ES2100125A1 - Process for the preparation of methanediol esters of dioxopenicillanic acid - Google Patents
Process for the preparation of methanediol esters of dioxopenicillanic acidInfo
- Publication number
- ES2100125A1 ES2100125A1 ES09501106A ES9501106A ES2100125A1 ES 2100125 A1 ES2100125 A1 ES 2100125A1 ES 09501106 A ES09501106 A ES 09501106A ES 9501106 A ES9501106 A ES 9501106A ES 2100125 A1 ES2100125 A1 ES 2100125A1
- Authority
- ES
- Spain
- Prior art keywords
- preparation
- esters
- dioxopenicillanic acid
- atom
- amine group
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title abstract 3
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical class OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract 1
- 239000003781 beta lactamase inhibitor Substances 0.000 abstract 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002132 β-lactam antibiotic Substances 0.000 abstract 1
- 229940124586 β-lactam antibiotics Drugs 0.000 abstract 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Process for the preparation of methanediol esters of dioxopenicillanic acid 57 Process for the preparation of methandiol esters of 1,1-dioxopenicillanic acid and its pharmaceutically acceptable salts of formula I (Figure I) in which R1 is a hydrogen atom, a lower alkyl residue or with R2 comprises a 5 or 6 carbon ring. R2 is an atom of hydrogen, a lower alkyl, cycloalkenynl or aryl residue which may or may not be substituted by hydroxyl or lower alkoxyl residues and R3 is a free amine group. Compound II, in which R1 and R2 have the meanings above, R3 is a free or protected amine group and R4 is a bromine atom is obtained by hydrogenation in the presence of a noble metal catalyst. Useful in the treatment of bacterial infections. They combine a betalactam antibiotic with a betalactamase inhibitor in a single molecule. <IMAGE>
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9501106A ES2100125B1 (en) | 1995-06-02 | 1995-06-02 | PROCEDURE FOR THE PREPARATION OF METHANODIOL ESTERS OF DIOXOPENICILANIC ACID. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9501106A ES2100125B1 (en) | 1995-06-02 | 1995-06-02 | PROCEDURE FOR THE PREPARATION OF METHANODIOL ESTERS OF DIOXOPENICILANIC ACID. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2100125A1 true ES2100125A1 (en) | 1997-06-01 |
| ES2100125B1 ES2100125B1 (en) | 1998-04-01 |
Family
ID=8290613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9501106A Expired - Fee Related ES2100125B1 (en) | 1995-06-02 | 1995-06-02 | PROCEDURE FOR THE PREPARATION OF METHANODIOL ESTERS OF DIOXOPENICILANIC ACID. |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2100125B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2161602A1 (en) * | 1999-04-08 | 2001-12-01 | Astur Pharma Sa | SYNTHESIS OF 1,1-DIOXOPENICILLANOYLOXYMETHYL 6-[D-alpha-(BENZYLIDENEAMINOPHENYLACETAMIDO)-PENICILLINATE AND ITS ANALOGUE, AND NEW INTERMEDIATE IN SYNTHESIS OF SULTAMICILLIN |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8305767A1 (en) * | 1981-03-23 | 1983-04-16 | Pfizer | Process for preparing penicillanic acid 1,1-dioxide derivatives and certain intermediates useful therein. |
| ES8403132A1 (en) * | 1981-03-23 | 1984-03-01 | Pfizer | Process and intermediates for production of 1,1-dioxopenicillanoyloxymethyl 6-(2-amino-2-phenylacetamido)penicillanates. |
| ES8504824A1 (en) * | 1982-12-06 | 1985-05-01 | Pfizer | A PROCEDURE FOR THE PREPARATION OF A SULTAMICILIN COMPOUND |
| ES2039299A1 (en) * | 1991-10-04 | 1993-09-16 | Asturpharma S A | Process for obtaining 1,1-dioxopenicillanic acid esters and their salts |
-
1995
- 1995-06-02 ES ES9501106A patent/ES2100125B1/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8305767A1 (en) * | 1981-03-23 | 1983-04-16 | Pfizer | Process for preparing penicillanic acid 1,1-dioxide derivatives and certain intermediates useful therein. |
| ES8403132A1 (en) * | 1981-03-23 | 1984-03-01 | Pfizer | Process and intermediates for production of 1,1-dioxopenicillanoyloxymethyl 6-(2-amino-2-phenylacetamido)penicillanates. |
| ES8504824A1 (en) * | 1982-12-06 | 1985-05-01 | Pfizer | A PROCEDURE FOR THE PREPARATION OF A SULTAMICILIN COMPOUND |
| ES2039299A1 (en) * | 1991-10-04 | 1993-09-16 | Asturpharma S A | Process for obtaining 1,1-dioxopenicillanic acid esters and their salts |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2161602A1 (en) * | 1999-04-08 | 2001-12-01 | Astur Pharma Sa | SYNTHESIS OF 1,1-DIOXOPENICILLANOYLOXYMETHYL 6-[D-alpha-(BENZYLIDENEAMINOPHENYLACETAMIDO)-PENICILLINATE AND ITS ANALOGUE, AND NEW INTERMEDIATE IN SYNTHESIS OF SULTAMICILLIN |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2100125B1 (en) | 1998-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 19970601 Kind code of ref document: A1 Effective date: 19970601 |
|
| FD1A | Patent lapsed |
Effective date: 20050603 |