SU1516013A3 - Method of producing thermally stable crystalline sulfuric acid-additive salts of 7-/-alpha-(2-aminothiazol-4-yl)-alpha-(z)-methoxyiminoacetamido/-3-/(1-methyl-1-pyrrolidinio)-methyl/-3-cephem-4-carboxylate - Google Patents
Method of producing thermally stable crystalline sulfuric acid-additive salts of 7-/-alpha-(2-aminothiazol-4-yl)-alpha-(z)-methoxyiminoacetamido/-3-/(1-methyl-1-pyrrolidinio)-methyl/-3-cephem-4-carboxylate Download PDFInfo
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- SU1516013A3 SU1516013A3 SU864027914A SU4027914A SU1516013A3 SU 1516013 A3 SU1516013 A3 SU 1516013A3 SU 864027914 A SU864027914 A SU 864027914A SU 4027914 A SU4027914 A SU 4027914A SU 1516013 A3 SU1516013 A3 SU 1516013A3
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- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- sulfuric acid
- cephem
- alpha
- carboxylate
- Prior art date
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- 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
Abstract
Изобретение относитс к гетероциклическим соединени м, в частности к получению термически стабильной кристаллической аддитивной соли с серной кислотой 7-[α-(2-аминотиазол-4-ил)-α-(Z)-метоксииминоацетамидо]-3-[(1-метил-1-пирролидинио)-метил]-3-цефем-4-карбоксилата, имеющей диффракционную рентгеновскую решетку, сн тую дл порошка на медной трубке с никелевым фильтром (CU:NI) с определенными значени ми межплоскостных рассто ний D и относительных интенсивностей 1/1°, котора может найти применение в медицине. Цель - разработка способа получени новой кристаллической формы цефалоспоринового антибиотика. Получение целевого продукта ведут реакцией амфотерного 7-[α-(2-аминотиазол-4-ил)-α-(Z)-метоксииминоацетамидо]-3-[(1-метил-1-пирролидинио)-метил]-3-цефем-4-карбоксилата с концентрацией 100-200 мг/мл с H2SO4 (1-2 мол. экв.) в водной среде. Затем инициируют кристаллизацию целевого продукта из реакционной смеси и выдел ют его. 1 табл.The invention relates to heterocyclic compounds, in particular to the preparation of a thermally stable crystalline addition salt with 7- [α- (2-aminothiazol-4-yl) -α- (Z) methoxyiminoacetamido] -3 - [(1-methyl -1-pyrrolidinio) -methyl] -3-cephem-4-carboxylate, having a diffraction X-ray lattice, removed for powder on a copper tube with a nickel filter (CU: NI) with specific values of interplanar spacing D and relative intensities 1 / 1 °, which can be used in medicine. The goal is to develop a method for obtaining a new crystalline form of a cephalosporin antibiotic. The production of the target product is carried out by the reaction of amphoteric 7- [α- (2-aminothiazol-4-yl) -α- (Z) -methoxyiminoacetamido] -3 - [(1-methyl-1-pyrrolidinio) methyl] -3-cephem- 4-carboxylate with a concentration of 100-200 mg / ml with H 2 SO 4 (1-2 mol. Eq.) In an aqueous medium. The crystallization of the desired product from the reaction mixture is then initiated and recovered. 1 tab.
Description
1,5 г амфотерных ионов медленно добавл ют в 10 мл энергетично перемешиваемого 1 н, раствора серной кислоты (1,59 моль-экв) при 20-26 С, Получают раствор. Затем кристаллизацию инициируют при помощи затравки с использованием кристаллической аддитивной соли серной кислоты и вьщержи вают кристаллическую массу в виде шлама в течение 0,5 ч. Далее кристаллы отдел ют при помощи вакуумной фильтрации, промывают при помощи 3 мл смеси ацетона: вода (1:1 по объему ) и двух порций по 5 мл ацетона; затем осуществл ют вакуумную сугоку при 40-50 0 в течение ночи,1.5 g of amphoteric ions are slowly added to 10 ml of energetically stirred 1 N, sulfuric acid solution (1.59 mol eq) at 20-26 ° C. A solution is obtained. Then, the crystallization is initiated by means of a seed using a crystalline sulfuric acid addition salt, and the crystalline mass is held in the form of a slurry for 0.5 h. Next, the crystals are separated by vacuum filtration, washed with 3 ml of acetone: water (1: 1 by volume) and two servings of 5 ml of acetone; then vacuum sugoku is performed at 40-50 ° overnight,
Выход составл ет 1,3 г аддитивной соли серной кислоты.The yield is 1.3 g of the sulfuric acid addition salt.
