JPS604165A - Sulfonium derivatives - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R1 and R2 are lower alkyl; R3 is H or lower alkyl; R4 is H, lower alkyl, cycloalkyl, carboxymethyl, etc.; R3 and R4 may together form a methylene chain which may together with N bonded thereto form a heterocyclic group; n is 1-3; Y is acid residue). EXAMPLE:Dimethyl-2-cyclohexylcarbamoylethylsulfonium p-toluenesulfonate. USE:It has antiallergic, carcinostatic, anti-inflammatory, analgesic and immunoregulating activities, and is useful as pharmaceuticals and agricultural chemicals. PREPARATION:The compound of formula I can be prepared by reacting the sulfide compound of formula II with the compound of formula R2Y in a solvent or in the absence of solvent at -30-+150 deg.C for about 0.5-72hr.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel sulfonium compound and a method for producing the same.

The sulfonium compound of the present invention is represented by the following general formula (I).

[In the formula, R□ and R2 are the same or different and lower alk+
R3 is a hydrogen atom or a lower alkyl group is a hydrogen atom or a carboxyl group, R6 is a hydrogen atom, a lower alkyl group, a halogen atom, a hydroxyl group, a trifluoromethyl group, a lower acyl group, lower alkyl group, tetrasilylcarbamoyl group, carboxydimethyl group, 3-(2-hydro4-hydro+cytetrahydrofuryl)o+cy group or lower alkoxy+dicarbonylmethylcarbatyl group) are shown respectively. Further, R3 and R1 may be bonded to each other to form a methylene chain, and together with the nitrogen atoms to which they are bonded, form a heterocyclic group. R represents an integer of I-3, and Y represents an acid residue. ] In the above general formula (I), the lower alkyl groups represented by R□, R2, R3, R4 and R6 include alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, -5o hyal, iso''5
D pill, butyl, isobutyl, -butyl, pentyl,
Examples include hexyl group.

In the general formula (I), R4 represents a cycloalyl group having 5 to 7 carbon atoms, pentyl, cycloh+sil, and a co+cy group. C 1 to 6 Al]+ groups, such as methoxy, etho+
shi, zu D piluo + shi, isozuro piluo tenshi, zuto tenshi,
Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms; examples of lower acyl groups include acyl groups having 2 to 6 carbon atoms, e.g. Acetyl, 50-hydroxyl, dityryl, hivaloyl, 50-yl group, etc., can be used as a lower alkyl group and a dicarbonylmethylcarbatyl group having 4 to 9 carbon atoms. , for example, meth-10-dicarbonylmethylcarb7yl, etho-10-dicarbonylmethylcarbamoyl, '50-pyruo + dicarbonylmethyl-carb7yl, isozy-dicarbonylmethyl-carb7yl, d-1-10-dicarbonylmethylcarb7yl, , and dicarbonylmethylcarbatyyl, and dicarbonylmethylcarba7yl, and the like, respectively.

In the general formula (I), R3 and R4 may be bonded to each other to form a methylated chain, such as ethylene, trimethylene,
Examples include tetramethylene chain, beshitamethylene chain, and hesyl methylene chain.

In general formula (I), the acid residue represented by Y may be any acid residue that can be used as a pharmaceutical, and specific examples include the following inorganic acid residues and organic acid residues.

Inorganic acid residues --- hydrogen chloride, hydrogen iodide, hydrogen bromide,
Acid residues such as tetrafluoroboric acid, perchloric acid, and ricic acid.

Organic acid residues: metal sulfonic acid, toluene sulfosic acid, cassifer sulfoshie, 1.5-4'near'2
Organic sulfonic acid residues such as 1- and 7-disulfosic acids, and carpositic acid residues such as lactic acid, maleic acid, and maronic acid.

The sulfonium compound represented by the above general formula (I) of the present invention has antiallergic effects and is useful as a pharmaceutical.

The method for producing the compound of the present invention will be explained below.

The compounds of the present invention can be produced, for example, by the following various methods.

[Manufacturing method A]

A sulfide compound represented by the general formula (in which R□, R3, R4, and R have the same meanings as above) and the general formula % (%) (in which R2 and Y have the same meanings as above) .) is reacted with the compound represented by.

This reaction is carried out in a solvent or without a solvent at -30 to 150°C, preferably 0 to 100°C or less, for a reaction time of 0.5 to 72 hours. Compound (III) may be used in an excess amount relative to sulfide compound (II), but is preferably used in an amount of about 1 to 4 times the theoretical amount. Examples of solvents include alcohols such as methanol, ethanol, and panol; polar solvents such as acetonitrile, dimethylformamide, dimethylsulfonamide, and dimethylsulfonamide; halogenated hydrocarbons such as methylinolide and riOOform; Aromatic hydrocarbons such as beetroot, toluene, and beef sardine; ethers such as ethyl ether and sulfur ether; other acetate, petroleum ether, ethyl acetate, water,
A mixed solvent of these solvents can also be used. The reaction can be carried out in a closed container if necessary.

The sulfide compound (II) used as a raw material is
For example, the general formula % formula % () (wherein R□ and R have the same meanings as above, hal-
indicates a halogen atom. ) and the compound represented by the general formula (in which R3 and R4 have the same meanings as above) are preferably combined with basic compounds, such as alkali metals such as sodium and potassium, and hydrogen thereof. compounds, hydroxides thereof, or carbonates thereof, or in the presence of hydroxides, t-sulfoline, peroxides, pipera, triethylamine, etc., without a solvent or in an appropriate solvent.
It is usually synthesized by reacting at a temperature of about 0°C. Details of the synthesis of the sulfide compound (n) will be described in Reference Examples below.

[Manufacturing method B]

A sulfonium halide represented by the general formula (R1%R2, R3, Ra, and R have the same meanings as above, and X represents a halogen atom) and a sulfonium halide represented by the general formula Z represents a silver atom or an alkali metal atom, and Y□ represents an acid residue other than the halogen atom represented by X.

This method utilizes a salt exchange reaction of a sulfonium halide (■) (in the compound represented by the general formula (I) of the present invention, Y represents a hydrohalic acid residue), and the raw material compound is produced according to production method A above. The sulfonium halide (Vl) can be advantageously used in this reaction in the form of a reaction mixture without being isolated from the reaction system.

Of course, it can also be used after being isolated and purified from the reaction system.

As the compound (■) used as the other raw material compound, silver salts or alkali metal salts of acids capable of providing the acid residue corresponding to Y in the general formula (I) of the present invention can be used. Examples of the above-mentioned acids include inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, perchloric acid, and tetrafluoroboric acid; maleic acid, malonic acid;
Examples include organic acids such as lactic acid, camphorsulfonic acid, metacisulfosic acid, tosylic acid, picrylsulfosic acid, and 1,5-naphthalenedisulfonic acid. Examples of the alkali metals include sodium, potassium, and lithium.

The water-salt exchange reaction is carried out in a solvent at about -30 to 150°C, preferably about 0 to 100°C. Compound (■) is preferably used in a theoretical amount of about 1
~4 times the amount used. As the solvent, any of the same various solvents used in the reaction of production method A above can be used.

[Manufacturing method C]

This method also utilizes a salt exchange reaction, in which silver oxide and a compound represented by the general formula % (in the formula yi has the same meaning as above) are added to the sulfonium pallite (Vl). react with.

The sulfonium halide (Vl) used as a raw material is the same as that shown in Production Method B, and the compound (■) represented by BY□ is the compound represented by Y in the compound represented by the general formula (I) of the present invention. An organic or inorganic acid in free form that can provide the indicated acid residue. A specific example thereof is as shown in the manufacturing method B above.

