WO2009012679A1 - Composés de 2,2,3a,4-tétrahydrothiochromène[4,3-c]pyrazole, leur procédé de préparation et utilisation - Google Patents

Composés de 2,2,3a,4-tétrahydrothiochromène[4,3-c]pyrazole, leur procédé de préparation et utilisation Download PDF

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Publication number
WO2009012679A1
WO2009012679A1 PCT/CN2008/071435 CN2008071435W WO2009012679A1 WO 2009012679 A1 WO2009012679 A1 WO 2009012679A1 CN 2008071435 W CN2008071435 W CN 2008071435W WO 2009012679 A1 WO2009012679 A1 WO 2009012679A1
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Prior art keywords
formula
group
acetyl
compound
pyrazole
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PCT/CN2008/071435
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English (en)
Chinese (zh)
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Gengliang Yang
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Gengliang Yang
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Publication of WO2009012679A1 publication Critical patent/WO2009012679A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics

Definitions

  • the present invention relates to 2, 3, 3a, 4-tetrahydrothiochromene [ 4,3-c]pyrazoles 2, 3, 3a, 4-tetrahydrothiochromene pyrazole compounds, in particular, substituted 2, 3, 3a, 4-tetrahydrothiochromene [4, 3 - c] pyrazoles and their preparation and antifungal use.
  • a fungus is a eukaryotic cell organism having a similar structure and physiological metabolic process to a host cell, and is classified into a superficial infection and a deep infection according to the infection site caused by the fungus.
  • Shallow fungal infections are mainly caused by various sputum bacteria, such as hand, foot and sputum, head lice, body lice, etc.
  • gray mold, nystatin, ketoconazole, etc. are often used as therapeutic drugs.
  • Deep fungal infections can be dangerous, even in crisis and life.
  • examples of pathogenic fungi include Candida albicans, Cryptococcus neoformans, Aspergillus, and Mucor.
  • Some fungi that normally do not cause disease in the body may cause disease when used in a long-term or large-scale use of broad-spectrum antibiotics, hormones, and immunosuppressive agents.
  • the incidence of fungal infections has increased year by year in recent years.
  • R 2 and R 3 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, Cu-hydrocarbyl, Cu-hydrocarbyloxy, C-hydrocarbylcarbonyl, Cu-hydrocarbylcarbonyloxy, provided that At least one of Ri, R 2 , and R 3 is not hydrogen, wherein when the above group contains a hydrocarbyl moiety, the hydrocarbyl moiety may be optionally one or more independently selected from the group consisting of fluorine, chlorine, bromine, and iodine. Substituted by a halogen atom;
  • R 4 is selected from the group consisting of hydrogen and Cue-hydrocarbyl
  • R 5 is selected from Cwo-trans group, and the hydrocarbyl group may be optionally substituted by one or more halogen atoms independently selected from fluorine, chlorine, bromine and iodine;
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, Cwo-hydrocarbyl, Cu-hydrocarbyloxy, Cu-hydrocarbylthio, Cu-hydrocarbylcarbonyl, C-hydrocarbylcarbonyloxy a Cwo-hydrocarbylamino group, and a bis(Cwo-hydrocarbyl)-amine group, wherein when the above group contains a hydrocarbyl moiety, the hydrocarbyl moiety may be optionally one or more independently selected from the group consisting of fluorine, chlorine, Substituting bromine and iodine atoms; wherein the above CWQ-hydrocarbyl group may be an aromatic hydrocarbon group or a non-aromatic hydrocarbon group, or may be a linear hydrocarbon group or a branched hydrocarbon group, or may be a saturated hydrocarbon group or an unsaturated hydrocarbon group, or may
  • R 2 and R 3 may each independently be selected from the group consisting of Hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, decyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, heptyl, octyl , 2-ethylhexyl, vinyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, cyclopropyl, cyclohexyl, phenyl, benzyl, naphthyl, naphthoquinone ,
  • R 4 may be selected from the group consisting of hydrogen, decyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl. , n-pentyl, isopentyl, tert-amyl, n-hexyl, 2-ethylhexyl, n-octyl, decyl and fluorenyl.
  • R 6 , R 7 and R 8 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, decyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-pentyl, isuf.
  • the compound of formula (I) is a stereoisomer of formula (1,) and (1") or a mixture thereof, and the compound of formula (II) is of formula (II,) and ( Stereoisomers represented by II") or mixtures thereof,
  • Another aspect of the present invention provides a stereoisomer of a 2,3,3a,4-tetrahydrothiochromeno[4,3-c]pyrazole compound represented by the formula (I) or (11).
  • a method of racemic or non-racemic mixture of its stereoisomers or a pharmaceutically acceptable salt or solvate thereof, the method comprising the steps of:
  • R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are as defined above;
  • X in formula (III) and formula (V) may be independently selected from the group consisting of fluorine, chlorine, bromine and iodine, respectively.
  • the first acid It may be sulfuric acid, hydrochloric acid, preferably 2-6 M sulfuric acid; the second acid may be sulfuric acid, hydrochloric acid, preferably 2-6 M sulfuric acid; the third acid may be polyphosphoric acid, concentrated sulfuric acid, preferably concentrated sulfuric acid;
