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WO1992013842A1 - Compose de sulfonamidopyridine - Google Patents

Compose de sulfonamidopyridine Download PDF

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Publication number
WO1992013842A1
WO1992013842A1 PCT/JP1992/000011 JP9200011W WO9213842A1 WO 1992013842 A1 WO1992013842 A1 WO 1992013842A1 JP 9200011 W JP9200011 W JP 9200011W WO 9213842 A1 WO9213842 A1 WO 9213842A1
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WO
WIPO (PCT)
Prior art keywords
group
pyridyl
carbon atoms
cyclohexyloxy
methanesulfonamide
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/JP1992/000011
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English (en)
Japanese (ja)
Inventor
Kensei Yoshikawa
Yutaka Ohuchi
Shiuji Saito
Yoh-Ichi Shimazaki
Katsuo Hatayama
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Taisho Pharmaceutical Co Ltd
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Taisho Pharmaceutical 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 Taisho Pharmaceutical Co Ltd filed Critical Taisho Pharmaceutical Co Ltd
Publication of WO1992013842A1 publication Critical patent/WO1992013842A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached

Definitions

  • the present invention relates to a sulfonamidoviridine compound having an anti-inflammatory action, an antipyretic action, an analgesic action, and an anti-allergic action.
  • Honoki The purpose of Honoki is to provide a new, highly safe, sulfonamide-type compound that has anti-inflammatory, antipyretic, analgesic and anti-allergic activities.
  • the inventors of the present invention have conducted extensive research and found that certain sulfonamidoviridine compounds have strong anti-inflammatory, antipyretic, analgesic and anti-allergic effects, and completed the present invention.
  • the present invention provides a formula
  • the halogen atom is a fluorine atom, a chlorine atom, a bromine atom or a chlorine atom.
  • the alkyl group having 1 to 3 carbon atoms is a linear or branched alkyl group, a methyl group, an ethyl group, a propyl group or an isopropyl group.
  • An alkyl group having ⁇ to 5 carbon atoms is a straight-chain or branched-chain allyl ⁇ . Examples are a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an ethylpropyl group.
  • the alkenyl group having 3 to 5 carbon atoms is a linear or branched alkenyl group, for example, a diaryl group, a propenyl group, or a 3-methyl-2-butenyl group.
  • An alkanoyl group having 1 to 5 carbon atoms is a linear or branched alkynyl tumor such as formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl. , Is an ispareryl group.
  • Alkyl groups having 2 to 5 carbon atoms which are S-substituted by alkoxy groups having 1 to 3 carbon atoms, are, for example, methoxyacetyl, ethoxyacetyl, propoxycetyl, methoxypropionyl, d Toxidipropionyl group, propoxypropionyl group, methoxybutyryl group, ethoxybutyryl group, propoxybutyryl group, methoxyvaleryl group, ethoxyvaleryl group, and propoxyvaleryl group.
  • alkanoyl group having 2 to 5 carbon atoms substituted by an alkanoyloxy group having 1 to 4 carbon atoms is, for example, a formyloxyacetyl group, an acetoxyacetyl group, a propionyloxyacetyl group.
  • petyryl xyl acetyl formyl xyl propionyl, acetoxypropionyl, propyl niloxy dipropionyl, petyryl xyl propionyl, formyl xiptyril, acetoxy butyryl, propionyl Xylbutyryl group, Butyryloxybutyryl group, Formyl Xylivaleryl group, Acetoxyvaleryl group, Propionyl group Xipaleryl group, and Petyryloxyvaleryl group.
  • Alkenyl groups having 3 to 7 carbon atoms are straight-chain or branched-chain alkenoyl groups, such as acryloyl, crotonyl, 3-butenoyl, and methyl alcohol. Loyl, 3-pentenyl, 4-pentenyl, 3-methylcrotenyl, and 2-heptenoyl.
  • An alkoxycarbonyl group having 2 to 7 carbon atoms is a straight-chain or branched-chain alkoxycarbonyl group, such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, and isopropoxycarbonyl.
  • the alkoxyalkyl group having several carbon atoms is, for example, a methoxydimethyl group, an ethoxymethyl group, a proviroxymethyl group, a methoxethyl group, or an ethoxyethyl group.
  • the cycloalkyl group having 4 to 7 carbon atoms is a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group or a cyclohexylcarbonyl group.
  • An alkanesulfonyl group having 1 to 3 carbon atoms is a methylsulfonyl group, an ethanesulfonyl group, a propanesulfinyl group or an isopropylsulfonyl group.
