JPS5813545B2 - Sinquinapiride % 2 3 - D @ pyrimidinedione - Google Patents
Sinquinapiride % 2 3 - D @ pyrimidinedioneInfo
- Publication number
- JPS5813545B2 JPS5813545B2 JP7437A JP3774A JPS5813545B2 JP S5813545 B2 JPS5813545 B2 JP S5813545B2 JP 7437 A JP7437 A JP 7437A JP 3774 A JP3774 A JP 3774A JP S5813545 B2 JPS5813545 B2 JP S5813545B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrimidine
- dione
- pyrido
- melting point
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- -1 vinyloxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 150000008512 pyrimidinediones Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- JQPYINKVAWEQDQ-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidine-2,4-dione Chemical class C1=CC=C2C(=O)NC(=O)NC2=N1 JQPYINKVAWEQDQ-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
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- STGJVEFKIDCORV-UHFFFAOYSA-N acetic acid;1,1-dichloroethane Chemical compound CC(Cl)Cl.CC(O)=O STGJVEFKIDCORV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229960002944 cyclofenil Drugs 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は一般式（Ｉ）
（式中、Ｒはフエニル基又はハロゲン原子、低級アルギ
ル基、ニトロ基、トリフルオロメチル基で置換されたフ
エニル基、シクロアルキル基及びアルアルキル基を、Ａ
は炭素数２〜３のアルキレン基を、Ｘはハロゲン原子を
意味する）で表わされる新規なピリド（２，３−ｄ）ピ
リミジ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 phenyl group or a halogen atom, a lower argyl group, a nitro group, a phenyl group substituted with a trifluoromethyl group, a cycloalkyl group, and an alkyl group substituted with a trifluoromethyl group). The alkyl group, A
The present invention relates to a method for producing a novel pyrido(2,3-d)pyrimidinedione derivative represented by an alkylene group having 2 to 3 carbon atoms, and X means a halogen atom.
更に詳しくは一般式（■）
（式中、Ｒ及びＡは前記と同じ意味を有し、Ｙは水酸基
、ビニールオキシ基、アシルオキシ基，アルコキシカル
ボニルオキシ基、アルコキシ基及びテトラヒドロピラノ
キシ基を意味する）で表わされる化合物をハロゲン化し
て前記一般式（Ｉ）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。More specifically, the general formula (■) (wherein R and A have the same meanings as above, and Y represents a hydroxyl group, a vinyloxy group, an acyloxy group, an alkoxycarbonyloxy group, an alkoxy group, and a tetrahydropyranoxy group. The present invention relates to a method for producing a compound represented by the general formula (I) by halogenating a compound represented by the formula (I).
前記一般式（Ｉ）及び（■）におけるＲを更に詳しく説
明すると、Ｒはフエニル基、又は塩素、臭素、弗素、沃
素等のハロゲン原子、メチル、エチル等の低級アルキル
基、ニトロ基及びトリフルオロメチル基等が任意の位置
に１〜２個置換したフエニル基を、シクロアルキル基は
シクロヘキシル基又は低級アルキル置換シクロヘキシル
基を、アルアルキル基はベンジル及びフエネチル基、又
はハロゲン原子、低級アルキル基あるいは低ｉアルコキ
シ基で置換されたベンジル及びフエネチル基を表わす。To explain R in the general formulas (I) and (■) in more detail, R is a phenyl group, a halogen atom such as chlorine, bromine, fluorine, or iodine, a lower alkyl group such as methyl or ethyl, a nitro group, or a trifluoro group. A phenyl group substituted with one or two methyl groups, etc. at any position, a cycloalkyl group is a cyclohexyl group or a lower alkyl-substituted cyclohexyl group, an aralkyl group is a benzyl and phenethyl group, or a halogen atom, a lower alkyl group, or a lower alkyl group. i represents a benzyl and phenethyl group substituted with an alkoxy group.
出発原料である一般式（■）の化合物は１−置換ピリド
（２．３−ｄ）ピリミジン−２，４（１Ｈ，３Ｈ）−ジ
オン誘導体に相当するアルキル化剤を反応させることに
よって好収率で得られる。The starting material, the compound of general formula (■), can be obtained in good yield by reacting a 1-substituted pyrido(2.3-d)pyrimidine-2,4(1H,3H)-dione derivative with a corresponding alkylating agent. It can be obtained with
本発明の反応はベンゼン、トルエン、キシレンアセトン
、テトラヒドロフラン、ジクロロエタン酢酸等の不活性
溶媒中、チオニルクロライド、オキシ塩化リン，三塩化
リン、五塩化リン、濃塩酸塩化水素ガス、三臭化リン、
臭化水素酸、臭化水素ガス等を使用して行なわれる。The reaction of the present invention is carried out in an inert solvent such as benzene, toluene, xylene acetone, tetrahydrofuran, dichloroethaneacetic acid, etc., using thionyl chloride, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, concentrated hydrochloride, hydrogen chloride gas, phosphorus tribromide,
It is carried out using hydrobromic acid, hydrogen bromide gas, etc.