  • the first base may be sodium hydroxide or potassium hydroxide, preferably 1 to 3 M sodium hydroxide; the second base may be an aqueous solution of sodium carbonate, sodium hydrogencarbonate or carbonic acid, preferably an aqueous solution of potassium carbonate;
  • the third base may be sodium hydroxide, potassium hydroxide or calcium hydroxide, preferably 5 to 20% sodium hydroxide.
  • the first acid may be sulfuric acid, hydrochloric acid, preferably 2-6 M sulfuric acid;
  • the second acid may be sulfuric acid, Hydrochloric acid, preferably 2-6 M sulfuric acid;
  • the third acid may be omelic acid, concentrated sulfuric acid, preferably concentrated sulfuric acid;
  • the first base may be sodium hydroxide, potassium hydroxide, preferably 1 to 3 M sodium hydroxide;
  • the second base may be an aqueous solution of sodium carbonate, sodium hydrogencarbonate or carbonic acid, preferably an aqueous solution of potassium carbonate; and
  • the third base may be sodium hydroxide, potassium hydroxide or calcium hydroxide, preferably 5 to 20% hydrogen.
  • the first acid in step 1) may be added dropwise to the mixture of the compound of formula (III) and the metal zinc with stirring.
  • an alcohol such as ethanol may be added as a solvent in the step 2), and the ester of the compound of the formula (V) may be a mercaptoester or a
  • the base ester, in some cases, step 2) is carried out under reflux.
  • the compound of formula (VII) in step 4) is added dropwise at room temperature to a compound comprising a formula (Villa ) or (VHIb ), such as ethanol.
  • the solvent is reacted with a mixture of the third base.
  • step 5 is carried out under heating under reflux.
  • the compound of formula (I) or ( ⁇ ) obtained in step 5) is further isolated to give formula (1,) and (1"
  • Suitable pharmaceutically acceptable salts are readily apparent to those skilled in the art and include, for example, mineral acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid or phosphoric acid, or with, for example, succinic acid, maleic acid. , acetic acid, fumaric acid, citric acid, tartaric acid, benzoic acid, An acid addition salt formed from an organic acid of nonylbenzenesulfonic acid, mercaptosulfonic acid or naphthalenesulfonic acid.
  • the pharmaceutically acceptable salt includes all possible stoichiometric and non-stoichiometric forms.
  • the compounds of formula (I) and formula (II) may be prepared in crystalline or amorphous form, and if crystalline, they may optionally be solvates, for example as hydrates.
  • the invention includes within its scope stoichiometric solvates (e.g., hydrates) as well as compounds containing variable amounts of solvents (e.g., water).
  • a metal zinc is added to the compound of the formula (III), and then 4MH 2 S0 4 is added dropwise thereto while stirring,
  • the compound of formula (IV) is isolated and purified.
  • the obtained compound of the formula (IV) is dissolved in a 2 M NaOH solution (a suitable amount of ethanol may be added), and the compound of the formula (V) (or its mercaptoester or ethyl ester) is dissolved in a stoichiometric amount of Na 2 CO 3 solution.
  • the compound of the formula (VII) obtained above is added dropwise at room temperature in a mixed solution of a compound of the formula (Villa) or (Vlllb) (an aromatic aldehyde or a substituted aromatic aldehyde) and 10% NaOH, and the temperature is maintained for 1 hour after the addition.
  • the mixture was filtered off with suction and washed with water to give a compound of formula (IXa) or (IXb) (substituted fluorene substituted for selemannone).
  • the obtained product is heated under reflux with a compound of the formula (X) (for example, glacial acetic acid) for 15 hours, and then poured into ice water to give a compound of the formula (I) or (II).
  • the compound of the formula (I) or (II) is subjected to column separation to obtain a stereoisomer represented by the formula (1,) and (1") or a stereoisomer represented by the formula (?) and (II").
  • the synthetic route for the preparation of a compound of formula (I) or (11) is as follows:
  • the antifungal pharmaceutical composition can be formed into a dosage form for the treatment or prevention of a fungal infection.
  • the compound represented by the formula (I) or (II) may be present in various suitable amounts.
  • the antifungal pharmaceutical composition contains a synergistically effective amount of a compound of formula (I) or (II).
  • a synergistically effective amount means an amount capable of enhancing the antifungal therapeutic effect of the antifungal pharmaceutical composition.
  • the compound represented by the formula (I) or (II) is from 0.01 to 30% by weight, preferably from 0.01 to 20%, more preferably from 0.2 to 10% by weight based on the total weight of the composition. It is particularly preferably from 0.5 to 5%, for example from 1 to 2%.
  • the pharmaceutical adjuvant or carrier is any conventional pharmaceutical excipient or carrier suitable for the preparation of the formulation.
  • the pharmaceutical adjuvant or carrier is selected from one or more of an oily base, a water soluble base, a gel base, a preservative, an antioxidant, and distilled water.
  • the adjuvant or carrier may also include emulsifiers, odorants, pigments, dyes, propellants and the like, and other common types suitable for various different types of preparations, and if necessary, humectants such as glycerin, thioglycoside , propylene glycol and the like, preferably glycerin and propylene glycol.
  • the compositions of the present invention may be in a variety of suitable dosage forms.
  • the dosage form is a topical dosage form conventionally used in the art, such as an ointment, cream, gel, cream, lotion, suppository, oil or spray.
  • the antifungal compositions of the invention can be prepared by a variety of methods.
  • the antifungal pharmaceutical compositions of the invention can be administered to a variety of animals, including mammals, particularly humans.
  • the dosage can be determined by the medical practitioner depending on the condition of the subject, including, for example, the patient's disease severity, general health, weight, age, and the like.
  • the antifungal pharmaceutical compositions of the present invention can be administered by a variety of suitable routes including, for example, transdermal, transdermal, and topical administration and the like.
  • the antifungal pharmaceutical composition of the present invention can be formulated into an ointment, a gel, a cream, or the like, applied to the affected part of the skin surface by application, for treating a fungal infection or the like.
  • the frequency of administration of the antifungal pharmaceutical composition of the present invention can also be determined by a variety of factors including, for example, the particular disease to be treated, the general health of the subject, and the like. Usually, human subjects are administered 1 to 2 times a day.
  • Antifungal use of a racemic mixture or a pharmaceutically acceptable salt or solvate thereof including topical administration of the compound to a patient, or systemic administration of the compound to a patient.
  • the fungus comprises Candida albicans, Candida tropicalis, Saccharomyces cerevisiae, Cryptococcus neoformans, Fusarium oxysporum, Trichophyton rubrum, Trichophyton rubrum, Trichophyton rubrum, Gypsum-like microspores, Trichoderma, Aspergillus, Aspergillus oryzae, Penicillium spp., Penicillium militaris, Cladosporium carbendazim, Phytophthora, Streptomyces and S. sphaeroides.
  • BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be further illustrated by the following Preparation Examples and Examples.
  • Preparation Example 1 Preparation of the compound of the formula (IV) 0.2 mol of 4-fluorobenzenesulfonyl chloride was placed in a three-necked flask, and another 26 g of metal zinc powder was added and stirred uniformly. O: 4 M H 2 S0 was added dropwise to the ice water bath. 4 , stirring while stirring, after 6-8 hours of reaction, separation by filtration, washing, drying, and recrystallization to obtain 4-fluorothiophenol (a compound of formula (IV)). The yield is 85 - 88% and the boiling point is 164-168X:.
  • Example 1 2-Acetyl-3-phenyl-8-fluoro-2,3,3a,4-tetrahydrothiochromeno[4,3-c]pyrazole lOOmmol p-fluorophenephenol, 120 mmol ⁇ - Chloropropionic acid, add 250mmol 20% NaOH solution, stir well, put in 500ml Erlenmeyer flask, mix well, microwave radiation for 4 ⁇ 5min, get white viscous liquid, hydrochloric acid adjust pH « l, there are a lot of light yellow precipitate It was produced, suction filtered, dried and recrystallized from 95% ethanol/water.
  • the white solid 3-(4-fluoro-phenylhydrazino)-propionic acid was obtained in a yield of 65-75%.
  • the prepared 3-(4-fluoro-phenylhydrazinyl)-propionic acid 13 mmol was dissolved in 20 ml of concentrated sulfuric acid and allowed to stand at room temperature for 18 h.
  • the reaction solution was ice-dissolved, filtered, and the filter cake was washed with 5-10% NaHCO 3 solution, washed to neutral, and dried by suction filtration to give a pale yellow solid 6-fluoro-thiochromanone in a yield of 80-85%.
  • pedrosoi C. carionii, P. comaitum, and bottle mold ( P. verrcosa) and S. schenekn.
  • the fungi used above were purchased from the Dermatology Hospital of the Chinese Academy of Medical Sciences, Nanjing, China.
  • Preparation of bacterial solution Transfer the fully developed test species to 5ml sterile saline, smash and ultrasonic, fully oscillate, remove the blocky insoluble matter, mix the hook, as the original bacterial solution, adjust the concentration to 10 during the test. Use after 6 cells/ml.
  • test compound was dissolved in an appropriate amount of disulfoxide, diluted with sterile distilled water, and added to the sterile 1% (hot) glucose protein agar medium at a concentration of 200, 100, 50, 25 , 12.5, 6.25, 3.12, 1.60 mg/mL. After the test bacteria were inoculated, the highest dilution concentration without fungal growth was set as the minimum inhibitory concentration MIC for 5-7 days in a constant temperature oven.
  • the 2,3,3a,4-tetrahydrothiochromeno[4,3-c]pyrazole series compounds have different degrees of inhibitory activity against fungi, and some of them have antifungal activity and The control substance is similar to clotrimazole; some are even superior to the antifungal activity of clotrimazole.
  • the medicaments of the present invention are synthesized by using benzenesulfonyl chloride (or substituted benzenesulfonyl chloride) as a raw material, and various chemical reagents used in the synthesis reaction are common and simple and easy to obtain. The yield is also ideal.
  • P.comaitum 100 100 25 25 50 50 25 25 50 50 100 100 25 25 50 50 12.5 12.5 25 25 25 12.5

