ｎ，3.71
実施例 ７
２−（４−メトキシフエニルメチリデン）−４−
（２−ジメチルアミノエチル）−2H−１，４−ベ
ンゾチアジン−３（4H）−オン20ｇを塩化メチレ
ン300mlに溶かし、トリメチルクロロシラン19.5
ｇを加え、−５℃ないし−10℃に冷却して30％過
酸化水素水6.38ｇを徐々に滴下した後、同温度に
て30分撹拌、これを冷却した10％食塩水500mlで
２回洗浄する。洗浄した塩化メチレンを無水硫酸
マグネシウムで乾燥後、室温下減圧にて留去する
と２−（４−メトキシ−α−クロロベンジル）−２
−ヒドロキシ−2H−４−（２−ジメチルアミノエ
チル）−１，４−ベンゾチアジン−３（4H）−オ
ン・塩酸塩の淡黄色粉末24ｇを得る。 IR spectrum: (Neat, cm -1 ) 3300, 1690,
1605, 1580. NMR spectrum: (CDCl 3 , ppm) 3.44 (s,
1H), 3.49 (s, 3H), 3.82 (s, 3H), 5.45
(quartet, 2H), 6.03 (s, 1H), 6.80−7.70 (m,
8H). Elemental analysis value (%) C 18 H 18 NO 4 As SCl Theoretical value C, 56.91; H, 4.77; N, 3.68 Actual value C, 57.03; H, 4.79; N, 3.71 Example 7 2-(4-methoxyph) enylmethylidene)-4-
Dissolve 20 g of (2-dimethylaminoethyl)-2H-1,4-benzothiazin-3(4H)-one in 300 ml of methylene chloride, and dissolve 19.5 g of trimethylchlorosilane.
After cooling to -5℃ to -10℃ and gradually dropping 6.38g of 30% hydrogen peroxide solution, stir at the same temperature for 30 minutes, and add 500ml of cooled 10% saline solution twice. Wash. After drying the washed methylene chloride over anhydrous magnesium sulfate and distilling it off under reduced pressure at room temperature, 2-(4-methoxy-α-chlorobenzyl)-2
24 g of pale yellow powder of -hydroxy-2H-4-(2-dimethylaminoethyl)-1,4-benzothiazin-3(4H)-one hydrochloride is obtained.
本品はアセトンから再結晶すると融点189−194
℃の無色粉末晶となる。 This product has a melting point of 189-194 when recrystallized from acetone.
It becomes a colorless powder crystal at ℃.
I.R.スペクトル：（Nujol，cm-1）3350（br.），
2580，2450，1690，1608，1580，1485，1250，
1175，1065，765.
N.M.R.スペクトル：（DMSO−d6，ppm）2.95
（br.s，6H），3.64−3.30（ｍ，2H），3.88（ｓ，
3H），4.90−4.50（ｍ，2H），6.07（ｓ，1H），8.17
−6.96（ｍ，8H）． IR spectrum: (Nujol, cm -1 ) 3350 (br.),
2580, 2450, 1690, 1608, 1580, 1485, 1250,
1175, 1065, 765. NMR spectrum: (DMSO-d 6 , ppm) 2.95
(br.s, 6H), 3.64-3.30 (m, 2H), 3.88 (s,
3H), 4.90-4.50 (m, 2H), 6.07 (s, 1H), 8.17
-6.96 (m, 8H).
Claims (1)
シアルキル基、水酸基もしくはハロゲン原子で置
換された低級アルキル基、又は低級ジアルキルア
ミノアルキル基、R2は水素原子、ハロゲン原子
又は低級アルコキシ基、R3はハロゲン原子、R4
は水素原子、R5は水酸基、アシルオキシ基又は
低級アルコキシ基を表す）で示される２，２−ジ
置換−４−置換−2H−１，４−ベンゾチアジン
−３（4H）−オン又はその酸付加塩。 ２ 式 （式中、R1は低級アルキル基、低級アルコキ
シアルキル基、水酸基もしくはハロゲン原子で置
換された低級アルキル基、又は低級ジアルキルア
ミノアルキル基、R2は水素原子、ハロゲン原子
又は低級アルコキシ基を表す）で示される化合物
又はその酸付加塩に、過酸化水素、水及びトリメ
チルハロゲノシランを作用させ、及び場合により
更にアシル化又はアルキル化することを特徴とす
る、式 （式中、R1は低級アルキル基、低級アルコキ
シアルキル基、水酸基もしくはハロゲン原子で置
換された低級アルキル基、又は低級ジアルキルア
ミノアルキル基、R2は水素原子、ハロゲン原子
又は低級アルコキシ基、R3はハロゲン原子、R4
は水素原子、R5は水酸基、アシルオキシ基又は
低級アルコキシ基を表す）で示される２，２−ジ
置換−４−置換−2H−１，４−ベンゾチアジン
−３−（4H）−オン又はその酸付加塩の製造方法。[Claims] 1 formula (In the formula, R 1 is a lower alkyl group, a lower alkoxyalkyl group, a lower alkyl group substituted with a hydroxyl group or a halogen atom, or a lower dialkylaminoalkyl group, R 2 is a hydrogen atom, a halogen atom, or a lower alkoxy group, R 3 is a halogen atom, R 4
2,2-disubstituted-4-substituted-2H-1,4-benzothiazin-3(4H)-one or its acid addition, represented by hydrogen atom, R 5 represents a hydroxyl group, acyloxy group or lower alkoxy group) salt. 2 formulas (In the formula, R 1 represents a lower alkyl group, a lower alkoxyalkyl group, a lower alkyl group substituted with a hydroxyl group or a halogen atom, or a lower dialkylaminoalkyl group, and R 2 represents a hydrogen atom, a halogen atom, or a lower alkoxy group) A compound represented by the formula or an acid addition salt thereof is reacted with hydrogen peroxide, water and trimethylhalogenosilane, and optionally further acylated or alkylated. (In the formula, R 1 is a lower alkyl group, a lower alkoxyalkyl group, a lower alkyl group substituted with a hydroxyl group or a halogen atom, or a lower dialkylaminoalkyl group, R 2 is a hydrogen atom, a halogen atom, or a lower alkoxy group, R 3 is a halogen atom, R 4
2,2-disubstituted- 4 -substituted-2H-1,4-benzothiazin-3-(4H)-one or an acid thereof Method for producing addition salts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5845783A JPS59184170A (en) | 1983-04-01 | 1983-04-01 | 1,4-benzothiazine derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5845783A JPS59184170A (en) | 1983-04-01 | 1983-04-01 | 1,4-benzothiazine derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59184170A JPS59184170A (en) | 1984-10-19 |
| JPH0559113B2 true JPH0559113B2 (en) | 1993-08-30 |
Family
ID=13084947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5845783A Granted JPS59184170A (en) | 1983-04-01 | 1983-04-01 | 1,4-benzothiazine derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59184170A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0730058B2 (en) * | 1988-05-14 | 1995-04-05 | 参天製薬株式会社 | 3-oxo-1,4-benzothiazine derivative |
-
1983
- 1983-04-01 JP JP5845783A patent/JPS59184170A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59184170A (en) | 1984-10-19 |
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