JPS6141511B2 - - Google Patents
Info
- Publication number
- JPS6141511B2 JPS6141511B2 JP11537579A JP11537579A JPS6141511B2 JP S6141511 B2 JPS6141511 B2 JP S6141511B2 JP 11537579 A JP11537579 A JP 11537579A JP 11537579 A JP11537579 A JP 11537579A JP S6141511 B2 JPS6141511 B2 JP S6141511B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- aromatic ring
- formula
- chloroform
- lower alkyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical class [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- -1 N-[2-(1-oxo-2-propenyl)phenylthio]-p-toluenesulfonamide Chemical compound 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YSYYFHVHCXBCCS-UHFFFAOYSA-N 2-methyl-2,3-dihydrothiochromen-4-one Chemical compound C1=CC=C2SC(C)CC(=O)C2=C1 YSYYFHVHCXBCCS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- HMTBCHSNSIHQHU-UHFFFAOYSA-N N-(2-but-2-enoylphenyl)sulfanyl-4-methylbenzenesulfonamide Chemical compound O=C(C=CC)C1=C(C=CC=C1)SNS(=O)(=O)C1=CC=C(C=C1)C HMTBCHSNSIHQHU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 description 1
- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
Description
本発明は次の一般式（）
〔式中R1は水素、ハロゲン又は低級アルキル
を、R2，R3は同一又は異なつて水素又は低級ア
ルキルを、Tsは
The present invention is based on the following general formula () [In the formula, R 1 is hydrogen, halogen or lower alkyl, R 2 and R 3 are the same or different and represent hydrogen or lower alkyl, and Ts is
【式】を表わ
す。〕で示されるスルフエンアミド誘導体に関す
る。
該物質は種々の方法で製造することができる
が、たとえば次の一般式（）
〔式中R1，R2，R3，Tsは前記と同じ。ｎは０
あるいは１を表わす。〕で表わされる化合物をｎ
＝０の場合はメチルアルコール中酢酸触媒で冷却
下あるいは室温でクロラミン―Ｔと反応させるこ
とにより、ｎ＝１の場合はクロロホルムあるいは
アセトニトリル溶媒中でトリエチルアミンと反応
させるか、あるいはジメチルスルホキシド溶媒中
で加熱することにより、収率よく製造することが
できる。別法として、たとえば次の一般式（）
〔式中R1，R3，Ts，ｎは前記と同じ。〕で表わ
される化合物をｎ＝０の場合はメチルアルコール
中酢酸触媒で冷却下あるいは室温でクロラミン―
Ｔと反応させることにより、ｎ＝１の場合は、ク
ロロホルムあるいはベンゼン中で加熱還流するこ
とによつても目的とする（）を収率よく製造す
ることができる。
次に実施例において詳述する方法によつて合成
された本発明化合物の一部を以下に示す。
Represents [formula]. ] The present invention relates to a sulfenamide derivative represented by This substance can be produced by various methods, for example, the following general formula () [In the formula, R 1 , R 2 , R 3 , and Ts are the same as above. n is 0
Or it represents 1. ] for the compound represented by n
If n = 0, react with chloramine-T in methyl alcohol with an acetic acid catalyst under cooling or at room temperature; if n = 1, react with triethylamine in chloroform or acetonitrile solvent, or heat in dimethyl sulfoxide solvent. By doing so, it can be produced with good yield. Alternatively, for example the following general formula () [In the formula, R 1 , R 3 , Ts, and n are the same as above. ] When n=0, the compound represented by chloramine-
By reacting with T, when n=1, the desired compound () can also be produced in good yield by heating and refluxing in chloroform or benzene. Next, some of the compounds of the present invention synthesized by the method detailed in Examples are shown below.
【表】
本発明の化合物（）は文献未載の新規物質で
あつて、これをたとえばベンゼン、アセトニトリ
ル等に溶かしてシリカゲル、トリエチルアミン等
と撹拌することにより、下記化合物
〔R1，R2，R3，Tsは然記と同じ。〕を合成す
ることができ、この化合物は自発運動抑制作用、
鎮痛消炎作用、抗菌作用を有する極めて有用な物
質である。従つて本発明の化合物（）は医薬品
の合成中間体として極めて有用である。
以下に本発明の製造に係る実施例を掲げる。
実施例 １
Ｎ―〔２―（１―オキソ―２―プロペニル）フ
エニルチオ〕―ｐ―トルエンスルホンアミド
（化合物番号１）
Ｓ―（ｐ―トルエンスルホニルイミノ）―２，
２―ジメチル―２，３―ジヒドロベンゾ〔ｂ〕チ
オフエン―３―オン150mgをベンゼン６mlに溶か
し１時間還流する。ベンゼンを留去するとスルフ
エンアミド誘導体（化合物番号１）138mgが油状
物質として得られた。NMR（CDCl3）δ2.02（br.
s.3H），2.40（s.3H），5.18（br.1H NH），5.45
（br.s.1H），5.78（br.s.1H），6.9―8.0（m.8H）。
実施例 ２
Ｎ―〔２―（１―オキソ―２―ブテニル）フエ
ニルチオ〕―ｐ―トルエンスルホンアミド（化
合物番号２）
Ｓ―（ｐ―トルエンスルホニルイミノ）―２―
メチル―チオクロマン―４―オン3.0ｇをクロロ
ホルムに溶かしトリエチルアミン0.1mlを加え
る。室温で１時間撹拌し、クロロホルムを希塩酸
で洗い硫酸マグネシウムにて乾燥、クロロホルム
を留去し、残渣に2.5ｇの化合物（化合物番号
２）を得る。
融点130.6℃。
ＮMR（CDCl3）1.95（3H，d.CH3 Ｊ＝５Hz．），
2.36（3H，s.Ts―CH3），6.23（1H，br.s.
NH），6.88―8.05（6H，m.芳香環，―CH＝
CH―），7.18（2H，d.芳香環，Ｊ＝８Hz．），
7.72（2H，d.芳香環，Ｊ＝８Hz．）
元素分析値（％）
計算値 C58.76 H4.93 N4.03
実測値 C57.98 H4.63 N4.25
実施例 ３
Ｎ―〔２―（オキソ―２―ブテニル）―４―メ
チルフエニルチオ〕―ｐ―トルエンスルホンア
ミド（化合物番号３）
Ｓ―（ｐ―トルエンスルホニルイミノ）―２，
６―ジメチル―チオクロマン―４―オン5.3ｇを
250mlのアセトニトリルに溶かし、２mlのトリエ
チルアミンを加える。室温で２時間撹拌をし、ア
セトニトリルを留去、残渣をベンゼンに溶かし、
水洗、硫酸マグネシウムにて乾燥、ベンゼンを大
部分留去し析出晶を取し、化合物（化合物番号
３）を754mg得る。
融点152〜154℃。
ＮMR（CDCl8―DMSO―d6）δ 1.95（3H，d.
CH3，Ｊ＝５Hz．），2.36（6H，s.CH3），6.25―
7.85（5H，m.芳香環，―CH＝CH―），7.16
（2H，d.芳香環，Ｊ＝８Hz．），7.67（2H，d.芳
香環，Ｊ＝８Hz．）
元素分析値
計算値 C59.81 H5.31 N3.88
実測値 C59.73 H5.55 N4.10
実施例 ４
Ｎ―〔４―クロロ―２―（１―オキソ―２―ブ
テニル）フエニルチオ〕―ｐ―トルエンスルホ
ンアミド（化合物番号４）
Ｓ―（ｐ―トルエンスルホニルイミノ）―６―
クロロ―２―メチルチオクロマン―４―オン
200mgを30mlのジメチルスルホキシドに溶かし、
80℃で２時間加熱する。反応終了後、ジメチルス
ルホキシドの溶液を水に投入し、クロロホルム抽
出、水洗を５回行い、硫酸マグネシウムで乾燥、
クロロホルム留去、残渣をエーテルより再結晶
し、化合物（化合物番号４）を112mg得る。融点
166.5℃。
ＮMR（CDCl3）δ 1.95（3H，d.CH3，Ｊ＝５
Hz．），2.36（3H，s.CH3），6.35（1H，m.
