JPS60501257A - An aziridino derivative of a tetrameric cyclophosphazene chloride compound, a method for producing the same, and an aziridino derivative obtained by substituting the chlorine atom of this compound - Google Patents
An aziridino derivative of a tetrameric cyclophosphazene chloride compound, a method for producing the same, and an aziridino derivative obtained by substituting the chlorine atom of this compoundInfo
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- JPS60501257A JPS60501257A JP59501896A JP50189684A JPS60501257A JP S60501257 A JPS60501257 A JP S60501257A JP 59501896 A JP59501896 A JP 59501896A JP 50189684 A JP50189684 A JP 50189684A JP S60501257 A JPS60501257 A JP S60501257A
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- JP
- Japan
- Prior art keywords
- compound
- azirizoino
- chemical formula
- reaction
- tetrameric
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Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 title claims description 6
- 229910052801 chlorine Inorganic materials 0.000 title description 6
- 150000001805 chlorine compounds Chemical class 0.000 title description 2
- 239000000126 substance Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 7
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 6
- 238000007098 aminolysis reaction Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 claims description 2
- 229910000063 azene Inorganic materials 0.000 claims 2
- 241001137251 Corvidae Species 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- WDEFWOPTRFWZLM-LEQGEALCSA-N (2,5-dioxopyrrolidin-1-yl) (2r)-2,5,7,8-tetramethyl-6-(oxan-2-yloxy)-3,4-dihydrochromene-2-carboxylate Chemical compound C([C@@](C)(OC=1C(C)=C2C)C(=O)ON3C(CCC3=O)=O)CC=1C(C)=C2OC1CCCCO1 WDEFWOPTRFWZLM-LEQGEALCSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 210000003323 beak Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000002468 fat body Anatomy 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65817—Cyclic phosphazenes [P=N-]n, n>=3 n = 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cephalosporin Compounds (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるため要約のデータは記録されません。 (57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】 四量体塩化シクロフォスフアゼン化合物のアジリゾイノ舖導坏、その製造方法、 及びこの化合−物の塩゛素原子ｌ置換し二て得、られろアジリグイノ誘導体 本発明は四量体シクロクロロフォスフアゼン化合物のアジリゾイノ肪褥体に関す る。[Detailed description of the invention] Azirizoino derivative of tetrameric cyclophosphazene chloride compound, method for producing the same, And, by substituting the chlorine atom of this compound with 1, a rairo aziligino derivative is obtained. The present invention relates to azirizoino fat bodies of tetrameric cyclochlorophosphazene compounds. Ru.
化学式Ｎ４Ｐ４ＣＡ’ｓ Ｙ有する（ＮＰＣＡ’２）四量体およびＡｚ ’Ｊ（ アシリゾイノとしてそれから誘碑された化合物Ｎ４Ｐ４ＡＺ８は雑誌Ｆａｒｍａ ｋｏ１．Ｔｏｋｓｉｋｏ１． （モス＝＋ −）Ｚ、３６５（１９５９）［ＮＪ 載されたＶ、Ａ、Ｃｈｅｒ−ｎＯＶ＋ ｖ、 Ｂ、 ＬｙＬｋｉｎａ、 Ｓ、 Ｉ−Ｓｅｒｇｉｅｖｓｋａｙａ＋ Ａ、 Ａ−Ｋｒｏｐａｃｈｅｖａ、 Ｖ、 Ａ、 Ｐａｒｓｈ”ｉｎａおよびＬ−Ｅ、 ５ｖｅｎｔｓｉ−１ｓｋａｙａによ る論文から公知である。化合物Ｎ４Ｐ４ＡｚＢについては、それがラットにおけ る５−４５肉ｊ厘に対して抗腫瘍活性乞持っていることが示されている。(NPCA’2) tetramer with the chemical formula N4P4CA’s Y and Az’J ( The compound N4P4AZ8, which was then coined as acyrhizoino, was published in the magazine Farma ko1. Toksiko1. (Moss = + -) Z, 365 (1959) [NJ Listed V, A, Cher-nOV+ v, B, LyLkina, S, I-Sergievskaya + A, A-Kropacheva, V, By A, Parsh”ina and L-E, 5ventsi-1skaya It is publicly known from a paper published by For the compound N4P4AzB, it was found that in rats It has been shown that it has antitumor activity against 5-45 meat.
