NL8501030A - Nieuwe cyklische fosfonieten, bereidingswerkwijze en toepassingen daarvan. - Google Patents
Nieuwe cyklische fosfonieten, bereidingswerkwijze en toepassingen daarvan. Download PDFInfo
- Publication number
- NL8501030A NL8501030A NL8501030A NL8501030A NL8501030A NL 8501030 A NL8501030 A NL 8501030A NL 8501030 A NL8501030 A NL 8501030A NL 8501030 A NL8501030 A NL 8501030A NL 8501030 A NL8501030 A NL 8501030A
- Authority
- NL
- Netherlands
- Prior art keywords
- ppm
- compound according
- compound
- preparation
- equals
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 29
- 238000000034 method Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 45
- -1 5 -methyl-2-phenyl-1,3,2-dioxaphosphonane Chemical group 0.000 claims description 20
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 19
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002524 organometallic group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002596 lactones Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001414 amino alcohols Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims 3
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000004437 phosphorous atom Chemical group 0.000 claims 2
- LYJRZCAPLHKSLN-UHFFFAOYSA-N 4-(4-nitrophenyl)-2-phenyl-1,3,2-dioxaphosphinane Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C1OP(OCC1)C1=CC=CC=C1 LYJRZCAPLHKSLN-UHFFFAOYSA-N 0.000 claims 1
- 125000004956 cyclohexylene group Chemical group 0.000 claims 1
- 125000004979 cyclopentylene group Chemical group 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000003106 haloaryl group Chemical group 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- HWSUUGHIDOOOOJ-UHFFFAOYSA-N dioxaphosphinane Chemical compound C1COOPC1 HWSUUGHIDOOOOJ-UHFFFAOYSA-N 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- KFGFLEOUNBSLSO-UHFFFAOYSA-N dioxaphosphonane Chemical compound C1CCCPOOCC1 KFGFLEOUNBSLSO-UHFFFAOYSA-N 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WIIZWVCIJKGZOK-IUCAKERBSA-N 2,2-dichloro-n-[(1s,2s)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide Chemical compound ClC(Cl)C(=O)N[C@@H](CO)[C@@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-IUCAKERBSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- OPROPKSUNRYUKN-UHFFFAOYSA-N 1,3,2-oxazaphospholidine Chemical class C1COPN1 OPROPKSUNRYUKN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical group PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- FUBHSOBGYKRCKQ-UHFFFAOYSA-N 1,3,2-oxazaphosphole Chemical compound C1=COP=N1 FUBHSOBGYKRCKQ-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- QJTACWHLSGWVPR-UHFFFAOYSA-N 2-(2-methoxyphenyl)ethyl-phenylphosphane Chemical compound COC1=CC=CC=C1CCPC1=CC=CC=C1 QJTACWHLSGWVPR-UHFFFAOYSA-N 0.000 description 1
- GPRQVQIDIJJIHD-UHFFFAOYSA-N 2-phenylethylphosphinic acid Chemical compound OP(=O)CCC1=CC=CC=C1 GPRQVQIDIJJIHD-UHFFFAOYSA-N 0.000 description 1
- PMHOWXRNJXWYIP-UHFFFAOYSA-N 4,5-dihydrooxazaphosphole Chemical compound C1CP=NO1 PMHOWXRNJXWYIP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTAZHTQUJLHLMT-UHFFFAOYSA-N Cc1ccccc1O[PH2]=O Chemical compound Cc1ccccc1O[PH2]=O OTAZHTQUJLHLMT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SHBHXOXBWWDHLT-UHFFFAOYSA-N [3-(hydroxymethyl)-2,2,3-trimethylcyclopentyl]methanol Chemical compound CC1(C)C(CO)CCC1(C)CO SHBHXOXBWWDHLT-UHFFFAOYSA-N 0.000 description 1