NH），6.88―7.98（5H，m.芳香環，―CH＝
CH―），7.21（2H，d.芳香環，Ｊ＝８Hz．），
7.71（2H，d.芳香環，Ｊ＝８Hz．）[Table] The compound () of the present invention is a new substance that has not been described in any literature, and by dissolving it in, for example, benzene, acetonitrile, etc. and stirring it with silica gel, triethylamine, etc., the following compound can be obtained. [R 1 , R 2 , R 3 , and Ts are the same as in the above. ] can be synthesized, and this compound has locomotor activity suppressing effects,
It is an extremely useful substance that has analgesic, anti-inflammatory, and antibacterial effects. Therefore, the compound () of the present invention is extremely useful as a synthetic intermediate for pharmaceuticals. Examples related to the production of the present invention are listed below. Example 1 N-[2-(1-oxo-2-propenyl)phenylthio]-p-toluenesulfonamide (compound number 1) S-(p-toluenesulfonylimino)-2,
150 mg of 2-dimethyl-2,3-dihydrobenzo[b]thiophen-3-one was dissolved in 6 ml of benzene and refluxed for 1 hour. When benzene was distilled off, 138 mg of a sulfenamide derivative (compound number 1) was obtained as an oily substance. NMR (CDCl 3 ) δ2.02 (br.
s.3H), 2.40 (s.3H), 5.18 (br.1H NH), 5.45
(br.s.1H), 5.78 (br.s.1H), 6.9―8.0 (m.8H). Example 2 N-[2-(1-oxo-2-butenyl)phenylthio]-p-toluenesulfonamide (compound number 2) S-(p-toluenesulfonylimino)-2-
Dissolve 3.0 g of methyl-thiochroman-4-one in chloroform and add 0.1 ml of triethylamine. Stir at room temperature for 1 hour, wash the chloroform with diluted hydrochloric acid, dry over magnesium sulfate, and distill off the chloroform to obtain 2.5 g of a compound (Compound No. 2) as a residue. Melting point: 130.6℃. NMR (CDCl 3 ) 1.95 (3H, d.CH 3 J=5Hz.),
2.36 (3H, s.Ts―CH 3 ), 6.23 (1H, br.s.
NH), 6.88-8.05 (6H, m. aromatic ring, -CH=
CH―), 7.18 (2H, d. aromatic ring, J = 8Hz.),
7.72 (2H, d. aromatic ring, J=8Hz.) Elemental analysis value (%) Calculated value C58.76 H4.93 N4.03 Actual value C57.98 H4.63 N4.25 Example 3 N-[2- (oxo-2-butenyl)-4-methylphenylthio]-p-toluenesulfonamide (compound number 3) S-(p-toluenesulfonylimino)-2,
5.3g of 6-dimethyl-thiochroman-4-one
Dissolve in 250ml of acetonitrile and add 2ml of triethylamine. After stirring at room temperature for 2 hours, acetonitrile was distilled off, and the residue was dissolved in benzene.
Wash with water, dry with magnesium sulfate, distill off most of the benzene, and collect the precipitated crystals to obtain 754 mg of a compound (Compound No. 3). Melting point 152-154℃. NMR (CDCl 8 -DMSO-d 6 ) δ 1.95 (3H, d.
CH 3 , J=5Hz. ), 2.36 (6H, s.CH 3 ), 6.25―
7.85 (5H, m. aromatic ring, -CH=CH-), 7.16
(2H, d. aromatic ring, J = 8Hz.), 7.67 (2H, d. aromatic ring, J = 8Hz.) Elemental analysis value Calculated value C59.81 H5.31 N3.88 Actual value C59.73 H5.55 N4.10 Example 4 N-[4-chloro-2-(1-oxo-2-butenyl)phenylthio]-p-toluenesulfonamide (compound number 4) S-(p-toluenesulfonylimino)-6-
Chloro-2-methylthiochroman-4-one
Dissolve 200mg in 30ml dimethyl sulfoxide,
Heat at 80℃ for 2 hours. After the reaction, the dimethyl sulfoxide solution was poured into water, extracted with chloroform, washed with water 5 times, dried over magnesium sulfate,
Chloroform was distilled off, and the residue was recrystallized from ether to obtain 112 mg of a compound (Compound No. 4). melting point
166.5℃. NMR (CDCl 3 ) δ 1.95 (3H, d.CH 3 , J=5
Hz. ), 2.36 (3H, s.CH 3 ), 6.35 (1H, m.