そのうえ、Ｉｎｏｒｇ、 Ｃｈｅｍ−３（１９６４） ７５７−７６１は、化合 物” ４ Ｐ ４ Ａ ｚ ４が反応媒体として芳香族灰化水素および酸性受容 体としてトリエチルアミンの中のアジリゾインおよびその向族体乞使った四量体 Ｎ４Ｐ４Ｃ７１！８の先金なアミノ分解によって作られることができることを開 示している。Moreover, Inorg, Chem-3 (1964) 757-761 describes the compound Aromatic hydrogen ash and acid acceptor as reaction medium Azirizoin in triethylamine as a body and its homologous tetramer It has been discovered that N4P4C71!8 can be made by preliminary aminolysis. It shows.
本発明の目的は、四量体のシクロクロロフォスフアゼンのアジリグイノ誘導体を 提供することである。それは、塩素原子を適当に退択された置換体で置き侠える ことによって、それから訪得され、単数またをま板数のアジリゾイノ群？含む四 量体シクロフォスフアゼン化合物の合成における出発物質の役をする。佐省の化 合物もまた抗腫瘍活性を待っていることが期待される。The object of the present invention is to prepare aziligino derivatives of tetrameric cyclochlorophosphazene. It is to provide. It can place the chlorine atom with a suitably depleted substitution. By which is it then visited and the singular or cutting number azirizoino group? including four It serves as a starting material in the synthesis of meric cyclophosphazene compounds. Sasho's transformation It is expected that the compounds would also exhibit anti-tumor activity.
このため、本発明は、ｎ＝１． ２，３ｔ ４，５．６または７として化学式Ｎ ４Ｐ４ＣＩＢ−ＯＡｚＨによって特牽づけられる、冒頭の如で延在された糧類の 化合物を提供する。Therefore, in the present invention, n=1. 2,3t 4,5.6 or 7 as chemical formula N 4P4CIB-OAzH specifically promotes food products as mentioned in the beginning. provide a compound.
本発明による化合物の製造は良く用心して４ろ容易に行なわれるけれども、いろ いろの大部分異性体の生成物の分離は容易ではない。圀えはアシリティンとの（ ＮＰＣ＃ｔ２）４ の反応は、沢山の生成物Ｎ４Ｐ４（Ｊ’５Ａｚ３に加えて、 ｌ：３．５のモル比で王としてつき０６つの生成物を与える。Although the preparation of the compounds according to the invention is carried out with great care and ease, there are many Separation of the predominantly isomeric products is not easy. The story is with Asiritin ( The reaction of NPC#t2)4 produces many products, N4P4 (J'5Az3), as well as A molar ratio of l:3.5 gives a total of 06 products.
Ｎ４Ｐ４Ｃ１７Ａｚ ジェム−Ｎ４Ｐ４Ｃ１６ＡＺ２ １．３−シス−Ｎ４Ｐ４Ｃｊ？６Ａｚ２１．５−シス−Ｎ４Ｐ４ＣＡ！６ＡＺ２ １．３−トラ）’ス、−Ｎ４Ｐ４Ｃ１６Ａｚ２１．５−トラ、：／ノーＮ４Ｐ４ ＣＪ６ＡＺ２これらの化合物の構造式の図式的な表示か化学式の厭來の化学式１ −６によって与えられている。そこでリングのＮ原子およびＣノ原子は省略され ている。N4P4C17Az Gem-N4P4C16AZ2 1.3-cis-N4P4Cj? 6Az21.5-cis-N4P4CA! 6AZ2 1.3-Tora)’s, -N4P4C16Az21.5-Tora, :/No N4P4 CJ6AZ2 Schematic representation of the structural formulas of these compounds or chemical formulas of the disgusting chemical formula 1 −6. Therefore, the N and C atoms of the ring are omitted. ing.
したがって、前の節の中で述べられたこと忙合致して、本発明はまた、シクロポ リクσロンオスンアゼンの反応溶液の中でのアミノ分解および反応混合物の処理 によって、本発明によるアジリゾイノ肪導体ヲ裳造するための方法に関し、その 方法はｎ”” ０ ＋ １ ＋ ２＋３．４．５または６として化学式Ｎ４Ｐ４ ＣＩ１８’−ｎＡｚｎ ？有する化合物にお（・てｌ−７塩素原子かアシリゾイ ノ群によって置換されること、およびその結果生じるアジリゾイノＮｏ体かＨＰ Ｌ Ｃ（”ｈｉｇｈ ｐｅｒｆｏｒｍａｎｃｅｌｉｑｕｉｄ ｃｈｒｏｍａｔ ｏｇｒａｐｈｙ （＝性能液体クロマトグランイ））乞使って反応混合物の処理 の後行られる生成物から回収されることヲ軸承とする。本発明による方法におい てコラム材料および浴離液の退択は、ＨＰ Ｌ Ｃ技術の応用の範囲内で、分析 しようと１−る反応混合物に依存する。Therefore, consistent with what was stated in the previous section, the present invention also Aminolysis of Rikuσlonosunazene in the reaction solution and treatment of the reaction mixture describes a method for fabricating an azirizoino fat conductor according to the present invention. The method is n"" 0 + 1 + 2 + 3.4.5 or 6 as chemical formula N4P4 CI18'-nAzn? In the compound that has (・l-7 chlorine atom or and the resulting azirizoino No body or HP L C (high performance liquid chromat Ography (= performance liquid chromatography)) is used to process reaction mixtures. It is assumed that it will be recovered from the product produced after the process. In the method according to the invention The removal of column material and bath separation liquid is analyzed within the scope of the application of HPLC technology. It depends on the reaction mixture being attempted.
