KR20050085831A - 포스포로디아미디트의 제조방법 - Google Patents
포스포로디아미디트의 제조방법 Download PDFInfo
- Publication number
- KR20050085831A KR20050085831A KR1020057011547A KR20057011547A KR20050085831A KR 20050085831 A KR20050085831 A KR 20050085831A KR 1020057011547 A KR1020057011547 A KR 1020057011547A KR 20057011547 A KR20057011547 A KR 20057011547A KR 20050085831 A KR20050085831 A KR 20050085831A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- phosphorodiamidite
- solvent
- dialkyl amine
- polar solvent
- Prior art date
Links
- ZLRAAUUPULJGTL-UHFFFAOYSA-N diaminophosphinous acid Chemical class NP(N)O ZLRAAUUPULJGTL-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 21
- -1 hydroxyalkyl compound Chemical class 0.000 claims abstract description 14
- 239000002798 polar solvent Substances 0.000 claims abstract description 12
- 125000005265 dialkylamine group Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000006184 cosolvent Substances 0.000 claims abstract description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 239000011574 phosphorus Substances 0.000 claims abstract description 7
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical group CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 12
- RKVHNYJPIXOHRW-UHFFFAOYSA-N 3-bis[di(propan-2-yl)amino]phosphanyloxypropanenitrile Chemical compound CC(C)N(C(C)C)P(N(C(C)C)C(C)C)OCCC#N RKVHNYJPIXOHRW-UHFFFAOYSA-N 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 4
- 229940043279 diisopropylamine Drugs 0.000 claims description 4
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 claims description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical group ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 4
- 108091034117 Oligonucleotide Proteins 0.000 claims description 3
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 claims description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical group CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical group CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 7
- 239000007787 solid Substances 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 150000005690 diesters Chemical class 0.000 description 7
- 239000012535 impurity Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Luminescent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (19)
- 다음의 단계를 포함하는 포스포로디아미디트(phosphorodiamidite)의 제조방법1) 삼할로겐화인을 극성 용매에 용해된 디알킬 아민과 반응시켜 중간체 화합물을 형성하는 단계 ; 및2) 비극성 공-용매의 존재 하에서 상기 중간체 화합물을 히드록시알킬 화합물 및 디알킬 아민과 반응시키는 단계.
- 제 1 항에 있어서, 삼할로겐화인은 삼염화인임을 특징으로 하는 방법.
- 제 1 항에 있어서, 삼할로겐화인은 삼브롬화인임을 특징으로 하는 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서, 디알킬 아민은 디이소프로필아민임을 특징으로 하는 방법.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서, 디알킬 아민은 디메틸아민, 디에틸아민, 디-n-프로필아민, 디-n-부틸아민, 디-이소부틸아민 또는 디-3차-부틸아민 중에서 선택한 것임을 특징으로 하는 방법.
- 상기 전 항 중 어느 한 항에 있어서, 극성 용매는 니트릴 화합물임을 특징으로 하는 방법.
- 제 6 항에 있어서, 니트릴 화합물은 아세토니트릴임을 특징으로 하는 방법.
- 제 6 항에 있어서, 극성 용매는 프로피오니트릴 또는 벤조니트릴임을 특징으로 하는 방법.
- 상기 전 항 중 어느 한 항에 있어서, 히드록시알킬 화합물은 히드록시프로피오니트릴임을 특징으로 하는 방법.
- 제 1 항 내지 제 8 항 중 어느 한 항에 있어서, 히드록시알킬 화합물은 메탄올 또는 3차-부틸 알콜임을 특징으로 하는 방법.
- 제 1 항 내지 제 10 항 중 어느 한 항에 있어서, 알칸 공-용매는 C5 내지 C9 지방족 탄화수소임을 특징으로 하는 방법.
- 제 1 항 내지 제 10 항 중 어느 한 항에 있어서, 알칸 공-용매는 지방족 고리 탄화수소임을 특징으로 하는 방법.
- 상기 전 항 중 어느 한 항에 있어서, 극성 용매와 비극성 용매의 비율이 1:1 임을 특징으로 하는 방법.
- 제 1 항 내지 제 13 항 중 어느 한 항의 방법에 의해 제조한, 다음 화학식 I 을 갖는 포스포로디아미디트 화합물화학식 I(R2N)2-P-O(CH2)n-CN이 식에서,R 은 C1 내지 C4 알킬, 히드록시알킬 또는 옥시알킬기이며 ; n 은 1 내지 4 의 범 자연수이다.
- 제 14 항에 있어서, 화합물이 2-시아노에틸 테트라이소프로필 포스포로디아미디트임을 특징으로 하는 화합물.
- 올리고누클레오티드의 합성시 제 1 항의 방법에 의해 만들어진 제 14 항 또는 제 15 항의 화합물의 용도.