反応は一般には５０℃から使用する溶媒の沸点までの温
度で加熱することによって行なわれる。The reaction is generally carried out by heating at a temperature from 50°C to the boiling point of the solvent used.
生成した反応混合物は、これより有機溶媒を留去し残渣
に水を加え析出した結晶を沢取し、メタノール等の有機
容媒より再結晶して純品を得ることができる。From the generated reaction mixture, the organic solvent is distilled off, water is added to the residue, the precipitated crystals are collected, and a pure product can be obtained by recrystallizing from an organic medium such as methanol.
本発明の方法で得られる前記一般式（Ｉ）で表わされる
化合物は文献未載の新規化合物であり、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 compound represented by the general formula (I) obtained by the method of the present invention is a new 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 industrially available as a pharmaceutical. It is a very useful compound.
以下に本発明の実施例を示す。Examples of the present invention are shown below.
実施例 １
１−（ｍ−トリフルオロメチルフエニル）−３−（２−
エトキシカルボニルオキシエチル）ピリド（２， ３−
ｄ）ピリミジン−２．４（１Ｈ，３Ｈ）−ジオン４．２
ｇに氷酢酸−濃塩酸（１：１）１００ｍｌを加え摸酸ガ
スを吹き込みながら還流下で５時間加熱した。Example 1 1-(m-trifluoromethylphenyl)-3-(2-
ethoxycarbonyloxyethyl)pyrido(2,3-
d) Pyrimidine-2.4(1H,3H)-dione 4.2
100 ml of glacial acetic acid-concentrated hydrochloric acid (1:1) was added to the mixture, and the mixture was heated under reflux for 5 hours while blowing in anhydrous acid gas.
反応終了後、溶媒を減圧下で留去し残渣に水を加えて析
出した結晶をメタノールーエーテルより再結晶して、無
色プリズム晶の１−（ｍ−トリフルオロメチルフエニル
）−３−（２−クロロエチル）−ピリド〔２，３′−ｄ
〕ピリミジン−２，４（１Ｈ，３Ｈ）−ジオン２．７ｇ
を得た。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, and the precipitated crystals were recrystallized from methanol-ether to give colorless prismatic crystals of 1-(m-trifluoromethylphenyl)-3-( 2-chloroethyl)-pyrido[2,3'-d
]Pyrimidine-2,4(1H,3H)-dione 2.7g
I got it.
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 １４３〜１４４℃
元素分析値 Ｃ１６Ｈ１１Ｆ３ＣｌＮ３Ｏ２理論値Ｃ：
５１．９７ Ｈ：３．００ Ｎ：１１．３７実測値Ｃ：
５１．８２ Ｈ：２．９６ Ｎ：１１．２１実施例 ２
１−（ｍ−プロモフエニル） −３−（２−（．２−テ
トラヒドロピラノキシ）エチル〕ピリドシ，３−ｄ〕ピ
リミジン−２，４（ＩＨ，３Ｈ）−ジオン４，２ｇに氷
酢酸−濃塩酸（１：１）１００ｍｌを加え塩酸ガスを吹
き込みながら還流下で５時間加熱した。Melting point 143-144℃ Elemental analysis value C16H11F3ClN3O2 Theoretical value C:
51.97 H: 3.00 N: 11.37 Actual value C:
51.82 H: 2.96 N: 11.21 Example 2 1-(m-promophenyl)-3-(2-(.2-tetrahydropyranoxy)ethyl]pyridosy, 3-d]pyrimidine-2, 100 ml of glacial acetic acid-concentrated hydrochloric acid (1:1) was added to 4.2 g of 4(IH,3H)-dione, and the mixture was heated under reflux for 5 hours while blowing hydrochloric acid gas.
反応終了後、溶媒を減圧下で留去し残渣に水を加え析出
した結晶を濾取しメタノールーエーテルより再結晶して
、無色プリズム晶の１−（ｍ−プロモフエニル）−３−
（２−クロロエチル）−ピリド（２．３−ｄ）ピリミジ
ン−２，４（１Ｈ，３Ｈ）−ジオン３．５ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, and the precipitated crystals were collected by filtration and recrystallized from methanol-ether to give colorless prism crystals of 1-(m-promophenyl)-3-
3.5 g of (2-chloroethyl)-pyrido(2.3-d)pyrimidine-2,4(1H,3H)-dione was obtained.
