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WO1996017841A1 - Composes de pyridylpyrrole, processus de production et bactericide agro-horticole - Google Patents

Composes de pyridylpyrrole, processus de production et bactericide agro-horticole Download PDF

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Publication number
WO1996017841A1
WO1996017841A1 PCT/JP1995/002479 JP9502479W WO9617841A1 WO 1996017841 A1 WO1996017841 A1 WO 1996017841A1 JP 9502479 W JP9502479 W JP 9502479W WO 9617841 A1 WO9617841 A1 WO 9617841A1
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WIPO (PCT)
Prior art keywords
group
formula
same meaning
represent
alkyl
Prior art date
Application number
PCT/JP1995/002479
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English (en)
Japanese (ja)
Inventor
Kenji Hagiwara
Haruo Saso
Kosuke Ichinose
Chinami Yokota
Shinsuke Sano
Original Assignee
Nippon Soda 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 Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Priority to AU39947/95A priority Critical patent/AU3994795A/en
Publication of WO1996017841A1 publication Critical patent/WO1996017841A1/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
    • A01N43/34—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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring

Definitions

  • the present invention relates to a novel pyridylpyrrole compound, a production method, and an agricultural and horticultural fungicide.
  • Conventional technology :
  • J. Med. Chem., 36, 36558 (1993) describes the synthesis of the following compound ( ⁇ ) as a synthesis intermediate. However, its biological activity is not described.
  • An object of the present invention is to provide a novel compound that can be synthesized industrially advantageously, is a fungicide for agricultural and horticultural use that is safe and can be used safely.
  • the present invention is a pyridylpyrrole compound represented by the formula [I] or a salt thereof, a production method, and a fungicide for agriculture and horticulture.
  • R 1 is a hydrogen atom, methyl, ethyl, propyl, isopropyl, butyl, t_butyl, pentyl, hexyl, heptyl, octyl, nonyl, nonyl, decyl, or other straight-chain or branched C, to C, (, Alkyl group (this alkyl group is a halogen atom such as fluorine, chlorine and bromine, methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-butoxy, pentyloxy, hexyloxy and other C, — 1; which may be substituted by a C, -alkoxycarbonyl group such as an alkoxy group, a methoxycarbonyl, an ethoxyquincarbonyl, a propoxycarbonyl, a t-butoxycarbonyl or a cyano group), a cyclopropyl
  • Alkylthio groups such as thiocyanato group (SCN), methylthio, ethylthio, propylthio and isopropylthio; C alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl and isopropylsulfinyl; methylsulfonyl, ethylsulfonyl and propyl It represents a C alkylsulfonyl group such as sulfonyl and isopropylsulfonyl.
  • R 2 is a hydrogen atom, a substituent which is easily hydrolyzed as shown below, for example, a holyl group,
  • propionyl, C alkyl group such as propyl carbonyl, main Bok alkoxycarbonyl, et butoxycarbonyl, propoxycarbonyl, i Sopu port Po alkoxycarbonyl, blanking butoxycarbonyl, t part Tokishikarubo C such as a secondary le, - e alkoxy force Rubonyl group,
  • C alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, t-butylsulfonyl, pentylsulfonyl, and hexylsulfonyl;
  • Alkylthiomethyl groups such as methylthiomethyl, ethylthiomethyl, propylthiomethyl, and butylthiomethyl;
  • D alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio, butylthio, t-butylthio,
  • Halogen atom lower alkyl group, lower alkoxy group, nitro group, cyano group, alkylthio group, alkylsulfonyl group, haloalkyl group, alkylamino group, alkoxycarbonyl group, alkylcarbonyl group
  • N-phenylcarbamoyl group N-phenylcarbamoyl group
  • ⁇ Se Tokishime chill C, such as pro Pioniruokishime chill, - 6 alkylcarbonyl Okishime butyl group,
  • X represents a hydrogen atom, a halogen atom such as fluorine, chlorine, or bromine; a straight-chain or branched C, such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, and hexyl; -(; Alkyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-butoxy, pentyloxy, hexyloxy and other C> - ⁇ alkoxy groups, trifluoromethyl, trifluorethyl, pentafluoroethyl C, haloalkyl, trifluoromethoxy, difluoromethoxy, trichloromethoxy, trifluoroethoxy, difluoroethoxy, penfluorofluoroalkoxy, cyano, etc. , Nitro group, formyl group
