JPH0317053A - Production of alkylamide - Google Patents
Production of alkylamideInfo
- Publication number
- JPH0317053A JPH0317053A JP15073089A JP15073089A JPH0317053A JP H0317053 A JPH0317053 A JP H0317053A JP 15073089 A JP15073089 A JP 15073089A JP 15073089 A JP15073089 A JP 15073089A JP H0317053 A JPH0317053 A JP H0317053A
- Authority
- JP
- Japan
- Prior art keywords
- sulfonamide
- alkylamide
- toluenesulfonamide
- acid ester
- phenoxyethyl
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 amine compounds Chemical class 0.000 claims abstract description 20
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 9
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 12
- 150000002148 esters Chemical class 0.000 abstract description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- 239000000654 additive Substances 0.000 abstract description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 230000000996 additive effect Effects 0.000 abstract description 2
- 239000002798 polar solvent Substances 0.000 abstract description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- MSIGTXLXMVOOQD-UHFFFAOYSA-N 2-phenoxyethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOC1=CC=CC=C1 MSIGTXLXMVOOQD-UHFFFAOYSA-N 0.000 abstract 1
- GFWIFFQPVZMFJC-UHFFFAOYSA-N 4-(3-phenoxypropyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCCOC1=CC=CC=C1 GFWIFFQPVZMFJC-UHFFFAOYSA-N 0.000 abstract 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- MROCYLWEFRCECF-UHFFFAOYSA-N 2-(2-phenylethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1CCC1=CC=CC=C1 MROCYLWEFRCECF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NMBWXBWFDHVLGS-UHFFFAOYSA-N 2-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1S(N)(=O)=O NMBWXBWFDHVLGS-UHFFFAOYSA-N 0.000 description 1
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- VJDZMZAZDFKMSV-UHFFFAOYSA-N benzene-1,2-disulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1S(N)(=O)=O VJDZMZAZDFKMSV-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LQSREEOMSMIKAX-UHFFFAOYSA-N hexane-1,6-disulfonamide Chemical compound NS(=O)(=O)CCCCCCS(N)(=O)=O LQSREEOMSMIKAX-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- OHPZPBNDOVQJMH-UHFFFAOYSA-N n-ethyl-4-methylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=C(C)C=C1 OHPZPBNDOVQJMH-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（ 発明の分野 ）
本発明は中間体および添加剤として有用なアルキルアミ
ドの製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention This invention relates to a process for producing alkylamides useful as intermediates and additives.
（ 従来の技術 ）
トルエンスルホニルクロリドの如き酸クロリドとアミン
化合物を反応させてアミドを得る事は良く知られている
。たとえば Ｍａｒｖｅｌら ＪＡＣＳ ５１ １
２７３ など
またアミド化合物を鹸化してアミンに導く事もよくしら
れている。たとえば 浜田らＪＡＣＳ１０２ ３９８
７ など
ところが従来アミン化合物は非常に人手しにくく，特に
Ｗ１換基を持つアミン化合物は極めて限られていた。(Prior Art) It is well known that an amide can be obtained by reacting an acid chloride such as toluenesulfonyl chloride with an amine compound. For example, Marvel et al. JACS 51 1
It is also well known that amide compounds such as 273 can be saponified to form amines. For example, Hamada et al. JACS102 398
However, in the past, amine compounds such as those with W1 substituents were extremely difficult to handle, and in particular, amine compounds with a W1 substituent were extremely limited.
従って．ｉ換していてもよいアルキルアミドの簡便な合
成方法の開発が待たれていた。Therefore. The development of a simple method for synthesizing alkylamides which may be substituted with i has been awaited.
また本発明の化合物は電子供与性無色染料と電子受容性
化合物との接触を利用した記録材料の添加剤としても有
用である。The compound of the present invention is also useful as an additive for recording materials that utilize contact between an electron-donating colorless dye and an electron-accepting compound.
従って，本発明の目的は簡便なアルキルアミドの製造方
法を提供するものである。Therefore, an object of the present invention is to provide a simple method for producing an alkylamide.
（ 発明の構戊 ）
本発明の上述の目的は，塩基の存在下に，スルホンアミ
ドと置換していてもよいアルキルスルホン酸エステルを
反応させる事を特徴とするアルキルアミドの製造方法を
開発する事により達成された。(Structure of the Invention) The above-mentioned object of the present invention is to develop a method for producing an alkyl amide, which is characterized by reacting a sulfonamide with an optionally substituted alkyl sulfonic acid ester in the presence of a base. achieved by.
本発明でスルホンアミドとしてはアルキルまたはアリー
ルスルホンアミドが好ましく，とくに少なくとも１個の
水素原子を持つスルホンアミドが好ましい。In the present invention, the sulfonamide is preferably an alkyl or aryl sulfonamide, particularly a sulfonamide having at least one hydrogen atom.
メタンスルホンアミド、ブタンスルホンアミド２ エチ
ルヘキサンスルホンアミド、１．６ ヘキサンジスル
ホンアミド等の脂肪族スルホンアミド，核が１個以上の
アルキル基，アルコキシ基，ハロゲン原子、スルホ基，
カルボキシ基，アシル基，等で置換していてもよいアリ
ールスルホンアミド例えばベンゼンスルホンアミド，ト
ルエンスルホンアミド，メトキシベンゼンスルホンアミ
ドＮ−メチルトルエンスルホンアミド． ｌ， ３
ベンゼンジスルホンアミド等がある。なかでも○／Ｐ一
またはＰ−｝ルエンスルホンアミドが好都合にもちいら
れる。Methanesulfonamide, butanesulfonamide 2 Ethylhexane sulfonamide, 1.6 Aliphatic sulfonamides such as hexanedisulfonamide, alkyl groups with one or more nuclei, alkoxy groups, halogen atoms, sulfo groups,
Arylsulfonamides optionally substituted with carboxy groups, acyl groups, etc., such as benzenesulfonamide, toluenesulfonamide, methoxybenzenesulfonamide N-methyltoluenesulfonamide. l, 3
Examples include benzenedisulfonamide. Among them, ○/P- or P-}luenesulfonamide is conveniently used.
アルキルスルホン酸エステルとしては，炭素原子数約五
四以下の置換していてもよい固体若しくは液体等があげ
られる。工業的な見地からは．エーテル，エステル，カ
ルボニル又はハロケン原子などから選ばれた官能基を一
個以上持つ置換アルキルが好ましい。エーテル結合は，
２、３または４位にあることが好ましい。とくに２位に
．アルコキシまたはアリールオキシなどから選ばれたエ
ーテル結合のある化合物は出発原料のアルコールが．ア
ルキレンオキシド．アルキレンカーボネート等を利用し
て合或し易く．入手の点から好都合である。アルキルス
ルホン酸エステルは定法に従って，アルコールとスルホ
ニルクロリドとを塩基の存在下に反応させる事により得
られる。Examples of the alkyl sulfonic acid esters include optionally substituted solids or liquids having about 54 or less carbon atoms. From an industrial standpoint. Substituted alkyl having one or more functional groups selected from ether, ester, carbonyl, haloken, etc. is preferred. The ether bond is
Preferably in the 2nd, 3rd or 4th position. Especially in second place. Compounds with an ether bond selected from alkoxy or aryloxy, etc., have a starting material of alcohol. Alkylene oxide. Easy to combine using alkylene carbonate, etc. It is convenient in terms of availability. Alkyl sulfonate esters can be obtained by reacting alcohol and sulfonyl chloride in the presence of a base according to a conventional method.
スルホニルクロリドのスルホン酸部分としては、上で述
べたと同様にアルヰル又はアリールスルホン酸例えばＰ
−｝ルエンスルホン酸が好都合に用いられる。従って，
置換基を持つアルコールのトルエンスルホン酸エステル
が最も好都合で有ることが，理解されよう。As the sulfonic acid moiety of the sulfonyl chloride, alwyl or aryl sulfonic acids such as P
-}Luenesulfonic acid is advantageously used. Therefore,
It will be appreciated that toluenesulfonic esters of substituted alcohols are most advantageous.