- JAWXUPLHVUBFNX-UHFFFAOYSA-M [Br-].COC1=CC=CC=C1C[Mg+] Chemical compound [Br-].COC1=CC=CC=C1C[Mg+] JAWXUPLHVUBFNX-UHFFFAOYSA-M 0.000 description 1
- XPEOWXUBQPKDLK-UHFFFAOYSA-N [Li]CC1=CC=CC=C1OC Chemical compound [Li]CC1=CC=CC=C1OC XPEOWXUBQPKDLK-UHFFFAOYSA-N 0.000 description 1
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical group [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- OXJVPEPMGZHRJB-UHFFFAOYSA-N aminophosphinoamine Chemical class NPN OXJVPEPMGZHRJB-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 description 1
- QKZWXPLBVCKXNQ-ROJLCIKYSA-N dipamp Chemical compound COC1=CC=CC=C1[P@@](C=1C=CC=CC=1)CC[P@@](C=1C(=CC=CC=1)OC)C1=CC=CC=C1 QKZWXPLBVCKXNQ-ROJLCIKYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011982 enantioselective catalyst Substances 0.000 description 1
- YJSXLGKPMXKZJR-UHFFFAOYSA-N ethoxy-oxo-phenylphosphanium Chemical compound CCO[P+](=O)C1=CC=CC=C1 YJSXLGKPMXKZJR-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ZUYQAYFMISSPTF-UHFFFAOYSA-N methoxy-oxo-phenylphosphanium Chemical compound CO[P+](=O)C1=CC=CC=C1 ZUYQAYFMISSPTF-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- IIWVFLOQEJCOIX-UHFFFAOYSA-N oxathiaphospholane Chemical compound C1CPSO1 IIWVFLOQEJCOIX-UHFFFAOYSA-N 0.000 description 1
- UQZZQHGRZPTZME-UHFFFAOYSA-N oxazaphospholidine Chemical group C1CPNO1 UQZZQHGRZPTZME-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- CGNKSELPNJJTSM-UHFFFAOYSA-N phenylphosphonous acid Chemical compound OP(O)C1=CC=CC=C1 CGNKSELPNJJTSM-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- JRPGPMLROWPYLX-UHFFFAOYSA-N phosphorosooxymethylbenzene Chemical compound O=POCC1=CC=CC=C1 JRPGPMLROWPYLX-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
- C07F9/6571—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 oxygen atoms as the only ring hetero atoms
- C07F9/657163—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 oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/65719—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 oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonous acid derivative
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl compounds
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3276—Esters with cycloaliphatic alcohols
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
-
- 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
- C07F9/6571—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 oxygen atoms as the only ring hetero atoms
- C07F9/657163—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 oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—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 oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8405622 | 1984-04-10 | ||
| FR8405622A FR2562543B1 (fr) | 1984-04-10 | 1984-04-10 | Nouveaux phosphonites cycliques, leur preparation et applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8501030A true NL8501030A (nl) | 1985-11-01 |
Family
ID=9303009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8501030A NL8501030A (nl) | 1984-04-10 | 1985-04-09 | Nieuwe cyklische fosfonieten, bereidingswerkwijze en toepassingen daarvan. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4952740A (fr) |
| JP (1) | JPH0662649B2 (fr) |
| BE (1) | BE902124A (fr) |
| CA (1) | CA1258266A (fr) |
| CH (1) | CH665644A5 (fr) |
| DE (1) | DE3512781C2 (fr) |