- 실질적으로 실시예와 관련하여 전술한 바와 같은, 포스포로디아미디트 화합물.
- 실질적으로 실시예와 관련하여 전술한 바와 같은, 포스포로디아미디트의 제조방법.
- 실질적으로 실시예와 관련하여 전술한 바와 같은, 포스포로디아미디트 화합물의 용도.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0230095.2A GB0230095D0 (en) | 2002-12-24 | 2002-12-24 | Phosphorodiamidite |
GB0230095.2 | 2002-12-24 | ||
PCT/GB2003/005544 WO2004058779A1 (en) | 2002-12-24 | 2003-12-18 | Process for preparing phosphorodiamidites |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20050085831A true KR20050085831A (ko) | 2005-08-29 |
KR100889897B1 KR100889897B1 (ko) | 2009-03-20 |
Family
ID=9950379
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020057011547A KR100889897B1 (ko) | 2002-12-24 | 2003-12-18 | 포스포로디아미디트의 제조방법 |
Country Status (11)
Country | Link |
---|---|
US (1) | US7276620B2 (ko) |
EP (1) | EP1583766B1 (ko) |
JP (1) | JP4511368B2 (ko) |
KR (1) | KR100889897B1 (ko) |
CN (1) | CN100338078C (ko) |
AT (1) | ATE404571T1 (ko) |
AU (1) | AU2003290281A1 (ko) |
CA (1) | CA2511609C (ko) |
DE (1) | DE60322960D1 (ko) |
GB (1) | GB0230095D0 (ko) |
WO (1) | WO2004058779A1 (ko) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9896463B2 (en) * | 2014-01-15 | 2018-02-20 | Rhodia Operations | Preparation of purified phosphorodiamidite |
EP3733680A4 (en) | 2017-12-27 | 2021-12-29 | KNC Laboratories Co., Ltd | Production of highly fat-soluble phosphoramidite |
CN111057108B (zh) * | 2018-10-16 | 2023-08-15 | 中国石油化工股份有限公司 | 一种胺基磷酸酯化合物及其制备方法、用途 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62212395A (ja) | 1986-03-11 | 1987-09-18 | Nippon Zeon Co Ltd | リンアミド化合物の製造法 |
DE10208828A1 (de) | 2002-03-01 | 2003-09-11 | Bayer Ag | Verfahren zur Reduktion von 3-Heteroaryl-3-oxopropionsäurederivaten |
US7057062B2 (en) | 2002-04-11 | 2006-06-06 | Isis Pharmaceuticals, Inc. | Process for manufacturing purified phosphorodiamidite |
JP2005529957A (ja) | 2002-06-13 | 2005-10-06 | ローディア インク. | リン・ジアミダイト合成物を生成する工程 |
-
2002
- 2002-12-24 GB GBGB0230095.2A patent/GB0230095D0/en not_active Ceased
-
2003
- 2003-12-18 JP JP2004563342A patent/JP4511368B2/ja not_active Expired - Lifetime
- 2003-12-18 US US10/540,160 patent/US7276620B2/en not_active Expired - Lifetime
- 2003-12-18 EP EP03782645A patent/EP1583766B1/en not_active Expired - Lifetime
- 2003-12-18 AT AT03782645T patent/ATE404571T1/de not_active IP Right Cessation
- 2003-12-18 DE DE60322960T patent/DE60322960D1/de not_active Expired - Lifetime
- 2003-12-18 AU AU2003290281A patent/AU2003290281A1/en not_active Abandoned
- 2003-12-18 CN CNB2003801074642A patent/CN100338078C/zh not_active Expired - Fee Related
- 2003-12-18 CA CA2511609A patent/CA2511609C/en not_active Expired - Lifetime
- 2003-12-18 KR KR1020057011547A patent/KR100889897B1/ko active IP Right Grant
- 2003-12-18 WO PCT/GB2003/005544 patent/WO2004058779A1/en active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
CA2511609A1 (en) | 2004-07-15 |
EP1583766B1 (en) | 2008-08-13 |
KR100889897B1 (ko) | 2009-03-20 |
WO2004058779A1 (en) | 2004-07-15 |
US20060128951A1 (en) | 2006-06-15 |
CA2511609C (en) | 2012-09-25 |
JP2006512386A (ja) | 2006-04-13 |
ATE404571T1 (de) | 2008-08-15 |
US7276620B2 (en) | 2007-10-02 |
CN100338078C (zh) | 2007-09-19 |
DE60322960D1 (de) | 2008-09-25 |
AU2003290281A1 (en) | 2004-07-22 |
JP4511368B2 (ja) | 2010-07-28 |
EP1583766A1 (en) | 2005-10-12 |
GB0230095D0 (en) | 2003-01-29 |
CN1732176A (zh) | 2006-02-08 |
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