モル比は１：１乃至０・５：４程度で用いられる。The molar ratio used is about 1:1 to 0.5:4.
塩基には、有機又は無機の塩基例えば、Ｎａ，Ｋ等．水
酸化物，炭酸塩やアルコラート，アムモニア或いはピリ
ジン．トリエチルアミンなどは有効なかごうぶつの代表
例である。Examples of the base include organic or inorganic bases such as Na, K, etc. Hydroxide, carbonate or alcoholate, ammonia or pyridine. Triethylamine is a typical example of an effective container.
反応に際しては，溶媒を用いる事も出来る。特に、極性
の溶剤例えば，アルコール．アセトニトリル．スルホラ
：／，ＴＨＦ，ＤＭＡｃ，ＤＭＳＯジメトキシエタン等
から選ばれた１種以上が好都合にもちいられる。中でも
、アセトニトリル，スルホラン． Ｄ Ｍ Ａ ｃ等
は反応が早く良い結果を与える。水は含まれていても良
い。A solvent can also be used during the reaction. In particular, polar solvents such as alcohols. Acetonitrile. One or more selected from sulfora:/, THF, DMAc, DMSO dimethoxyethane, etc. are conveniently used. Among them, acetonitrile and sulfolane. DMAC etc. react quickly and give good results. Water may be included.
反応の温度は．３０度乃至１２０度程度が好ましい。特
に６０度乃至９５度が好ましい。The temperature of the reaction is. The angle is preferably about 30 degrees to 120 degrees. Particularly preferred is 60 degrees to 95 degrees.
本発明で得られる化合物の例を以下に示す。Examples of compounds obtained by the present invention are shown below.
２−フエノキシエチルーＰ一トルエンスルホンアミド、
２−パラメトキシフエノキ，シエチル−Ｐ−トルエンス
ルホンアミド，２−メチルフェノキシエチルベンゼンス
ルホンアミド、２−メチルフェノキシプロピルーＰ一ト
ルエンスルホンアミド３−７エノキシプロピルーＰ−｝
ルエンスルホンアミド、４−（２−メトキシフェノヰシ
）フチルーＰ−｝ルエンスルホンアミド、４−１ロロ
ブチルベンゼンスルホンアミド、３−７エノキシアセト
キシブロビルベンゼンスルホンアミド、３−クロロー４
−メトキシブチルーＰ一トルエンスルホンアミド、４−
Ｎ−メチルーＮ−フルフルフリルカルバモイルブチルメ
タンスルホンアミド２−パラメチルチオフエノキシエチ
ルトルエンスルホンアミド、２−メチルインドール−３
−イルメチルベンゼンスルホンアミド、２−ブトキンエ
トキシメタンスルホンアミド、ノニルフェノヰシポリエ
チレンオキシエチルーＰ一トルエンスルホンシミド、３
オキサー５−メトキシペンチルーＰ一トルエンスルホ
ンアミド、３−７エニルチオプロビルベンゼンスルホン
アミド、フェノキシエトキシプロポキシエチルベンゼン
ロルホンアミド等が挙げられる。2-phenoxyethyl-P-toluenesulfonamide,
2-paramethoxyphenoxy, ethyl-P-toluenesulfonamide, 2-methylphenoxyethylbenzenesulfonamide, 2-methylphenoxypropyl-P-toluenesulfonamide 3-7enoxypropyl-P-}
luenesulfonamide, 4-(2-methoxyphenolicy)phthyl-P-}luenesulfonamide, 4-1 lobutylbenzenesulfonamide, 3-7 enoxyacetoxybrobylbenzenesulfonamide, 3-chloro4
-methoxybutyl-P-toluenesulfonamide, 4-
N-Methyl-N-furfurfurylcarbamoylbutyl methanesulfonamide 2-paramethylthiophenoxyethyltoluenesulfonamide, 2-methylindole-3
-ylmethylbenzenesulfonamide, 2-butquinethoxymethanesulfonamide, nonylphenolic polyethyleneoxyethyl-P-toluenesulfonamide, 3
Oxer-5-methoxypentyl-P-toluenesulfonamide, 3-7enylthiopropylbenzenesulfonamide, phenoxyethoxypropoxyethylbenzenolphonamide, and the like.
これらは、加水分解してアミン化合物に導く事も出来る
。また融点が７５度乃至１１０度の水非混和性Ｎ−アル
キルアリールスルホンアミドは先に述べた様に、記録材
料用の添加剤として有用である。These can also be hydrolyzed to lead to amine compounds. Also, water-immiscible N-alkylaryl sulfonamides having a melting point of 75 to 110 degrees are useful as additives for recording materials, as mentioned above.
以下に実施例をあげて、本発明の手法を説明する。The method of the present invention will be explained below with reference to Examples.
実施例−１
かきまぜ機をつけたフラスコに、０・ｌモルの２−フェ
ノキ，シエチル−Ｐ−｝ルエンスルホネート、０・１モ
ルのＰ−｝ルエンスルホンアミド及？Ｏ−１１モルの炭
酸加里を８０ＣＣのスルホラン中に量り取った。かきま
ぜながら、７０度乃至９５度に３時間保持した後定法に
従っ■て処理した。融点１ ０ ４−５度の結晶として
２−フエノキシエチルーＰ−｝ルエンスルホンアミドを
えた。収率６５％あった。アセトニトリルを溶媒に用い
た時は同じ収量を得るのに．反応時間が長くかかった実
施例−２
Ｐ〜エチルベンゼンスルホンアミドを用いた他は同様に
して２−フェノキシエチルエチルベンゼンスルホンアミ
ドを得た。粗収率は７０％であった。Example-1 In a flask equipped with a stirrer, 0.1 mol of 2-phenoxyethyl-P-}luenesulfonate, 0.1 mol of P-}luenesulfonamide, and 2-phenoxyethyl-P-}luenesulfonamide were added. O-11 moles of potassium carbonate were weighed into 80 cc of sulfolane. The mixture was kept at 70 to 95 degrees for 3 hours while stirring, and then processed according to the conventional method. 2-Phenoxyethyl-P-}luenesulfonamide was obtained as crystals with a melting point of 104-5 degrees. The yield was 65%. The same yield was obtained when acetonitrile was used as the solvent. Example 2 in which the reaction time was long 2-phenoxyethylethylbenzenesulfonamide was obtained in the same manner except that P~ethylbenzenesulfonamide was used. The crude yield was 70%.
実施例−３
２−７ェネチルーＰ−トルエンスルホ＊−｝トベンゼン
スルホンアミドを用いた他は同様にして２−フェネチル
ベンゼンスルホンアミドを得た融点６７度であった。Example 3 2-Phenethylbenzenesulfonamide was obtained in the same manner except that 2-7enethyl-P-toluenesulfo*-}tobenzenesulfonamide was used, and the melting point was 67 degrees.
Claims (1)
アルキルスルホン酸エステルを反応させる事を特徴とす
るアルキルアミドの製造方法。A method for producing an alkyl amide, which comprises reacting a sulfonamide with an optionally substituted alkyl sulfonic acid ester in the presence of a base.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15073089A JPH0317053A (en) | 1989-06-14 | 1989-06-14 | Production of alkylamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15073089A JPH0317053A (en) | 1989-06-14 | 1989-06-14 | Production of alkylamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0317053A true JPH0317053A (en) | 1991-01-25 |
Family
ID=15503160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15073089A Pending JPH0317053A (en) | 1989-06-14 | 1989-06-14 | Production of alkylamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0317053A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001068592A1 (en) * | 2000-03-13 | 2001-09-20 | Eli Lilly And Company | Sulfonamide derivatives |
-
1989
- 1989-06-14 JP JP15073089A patent/JPH0317053A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001068592A1 (en) * | 2000-03-13 | 2001-09-20 | Eli Lilly And Company | Sulfonamide derivatives |
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