| FR (1) | FR2562543B1 (fr) |
| GB (1) | GB2158441B (fr) |
| IT (1) | IT1201414B (fr) |
| NL (1) | NL8501030A (fr) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2562543B1 (fr) * | 1984-04-10 | 1987-09-25 | Elf Aquitaine | Nouveaux phosphonites cycliques, leur preparation et applications |
| FR2603286B1 (fr) * | 1986-08-27 | 1988-12-09 | Elf Aquitaine | Procede de preparation de derives de l'acide phosphineux et produit intermediaire utilise a cet effet |
| EP0472564B1 (fr) * | 1989-05-20 | 1994-09-21 | Hoechst Aktiengesellschaft | Arylesters d'acide phosphoneux, procede pour les preparer et leur utilisation pour stabiliser des matieres synthetiques, en particulier des matieres moulables polyolefiniques |
| DE3923492A1 (de) * | 1989-05-20 | 1991-02-07 | Hoechst Ag | Kunststoff-formmasse |
| FR2649109B1 (fr) * | 1989-06-30 | 1991-09-13 | Elf Aquitaine | Composes organiques du phosphore complexes par du bore, leur preparation et applications |
| US5767276A (en) * | 1995-10-13 | 1998-06-16 | The Penn State Research Foundation | Asymmetric synthesis catalyzed by transition metal complexes with new chiral ligands |
| DE19608006A1 (de) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Salze von phosphonigen Säuren und deren Verwendung als Flammschutzmittel in Kunststoffen |
| US5962440A (en) * | 1996-05-09 | 1999-10-05 | Bristol-Myers Squibb Company | Cyclic phosphonate ester inhibitors of microsomal triglyceride transfer protein and method |
| JP2001521001A (ja) * | 1997-10-28 | 2001-11-06 | ブリストル−マイヤーズ スクイブ カンパニー | ミクロソーム・トリグリセリド転移たんぱくの環式ホスホネートエステル抑制剤および抑制方法 |
| US6312662B1 (en) | 1998-03-06 | 2001-11-06 | Metabasis Therapeutics, Inc. | Prodrugs phosphorus-containing compounds |
| US7205404B1 (en) | 1999-03-05 | 2007-04-17 | Metabasis Therapeutics, Inc. | Phosphorus-containing prodrugs |
| MXPA01008937A (es) | 1999-03-05 | 2004-04-05 | Metabasis Therapeutics Inc | Nuevos profarmacos que contienen fosforo. |
| AU7361400A (en) | 1999-09-08 | 2001-04-10 | Metabasis Therapeutics, Inc. | Prodrugs for liver specific drug delivery |
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| EP1736478B1 (fr) | 2000-05-26 | 2015-07-22 | IDENIX Pharmaceuticals, Inc. | Procédés et compositions de traitement des flavivirus et des pestivirus |
| EP1435974A4 (fr) | 2001-09-28 | 2006-09-06 | Idenix Cayman Ltd | Procedes et compositions pour le traitement du virus de l'hepatite c au moyen de nucleosides modifies en 4' |
| EP2223927B1 (fr) * | 2002-05-13 | 2014-10-15 | Metabasis Therapeutics, Inc. | Sels d' un Pro-médicament de PMEA à base d'acide phosphonique |
| WO2003095665A2 (fr) * | 2002-05-13 | 2003-11-20 | Metabasis Therapeutics, Inc. | Procede d'elaboration de promedicaments cycliques de pmea et de pmpa |
| TW200500375A (en) | 2002-06-28 | 2005-01-01 | Idenix Cayman Ltd | Modified 2' and 3'-nucleoside prodrugs for treating flaviviridae |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| NZ537662A (en) | 2002-06-28 | 2007-10-26 | Idenix Cayman Ltd | 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| CN1678326A (zh) | 2002-06-28 | 2005-10-05 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2'-c-甲基-3'-o-l-缬氨酸酯核糖呋喃基胞苷 |
| BR0315795A (pt) | 2002-10-31 | 2005-09-13 | Metabasis Therapeutics Inc | Pró-medicamentos de monofosfato de citarabina |
| LT1576138T (lt) | 2002-11-15 | 2017-06-26 | Idenix Pharmaceuticals Llc | 2`-šakoti nukleozidai derinyje su interferonu ir flaviviridae mutacija |
