WO1993008167A1 - Nouveau derive heterocyclique et bactericide agrohorticole le renfermant - Google Patents

Nouveau derive heterocyclique et bactericide agrohorticole le renfermant Download PDF

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Publication number
WO1993008167A1
WO1993008167A1 PCT/JP1992/001384 JP9201384W WO9308167A1 WO 1993008167 A1 WO1993008167 A1 WO 1993008167A1 JP 9201384 W JP9201384 W JP 9201384W WO 9308167 A1 WO9308167 A1 WO 9308167A1
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Prior art keywords
group
substituted
phenyl
optionally substituted
formula
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PCT/JP1992/001384
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English (en)
Japanese (ja)
Inventor
Nobuhiro Umeda
Kenji Saito
Hiroyasu Hosokawa
Sho Hashimoto
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Nippon Soda Co., Ltd.
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Publication of WO1993008167A1 publication Critical patent/WO1993008167A1/fr

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    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a novel heterocyclic derivative and a fungicide for agricultural and horticultural use.
  • An object of the present invention is to provide a novel compound which can be advantageously synthesized industrially and which can be used as a fungicide for agricultural and horticultural use which is effective and secure and can be used safely.
  • the present invention has the general formula (I)
  • m is an integer of 1 to 4
  • R 1 is the same or different and is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group, a lower haloalkyl group, a lower alkoxycarbonyl group, a nitro group, a mono- or di-optionally substituted force be Rubamoiru group or a halogen atom lower alkyl
  • Nr 3 is a lower alkyl group, may be substituted A phenyl group, a lower alkoxy group, a lower alkylamino group, a hydroxy group, a phenylamino group and a lower alkoxycarbonylamino group which may be substituted.
  • R 4 represents a hydrogen atom or a lower alkoxycarbonyl group.
  • R 2 represents a hydrogen atom
  • S (0) Strukturr 5 (r 5 is a lower alkyl group which may be substituted, n represents 0, 1 or 2), a lower alkoxy group, a lower alkylsulfonylamino group, or a substituted
  • R 3 represents a hydrogen atom, a phenylsulfonylamino group, a cyano group, a halogen atom, a hydroxy group, a morpholino group, or an amino group optionally substituted with phenylalkyl or lower alkyl which may be substituted;
  • r 3 represents a phenyl group which may be substituted or a phenylamino group which may be substituted
  • substituents include a halogen atom, an alkyl group, an alkoxy group, an alkylamino group, an alkylthio group, a cyano group, and a nitro group.
  • R 5 may be substituted, and when it represents a lower alkyl group, examples of the substituent include a halogen atom, an alkoxy group, an alkylthio group, an alkylamino group, a phenyl group, an alkoxycarbonyl group, and a substituent. Power such as canolebamoinole group.
  • examples of the substituent include a halogen atom, an alkyl group, an alkoxy group, an alkylamino group, an alkylthio group, a nitro group, a cyano group, and a substituent. And a carbamoyl group which may be used.
  • R 3 is a benzoyl group which may be substituted, a phenyl group which may be substituted, a phenyl group which may be substituted, a phenyl group which may be substituted, an alkyl substituted by a phenyl which may be substituted.
  • Examples of the type of the substituent include a halogen atom, an alkyl group, an alkoxy group, an alkylamino group, an alkylthio group, a nitro group, and a substituted rubamoyl group.
  • heterocyclic ring represents an amino group which may be substituted with alkyl substituted with, thiophene, furan, imidazole, thiazol, oxazole, pyrazole, pyridine, pyrimidine, virazine, pyrrolidine, piperidine, piperazine
  • substituent include halogen atoms, alkyl groups, alkoxy groups, alkylthio groups, alkylamino groups, nitro groups, carbamoyl groups which may be substituted, and the like.
  • 5 is a lower alkyl group, a cycloalkyl group, a lower alkoxyalkyl group, an optionally substituted phenyl group, an optionally substituted N, S, or a 5- to 6-membered hetero ring containing 1 or 2 N, S, 0 (But bonded by an atom), an alkyl group substituted with an optionally substituted phenyl, an alkyl group substituted with an optionally substituted phenyl, and an alkyl group substituted with an optionally substituted pyridyl.
  • R 1 m has the same meaning as described above.
  • [— ⁇ ] can be obtained by reacting mn with an ammonium salt such as ammonium diacid in a solvent such as drip acid at a reaction temperature of 10 to 10 ° C.
