JPS5829310B2 - Synquina 4-oxo-1234-tetrahydropyrido (2,3-D) pyrimidine - Google Patents
Synquina 4-oxo-1234-tetrahydropyrido (2,3-D) pyrimidineInfo
- Publication number
- JPS5829310B2 JPS5829310B2 JP49067791A JP6779174A JPS5829310B2 JP S5829310 B2 JPS5829310 B2 JP S5829310B2 JP 49067791 A JP49067791 A JP 49067791A JP 6779174 A JP6779174 A JP 6779174A JP S5829310 B2 JPS5829310 B2 JP S5829310B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrimidine
- tetrahydropyrido
- same meanings
- 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- VKXUCROJMDAHJO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine Chemical class C1=CN=C2NCNCC2=C1 VKXUCROJMDAHJO-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 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
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TZCIBBDRNICUNU-UHFFFAOYSA-N 2,3-dihydro-1h-pyrido[2,3-d]pyrimidin-4-one Chemical class C1=CC=C2C(=O)NCNC2=N1 TZCIBBDRNICUNU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 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
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- -1 methoxy, ethoxy Chemical group 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【発明の詳細な説明】
本発明は一般式（Ｉ）
（式中、Ｒ１は（１）フェニル基、又は（２）ハロゲン
原子、低級アルキル基、ニトロ基又はトリフルオロメチ
ル基で置換されたフェニル基を、Ｒ２は（１）水素原子
、（２）低級アルキル基、（３）・・ロゲン原子、低級
シクロアルキル基、アルコキシ基、水酸基、アセトキシ
基又はフェニル基で置換された低級アルキル基、（４）
アルケニル基又はアルキニル基を意味する）で表わされ
る新規な４−オキソ〜１・２・３・４−テトラヒドロピ
リド〔２・３−ｄ〕ピリミジン誘導体及びその酸付加塩
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 R1 is (1) a phenyl group, or (2) a phenyl group substituted with a halogen atom, a lower alkyl group, a nitro group, or a trifluoromethyl group). group, R2 is (1) a hydrogen atom, (2) a lower alkyl group, (3) a lower alkyl group substituted with a rogen atom, a lower cycloalkyl group, an alkoxy group, a hydroxyl group, an acetoxy group, or a phenyl group, ( 4)
This invention relates to a method for producing a novel 4-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine derivative represented by an alkenyl group or an alkynyl group, and an acid addition salt thereof. .
更に詳細には一般式（ＩＩ）
（式中、Ｒ１及びＲ２は前記と同じ意味を有し、Ｘは硫
黄原子及びイミノ基を意味する）で表わされる化合物を
酸化又は加水分解して、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, a compound represented by the general formula (II) (wherein R1 and R2 have the same meanings as above, and X means a sulfur atom and an imino group) is oxidized or hydrolyzed to obtain the general formula (II). The present invention relates to a method for producing a compound represented by formula (I).
前記一般式（Ｉ）及び（ｎ）におけるＲ１及びＲ２に就
いて更に詳細に説明すると、Ｒ１はフェニル基又は塩素
、臭素、弗素、沃素等のハロゲン原子、メチル、エチル
、プロピル等の低級アルキル基、メトキシ、エトキシ、
プロポキシ等の低級アルコキシ基、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個置換したフェ
ニル基を、表わす。To explain R1 and R2 in the general formulas (I) and (n) in more detail, R1 is a phenyl group, a halogen atom such as chlorine, bromine, fluorine, or iodine, or a lower alkyl group such as methyl, ethyl, or propyl. , methoxy, ethoxy,
It represents a phenyl group substituted with 1 or 2 lower alkoxy groups such as propoxy, nitro group, trifluoromethyl group, etc. at any position.
又、Ｒ２の低級アルキル基はメチル、エチル、ｎ−プロ
ピル、イソプロピル、ｎ−ブチル、イソブチル、ｎ−ペ
ンチル等の低級アルキル基を、置換低級アルキル基は・
・ロゲン原子、低級シクロアルキル基、アルコキシ基、
水酸基、アセトキシ基、フェニル基等で置換された低級
アルキル基を、アリル、３−メチルアリル、３・３−ジ
メチルアリル等のアルケニル基又はプロパルギル等のア
ルキニル基を表わす。In addition, the lower alkyl group of R2 is a lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, etc., and the substituted lower alkyl group is
・Rogen atom, lower cycloalkyl group, alkoxy group,
A lower alkyl group substituted with a hydroxyl group, an acetoxy group, a phenyl group, etc. represents an alkenyl group such as allyl, 3-methylallyl, 3,3-dimethylallyl, or an alkynyl group such as propargyl.
