JPS60501257A - 四量体塩化シクロフオスフアゼン化合物のアジリデイノ誘導体、その製造方法、及びこの化合物の塩素原子を置換して得られるアジリデイノ誘導体 - Google Patents
四量体塩化シクロフオスフアゼン化合物のアジリデイノ誘導体、その製造方法、及びこの化合物の塩素原子を置換して得られるアジリデイノ誘導体Info
- Publication number
- 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
- Authority
- JP
- Japan
- Prior art keywords
- compound
- azirizoino
- chemical formula
- reaction
- tetrameric
- 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
- 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)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8301626A NL8301626A (nl) | 1983-05-06 | 1983-05-06 | Aziridinoderivaat van een tetramere cyclochloorfosfazeenverbinding, werkwijze ter bereiding daarvan, en een door substitutie van de chlooratomen van de tetramere chloorfosfazeenverbinding afgeleid aziridinoderivaat. |
| NL8301626 | 1983-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60501257A true JPS60501257A (ja) | 1985-08-08 |
Family
ID=19841823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59501896A Pending JPS60501257A (ja) | 1983-05-06 | 1984-05-07 | 四量体塩化シクロフオスフアゼン化合物のアジリデイノ誘導体、その製造方法、及びこの化合物の塩素原子を置換して得られるアジリデイノ誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0142543A1 (da) |
| JP (1) | JPS60501257A (da) |
| AU (1) | AU560606B2 (da) |
| DK (1) | DK7485A (da) |
| NL (1) | NL8301626A (da) |
| WO (1) | WO1984004523A1 (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19947440A1 (de) * | 1999-09-24 | 2001-04-05 | Analyticon Discovery Gmbh | 1-Aziridino-1-hydroxyiminomethyl-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| CN110954628B (zh) * | 2019-12-19 | 2022-05-03 | 山东泰星新材料股份有限公司 | 一种六苯氧基环三磷腈的高效液相检测方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1493736A (fr) * | 1966-07-22 | 1967-09-01 | Soc Etu Chimiques Ind Et Agri | Nouveaux dérivés du chlorure de phosphonitrile |
-
1983
- 1983-05-06 NL NL8301626A patent/NL8301626A/nl not_active Application Discontinuation
-
1984
- 1984-05-07 WO PCT/NL1984/000013 patent/WO1984004523A1/en not_active Application Discontinuation
- 1984-05-07 JP JP59501896A patent/JPS60501257A/ja active Pending
- 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
-
1985
- 1985-01-07 DK DK7485A patent/DK7485A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2867984A (en) | 1984-12-04 |
| NL8301626A (nl) | 1984-12-03 |
| AU560606B2 (en) | 1987-04-09 |
| WO1984004523A1 (en) | 1984-11-22 |
| EP0142543A1 (en) | 1985-05-29 |
| DK7485D0 (da) | 1985-01-07 |
| DK7485A (da) | 1985-01-07 |
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