JPS6320238B2 - - Google Patents
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- Publication number
- JPS6320238B2 JPS6320238B2 JP1793980A JP1793980A JPS6320238B2 JP S6320238 B2 JPS6320238 B2 JP S6320238B2 JP 1793980 A JP1793980 A JP 1793980A JP 1793980 A JP1793980 A JP 1793980A JP S6320238 B2 JPS6320238 B2 JP S6320238B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- represented
- salt
- hydrate
- compound according
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000002246 antineoplastic agent Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- SIFHZKKXWMJWOB-UHFFFAOYSA-N 2-(hexadecylamino)ethanol Chemical compound CCCCCCCCCCCCCCCCNCCO SIFHZKKXWMJWOB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000022534 cell killing Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明は、新規な燐化合物、すなわち、一般式
「式中、R1は水素原子またはアルキル基を；
R2は水素原子、ヒドロキシル基または低級アル
コキシ基を；A1は低級アルキレン基を；Ｘは式
The present invention provides novel phosphorus compounds, namely the general formula "In the formula, R 1 is a hydrogen atom or an alkyl group;
R 2 is a hydrogen atom, hydroxyl group or lower alkoxy group; A 1 is a lower alkylene group; X is a formula
【式】または[expression] or
【式】（R3，R4，R5，
R6およびR7は低級アルキル基を示す。）で表わさ
れる基またはＮ―ピリジニウム基を；Ｚは水素原
子、アルキル基またはフエニル基またはハロゲン
原子もしくはヒドロキシルもしくはアセチルオキ
シ基で置換された低級アルキル基または、
式[Formula] (R 3 , R 4 , R 5 , R 6 and R 7 are lower alkyl groups) or N-pyridinium group; Z is a hydrogen atom, an alkyl group, a phenyl group, or a halogen atom or a lower alkyl group substituted with a hydroxyl or acetyloxy group, or a lower alkyl group substituted with a hydroxyl or acetyloxy group, or
【式】
（A2は低級アルキレン基を、R8およびR9は同
一または異なつて、水素原子またはアルキル基ま
たはハロゲン原子で置換された低級アルキル基を
示す。）で表わされる基を；Y1は酸素原子を；Y2
はヒドロキシル基またはOを；およびｌはＯま
た１をそれぞれ表わす。」
で表わされる化合物、その塩および水和物並びに
それらを含有する抗腫瘍剤に関する。
本発明者等は長年・抗腫瘍効果を有する物質を
見出すべく鋭意研究をしたところ、本発明の化合
物が生体内で、殺細胞効果を示し、強い抗腫瘍作
用を発揮し、また宿主介在性の作用（免疫賦活作
用）を発揮するという有用な性質を有することを
見出し、本発明を完成するに至つた。
一般式〔〕で表わされる化合物について詳説
する。R1におけるアルキル基としては、たとえ
ば、C1〜22アルキル基を；R2における低級アルコ
キシ基としては、たとえばC1〜4アルキルオキシ基
を；A1およびA2における低級アルキレン基とし
ては、たとえば、C1〜4アルキレン基を；R3，R4，
R5，R6およびR7における低級アルキル基として
は、たとえば、C1〜4アルキル基を挙げることがで
きる。また、Ｚにおけるアルキル基としては、た
とえば、C1〜22アルキル基が挙げられる。また、
低級アルキル基としては、たとえば、C1〜4アルキ
ル基が挙げられ、これはハロゲン原子、ヒドロキ
シルもしくはアセチルオキシ基で置換されていて
もよい。R8およびR9におけるアルキル基として
は、C1〜22アルキル基が挙げられ、また、ハロゲ
ン原子で置換されていた低級アルキル基として
は、ハロゲン原子置換C1〜4アルキル基が挙げられ
る。
以上、説明した化合物中で、R1が炭素原子14
〜20個を有する基で、Ｚが水素原子または炭素原
子１〜８個を有する基の場合が好ましく、更には
R1がC14〜20アルキル基、Ｘが式[Formula] (A 2 is a lower alkylene group, R 8 and R 9 are the same or different and represent a hydrogen atom, an alkyl group, or a lower alkyl group substituted with a halogen atom.); Y 1 is an oxygen atom; Y 2
represents a hydroxyl group or O; and l represents O or 1, respectively. ”, salts and hydrates thereof, and antitumor agents containing them. The present inventors have conducted intensive research for many years to find substances with antitumor effects, and have found that the compounds of the present invention exhibit cell-killing effects in vivo, exhibit strong antitumor effects, and exhibit host-mediated antitumor effects. The present inventors discovered that they have a useful property of exerting an immunostimulating effect, and completed the present invention. The compound represented by the general formula [] will be explained in detail. The alkyl group in R 1 is, for example, a C 1-22 alkyl group; the lower alkoxy group in R 2 is, for example, a C 1-4 alkyloxy group; the lower alkylene group in A 1 and A 2 is, for example, , C 1-4 alkylene group; R 3 , R 4 ,
