JPS5924994B2 - Novel pyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine derivatives - Google Patents
Novel pyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine derivativesInfo
- Publication number
- JPS5924994B2 JPS5924994B2 JP51001316A JP131676A JPS5924994B2 JP S5924994 B2 JPS5924994 B2 JP S5924994B2 JP 51001316 A JP51001316 A JP 51001316A JP 131676 A JP131676 A JP 131676A JP S5924994 B2 JPS5924994 B2 JP S5924994B2
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- pyrimidine
- melting point
- dihydropyrido
- reaction
- 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
- YUUJQXSULZBIKH-UHFFFAOYSA-N 2,3,5,7,13-pentazatricyclo[7.4.0.01,5]trideca-3,6,8,10,12-pentaene Chemical class C1=CC=NC23NN=CN3C=NC=C21 YUUJQXSULZBIKH-UHFFFAOYSA-N 0.000 title 1
- -1 hydrogen pyrido [2,3-d ]-S-triazolo[4,3-c]pyrimidine derivative Chemical class 0.000 claims description 15
- 239000000126 substance Substances 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
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical group 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000000921 elemental analysis Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940117975 chromium trioxide Drugs 0.000 description 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent 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
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- 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）
□Ｒ２（Ｉ）
（式中、Ｒ１はフェニル基又はハロゲン原子、トリフル
オロメチル基で置換されたフェニル基を、Ｒ２は水素原
子、低級アルキル基又はハロゲン原子、シアノ基で置換
された低級アルキル基を、Ｘはメチレン基又はカルボニ
ル基を意味する）で表わされる新規なピリド〔２、３−
ｄ〕−５−トリアゾロ〔４、３−ｃ〕ピリミジン誘導体
に関するものである。Detailed Description of the Invention The present invention is based on the general formula (I) □R2(I) (wherein, R1 is a phenyl group, a halogen atom, or a phenyl group substituted with a trifluoromethyl group, and R2 is a hydrogen atom, a lower A new pyrido [2,3-
d]-5-triazolo[4,3-c]pyrimidine derivatives.
本発明の新規化合物群は顕著な鎮痛作用、抗炎症作用、
解熱作用、中枢神経抑制作用、坑潰瘍作用、抗ヒスタミ
ン作用、利尿作用及び制服作用等の薬理作用を有し、新
規医薬品として産業上非常に有用な化合物である。The novel compound group of the present invention has remarkable analgesic and anti-inflammatory effects,
It has pharmacological effects such as antipyretic action, central nervous system depressant action, anti-ulcer action, antihistamine action, diuretic action, and uniform action, and is an industrially very useful compound as a new drug.
さて、ここで前記一般式（Ｉ）におけるＲ１及びＲ２に
ついて更に詳細に説明すると、Ｒ１はフェニル基又は置
換フェニル基等のアリール基を表わし、Ｒ２は水素原子
又はトリハロゲノメチル基、低級アルキル基及び置換低
級アルキル基等のアルキル基を表わす。Now, to explain R1 and R2 in the general formula (I) in more detail, R1 represents an aryl group such as a phenyl group or a substituted phenyl group, and R2 represents a hydrogen atom, a trihalogenomethyl group, a lower alkyl group, or Represents an alkyl group such as a substituted lower alkyl group.
更に具体的には、Ｒ１はフェニル基、塩素、臭素、弗素
、沃素等のハロゲン原子又はトリフルオロメチル基が任
意の位置に１〜２個置換したフ工ニル基を表わす。More specifically, R1 represents a phenyl group, a phenyl group substituted with one or two halogen atoms such as chlorine, bromine, fluorine, and iodine, or trifluoromethyl groups at arbitrary positions.
又Ｒ２は水素原子、メチル、エチル、ｎ−プロピル、イ
ソプロピル、ｎ−ブチル、イソブチル等の低級アルキル
基、塩素、臭素、弗素、沃素等のハロゲン原子又はシア
ノ基で置換された低級アルキル基を表わす。次に、本発
明に係る化合物の製造方法について述べる。R2 represents a hydrogen atom, a lower alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, a halogen atom such as chlorine, bromine, fluorine, iodine, or a lower alkyl group substituted with a cyano group. . Next, a method for producing the compound according to the present invention will be described.
但し、以下に記載の方法は一例にすぎず、これに限定さ
れるものではなく、当然、他の化学的類似方法によつて
も製造出来るものである。製造方法 １反応式中、Ｒｌ
，Ｒ２及びＸは前記と同じ意味を有し、Ｒ３は低級アル
キル基を表わす。However, the method described below is only an example, and the invention is not limited thereto. Naturally, it can also be produced by other chemically similar methods. Manufacturing method 1 In the reaction formula, Rl
, R2 and X have the same meanings as above, and R3 represents a lower alkyl group.
