DK174331B1 - Krystalliserede cephem-syreadditionssalte, dets fremstilling og anvendelse til fremstilling af et lægemiddel samt lægemiddel indeholdende saltet - Google Patents

Krystalliserede cephem-syreadditionssalte, dets fremstilling og anvendelse til fremstilling af et lægemiddel samt lægemiddel indeholdende saltet Download PDF

Info

Publication number: DK174331B1
Authority: DK; Denmark
Prior art keywords: salt; formula; medicament; compound; acid addition
Prior art date: 1987-02-25

Application number

DK198800957A

Other languages

Danish (da)

English (en)

Other versions

DK95788D0 (da

DK95788A (da

Inventor

Rudolf Lattrell

Walter Duerckheimer

Reiner Kirrstetter

Original Assignee

Aventis Pharma Gmbh

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.)

1987-02-25

Filing date

1988-02-24

Publication date

2002-12-09

1988-02-24 Application filed by Aventis Pharma Gmbh filed Critical Aventis Pharma Gmbh

1988-02-24 Publication of DK95788D0 publication Critical patent/DK95788D0/da

1988-08-26 Publication of DK95788A publication Critical patent/DK95788A/da

2002-12-09 Application granted granted Critical

2002-12-09 Publication of DK174331B1 publication Critical patent/DK174331B1/da

Links

150000003839 salts Chemical class 0.000 title claims description 24
239000002253 acid Substances 0.000 title claims description 10
239000003814 drug Substances 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 14
229960003237 betaine Drugs 0.000 claims description 7
208000035143 Bacterial infection Diseases 0.000 claims description 2
208000022362 bacterial infectious disease Diseases 0.000 claims description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
150000001875 compounds Chemical class 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
239000000243 solution Substances 0.000 description 7
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 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000000203 mixture Substances 0.000 description 5
238000000034 method Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
-1 N ' Chemical class 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000872 buffer Substances 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001914 filtration Methods 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
229910000043 hydrogen iodide Inorganic materials 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YZCGETRSFFIJTC-OFNLCGNNSA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydroxide Chemical compound [OH-].N([C@@H]1C(N2C(=C(C[N+]=3C=4CCCCC=4C=CC=3)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 YZCGETRSFFIJTC-OFNLCGNNSA-N 0.000 description 1
YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
229930186147 Cephalosporin Chemical class 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
229940126575 aminoglycoside Drugs 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- C07D501/38—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)
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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK198800957A 1987-02-25 1988-02-24 Krystalliserede cephem-syreadditionssalte, dets fremstilling og anvendelse til fremstilling af et lægemiddel samt lægemiddel indeholdende saltet DK174331B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19873706020 DE3706020A1 (de)	1987-02-25	1987-02-25	Kristallisierte cephem-saeureadditionssalze und verfahren zu ihrer herstellung
DE3706020		1987-02-25

Publications (3)

Publication Number	Publication Date
DK95788D0 DK95788D0 (da)	1988-02-24
DK95788A DK95788A (da)	1988-08-26
DK174331B1 true DK174331B1 (da)	2002-12-09

Family

ID=6321729

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198800957A DK174331B1 (da)	1987-02-25	1988-02-24	Krystalliserede cephem-syreadditionssalte, dets fremstilling og anvendelse til fremstilling af et lægemiddel samt lægemiddel indeholdende saltet

Country Status (27)

Country	Link
US (1)	US4845087A (fr)
EP (1)	EP0280157B1 (fr)
JP (1)	JP2635078B2 (fr)
KR (1)	KR960003617B1 (fr)
AR (1)	AR243193A1 (fr)
AT (1)	ATE128469T1 (fr)
AU (1)	AU621040B2 (fr)
CA (1)	CA1297473C (fr)
CS (1)	CS274422B2 (fr)
CY (1)	CY2023A (fr)
DD (1)	DD287505A5 (fr)
DE (2)	DE3706020A1 (fr)
DK (1)	DK174331B1 (fr)
ES (1)	ES2079349T3 (fr)
FI (1)	FI91530C (fr)
GR (1)	GR3017917T3 (fr)
HU (1)	HU200186B (fr)
IE (1)	IE69040B1 (fr)
IL (1)	IL85521A0 (fr)
MA (1)	MA21193A1 (fr)
MX (1)	MX10537A (fr)
NO (1)	NO880811L (fr)
NZ (1)	NZ223594A (fr)
PH (1)	PH26857A (fr)
PT (1)	PT86826B (fr)
TN (1)	TNSN88018A1 (fr)
ZA (1)	ZA881282B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3118732A1 (de) *	1981-05-12	1982-12-02	Hoechst Ag, 6000 Frankfurt	Cephalosporinderivate und verfahren zu ihrer herstellung
US4921851A (en) *	1986-06-09	1990-05-01	Takeda Chemical Industries, Ltd.	Cephem compounds, their production and use
IE61679B1 (en) *	1987-08-10	1994-11-16	Fujisawa Pharmaceutical Co	Water-soluble antibiotic composition and water-soluble salts of new cephem compounds
EP0997466A1 (fr) *	1988-10-24	2000-05-03	PROCTER & GAMBLE PHARMACEUTICALS, INC.	Lactam-quinolones antimicrobiennes
DE4440141A1 (de)	1994-11-10	1996-05-15	Hoechst Ag	Neue kristalline Cephem-Säureadditionssalze und Verfahren zu ihrer Herstellung
KR100389284B1 (ko) *	1999-09-30	2003-06-27	(주)정인종합건축사사무소	경첩
CA2626273C (fr) *	2005-10-29	2013-05-14	Intervet International Bv	Compositions de cefquinome et procedes d'utilisation de celles-ci
TWI400243B (zh) *	2009-07-20	2013-07-01	Intervet Int Bv	製造西喹諾（ｃｅｆｑｕｉｎｏｍｅ）粒子的方法
CN102002058B (zh) *	2010-11-05	2012-04-04	山东鲁抗立科药物化学有限公司	硫酸头孢喹肟的合成方法
WO2012095438A1 (fr)	2011-01-12	2012-07-19	Intervet International B.V.	Particules et suspensions d'antibiotiques céphalosporine
CN104031069B (zh) *	2014-05-19	2016-05-18	浙江工业大学	一种硫酸头孢喹肟的制备方法
CN111072686B (zh) *	2019-12-30	2021-02-12	济宁市化工研究院(淮海化工研究院)	一种硫酸头孢喹肟的制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH644609A5 (de) *	1979-10-02	1984-08-15	Glaxo Group Ltd	Cephalosporinantibiotikum.
DE3118732A1 (de) *	1981-05-12	1982-12-02	Hoechst Ag, 6000 Frankfurt	Cephalosporinderivate und verfahren zu ihrer herstellung
DE3248281A1 (de) *	1982-12-28	1984-06-28	Hoechst Ag, 6230 Frankfurt	Kristalisierte cephem-saeureadditionssalze und verfahren zu ihrer herstellung
DE3316798A1 (de) *	1983-05-07	1984-11-08	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von cephemverbindungen
US4537959A (en) *	1984-03-26	1985-08-27	Eli Lilly And Company	Crystalline cephalosporin antibiotic salt
DE3419015A1 (de) *	1984-05-22	1985-11-28	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von cephalosporinen

1987
- 1987-02-25 DE DE19873706020 patent/DE3706020A1/de not_active Ceased
1988
- 1988-02-16 DE DE3854507T patent/DE3854507D1/de not_active Expired - Lifetime
- 1988-02-16 ES ES88102230T patent/ES2079349T3/es not_active Expired - Lifetime
- 1988-02-16 AT AT88102230T patent/ATE128469T1/de not_active IP Right Cessation
- 1988-02-16 EP EP88102230A patent/EP0280157B1/fr not_active Expired - Lifetime
- 1988-02-23 FI FI880842A patent/FI91530C/fi active IP Right Grant
- 1988-02-23 IL IL85521A patent/IL85521A0/xx unknown
- 1988-02-23 CS CS113688A patent/CS274422B2/cs not_active IP Right Cessation
- 1988-02-23 US US07/159,395 patent/US4845087A/en not_active Expired - Lifetime
- 1988-02-23 AR AR88310143A patent/AR243193A1/es active
- 1988-02-23 NZ NZ223594A patent/NZ223594A/xx unknown
- 1988-02-23 DD DD88313117A patent/DD287505A5/de unknown
- 1988-02-23 PH PH36546A patent/PH26857A/en unknown
- 1988-02-23 MA MA21432A patent/MA21193A1/fr unknown
- 1988-02-24 DK DK198800957A patent/DK174331B1/da not_active IP Right Cessation
- 1988-02-24 IE IE50388A patent/IE69040B1/en not_active IP Right Cessation
- 1988-02-24 MX MX1053788A patent/MX10537A/es unknown
- 1988-02-24 ZA ZA881282A patent/ZA881282B/xx unknown
- 1988-02-24 HU HU88890A patent/HU200186B/hu unknown
- 1988-02-24 PT PT86826A patent/PT86826B/pt not_active IP Right Cessation
- 1988-02-24 JP JP63041778A patent/JP2635078B2/ja not_active Expired - Lifetime
- 1988-02-24 KR KR88001897A patent/KR960003617B1/ko not_active Expired - Lifetime
- 1988-02-24 AU AU12106/88A patent/AU621040B2/en not_active Expired
- 1988-02-24 NO NO880811A patent/NO880811L/no unknown
- 1988-02-24 CA CA000559732A patent/CA1297473C/fr not_active Expired - Lifetime
- 1988-02-25 TN TNTNSN88018A patent/TNSN88018A1/fr unknown
1995
- 1995-10-30 GR GR950403022T patent/GR3017917T3/el unknown
1998
- 1998-02-20 CY CY202398A patent/CY2023A/xx unknown