| AU2003300901A1 (en) | 2002-12-12 | 2004-06-30 | Idenix (Cayman) Limited | Process for the production of 2'-branched nucleosides |
| NZ540913A (en) * | 2002-12-23 | 2008-02-29 | Idenix Cayman Ltd | Process for the production of 3'-nucleoside prodrugs |
| HUE029877T2 (en) | 2003-05-30 | 2017-04-28 | Gilead Pharmasset Llc | Modified fluorinated nucleoside analogues |
| AR046970A1 (es) * | 2003-12-23 | 2006-01-04 | Schering Plough Ltd | Esteres de fosfato de florfenicol |
| CA2565966A1 (fr) * | 2004-06-08 | 2005-12-29 | Metabasis Therapeutics, Inc. | Synthese d'esters cycliques induite par l'acide de lewis |
| CA2571675A1 (fr) * | 2004-06-23 | 2006-01-05 | Idenix (Cayman) Limited | Derives de 5-aza-7-deazapurine pour le traitement des infections avec flaviviridae |
| JP4516863B2 (ja) * | 2005-03-11 | 2010-08-04 | 株式会社ケンウッド | 音声合成装置、音声合成方法及びプログラム |
| ES2422290T3 (es) | 2005-12-23 | 2013-09-10 | Idenix Pharmaceuticals Inc | Procedimiento para preparar un producto intermedio sintético para la preparación de nucleósidos ramificados |
| WO2009129120A2 (fr) | 2008-04-15 | 2009-10-22 | Rfs Pharma, Llc | Dérivés nucléosidiques destinés au traitement d’infections par un virus de la famille des caliciviridae, y compris d’infections par le norovirus |
| WO2012079035A1 (fr) | 2010-12-10 | 2012-06-14 | Sigmapharm Laboratories, Llc | Compositions très stables d'analogues nucléotidiques actifs par voie orale ou de promédicaments sous forme d'analogues nucléotidiques actifs par voie orale |
| AU2015217221A1 (en) | 2014-02-13 | 2016-08-11 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and their uses |
| CN106687118A (zh) | 2014-07-02 | 2017-05-17 | 配体药物公司 | 前药化合物及其用途 |
| CA3087932A1 (fr) | 2018-01-09 | 2019-07-18 | Ligand Pharmaceuticals, Inc. | Composes acetal et leurs utilisations therapeutiques |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297631A (en) * | 1965-10-24 | 1967-01-10 | Exxon Research Engineering Co | Novel phenolic phosphorus stabilizers for polyolefins |
| FR2518100A1 (fr) * | 1981-12-11 | 1983-06-17 | Elf Aquitaine | Procede de preparation de phosphinamides, applications et nouveaux produits |
| FR2562543B1 (fr) * | 1984-04-10 | 1987-09-25 | Elf Aquitaine | Nouveaux phosphonites cycliques, leur preparation et applications |
-
1984
- 1984-04-10 FR FR8405622A patent/FR2562543B1/fr not_active Expired
-
1985
- 1985-04-03 GB GB08508730A patent/GB2158441B/en not_active Expired
- 1985-04-04 CH CH1476/85A patent/CH665644A5/fr not_active IP Right Cessation
- 1985-04-04 BE BE0/214797A patent/BE902124A/fr not_active IP Right Cessation
- 1985-04-09 IT IT20279/85A patent/IT1201414B/it active
- 1985-04-09 NL NL8501030A patent/NL8501030A/nl not_active Application Discontinuation
- 1985-04-09 CA CA000478571A patent/CA1258266A/fr not_active Expired
- 1985-04-10 DE DE3512781A patent/DE3512781C2/de not_active Expired - Fee Related
- 1985-04-10 JP JP60074524A patent/JPH0662649B2/ja not_active Expired - Lifetime
-
1989
- 1989-09-12 US US07/407,702 patent/US4952740A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3512781A1 (de) | 1985-10-17 |
| JPH0662649B2 (ja) | 1994-08-17 |
| GB8508730D0 (en) | 1985-05-09 |
| CA1258266A (fr) | 1989-08-08 |
| BE902124A (fr) | 1985-10-04 |
| FR2562543A1 (fr) | 1985-10-11 |
| US4952740A (en) | 1990-08-28 |
| GB2158441B (en) | 1988-08-10 |
