WO1996020199A3 - Diclavulanate salt with a diamino ether and process of preparation - Google Patents

Diclavulanate salt with a diamino ether and process of preparation Download PDF

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Publication number
WO1996020199A3
WO1996020199A3 PCT/GB1995/003039 GB9503039W WO9620199A3 WO 1996020199 A3 WO1996020199 A3 WO 1996020199A3 GB 9503039 W GB9503039 W GB 9503039W WO 9620199 A3 WO9620199 A3 WO 9620199A3
Authority
WO
WIPO (PCT)
Prior art keywords
salt
optionally
clavulanic acid
ether
inert substituents
Prior art date
Application number
PCT/GB1995/003039
Other languages
French (fr)
Other versions
WO1996020199A2 (en
Inventor
George Leo Callwaert
Original Assignee
Spurcourt Ltd
George Leo Callwaert
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
Priority to SI9520145A priority Critical patent/SI9520145A/en
Priority to PL95321092A priority patent/PL182364B1/en
Application filed by Spurcourt Ltd, George Leo Callwaert filed Critical Spurcourt Ltd
Priority to JP8520309A priority patent/JPH10511386A/en
Priority to AU43110/96A priority patent/AU702968B2/en
Priority to SI9530245T priority patent/SI0799233T1/en
Priority to SK776-97A priority patent/SK282663B6/en
Priority to MD97-0230A priority patent/MD1738F2/en
Priority to NZ297857A priority patent/NZ297857A/en
Priority to DE69508962T priority patent/DE69508962T2/en
Priority to DK95941809T priority patent/DK0799233T3/en
Priority to TJ97000473A priority patent/TJ269B/en
Priority to BR9510250A priority patent/BR9510250A/en
Priority to APAP/P/1997/001013A priority patent/AP670A/en
Priority to CA002208520A priority patent/CA2208520C/en
Priority to EP95941809A priority patent/EP0799233B1/en
Priority to EE9700139A priority patent/EE9700139A/en
Priority to RO97-01119A priority patent/RO118429B1/en
Priority to US08/737,891 priority patent/US5786351A/en
Publication of WO1996020199A2 publication Critical patent/WO1996020199A2/en
Publication of WO1996020199A3 publication Critical patent/WO1996020199A3/en
Priority to IS4501A priority patent/IS4501A/en
Priority to FI972464A priority patent/FI972464A/en
Priority to SE9702306A priority patent/SE520665C2/en
Priority to NO19972946A priority patent/NO313200B1/en
Priority to BG101671A priority patent/BG62971B1/en
Priority to GR990401715T priority patent/GR3030629T3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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
    • 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

Abstract

A di-clavulanate salt derived from clavulanic acid and a diamino ether of formula (I), where R1 is an alkylene group, optionally having one or more inert substituents; and each of R?2 and R3¿ is a hydrogen atom or an alkyl group, optionally having one or more inert substituents, or R?2 and R3¿ together complete a heterocyclic ring having 4 to 7 carbon atoms, again optionally having one or more inert substituents. The salt is prepared by reacting a bis(2-dialkylaminoalkylene)ether (or a salt thereof) with clavulanic acid in an organic solvent and isolating the resulting salt. The clavulanic acid salt can be used in pharmaceutical formulations together with a pharmaceutically acceptable carrier, and, optionally, a beta-lactam antibiotic, and is useful as an intermediate for the potassium salt.
PCT/GB1995/003039 1994-12-24 1995-12-22 Diclavulanate salt with a diamino ether and process of preparation WO1996020199A2 (en)

Priority Applications (24)