Also Published As

Publication number	Publication date
KR960003617B1 (en)	1996-03-20
ES2079349T3 (es)	1996-01-16
IE69040B1 (en)	1996-08-07
EP0280157A2 (fr)	1988-08-31
HUT46695A (en)	1988-11-28
IL85521A0 (en)	1988-08-31
CS113688A2 (en)	1990-08-14
CY2023A (en)	1998-02-20
CS274422B2 (en)	1991-04-11
DD287505A5 (de)	1991-02-28
CA1297473C (fr)	1992-03-17
MA21193A1 (fr)	1988-10-01
KR880009973A (ko)	1988-10-06
JP2635078B2 (ja)	1997-07-30
HU200186B (en)	1990-04-28
NZ223594A (en)	1990-03-27
IE880503L (en)	1988-08-25
GR3017917T3 (en)	1996-01-31
TNSN88018A1 (fr)	1990-07-10
DK95788D0 (da)	1988-02-24
FI91530B (fi)	1994-03-31
NO880811D0 (no)	1988-02-24
AU1210688A (en)	1988-09-01
DE3854507D1 (de)	1995-11-02
MX10537A (es)	1993-08-01
FI880842A0 (fi)	1988-02-23
EP0280157A3 (en)	1990-07-18
US4845087A (en)	1989-07-04
PT86826A (pt)	1988-03-01
ZA881282B (en)	1988-08-23
AU621040B2 (en)	1992-03-05
FI880842L (fi)	1988-08-26
EP0280157B1 (fr)	1995-09-27
DK95788A (da)	1988-08-26
AR243193A1 (es)	1993-07-30
ATE128469T1 (de)	1995-10-15
PH26857A (en)	1992-11-16
PT86826B (pt)	1992-05-29
DE3706020A1 (de)	1988-09-08
NO880811L (no)	1988-08-26
FI91530C (fi)	1994-07-11
JPH01216995A (ja)	1989-08-30

Legal Events

Date	Code	Title	Description
2002-12-09	B1	Patent granted (law 1993)
2008-03-10	PUP	Patent expired

Publication	Publication Date	Title
DK174331B1 (da)	2002-12-09	Krystalliserede cephem-syreadditionssalte, dets fremstilling og anvendelse til fremstilling af et lægemiddel samt lægemiddel indeholdende saltet
JP6144669B2 (ja)	2017-06-07	新規セファロスポリン誘導体およびその医薬組成物
JPS5858354B2 (ja)	1983-12-24	セフェム誘導体
CS209878B2 (en)	1981-12-31	Method of making the new alcyloxime derivatives of the 7-/2-(2-amino-4-thiazolyl)acetamido/cephalosporan acid
US3828037A (en)	1974-08-06	Trifluoromethylmercaptoacetamidocephalosporins
DK166211B (da)	1993-03-22	Krystalliseret cephem-syreadditionssalt, dets fremstilling og anvendelse
DK159156B (da)	1990-09-10	Analogifremgangsmaade til fremstilling af (2-(2-aminothiazol-4-yl)-2-(0-substitueret)-oxyiminoacetamido)-7-cephalosporan-syre og fysiologisk acceptable salte deraf
FI65623C (fi)	1984-06-11	Foerfarande foer framstaellning av antibiotiskt aktiv (6r 7r)-3-karbamoyloximetyl-7-(2-(fur-2-yl)-2-metoxiiminoacetamido)-cef-3-em-4-karboxylsyra samt dennas icke-giftiga salter
DK174730B1 (da)	2003-10-06	Diastereomer af 7-[2-(2-aminothiazol-4-yl)-2-(Z)-hydroxyiminoacetamido]-3-(methoxymethyl)-3-cephem-4-carboxylsyre-[alfa-(2,2-dimethylptopionyloxy)-ethyl]-ester, fremgangsmåde til fremstilling deraf, et lægemiddel indeholdende den nævnte diastereomer,
JPS63107989A (ja)	1988-05-12	セファロスポリン化合物
JPH01110690A (ja)	1989-04-27	水溶性抗生物質組成物および新規セフェム化合物の水溶性塩類
JPS6141517B2 (fr)	1986-09-16
DK162718B (da)	1991-12-02	Analogifremgangsmaade til fremstilling af 7-substitueret-3-vinyl-3-cephemforbindelser
EP0449515B1 (fr)	1995-05-24	Intermédiaires de céphalosporine et procédé pour leur préparation ainsi que la préparation de leurs produits finaux
PT98703A (pt)	1992-07-31	Processo para a preparacao de novas cefalosporinas
US4007176A (en)	1977-02-08	Cephalosporin derivatives
US4311842A (en)	1982-01-19	Cephalosporin compounds
JP2000514832A (ja)	2000-11-07	抗菌性の置換７−アシルアミノ−３−（メチルヒドラゾノ）メチルセファロスポリンおよび中間体
US4034088A (en)	1977-07-05	Cephalosporin derivatives, and compositions containing them
DK157684B (da)	1990-02-05	Fremgangsmaade til fremstilling af krystallinske penicillinsyrer
KR800001595B1 (ko)	1980-12-29	세팔로스포린 유도체의 제조방법
NO791788L (no)	1979-12-04	Cefalosporiner og fremgangsmaate til deres fremstilling
JPS6129956B2 (fr)	1986-07-10
DK150600B (da)	1987-04-06	Cephalosporinderivater
JPH0616675A (ja)	1994-01-25	新規セフェム化合物およびその塩