JPS5962593A - 3-substituted-5,7-dichlorotriazolopyrimidine derivative and its preparation - Google Patents
3-substituted-5,7-dichlorotriazolopyrimidine derivative and its preparationInfo
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- JPS5962593A JPS5962593A JP17117182A JP17117182A JPS5962593A JP S5962593 A JPS5962593 A JP S5962593A JP 17117182 A JP17117182 A JP 17117182A JP 17117182 A JP17117182 A JP 17117182A JP S5962593 A JPS5962593 A JP S5962593A
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Abstract
Description
【発明の詳細な説明】
本発明は新規な３−置換−５，７−ジクロルトリアゾロ
ピリミジン誘導体、更に詳細には、次の−（式中、Ｒは
水酸基を有することのある低級アルキル１１（、ベンジ
ル基又は置換基を有することのあるツーｎニル基を示す
）
で表わさｔしる。３−置換−５，７−シクロルトリアゾ
ロヒリミジン誘導体およびその製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel 3-substituted-5,7-dichlorotriazolopyrimidine derivatives, more specifically, the following - (wherein R is lower alkyl 11 which may have a hydroxyl group) (represents a benzyl group or a two-nyl group that may have a substituent) The present invention relates to a 3-substituted-5,7-cyclotriazolohyrimidine derivative and a method for producing the same.
従来、トリアゾＩ］ピリミジン誘導体としては、８−ア
ザグアニンが抗１ｉｆｆ瘍作用を有することが知られて
いる。然しなから、５，７−ジクロル体については、未
だその合；戊例はなく、従ってその抗腫瘍作用について
は全く検討されていないのが現状であった。Conventionally, as a triazo I]pyrimidine derivative, 8-azaguanine is known to have anti-Iff tumor activity. However, as for 5,7-dichlor, there has been no case yet, and therefore, its antitumor effect has not been investigated at all.
そこで、本発明者らは一連の５．７−ジクロル体を合成
し、そのＩ：ｉｉ： 畦瘍作用を検討した結果、式（１
）で表わされる：う一置換−５，７−シクロルトリアゾ
ロビＩＪ ミジン誘導体が優れた抗）相場作用を有する
ことを見出し、本発明を完成した。Therefore, the present inventors synthesized a series of 5,7-dichlor compounds, and investigated their I:ii: urticaria effect. As a result, the formula (1
The present invention has been completed based on the discovery that a monosubstituted-5,7-cyclotriazolobiIJ midine derivative represented by ) has an excellent anti-competitive effect.
すなわち、本発明の第一の目的は、優れた抗腫瘍作用を
有する新却な３−置換−５，７−ジクロルトリアゾロピ
リミジン誘導体（１）を提供せんとするにある。That is, the first object of the present invention is to provide a novel 3-substituted-5,7-dichlorotriazolopyrimidine derivative (1) having excellent antitumor activity.
また、本発明の他の目的は、新規な３−Ｉを換−５，７
−ジクロルトリアゾロピリミジン誘導体（１）を製造す
る方法を提供せんとするにある。Another object of the present invention is to replace the novel 3-I with -5,7
- It is an object of the present invention to provide a method for producing a dichlorotriazolopyrimidine derivative (1).
本発明の：ウー置換−５．７−シクロルトリアゾロビリ
ミジン誘導体（１）は、ｌ（の種類により次の（１ａ）
及び（Ｉｂ）に大別できる。The woo-substituted-5,7-cyclotriazolopyrimidine derivative (1) of the present invention may be the following (1a) depending on the type of l().
and (Ib).
ｋ
ｈ・
（式中、Ｗは水酸基を有することのある低級アルキル基
又はベンジル基を示す）
−ｅ
）Ｌり
（式中、ｌセは置換基を有することのあるフェニル基を
示す）
本発明の化合物Ｉ ［ａ）は、次式（Ｉ）で表わされる
ピリミジン誘導体を次の一般式（ＩＶ）Ｉｔ’ ＮＨ２
ＱＶ）
１式中、Ｒは前記と同じ）
で表わされるアミン類と反応させて次の一般式（１）（
式中、ｌ（は前記と同じ）
で表わされる化合物となし、次いでこれをジアゾ化して
閉環することにより製造される。〜原料の化合物（１）
は、公知の５−二トロー２．４．６−ドリクロルビリミ
ジン（資）
を塩化第一スズ等の還元剤により還元することにより容
易に製造される。k h (In the formula, W represents a lower alkyl group or a benzyl group that may have a hydroxyl group) -e)L (In the formula, I represents a phenyl group that may have a substituent) The present invention Compound I [a) is a pyrimidine derivative represented by the following formula (I) with the following general formula (IV) It' NH2
QV) In formula 1, R is the same as above) to react with amines represented by the following general formula (1) (
In the formula, l (same as above) is prepared as a compound, and then this is diazotized and ring-closed. ~Raw material compound (1)
is easily produced by reducing the known 5-nitro-2.4.6-dolychloropyrimidine with a reducing agent such as stannous chloride.