  • the cycloalkyl group having 4 to 8 carbon atoms is a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group or a cyclooctyl group.
  • R 1 is a methyl group or an ethyl group
  • R 2 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms.
  • R 3 is a cycloalkyl group having 5-7 carbon atoms, off I nil Or a compound that is a phenyl group "substituted with one or two halogen atoms".
  • the most preferred compounds of the present invention are N- (2-cyclohexyloxy-1-6-nitro-3-pyridyl) -N-methylmethanesulfonamide, N-
  • R 1 is R 2 is a hydrogen atom
  • R 3 is a cycloalkyl group having 5 to 7 carbon atoms, a phenyl group or a phenyl group ⁇ substituted with one or two halogen atoms ''
  • the compound of formula (1) is not only highly potent in itself, but also preferable in that it is an intermediate for the production of the above-mentioned N-substituted sulfonamide pyridine compound [compound of formula (I) wherein R 2 is other than a hydrogen atom].
  • particularly preferred compounds are N- (2-cyclohexyloxy-6-nitro-3-pyridyl) methansulfonamide and N- (2-cyclohexyloxy-1-6-2-trough-3-bi). Lysyl) ethanesulfonamide, N- (2-cycloheptyl 6-nitro-13-pyridyl) methanesulfonamide, N— (6-nitro1-2-phenoxy-13-pyridyl) methanesulfone Amid, N— [2- (2-fluorophenoxy) -1-6-nitro-3-pyridyl] methanesulfonamide, N— [2-(3-fluorophenoxy) -16-two tro-3-pyrid [Jil] methanesulfonamide, N— [2- (4-fluorophenoxy) -16-2 tro-3-pyridyl] methansulfonamide, N— [2- (4-chlorophenoxy) -16— Two Toro 3 — Pyrid
  • the compound of the formula (I) of the present invention can be produced, for example, as follows.
  • R 1 and R 3 have the same meanings as above, and R 2 ′ is R 2 ⁇ other than a hydrogen atom.
  • Examples of the base in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrides such as sodium hydride and potassium hydride, sodium carbonate and potassium carbonate.
  • Alkali gold / carbon bicarbonate such as alkali gold bicarbonate, sodium bicarbonate, potassium bicarbonate, sodium metal, sodium amide and the like can be used.
  • This reaction is carried out without solvent or water, dihydroquinone, tetrahydrofuran, ethyl ether, Ishidomari ether, hexane,
  • the reaction can be performed with a solvent such as hexane, benzene, toluene, xylene, pyridine, N, N-dimethylformamide ', dimethylsulfoxide, dichloromethane, and chloroform.
  • the reaction can be accelerated by adding a quaternary ammonium salt such as potassium iodide or triethylbenzylammonium chloride, or a crown ether such as 18-crown-16 ether.
  • the reduction method may be a normal reduction method of reducing the nitro group to an amino form, such as catalytic reduction using palladium-carbon, Raney-nickel, platinum or the like as a catalyst, reduction using iron or tin, sodium sulfide, or the like. Reduction using ammonium chloride, reduction using sodium borohydride, lithium aluminum hydride, or the like can be used.
  • the solvent used in this reaction may be arbitrarily selected by a reduction method, but generally, alcohols such as methanol, ethanol, and propanol, water, acetic acid, ethyl ethyl dichloride, dioxane, tetrahydrofuran, and acetonitrile are used. Setonitrile or the like can be used.
  • the reaction When a sulfonic acid compound is used in this reaction, it is preferable to carry out the reaction in the presence of a box mixture such as N, N'dicyclohexylcarposimide.
  • a reactive derivative When a reactive derivative is used, it is preferably carried out in the presence of a base.
  • the base may be an inorganic base such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like, or triethylamine, 4- methylmorpholine, 1-methylbiperidine, viridin.
  • an organic base such as N.N-dimethylaminoviridine.
  • this reaction is usually carried out using dichloromethane, chloroform, ethyl acetate, dioxane, tetrahydrofuran, ethyl ether, benzene, toluene, xylene, acetone, acetone, water, viridin, N In a solvent such as dimethylformamide, dimethylsulfoxide, etc .: Then, the compound of the formula (V) is converted into a compound using nitric acid or a nitrate to form a compound of the present invention wherein R 2 is a hydrogen atom in the formula (I) [the compound of the formula (Ia) ] Can be obtained.
  • the nitrate in this reaction includes sodium nitrate, potassium nitrate, iron nitrate and the like.
  • the reaction is carried out without a solvent or using acetic acid, acetic anhydride, trifluoroacetic acid, sulfuric acid, dichloromethane, chloroform, benzene, dioxane, ethanol or the like as a solvent.
