GB1038523A - Process for preparing organic phosphates - Google Patents
Process for preparing organic phosphatesInfo
- Publication number
- GB1038523A GB1038523A GB12564/63A GB1256463A GB1038523A GB 1038523 A GB1038523 A GB 1038523A GB 12564/63 A GB12564/63 A GB 12564/63A GB 1256463 A GB1256463 A GB 1256463A GB 1038523 A GB1038523 A GB 1038523A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- phosphate
- organic
- adenosine
- aralkyl
- 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.)
- Expired
Links
- 229910019142 PO4 Inorganic materials 0.000 title abstract 6
- 235000021317 phosphate Nutrition 0.000 title abstract 6
- 150000003013 phosphoric acid derivatives Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 methylene compound Chemical class 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 235000019441 ethanol Nutrition 0.000 abstract 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 abstract 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001720 carbohydrates Chemical class 0.000 abstract 2
- 235000014633 carbohydrates Nutrition 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 150000001721 carbon Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002777 nucleoside Substances 0.000 abstract 2
- 125000003835 nucleoside group Chemical group 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical group [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 235000007586 terpenes Nutrition 0.000 abstract 2
- 239000011782 vitamin Substances 0.000 abstract 2
- 229940088594 vitamin Drugs 0.000 abstract 2
- 229930003231 vitamin Natural products 0.000 abstract 2
- 235000013343 vitamin Nutrition 0.000 abstract 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 abstract 1
- DSNRZTVNAUGXKR-UHFFFAOYSA-N (2,3-diethyl-4-nitrophenyl) dihydrogen phosphate Chemical compound CCC1=C(OP(O)(O)=O)C=CC([N+]([O-])=O)=C1CC DSNRZTVNAUGXKR-UHFFFAOYSA-N 0.000 abstract 1
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 abstract 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 abstract 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 abstract 1
- RURWLUVLDBYUEN-UHFFFAOYSA-N 2-cyano-n-cyclohexylacetamide Chemical class N#CCC(=O)NC1CCCCC1 RURWLUVLDBYUEN-UHFFFAOYSA-N 0.000 abstract 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 abstract 1
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 abstract 1
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 abstract 1
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 abstract 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 abstract 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract 1
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 abstract 1
- 229930091371 Fructose Natural products 0.000 abstract 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 abstract 1
- 239000005715 Fructose Substances 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 abstract 1
- 229930010555 Inosine Natural products 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 1
- 238000003434 Perkow synthesis reaction Methods 0.000 abstract 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 abstract 1
- 229930182558 Sterol Natural products 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 229960005305 adenosine Drugs 0.000 abstract 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 159000000009 barium salts Chemical class 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 1
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 235000012000 cholesterol Nutrition 0.000 abstract 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 abstract 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 abstract 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 abstract 1
- QPQCZRFLLSNBAV-UHFFFAOYSA-N ethyl bis(4-nitrophenyl) phosphite Chemical compound P(OCC)(OC1=CC=C(C=C1)[N+](=O)[O-])OC1=CC=C(C=C1)[N+](=O)[O-] QPQCZRFLLSNBAV-UHFFFAOYSA-N 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 229940029575 guanosine Drugs 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 229960003786 inosine Drugs 0.000 abstract 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 abstract 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 abstract 1
- 229940041616 menthol Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- GESBKELMKMNZLZ-UHFFFAOYSA-N n-diethoxyphosphorylaniline Chemical compound CCOP(=O)(OCC)NC1=CC=CC=C1 GESBKELMKMNZLZ-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004027 organic amino compounds Chemical class 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 150000008298 phosphoramidates Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002212 purine nucleoside Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 150000003432 sterols Chemical class 0.000 abstract 1
- 235000003702 sterols Nutrition 0.000 abstract 1
- 229960003604 testosterone Drugs 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 abstract 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 abstract 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 abstract 1
- 229940045145 uridine Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/04—Phosphates; Phosphites; Polyphosphates
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/02—Phosphorylation
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)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1213162 | 1962-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1038523A true GB1038523A (en) | 1966-08-10 |
Family
ID=11796964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12564/63A Expired GB1038523A (en) | 1962-03-31 | 1963-03-29 | Process for preparing organic phosphates |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3188309A (US08088918-20120103-C00485.png) |
| DE (1) | DE1200818B (US08088918-20120103-C00485.png) |
| GB (1) | GB1038523A (US08088918-20120103-C00485.png) |
| NL (1) | NL290813A (US08088918-20120103-C00485.png) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH521997A (de) * | 1969-04-02 | 1972-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung von Phosphorsäure- und Phosphonsäure-Estern |
| US3671549A (en) * | 1970-03-05 | 1972-06-20 | Merck & Co Inc | Process for preparing ascorbyl-3-phosphate and salts thereof |
| US4164444A (en) * | 1976-03-15 | 1979-08-14 | Massachusetts Institute Of Technology | Method for preparing adenosine triphosphate |
| IT1065240B (it) * | 1976-08-04 | 1985-02-25 | Stabil Bioterapico Farmachim | Procedimento di fabbricazione di fosfomicina |
| US4816570A (en) * | 1982-11-30 | 1989-03-28 | The Board Of Regents Of The University Of Texas System | Biologically reversible phosphate and phosphonate protective groups |
| US4916217A (en) * | 1987-01-08 | 1990-04-10 | Bristol-Myers Company | Phosphorus containing derivatives of epipodophyllotoxin |
| JPH0291088A (ja) * | 1988-09-29 | 1990-03-30 | Central Glass Co Ltd | ホスファイトおよびヌクレオシド‐３’‐ホスファイト誘導体およびこれを用いるオリゴヌクレオチドの合成法 |
| US5597573A (en) * | 1989-05-04 | 1997-01-28 | Igen, Inc. | Lipid-A analogs: new monosaccharide and disaccharide intermediates for eliciting therapeutic antibodies and for antitumor and antiviral activities |
| JPH04118053A (ja) * | 1989-12-29 | 1992-04-20 | Tokyo Roki Kk | エンジンの排気ガス浄化用触媒 |
| US5593969A (en) * | 1991-09-03 | 1997-01-14 | Igen Incorporated | Lipid-A analogs: monosaccharide and dissaccharide compounds for inhibiting binding of lipid A receptors to lipid A receptors |
| IL105131A (en) * | 1992-03-27 | 2000-06-01 | Igen Inc | Compounds and compositions containing such compounds comprising lipid-A analogs for eliciting therapeutic antibodies |
| US8088918B2 (en) * | 2004-08-11 | 2012-01-03 | Williamsburg Holdings Llc | Noncardiotoxic pharmaceutical compounds |
-
0
- NL NL290813D patent/NL290813A/xx unknown
-
1963
- 1963-03-29 GB GB12564/63A patent/GB1038523A/en not_active Expired
- 1963-03-30 DE DEA42772A patent/DE1200818B/de active Pending
- 1963-04-01 US US269717A patent/US3188309A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1200818B (de) | 1965-09-16 |
| NL290813A (US08088918-20120103-C00485.png) | |
| US3188309A (en) | 1965-06-08 |
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