以下に明らかにされるよう釦、ポリアジリゾイノ置換に対するモノアジリゾイノ の比は、向えは（ＮＰＣ７２）４から出発する場合、反応成分のモル比および必 要な場合には反応時間に作用乞及はすことによって変化させられるディアジリゾ イノ瀘換に則するモノアジリゾイノの反応缶底物中の比である。Button, monoazirizoino to polyazirizoino substitution as revealed below When starting from (NPC72)4, the molar ratio of the reactants and the required Diazilyso, which can be varied by influencing the reaction time if necessary. This is the ratio of monoazirizoino in the bottom of the reactor according to inofiltration.
本発明による方法か実行されることかできる過半な溶媒は乾燥したティエチルエ ーテルである。しかし、ベンゼン、ペンタン、ヘキサンおよびＴＨＦ（テトラハ イドロフラン）がその中で反応を行なわせるのに過半である。The majority solvent in which the process according to the invention can be carried out is dry thiethyl ethyl ether. - Tel. However, benzene, pentane, hexane and THF (tetrahalyl Hydrofuran) accounts for the majority of the reactions in it.
塩素原子か適切に選択された他の置換体によって置き換えられるので、本発明に よる四量体のシクロクロロフォスフアゼンのアシリゾイノ＝Ｓ体はそれから化合 物を製造するための適当な出発材料である。後に公開されたオランダ特願第８３ ．’ｏｏ５７３号からの教えに鑑みて、このような化合物か抗腫瘍活性を待って いることか期待される。In the present invention, the chlorine atom is replaced by another appropriately selected substituent. The acyrizoino=S form of tetrameric cyclochlorophosphazene is then compounded by It is a suitable starting material for manufacturing products. Dutch Patent Application No. 83, later published ．． In light of the teachings from 'oo573, we are waiting for such compounds to have anti-tumor activity. It is expected that there will be.
したがって、本発明はまた、ｎ＝１．’２，３，４゜５．６または７であり、Ｒ は四じまたは異ったに換体乞表わすものとして抗腫瘍活性を有する四量体の置換 されたシクロンオスファセン化合物のアジリグイノ誘導体にも開する。Therefore, the present invention also provides that n=1. ’2,3,4°5.6 or 7, R Substitution of the tetramer with antitumor activity as a substitute for four or a different substitution The aziligino derivatives of the cycloosphacene compounds are also developed.
Ｒは数回く加水分層に対して低い感度を有する４市。R is 4 cities with low sensitivity to the hydrolysis layer several times.
子群である。It is a child group.
本発明か以下に示される実施的によって明らかにされるだろう。The present invention will be made clearer by the implementation shown below.
実施的 ｌ Ｎ４Ｐ４ＡｚｎＧＡ’５−ｎ（ｎ−１＋ ２ ）の製造（ＮＰＣＡ＋２）４（Ｏ ｌｓｕｋａ Ｃｈｅｍ、 ）は使用前ニヘキサンから再結晶さセられた。アジリ ゾインは使用直前に乾燥象累の下でＫＯＨのビルから蒸溜された。溶媒は通常の 方法で純化され、乾燥させられた。反応は乾燥窒素雰囲気中で行なわれた。３１ ＦおよびＩＨＮＭＲスペクトルがＮＴＣＦＴ−１１８０データシステムを備え たＮ１ｃｏｌｅｔ ２８３Ａ Ｆ Ｔ ヌペクトロメータを使って２５Ｃで１０ １１１のチューブの中で測定された。溶て使用された。ＨＰＬＣ分離が二つのＷ ａｔｅ’ｒβ６０００Ａ液体ポンプ（各々は２０勃 ／ｍＪｎ、の容量を持って （・る）およびＷａｔｅｒｓ屈折計？用いて行なわれた。Practical l Production of N4P4AznGA'5-n (n-1+2) (NPCA+2)4(O lsuka Chem, ) was recrystallized from nihexane before use. Ajiri Zoin was distilled from the KOH building under dry conditions immediately before use. Solvent is normal method and dried. The reaction was carried out in a dry nitrogen atmosphere. 31 F and IH NMR spectra equipped with NTCFT-1180 data system 10 at 25C using a N1colet 283A FT Nupectrometer. Measured in 111 tubes. It was melted and used. HPLC separation is two W ate'rβ6000A liquid pump (each has a capacity of 20 e/mJn) (・ru) and Waters refractometer? It was done using
Ｌｉｃｈｒｏｓｏｒｂ Ｓ’ｉ ６０／１０がコラム材料の役をした。Lichrosorb S'i 60/10 served as column material.