In this reaction, the amount of silver oxide is usually at least equimolar, preferably about 1 mole or more, based on the sulfonium halide (Vl) used as the raw material.
- Can be used in a 4-fold molar ratio. In addition, the ratio of the acid represented by ff□ is the sulfonium halide (V
It is preferable that the amount is equal to or more, preferably about 1 to 4 times the molar ratio relative to I). This reaction is usually carried out in a solvent from about -30 to 1
It is carried out at 50°C, preferably about 0-100°C. The solvent may be the same as that used in Production Method A above.

The sulfonium compound of the present invention obtained according to the above production method A-CK can be isolated according to a conventional separation method after the reaction is completed. The separation methods include - for example, recrystallization, extraction,
Concentration methods, column filters, etc. can be adopted.

The compound of the present invention has anti-allele f-action as well as K-transmitting action on the immune system of the living body; anticancer action; immunomodulatory action:
Anti-inflammatory and analgesic effect: Liver function improvement effect; Anti-autoimmune effect: Infection protection effect: Side effect prevention of active ingredient compounds such as steroids and anticancer drugs that have immunosuppressive effects as side effects; Adjunct effect for immunotherapy; Platelets Aggregation prevention effect;
It has biological growth regulating effects and is useful as medicines and agricultural chemicals.

When using the compound of the present invention as a medicine,
Various dosage forms can be adopted depending on the therapeutic purpose. Such forms may be, for example, oral preparations, injections, rectal suppositories, inhalants, etc., and the secondary dosage forms can be manufactured by conventional formulation methods known to those skilled in the art. When preparing a solid preparation for oral use, after adding an excipient, if necessary, a binder, a disintegrant, a lubricant, a coloring agent, a flavoring agent, a flavoring agent, etc. to the compound of the present invention, By this method, tablets, coated tablets, granules, powders, force cells, etc. can be manufactured. When preparing an oral liquid preparation, the compound of the present invention may be added with a flavoring agent, a buffering agent,
Oral liquid preparations, ointment preparations, etc. can be manufactured by adding stabilizers, flavoring agents, etc., by conventional methods. When preparing an injection, a pH adjuster, a buffer, a stabilizer, a tonicity agent, a local anesthetic, etc. are added to the compound of the present invention, and a subcutaneous, intramuscular, or intravenous injection is prepared using a conventional method. can be manufactured. When preparing a rectal suppository, the compound of the present invention is added with an excipient and, if necessary, a surfactant and the like, and then the suppository can be produced in a conventional manner. When preparing an inhalant, an excipient, a propellant, etc. may be added to the compound of the present invention as necessary, and the inhalant can be manufactured by a conventional method.

The amount of the compound of the present invention to be incorporated into each of the above dosage unit forms is not constant depending on the symptoms of the patient to whom it is applied or the dosage form, but generally it is about 5 to 5 to 1000■, approximately 0.1 to 500 for injections
■、Approx. 5~1000■ when fully opened, approx. 1~50 when using an inhaler.
It is desirable to set it to 0■. Further, the daily dosage of the drug having the above dosage form cannot be determined unconditionally depending on the symptoms, etc., but it is usually preferably about 0.1 to 5,000 μl.

Next, in order to further explain the present invention, an example of the production of a raw material compound (sulfide compound (■)) for producing the compound of the present invention will be given as a reference example, and then an example of the production of the compound of the present invention will be given as an example.

Reference Example I Synthesis of 2-Schiff O to Zylcarba7ylethyl Methyl Sulfide Ether 1001m to Schiff D to Bovine Siluatrines 21.4F
and triethylamine24. Dissolve Of. To this, under ice cooling, add 30. Add Of. Stir at room temperature for 2 hours and wash the reaction solution with water. After dehydration of Glauber's salt, the ether layer was concentrated, and the residue was recrystallized from beef tenderloin to Schiff D and converted to 2-Schif 0 + zilcarba 7ylethyl methyl sulfide + 2.5 fC yield 97
．． 7%).

rILP93-94℃ Reference Example 2 Synthesis of 2-(methylphenylcarbayl)ethylmethyl sulfide Ji! 10.79 of methylaniline and 9.48 f of hyridyl are dissolved in 100-. To this, under ice cooling, β
-Methyl Mercato''50 Hionilku0 Light 13.9
Add 9. Stir at room temperature for 1 hour, and wash the reaction solution with water.

