ZA200507760B - Cephalosporin in crystalline form - Google Patents

Cephalosporin in crystalline form Download PDF

Info

Publication number: ZA200507760B
Authority: ZA; South Africa
Prior art keywords: cephalosporin; composition; formula; substance; crystalline
Prior art date: 2003-03-27

Application number

ZA200507760A

Other languages

English (en)

Inventor

Berghausen Joerg

Original Assignee

Basilea Pharmaceutica Ag

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.)

2003-03-27

Filing date

2005-09-26

Publication date

2007-06-27

2005-09-26 Application filed by Basilea Pharmaceutica Ag filed Critical Basilea Pharmaceutica Ag

2007-06-27 Publication of ZA200507760B publication Critical patent/ZA200507760B/en

Links

229930186147 Cephalosporin Natural products 0.000 title claims abstract description 65
229940124587 cephalosporin Drugs 0.000 title claims abstract description 65
150000001780 cephalosporins Chemical class 0.000 title claims abstract description 55
150000001875 compounds Chemical class 0.000 claims abstract description 25
239000000203 mixture Substances 0.000 claims description 28
238000000034 method Methods 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
239000003960 organic solvent Substances 0.000 claims description 13
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 11
-1 cephalosporin compounds Chemical class 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
238000000634 powder X-ray diffraction Methods 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 6
238000011321 prophylaxis Methods 0.000 claims description 6
238000003756 stirring Methods 0.000 claims description 6
208000035473 Communicable disease Diseases 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 2
GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical compound O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 claims description 2
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims 8
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 abstract description 2
241000589517 Pseudomonas aeruginosa Species 0.000 abstract description 2
241000295644 Staphylococcaceae Species 0.000 abstract description 2
239000003242 anti bacterial agent Substances 0.000 abstract description 2
230000000844 anti-bacterial effect Effects 0.000 abstract description 2
229940088710 antibiotic agent Drugs 0.000 abstract description 2
229960003085 meticillin Drugs 0.000 abstract description 2
230000003389 potentiating effect Effects 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
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 description 9
239000011575 calcium Substances 0.000 description 8
238000000113 differential scanning calorimetry Methods 0.000 description 8
235000002639 sodium chloride Nutrition 0.000 description 8
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
239000012876 carrier material Substances 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
238000003860 storage Methods 0.000 description 5
239000001828 Gelatine Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000002178 crystalline material Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000725 suspension Substances 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
229920005862 polyol Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
235000019759 Maize starch Nutrition 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000003925 fat Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000006186 oral dosage form Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
239000001993 wax Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229920000858 Cyclodextrin Polymers 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002065 inelastic X-ray scattering Methods 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000004684 trihydrates Chemical group 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/48—Methylene radicals, substituted by hetero rings
- C07D501/56—Methylene radicals, substituted by hetero rings with the 7-amino radical acylated by carboxylic acids containing hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; 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)
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)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ZA200507760A 2003-03-27 2005-09-26 Cephalosporin in crystalline form ZA200507760B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP03006815		2003-03-27

Publications (1)

Publication Number	Publication Date
ZA200507760B true ZA200507760B (en)	2007-06-27

Family

ID=33040912

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200507760A ZA200507760B (en)	2003-03-27	2005-09-26	Cephalosporin in crystalline form

Country Status (21)

Country	Link
US (2)	US7531650B2 (pl)
EP (1)	EP1606293B1 (pl)
JP (1)	JP5230934B2 (pl)
KR (1)	KR101121942B1 (pl)
CN (1)	CN1751051B (pl)
AT (1)	ATE440101T1 (pl)
AU (1)	AU2004224181B2 (pl)
BR (1)	BRPI0408716B1 (pl)
CA (1)	CA2519272C (pl)
CY (1)	CY1109615T1 (pl)
DE (1)	DE602004022643D1 (pl)
DK (1)	DK1606293T3 (pl)
ES (1)	ES2329244T3 (pl)
HK (1)	HK1085479A1 (pl)
MX (1)	MXPA05010083A (pl)
PL (1)	PL1606293T3 (pl)
PT (1)	PT1606293E (pl)
SI (1)	SI1606293T1 (pl)
TW (1)	TWI346117B (pl)
WO (1)	WO2004085444A1 (pl)
ZA (1)	ZA200507760B (pl)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2006059753A1 (en) *	2004-11-30	2006-06-08	Astellas Pharma Inc.	Novel oral pharmaceutical suspension of cefdinir crystal