Элементный анализElemental analysis
Рассчитано, .%: С 39-,44; И 4,53; N 14,52; S -16,62; - не обнаружена ,Calculated,%: C 39-, 44; And 4.53; N 14.52; S -16.62; - not detected
. .
Найдено, %: С 38,91; Н 4,57; N 14,64; S 16,71; 1,42.Found,%: C 38.91; H 4.57; N 14.64; S 16.71; 1.42.
Пример 2. Получение аддитивной соли серной кислоты,Example 2. Obtaining additive sulfuric acid,
1,5 г амфотерных ионов раствор ют в 5 мл воды, Б полученный раствор добавл ют при перемешивании 5 мл 1 М раствора HjiSO. Затем кристаллизацию инициируют при помощи затравки кристаллической аддитивной соли кислоты, далее кристаллы выдерживают в гпламе в течение 0,5 ч. Затем кристаллы отдел ют при помощи вакуумной фильтрации, промывают 3 мл смеси ацетон:вода (1:1 по объему) и двум порци ми по 5 мл ацетона; затем сушат под вакуумом при 40-50 С в течение ночи.1.5 g of amphoteric ions are dissolved in 5 ml of water; B, the resulting solution is added with stirring 5 ml of 1 M solution of HjiSO4. Then, the crystallization is initiated by priming the crystalline acid addition salt, then the crystals are incubated in hplame for 0.5 h. Then the crystals are separated by vacuum filtration, washed with 3 ml of a mixture of acetone: water (1: 1 by volume) and two portions 5 ml of acetone; then dried under vacuum at 40-50 ° C overnight.
Выход составл ет 1,3 г аддитивной соли серной кислоты.The yield is 1.3 g of the sulfuric acid addition salt.
Дифракционную решетку порошка в рентгеновских лучах кристаллической сульфатной соли (-(2-аминотиазол- 4-ил)-о/-(Е) -метоксиминоацетамидоД- 3 (1-метил-1-пирролидинио)-метил - : З-цефем-4-карбоксилата, полученной в соответствии с примерами 1 и 2, определ ли при помошд дифрактометра дл порошкообразных материалов типа Ригаку с использованием в качестве мишеш дл рентгеновских лучей медной трубки, никелевого фильтра и пробы, содержащейс в стекл нной чашке. Скорость сканировани составл ла 2/мин в области изменени отX-ray diffraction grating of crystalline sulfate salt (- (2-aminothiazol-4-yl) -o / - (E) -methoxyminoacetamido D-3 (1-methyl-1-pyrrolidino) -methyl -: Z-cepham-4- the carboxylate prepared according to examples 1 and 2 was determined using a diffractometer for powdered Rigaku materials using a copper tube, a nickel filter and a sample contained in a glass cup as x-ray targets. The scan rate was 2 / min in the field of change from
4four
40, при этом механически запи40, while mechanically recording
00
5five
00
5five
00
5five
00
5five
сывали диаграмму с тем, чтобы зафиксировать углы с максимальной дифракцией . На основании этих данных определ ли промежутки (d) и относитель- .ные интенсивности (1/1°), Эти данные приведены ниже, d-пpoмeжyткИ| А 1/1°, %The diagram was drawn in order to fix the angles with the maximum diffraction. On the basis of these data, the intervals (d) and relative intensities (1/1 °) were determined. These data are given below, d-intercept | А 1/1 °,%
9,201009,20100
6,89506.8950
5,50285.5028
5,09225.0922
4,50384.5038
4,41444,4144
4,19644.1964
3,78383.7838
3,64443.6444
3,39253.3925
3,31313.3131
3,15473.1547
Пример 3. Изучение стабильности при повышенных температурах .Example 3. The study of stability at elevated temperatures.
Термическую стабильность определ ли при хранении композиций в сухих контейнерах при различных температурах, а изменение эффективности определ ли с использованием ВЧЖХ,The thermal stability was determined by storing the compositions in dry containers at different temperatures, and the change in efficiency was determined using HPLC,
Полученные результаты представлены в таблице.(увеличение эффективности указано знаком плюс перед числом; потер эффективности менее 10% в течение 2-4 недель при 45-56 С в общем случае указывает на снижение эффективности менее чем на 10% в течение 2-3 лет при комнатной температуре ) ,The results are presented in the table. (The increase in efficiency is indicated by a plus sign in front of a number; a loss of efficiency of less than 10% for 2-4 weeks at 45-56 C generally indicates a decrease in efficiency of less than 10% for 2-3 years with room temperature)
Пример 4, Испытание физических смесей.Example 4, Testing physical mixtures.
