GB1355791A - Process for the preparation of cephalosporanic acid derivatives application - Google Patents
Process for the preparation of cephalosporanic acid derivatives applicationInfo
- Publication number
- GB1355791A GB1355791A GB789270A GB789270A GB1355791A GB 1355791 A GB1355791 A GB 1355791A GB 789270 A GB789270 A GB 789270A GB 789270 A GB789270 A GB 789270A GB 1355791 A GB1355791 A GB 1355791A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- alkyl
- sulphoxide
- phenyl
- ester
- 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
1355791 Preparation of cephalosporanic acid compounds KONINKLIJKE NEDERLANDSCHE GIST-EN SPIRITUSFABRIEK NV 19 April 1971 [18 Feb 1970 23 July 1970] 7892/70 and 35796/70 Heading C2A [Also in Division C3] The invention comprises a process for the transformation of a 6-substituted aminopenicillanic sulphoxide in the form of an acid or a derivative thereof, including a thiocarboxylic acid derivative, salt, ester or amide, into a 7- substituted aminodesacetoxycephalosporanic derivative characterized in that the penicillanic sulphoxide compound is heated up to a temperature not greater than 160‹ C. under anhydrous conditions in the presence of at least one nitrogen containing organic base and a silicon compound having a silicon-halogen bond, at least 5 moles of base being present for each mole of penicillanic sulphoxide compound. The penicillanic sulphoxide starting material may be of the general Formula I and the 7-substituted amino-desacetoxycephalosporanic acid derivative obtained as product may be of the Formula II wherein R 1 represents a group linked to the nitrogen atom by a carbon or sulphur atom, R 2 represents a hydrogen or an alkyl or phenylalkyl group, or R 1 and R 2 together with the nitrogen atom to which they are attached represent a heterocyclic group which may carry one or more substituents, and R 3 represents (a) a radical linked to the carbon atom by nitrogen, the nitrogen atom having attached to it atoms or groups selected from hydrogen, alkyl and aryl groups or a combination of two carbonyl groups on the nitrogen atom may be joined through the agency of a phenyl group; or R 3 represents (b) a group -SR 4 wherein R 4 is hydrogen, alkyl or phenyl; or R 3 represents (c) a group -OR 5 wherein R 5 is hydrogen, a cation which is preferably pharmaceutically acceptable, an alkyl group, a cycloalkyl group containing 4 to 7 carbon atoms, phenyl, phenylalkyl or diphenylalkyl or aroylalkyl group, the alkyl radicals of which contain 1 or 2 carbon atoms, or a stannyl group (R 6 R 7 R 8 )#Snwherein R 6 , R, and R 8 each represent an alkyl group, a phenyl group or a phenylalkyl group containing 1 or 2 carbon atoms in the alkyl radical, or a silyl group (R 9 R 10 R 11 )#Siwherein R 9 , R 10 and R 11 each represent a halogen atom, an alkyl group, phenyl or phenylalkyl group containing one or two carbon atoms in the alkyl radical, or one of R 9 , R 10 and R 11 represents the group connected to symbol R 3 in Formula II and linked via oxygen to the silicon atom, the alkyl and aryl groups within the definitions of R 2 and R 3 optionally carrying as substituents halogen atoms and in the case of aryl groups, alkyl, alkoxy or dialkylamino groups. The invention also comprises 6-aminopenicillanic sulphoxide silyl esters of the general Formula III wherein R 1 and R 2 are as previously defined, Y 1 , Y 2 and Y 3 each may be the same or different and each represents a halogen atom, an alkyl group, or a phenyl or a phenylalkyl group containing one or two carbon atoms in the alkyl radical, the alkyl and phenyl groups optionally carrying substituents such as halogen atoms and, in the case of phenyl groups, alkyl, alkoxy, or dialkylamino groups or one of Y 1 , Y 2 and Y 3 represents the 6-aminopenicillanyl-carbonyloxy group attached to the silicon atom in the formula. Particular examples of these compounds are benzylpenicillin sulphoxide trimethylsilyl ester, benzylpenicillin sulphoxide dimethyl chlorosilyl ester, di-(benzylpenicillin sulphoxide)dimethylsilyl ester, phenoxymethyl. penicillin sulphoxide trimethylsilyl ester, phenoxymethylpenicillin dimethylchlorosilyl ester and di-(phenoxymethylpenicillin sulphoxide) dimethylsilyl ester. Reference has been directed by the Comptroller to Specification 1,174,335.
Priority Applications (35)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB789270A GB1355791A (en) | 1970-02-18 | 1970-02-18 | Process for the preparation of cephalosporanic acid derivatives application |
US00115883A US3852281A (en) | 1970-02-18 | 1971-02-16 | Process for the preparation of 7-substituted amino-desacetoxycephalosporanic acid compounds |
YU382/71A YU35448B (en) | 1970-02-18 | 1971-02-16 | Process for obtaining 7-substituted amino-deacetoxy cephalosporanic acids |
DE2107650A DE2107650B2 (en) | 1970-02-18 | 1971-02-17 | Process for the preparation of 7-acylamido-S-methyl-ceph-S-em ^ -carboxylic acid derivatives |
NO580/71A NO144170C (en) | 1970-02-18 | 1971-02-17 | PROCEDURE FOR THE PREPARATION OF DESACETOXY-CEPHALOSPORANIC ACID DERIVATIVES. |
IE191/71A IE35010B1 (en) | 1970-02-18 | 1971-02-17 | New process for the preparation of cephalosporanic acid derivatives |
ES388373A ES388373A1 (en) | 1970-02-18 | 1971-02-17 | Process for the preparation of 7-substituted amino-desacetoxycephalosporanic acid compounds |
HU71KO2699A HU170715B (en) | 1970-02-18 | 1971-02-17 | Process for production of subsituated 1-oxo-2,2-dimethil-6-amin-penam-carbonic acid silil esthers |
LU62618D LU62618A1 (en) | 1970-02-18 | 1971-02-17 | |
DE19712166561 DE2166561A1 (en) | 1970-02-18 | 1971-02-17 | 6-AMINOPENICILLANSULFOXIDE SILYLESTER |
NLAANVRAGE7102131,A NL170148C (en) | 1970-02-18 | 1971-02-17 | PROCESS FOR PREPARING A 7- (SUBSTITUTED AMINO) DESACETOXYCEPHALOSPORANIC ACID DERIVATIVE. |
ZA711014A ZA711014B (en) | 1970-02-18 | 1971-02-17 | Process for the preparation of desacetoxycephalosporines |
DK72671AA DK140639B (en) | 1970-02-18 | 1971-02-17 | Process for the preparation of 7beta-acylamino-3-methyl-ceph-3-em-4-carboxylic acids or their salts, esters or amides. |
CS711203A CS191866B2 (en) | 1970-02-18 | 1971-02-17 | Method of producing 7-substituted amino-deacetoxycephalosporanic acids |
BE763104A BE763104A (en) | 1970-02-18 | 1971-02-17 | NEW PROCESS FOR PREPARING CEPHALOSPORANIC ACID DERIVATIVES |
HUKO2402A HU166587B (en) | 1970-02-18 | 1971-02-17 | |
SE7102038A SE395897B (en) | 1970-02-18 | 1971-02-17 | PROCEDURE FOR THE PREPARATION OF 7BETA-ACYLAMIDO-3-METHYL-CEF-3-EM-4-CARBONIC ACIDS |
CA105,608A CA976546A (en) | 1970-02-18 | 1971-02-17 | Process for the preparation of cephalosporanic acid derivatives |
AT134671A AT317420B (en) | 1970-02-18 | 1971-02-17 | Process for the conversion of a 6-substituted aminopenicillan sulfoxide |
IL36217A IL36217A (en) | 1970-02-18 | 1971-02-17 | The preparation of cephalosporanic acid derivatives and new intermediate penicillin sulphoxide silyl esters |
CH228371A CH570408A5 (en) | 1970-02-18 | 1971-02-17 | |
FR7105387A FR2078715A5 (en) | 1970-02-18 | 1971-02-17 | |
FI450/71A FI55205C (en) | 1970-02-18 | 1971-02-17 | FREQUENCY REFRIGERATION OF ANTIBIOTICS VERKSAMMA 7BETA-ACYLAMIDO-3-METHYLCEF-3-EM-4-CARBOXYL SYROR |
