CS219291B2 - Method of making the new derivatives of the 6 beta-hydroxyalcylpeniciline acid - Google Patents

Method of making the new derivatives of the 6 beta-hydroxyalcylpeniciline acid Download PDF

Info

Publication number: CS219291B2
Authority: CS; Czechoslovakia
Prior art keywords: benzyl; acid; added; ethyl acetate; mixture
Prior art date: 1979-10-22

Application number

CS807098A

Other languages

Czech (cs)

English (en)

Inventor

Michal S Kellog

Original Assignee

Pfizer

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.)

1979-10-22

Filing date

1980-10-20

Publication date

1983-03-25

1980-10-20 Application filed by Pfizer filed Critical Pfizer

1981-06-05 Priority to CS814222A priority Critical patent/CS219292B2/cs

1983-03-25 Publication of CS219291B2 publication Critical patent/CS219291B2/cs

Links

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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- C07D499/08—Modification of a carboxyl radical directly attached in position 2, e.g. esterification
- 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/74—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with carbocyclic rings directly attached to the carboxamido radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Catalysts (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CS807098A 1979-10-22 1980-10-20 Method of making the new derivatives of the 6 beta-hydroxyalcylpeniciline acid CS219291B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS814222A CS219292B2 (en)	1979-10-22	1981-06-05	Method of making the ester of the 6 beta-hydroxymethylpeniciline acid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/086,864 US4287181A (en)	1979-10-22	1979-10-22	Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors

Publications (1)

Publication Number	Publication Date
CS219291B2 true CS219291B2 (en)	1983-03-25

Family

ID=22201393

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CS807098A CS219291B2 (en)	1979-10-22	1980-10-20	Method of making the new derivatives of the 6 beta-hydroxyalcylpeniciline acid
CS814222A CS219292B2 (en)	1979-10-22	1981-06-05	Method of making the ester of the 6 beta-hydroxymethylpeniciline acid

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CS814222A CS219292B2 (en)	1979-10-22	1981-06-05	Method of making the ester of the 6 beta-hydroxymethylpeniciline acid

Country Status (38)

Country	Link
US (1)	US4287181A (no)
JP (2)	JPS5665892A (no)
KR (1)	KR840000797B1 (no)
AR (1)	AR227164A1 (no)
AT (2)	AT369372B (no)
AU (1)	AU519578B2 (no)
BE (1)	BE885812A (no)
BG (2)	BG38639A3 (no)
CA (2)	CA1144159A (no)
CH (2)	CH646175A5 (no)
CS (2)	CS219291B2 (no)
DD (1)	DD154542A5 (no)
DE (1)	DE3039504C2 (no)
DK (1)	DK389480A (no)
ES (1)	ES8204437A1 (no)
FI (1)	FI71156C (no)
FR (1)	FR2467852A1 (no)
GB (3)	GB2061930B (no)
GR (1)	GR70714B (no)
GT (1)	GT198065892A (no)
HU (1)	HU183236B (no)
IE (3)	IE51026B1 (no)
IL (1)	IL61307A (no)
IN (1)	IN154918B (no)
IT (1)	IT1149259B (no)
LU (1)	LU82880A1 (no)
MX (1)	MX6094E (no)
NL (1)	NL183358C (no)
NO (1)	NO159019C (no)
NZ (1)	NZ195307A (no)
PH (5)	PH16219A (no)
PL (2)	PL129534B1 (no)
PT (1)	PT71946B (no)
RO (2)	RO81225B (no)
SE (1)	SE451455B (no)
SU (2)	SU1122227A3 (no)
YU (2)	YU41743B (no)
ZA (1)	ZA806452B (no)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE49768B1 (en) *	1979-05-21	1985-12-11	Leo Pharm Prod Ltd	6beta-halopenicillanic acid derivatives
GB2076812A (en) *	1980-05-22	1981-12-09	Ciba Geigy Ag	Penam-dioxide compounds, processes for their manufacture, and their use
US4444687A (en) *	1981-06-08	1984-04-24	Bristol-Myers Company	2β-Chloromethyl-2α-methylpenam-3α-carboxylic acid sulfone methylene diol mixed esters
ZA826687B (en) *	1981-09-14	1983-07-27	Pfizer	Beta-lactamase inhibiting 2-beta-substituted-2-alpha-methyl 5(r)penam-3-alpha-carboxylic acid 1,1-dioxides and intermediates therefor
US4351840A (en)	1981-09-18	1982-09-28	Pfizer Inc.	Antibacterial esters of resorcinol with ampicillin and penicillanic acid 1,1-dioxide derivatives
JPS58109490A (ja) *	1981-12-21	1983-06-29	Sankyo Co Ltd	ペニシリン誘導体
US4452796A (en) *	1982-06-14	1984-06-05	Pfizer Inc.	6-Aminoalkylpenicillanic acid 1,1-dioxides as beta-lactamase inhibitors
RO87705A (ro) *	1982-01-11	1985-10-31	Pfizer Inc,Us	Procedeu pentru prepararea unor derivati ai acidului 6-aminoalchilpenicilanic 1,1-dioxid
US4377590A (en) *	1982-05-10	1983-03-22	Pfizer Inc.	Derivatives of ampicillin and amoxicillin with beta-lactamase inhibitors
US4502990A (en) *	1983-06-06	1985-03-05	Pfizer Inc.	Process for 6-(aminomethyl)penicillanic acid 1,1-dioxide and derivatives thereof
US4536393A (en) *	1983-06-06	1985-08-20	Pfizer Inc.	6-(Aminomethyl)penicillanic acid 1,1-dioxide esters and intermediates therefor
US4499017A (en) *	1983-06-06	1985-02-12	Pfizer Inc.	Beta-lactamase inhibiting 6-(alkoxyamino-methyl) penicillanic acid 1,1-dioxide and derivatives
US4588527A (en) *	1983-06-06	1986-05-13	Pfizer Inc.	Process for preparing penicillanic acid 1,1-dioxide derivatives
US4502988A (en) *	1983-08-08	1985-03-05	Eli Lilly And Company	Oxidation process
EP0150984B1 (en) *	1984-01-30	1991-09-11	Pfizer Inc.	6-(substituted) methylenepenicillanic and 6-(substituted) hydroxymethylpenicillanic acids and derivatives thereof
US4826833A (en) *	1984-01-30	1989-05-02	Pfizer Inc.	6-(Substituted)methylene-penicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof
US5015473A (en) *	1984-01-30	1991-05-14	Pfizer Inc.	6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof
DD234015A5 (de) *	1984-01-30	1986-03-19	Pfizer	Verfahren zur herstellung von 6-(subst.)-methylen-penicillan-und 6-(subst.)-hydroxymethyl-penicillansaeure und deren derivaten
US4503040A (en) *	1984-02-27	1985-03-05	Pfizer Inc.	6-(Aminoacyloxymethyl)penicillanic acid 1,1-dioxides as beta-lactamase inhibitors
US4847247A (en) *	1984-07-30	1989-07-11	Merck & Co., Inc.	Penicillin derivatives as anti-inflammatory and antidegenerative agents
US4590073A (en) *	1984-10-22	1986-05-20	Pfizer Inc.	6-substituted penicillanic acid 1,1-dioxide compounds
US4591459A (en) *	1984-12-03	1986-05-27	Pfizer Inc.	Intermediates for 6-(aminoacyloxymethyl) penicillanic acid 1,1-dioxides
US4762921A (en) *	1985-04-18	1988-08-09	Pfizer Inc.	6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives
US4675186A (en) *	1985-04-18	1987-06-23	Pfizer Inc.	6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives
US4613462A (en) *	1985-07-02	1986-09-23	Pfizer, Inc.	6-substituted penicillanic acid 1,1-dioxide compounds
US4782050A (en) *	1987-01-27	1988-11-01	Pfizer Inc.	6-beta(substituted)-(S)-hydroxymethylpenicillanic acids and derivatives thereof
EP0276942B1 (en) *	1987-01-27	1992-04-01	Pfizer Inc.	6-beta(substituted)-(s)-hydroxymethylpenicillanic acids and derivatives thereof
US6395726B1 (en)	1999-01-26	2002-05-28	American Cyanamid Company	3,6-disubstituted penam sulfone derivatives
PA8579701A1 (es) *	2002-08-23	2005-05-24	Pfizer Prod Inc	Profarmaco inhibidor de beta-lactamasa
EP1636240A1 (en) *	2003-06-05	2006-03-22	Pfizer Products Inc.	Beta-lactamase inhibitor prodrug
CN101646680B (zh) *	2007-03-09	2013-02-20	大塚化学株式会社	制备6-羟乙基青霉烷化合物的方法
CN109422765B (zh) *	2017-09-05	2020-08-28	香港理工大学深圳研究院	C类β-内酰胺酶抑制剂及其制备方法和应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5749555B2 (no) *	1973-04-04	1982-10-22
US4207323A (en) *	1975-11-21	1980-06-10	Merck & Co., Inc.	6-Substituted methyl penicillins, derivatives and analogues thereof
US4053468A (en) *	1976-02-25	1977-10-11	Smithkline Corporation	Process for preparing 7-oxo cephalosporins and 6-oxo penicillins
US4093625A (en) *	1976-08-09	1978-06-06	Massachusetts Institute Of Technology	6-Sulfur analogs of penicillins and cephalosporins
US4123539A (en) *	1977-12-29	1978-10-31	Merck & Co., Inc.	6-Ethylpenicillanic acid
US4272439A (en) *	1978-06-02	1981-06-09	Schering Corporation	6-(Substituted-hydroxymethylene penams)
JPS5598186A (en) *	1979-01-10	1980-07-25	Beecham Group Ltd	Manufacture of penicillin derivative
GB2076812A (en) *	1980-05-22	1981-12-09	Ciba Geigy Ag	Penam-dioxide compounds, processes for their manufacture, and their use

1979
- 1979-10-22 US US06/086,864 patent/US4287181A/en not_active Expired - Lifetime
1980
- 1980-09-12 DK DK389480A patent/DK389480A/da not_active Application Discontinuation
- 1980-10-08 IN IN736/DEL/80A patent/IN154918B/en unknown
- 1980-10-11 GR GR63135A patent/GR70714B/el unknown
- 1980-10-16 GB GB33342A patent/GB2061930B/en not_active Expired
- 1980-10-17 GT GT198065892A patent/GT198065892A/es unknown
- 1980-10-20 AT AT0518580A patent/AT369372B/de not_active IP Right Cessation
- 1980-10-20 AR AR282932A patent/AR227164A1/es active
- 1980-10-20 SE SE8007354A patent/SE451455B/sv not_active IP Right Cessation
- 1980-10-20 JP JP14677480A patent/JPS5665892A/ja active Granted
- 1980-10-20 CA CA000362762A patent/CA1144159A/en not_active Expired
- 1980-10-20 YU YU2676/80A patent/YU41743B/xx unknown
- 1980-10-20 IL IL61307A patent/IL61307A/xx unknown
- 1980-10-20 PH PH24748A patent/PH16219A/en unknown
- 1980-10-20 NZ NZ195307A patent/NZ195307A/en unknown
- 1980-10-20 CS CS807098A patent/CS219291B2/cs unknown
- 1980-10-20 DE DE3039504A patent/DE3039504C2/de not_active Expired
- 1980-10-21 SU SU802999190A patent/SU1122227A3/ru active
- 1980-10-21 FR FR8022477A patent/FR2467852A1/fr active Granted
- 1980-10-21 PL PL1980227420A patent/PL129534B1/pl unknown
- 1980-10-21 IE IE2174/80A patent/IE51026B1/en unknown
- 1980-10-21 IE IE293/85A patent/IE51027B1/en unknown
- 1980-10-21 AU AU63548/80A patent/AU519578B2/en not_active Ceased
- 1980-10-21 BE BE0/202544A patent/BE885812A/fr not_active IP Right Cessation
- 1980-10-21 PL PL1980235907A patent/PL129638B1/pl unknown
- 1980-10-21 BG BG8361372A patent/BG38639A3/xx unknown
- 1980-10-21 PT PT71946A patent/PT71946B/pt unknown
- 1980-10-21 FI FI803311A patent/FI71156C/fi not_active IP Right Cessation
- 1980-10-21 KR KR1019800004041A patent/KR840000797B1/ko active
- 1980-10-21 IT IT25488/80A patent/IT1149259B/it active
- 1980-10-21 MX MX809112U patent/MX6094E/es unknown
- 1980-10-21 NO NO803136A patent/NO159019C/no unknown
- 1980-10-21 IE IE2229/85A patent/IE51028B1/en unknown
- 1980-10-21 ZA ZA00806452A patent/ZA806452B/xx unknown
- 1980-10-21 BG BG8049416A patent/BG35189A3/xx unknown
- 1980-10-21 HU HU802552A patent/HU183236B/hu not_active IP Right Cessation
- 1980-10-22 ES ES496166A patent/ES8204437A1/es not_active Expired
- 1980-10-22 NL NLAANVRAGE8005810,A patent/NL183358C/xx not_active IP Right Cessation
- 1980-10-22 RO RO102404A patent/RO81225B/ro unknown
- 1980-10-22 LU LU82880A patent/LU82880A1/fr unknown
- 1980-10-22 RO RO108549A patent/RO86176B/ro unknown
- 1980-10-22 CH CH788180A patent/CH646175A5/fr not_active IP Right Cessation
- 1980-10-22 DD DD80224691A patent/DD154542A5/de unknown
1981
- 1981-06-05 CS CS814222A patent/CS219292B2/cs unknown
- 1981-08-26 SU SU813325756A patent/SU1026654A3/ru active
- 1981-11-06 PH PH26450A patent/PH17458A/en unknown
- 1981-11-06 PH PH26449A patent/PH17317A/en unknown
- 1981-11-06 PH PH26451A patent/PH18316A/en unknown
- 1981-11-06 PH PH26448A patent/PH17315A/en unknown
1982
- 1982-01-13 AT AT0010882A patent/AT374479B/de not_active IP Right Cessation
- 1982-12-17 CA CA000418062A patent/CA1163924A/en not_active Expired
1983
- 1983-03-21 YU YU671/83A patent/YU42075B/xx unknown
- 1983-06-21 GB GB08316830A patent/GB2129421B/en not_active Expired
- 1983-06-21 GB GB08316829A patent/GB2128986B/en not_active Expired
1984
- 1984-03-06 CH CH1089/84A patent/CH647242A5/fr not_active IP Right Cessation
1986
- 1986-02-06 JP JP61024914A patent/JPS61178988A/ja active Pending

