LU85650A1 - Perfectionnements relatifs a des derives de cephalosporine - Google Patents

Perfectionnements relatifs a des derives de cephalosporine Download PDF

Info

Publication number: LU85650A1
Authority: LU; Luxembourg
Prior art keywords: cephalexin; monohydrate; solvate; hydrochloride; crystalline
Prior art date: 1983-12-01

Application number

LU85650A

Other languages

English (en)

French (fr)

Inventor

Joseph Michael Indelicato

Gary Lowell Engel

Harry Albert Rose

Lawrence Joseph Mcshane

Kuo Shang Yang

Original Assignee

Lilly Co Eli

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.)

1983-12-01

Filing date

1984-11-27

Publication date

1985-07-17

1984-11-27 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1985-07-17 Publication of LU85650A1 publication Critical patent/LU85650A1/fr

Links

229930186147 Cephalosporin Natural products 0.000 title description 4
229940124587 cephalosporin Drugs 0.000 title description 4
150000001780 cephalosporins Chemical class 0.000 title description 4
LSBUIZREQYVRSY-CYJZLJNKSA-N (6r,7r)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrochloride Chemical compound Cl.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 LSBUIZREQYVRSY-CYJZLJNKSA-N 0.000 claims description 48
229940084959 cephalexin hydrochloride Drugs 0.000 claims description 48
239000012453 solvate Substances 0.000 claims description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
150000004682 monohydrates Chemical class 0.000 claims description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
239000004615 ingredient Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 7
239000012298 atmosphere Substances 0.000 claims description 7
229940106164 cephalexin Drugs 0.000 claims description 7
AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 6
239000013078 crystal Substances 0.000 claims description 5
238000007614 solvation Methods 0.000 claims description 5
230000036571 hydration Effects 0.000 claims description 4
238000006703 hydration reaction Methods 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 2
230000000887 hydrating effect Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
229940047526 cephalexin monohydrate Drugs 0.000 description 14
YGZIWEZFFBPCLN-UHFFFAOYSA-N n,3-bis(2-chloroethyl)-4-hydroperoxy-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine Chemical compound OOC1CCOP(=O)(NCCCl)N1CCCl YGZIWEZFFBPCLN-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
230000003204 osmotic effect Effects 0.000 description 13
239000000203 mixture Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000000463 material Substances 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
239000002775 capsule Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 6
239000002002 slurry Substances 0.000 description 6
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
229940069328 povidone Drugs 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
235000021355 Stearic acid Nutrition 0.000 description 4
238000002441 X-ray diffraction Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000010949 copper Substances 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
-1 phenylacetamido Chemical group 0.000 description 4
239000008117 stearic acid Substances 0.000 description 4
230000009466 transformation Effects 0.000 description 4
238000005169 Debye-Scherrer Methods 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000013270 controlled release Methods 0.000 description 3
238000010586 diagram Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
239000012729 immediate-release (IR) formulation Substances 0.000 description 3
238000000634 powder X-ray diffraction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000004580 weight loss Effects 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000009826 distribution Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
239000002245 particle Substances 0.000 description 2
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000008107 starch Substances 0.000 description 2
NPHULPIAPWNOOH-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(2,3-dihydroindol-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCC2=CC=CC=C12 NPHULPIAPWNOOH-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
101100230604 Caenorhabditis elegans hcp-3 gene Proteins 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000068988 Glycine max 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
238000005481 NMR spectroscopy Methods 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
239000002253 acid Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000012296 anti-solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036765 blood level Effects 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004455 differential thermal analysis Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000004513 sizing Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
230000017105 transposition Effects 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000004457 water analysis Methods 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
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
- 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)
Medicinal Preparation (AREA)

LU85650A 1983-12-01 1984-11-27 Perfectionnements relatifs a des derives de cephalosporine LU85650A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/556,887 US4600773A (en)	1983-12-01	1983-12-01	Crystalline cephalexin hydrochloride monohydrate
US55688783		1983-12-01

Publications (1)

Publication Number	Publication Date
LU85650A1 true LU85650A1 (fr)	1985-07-17

Family

ID=24223233

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU85650A LU85650A1 (fr)	1983-12-01	1984-11-27	Perfectionnements relatifs a des derives de cephalosporine