当該方法はジメチルホルムアミド、テトラヒドロフラン
、ジオキサン、ジグリム、ベンゼン、トルエン、キシレ
ン等の有機溶媒中、一般式（）で表わされる化合物１モ
ルに対して一般式（１）で表わされる化合物を２〜５モ
ル使用、還流下２〜３時間反応させればすみやかに進行
する。又、一般式（ｌ）で表わされる反応試薬を過剰モ
ル使用、無溶媒下に反応させてもよい。製造方法 ２
反応式中、Ｒｌ，Ｒ２及びＸは前記と同じ意味を有する
。The method involves adding 2 to 5 mol of the compound represented by general formula (1) per 1 mol of the compound represented by general formula () in an organic solvent such as dimethylformamide, tetrahydrofuran, dioxane, diglyme, benzene, toluene, or xylene. When used, the reaction proceeds quickly by allowing the reaction to proceed under reflux for 2 to 3 hours. Further, the reaction reagent represented by the general formula (l) may be used in an excess molar amount and the reaction may be carried out without a solvent. Manufacturing method 2 In the reaction formula, Rl, R2 and X have the same meanings as above.
当該方法はテトラヒドロフラン、クロロホルム、ベンゼ
ン、トルエン、キシレン等の反応に関与しない有機溶媒
中、一般式（）で表わされる化合物１モルに対して一般
式（ＩＶ）で表わされる化合物又はその反応性誘導体を
１〜３モル使用し、還流下反応させればすみやかに進行
する。又一般式（ＩＶ）で表わされる化合物を過剰モル
使用し無溶媒下に反応させてもよい。更に、一般式（Ｉ
Ｖ）で表わされる化合物が固体の場合は溶融下に反応さ
せればよい。製造方法 ３
反応式中、Ｒ１及びＲ２は前記と同じ意味を有するが、
Ｘはこの方法に限りカルボニル基のみの意味を有する。The method involves adding a compound represented by the general formula (IV) or a reactive derivative thereof to 1 mole of the compound represented by the general formula () in an organic solvent that does not participate in the reaction, such as tetrahydrofuran, chloroform, benzene, toluene, or xylene. If 1 to 3 moles are used and the reaction is carried out under reflux, the reaction proceeds quickly. Alternatively, the compound represented by the general formula (IV) may be used in an excess molar amount and the reaction may be carried out without a solvent. Furthermore, the general formula (I
When the compound represented by V) is a solid, the reaction may be carried out in a molten state. Production method 3 In the reaction formula, R1 and R2 have the same meanings as above,
X has the meaning only of a carbonyl group only in this method.
当該方法は前記一般式（で表わされる化合物を各種の酸
化剤（例えば過マンガン酸塩、クロム酸塩、重クロム酸
塩、二酸化セレン又は酢酸第二水銀等）で酸化すること
によつて行なわれる。反応温度は特に限定されず室温か
ら溶媒の沸点まであり、溶媒としてはベンゼン、トルエ
ン、テトラヒドロフラン、アセトン、エタノール、酢酸
等の不活性溶媒から適宜選択することが出来る。製造方
法 ４反応式中、Ｚはハロゲン原子、メルカプト基、低
級アルコキシ基又は低級アルキルチオ基を、Ｘ，Ｒｌ及
びＲ２は前記と同じ意味を有する。The method is carried out by oxidizing the compound represented by the general formula () with various oxidizing agents (e.g. permanganate, chromate, dichromate, selenium dioxide or mercuric acetate). The reaction temperature is not particularly limited and ranges from room temperature to the boiling point of the solvent, and the solvent can be appropriately selected from inert solvents such as benzene, toluene, tetrahydrofuran, acetone, ethanol, and acetic acid.Production method In the 4 reaction formulas, Z represents a halogen atom, a mercapto group, a lower alkoxy group or a lower alkylthio group, and X, Rl and R2 have the same meanings as above.
