GB1239987A - Phosphonic acid derivatives - Google Patents
Phosphonic acid derivativesInfo
- Publication number
- GB1239987A GB1239987A GB50635/68A GB5063568A GB1239987A GB 1239987 A GB1239987 A GB 1239987A GB 50635/68 A GB50635/68 A GB 50635/68A GB 5063568 A GB5063568 A GB 5063568A GB 1239987 A GB1239987 A GB 1239987A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- prepared
- phosphonic acid
- reacting
- propenyl
- 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
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 title abstract 3
- 150000003007 phosphonic acid derivatives Chemical class 0.000 title abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- -1 peroxy compound Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- ZOIRMVZWDRLJPI-UHFFFAOYSA-N 4-oxobut-2-enoic acid Chemical compound OC(=O)C=CC=O ZOIRMVZWDRLJPI-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- XWCIXXXLOAAWPU-IHWYPQMZSA-N [(z)-prop-1-enyl]phosphonic acid Chemical compound C\C=C/P(O)(O)=O XWCIXXXLOAAWPU-IHWYPQMZSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- LRYANVPYFCKCCR-UHFFFAOYSA-N benzyl 2,5-dihydroxybenzoate Chemical compound OC1=CC=C(O)C(C(=O)OCC=2C=CC=CC=2)=C1 LRYANVPYFCKCCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- RGBRNLMBUNZLQD-UHFFFAOYSA-N dibutoxy(chloro)phosphane Chemical compound CCCCOP(Cl)OCCCC RGBRNLMBUNZLQD-UHFFFAOYSA-N 0.000 abstract 1
- ADKVAUBLWGHZIU-UHFFFAOYSA-N dibutoxy(prop-1-ynyl)phosphane Chemical compound C(CCC)OP(OCCCC)C#CC ADKVAUBLWGHZIU-UHFFFAOYSA-N 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000002432 hydroperoxides Chemical class 0.000 abstract 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- QBNOPZJAURRQCE-UHFFFAOYSA-M magnesium;prop-1-yne;bromide Chemical compound [Mg+2].[Br-].CC#[C-] QBNOPZJAURRQCE-UHFFFAOYSA-M 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 1
- 238000005502 peroxidation Methods 0.000 abstract 1
- 125000005342 perphosphate group Chemical group 0.000 abstract 1
- IPRNUNQRIQCSAX-UHFFFAOYSA-N prop-1-ynylphosphonous acid Chemical compound C(#CC)P(O)O IPRNUNQRIQCSAX-UHFFFAOYSA-N 0.000 abstract 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3826—Acyclic unsaturated 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
-
- 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,239,987. Epoxy phosphonic acid derivatives. MERCK & CO. Inc. 24 Oct., 1968 [30 Oct., 1967; 15 May, 1968], No. 50635/68. Heading C2C. [Also in Division A5] Novel phosphonic acid derivatives of the general formula where R and R 1 are hydrogen, or substituted or unsubstituted hydrocarbyl, acyl or heterocyclic radicals or R and R 1 together form a cyclic ester group, are prepared by epoxidation of the corresponding propenyl derivatives, preferably with a peroxy compound. The invention also comprises the salts of the above compounds which are acidic, and also the compounds of formulµ Specified peroxidation reagents are hydrogen peroxide, inorganic peracids, perorganic acids, organic hydroperoxides, peroxy imidates, oxygen in the presence of a catalyst, oxidizing metal salts, alkali metal hypohalites, ozone and alkyl perborates or perphosphates. The sodium salt of cis - 1 - propenylphosphonous acid is prepared by reacting dibutylchlorophosphite with 1 - propynyl magnesium bromide, heating the resulting dibutyl - 1 - propynyl - phosphonite with an ion exchange resin, and subjecting the resulting 1 -propynylphosphonous acid to neutralization with sodium bicarbonate and catalytic hydrogenation. Di - 2<SP>1</SP> - (methyl - 21 - butenoate) - cis - propenyl phosphonate is prepared by reacting methyl - 3 keto - butenoate, sodium hydride and diethyl ether and treating the resulting product with cis-propenylphosphonic dichloride. The bis - p - benzoquinone ester of cis - propenyl - phosphonic acid is prepared by reacting cis - propenylphosphonic dichloride with monocarbobenzoxy hydroquinone, followed by hydrogenation.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67920367A | 1967-10-30 | 1967-10-30 | |
| US72946668A | 1968-05-15 | 1968-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1239987A true GB1239987A (en) | 1971-07-21 |