Country Status (46)

Country	Link
US (1)	US4600773A (el)
EP (1)	EP0143658B1 (el)
JP (1)	JPS60132990A (el)
KR (1)	KR870000527B1 (el)
AT (1)	AT390616B (el)
AU (1)	AU566080B2 (el)
BE (1)	BE901142A (el)
BG (1)	BG40966A3 (el)
BR (1)	BR8406037A (el)
CH (1)	CH661732A5 (el)
CS (1)	CS248725B2 (el)
CY (1)	CY1505A (el)
DD (1)	DD229410A5 (el)
DE (1)	DE3443065A1 (el)
DK (1)	DK158354C (el)
ES (1)	ES8602011A1 (el)
FI (1)	FI80274C (el)
FR (1)	FR2555990B1 (el)
GB (1)	GB2150566B (el)
GR (1)	GR81043B (el)
GT (1)	GT198400146A (el)
HK (1)	HK92089A (el)
HU (1)	HU192516B (el)
IE (1)	IE57886B1 (el)
IL (1)	IL73639A (el)
IN (1)	IN163078B (el)
IT (1)	IT1177329B (el)
JO (1)	JO1347B1 (el)
LU (1)	LU85650A1 (el)
MA (1)	MA20279A1 (el)
MX (1)	MX159670A (el)
MY (1)	MY102966A (el)
NL (1)	NL8403588A (el)
NO (1)	NO844711L (el)
NZ (1)	NZ210357A (el)
OA (1)	OA07876A (el)
PH (1)	PH20849A (el)
PL (1)	PL146014B1 (el)
PT (1)	PT79553B (el)
SE (1)	SE464026B (el)
SG (1)	SG59789G (el)
SU (1)	SU1251807A3 (el)
YU (1)	YU45680B (el)
ZA (1)	ZA849224B (el)
ZM (1)	ZM6384A1 (el)
ZW (1)	ZW19084A1 (el)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2555989B1 (fr) *	1983-12-06	1987-02-20	Bristol Myers Sa	Monohydrate de chlorocephadroxyle
DE150507T1 (de) *	1983-12-29	1987-02-26	Mochida Pharmaceutical Co., Ltd., Tokio/Tokyo	Cephalosporinverbindungen, verfahren zu ihrer herstellung und pharmazeutishe praeparate.
JPS60142987A (ja) *	1983-12-29	1985-07-29	Mochida Pharmaceut Co Ltd	セフアロスポリン誘導体
US4840945A (en) *	1985-04-01	1989-06-20	Mochida Pharmaceutical Co., Ltd.	Cephalosporin derivatives
US4775751A (en) *	1985-06-03	1988-10-04	Eli Lilly & Company	Process for cephalexin hydrochloride alcoholates
JPS63132893A (ja) *	1986-11-25	1988-06-04	Mochida Pharmaceut Co Ltd	新規セフアロスポリン誘導体、その製法およびそれらを有効成分とする抗菌剤
US4880798A (en) *	1986-11-25	1989-11-14	Mochida Pharmaceutical Co., Ltd.	Cephalosporin derivatives
US5721229A (en) *	1995-12-26	1998-02-24	Veterinary Pharmacy Corporation	Soluble forms of cephalosporins and treatment of animals
GB9717629D0 (en)	1997-08-21	1997-10-22	Johnson Matthey Plc	Removal of residual organic solvents
AT413282B (de) *	2002-02-01	2006-01-15	Sandoz Ag	Kristalline salze der 7-(((5-amino-1,2,4-thiadiazol-3-yl) (fluoromethoxy-imino)acetyl)amino)-3- ((imino-1-piperazinylmethyl)
US20040033262A1 (en) *	2002-08-19	2004-02-19	Orchid Health Care	Sustained release pharmaceutical composition of a cephalosporin antibiotic