アミン類（５）による化合物（１）のアミノ化は、化合
物（ｌｌＩ）１モルに対し、アミン類（閏を１．５〜３
．０モル用い、ジオキサン等の溶媒中４０〜６０℃で２
〜３０時間加温すれば良い。また、アミン類が低沸点の
場合には封管中９０〜１１０℃で行なっても良い。反応
後、例えば溶媒を留去し、水で希釈すれば、化合物（１
）が結晶として得られる。これは更にカラムクロマトグ
ラフィー等で精製しても良い。Amination of compound (1) with amines (5) is carried out using 1 mole of compound (llI),
．． 2 at 40-60°C in a solvent such as dioxane using 0 mol.
It is sufficient to heat it for ~30 hours. Further, when the amine has a low boiling point, the reaction may be carried out in a sealed tube at 90 to 110°C. After the reaction, for example, if the solvent is distilled off and diluted with water, the compound (1
) is obtained as a crystal. This may be further purified by column chromatography or the like.
化合物（Ｉｔ）のジアゾ化による閉環は、亜硝酸ナトリ
ウム−塩酸等の通常のジアゾ化の条件で容易に行なうこ
とができる。すなわら、化合物（ＩＩ）を希塩酸に溶解
し、これに−５〜１０℃で化合物（■）１モルに対し、
亜硝酸ナトリウム１．０〜１．５モルを水に溶解したも
のを滴下し、室温にて１〜３時間攪拌すると目的化合物
（Ｉａ）の結晶が得られる。これン、トルエン、石油ベ
ンジン、石油エーテル、ｎ−ヘキサン等の炭化水素ある
いはエーテル、イソプロピルエーテル等のエーテル類ま
たはこれらの混液が使用される。Ring closure by diazotization of compound (It) can be easily carried out under usual diazotization conditions such as sodium nitrite-hydrochloric acid. That is, compound (II) is dissolved in dilute hydrochloric acid, and in this solution at -5 to 10°C, for 1 mole of compound (■),
A solution of 1.0 to 1.5 moles of sodium nitrite in water is added dropwise and stirred at room temperature for 1 to 3 hours to obtain crystals of the target compound (Ia). Hydrocarbons such as toluene, petroleum benzine, petroleum ether, n-hexane, ethers, ethers such as isopropyl ether, or mixtures thereof are used.
本発明の化合物（（ｂ）は、次の一般式（■Ｈ
Ｒ″Ｉ
（式中、ＩｔＩは前記と同じ）
で表わされるトリアゾロピリミジン誘導体をハロゲン化
試薬と反応させることにより製造される。The compound (b) of the present invention is produced by reacting a triazolopyrimidine derivative represented by the following general formula (■HR''I (in the formula, ItI is the same as above) with a halogenating reagent.
原料の化合物（９）は、下式に従って、化合物ＩＶＩＤ
１モルに尿素６〜９モルを１８０〜２００℃で１〜６
時間加熱することによって製造される。The starting material compound (9) is compound IVID according to the following formula.
6 to 9 moles of urea to 1 mole at 180 to 200℃
Produced by heating for a period of time.
（ＶＩＤ （Ｖ）ハロゲ
ン化試薬としては、オキシ塩化リン、五塩化リン、三塩
化リン等が挙げられる。ノ・ロゲン化反応は、化合物（
Ｖ） １モルに対してオキシ塩化リン４〜８モルと五塩
化リン３０〜５０モルとの混合物を使用し、１〜３時間
還流するのが好ましい。(VID) Examples of halogenating reagents include phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, etc.
V) It is preferable to use a mixture of 4 to 8 mol of phosphorus oxychloride and 30 to 50 mol of phosphorus pentachloride per mol and reflux for 1 to 3 hours.
また、ジメチルアニリン、ジエチルアニリン等のアミン
類を塩基触媒として数モル併用しても良い。Furthermore, several moles of amines such as dimethylaniline and diethylaniline may be used in combination as a base catalyst.
