IE35973B1 - Pentavalent-phosphorus amides of cephalosporins - Google Patents
Pentavalent-phosphorus amides of cephalosporinsInfo
- Publication number
- IE35973B1 IE35973B1 IE43/72A IE4372A IE35973B1 IE 35973 B1 IE35973 B1 IE 35973B1 IE 43/72 A IE43/72 A IE 43/72A IE 4372 A IE4372 A IE 4372A IE 35973 B1 IE35973 B1 IE 35973B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- formula
- cephalosporin
- phosphorus
- cephalosporins
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 title abstract 9
- 229940124587 cephalosporin Drugs 0.000 title abstract 9
- 150000001780 cephalosporins Chemical class 0.000 title abstract 8
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 7
- 239000011574 phosphorus Substances 0.000 title abstract 7
- -1 Phosphorus amides Chemical class 0.000 abstract 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000003946 cyclohexylamines Chemical class 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229960004424 carbon dioxide Drugs 0.000 abstract 1
- 235000011089 carbon dioxide Nutrition 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material 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
1383431 Phosphorus amides of cephalosporins ELI LILLY & CO 10 Jan 1972 [11 Jan 1971] 1095/72 Headings C2C and C2P Novel phosphorus amides of cephalosporins, having the general Formula (I) wherein each of R 1 and R 2 is a C 1-15 hydrocarbon 'or O-hydrocarbon radical which is free of aliphatic unsaturation; m is 1, 2 or 3; R 3 is -H or -OCH 3 ; R 4 is a group of formula in which R 5 is hydrogen, an alkali metal cation, an ammonium or amine cation, a negative charge or an ester group, and R 6 is hydrogen, O-(C 1-4 alkyl), S-(C 1-4 alkyl), where n and m are independently 1, 2 or 3, pyridyl, amino-pyridyl, where R 1 and R 2 are as defined above, or and Y is a group of formula in which M is H, an alkali metal cation or a group forming a C 1-4 alkyl mixed carbonic anhydride with the carboxylic group; R 10 is NH 2 or NH 3 <SP>(+)</SP>, or may be hydrogen when there is an amino group in another part of Y or the group R 4 , and the phenyl ring may be substituted with Cl, OH, NH 2 , #-amino-C 2-3 alkyl or NO 2 ; and cyclohexylamine salts thereof, are prepared by reacting a phosphorus compound of formula with a primary amino group-containing cephalosporin of Formula (II) wherein R 1 , R 2 , R 3 , R 4 and Y are as defined above and X is Cl or Br, in a liquid reaction medium at a pH of 7À5 to 12. The phosphorus amides may be decomposed to give the cephalosporin starting material (II) by allowing to stand in solution in cyclohexanone, when the said cephalosporin precipitates. This property provides a further aspect of the invention whereby cephalosporins of Formula (II) may be recovered from their impure solutions by conversion to the phosphorus amide (I) by the reaction described above, extracting with cyclohexanone and allowing the extract to stand at room temperature to precipitate the original cephalosporin (II). Alternatively, the cyclohexanone solution may be treated with cyclohexylamine to precipitate the cyclohexylamine salt of the cephalosporin phosphorus amide. This salt may be subjected to a conventional de-amidation procedure (e.g. reaction with PCl 5 , then methanol followed by hydrolysis) to give 7-aminocephalosporanic acid.
[GB1383431A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10567371A | 1971-01-11 | 1971-01-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35973L IE35973L (en) | 1972-07-11 |
| IE35973B1 true IE35973B1 (en) | 1976-07-07 |
Family
ID=22307142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE43/72A IE35973B1 (en) | 1971-01-11 | 1972-01-11 | 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 ES ES398734A patent/ES398734A1/en not_active Expired
- 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
- 1972-01-10 GB GB109572A patent/GB1383431A/en not_active Expired
- 1972-01-10 CH CH32772A patent/CH582194A5/xx not_active IP Right Cessation
- 1972-01-10 PL PL1972152837A patent/PL87129B1/pl unknown
- 1972-01-11 CS CS7200000164A patent/CS179376B2/en unknown
- 1972-01-11 IE IE43/72A patent/IE35973B1/en unknown
- 1972-01-11 DE DE19722201074 patent/DE2201074A1/en active Pending
- 1972-01-11 FR FR7200785A patent/FR2121746B1/fr not_active Expired
- 1972-01-11 NL NL7200432A patent/NL7200432A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL38508A0 (en) | 1972-03-28 |
| CA1006503A (en) | 1977-03-08 |
| ES398734A1 (en) | 1975-06-01 |
| AT321459B (en) | 1975-04-10 |
| PL87129B1 (en) | 1976-06-30 |
| CS179376B2 (en) | 1977-10-31 |
| DE2201074A1 (en) | 1972-08-03 |
| AU464424B2 (en) | 1975-08-28 |
| HU165335B (en) | 1974-08-28 |
| ZA718666B (en) | 1973-08-29 |
| FR2121746A1 (en) | 1972-08-25 |
| AU3755572A (en) | 1973-07-05 |
| NL7200432A (en) | 1972-07-13 |
| CH582194A5 (en) | 1976-11-30 |
| BE777580A (en) | 1972-06-30 |
| IL38508A (en) | 1975-11-25 |
| IE35973L (en) | 1972-07-11 |
| GB1383431A (en) | 1974-02-12 |
| FR2121746B1 (en) | 1974-12-13 |
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