FR2429221A1 - 3-Carbamoyloxy:methyl cephalosporin antibiotics prodn. - from 3-hydroxymethyl cpd. and di:halo-phosphinyl isocyanate, and new intermediates - Google Patents
3-Carbamoyloxy:methyl cephalosporin antibiotics prodn. - from 3-hydroxymethyl cpd. and di:halo-phosphinyl isocyanate, and new intermediatesInfo
- Publication number
- FR2429221A1 FR2429221A1 FR7908746A FR7908746A FR2429221A1 FR 2429221 A1 FR2429221 A1 FR 2429221A1 FR 7908746 A FR7908746 A FR 7908746A FR 7908746 A FR7908746 A FR 7908746A FR 2429221 A1 FR2429221 A1 FR 2429221A1
- Authority
- FR
- France
- Prior art keywords
- prodn
- isocyanate
- ceph
- phosphinyl
- carbamoyloxy
- 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.)
- Granted
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract 3
- 229940088710 antibiotic agent Drugs 0.000 title abstract 3
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 title abstract 2
- 229930186147 Cephalosporin Natural products 0.000 title 1
- -1 methyl cephalosporin Chemical class 0.000 title 1
- FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical group S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical group S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/547—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)
Abstract
Prodn. of 3-carbamoyloxymethyl-cephalosporins (I) comprises reacting 3-hydroxymethylcephalosporins (II) with a dihalophosphinyl isocyanate (II), then converting the reaction prod., pref. by hydrolysis, to (I). Cpds. of formula (N) and their salts are new (where is R1 protected amino R2 is H or blocking gp. R3 is H, lower alkyl, alkylthio or alkoxy. Z is S or S right arrow O (alpha or beta). The dotted line indicates a ceph-3-em or ceph-2-em ring). Esp. Z is S,R2, is H and the ring is ceph-3-em. (I) are known antibiotics. (III) are easy to prepare and can be used without purificn. (IV) are intermediates during reaction of (II) and (III) and some also have activity against Gram negative and positive bacteria. They are very soluble in water and are esp. useful for treating humans and animals requiring amts of antibiotics in soln.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1380178 | 1978-04-07 | ||
| GB1379978 | 1978-04-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2429221A1 true FR2429221A1 (en) | 1980-01-18 |
| FR2429221B1 FR2429221B1 (en) | 1983-04-22 |
Family
ID=26250016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7908746A Granted FR2429221A1 (en) | 1978-04-07 | 1979-04-06 | 3-Carbamoyloxy:methyl cephalosporin antibiotics prodn. - from 3-hydroxymethyl cpd. and di:halo-phosphinyl isocyanate, and new intermediates |
Country Status (11)
| Country | Link |
|---|---|
| AU (1) | AU534617B2 (en) |
| DE (1) | DE2914000A1 (en) |
| DK (1) | DK143679A (en) |
| FI (1) | FI791148A (en) |
| FR (1) | FR2429221A1 (en) |
| IE (1) | IE48286B1 (en) |
| IT (1) | IT1117214B (en) |
| NL (1) | NL7902732A (en) |
| NZ (1) | NZ190128A (en) |
| SE (1) | SE7903096L (en) |
| YU (1) | YU82379A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL58287A (en) * | 1979-04-06 | 1982-08-31 | Glaxo Group Ltd | Process for the preparation of 3-carbamoyloxymethyl cephalosporin compounds |
-
1979
- 1979-04-06 FI FI791148A patent/FI791148A/en not_active Application Discontinuation
- 1979-04-06 NL NL7902732A patent/NL7902732A/en not_active Application Discontinuation
- 1979-04-06 FR FR7908746A patent/FR2429221A1/en active Granted
- 1979-04-06 DK DK143679A patent/DK143679A/en not_active Application Discontinuation
- 1979-04-06 AU AU45896/79A patent/AU534617B2/en not_active Ceased
- 1979-04-06 DE DE19792914000 patent/DE2914000A1/en not_active Withdrawn
- 1979-04-06 NZ NZ190128A patent/NZ190128A/en unknown
- 1979-04-06 YU YU00823/79A patent/YU82379A/en unknown
- 1979-04-06 IT IT48658/79A patent/IT1117214B/en active
- 1979-04-06 SE SE7903096A patent/SE7903096L/en not_active Application Discontinuation
- 1979-08-08 IE IE752/79A patent/IE48286B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7903096L (en) | 1979-12-17 |
| IE790752L (en) | 1979-10-07 |
| AU4589679A (en) | 1979-10-11 |
| AU534617B2 (en) | 1984-02-09 |
| FI791148A (en) | 1979-10-08 |
| NL7902732A (en) | 1979-10-09 |
| FR2429221B1 (en) | 1983-04-22 |
| YU82379A (en) | 1983-01-21 |
| DE2914000A1 (en) | 1979-11-15 |
| DK143679A (en) | 1979-10-08 |
| NZ190128A (en) | 1982-03-16 |
| IT1117214B (en) | 1986-02-17 |
| IE48286B1 (en) | 1984-11-28 |
| IT7948658A0 (en) | 1979-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |