JPS587630B2 - Shinkina Quinazorindion Yudou Taino Seizouhou - Google Patents
Shinkina Quinazorindion Yudou Taino SeizouhouInfo
- Publication number
- JPS587630B2 JPS587630B2 JP49067379A JP6737974A JPS587630B2 JP S587630 B2 JPS587630 B2 JP S587630B2 JP 49067379 A JP49067379 A JP 49067379A JP 6737974 A JP6737974 A JP 6737974A JP S587630 B2 JPS587630 B2 JP S587630B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- yudou
- shinkina
- seizouhou
- quinazorindion
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000008515 quinazolinediones Chemical class 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- -1 nitroanilinobenzoic acid amide Chemical compound 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XNPOFXIBHOVFFH-UHFFFAOYSA-N N-cyclohexyl-N'-(2-(4-morpholinyl)ethyl)carbodiimide Chemical compound C1CCCCC1N=C=NCCN1CCOCC1 XNPOFXIBHOVFFH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は一般式（Ｉ）
（式中、Ｒは低級アルキル基、及びハロゲン原子、低級
シクロアルキル基、水酸基、低級アルコキシ基、アセト
キシ基、アルコキシカルボニル基、フエニル基又は置換
フエニル基で置換された低級アルキル基、及びアルケニ
ル基及びアルキニル基を意味する）で表わされる新規な
キナゾリンジオン誘導体の製造法に関するものである。Detailed Description of the Invention The present invention is based on the general formula (I) (wherein R is a lower alkyl group, and a halogen atom, a lower cycloalkyl group, a hydroxyl group, a lower alkoxy group, an acetoxy group, an alkoxycarbonyl group, a phenyl group, or The present invention relates to a method for producing a novel quinazolinedione derivative represented by a lower alkyl group substituted with a substituted phenyl group, and an alkenyl group and an alkynyl group.
更に詳シ《はＩ−（ｍ−ニトロフエニル）キナゾリンー
２４（ＩＨ，３Ｈ）一ジオン（■）に一般式（■）
ＲＯＨ （■）
（式中、Ｒは前記と同じ意味を有する）で表わされるア
ルコール類を反応させて、前記一般式（１）で表わされ
る化合物を製造する方法に関するものである。In more detail, I-(m-nitrophenyl)quinazoline-24(IH,3H) monodione (■) is represented by the general formula (■) ROH (■) (wherein R has the same meaning as above) The present invention relates to a method for producing a compound represented by the general formula (1) by reacting alcohols.
前記一般式（１）及び（■）におけるＲについて更に具
体的に説明すると、Ｒの低級アルキル基はメチル、エチ
ル、ｎ−プロビル、イソプロビル、ｎ−ブチル、イソブ
チル、ｎ−ペンチル等の低級アルキル基を、置換された
低級アルキル基の低級シクロアルキル基は炭素原子３〜
６からなる低級シクロアルキル基、置換フエニル基はハ
ロゲン原子、低級アルキル基、低級アルコキシ等で置換
されたフエニル基を、アルケニル基はアリル、３，３−
ジメチルアリル、ぺクロチル等を、アルキニル基はプ０
パルギル等を表わす。To explain R in the above general formulas (1) and (■) more specifically, the lower alkyl group of R is lower alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, etc. The lower cycloalkyl group of the substituted lower alkyl group has 3 to 3 carbon atoms.
A lower cycloalkyl group consisting of 6, a substituted phenyl group is a phenyl group substituted with a halogen atom, a lower alkyl group, a lower alkoxy group, etc., an alkenyl group is an allyl, 3,3-
dimethylallyl, pecrotyl, etc., and the alkynyl group is
Representing Pargil et al.
本発明により得られた前記一般式（Ｉ）で表わされるキ
ナゾリンジオン誘導体は文献未載の新規化合物であって
、顕著な鎮痛作用、抗炎症作用及び中枢神経抑制作用等
の薬理作用を有し医薬品として産業上有用な化合物であ
る。The quinazolinedione derivative represented by the general formula (I) obtained by the present invention is a novel compound that has not been described in any literature, and has pharmacological effects such as remarkable analgesic effect, anti-inflammatory effect, and central nervous system depressing effect, and is a pharmaceutical drug. It is an industrially useful compound.
本発明の目的化合物は、昭和４５年特許出願公告第２４
０３１号公報等に記載される公知類似化合物に比し強い
鎮痛作用及び抗炎症作用を有するものである。The object compound of the present invention is disclosed in Patent Application Publication No. 24 of 1971.
It has stronger analgesic and anti-inflammatory effects than the known similar compounds described in Publication No. 031 and the like.
このことを例を挙げて次表で具体的に示す。This is illustrated in the following table with examples.
実験方法
（１）抗炎症作用
１２０〜１５０ＩのＷｉｓｔａｒ系雄ラット（１群５匹
）に水５ｍｌを強制投与して３０分後に被検化合物を経
口投与した。Experimental method (1) Anti-inflammatory effect 5 ml of water was forcibly administered to 120-150 I Wistar male rats (5 rats per group), and 30 minutes later, the test compound was orally administered.
更に１時間後、１％力ラゲニンー注射用蒸留水液０．１
ｍｌを足跪皮下に注入し、３時間後の浮腫抑制率を求め
た。After another hour, 1% lagenin-distilled water for injection 0.1
ml was injected subcutaneously into the knee of the foot, and the edema suppression rate was determined 3 hours later.
（２）鎮痛作用
１７〜２２ｇのｄｄＹ系雄マウス（１群１０匹）に０．
５％ｌ−ラガントに懸濁した被検化合物を０．１ｍｌ／
ｌ０ｇの容量で経口投与し、３０分後に０．６％酢酸水
溶液を腹腔内に注入し、更に１０分後より１０分間のス
トレツチング（身よじり運動）の数を数え５０チ鎮痛量
及びその信頼限界を求めた（Ｐ＝０．０５）。(2) Analgesic effect 0.0.
0.1 ml of test compound suspended in 5% l-lagant
Orally administered in a volume of 10 g, 30 minutes later, 0.6% acetic acid aqueous solution was injected intraperitoneally, and after another 10 minutes, the number of stretching movements (twisting movements) for 10 minutes was counted to calculate the 50-chi analgesic amount and its confidence limit. was calculated (P=0.05).
以上の表から明らかな様に本発明の新規化合物は公知類
似化合物に比べて非常に強い薬理活性を有し、鎮痛剤及
び抗炎症剤として極めて有用な化合物である。As is clear from the above table, the novel compounds of the present invention have much stronger pharmacological activity than known similar compounds, and are extremely useful compounds as analgesics and anti-inflammatory agents.
本発明の出発原料である１−（ｍ−ニトロフエニル）キ
ナゾリンー２，４（ＩＨ，３Ｈ）一ジオンは２−（ｍ−
ニトロアニリノ）安息香酸アミドに尿素を反応させるこ
とによって得られる。The starting material of the present invention, 1-(m-nitrophenyl)quinazoline-2,4(IH,3H) monodione, is 2-(m-
Obtained by reacting urea with nitroanilinobenzoic acid amide.
本発明を反応式で示すと次の通りである。The reaction formula of the present invention is as follows.
本発明の反応はテトラヒド口フラン、クロロホルム、塩
化メチレン、シクロ口エタン、ベンゼン、トルエン、キ
シレン等の不活性溶媒中か又は反応させるアルコール類
を過剰に使用して、Ｎ，Ｎ’一ジシクロへキシル力ルポ
ジイミド、Ｎ−シクロへキシルーＮ’−（２−モルホリ
ノエチル）カルボジイミド、Ｎ，Ｎ’−ジパラトリル力
ルポジイミド、三塩化燐、パラトルエンスルホン酸等の
脱水剤の存在下で行なうのが好ましく、特にカルボジイ
ミド誘導体を脱水剤として使用すると収量よく目的化合
物を得ることができる。The reaction of the present invention is carried out in an inert solvent such as tetrahydrofuran, chloroform, methylene chloride, cycloethane, benzene, toluene, xylene, etc. or by using an excess of the alcohol to be reacted. Preferably, the reaction is carried out in the presence of a dehydrating agent such as lupodiimide, N-cyclohexyl-N'-(2-morpholinoethyl)carbodiimide, N,N'-diparatolylpodiimide, phosphorus trichloride, and para-toluenesulfonic acid. When a carbodiimide derivative is used as a dehydrating agent, the target compound can be obtained in good yield.
