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.Info
- 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
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000003786 synthesis reaction Methods 0.000 title abstract 4
- OPYGFNJSCUDTBT-PMLPCWDUSA-N sultamicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OCOC(=O)[C@H]2C(S(=O)(=O)[C@H]3N2C(C3)=O)(C)C)(C)C)=CC=CC=C1 OPYGFNJSCUDTBT-PMLPCWDUSA-N 0.000 title abstract 3
- 229960001326 sultamicillin Drugs 0.000 title abstract 3
- 239000000543 intermediate Substances 0.000 title abstract 2
- MSAYBZSAGIIHHG-UHFFFAOYSA-N 2-(benzylideneamino)-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)N=CC1=CC=CC=C1 MSAYBZSAGIIHHG-UHFFFAOYSA-N 0.000 abstract 2
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 abstract 2
- 229960000723 ampicillin Drugs 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- 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.
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)
| 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)
| 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-dioxophenylsilanoyl oxymethyl D-6- [α- (methyleneamino) phenyl-acetamido] -phenylanate and its para-toluenesulfonate salts |
| ES2100125B1 (en) * | 1995-06-02 | 1998-04-01 | Asturpharma S A | PROCEDURE FOR THE PREPARATION OF METHANODIOL ESTERS OF DIOXOPENICILANIC ACID. |
-
1999
- 1999-04-08 ES ES9900717A patent/ES2161602B1/en not_active Expired - Lifetime
-
2000
- 2000-04-10 JP JP2000108544A patent/JP2000344783A/en active Pending
- 2000-04-10 TR TR2000/00952A patent/TR200000952A3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000344783A (en) | 2000-12-12 |
| ES2161602A1 (en) | 2001-12-01 |
| TR200000952A2 (en) | 2000-11-21 |
| TR200000952A3 (en) | 2000-11-21 |
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Legal Events
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| EC2A | Search report published |
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