Ａ０モル比１：２．５での（ＮＰＣＩ２）、のアシリゾインとの反応 １５０ＯＮの乾燥ディエルチルエーテルの中の１．４１ のアジリゾインの浴Ｋ （２７，１ｍｍｏ Ｉ！ ）が３００１ の乾燥ディエチルエーテルの中の５ ．Ｏｇの（ＮＰＣＩ ２ ） ４の溶液（’ １０．８ｍｍｏＡりＬ、撒しく撹 拌し、−２０Ｃに冷却しながら、３０−４５分間滴下して加えられた。反応波混 合物がゆっくり室温まで加熱された。１８時間の反応時間の後、重合アミノＨ（ Ｊ塩の濾過および２Ｆ液の蒸発は５．１ｇの白色隙状のオイルを与えた゛。それ は加水分ｐ＃に対して僅かに感じることがわかった（ 生成物Ａ）。Reaction of (NPCI2) with acyrizoin in A0 molar ratio 1:2.5 1.41 azirizoin bath K in 150 ON dry diethyl ether (27,1 mmo I!) is 5 in 3001 dry diethyl ether ．． A solution of Og (NPCI 2) 4 (’10.8 mmoA L, stir thoroughly Added dropwise over 30-45 minutes while stirring and cooling to -20C. reaction wave mixture The compound was slowly heated to room temperature. After a reaction time of 18 hours, polymerized amino H ( Filtration of the J salt and evaporation of the 2F solution gave 5.1 g of a white powdery oil. that was found to be slightly sensitive to hydrolyzed p# (Product A).
Ｂ１モル比１：３．５での（ＮＰＣＡ’２）４ のアジリゾインとの反応 １０００１１ の乾燥ディエチルエーテルの中の３．９（Ｆｌ１３のアジリゾイ ンの溶液（７７，８ｍｍｏｌ ）が４００＠”の乾燥ディエテルエーテルの１０ ．０ｇの（ＮＰＣＩ２）４のｆｆＩ液（２１，６ｍｍｏ／ ）に、激しく攪拌し 、−ＯＣに冷却しながら、３０−４５分間滴下して加えられた。Reaction of (NPCA'2)4 with azirizoin in B1 molar ratio 1:3.5 3.9 (Fl13 azirizoi) in dry diethyl ether of 100011 A solution (77.8 mmol) of 400@” dry diether ether ．． 0 g of (NPCI2)4 ffI solution (21.6 mmo/) was stirred vigorously. , -OC was added dropwise over 30-45 minutes with cooling.
反応混合物がゆっくり室温まで加熱され、７時間の全反応時間までさらに攪拌さ れた。Ａ、で述べられた処理方法は加水分解に対して感じる１０．５ｇの濁った オイルを与えた（生成物Ｂ）。The reaction mixture was slowly heated to room temperature and stirred further for a total reaction time of 7 hours. It was. The treatment method described in A. gave an oil (Product B).
Ｃ０住成物の分析 ３１ ｐ ＮＭＲ，質量スペクトルおよびＨＰＬＣダイヤグラムの分析（第１図 および第２図）は生成物ＡとＢが原理的に同じ組成を持っていることを示した。Analysis of C0 residential components 31p Analysis of NMR, mass spectra and HPLC diagrams (Fig. 1 and FIG. 2) showed that products A and B had essentially the same composition.
Ａは特にＮ４Ｐ４ＡｚＣｊ１７ン含んだ。他方Ｂは、この成分に加え、特にＮ４ Ｐ４Ａｚ２ＣＡｔｓ （すなわち５異性体）を含んだ。モノｌディｆＩｊＬ換の 比はモル比および反応時間を変化させることによって影響を及はされた。生成物 Ｂのような反応混合物はまた、乾燥ディエチルエーテルの中のアジリゾインとの ｌ：・２反応でＮ４Ｐ４ＡｚＣ１ｔから出発しても得られることがわかった。A specifically contained N4P4AzCj17. On the other hand, B, in addition to this component, contains especially N4 P4Az2CAts (i.e. 5 isomers). Mono ldi fIjL conversion The ratio was influenced by varying the molar ratio and reaction time. product Reaction mixtures such as B also include azirizoin in dry diethyl ether. It was found that it could also be obtained starting from N4P4AzClt in the l:.2 reaction.
