MXPA97001032A - Preparation and utilization of magnesium chloride (3 alcoxi fen - Google Patents
Preparation and utilization of magnesium chloride (3 alcoxi fenInfo
- Publication number
- MXPA97001032A MXPA97001032A MXPA/A/1997/001032A MX9701032A MXPA97001032A MX PA97001032 A MXPA97001032 A MX PA97001032A MX 9701032 A MX9701032 A MX 9701032A MX PA97001032 A MXPA97001032 A MX PA97001032A
- Authority
- MX
- Mexico
- Prior art keywords
- magnesium
- alkyl
- chloride
- magnesium chloride
- alkoxyphenyl
- Prior art date
Links
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L MgCl2 Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 title claims abstract description 49
- 229910001629 magnesium chloride Inorganic materials 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- -1 magnesium halides Chemical class 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 150000002680 magnesium Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000011777 magnesium Substances 0.000 claims abstract description 9
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract description 8
- 230000000875 corresponding Effects 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000006606 n-butoxy group Chemical group 0.000 claims 1
- 235000011147 magnesium chloride Nutrition 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- MJGVPJDEMMMUFN-UHFFFAOYSA-N 1-chloro-3-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=CC(Cl)=C1 MJGVPJDEMMMUFN-UHFFFAOYSA-N 0.000 description 1
- YUKILTJWFRTXGB-UHFFFAOYSA-N 1-chloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1 YUKILTJWFRTXGB-UHFFFAOYSA-N 0.000 description 1
- QDHLEFBSGUGHCL-UHFFFAOYSA-N 2-[(dimethylamino)methyl]cyclohexan-1-one Chemical compound CN(C)CC1CCCCC1=O QDHLEFBSGUGHCL-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N Diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L Magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
The present invention relates to a process for the preparation of magnesium chloride (3-alkoxyphenyl) with 1 to 5 carbon atoms in an alkoxy radical by the reaction of a corresponding chloride (3-alkoxyphenyl) with activated magnesium, obtained by the reduction of magnesium halides with an alkali metal
Description
PREPARATION AND UTILIZATION OF MAGNESIUM CHLORIDE (3-ALCOXY-KNIL) DESCRIPTION OF THE INVENTION The invention relates to a process for the preparation of magnesium chloride (3-alkoxy phenyl), as well as to the use of these compounds, numerous substances Active pharmaceutical and agrochemicals contain the m-anicyl group. This is preferably introduced by means of an organic metal m -anicyl compound, especially by means of a Grignard m -anicyl compound, into the compound to be synthesized. As the Grignard compound, a m -anicyl magnesium bromide, which is obtained by reacting m -anicyl bromide, with metallic magnesium, in a solvent (Arzn. Forsch. / Drug Res. 28 (I), 107) is used for this. (1978) It is usually used in the preparation of the Grignard compounds, the reactive bromides For economic and ecological reasons, it is advantageous to replace the bromides with the less reactive chlorides in the manufacture of Grignard reactants, since the chlorides have a good cost, and otherwise due to their lower molecular weight cause lower salt amounts.In addition, with the use of the chlorides less byproducts are formed.From US Patent 2,959,596 and J. Chem. Soc. 1968, 1265, the preparation and utilization of o- and p-anilyl magnesium chloride is known.In Japanese 60/72833, mentioned in Derwent WPI Scc No. 85-137805 / 23, magnesium chloride (4-ethoxy phenyl) is presented. , without indication of the p manufacturing process. The manufacture and use of magnesium chloride (3-methoxy phenyl) - and (3-ethoxy phenyl), has not been described so far, this is made clear with the electronic deactivation of the aromatics by the alkoxy group in the meta position. The aim pursued basically by the present invention, therefore, consists in the development of a process for the preparation of magnesium chloride (3-alkoxy phenyl). Surprisingly it was now found that the magnesium chloride (3-alkoxy phenyl) can be obtained with carbon atoms of 1 to 5 in an alkoxy radical by the reaction of the corresponding 3-alkoxy phenyl chloride with activated magnesium, obtaining high yields. According to the invention, there is a process for the preparation of magnesium chlorides (3-alkoxy phenyl), with 1 to 5 carbon atoms, in alkoxy radical, which takes place by the reaction of a 3-alkoxy chloride. phenyl, with activated magnesium, obtained by reducing the magnesium halides with an alkali metal. For the process according to the invention, activated magnesium is particularly suitable, which is obtained by reduction of magnesium halides with lithium, sodium or potassium, J. Org. Chem. 52, 3674 (1987), J. Am. Chem. Soc. 96, 1775 (1974).