  • alkylthio group such as a phenyl group which may have a substituent, methylthio, ethylthio, propylthio, isopropylthio, butylthio, t-butylthio, pentylthio, hexylthio, etc., methylsulfinyl, Etilsulfinyl
  • Y is a hydrogen atom, methyl, Echiru, propyl, i Sopuro pills, heptyl, t chromatography Bed chill, straight or branched, such as hexyl pentyl, C, - 6 alkyl group, Application Benefits Furuoromechiru, Application Benefits chloro C, -G haloalkyl groups such as methyl, trifluoroethyl, pentafluoroethyl,
  • alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, s-butoxy, t-butoxy,
  • Or represents a halogen atom such as fluorine, chlorine, or bromine.
  • Z is a halogen atom such as a hydrogen atom, fluorine, chlorine, bromine,
  • Straight or branched C alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, etc.
  • n represents an integer of 0 to 4, and when 2 or more, Y may be different.
  • the salt of the compound represented by the formula [I] is not particularly limited as long as it is acceptable in agriculture and horticulture, and examples thereof include salts of mineral acids such as hydrochloric acid and sulfuric acid, and salts such as acetic acid. Salts of mechanical acids, salts of alkali metals such as sodium, potassium and lithium, salts of alkaline earth metals such as calcium and magnesium, and salts of transition metals such as copper, zinc and manganese. Can be mentioned.
  • the compound of the present invention can be produced by the following method.
  • R 1 ′ is a hydrogen atom, (which may be substituted by a halogen atom, an alkoxy group, a d-ii alkoxycarbonyl group, or a cyano group)) C! -I.
  • C alkoxycarbonyl group, C 3 - represents a cycloalkyl group or Ararukiru group
  • X, Y, m, n are as defined above.
  • Z ' is a hydrogen atom, main Bok kill carbonyl, et butoxycarbonyl, propoxy force carbonyl, Lee Sopuropokishikaru Boniru, blanking butoxycarbonyl, C have G alkoxy carbonyl group such as t part butoxycarbonyl, 6 alkyl group or a carboxyl group Represents
  • Solvents that can be used include hydrocarbons such as benzene and toluene, ethers such as THF, amides such as DMF, esters such as ethyl acetate, DMSO, and acetate. And nitrometan.
  • trivalent phosphine compound examples include trialkylphosphine such as trimethylphosphine, triethylphosphine, tripropylphosphine, and tributylphosphine.
  • trialkylphosphine such as trimethylphosphine, triethylphosphine, tripropylphosphine, and tributylphosphine.
  • trialkyl phosphites such as tributyl, etc., and tributyl phosphine is particularly preferred.
  • Examples of the dehydrating agent include an acid anhydride and dicyclohexylcarpoimide, and a compound represented by the formula [III] is preferably used.
  • Trivalent phosphorus compound Trivalent phosphorus compound
  • the compound [VI] and the compound [VII] are reacted in a solvent-free or suitable organic solvent at 0 ° C to 200 ° C.
  • Solvents that can be used in the reaction include hydrocarbons such as benzene and toluene, ethers such as THF, amides such as DMF, esters such as ethyl acetate, DMSO, and acetate. Nitriles, nitrometers and the like can be mentioned.
  • the amines include tertiary amines such as triethylamine and ethyldiisopropylamine.
  • trivalent linoleic compound examples include trialkylphosphine such as trimethylphosphine, triethylphosphine, tripropylphosphine, and tributylphosphine; Trialkyl phosphites such as triphenyl phosphine, trimethyl phosphite, triethyl phosphite, tripropyl phosphite, and triptyl phosphite which may have And the like. Manufacturing method (4)
  • R 1 ′ is a haloalkyl group such as CF 3 or C 2 F 5
  • Z is a nitrogen group, an amino group or a halogen atom, it can also be produced by the following method.
  • a compound in which Z is a nitrogen group or a halogen compound can be produced by di- or halogenating a compound in which Z is a hydrogen atom by an ordinary synthetic chemistry technique. Further, a compound in which Z is a nitrogen group can be reduced to a compound in which Z is an amino group by reducing the compound by a general synthetic chemistry technique.
  • R ′ is a two-mouth
  • R 1 is amino.
  • Compound of R 1 is Chioshina one I wherein R 1 is SR 4 in a conventional manner (R 4 is C, -. Representing the B group) and a Ki out to induce the compounds, R 1 by further oxidation Wherein S is SOR 4 or S 0 2 R 4 .
  • a compound in which R 1 is a cyano group can be produced by reacting a compound in which R] is CF 3 with aqueous ammonia in an autoclave.
  • alkylthio, alkoxycarbonyl or formyl group it can also be produced by the method shown below.
  • a compound in which R 1 'is a hydroxyl group can be produced by the following method. [Wherein, X, Y, m, and n represent the same meaning as described above, and represent an alkyl group of R 8 it C]. Production method (1 1)
  • R 2 is other than a hydrogen atom and R 2 is a substituent that easily becomes a hydrogen atom by hydrolysis, those compounds can be produced by a general synthetic chemistry method as described below.
  • the structure of the compound of the present invention was determined by two-dimensional NMR, IR, MS and the like in addition to ordinary NMR. BEST MODE FOR CARRYING OUT THE INVENTION
  • 2—hydroxyminoketone (A) has the following formula: 2—Pyridine carboxy cyanoaldehyde, et al., J. Chem. Soc., Chem. Commun. With reference to 73, 55 and Synthesis 1975, 391, 2 — (3 — cyanophenyl) 1 1 induced by reaction with 3 — cyanobenzyl bromide — (2_pyridyl) ethanonone is reacted with nitrite in the presence of a base (sodium ethoxide) to give 2 — hydroxymino 2 — (3 — Cyanophenyl) 1 1- (2-pyridyl) ethanone was synthesized.
  • Ethyl 3- (2-pyridyl) propiolate is obtained by reacting 2-ethynylviridine with nBuLi in THF at — ⁇ 8 ° C and then condensing it with ethyl chloroformate. Obtained by
  • Table 1 shows typical examples of the compounds of the present invention synthesized in the same manner.
  • X m the phrase H during column Y ", refers to the case of all hydrogen atoms. If a substituent is shown with substitution positions, other The substituent at the position is a hydrogen atom. Since the compound of the present invention has excellent bactericidal activity against a wide variety of fungi, it can be used for controlling various diseases that occur when cultivating agricultural and horticultural crops including flowers, turf, and pasture. . For example,
  • Noksaibe disease Pernospora brass ikae
  • It can be used for pest control.
  • the compound of the present invention is an agent having an excellent bactericidal effect not only on sensitive strains but also on pathogenic bacteria of the asialalanin resistant strain.
  • Diseases that are more preferable to apply include downy mildew of cucumber, downy mildew of bud, potato blight, and the like.
  • the compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to aquatic organisms such as ship bottoms and fish nets.
  • the compound of the present invention can be used as a fungicidal or fungicidal agent for walls and bathtubs, or shoes and clothes by mixing it with paints and fibers.
  • the thus-obtained compound of the present invention When the thus-obtained compound of the present invention is actually applied, it can be used in a pure form without adding other components, and can be in a form that a general pesticide can take for the purpose of being used as a pesticide, that is, It can also be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like.
  • solid additives are used as additives and carriers, soybean grains, vegetable powders such as flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc.
  • Organic and inorganic compounds such as mineral fine powder, sodium benzoate, urea, and sodium sulfate are used.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, aceton,
  • chloroethylene, methylisobutyl ketone, mineral oil, vegetable oil, water, etc. as solvents.
  • Surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.
  • the wettable powder, emulsion and flowable thus obtained are diluted with water to a predetermined concentration to form a suspension or emulsion, and the powder and granules are used as they are by spraying them on plants. You.
  • the compound of the present invention exerts a sufficient effect even when used alone, but can also be used as a mixture with one or more of various fungicides, insecticides, acaricides, or synergists.