Also Published As

Publication number	Publication date
IT8025488A0 (it)	1980-10-21
FI71156C (fi)	1986-11-24
GB2129421B (en)	1984-11-14
KR840000797B1 (ko)	1984-06-12
NO803136L (no)	1981-04-23
CH647242A5 (fr)	1985-01-15
MX6094E (es)	1984-11-12
IE850293L (en)	1981-04-22
GB2128986A (en)	1984-05-10
JPS6135197B2 (no)	1986-08-12
AU6354880A (en)	1981-04-30
RO86176B (ro)	1985-03-31
AT374479B (de)	1984-04-25
CA1163924A (en)	1984-03-20
PL235907A1 (no)	1982-09-13
PH17317A (en)	1984-07-20
PL227420A1 (no)	1982-08-30
AU519578B2 (en)	1981-12-10
IE852229L (en)	1981-04-22
GB2061930B (en)	1984-06-13
IE802174L (en)	1981-04-22
PL129638B1 (en)	1984-05-31
CH646175A5 (fr)	1984-11-15
BE885812A (fr)	1981-04-21
YU42075B (en)	1988-04-30
DE3039504C2 (de)	1984-10-11
RO86176A (ro)	1985-03-15
BG38639A3 (en)	1986-01-15
YU267680A (en)	1983-09-30
HU183236B (en)	1984-04-28
CA1144159A (en)	1983-04-05
DE3039504A1 (de)	1981-04-30
IE51027B1 (en)	1986-09-17
NL183358C (nl)	1988-10-03
ES496166A0 (es)	1982-05-01
GB8316830D0 (en)	1983-07-27
US4287181A (en)	1981-09-01
FR2467852B1 (no)	1983-10-07
FI71156B (fi)	1986-08-14
NO159019C (no)	1988-11-23
GB2061930A (en)	1981-05-20
PH16219A (en)	1983-08-09
NO159019B (no)	1988-08-15
GB8316829D0 (en)	1983-07-27
NL8005810A (nl)	1981-04-24
GB2129421A (en)	1984-05-16
GT198065892A (es)	1982-04-10
CS219292B2 (en)	1983-03-25
FR2467852A1 (fr)	1981-04-30
SE451455B (sv)	1987-10-12
SE8007354L (sv)	1981-04-23
IL61307A (en)	1984-03-30
RO81225A (ro)	1983-02-15
PH18316A (en)	1985-05-29
YU67183A (en)	1984-02-29
ZA806452B (en)	1981-10-28
BG35189A3 (en)	1984-02-15
ES8204437A1 (es)	1982-05-01
ATA518580A (de)	1982-05-15
GR70714B (no)	1983-01-18
LU82880A1 (fr)	1981-06-04
SU1122227A3 (ru)	1984-10-30
SU1026654A3 (ru)	1983-06-30
PH17315A (en)	1984-07-20
NL183358B (nl)	1988-05-02
PT71946A (en)	1980-11-01
KR830004309A (ko)	1983-07-09
IE51026B1 (en)	1986-09-17
AR227164A1 (es)	1982-09-30
GB2128986B (en)	1985-06-19
IT1149259B (it)	1986-12-03
IL61307A0 (en)	1980-12-31
JPS61178988A (ja)	1986-08-11
RO81225B (ro)	1983-02-28
PH17458A (en)	1984-08-29
PL129534B1 (en)	1984-05-31
IE51028B1 (en)	1986-09-17
JPS5665892A (en)	1981-06-03
NZ195307A (en)	1984-08-24
AT369372B (de)	1982-12-27
DK389480A (da)	1981-04-23
IN154918B (no)	1984-12-22
ATA10882A (de)	1983-09-15
YU41743B (en)	1987-12-31
PT71946B (en)	1981-08-31
FI803311L (fi)	1981-04-23
DD154542A5 (de)	1982-03-31