  • R 6 represents a lower alkoxycarbonyl group
  • R 1 and m have the same meaning as described above.
  • Examples of the solvent include alcohols such as methanol, ethanol and n-butanol, Ethers such as dioxane; aromatic hydrocarbons such as benzene and toluene; pyridine; DMF;
  • Examples of the base include sodium methoxide, potassium metal butoxide and other metal alkoxides, organic bases such as triethylamine, N, N-dimethylaniline, pyridine and DBU, metal hydrides such as sodium hydride, and the like.
  • Inorganic bases such as carbonated lime, sodium hydroxide, and silver carbonate are exemplified.
  • R 7 is a lower alkoxy group, a cyano group, a halogen atom, a hydroxy group, a morpholino group, or an amino which may be substituted with a phenylalkyl or a lower alkyl which may be substituted.
  • R 1 , m, and n have the same meaning as described above.
  • [1′-4] can be obtained by reacting [ ⁇ 1] with an oxidizing agent such as metachloroperbenzoic acid and hydrogen peroxide in a solvent such as chloroform and sulfonic acid.
  • an oxidizing agent such as metachloroperbenzoic acid and hydrogen peroxide
  • a solvent such as chloroform and sulfonic acid.
  • [I'-5] can be obtained by reacting [I'1-1] with a reducing agent such as sodium borohydride in a solvent such as methanol or ethanol.
  • [I'16] can be obtained by reacting [ ⁇ 4] with a nucleophile in a solvent in the presence of a base.
  • R 8 is a hydrogen atom, a lower alkoxy group, a lower alkyl group, a cycloalkyl group, a lower alkoxyalkyl group, a lower alkylthio group, a phenyl group which may be substituted.
  • R 8 is a hydrogen atom, a lower alkoxy group, a lower alkyl group, a cycloalkyl group, a lower alkoxyalkyl group, a lower alkylthio group, a phenyl group which may be substituted.
  • R represents an amino group which may be substituted with phenyl, lower alkoxy or lower alkyl which may be substituted
  • R fl represents a lower alkyl group or a phenyl group which may be substituted
  • R 1 and m are as defined above. Indicates the same meaning.
  • [I ′ — 7] is a reaction of [ ⁇ ] and [Cor] in a solvent in the presence of a base at a reaction temperature of 10 It is obtained by reacting at 1010 ° C.
  • the solvent examples include water, alcohols such as methanol, ethanol and n-butanol, ethers such as dioxane, aromatic hydrocarbons such as benzene and toluene, pyridine, DMF, and DMS0.
  • Bases include sodium metal alkoxides such as sodium methoxide and potassium t-butoxide; organic bases such as triethylamine, N, N-dimethylaniline, pyridine and DBU; metal hydrides such as sodium hydride; And inorganic bases such as sodium hydroxide.
  • [ ⁇ -8] can be obtained by reacting [ ⁇ -7] with a reducing agent such as sodium borohydride in a solvent such as methanol or ethanol.
  • [1 'single 9] is [1' -7] and the R e S0 2 NH 2, DMF , in a solvent such as DMS 0, the reaction using a metal hydride such as hydride Natoriumu as base temperature 10-150 It is obtained by reacting at ° C.
  • R 11 represents an optionally substituted phenyl group, an optionally substituted phenyl group or an optionally substituted pyridyl group
  • R 1 , m, and R 2 each represent Has the same meaning as
  • [— 12] is [1'-11] (synthesized under the same conditions as when [ ⁇ – 7] is produced using [ ⁇ ] as a raw material).
  • Ethers such as dioxane and alcohols such as ethanol. It is obtained by heating to reflux for 1 to 24 hours with selenium dioxide in a solvent of benzene, water and mixtures thereof. Further, it can also be obtained by using an oxidizing agent such as chromic anhydride and manganese dioxide described in ACS Monograph 186 "Oxidations in Organic Chemistry 1990, 103-104.”
  • R 1 , m and R 8 have the same meanings as described above.
  • the compound of the formula [XII] is known or can be synthesized by a conventional method (for example, Tetrahedron, 42 (12), 3029-96 (1986)).
