ES398734A1 - Pentavalent phosphorus amides of cephalosporins - Google Patents
Pentavalent phosphorus amides of cephalosporinsInfo
- Publication number
- ES398734A1 ES398734A1 ES398734A ES398734A ES398734A1 ES 398734 A1 ES398734 A1 ES 398734A1 ES 398734 A ES398734 A ES 398734A ES 398734 A ES398734 A ES 398734A ES 398734 A1 ES398734 A1 ES 398734A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- group
- see formula
- compound
- cephalosporin
- 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
- -1 phosphorus amides Chemical class 0.000 title abstract 9
- 229930186147 Cephalosporin Natural products 0.000 title abstract 5
- 229940124587 cephalosporin Drugs 0.000 title abstract 5
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 3
- 150000001780 cephalosporins Chemical class 0.000 title abstract 2
- 239000011574 phosphorus Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229930182555 Penicillin Natural products 0.000 abstract 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 229940049954 penicillin Drugs 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 150000003946 cyclohexylamines Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- SXADIBFZNXBEGI-UHFFFAOYSA-N phosphoramidous acid Chemical class NP(O)O SXADIBFZNXBEGI-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 230000003381 solubilizing effect Effects 0.000 abstract 1
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
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)
- Cephalosporin Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for the preparation of a new pentavalent phosphorous amide derivative of a cephalosporin-like compound containing a primary amino group, of general formula VI, ** (See formula) ** where each of the groups R1 and R2 is selected from the group consisting of hydrocarbon and -O-hydrocarbon radicals containing from 1 to 15 carbon atoms, the radicals of which are free of aliphatic unsaturation; m is 1 to 5 corresponding to the number of primary amino groups in the penicillin or cephalosporin compound; the indicated free valence of the pentavalent phosphorus atom is bound to nitrogen derived from the primary amino group of the penicillin or cephalosporin compound; Y is selected from the group consisting of the remainder of an acrylamido group of the starting penicillin or cephalosporin, which may contain a pentavalent phosphorous amide of any of the free amino groups of said acylamido group; R3 is hydrogen or -OCH3; R4 is selected from the group consisting of ** (See formula) ** where R5 is hydrogen, an alkali metal cation, a solubilizing ammonium or amine cation, a negative charge, or an ester group that is easily removed by zinc reduction in an acidic medium or by hydrogenation processes; and R6 is hydrogen, -X-alkyl where X is oxygen or sulfur and the alkyl group contains 1 to 4 carbon atoms, ** (See formula) ** from 1 to 7 carbon atoms, ** (See formula) ** where n and m are independently 1 to 3, - pyridyl, an aminopyridine radical, - (see formula) where R1 and R2 are the ones defined above, or (see formula), or the cyclohexylamine salts of said compounds and the compounds defined above where R4 is ** (See formula) ** whose procedure includes the steps of: (1) reacting a cephalosporin compound of the formula: ** (See formula) ** where Y, R3 and R4 are as described above, with a pentavalent phosphorus compound of the formula: ** (See formula) ** where X is chlorine or bromine and R1 and R2 are as previously described; (2) Extracting the compound of formula VI in cyclohexanone; and (3) converting the compound of formula VI to the cyclohexylamine salt. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10567371A | 1971-01-11 | 1971-01-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES398734A1 true ES398734A1 (en) | 1975-06-01 |
Family
ID=22307142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES398734A Expired ES398734A1 (en) | 1971-01-11 | 1972-01-10 | Pentavalent phosphorus amides of cephalosporins |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT321459B (en) |
| AU (1) | AU464424B2 (en) |
| BE (1) | BE777580A (en) |
| CA (1) | CA1006503A (en) |
| CH (1) | CH582194A5 (en) |
| CS (1) | CS179376B2 (en) |
| DE (1) | DE2201074A1 (en) |
| ES (1) | ES398734A1 (en) |
| FR (1) | FR2121746B1 (en) |
| GB (1) | GB1383431A (en) |
| HU (1) | HU165335B (en) |
| IE (1) | IE35973B1 (en) |
| IL (1) | IL38508A (en) |
| NL (1) | NL7200432A (en) |
| PL (1) | PL87129B1 (en) |