| FR2562543B1 (fr) | 1987-09-25 |
| GB2158441A (en) | 1985-11-13 |
| IT8520279A0 (it) | 1985-04-09 |
| JPS60228492A (ja) | 1985-11-13 |
| CH665644A5 (fr) | 1988-05-31 |
| DE3512781C2 (de) | 1995-07-27 |
| IT1201414B (it) | 1989-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL8501030A (nl) | Nieuwe cyklische fosfonieten, bereidingswerkwijze en toepassingen daarvan. | |
| Prishchenko et al. | Synthesis of 2‐substituted O, O‐bis (trimethylsilyl) alkylphosphonites with aryl and heterocyclic fragments and their amino or amido derivatives | |
| Prishchenko et al. | Synthesis of ferrocene-containing phosphonous and phosphinic acids based on alkenylferrocenes | |
| Brunner et al. | Asymmetric catalyses: XXXIII. New optically active phospholanes derived from tartaric acid | |
| Mondal et al. | Recent advances in organophosphorus–chalcogen and organophosphorus–pincer based macrocyclic compounds and their metal complexes | |
| Bubnov et al. | Synthesis of functionalized organophosphorus analogs of glycine containing PCH2N units | |
| Winters et al. | Evaluation and development of methodologies for the synthesis of thiophosphinic acids | |
| Perlikowska et al. | Enantiomerically pure disulfides: key compounds in the kinetic resolution of chiral PIII-derivatives with stereogenic phosphorus | |
| Lu et al. | Inhibition of glutamate carboxypeptidase by phosphoryl and thiophosphoryl derivatives of glutamic and 2-hydroxyglutaric acid | |
| Zubiri et al. | Synthesis and uses of phosphines containing PN bonds | |
| Brauer et al. | Chiral Phosphine Ligands from Amino Acids. II. A Facile Synthesis of Phosphinoserines by Nucleophilic Phosphination Reactions–X‐Ray Structure Analyses of Ar2P–CH2–CH (NHBOC)(COOMe)(Ar= Ph, m‐xylyl) | |
| Freeman et al. | Influence of ortho methyl and isopropyl substituents on the reactivity of N-t-butyl P-arylphosphonamidic chlorides with isopropylamine and t-butylamine: steric acceleration of metaphosphonimidate formation by an elimination addition mechanism; contrasting behaviour of N, N-dimethyl P-arylphosphonamidic chlorides | |
| NL8501355A (nl) | Cyclische disfosfonieten, en bereiding en toepassingen daarvan. | |
| Mitchell et al. | Recent developments in phosphono-transfer chemistry | |
| US20080091040A1 (en) | Optically active alkenylphosphinic acid ester and process for producing the same | |
| JP3564503B2 (ja) | アルケニルホスホン酸エステル類およびその製造方法 | |
| Hatam et al. | Phosphinic acid analogues of thiaproline and the related heterocyclic aminophosphinic acids | |
| SU943243A1 (ru) | Способ получени диарилгалогенфосфинов | |
| Froneman et al. | Dialkylamino group transfer from titanium (IV) to phosphoryl centre. Structure-reactivity studies | |
| Olszewski et al. | Synthesis of new imidazole aminophosphine oxides | |
| SU1715811A1 (ru) | Способ получени N-дизамещенных 0,0,0,0-тетраэтиламинометилендифосфонитов | |
| Yadav et al. | METAL AND ORGANOMETAL COMPLEXES OF OXY-AND THIOPHOSPHORUS ACIDS. VIII. REACTIONS OF O, O-DIISOPROPYL AND O, O-ALKYLENE DITHIOPHOSPHORIC ACIDS WITH TITANIUM AND TIN TETRACHLORIDE | |
| Lindell et al. | The combinatorial synthesis of organophosphorus compounds | |
| Mazzacurati | Advanced studies on the synthesis of organophosphorus compounds | |
| SU753851A1 (ru) | Способ получени ди(0,0-диизопропилдитиофосфорил)дигалогенстаннанов |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |