AP670A - Diclavulanate salt with a diamino ether and process of preparation. - Google Patents

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

Info

Publication number: AP670A
Authority: AP; ARIPO
Prior art keywords: salt; clavulanic acid; ether; process according; solvent
Prior art date: 1994-12-24

Application number

APAP/P/1997/001013A

Other languages

English (en)

Other versions

AP9701013A0 (en

Inventor

George Leo Callewaert

Original Assignee

Spurcourt Ltd

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.)

1994-12-24

Filing date

1995-12-22

Publication date

1998-09-04

1995-12-22 Application filed by Spurcourt Ltd filed Critical Spurcourt Ltd

1997-07-31 Publication of AP9701013A0 publication Critical patent/AP9701013A0/xx

1998-09-04 Application granted granted Critical

1998-09-04 Publication of AP670A publication Critical patent/AP670A/en

Links

150000003839 salts Chemical class 0.000 title claims abstract description 39
SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title description 7
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 claims abstract description 45
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims abstract description 39
229960003324 clavulanic acid Drugs 0.000 claims abstract description 39
239000003960 organic solvent Substances 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
125000001424 substituent group Chemical group 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
239000003937 drug carrier Substances 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 29
239000013078 crystal Substances 0.000 claims description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 13
-1 aliphatic carboxylic ester Chemical class 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
230000003115 biocidal effect Effects 0.000 claims description 4
239000006184 cosolvent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
229930186147 Cephalosporin Natural products 0.000 claims description 3
229930182555 Penicillin Natural products 0.000 claims description 3
229940124587 cephalosporin Drugs 0.000 claims description 3
150000001780 cephalosporins Chemical class 0.000 claims description 3
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229940049954 penicillin Drugs 0.000 claims description 2
150000001733 carboxylic acid esters Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
239000003782 beta lactam antibiotic agent Substances 0.000 abstract description 3
239000002132 β-lactam antibiotic Substances 0.000 abstract description 3
229940124586 β-lactam antibiotics Drugs 0.000 abstract description 3
239000000243 solution Substances 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000002425 crystallisation Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
229960004592 isopropanol Drugs 0.000 description 4
239000012453 solvate Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
230000003226 decolorizating effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
102000006635 beta-lactamase Human genes 0.000 description 1
125000003460 beta-lactamyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229940090805 clavulanate Drugs 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000011109 contamination Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
VXPJBVRYAHYMNY-UHFFFAOYSA-N n-methyl-2-[2-(methylamino)ethoxy]ethanamine Chemical compound CNCCOCCNC VXPJBVRYAHYMNY-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
230000006911 nucleation Effects 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001052 transient effect Effects 0.000 description 1

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cephalosporin Compounds (AREA)

APAP/P/1997/001013A 1994-12-24 1995-12-22 Diclavulanate salt with a diamino ether and process of preparation. AP670A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9426261.5A GB9426261D0 (en)	1994-12-24	1994-12-24	Clavulanic acid salts
PCT/GB1995/003039 WO1996020199A2 (en)	1994-12-24	1995-12-22	Diclavulanate salt with a diamino ether and process of preparation

Publications (2)

Publication Number	Publication Date
AP9701013A0 AP9701013A0 (en)	1997-07-31
AP670A true AP670A (en)	1998-09-04

Family

ID=10766624

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1997/001013A AP670A (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 (de)
EP (1)	EP0799233B1 (de)
JP (1)	JPH10511386A (de)
KR (1)	KR100416946B1 (de)
CN (1)	CN1081640C (de)
AP (1)	AP670A (de)
AR (1)	AR004165A1 (de)
AT (1)	ATE178606T1 (de)
AU (1)	AU702968B2 (de)
BG (1)	BG62971B1 (de)
BR (1)	BR9510250A (de)
CA (1)	CA2208520C (de)
CZ (1)	CZ289287B6 (de)
DE (1)	DE69508962T2 (de)
DK (1)	DK0799233T3 (de)
EE (1)	EE9700139A (de)
ES (1)	ES2132756T3 (de)
FI (1)	FI972464A (de)
GB (1)	GB9426261D0 (de)
GE (1)	GEP20002212B (de)
GR (1)	GR3030629T3 (de)
HU (1)	HUT77090A (de)
IL (1)	IL116498A (de)
IS (1)	IS4501A (de)
MD (1)	MD1738F2 (de)
MY (1)	MY114213A (de)
NO (1)	NO313200B1 (de)
NZ (1)	NZ297857A (de)
OA (1)	OA10861A (de)
PL (1)	PL182364B1 (de)
RO (1)	RO118429B1 (de)
RU (1)	RU2152948C1 (de)
SE (1)	SE520665C2 (de)
SI (2)	SI0799233T1 (de)
SK (1)	SK282663B6 (de)
TJ (1)	TJ269B (de)
TR (1)	TR199501675A2 (de)
TW (1)	TW401409B (de)
WO (1)	WO1996020199A2 (de)
ZA (1)	ZA9510880B (de)

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 (sl)	1995-04-20	2004-04-30	Lek,	Postopek za pripravo čistih alkalijskih soli klavulanske kisline
CN1238776A (zh) *	1996-11-11	1999-12-15	吉斯特-布罗卡迪斯有限公司	制备棒酸盐和酯的方法
AT404728B (de) *	1996-11-27	1999-02-25	Biochemie Gmbh	Verfahren zur herstellung von clavulansäure-aminsalzen
CA2408853C (en)	2000-05-13	2012-01-10	Smithkline Beecham P.L.C.	Process
CN102046800A (zh) *	2008-04-02	2011-05-04	帝斯曼知识产权资产管理有限公司	羧酸的二胺盐

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0562583A1 (de) *	1992-03-26	1993-09-29	LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d.	Neue Alkylendiammonium-diclavulanat-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung
WO1993025557A1 (en) *	1992-06-11	1993-12-23	Smithkline Beecham Plc	Process for the preparation of clavulanic acid
WO1996020199A2 (en) *	1994-12-24	1996-07-04	Spurcourt Limited	Diclavulanate salt with a diamino ether and process of preparation

Family Cites Families (11)

* 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
EP0026044B1 (de) *	1979-08-24	1983-06-08	Beecham Group Plc	Aminsalz der Clavulansäure, seine Herstellung und Verwendung
US4454069A (en) *	1979-08-24	1984-06-12	Beecham Group Limited	Clavulanic acid salts and their preparation from the tertiary butyl amine salt
US5288861A (en)	1987-01-29	1994-02-22	Beecham Group Plc	Potassium clavulanate in rosette form
NZ223316A (en)	1987-01-29	1989-10-27	Beecham Group Plc	Crystalline potassium clavulanate and pharmaceutical compositions
ES2010143A6 (es)	1989-03-01	1989-10-16	Pharma Mar S A Pharmar	Un nuevo procedimiento de obtencion del acido z(2r,5r)-3-(2-hiadroxietiliden)-7- oxo-4-oxa-1-azabiciclo(3,2,0) -heptano-2-carboxilico y de sales estares farmaceutiacamente aceptables del mismo,a partir de caldos de fermentacion de streptomyces, sp.
AT400033B (de) *	1992-03-10	1995-09-25	Biochemie Gmbh	Neues verfahren zur isolierung und reinigung von clavulansäure und zur herstellung von pharmakologisch verträglichen salzen derselben
GB9305565D0 (en) *	1993-03-18	1993-05-05	Smithkline Beecham Plc	Novel compounds and processes
DE647229T1 (de) *	1993-03-26	1996-01-18	Gist Brocades Nv	Diaminsalze von clavulansäure.

1994
- 1994-12-24 GB GBGB9426261.5A patent/GB9426261D0/en active Pending
1995
- 1995-12-21 AR ARP950100702A patent/AR004165A1/es active IP Right Grant
- 1995-12-21 ZA ZA9510880A patent/ZA9510880B/xx unknown
- 1995-12-21 IL IL11649895A patent/IL116498A/xx not_active IP Right Cessation
- 1995-12-22 AP APAP/P/1997/001013A patent/AP670A/en active
- 1995-12-22 SK SK776-97A patent/SK282663B6/sk unknown
- 1995-12-22 MD MD97-0230A patent/MD1738F2/ro unknown
- 1995-12-22 PL PL95321092A patent/PL182364B1/pl not_active IP Right Cessation
- 1995-12-22 ES ES95941809T patent/ES2132756T3/es not_active Expired - Lifetime
- 1995-12-22 RU RU97112159/04A patent/RU2152948C1/ru not_active IP Right Cessation
- 1995-12-22 CA CA002208520A patent/CA2208520C/en not_active Expired - Fee Related
- 1995-12-22 WO PCT/GB1995/003039 patent/WO1996020199A2/en active IP Right Grant
- 1995-12-22 GE GEAP19953795A patent/GEP20002212B/en unknown
- 1995-12-22 SI SI9530245T patent/SI0799233T1/xx unknown
- 1995-12-22 EP EP95941809A patent/EP0799233B1/de not_active Expired - Lifetime
- 1995-12-22 AU AU43110/96A patent/AU702968B2/en not_active Ceased
- 1995-12-22 AT AT95941809T patent/ATE178606T1/de not_active IP Right Cessation
- 1995-12-22 TR TR95/01675A patent/TR199501675A2/xx unknown
- 1995-12-22 KR KR1019970704332A patent/KR100416946B1/ko not_active IP Right Cessation
- 1995-12-22 HU HU9701685A patent/HUT77090A/hu not_active Application Discontinuation
- 1995-12-22 SI SI9520145A patent/SI9520145A/sl unknown
- 1995-12-22 JP JP8520309A patent/JPH10511386A/ja active Pending
- 1995-12-22 NZ NZ297857A patent/NZ297857A/en unknown
- 1995-12-22 DE DE69508962T patent/DE69508962T2/de not_active Expired - Fee Related
- 1995-12-22 BR BR9510250A patent/BR9510250A/pt not_active IP Right Cessation
- 1995-12-22 RO RO97-01119A patent/RO118429B1/ro unknown
- 1995-12-22 DK DK95941809T patent/DK0799233T3/da active
- 1995-12-22 US US08/737,891 patent/US5786351A/en not_active Expired - Fee Related
- 1995-12-22 CN CN95197032A patent/CN1081640C/zh not_active Expired - Fee Related
- 1995-12-22 EE EE9700139A patent/EE9700139A/xx unknown
- 1995-12-22 CZ CZ19971920A patent/CZ289287B6/cs not_active IP Right Cessation
- 1995-12-22 TJ TJ97000473A patent/TJ269B/xx unknown
- 1995-12-23 MY MYPI95004076A patent/MY114213A/en unknown
1996
- 1996-01-06 TW TW085100132A patent/TW401409B/zh not_active IP Right Cessation
1997
- 1997-06-09 IS IS4501A patent/IS4501A/is unknown
- 1997-06-10 FI FI972464A patent/FI972464A/fi unknown
- 1997-06-17 SE SE9702306A patent/SE520665C2/sv not_active IP Right Cessation
- 1997-06-23 NO NO19972946A patent/NO313200B1/no not_active IP Right Cessation
- 1997-06-24 OA OA70038A patent/OA10861A/en unknown
- 1997-06-25 BG BG101671A patent/BG62971B1/bg unknown
1999
- 1999-06-30 GR GR990401715T patent/GR3030629T3/el unknown

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0562583A1 (de) *	1992-03-26	1993-09-29	LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d.	Neue Alkylendiammonium-diclavulanat-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung
WO1993025557A1 (en) *	1992-06-11	1993-12-23	Smithkline Beecham Plc	Process for the preparation of clavulanic acid
WO1996020199A2 (en) *	1994-12-24	1996-07-04	Spurcourt Limited	Diclavulanate salt with a diamino ether and process of preparation

Also Published As

Publication number	Publication date
EP0799233A2 (de)	1997-10-08
SE9702306D0 (sv)	1997-06-17
NO972946L (no)	1997-06-23
CZ192097A3 (cs)	1998-08-12
TJ269B (en)	2000-08-07
ES2132756T3 (es)	1999-08-16
SI9520145A (sl)	1998-02-28
WO1996020199A3 (en)	1996-09-12
MD1738F2 (ro)	2001-09-30
AU4311096A (en)	1996-07-19
SI0799233T1 (en)	1999-08-31
ZA9510880B (en)	1996-08-07
PL182364B1 (pl)	2001-12-31
KR100416946B1 (ko)	2004-05-10
SK282663B6 (sk)	2002-11-06
IL116498A (en)	2000-07-26
BR9510250A (pt)	1997-11-04
DE69508962T2 (de)	1999-08-12
BG62971B1 (bg)	2000-12-29
EE9700139A (et)	1997-12-15
ATE178606T1 (de)	1999-04-15
CN1171111A (zh)	1998-01-21
IS4501A (is)	1997-06-09
WO1996020199A2 (en)	1996-07-04
HUT77090A (hu)	1998-03-02
MX9704693A (es)	1998-06-30
AP9701013A0 (en)	1997-07-31
SK77697A3 (en)	1998-01-14
US5786351A (en)	1998-07-28
NZ297857A (en)	1997-11-24
EP0799233B1 (de)	1999-04-07
OA10861A (en)	2003-02-17
SE520665C2 (sv)	2003-08-05
JPH10511386A (ja)	1998-11-04
MY114213A (en)	2002-08-30
PL321092A1 (en)	1997-11-24
MD970230A (en)	1999-05-31
SE9702306L (sv)	1997-08-25
RO118429B1 (ro)	2003-05-30
GR3030629T3 (en)	1999-10-29
FI972464A0 (fi)	1997-06-10
CZ289287B6 (cs)	2001-12-12
TW401409B (en)	2000-08-11
NO972946D0 (no)	1997-06-23
FI972464A (fi)	1997-08-21
CA2208520A1 (en)	1996-07-04
NO313200B1 (no)	2002-08-26
DK0799233T3 (da)	1999-10-18
CA2208520C (en)	2003-10-07
AU702968B2 (en)	1999-03-11
BG101671A (en)	1998-09-30
IL116498A0 (en)	1996-03-31
TR199501675A2 (tr)	1997-07-21
AR004165A1 (es)	1998-11-04
GB9426261D0 (en)	1995-02-22
CN1081640C (zh)	2002-03-27
GEP20002212B (en)	2000-08-25
DE69508962D1 (de)	1999-05-12
RU2152948C1 (ru)	2000-07-20

Publication	Publication Date	Title
CA2092330C (en)	2002-01-29	Novel alkylenediammonium diclavulanate derivatives, a process for the preparation thereof as well as the use thereof
AP670A (en)	1998-09-04	Diclavulanate salt with a diamino ether and process of preparation.
EP0131147A1 (de)	1985-01-16	Kristallines Amoxycillin-Salz
US5726170A (en)	1998-03-10	Clavulanic acid salts
EP0719778A1 (de)	1996-07-03	Clavulansäure Diaminsalze
EP0044238B1 (de)	1984-02-01	Cephalosporinsulfoxyd-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
RU97112159A (ru)	1999-06-27	Диклавулановая соль диаминового эфира и способ ее приготовления
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