本発明により得られた前記一般式（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活性を有し医
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 present invention is a new compound that has not been described in any literature, and has a remarkable analgesic effect,
It is an industrially useful compound as a pharmaceutical, having pharmacological activities such as anti-inflammatory and central nervous system depressing effects.
又、前記化合物は通常の薬学上許容せられる方法によっ
て無機酸及び有機酸との付加塩に導くことができる。The above compounds can also be converted into addition salts with inorganic and organic acids by conventional pharmaceutically acceptable methods.
本発明を実施するには前記一般式（ｎ）の化合物を酸又
は塩基の存在下に適当な溶媒中で加水分解するか、又は
酸化剤で酸化することによって行なわれる。The present invention is carried out by hydrolyzing the compound of general formula (n) in a suitable solvent in the presence of an acid or base, or by oxidizing it with an oxidizing agent.
本反応で使用する溶媒としては例えば水、メタノール、
エタノール、ジオキサン、テトラヒドロフラン、アセト
ン及びジメチルスルホキシド等が挙げられる。Examples of solvents used in this reaction include water, methanol,
Examples include ethanol, dioxane, tetrahydrofuran, acetone and dimethyl sulfoxide.
又、酸としては塩酸、硫酸、燐酸などの鉱酸が、塩基と
しては水酸化す） Ｉ）ラム、水酸化カリウム等の水酸
化アルカリ金属、炭酸ナトリウム、炭酸カリウム等の炭
酸アルカリ金属、水酸化カルシウム、水酸化バリウム等
の水酸化アルカリ土類金属あるいは水酸化アンモニウム
等が、又、酸化剤としては過酸化水素、過マンガン酸塩
、クロム酸塩、重クロム酸塩等が挙げられるが、好まし
くは過酸化水素を使用するのが望ましい。In addition, mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid can be used as acids, and hydroxide can be used as bases. Calcium, alkaline earth metal hydroxides such as barium hydroxide, ammonium hydroxide, etc., and oxidizing agents include hydrogen peroxide, permanganates, chromates, dichromates, etc., but are preferred. It is preferable to use hydrogen peroxide.
又、反応は室温でも進行するが加熱すると短時間で完結
する。Furthermore, although the reaction proceeds at room temperature, it is completed in a short time when heated.
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 １
１−フェニル−３−メチル−４−チオ−１・２・３・４
−テトラヒドロピリド〔２・３−ｄ〕ピリミジン２．５
１、テトラヒドロフラン２０ｍ１と３０％の過酸化水素
２０Ｔｎｌを還流下２時間反応させた。Example 1 1-phenyl-3-methyl-4-thio-1,2,3,4
-tetrahydropyrido[2,3-d]pyrimidine 2.5
1. 20ml of tetrahydrofuran and 20Tnl of 30% hydrogen peroxide were reacted under reflux for 2 hours.
反応終了後、減圧下に溶媒を留去し残渣をエーテルより
再結晶して、無色プリズム晶の１−フェニル−３−メチ
ル−４−オキノート２・３・４テトラヒドロピリド〔２
・３−ｄ〕ピリミジン２．１１を得た。After the reaction, the solvent was distilled off under reduced pressure and the residue was recrystallized from ether to give colorless prismatic crystals of 1-phenyl-3-methyl-4-oquinote 2,3,4 tetrahydropyride [2
・3-d] Pyrimidine 2.11 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 １４０〜１４１ ’Ｃ
元素分析値 Ｃ１４Ｈ１３Ｎ３０
理論値 Ｃニア０．２７ Ｈ：５．４８Ｎ：１７．５
６
実測値 Ｃニア０．１２ Ｈ：５．４２Ｎ：１７．５
４
実施例 ２
１−（ｍ−トリフルオロメチルフェニル）−３エチル−
４−エチルイミノピリド−１・２・３・４−テトラヒド
ロピリド〔２・３−ｄ〕ピリミジン３．４２と１５％塩
酸４０ｒｒＬｌを還流下３時間反応させた。Melting point 140-141'C Elemental analysis value C14H13N30 Theoretical value Cnea 0.27 H:5.48N:17.5
6 Actual value C near 0.12 H: 5.42 N: 17.5
4 Example 2 1-(m-trifluoromethylphenyl)-3ethyl-
3.42 liters of 4-ethyliminopyrido-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 40 rrLl of 15% hydrochloric acid were reacted under reflux for 3 hours.
反応終了後、５％の炭酸ソーダ溶液で中和し、次にエー
テルで抽出してエーテル層を濃縮放置すると、無色針状
晶の１−（ｍ−）’Ｊフルオロメチルフェニル）−３−
エチル−４−オキノド２・３・４−テトラヒドロピリド
〔２・３ｄ〕ピリミジン２．４１を得た。After the reaction is completed, the reaction is neutralized with a 5% sodium carbonate solution, extracted with ether, and the ether layer is concentrated and left to stand, yielding colorless needle-like crystals of 1-(m-)'Jfluoromethylphenyl)-3-.
Ethyl-4-oquinodo 2,3,4-tetrahydropyrido[2,3d]pyrimidine 2.41 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 １０８〜１０９℃
元素分析値 Ｃ１６Ｈ１４Ｆ３Ｎ３０
理論値 Ｃ：５９．８１ Ｈ：４．３９Ｎ：１３．０
８
実測値 Ｃ：５９．６９ Ｈ：４．３６Ｎ：１３．０
９
実施例 ３
１− （ｐ−クロロフェニル）−３−エチル−４チオー
ト２・３・４−テトラヒドロピリド〔２・３−ｄ〕ピリ
ミジン３グをメタノール１００ｗ１ｌに溶解し、これに
５％水酸化ナトリウム溶液４０ｒｒＬｌを加えて３時間
還流した。Melting point 108-109℃ Elemental analysis value C16H14F3N30 Theoretical value C: 59.81 H: 4.39 N: 13.0
8 Actual value C: 59.69 H: 4.36 N: 13.0
9 Example 3 3 g of 1-(p-chlorophenyl)-3-ethyl-4thioto 2,3,4-tetrahydropyrido[2,3-d]pyrimidine was dissolved in 100w1l of methanol, and 5% hydroxide was added to the solution. 40rrLl of sodium solution was added and refluxed for 3 hours.
次いで反応液を濃縮し残渣を水で稀釈して生じた結晶を
１取し、水洗、乾燥後エチルエーテルより再結晶すると
、１−（ｐ−クロロフェニル）−３−エチル４−オキソ
−１・２・３・４−テトラヒドロピリド〔２・３−ｄ〕
ピリミジン２．６１を得た。Next, the reaction solution was concentrated, the residue was diluted with water, and one portion of the resulting crystals was taken, washed with water, dried, and recrystallized from ethyl ether to give 1-(p-chlorophenyl)-3-ethyl 4-oxo-1.2.・3,4-tetrahydropyride [2,3-d]
2.61 pyrimidines 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 １００〜１０１ ’Ｃ
元素分析値 Ｃ１５Ｈ１４ＣＩＮ３０
理論値 Ｃ：６２．６１ Ｈ：４．９ＯＮ：１４．６
０
実測値 Ｃ：６２．４８ Ｈ：４８２
Ｎ：１４．５３
実施例 ４〜９１
実施例１〜３の方法に準じて次表の化合物を合成した。Melting point 100-101'C Elemental analysis value C15H14CIN30 Theoretical value C: 62.61 H: 4.9 ON: 14.6
0 Actual value C: 62.48 H: 482 N: 14.53 Examples 4 to 91 The compounds shown in the following table were synthesized according to the methods of Examples 1 to 3.