After mirabilite dehydration, beni, l'l! The filtrate layer was concentrated, and the residue was distilled under reduced pressure to obtain 19.94 g of 2-(methylphenylcarbayl)ethyl methyl sulfide (yield: 95.2 g).

1'P149=I50℃/2 tuH? Example 1 Synthesis of dimethyl-2-cyclohexylcarbyl ethylsulfonium P-toluenesulfonate (compound l) 2-Schiff Dhylcarbyl ethylmethylsulfide 2. After dissolving Olf in Methilink 0 Light 30 Go,
To this was added 5.58 t of methyl p-toluenesulfonate, and the mixture was stirred at room temperature for 48 hours. Ether was added to the reaction solution, the insoluble portion was collected, and recrystallized from ethanol-ether.
Dimethyl-2-cyclo+dylcarbamoylethylsulfonium P-tornidisulfonate (compound 1) 3
-68F (yield 94.8%) is obtained.

mp187-188°C Example 2 Compound 6.
8.12.13.22.23.24 and 25 were synthesized.

Example 3 Synthesis of dimethyl-2-(3-(5-tetrasolyl)phenyl)carbanetylsulfonium p-toluenesulfonate (compound 16) 213-(
3.06 g of 5-tetrasolyl)phenyl 11thylmethyl sulfide was dissolved in 30 g of dimethylformamide.
After dissolving in 11/, 5.58 g of methyl toluenesulfonate was added thereto, and the mixture was stirred at room temperature for 48 hours. Ether was added to the reaction solution, the insoluble portion was removed, and dimethylforma 3F was added.
-Recrystallize from dimethyl-2-(3-(5-
Detrazolyl(phenyl)carb7ylethylsulfonium toluenesulfonate (compound 16) 4.55 F (yield 92.3%) is obtained.

ffi/194-195°C Example 4 Compound 1 shown in Table 1 below was prepared in the same manner as in Example 3.
7 was synthesized.

Example 5 Dimethyl-2-(methylphenylcarb7yl)ethylsulfonium /'-)luenesulfonate (compound 2
) Synthesis of 2-(methylphenylcarb7yl)ethylmethylsulfite 2.09f and methyl p-toluenesulfosinate 6
．． Add 07 and stir at room temperature for 12 hours. Ether was added to the reaction solution, the insoluble portion was separated, and recrystallized from ethanol-ether to give dimethyl-2-(methylphenylcarb7yl)ethylsulfonium p-tornidisulfonate (compound 2) 3.822 (yield 96.5%).

7i7)! 50-151°C Example 6 Compound 4 shown in Table 1 below was prepared in the same manner as in Example 5.
5.9 and 18 were synthesized.

Example 7 Synthesis of dimethyl-2-(4-(5-tetrasilylcarb7yl)phenyl)carbatylethylsulfonium iotide (compound +4) 2-(4-(5-tetralylylcarb7yl)phenyl) ) 3.06f of carbatyl methyl sulfide in dimethylformamide lO
Dissolve in m/. Add 4.21 g of methyl iotide to this and stir at room temperature for 12 hours. Ether was added to the reaction solution, the insoluble portion was scraped off, and recrystallized from methanol-ether to obtain 1. ; Methyl-2-(4-(5-tetrazolylcarbazoyl)phenyljcarba7ylethylsulfonium iotide (compound ++) 4.255' (yield 94.
9ch).

"P264-265°C Example 8 Compound 1 shown in Table ■ below was prepared by the same operation as in Example 7.
9 was synthesized.