反応を大気中で行なう場合は着色及び副反応を抑制する
ために窒素雰囲気下で行なうのがよい。When the reaction is carried out in the atmosphere, it is preferably carried out under a nitrogen atmosphere in order to suppress coloring and side reactions.
又、低沸点の溶媒を使用する場合は封管中で行なうのが
有利である。Furthermore, when using a solvent with a low boiling point, it is advantageous to carry out the reaction in a sealed tube.
反応温度は特に限定されず、通常使用する溶媒の沸点か
ら２００℃の温度範囲で反応させられる。The reaction temperature is not particularly limited, and the reaction is carried out in a temperature range from the boiling point of the commonly used solvent to 200°C.
反応生成物は溶媒を留去し、過剰の脱水剤を分解後メタ
ノール、エタノール等の有機溶媒で再結晶するか、又は
カラムクロマト法によって分離精製することによって純
品を得ることができる。A pure product can be obtained from the reaction product by distilling off the solvent, decomposing excess dehydrating agent, and then recrystallizing it with an organic solvent such as methanol or ethanol, or separating and purifying it by column chromatography.
以下に実施例を示し本発明を更に具体的に説明する。EXAMPLES The present invention will be explained in more detail with reference to Examples below.
実施例ｌ
１−（ｍ−ニトロフエニル）キナゾリンー２，４（ＩＨ
，３Ｈ）一ジオン２．８ｇ、メタノール３０ｍｌとＮ，
Ｎ’−ジシクロへキシル力ルポジイミド６．２ｇの混合
物を封管中１２０〜１３０℃で１０時間反応させた。Example l 1-(m-nitrophenyl)quinazoline-2,4(IH
,3H) monodione 2.8g, methanol 30ml and N,
A mixture of 6.2 g of N'-dicyclohexyllupodiimide was reacted in a sealed tube at 120-130°C for 10 hours.
反応終了後、減圧下に溶媒を留去し残渣に水を加え析出
した結晶をクロロホルムに溶解し、アルミナを充填した
カラムに吸着させクロロホルムで展開し、溶出液の溶媒
を留去し残渣をメタノールにより再結晶して、無色針状
晶の１−（ｍ−ニトロフエニル）−３−メチルキナソリ
ン−２．４（１Ｈ，３Ｈ）一ジオン２．１ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, the precipitated crystals were dissolved in chloroform, adsorbed on a column packed with alumina, developed with chloroform, the solvent of the eluate was distilled off, and the residue was dissolved in methanol. Recrystallization was performed to obtain 2.1 g of 1-(m-nitrophenyl)-3-methylquinasoline-2.4(1H,3H) monodione in the form of colorless needles.
この物質の融点及び元素分析値は次の通りであった。The melting point and elemental analysis values of this substance were as follows.
融 点 ２４１〜２４２℃
元素分析値 ＣＩ５Ｈ１１Ｎ３０４
理論値Ｃ：６０．６０ Ｈ：３．７３ Ｎ：１４．１４
実測値Ｃ：６０．５１ Ｈ：３．７２ Ｎ：１４．０９
実施例 ２
１−（ｍ−ニトロフエニル）キナソリンー２，４（ＩＨ
，３Ｈ）一ジオン２．８ｇ、エタノール３０ｍｌとＮ，
Ｎ’−ジシクロへキシル力ルポジイミド６．２ｇを封管
中１３０〜１４０℃で１２時間反応させた。Melting point 241-242℃ Elemental analysis value CI5H11N304 Theoretical value C: 60.60 H: 3.73 N: 14.14
Actual value C: 60.51 H: 3.72 N: 14.09
Example 2 1-(m-nitrophenyl)quinasoline-2,4(IH
,3H) monodione 2.8g, ethanol 30ml and N,
6.2 g of N'-dicyclohexyllupodiimide was reacted in a sealed tube at 130-140°C for 12 hours.
