RO81225B - Procedeu pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpenicilanic - Google Patents

Procedeu pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpenicilanic

Info

Publication number
RO81225B
RO81225B RO102404A RO10240480A RO81225B RO 81225 B RO81225 B RO 81225B RO 102404 A RO102404 A RO 102404A RO 10240480 A RO10240480 A RO 10240480A RO 81225 B RO81225 B RO 81225B
Authority
RO
Romania
Prior art keywords
beta
general formula
substituted
benzyl
derivatives
Prior art date
Application number
RO102404A
Other languages
English (en)
Other versions
RO81225A (ro
Inventor
Michael Stephen Kellogg
Original Assignee
Pfizer Inc.
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 Inc. filed Critical Pfizer Inc.
Publication of RO81225A publication Critical patent/RO81225A/ro
Publication of RO81225B publication Critical patent/RO81225B/ro

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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Catalysts (AREA)

Abstract

Procedeul pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpencilanic cu formula generala I: (vezi formula) sau a unei sari acceptabile farmaceutic, în care Y reprezinta R sau R3, R reprezinta 1-hidroxi-3-fenil-propil, alchilsulfoniloxi cu 1...4 atomi de carbon în grupa alchil, fenilsulfoniloximetil sau fenilsulfoniloximetilsubstituit cu metil, metoxi, fluor, clor, brom sau trifluormetil, R2 reprezinta O - OR R4 - CH - în care R3 reprezinta sulf, hidrogen, alcoxicarbonil, cu 2...4 atomi de carbon, benzil, fenilsulfonil substituit cu un radical amino, fluormetil, iar n reprezinta 2, consta în îndepartarea grupei benzil din compusul cu formula generalp II: (vezi formula) în care Y si n au semnificatiile de mai sus, cu conditia ca atunci cînd Y reprezinta R1, n care valoarea zero, prin hidrogenare în prezenta unui catalizator de paladiu în mediu de solvent organic inert ales dintre benzen, toluen sau maestecurile acestora la temepratura ambinata dupa care produsul astfel obtinut se transforma într-o sare bazica a acestuia prin metode cunoscute.
RO102404A 1979-10-22 1980-10-22 Procedeu pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpenicilanic RO81225B (ro)

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 (2)

Publication Number Publication Date
RO81225A RO81225A (ro) 1983-02-15
RO81225B true RO81225B (ro) 1983-02-28

Family

ID=22201393

Family Applications (2)

Application Number Title Priority Date Filing Date
RO102404A RO81225B (ro) 1979-10-22 1980-10-22 Procedeu pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpenicilanic
RO108549A RO86176B (ro) 1979-10-22 1980-10-22 Procedeu pentru prepararea unor esteri ai acidului 6-beta-hidroxialchilpenicilanic

Family Applications After (1)

Application Number Title Priority Date Filing Date
RO108549A RO86176B (ro) 1979-10-22 1980-10-22 Procedeu pentru prepararea unor esteri ai acidului 6-beta-hidroxialchilpenicilanic

Country Status (38)

Country Link
US (1) US4287181A (ro)
JP (2) JPS5665892A (ro)
KR (1) KR840000797B1 (ro)
AR (1) AR227164A1 (ro)
AT (2) AT369372B (ro)
AU (1) AU519578B2 (ro)
BE (1) BE885812A (ro)
BG (2) BG38639A3 (ro)
CA (2) CA1144159A (ro)
CH (2) CH646175A5 (ro)
CS (2) CS219291B2 (ro)
DD (1) DD154542A5 (ro)
DE (1) DE3039504C2 (ro)
DK (1) DK389480A (ro)
ES (1) ES8204437A1 (ro)
FI (1) FI71156C (ro)
FR (1) FR2467852A1 (ro)
GB (3) GB2061930B (ro)
GR (1) GR70714B (ro)
GT (1) GT198065892A (ro)
HU (1) HU183236B (ro)
IE (3) IE51028B1 (ro)
IL (1) IL61307A (ro)
IN (1) IN154918B (ro)
IT (1) IT1149259B (ro)
LU (1) LU82880A1 (ro)
MX (1) MX6094E (ro)
NL (1) NL183358C (ro)
NO (1) NO159019C (ro)
NZ (1) NZ195307A (ro)
PH (5) PH16219A (ro)
PL (2) PL129534B1 (ro)
PT (1) PT71946B (ro)
RO (2) RO81225B (ro)
SE (1) SE451455B (ro)
SU (2) SU1122227A3 (ro)
YU (2) YU41743B (ro)
ZA (1) ZA806452B (ro)

Families Citing this family (33)

* 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
US4452796A (en) * 1982-06-14 1984-06-05 Pfizer Inc. 6-Aminoalkylpenicillanic acid 1,1-dioxides as beta-lactamase inhibitors
RO84910B (ro) * 1982-01-11 1984-09-30 Pfizer Inc. Procedeu pentru prepararea unor derivati 1, 1-dioxizi ai acidului 6-aminoalchilpenicilanic
US4427678A (en) 1982-01-11 1984-01-24 Pfizer Inc. 6-Aminomethylpenicillanic acid 1,1-dioxide derivatives as beta-lactamase inhibitors
US4377590A (en) * 1982-05-10 1983-03-22 Pfizer Inc. Derivatives of ampicillin and amoxicillin with beta-lactamase inhibitors
US4499017A (en) * 1983-06-06 1985-02-12 Pfizer Inc. Beta-lactamase inhibiting 6-(alkoxyamino-methyl) penicillanic acid 1,1-dioxide and derivatives
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
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
PT79893B (en) * 1984-01-30 1987-02-03 Pfizer Process for preparing 6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicilanic and derivatives thereof
US5015473A (en) * 1984-01-30 1991-05-14 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
DE3584015D1 (de) * 1984-01-30 1991-10-17 Pfizer 6-(substituierte) methylen-penicillansaeure und 6-(substituierte) hydroxymethyl-penicillansaeure und deren derivate.
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
US4675186A (en) * 1985-04-18 1987-06-23 Pfizer Inc. 6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives
US4762921A (en) * 1985-04-18 1988-08-09 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
DE3869630D1 (de) * 1987-01-27 1992-05-07 Pfizer 6-beta(substituierte)-(s)-hydroxymethylpenicillansaeure und deren derivate.
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
JP2006526612A (ja) * 2003-06-05 2006-11-24 ファイザー・プロダクツ・インク ベータ−ラクタマーゼ阻害剤・プロドラッグ
EP2123657B1 (en) * 2007-03-09 2012-11-21 Otsuka Chemical Co., Ltd. Method for producing 6-hydroxyethylpenam compound
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 (ro) * 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
SU1026654A3 (ru) 1983-06-30
YU267680A (en) 1983-09-30
NL183358B (nl) 1988-05-02
NZ195307A (en) 1984-08-24
IE852229L (en) 1981-04-22
NO159019C (no) 1988-11-23
PL227420A1 (ro) 1982-08-30
FR2467852A1 (fr) 1981-04-30
PH18316A (en) 1985-05-29
YU41743B (en) 1987-12-31
ZA806452B (en) 1981-10-28
US4287181A (en) 1981-09-01
PL129638B1 (en) 1984-05-31
ATA518580A (de) 1982-05-15
FI71156B (fi) 1986-08-14
GT198065892A (es) 1982-04-10
PH17317A (en) 1984-07-20
PH16219A (en) 1983-08-09
PL129534B1 (en) 1984-05-31
IN154918B (ro) 1984-12-22
IE802174L (en) 1981-04-22
NO159019B (no) 1988-08-15
DD154542A5 (de) 1982-03-31
MX6094E (es) 1984-11-12
PH17315A (en) 1984-07-20
FI71156C (fi) 1986-11-24
BE885812A (fr) 1981-04-21
SU1122227A3 (ru) 1984-10-30
IT1149259B (it) 1986-12-03
AU6354880A (en) 1981-04-30
KR830004309A (ko) 1983-07-09
KR840000797B1 (ko) 1984-06-12
BG35189A3 (en) 1984-02-15
GR70714B (ro) 1983-01-18
SE8007354L (sv) 1981-04-23
CS219292B2 (en) 1983-03-25
DK389480A (da) 1981-04-23
RO86176A (ro) 1985-03-15
YU67183A (en) 1984-02-29
LU82880A1 (fr) 1981-06-04
FI803311L (fi) 1981-04-23
CH646175A5 (fr) 1984-11-15
YU42075B (en) 1988-04-30
CH647242A5 (fr) 1985-01-15
PT71946A (en) 1980-11-01
JPS6135197B2 (ro) 1986-08-12
HU183236B (en) 1984-04-28
GB8316829D0 (en) 1983-07-27
AT374479B (de) 1984-04-25
CA1163924A (en) 1984-03-20
AU519578B2 (en) 1981-12-10
BG38639A3 (en) 1986-01-15
GB2061930B (en) 1984-06-13
NL183358C (nl) 1988-10-03
IT8025488A0 (it) 1980-10-21
PH17458A (en) 1984-08-29
FR2467852B1 (ro) 1983-10-07
RO86176B (ro) 1985-03-31
NO803136L (no) 1981-04-23
ES496166A0 (es) 1982-05-01
AT369372B (de) 1982-12-27
GB2129421A (en) 1984-05-16
NL8005810A (nl) 1981-04-24
IE51026B1 (en) 1986-09-17
GB2129421B (en) 1984-11-14
IE850293L (en) 1981-04-22
JPS5665892A (en) 1981-06-03
PL235907A1 (ro) 1982-09-13
IE51028B1 (en) 1986-09-17
IL61307A0 (en) 1980-12-31
DE3039504A1 (de) 1981-04-30
GB2128986A (en) 1984-05-10
IE51027B1 (en) 1986-09-17
GB8316830D0 (en) 1983-07-27
ES8204437A1 (es) 1982-05-01
CA1144159A (en) 1983-04-05
CS219291B2 (en) 1983-03-25
GB2128986B (en) 1985-06-19
DE3039504C2 (de) 1984-10-11
RO81225A (ro) 1983-02-15
JPS61178988A (ja) 1986-08-11
AR227164A1 (es) 1982-09-30
SE451455B (sv) 1987-10-12
GB2061930A (en) 1981-05-20
ATA10882A (de) 1983-09-15
IL61307A (en) 1984-03-30
PT71946B (en) 1981-08-31

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