JPS6257181B2 - - Google Patents
Info
- Publication number
- JPS6257181B2 JPS6257181B2 JP14707280A JP14707280A JPS6257181B2 JP S6257181 B2 JPS6257181 B2 JP S6257181B2 JP 14707280 A JP14707280 A JP 14707280A JP 14707280 A JP14707280 A JP 14707280A JP S6257181 B2 JPS6257181 B2 JP S6257181B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- dialkylcarbamate
- esters
- formula
- represented
- 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.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- -1 terpene alcohols Chemical class 0.000 description 4
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 3
- 239000005792 Geraniol Substances 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 description 3
- 229940113087 geraniol Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FKKLUOCEIANSFL-UHFFFAOYSA-N 4-methylpent-3-en-1-ol Chemical compound CC(C)=CCCO FKKLUOCEIANSFL-UHFFFAOYSA-N 0.000 description 1
- XEFQCLXNSJBVNZ-UHFFFAOYSA-N 5,9,13-trimethyltetradeca-4,8,12-trien-1-ol Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCCO XEFQCLXNSJBVNZ-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VUYCBBHNGBWOJM-UHFFFAOYSA-N NCOCl Chemical compound NCOCl VUYCBBHNGBWOJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940036350 bisabolol Drugs 0.000 description 1
- HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940043259 farnesol Drugs 0.000 description 1
- 229930002886 farnesol Natural products 0.000 description 1
- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Description
本発明は次の一般式（）
（式中ｎは１〜３の整数を表わし、R1および
R2は低級アルキル基を表わす）で示されるＮ，
Ｎ−ジアルキルカルバミン酸エステルに関する。
従来、テルペンアルコールのカルバミン酸エス
テルについては、ゲラニオールのジフエニルカル
バミン酸エステルが幾何異性体の分離のための誘
導体として知られており、またある種のテルペン
アルコールのカルバミン酸エステルは消炎作用あ
るいは抗けいれん作用を有することが知られてい
る。たとえば特公昭44−20086号公報には、消炎
作用を有する化合物として、ビサボロール、ゲラ
ニオール、シトロネロール、ボルネオールおよび
α−テルピネオールのカルバミル酸エステルが記
載され、ジヤーナル・オブ・メデイシナル・ケミ
ストリ（Journal of Medicinal Chemistry），
1972，Vol.15，No.９，第998頁にはプレノール、
ホモプレノール、シトロネロール、ゲラニオー
ル、ネロールおよびフアルネソールの非置換カル
バミン酸エステルの抗けいれん作用について記載
されている。
本発明者らは、前記した一般式（）で示され
る新規なＮ，Ｎ−ジアルキルカルバミン酸エステ
ルが抗腫瘍作用を有することを見出し、本発明を
完成するに至つた。
一般式（）において低級アルキル基を表わす
R1およびR2はたとえばメチル、エチル、ｎ−プ
ロピル、イソプロピル、ｎ−ブチル、イソブチ
ル、sec−ブチル、tert−ブチルなどであること
ができる。一般式（）で示される本発明のＮ，
Ｎ−ジアルキルカルバミン酸エステルとして下記
の化合物が例示される。ただし下記においてＧ
−、Fa−およびＧ・Ｇ−はそれぞれ３，７−ジ
メチルオクタ−２，６−ジエン−１−イル基、
３，７，11−トリメチルドデカ−２，６，10−ト
リエン−１−イル基および３，７，11，15−テト
ラメチルヘキサデカ−２，６，10，14−テトラエ
ン−１−イル基を意味する。
一般式（）で示されるＮ，Ｎ−ジアルキルカ
ルバミン酸エステルは、対応する出発物質を用い
ること以外は公知のカルバミン酸エステルの製法
として知られた各種の方法により製造することが
できる。たとえば、下記の一般式（）
（式中ｎは一般式（）中のそれと同じ意味を
有する）で示されるテルペンアルコールと下記の
一般式（）
（式中R1およびR2は一般式（）中のそれら
と同じ意味を有し、Ｘはハロゲン原子を表わす）
で示されるＮ，Ｎ−ジアルキルカルバモイルハラ
イドをピリジン、水素化ナトリウムなどの塩基性
縮合剤の存在下で反応させることにより一般式
（）で示されるＮ，Ｎ−ジアルキルカルバミン
酸エステルを得ることができる。この反応は、通
常、たとえばジオキサン、テトラヒドロフラン、
芳香族炭化水素、ジメチルスルホキシドなどの適
当な溶媒の存在下、約０〜150℃の温度で行われ
る。
本発明により提供される一般式（）で示され
るＮ，Ｎ−ジアルキルカルバミン酸エステルは前
記のように抗腫瘍作用を有し、したがつて抗腫瘍
剤などの医薬品として有用である。たとえば一般
式（）においてｎ＝２、R1＝R2＝CH3の化合
物すなわちフアルネシルエチル Ｎ，Ｎ−ジメチ
ルカルバメートについてその薬理データを示せば
次のとおりである。
抗腫瘍作用
ddY−マウス（雄、５週令）の腹腔内にエーリ
ツヒ腹水腫瘍細胞2.5×106個を移植し、移植後24
時間経過後より表１に示す投与スケジユールによ
つてフアルネシルエチル Ｎ，Ｎ−ジメチルカル
バメートを腹腔内に投与した。各マウスの生存日
数を観察し、中央値によつて延命率を算出した。
The present invention is based on the following general formula () (In the formula, n represents an integer of 1 to 3, R 1 and