Application Number Priority Date Filing Date Title
APAP/P/1997/001013A AP670A (en) 1994-12-24 1995-12-22 Diclavulanate salt with a diamino ether and process of preparation.
BR9510250A BR9510250A (en) 1994-12-24 1995-12-22 Diclavulanate salt Process for preparing clavulanic acid salt and pharmaceutical composition
JP8520309A JPH10511386A (en) 1994-12-24 1995-12-22 Diclavulanate with diaminoether and preparation process
AU43110/96A AU702968B2 (en) 1994-12-24 1995-12-22 Clavulanic acid salts
SI9530245T SI0799233T1 (en) 1994-12-24 1995-12-22 Diclavulanic acid salts with diamino ethers and process for their preparation
SK776-97A SK282663B6 (en) 1994-12-24 1995-12-22 Diaminoether diclavulanate, its preparation method and pharmaceut ical composition containing it
MD97-0230A MD1738F2 (en) 1994-12-24 1995-12-22 Diclavulanate salt, process for obtaining and pharmaceutical composition on base thereof
NZ297857A NZ297857A (en) 1994-12-24 1995-12-22 Di-clavulanate salt of bis(aminoalkyl)ethers
PL95321092A PL182364B1 (en) 1994-12-24 1995-12-22 Diclavulanic salts of diamine ethers and method of obtaining them
DK95941809T DK0799233T3 (en) 1994-12-24 1995-12-22 Diclavulanic acid salts with diamino ethers and process for their preparation
TJ97000473A TJ269B (en) 1994-12-24 1995-12-22 Diclavulanate with a diamino ether and process of preparation
SI9520145A SI9520145A (en) 1994-12-24 1995-12-22 Diclavulanate salt with a diamino ether and process of preparation
CA002208520A CA2208520C (en) 1994-12-24 1995-12-22 Diclavulanate salt with a diamino ether and process of preparation
DE69508962T DE69508962T2 (en) 1994-12-24 1995-12-22 DICLAVULANATE SALTS WITH DIAMINOETHER AND METHOD FOR THE PRODUCTION THEREOF
EP95941809A EP0799233B1 (en) 1994-12-24 1995-12-22 Diclavulanic acid salts with diamino ethers and process for their preparation
EE9700139A EE9700139A (en) 1994-12-24 1995-12-22 Diclavulanate salt of diaminoether and method for its preparation
RO97-01119A RO118429B1 (en) 1994-12-24 1995-12-22 Salts of clavulanic acid with diamino ethers and process for preparing the same
US08/737,891 US5786351A (en) 1994-12-24 1995-12-22 Clavulanic acid salts
IS4501A IS4501A (en) 1994-12-24 1997-06-09 Diclavulan salt with a diamine ether production process
FI972464A FI972464A (en) 1994-12-24 1997-06-10 Diclavulanate salt of diamino ether and process for its preparation
SE9702306A SE520665C2 (en) 1994-12-24 1997-06-17 Diclavulanate salt with a diamino ether and process of preparation
NO19972946A NO313200B1 (en) 1994-12-24 1997-06-23 Diclavulanate salt with a diamino ether, process for preparing a clavulanic acid salt, and pharmaceutical composition containing such a salt
BG101671A BG62971B1 (en) 1994-12-24 1997-06-25 Diclavulanic salt with diaminoether and method for its preparation
GR990401715T GR3030629T3 (en) 1994-12-24 1999-06-30 Clavulanic acid salts

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9426261.5A GB9426261D0 (en) 1994-12-24 1994-12-24 Clavulanic acid salts
GB9426261.5 1994-12-24

Publications (2)

Publication Number Publication Date
WO1996020199A2 WO1996020199A2 (en) 1996-07-04
WO1996020199A3 true WO1996020199A3 (en) 1996-09-12

Family

ID=10766624

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1995/003039 WO1996020199A2 (en) 1994-12-24 1995-12-22 Diclavulanate salt with a diamino ether and process of preparation

Country Status (40)