  • Fungicides, insecticides, acaricides, nematicides, and plant growth regulators that can be used by mixing with the compound of the present invention include the following. Fungicide :
  • Organic phosphorus agents such as chlorothalonil and fusaride:
  • IBP IBP
  • EDDPP Torque mouth phosmethyl
  • pyrazophos pyrazophos
  • josetyl etc.
  • Triazimefone triazimenol, vitelenol, microbutanil, hexaconazole, propiconazole, trifmizole, prochloraz, perfrazolone, fenarimol , Pyrifenox, trifluorin, flusilazole, etaconazole, dichlorbutrazole, fluotrimazole, flutriafene, penconazole, giniconazole, Cyproconazole, imazalil, tridemorph, fenpropimorph, pthiobate, etc.
  • Antibiotics Polyoxin, blasticidin S, kasugamycin, noridamicin, dihydrosulfate streptomycin sulfate, etc.
  • Insecticides and miticides :
  • Nematicide Nematicide:
  • Plant growth regulator Plant growth regulator
  • Jibere Li emissions (such Jibere Li down A 3, Jibere Li down A 4, Jibere Li down A 7) IAA, NAA.
  • Example 15 5 wettable powder Compound of the present invention 40 parts
  • Test Examples show that the compounds of the present invention are useful as effective components of various plant disease controlling agents. The control effect was determined by visually observing the growth degree of the diseased flora that appeared on the leaves and stems at the time of the survey.
  • An emulsion of the compound of the present invention was sprayed at a concentration of 200 ppm on the young seedlings of cucumber (cultivar “Sagami Hanshiro”) cultivated in unglazed pots. After spraying, air-dry at room temperature, cucumber and disease (Pseudoperonosporacuben sis) The spore suspension was spray-inoculated, and kept in a constant temperature room (25 te) where light, darkness and dryness were repeated every 12 hours for 4 days. The following compound showed an excellent control effect of 80% or more.
  • Leaves of field-grown vines (variety “Kaiji”, 3rd grade) were punched into a disk having a diameter of 3 O mm, and immersed in an emulsion of the compound of the present invention and a chemical solution having a concentration of 200 ppm of the active ingredient. After immersion, air-dry at room temperature, inoculate with a zoospore suspension of P. asparagus downy mildew (P1 asm 0 paraviticola), and keep in a constant temperature room (20 ° C) under lighting for 10 days did. As a result of comparing and investigating the appearance of lesions on the leaves with no treatment, the following compounds showed an excellent control effect of 80% or more.
  • the compound of the present invention has an excellent control effect on plant diseases, and a drug containing the compound of the present invention is useful as a fungicide for agricultural and horticultural use.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un composé de pyridylpyrrole, représenté par la formule générale (I), ou un sel de ce composé où R1 représente l'hydrogène ou, en variante, le C¿1?-C10 alkyle substitué, le C3-C7 cycloalkyle, l'hyxdroxyle, l'aralkyle, le carboxyle, l'alcoxycarbonyle, le nitro, amino, halogéno, le C1-C6 alkylthio, le C1-C6 alkylsulfinyle, le C1-C6 alkylsulfonyle, le thiocyanato ou cyano; R?2¿ représente l'hydrogène, le formyle, le C¿1?-C6 alcoxyméthyle, le C1-C6 alkylcarbonyle, le C1-C6 alkylcarbonyle, le C1-C6 alcoxycarbonyle, le C1-C6 alkylsulfonyle, le benzoyle substitué, le sulfonyle de benzène substitué, le carbamoyle N-substitué, le C1-C6 alkylcarbonyloxyméthyle, le C1-C6 alkylthiométhyle, le C1-C6 alkylsulfonylméthyle ou le C1-C6 alkylthio; X représente l'hydrogène, l'halogéno, le C1-C6 alkyle, le C1-C6 alcoxy, le C1-C6 haloalkyle, le cyano, le nitro, le formyle, le C1-C6 haloalcoxy, le phénoxy, le C1-C6 alkylthio, le C1-C6 alkylsulfinyle, le C1-C6 alkylsulfonyle, le C1-C6 alcoxycarbonyle, etc.; Y représente l'hydrogène, le C1-C6 alkyle, le C1-C6 haloalkyle, le C1-C6 alcoxy ou halogéno; Z représente l'hydrogène, l'halogéno, le C1-C6 alkyle, le cyano, nitro, carboxyle, le C1-C6 alcoxycarbonyle ou amino; m représente un nombre entier de 0 à 5, et n est un nombre entier de 0 à 4.
PCT/JP1995/002479 1994-12-06 1995-12-05 Composes de pyridylpyrrole, processus de production et bactericide agro-horticole WO1996017841A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU39947/95A AU3994795A (en) 1994-12-06 1995-12-05 Pyridylpyrrole compounds, process for production, and agrohorticultural bactericide

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JP33015494 1994-12-06
JP6/330154 1994-12-06
JP21247395 1995-07-28
JP6/212473 1995-07-28
JP6/255658 1995-09-07
JP25565895 1995-09-07

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997005877A1 (fr) * 1995-08-10 1997-02-20 Merck & Co., Inc. Pyrroles d'aryle substitues en position 2, compositions contenant de tels composes et leurs modes d'utilisation
US5776954A (en) * 1996-10-30 1998-07-07 Merck & Co., Inc. Substituted pyridyl pyrroles, compositions containing such compounds and methods of use
US5792778A (en) * 1995-08-10 1998-08-11 Merck & Co., Inc. 2-substituted aryl pyrroles, compositions containing such compounds and methods of use
US5837719A (en) * 1995-08-10 1998-11-17 Merck & Co., Inc. 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use
JP2003527336A (ja) * 1999-11-12 2003-09-16 メルク エンド カムパニー インコーポレーテッド 抗原虫薬としてのジアリールピペリジルピロール誘導体
EP1451147A4 (fr) * 2001-07-24 2007-06-06 Pharmacore Inc Derives d'amino acides
WO2014199164A1 (fr) * 2013-06-12 2014-12-18 Ampla Pharmaceuticals, Inc. Composés hétéroaromatiques diaryle substitués

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6137705A (ja) * 1984-07-31 1986-02-22 Hokko Chem Ind Co Ltd ヘテロアレンオリゴマ−誘導体を含む農園芸用殺菌剤
JPH04145078A (ja) * 1990-10-04 1992-05-19 Hokko Chem Ind Co Ltd ピロールジカルボン酸誘導体および除草剤
JPH04234849A (ja) * 1990-04-07 1992-08-24 Bayer Ag ２−アリール−６−ヘタリールピリジン誘導体類

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6137705A (ja) * 1984-07-31 1986-02-22 Hokko Chem Ind Co Ltd ヘテロアレンオリゴマ−誘導体を含む農園芸用殺菌剤
JPH04234849A (ja) * 1990-04-07 1992-08-24 Bayer Ag ２−アリール−６−ヘタリールピリジン誘導体類
JPH04145078A (ja) * 1990-10-04 1992-05-19 Hokko Chem Ind Co Ltd ピロールジカルボン酸誘導体および除草剤

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997005877A1 (fr) * 1995-08-10 1997-02-20 Merck & Co., Inc. Pyrroles d'aryle substitues en position 2, compositions contenant de tels composes et leurs modes d'utilisation
US5792778A (en) * 1995-08-10 1998-08-11 Merck & Co., Inc. 2-substituted aryl pyrroles, compositions containing such compounds and methods of use
US5837719A (en) * 1995-08-10 1998-11-17 Merck & Co., Inc. 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use
US5776954A (en) * 1996-10-30 1998-07-07 Merck & Co., Inc. Substituted pyridyl pyrroles, compositions containing such compounds and methods of use
JP2003527336A (ja) * 1999-11-12 2003-09-16 メルク エンド カムパニー インコーポレーテッド 抗原虫薬としてのジアリールピペリジルピロール誘導体
EP1451147A4 (fr) * 2001-07-24 2007-06-06 Pharmacore Inc Derives d'amino acides
WO2014199164A1 (fr) * 2013-06-12 2014-12-18 Ampla Pharmaceuticals, Inc. Composés hétéroaromatiques diaryle substitués

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