Example 9 Dimethyl-2-(4-(5-tetrasilylcarba7yl)phenyl)carba7ylethylsulfonium F-)
Synthesis of 2-(4-(5-tetrasilylcarba7yl)phenyl)carba7ylethyldimethylsulfonium iotide (compound 14) synthesized in Example 7 4.48f was synthesized in Example 7. Dissolve in 30ml of formamide, add 2,79ml of silver P-tornidisulfonate, and stir at room temperature for 1 hour. The reaction solution is filtered, hydrogen sulfide and activated carbon are added to solution F, and the mixture is filtered. The P solution was concentrated, and the residue was purified with dimethylformamide-ether to give dimethyl-2-r4-(5-tetrasilylcarb7yl)phenyl)carb7ylethylsulfonium F-)luenesulfonate (compound +5) 4
．． 52f (yield 91.7%) is obtained.

rILP21B-219°C Example lO Dimethyl-214-(etho+dicarbonylmethylcarb7yl)phenylcarb7yl)ethylsulfonium
Synthesis of p-1-ruenesulfonate (compound 20) 2-(4-(dicarbonylmethylcarbamoyl)phenyl'-carb7yl)ethyldimethylsulfonium acid Tide 4.66F synthesized in Example 8 was dissolved in ethanol 20H. 2.31 r of silver oxide is added thereto, stirred at room temperature for 30 minutes, and then filtered. Add 5 ethanol to solution F
After adding a solution in which 3.44 g of m1VCp-1-luethysulfosic acid was dissolved, the mixture was concentrated. The residue was dissolved in acetonitrile.
Purification with ether gives dimethyl-2-(4-(ethodeca-dicarbonylmethylcarbayl)phenylcarb7yl)
Ethylsulfonium p-tornidisulfonate (compound 20) 4.95F (yield 96.9%) is obtained.

71LP132-135°C Example 11 2-(Carbodimethylcarba7yl)ethyldimethylsulfonium F-tornidisulfonate (Compound 3)
Synthesis of 2-To a solution of 1.77f of (carbodimethylcarbayl)ethyl methyl sulfide in acetate, 73Qm/solution, 4.26f of methyl iotide and then 2.79F of silver p-toluenesulfonate were added, and 12 Stir for an hour.

The reaction solution is filtered, hydrogen sulfide and activated carbon are added to solution F, and the mixture is filtered. The filtrate was concentrated and recrystallized from acetonitrile-ether to give 2-(dimethylcarbamoyl)ethyldimethylsulfonium F-)lecissulfonate,
(Compound 3) 3.45F (yield 95.0%) is obtained.

mP85-86°C Example 12 Dimethyl-2-(4-methoxydiphenylcarb7yl)
Synthesis of ethylsulfonium p-toluenesulfonate (compound 7) 2-(diphenylcarbamoyl in 4-meth)ethyl dimethyl sulfide 2.25F methylinolide 50
Add 4.265' of methyl iotide and then 2-79r of silver P-toluenesulfonate to the solution and stir at room temperature for 12 hours. After filtering the reaction solution, it was treated in the same manner as in Example 1O to obtain dimethyl-2-(diphenylcarbamoyl)ethylsulfonium pt-ruenesulfonate (compound 7) 3.95F (yield 95.9%). ).

mP119-123°C Example 13 Compound 1 shown in Table 1 below was prepared in the same manner as in Example 12.
O111 and 21 were synthesized.

Along with the structure of the compounds (compounds 1 to 25) obtained in each of the above examples, the yield (%) on each side and m of each compound
p (℃), elemental analysis values and nuclear magnetic resonance spectra (N
MR) analysis results (δ value, pprrt) are shown in Table 1 below. In Table 1, the numerical values shown in parentheses in the elemental analysis values are calculated values (h), and the numerical values shown without parentheses are actually measured values (4). 4 NMR
This is a value measured in FiDMSO-d6 using TMS as an internal standard.