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des composés de 2,2,3a,4-tétrahydro-thiochromène[4,3-c]pyrazole de formule (I) ou (II) et leurs stéréo-isomères, mélanges racémiques ou mélanges non racémiques des stéréo-isomères, ou des sels acceptables sur le plan pharmaceutique ou des solvates. L'invention concerne également leur procédé de préparation, des compositions pharmaceutiques et l'utilisation antifongique.
PCT/CN2008/071435 2007-07-25 2008-06-26 Composés de 2,2,3a,4-tétrahydrothiochromène[4,3-c]pyrazole, leur procédé de préparation et utilisation WO2009012679A1 (fr)

Applications Claiming Priority (2)

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CN200710129732.0 2007-07-25
CNA2007101297320A CN101353351A (zh) 2007-07-25 2007-07-25 新的2,3,3a,4-四氢硫色烯并[4,3-c]吡唑类抗炎、抗真菌化合物

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WO2009012679A1 true WO2009012679A1 (fr) 2009-01-29

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014167552A1 (fr) 2013-04-11 2014-10-16 Ofta Sp. Z O. O. Huile essentielle et aloès pour le traitement et la prophylaxie d'inflammations provoquées par demodex, notamment la blépharite marginale, composition pharmaceutique contenant une huile essentielle et/ou de l'aloès et utilisation de l'huile essentielle et de l'aloès et de leurs compositions pour la production d'une préparation utilisée dans le traitement et la prophylaxie des inflammations mentionnées

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102086212B (zh) * 2009-12-03 2013-06-12 沈阳药科大学 抗真菌剂-2，3，4，5-四氢-4H-苯并[b]噻喃并[4，3-c]吡唑-2-甲酰胺衍生物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990003969A1 (fr) * 1988-10-11 1990-04-19 E.I. Du Pont De Nemours And Company Indazoles substitues en tant qu'arthropodicides
CN1069272A (zh) * 1991-08-02 1993-02-24 布茨公司 制备苯并吡或噻喃并吡唑的方法
WO2007075772A2 (fr) * 2005-12-20 2007-07-05 President And Fellows Of Harvard College Composes, essais et methodes de traitement

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990003969A1 (fr) * 1988-10-11 1990-04-19 E.I. Du Pont De Nemours And Company Indazoles substitues en tant qu'arthropodicides
CN1069272A (zh) * 1991-08-02 1993-02-24 布茨公司 制备苯并吡或噻喃并吡唑的方法
WO2007075772A2 (fr) * 2005-12-20 2007-07-05 President And Fellows Of Harvard College Composes, essais et methodes de traitement

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014167552A1 (fr) 2013-04-11 2014-10-16 Ofta Sp. Z O. O. Huile essentielle et aloès pour le traitement et la prophylaxie d'inflammations provoquées par demodex, notamment la blépharite marginale, composition pharmaceutique contenant une huile essentielle et/ou de l'aloès et utilisation de l'huile essentielle et de l'aloès et de leurs compositions pour la production d'une préparation utilisée dans le traitement et la prophylaxie des inflammations mentionnées

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