  • the compound of the present invention in which R 2 is other than a hydrogen atom [the compound of the formula (Ib)] can be obtained from the compound of the formula (Ia) as follows.
  • R 2 is an alkyl group having 5 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 4 carbon atoms, an acetonyl group or a benzyl group.
  • a compound of the formula (lb) is prepared by converting a compound of the formula (Ia) into a compound of the formula (Ia) in the presence of a base.
  • R 4 is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 4 carbon atoms, an acetonyl group or a benzyl group.
  • X represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyl pheasant group or a P-toluenesulfonyl xy group.
  • examples of the base include sodium hydride, potassium hydride, calcium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, and the like.
  • Inorganic base or sodium methoxide, sodium ethoxide, potassium ptoxide, triethylamine, 4-methylmorpholine, 1-methylbiperidine, pyridine, ', N-dimethy Organic bases such as ruaminoviridine can be used.
  • this reaction was carried out in the following manner: a) Dichloromethane, black form, ethyl ethyl sulphate, dioxane, tetrahydrofuran, ethyl ether, benzene, toluene, xylene, acetone, acetonitrile, water, pyridine, It is performed in a solvent such as N, N-dimethylformamide and dimethylsulfoxide.
  • R 2 is replaced by an alkanoyl group having 1 to 5 carbon atoms, or an ⁇ alkanoyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 4 carbon atoms ''
  • a compound of the formula (lb), which is a benzyloxycarbonyl group or an C1-C3 alkenyl sulfonyl group (the compound of the formula (Ia) is
  • R 5 is an alkanoyl group having 1 to 5 carbon atoms, ⁇ substituted by an alkoxy group having 1 to 3 carbon atoms or an alkanoyloxy group having 1 to 4 carbon atoms.
  • atoms 2-5 Arukanoiru group, three to seven carbon atoms amino Arukenoiru group, carbon atoms 2-7 amino alkoxy Cal Poni group, Shikuroa Rukirukaruponiru group having 4 to 7 carbon atoms, Benzoiru group, benzyl A carboxycarbonyl group or an alkanesulfonyl group having 1 to 3 carbon atoms.
  • a reactive derivative thereof for example, an acid halide, an acid anhydride or the like.
  • the reaction when the compound of the formula (Ia) is reacted with the compound of the formula (VII), is the reaction carried out in the presence of a condensing agent such as K-dicyclohexylcarpoimide? I like it.
  • a condensing agent such as K-dicyclohexylcarpoimide? I like it.
  • the reaction is preferably carried out in the presence of a base.
  • sodium hydride, lithium hydride, calcium hydride, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, carbonate are used as bases.
  • Inorganic bases such as potassium, sodium hydrogencarbonate, and potassium hydrogencarbonate, or sodium methoxide, sodium ethoxide, potassium butoxide, triethylamine, 4-methylmorpholine, 1-methylbiperi Organic bases such as gin, pyridine, N, N-dimethylamino pyridine, 1,8-diazabicyclo [5,4,0] -17-decene can be used.
  • this reaction is usually carried out with dichloromethane, chloroform, ethyl citrate, dioxane, tetrahydrofuran, ethyl ether, benzene, toluene, zidylene, acetate, and acetate nitrile.
  • the reaction is performed in a solvent such as water, viridine, N, N-dimethylformamide, dimethylsulfoxide.
  • Y represents a chlorine atom, a bromine atom or an iodine atom, and ⁇ has the same meaning as described above.
  • the compound can be obtained by subjecting a compound represented by the formula to a ring closure reaction in the presence of a base [ Formula (IX)].
  • examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrides such as sodium hydride and potassium hydride, and alkali metal carbonates such as sodium carbonate and potassium carbonate. Salts, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate, inorganic bases such as sodium metal, potassium potassium and sodium amide or triethylamine, 4-methylmorpholine, 1-methylbiperidine, pyridine, N And organic bases such as N-dimethylaminopyridine.
  • This reaction is carried out without solvent, or in water, dioxane, tetrahydrofuran, ethyl ether, petroleum ether, hexane, cyclohexane, benzene, toluene, xylene, pyridine, N, N-dimethylformamide, dimethyl
  • the reaction can be carried out in a solvent such as sulfoxide, acetonitril, dichloromethane, and 1-port form.
  • the reaction is accelerated by adding a quaternary ammonium salt such as potassium iodide, triethylbenzylammonium chloride, or a crown ether such as 18-crown-16 ether. You can also.
  • the compounds of the present invention can be administered orally or parenterally in conventional dosage forms.
  • Dosage forms include tablets, powders, granules, powders, capsules, solutions, emulsions, suspensions, and injections, all of which can be manufactured by conventional methods.
  • the dosage When used as an anti-inflammatory, antipyretic or analgesic in humans, the dosage varies depending on age, body weight, symptoms, administration route, etc., but is usually 20 to 100 mg per day.
  • Chloromethanesulfonylk was added to a solution of 16 g of pyridine containing 3.0 g of 3-amino-2-cyclohexylpyruxylidine obtained in Example 1 (1) to (2) under ice-cooling. 2.6 g of chloride was added, and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction solution, and the precipitate was collected by filtration and recrystallized from ethanol to obtain 3.2 g of colorless prism crystals of N- (2-cyclohexylhexyl-3-pyridyl) chloromethansulfonamide. Obtained.
  • Acetic anhydride was added to the viridin 6.5 ml solution containing 1.0 g of N- (2-cyclohexyloxy-6-nitro-13-pyridyl) methansulfonamide obtained in Example 1 at room temperature at room temperature. 49 g, and after stirring for 2.5 hours, water was added to the reaction solution, and the precipitate was collected by filtration. The crystals were recrystallized from nor-pi-hexane to obtain yellow plate-like ⁇ -acetyl- ⁇ - (2-cyclohexylhexyl-1-6--2-tro-3-pyridyl) methanesulfonamide 0.95 s. .
  • Example 2 A solution of N- (2-cyclohexyloxy-1-6-thro-3-pyridyl) methanesulfonamide (1.0 g) and triethylamine (0.64 g) obtained in Example 1 was added to a 13 ml solution of dichloromethan ice-cooled. Below, 0.64 g of kuguchi ⁇ carbonate was added and the mixture was stirred at room temperature for 45 minutes. Water was added to the reaction solution, and after extraction with dichloromethane, the organic layer was washed with water and saturated brine in that order, and dried over anhydrous magnesium sulfate.
  • N- (2-cyclohexyl-1-6-tert-pyridyl) chloromethansulfonamide obtained in Example 3, methoxymethyl chloride was reacted instead of methyl iodide.
  • N- (2-cyclohexyloxy-6-2-tro-3-pyridyl) -1-N-methoxymethylchloromethansulfonamide was obtained in the same manner as in Example 5.
  • N- (6-nitro-2-phenoxy-13-pyridyl) methylsulfonamide obtained in the same manner as in Example 2 was used, except that acrylyl iodide was reacted instead of methyl iodide.
  • N-aryl.N- (6-nitro-2-furinoxy-13-pyridyl) methanesulfonamide was obtained.
  • N- (2-cycloheptyl-6-2-di-3-1-pyridyl) methansulfonamide obtained in the same manner as in Example 1, N-acetyl--(2- Cycloheptyloxy 6-nitro 3-pyridyl) methansulfonamide was obtained.
  • N— [2- (4-fluorophenoxy) -16-nitro-3-pyridyl] methanesulfonamide obtained in Example 2 or the N— [2 -— ( 4-Chlorophenoxy) 1 6 -2 Tro 3 -pyridyl] Methanesulfonamide is the same as in Example 6, except that ⁇ -benzoic anhydride is reacted with brobionic anhydride or benzoic chloride instead of anhydride. The following compounds were obtained.
  • This compound has anti-inflammatory, antipyretic, analgesic, and anti-allergic effects, and has few side effects such as gastrointestinal disorders. It is.
  • Table 1 shows the results and the administered doses of the specimens.
  • Adjuvant arthritis was induced by subcutaneous injection of 0.7% mycobacterium tuberculosis suspended in liquid paraffin into the left leg of a Louis rat (7 per group). 15 to 18 days after adjuvant administration, using a well-developed arthritis rat, a sample suspended in a 5% aqueous solution of arabic gum was orally administered once a day for 4 days at a dose of 1 ml per 100 g body weight. The day after the final administration, the paw volume was measured, and the swelling inhibition rate was determined to examine the therapeutic effect. The dose of the test sample was 1 mg Z kg.
  • the adjuvant arthritis (pain) test was performed according to the method of Katsuno et al. [Chem. Pharm. Bui I., Vol. 23, No. 6, pp. 1184 (1975)]. Conducted in compliance. Lewis rats (10 per group) were injected subcutaneously with 0.7% mycopacteriam bergberg-Isis suspended in liquid paraffin into the left foot of the leg (adjuvant arthritis). Was triggered.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