NH), 6.88-7.98 (5H, m. aromatic ring, -CH=
CH―), 7.21 (2H, d. aromatic ring, J = 8Hz.),
7.71 (2H, d. aromatic ring, J=8Hz.)
Claims (1)
を、R2，R3は同一又は異なつて水素又は低級ア
ルキルを、Tsは【式】を表わ す。〕で表わされるスルフエンアミド誘導体。 ２ 低級アルキルがメチルである特許請求の範囲
第１項記載の化合物。[Claims] First-order general formula [In the formula, R 1 represents hydrogen, halogen or lower alkyl, R 2 and R 3 are the same or different and represent hydrogen or lower alkyl, and Ts represents [Formula]]. ] A sulfenamide derivative represented by 2. The compound according to claim 1, wherein lower alkyl is methyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11537579A JPS5639062A (en) | 1979-09-08 | 1979-09-08 | Slufenamide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11537579A JPS5639062A (en) | 1979-09-08 | 1979-09-08 | Slufenamide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5639062A JPS5639062A (en) | 1981-04-14 |
| JPS6141511B2 true JPS6141511B2 (en) | 1986-09-16 |
Family
ID=14660962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11537579A Granted JPS5639062A (en) | 1979-09-08 | 1979-09-08 | Slufenamide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5639062A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4513309A (en) * | 1982-11-03 | 1985-04-23 | Westinghouse Electric Corp. | Prevention of latch-up in CMOS integrated circuits using Schottky diodes |
| JPS61168953A (en) * | 1985-01-22 | 1986-07-30 | Nec Corp | Semiconductor integrated circuit device |
| JPS61187265A (en) * | 1985-02-14 | 1986-08-20 | Nec Corp | Semiconductor integrated circuit device |
| JPS61263262A (en) * | 1985-05-17 | 1986-11-21 | Nec Corp | Semiconductor integrated circuit device |
-
1979
- 1979-09-08 JP JP11537579A patent/JPS5639062A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5639062A (en) | 1981-04-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6566372B1 (en) | Bicyclic androgen and progesterone receptor modulator compounds and methods | |
| MX2012006654A (en) | New process for the preparation of dronedarone. | |
| EA016914B1 (en) | Method for preparing 2,6-diethyl-4-methylphenylacetic acid | |
| JP2013532653A (en) | New production method for dronedarone | |
| JP3393891B2 (en) | Method for producing imidazoles | |
| JPH02207083A (en) | Production of 2-nitroiminoimidazolidines | |
| JPH0489464A (en) | Production of methoxyiminoacetamide compound and intermediate used therein | |
| JP2004512326A5 (en) | ||
| EP0094102B1 (en) | 1-(1-cyclohexanyl-methyl) pyrrolidine derivatives, and process for their preparation | |
| JPS6141511B2 (en) | ||
| BR112014018985B1 (en) | method for preparing a compound | |
| JP2009242244A (en) | Method for producing pyrazine derivative and intermediate of the same | |
| KR840002267B1 (en) | Process for the preparation of sulfonamide derivation | |
| JP2517991B2 (en) | 4-acetylamino-3-fluorophenoxyacetic acid | |
| JP2527961B2 (en) | Benzoic acid ester derivative and method for producing the same | |
| JPS6241510B2 (en) | ||
| JPH0511115B2 (en) | ||
| JPH0350748B2 (en) | ||
| JP2508152B2 (en) | 4-amino-5-fluoro-2-nitrophenoxyacetic acid ester | |
| JPH0768194B2 (en) | 5- (1-butyn-3-yl) oxy-4-chloro-2-fluoroacetanilide and process for producing the same | |
| JP2001505562A (en) | Processes and intermediates for the preparation of oxazoline derivatives | |
| BR112020019277B1 (en) | PROCESS FOR PRODUCING 2,6-DIALKYLPHENYL ACETIC ACIDS, AND THEIR INTERMEDIATES | |
| JP4828740B2 (en) | Process for producing 1,2,5-thiadiazoylmethanone derivative and dioxime derivative | |
| JPH06135883A (en) | Production of aromatic acyl compound | |
| JP2526937B2 (en) | 4-acetylamino-3-fluorophenol |