当該方法は一般式（Ｖｌ）で表わされる化合物に一般式
（４）で表わされるアシルヒドラジン類を反応させ、一
挙に目的化合Ｆｊｆ！！ｊｌ）又は中間体として一般式
（４）で表わされるアシルヒドラジノ誘導体とし、更に
脱水閉環して化合物（１）にする方法である。本反応は
メタノール、エタノール、テトラヒドロフラン、ジメチ
ルホルムアミド等の有機溶媒中、化合撫ＶＯｌモルに対
して化合物（４）を２〜５モル程度使用する。本反応は
室温でも十分進行するが、必要に応じて加温又は加熱下
に行なつてもよい。かくして得られた中間体（４）の目
的化合物（１）への閉環反応は通常加熱することによつ
て容易に行なわれる。例えば無溶媒下にその物質の融点
又は融点より１０〜２０℃高い温度で加熱すると目的を
達することが出来るし、又高沸点溶媒中（例えば、トル
エン、キシレン、ピリジン、ジメチルホルムアミド、テ
トラリン等）中、その溶媒の沸点又は沸点付近で加熱す
ると反応は進行する。又本反応は通常使用される脱水剤
（例えば、オキシ塩化燐、五酸化燐、ポリリン酸等）で
処理しても進行する。前記製造方法１，２，３及び４で
得られた反応生成物は減圧下に溶媒又は過剰の反応試薬
を留去し残渣に水を加え、得られた結晶をメタノール、
エタノール、エーテル、酢酸エステル等の有機溶媒より
再結晶するか又はカラムクロマト法で分離精製すること
によつて本発明の化合物の純品を得ることが出来る。In this method, a compound represented by general formula (Vl) is reacted with an acylhydrazine represented by general formula (4), and the target compound Fjf! ! jl) or an acylhydrazino derivative represented by general formula (4) as an intermediate, and further dehydration and ring closure to form compound (1). In this reaction, about 2 to 5 moles of compound (4) are used per mole of VOl of the compound in an organic solvent such as methanol, ethanol, tetrahydrofuran, dimethylformamide, etc. Although this reaction proceeds satisfactorily at room temperature, it may be carried out with or under heating if necessary. The ring-closing reaction of the thus obtained intermediate (4) to the target compound (1) is usually easily carried out by heating. For example, the purpose can be achieved by heating at the melting point of the substance in the absence of a solvent or at a temperature 10 to 20°C higher than the melting point, or in a high boiling point solvent (for example, toluene, xylene, pyridine, dimethylformamide, tetralin, etc.). , the reaction proceeds when heated at or near the boiling point of the solvent. This reaction also proceeds even when treated with a commonly used dehydrating agent (for example, phosphorus oxychloride, phosphorus pentoxide, polyphosphoric acid, etc.). The reaction products obtained in Production Methods 1, 2, 3, and 4 are distilled off under reduced pressure to remove the solvent or excess reaction reagent, water is added to the residue, and the resulting crystals are dissolved in methanol,
A pure product of the compound of the present invention can be obtained by recrystallizing it from an organic solvent such as ethanol, ether, or acetate, or by separating and purifying it by column chromatography.
さて、ここで前記各製造方法における出発物質について
説明する。Now, the starting materials in each of the above manufacturing methods will be explained.
製造方法１及び２の出発物質である一般式（）で表わさ
れる化合物は、１一置換一４−オキソ一１，２，３，４
−テトラヒドロピリド〔２，３−ｄ〕ピリミジン誘導体
又は１一置換−２ーオキソ一４−チオ−１，２，３，４
−テトラヒドロピリド〔２，３−ｄ〕ピリミジン誘導体
にオキシ塩化燐又は五塩化燐を反応させ、４−クロル体
とした後、ヒドラジンを反応させることによつて収量よ
く得ることが出来る。又、製造方法３の出発物質である
一般式（で表わされる化合物は、１一置換−３−ヒドラ
ジノ１，２−ジヒドロピリド〔２，３−ｄ〕ピリミジン
誘導体にカルボン酸誘導体又はその反応性誘導体を反応
させることによつて収量よく得られる。The compound represented by the general formula (), which is the starting material for Production Methods 1 and 2, is a 1-substituted 1-4-oxo-1,2,3,4
-tetrahydropyrido[2,3-d]pyrimidine derivative or 1-substituted-2-oxo-4-thio-1,2,3,4
-Tetrahydropyrido[2,3-d]pyrimidine derivatives can be reacted with phosphorus oxychloride or phosphorus pentachloride to form a 4-chloride, and then reacted with hydrazine to obtain a good yield. In addition, the compound represented by the general formula (which is the starting material for Production Method 3) is obtained by adding a carboxylic acid derivative or a reactive derivative thereof to a 1-monosubstituted-3-hydrazino-1,2-dihydropyrido[2,3-d]pyrimidine derivative. It can be obtained in good yield by reaction.
製造方法４の出発物質である一般式（ＶＤで表わされる
化合物は１一置換−４−オキソ一１，２，３，４−テト
ラヒドロピリド〔２，３−ｄ〕ピリミジン誘導体又は１
一置換−２−オキソ一４−チオ−１，２，３，４−テト
ラヒドロピリド〔２，３−ｄ〕ピリミジン誘導体にオキ
シ臭化燐、オキシ塩化燐又は五塩化燐を反応させるか、
ここで得られた４−ハロゲノ体に水硫化ナトリウム、ナ
トリウムアルコラード又はナトリウムアルキルスルフイ
ツドを反応させることによつて収量良く合成できる。以
下実施例により本発明を更に詳細に説明する。The starting material for production method 4, the compound represented by the general formula (VD), is a 1-substituted-4-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine derivative or a 1
Reacting a monosubstituted-2-oxo-4-thio-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine derivative with phosphorus oxybromide, phosphorus oxychloride or phosphorus pentachloride,
It can be synthesized in good yield by reacting the 4-halogen compound obtained here with sodium hydrosulfide, sodium alcoholade, or sodium alkyl sulfide. The present invention will be explained in more detail with reference to Examples below.