The reduction is usually carried out with a molar excess of 1 to 5% magnesium halide in a solvent or solvent mixture, for example aliphatic ethers such as tetrahydrofuran, subfluoritric tetraflurane, dimethoxy ethane and / or dimethyl diglycol at temperatures between 65 and 162 °. C. It may be advantageous to carry out the reduction in precensia of alkaline-earth or alkaline salts, for example alkali iodides, alkaline sulfates and alkaline-earth sulfates. The activated magnesium obtained by reduction, without isolation and preferably is reacted with a 3-alkoxy-phenyl chloride having from 1 to 5 carbon atoms in an alkoxy residue to obtain the Gridnard compound. The alkoxy radical with 1 to 5 carbon atoms in the phenyl chloride compound can be branched or cyclic straight chain. Preference is given to using phenyl chloride compounds with an alkoxy radical in the net position, selected from the group methoxy, ethoxy, isopropoxy, n-butoxy and cyclopentoxy, 3-methoxyphenyl chloride and 3-chloro-3-chloro are especially suitable for the reaction with active magnesium. -ethoxyphenyl. According to the process according to the invention, the magnesium chloride compounds can be produced without the formation of side products with high yields. If, on the other hand, 3-alkoxyphenyl chlorides are reacted with non-activated magnesium in the presence of small amounts of dibromethane or according to the process described in European patent 307, 106 for 3-t-butoxyphenyl chloride, with magnesium not activated in the presence of ethyl bromide, the corresponding Grignard components will be obtained only with unsatisfactory yields. On this it is presented that the formation of secondary products grows. With magnesium (3-alkoxyphenyl) chlorides, aldheides and ketones are reacted with good yields to obtain corresponding alcohols. Another object of the present invention is the use of a magnesium chloride (3-alkoxyphenyl) with 1 to 5 carbon atoms in the alkoxy moiety to react with a β-aminoaldheido or 13-amino ketone of the formula I:
wherein R1 is H or C? -4 alkyl, R2 H or C? -4 alkyl or R2 together with R1 - (CH: z) 4 or R2 together with R3 cycloalkyl CA-? Or R2 together with R4 cycloalkyl Cs-β or R2 together with RB a heterocycle with 5 to 8 members, R3 H or straight chain C? -4 alquilo alkyl, R 4 is H and Rß is C 1-3 alkyl, and Rß is C alkyl ? -3, or for the reaction with an aldheido or ketone of Formula II.