Country Link
US (1) US5786351A (en)
EP (1) EP0799233B1 (en)
JP (1) JPH10511386A (en)
KR (1) KR100416946B1 (en)
CN (1) CN1081640C (en)
AP (1) AP670A (en)
AR (1) AR004165A1 (en)
AT (1) ATE178606T1 (en)
AU (1) AU702968B2 (en)
BG (1) BG62971B1 (en)
BR (1) BR9510250A (en)
CA (1) CA2208520C (en)
CZ (1) CZ289287B6 (en)
DE (1) DE69508962T2 (en)
DK (1) DK0799233T3 (en)
EE (1) EE9700139A (en)
ES (1) ES2132756T3 (en)
FI (1) FI972464A (en)
GB (1) GB9426261D0 (en)
GE (1) GEP20002212B (en)
GR (1) GR3030629T3 (en)
HU (1) HUT77090A (en)
IL (1) IL116498A (en)
IS (1) IS4501A (en)
MD (1) MD1738F2 (en)
MY (1) MY114213A (en)
NO (1) NO313200B1 (en)
NZ (1) NZ297857A (en)
OA (1) OA10861A (en)
PL (1) PL182364B1 (en)
RO (1) RO118429B1 (en)
RU (1) RU2152948C1 (en)
SE (1) SE520665C2 (en)
SI (2) SI0799233T1 (en)
SK (1) SK282663B6 (en)
TJ (1) TJ269B (en)
TR (1) TR199501675A2 (en)
TW (1) TW401409B (en)
WO (1) WO1996020199A2 (en)
ZA (1) ZA9510880B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI9400107A (en) 1994-03-02 1995-10-31 Lek Tovarna Farmacevtskih New process of the isolation of clavulanic acid and its pharmaceutical salts from fermented broth of streptomyces sp.p 6621 ferm p 2804.
GB9426261D0 (en) * 1994-12-24 1995-02-22 Spurcourt Ltd Clavulanic acid salts
SI9500134B (en) 1995-04-20 2004-04-30 Lek, Preparation procedure of pure alkali salts of clavulanic acid
WO1998021212A1 (en) * 1996-11-11 1998-05-22 Gist-Brocades B.V. Process for the preparation of salts and esters of clavulanic acid
AT404728B (en) * 1996-11-27 1999-02-25 Biochemie Gmbh METHOD FOR PRODUCING CLAVULIC ACID AMINE SALTS
JP4954421B2 (en) 2000-05-13 2012-06-13 スミスクライン ビーチャム リミテッド Purification method of clavulanate
US8461327B2 (en) * 2008-04-02 2013-06-11 Dsm Sinochem Pharmaceuticals Netherlands B.V. Diamine salts of carboxylic acids

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0277008A1 (en) * 1987-01-29 1988-08-03 Beecham Group Plc Process for crystallization of potassium clavulanate
EP0562583A1 (en) * 1992-03-26 1993-09-29 LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d. Alkylene diammonium diclavulanate derivatives, process for their preparation and for their use
WO1993025557A1 (en) * 1992-06-11 1993-12-23 Smithkline Beecham Plc Process for the preparation of clavulanic acid
US5288861A (en) * 1987-01-29 1994-02-22 Beecham Group Plc Potassium clavulanate in rosette form
WO1994021647A1 (en) * 1993-03-18 1994-09-29 Smithkline Beecham Plc Diclavulanate salt with a diamine and process of preparation
WO1994022873A1 (en) * 1993-03-26 1994-10-13 Gist-Brocades N.V. Diamine salts of clavulanic acid

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4144242A (en) * 1975-02-07 1979-03-13 Glaxo Laboratories Limited Process for the purification of clavulanic acid
GB1578739A (en) * 1976-07-23 1980-11-05 Beecham Group Ltd Amine salts of clavulanic acid methods for their preparation and compositions containing them
US4255332A (en) * 1977-09-01 1981-03-10 Beecham Group Limited Process for the preparation of potassium clavulanate from lithium clavulanate
US4454069A (en) * 1979-08-24 1984-06-12 Beecham Group Limited Clavulanic acid salts and their preparation from the tertiary butyl amine salt
EP0026044B1 (en) * 1979-08-24 1983-06-08 Beecham Group Plc Amine salt of clavulanic acid, its preparation and use
ES2010143A6 (en) * 1989-03-01 1989-10-16 Pharma Mar S A Pharmar A new process for obtainment of Z(2R,5R)-3-(2-hydroxyethyliden)-7-oxo-4-oxa-1-azabicyclo(3,2,0)-heptane-2-carboxylic acid and pharmaceutically acceptable salts and esters thereof, from fermentation broths of Streptomyces sp.
AT400033B (en) * 1992-03-10 1995-09-25 Biochemie Gmbh NEW METHOD FOR ISOLATING AND PURIFYING CLAVULANIC ACID AND FOR PRODUCING PHARMACOLOGICALLY COMPATIBLE SALTS THEREOF
GB9426261D0 (en) * 1994-12-24 1995-02-22 Spurcourt Ltd Clavulanic acid salts

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0277008A1 (en) * 1987-01-29 1988-08-03 Beecham Group Plc Process for crystallization of potassium clavulanate
US5288861A (en) * 1987-01-29 1994-02-22 Beecham Group Plc Potassium clavulanate in rosette form
EP0562583A1 (en) * 1992-03-26 1993-09-29 LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d. Alkylene diammonium diclavulanate derivatives, process for their preparation and for their use
WO1993025557A1 (en) * 1992-06-11 1993-12-23 Smithkline Beecham Plc Process for the preparation of clavulanic acid
WO1994021647A1 (en) * 1993-03-18 1994-09-29 Smithkline Beecham Plc Diclavulanate salt with a diamine and process of preparation
WO1994022873A1 (en) * 1993-03-26 1994-10-13 Gist-Brocades N.V. Diamine salts of clavulanic acid

Also Published As

Publication number Publication date
AP9701013A0 (en) 1997-07-31
RU2152948C1 (en) 2000-07-20
CA2208520C (en) 2003-10-07
DK0799233T3 (en) 1999-10-18
BG62971B1 (en) 2000-12-29
TJ269B (en) 2000-08-07
RO118429B1 (en) 2003-05-30
CA2208520A1 (en) 1996-07-04
KR100416946B1 (en) 2004-05-10
PL321092A1 (en) 1997-11-24
JPH10511386A (en) 1998-11-04
IL116498A0 (en) 1996-03-31
CN1081640C (en) 2002-03-27
GR3030629T3 (en) 1999-10-29
SE520665C2 (en) 2003-08-05
TW401409B (en) 2000-08-11
MD1738F2 (en) 2001-09-30
CZ289287B6 (en) 2001-12-12
US5786351A (en) 1998-07-28
SK282663B6 (en) 2002-11-06
DE69508962T2 (en) 1999-08-12
AR004165A1 (en) 1998-11-04
MX9704693A (en) 1998-06-30
SI0799233T1 (en) 1999-08-31
DE69508962D1 (en) 1999-05-12
NO313200B1 (en) 2002-08-26
TR199501675A2 (en) 1997-07-21
ZA9510880B (en) 1996-08-07
NO972946L (en) 1997-06-23
ATE178606T1 (en) 1999-04-15
OA10861A (en) 2003-02-17
AP670A (en) 1998-09-04
HUT77090A (en) 1998-03-02
SI9520145A (en) 1998-02-28
WO1996020199A2 (en) 1996-07-04
IL116498A (en) 2000-07-26
PL182364B1 (en) 2001-12-31
AU702968B2 (en) 1999-03-11
NO972946D0 (en) 1997-06-23
EP0799233A2 (en) 1997-10-08
CZ192097A3 (en) 1998-08-12
SK77697A3 (en) 1998-01-14
CN1171111A (en) 1998-01-21
IS4501A (en) 1997-06-09
BR9510250A (en) 1997-11-04
FI972464A0 (en) 1997-06-10
SE9702306D0 (en) 1997-06-17
MY114213A (en) 2002-08-30
GB9426261D0 (en) 1995-02-22
MD970230A (en) 1999-05-31
GEP20002212B (en) 2000-08-25
NZ297857A (en) 1997-11-24
EE9700139A (en) 1997-12-15
FI972464A (en) 1997-08-21
ES2132756T3 (en) 1999-08-16
EP0799233B1 (en) 1999-04-07
SE9702306L (en) 1997-08-25
BG101671A (en) 1998-09-30
AU4311096A (en) 1996-07-19

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