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 １６８〜１７０℃
元素分析値 Ｃ１５Ｈ１１ＢｒＣｌＮ３Ｏ２理論値Ｃ：
４７．３３ Ｈ：２．９１ Ｎ：１１．０４実測値Ｃ：
４７．３１ Ｈ：２．８９ Ｎ：１１．０３実施例 ３
１−（ｍ−トリフルオロメチルフェニル）−３−（２−
ハイドロキシエチル）ピリド〔２，３−ｄ〕ピリミジン
−２，４（１Ｈ，３Ｈ）−ジオン３．５ｇ乾燥ベンゼン
３０ｍｌと三臭化燐８．１ｇの混合溶液を還流下８時間
反応後、溶媒を減圧下に留去し残渣を炭酸水素ナトリウ
ムで中和後エーテルで抽出、シリカゲルを充填したカラ
ムに吸着させ酢酸エチルで展開し、流出液を留去し残渣
をメタノールより再結晶して、無色プリズム晶の１−（
ｍ−トリフルオロメチルフエニル）−３−（２−プロモ
エチル）ピリド（２．３−ｄ）ピリミジン−２，４（１
Ｈ，３Ｈ）−ジオン３．４ｇを得た。Melting point 168-170℃ Elemental analysis value C15H11BrClN3O2 theoretical value C:
47.33 H: 2.91 N: 11.04 Actual value C:
47.31 H: 2.89 N: 11.03 Example 3 1-(m-trifluoromethylphenyl)-3-(2-
After reacting a mixed solution of 3.5 g of dry benzene (30 ml) and 8.1 g of phosphorus tribromide under reflux for 8 hours, the solvent was removed. Distilled under reduced pressure, neutralized the residue with sodium hydrogen carbonate, extracted with ether, adsorbed on a column packed with silica gel, developed with ethyl acetate, distilled off the effluent, recrystallized the residue from methanol, and obtained a colorless prism. Akira no 1-(
m-trifluoromethylphenyl)-3-(2-promoethyl)pyrido(2.3-d)pyrimidine-2,4(1
3.4 g of H,3H)-dione were obtained.
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 １５８〜１６０℃
元素分析値 Ｃ１５Ｈ１１ＢｒＦ３Ｎ３Ｏ２理論値Ｃ：
４６．３９ Ｈ：２６７ Ｎ：１０．１４実測値Ｃ：４
６．２１ Ｈ：２５３ Ｎ： ９．９８実施例 ４
１−（３．４−ジクロロフエニル）−３−（２−ハイド
ロキシエチル）ピリド（２．３−ｄ）ピリミジン−２．
４（１Ｈ，３Ｈ）−ジオン３．４ｇ、乾燥トルエン３０
ｍｌ．とチオニルクロライド１０ｍｌの混合溶液を還流
下５時間反応させた。Melting point 158-160℃ Elemental analysis value C15H11BrF3N3O2 Theoretical value C:
46.39 H: 267 N: 10.14 Actual value C: 4
6.21 H: 253 N: 9.98 Example 4 1-(3.4-dichlorophenyl)-3-(2-hydroxyethyl)pyrido(2.3-d)pyrimidine-2.
3.4 g of 4(1H,3H)-dione, 30 g of dry toluene
ml. A mixed solution of 10 ml of and thionyl chloride was reacted under reflux for 5 hours.
反応終了後、減圧下に溶媒を留去し残渣を５％の炭酸水
素ナトリウム溶液で中和し、析出した結晶をメタノール
で再結晶して、無色プリズム晶の１−（３．４−シクロ
ロフエニル）−３−（２−クロロエチル）ピリド（ ２
， ３−ｄ ’：ｌピリミジン−２，４（１Ｈ，３Ｈ
）−ジオン３．１ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, the residue was neutralized with 5% sodium bicarbonate solution, and the precipitated crystals were recrystallized with methanol to obtain colorless prismatic crystals of 1-(3.4-cyclophenyl). -3-(2-chloroethyl)pyrido (2
, 3-d':l pyrimidine-2,4(1H,3H
)-dione (3.1 g) was obtained.