| ZA (1) | ZA718666B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5941999B2 (en) | 1975-07-24 | 1984-10-11 | 武田薬品工業株式会社 | Method for producing cefem or venam compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL120301C (en) * | 1959-06-09 | |||
| US3173916A (en) * | 1960-06-28 | 1965-03-16 | Pfizer & Co C | Derivatives of 7-aminocephalosporanic acid |
| US3144444A (en) * | 1960-09-27 | 1964-08-11 | Pfizer & Co C | Novel derivatives of 6-aminopenicillanic acid |
| GB924612A (en) * | 1960-12-19 | 1963-04-24 | Ici Ltd | Penicillins |
-
1971
- 1971-12-28 ZA ZA718666A patent/ZA718666B/en unknown
- 1971-12-30 BE BE777580A patent/BE777580A/en unknown
-
1972
- 1972-01-04 AU AU37555/72A patent/AU464424B2/en not_active Expired
- 1972-01-04 IL IL38508A patent/IL38508A/en unknown
- 1972-01-10 CH CH32772A patent/CH582194A5/xx not_active IP Right Cessation
- 1972-01-10 ES ES398734A patent/ES398734A1/en not_active Expired
- 1972-01-10 GB GB109572A patent/GB1383431A/en not_active Expired
- 1972-01-10 PL PL1972152837A patent/PL87129B1/pl unknown
- 1972-01-10 CA CA132,029A patent/CA1006503A/en not_active Expired
- 1972-01-10 HU HUEI401A patent/HU165335B/hu unknown
- 1972-01-10 AT AT15572A patent/AT321459B/en not_active IP Right Cessation
- 1972-01-11 CS CS7200000164A patent/CS179376B2/en unknown
- 1972-01-11 IE IE43/72A patent/IE35973B1/en unknown
- 1972-01-11 FR FR7200785A patent/FR2121746B1/fr not_active Expired
- 1972-01-11 NL NL7200432A patent/NL7200432A/xx unknown
- 1972-01-11 DE DE19722201074 patent/DE2201074A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU3755572A (en) | 1973-07-05 |
| IL38508A0 (en) | 1972-03-28 |
| BE777580A (en) | 1972-06-30 |
| AT321459B (en) | 1975-04-10 |
| DE2201074A1 (en) | 1972-08-03 |
| NL7200432A (en) | 1972-07-13 |
| CS179376B2 (en) | 1977-10-31 |
| CA1006503A (en) | 1977-03-08 |
| CH582194A5 (en) | 1976-11-30 |
| IE35973B1 (en) | 1976-07-07 |
| HU165335B (en) | 1974-08-28 |
| AU464424B2 (en) | 1975-08-28 |
| GB1383431A (en) | 1974-02-12 |
| IL38508A (en) | 1975-11-25 |
| FR2121746B1 (en) | 1974-12-13 |
| IE35973L (en) | 1972-07-11 |
| FR2121746A1 (en) | 1972-08-25 |
| ZA718666B (en) | 1973-08-29 |
| PL87129B1 (en) | 1976-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GR78508B (en) | ||
| KE2923A (en) | Novel penicillins and cephalosporine and process for producing the same | |
| CA1238910A (en) | Carboxyalkenoic acids | |
| ES396223A1 (en) | Herbicidal phosphonomethylglycine compounds and compositions containing them | |
| ES444804A1 (en) | Process for preparing (1-acylaminomethyl)-1,2,3,4-tetrahydroisoquinolines | |
| ES398734A1 (en) | Pentavalent phosphorus amides of cephalosporins | |
| ES438234A1 (en) | Oxacyclohexane derivatives | |
| ES443590A1 (en) | Method for the preparation of n-substituted carbamic acid salts | |
| ES437842A1 (en) | Process for preparing thiohydrozoazetidiones | |
| ES317862A1 (en) | Method for the production of new penicillins. (Machine-translation by Google Translate, not legally binding) | |
| ES8104309A1 (en) | Process for preparing enamine derivatives, compounds so produced and process for preparing a 3-hydroxy-cephalosporin. | |
| ES414340A1 (en) | Piperazine derivatives | |
| MX3396E (en) | PROCEDURE FOR PRODUCING A COPPER COMPLEX (II) | |
| GB1482388A (en) | Method of producing 6-beta-amidinopenicillanic acid derivatives | |
| ES454265A1 (en) | Method for preparing novel cephalosporins | |
| ES296119A1 (en) | Procedure for obtaining new heterocyclic compounds (Machine-translation by Google Translate, not legally binding) | |
| ES386042A1 (en) | A procedure for the preparation of 3-hydroxy-3-methyl-7-aminocefam-carboxylic compounds. (Machine-translation by Google Translate, not legally binding) | |
| GB1332989A (en) | Preparation of quaternary immonium salts | |
| ES437134A1 (en) | Process for the manufacture of 2-aminobenzenesulphonamides | |
| ES398740A1 (en) | Method for the production of new olefinic aliphatic compounds. (Machine-translation by Google Translate, not legally binding) | |
| ES478919A1 (en) | A procedure for the production of cefalosporine analogs. (Machine-translation by Google Translate, not legally binding) | |
| ES291879A1 (en) | Procedure for the manufacture of new basic 1,3-dioxanes and their salts (Machine-translation by Google Translate, not legally binding) | |
| ES391146A3 (en) | A procedure for preparing an aminopropionil-orto-totoludine. (Machine-translation by Google Translate, not legally binding) | |
| ES8302712A1 (en) | Imidazobenzodiazepines | |
| ES207773A1 (en) | A procedure for the preparation of anesthetics (Machine-translation by Google Translate, not legally binding) |