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WO1994001423A1 - Derive de thiazol - Google Patents

Derive de thiazol Download PDF

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Publication number
WO1994001423A1
WO1994001423A1 PCT/JP1993/000926 JP9300926W WO9401423A1 WO 1994001423 A1 WO1994001423 A1 WO 1994001423A1 JP 9300926 W JP9300926 W JP 9300926W WO 9401423 A1 WO9401423 A1 WO 9401423A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
halogen atom
mono
general formula
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP1993/000926
Other languages
English (en)
Japanese (ja)
Inventor
Izumi Kumita
Kaoru Noda
Sho Hashimoto
Michihiko Matsuda
Takao Iwasa
Takashi NUKUI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Soda Co Ltd
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
Publication of WO1994001423A1 publication Critical patent/WO1994001423A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
    • 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

Definitions

  • the present invention relates to a novel thiazole derivative and a method for producing the same.
  • Technical background :
  • antibiotics such as penicillin and cephalosporin derivatives have been researched and developed at a remarkable rate, and drugs that show a remarkable effect on infections caused by Gram-positive or Gram-negative pathogenic bacteria have been released one after another.
  • drugs that show a remarkable effect on infections caused by Gram-positive or Gram-negative pathogenic bacteria have been released one after another.
  • refractory persistent dermatomycosis and visceral mycosis are increasing steadily, but currently marketed antifungal agents have limited indications due to side effects. Therefore, development of antifungal drugs that are harmless to humans and have few side effects is awaited.
  • An object of the present invention is to provide a novel compound having antibacterial activity and insecticidal activity which can be synthesized industrially advantageously, has a certain effect and can be used safely.
  • the present invention has the general formula (I)
  • R ′, R 2 and X are the same or different and represent a halogen atom, a —C 6 alkyl group, a —C 6 alkoxy group or a d-Ce alkylthio group, and n is 0, 1, 2, or Represents 3,
  • R 3 represents a hydrogen atom or an amino-protecting group
  • R is ⁇ C, - Ce alkyl group, d - C 6 haloalkyl group, d - C 6 alkoxy group, d - C 6 haloalkoxy group, d - Ce Arukeniruokishi groups, - C Arukiniruokishi groups, C] - Ce alkylthio group, C, - C e alkyl sulfates Finiru group, C -!
  • the protecting group of ⁇ Mi amino group of R 3 example, d - C 6 alkyl group, C 2 - C e alkenyl group,
  • r 1 represents a C 1 -C 6 alkyl group.
  • C r 2 r 3 O r 4 (where r 2 and r 3 are the same or different and are a hydrogen atom or d-C 6 alkyl represents a group, r 4 Haji, - C e alkyl group, d - C alkylcarbonyl, C -!
  • C alkoxycarbonyl group, C, _ C 6 alkyl mono Moshiku good Ami no be disubstituted Represents a C, -C alkylcarbonyl group.
  • C 0 r 5 (wherein, r 5 is a C -C alkyl group, a C 1 -C CB alkoxy group, a C, 1 C s alkyl or a mono- or C -alkyl group) Represents an amino group which may be di-substituted.)
  • a sulfamoyl group which may be mono- or di-substituted with C! -C alkyl.
  • the production method of the compound of the present invention is as follows.
  • R 1 , R 2 , R 3 , R 4 , X and n have the same meaning as described above, and Ha 1 represents a halogen atom.
  • the corresponding acetophenone derivative is halogenated, and the ⁇ -haloacetophenone derivative [II] is reacted with the corresponding thioperea [III].
  • the reaction is carried out in a solvent such as alcohol, DMF, acetonitrile, DMS 0 or halogenated hydrocarbons such as chloroform, methylene chloride, etc., or ethers such as dimethyl ether, dioxane, etc., and in some cases, triethylamine, pyridine.
  • an organic base such as N, N-N-dimethylaniline or DBU or an inorganic base such as potassium carbonate, sodium carbonate or sodium hydroxide.
  • an organic base such as N, N-N-dimethylaniline or DBU
  • an inorganic base such as potassium carbonate, sodium carbonate or sodium hydroxide.
  • R 1 , R 2 , R 4 , X and n have the same meaning as described above, R 3 ′ represents a protecting group for an amino group, and ha 1 represents a halogen atom.
  • inorganic bases such as potassium carbonate, sodium carbonate and sodium hydroxide or organic tertiary amines such as triethylamine, DBU, etc., and halogens such as acetonitrile, chloroform, methylene chloride, etc.
  • the reaction is carried out in a solvent such as a hydrogenated hydrocarbon or DMF at a temperature of from 20 ° C to room temperature, preferably from 15 ° C to 5 ° C.
  • a target substance can be obtained by performing ordinary post-treatment.
  • Table 1 shows typical examples of the compounds of the present invention, including the above Examples. £ 6df / Did ⁇ 1 / 0 OM,
  • the compound of the present invention exhibits excellent antibacterial activity. Some of the compounds of the present invention exhibit insecticidal activity, antifouling effect on aquatic organisms, or antihyperlipidemic effect.
  • the antifungal agent containing the compound of the present invention is useful as a therapeutic agent for mycosis involving fungi such as molds and yeasts contained in humans and for treating mammals.
  • Ointments, emulsions, suspensions, powders, solutions, tinctures, aerosols, tablets, capsules, elixirs, etc. for use as antifungal agents, and various dosage forms similar to known antifungal agents can be used with Dosages may vary depending on the severity of the illness, the weight of the patient and other factors recognized by those skilled in the art.
  • the compounds of the present invention are mixed with physiologically acceptable vehicles, carriers, excipients, binders, preservatives, stabilizers, flavoring agents and the like in the usual unit dosage forms.
  • the amount of active substance in these compositions or preparations is such that a suitable dosage in the range indicated is obtained.
  • Specific agents that can be mixed with tablets and capsules include binders such as arabia gum, excipients such as microcrystalline cellulose, leavening agents such as alginic acid, lubricants such as magnesium stearate, sodium, and the like. Examples include solubilizing agents such as desoxycholate, sweeteners such as sucrose, flavoring agents such as peppermint, etc.
  • binders such as arabia gum
  • excipients such as microcrystalline cellulose
  • leavening agents such as alginic acid
  • lubricants such as magnesium stearate, sodium, and the like.
  • solubilizing agents such as desoxycholate
  • sweeteners such as sucrose
  • flavoring agents such as peppermint, etc.
  • liquids such as oils and fats are added to the above-mentioned materials. Simple substance can be contained.
  • Various other materials can be present as coatings or to otherwise alter the physical form of the dosage unit.
  • tablets may be coated with shellac, sucrose or both.
  • Sterile compositions for injection can be formulated according to the normal pharmaceutical practice of dissolving or suspending the active substance in vehicles, such as water for injection, naturally occurring vegetable oils such as sesame oil, or synthetic fat vehicles such as ethyl ester. it can. Buffers, preservatives, antioxidants, and the like can be combined as needed.
  • the compound of the present invention when it is actually applied as a pesticide, it can be used in a pure form without adding other components, and a form that can be taken by a general pesticide for the purpose of using as a pesticide, that is, It can also be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions and the like.
  • a general pesticide for the purpose of using as a pesticide that is, It can also be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions and the like.
  • solid additives are used as additives and carriers, vegetable powders such as soybean flour and flour, diatomaceous earth, limestone, gypsum, talc, pyrophyllite, clay, and mineral oils such as mineral oil-vegetable oil Fine powder is used.
  • mineral oil, vegetable oil, water, etc. as solvent.
  • Surfactants can be added, if necessary, to obtain a uniform and stable form in these preparations.
  • the wettable powder and emulsion thus obtained are used as a suspension or an emulsion by diluting to a predetermined concentration with water, and the powder and granules are used as they are by spraying them on plants.
  • Example 4 wettable powder
