ES2161602B1 - SYNTHESIS OF 6- (D-ALPHA- (BENCILIDENAMINOPHENYLACETAMIDE)) PENICILANATE 1,1-DIOXOPENICILANLANILOXIMETILO AND ANALOGS. NEW INTERMEDIATES FOR SYNTHESIS OF SULTAMICILLIN. - Google Patents

SYNTHESIS OF 6- (D-ALPHA- (BENCILIDENAMINOPHENYLACETAMIDE)) PENICILANATE 1,1-DIOXOPENICILANLANILOXIMETILO AND ANALOGS. NEW INTERMEDIATES FOR SYNTHESIS OF SULTAMICILLIN.

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Publication number
ES2161602B1
ES2161602B1 ES9900717A ES9900717A ES2161602B1 ES 2161602 B1 ES2161602 B1 ES 2161602B1 ES 9900717 A ES9900717 A ES 9900717A ES 9900717 A ES9900717 A ES 9900717A ES 2161602 B1 ES2161602 B1 ES 2161602B1
Authority
ES
Spain
Prior art keywords
synthesis
sultamicillin
alpha
analogs
dioxopenicilanlaniloximetilo
Prior art date
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 - Lifetime
Application number
ES9900717A
Other languages
Spanish (es)
Other versions
ES2161602A1 (en
Inventor
Jasanada Miguel Santos Bayod
Mari Felix Fernandez
Fernandez Francisco Gonzalez
Pozo Losada Carlos Del
Fernandez Eduardo Alonso
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.)
AsturPharma SA
Universidad de Oviedo
Original Assignee
AsturPharma SA
Universidad de Oviedo
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 AsturPharma SA, Universidad de Oviedo filed Critical AsturPharma SA
Priority to ES9900717A priority Critical patent/ES2161602B1/en
Priority to TR2000/00952A priority patent/TR200000952A3/en
Priority to JP2000108544A priority patent/JP2000344783A/en
Publication of ES2161602A1 publication Critical patent/ES2161602A1/en
Application granted granted Critical
Publication of ES2161602B1 publication Critical patent/ES2161602B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Síntesis de 6[D-alfa-(bencilidenaminofenilacetamido)] penicilanato de 1,1-dioxopenicilanoiloximetilo y análogos. Nuevos intermedios para la síntesis de sultamicilina. 6-[D-alfa- (bencilidenaminofenilacetamido)]penicilanato de 1,1- dioxopenicilanoiloximetilo y análogos del mismo (1), donde R1 es arilo opcionalmente sustituido por grupos nitro o halógeno, alquilo o heteroarilo, pueden obtenerse mediante un procedimiento que comprende hacer reaccionar ampicilina con un aldehído, generándose una ampicilina N-protegida, que se hace reaccionar con 1,1-dioxopenicilanato de iodemetilo. A partir de dichos iminoderivados (1) se puede obtener el antibiótico sultamicilina base o su correspondiente tosilato.Synthesis of 6 [D-alpha- (benzylidenaminophenylacetamide)] 1,1-dioxopenicillanoyloxymethyl penicillate and the like. New intermediates for the synthesis of sultamicillin. 6- [D-alpha- (benzylidenaminophenylacetamide)] 1,1-dioxopenicillanoyloxymethyl penicillate and analogs thereof (1), where R 1 is aryl optionally substituted by nitro or halogen, alkyl or heteroaryl groups, can be obtained by a process comprising making reacting ampicillin with an aldehyde, generating an N-protected ampicillin, which is reacted with iodemethyl 1,1-dioxopenicillate. From said iminoderivatives (1), the antibiotic sultamicillin base or its corresponding tosylate can be obtained.

