JPH08176111A - N, N'-disubstituted ethylenediamine derivatives and process for producing N, N'-disubstituted imidazolidinone derivatives using them - Google Patents
N, N'-disubstituted ethylenediamine derivatives and process for producing N, N'-disubstituted imidazolidinone derivatives using themInfo
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- JPH08176111A JPH08176111A JP6334956A JP33495694A JPH08176111A JP H08176111 A JPH08176111 A JP H08176111A JP 6334956 A JP6334956 A JP 6334956A JP 33495694 A JP33495694 A JP 33495694A JP H08176111 A JPH08176111 A JP H08176111A
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Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
(57)【要約】
【目的】 Ｎ，Ｎ′−ジ置換エチレンジアミン誘導体、
それらの製造法並びにそれらを用いた医薬品等の原料と
して有用なＮ，Ｎ′−ジ置換イミダゾリジノン誘導体の
製造法の提供。
【構成】 一般式（１）
（式中、Ｘは水素原子又はハロゲン原子を示し、Ｙはメ
チレン基又はカルボニル基を示す）で表されるＮ，Ｎ′
−ジ置換エチレンジアミン誘導体。(57) [Abstract] [Purpose] N, N'-disubstituted ethylenediamine derivatives,
A method for producing them and a method for producing an N, N'-di-substituted imidazolidinone derivative which is useful as a raw material for pharmaceuticals and the like using them. [Structure] General formula (1) (In the formula, X represents a hydrogen atom or a halogen atom, and Y represents a methylene group or a carbonyl group).
A di-substituted ethylenediamine derivative.
Description
【０００１】[0001]
【産業上の利用分野】本発明は、Ｎ，Ｎ′−ジ置換エチ
レンジアミン誘導体、それらの製造法並びにそれらを用
いた医薬品等の原料として有用なＮ，Ｎ′−ジ置換イミ
ダゾリジノン誘導体の製造法に関する。FIELD OF THE INVENTION The present invention relates to an N, N'-disubstituted ethylenediamine derivative, a process for producing the same, and a process for producing the N, N'-disubstituted imidazolidinone derivative useful as a raw material for pharmaceuticals and the like. Concerning the law.
【０００２】[0002]
【従来の技術】本発明に係わるＮ，Ｎ′−ジ置換エチレ
ンジアミン誘導体は、文献未記載の新規化合物である。2. Description of the Related Art The N, N'-disubstituted ethylenediamine derivative according to the present invention is a novel compound not described in the literature.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は、新規
なＮ，Ｎ′−ジ置換エチレンジアミン誘導体並びにそれ
らの製造法を提供することにある。更に本発明化合物
は、従来複雑な工程を経由したり、工業的に危険な試薬
を用いなければ製造できなかった、医薬品等の原料とし
有用なＮ，Ｎ′−ジ置換イミダゾリジノン誘導体の製造
法を改良することを目的とする。SUMMARY OF THE INVENTION It is an object of the present invention to provide novel N, N'-disubstituted ethylenediamine derivatives and processes for their production. Furthermore, the compound of the present invention can be produced through a complicated process or can be produced without using an industrially dangerous reagent, and is useful as a raw material for pharmaceuticals, etc. for producing N, N′-disubstituted imidazolidinone derivatives. The purpose is to improve the law.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、医薬品等
の原料として有用なＮ，Ｎ′−ジ置換イミダゾリジノン
誘導体の製造法に関して鋭意研究を重ねた結果、新規な
Ｎ，Ｎ′−ジ置換エチレンジアミン誘導体を用いること
により、工業的に有利でしかも効率よくＮ，Ｎ′−ジ置
換イミダゾリジノン誘導体が得られることを見出し、本
発明を完成した。Means for Solving the Problems The inventors of the present invention have conducted extensive studies as to a method for producing an N, N′-disubstituted imidazolidinone derivative useful as a raw material for pharmaceuticals and the like, and as a result, novel N, N ′ The present invention has been completed by finding that an N, N'-di-substituted imidazolidinone derivative is industrially advantageous and efficiently obtained by using a -di-substituted ethylenediamine derivative.