Ｄ０分離方法 生成物Ａも生成物Ｂも２５％ディエチルエーテル１７５％ヘキサン浴能液を使っ てＨＰＬＣで分離できることがわかった。生成物Ａは、最大の部分（第１図部分 ｌ）として、（Ｊ４Ｐ４ＡＺＣＡ！７を与える。全体で２．５６ ｇが得られた （収率５０％）。ペンタンからの再結晶は１．９ｇの分析的に純粋な物質：融点 ６８−５−７０．０Ｃを与えた。対応する条件の下で生成物Ｂは７つの部分を与 えた（第２図）。D0 separation method For both product A and product B, a 25% diethyl ether 175% hexane solution was used. It was found that it can be separated by HPLC. Product A is the largest part (Fig. 1 part l), give (J4P4AZCA!7. 2.56 g was obtained in total. (Yield 50%). Recrystallization from pentane yields 1.9 g of analytically pure material: melting point 68-5-70.0C was given. Under the corresponding conditions product B gives 7 parts (Figure 2).
計 ： ８．１５ｇ＝７７．８％ 生成物Ｂで部分５は二つの構成成分ρ・ら成っており、それらは後に同じ浴駆Ｉ Ｆｉを使って丹び分解されることがわかった（第３図）。Total: 8.15g = 77.8% In product B, part 5 consists of two constituents ρ, which are later treated with the same bath driver I. It was found that it can be decomposed using Fi (Figure 3).
収率 部分萱号二５’ ： Ｎ４Ｐ４Ａｚ２ＣＩ６０．２０ ｇ５” ： Ｎ、４Ｐ４ Ａｚ２Ｃ／６ １．０２ ｇ計 １．２２ｇ＝７５％ 部分５につ℃・て計算され た（ １．６３ ｇ ） Ｅ、特性記述 ｊＸ量スペクトル Ｎ４Ｐ４ＡｚＣ１７およびＮ４Ｐ４ＡＺ２Ｃ／６の両方のｘｉスペクトルはそれ ぞれＭ ＝４６７（３５Ｃ１！について）およびＭ＝４７４（Ｃ）について）の 栽ビークに加えているいろの塩素同位元素を示した。yield Part No. 2 5’: N4P4Az2CI60.20 g5”: N, 4P4 Az2C/6 1.02g total 1.22g = 75% Part 5 is calculated by °C. (1.63 g) E. Characteristic description jX amount spectrum The xi spectra of both N4P4AzC17 and N4P4AZ2C/6 are that M = 467 (for 35C1!) and M = 474 (C)), respectively. The various chlorine isotopes added to the cultivation beak are shown.
Ｎ４Ｐ４Ａｚ２ＣＡ？６のいろいろの異性体の形のスペクトルは区別できなかっ た。N4P4Az2CA? The spectra of the various isomeric forms of 6 are indistinguishable. Ta.
赤外線スペクトル Ｎ４Ｐ４ＡｚＣ１７は１３１６（幅広υ・）またはＪ２７９ａｍ（鋭い）にリン ク周波数Ｚ与えた。１′アジリゾイノ バンドは９６５ｃＲＸ（鋭い）にあった 。異性体化合物Ｎ４Ｐ４Ａｚ２Ｃ１６のＩＲスペクトルは明瞭に分離することが できた。リング周彼数は１３１０−１３３４ｒｎ（幅広い）または１２７５−１ ２７９ｍ （鋭い）から変化した。アジリゾイノバンドは９６３から９７６川 まで（鋭い）眼に見えた。infrared spectrum N4P4AzC17 is linked to 1316 (wide υ・) or J279am (sharp) frequency Z was given. 1'Ajirizoino band was at 965cRX (sharp) . The IR spectra of the isomeric compounds N4P4Az2C16 can be clearly separated. did it. Ring circumference is 1310-1334rn (wide) or 1275-1 It changed from 279m (sharp). Ajirizoino band is from 963 to 976 rivers I could see it with my (sharp) eyes.