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE758350A (fr) *	1969-12-30	1971-05-03	Pfizer	Procede de fabrication des sels mono- et bi-metalliques alcalins de l'alpha-carboxybenzylpenicilline
US3697506A (en) *	1970-08-07	1972-10-10	Pfizer	Crystalline alkali metal salts of {60 -carboxybenzylpenicillin and process therefor
JPS5579393A (en) *	1978-12-11	1980-06-14	Takeda Chem Ind Ltd	Cephalosporin derivative and its preparation
GR78221B (pl)	1980-02-01	1984-09-26	Ciba Geigy Ag
US4432987A (en) *	1982-04-23	1984-02-21	Pfizer Inc.	Crystalline benzenesulfonate salts of sultamicillin
FR2532315A1 (fr)	1982-08-27	1984-03-02	Rhone Poulenc Sante	Formes cristallisees de sels d'addition avec des acides, de l'((amino-2-thiazolyl-4)-2 methoxyimino-2 acetamido)-7 carboxy-2 (dioxo-5,6 formylmethyl-4 tetrahydro-1,4,5,6 triazine-1,2,4 yl-3) thio-2 vinyl)-3 oxo-8 thia-5 aza-1 bicyclo(4.2.0) octene-2 isomere syn, forme e et leur preparation
US4634556A (en) *	1985-05-10	1987-01-06	Schering Corporation	Crystalline sodium (5R, 6S, 8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxylate and process for making same
AU615966B2 (en) *	1987-12-04	1991-10-17	Takeda Chemical Industries Ltd.	Crystals of cephem hydrochloride
JPH02101081A (ja) *	1988-10-08	1990-04-12	Meiji Seika Kaisha Ltd	セファロスポリン誘導体結晶性二塩酸塩及びその製造法
CA2011116C (en) *	1989-03-06	1999-11-16	Murray A. Kaplan	Lyophilized bmy-28142 dihydrochloride for parenteral use
US5492903A (en) *	1990-06-19	1996-02-20	Takeda Chemical Industries Ltd.	Crystalline esters of (+)-(5R, 6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]he
JP2575590B2 (ja) *	1992-07-31	1997-01-29	塩野義製薬株式会社	トリアゾリルチオメチルチオセファロスポリン塩酸塩およびその水和物結晶ならびにそれらの製法
EP0581552B1 (en)	1992-07-31	1998-04-22	Shionogi & Co., Ltd.	Triazolylthiomethylthio cephalosporin hyrochloride, its crystalline hydrate and the production of the same
KR100296810B1 (ko) *	1993-03-12	2001-10-24	로렌스 티. 마이젠헬더	결정성세프티오퍼유리산
HU224196B1 (hu) *	1996-09-20	2005-06-28	Meiji Seika Kaisha Ltd.	Cefditoren-pivoxil kristályos formája, és eljárás annak előállítására
TW415949B (en)	1996-12-19	2000-12-21	Hoffmann La Roche	Vinyl pyrrolidine cephalosporin derivatives with basic substituents
AU754732B2 (en) *	1998-06-15	2002-11-21	Basilea Pharmaceutica International Ag, Allschwil	Derivatives of 3-(2-oxo-(1,3')bipyrrolidinyl-3-ylidenemethyl)-cephems
US6232306B1 (en)	1998-06-15	2001-05-15	Hoffmann-La Roche Inc.	Derivatives of 3-(2-oxo-[1,3′]bipyrrolidinyl-3-ylidenemethyl)-cephams
US6504025B2 (en) *	2000-05-24	2003-01-07	Basilea Pharmaceutica Ag	Process for the preparation of vinyl-pyrrolidinone cephalosporin derivatives
USRE40794E1 (en) *	2001-09-26	2009-06-23	Merck & Co., Inc.	Crystalline forms of carbapenem antibiotics and methods of preparation

2004
- 2004-03-15 SI SI200431215T patent/SI1606293T1/sl unknown
- 2004-03-15 CN CN2004800042140A patent/CN1751051B/zh not_active Expired - Lifetime
- 2004-03-15 PL PL04720595T patent/PL1606293T3/pl unknown
- 2004-03-15 BR BRPI0408716-0A patent/BRPI0408716B1/pt active IP Right Grant
- 2004-03-15 US US10/547,648 patent/US7531650B2/en active Active
- 2004-03-15 AT AT04720595T patent/ATE440101T1/de active
- 2004-03-15 JP JP2006504690A patent/JP5230934B2/ja not_active Expired - Lifetime
- 2004-03-15 PT PT04720595T patent/PT1606293E/pt unknown
- 2004-03-15 EP EP04720595A patent/EP1606293B1/en not_active Expired - Lifetime
- 2004-03-15 DK DK04720595T patent/DK1606293T3/da active
- 2004-03-15 CA CA2519272A patent/CA2519272C/en not_active Expired - Fee Related
- 2004-03-15 MX MXPA05010083A patent/MXPA05010083A/es active IP Right Grant
- 2004-03-15 ES ES04720595T patent/ES2329244T3/es not_active Expired - Lifetime
- 2004-03-15 AU AU2004224181A patent/AU2004224181B2/en not_active Ceased
- 2004-03-15 WO PCT/EP2004/002667 patent/WO2004085444A1/en active Application Filing
- 2004-03-15 DE DE602004022643T patent/DE602004022643D1/de not_active Expired - Lifetime
- 2004-03-26 TW TW093108308A patent/TWI346117B/zh not_active IP Right Cessation
2005
- 2005-09-26 ZA ZA200507760A patent/ZA200507760B/en unknown
- 2005-09-26 KR KR1020057018075A patent/KR101121942B1/ko active IP Right Grant
2006
- 2006-05-15 HK HK06105568.5A patent/HK1085479A1/xx not_active IP Right Cessation
2009
- 2009-04-01 US US12/416,461 patent/US8093377B2/en active Active
- 2009-11-12 CY CY20091101186T patent/CY1109615T1/el unknown