Examples of lower alkyl groups in R 5 , R 6 and R 7 include C 1-4 alkyl groups. Further, examples of the alkyl group in Z include a C 1-22 alkyl group. Also,
Examples of lower alkyl groups include C 1-4 alkyl groups, which may be substituted with halogen atoms, hydroxyl or acetyloxy groups. Examples of the alkyl group in R 8 and R 9 include a C 1-22 alkyl group, and examples of the lower alkyl group substituted with a halogen atom include a halogen atom-substituted C 1-4 alkyl group. In the compounds explained above, R 1 is a carbon atom of 14
It is preferable that Z is a hydrogen atom or a group having 1 to 8 carbon atoms, and more preferably
R 1 is a C 14-20 alkyl group, X is the formula
【式】で示
される基およびＺが水素原子またはヒドロキシル
基もしくはハロゲン原子で置換されたC1〜4のアル
キル基の場合が好ましく、特にR5，R6およびR7
がメチルまたはエチル基で、ｌ＝０の場合が好ま
しい。
本発明の一般式〔〕で表わされれる化合物の
塩としては、たとえば、Ｘが式The group represented by [Formula] and Z are preferably C 1-4 alkyl groups substituted with a hydrogen atom, a hydroxyl group, or a halogen atom, particularly R 5 , R 6 and R 7
is a methyl or ethyl group and l=0 is preferred. As a salt of the compound represented by the general formula [] of the present invention, for example, X is the formula
【式】または[expression] or
【式】で示される基と、鉱酸（たとえば、
塩酸または硫酸など）から形成される塩；式
A salt formed from a group represented by the formula and a mineral acid (such as hydrochloric acid or sulfuric acid);
【式】で示される基とMn〔Mnはｎ
価（ｎは１または２）の陽イオンを示し、たとえ
ばN+ a，K+C2+ a，Z2+ oまたはM2+ gなどが挙げられ
る〕とから形成されるA group represented by [Formula] and M n [M n represents a cation with n valence (n is 1 or 2), such as N + a , K + C 2+ a , Z 2+ o or M 2+ g etc.] is formed from
【式】型の塩もし
くはトリエチルアミンなどの有機塩基とから形成
されるFormed from a salt of the formula or an organic base such as triethylamine
【式】（はトリエチルアミンな
どの有機塩基を示す）型の塩；または一般式
〔〕で表わされる化合物がカルボキシル基など
の塩を形成し得る基を有する場合、たとえばN+ a，
K+，C2+ a，Z2+ oまたはM2+ gなどとから形成される
塩もしくはトリエチルアミンなどの有機塩基とか
ら形成される塩を挙げることができ、更には、塩
化水素酸塩または臭化水素酸塩などのハロゲン化
水素酸塩をも挙げることができる。
また、一般式〔〕で表わされる化合物、その
塩並びにその水和物の全ての異性体および結晶形
も本発明に包含される。
次に、本発明化合物の製造法について述べる。
一般式〔〕で表わされる化合物を得る方法は
種々あるが、それらのうちで代表的製造法を次の
反応経路図に示す。原料の一般式〔〕または
〔〕で表わされる化合物は、自体公知の方法に
より製造され、たとえば、ｌ＝０の場合、エタノ
ールアミン、Ｎ―メチルエタノールアミン、Ｎ―
エチルエタノールアミン、Ｎ―セチルエタノール
アミンもしくはそれらの置換体、ｌ＝１の場合、
プロパノールアミンもしくはそれの置換体などの
化合物を原料として製造される。[Formula] (represents an organic base such as triethylamine) type salt; or when the compound represented by the general formula [] has a group capable of forming a salt such as a carboxyl group, for example, N + a ,
Examples include salts formed with K + , C 2+ a , Z 2+ o or M 2+ g , or salts formed with organic bases such as triethylamine; furthermore, hydrochloride or Mention may also be made of hydrohalides such as hydrobromide. The present invention also includes all isomers and crystal forms of the compound represented by the general formula [], its salts, and its hydrates. Next, a method for producing the compound of the present invention will be described. There are various methods for obtaining the compound represented by the general formula [], and among them, a typical manufacturing method is shown in the following reaction route diagram. The compound represented by the general formula [] or [] as a raw material is produced by a method known per se. For example, when l=0, ethanolamine, N-methylethanolamine, N-
Ethylethanolamine, N-cetylethanolamine or substituted products thereof, when l = 1,
It is manufactured using compounds such as propanolamine or its substituted products as raw materials.
【表】
アミノ化
O−P(O)−O−Z
【table】
Amination
O−P(O)−O−Z
Claims (1)
R2は水素原子、ヒドロキシル基または低級アル
コキシ基を；A1は低級アルキレン基を；Ｘは式
【式】または【式】（R3，R4，R5， R6およびR7は低級アルキル基を示す。）で表わさ
れる基またはＮ―ピリジニウム基を；Ｚは水素原
子、アルキル基またはフエニル基またはハロゲン
原子もしくはヒドロキシルもしくはアセチルオキ
シ基で置換された低級アルキル基または式
【式】 （A2は低級アルキレン基を、R8およびR9は同
一または異なつて、水素原子またはアルキル基ま
たはハロゲン原子で置換された低級アルキル基を
示す。）で表わされる基を；Y1は酸素原子を；Y2
はヒドロキシル基またはOを；およびｌはＯま
たは１をそれぞれ表わす。」 で表わされる化合物およびその塩並びにその水和
物。 ２ 一般式 「式中、R1，R2およびＺは前記した意味を有
する。」 で表わされる特許請求の範囲第１項記載の化合物
およびその塩並びにその水和物。 ３ 式 で表わされる特許請求の範囲第２項記載の化合物
およびその塩並びにその水和物。 ４ 式 で表わされる特許請求の範囲第２項記載の化合物
およびその塩並びにその水和物。 ５ 式 で表わされる特許請求の範囲第２項記載の化合物
およびその塩並びにその水和物。 ６ 式 で表わされる特許請求の範囲第２項記載の化合物
およびその塩並びにその水和物。 ７ 一般式 「式中、R1，A1，ＸおよびＺは前記した意味
を有する。」 で表わされる特許請求の範囲第１項記載の化合物
およびその塩並びにその水和物。 ８ 式 で表わされる特許請求の範囲第７項記載の化合物
およびその塩並びにその水和物。 ９ 式 で表わされる特許請求の範囲第７項記載の化合物
およびその塩並びにその水和物。 １０ 式 で表わされる特許請求の範囲第７項記載の化合物
およびその塩並びにその水和物。 １１ 式 で表わされる特許請求の範囲第７項記載の化合物
およびその塩並びにその水和物。 １２ 式 で表わされる特許請求の範囲第７項記載の化合物
およびその塩並びにその水和物。 １３ 式 で表わされる特許請求の範囲第７項記載の化合物
およびその塩並びにその水和物。 １４ 式 で表わされる特許請求の範囲第７項記載の化合物
およびその塩並びにその水和物。 １５ 一般式 「式中、R1は水素原子またはアルキル基を；
R2は水素原子、ヒドロキシル基または低級アル
コキシ基を；A1は低級アルキレン基を；Ｘは式
【式】または【式】（R3，R4，R5， R6およびR7は低級アルキル基を示す。）で表され
る基またはＮ―ピリジニウム基を；Ｚは水素原
子、アルキル基またはフエニル基またはハロゲン
原子もしくはヒドロキシルもしくはアセチルオキ
シ基で置換された低級アルキル基または式
【式】 （A2は低級アルキレン基を、R8およびR9は同
一または異なつて、水素原子またはアルキル基ま
たはハロゲン原子で置換された低級アルキル基を
示す。）で表わされる基を；Y1は酸素原子を；Y2
はヒドロキシル基またはOを；およびｌはＯま
たは１をそれぞれ表わす。」 で表わされる化合物およびその塩並びにその水和
物を含有する抗腫瘍剤。 １６ 一般式 「式中、R1，R2およびＺは前記した意味を有
する。」 で表わされる特許請求の範囲第１５項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 １７ 式 で表わされる特許請求の範囲第１６項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 １８ 式 で表わされる特許請求の範囲第１６項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 １９ 式 で表わされる特許請求の範囲第１６項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２０ 式 で表わされる特許請求の範囲第１６項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２１ 一般式 「式中、R1，A1，ＸおよびＺは前記した意味
を有する。」 で表わされる特許請求の範囲第１５項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２２ 式 で表わされる特許請求の範囲第２１項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２３ 式 で表わされる特許請求の範囲第２１項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２４ 式 で表わされる特許請求の範囲第２１項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２５ 式 で表わされる特許請求の範囲第２１項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２６ 式 で表わされる特許請求の範囲第２１項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２７ 式 で表わされる特許請求の範囲第２１項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。 ２８ 式 で表わされる特許請求の範囲第２１項記載の化合
物およびその塩並びにその水和物を含有する抗腫
瘍剤。[Claims] 1. General formula "In the formula, R 1 is a hydrogen atom or an alkyl group;