ES9900717A 1999-04-08 1999-04-08 SYNTHESIS OF 6- (D-ALPHA- (BENCILIDENAMINOPHENYLACETAMIDE)) PENICILANATE 1,1-DIOXOPENICILANLANILOXIMETILO AND ANALOGS. NEW INTERMEDIATES FOR SYNTHESIS OF SULTAMICILLIN. Expired - Lifetime ES2161602B1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
ES9900717A ES2161602B1 (en) 1999-04-08 1999-04-08 SYNTHESIS OF 6- (D-ALPHA- (BENCILIDENAMINOPHENYLACETAMIDE)) PENICILANATE 1,1-DIOXOPENICILANLANILOXIMETILO AND ANALOGS. NEW INTERMEDIATES FOR SYNTHESIS OF SULTAMICILLIN.
TR2000/00952A TR200000952A3 (en) 1999-04-08 2000-04-10 Synthesis of 1,1-dioxopenicillaniloxymethyl 6- [D-alpha- (benzylideneamino-phenylacetamido)] penicillanate and the like. New intermediates suitable for the synthesis of sultamicillin.
JP2000108544A JP2000344783A (en) 1999-04-08 2000-04-10 SYNTHESIS OF 1,1-DIOXOPENICILLANOYLOXYMETHYL 6-[D-alpha-(BENZYLIDENEAMINOPHENYLACETAMIDO)-PENICILLINATE AND ITS ANALOGUE, AND NEW INTERMEDIATE IN SYNTHESIS OF SULTAMICILLIN

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES9900717A ES2161602B1 (en) 1999-04-08 1999-04-08 SYNTHESIS OF 6- (D-ALPHA- (BENCILIDENAMINOPHENYLACETAMIDE)) PENICILANATE 1,1-DIOXOPENICILANLANILOXIMETILO AND ANALOGS. NEW INTERMEDIATES FOR SYNTHESIS OF SULTAMICILLIN.

Publications (2)

Publication Number Publication Date
ES2161602A1 ES2161602A1 (en) 2001-12-01
ES2161602B1 true ES2161602B1 (en) 2003-02-16

Family

ID=8307946

Family Applications (1)

Application Number Title Priority Date Filing Date
ES9900717A Expired - Lifetime ES2161602B1 (en) 1999-04-08 1999-04-08 SYNTHESIS OF 6- (D-ALPHA- (BENCILIDENAMINOPHENYLACETAMIDE)) PENICILANATE 1,1-DIOXOPENICILANLANILOXIMETILO AND ANALOGS. NEW INTERMEDIATES FOR SYNTHESIS OF SULTAMICILLIN.

Country Status (3)

Country Link
JP (1) JP2000344783A (en)
ES (1) ES2161602B1 (en)
TR (1) TR200000952A3 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007004239A1 (en) * 2005-07-06 2007-01-11 Morepen Laboratories Limited New polymorphic form of sultamicillin tosylate and a process therefor
CN100336816C (en) * 2005-12-14 2007-09-12 广州大学 Preparation method of sulbactam

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2052992A1 (en) * 1969-06-20 1971-04-16 Clin Midy Alpha aldimino benzyl penicillins
FR2230649A1 (en) * 1973-05-23 1974-12-20 Aries Robert Alkanoyloxymethyl esters of penicillins - with alpha-(methyleneimino)phenylacetamido side-chain with long duration of action
GB1461860A (en) * 1974-10-22 1977-01-19 Prodotti Antibiotici Spa Semi-synthetic penicillin
IE49880B1 (en) * 1979-02-13 1986-01-08 Leo Pharm Prod Ltd Penicillin derivatives
IL64009A (en) * 1980-10-31 1984-09-30 Rech Applications Therap Crystalline 1,1-dioxopenicillanoyloxymethyl 6-(d-alpha-amino-alpha-phenylacetamido)penicillanate tosylate hydrates,their production and pharmaceutical compositions containing them
US4381263A (en) * 1981-03-23 1983-04-26 Pfizer Inc. Process for the preparation of penicillanic acid esters
PH20068A (en) * 1982-12-06 1986-09-18 Pfizer Process and intermediates for sultamicillin and analogs
KR910009271B1 (en) * 1989-06-20 1991-11-08 김영설 1,1-dioxopenicillanoyl oxymethyl d-6-(alpha-cmethyleneamino phenylacetamide)-penicillanate and p-tolluenesulfonic acid salts
ES2100125B1 (en) * 1995-06-02 1998-04-01 Asturpharma S A PROCEDURE FOR THE PREPARATION OF METHANODIOL ESTERS OF DIOXOPENICILANIC ACID.

Also Published As

Publication number Publication date
TR200000952A2 (en) 2000-11-21
ES2161602A1 (en) 2001-12-01
TR200000952A3 (en) 2000-11-21
JP2000344783A (en) 2000-12-12

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