Also Published As

Publication number	Publication date
MXPA05010083A (es)	2005-11-23
TW200502237A (en)	2005-01-16
DE602004022643D1 (de)	2009-10-01
CA2519272C (en)	2010-06-08
EP1606293A1 (en)	2005-12-21
ES2329244T3 (es)	2009-11-24
BRPI0408716B8 (pl)	2021-05-25
TWI346117B (en)	2011-08-01
US7531650B2 (en)	2009-05-12
CY1109615T1 (el)	2014-08-13
BRPI0408716A (pt)	2006-03-07
CN1751051A (zh)	2006-03-22
CA2519272A1 (en)	2004-10-07
AU2004224181B2 (en)	2011-06-02
JP5230934B2 (ja)	2013-07-10
KR101121942B1 (ko)	2012-03-09
PL1606293T3 (pl)	2010-01-29
WO2004085444A1 (en)	2004-10-07
HK1085479A1 (en)	2006-08-25
DK1606293T3 (da)	2009-10-05
EP1606293B1 (en)	2009-08-19
PT1606293E (pt)	2009-10-14
AU2004224181A1 (en)	2004-10-07
US20060167242A1 (en)	2006-07-27
SI1606293T1 (sl)	2009-10-31
JP2006521309A (ja)	2006-09-21
ATE440101T1 (de)	2009-09-15
CN1751051B (zh)	2010-06-09
BRPI0408716B1 (pt)	2017-08-29
US8093377B2 (en)	2012-01-10
US20090192306A1 (en)	2009-07-30
KR20050111787A (ko)	2005-11-28

Publication	Publication Date	Title
AU2018203806B2 (en)	2020-04-02	Tazobactam arginine antibiotic compositions
EP0581552A2 (en)	1994-02-02	Triazolylthiomethylthio cephalosporin hyrochloride, its crystalline hydrate and the production of the same
SK287375B6 (sk)	2010-08-09	Kryštalická forma N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H- pyrolo[2,3-d]pyrimidín-5-yl) etyl]benzoyl]-L-glutámovej kyseliny a spôsob jej prípravy
NZ508303A (en)	2001-07-27	Mesylate trihydrate salt of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)-ethyl)-6-chloro-1,3-dihydro-2(1H)-indol-2-one (ziprasidone) useful as a dopamine D2 antagonist
CA1298288C (en)	1992-03-31	Cephalosporin salts and injectable compositions
US8476425B1 (en)	2013-07-02	Tazobactam arginine compositions
IE861984L (en)	1987-01-27	Crystalline salt of guanine derivative
HU187068B (en)	1985-11-28	Process for preparing crystallic benzenesulphonates of sulfamicilline
CA1338780C (en)	1996-12-10	Water-soluble antibiotic composition and water-soluble salts of new cephem compounds
HU210716A9 (en)	1995-06-28	Rifapentine hydrohalides
EP1277750B1 (en)	2004-10-13	Hydrates and crystals of a neuraminic acid compound
ZA200507760B (en)	2007-06-27	Cephalosporin in crystalline form
GB1589841A (en)	1981-05-20	Solid cephalosporin salt
EP0587121B1 (en)	1998-11-11	Crystalline dihydrate of a cephalosporin dihydrochloride salt and injectable compositions thereof
SK18922001A3 (sk)	2002-04-04	Difosfátová soľ 4''substituovaného 9-deoxo-9-aza- 9a-homoerytromycínového derivátu a farmaceutické kompozície s jej obsahom
US20080227768A1 (en)	2008-09-18	Crystal of 1-Methylcarbapenem Compound
IE61325B1 (en)	1994-11-02	Crystalline salts of [3s(z)]-2[[[1-(2-amino-4-thiazolyl)-2-[[2,2-dimethyl-4-oxo-1 -(sulfooxy)-3-azetidinyl]amino]-2-oxoethylidene] amino]oxy]acetic acid
HU182498B (en)	1984-01-30	Process for producing 7-bracket-iminoacetamido-bracket closed-3-thiomethyl-ceph-3-eme-4-caraoxylic acid
PL196046B1 (pl)	2007-11-30	Postać krystaliczna monohydratu cytrynianu (2S,3S)-N-(2-metoksy-5-t-butylofenylo)metylo-2-difenylometylo-1-azabicyklo[2.2.2]oktano-3-aminy, środek farmaceutyczny, zastosowanie tej postaci krystalicznej i sposób wytwarzania tej postaci krystalicznej
PT96531A (pt)	1991-10-15	Processo para a preparacao de um hidrocloreto cristalino de um antibiotico beta-lactamico
US5391729A (en)	1995-02-21	Crystalline dihydrate of a cephalosporin salt
US4094979A (en)	1978-06-13	Orally active cephalosporins
JPH09104694A (ja)	1997-04-22	アルベカシンと（−）−シス−１，２−エポキシプロピルホスホン酸との付加塩およびその製造法、ならびに抗菌剤