  • the compound of the formula [1′-1 9] can be obtained by reacting under the same conditions as in the production of the compound of the [1′-1 7]. 8
  • the compound of [1'-11] is heated in a solvent such as DMF, DMSO, or the like, or without solvent, with the compound of CI'10] and N, N-dimethylformamide dimethyl acetal, and then subjected to silica gel column chromatography. It is obtained by purification.
  • the compound of the formula (xm) represents an active methylene compound, and R 12 and R 13 are the same or different and each represents a carbamoyl group which may be mono- or di-substituted by a cyano group, an alkoxycarbonyl group, or a lower alkyl group.
  • the compound of the formula [1′—13] can be synthesized by a conventional method (Liebigs Ann. Chen 1984, 618-21).
  • the compound of the formula ⁇ represents a primary amine, hydrazine, hydroxyamine or alkoxyamine, and R 14 is a lower alkyl group, an optionally substituted phenyl group, a lower alkoxy group, a lower alkylamino group, a hydroxy group, A phenylamino group and a lower alkoxycarbonylamino group.
  • the compound [114] can be obtained by reacting a solvent in a solvent in the presence of an acid at a reaction temperature of 10 to 150 ° C.
  • the solvent examples include alcohols such as methanol, ethanol and n-butanol, ethers such as dioxane, aromatic hydrocarbons such as benzene and toluene, halogenated carbons such as dichloromethane, chloroform, and 1,2-dichloroethane. Hydrogens, DMF, DMSO and the like.
  • the acid examples include an inorganic acid such as hydrochloric acid and sulfuric acid, an organic acid such as oxalic acid and p-toluenesulfonic acid, and a Lewis acid such as boron trifluoride etherate.
  • Examples of the solvent include water and halogenated hydrocarbons such as dichloromethane.
  • Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid.
  • the desired product can be obtained by performing ordinary post-treatment.
  • the structure of the compound of the present invention was determined from IR, NMR, MASS and the like. BEST MODE FOR CARRYING OUT THE INVENTION
  • the chloroform layer was washed with water (5 Om 1 X 2) and dried over anhydrous magnesium sulfate, and chloroform was distilled off under reduced pressure.
  • the SiE solution was poured into water (200 ml), extracted with black-mouthed form (3 Oml x 3), the mouth-shaped form layer was washed with water (5 Oml X2), dried over anhydrous magnesium sulfate, and then left on the mouth under ffi. I left.
  • the residue was purified by column chromatography, and 0.55 g (m 155-6 ° C) of the 7-force rubamoinole form and 0.45 g (mp l 69- °) obtained.
  • the mixture was washed with a 1 N hydrochloric acid, a 1 N aqueous sodium hydroxide solution and then with a saturated saline solution, and dried over anhydrous magnesium sulfate.
  • the solvent was distilled off, and the resulting & ⁇ product was purified by silica gel column chromatography (eluent, glo-mouth form) to obtain the desired product (0.5 & 6 g, mp 15 3-6 ° C).
  • the compound of the present invention has excellent bactericidal activity against a wide variety of fungi, various kinds of diseases that occur when agricultural and horticultural crops including flowers, grasses, grasses, and pastures are separated, especially powdery mildew Can be used to control downy mildew.
  • powdery mildew of cucumber (Spha er 0 the c_a fu 1 iginea), powdery mildew of tomato (E rysipecico racea rum.), Powdery mildew of strawberry (Sphae ro the ca humu 1i), and tobacco Powdery mildew (E rysipheci cho racear um), Rinko's picky's disease CP odosphaera I euco tri cha), Oyster's powdery mildew (P hy 1 1 actinia kaki co la), Budow's picky vine (Uncinu) 1 an eca to r), downy mildew (P 1 as mo para viti co la), powdery mildew of pear CPhyl l ac t in iapyr)), powdery mildew of barley CErys iphe grami nisf.
  • fungicides such as Sphae ro th eca iu ligi nea, which are resistant to benzimidazole fungicides (eg, thiophanate mel, benomyl, carbendazim), and ergosterol biosynthesis inhibiting fungicides (eg,
  • the compounds of the present invention can be used against the fungus powdery mildew (Sha er 0t_t_he c_a fu 1 igi n_e a), which has reduced susceptibility to triadimefon and triflumizol, as well as the susceptible bacteria of these bacteria. It is valid.
  • the compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater objects such as ship bottoms and fishing nets.
  • the thus-obtained compound of the present invention When the thus-obtained compound of the present invention is actually applied, no other component is added. It can be used in pure form or in the form of general pesticides for pesticide use, i.e., in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, etc. it can. When a solid agent is used as an additive or carrier, it is possible to use soy flour, wheat flour and other vegetable powders, diatomaceous earth, limestone, gypsum, talc, pyrophyllite, clay, mineral oil, vegetable oil, etc. Mineral fine powder is used.
  • liquid dosage forms use kerosene, mineral oil, petroleum, solvent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, mineral oil, vegetable oil, ⁇ , etc. Used as a solvent. Surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.
  • the wettable powders, emulsions and suspensions thus obtained are diluted with water to a predetermined concentration and used as suspensions or emulsions. .
  • the above mixture is mixed and wet-milled until the knee is less than 1 micron to obtain a 10% active ingredient suspension.
  • the compound of the present invention is sufficiently effective alone, but it is one or two of various fungicides and insecticides and acaricides against inadequate or weak diseases or harmful insects and mites. It can be used in combination with the above.
  • fungicides insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.
  • Gibberellins (eg Gibberellin A 3 , Gibberellin A 4 , Gibberellin A 7 ) I AA, NAA.
  • Test Examples show that the compound of the present invention is useful as a crane component of various plant disease controlling agents.
  • the control effect was evaluated by visually observing the diseased state of the test plant at the time of the survey, i.e., the appearance of the lesions on the leaves, stems, etc. Compared to untreated plots, 4% if recognized about 10%, 25%; 3J if recognized; 2% if about 50% recognized; 1J if 75% recognized, If there is no difference from the state, it is set to “0” and the efficiency is evaluated in six stages from 0 to 5, and is indicated by 0, 1, 2, 3, 4, and 5.
  • Test Example 1 Wheat powdery mildew control test (prevention test)
  • Leaves of open-grown grapes (variety "Kaiji", 3rd grade) cut out and punched into a 3 Omm-diameter disc are exposed to a chemical solution of a predetermined concentration of a wettable powder of the compound of the present invention.
  • a suspension of zoospores of (P la sipop araviticola) was sprayed and inoculated, kept in a humidified room at 20 ° C under illumination, and the disease status was examined 10 days after the inoculation.
  • Table 6 shows the results. Table 6

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Sont décrits un composé représenté par la formule générale [I], un sel de celui-ci, un procédé pour sa production, et un bactéricide agrohorticole le contenant. Dans ladite formule, m représente un entier compris entre 1 et 4; R1 représente hydrogène, alkyle inférieur, alcoxy inférieur, etc.; X représente C=Z [où Z représente oxygène, CH(OH), Cr?1(r2) (où r1 et r2¿ représentent chacun cyano, alcoxycarbonyl, carbamoyl, etc.) ou bien Nr?3 (où r3¿ représente alkyle inférieur, phényle, alcoxy inférieur, alkylamino inférieur, hydroxy, phénylamino, alcoxycarbonylamino inférieur, etc.)], CH(OH) ou CH¿2?; Y représente N ou C(R?4) (où R4¿ représente hydrogène ou alcoxycarbonyl inférieur); R2 représente hydrogène, S(O)¿n?r?5 (où r5¿ représente alkyle inférieur, et n vaut 0, 1 ou 2), alcoxy inférieur, etc.; et R3 représente hydrogène, alcoxy inférieur, alkyle inférieur, phényle, un groupe hétérocyclique penta ou hexagonal contenant un ou deux atomes choisis parmi N, S et O, etc.
PCT/JP1992/001384 1991-10-24 1992-10-23 Nouveau derive heterocyclique et bactericide agrohorticole le renfermant WO1993008167A1 (fr)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003088963A1 (fr) * 2002-04-16 2003-10-30 Ortho-Mcneil Pharmaceutical, Inc. Derives 5-oxo et 5-thio de 5h-indeno'1,2-bipyridine avec liaison du recepteur d'adenosine a2a et inhibition de l'activite de phosphodiesterase pour le traitement de troubles neurodegeneratifs et de maladies a caractere inflammatoire
WO2005042500A1 (fr) * 2003-10-03 2005-05-12 Ortho-Mcneil Pharmaceutical, Inc. Arylindenopyridines et arylindenopyrimidines et leur utilisation en tant qu'antagoniste des recepteurs d'adenosine a2a
US6903109B2 (en) 2001-04-18 2005-06-07 Ortho-Muniel Pharmaceutical, Inc. Arylindenopyridines and related therapeutic and prophylactic methods
US7122544B2 (en) 2000-12-06 2006-10-17 Signal Pharmaceuticals, Llc Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto
US7129242B2 (en) 2000-12-06 2006-10-31 Signal Pharmaceuticals, Llc Anilinopyrimidine derivatives as JNK pathway inhibitors and compositions and methods related thereto
US7345052B2 (en) 2002-04-16 2008-03-18 Ortho-Mcneil Pharmaceutical, Inc. Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods
US7351729B2 (en) 2002-03-08 2008-04-01 Signal Pharmaceuticals, Llc JNK inhibitors for use in combination therapy for treating or managing proliferative disorders and cancers
JP2016502529A (ja) * 2012-11-30 2016-01-28 エルジー・ケム・リミテッド 新規な化合物およびそれを用いた有機電子素子
EP4039094A1 (fr) * 2021-02-03 2022-08-10 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Nouveaux composés antifongiques

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Publication number Priority date Publication date Assignee Title
US4717725A (en) * 1984-04-11 1988-01-05 Alcon Laboratories, Inc. Ophthalmic wound healing with aldose reductase inhibitors

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
US4717725A (en) * 1984-04-11 1988-01-05 Alcon Laboratories, Inc. Ophthalmic wound healing with aldose reductase inhibitors

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7129242B2 (en) 2000-12-06 2006-10-31 Signal Pharmaceuticals, Llc Anilinopyrimidine derivatives as JNK pathway inhibitors and compositions and methods related thereto
US7442699B2 (en) 2000-12-06 2008-10-28 Signal Pharmaceuticals, Llc Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto
US7122544B2 (en) 2000-12-06 2006-10-17 Signal Pharmaceuticals, Llc Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto
US6903109B2 (en) 2001-04-18 2005-06-07 Ortho-Muniel Pharmaceutical, Inc. Arylindenopyridines and related therapeutic and prophylactic methods
US6958328B2 (en) 2001-04-18 2005-10-25 Ortho-Mcneil Pharmaceutical, Inc Arylindenopyridines and related therapeutic and prophylactic methods
US7351729B2 (en) 2002-03-08 2008-04-01 Signal Pharmaceuticals, Llc JNK inhibitors for use in combination therapy for treating or managing proliferative disorders and cancers
US7345052B2 (en) 2002-04-16 2008-03-18 Ortho-Mcneil Pharmaceutical, Inc. Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods
WO2003088963A1 (fr) * 2002-04-16 2003-10-30 Ortho-Mcneil Pharmaceutical, Inc. Derives 5-oxo et 5-thio de 5h-indeno'1,2-bipyridine avec liaison du recepteur d'adenosine a2a et inhibition de l'activite de phosphodiesterase pour le traitement de troubles neurodegeneratifs et de maladies a caractere inflammatoire
US7468373B2 (en) 2002-04-16 2008-12-23 Ortho-Mcneil Pharmaceutical, Inc. Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods
US7754730B2 (en) 2002-04-16 2010-07-13 Ortho-Mcneil Pharmaceutical, Inc. Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods
JP2007521243A (ja) * 2003-10-03 2007-08-02 オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド アリールインデノピリジンおよびアリールインデノピリミジンならびにアデノシンＡ２ａ受容体アンタゴニストとしてのそれらの使用
WO2005042500A1 (fr) * 2003-10-03 2005-05-12 Ortho-Mcneil Pharmaceutical, Inc. Arylindenopyridines et arylindenopyrimidines et leur utilisation en tant qu'antagoniste des recepteurs d'adenosine a2a
JP4725963B2 (ja) * 2003-10-03 2011-07-13 オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド アリールインデノピリジンおよびアリールインデノピリミジンならびにアデノシンＡ２ａ受容体アンタゴニストとしてのそれらの使用
JP2016502529A (ja) * 2012-11-30 2016-01-28 エルジー・ケム・リミテッド 新規な化合物およびそれを用いた有機電子素子
US10790453B2 (en) 2012-11-30 2020-09-29 Lg Chem, Ltd. Compounds and organic electronic device using the same
EP4039094A1 (fr) * 2021-02-03 2022-08-10 Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. Nouveaux composés antifongiques
WO2022167503A1 (fr) * 2021-02-03 2022-08-11 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Nouveaux composés antifongiques

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