GB1536288A - Method of preparation of 3-methylene-cephams - Google Patents
Method of preparation of 3-methylene-cephamsInfo
- Publication number
- GB1536288A GB1536288A GB51980/75A GB5198075A GB1536288A GB 1536288 A GB1536288 A GB 1536288A GB 51980/75 A GB51980/75 A GB 51980/75A GB 5198075 A GB5198075 A GB 5198075A GB 1536288 A GB1536288 A GB 1536288A
- Authority
- GB
- United Kingdom
- Prior art keywords
- friedel
- bronsted
- compounds
- crafts catalyst
- acid type
- 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
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
3-Methylenecepham 1-sulphoxides of the formula <IMAGE> in which the substituents are defined in Claim 1 are prepared. These compounds are prepared by bringing about ring closure in a corresponding sulphinylazetidinone of the formula <IMAGE> in which X is chlorine or bromine, an alcohol or thioalcohol residue, an ester or a thioester residue, or an amino radical. If X is chlorine or bromine, the compound II is reacted with a Friedel-Crafts catalyst of the Lewis acid type, with a Friedel-Crafts catalyst of the Bronsted protonic acid type or with a metathetical cation former in a dry inert organic solvent, or is dissolved in an organic Bronsted acid. If X in compounds II is an alcohol, thioalcohol, ester or thioester residue or an amino radical, reaction is carried out with a Friedel-Crafts catalyst of the Bronsted protonic acid type in a dry inert organic solvent, or the compound is dissolved in an organic Bronsted acid. The resulting compounds can be used for the preparation of cephem antibiotics.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US53628074A | 1974-12-24 | 1974-12-24 | |
US63273375A | 1975-11-19 | 1975-11-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1536288A true GB1536288A (en) | 1978-12-20 |
Family
ID=27065082
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB51980/75A Expired GB1536288A (en) | 1974-12-24 | 1975-12-18 | Method of preparation of 3-methylene-cephams |
Country Status (25)
Country | Link |
---|---|
JP (1) | JPS606960B2 (en) |
AR (1) | AR220505A1 (en) |
AT (1) | AT341672B (en) |
AU (1) | AU503202B2 (en) |
BE (1) | BE837041A (en) |
BG (2) | BG31072A4 (en) |
CA (1) | CA1056372A (en) |
CH (3) | CH625528A5 (en) |
CS (1) | CS191291B2 (en) |
DD (2) | DD124985A5 (en) |
DE (1) | DE2556045A1 (en) |
DK (1) | DK157137C (en) |
ES (2) | ES443829A1 (en) |
FR (2) | FR2333804A1 (en) |
GB (1) | GB1536288A (en) |
GR (1) | GR59922B (en) |
HU (2) | HU177431B (en) |
IE (1) | IE42190B1 (en) |
IL (1) | IL48565A (en) |
NL (1) | NL182880C (en) |
PL (2) | PL114521B1 (en) |
RO (2) | RO74273A (en) |
SE (2) | SE431547B (en) |
SU (1) | SU799667A3 (en) |
YU (2) | YU324875A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0109816A1 (en) * | 1982-11-16 | 1984-05-30 | Eli Lilly And Company | N-substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamido)-4-oxo-azetidines and process |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4289695A (en) * | 1978-11-13 | 1981-09-15 | Eli Lilly And Company | Process for preparing 2-chlorosulfinylazetidinones |
US4190724A (en) * | 1978-11-13 | 1980-02-26 | Eli Lilly And Company | Process for 3-exomethylenecepham sulfoxides |
GB2099817B (en) * | 1981-04-10 | 1985-05-15 | Otsuka Kagaku Yakuhin | Azetidinone derivatives and process for the preparation of the same |
DE4230053A1 (en) * | 1992-09-08 | 1994-03-10 | Pliva Handels Gmbh | 4-oxo-azetidine-2-sulfonic acid amides and their salts, process for their preparation and their use |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3843682A (en) * | 1972-05-15 | 1974-10-22 | Lilly Co Eli | 2-chlorosulfinyl-3-imido-azetedin-4-ones |
-
1975
- 1975-11-27 CA CA240,644A patent/CA1056372A/en not_active Expired
- 1975-11-27 GR GR49473A patent/GR59922B/en unknown
- 1975-11-28 IL IL48565A patent/IL48565A/en unknown
- 1975-11-28 IE IE2596/75A patent/IE42190B1/en unknown
- 1975-11-28 AU AU87084/75A patent/AU503202B2/en not_active Expired
- 1975-12-12 DE DE19752556045 patent/DE2556045A1/en active Granted
- 1975-12-16 CH CH1630475A patent/CH625528A5/en not_active IP Right Cessation
- 1975-12-17 DD DD190224A patent/DD124985A5/xx unknown
- 1975-12-17 DD DD7500198426A patent/DD130933A5/en unknown
- 1975-12-18 GB GB51980/75A patent/GB1536288A/en not_active Expired
- 1975-12-19 YU YU03248/75A patent/YU324875A/en unknown
- 1975-12-22 JP JP50153926A patent/JPS606960B2/en not_active Expired
- 1975-12-22 SE SE7514550A patent/SE431547B/en not_active IP Right Cessation
- 1975-12-22 DK DK585875A patent/DK157137C/en not_active IP Right Cessation
- 1975-12-23 AT AT980475A patent/AT341672B/en not_active IP Right Cessation
- 1975-12-23 SU SU752301511A patent/SU799667A3/en active
- 1975-12-23 HU HU75EI662A patent/HU177431B/en unknown
- 1975-12-23 PL PL1975185927A patent/PL114521B1/en unknown
- 1975-12-23 HU HU75EI686A patent/HU175226B/en unknown
- 1975-12-23 ES ES443829A patent/ES443829A1/en not_active Expired
- 1975-12-23 AR AR261750A patent/AR220505A1/en active
- 1975-12-23 CS CS758835A patent/CS191291B2/en unknown
- 1975-12-23 BE BE1007103A patent/BE837041A/en not_active IP Right Cessation
- 1975-12-23 PL PL1975212224A patent/PL113883B1/en unknown
- 1975-12-24 BG BG7536782A patent/BG31072A4/en unknown
- 1975-12-24 RO RO7594622A patent/RO74273A/en unknown
- 1975-12-24 RO RO7584303A patent/RO68478A/en unknown
- 1975-12-24 FR FR7539714A patent/FR2333804A1/en active Granted
- 1975-12-24 BG BG7531908A patent/BG27236A3/en unknown
- 1975-12-24 NL NLAANVRAGE7515069,A patent/NL182880C/en not_active IP Right Cessation
-
1976
- 1976-05-04 FR FR7613230A patent/FR2300080A1/en active Granted
-
1977
- 1977-04-15 ES ES457884A patent/ES457884A1/en not_active Expired
-
1979
- 1979-08-17 SE SE7906899A patent/SE444810B/en not_active IP Right Cessation
-
1980
- 1980-11-21 CH CH862880A patent/CH626604A5/en not_active IP Right Cessation
-
1981
- 1981-04-24 CH CH271381A patent/CH628620A5/en not_active IP Right Cessation
- 1981-08-26 YU YU02064/81A patent/YU206481A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0109816A1 (en) * | 1982-11-16 | 1984-05-30 | Eli Lilly And Company | N-substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamido)-4-oxo-azetidines and process |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19951217 |