ＮＭＲスペクトル １Ｊ４Ｐ４Ａｚｏ１７ １ ＡＭ２Ｘ ＆５７−４．６８−７．１７２７．６３ ０．６２．３５２２Ｎ４Ｐ４Ａｚ２０１６ ２ Ａ２Ｘ２８．３７ −１．９２ ２７、ｇ ：ｚ３２２ｚ（ｔ、５）Ｎ４Ｐ４ＡＺ２０１６ ３ ＡＸ ａ、７１ −２．６１２８．４ ２．３２２２（１−５）２ Ｎ４：Ｐ４ＡＺ２（１１６４ＡＡ’ＸＸ’ １１．８８ −４．６７ ２．３０ ２２（１，３）Ｎ４Ｐ、Ａ、２（ＩＩ６５ＩＩ ＡＡ’ＸＸ’ ＋０．３ｓ − ４，８５２，２９２２（１，３）Ｎ４Ｐ４ＡＺ２０１６ ５工 ＡＭ２Ｘ １ Ｂ−，８０−６，２（１強） ２−２６１６．５角、３１Ｐ８５％Ｈ３ＰＯ４に 対するｐｐｍを準位として表わした゛化学シフト″；Ｈ基準としてＴ ｋｉ Ｓ ’＆使ったｐｐｍを単位として表わした゛化学シント″実施例 ■ 化学式Ｎ４Ｐ４Ｒｓ−ｎ Ａｚｎ ’ｌ”有するいくつかのアジリゾイノ誘導体 の製造 以上述べられたアジリゾイノ誘導体の製造において結果として生じる反応混合物 が以下に述べる方法（ａ）にしたがって処理された。NMR spectrum 1J4P4Azo17 1 AM2X &57-4.68-7.1727.63 0.62.3522N4P4Az2016 2 A2X28.37 -1.92 27, g: z322z (t, 5) N4P4AZ2016 3 AX a, 71 -2.6128.4 2.3222(1-5)2 N4: P4AZ2 (1164AA'XX' 11.88 -4.67 2.30 22 (1, 3) N4P, A, 2 (II65II AA'XX' +0.3s - 4,852,2922 (1,3) N4P4AZ2016 5th grade AM2X 1 B-, 80-6,2 (1 strength) 2-2616.5 square, 31P85%H3PO4 "Chemical shift" expressed as a level in ppm to &Example of ``Chemical Synthesis'' expressed in units of ppm ■ Some azirizoino derivatives with the chemical formula N4P4Rs-nAzn’l” Manufacturing of The resulting reaction mixture in the production of the above-mentioned azirizoino derivatives was processed according to method (a) described below.
大部分の反応は、沈澱しているか浴液として、著しい量の塩酸塩を与えた。塩酸 スカベンジャとしてのアジリゾインの使用は、どちらかと言うと不安定で、つい で重合する塩化アジリゾイノ塩となった。Most reactions gave significant amounts of the hydrochloride salt either as precipitate or as a bath solution. hydrochloric acid The use of azirizoin as a scavenger is rather unstable and It became a chloride azirizoino salt that polymerized with.
沈澱させられた（重合した）塩は２濾過によって除去され、溶媒で完全に洗った 後、Ｐ−Ｎ環状化合物を含んで℃・る組み合わされたｆＩａ物がＸ窒中で蒸発さ せられる。溶媒としてアセトニトリルまたはＴＨＦが使用されるときは、完全な 反応混合物が真空中で蒸発させられる。ディエチルエーテルまたはベンゼンヲ使 った抽出は塩乞含まない生の生成物の浴数を生じる。Precipitated (polymerized) salts were removed by 2 filtration and washed thoroughly with solvent. Afterwards, the combined fIa compound containing the P-N ring compound is evaporated in X nitrogen. be given When acetonitrile or THF is used as a solvent, complete The reaction mixture is evaporated in vacuo. Diethyl ether or benzene The extraction yields a raw product bath containing no salt.
すべての生の生成物は適白な溶媒から再結晶によって純化される。混合物はＨＰ ＬＣによって分離され、その結果生じる複数の部分がついで再結晶させられる。All raw products are purified by recrystallization from appropriate solvents. The mixture is on HP Separated by LC and the resulting portions are then recrystallized.
Ｎ４Ｐ４ＡＺ２ｍ７およびＮ４Ｐ４ＡＺ２Ａｍ６ （Ａｍ＝ＮＨＭｅ 。N4P4AZ2m7 and N4P4AZ2Am6 (Am=NHMe.
Ｎ Ｍ ｅ ２、ここでＭｅ−メチル、化合物／ｌ６ｘｌ−２２）■ の製造。化学式の紙条の化学式１−５ を持った化合物が出発化合物として使用 された。N M e 2, where Me-methyl, compound/l6xl-22) ■ Manufacturing of. Compounds with chemical formulas 1-5 in the chemical formula paper strip are used as starting compounds It was done.
