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

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Publication number
CS219291B2
CS219291B2 CS807098A CS709880A CS219291B2 CS 219291 B2 CS219291 B2 CS 219291B2 CS 807098 A CS807098 A CS 807098A CS 709880 A CS709880 A CS 709880A CS 219291 B2 CS219291 B2 CS 219291B2
Authority
CS
Czechoslovakia
Prior art keywords
benzyl
acid
added
ethyl acetate
mixture
Prior art date
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.)
Filing date
Publication date
Application filed by Pfizer filed Critical Pfizer
Priority to CS814222A priority Critical patent/CS219292B2/cs
Publication of CS219291B2 publication Critical patent/CS219291B2/cs

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    • 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

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  • 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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (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 (ko)
JP (2) JPS5665892A (ko)
KR (1) KR840000797B1 (ko)
AR (1) AR227164A1 (ko)
AT (2) AT369372B (ko)
AU (1) AU519578B2 (ko)
BE (1) BE885812A (ko)
BG (2) BG38639A3 (ko)
CA (2) CA1144159A (ko)
CH (2) CH646175A5 (ko)
CS (2) CS219291B2 (ko)
DD (1) DD154542A5 (ko)
DE (1) DE3039504C2 (ko)
DK (1) DK389480A (ko)
ES (1) ES8204437A1 (ko)
FI (1) FI71156C (ko)
FR (1) FR2467852A1 (ko)
GB (3) GB2061930B (ko)
GR (1) GR70714B (ko)
GT (1) GT198065892A (ko)
HU (1) HU183236B (ko)
IE (3) IE51028B1 (ko)
IL (1) IL61307A (ko)
IN (1) IN154918B (ko)
IT (1) IT1149259B (ko)
LU (1) LU82880A1 (ko)
MX (1) MX6094E (ko)
NL (1) NL183358C (ko)
NO (1) NO159019C (ko)
NZ (1) NZ195307A (ko)
PH (5) PH16219A (ko)
PL (2) PL129534B1 (ko)
PT (1) PT71946B (ko)
RO (2) RO86176B (ko)
SE (1) SE451455B (ko)
SU (2) SU1122227A3 (ko)
YU (2) YU41743B (ko)
ZA (1) ZA806452B (ko)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL59948A0 (en) * 1979-05-21 1980-06-30 Rech Applications Therap Penicillanic acid derivatives,their production and pharmaceutical compositions containing them
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
RO87705A (ro) * 1982-01-11 1985-10-31 Pfizer Inc,Us Procedeu pentru prepararea unor derivati ai acidului 6-aminoalchilpenicilanic 1,1-dioxid
US4452796A (en) * 1982-06-14 1984-06-05 Pfizer Inc. 6-Aminoalkylpenicillanic acid 1,1-dioxides as beta-lactamase inhibitors
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
SU1395144A3 (ru) * 1984-01-30 1988-05-07 Пфайзер Инк. (Фирма) Способ получени 6-замещенных метиленпенициллановых кислот,или их сложных эфиров,или их солей с щелочными металлами
US5015473A (en) * 1984-01-30 1991-05-14 Pfizer Inc. 6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof
DE3584015D1 (de) * 1984-01-30 1991-10-17 Pfizer 6-(substituierte) methylen-penicillansaeure und 6-(substituierte) hydroxymethyl-penicillansaeure und deren derivate.
US4826833A (en) * 1984-01-30 1989-05-02 Pfizer Inc. 6-(Substituted)methylene-penicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof
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
MY102312A (en) * 1987-01-27 1992-05-28 Pfizer 6-beta (substituted)-c-hydroxymethyl-penicillanic 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
WO2004108733A1 (en) * 2003-06-05 2004-12-16 Pfizer Products Inc. Beta-lactamase inhibitor prodrug
WO2008111487A1 (ja) * 2007-03-09 2008-09-18 National University Corporation Okayama University ６－ヒドロキシエチルペナム化合物の製造方法
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 (ko) * 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

Also Published As

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

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