Table 1 Examples of formulations using the compounds of the present invention are listed below.

Formulation example 1 tablet Compound 13 toorn9 Lactose 47■ Tou 7a Koshidampusi 5019 Crystalline cellulose 50■ Human 0 Bovine Cydulopyl Cellulose 15 ■ Talc 2 Misaki Magnesium stearate 2mg Ethylcellulose 30 Misaki Fatty acid glycerin ester 2 Misaki 300 capes per summer tablet Tablets are prepared at the above mixing ratio.

Formulation Example 2 Granule Compound 7 200 ways Mannitol 540 ■ Tou 70 Koshidenzu / 100 ■ Crystalline Cellulose 100 Misaki Human 0 + Dipropyl Cell 0-su 50 Misaki Talc 10 W
I? 1000 ml per 1 pack Granules are prepared at the above blending ratio.

Formulation example 3 fine granules Compound 12 200■ Mannitol 520■ Bean starch 100■ Crystal Ce Jl/[1-su 1ooq Hydro+Sizu0 Pill Cellulose 70 Misaki Talc 10 Misaki 1000 Misaki Fine granules are prepared at the above blending ratio.

Formulation example: Capsules Compound 10 100■ Lactose 50■ Tow 70 Koshidenzun 47W Crystalline cellulose 50my Talc 2■ ! 250+II per power cell! A force cell agent is prepared using the above blending ratio.

Formulation Example 5 Dropper Compound 8 1F Refined white sugar 60f Para-hydrochloride + ethyl benzoate 5η Paushido O+Dutyl Cybenzoate 5η Appropriate amount of fragrance coloring agent Total amount +0014! A disinfectant is prepared at the above blending ratio.

Formulation example 6 Injection Compound 1 100■ Appropriate amount of distilled water for injection l tube middle 2d An injection is prepared at the above mixing ratio.

Formulation example 7 Suppositories Compound 11 100■ Uitetspujil F-351400■ 1 piece cost 1500■ Prepare full opening with the above mixing ratio.

Formulation example 8 Inhalant Compound 5 I00■ Sorbitan Seven Oleate 10■ Fu0shi12 9890~ Total amount 10f An inhaler is prepared at the above mixing ratio.

Next, the results of pharmacological action tests and acute toxicity tests of the compounds of the present invention will be shown.

(1) The tissue-tropic antibody used in the shadow spring experiment for allogeneic passive cutaneous anaphylaxis (PCA) is made by binding a dinitrophenyl group to a roundworm body extract (DNP-
A! method by immunizing rats with > and pertussis vaccine [Journal Ozu Immuno [1, ; (J, ImnubnoLagy) 10]
6.1002 (197+)). The serum containing this tissue-affinity antibody was intradermally injected into four points on the back of male Wistar rats (weight 180-200 kg) whose hair had been shaved in advance. DNP-AJ in 48 hours? 1.5
Physiological saline containing yny and Evasys Blue 2.52 1
A reaction was induced by intravenous injection of t/, and 30 minutes later, the rats were sacrificed by exsanguination, using the method of Katayama et al.
-(MicrohioLogy and Immuno
The amount of leaked dye was measured in accordance with 22.89 (+978)) and used as an index of PCA. Compounds were administered intraperitoneally 30 minutes before antigen challenge. The results are shown in Table 2.

Table 2 (2) Acute toxicity test Using tLdY male mice (body weight: 201 kg), the compound was dissolved in physiological saline and administered intraperitoneally, and a lethal dose of 50 L was administered.
D5o (9 in η/) was calculated using the Arazu Taushi method. The results are shown in Table 3 below.

