KR840001669B1 - Process for the preparation of octadecenic acid amide - Google Patents

Process for the preparation of octadecenic acid amide Download PDF

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KR840001669B1
KR840001669B1 KR1019800004751A KR800004751A KR840001669B1 KR 840001669 B1 KR840001669 B1 KR 840001669B1 KR 1019800004751 A KR1019800004751 A KR 1019800004751A KR 800004751 A KR800004751 A KR 800004751A KR 840001669 B1 KR840001669 B1 KR 840001669B1
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trans
dioxo
octadecenoic acid
chloroform
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KR830004209A (en
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신고 마쓰무라
히로시 에노모도
미쓰히로 마에하라
마사구니 오자끼
히데야 하야시
마사도 마쓰다
유끼오 후지다
이찌로오 시라하세
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닛본신야꾸 가부시기가이샤
모리시다 히로무
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton

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Abstract

Title compds. (I; R=alkyl, alkenyl, cycloalkyl, aralkyl, furfuryl, Ph, (CH2)3-X; X=heterocycle; n=0-3), useful as blood platelet aggregation inhibitors, were prepd. by the reaction of II with III. Thus, stirring 1.55g 9,12-dioxo-trans-10-octadecenoic acid with 300mg isoproplamine in chloroform in the presence of 610mg trienthylamine and 760mg isobutylchlorocarboxylic acid gave 1.65g N-isopropyl-9, 12-dioxo-trans-10-octadecenide(93.9% yield).

Description

옥타데센산 아미드의 제법Preparation of octadecenoic acid amide

본 발명은 일반식[Ⅰ]The present invention is a general formula [Ⅰ]

Figure kpo00001
(Ⅰ)
Figure kpo00001
(Ⅰ)

로서 표시되는 9,12-디옥소-트란스-10-옥타데센산 아미드의 제법에 관한 것이다.It relates to the preparation of 9,12-dioxo-trans-10-octadecenoic acid amide represented as.

단, 식중 R은 알킬기, 알케닐기, 시클로알킬기, 알랄킬기, 치환기를 각지고 있어도 좋은 페닐기 또는-(CH2)n-X를 표시함. 여기서 n은 0∼3까지의 정수(整數)를 표시하며, X는Wherein R represents an alkyl group, an alkenyl group, a cycloalkyl group, an alalkyl group, or a phenyl group which may have a substituent, or-(CH 2 ) n -X. Where n represents an integer from 0 to 3 , where X is

Figure kpo00002
Figure kpo00002

또는 OH를 표시함. 단, 여기서 m은 1또는 2를 표시함.Or OH. Where m represents 1 or 2.

본 발명은 포함되는, 9, 12-디옥스-트란스-10-옥타센신아미드의 구체적인 예를 든다면 제1표에 나타낸 화합물을 예거할 수 있다.The present invention may include the compounds shown in the first table, given specific examples of the 9, 12-diox-trans-10-octacecincinamide included.

[표 1]TABLE 1

Figure kpo00003
Figure kpo00003

본 발명의 전기한 일반식 [Ⅰ]로서 표시되는 9,12-디옥스-트란스-옥타데센산아미드는 식 [Ⅱ]The 9,12-diox-trans-octadecenoic acid amide represented by the above general formula [I] of the present invention is represented by the formula [II]

Figure kpo00004
Figure kpo00004

으로 표시되는 9,12-디옥소-트란스-10-옥타데센산의 카르복실기를 반응성 유도체에 안내하고, 일반식 [Ⅲ]The carboxyl group of 9,12-dioxo-trans-10-octadecenoic acid represented by the above is introduced to the reactive derivative, and the general formula [III]

R-NH2[Ⅲ]R-NH 2 [III]

(식중의 R은 전기한 바와 같음)(Wherein R is as described above)

로서 표시되는 화합물과 반응시킴으로서 제조할 수 있다. 이런 경우 식[Ⅱ]로 표시되는 9,12-디옥스-트란스-10-옥타데센산은 공지된 화합물이며, 문헌(J, A m, chem, Soc, 80, 5705)기재의 방법으로 합성할 수 있다.It can be prepared by reacting with the compound represented as. In this case, 9,12-diox-trans-10-octadecenoic acid represented by the formula [II] is a known compound and can be synthesized by the method described in the literature (J, Am, chem, Soc, 80, 5705). have.