反応後、過剰のハロゲン化試薬を減圧留去し、クロロホ
ルム等の有機溶媒で抽出し、水洗後溶媒を留去すれば目
的化合物（Ｉｂ）が結晶として得られる。この結晶は、
そのまま再結晶するか、あるいはカラムクロマトグラフ
ィーで精製したのち再結晶しても良い。再結晶溶媒とし
ては、ベンゼン、トルエン、石油ベンジン、石油エーテ
ル、ｎ−ヘキサン等の炭化水素あるいはエーテル、イソ
プロピルエーテル等のエーテル類またはこれらの混液が
用いられる。After the reaction, excess halogenating reagent is distilled off under reduced pressure, extracted with an organic solvent such as chloroform, washed with water, and the solvent is distilled off to obtain the target compound (Ib) as crystals. This crystal is
It may be recrystallized as it is, or it may be purified by column chromatography and then recrystallized. As the recrystallization solvent, hydrocarbons such as benzene, toluene, petroleum benzine, petroleum ether, and n-hexane, ethers such as ethers and isopropyl ether, or mixtures thereof are used.
次に斯くして得られる本発明化合物の代表的なものにつ
いて抗腫瘍作用を試験した結果を示す。Next, the results of testing the antitumor activity of representative compounds of the present invention thus obtained are shown.
Ｉ）ｔｃ雄性マウス（５週令）を１群８匹とし、１匹あ
たりＳａｒｃｏｍａ １８０腹水癌細胞５ Ｘ １．０
６個を腹腔内に移植し−Ｃ用いた。被検化合′吻は、ド
表に示す川１■１：を０．５チＣＭ Ｃ含有生理食塩液
に懸濁し、移植後２・１時間後より、１日１回、合計６
回腹腔内に投与した。薬理作用は次式により延命率を求
め評価した。I) TC male mice (5 weeks old), 8 mice per group, Sarcoma 180 ascites cancer cells 5 x 1.0 per mouse
Six pieces were implanted intraperitoneally and used as -C. The test compound's proboscis was prepared by suspending the river shown in Table 1 in physiological saline containing 0.5 CM C, and starting 2.1 hours after transplantation, once a day for a total of 6
It was administered intraperitoneally. Pharmacological effects were evaluated by calculating the survival rate using the following formula.
結果は第１表に示すとおりである。The results are shown in Table 1.
１す、 １・“ 〈ｉ 臼 第１表 （＊）実施例中に表示した。1. Table 1 (*) Displayed in the examples.
１Δ１表から明らかな如く、本発明化合物には」二記の
癌１間胞を移植されたマウスにおいて、延命効果がある
ことが認められた。As is clear from the 1Δ1 table, the compound of the present invention was found to have a survival effect on mice transplanted with the cancer cells described in "2".
次に本発明の実施例を挙げて説明する。Next, examples of the present invention will be described.
実施例１
５−アミノ−２，４，６−ドリクロルビリミジン１．０
？と４０チメチルアミン水溶液１０．ＯＦをジオキサン
４０ｒｎｌに溶解し、封管中１００ ’Ｃで２４時間加
熱攪拌する。次いで溶媒を減圧留去し、水で希釈し、結
晶をｆ取する。四にこれを水、メタノールで洗浄したの
ち風乾すると、５−アミノ−４−メチルアミノ−２，６
−ジクロルピリミジン（化合物番号１）を０．６２ｆｉ
’（収率６４チ）得る。Example 1 5-amino-2,4,6-dolychlorpyrimidine 1.0
? and 40 dimethylamine aqueous solution 10. OF is dissolved in 40 rnl of dioxane and heated and stirred in a sealed tube at 100'C for 24 hours. Then, the solvent was distilled off under reduced pressure, diluted with water, and the crystals were collected. Fourth, this was washed with water and methanol and air-dried to give 5-amino-4-methylamino-2,6
-dichloropyrimidine (compound number 1) at 0.62fi
'(yield: 64 cm).
実施例２
５−アミノ−２，４，６−）ジクロルピリミジンｉ、ｏ
ｙ−とベンジルアミン１．１ｆ！−をジオキサン５０ｍ
１ｌに溶解し、５０℃にて２４時間攪拌する。次いで実
施例１と同様に処理すると５−アミノ−４−ベンジルア
ミノ−２，６−ジクロルピリミジン（化合物番号３）を
１．２８７（収率９５チ）得る。Example 2 5-amino-2,4,6-)dichloropyrimidine i,o
y- and benzylamine 1.1f! - Dioxane 50m
Dissolve in 1 liter and stir at 50°C for 24 hours. Then, treatment was carried out in the same manner as in Example 1 to obtain 1.287 g of 5-amino-4-benzylamino-2,6-dichloropyrimidine (Compound No. 3) (yield: 95 g).
