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WO2001019815A1 - Nouveaux derives de 2-(2-pyridyl)pyrimidine - Google Patents

Nouveaux derives de 2-(2-pyridyl)pyrimidine Download PDF

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Publication number
WO2001019815A1
WO2001019815A1 PCT/JP2000/006233 JP0006233W WO0119815A1 WO 2001019815 A1 WO2001019815 A1 WO 2001019815A1 JP 0006233 W JP0006233 W JP 0006233W WO 0119815 A1 WO0119815 A1 WO 0119815A1
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WO
WIPO (PCT)
Prior art keywords
group
pyridyl
general formula
alkyl group
phenyl
Prior art date
Application number
PCT/JP2000/006233
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English (en)
Japanese (ja)
Inventor
Taichi Shintou
Original Assignee
Sankio Chemical Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sankio Chemical Co., Ltd. filed Critical Sankio Chemical Co., Ltd.
Priority to AU68785/00A priority Critical patent/AU6878500A/en
Publication of WO2001019815A1 publication Critical patent/WO2001019815A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Definitions

  • the present invention relates to novel 2- (2-pyridyl) pyrimidine derivatives that are useful compounds and intermediates in the fields of pharmaceuticals, agricultural chemicals, ligands, liquid crystals, surfactants, electrophotography and organic electroluminescence. is there. Background technology>
  • bilimidine derivatives have high affinity for endothelin receptors as endothelin antagonists (Japanese Patent Application Laid-Open Nos. 221223/1991, 162449/1991, and 449/1992). — 1 94972, JP-A-11-92458) are disclosed. However, the affinity of the receptor is insufficient, and the creation of an endothelin antagonist having a stronger receptor affinity is eagerly desired.
  • dendrimer-type polynuclear metal complexes contained in dendrimer-type compounds have been studied because strong interaction between the subunits causes new properties to appear as polynuclear metal complexes. Is being actively conducted.
  • One of them is a polynuclear complex using a ruthenium (II) polypyridine complex with photoredox activity as a subunit and a virazine with an electron interaction between skeletons as a bridging ligand (Chemistry and Industry, (7), 890 (1 999), J. Am. Chem. Soc., 120, 5480 (1998)), and its electrochemical properties have been reported.
  • ruthenium (II) polypyridine complex with photoredox activity as a subunit and a virazine with an electron interaction between skeletons as a bridging ligand
  • the object of the present invention is to provide pharmaceuticals, pesticides, ligands, liquid crystals, surfactants.
  • An object of the present invention is to provide a novel 2- (2-viridyl) pyrimidine derivative as a useful substance or intermediate in the field of electroluminescence.
  • R 1 and R 2 may be the same or different and represent a hydrogen atom, an alkyl group, or an aryl group. However, when R 2 is a phenyl group, R 1 represents an alkyl group or a aryl group.
  • R 1 and R 2 may be the same or different and each represent a hydrogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, or an aryl group;
  • R 1 represents a linear or branched alkyl group having 1 to 18 carbon atoms or an aryl group, or the 2- (2-pyridyl) pyrimidine according to the above (1). Derivatives.
  • R 1 and R 2 may be the same or different and each represent a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or an aryl group;
  • R1 represents a linear or branched alkyl group having 1 to 4 carbon atoms or an aryl group, or the 2- (2-pyridyl) pyrimidine according to the above (1).
  • R 1 and R 2 represent a hydrogen atom, a linear or branched alkyl group or aryl group having 1 to 4 carbon atoms, and 11 and 1 ⁇ 2 are the same groups.
  • the 2- (2-pyridyl) pyrimidine derivative according to the above (1) which represents:
  • R 1 and R 2 may be the same or different and represent a hydrogen atom, a methyl group, a phenyl group, a p-tolyl group or a naphthyl group, provided that R 2 is a phenyl group
  • R 1 represents a methyl group, a phenyl group, a p-tolyl group, or a naphthyl group, wherein the 2- (2-pyridyl) pyrimidine derivative according to the above (1).
  • examples of the alkyl group include a linear or branched alkyl group having 1 to 18 carbon atoms, preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, It is an alkyl group having 1 to 4 carbon atoms such as sec-butyl group and tert-butyl group, and more preferably a methyl group which can be induced to carboxylic acid or aldehyde.
  • examples of the aryl group include a phenyl group, a p-tolyl group, and a naphthyl group. Preferred are a phenyl group and a p-tolyl group, and more preferred is a phenyl group.
  • R 1 and R 2 may be the same or different, but preferably, R 1 and R 2 are the same.
  • R 1 and R 2 may be bonded to each other to form a ring.
  • the ring formed is specifically a cycloalkane such as cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc., and preferably cyclohexane.
  • Preferred specific examples (1-1) and (1-18) of the compound represented by formula (I) of the present invention are shown below, but the present invention is not limited thereto.
  • R 1 and R 2 represent the same meaning as described above.
  • amidrazone compound (III) can be obtained by the method described in Japanese Patent Application No. 11-167308 or a method analogous thereto.
  • the 1,2,4-triazine compound represented by the general formula (V) is obtained by reacting the amidrazone compound (III) with the aldehyde or ketone compound represented by the general formula (IV).
  • the 1,2,4-triazine compound (V) is prepared by the method described in Japanese Patent Application No. 11-167308, Tetra hedron Lett., 39, 8817, 8821, 8825 (1998), or a method analogous thereto. Can be obtained at
  • glyoxal aqueous solution examples include glyoxal aqueous solution, glyoxal di (sodium hydrogen sulfite), 1,4-dioxane-2,3-diol which is an equivalent of glyoxal, and glioxal trimeric dihydrate.
  • aqueous glyoxal solutions and 1,4-dioxane-1,2,3-diol, and more preferred are aqueous glyoxal solutions which are inexpensive and easy to obtain and handle.
  • R 1 and R 2 are the same alkyl group or aryl group. Further, R 1 and R 2 may be bonded to each other to form a ring.
  • the alkyl group includes an alkyl group having 1 to 4 carbon atoms
  • the aryl group includes a phenyl group and a 4-methylphenyl group.
  • R 1 and R 2 are different alkyl groups or aryl groups, each of which is represented by the compound represented by the general formula (IV).
  • the alkyl group includes an alkyl group having 1 to 4 carbon atoms
  • the aryl group includes a phenyl group and a 4-methylphenyl group.
  • 2,3-pentanedione 2,3-hexanedione, 2,3-heptanedione, 1-phenyl-1,2-propanedione, and 1-phenyl-1,1,2-butanedione.
  • Ketoaldehyde compound (when one of R 1 and R 2 is a hydrogen atom and the other is an alkyl group)
  • R 1 and R 2 represents a hydrogen atom
  • the other represents an alkyl group or an aryl group represented by the general formula (IV).
  • the alkyl group is an alkyl group having 1 to 4 carbon atoms
  • the aryl group is a phenyl group.
  • methyl glyoxal (pyruvic aldehyde), ethyl glyoxal, propyl glyoxal, isopropyl glyoxal, Butylglyoxal, t-butylglyoxal, isobutylglyoxal, sec-butylglyoxal, phenylglyoxal and the like.
  • Particularly preferred are methylglyoxal and phenylglyoxal.
  • the 1,2,4-triazine compound represented by the general formula (V) is reacted with 2,5-norbornadiene to obtain a 2- (2-pyridyl) pyrimidine derivative represented by the general formula (I) .
  • the 2- (2-pyridyl) pyrimidine derivative represented by the general formula (I) can be obtained by the method described in T et rahedron Lett., 39, 8817, 8821, 8825 (1998), or a method analogous thereto. Can be. ⁇ Example>
  • Example 1 The purity was evaluated by high performance liquid chromatography (abbreviated as HPLC).
  • HPLC high performance liquid chromatography
  • Example 2 The same operation as in Example 1 was carried out except that 2 _ (5,6-dimethyl-2-pyridyl) pyrimidine (A-12) was not added in Application Example 1, and N, N, diphenyl-N, N, diphenyl was added. (3-Methylphenyl) 1-1,4-phenylenediamine was synthesized, and its accelerating effect by reaction time, yield and purity were evaluated by HPLC.
  • a novel compound a 2- (2-pyridyl) pyrimidine derivative, a particularly novel drug, agricultural chemical, ligand, liquid crystal, surfactant having a pyridine and pyrimidine nucleus is provided.
  • the route to acquire luminescence from electrophotography and organic electrification has been expanded, and it is very important for research and development in these research fields, and also for industrial and practical applications.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

L'invention traite de nouveaux dérivés de 2-(2-pyridyl)pyrimidine de la formule générale (I), utilisés comme matériaux ou intermédiaires dans les domaines des médicaments, des produits chimiques agricoles, des ligands, des cristaux liquides, des tensioactifs, de l'électrophotographie et de l'électroluminescence organique. R1 et R2 représentent chacun indépendamment hydrogène, alkyle ou aryle, pour autant que, lorsque R2 est phényle, R1 soit alkyle ou aryle.
PCT/JP2000/006233 1999-09-13 2000-09-12 Nouveaux derives de 2-(2-pyridyl)pyrimidine WO2001019815A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU68785/00A AU6878500A (en) 1999-09-13 2000-09-12 Novel 2-(2-pyridyl)pyrimidine derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/259456 1999-09-13
JP25945699A JP2001081087A (ja) 1999-09-13 1999-09-13 新規な２−（２−ピリジル）ピリミジン誘導体

Publications (1)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1582516A1 (fr) * 2003-01-10 2005-10-05 Idemitsu Kosan Co., Ltd. Derive heterocyclique azote et element electroluminescent organique utilisant ce derive
US8142911B2 (en) 2008-05-16 2012-03-27 Semiconductor Energy Laboratory Co., Ltd. Organic compound, benzoxazole derivative, and light-emitting element, light-emitting device, and electronic device using the benzoxazole derivative
US9105852B2 (en) 2012-02-17 2015-08-11 Semiconductor Energy Laboratory Co., Ltd. Bipyridine compound, light-emitting element material, organic semiconductor material, light-emitting element, display module, lighting module, light-emitting device, lighting device, display device and electronic device
CN104870602A (zh) * 2012-12-31 2015-08-26 第一毛织株式会社 用于有机光电子元件的化合物、包含所述化合物的有机发光元件、以及包含所述有机发光元件的显示装置
JP2016500671A (ja) * 2012-10-05 2016-01-14 ライジェル ファーマシューティカルズ， インコーポレイテッド Ｇｄｆ−８阻害剤
US9825235B2 (en) 2013-07-19 2017-11-21 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, display module, lighting module, light-emitting device, display device, lighting device, and electronic device

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5544775B2 (ja) 2008-07-29 2014-07-09 住友化学株式会社 燐光発光性化合物を含む組成物及び該組成物を用いてなる発光素子

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0259139A2 (fr) * 1986-09-05 1988-03-09 Sumitomo Chemical Company, Limited Dérivés de pyrimidine, leur méthode de préparation et un agent de protection contre les maladies des plantes les contenant comme produits actifs
US4927827A (en) * 1987-05-19 1990-05-22 Sumitomo Chemical Company, Limited Pyridinylpyrimidine derivatives, method for production thereof and a fungicide containing them as the active ingredient
EP0459662A1 (fr) * 1990-05-30 1991-12-04 Zeneca Limited Composés fungicides
GB2250286A (en) * 1990-06-11 1992-06-03 Ici Plc Aromatic zinc compound and their use in the preparation of phenylpyridylpyrimidines

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0259139A2 (fr) * 1986-09-05 1988-03-09 Sumitomo Chemical Company, Limited Dérivés de pyrimidine, leur méthode de préparation et un agent de protection contre les maladies des plantes les contenant comme produits actifs
US4927827A (en) * 1987-05-19 1990-05-22 Sumitomo Chemical Company, Limited Pyridinylpyrimidine derivatives, method for production thereof and a fungicide containing them as the active ingredient
EP0459662A1 (fr) * 1990-05-30 1991-12-04 Zeneca Limited Composés fungicides
GB2250286A (en) * 1990-06-11 1992-06-03 Ici Plc Aromatic zinc compound and their use in the preparation of phenylpyridylpyrimidines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GROEN J.H. ET AL.: "Synthesis, characterization and dynamic behavior of palladium complexes containing the novel terdentate nitrogen ligand 2,6-bis(pyrimidin-2-yl)pyridine", J. CHEM. SOC., DALTON TRANS., no. 1, 1998, pages 113 - 118, SCHEME 1 ETC., XP002934284 *
HOFMANN H.J. ET AL.: "Quantum chemical calculations for the determination of the molecular structure of conjugated compounds. XIX. Lone pairs and molecular structure: the conformation of the O,O'-azabiphenyls", J. PRAKT. CHEM., vol. 327, no. 6, 1985, pages 937 - 944, TABLE 1 ETC., XP002934285 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1582516A1 (fr) * 2003-01-10 2005-10-05 Idemitsu Kosan Co., Ltd. Derive heterocyclique azote et element electroluminescent organique utilisant ce derive
EP1582516A4 (fr) * 2003-01-10 2008-02-20 Idemitsu Kosan Co Derive heterocyclique azote et element electroluminescent organique utilisant ce derive
US7867629B2 (en) 2003-01-10 2011-01-11 Idemitsu Kosan Co., Ltd. Nitrogenous heterocyclic derivative and organic electroluminescent element employing the same
KR101064077B1 (ko) 2003-01-10 2011-09-08 이데미쓰 고산 가부시키가이샤 질소-함유 헤테로환 유도체 및 이를 이용한 유기 전기발광소자
US8142911B2 (en) 2008-05-16 2012-03-27 Semiconductor Energy Laboratory Co., Ltd. Organic compound, benzoxazole derivative, and light-emitting element, light-emitting device, and electronic device using the benzoxazole derivative
US8450485B2 (en) 2008-05-16 2013-05-28 Semiconductor Energy Laboratory Co., Ltd. Organic compound, benzoxazole derivative, and light-emitting element, light-emitting device, and electronic device using benzoxazole derivative
US9209408B2 (en) 2008-05-16 2015-12-08 Semiconductor Energy Laboratory Co., Ltd. Organic compound, benzoxazole derivative, and light-emitting element, light-emitting device, and electronic device using the benzoxazole derivative
US9105852B2 (en) 2012-02-17 2015-08-11 Semiconductor Energy Laboratory Co., Ltd. Bipyridine compound, light-emitting element material, organic semiconductor material, light-emitting element, display module, lighting module, light-emitting device, lighting device, display device and electronic device
JP2016500671A (ja) * 2012-10-05 2016-01-14 ライジェル ファーマシューティカルズ， インコーポレイテッド Ｇｄｆ−８阻害剤
CN104870602A (zh) * 2012-12-31 2015-08-26 第一毛织株式会社 用于有机光电子元件的化合物、包含所述化合物的有机发光元件、以及包含所述有机发光元件的显示装置
US9825235B2 (en) 2013-07-19 2017-11-21 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, display module, lighting module, light-emitting device, display device, lighting device, and electronic device

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JP2001081087A (ja) 2001-03-27
AU6878500A (en) 2001-04-17

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