본 발명의 화합물에 잘 알맞는 제조방법을 더 상세하게 설명한다면, 예컨데, [Ⅱ] 물질 및 [Ⅱ]물질의 1.1∼1.2배 몰양의 염기를 불활성 유기용매에 용해 또는 현탁하고, -5℃∼실온에서 저어 섞어가면서[Ⅱ] 물질의 1.1배몰의 알킬클로로 카르보네이트를 가하고, 30분∼2시간 저어 섞는다. 이어서 [Ⅱ] 물질과 같은 몰의 일반식 [Ⅱ]으로 표시되는 화합물을 -5℃∼실온에서 가하여 30분∼2주야(밤낮) 반응시킨다.If the preparation method suitable for the compound of the present invention is described in more detail, for example, 1.1 to 1.2-fold molar amount of the base of [II] and [II] is dissolved or suspended in an inert organic solvent, Stir at room temperature, add 1.1 times mole of alkylchloro carbonate of the [II] substance, and stir for 30 minutes to 2 hours. Subsequently, the compound represented by the general formula [II] of the same mole as the [II] substance is added at -5 ° C to room temperature, and reacted for 30 minutes to 2 nights (night and day).

반응종료후, 수세하여 건조한다음 용매를 유거(留去)하면 목적물이 얻어진다. 또[Ⅱ]물질과, [Ⅱ]물질과 같은몰의 일반식[Ⅱ]로서 표시되는 화합물과, [Ⅱ]물질의 2.5배몰의 염기를 불활성용매에 용해한 후 -10℃이하에서 교반해가면서 옥시염환인, 알킬설폰산클로라이드등의 카르복실기 활성화제를 가하여 1∼2시간 같은 온도에서 교반한후 수세하여 건조한다음 용매를 유기하면 목적물이 얻어진다.After completion of the reaction, the mixture is washed with water, dried and the solvent is distilled off to obtain the desired product. Furthermore, after dissolving the [II] substance, the compound represented by the general formula [II] of the same mole as the [II] substance, and the 2.5 times molar base of the [II] substance in an inert solvent, the mixture was stirred at -10 ° C or lower. A carboxyl group activator, such as an alkylsulfonic acid chloride, which is a salt ring, is added, stirred at a temperature of about 1 to 2 hours, washed with water and dried, and then the organic solvent is obtained.

그런데 본 발명에 포함되는 화합물은, 모두 문헌에 기재된바 없는 신규화합물이지만, 본 발명자들에 의한 여러가지 생화학적 약리학적인 검토 결과 강한 혈소판응집의 억제작용과 제암(制癌)작용을 가지고 있다는 것이 명백해졌다.By the way, the compounds included in the present invention are all novel compounds that have not been described in the literature, but the results of various biochemical pharmacological studies by the present inventors revealed that they have a strong inhibitory and anticancer action of platelet aggregation. .

혈소틈응집기구(機構)에 프로스타글라딘 엔도 퍼옥사이드 나트롬 복산을 위시하여 프로스다글란딘(prostaglandin)류가 깊이 관여하고 있다는 것은 잘 알려지고 있으며, 혈소판응집의 이상한 항진(亢進)이 혈전증, 뇌경새(腦梗塞), 신액(腎炎), 당뇨병, 동맥경화, 협심증, 심근경새(心筋梗塞)등과 같은 병태발증(病態發症)의 하나의 원인으로 되고 있다는 것도 주지의 사실이다. 따라서 이를 저해하는 본 발명화합물은 상기한 각종 질환의 예방 및 치료제로서 매우 유용하다. 본 발명에 의한 화합물의 원료물질인 9,12-디옥소-트란스-옥타데센산[Ⅱ]은 그 자신 약한 제암작용을 가지고 있지만 본 발명에 의한 화합물은 어느 화합물에 있어서도, [Ⅱ]물질보다 훨씬 강한 제암작용을 가지고 있으며 따라서 제암제로서도 매우 유용하다. 제2표에 본 발명에 포함되는 대표적인 화합물에 대하여, 그들의 혈소판응집 억제활성, 제암활성은 나타냄.It is well known that prostaglandins are deeply involved, including prostaglandin endo peroxide nitrate, in the blood clotting mechanism, and the abnormal hyperplasia of platelet aggregation is thrombosis. It is also known that cerebral striation, kidney fluid, diabetes mellitus, arteriosclerosis, angina pectoris, myocardial celiac, and other causes of the onset of the disease. Therefore, the compound of the present invention which inhibits this is very useful as a prophylactic and therapeutic agent for various diseases described above. 9,12-dioxo-trans-octadecenoic acid [II], a raw material of the compound according to the present invention, has its own weak anticancer activity, but the compound according to the present invention is far more effective than the [II] substance in any compound. It has strong anticancer activity and is therefore very useful as an anticancer agent. Representative compounds included in the present invention in Table 2 show their platelet aggregation inhibitory activity and anticancer activity.

혈소판응집 저해활성은 가토다혈소판혈장(家免多價小板血漿)에서의 ADP응질 및 아라키돈산(arachidonicaid)응집의 50% 저해 농도(ⅠC50(㎍/m))로서 표시한다. 제암활성은 에를리히 복수암이식(腹水癌移植) 마우스에 이식한 다음날로부터 1일양 mg/kg을 연속 5일간 복강내에 투여하고, 평균생존일수의 대(對) 콘트롤비(T/C), 및 이식 40일째의 생존율(S.R.)로 표시한다.Platelet aggregation inhibitory activity is expressed as 50% inhibitory concentration (IC 50 (µg / m)) of ADP coagulation and arachidonicaid aggregation in Gatoda platelet plasma. The anticancer activity is administered in an intraperitoneal dose of mg / kg per day for 5 consecutive days from the day following transplantation to Erlich's ascites cancer transplantation mice, and the control ratio (T / C) of the average survival days, and the transplantation Expressed as survival rate (SR) on day 40.

[표 2]TABLE 2

Figure kpo00005
Figure kpo00005

이어서 본 발명의 실시예에 의해서 보다 상세히 설명하면 다음과 같다.Next, the embodiment of the present invention will be described in detail.

[실시예 1]Example 1

N-이소프로필-9,12-디옥소-트란스-10-옥타데세나미드(1)의 합성 9,12-디옥소-트란스-10-옥타데센산 1.55g을 건조 클로로포름 30ml에 용해하여 이것에 트리에탈아민 610mg을 가하여 0℃이하에서 교반해가면서 클로르탄산 이소부틸 760mg을 적하하였다. 적하종료후 다시 30분간 냉각하 교반후에 0∼5℃에서 이소프로필아민 300mg을 적하하였다. 적하종료후 실온에서 2시간 교반한 후에 수세하고, MgSO4로서 건조한후에 클로로포름을 감압유거하였던바 결정이 석출하였다. 석출된 결정은 이소프로판올로서 재결정하여 융점 116∼7℃의 N-이소프로필-9,12-디옥소-트란스-10-옥타데세나이드(1)를 1.65g(수율 93.9%)을 얻었다.Synthesis of N-isopropyl-9,12-dioxo-trans-10-octadecenamid (1) 1.55 g of 9,12-dioxo-trans-10-octadecenoic acid was dissolved in 30 ml of dry chloroform and dissolved in it. 610 mg of triethanamine was added, and 760 mg of isobutyl chlorates were added dropwise while stirring at 0 ° C or lower. After completion of the dropwise addition, 300 mg of isopropylamine was added dropwise at 0? 5 占 폚 after stirring under cooling for 30 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours, washed with water, dried with MgSO 4 , and chloroform was distilled off under reduced pressure to precipitate crystals. The precipitated crystals were recrystallized as isopropanol to obtain 1.65 g (yield 93.9%) of N-isopropyl-9,12-dioxo-trans-10-octadecenide (1) having a melting point of 116 to 7 ° C.

원소분석치(C21H37NO3로서)Elemental Analysis Values (as C 21 H 37 NO 3 )

C% H% N%C% H% N%

계산치 71.75 10.61 3.99Calculated 71.75 10.61 3.99

실측치 71.62 10.82 4.08Found 71.62 10.82 4.08

N-시클로헥실-9,12-디옥소-트란스-10-옥타데세나미드(3)의 합성 9, 12-디옥소-트란스-10-옥타데센산 2.17g을 건조, 클로로포름 35ml을 용해하고 이것에 트리에틸아민 810mg을 가하여 0∼5℃에서 교반해 가면서 클로로탄산이소부틸 1.02g을 적하하였다. 적하종료후 다시 30분간 실온으로 반한후에 0∼5℃에서 시클로헥실아민 700mg을 적하하였다. 적하종료후 2주야(밤낮)실온에서 교반한후에 수세하고 MgSO4로 건조한후에 클로로포름을 감압 유거하였던바 결정이 석출하였다. 석출된 결정은 이소프로판올로서 재결정하여 융점 129∼30.5℃의 N-시클로헥실-9,12-디옥스-트란스-10-옥클데세나미드(3)를 2.30g(수율 83.9%)을 얻었다.Synthesis of N-cyclohexyl-9,12-dioxo-trans-10-octadecenamid (3) 9,12-dioxo-trans-10-octadecenoic acid was dried to 2.17 g, and 35 ml of chloroform was dissolved. 810 mg of triethylamine was added thereto, and 1.02 g of isobutyl chlorocarbonate was added dropwise while stirring at 0? 5 占 폚. After completion of the dropwise addition, the mixture was returned to room temperature for 30 minutes, and 700 mg of cyclohexylamine was added dropwise at 0? 5 占 폚. After completion of the dropwise addition, the mixture was stirred at room temperature for two nights (night and day), washed with water, dried over MgSO 4 , and chloroform was distilled off under reduced pressure to precipitate crystals. Precipitated crystals were recrystallized as isopropanol to obtain 2.30 g (yield 83.9%) of N-cyclohexyl-9,12-diox-trans-10-oxckledenamide (3) having a melting point of 129 to 30.5 ° C.

원소분석치(C24H41NO3로서)Elemental Analysis Values (as C 24 H 41 NO 3 )

C% H% N%C% H% N%

계산치 73.61 10.55 3.58Calc 73.61 10.55 3.58

실측치 73.59 10.85 3.33Found 73.59 10.85 3.33

[실시예 3]Example 3

N-페닐-9,12-디옥소-트란스-10-옥타데세나미드(8)의 합성 9,12-디옥소-트란토-10-옥타데센산 2.17g과 트리에틸아민 2g과 아닐린 750mg을 클로로포름 40ml에 용해하고, -10℃ 이하에서 교반해가면서 옥시염화인 1.3g 을 적하하였다. 적하종료후 같은 온도에서 1시간 교반한후에 수세하고, MgSO4로서 건조한후에 클로로포름을 감압유거하였던바 결정이 석출하였다. 석출된 결정은 이소프로판올로서 재결정하여 융점 121∼2℃의 N-페닐-9,12-디옥소-트란스-10-옥타데세나미드(8)을 2.45g(수율 90.7%)을 얻었다.Synthesis of N-phenyl-9,12-dioxo-trans-10-octadecenamid (8) 2.17 g of 9,12-dioxo-tranto-10-octadecenoic acid, 2 g of triethylamine and 750 mg of aniline It dissolved in 40 ml of chloroforms, and 1.3 g of phosphorus oxychlorides was dripped, stirring at -10 degrees C or less. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour, washed with water, dried with MgSO 4 , and chloroform was distilled off under reduced pressure to precipitate crystals. The precipitated crystals were recrystallized as isopropanol to obtain 2.45 g (yield 90.7%) of N-phenyl-9,12-dioxo-trans-10-octadecenamid (8) having a melting point of 121 to 2 ° C.

원소분석치(C24H35O3N로서)Elemental analysis value (as C 24 H 35 O 3 N)

C% H% N%C% H% N%

계산치 74.76 9.15 3.63Calculated 74.76 9.15 3.63

실측치 74.65 9.40 3.78Found 74.65 9.40 3.78

[실시예 4]Example 4

N-(4-히드록디에틸페닐)-9.12-디옥소-트란스-10-옥타데세나미드 (14)의 합성 9,12-디옥소-트란스-10-옥타데센산 2.17g과 트리에틸아민 2g과 4-히드록시에틸아닐린 1.1g을 클로로포름 40ml에 용해하여 -10℃이하에서 교반해가면서 옥시염화인 1.3g을 적하하였다. 적하종료후 같은온도에서 1시간 교반한 후에 수세하고, MgSO4로 건조한후에 클로로포름을 감압유거하였던바 결정이 석출하였다. 석출된 결정은 DMF와 메탄올의 혼합용매로서 재결정하여 용접 149.5∼51℃의 N-(4-히드록시에틸페닐)-9,12-디옥스-트란스-10-옥타데세나미드를 2.53g(수율 84.1%)을 얻었다.Synthesis of N- (4-hydroxydiethylphenyl) -9.12-dioxo-trans-10-octadecenamid (14) 2.17 g of 9,12-dioxo-trans-10-octadecenoic acid and 2 g of triethylamine And 1.1 g of 4-hydroxyethyl aniline were dissolved in 40 ml of chloroform, and 1.3 g of phosphorus oxychloride was added dropwise while stirring at −10 ° C. or lower. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour, washed with water, dried with MgSO 4 , and chloroform was distilled off under reduced pressure to precipitate crystals. The precipitated crystals were recrystallized as a mixed solvent of DMF and methanol, and 2.53 g of N- (4-hydroxyethylphenyl) -9,12-diox-trans-10-octadecenamid at 149.5-51 ° C. (yield by welding) was obtained. 84.1%).

원소분석치(C26H39NO4로서)Elemental Analysis Values (as C 26 H 39 NO 4 )

C% H% N%C% H% N%

계산치 72.69 9.15 3.26Calculated 72.69 9.15 3.26

실측치 72.45 9.40 3.38Found 72.45 9.40 3.38

[실시예 5]Example 5

N-(N-에틸-2-피로티디닐메틸))-9,12-디옥소-트란스-10-옥타데세나미드(20)의 합성 9,12-디옥소-트란스-10-옥타데센산 2.17g을 건조, 클로로포름 40ml에 용해하고, 이것에 트리에틸아민 810mg을 가하여 0℃이하에서 교반해가면서 클로로이소부틸 1.02g 을 적하하였다. 적하종료후 다시 1시간 실온에서 교반한 다음, 0∼5℃에서 교반해가면서 N-에틸-2-아미노메틸피로딘 1.03g을 적하하였다. 적하종료후 실온에서 1시간 교반한후에 수세하고, MgSO4으로 건조한후에 클로로포름을 감압유거하였던바 결정이 석출하였다. 이 석출결정은 이소프로판올로서 재결정하여 융점 95∼55℃의 N-(N-에틸-2-피로리디닐메틸)-9,12-디옥소-트란스-10-옥타데세나미드(20)을 2.43g(수율 8.7%)얻었다.Synthesis of N- (N-ethyl-2-pyrotidinylmethyl))-9,12-dioxo-trans-10-octadecenamide (20) 9,12-dioxo-trans-10-octadecenoic acid 2.17 g was dried, dissolved in 40 ml of chloroform, and 810 mg of triethylamine was added thereto, and 1.02 g of chloroisobutyl was added dropwise while stirring at 0 ° C or lower. After completion of the dropwise addition, the mixture was stirred for 1 hour at room temperature, and then 1.03 g of N-ethyl-2-aminomethylpyrrodine was added dropwise while stirring at 0? 5 占 폚. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour, washed with water, dried over MgSO 4 , and chloroform was distilled off under reduced pressure, and crystals precipitated. This precipitated crystal was recrystallized as isopropanol, and 2.43 g of N- (N-ethyl-2-pyrrolidinylmethyl) -9,12-dioxo-trans-10-octadecenamid (20) having a melting point of 95 to 55 占 폚. (Yield 8.7%).

원소분석치(C25H34O3N2로서)Elemental analysis value (as C 25 H 34 O 3 N 2 )

C% H% N%C% H% N%

계산치 71.38 10.54 6.66Calculated 71.38 10.54 6.66

실측치 71.12 10.71 6.45Found 71.12 10.71 6.45

[실시예 6]Example 6

N-(2-히드록시에틸)-9,12-디옥소-트란스-10-옥타데세나미드(23)의 합성 9,12-디옥소-트란스-10-옥타데센산 2.17g을 건조, 클로로포름 40ml에 용해하고, 이것에 트리에틸아민 810ml을 가하고, 0∼5℃에서 교반해가면서 클로르탄산이소부틸 1.02g을 적하하였다. 적하종료후 다시 같은 온도에서 1시간 교반한후에 0∼3℃에서 교반해가면서 모노에탄올아민 430mg을 적하하였다. 적하종료후 실온에서 1시간 교반한후에, MgSO4로 건조한 후에, 클로로포름을 감압유거하였던바 결정이 석출하였다.Synthesis of N- (2-hydroxyethyl) -9,12-dioxo-trans-10-octadecenamide (23) 2.17 g of 9,12-dioxo-trans-10-octadecenoic acid was dried and chloroform It melt | dissolved in 40 ml, 810 ml of triethylamines were added to this, and 1.02 g of isobutyl chlorates were dripped, stirring at 0-5 degreeC. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hour, and then 430 mg of monoethanolamine was added dropwise while stirring at 0 to 3 ° C. After completion of the dropwise addition, the mixture was stirred at room temperature for 1 hour, and then dried over MgSO 4 , after which chloroform was distilled off under reduced pressure to precipitate crystals.

석출된 결정은 에탄올로서 재결정하여 융점 125∼6℃의 N-(2-히드록시에틸)-9,12-디옥소-트란스-10-옥타데세나미드(23)를 2.09g(수율 84.6%)을 얻었다.The precipitated crystals were recrystallized as ethanol and 2.09 g (yield 84.6%) of N- (2-hydroxyethyl) -9,12-dioxo-trans-10-octadecenamid (23) having a melting point of 125 to 6 ° C. Got.

원소분석치(C20H35NO4로서)Elemental Analysis Values (as C 20 H 35 NO 4 )

C% H% N%C% H% N%

계산치 67.95 9.98 3.96Calculation 67.95 9.98 3.96

실측치 67.75 10.12 3.86Found 67.75 10.12 3.86

Claims (1)

일반식(Ⅱ)의 9,12-디옥소-트란스-10-옥타데센산을 일반식(Ⅲ)의 화합물과 반응시킴을 특징으로 하는 일반식(Ⅰ)의 9,12-디옥소-트란스-10-옥타데센산아미드 유도체의 제법.9,12-dioxo-trans- of general formula (I) characterized by reacting 9,12-dioxo-trans-10-octadecenoic acid of general formula (II) with a compound of general formula (III) Preparation of 10-octadecenoic acid amide derivatives.
Figure kpo00006
Figure kpo00006
 R-NH2(Ⅲ)R-NH 2 (III) 식중에서, R은 알킬기, 알케닐기, 시클로알킬기, 아랄킬기, 푸르푸릴기, 치환기를 가지고 있어도 좋은 페닐기 또는 -(CH2)3-X를 표시한다.In the formula, R represents an alkyl group, alkenyl group, cycloalkyl group, aralkyl group, furfuryl group, phenyl group which may have a substituent, or-(CH 2 ) 3 -X. n은 0-3의 정수.n is an integer of 0-3. X는X is
Figure kpo00007
Figure kpo00007
 또는 OH를 표시한다. m은 1 또는 2.Or OH. m is 1 or 2.
KR1019800004751A 1980-07-29 1980-12-13 Process for the preparation of octadecenic acid amide KR840001669B1 (en)

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JP10470780A JPS5728037A (en) 1980-07-29 1980-07-29 Octadecenoic acid amide
JP104707 1980-07-29

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