反応終了後、減圧下溶媒を留去し残渣に水を加えて析出
した結晶をクロロホルムに溶解し、アルミナを充填した
カラムに吸着させクロロホルムで展開し、溶出液の溶媒
を留去し残渣をメタノールで再結晶して、無色プリズム
晶の１−（ｍ＝ニトロフエニル）−３−エチルキナソリ
ン−２，４（ＩＨ，３Ｈ）一ジオン１．７ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, the precipitated crystals were dissolved in chloroform, adsorbed on a column packed with alumina, developed with chloroform, the solvent of the eluate was distilled off, and the residue was dissolved in methanol. Recrystallization was performed to obtain 1.7 g of colorless prismatic crystals of 1-(m=nitrophenyl)-3-ethylquinasoline-2,4(IH,3H)-dione.
この物質の融点及び元素分析値は次の通りであった。The melting point and elemental analysis values of this substance were as follows.
融 点 １９３〜１９４℃
元素分析値 Ｃ，６Ｈ１３Ｎ３０４
理論値Ｃ：６１．７３ Ｈ：４．２１ Ｎ：１３．５０
実測値Ｃ：６１．５８ Ｈ：４．１９ Ｎ：ｌ３．４７
実施例 ３〜１６
実施例１〜２の方法に準じて次表の化合物を得た。Melting point 193-194℃ Elemental analysis value C, 6H13N304 Theoretical value C: 61.73 H: 4.21 N: 13.50
Actual value C: 61.58 H: 4.19 N: l3.47
Examples 3-16 The compounds shown in the following table were obtained according to the methods of Examples 1-2.
Claims (1)
ＩＨ，３Ｈ，ｌ−ジオンに一般式 ＲＯＨ （式中、Ｒは低級アルキル基、又はハロゲン原子、低級
シクロアルキル基、水酸基、低級アルコキシ基、アセト
キシ基、アルコキシカルボニル基、フエニル基又は置換
フエニル基で置換された低級アルキル基、又はアルケニ
ル基又はアルキニル基を意味する）で表わされる化合物
を反応させるこ（式中、Ｒは前記と同じ意味を有する）
で表わされる新規なキナゾリンジオン誘導体の製造法。[Claims] 1 1-(m-nitrophenyl)quinazoline-2,4(
IH, 3H, l-dione with the general formula ROH (wherein R is a lower alkyl group, or a halogen atom, a lower cycloalkyl group, a hydroxyl group, a lower alkoxy group, an acetoxy group, an alkoxycarbonyl group, a phenyl group or a substituted phenyl group) a substituted lower alkyl group, or an alkenyl group or an alkynyl group (wherein R has the same meaning as above).
A method for producing a novel quinazolinedione derivative represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49067379A JPS587630B2 (en) | 1974-06-11 | 1974-06-11 | Shinkina Quinazorindion Yudou Taino Seizouhou |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49067379A JPS587630B2 (en) | 1974-06-11 | 1974-06-11 | Shinkina Quinazorindion Yudou Taino Seizouhou |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS514187A JPS514187A (en) | 1976-01-14 |
| JPS587630B2 true JPS587630B2 (en) | 1983-02-10 |
Family
ID=13343307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49067379A Expired JPS587630B2 (en) | 1974-06-11 | 1974-06-11 | Shinkina Quinazorindion Yudou Taino Seizouhou |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS587630B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0433771A (en) * | 1990-05-29 | 1992-02-05 | Kurosaki Refract Co Ltd | Device for closing nozzle for molten metal |
-
1974
- 1974-06-11 JP JP49067379A patent/JPS587630B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS514187A (en) | 1976-01-14 |
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