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 １９３〜１９５℃
元素分析値 Ｃ１５Ｈ１０Ｃｌ３Ｎ３Ｏ２理論値Ｃ：４
８．６１ Ｈ：２．７２ Ｎ：１１．３４実測値Ｃ：４
８．５２ Ｈ：２．７５ Ｎ：１１．４２実施例 ５
１−（ｍ−クロロフエニル）−３−（２−ハイドロキシ
エチル）ピリドＣ２．３−ｄ）ピリミジン−２．４（１
Ｈ，３Ｈ）−ジオン３．２ｇに氷酢酸−濃塩酸（１：１
）１００ｍｌを加え塩酸ガスを吹き込みながら還流下４
時間加熱した。Melting point 193-195℃ Elemental analysis value C15H10Cl3N3O2 Theoretical value C: 4
8.61 H: 2.72 N: 11.34 Actual value C: 4
8.52 H: 2.75 N: 11.42 Example 5 1-(m-chlorophenyl)-3-(2-hydroxyethyl)pyrido C2.3-d) Pyrimidine-2.4(1
To 3.2 g of H,3H)-dione was added glacial acetic acid-concentrated hydrochloric acid (1:1).
) and refluxed while blowing in hydrochloric acid gas.
heated for an hour.
反応終了後、減圧下に宕媒を留去し残渣に水を加え析出
した結晶をメタノールより再結晶して、無色プリズム晶
の１−（ｍ−クロロフエニル）−３−（２−クロロエチ
ル）ピリド〔２．３−ｄ〕ピリミジン−２．４（１Ｈ，
３Ｈ）−ジオン２．９ｇを得た。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, and the precipitated crystals were recrystallized from methanol to obtain colorless prismatic crystals of 1-(m-chlorophenyl)-3-(2-chloroethyl)pyrid [ 2.3-d]pyrimidine-2.4(1H,
2.9 g of 3H)-dione were obtained.
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 １８１〜１８２℃
元素分析値 Ｃ１５Ｈ１１Ｃｌ２Ｎ３０２理論値Ｃ：５
３．５９ Ｈ：３．３０ Ｎ：１２５０実測値Ｃ：５３
．４８ Ｈ：３．２１ Ｎ：１２３９実施例 ６〜１９
実施例１〜５の方法に準じて次表の化合物を好収率で得
た。Melting point 181-182℃ Elemental analysis value C15H11Cl2N302 Theoretical value C: 5
3.59 H: 3.30 N: 1250 Actual value C: 53
．． 48 H: 3.21 N: 1239 Examples 6 to 19 According to the method of Examples 1 to 5, the compounds shown in the following table were obtained in good yields.
Claims (1)
基、ニトロ基、トリフルオロメチル基が置換シたフエニ
ル基、シクロアルキル基又はアルアルキル基を、Ａは炭
素数２〜３のアルキレン基を、Ｙは水酸基、ビニールオ
キシ基、アシルオキシ基、アルコキシカルボニル基、ア
ルコキシ基又はテトラヒドロピラノキシ基を意味する）
で表わされる化合物をハロゲン化することを特徴とする
一般式 （式中、Ｒ及びＡは前記と同じ意味を有し、Ｘはハロゲ
ン原子を意味する）で表わされる新規なピリド（２．３
−ｄ）ピリミジンジオン誘導体の製造法。[Scope of Claims] 1 General formula (wherein R is a phenyl group, a halogen atom, a lower alkyl group, a nitro group, a phenyl group substituted with a trifluoromethyl group, a cycloalkyl group, or an aralkyl group, and A is a phenyl group, a cycloalkyl group, or an aralkyl group) (Y means a hydroxyl group, vinyloxy group, acyloxy group, alkoxycarbonyl group, alkoxy group or tetrahydropyranoxy group)
A novel pyrido (2.3
-d) Method for producing a pyrimidinedione derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7437A JPS5813545B2 (en) | 1973-12-26 | 1973-12-26 | Sinquinapiride % 2 3 - D @ pyrimidinedione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7437A JPS5813545B2 (en) | 1973-12-26 | 1973-12-26 | Sinquinapiride % 2 3 - D @ pyrimidinedione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5095295A JPS5095295A (en) | 1975-07-29 |
| JPS5813545B2 true JPS5813545B2 (en) | 1983-03-14 |
Family
ID=11463119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7437A Expired JPS5813545B2 (en) | 1973-12-26 | 1973-12-26 | Sinquinapiride % 2 3 - D @ pyrimidinedione |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5813545B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0519150B2 (en) * | 1983-09-16 | 1993-03-15 | Canon Kk |
-
1973
- 1973-12-26 JP JP7437A patent/JPS5813545B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0519150B2 (en) * | 1983-09-16 | 1993-03-15 | Canon Kk |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5095295A (en) | 1975-07-29 |
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