Table 3 (that's all) Satozuka Nishi, Kamita-cho, Itano-gun, Tokushima Prefecture 261-1 0 shots clear person Hiroshi Matsumoto Tokushima Prefecture Itano District Kamiita Town Hikinoji Temple Bundle 31-2 0 shots, part of both sides 3-30-5 Kamiyoshinocho, Tokushima City

Claims (1)

[Claims] ■ General formula [In the formula, R1 and R2 are the same or different and represent a lower alkyl group, R3 is a hydrogen atom or a lower alkyl group, R1,
is a hydrogen atom, a lower alkyl group, a Schiff group, R6 is a hydrogen atom, a lower alkyl group, a halogen atom, a hydroxyl group, a trifluoromethyl group, a lower acyl group, a lower alkyl group, a tetralylyl group group, carboxydimethyl group, 3-
(2-hydro, 4-hydro+cytetrahydrofuryl) or lower alkoxy, luponylmethyl, and hydroxyl, respectively. In addition, R3 and R4 combine with each other to form a methylated chain,
A heterocyclic group may be formed together with the bonded nitrogen atom. R represents an integer of 1 to 3, and Y represents an acid residue. ] A sulfonium derivative represented by ■ General formula [In the formula, R□ is a lower alkyl group, R3 is a hydrogen atom or a lower alkyl group, R4 is a hydrogen atom or a lower lupocyl group, R6 is a hydrogen atom, a lower alkyl group, Halogen atom, hydroxyl group, trifluoromethyl group, lower acyl group, lower alkyl group, tetralylyl group, carboxydimethyl group, 3-(2-o+so-4-hydro, tetrahydrofuryl)o 10-cy group or lower alkoxy+cyclocarbonylmethylcarbayl group) respectively. Also R
3 and R4 may be bonded to each other to form a methylene chain, and may form a heterocyclic group together with the nitrogen atoms to which they are bonded. indicates an integer from 1 to 3. ] A sulfide compound represented by the general formula 2Y [wherein R2 represents a lower alkyl group and Y represents an acid residue. [In the formula, R1%R2, R3, R4, Y and R have the same meanings as above. ] A method for producing a sulfonium compound represented by ■ General formula [In the formula, R□ and R2 are the same or different, lower alk +
R3 is a hydrogen atom or a lower alkyl group, R4 is
is a hydrogen atom, a lower alkyl group, a cycloalkyl group, a carboxydimethyl group, or a group; A lower alkyl group, a tetralylyl group, a carboxydimethyl group, a 3-(2-o+so-4-hydro+cytetrahydrofuryl)oxy group or a lower alk]+dicarbonylmethylcarbayl group show. Further, R3 and R1° may be bonded to each other to form a methylated chain, and together with the nitrogen atoms to which they are bonded, a heterocyclic group may be formed. Path is an integer from 1 to 3 and X is 〇, 'f
'JJgr, indicates child. ] Sulfonium pallite represented by the general formula [where Z is a silver atom or an alkali metal atom and Y□ represents an acid residue other than the halogen atom represented by X]. [In the formula, R□, R2, R3, R4, Y□ and R have the same meanings as above. ] A method for producing a sulfonium compound represented by ■ General formula [In the formula, R□ and R2 are the same or different, lower alk +
R3 is a hydrogen atom or a lower alkyl group, R4 is
represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, a carboxydimethyl group or group, a hydrogen atom, a lower alkyl group, a halogen atom, a hydroxyl group, a trifluoromethyl group, a lower acyl group, Indicates a lower alkyl group, a tetralylylcarb7yl group, a carboxydimethyl group%3-(2-o+so4-hydro+cytetrahydrofuryl)oxy group or a lower alkoxy+dicarbonylmethylcarbatyl group ) are shown respectively. In addition, R3 and R4 combine with each other to form a methylated chain,
A heterocyclic group may be formed together with the bonded nitrogen atom. rL represents an integer of 1 to 3, and X represents a halogen atom. ] In the sulfonium halide represented by the formula, silver oxide and the general formula [wherein, Yi and X represent acid residues other than the hydrogen atom. [In the formula, R1, R2, R3, R4, Y□ and rL have the same meanings as above. ] A method for producing a sulfonium compound represented by