  • the active ingredient 10 If the above ingredients are mixed and wet-pulverized until the particle size becomes 1 micron or less, the active ingredient 10
  • the compound of the present invention alone is sufficiently effective, but it is one of various fungicides and insecticides ⁇ ⁇ acaricides against inadequate or weak diseases or harmful insects and mites. It can be used as a mixture with two or more kinds.
  • fungicides insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.
  • Capbutane Forpet, Thiuram, Zineb, Maneb, Mangozeb, Provineb, Polycarbamate, Chlorothalonil, Kindzensen, Captahor, Prodione, Procymidone, Vinclozolin, Fluoroymid, Thymoxanil, Mepronil, Flutolanil, Pencyclon, Oxycarboxin, Josetyl Aluminum, Propamocarb, Triazimefone, Triazimenol, Propiconazole, Diclobutrazol, Vitel X Knol, Hexaconazole, Micronil, Flusilazole, Ethaconazole, Fluo Trimazole, Flutriaphen, Penconazol, Giniconazole, Cyproconazole, Fenarimol, Triflumizol, Prochloraz, Imazalil, ⁇ Frazoet, Tridemolph, Fenpropimorph, Trifolin, Petiobate, Pyrifenox, Arazine,
  • Jibereri emissions (such Jibereri down A 3, Jibereri emissions A 4, Jibereri emissions A 7) I AA, NAA.
  • the MIC minimum growth inhibitory concentration gZml
  • the compound dissolved in DMSO was diluted with a sub-mouth glucose medium so that the DMSO concentration did not exceed 1%.
  • a spore suspension (200,000-500,000 spores Zm 1) of T rychophyton me ntagrop hy tes (Trichophyton) was inoculated, and 3-7 days later, the absorbance at 450 nm was measured using a microplate photometer. The concentration at which the concentration became 0.02 or less was defined as the MIC.
  • Table 2 shows the results. Table 2
  • MIC minimum growth inhibition
  • the concentration (g / ml) was determined.
  • the compound dissolved in DMS ⁇ was diluted with a potato dextrin medium so that the concentration of DMS0 did not exceed 1%.
  • B 0 trytiscinerea Ingen gray mold fungus
  • a spore suspension (20 to 500,000 spores Zm 1) was inoculated, and 3 to 7 days later, the absorbance at 450 nm was measured using a microplate photometer. The concentration at which the concentration fell below 0.02 was taken as the MIC. Table 3 shows the results.
  • Control compound A same as control compound A in Table 2
  • Control compound A same as control compound A in Table 2
  • the compound was diluted with water so that the compound concentration was 125 ppm.
  • Corn leaves were immersed in the chemical solution for 30 seconds, air-dried, and then placed in a petri dish containing five Atoto 3rd instar larvae. They were covered with a glass lid and placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65% ', and the insecticidal rate was examined after 5 days. Two repetitions. The results are shown in Table 5. 5 Table Compound No. Insecticidal rate after 5 days 1 2 5 ppm
  • N CHN (CH 3 ) 2 , CH 3 Test Example 5 Therapeutic effect of guinea pig on experimental ringworm
  • the 13-week-old guinea pig was provided with a 2 cm square inoculation site on each side of the back of the guinea pig, and the hair was removed and the stratum corneum was separated using a gum tape. Then the T rich 0 phtyon me spore suspension ntagrophytes (2 xl 0 7 conidia / ml) 0. 0 5m 1 was coated inoculation. Treatment was started on day 4 after inoculation, and application of the solution at 0.1 ml / animal / day and observation of skin lesions were continued until day 16. Dissection was carried out on the 18th day, and bacterial culture was performed on the skin at the bacterial inoculation site. Table 6 shows the results.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Nouveau dérivé de thiazol représenté par la formule générale (I) et possédant une excellente efficacité antibactérienne et insecticide, ainsi que procédé de préparation. Dans la formule (I), R1, R2 et X peuvent être similaires ou différents les uns des autres, chacun représentant halogène, alkyle, alcoxy ou alkylthio; n représente 0, 1, 2 ou 3; R3 représente hydrogène ou un groupe de protection amino et R4 représente phényle, pyridyle ou cycloalkyle, chacun pouvant être substitué.
PCT/JP1993/000926 1992-07-07 1993-07-06 Derive de thiazol Ceased WO1994001423A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP4/201787 1992-07-07
JP20178792 1992-07-07

Publications (1)

Publication Number Publication Date
WO1994001423A1 true WO1994001423A1 (fr) 1994-01-20

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1993/000926 Ceased WO1994001423A1 (fr) 1992-07-07 1993-07-06 Derive de thiazol

Country Status (1)

Country Link
WO (1) WO1994001423A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2754258A1 (fr) * 1996-10-08 1998-04-10 Sanofi Sa Derives d'aminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant
US6586423B2 (en) 1999-09-10 2003-07-01 Merck & Co., Inc. Tyrosine kinase inhibitors
US6872724B2 (en) 2002-07-24 2005-03-29 Merck & Co., Inc. Polymorphs with tyrosine kinase activity
US6875767B2 (en) 2001-06-22 2005-04-05 Merck & Co., Inc. (5-cyano-2-thiazolyl)amino-4-pyridine tyrosine kinase inhibitors
EP1500655A4 (fr) * 2002-04-02 2006-03-29 Shanghai Inst Materia Medica Nouvel inhibiteur de la methionine aminopeptidase
JP2016040276A (ja) * 2010-11-12 2016-03-24 デューク ユニバーシティDuke University 熱ショック転写因子活性化化合物及びそのターゲットに関連する組成物及び方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025413A2 (fr) * 1979-09-11 1981-03-18 Ciba-Geigy Ag Sels de 3-méthyl-2-(2',4'-diméthyl-phénylimino)-4-thiazoline avec des polymères ayant des groupes acide sulfonique, et leur application comme pesticides
EP0111904A2 (fr) * 1982-12-21 1984-06-27 Shionogi & Co., Ltd. Dérivés de propynylaminothiazole
EP0331966A1 (fr) * 1988-03-05 1989-09-13 Bayer Ag Esters d'acide acrylique substituées

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025413A2 (fr) * 1979-09-11 1981-03-18 Ciba-Geigy Ag Sels de 3-méthyl-2-(2',4'-diméthyl-phénylimino)-4-thiazoline avec des polymères ayant des groupes acide sulfonique, et leur application comme pesticides
EP0111904A2 (fr) * 1982-12-21 1984-06-27 Shionogi & Co., Ltd. Dérivés de propynylaminothiazole
EP0331966A1 (fr) * 1988-03-05 1989-09-13 Bayer Ag Esters d'acide acrylique substituées

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
INDIAN J. CHEM., Sect. B, Vol. 26B, No. 1, p. 88-90, (1987), AHLUWALIA, V.K. et al., "Synthesis and Antimicrobial and Antifungal Activities of Some New 2-(N-(2'-Mercapto-1',3',4'-Thiadiazol-5'-yl) Amino)-4-Arylthiazole Derivatives". *
J. CHEM. SOC., Perkin Trans. 1, No. 3, p. 639-643, (1987), BRAMLEY, SUSAN E. et al., "Hantzsch Thiazole Synthesis under Acidic Conditions; Change of Regioselectivity". *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2754258A1 (fr) * 1996-10-08 1998-04-10 Sanofi Sa Derives d'aminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant
WO1998015543A1 (fr) * 1996-10-08 1998-04-16 Sanofi Derives d'aminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant
US6344470B1 (en) 1996-10-08 2002-02-05 Sanofi-Synthelabo Aminothiazole derivatives, method of preparation and pharmaceutical compositions containing same
US6586423B2 (en) 1999-09-10 2003-07-01 Merck & Co., Inc. Tyrosine kinase inhibitors
US6586424B2 (en) 1999-09-10 2003-07-01 Merck & Co., Inc. Tyrosine kinase inhibitors
US6875767B2 (en) 2001-06-22 2005-04-05 Merck & Co., Inc. (5-cyano-2-thiazolyl)amino-4-pyridine tyrosine kinase inhibitors
EP1500655A4 (fr) * 2002-04-02 2006-03-29 Shanghai Inst Materia Medica Nouvel inhibiteur de la methionine aminopeptidase
US6872724B2 (en) 2002-07-24 2005-03-29 Merck & Co., Inc. Polymorphs with tyrosine kinase activity
JP2016040276A (ja) * 2010-11-12 2016-03-24 デューク ユニバーシティDuke University 熱ショック転写因子活性化化合物及びそのターゲットに関連する組成物及び方法

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