実施例３
実施例１と同様にして５−アミノ−４−ヒドロキシエチ
ルアミノ−２，６−ジクロルピリミジン（化合物番号２
）を得た。Example 3 5-amino-4-hydroxyethylamino-2,6-dichloropyrimidine (compound number 2) was prepared in the same manner as in Example 1.
) was obtained.
実施例１〜３で得た化合物の物性を第２表に示す。Table 2 shows the physical properties of the compounds obtained in Examples 1 to 3.
実施例
５−アミノ−４−メチルアミノル２，６−ジクロルピリ
ミジン（化合物番号１）０．３０Ｐに水１０ｍ１および
２規定ｊＨ酸１．０コ加え、氷冷下水５ ｒｎｌに溶精
したＩ１１工硝酸すトリウム０．１２ ！／□を滴下し
、１５分攪拌する。次いで室温にて２時間攪拌し、析出
する結晶をｄ：Ｉ取し水洗したのち風乾する。次いで、
ベンゼン−ｎ−ヘキサンの混液より再結晶し、無色プリ
ズム晶の５．７−ジクロル−３−メチル−３１−（−１
，２，３−）リアゾロ（４，５−ｄ）ピリミジン（化合
物番号４）を０．２３５Ｍ収率７３チ）イＬする。Example 5 - Amino-4-methylaminol 2,6-dichloropyrimidine (Compound No. 1) To 0.30 P was added 10 ml of water and 1.0 g of 2N JH acid, and dissolved in 5 rnl of water under ice-cooling to give I11 engineered nitric acid. Storium 0.12! /□ dropwise and stirred for 15 minutes. Next, the mixture was stirred at room temperature for 2 hours, and the precipitated crystals were taken out as d:I, washed with water, and then air-dried. Then,
Recrystallization from a mixture of benzene-n-hexane gave colorless prismatic crystals of 5,7-dichloro-3-methyl-31-(-1
,2,3-)riazolo(4,5-d)pyrimidine (Compound No. 4) in 0.235M yield, 73%.
実施例
３−フェニル−３１−（−１，２，３−）リアゾロ〔４
゜５−ｄ〕ピリミジン−５，７Ｉ ４１−１ 、６ Ｈ
）−ジオン２．９０！／−に五塩化リン１２．０ Ｖ−
およびオキシ塩化リン４０ｒｎｌ加え、２時間速流する
。過剰のオキン塩化リンを減圧留去したのち、氷水を加
えクロロホルムで抽出し、これを水洗後無水硫酸ナトリ
ウムで乾燥する。次いでクロロホルムを留去し、ンリ力
ゲルカラムクロマトグラフイー（ベンゼン：クロロホル
ム−１：１）で精製する。史にベンゼン−石油ベンジン
の混液から再結晶し、無色釧状晶の５，７−ジクロル−
３−７二二ルー３１−１−１゜２．３−１−リアゾロ（
４，５−ｄ’）ピリミジン（化合物番号７）を１．４８
５１収率４４チ）得る。Example 3-Phenyl-31-(-1,2,3-)riazolo[4
゜5-d]Pyrimidine-5,7I 41-1 , 6H
) - Zeon 2.90! /- to phosphorus pentachloride 12.0 V-
and 40 rnl of phosphorus oxychloride were added, and the mixture was rapidly flowed for 2 hours. After removing excess oquine phosphorus chloride by distillation under reduced pressure, ice water is added and extracted with chloroform, which is washed with water and dried over anhydrous sodium sulfate. Next, chloroform is distilled off, and the residue is purified by gel column chromatography (benzene:chloroform-1:1). In history, it was recrystallized from a mixture of benzene and petroleum benzene to form colorless cylindrical crystals of 5,7-dichloro-
3-722ru31-1-1゜2.3-1-Riazolo(
4,5-d')pyrimidine (compound no. 7) at 1.48
51 yield 44 h) is obtained.
実施例６
実施例４又は５と同様にして第４表の化合物を得た。尚
表中には実施例４及び５で得た化合物もあわせて記載し
た。Example 6 The compounds shown in Table 4 were obtained in the same manner as in Example 4 or 5. The compounds obtained in Examples 4 and 5 are also listed in the table.
Ｌ）、１子白
千続補正書（自発）
昭和５７年１１月９ 日
１・１ｊ１・’Ｉ’ ｌｉ’ Ｉそ官若杉和夫殿１ 十
イ１１の表小
昭和５７年 特 許 ＋ｐｒ［第１７１１７１ 号
２ グれ明の名称
３−直換−５，７−シクロルトリアゾロピリミジン誘専
体およびその製造法
３ ＋重重をする考
中イ′１との関係 出願人
ｆＬ 所 東京都中央区日本稿浜町２丁目１２番４号
名 ４４． ニスニス製系株式会社
代表者泰道直方
４ 代 Ｊ−１１ｊ 人
自 発
６、 補正の対象
明細書の「発明の詳細な説明」の欄
７、補正の内容
（１） 明細１．中、第１４負、第２表中、化合物番
桝３のＮＲＩＩＲδｐｐｍ ｉｎ ｄ６−ＤＭＳＯとあ
る個で、［７，９０−７，３０（ｂｒｏａｄ、ＩＨ）
、７．２７（ｇ、５Ｈ） 、４．６０（ｄ、２Ｈ） 、
５．３０−４．００ （ｂｒｏａｄ、２Ｈ） Ｊとある
を
ｒ７．９０−７．３０ （ｂｒｏａｄ、ＩＨ） 、７．
２７ （ｓ、５）１） 、４．６０（ｄ、２Ｈ） 、
５．３０−４．００ （ｂｒｏａｄ、２Ｈ） Ｊと訂正
する。L), 1st child Hakusenji amendment (spontaneous) November 9, 1981 1・1j1・'I'li' ISokan Wakasugi Kazuo 1 Table of 11, 1981 Patent +pr [No. 171171 No. 2 Name of Gremei 3 - Directly converted -5,7-cyclotriazolopyrimidine diamine and method for producing the same 3 + Relationship with important consideration A'1 Applicant fL Place Chuo-ku, Tokyo, Japan Karahama-cho 2-12-4 Name 44. Nisnis Seikei Co., Ltd. Representative Nookata Yasumichi 4th J-11j Voluntary action 6, "Detailed explanation of the invention" column 7 of the specification to be amended, Contents of the amendment (1) Specification 1. NRIIRδppm in d6-DMSO of compound number 3 in Table 2, [7,90-7,30 (broad, IH)
, 7.27 (g, 5H) , 4.60 (d, 2H) ,
5.30-4.00 (broad, 2H) J and r7.90-7.30 (broad, IH), 7.
27 (s, 5) 1), 4.60 (d, 2H),
5.30-4.00 (broad, 2H) Correct as J.
（２） 同、第１５頁、第１７行 「４〇−加え、」とあるを 「４０−を加え、」と訂正する。(2) Same, page 15, line 17 It says “40-addition.” Correct it by saying, "Add 40-."
（３） 同、駆１７頁、第３表中、化合物番号７のｍ
ｐｃｏとめる佃で、
ｒ１５８−１６１Ｊとあるを(3) Ibid., p. 17, m of compound number 7 in Table 3
At pco stop Tsukuda, it says r158-161J.
Claims (1)
基、ベンジル基又は置換基を有することのあるフェニル
基を示す） で表わされる３−置換−５，７−シクロルトリアゾロビ
リミジン誘導体。 ２ 次の一般式（１１） （ （式中、Ｉ（′は水酸基を有することのある低級アルキ
ル基又はベンジル基を示す） で表わされる化合物なジアゾ化により閉環することを特
徴とする次の一般式（ｌａ） Ｒ’ （式中、Ｒ′は前記と同じ） で表わされる３−置換−５，７−シクロルトリアゾロピ
リミジン誘導体の製造法。 ３ 次式（Ｉｆ） Ａ で表わされるピリミジン誘導体を、次の一般式（閏＋ｔ
′Ｎｌ １２（ＩＶ） （式中、１（は水酸基を有することのある低級アルキル
基又はベンジル基を示す） で表わされるアミン類と反応させて次の一般式（１）Ｒ
’ （式中、Ｒ′は前記と同じ） で表わされる化合物となし、次いでこれをジアゾ化によ
り閉環することを特徴とする次の一般式ｆｌａ）Ｋ・ （式中、Ｒ′は前記と同じ） で表わされる３−置換−５，７−ジクロルトリアゾロビ
リミジン誘導体の製造法。 ４ 次の一般式（■ １（、ゲ （式中、ＲＶは置換基を有することのあるフェニル基を
示す） で表わされるトリアゾロピリミジン誘導体イｓノ・ロゲ
ン化試薬と反応させることを特徴とする次の一般式（Ｉ
ｂ Ｉ Ａ ｔｖ （式中、Ｒｑは前記と同じ） で表わされる３−置換−５，７−ジクロルトリアゾロピ
リミジン誘導体の製造法。[Scope of Claims] 1 Represented by the following general formula (1) (where 1 represents a lower alkyl group that may have a hydroxyl group, a benzyl group, or a phenyl group that may have a substituent) 3-substituted-5,7-cyclotriazolopyrimidine derivative. Represented by the following general formula (11) (wherein I (' represents a lower alkyl group or benzyl group that may have a hydroxyl group) Production of a 3-substituted-5,7-cyclotriazolopyrimidine derivative represented by the following general formula (la) R' (wherein R' is the same as above), which is characterized by ring closure by diazotization of the compound. The pyrimidine derivative represented by the tertiary formula (If)
'Nl 12(IV) (wherein 1 (represents a lower alkyl group or benzyl group that may have a hydroxyl group)
' (wherein R' is the same as above) and then ring-closed by diazotization. ) A method for producing a 3-substituted-5,7-dichlorotriazolopyrimidine derivative. 4 A triazolopyrimidine derivative represented by the following general formula (■ 1(, GE (in the formula, RV represents a phenyl group that may have a substituent)) is reacted with an isno-rogensing reagent. The following general formula (I
b A method for producing a 3-substituted-5,7-dichlorotriazolopyrimidine derivative represented by IAtv (wherein Rq is the same as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17117182A JPS5962593A (en) | 1982-09-30 | 1982-09-30 | 3-substituted-5,7-dichlorotriazolopyrimidine derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17117182A JPS5962593A (en) | 1982-09-30 | 1982-09-30 | 3-substituted-5,7-dichlorotriazolopyrimidine derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5962593A true JPS5962593A (en) | 1984-04-10 |
| JPH033674B2 JPH033674B2 (en) | 1991-01-21 |
Family
ID=15918308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17117182A Granted JPS5962593A (en) | 1982-09-30 | 1982-09-30 | 3-substituted-5,7-dichlorotriazolopyrimidine derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5962593A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5204353A (en) * | 1987-04-07 | 1993-04-20 | Ciba-Geigy Corporation | 3-benzyl-3H-1,2,3-triazolo[4,5-d]pyrimidines, compositions thereof, and method of treating epilepsy therewith |
| US5359078A (en) * | 1989-05-19 | 1994-10-25 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor compounds |
| US5498620A (en) * | 1989-05-19 | 1996-03-12 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor 1,2,3-triazolo compounds |
| US5880129A (en) * | 1989-05-19 | 1999-03-09 | The United States Of America As Represented By The Department Of Health And Human Services | Methods of inhibiting invasion and metastasis of malignant solid tumors |
| KR100443182B1 (en) * | 1995-10-27 | 2005-04-19 | 바스프 악티엔게젤샤프트 | Process for the preparation of dihaloazulopyrimidines |
-
1982
- 1982-09-30 JP JP17117182A patent/JPS5962593A/en active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5204353A (en) * | 1987-04-07 | 1993-04-20 | Ciba-Geigy Corporation | 3-benzyl-3H-1,2,3-triazolo[4,5-d]pyrimidines, compositions thereof, and method of treating epilepsy therewith |
| US5359078A (en) * | 1989-05-19 | 1994-10-25 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor compounds |
| US5482954A (en) * | 1989-05-19 | 1996-01-09 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor triazole and diazole compounds |
| US5498620A (en) * | 1989-05-19 | 1996-03-12 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor 1,2,3-triazolo compounds |
| US5705514A (en) * | 1989-05-19 | 1998-01-06 | The United States Of America As Represented By The Department Of Health And Human Services | Signal transduction inhibitor compounds |
| US5880129A (en) * | 1989-05-19 | 1999-03-09 | The United States Of America As Represented By The Department Of Health And Human Services | Methods of inhibiting invasion and metastasis of malignant solid tumors |
| KR100443182B1 (en) * | 1995-10-27 | 2005-04-19 | 바스프 악티엔게젤샤프트 | Process for the preparation of dihaloazulopyrimidines |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH033674B2 (en) | 1991-01-21 |
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