GB1342242A - Cephalosporin compounds - Google Patents
Cephalosporin compoundsInfo
- Publication number
- GB1342242A GB1342242A GB1342242DA GB1342242A GB 1342242 A GB1342242 A GB 1342242A GB 1342242D A GB1342242D A GB 1342242DA GB 1342242 A GB1342242 A GB 1342242A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- compound
- compounds
- groups
- hydrogen
- 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 Cephalosporin compounds Chemical class 0.000 title abstract 13
- 229930186147 Cephalosporin Natural products 0.000 title abstract 5
- 229940124587 cephalosporin Drugs 0.000 title abstract 5
- 239000002585 base Substances 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 abstract 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 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 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 abstract 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 abstract 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002222 fluorine compounds Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 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
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
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
1342242 3 - Organophosphorus - cephalo- Sporins GLAXO LABORATORIES Ltd 12 Jan 1971 [23 Jan 1970] 33339/73 Divided out of 1342241 Heading C2A The invention comprises novel cephalosporin compounds having the general formulµ (II) and (III) wherein R<SP>8</SP> is hydrogen or a carboxylic acyl group; Z is either -S- or R<SP>6</SP> is hydrogen or a carboxyl-blocking group; Y is -#PR 3 or -PO(OR) 2 ; R is an organic substituent group; the dotted line indicates a double bond in either the 2,3-position or the + 3,4-position; and when Y is -PR 3 , then the compound includes an anion or the group at the 4-position is -COO-. The compounds (II) are prepared by reacting a corresponding 3-halomethyl cephalosporin with (a) a phosphine of formula PR 3 when the compound (II) in which Y is -#PR 3 is desired, or (b) a phosphite triester of formula P(OR) 3 when the compound (II) in which Y is is desired, preferably in an inert organic solvent in the presence of an alkali metal bromide or iodide. The phosphoranylidene compounds (III) are prepared by abstracting an acidic proton from a phosphonium compound of formula (II) (i.e. + wherein Y is -PR 3 ) by treating the latter with a base. Suitable bases are alkali metal and alkaline earth metal hydroxides, carbonates, and hydrogen carbonates, disodium hydrogen phosphate and sodium hydride. Other bases used can be tert. nitrogen bases, onium and alkali metal alkoxides and fluorides, a conjugate base of dimethylsulphoxide, dimethylacetamide or dimethylformamide, sodio and lithio derivatives of hexadimethylsilazane, a phosphoranylidene which is more basic than the phosphoranylidene being produced, and alkylene oxides in the presence of halide ion. The use of a base in this procedure when the starting phosphonium compound (III) is a ceph-2-em compound will conjointly effect isomerization thereof to the ceph-3-em isomer. The groups R may be identical or different alkyl, aralkyl or aryl groups which may be substituted by one or more halogen atoms, or nitro, cyano, amino, acyl and acylamino groups. The acyl group R<SP>8</SP> may be any of the acylating groups on the 6- or 7-amino nitrogen of a penicillin or cephalosporin antibiotic. The carboxylblocking group R<SP>6</SP> may be the residue of an aliphatic, araliphatic or aromatic alcohol, or of a silanol, stannanol or acid, preferably being a group which is easily removable at a later stage if desired. Anions in compounds II wherein + Y is -PR 3 are usually halide ions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3333973 | 1971-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1342242A true GB1342242A (en) | 1974-01-03 |
Family
ID=10351685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1342242D Expired GB1342242A (en) | 1971-01-12 | 1971-01-12 | Cephalosporin compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1342242A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3005888A1 (en) * | 1979-02-19 | 1980-08-28 | Fujisawa Pharmaceutical Co | 3-PHOSPHONOCEPHALOSPORANIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME |
-
1971
- 1971-01-12 GB GB1342242D patent/GB1342242A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3005888A1 (en) * | 1979-02-19 | 1980-08-28 | Fujisawa Pharmaceutical Co | 3-PHOSPHONOCEPHALOSPORANIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THE SAME |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |