GB1315379A - 3-halomethyl-delta3-cephalosporin ester compounds - Google Patents
3-halomethyl-delta3-cephalosporin ester compoundsInfo
- Publication number
- GB1315379A GB1315379A GB4957870A GB4957870A GB1315379A GB 1315379 A GB1315379 A GB 1315379A GB 4957870 A GB4957870 A GB 4957870A GB 4957870 A GB4957870 A GB 4957870A GB 1315379 A GB1315379 A GB 1315379A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphorus
- halomethyl
- cephalosporin
- amino
- formula
- 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
- 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- 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
1315379 3-Halomethyl-cephalosporin esters ELI LILLY & CO 19 Oct 1970 [10 Aug 1970] 49578/70 Addition to 1295908 Headings C2A and C2C The invention comprises 3-halomethyl-#<SP>3</SP> cephalosporin esters of Formula II wherein R 1 is C 1 to C 6 alkanoyl, C 2 -C 6 chloroalkanoyl, or an acyl group of Formula III where Ar is 2-thienyl, wherein m is an integer of from 0 to 4, n is an integer of from 1 to 4, Z is oxygen or sulphur or a chemical bond, R<SP>3</SP> and R<SP>4</SP> are, separately, hydrogen or methyl, or when R<SP>3</SP> is hydrogen, R<SP>4</SP> can also be an N-protected amino group selected from N-tert-butoxycarbonylamino, N - (benzyloxycarbonyl) - amino, N - (allyloxycarbonyl) - amino, N - (cyclopentyloxycarbonylamino, and N - (2 - methoxycarbonyl-1-methylvinyl)-amino and n is 1; or when R<SP>4</SP> is N-protected amino as defined above, Ar can also be a group of Formula IV wherein Y is hydrogen or a substituent on the phenyl ring carbon atoms, such as fluorine, chlorine, bromine, iodine, C 1 -C 2 alkyl, C 1 -C 2 alkyloxy, N - protected - alpha - amino - C 1 - C 3 alkyl, butoxycarbonyl, nitro, cyano or trifluoromethyl, and w is an integer of from 1 to 2, X is chloro, bromo or iodo; and R<SP>1</SP> is 2,2,2-trichloroethyl, C 4 -C 6 tert-alkyl, C 5 -C 7 tertalkenyl, C 5 -C 7 -tert-alkynyl, benzyl, methoxybenzyl, nitrobenzyl, phenacyl, phthalimidomethyl or succinimidomethyl. A process for preparing compounds of Formula I or Formula II comprises reacting phosphorus trichloride, phosphorus tribromide, phosphorupentachloride, phosphorus oxychloride or phosphorus oxybromide with a 3-hydroxymethyls #<SP>3</SP>-cephalosporin sulphoxide ester in the presence of a tertiary amine in a substantially anhydrous liquid diluent at a temperature of from - 75‹ to 50‹ C. to form as product the following compounds: (1) 3-halomethyl-#<SP>3</SP>-cephalosporin ester from at least an equimolar amount of phosphorus trichloride or phosphorus tribromide when temperatures above - 25‹ C. are used, or (2) 3-halomethyl-#<SP>3</SP>-cephalosporin sulphoxide ester from an approximately equimolar amount of phosphorus tribromide or phosphorus trichloride when temperatures below -25‹ C. are used, or (3) 3-halomethyl-#<SP>3</SP>- cephalosporin sulphoxide ester from phosphorus pentachloride, phosphorus pentabromide, phosphorus oxychloride or phosphorus oxybromide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US062699A US3922268A (en) | 1969-12-08 | 1970-08-10 | 3-Halomethyl-{66 {hu 3-Cephalosporin esters |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1315379A true GB1315379A (en) | 1973-05-02 |
Family
ID=22044223
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4957870A Expired GB1315379A (en) | 1970-08-10 | 1970-10-19 | 3-halomethyl-delta3-cephalosporin ester compounds |
Country Status (5)
Country | Link |
---|---|
CH (2) | CH589659A5 (en) |
DE (2) | DE2065718A1 (en) |
GB (1) | GB1315379A (en) |
HK (1) | HK54876A (en) |
MY (1) | MY7600286A (en) |
-
1970
- 1970-10-19 GB GB4957870A patent/GB1315379A/en not_active Expired
- 1970-10-23 CH CH1573170A patent/CH589659A5/xx not_active IP Right Cessation
- 1970-10-26 DE DE19702065718 patent/DE2065718A1/en active Pending
- 1970-10-26 DE DE19702052531 patent/DE2052531A1/en active Pending
-
1976
- 1976-04-28 CH CH535876A patent/CH598264A5/xx not_active IP Right Cessation
- 1976-09-08 HK HK54876A patent/HK54876A/en unknown
- 1976-12-30 MY MY7600286A patent/MY7600286A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH589659A5 (en) | 1977-07-15 |
MY7600286A (en) | 1976-12-31 |
HK54876A (en) | 1976-09-17 |
DE2065718A1 (en) | 1975-07-17 |
CH598264A5 (en) | 1978-04-28 |
DE2052531A1 (en) | 1972-02-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed |