GB1388979A – Process for preparing penicillin sulphoxide
– Google Patents
GB1388979A – Process for preparing penicillin sulphoxide
– Google Patents
Process for preparing penicillin sulphoxide
Info
Publication number
GB1388979A
GB1388979A
GB3960373A
GB3960373A
GB1388979A
GB 1388979 A
GB1388979 A
GB 1388979A
GB 3960373 A
GB3960373 A
GB 3960373A
GB 3960373 A
GB3960373 A
GB 3960373A
GB 1388979 A
GB1388979 A
GB 1388979A
Authority
GB
United Kingdom
Prior art keywords
penicillin
per
sulphoxide
acid
organic liquid
Prior art date
1972-09-12
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
Application number
GB3960373A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date 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 date listed.)
1972-09-12
Filing date
1973-08-21
Publication date
1975-04-03
1973-08-21
Application filed by Eli Lilly and Co
filed
Critical
Eli Lilly and Co
1975-04-03
Publication of GB1388979A
publication
Critical
patent/GB1388979A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
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
C07D499/04—Preparation
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
Abstract
1388979 Preparing penicillin sulphoxides ELI LILLY & CO 21 Aug 1973 [12 Sept 1972] 39603/73 Heading C2C Penicillin sulphoxides are prepared from a penicillin-containing fermentation broth by filtering off the mycelium and adding a miscible organic liquid to the filtrate to precipitate non- penicillin impurities, oxidizing the penicillin in the solution with a per-acid oxidizing agent at -20 to 25 C., to produce the sulphoxide, lowering the pH of the resulting solution and adding water to induce crystallization of the sulphoxide, and separating the crystallized sulphoxide from the supernatant. The filtered broth containing the penicillin (e.g. phenoxymethyl- or benzyl-penicillin), is preferably concentrated to 200-400 mg. solid per ml. before adding the organic liquid, which is preferably acetone in ¢-3 volumes or may be methanol, ethanol, methyl ethyl ketone, acetonitrile, isopropanol, tert.-butanol or propionitrile. The precipitated impurities are usually filtered off, and if desired the organic liquid may then be removed. Oxidation is effected with an at least partially soluble oxidizing agent, in sufficient amount to convert all the penicillin content to the sulphoxide, e.g. 1-3 moles per mole of penicillin; the preferred agents are per-acetic acid, per-propionic acid, per-benzoic acid and per-succinic acid. The pH is then lowered to a crystallization point of the penicillin (i.e. about the iso-electric point), usually about pH 1À5-2À5, preferably with one of the following: methanesulphonic, p-toluenesulphonic, hydrochloric, sulphuric, o-phosphoric or nitric acid, and water is added to assist crystallization. The penicillin oxide crystallizes in pure form and is separated from the supernatant liquid.
GB3960373A
1972-09-12
1973-08-21
Process for preparing penicillin sulphoxide
Expired
GB1388979A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
US288459A
US3904605A
(en)
1972-09-12
1972-09-12
Penicillin oxidation process
Publications (1)
Publication Number
Publication Date
GB1388979A
true
GB1388979A
(en)
1975-04-03
Family
ID=23107189
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB3960373A
Expired
GB1388979A
(en)
1972-09-12
1973-08-21
Process for preparing penicillin sulphoxide
Country Status (24)
Country
Link
US
(1)
US3904605A
(en)
JP
(1)
JPS4962495A
(en)
KR
(1)
KR780000146B1
(en)
AR
(1)
AR201835A1
(en)
AT
(1)
AT330348B
(en)
AU
(1)
AU472678B2
(en)
BE
(1)
BE804710A
(en)
BG
(1)
BG21231A3
(en)
CA
(1)
CA1007635A
(en)
CH
(1)
CH583737A5
(en)
DD
(1)
DD107049A5
(en)
DE
(1)
DE2344812A1
(en)
ES
(1)
ES418639A1
(en)
FR
(1)
FR2198948B1
(en)
GB
(1)
GB1388979A
(en)
HU
(1)
HU166395B
(en)
IE
(1)
IE38106B1
(en)
IL
(1)
IL43065A
(en)
NL
(1)
NL7312145A
(en)
PH
(1)
PH9481A
(en)
PL
(1)
PL89405B1
(en)
RO
(1)
RO63002A
(en)
SU
(1)
SU495840A3
(en)
ZA
(1)
ZA735720B
(en)
Families Citing this family (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US4354971A
(en)
*
1981-06-22
1982-10-19
Eli Lilly And Company
Non-extractive penicillin V recovery process
US7028687B1
(en)
1999-08-26
2006-04-18
Precious Life, Llc
Escape hood
Family Cites Families (5)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3047467A
(en)
*
1957-08-02
1962-07-31
Beecham Res Lab
Process for the preparation of penicillins
US3025290A
(en)
*
1959-06-09
1962-03-13
Doyle Frank Peter
Synthetic penicillin and salts thereof
US3197466A
(en)
*
1961-10-30
1965-07-27
Smith Kline French Lab
Penicillin sulfoxides and process
US3586667A
(en)
*
1967-12-22
1971-06-22
Lilly Co Eli
Penicillin esterification process
US3647787A
(en)
*
1969-07-02
1972-03-07
Lilly Co Eli
Process improvement for converting penicillin sulfoxide esters to cephem compounds
1972
1972-09-12
US
US288459A
patent/US3904605A/en
not_active
Expired – Lifetime
1973
1973-08-20
IE
IE1445/73A
patent/IE38106B1/en
unknown
1973-08-21
GB
GB3960373A
patent/GB1388979A/en
not_active
Expired
1973-08-21
ZA
ZA00735720A
patent/ZA735720B/en
unknown
1973-08-23
CA
CA179,462A
patent/CA1007635A/en
not_active
Expired
1973-08-24
PH
PH14949*UA
patent/PH9481A/en
unknown
1973-08-24
IL
IL43065A
patent/IL43065A/en
unknown
1973-08-27
AU
AU59661/73A
patent/AU472678B2/en
not_active
Expired
1973-09-03
NL
NL7312145A
patent/NL7312145A/xx
not_active
Application Discontinuation
1973-09-05
DE
DE19732344812
patent/DE2344812A1/en
active
Pending
1973-09-07
AR
AR249970A
patent/AR201835A1/en
active
1973-09-10
ES
ES418639A
patent/ES418639A1/en
not_active
Expired
1973-09-11
BE
BE1005350A
patent/BE804710A/en
unknown
1973-09-11
HU
HUEI495A
patent/HU166395B/hu
unknown
1973-09-11
SU
SU1959496A
patent/SU495840A3/en
active
1973-09-11
AT
AT786773A
patent/AT330348B/en
not_active
IP Right Cessation
1973-09-11
JP
JP48102573A
patent/JPS4962495A/ja
active
Pending
1973-09-12
DD
DD173425A
patent/DD107049A5/xx
unknown
1973-09-12
FR
FR7332798A
patent/FR2198948B1/fr
not_active
Expired
1973-09-12
CH
CH1308673A
patent/CH583737A5/xx
not_active
IP Right Cessation
1973-09-12
RO
RO7300076059A
patent/RO63002A/en
unknown
1973-09-12
BG
BG24528A
patent/BG21231A3/xx
unknown
1973-09-12
KR
KR7301518A
patent/KR780000146B1/en
active
1973-09-12
PL
PL1973165173A
patent/PL89405B1/pl
unknown
Also Published As
Publication number
Publication date
DE2344812A1
(en)
1974-03-21
KR780000146B1
(en)
1978-05-02
RO63002A
(en)
1978-05-15
IL43065A0
(en)
1973-11-28
AT330348B
(en)
1976-06-25
JPS4962495A
(en)
1974-06-17
AU5966173A
(en)
1975-02-27
PL89405B1
(en)
1976-11-30
CH583737A5
(en)
1977-01-14
FR2198948B1
(en)
1977-08-05
IL43065A
(en)
1976-01-30
DD107049A5
(en)
1974-07-12
IE38106B1
(en)
1977-12-21
US3904605A
(en)
1975-09-09
AR201835A1
(en)
1975-04-24
CA1007635A
(en)
1977-03-29
FR2198948A1
(en)
1974-04-05
ZA735720B
(en)
1975-04-30
AU472678B2
(en)
1976-06-03
PH9481A
(en)
1976-01-08
SU495840A3
(en)
1975-12-15
ES418639A1
(en)
1976-02-16
HU166395B
(en)
1975-03-28
BE804710A
(en)
1974-03-11
NL7312145A
(en)
1974-03-14
BG21231A3
(en)
1976-03-20
IE38106L
(en)
1974-03-12
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Legal Events
Date
Code
Title
Description
1975-08-13
PS
Patent sealed [section 19, patents act 1949]
1979-03-21
PCNP
Patent ceased through non-payment of renewal fee