PH12203*UA PH9353A (en) | 1970-02-18 | 1971-02-17 | Process for the preparation of 7-substituted aminodesacetoxycephalosporanic acids |
JP46007332A JPS5139234B1 (en) | 1970-02-18 | 1971-02-17 | |
PL1971146306A PL82809B1 (en) | 1970-02-18 | 1971-02-17 | Process for the preparation of 7-substituted amino-desacetoxycephalosporanic acid compounds[us3852281a] |
RO65983A RO58059A (en) | 1970-02-18 | 1971-02-18 | |
NO3114/71A NO144168C (en) | 1970-02-18 | 1971-08-20 | 6-ACYLAMINOPENICILLANIC ACID SULPHOXIDE SILYL ESTERS FOR USE AS OUTCOMES IN THE PREPARATION OF 7-ACYLAMINODESACETOXYCE PHALOSPORAN ACIDS |
CA131,725A CA988512A (en) | 1970-02-18 | 1972-01-05 | Process for the preparation of cephalosporanic acid derivatives |
PH14720*UA PH9418A (en) | 1970-02-18 | 1973-06-11 | 6-b-acylamidopenicillanic sulfoxide silyl esters |
SE7402023A SE411549B (en) | 1970-02-18 | 1974-02-15 | 6-AMINOPENICILLIN SULPHXIDE SILYL ESTERS FOR USE AS INTERMEDIATES IN THE PREPARATION OF 7-AMINODESACETOXICE PHALOSPORANIC ACID DERIVATIVES |
US05/500,261 US4000129A (en) | 1970-02-18 | 1974-08-26 | 6-aminopenicillanic acid sulfoxide silyl esters |
JP51046075A JPS5217490A (en) | 1970-02-18 | 1976-04-19 | Production of 66aminopenicillanic acid sulpaoxidosilylesters |
FI761214A FI58777C (en) | 1970-02-18 | 1976-04-29 | 6BETA-ACYLAMIDOPENICILLANSYRASULFOXIDSILYLESTRAR VILKA ANVAENDES SOM MELLANPRODUKTER VID FRAMSTAELLNING AV 7BETA-ACYLAMIDO-3-METHYL-CEF-3-EMKARBOXYLSYROR |
DK330777A DK140482B (en) | 1970-02-18 | 1977-07-21 | 6beta-Acylaminopenicillanic acid sulfoxide silyl esters for use as intermediates. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB789270A GB1355791A (en) | 1970-02-18 | 1970-02-18 | Process for the preparation of cephalosporanic acid derivatives application |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1355791A true GB1355791A (en) | 1974-06-05 |
Family
ID=9841818
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB789270A Expired GB1355791A (en) | 1970-02-18 | 1970-02-18 | Process for the preparation of cephalosporanic acid derivatives application |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE763104A (en) |
GB (1) | GB1355791A (en) |
HU (1) | HU170715B (en) |
ZA (1) | ZA711014B (en) |
-
1970
- 1970-02-18 GB GB789270A patent/GB1355791A/en not_active Expired
-
1971
- 1971-02-17 BE BE763104A patent/BE763104A/en not_active IP Right Cessation
- 1971-02-17 HU HU71KO2699A patent/HU170715B/en unknown
- 1971-02-17 ZA ZA711014A patent/ZA711014B/en unknown
Also Published As
Publication number | Publication date |
---|---|
ZA711014B (en) | 1971-10-27 |
BE763104A (en) | 1971-08-17 |
HU170715B (en) | 1977-08-26 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
429A | Application made for amendment of specification (sect. 29/1949) | ||
429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
PS | Patent sealed | ||
PE20 | Patent expired after termination of 20 years |