GB1213571A – Derivatives of cephalosporanic acid
– Google Patents
GB1213571A – Derivatives of cephalosporanic acid
– Google Patents
Derivatives of cephalosporanic acid
Info
Publication number
GB1213571A
GB1213571A
GB871/68A
GB87168A
GB1213571A
GB 1213571 A
GB1213571 A
GB 1213571A
GB 871/68 A
GB871/68 A
GB 871/68A
GB 87168 A
GB87168 A
GB 87168A
GB 1213571 A
GB1213571 A
GB 1213571A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
compounds
pyridylthio
cephalosporanic acid
Prior art date
1967-01-05
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
GB871/68A
Inventor
Leonard Bruce Crast Jr
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.)
Bristol Myers Co
Original Assignee
Bristol Myers 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.)
1967-01-05
Filing date
1968-01-05
Publication date
1970-11-25
1968-01-05
Application filed by Bristol Myers Co
filed
Critical
Bristol Myers Co
1970-11-25
Publication of GB1213571A
publication
Critical
patent/GB1213571A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
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
C07D501/36—Methylene radicals, substituted by sulfur atoms
A—HUMAN NECESSITIES
A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
A61K31/00—Medicinal preparations containing organic active ingredients
A61K31/33—Heterocyclic compounds
A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
A61K31/545—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, cefaclor, or cephalexine
Abstract
1,213,571. Cephalosporins. BRISTOLMYERS CO. 5 Jan., 1968 [5 Jan., 1967], No. 871/68. Heading C2A. The invention comprises an α-pyridylthioacetamido cephalosporanic acid derivative of formula wherein A is H, OH, C 2-8 alkanoyloxy, benzyloxy, a quaternary ammonium radical especially pyridinium, quinolinium, picolinium or lutidinium, or, when taken together with M is a monovalent C-O bond; and M is H, a pharmaceutically acceptable non-toxic cation, an anionic charge when A is a quaternery NH 4 radical or, when taken together with A, is a monovalent C-O bond; and Z is 2,- 3,- or 4- pyridyl. The compounds are prepared by (a) reacting a compound of formula: wherein A and M have the above meaning, with an α-haloacetyl halide of formula in which Hal is chloro, bromo or iodo, or its functional equivalent as an acylating agent, in the presence of a base, to produce an α- haloacetamido compound of formula wherein A and M are as defined above, and (b) reacting the thus-prepared α-haloacetamido compound in the presence of a base with a mercaptan of formula Z-SH wherein Z has the above meaning. Salts are formed with inorganic cations e.g. sodium and potassium, organic amine cations e.g. triethylamine, procaine and N-ethylpiperidine and with inorganic acids e.g. hydrochloric and organic acids e.g. acetic and ascorbic. Typical compounds are 7-[a-(4-pyridylthio)-acetamido]cephalosporanic acid and 3-methyl-7-[α-(4-pyridylthio) acetamido-]-3-cephem-4-carboxylic acid monophosphate. The 3- and 4-pyridyl compounds are more active against gram-negative bacteria than the 2-pyridyl compound. A pharmaceutical composition for parenteral or oral administration to man and animals comprises an α-pyridylthio acetamido cephalosporanic acid of Formula I and a carrier. The compositions may be used for treating mastitis in cattle. The compounds may be used as nutritional supplements in animal feeds.