Publication	Publication Date	Title
CS219291B2 (en)	1983-03-25	Method of making the new derivatives of the 6 beta-hydroxyalcylpeniciline acid
US4234579A (en)	1980-11-18	Penicillanic acid 1,1-dioxides as β-lactamase inhibitors
HU180042B (en)	1983-01-28	Process for producing 2,2-dimethyl-pename-3-carboxylic acid-1,1-dioxide derivatives
JP2642314B2 (ja)	1997-08-20	β−ラクタマーゼ阻害剤としての２−β−アルケニルペナムスルホン
US4276285A (en)	1981-06-30	Combinations of penicillanic acid 1,1-dioxide with 7-(D-2-[4-ethylpiperazin-2,3-dione-1-carboxamido]-2-[4-hydroxyphenyl]acetamido)-3-([1-methyl-5-tetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid
EP0013617A1 (en)	1980-07-23	Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds
US4256733A (en)	1981-03-17	Acetoxymethyl penam compounds as β-lactamase inhibitors
US4241050A (en)	1980-12-23	Penam 1,1-dioxides as beta-lactamase inhibitors
US4420426A (en)	1983-12-13	6-Alpha-halopenicillanic acid 1,1-dioxides
EP0074783B1 (en)	1985-07-31	Beta-lactamase inhibiting 2-beta-substituted-2-alpha-methyl-(5r) penam-3-alpha-carboxylic acid 1,1-dioxides and intermediates therefor
US4590073A (en)	1986-05-20	6-substituted penicillanic acid 1,1-dioxide compounds
US4260598A (en)	1981-04-07	Method for increasing antibacterial effectiveness of a β-lactam antibiotic
SU1192626A3 (ru)	1985-11-15	Способ получени 1,1-диоксида пенициллановой кислоты или ее эфира
EP0083977A1 (en)	1983-07-20	6-Alpha-hydroxymethylpenicillanic acid sulfone as a beta-lactamase inhibitor
EP0287734A1 (en)	1988-10-26	2-Beta-substituted methyl-penam derivatives
EP0002927B1 (en)	1981-02-25	Penicillanic acid derivatives, processes for their preparation and pharmaceutical compositions containing them
EP0114751B1 (en)	1987-12-09	Beta-lactam antibacterial agents
NZ199601A (en)	1984-07-06	Coadministration of a cephalosporin derivative and a penicillin