【０００５】すなわち本発明は、一般式（１） （式中、Ｘは水素原子又はハロゲン原子を示し、Ｙはメ
チレン基又はカルボニル基を示す）で表されるＮ，Ｎ′
−ジ置換エチレンジアミン誘導体に関する。That is, the present invention is based on the general formula (1) (In the formula, X represents a hydrogen atom or a halogen atom, and Y represents a methylene group or a carbonyl group).
A di-substituted ethylenediamine derivative.
【０００６】一般式（１）で表される化合物は以下の工
程により製造することができる。 （Ａ） 一般式（１）において、Ｙがカルボニル基であ
る化合物、すなわち一般式（１ａ）で表される化合物
は、一般式（２） （式中、Ｘは前記の通り、Ｚはアミノ基の保護基を示
す）で表される化合物と、式（３） で表される３−アミノピリジンを縮合させ、一般式
（４） （式中、Ｘ、Ｚは前記の通り）で表される化合物を得、
次いでアミノ基の保護基を除去することにより製造する
ことができる。The compound represented by the general formula (1) can be produced by the following steps. (A) In the general formula (1), the compound in which Y is a carbonyl group, that is, the compound represented by the general formula (1a) has the general formula (2) (Wherein X represents a protecting group for an amino group as described above) and a compound represented by the formula (3) By condensing 3-aminopyridine represented by the general formula (4) (Wherein X and Z are as described above),
Then, it can be produced by removing the protecting group of the amino group.
【０００７】一般式（２）で表される化合物と一般式
（３）で表される化合物との反応は、例えばジシクロヘ
キシルカルボジイミド（ＤＣＣ）等の縮合剤の存在下又
は非存在下に、例えばジクロロメタン等の反応に関与し
ない溶媒中、−50℃〜室温、好ましくは−10℃〜０℃で
反応させることにより製造することができる。Ｚで表さ
れるアミノ基の保護基は、例えばベンジルオキシカルボ
ニル基等のアルコキシカルボニル基を用いることが好ま
しい。The reaction between the compound represented by the general formula (2) and the compound represented by the general formula (3) is carried out in the presence or absence of a condensing agent such as dicyclohexylcarbodiimide (DCC), for example, dichloromethane. It can be produced by reacting in a solvent that does not participate in the reaction such as -50 ° C to room temperature, preferably -10 ° C to 0 ° C. As the amino-protecting group represented by Z, an alkoxycarbonyl group such as a benzyloxycarbonyl group is preferably used.
【０００８】一般式（４）で表される化合物は、例えば
臭化水素酸−酢酸を用いて、酢酸等の溶媒中、０〜30
℃、好ましくは10℃〜25℃で反応させることにより、一
般式（１ａ）で表される化合物に変換することができ
る。The compound represented by the general formula (4) is prepared by using, for example, hydrobromic acid-acetic acid in a solvent such as acetic acid in an amount of 0 to 30.
The compound represented by the general formula (1a) can be converted by reacting at 0 ° C, preferably 10 ° C to 25 ° C.
【０００９】（Ｂ） 一般式（１）において、Ｙがメチ
レン基である化合物、すなわち一般式（１ｂ）で表され
る化合物は、一般式（１ａ）で表される化合物を還元す
ることにより製造することができる。(B) In the general formula (1), the compound in which Y is a methylene group, that is, the compound represented by the general formula (1b) is produced by reducing the compound represented by the general formula (1a). can do.
【００１０】還元剤としては、例えばリチウムアルミニ
ウムヒドリド、ナトリウム水素化ビス（２−メトキシエ
トキシ）アルミニウム等を用いることができるが、ナト
リウム水素化ビス（２−メトキシエトキシ）アルミニウ
ムのトルエン溶液の使用が好ましい。反応は、例えばテ
トラヒドロフラン、エーテル、トルエン等の不活性溶媒
中、０℃〜溶媒の沸点、好ましくは10℃〜40℃で反応さ
せることにより製造することができる。As the reducing agent, for example, lithium aluminum hydride, sodium bis (2-methoxyethoxy) aluminum hydride or the like can be used, but it is preferable to use a toluene solution of sodium bis (2-methoxyethoxy) aluminum. . The reaction can be carried out by reacting in an inert solvent such as tetrahydrofuran, ether or toluene at 0 ° C to the boiling point of the solvent, preferably 10 ° C to 40 ° C.
【００１１】一般式（１ｂ）で表される化合物は、カル
ボニル化剤で処理することにより、一般式（５） （式中、Ｘは前記の通り）で表されるＮ，Ｎ′−ジ置換
イミダゾリジノン誘導体に変換することができる。The compound represented by the general formula (1b) is treated with a carbonylating agent to give the compound represented by the general formula (5). (Wherein X is as described above) can be converted into an N, N′-di-substituted imidazolidinone derivative.
【００１２】カルボニル化剤としては、例えば、Ｎ，
Ｎ′−カルボニルジイミダゾール、ホスゲンダイマー、
ハロゲノ炭酸アルキル等を用いることができるが、Ｎ，
Ｎ′−カルボニルジイミダゾールの使用が好ましい。反
応は、例えばトルエン等の不活性溶媒中、70℃〜溶媒の
沸点、好ましくは90℃〜 110℃の範囲で実施される。Examples of the carbonylating agent include N,
N'-carbonyldiimidazole, phosgene dimer,
Alkyl halogenocarbonate or the like can be used, but N,
The use of N'-carbonyldiimidazole is preferred. The reaction is carried out in an inert solvent such as toluene at 70 ° C to the boiling point of the solvent, preferably 90 ° C to 110 ° C.
【００１３】[0013]
【実施例】以下に実施例を示して、本発明を更に詳細に
説明するが、本発明はこれら実施例によって何らの制限
を受けるものではない。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
【００１４】（実施例１）Ｎ−ベンジルオキシカルボニ
ル−Ｎ−（４−クロロフェニル）グリシン(295ｇ）をジ
クロロメタン(1.5Ｌ）に溶解し、３−アミノピリジン(8
6.84ｇ）を加えた。この溶液に、氷冷下、ＤＣＣ（190.
37ｇ）をジクロロメタン(380ml）に溶かした溶液を74分
かけて滴下した。７℃で20分間攪拌後、氷浴をはずして
2.5時間攪拌した。有機層を飽和塩化アンモニウム水溶
液(1.5Ｌ）、ＲＯ水(1.5Ｌ）×２、飽和食塩水(1.5Ｌ）
で順次洗浄し、無水硫酸ナトリウムで乾燥後、溶媒を留
去した。残留物をｎ−ヘキサン(1.9Ｌ）に懸濁して 2.5
時間攪拌後、析出晶を濾取、ｎ−ヘキサン（１Ｌ）で洗
浄した。30℃で 2.5時間減圧乾燥し、Ｎ−ベンジルオキ
シカルボニル−Ｎ−（４−クロロフェニル）−Ｎ′−
（３−ピリジル）グリシンアミド(299.8ｇ）を得た。(Example 1) N-benzyloxycarbonyl-N- (4-chlorophenyl) glycine (295 g) was dissolved in dichloromethane (1.5 L), and 3-aminopyridine (8
6.84 g) was added. DCC (190.
A solution of 37 g) in dichloromethane (380 ml) was added dropwise over 74 minutes. After stirring for 20 minutes at 7 ℃, remove the ice bath
Stir for 2.5 hours. The organic layer was saturated ammonium chloride aqueous solution (1.5 L), RO water (1.5 L) x 2, saturated saline solution (1.5 L)
After that, the extract was washed successively with, dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was suspended in n-hexane (1.9 L) to give 2.5.
After stirring for an hour, the precipitated crystals were collected by filtration and washed with n-hexane (1 L). After drying under reduced pressure at 30 ° C for 2.5 hours, N-benzyloxycarbonyl-N- (4-chlorophenyl) -N'-
(3-Pyridyl) glycinamide (299.8 g) was obtained.
【００１５】融点： 106−109 ℃ ＮＭＲ（ＣＤＣｌ3 ：60MHz) δ： 4.3（ｓ、２Ｈ）、
5.15（ｓ、２Ｈ）、7.0 −7.4 （ｍ、10Ｈ）、 7.9−8.