Ｎ４Ｐ４Ａｚ （ＮＨＭｅ） ７およびＮ４Ｐ４ＡＺ２ （ＮＨＮｅ ） ６０ Ｃに冷却された１５ａＡのクロロフォルムに０．５ｇの環状化合物（約１ｍｍｏ Ａ）の撹拌された溶液にベンゼン中のメチルアミンの１５閤３の１Ｍ溶液がゆつ く］えられた。室温まで加熱し、１８ｈの反応時間の後、方法（ａ）の適用は生 の生成物を与えた。化学式の紙葉の化学式２ヶ持った化合物が出発化合物として 使用されたとぎ、白（・固体が得られた。他のすべての場合に生成物は樹脂状の オイルから成っていた。すべての化合物はティエチルエーテルと塩化メチレンの 混合物から数回再結晶させられた。１じ字式のｉｒ＆、案の化学式５ＩＩを持っ た化合物が出発材料として使用されたとぎは、汚染されたオイルが得られた。質 量およびＮＭＲヌベクトルは完全にアミノ分解された生成物の存在を示した。そ のほかのテークは以下に示される第り衣に表にされている。N4P4Az (NHMe) 7 and N4P4AZ2 (NHNe) 60 Add 0.5 g of a cyclic compound (approximately 1 mmol) to 15 aA of chloroform cooled to To the stirred solution of A) is added a 1M solution of 15 g of methylamine in benzene. [ku] was given. After heating to room temperature and a reaction time of 18 h, application of method (a) gave a product of The compound with two chemical formulas on the chemical formula sheet is the starting compound. When used, a white (solid) was obtained; in all other cases the product was resinous. It consisted of oil. All compounds are of thiethyl ether and methylene chloride. The mixture was recrystallized several times. It has the 1-character formula ir&, and the proposed chemical formula 5II. When this compound was used as starting material, a contaminated oil was obtained. quality Quantity and NMR Nuvector showed the presence of completely aminolyzed product. So The other takes are listed in the first order shown below.
Ｎ４Ｐ４Ａｚ （ＮＭｅ２） ７およびＮ４Ｐ４Ａｚ２（ＮＭｅ２）６０Ｃに冷 却された２５０１３ のディ韮チーーーテルににディエチルエーテル中のディメ チルアミンの１５閤３０３Ｍ溶液が滴下して加えられた。室温まで加熱し、１８ ｈの反応時間の彼、方法（ａ）ｙ＜使っての死神は０、５７ ｇのオイル状の材 料を生じた。これが２５硼３のディエチルエーテルの中ＶＣ１＃ｒかされ、ディ エチルエーテル中の３Ｍのディエチルアミン浴ＮｋｌＯｃｙｘ ｖ加えた後、夜 を倣して還流させられた。ついで方法（ａ）がもう１度使用され、０．５４ｇの 白い固体（出発材料が化学式の紅葉の化学式１または化学式２を持った化合物で あるとき）またはねばねはしたオイル（出発材料か化学式の紅葉の化学式３また は化学式５１ｉ乞持った化合物であるとき）を生じる。固体ヘキャンから容易に 結晶化された。それに反してオイルは一７０Ｃで小量のへキサンからの数回の８ Ｍ晶を必振とした。N4P4Az (NMe2) 7 and N4P4Az2 (NMe2) cooled to 60C The dimethyl ether in the rejected 25013 Fifteen volumes of a 303M solution of thylamine were added dropwise. Heat to room temperature, 18 The reaction time of h, method (a) y< using the Grim Reaper is 0, 57 g of oily material This resulted in a fee. This was mixed with VC1#r in 25 liters of diethyl ether and diluted. 3M diethylamine bath in ethyl ether, night after adding NklOcyx v. It was refluxed in imitation. Method (a) was then used once more and 0.54 g of A white solid (the starting material is a compound with the chemical formula 1 or 2 of the chemical formula Autumn Leaves) ) or sticky oil (starting material or chemical formula of autumn leaves chemical formula 3 or is a compound with formula 51i). Easily removed from solid particles crystallized. Oil, on the other hand, is made from a small amount of hexane at -70C several times 8 M-crystal was a must-swing.
化学式の紅葉の化学式２を持った化合物から出発して得られた生成物は不満足な 細度のオイルのままであった。質量およびＮＭＲスペクトルは先金にアミノ分解 された化合物４２２と一致した。そのほかのデータは以下の第ｆ１表に表にされ ている。Starting from a compound with the chemical formula 2, the product obtained is unsatisfactory. It remained a fine oil. Mass and NMR spectra were pre-aminolyzed. The result was consistent with compound 422. Other data are tabulated in Table f1 below. ing.