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3507861A (en) *	1966-09-14	1970-04-21	Lilly Co Eli	Certain 3-methyl-cephalosporin compounds
US3655656A (en) *	1970-06-04	1972-04-11	Lilly Co Eli	Crystalline cephalexin monohydrate
DE2317179C2 (de) *	1973-04-05	1982-11-25	Bristol-Myers Co., 10154 New York, N.Y.	Verfahren zur Herstellung der relativ wasserunlöslichen kristallinen Form von Cefalexinmonohydrat
US3985747A (en) *	1974-05-24	1976-10-12	Bristol-Myers Company	Crystalline sesquihydrate of 7-[D-α-amino-α-(p-hydroxyphenyl)acetamido]-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid
JPS50151890A (el) *	1974-05-30	1975-12-06
CH642850A5 (it) *	1978-10-20	1984-05-15	Ausonia Farma Srl	Composizioni farmaceutiche ad attivita antibatterica contro infezioni da germi gram-positivi e gram-negativi.
NZ206600A (en) *	1983-05-11	1987-01-23	Alza Corp	Osmotic drug delivery device

1983
- 1983-12-01 US US06/556,887 patent/US4600773A/en not_active Expired - Lifetime
1984
- 1984-09-18 ZM ZM63/84A patent/ZM6384A1/xx unknown
- 1984-11-26 GT GT198400146A patent/GT198400146A/es unknown
- 1984-11-26 ZW ZW190/84A patent/ZW19084A1/xx unknown
- 1984-11-26 IL IL73639A patent/IL73639A/xx not_active IP Right Cessation
- 1984-11-26 ZA ZA849224A patent/ZA849224B/xx unknown
- 1984-11-26 PL PL1984250593A patent/PL146014B1/pl unknown
- 1984-11-26 AT AT0373284A patent/AT390616B/de not_active IP Right Cessation
- 1984-11-26 GR GR81043A patent/GR81043B/el unknown
- 1984-11-26 MX MX5772A patent/MX159670A/es unknown
- 1984-11-26 BG BG067674A patent/BG40966A3/xx unknown
- 1984-11-26 PT PT79553A patent/PT79553B/pt not_active IP Right Cessation
- 1984-11-26 NL NL8403588A patent/NL8403588A/nl not_active Application Discontinuation
- 1984-11-26 SU SU843815402A patent/SU1251807A3/ru active
- 1984-11-26 JO JO19841347A patent/JO1347B1/en active
- 1984-11-26 IN IN810/CAL/84A patent/IN163078B/en unknown
- 1984-11-26 YU YU199684A patent/YU45680B/sh unknown
- 1984-11-26 DE DE19843443065 patent/DE3443065A1/de active Granted
- 1984-11-26 SE SE8405954A patent/SE464026B/sv not_active IP Right Cessation
- 1984-11-26 KR KR1019840007392A patent/KR870000527B1/ko not_active IP Right Cessation
- 1984-11-26 CH CH5638/84A patent/CH661732A5/de not_active IP Right Cessation
- 1984-11-26 FI FI844631A patent/FI80274C/fi not_active IP Right Cessation
- 1984-11-27 IT IT23746/84A patent/IT1177329B/it active
- 1984-11-27 NZ NZ210357A patent/NZ210357A/en unknown
- 1984-11-27 FR FR8418042A patent/FR2555990B1/fr not_active Expired
- 1984-11-27 OA OA58453A patent/OA07876A/xx unknown
- 1984-11-27 DD DD84269940A patent/DD229410A5/de not_active IP Right Cessation
- 1984-11-27 LU LU85650A patent/LU85650A1/fr unknown
- 1984-11-27 IE IE3033/84A patent/IE57886B1/en not_active IP Right Cessation
- 1984-11-27 AU AU35897/84A patent/AU566080B2/en not_active Ceased
- 1984-11-27 BE BE6/48038A patent/BE901142A/fr not_active IP Right Cessation