Claims (1)
原子、低級アルキル基、ニトロ基又はトリフルオロメチ
ル基で置換されたフェニル基を、Ｒ２は（１）水素原子
、（２）低級アルキル基、（３）ハロゲン原子、低級シ
クロアルキル基、アルコキシ基、水酸基、アセトキシ基
又はフェニル基で置換された低級アルキル基、（４）ア
ルケニル基又はアルキニル基を、Ｘは硫黄原子を意味す
る）で表わされる化合物を酸化することを特徴とする一
般式 （式中、Ｒ１及びＲ２は前記と同じ意味を有する）で表
わされる新規な４−オキンート２・３・４テトラヒドロ
ピリド〔２・３−ｄ〕ピリミジン誘導体及びその酸付加
塩の製造法。 ２一般式 （式中、Ｒ１及びＲ２、特許請求の範囲第１項における
と同じ意味を有し、Ｘはイミノ基を意味する）で表わさ
れる化合物を加水分解することを特徴とする特許 （式中、Ｒ１及びＲ２は前記と同じ意味を有する）で表
わされる新規な４−オキソート２・３・４−テトラヒド
ロピリド〔２・３−ｄ〕ピリミジン誘導体及びその酸付
加塩の製造法。[Scope of Claims] (In the formula, R1 is (1) a phenyl group, or (2) a phenyl group substituted with a halogen atom, lower alkyl group, nitro group, or trifluoromethyl group, and R2 is (1) hydrogen X is A novel 4-ochineto-2,3,4-tetrahydropyrylene compound represented by the general formula (wherein R1 and R2 have the same meanings as above), which is characterized by oxidizing a compound represented by a sulfur atom). Method for producing do[2,3-d]pyrimidine derivatives and acid addition salts thereof. 2 (wherein R1 and R2 have the same meanings as in claim 1 and X means an imino group) A method for producing a novel 4-oxoto 2,3,4-tetrahydropyrido[2,3-d]pyrimidine derivative represented by (wherein R1 and R2 have the same meanings as above) and an acid addition salt thereof.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49067791A JPS5829310B2 (en) | 1974-06-12 | 1974-06-12 | Synquina 4-oxo-1234-tetrahydropyrido (2,3-D) pyrimidine |
| SE7505641A SE420608B (en) | 1974-06-12 | 1975-05-16 | ANALOGY PROCEDURE FOR PREPARATION OF 4-OXO-1,2,3,4-TETRAHYDROPYRIDO (2,3-D) -PYRIMIDINES |
| AU81468/75A AU491721B2 (en) | 1974-06-12 | 1975-05-23 | PYRIDO [2,3-d] PYRIMIDINONES |
| DE19752523730 DE2523730A1 (en) | 1974-06-12 | 1975-05-28 | PYRIDO SQUARE CLAMP ON 2.3-D SQUARE CLAMP FOR PYRIMIDINONS |
| US05/582,889 US4009166A (en) | 1974-06-12 | 1975-06-02 | Pyrido(2,3-d) pyrimidinones |
| CH723775A CH621120A5 (en) | 1974-06-12 | 1975-06-05 | Process for the preparation of 4-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidines |
| NL7506720A NL7506720A (en) | 1974-06-12 | 1975-06-06 | 2- or 4-oxo-1,2,3,4-tetrahydropyrido(2,3-d)pyrimidins - with e.g. anti-inflammatory analgesic and CNS-depressive activity |
| FR7518214A FR2274304A1 (en) | 1974-06-12 | 1975-06-11 | PYRIDO (2,3D) PYRIMIDINONES |
| CA229,202A CA1039723A (en) | 1974-06-12 | 1975-06-12 | Process for preparing 4-oxo-1,2,3,4-tetrahydropyrido 2,3-d pyrimidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49067791A JPS5829310B2 (en) | 1974-06-12 | 1974-06-12 | Synquina 4-oxo-1234-tetrahydropyrido (2,3-D) pyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS514198A JPS514198A (en) | 1976-01-14 |
| JPS5829310B2 true JPS5829310B2 (en) | 1983-06-22 |
Family
ID=13355114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49067791A Expired JPS5829310B2 (en) | 1974-06-12 | 1974-06-12 | Synquina 4-oxo-1234-tetrahydropyrido (2,3-D) pyrimidine |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5829310B2 (en) |
| CA (1) | CA1039723A (en) |
| CH (1) | CH621120A5 (en) |
| SE (1) | SE420608B (en) |
-
1974
- 1974-06-12 JP JP49067791A patent/JPS5829310B2/en not_active Expired
-
1975
- 1975-05-16 SE SE7505641A patent/SE420608B/en unknown
- 1975-06-05 CH CH723775A patent/CH621120A5/en not_active IP Right Cessation
- 1975-06-12 CA CA229,202A patent/CA1039723A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE420608B (en) | 1981-10-19 |
| JPS514198A (en) | 1976-01-14 |
| CH621120A5 (en) | 1981-01-15 |
| CA1039723A (en) | 1978-10-03 |
| SE7505641L (en) | 1975-12-15 |
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