IE34055B1 - 3-halomethyl-delta3-cephalosporin esters and sulfoxides thereof useful in the production of antibiotics,and process for preparing the intermediates and antibiotics - Google Patents
3-halomethyl-delta3-cephalosporin esters and sulfoxides thereof useful in the production of antibiotics,and process for preparing the intermediates and antibioticsInfo
- Publication number
- IE34055B1 IE34055B1 IE337/70A IE33770A IE34055B1 IE 34055 B1 IE34055 B1 IE 34055B1 IE 337/70 A IE337/70 A IE 337/70A IE 33770 A IE33770 A IE 33770A IE 34055 B1 IE34055 B1 IE 34055B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- cephalosporin
- esters
- antibiotics
- tribromide
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1295908 Cephalosporin esters and sulphoxides ELI LILLY & CO 26 March 1970 [28 March 1969 8 Dec 1969] 14835/70 Headings C2A and C2C Novel cephalosporin sulphoxide esters of Formula (I). and also cephalosporin esters of Formula (II) wherein X is Cl, Br or I, R has the formula in which m is 0-4, n is 1-4, Z is oxygen, sulphur or a chemical bond, R<SP>3</SP> and R<SP>4</SP> are each H or CH 3 , Y is H or a substituent on the phenyl ring and z is 1 or 2; and R<SP>1</SP> is 2,2,2-trichloroethyl, C 4 -C 6 tert-alkyl, C 5 -C 7 tent.alkenyl, C 5 -C 7 tert-alkynyl, benzyl, methoxybenzyl, nitrobenzyl, phenacyl, phthalimidomethyl or succinimidoniethyl, are prepared by reacting phosphorus trichloride, tribromide, pentachloride, pentabromide, oxychloride or oxybromide with a corresponding 3-hydroxymethyl #<SP>3</SP>-cephalosporin sulphoxide ester in the presence of a tertiary amine in an anhydrous aprotic organic liquid diluent at a temperature of -75 C. to 50 C. When temperatures above -25 C. are employed and the reactant is phosphorus trichloride or tribromide in excess of the theoretical equimolar amount, the product has the Formula (II) above. Use of (a) an equimolar amount of phosphorus trichloride or tribromide at below -25 C., and (b) phosphorus penta-bromide or -chloride or oxybromide or - chloride, results in a sulphoxide product of Formula (I). The resulting 3-chloro- or 3- bromomethyl compounds may be -converted to the 3-iodomethyl compound by treatment with alkali metal iodide.
[GB1295908A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81164069A | 1969-03-28 | 1969-03-28 | |
| US88323169A | 1969-12-08 | 1969-12-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34055L IE34055L (en) | 1970-09-28 |
| IE34055B1 true IE34055B1 (en) | 1975-01-22 |
Family
ID=27123508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE337/70A IE34055B1 (en) | 1969-03-28 | 1970-03-16 | 3-halomethyl-delta3-cephalosporin esters and sulfoxides thereof useful in the production of antibiotics,and process for preparing the intermediates and antibiotics |
Country Status (14)
| Country | Link |
|---|---|
| JP (2) | JPS5112635B1 (en) |
| BE (1) | BE748055A (en) |
| CA (1) | CA986094A (en) |
| CH (2) | CH562828A5 (en) |
| DE (1) | DE2065708C3 (en) |
| ES (1) | ES377938A1 (en) |
| FR (1) | FR2035977A1 (en) |
| GB (1) | GB1295908A (en) |
| IE (1) | IE34055B1 (en) |
| IL (1) | IL34093A (en) |
| NL (1) | NL7004479A (en) |
| PL (2) | PL83186B1 (en) |
| RO (1) | RO56339A (en) |
| SE (1) | SE412237B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE755256A (en) * | 1969-08-26 | 1971-02-25 | Glaxo Lab Ltd | |
| JPS5832884A (en) * | 1981-08-20 | 1983-02-25 | Otsuka Chem Co Ltd | Production of 3-exomethylenecepham derivative |
-
1970
- 1970-03-16 IE IE337/70A patent/IE34055B1/en unknown
- 1970-03-16 CA CA077,518A patent/CA986094A/en not_active Expired
- 1970-03-18 IL IL34093A patent/IL34093A/en unknown
- 1970-03-26 CH CH466570A patent/CH562828A5/xx not_active IP Right Cessation
- 1970-03-26 NL NL7004479A patent/NL7004479A/xx unknown
- 1970-03-26 SE SE7004235A patent/SE412237B/en unknown
- 1970-03-26 GB GB1295908D patent/GB1295908A/en not_active Expired
- 1970-03-27 PL PL1970139661A patent/PL83186B1/en unknown
- 1970-03-27 RO RO62914A patent/RO56339A/ro unknown
- 1970-03-27 FR FR7011274A patent/FR2035977A1/fr active Pending
- 1970-03-27 BE BE748055D patent/BE748055A/en not_active IP Right Cessation
- 1970-03-27 PL PL1970176080A patent/PL92638B1/en unknown
- 1970-03-28 JP JP45026434A patent/JPS5112635B1/ja active Pending
- 1970-03-31 DE DE2065708A patent/DE2065708C3/en not_active Expired
-
1971
- 1971-03-25 ES ES377938A patent/ES377938A1/en not_active Expired
-
1975
- 1975-01-20 CH CH466570D patent/CH564023A5/xx not_active IP Right Cessation
- 1975-08-27 JP JP50103874A patent/JPS5136277B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE412237B (en) | 1980-02-25 |
| DE2065708C3 (en) | 1978-06-08 |
| DE2065708B2 (en) | 1977-10-20 |
| GB1295908A (en) | 1972-11-08 |
| IL34093A (en) | 1975-10-15 |
| CA986094A (en) | 1976-03-23 |
| IL34093A0 (en) | 1970-05-21 |
| JPS5112635B1 (en) | 1976-04-21 |
| NL7004479A (en) | 1970-09-30 |
| RO56339A (en) | 1975-03-15 |
| IE34055L (en) | 1970-09-28 |
| DE2015317B2 (en) | 1975-08-28 |
| JPS5136277B1 (en) | 1976-10-07 |
| CH562828A5 (en) | 1975-06-13 |
| DE2015317A1 (en) | 1971-02-18 |
| DE2065708A1 (en) | 1975-04-10 |
| CH564023A5 (en) | 1975-07-15 |
| PL83186B1 (en) | 1975-12-31 |
| FR2035977A1 (en) | 1970-12-24 |
| ES377938A1 (en) | 1973-01-01 |
| BE748055A (en) | 1970-09-28 |
| PL92638B1 (en) | 1977-04-30 |
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