- 1984-11-27 JP JP59251491A patent/JPS60132990A/ja active Granted
- 1984-11-27 NO NO844711A patent/NO844711L/no unknown
- 1984-11-27 DK DK561284A patent/DK158354C/da not_active IP Right Cessation
- 1984-11-27 ES ES538019A patent/ES8602011A1/es not_active Expired
- 1984-11-27 PH PH31493A patent/PH20849A/en unknown
- 1984-11-28 MA MA20503A patent/MA20279A1/fr unknown
- 1984-11-28 CS CS849120A patent/CS248725B2/cs unknown
- 1984-11-28 HU HU844394A patent/HU192516B/hu not_active IP Right Cessation
- 1984-11-28 EP EP84308266A patent/EP0143658B1/en not_active Expired
- 1984-11-28 BR BR8406037A patent/BR8406037A/pt unknown
- 1984-11-28 CY CY1505A patent/CY1505A/xx unknown
- 1984-11-28 GB GB08430073A patent/GB2150566B/en not_active Expired
1987
- 1987-10-01 MY MYPI87002808A patent/MY102966A/en unknown
1989
- 1989-09-07 SG SG597/89A patent/SG59789G/en unknown
- 1989-11-16 HK HK920/89A patent/HK92089A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU3589784A (en)	1985-06-06
DK158354C (da)	1990-10-01
NL8403588A (nl)	1985-07-01
FI844631A0 (fi)	1984-11-26
OA07876A (fr)	1986-11-20
CY1505A (en)	1990-08-03
DD229410A5 (de)	1985-11-06
HU192516B (en)	1987-06-29
PT79553B (en)	1986-12-15
FI80274B (fi)	1990-01-31
IT1177329B (it)	1987-08-26
FI80274C (fi)	1990-05-10
PL250593A1 (en)	1985-07-30
IL73639A0 (en)	1985-02-28
MY102966A (en)	1993-03-31
JPH0548234B2 (el)	1993-07-20
ZM6384A1 (en)	1985-07-22
ES538019A0 (es)	1985-11-01
IT8423746A1 (it)	1986-05-27
FI844631L (fi)	1985-06-02
PH20849A (en)	1987-05-08
DK561284D0 (da)	1984-11-27
GR81043B (en)	1985-03-27
IN163078B (el)	1988-08-06
BE901142A (fr)	1985-05-28
NZ210357A (en)	1988-05-30
BR8406037A (pt)	1985-08-27
ATA373284A (de)	1989-11-15
JPS60132990A (ja)	1985-07-16
EP0143658A3 (en)	1986-02-12
US4600773A (en)	1986-07-15
BG40966A3 (en)	1987-03-14
PL146014B1 (en)	1988-12-31
DK158354B (da)	1990-05-07
CS248725B2 (en)	1987-02-12
KR850004765A (ko)	1985-07-27
SE8405954D0 (sv)	1984-11-26
GB2150566B (en)	1987-08-26
JO1347B1 (en)	1986-11-30
NO844711L (no)	1985-06-03
SE8405954L (sv)	1985-06-02
CH661732A5 (de)	1987-08-14
MA20279A1 (fr)	1985-07-01
ZW19084A1 (en)	1985-06-12
SG59789G (en)	1989-12-29
SE464026B (sv)	1991-02-25
YU199684A (en)	1987-02-28
PT79553A (en)	1984-12-01
AT390616B (de)	1990-06-11
DE3443065A1 (de)	1985-06-20
ES8602011A1 (es)	1985-11-01
KR870000527B1 (ko)	1987-03-14
EP0143658A2 (en)	1985-06-05
GB2150566A (en)	1985-07-03
EP0143658B1 (en)	1989-03-22
GB8430073D0 (en)	1985-01-09
YU45680B (sh)	1992-07-20
SU1251807A3 (ru)	1986-08-15
GT198400146A (es)	1986-05-20
HK92089A (en)	1989-11-24
IE57886B1 (en)	1993-05-05
ZA849224B (en)	1986-07-30
HUT35685A (en)	1985-07-29
FR2555990A1 (fr)	1985-06-07
DE3443065C2 (el)	1989-03-23
IE843033L (en)	1985-06-01
FR2555990B1 (fr)	1986-12-26
AU566080B2 (en)	1987-10-08
IL73639A (en)	1988-06-30
DK561284A (da)	1985-06-02
MX159670A (es)	1989-08-02
IT8423746A0 (it)	1984-11-27

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