0
R
wherein R and Rs are the same or different and each time they mean H, Ci-β alkyl or C3-T cycloalkyl. Preferably, a magnesium chloride (3-alkoxyphenyl) is used in which the alkoxy radical means methoxy, ethoxy propoxy, isopropoxy, n-Butoxy or cyclopentoxy, preferably magnesium chloride 3-methoxyphenyl or magnesium chloride 3-ethoxyphenyl, to react with a β-aminoaldheido or β-amino ketone, especially suitable β-aminoaldheido or β-amino ketone are those of the formula I, in which R 1 is C 1-4 alkyl. R2 H or C? -4 alkyl or R2 together with R1 - (CHj2) 4, R3 means H or straight chain C1-4 alkyl and R4 H, RB CH3 and Rß signifies CH3. The reaction of a β-magnesium chloride compound produced according to the invention is carried out in a known manner, when the Grignard compound is reacted in a solvent or in a solvent mixture, for example aliphatic ethers such as tetrafluorane, tetrafluran substituted, dialkyl or dioxane ethers, and / or aromatic hydrocarbons such as benzole, toluene and / or xylene at temperatures between -78 ° and 120 * with a compound of Formula I or II. EXAMPLES All the works were carried out with dry solvents and the reactions were carried out under an atmosphere of a protective gas. EXAMPLE 1 PREPARATION OF MAGNESIUM CHLORIDE (3-METOXYPENYL). 2.04 g (21.4 mmol) of magnesium chloride were placed in a 100 ml three neck flask, equipped with a thermometer reflux cooler and dropping funnel, and covered with 50 ml of tetrahydrofuran (THF) 0.82 g (21.0 g) were added. mmol) of potassium finished cutting and heated with stirring for 90 minutes at reflux. Then 3.05 g (21.4 mmol) of 3-chloroanisole, dissolved in 20 ml THF under reflux, were dripped in 30 minutes. At the end of the reaction, it was stirred for 20 hours at room temperature and the obtained Grignard compound was applied to another reaction. EXAMPLE 2 PREPARATION OF 2- ((DIMETHYLAMIN) METHYL) -l- (3-MET0XI-PHENYL) -CICLOHKXANOL. To the solution of the magnesium chloride (3-methoxyphenyl) obtained in Example 1, 3.32 g (21.4 mmol) of 2- (dimethylamino) methyl-cyclohexanone dissolved in 10 ml THF in an ice bath was dripped in an ice bath cooling. 40 minute period. After stirring for 24 hours at room temperature under cooling of ice bath, it was hydrolysed with 20 ml of a 20% ammonium chloride solution. The organic phase was separated and the aqueous phase was still extracted twice with ethyl esters of acetic acid. The combined organic phases were dried over magnesium sulfate and filtered. After removal by distillation of the solvent 3.4 g (60% of the theory) of the cyclohexanol compound were obtained.
Claims (8)
- CLAIMS 1.- Process for the preparation of magnesium chloride (3-alkoxyphenyl) with the 5 carbon atoms in an alkoxy radical by the reaction of a corresponding chloride (3-alkoxyphenyl) with activated magnesium, obtained by the reduction of halogenides of magnesium with an alkali metal.
- 2. Method according to claim 1, characterized in that the activated magnesium obtained by the reduction of magnesium chloride is carried out with lithium, sodium or potassium.
- 3. Process according to one or both of the preceding claims characterized in that a chloride (3-alkoxyphenyl) in which the alkoxy radical means methoxy, ethoxy, propoxy, isoproxy, n-butoxy or cyclopentoxy is reacted with activated magnesium.
- 4. Process according to one or more of the preceding claims, characterized in that chloride (3-methoxyphenyl) or chloride (3-ethoxyphenyl) has been reacted with activated magnesium.
- 5. Use of a magnesium chloride (3-alkoxyphenyl) of 1 to 5 carbon atoms in an alkoxy radical for the reaction with a β-aminoaldheido or β-amino ketone of the formula I: R 2 H 5 in which R 1 is H or C 1-4 alkyl, R 2 H or CX-A alkyl. O R2 together with R3- - (CH = or R2 together with R3 cycloalkyl C * -to R2 together with R4 cycloalkyl Cß-β or R2 together with Rβ a heterocycle with 5- to 8-membered, R3 H or C1-4 alkyl of straight chain, R 4 is H and R 3 is C 1-3 alkyl, and R 3 is C 1-3 alkyl, or for the reaction with an aldheido or ketone of Formula II.0. il R7 Rß in which R "7 and Re are the same or different and each time they mean H, Ci-β alkyl or Cß-β cycloalkyl