GB871/68A
1967-01-05
1968-01-05
Derivatives of cephalosporanic acid
Expired
GB1213571A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
US60737867A
1967-01-05
1967-01-05
Publications (1)
Publication Number
Publication Date
GB1213571A
true
GB1213571A
(en)
1970-11-25
Family
ID=24432009
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB871/68A
Expired
GB1213571A
(en)
1967-01-05
1968-01-05
Derivatives of cephalosporanic acid
Country Status (11)
Country
Link
AT
(1)
AT276626B
(en)
BE
(1)
BE709019A
(en)
CH
(1)
CH487181A
(en)
DE
(1)
DE1670301C3
(en)
DK
(1)
DK126595B
(en)
FR
(2)
FR1580837A
(en)
GB
(1)
GB1213571A
(en)
IL
(1)
IL29235A
(en)
NL
(1)
NL6800176A
(en)
NO
(1)
NO140269C
(en)
SE
(1)
SE349564B
(en)
Cited By (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
GB2122603A
(en)
*
1982-06-25
1984-01-18
Lark Spa
7-Ä???-(substituted-thio)-acylamidoÜ-cephalosporanic acids
EP0953570A1
(en)
*
1998-04-30
1999-11-03
Eli Lilly And Company
Fluorinated cephalosporin antibiotics and their use for the treatment of mastitis
Families Citing this family (5)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
BE758764A
(en)
*
1969-11-13
1971-05-10
Bristol Myers Co
PROCESS FOR PREPARING ANTIBACTERIAL AGENTS
US3631027A
(en)
*
1970-03-27
1971-12-28
Bristol Myers Co
Cephalosporanic acids
JPS5854157B2
(en)
*
1977-06-10
1983-12-02
山之内製薬株式会社
New derivatives of cephalosporin compounds and their production method
DE2824559C2
(en)
1977-06-10
1985-01-10
Yamanouchi Pharmaceutical Co., Ltd., Tokio / Tokyo
7α-methoxy-7β- (4-substituted-methylen-1,3-dithietan-2-yl) -carboxamido-3-Δ 3 -cephem-4-carboxylic acids, processes for their preparation and their use
IT1141406B
(en)
*
1980-04-01
1986-10-01
Dob Far Spa
SALTS OF CEPHAPIRINE WITH AMINO ACIDS
1967
1967-12-28
IL
IL2923567A
patent/IL29235A/en
unknown
1968
1968-01-03
DE
DE19681670301
patent/DE1670301C3/en
not_active
Expired
1968-01-03
DK
DK1368A
patent/DK126595B/en
not_active
IP Right Cessation
1968-01-04
NO
NO3568A
patent/NO140269C/en
unknown
1968-01-05
GB
GB871/68A
patent/GB1213571A/en
not_active
Expired
1968-01-05
CH
CH15068A
patent/CH487181A/en
not_active
IP Right Cessation
1968-01-05
SE
SE14068A
patent/SE349564B/xx
unknown
1968-01-05
AT
AT13268A
patent/AT276626B/en
active
1968-01-05
FR
FR1580837D
patent/FR1580837A/fr
not_active
Expired
1968-01-05
BE
BE709019D
patent/BE709019A/xx
not_active
IP Right Cessation
1968-01-05
NL
NL6800176A
patent/NL6800176A/xx
unknown
1968-02-02
FR
FR138533A
patent/FR8381M/fr
not_active
Expired
Cited By (3)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
GB2122603A
(en)
*
1982-06-25
1984-01-18
Lark Spa
7-Ä???-(substituted-thio)-acylamidoÜ-cephalosporanic acids
EP0953570A1
(en)
*
1998-04-30
1999-11-03
Eli Lilly And Company
Fluorinated cephalosporin antibiotics and their use for the treatment of mastitis
US6369049B1
(en)
1998-04-30
2002-04-09
Eli Lilly And Company
Treatment of mastitis
Also Published As
Publication number
Publication date
NO140269C
(en)
1979-08-01
SE349564B
(en)
1972-10-02
NO140269B
(en)
1979-04-23
DK126595B
(en)
1973-07-30
AT276626B
(en)
1969-11-25
BE709019A
(en)
1968-07-05
CH487181A
(en)
1970-03-15
DE1670301A1
(en)
1972-02-24
DE1670301B2
(en)
1975-05-07
DE1670301C3
(en)
1975-12-18
IL29235A
(en)
1971-10-20
FR1580837A
(en)
1969-09-12
FR8381M
(en)
1971-03-01
NL6800176A
(en)
1968-07-08
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Legal Events
Date
Code
Title
Description
1971-05-19
PS
Patent sealed
1988-02-10
PE20
Patent expired after termination of 20 years