実施例 １１−（ｐ−フルオロフエニル）−４−ヒドラ
ジノ一１，２−ジヒドロピリド〔２，３−ｄ〕ピリミジ
ン２．６９とオルトギ酸エチル７．０９の混合物をジメ
チルホルムアミド２０ｍ１中で３時間還流を行なつた。Example 11-(p-Fluorophenyl)-4-hydrazino-1,2-dihydropyrido[2,3-d]pyrimidine A mixture of 2.69% and 7.09% of ethyl orthoformate was refluxed in 20ml of dimethylformamide for 3 hours. I did this.
反応終了後溶媒を減圧下に留去し残渣に水を加えて得ら
れた結晶を淵取しメタノールから再結すると、６−（ｐ
−フルオロフエニノ（ハ）−１，２−ジヒドロピリド〔
２，３−ｄ〕−Ｓ−トリアゾロ〔４，３−ｃ〕ピリミジ
ン２．２９を得た。この物質の融点及び元素分析値は次
の通りであつた。融 点 １９９〜２００値Ｃ
元素分析値 Ｃｌ４ＨｌＯＦＮ５
理論値Ｃ：６２．９２Ｈ：３．７７Ｎ：２６．２０実測
値Ｃ：６２．９５Ｈ：３．７６Ｎ：２６．０５実施例
２１−（ｍ−トリフルオロメチルフエニル）−４ヒドラ
ジノ一２−オキソ一１，２−ジヒドロピリド〔２，３−
ｄ〕ピリミジン３．２ｆ１とオルト酢酸エチル８，０９
の混合物をジメチルホルムアミド２５ｍ１中で３時間還
流を行なつた。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, and the resulting crystals were filtered and reconsolidated from methanol to give 6-(p
-Fluorophenino(c)-1,2-dihydropyride [
2.29 of 2,3-d]-S-triazolo[4,3-c]pyrimidine was obtained. The melting point and elemental analysis values of this substance were as follows. Melting point 199-200 Value C Elemental analysis value Cl4HlOFN5 Theoretical value C: 62.92H: 3.77N: 26.20 Actual value C: 62.95H: 3.76N: 26.05 Example
21-(m-trifluoromethylphenyl)-4hydrazino-2-oxo-1,2-dihydropyrido[2,3-
d] Pyrimidine 3.2f1 and ethyl orthoacetate 8,09
The mixture was refluxed in 25 ml of dimethylformamide for 3 hours.
反応終了後、溶媒を減圧下に留去し、残渣に水を加えて
得た結晶を沢取しメタノールから再結すると、３−メチ
ル−６−（ｍ−トリフルオロメチルフエニル）−５オキ
ソ一５，６−ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリ
アゾロ〔４，３−ｃ〕ピリミジン２．８９を得た。この
物質の融点及び元素分析値は次の通りであつた。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, the resulting crystals were collected and reconstituted from methanol to give 3-methyl-6-(m-trifluoromethylphenyl)-5oxo. 2.89 of 15,6-dihydropyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine was obtained. The melting point and elemental analysis values of this substance were as follows.
融 点 ２９９〜３０２℃
元素分析値 Ｃｌ６ＨｌＯＦ３Ｎ５Ｏ
理論値Ｃ：５５，６５Ｈ：２．９２Ｎ：２０．２８実測
値Ｃ：５５．６８Ｈ：２．８７Ｎ：２０．２１実施例
３１−（ｍ−クロロフエニノ（ハ）−４−ヒドラジノ一
１，２−ジヒドロピリド〔２，３−ｄ〕ピリミジン２．
７ｇ、無水トリフルオロ酢酸５９とテトラヒドロフラン
１５ｍ１の混合物を８０℃で２時間封管反応を行なつた
。Melting point 299-302°C Elemental analysis value Cl6HlOF3N5O Theoretical value C: 55,65H: 2.92N: 20.28 Actual value C: 55.68H: 2.87N: 20.21 Example
31-(m-chloropheno(c)-4-hydrazino-1,2-dihydropyrido[2,3-d]pyrimidine)2.
A mixture of 7g of trifluoroacetic anhydride and 15ml of tetrahydrofuran was reacted in a sealed tube at 80°C for 2 hours.
反応終了後、減圧下に溶媒を留去し残渣に水を加えて得
た結晶を淵取しメタノールから再結すると、３−トリフ
ルオロメチル−６一（ｍ−クロロフエニル）−５，６−
ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４，
３−ｃ〕ピリミジン２．８９を得た。この物質の融点及
び元素分析値は次の通りであつた。After the reaction, the solvent was distilled off under reduced pressure, water was added to the residue, and the resulting crystals were filtered and reconsolidated from methanol to give 3-trifluoromethyl-6-(m-chlorophenyl)-5,6-
dihydropyrido[2,3-d]-S-triazolo[4,
3-c]pyrimidine 2.89 was obtained. The melting point and elemental analysis values of this substance were as follows.
融 点 １６４〜１６６℃
元素分析値 Ｃｌ５Ｈ９ＣｉＦ３Ｎ５
理論値Ｃ：５１．２２Ｈ：２．５８Ｎ：１９．９１実測
値Ｃ：５１．１３Ｈ：２．６８Ｎ：２０．１７実施例
４１−（ｍ−トリフルオロメチルフエニル）−４−ヒド
ラジノ一１，２−ジヒドロピリド〔２，３−ｄ〕ピリミ
ジン３．０９と無水酢酸３．０９の混合物を酢酸２０ｍ
１中で２時間還流を行なつた。Melting point 164-166°C Elemental analysis value Cl5H9CiF3N5 Theoretical value C: 51.22H: 2.58N: 19.91 Actual value C: 51.13H: 2.68N: 20.17 Example
A mixture of 41-(m-trifluoromethylphenyl)-4-hydrazino-1,2-dihydropyrido[2,3-d]pyrimidine (3.09 g) and acetic anhydride (3.09 g.) was added to 20 mL of acetic acid.
Refluxing was carried out in 1 for 2 hours.
反応終了後、減圧下に溶媒を留去し、水を加えて得られ
た結晶を済取しメタノールから再結すると、３−メチル
６−（ｍ−トリフルオロメチルフエニル）−５，６−ジ
ヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４，３
−ｃ〕ピリミジン１．７ｇを得た。この物質の融点及び
元素分析値は次の通りであつた。融 点 １９８〜
２０『Ｃ
元素分析値 Ｃｌ６Ｈｌ２Ｆ３Ｎ５
理論値Ｃ：５８．００Ｈ：３．６５Ｎ：２１，１４実測
値Ｃ：５８．２４Ｈ：３．８０Ｎ：２１．０９実施例
５１−（ｍ−トリフルオロメチルフエニル）−４一ヒド
ラジノ一２−オキソ一１，２−ジヒドロピリド〔２，３
−ｄ〕ピリミジン３９と無水酢酸３９の混合物を酢酸２
０ｍ１中で１時間還流を行なつた。After the reaction is complete, the solvent is distilled off under reduced pressure, water is added, the resulting crystals are collected and reconstituted from methanol, and 3-methyl6-(m-trifluoromethylphenyl)-5,6- Dihydropyrido[2,3-d]-S-triazolo[4,3
-c] 1.7 g of pyrimidine was obtained. The melting point and elemental analysis values of this substance were as follows. Melting point 198~
20'C Elemental analysis value Cl6Hl2F3N5 Theoretical value C: 58.00H: 3.65N: 21,14 Actual value C: 58.24H: 3.80N: 21.09 Example
51-(m-trifluoromethylphenyl)-4-hydrazino-2-oxo-1,2-dihydropyrido [2,3
-d] Mixture of pyrimidine 39 and acetic anhydride 39 with acetic acid 2
Refluxing was carried out in 0 ml for 1 hour.
反応終了後、反応混合物を過剰の水中に混ぜると結晶が
析出した。これを淵取し、メタノールから再結すると３
−メチル−６−（ｍ−トリフルオロメチルフエニル）−
５−オキソ一５，６−ジヒドロピリド〔２，３−ｄ〕−
Ｓ−トリアゾロ〔４，３−ｃ〕ピリミジン２．５ｆ１を
得た。この物質の融点及び元素分析値は次の通りであつ
た。After the reaction was completed, the reaction mixture was mixed into excess water to precipitate crystals. When this is extracted and reconstituted from methanol, 3
-Methyl-6-(m-trifluoromethylphenyl)-
5-oxo-5,6-dihydropyrido[2,3-d]-
S-triazolo[4,3-c]pyrimidine 2.5f1 was obtained. The melting point and elemental analysis values of this substance were as follows.
融 点 ２９９〜３０２℃
元素分析値 Ｃｌ６ＨｌＯＦ３Ｎ５Ｏ
理論値Ｃ：５５．６５Ｈ：２．９２Ｎ：２０．２８実測
値Ｃ：５５．５５Ｈ：２．８９Ｎ：２０．２１実施例
６３−トリフルオロメチル−６−（ｍ−トリフルオロメ
チルフエニル）−５，６−ジヒドロピリド〔２，３−ｄ
〕−Ｓ−トリアゾロ〔４，３−ｃ〕ピリミジン３．９９
と三酸化クロム２９の混合物を酢酸２５Ｗ１１中で２時
間還流を行なつた。Melting point 299-302°C Elemental analysis value Cl6HlOF3N5O Theoretical value C: 55.65H: 2.92N: 20.28 Actual value C: 55.55H: 2.89N: 20.21 Example
63-Trifluoromethyl-6-(m-trifluoromethylphenyl)-5,6-dihydropyrido [2,3-d
]-S-triazolo[4,3-c]pyrimidine 3.99
A mixture of chromium trioxide and chromium trioxide 29 was refluxed for 2 hours in acetic acid 25W11.
