LU87123A1 - Clavulanate de potassium - Google Patents

Clavulanate de potassium Download PDF

Info

Publication number: LU87123A1
Authority: LU; Luxembourg
Prior art keywords: clavulanate; potassium clavulanate; crystalline; rosettes; potassium
Prior art date: 1987-01-29

Application number

LU87123A

Other languages

English (en)

French (fr)

Original Assignee

Beecham Group Plc

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.)

1987-01-29

Filing date

1988-01-29

Publication date

1988-05-03

1988-01-29 Application filed by Beecham Group Plc filed Critical Beecham Group Plc

1988-05-03 Publication of LU87123A1 publication Critical patent/LU87123A1/fr

Links

ABVRVIZBZKUTMK-JSYANWSFSA-M potassium clavulanate Chemical compound [K+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 ABVRVIZBZKUTMK-JSYANWSFSA-M 0.000 title claims description 75
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 72
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
239000000463 material Substances 0.000 claims description 44
238000000034 method Methods 0.000 claims description 38
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 34
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims description 32
229940090805 clavulanate Drugs 0.000 claims description 26
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 description 26
239000013078 crystal Substances 0.000 claims description 25
238000001556 precipitation Methods 0.000 claims description 25
239000002245 particle Substances 0.000 claims description 18
230000000844 anti-bacterial effect Effects 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 16
-1 clavulanate ions Chemical class 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 14
229910001414 potassium ion Inorganic materials 0.000 claims description 12
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 12
229960004659 ticarcillin Drugs 0.000 claims description 12
OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims description 12
239000000843 powder Substances 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
208000035143 Bacterial infection Diseases 0.000 claims description 7
208000022362 bacterial infectious disease Diseases 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000000725 suspension Substances 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
229960003324 clavulanic acid Drugs 0.000 claims description 5
238000010899 nucleation Methods 0.000 claims description 5
230000006911 nucleation Effects 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical group C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
238000001953 recrystallisation Methods 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229960003022 amoxicillin Drugs 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims description 3
239000003125 aqueous solvent Substances 0.000 claims description 2
239000002775 capsule Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
238000001727 in vivo Methods 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
239000000829 suppository Substances 0.000 claims description 2
239000003826 tablet Substances 0.000 claims description 2
239000000243 solution Substances 0.000 description 25
239000000047 product Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
235000019580 granularity Nutrition 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
229930182555 Penicillin Natural products 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 description 7
238000010191 image analysis Methods 0.000 description 6
238000001000 micrograph Methods 0.000 description 6
150000002960 penicillins Chemical class 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229940057995 liquid paraffin Drugs 0.000 description 5
239000004570 mortar (masonry) Substances 0.000 description 5
208000035126 Facies Diseases 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
229930186147 Cephalosporin Natural products 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
150000001780 cephalosporins Chemical class 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000001802 infusion Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
241001465754 Metazoa Species 0.000 description 2
235000004789 Rosa xanthina Nutrition 0.000 description 2
241000109329 Rosa xanthina Species 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
210000003128 head Anatomy 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
238000010926 purge Methods 0.000 description 2
150000003952 β-lactams Chemical class 0.000 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
LLQHSBBZNDXTIV-UHFFFAOYSA-N 6-[5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-4,5-dihydro-1,2-oxazol-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC1CC(=NO1)C1=CC2=C(NC(O2)=O)C=C1 LLQHSBBZNDXTIV-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
101100022451 Mus musculus Mbnl3 gene Proteins 0.000 description 1
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 description 1
239000011149 active material Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229940098164 augmentin Drugs 0.000 description 1
238000013475 authorization Methods 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
229940038649 clavulanate potassium Drugs 0.000 description 1
238000011260 co-administration Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
210000000720 eyelash Anatomy 0.000 description 1
230000002550 fecal effect Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000007873 sieving Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000029305 taxis Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229940027257 timentin Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- 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
- A61P31/04—Antibacterial agents

Landscapes

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

LU87123A 1987-01-29 1988-01-29 Clavulanate de potassium LU87123A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US878187A	1987-01-29	1987-01-29
US878187		1987-01-29
US7494487A	1987-07-17	1987-07-17
US7494487		1987-07-17

Publications (1)

Publication Number	Publication Date
LU87123A1 true LU87123A1 (fr)	1988-05-03

Family

ID=26678616

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87123A LU87123A1 (fr)	1987-01-29	1988-01-29	Clavulanate de potassium

Country Status (19)