％似記述データ 第 厘 表 １ 化合物Ｎｏ、ｓ、 ６−２２の ＰＮＭＲデータ８７ １４１ １４．９ １２ −１ −１５ ２７−０ ２７−０ ２６．５ ２Ｆ＋、５１５ １３．８１ふ ８ ９．６ ９．６ ２７．２３３．０３東８３３．００１６ １ａ、５１３． ５ ９．５ ９．５ ２７．２３λ１３９．５３３．１ −０．２２１ １４． ０１４．０ ＆６ Ｅ＋、６ ３１．７３１Ｌ９４λ６３１Ｌ９ −０．４２２ １２．５１２．５ ＆３ ＆３ ３３．０３９．９４３．５３愼９−０・１第 ＩＶ 表 ９ １４８９（１４，９１） ２． ｓｔ （２，５０） ２０．３７（２０， ２８） ３６．７２（３６，６７）１２ ２６、９０（２７，ｏ３） ７．２６ （７，２す３７．４３（３７，８３）１ ａ ２６．９４（２７，０３） ７． ３７（７，２６） ３７．７９（３７，８３）＋ｊ つり リＪ／リク ＾す） け ＋電ｌ＋ ヘー％ −−−−／−−１試験管 生理学的活性 １１ １５０ ５６．９ １６−（試験されず） ２０ ２ 試Ｍ継続中% similar descriptive data Table of contents 1 PNMR data of compound No. s, 6-22 87 141 14.9 12 -1 -15 27-0 27-0 26.5 2F+, 515 13.81F 8 9.6 9.6 27.233.03 East 833.0016 1a, 513. 5 9.5 9.5 27.23λ139.533.1 -0.221 14. 014.0 &6 E+, 6 31.731L94λ631L9 -0.422 12.512.5 &3 &3 33.039.943.53 9-0/1st IV Table 9 1489 (14,91) 2. st (2,50) 20.37 (20, 28) 36.72 (36,67) 12 26, 90 (27, o3) 7.26 (7,2s 37.43 (37,83) 1 a 26.94 (27,03) 7. 37 (7, 26) 37.79 (37, 83) + j ke + electric l + h % −−−−/−−1 test tube physiological activity 11 150 56.9 16- (not tested) 20 2 Trial M continues
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8301626 | 1983-05-06 | ||
| NL8301626A NL8301626A (en) | 1983-05-06 | 1983-05-06 | AZIRIDINE DERIVATIVE OF A TETRAMIC CYCLOCHLOROPHOSPHOSPHENE COMPOUND, PROCESS FOR THE PREPARATION THEREOF, AND A AZIRIDINE DERIVATIVE DERIVED BY SUBSTITUTION OF THE CHLOROUS ATOMS OF THE TETRAMERIC CHLOROPHOSPHAZENE. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60501257A true JPS60501257A (en) | 1985-08-08 |
Family
ID=19841823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59501896A Pending JPS60501257A (en) | 1983-05-06 | 1984-05-07 | An aziridino derivative of a tetrameric cyclophosphazene chloride compound, a method for producing the same, and an aziridino derivative obtained by substituting the chlorine atom of this compound |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0142543A1 (en) |
| JP (1) | JPS60501257A (en) |
| AU (1) | AU560606B2 (en) |
| DK (1) | DK7485D0 (en) |
| NL (1) | NL8301626A (en) |
| WO (1) | WO1984004523A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19947440A1 (en) * | 1999-09-24 | 2001-04-05 | Analyticon Discovery Gmbh | 1-Aziridino-1-hydroxyiminomethyl derivatives, process for their preparation and medicaments containing these compounds |
| CN110954628B (en) * | 2019-12-19 | 2022-05-03 | 山东泰星新材料股份有限公司 | High performance liquid detection method of hexaphenoxycyclotriphosphazene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1493736A (en) * | 1966-07-22 | 1967-09-01 | Soc Etu Chimiques Ind Et Agri | New derivatives of phosphonitrile chloride |
-
1983
- 1983-05-06 NL NL8301626A patent/NL8301626A/en not_active Application Discontinuation
-
1984
- 1984-05-07 AU AU28679/84A patent/AU560606B2/en not_active Expired - Fee Related
- 1984-05-07 EP EP84902089A patent/EP0142543A1/en not_active Withdrawn
- 1984-05-07 WO PCT/NL1984/000013 patent/WO1984004523A1/en not_active Application Discontinuation
- 1984-05-07 JP JP59501896A patent/JPS60501257A/en active Pending
-
1985
- 1985-01-07 DK DK7485A patent/DK7485D0/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2867984A (en) | 1984-12-04 |
| NL8301626A (en) | 1984-12-03 |
| AU560606B2 (en) | 1987-04-09 |
| DK7485A (en) | 1985-01-07 |
| DK7485D0 (en) | 1985-01-07 |
| WO1984004523A1 (en) | 1984-11-22 |
| EP0142543A1 (en) | 1985-05-29 |
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