- 6. Use according to claim 5, characterized in that a magnesium chloride (3- alkoxyphenyl) for the reaction with a β-aminoaldheido or β-amino ketone
- 7. Use according to one of claims 5 or 6, characterized in that a magnesium chloride (3-alkoxyphenyl) is used for the reaction with a β- aldheido or β-amino ketone of Formula I, wherein R 1 is C 4 -4 alkyl, R 2 H or C 4 -4 alkyl or R 2 together with R * - (CH 2), R 3 means H or C 4 -4 alkyl of straight chain and R4 H, R ° CH3 and Rβ means CH3
- 8. Use according to one or more of claims 5 to 7, characterized in that a magnesium chloride (3-alkoxyphenyl) is used in which the alkoxy radical means methoxy, ethoxy, propoxy, isopropoxy, n-butoxy or cyclopentoxy 9.- Use according to one or more of claims 5 to 8, characterized because magnesium chloride (3-methoxyphenyl) or magnesium chloride (3-ethoxyphenyl) is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX9701032A MX9701032A (en) | 1997-02-10 | 1997-02-10 | Magnesium chlorides (3-alkoxy-phenyl) preparation and utilization. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19605778.7 | 1996-02-16 | ||
| MX9701032A MX9701032A (en) | 1997-02-10 | 1997-02-10 | Magnesium chlorides (3-alkoxy-phenyl) preparation and utilization. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MXPA97001032A true MXPA97001032A (en) | 1998-01-01 |
| MX9701032A MX9701032A (en) | 1998-01-31 |
Family
ID=39165506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX9701032A MX9701032A (en) | 1997-02-10 | 1997-02-10 | Magnesium chlorides (3-alkoxy-phenyl) preparation and utilization. |
Country Status (1)
| Country | Link |
|---|---|
| MX (1) | MX9701032A (en) |
-
1997
- 1997-02-10 MX MX9701032A patent/MX9701032A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK281765B6 (en) | Method for production finasteride and intermediate products for its realisation | |
| IE930475A1 (en) | Process for the preparation of¹N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine¹and acid addition salts thereof | |
| RU2017728C1 (en) | Method of n-alkylated ureas synthesis | |
| US7282517B2 (en) | Method of manufacturing glimepiride and the respective intermediate | |
| KR100541786B1 (en) | A method for preparing alcohols by using (3-alkoxyphenyl)magnesium chlorides | |
| US20020040164A1 (en) | High purity (1R, 2S, 4R) -(-) -2- [ (2' -{N,N-dimethylamino} -ethoxy) ] -2- [phenyl] -1, 7,7 -tri - [methyl] -bicyclo [2.2.1] heptane and pharmaceutically acceptable acid addition salts thereof and a process for the preparation of these compounds as well as medicaments containing 1 or more of these compounds and their use | |
| JP2008546818A (en) | Process for producing 1- [cyano (4-hydroxyphenyl) methyl] cyclohexanol compound | |
| JPH02306947A (en) | Preparation of chiral bata-amino acid | |
| MXPA97001032A (en) | Preparation and utilization of magnesium chloride (3 alcoxi fen | |
| JPH06340571A (en) | Preparation of cyclopentenone | |
| JPH11322643A (en) | Production of chloroalkyne and alkynylamine | |
| JPS63243070A (en) | Improved esterification of thiopropionate | |
| JPH02713A (en) | Optically active alcohol, cyanohydrin and production thereof | |
| JP4056187B2 (en) | Method for producing aromatic dihydroxy compound | |
| JP2002179612A (en) | Method for producing 2,3-dibromosuccinic acid compound | |
| JP3509419B2 (en) | Preparation of diaryl carbonate | |
| JP3799580B2 (en) | Process for producing N-substituted-N-sulfonylamides | |
| JP4081588B2 (en) | Process for producing N-trialkylmethylcarbonyl-2-alkyl-3,4-difluoroaniline | |
| JPH0710829B2 (en) | Method for producing benzyl mercaptan derivative | |
| JPH0674250B2 (en) | Method for producing thiocarbamate derivative | |
| WO1997045433A1 (en) | Process for the preparation of benzyl-metal compounds and process for the preparation of 4-phenyl-1-butenes by the use of the same | |
| JPH0240370A (en) | Production of pyrazine derivative | |
| JPS6121955B2 (en) | ||
| JPH08183773A (en) | Substituted pyridinesulfonylcarbamate-based compound and its production | |
| JPS6327338B2 (en) |