反応終了後溶媒を減圧下に留去し、残渣に水を加えて得
られた結晶を淵取し、エーテルから再結すると、３−ト
リフルオロメチル−６−（ｍ−トリフルオロメチルフエ
ニル）−５−オキソ一５，６−ジヒドロピリド〔２，３
−ｄ〕−Ｓ−トリアゾロ〔４，３−ｃ〕ピリミジン３．
０９を得た。この物質の融点及び元素分析値は次の通り
であつた。After the reaction was completed, the solvent was distilled off under reduced pressure, water was added to the residue, the resulting crystals were filtered out, and recrystallized from ether to give 3-trifluoromethyl-6-(m-trifluoromethylphenyl). -5-oxo-5,6-dihydropyrido [2,3
-d]-S-triazolo[4,3-c]pyrimidine3.
I got 09. The melting point and elemental analysis values of this substance were as follows.
融 点 １９３〜１９４℃
元素分析値 Ｃｌ６Ｈ７Ｆ６Ｎ５Ｏ
理論値Ｃ：４８．１３Ｈ：１．７７Ｎ：１７．５４実測
値Ｃ：４７．９６Ｈ：１．９８Ｎ：１７．７１実施例
７３−メチル−６−（ｐ−フルオロフエニル）一５，６
−ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４
，３−ｃ〕ピリミジン２．７ｇと三酸化クロム２．０９
の混合物を酢酸２５ｗＬ１中で９０℃で２時間加熱した
。Melting point 193-194°C Elemental analysis value Cl6H7F6N5O Theoretical value C: 48.13H: 1.77N: 17.54 Actual value C: 47.96H: 1.98N: 17.71 Example
73-Methyl-6-(p-fluorophenyl)-5,6
-dihydropyrido[2,3-d]-S-triazolo[4
, 3-c] 2.7 g of pyrimidine and 2.09 chromium trioxide
The mixture was heated at 90°C for 2 hours in 25wL1 acetic acid.
反応終了後溶媒を減圧下に留去し、水を加えて得られた
結晶を済取しメタノールから再結すると、３−メチル−
６−（ｐ−フルオロフエニル）−５−オキソ一５，６−
ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４，
３−ｃ〕ピリミジン１．４９を得た。この物質の融点及
び元素分析値は次の通りであつた。After the reaction was completed, the solvent was distilled off under reduced pressure, water was added, the resulting crystals were collected, and the crystals were reconstituted from methanol to give 3-methyl-
6-(p-fluorophenyl)-5-oxo-5,6-
dihydropyrido[2,3-d]-S-triazolo[4,
3-c]pyrimidine 1.49 was obtained. The melting point and elemental analysis values of this substance were as follows.
融 点 ２９７〜２９８値Ｃ
元素分析値 Ｃ，５ＨｌＯＦＮ５Ｏ
理論値Ｃ：６１．０２Ｈ：３．４１Ｎ：２３．７２実測
値Ｃ：６０．９６Ｈ：３．２６Ｎ：２３．７７更に実施
例１〜７の力法に準じて、次に示す本発明の化合物を合
成した。Melting point 297-298 value C Elemental analysis value C,5HlOFN5O Theoretical value C: 61.02H: 3.41N: 23.72 Actual value C: 60.96H: 3.26N: 23.77 Furthermore, Examples 1 to 7 The following compounds of the present invention were synthesized according to the force method.
６−（ｍ−トリフルオロメチルフエニル）５，６−ジヒ
ドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４，３−
ｃ〕ピリミジン融点２１２〜２１４℃
３−トリフルオロメチル−６−（ｍ−トリフルオロメチ
ルフエニル）−５，６−ジヒドロピリド〔２，３−ｄ〕
−Ｓ−トリアゾロ〔４，３−ｃ〕ピリミジン融点１６２
〜１６４−Ｃ
３−クロロメチル−６−（ｍ−トリフルオロメチルフエ
ニル）−５，６−ジヒドロピリド〔２，３一ｄ〕−Ｓ−
トリアゾロ〔４，３−ｃ〕ピリミジン融点１３７〜１３
９ロＣ３−シア／メチル−６−（ｍ−トリフルオロメチ
ルフエニル）−５，６−ジヒドロピリド〔２，３ｄ〕−
Ｓ−トリアゾロ〔４，３−ｃ〕ピリミジン融点１４４〜
１４７℃３−メチル−６−フエニル一５，６−ジヒドロ
ピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４，３−ｃ〕
ピリジン融点２０８〜２１１−Ｃ
３−トリフルオロメチル−６−フエニル一５，６−ジヒ
ドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４，３−
ｃ〕ピリミジン融点１６２〜１６５ミＣ
３−メチル−６−（ｐ−フルオロメチルフエニル）−５
，６−ジヒドロピリド〔２，３−ｄ〕−Ｓートリアゾロ
〔４，３−ｃ〕ピリミジン融 点 ２０７〜２０８℃（
分解）
３−クロロメチル−６−（ｍ−クロロフエニル）−５，
６−ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔
４，３−ｃ〕ピリミジン融点１７１〜１７２〕Ｃ
３−シアノメチル−６−（ｍ−クロロフエニル）−５，
６−ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔
４，３−ｃ〕ピリミジン融点１５９〜１６０℃
３−クロロメチル−６−（ｐ−フルオロフエニル）−５
，６−ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ
〔４，３−ｃ〕ピリミジン融点１７６〜１７８℃
３−シアノメチル−６−（ｐ−フルオロフエニル）−５
，６−ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ
〔４，３−ｃ〕ピリミジン融点２４１〜２４３℃
６−（ｍ−トリフルオロメチルフエニル）−５オキソ一
５，６−ジヒドロピリド〔２，３−ｄ〕一Ｓ−トリアゾ
ロ〔４，３−ｃ〕ピリミジン融点２２４〜２２６，Ｃ
３−メチル−６−フエニル一５−オキソ一５，６−ジヒ
ドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４，３−
ｃ〕ピリミジン融点２９８〜３０２℃
３−トリフルオロメチル−６−フエニル一５−オキソ一
５，６−ジヒドロピリド〔２，３−ｄ〕−Ｓートリアゾ
ロ〔４，３−ｃ〕ピリミジン融点２８３〜２８５℃
６−（ｐ−フルオロフエニル）−５−オキソ一５，６−
ジヒドロピリド〔２，３−ｄ〕−Ｓ−トリアゾロ〔４，
３−ｃ〕ピリミジン融点１９９〜２００℃
３−トリフルオロメチル−６−（ｍ−クロロフエニノ（
ハ）−５−オキソ一５，６−ジヒドロピリド〔２，３−
ｄ〕−Ｓ−トリアゾロ〔４，３−ｃ〕ピリミジン融点１
９１〜１９３−Ｃ6-(m-trifluoromethylphenyl)5,6-dihydropyrido[2,3-d]-S-triazolo[4,3-
c] Pyrimidine melting point 212-214°C 3-trifluoromethyl-6-(m-trifluoromethylphenyl)-5,6-dihydropyride [2,3-d]
-S-triazolo[4,3-c]pyrimidine Melting point 162
~164-C 3-chloromethyl-6-(m-trifluoromethylphenyl)-5,6-dihydropyrido[2,31d]-S-
Triazolo[4,3-c]pyrimidine melting point 137-13
9loC3-cya/methyl-6-(m-trifluoromethylphenyl)-5,6-dihydropyrido[2,3d]-
S-triazolo[4,3-c]pyrimidine melting point 144~
147℃3-Methyl-6-phenyl-5,6-dihydropyrido[2,3-d]-S-triazolo[4,3-c]
Pyridine melting point 208-211-C 3-trifluoromethyl-6-phenyl-5,6-dihydropyrido[2,3-d]-S-triazolo[4,3-
c] Pyrimidine melting point 162-165 miC 3-methyl-6-(p-fluoromethylphenyl)-5
,6-dihydropyrido[2,3-d]-S triazolo[4,3-c]pyrimidine Melting point 207-208°C (
decomposition) 3-chloromethyl-6-(m-chlorophenyl)-5,
6-dihydropyrido[2,3-d]-S-triazolo[
4,3-c]pyrimidine melting point 171-172]C 3-cyanomethyl-6-(m-chlorophenyl)-5,
6-dihydropyrido[2,3-d]-S-triazolo[
4,3-c]pyrimidine Melting point 159-160°C 3-chloromethyl-6-(p-fluorophenyl)-5
,6-dihydropyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine Melting point 176-178°C 3-cyanomethyl-6-(p-fluorophenyl)-5
,6-dihydropyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine Melting point 241-243°C 6-(m-trifluoromethylphenyl)-5oxo-5,6-dihydropyrido[2 ,3-d]-S-triazolo[4,3-c]pyrimidine Melting point 224-226, C 3-methyl-6-phenyl-5-oxo-5,6-dihydropyrido[2,3-d]-S- Triazolo [4,3-
c] Pyrimidine Melting point: 298-302°C 3-Trifluoromethyl-6-phenyl-5-oxo-5,6-dihydropyrido[2,3-d]-S triazolo[4,3-c]pyrimidine Melting point: 283-285°C 6-(p-fluorophenyl)-5-oxo-5,6-
dihydropyrido[2,3-d]-S-triazolo[4,
3-c] Pyrimidine Melting point 199-200°C 3-trifluoromethyl-6-(m-chlorofenino(
c) -5-oxo-5,6-dihydropyrido [2,3-
d]-S-triazolo[4,3-c]pyrimidine melting point 1
91-193-C
Claims (1)
ルオロメチル基で置換されたフェニル基を、Ｒ＾２は水
素原子、低級アルキル基又はハロゲン原子、シアノ基で
置換された低級アルキル基を、Ｘはメチレン基又はカル
ボニル基を意味する）で表わされるピリド〔２，３−ｄ
〕−Ｓ−トリアゾロ〔４，３−ｃ〕ピリミジン誘導体。[Claims] 1 General formula▲ Numerical formula, chemical formula, table, etc.▼ (In the formula, R^1 is a phenyl group or a phenyl group substituted with a halogen atom or a trifluoromethyl group, and R^2 is hydrogen pyrido [2,3-d
]-S-triazolo[4,3-c]pyrimidine derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51001316A JPS5924994B2 (en) | 1976-01-05 | 1976-01-05 | Novel pyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51001316A JPS5924994B2 (en) | 1976-01-05 | 1976-01-05 | Novel pyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5285194A JPS5285194A (en) | 1977-07-15 |
| JPS5924994B2 true JPS5924994B2 (en) | 1984-06-13 |
Family
ID=11498083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51001316A Expired JPS5924994B2 (en) | 1976-01-05 | 1976-01-05 | Novel pyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5924994B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61152990A (en) * | 1984-12-26 | 1986-07-11 | Hitachi Ltd | Screw vacuum pump |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2266985A1 (en) * | 2009-06-26 | 2010-12-29 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Tricyclic Pyrimidine Derivatives as Wnt antagonists |
