CA1284994C - Cephalosporin salts and injectable compositions - Google Patents

Cephalosporin salts and injectable compositions

Info

Publication number: CA1284994C
Authority: CA; Canada
Prior art keywords: admixture; crystalline; acid addition; zwitterion; alpha
Prior art date: 1985-08-05
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.): Expired - Lifetime

Application number

CA000514766A

Other languages

English (en)

French (fr)

Inventor

Murray Arthur Kaplan

Thomas W. Hudyma

Robert Alan Lipper

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Co

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.)

1985-08-05

Filing date

1986-07-28

Publication date

1991-06-18

1986-07-28 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1991-06-18 Application granted granted Critical

1991-06-18 Publication of CA1284994C publication Critical patent/CA1284994C/en

2008-06-18 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

-1 Cephalosporin salts Chemical class 0.000 title claims abstract description 10
239000007972 injectable composition Substances 0.000 title abstract description 7
229930186147 Cephalosporin Natural products 0.000 title abstract description 3
229940124587 cephalosporin Drugs 0.000 title abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 45
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
229910001868 water Inorganic materials 0.000 claims abstract description 32
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 12
238000002425 crystallisation Methods 0.000 claims abstract description 10
230000008025 crystallization Effects 0.000 claims abstract description 10
238000010790 dilution Methods 0.000 claims abstract description 9
239000012895 dilution Substances 0.000 claims abstract description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 9
235000011007 phosphoric acid Nutrition 0.000 claims description 8
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical group NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 6
229960003646 lysine Drugs 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 4
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical group OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
238000000634 powder X-ray diffraction Methods 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
239000012453 solvate Substances 0.000 claims 2
229910019142 PO4 Inorganic materials 0.000 claims 1
150000004677 hydrates Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 30
239000013078 crystal Substances 0.000 abstract description 10
238000005406 washing Methods 0.000 abstract description 4
238000000862 absorption spectrum Methods 0.000 abstract description 2
HVFLCNVBZFFHBT-ZKDACBOMSA-N cefepime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 HVFLCNVBZFFHBT-ZKDACBOMSA-N 0.000 abstract description 2
238000001035 drying Methods 0.000 abstract description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract description 2
235000011149 sulphuric acid Nutrition 0.000 abstract description 2
238000002329 infrared spectrum Methods 0.000 abstract 1
238000002360 preparation method Methods 0.000 description 14
101100059652 Mus musculus Cetn1 gene Proteins 0.000 description 11
101100059655 Mus musculus Cetn2 gene Proteins 0.000 description 11
238000003828 vacuum filtration Methods 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000843 powder Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
230000000694 effects Effects 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
DQSGVVGOPRWTKI-QVFAWCHISA-N atazanavir sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
239000004472 Lysine Substances 0.000 description 4
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000002585 base Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000002609 medium Substances 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
238000001291 vacuum drying Methods 0.000 description 4
239000004475 Arginine Substances 0.000 description 3
241000196224 Codium Species 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
239000000047 product Substances 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
238000010268 HPLC based assay Methods 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
108010013381 Porins Proteins 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
230000003139 buffering effect Effects 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
229960000484 ceftazidime Drugs 0.000 description 2
NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000010899 nucleation Methods 0.000 description 2
238000004806 packaging method and process Methods 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
102000007739 porin activity proteins Human genes 0.000 description 2
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000005057 refrigeration Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000008223 sterile water Substances 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 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
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
244000228957 Ferula foetida Species 0.000 description 1
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 description 1
241001465754 Metazoa Species 0.000 description 1
244000192897 Mitragyna stipulosa Species 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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241001237728 Precis Species 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
238000004380 ashing Methods 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
229960004261 cefotaxime Drugs 0.000 description 1
AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
GOHCTCOGYKAJLZ-UHFFFAOYSA-N ctep Chemical compound CC=1N(C=2C=CC(OC(F)(F)F)=CC=2)C(C)=NC=1C#CC1=CC=NC(Cl)=C1 GOHCTCOGYKAJLZ-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000003387 muscular Effects 0.000 description 1
208000004613 nanophthalmos 3 Diseases 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
- 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
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
- 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)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Medicinal Preparation (AREA)

CA000514766A 1985-08-05 1986-07-28 Cephalosporin salts and injectable compositions Expired - Lifetime CA1284994C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76223585A	1985-08-05	1985-08-05
US762,235		1985-08-05

Publications (1)

Publication Number	Publication Date
CA1284994C true CA1284994C (en)	1991-06-18

Family

ID=25064475

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000514766A Expired - Lifetime CA1284994C (en)	1985-08-05	1986-07-28	Cephalosporin salts and injectable compositions

Country Status (34)

Country	Link
JP (1)	JPH0615548B2 (de)
KR (1)	KR930003121B1 (de)
AR (1)	AR243894A1 (de)
AT (1)	AT390957B (de)
AU (1)	AU597262B2 (de)
BE (1)	BE905219A (de)
CA (1)	CA1284994C (de)
CH (1)	CH675581A5 (de)
CS (2)	CS276717B6 (de)
CY (1)	CY1614A (de)
DD (2)	DD254941A5 (de)
DE (1)	DE3626375A1 (de)
DK (1)	DK162053C (de)
EG (1)	EG18003A (de)
ES (1)	ES2002112A6 (de)
FI (1)	FI84484C (de)
FR (1)	FR2585705B1 (de)
GB (1)	GB2179936B (de)
GR (1)	GR862055B (de)
HK (1)	HK99691A (de)
HU (1)	HU196602B (de)
IE (1)	IE59222B1 (de)
IL (1)	IL79608A (de)
IT (1)	IT1197067B (de)
LU (2)	LU88574I2 (de)
MY (1)	MY102212A (de)
NL (1)	NL8601991A (de)
OA (1)	OA08672A (de)
PT (1)	PT83134B (de)
SE (1)	SE469633B (de)
SG (1)	SG79791G (de)
SU (1)	SU1516013A3 (de)
YU (1)	YU45793B (de)
ZA (1)	ZA865842B (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4883868A (en) *	1984-12-27	1989-11-28	Banyu Pharmaceutical Co., Ltd.	7-amino-3-(substituted isoindolinium)methyl-3-cephem derivatives
US4959469A (en) *	1984-12-27	1990-09-25	Banyu Pharmaceutical Company, Ltd.	Crystalline cephalosporin compounds
US5244891A (en) *	1985-08-05	1993-09-14	Bristol-Myers Squibb Company	Injectable compositions of cefepime dihydrochloride hydrate
US4910301A (en) *	1985-08-05	1990-03-20	Bristol-Myers Company	Cefepime cephalosporin salts
US4808617A (en) *	1985-12-18	1989-02-28	Bristol-Myers Company	Lyophilized or precipitated cephalosporin zwitterion and salt combination
KR950010084B1 (ko) *	1987-06-25	1995-09-06	반유세이야꾸 가부시끼가이샤	결정성 세팔로스포린 화합물, 그의 제조법 및 그의 제조 중간체
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
CA2101571A1 (en) *	1992-09-08	1994-03-09	Elizabeth A. Garofalo	Crystalline dihydrate of a cephalosporin dihydrate salt and injectable compositions thereof
ATE202109T1 (de) *	1993-03-12	2001-06-15	Upjohn Co	Kristallines ceftiofur (freie säure)
EP0638573A1 (de) *	1993-08-10	1995-02-15	Lucky Ltd.	Kristalline Hydrate eines Cephalosporins und Verfahren zu ihrer Herstellung
ES2298850T3 (es)	2003-12-23	2008-05-16	Sandoz Gmbh	Proceso para la produccion de intermedios para utilizar en la sintesis de la cefalosporina.
WO2008056221A2 (en) *	2006-11-06	2008-05-15	Orchid Chemicals & Pharmaceuticals Limited	Crystalline sulfate salt of cephalosporin antibiotic
DE102012101680A1 (de) *	2012-02-29	2013-08-29	Aicuris Gmbh & Co. Kg	Pharmazeutische Zubereitung enthaltend ein antiviral wirksames Dihydrochinazolinderivat

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS55151588A (en) *	1979-05-14	1980-11-26	Takeda Chem Ind Ltd	Preparation of cephalosporin salt crystal
CA1213882A (en) *	1982-03-04	1986-11-12	Jun Okumura	Cephalosporins
US4406899A (en) *	1982-03-04	1983-09-27	Bristol-Myers Company	Cephalosporins
US4525473A (en) *	1983-03-30	1985-06-25	Bristol-Myers Company	Cephalosporins
DE3419015A1 (de) *	1984-05-22	1985-11-28	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von cephalosporinen
GB8424692D0 (en) *	1984-10-01	1984-11-07	Glaxo Group Ltd	Chemical compounds
GB2165245B (en) *	1984-10-01	1988-05-25	Glaxo Group Ltd	Chemical compounds

1986
- 1986-07-28 CA CA000514766A patent/CA1284994C/en not_active Expired - Lifetime
- 1986-07-28 FR FR8610892A patent/FR2585705B1/fr not_active Expired
- 1986-07-29 AR AR86304717A patent/AR243894A1/es active
- 1986-07-30 AU AU60694/86A patent/AU597262B2/en not_active Expired
- 1986-07-31 YU YU137186A patent/YU45793B/sh unknown
- 1986-08-01 IE IE207886A patent/IE59222B1/en not_active IP Right Cessation
- 1986-08-01 FI FI863155A patent/FI84484C/fi not_active IP Right Cessation
- 1986-08-04 JP JP61183288A patent/JPH0615548B2/ja not_active Expired - Lifetime
- 1986-08-04 DE DE19863626375 patent/DE3626375A1/de not_active Ceased
- 1986-08-04 GR GR862055A patent/GR862055B/el unknown
- 1986-08-04 ZA ZA865842A patent/ZA865842B/xx unknown
- 1986-08-04 SE SE8603308A patent/SE469633B/sv not_active IP Right Cessation
- 1986-08-04 DK DK371886A patent/DK162053C/da not_active IP Right Cessation
- 1986-08-04 BE BE07217010A patent/BE905219A/fr not_active IP Right Cessation
- 1986-08-04 LU LU88574C patent/LU88574I2/fr unknown
- 1986-08-04 CS CS865827A patent/CS276717B6/cs unknown
- 1986-08-04 GB GB8618989A patent/GB2179936B/en not_active Expired
- 1986-08-04 CH CH3117/86A patent/CH675581A5/de not_active IP Right Cessation
- 1986-08-04 LU LU86540A patent/LU86540A1/fr unknown
- 1986-08-04 CS CS903570A patent/CS276849B6/cs unknown
- 1986-08-04 SU SU864027914A patent/SU1516013A3/ru active
- 1986-08-04 PT PT83134A patent/PT83134B/pt unknown
- 1986-08-04 IT IT21409/86A patent/IT1197067B/it active Protection Beyond IP Right Term
- 1986-08-04 IL IL79608A patent/IL79608A/xx not_active IP Right Cessation
- 1986-08-04 NL NL8601991A patent/NL8601991A/nl not_active Application Discontinuation
- 1986-08-05 ES ES8600872A patent/ES2002112A6/es not_active Expired
- 1986-08-05 AT AT0211086A patent/AT390957B/de not_active IP Right Cessation
- 1986-08-05 OA OA58918A patent/OA08672A/xx unknown
- 1986-08-05 DD DD86293433A patent/DD254941A5/de unknown
- 1986-08-05 HU HU863376A patent/HU196602B/hu unknown
- 1986-08-05 KR KR1019860006445A patent/KR930003121B1/ko not_active Expired - Lifetime
1987
- 1987-09-29 MY MYPI87002279A patent/MY102212A/en unknown
1988
- 1988-03-30 DD DD88314213A patent/DD268395A5/de unknown
1989
- 1989-08-04 EG EG489/86A patent/EG18003A/xx active
1991
- 1991-10-02 SG SG797/91A patent/SG79791G/en unknown
- 1991-12-05 HK HK996/91A patent/HK99691A/xx not_active IP Right Cessation
1992
- 1992-07-10 CY CY1614A patent/CY1614A/en unknown

Also Published As

Publication number	Publication date
AU6069486A (en)	1987-02-12
LU88574I2 (fr)	1995-03-01
ATA211086A (de)	1990-01-15
FI863155A7 (fi)	1987-02-06
CS276717B6 (en)	1992-08-12
SU1516013A3 (ru)	1989-10-15
CY1614A (en)	1992-07-10
SE8603308D0 (sv)	1986-08-04
BE905219A (fr)	1987-02-04
IL79608A (en)	1991-07-18
CH675581A5 (de)	1990-10-15
LU86540A1 (fr)	1987-03-06
DK162053B (da)	1991-09-09
DD268395A5 (de)	1989-05-31
IE862078L (en)	1987-02-05
AR243894A1 (es)	1993-09-30
DE3626375A1 (de)	1987-02-12
IT1197067B (it)	1988-11-25
DK371886D0 (da)	1986-08-04
ZA865842B (en)	1987-04-29
AU597262B2 (en)	1990-05-31
FR2585705A1 (fr)	1987-02-06
PT83134A (en)	1986-09-01
FI84484C (fi)	1991-12-10
KR930003121B1 (ko)	1993-04-19
SE8603308L (sv)	1987-02-06
YU137186A (en)	1987-12-31
OA08672A (en)	1989-03-31
GB8618989D0 (en)	1986-09-17
YU45793B (sh)	1992-07-20
AT390957B (de)	1990-07-25
JPH0615548B2 (ja)	1994-03-02
KR880002530A (ko)	1988-05-09
JPS62103090A (ja)	1987-05-13
HUT41802A (en)	1987-05-28
SE469633B (sv)	1993-08-09
NL8601991A (nl)	1987-03-02
IL79608A0 (en)	1986-11-30
HK99691A (en)	1991-12-13
HU196602B (en)	1988-12-28
DK162053C (da)	1992-02-10
DK371886A (da)	1987-02-06
CS276849B6 (en)	1992-08-12
FI863155A0 (fi)	1986-08-01
GB2179936B (en)	1989-04-26
FR2585705B1 (fr)	1989-01-13
MY102212A (en)	1992-05-15
PT83134B (pt)	1989-07-31
FI84484B (fi)	1991-08-30
SG79791G (en)	1991-11-15
IT8621409A0 (it)	1986-08-04
GB2179936A (en)	1987-03-18
EG18003A (en)	1991-08-30
IT8621409A1 (it)	1988-02-04
DD254941A5 (de)	1988-03-16
ES2002112A6 (es)	1988-07-16
IE59222B1 (en)	1994-01-26
GR862055B (en)	1986-12-24

Legal Events

Date	Code	Title	Description
2008-06-18	MKEX	Expiry

Publication	Publication Date	Title
US4910301A (en)	1990-03-20	Cefepime cephalosporin salts
AU597262B2 (en)	1990-05-31	Cephalosporin salts and injectable compositions
US4609653A (en)	1986-09-02	Crystalline cephem-acid addition salts and processes for their preparation
US5244891A (en)	1993-09-14	Injectable compositions of cefepime dihydrochloride hydrate
US4994451A (en)	1991-02-19	Cephalosporin salts and injectable compositions
DK151340B (da)	1987-11-23	Analogifremgangsmaade til fremstilling af et krystallinsk cephalosporinderivat
JPS61180789A (ja)	1986-08-13	セフブペラゾンの結晶性トリエチルアミン塩
CA1236089A (en)	1988-05-03	Ceftazidime
US4680389A (en)	1987-07-14	Temperature stable crystalline di(1-methyl-2-pyrralidinone) and di(N-formylpyrrolidine) adducts of cephalosporin derivatives
CA1282407C (en)	1991-04-02	Crystalline cephem carboxylic acid addition salt
WO2005094800A2 (en)	2005-10-13	A co-precipitated cefepime composition and process for preparation thereof
CA1254569A (en)	1989-05-23	Sulfonic acid salts of 6-amino-1,5-dihydro-4h- imidazo¬4,5-c\|pyridin-4-one