Family
ID=27102177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB50635/68A Expired GB1239987A (en) | 1967-10-30 | 1968-10-24 | Phosphonic acid derivatives |
Country Status (19)
| Country | Link |
|---|---|
| AT (1) | AT300828B (en) |
| BE (1) | BE723072A (en) |
| BG (1) | BG22841A3 (en) |
| CH (1) | CH537951A (en) |
| CS (1) | CS152311B2 (en) |
| ES (1) | ES359539A1 (en) |
| FI (1) | FI56016C (en) |
| FR (1) | FR1605540A (en) |
| GB (1) | GB1239987A (en) |
| IE (1) | IE32717B1 (en) |
| IL (1) | IL30918A (en) |
| IT (1) | IT974518B (en) |
| LU (1) | LU57183A1 (en) |
| MT (1) | MTP581B (en) |
| NL (1) | NL162079C (en) |
| OA (1) | OA03883A (en) |
| PL (1) | PL79406B1 (en) |
| SE (1) | SE372537B (en) |
| YU (1) | YU34531B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2372170A1 (en) * | 1976-09-06 | 1978-06-23 | Anvar | Antibilharzia (O)-methyl-(1)-propynyl-phosphonic acid derivs. - intermediates for (1,2)-epoxy-propyl-phosphonic acid anhydrides and other related cpds. |
| FR2507084A1 (en) * | 1981-06-04 | 1982-12-10 | Crinos Industria Farmaco | ANTIBIOTIC COMPOSITION FOR THE ADMINISTRATION OF PHOSPHOMYCIN IN THE FORM OF SLOWLY DISSOLVING TABLETS |
| WO2016029330A1 (en) * | 2014-08-26 | 2016-03-03 | 北京美倍他药物研究有限公司 | Novel phosphonate derivative and medical use thereof |
-
1968
- 1968-10-18 NL NL6814980.A patent/NL162079C/en not_active IP Right Cessation
- 1968-10-21 CH CH1569968A patent/CH537951A/en not_active IP Right Cessation
- 1968-10-21 IL IL30918A patent/IL30918A/en unknown
- 1968-10-22 IE IE1267/68A patent/IE32717B1/en unknown
- 1968-10-23 IT IT40662/68A patent/IT974518B/en active
- 1968-10-24 PL PL1968129720A patent/PL79406B1/en unknown
- 1968-10-24 GB GB50635/68A patent/GB1239987A/en not_active Expired
- 1968-10-25 ES ES359539A patent/ES359539A1/en not_active Expired
- 1968-10-28 YU YU2514/68A patent/YU34531B/en unknown
- 1968-10-29 BE BE723072D patent/BE723072A/xx not_active IP Right Cessation
- 1968-10-29 FI FI3066/68A patent/FI56016C/en active
- 1968-10-29 LU LU57183D patent/LU57183A1/xx unknown
- 1968-10-29 BG BG10915A patent/BG22841A3/xx unknown
- 1968-10-29 SE SE6814618A patent/SE372537B/xx unknown
- 1968-10-30 MT MT581A patent/MTP581B/en unknown
- 1968-10-30 CS CS7405A patent/CS152311B2/cs unknown
- 1968-10-30 FR FR172023A patent/FR1605540A/fr not_active Expired
- 1968-10-30 AT AT1055468A patent/AT300828B/en not_active IP Right Cessation
- 1968-10-30 OA OA53404A patent/OA03883A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2372170A1 (en) * | 1976-09-06 | 1978-06-23 | Anvar | Antibilharzia (O)-methyl-(1)-propynyl-phosphonic acid derivs. - intermediates for (1,2)-epoxy-propyl-phosphonic acid anhydrides and other related cpds. |
| FR2507084A1 (en) * | 1981-06-04 | 1982-12-10 | Crinos Industria Farmaco | ANTIBIOTIC COMPOSITION FOR THE ADMINISTRATION OF PHOSPHOMYCIN IN THE FORM OF SLOWLY DISSOLVING TABLETS |
| EP0067136A1 (en) * | 1981-06-04 | 1982-12-15 | Crinos Industria Farmacobiologica S.p.A. | Pharmaceutical composition of phosphonomicin in tablet form |
| WO2016029330A1 (en) * | 2014-08-26 | 2016-03-03 | 北京美倍他药物研究有限公司 | Novel phosphonate derivative and medical use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1805678B2 (en) | 1973-01-04 |
| CH537951A (en) | 1973-06-15 |
| FI56016C (en) | 1979-11-12 |
| IE32717L (en) | 1969-04-30 |
| FR1605540A (en) | 1979-02-23 |
| YU251468A (en) | 1979-02-28 |
| YU34531B (en) | 1979-09-10 |
| SE372537B (en) | 1974-12-23 |
| CS152311B2 (en) | 1973-12-19 |
| IE32717B1 (en) | 1973-11-14 |
| NL162079C (en) | 1980-04-15 |
| ES359539A1 (en) | 1970-11-01 |
| IT974518B (en) | 1974-07-10 |
| NL162079B (en) | 1979-11-15 |
| PL79406B1 (en) | 1975-06-30 |
| IL30918A0 (en) | 1968-12-26 |
| IL30918A (en) | 1973-03-30 |
| LU57183A1 (en) | 1969-05-16 |
| NL6814980A (en) | 1969-05-02 |
| MTP581B (en) | 1969-09-22 |
| AT300828B (en) | 1972-08-10 |
| OA03883A (en) | 1975-08-14 |
| BG22841A3 (en) | 1977-04-20 |
| DE1805678A1 (en) | 1969-12-11 |
| BE723072A (en) | 1969-04-29 |
| FI56016B (en) | 1979-07-31 |
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