US3852281A
Expired / Lapsed
US
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Process for the preparation of 7-substituted amino-desacetoxycephalosporanic acid compounds
Assignee: DSM Delft BV
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Filing: 1971-02-16
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Granted: 1974-12-03
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Expires: 1991-02-16
Abstract
Abstract Novel process for the preparation of 7-substituted aminodesacetoxycephalosporanic acids compounds by heating the corresponding 6-substituted amino-penicillanic sulfoxide compound in the presence of at least 5 moles of a nitrogen base per mole of sulfoxide compound and a silyl compound having a siliconhalide bond and to novel intermediates.
Inventors
- 👤 J Verweij
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 04:59
CPC Classifications
C; C07; C07D; C07D499/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
68 words
IN THE PROCESS FOR THE PREPARATION OF 7B-ACYLAMINO-3METHYL-CEPH-3-EM-4-CARBOXYLIC ACID COMPOUNDS BY HEATING BETWEEN 50* ANF 160* C. THE CORRESPONDING 6BACYLAMIDOPENICILLANIC SULFOXIDE, ESTER IR AMIDE THE IMPROVEMENT COMPRISING CONDUCTING THE HEATING UNDER ANHYDROUS CONDITIONS IN THE PRESENCE OF AT LEAST 10 MOLES OF A NITROGEN CONTAINING ORGANIC BASE WITH A PKA (IN WATER) BETWEEN 4 AND 10 PER MOLE OF PENICILLANIC SULFOXIDE AND A SILICON-HALOGEN COMPOUND OF THE FORMULA
Claim 2
Dependent Claim
68 words
IN THE PROCESS FOR THE PREPARATION OF 7B-ACYLAMINO-3METHYL-CEPH-3-EM-4-CARBOXYLIC ACID COMPOUNDS BY HEATING BETWEEN 50* ANF 160* C. THE CORRESPONDING 6BACYLAMIDOPENICILLANIC SULFOXIDE, ESTER IR AMIDE THE IMPROVEMENT COMPRISING CONDUCTING THE HEATING UNDER ANHYDROUS CONDITIONS IN THE PRESENCE OF AT LEAST 10 MOLES OF A NITROGEN CONTAINING ORGANIC BASE WITH A PKA (IN WATER) BETWEEN 4 AND 10 PER MOLE OF PENICILLANIC SULFOXIDE AND A SILICON-HALOGEN COMPOUND OF THE FORMULA
Claim 3
Dependent Claim
43 words
The process of claim 1 wherein the acylamido group is selected from the group consisting of phenylacetamido, phenoxyacetamido, Alpha -(benzyloxycarbamoyl)-phenylacetamido and 2-ethoxynaphthamido, and when the grouping is Alpha -benzyloxycarbamoyl-phenylacetamido removing from the resulting desacetoxycephalosporanic acid product the benzyloxycarbonyl group on the amino radical.
Claim 4
Dependent Claim
25 words
The process of claim 1 wherein the 6 Beta -penicillanic sulfoxide is present in the acid form or its lower alkyl, benzyl and benzhydryl ester.
Claim 5
Dependent Claim
14 words
The process of claim 1 in which the temperature is between 60* and 130*C.
Claim 6
Dependent Claim
14 words
The process of claim 1 in which the temperature is from 70* to 100*C.
Claim 7
Dependent Claim
46 words
The process of claim 1 in which the nitrogen containing base is selected from the group consisting of hexamethylenetetramine, N-methyl-aniline, dimethylaniline, pyridine and pyridine substituted with at least one member selected from the group consisting of lower alkyl, mono and di(lower) alkylamino, a collidine and quinoline.
Claim 8
Dependent Claim
23 words
The process of claim 1 wherein the nitrogen-containing base is selected from the group consisting of a picoline, 2-ethylpyridine, 2-propylpyridine, 2,3-dimethylpyridine and 2,6-dimethylpyridine.
Claim 9
Dependent Claim
22 words
The process of claim 1 wherein the nitrogen-containing base is selected from the group consisting of Alpha -picoline, 2,5-dimethylpyridine, 2-dimethylaminopyridine and 3-methylisoquinoline.
Claim 10
Dependent Claim
22 words
The process of claim 1 wherein the amount of nitrogen-containing base is 10 to 70 moles for each mole of penicillanic sulphoxide.
Claim 11
Dependent Claim
10 words
The process of claim 1 in which X is chlorine.
Claim 12
Dependent Claim
35 words
The process of claim 1 in which the silicon-halogen compound is selected from the group consisting of triethylchlorosilane, methyltrichlorosilane, trimethylbromosilane, tri-n-propylchlorosilane, triethylbromosilane, tri-n-propyl-bromo silane, bromomethyl-dimethylchlorosilane, tri-n-butyl-chlorosilane, methyldiethylchlorosilane, dimethylethylchlorosilane, phenyldimethylbromosilane, benzylmethylethylchlorosilane, phenylethylmeThylchlorosilane, triphenylchlorosilane, tri-o-tolyl-chlorosilane and tri-p-dimethylaminophenyl-chlorosilane.
Claim 13
Dependent Claim
19 words
The process of claim 1 wherein the silicon-halogen compound is selected from the group consisting of trimethylchlorosilane and dimethyldichlorosilane.
Claim 14
Dependent Claim
21 words
The process of claim 1, in which the silicon-halogen compound is present in molar excess in relation to the penicillanic sulphoxide.
Claim 15
Dependent Claim
21 words
The process of claim 13 in which 3 to 15 moles of silicon-halogen compound is present per mole of penicillanic sulphoxide.
Claim 16
Dependent Claim
15 words
The process of claim 1 wherein the reaction is effected in an inert organic solvent.
Claim 17
Dependent Claim
16 words
The process of claim 15 in which the organic solvent is benzyl cyanide or a haloalkane.
Claim 18
Dependent Claim
23 words
The process of claim 16 in which the halo alkane is selected from the group consisting of 1,2-dichloroethane, 1,1-dichloroethane, 1-bromo-1-chloroethane, 1,2,3-trichloropropane and chloroform.
Claim 19
Dependent Claim
35 words
The process of claim 15 wherein the solvent is selected from the group consisting of benzyl cyanide, 1,2-dichloroethane, 1-bromo-1-chloroethane and chloroform and the base is selected from the group consisting of Alpha -picoline and 2,5-dimethylpyridine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-02 | 1978-06-03 | 1978-12-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-02 | 1982-06-03 | 1982-12-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-02 | 1986-06-03 | 1986-12-03 | $7700.00 | Window Closed / Lapsed |