R 2 represents a lower alkyl group),
This invention relates to N-dialkylcarbamate esters. Conventionally, regarding carbamate esters of terpene alcohols, diphenylcarbamate ester of geraniol is known as a derivative for separation of geometric isomers, and some carbamate esters of terpene alcohols have anti-inflammatory or antispasmodic effects. It is known to have an effect. For example, Japanese Patent Publication No. 44-20086 describes carbamylic acid esters of bisabolol, geraniol, citronellol, borneol, and α-terpineol as compounds with anti-inflammatory effects, and the Journal of Medicinal Chemistry ，
1972, Vol. 15, No. 9, page 998, prenol,
The anticonvulsant action of unsubstituted carbamate esters of homoprenol, citronellol, geraniol, nerol and farnesol has been described. The present inventors have discovered that the novel N,N-dialkylcarbamate represented by the general formula () has an antitumor effect, and have completed the present invention. Represents a lower alkyl group in the general formula ()
R 1 and R 2 can be, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and the like. N of the present invention represented by general formula (),
The following compounds are exemplified as N-dialkylcarbamate esters. However, in the following G
-, Fa- and G.G- are each a 3,7-dimethyloct-2,6-dien-1-yl group,
3,7,11-trimethyldodeca-2,6,10-trien-1-yl group and 3,7,11,15-tetramethylhexadec-2,6,10,14-tetraen-1-yl group means. The N,N-dialkylcarbamate represented by the general formula () can be produced by various methods known as methods for producing carbamates, except for using the corresponding starting materials. For example, the general formula () below (In the formula, n has the same meaning as in the general formula ()) and the following general formula () (In the formula, R 1 and R 2 have the same meanings as in the general formula (), and X represents a halogen atom)
By reacting the N,N-dialkylcarbamoyl halide represented by in the presence of a basic condensing agent such as pyridine or sodium hydride, an N,N-dialkylcarbamate ester represented by the general formula () can be obtained. . This reaction is typically performed using e.g. dioxane, tetrahydrofuran,
It is carried out in the presence of a suitable solvent such as an aromatic hydrocarbon, dimethyl sulfoxide, etc. at a temperature of about 0 to 150°C. The N,N-dialkylcarbamate ester represented by the general formula () provided by the present invention has an antitumor effect as described above, and is therefore useful as a pharmaceutical agent such as an antitumor agent. For example, in the general formula (), n=2 and R 1 =R 2 =CH 3 , ie, a compound of pharnesylethyl N,N-dimethylcarbamate, the pharmacological data are as follows. Antitumor effect: 2.5 x 106 Ehritzch ascites tumor cells were intraperitoneally transplanted into ddY- mice (male, 5 weeks old), and 24 days after transplantation.
After a period of time had elapsed, pharnesylethyl N,N-dimethylcarbamate was intraperitoneally administered according to the administration schedule shown in Table 1. The number of days each mouse survived was observed, and the survival rate was calculated based on the median value.