Est décrit un nouveau composé de sulfonamide possédant des activités anti-inflammatoire, anti-pyrétique, analgésique et antiallergique. Ce composé de sulfonamidopyridine est représenté par la formule générale (I) où R1 représente alkyle C¿1? à C3 ou alkyle C1 à C3 à substitution halogène; R?2¿ représente hydrogène, alkyle C¿1? à C5, alcényle C3 à C5, alcanoyle C1 à C5, alcanoyle C2 à C5 substitué par alcoxy C1 à C3 ou alcanoyloxy C1 à C4, alcénoyle C3 à C7, alcoxycarbonyle C2 à C7, alcoxyalkyle C2 à C4, acétonyle, cycloalkyle carbonyle C4 à C7, benzyle, benzoyle, benzyloxycarbonyle ou alcanesulfonyle C1 à C3, ou bien en variante R?1 et R2¿ sont combinés l'un avec l'autre pour représenter alkylène C¿3? à C4; et R?3¿ représente cycloalkyle C¿4? à C8, phényle ou phényle à substitut ion halogène.
PCT/JP1992/000011 1991-02-09 1992-01-10 Compose de sulfonamidopyridine Ceased WO1992013842A1 (fr)

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JP10401191 1991-02-09
JP3/104011 1991-02-09

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WO1992013842A1 true WO1992013842A1 (fr) 1992-08-20

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995022528A1 (fr) * 1994-02-22 1995-08-24 Handforth Investments Ltd. 2-(4-methoxyphenoxy)-3-pyridineamine, sa preparation et son utilisation comme agent anti-inflammatoire
EP1962847A4 (fr) * 2005-12-05 2010-10-06 Glaxo Group Ltd Modulateurs de pyridinylsulfonamide de recepteurs de chimiokine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4962478A (fr) * 1972-08-10 1974-06-17

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4962478A (fr) * 1972-08-10 1974-06-17

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995022528A1 (fr) * 1994-02-22 1995-08-24 Handforth Investments Ltd. 2-(4-methoxyphenoxy)-3-pyridineamine, sa preparation et son utilisation comme agent anti-inflammatoire
US5672613A (en) * 1994-02-22 1997-09-30 Handforth Investments Ltd. 2-(4-methoxyphenoxy)-3-pyridineamine, its pharmaceutical compositions and therapeutic use
RU2141950C1 (ru) * 1994-02-22 1999-11-27 Хэндфорт Инвестментс Лтд. 3-амино-2-(4-метоксифенокси)пиридин или его фармацевтически приемлемая соль, используемые для изготовления лекарства для лечения воспалительных заболеваний, фармацевтическая композиция на их основе и способ получения
EP1962847A4 (fr) * 2005-12-05 2010-10-06 Glaxo Group Ltd Modulateurs de pyridinylsulfonamide de recepteurs de chimiokine

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