R 2 is a hydrogen atom, a hydroxyl group , or a lower alkoxy group ; A 1 is a lower alkylene group; ) or an N-pyridinium group; Z is a hydrogen atom, an alkyl group, a phenyl group, a halogen atom, or a lower alkyl group substituted with a hydroxyl or acetyloxy group, or a group represented by the formula [Formula] (A 2 represents a lower alkylene group; R 8 and R 9 are the same or different and represent a hydrogen atom, an alkyl group, or a lower alkyl group substituted with a halogen atom; Y 1 represents an oxygen atom; Y 2
represents a hydroxyl group or O; and l represents O or 1, respectively. ” Compounds, salts thereof, and hydrates thereof. 2 General formula The compound according to claim 1, represented by the following formula: "In the formula, R 1 , R 2 and Z have the meanings described above.", a salt thereof, and a hydrate thereof. 3 formulas The compound according to claim 2, which is represented by: and its salt and hydrate. 4 formula The compound according to claim 2, which is represented by: and its salt and hydrate. 5 formula The compound according to claim 2, which is represented by: and its salt and hydrate. 6 formula The compound according to claim 2, which is represented by: and its salt and hydrate. 7 General formula The compound according to claim 1, which is represented by the following formula: "In the formula, R 1 , A 1 , X and Z have the meanings described above.", a salt thereof, and a hydrate thereof. 8 formula The compound according to claim 7, represented by the above formula, a salt thereof, and a hydrate thereof. 9 formula The compound according to claim 7, represented by the above formula, a salt thereof, and a hydrate thereof. 10 formula The compound according to claim 7, represented by the above formula, a salt thereof, and a hydrate thereof. 11 formula The compound according to claim 7, represented by the above formula, a salt thereof, and a hydrate thereof. 12 formula The compound according to claim 7, represented by the above formula, a salt thereof, and a hydrate thereof. 13 formula The compound according to claim 7, represented by the above formula, a salt thereof, and a hydrate thereof. 14 formula The compound according to claim 7, represented by the above formula, a salt thereof, and a hydrate thereof. 15 General formula "In the formula, R 1 is a hydrogen atom or an alkyl group;
R 2 is a hydrogen atom, a hydroxyl group , or a lower alkoxy group ; A 1 is a lower alkylene group; ) or an N-pyridinium group; Z is a hydrogen atom, an alkyl group, a phenyl group, a halogen atom, or a lower alkyl group substituted with a hydroxyl or acetyloxy group, or a group represented by the formula [Formula] (A 2 represents a lower alkylene group; R 8 and R 9 are the same or different and represent a hydrogen atom, an alkyl group, or a lower alkyl group substituted with a halogen atom; Y 1 represents an oxygen atom; Y 2
represents a hydroxyl group or O; and l represents O or 1, respectively. An antitumor agent containing a compound represented by the following formula, a salt thereof, and a hydrate thereof. 16 General formula An antitumor agent containing the compound according to claim 15, a salt thereof, and a hydrate thereof, represented by the following formula: "In the formula, R 1 , R 2 and Z have the above-mentioned meanings." 17 formula An antitumor agent containing the compound according to claim 16, represented by the above formula, a salt thereof, and a hydrate thereof. 18 formula An antitumor agent containing the compound according to claim 16, represented by the above formula, a salt thereof, and a hydrate thereof. 19 formula An antitumor agent containing the compound according to claim 16, represented by the above formula, a salt thereof, and a hydrate thereof. 20 formula An antitumor agent containing the compound according to claim 16, represented by the above formula, a salt thereof, and a hydrate thereof. 21 General formula An antitumor agent containing the compound according to claim 15, a salt thereof, and a hydrate thereof, represented by the following formula: "In the formula, R 1 , A 1 , X and Z have the above-mentioned meanings." 22 formula An antitumor agent containing the compound according to claim 21, represented by the following formula, a salt thereof, and a hydrate thereof. 23 formula An antitumor agent containing the compound according to claim 21, represented by the following formula, a salt thereof, and a hydrate thereof. 24 formula An antitumor agent containing the compound according to claim 21, represented by the following formula, a salt thereof, and a hydrate thereof. 25 formula An antitumor agent containing the compound according to claim 21, represented by the following formula, a salt thereof, and a hydrate thereof. 26 formula An antitumor agent containing the compound according to claim 21, represented by the following formula, a salt thereof, and a hydrate thereof. 27 formula An antitumor agent containing the compound according to claim 21, represented by the following formula, a salt thereof, and a hydrate thereof. 28 formula An antitumor agent containing the compound according to claim 21, represented by the following formula, a salt thereof, and a hydrate thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1793980A JPS56115792A (en) | 1980-02-18 | 1980-02-18 | Novel phosphorus compound and antitumor agent containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1793980A JPS56115792A (en) | 1980-02-18 | 1980-02-18 | Novel phosphorus compound and antitumor agent containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56115792A JPS56115792A (en) | 1981-09-11 |
| JPS6320238B2 true JPS6320238B2 (en) | 1988-04-26 |
Family
ID=11957742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1793980A Granted JPS56115792A (en) | 1980-02-18 | 1980-02-18 | Novel phosphorus compound and antitumor agent containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56115792A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5130036A (en) * | 1990-05-18 | 1992-07-14 | The Elco Corporation | Phosphorous amine lubricant additives |
-
1980
- 1980-02-18 JP JP1793980A patent/JPS56115792A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56115792A (en) | 1981-09-11 |
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