【表】
以下、本発明を実施例により説明するが、本発
明はこれらの実施例によつて制限を受けるもので
はない。
実施例 １
温度計および還流冷却器を付けた300mlの三つ
口フラスコに５，９，13−トリメチルテトラデカ
−４，８，12−トリエン−１−オール（別名：フ
アルネシルエタノール）25.0ｇおよび乾燥ジオキ
サン100mlを入れ、氷冷下に油性水素化ナトリウ
ム（水素化ナトリウム含量約50重量％）5.0ｇを
徐々に加えた。ついで氷冷下にＮ，Ｎ−ジメチル
カルバモイルクロリド〔（CH3）2NCOCl〕12ｇを
徐々に滴下した。滴下終了後、加温してジオキサ
ン還流下に１時間反応を行なつた。反応終了後、
生成した塩を別し、液からジオキサンを留去
した。残留物を0.5重量％のイソプロパノールを
含むｎ−ヘキサンを展開溶媒とした液体クロマト
グラフイー（ウオータース社システム500を使
用）により処理して淡黄色の液体23.2ｇを分取し
た。この物質はプロトンNMRおよび質量分析に
より下記の構造式で示されるフアルネシルエチル
Ｎ，Ｎ−ジメチルカルバメートであることが確
認された。
NMRのデータを下記に示す。（90MHz，CDCl3
溶媒）[Table] The present invention will be explained below with reference to Examples, but the present invention is not limited by these Examples. Example 1 25.0 g of 5,9,13-trimethyltetradeca-4,8,12-trien-1-ol (also known as farnesylethanol) was placed in a 300 ml three-necked flask equipped with a thermometer and a reflux condenser. and 100 ml of dry dioxane were added thereto, and 5.0 g of oily sodium hydride (sodium hydride content: approximately 50% by weight) was gradually added under ice cooling. Then, 12 g of N,N-dimethylcarbamoyl chloride [(CH 3 ) 2 NCOCl] was gradually added dropwise under ice cooling. After the dropwise addition was completed, the mixture was heated and reacted for 1 hour under dioxane reflux. After the reaction is complete,
The generated salt was separated and dioxane was distilled off from the liquid. The residue was subjected to liquid chromatography (using Waters System 500) using n-hexane containing 0.5% by weight of isopropanol as a developing solvent, and 23.2 g of a pale yellow liquid was separated. This substance was confirmed by proton NMR and mass spectrometry to be pharnesylethyl N,N-dimethylcarbamate shown by the following structural formula. NMR data is shown below. (90MHz, CDCl 3
solvent)
【表】
＝
／
[Table] =
/
【表】【table】
【表】
実施例 ２〜４
表２に示すアルコールおよびＮ，Ｎ−ジアルキ
ルカルバモイルクロリドを表２に示す量で使用
し、油性水素化ナトリウム（NaH含量50重量％）
を５ｇ（実施例２）または2.5ｇ（実施例３およ
び４）使用し、実施例１と同様にして種々のＮ，
Ｎ−ジアルキルカルバミン酸エステルを合成し
た。反応後、生成した塩を別し、液から溶媒
を留去し、残留物を実施例１と同様の展開溶媒を
用いて液体クロマトグラフイーにより処理して目
的とするＮ，Ｎ−ジアルキルカルバミン酸エステ
ルを分取し、プロトンNMR（90MHz；CDCl3溶液
で測定）および質量分析によりそれらの構造確認
を行なつた。結果を表２にまとめて示す。なお、
表２中Ｇ−、Fa−およびＧ・Ｇ−はそれぞれ下
記の基を意味する。
[Table] Examples 2 to 4 The alcohols and N,N-dialkylcarbamoyl chlorides shown in Table 2 were used in the amounts shown in Table 2, and oily sodium hydride (NaH content 50% by weight) was prepared.
Using 5g (Example 2) or 2.5g (Examples 3 and 4), various N,
N-dialkylcarbamate ester was synthesized. After the reaction, the generated salt was separated, the solvent was distilled off from the liquid, and the residue was treated with liquid chromatography using the same developing solvent as in Example 1 to obtain the desired N,N-dialkylcarbamic acid. The esters were separated and their structures were confirmed by proton NMR (90 MHz; measured with CDCl 3 solution) and mass spectrometry. The results are summarized in Table 2. In addition,
In Table 2, G-, Fa- and GG- mean the following groups, respectively.
【表】【table】
Claims (1)
R2は低級アルキル基を表わす）で示されるＮ，
Ｎ−ジアルキルカルバミン酸エステル。[Claims] 1. General formula (In the formula, n represents an integer of 1 to 3, R 1 and
R 2 represents a lower alkyl group),
N-dialkylcarbamate ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14707280A JPS5770854A (en) | 1980-10-20 | 1980-10-20 | N,n-dialkyl carbamate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14707280A JPS5770854A (en) | 1980-10-20 | 1980-10-20 | N,n-dialkyl carbamate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5770854A JPS5770854A (en) | 1982-05-01 |
| JPS6257181B2 true JPS6257181B2 (en) | 1987-11-30 |
Family
ID=15421829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14707280A Granted JPS5770854A (en) | 1980-10-20 | 1980-10-20 | N,n-dialkyl carbamate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5770854A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01171384U (en) * | 1988-05-23 | 1989-12-05 | ||
| JPH01171383U (en) * | 1988-05-23 | 1989-12-05 | ||
| JPH0314408U (en) * | 1989-06-27 | 1991-02-14 |
-
1980
- 1980-10-20 JP JP14707280A patent/JPS5770854A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01171384U (en) * | 1988-05-23 | 1989-12-05 | ||
| JPH01171383U (en) * | 1988-05-23 | 1989-12-05 | ||
| JPH0314408U (en) * | 1989-06-27 | 1991-02-14 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5770854A (en) | 1982-05-01 |
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