-
1976
- 1976-01-05 JP JP51001316A patent/JPS5924994B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61152990A (en) * | 1984-12-26 | 1986-07-11 | Hitachi Ltd | Screw vacuum pump |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5285194A (en) | 1977-07-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU745579B2 (en) | Bicyclic kinase inhibitors | |
| Sakamoto et al. | Studies on pyrimidine derivatives. XXVIII. Synthesis of pyridopyrimidine derivatives by cross-coupling of halopyrimidines with olefins and acetylenes | |
| HU199472B (en) | Process for producing dihydroimidazo-pyrrolopyridine,-quinoline, -thienopyridine derivatives | |
| Estel et al. | Synthesis of ortho‐substituted aminopyridines. Metalation of pivaloylamino derivatives | |
| JPS5924994B2 (en) | Novel pyrido[2,3-d]-S-triazolo[4,3-c]pyrimidine derivatives | |
| HU186951B (en) | Process for producing substitited thizaolo-bracket-3,2-a-bracket closed-parimidines and pharmaceutical compositions containing them | |
| Tominaga et al. | Reactions of pyridinium or isoquinolinium ketene dithioacetals with aromatic N‐imines and S‐imines | |
| FI73680C (en) | Process for the preparation of therapeutically active 5,11-dihydro-11- [(4-methyl-1-piperazinyl) -acetyl] -6H-pyrido / 2,3-b // 1,4 / benzodiazepin-6-one. | |
| IT8319192A1 (en) | 1,3,4-THIADIAZOLE [3,2-a] SUBSTITUTED PYRIMIDINES AND PROCEDURE FOR THEIR PREPARATION | |
| Bracher | First synthesis of the benzo [f] pyrido [2′, 3′: 3, 4]‐pyrrolo [2, 1‐a][2, 7] naphthyridine ring system | |
| AU615260B2 (en) | 2-substituted carbonylimidazo(4,5-c) quinolines | |
| US5008390A (en) | Compounds for preparing 6-phenyl-2,3-dihydroimidazo[2,1-b]-thiazoles and corresponding thiazines | |
| JPS5827279B2 (en) | Method for producing new naphthyridine derivatives | |
| EP0203787A2 (en) | Process for preparing pyridyl-substituted imidazo[2,1-b]thiazoles and thiazines | |
| US4803279A (en) | 1.4-dihydro-4-pyridyl-substituted imidazo (2,1-b) thiazoles and the corresponding thiazines. | |
| KAKEHI et al. | Preparation of New Nitrogen-Bridged Heterocycles. XXIV.: Syntheses and Reactions of Pyrazolo [1, 5-a] pyridine-2-thiols.(2) | |
| US4347362A (en) | 1-Alkyl-4-amino-3-(3-aminotriazolo)-1,8 naphthyridine-2-ones | |
| JPS5818391A (en) | Substituted thiazolo(3,2-a)pyrimidines and manufacture | |
| FI80460C (en) | NYA 3- ELLER 5- (3-PYRIDYL-1H-3H-PYRROLO / 1,2-C / THIAZOL-7-S-ALKYLTHIOCARBOXIMIDATE, VILKA AER MELLANPRODUKT VID FRAMSTAELLNING AV MOTSVARANDE TERAPEUTISKT ANVAENDBARID 7-KARBOXID) | |
| EP0008610A1 (en) | Furonaphthyridine compounds, process for their preparation and pharmaceutical compositions containing them | |
| JPS60190776A (en) | Thiophenes and their production | |
| US3855232A (en) | Preparation of 1-(lower-alkyl)-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate | |
| JPS6011712B2 (en) | Novel 4H-pyrido[2,3-d][1,3]oxazin-4-one derivative | |
| Tisler et al. | Pyridazines. XXXVII. Pyrimido [1, 2-b] pyridazines | |
| Meng et al. | A general synthesis of furo [3, 2-c][1, 2, 4] triazolo [1, 5-a] azepine and furo [2, 3-f][1, 2, 4] triazolo [1, 5-a] azepine derivatives |