Country	Link
EP (1)	EP0277008B1 (de)
JP (2)	JP2648321B2 (de)
KR (1)	KR960004535B1 (de)
AT (1)	AT399154B (de)
AU (1)	AU620538B2 (de)
BE (1)	BE1000734A3 (de)
CA (1)	CA1326486C (de)
CH (1)	CH677671A5 (de)
DE (1)	DE3853962T2 (de)
DK (1)	DK175709B1 (de)
ES (2)	ES2008418A6 (de)
FR (1)	FR2610196B1 (de)
GB (1)	GB2200355B (de)
GR (1)	GR1000035B (de)
IE (1)	IE880217L (de)
IT (1)	IT1227072B (de)
LU (1)	LU87123A1 (de)
NZ (1)	NZ223316A (de)
PT (1)	PT86631B (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2435859A (en) *	1945-06-06	1948-02-10	John E Whitman	Garment hanger
US2494711A (en) *	1946-06-28	1950-01-17	Kusher Hyman	Garment hanger
US3474943A (en) *	1967-02-21	1969-10-28	Frank Mcbain	Skirt hanger
SE7805391L (sv) *	1978-05-11	1979-11-12	Karner & Co Ab	Kledhengare
GB9205071D0 (en) *	1992-03-09	1992-04-22	Wellcome Found	Therapeutic nucleosides
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
SE9401169L (sv) *	1994-04-08	1995-10-09	Corimed Gmbh	Förfarande för framställning av ett antibekteriellt aktivt ämne samt användning därav
GB9426261D0 (en)	1994-12-24	1995-02-22	Spurcourt Ltd	Clavulanic acid salts
GB9515809D0 (en) *	1995-08-02	1995-10-04	Smithkline Beecham Plc	Process
AT403375B (de) *	1995-11-15	1998-01-26	Biochemie Gmbh	Verfahren zur fällung von alkalisalzen der clavulansäure
US6414142B1 (en)	1996-06-13	2002-07-02	Smithkline Beecham Corporation	Process for preparing potassium clavulanate
US6979735B1 (en) *	1999-04-01	2005-12-27	Dsm N.V.	Agglomerates by crystallization
AU776184B2 (en)	2000-05-13	2004-09-02	Smithkline Beecham Plc	Process for the purification of a salt of clavulanic acid
EP1683560A4 (de) *	2003-06-10	2008-10-01	Taisho Pharmaceutical Co Ltd	Radiales sphärisches kristallisationsprodukt, verfahren zur herstellung desselben und das kristallisationsprodukt enthaltendes trockenpulver
CN100384853C (zh) *	2004-05-10	2008-04-30	河北张药股份有限公司	替卡西林钠的合成方法
KR102459377B1 (ko) *	2022-03-18	2022-10-28	주식회사 에이치투뉴트리션	무알콜 단백질 맥주의 제조방법

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1508977A (en) *	1974-04-20	1978-04-26	Beecham Group Ltd	Beta-lactam antibiotic from streptomyces clavuligerus
GB1504425A (en) *	1975-08-20	1978-03-22	Beecham Group Ltd	Salts of clavulanic acid
GB2003863B (en) *	1977-09-01	1982-03-31	Beecham Group Ltd	Chemical process
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
EP0080862B1 (de) *	1981-12-02	1985-09-25	Beecham Group Plc	Pharmazeutische Zubereitung die Beta-Lactam Antibiotika enthält
FR2586561B1 (fr) *	1985-09-05	1988-05-20	Rhone Poulenc Sante	Procede de preparation d'agglomerats spheriques de paracetamol et produits obtenus

1988
- 1988-01-27 DK DK198800404A patent/DK175709B1/da not_active IP Right Cessation
- 1988-01-27 ES ES8800226A patent/ES2008418A6/es not_active Expired
- 1988-01-27 EP EP88300704A patent/EP0277008B1/de not_active Expired - Lifetime
- 1988-01-27 IE IE880217A patent/IE880217L/xx not_active IP Right Cessation
- 1988-01-27 AT AT0016388A patent/AT399154B/de not_active IP Right Cessation
- 1988-01-27 ES ES88300704T patent/ES2074048T3/es not_active Expired - Lifetime
- 1988-01-27 IT IT8847572A patent/IT1227072B/it active
- 1988-01-27 NZ NZ223316A patent/NZ223316A/xx unknown
- 1988-01-27 GR GR880100031A patent/GR1000035B/el not_active IP Right Cessation
- 1988-01-27 DE DE3853962T patent/DE3853962T2/de not_active Expired - Lifetime
- 1988-01-27 CA CA000557422A patent/CA1326486C/en not_active Expired - Lifetime
- 1988-01-27 PT PT86631A patent/PT86631B/pt unknown
- 1988-01-27 GB GB8801765A patent/GB2200355B/en not_active Expired - Lifetime
- 1988-01-28 KR KR1019880000765A patent/KR960004535B1/ko not_active Expired - Lifetime
- 1988-01-28 AU AU10927/88A patent/AU620538B2/en not_active Expired
- 1988-01-28 BE BE8800098A patent/BE1000734A3/fr not_active IP Right Cessation
- 1988-01-28 CH CH299/88A patent/CH677671A5/de not_active IP Right Cessation
- 1988-01-29 FR FR888801033A patent/FR2610196B1/fr not_active Expired - Lifetime
- 1988-01-29 LU LU87123A patent/LU87123A1/fr unknown
- 1988-01-29 JP JP63021144A patent/JP2648321B2/ja not_active Expired - Lifetime
1996
- 1996-12-03 JP JP8339027A patent/JP2716966B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
KR960004535B1 (ko)	1996-04-06
JP2648321B2 (ja)	1997-08-27
JPH09169771A (ja)	1997-06-30
KR890002166A (ko)	1989-04-08
PT86631B (pt)	1992-01-31
GR880100031A (en)	1988-12-16
ES2074048T3 (es)	1995-09-01
PT86631A (pt)	1988-02-01
EP0277008B1 (de)	1995-06-14
GB2200355A (en)	1988-08-03
JPS63270687A (ja)	1988-11-08
DE3853962T2 (de)	1996-02-08
IT1227072B (it)	1991-03-14
DK40488A (da)	1988-07-30
GB2200355B (en)	1990-08-01
EP0277008A1 (de)	1988-08-03
AT399154B (de)	1995-03-27
ATA16388A (de)	1994-08-15
AU1092788A (en)	1988-08-04
CH677671A5 (de)	1991-06-14
IE880217L (en)	1988-07-29
DK175709B1 (da)	2005-01-31
ES2008418A6 (es)	1989-07-16
FR2610196B1 (fr)	1991-06-28
JP2716966B2 (ja)	1998-02-18
NZ223316A (en)	1989-10-27
DE3853962D1 (de)	1995-07-20
IT8847572A0 (it)	1988-06-27
DK40488D0 (da)	1988-01-27
BE1000734A3 (fr)	1989-03-21
GR1000035B (el)	1990-03-12
GB8801765D0 (en)	1988-02-24
FR2610196A1 (fr)	1988-08-05
AU620538B2 (en)	1992-02-20
CA1326486C (en)	1994-01-25

Publication	Publication Date	Title
LU87123A1 (fr)	1988-05-03	Clavulanate de potassium
CA2606875C (fr)	2015-12-15	Combinaison pharmaceutique comprenant un antibiotique et une substance active choisie parmi le carveol, le thymol, le carvacrol, l'alpha-ionone et beta-ionone
CN1119016A (zh)	1996-03-20	结晶性头孢噻夫游离酸
CN1469880A (zh)	2004-01-21	药物组合物
CH679857A5 (de)	1992-04-30
CN1355800A (zh)	2002-06-26	噻唑烷二酮衍生物及其作为抗糖尿病药的用途
WO2018015974A1 (en)	2018-01-25	Polymorphic forms and amorphous solid dispersion of selexipag
US5288861A (en)	1994-02-22	Potassium clavulanate in rosette form
US5679789A (en)	1997-10-21	Pharmaceutical compositions comprising potassium clavulanate and methods of using them
JP2007070341A (ja)	2007-03-22	少なくとも２種の有効成分を含有する、注射可能無菌薬物配合物
AU712904B2 (en)	1999-11-18	Improved process for preparing potassium clavulanate
CN1334081A (zh)	2002-02-06	含有星形细胞功能改进剂作为活性组分的帕金森氏病治疗剂
CN1274282A (zh)	2000-11-22	用噻唑烷二酮和α－葡糖苷酶抑制剂治疗糖尿病
SK1442003A3 (en)	2004-05-04	Tartrate salts of thiazolidinedione derivative
US20020004595A1 (en)	2002-01-10	Process for preparing potassium clavulanate
EP1052989B1 (de)	2003-07-30	Verwendung von 2-amino-6-trifluoromethoxybenzothiazol zur herstellung eines arzneimittels zur vorbeugung oder behandlung von zerebellumkrankheiten
US5750685A (en)	1998-05-12	Process for preparing potassium clavulanate in rossette form
CN1243749A (zh)	2000-02-09	环加氧酶抑制剂
DE69918826T2 (de)	2004-12-02	Arylnitron therapeutische mittel zur behandlung von entzündlichen darmerkrankungen
SK1462003A3 (en)	2004-06-08	Tartrate salt of thiazolidinedione derivative
SK1452003A3 (en)	2004-05-04	Tartrate salts of thiazolidinedione derivative
CN1751051B (zh)	2010-06-09	结晶形式的头孢菌素
SK1432003A3 (en)	2004-03-02	Tartrate salts of thiazolidinedione derivative
CN110684038A (zh)	2020-01-14	曲索芬头孢曲松钠药物制剂治疗盆腔炎的新适应症
BE475834A (de)