6 （ｍ、３Ｈ）、9.25（ｂｒｓ、１Ｈ）。Melting point: 106-109 ° C. NMR (CDCl 3 : 60 MHz) δ: 4.3 (s, 2H),
5.15 (s, 2H), 7.0-7.4 (m, 10H), 7.9-8.
6 (m, 3H), 9.25 (brs, 1H).
【００１６】（実施例２）30％臭化水素酢酸溶液（1300
ml）に、氷冷下、Ｎ−ベンジルオキシカルボニル−Ｎ−
（４−クロロフェニル）−Ｎ′−（３−ピリジル）グリ
シンアミド(260ｇ）を酢酸(520ml）に溶かした溶液を67
分かけて滴下した。滴下後、室温で１時間攪拌し、氷水
（９Ｌ）に注いだ。イソプロピルエーテル（３Ｌ）で洗
浄し、水槽に25％アンモニア水(1.5Ｌ）を加えてｐＨ
4.0として酢酸エチルで抽出した。有機層を無水硫酸ナ
トリウムで乾燥後、溶媒を留去し、残留物をイソプロピ
ルエーテル(350ml）で洗浄し、酢酸エチルで再結晶し
た。濾液を濃縮後、残留物をエーテルで懸濁洗浄し、Ｎ
−（４−クロロフェニル）−Ｎ′−（３−ピリジル）グ
リシンアミド（43.5ｇ）を得た。(Example 2) 30% hydrobromic acetic acid solution (1300
ml) under ice cooling, N-benzyloxycarbonyl-N-
A solution of (4-chlorophenyl) -N '-(3-pyridyl) glycinamide (260 g) in acetic acid (520 ml) was added to 67
It dripped over minutes. After the dropping, the mixture was stirred at room temperature for 1 hour and poured into ice water (9 L). Wash with isopropyl ether (3 L), add 25% aqueous ammonia (1.5 L) to the water bath and add pH.
Extracted with ethyl acetate as 4.0. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated, the residue was washed with isopropyl ether (350 ml), and recrystallized from ethyl acetate. After the filtrate was concentrated, the residue was suspended and washed with ether, and N
There was obtained-(4-chlorophenyl) -N '-(3-pyridyl) glycinamide (43.5g).
【００１７】融点： 180−182 ℃ ＮＭＲ（ＣＤＣｌ3 ：60MHz) δ：3.92（ｄ、２Ｈ、Ｊ
＝６Hz）、6.15（ｔ、１Ｈ、Ｊ＝６Hz）、 6.5−6.7
（ｍ、２Ｈ）、 7.0−7.4 （ｍ、３Ｈ）、 8.0−8.3
（ｍ、２Ｈ）、 8.7−8.9 （ｍ、１Ｈ）、 10.15（ｂｒ
ｓ、１Ｈ）。Melting point: 180-182 ° C. NMR (CDCl 3 : 60 MHz) δ: 3.92 (d, 2H, J
= 6Hz), 6.15 (t, 1H, J = 6Hz), 6.5-6.7
(M, 2H), 7.0-7.4 (m, 3H), 8.0-8.3
(M, 2H), 8.7-8.9 (m, 1H), 10.15 (br
s, 1H).
【００１８】（実施例３）ナトリウム水素化ビス（２−
メトキシエトキシ）アルミニウム（70％）トルエン溶液
（8.64ｇ）をトルエン（35ml）で希釈した。このトルエ
ン溶液にＮ−（４−クロロフェニル）−Ｎ′−（３−ピ
リジル）グリシンアミド（2.62ｇ）を攪拌下、24〜29℃
で投入し、同温度で３時間攪拌した。反応液を氷水(100
ml）に注加した後、５Ｎ水酸化ナトリウムを加えてセラ
イト濾過した。トルエン層を分液し、水槽はトルエンで
再度抽出して先のトルエン層と合一し、飽和食塩水で洗
浄した。溶媒を減圧留去して黄色粉末状のＮ−（４−ク
ロロフェニル）−Ｎ′−（３−ピリジニル）エチレンジ
アミン（2.12ｇ）を得た。Example 3 Sodium hydride bis (2-
A methoxyethoxy) aluminum (70%) toluene solution (8.64 g) was diluted with toluene (35 ml). N- (4-chlorophenyl) -N '-(3-pyridyl) glycinamide (2.62 g) was stirred in this toluene solution at 24 to 29 ° C.
And the mixture was stirred at the same temperature for 3 hours. Add the reaction solution to ice water (100
ml), 5N sodium hydroxide was added, and the mixture was filtered through Celite. The toluene layer was separated, and the water tank was extracted again with toluene, combined with the previous toluene layer, and washed with saturated saline. The solvent was distilled off under reduced pressure to obtain N- (4-chlorophenyl) -N '-(3-pyridinyl) ethylenediamine (2.12 g) as a yellow powder.
【００１９】融点：95−100 ℃ ＮＭＲ（ＣＤＣｌ3 ：60MHz) δ： 3.3（ｂｒ、４
Ｈ）、 4.0（ｂｒ、２Ｈ）、 6.3−6.7 （ｍ、２Ｈ）、
6.9−7.4 （ｍ、４Ｈ）、 7.8−8.2 （ｍ、２Ｈ）。Melting point: 95-100 ° C. NMR (CDCl 3 : 60 MHz) δ: 3.3 (br, 4
H), 4.0 (br, 2H), 6.3-6.7 (m, 2H),
6.9-7.4 (m, 4H), 7.8-8.2 (m, 2H).
【００２０】（実施例４）Ｎ−（４−クロロフェニル）
−Ｎ′−（３−ピリジニル）エチレンジアミン（1.0
ｇ）、Ｎ，Ｎ′−カルボニルジイミダゾール（0.84ｇ）
をトルエン（2.0ml)に投入し、 100〜107 ℃で５時間攪
拌した。反応液を冷却した後、エタノール（15ml）を加
えて加熱攪拌した。冷却し、析出晶を濾取して３−（４
−クロロフェニル）−１−（３−ピリジニル）−２−イ
ミダゾリジノン（0.90ｇ）を得た。(Example 4) N- (4-chlorophenyl)
-N '-(3-pyridinyl) ethylenediamine (1.0
g), N, N'-carbonyldiimidazole (0.84 g)
Was added to toluene (2.0 ml), and the mixture was stirred at 100 to 107 ° C. for 5 hours. After cooling the reaction mixture, ethanol (15 ml) was added and the mixture was heated with stirring. After cooling, the precipitated crystals were collected by filtration to 3- (4
-Chlorophenyl) -1- (3-pyridinyl) -2-imidazolidinone (0.90 g) was obtained.
【００２１】融点： 162.5−163.5 ℃ ＮＭＲ（ＣＤＣｌ3 −ＣＤ3 ＯＤ：60MHz) δ： 4.0
（ｓ、４Ｈ）、7.23−7.67（ｍ、５Ｈ）、8.02−8.37
（ｍ、２Ｈ）、8.83（ｄ、１Ｈ）。Melting point: 162.5-163.5 ° C. NMR (CDCl 3 -CD 3 OD: 60 MHz) δ: 4.0
(S, 4H), 7.23-7.67 (m, 5H), 8.02-8.37
(M, 2H), 8.83 (d, 1H).
【００２２】[0022]
【発明の効果】本発明によれば、Ｎ，Ｎ′−ジ置換エチ
レンジアミン誘導体を用いることにより、医薬品等の原
料として有用なＮ，Ｎ′−ジ置換イミダゾリジノン誘導
体を工業的に有利でしかも効率よく得ることができる。INDUSTRIAL APPLICABILITY According to the present invention, by using an N, N'-di-substituted ethylenediamine derivative, an N, N'-di-substituted imidazolidinone derivative useful as a raw material for medicines and the like is industrially advantageous and It can be obtained efficiently.
フロントページの続き (72)発明者 相沢 靖浩 長野県岡谷市川岸中２丁目７番６号 (72)発明者 吉田 典敬 長野県岡谷市川岸中２丁目７番６号Front page continued (72) Inventor Yasuhiro Aizawa 2-7-6 Kawagishi, Okaya, Nagano Prefecture (72) Noritaka Yoshida 2-7-6 Kawaganaka, Okaya, Nagano Prefecture
Claims (4)
チレン基又はカルボニル基を示す）で表されるＮ，Ｎ′
−ジ置換エチレンジアミン誘導体。1. The general formula (1) (In the formula, X represents a hydrogen atom or a halogen atom, and Y represents a methylene group or a carbonyl group).
A di-substituted ethylenediamine derivative.
ミノ基の保護基を示す）で表される化合物と、式（３） で表される３−アミノピリジンを縮合させ、一般式
（４） （式中、Ｘ、Ｚは前記の通り）で表される化合物を得、
次いでアミノ基の保護基を除去することを特徴とする、
一般式（１ａ） （式中、Ｘは前記の通り）で表されるＮ，Ｎ′−ジ置換
エチレンジアミン誘導体の製造法。2. The general formula (2) (Wherein, X represents a hydrogen atom or a halogen atom and Z represents an amino-protecting group), and a compound represented by the formula (3) By condensing 3-aminopyridine represented by the general formula (4) (Wherein X and Z are as described above),
Then, the protecting group of the amino group is removed,
General formula (1a) (In the formula, X is as described above) A method for producing an N, N′-disubstituted ethylenediamine derivative.
れる化合物を還元することを特徴とする、一般式（１
ｂ） （式中、Ｘは前記の通り）で表されるＮ，Ｎ′−ジ置換
エチレンジアミン誘導体の製造法。3. The general formula (1a) (Wherein, X represents a hydrogen atom or a halogen atom), and a compound represented by the general formula (1
b) (In the formula, X is as described above) A method for producing an N, N′-disubstituted ethylenediamine derivative.
れる化合物をカルボニル化剤で処理することを特徴とす
る、一般式（５） （式中、Ｘは前記の通り）で表されるＮ，Ｎ′−ジ置換
イミダゾリジノン誘導体の製造法。4. The general formula (1b) A compound represented by the formula (wherein X represents a hydrogen atom or a halogen atom) is treated with a carbonylating agent. (In the formula, X is as described above) A method for producing an N, N′-di-substituted imidazolidinone derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6334956A JPH08176111A (en) | 1994-12-20 | 1994-12-20 | N, N'-disubstituted ethylenediamine derivatives and process for producing N, N'-disubstituted imidazolidinone derivatives using them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6334956A JPH08176111A (en) | 1994-12-20 | 1994-12-20 | N, N'-disubstituted ethylenediamine derivatives and process for producing N, N'-disubstituted imidazolidinone derivatives using them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08176111A true JPH08176111A (en) | 1996-07-09 |
Family
ID=18283118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6334956A Pending JPH08176111A (en) | 1994-12-20 | 1994-12-20 | N, N'-disubstituted ethylenediamine derivatives and process for producing N, N'-disubstituted imidazolidinone derivatives using them |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08176111A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8263635B2 (en) | 2009-06-26 | 2012-09-11 | Novartis Ag | Inhibitors of CYP 17 |
| US9029399B2 (en) | 2011-04-28 | 2015-05-12 | Novartis Ag | 17α-hydroxylase/C17,20-lyase inhibitors |
-
1994
- 1994-12-20 JP JP6334956A patent/JPH08176111A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8263635B2 (en) | 2009-06-26 | 2012-09-11 | Novartis Ag | Inhibitors of CYP 17 |
| JP2012530763A (en) * | 2009-06-26 | 2012-12-06 | ノバルティス アーゲー | 1,3-disubstituted imidazolidin-2-one derivatives as CYP17 inhibitors |
| USRE45173E1 (en) | 2009-06-26 | 2014-09-30 | Novartis Ag | Inhibitors of CYP 17 |
| US9029399B2 (en) | 2011-04-28 | 2015-05-12 | Novartis Ag | 17α-hydroxylase/C17,20-lyase inhibitors |
| US9339501B2 (en) | 2011-04-28 | 2016-05-17 | Novartis Ag | 17a-hydroxylase/C17,20-lyase inhibitors |
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