Физические смеси получали из кристаллической аддитивной соли серной кислоты с тринатрий ортофосфатом, бикарбонатом натри , Ь(+)-лизином и Ь()-аргинином. Основани добавл ли в таких пропорци х, чтобы обеспечить значени рН при разбавлении смеси водой до активности амфотерных ионов 250 мг/кг (которую определ ли при помощи ВЧЖХ) в следующих преде- лах:тринатрий ортофосфат (рН 6,0); бикарбонат натри (рН 6,0); Lr-(-f)- лизин (рН 6,0); L--(+)-аргинин (рН 6,0/,Physical mixtures were obtained from a crystalline sulfuric acid addition salt with trisodium orthophosphate, sodium bicarbonate, L (+) - lysine and L () - arginine. The bases were added in such proportions as to ensure that the pH of the mixture was diluted with water until amphoteric ions activity was 250 mg / kg (as determined by HPLC) in the following limits: trisodium orthophosphate (pH 6.0); sodium bicarbonate (pH 6.0); Lr - (- f) - lysine (pH 6.0); L - (+) - arginine (pH 6.0 /,
Композиции дл инъекций получки с использованием стерильной воды, чтобы довести активность амфотер5 1516013, 6Injection compositions of wages using sterile water to bring amphoter5 activity 1516013, 6
ных ионов до 250 мг/мл, которую оп-d, А ions up to 250 mg / ml, which op-d, A
редел ли при помощи ВЧЖХ, Трудностей. 9,20 100Determined by HPLC, Difficulties. 9.20 100
с растворимостью не было, 50with solubility was not 50
Инъекции проводили (в дозе 100 мг/кг) 5,50 28Injections were performed (at a dose of 100 mg / kg) 5.50 28
внутримышечным способом кроликам,5,09 22by intramuscular method to rabbits, 5.09 22
при этом болезненные ощущени были в4,50 38while the pain was 4.50 38
допустимых пределах. Минимальные4,41 А4allowable limits. Minimum4,44 A4
болезненные ощущени наблюдали при4,19 63pain sensations observed at 4,19 63
применении композиции, содержащей ар-Ю 3,78 38the use of a composition containing ar-S 3.78 38
гинин,3,64 4Аginin, 3.64 4A
Claims (1)
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Application Number | Priority Date | Filing Date | Title |
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US76223585A | 1985-08-05 | 1985-08-05 |
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SU1516013A3 true SU1516013A3 (en) | 1989-10-15 |
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SU864027914A SU1516013A3 (en) | 1985-08-05 | 1986-08-04 | Method of producing thermally stable crystalline sulfuric acid-additive salts of 7-/-alpha-(2-aminothiazol-4-yl)-alpha-(z)-methoxyiminoacetamido/-3-/(1-methyl-1-pyrrolidinio)-methyl/-3-cephem-4-carboxylate |
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JP (1) | JPH0615548B2 (en) |
KR (1) | KR930003121B1 (en) |
AR (1) | AR243894A1 (en) |
AT (1) | AT390957B (en) |
AU (1) | AU597262B2 (en) |
BE (1) | BE905219A (en) |
CA (1) | CA1284994C (en) |
CH (1) | CH675581A5 (en) |
CS (2) | CS276717B6 (en) |
CY (1) | CY1614A (en) |
DD (2) | DD254941A5 (en) |
DE (1) | DE3626375A1 (en) |
DK (1) | DK162053C (en) |
EG (1) | EG18003A (en) |
ES (1) | ES2002112A6 (en) |
FI (1) | FI84484C (en) |
FR (1) | FR2585705B1 (en) |
GB (1) | GB2179936B (en) |
GR (1) | GR862055B (en) |
HK (1) | HK99691A (en) |
HU (1) | HU196602B (en) |
IE (1) | IE59222B1 (en) |
IL (1) | IL79608A (en) |
IT (1) | IT1197067B (en) |
LU (2) | LU86540A1 (en) |
MY (1) | MY102212A (en) |
NL (1) | NL8601991A (en) |
OA (1) | OA08672A (en) |
PT (1) | PT83134B (en) |
SE (1) | SE469633B (en) |
SG (1) | SG79791G (en) |
SU (1) | SU1516013A3 (en) |
YU (1) | YU45793B (en) |
ZA (1) | ZA865842B (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
WO1988010263A1 (en) * | 1987-06-25 | 1988-12-29 | Banyu Pharmaceutical Co., Ltd. | Crystalline cephalosporin compounds, process for their preparation, and intermediates for their preparation |
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 |
JPH02101081A (en) * | 1988-10-08 | 1990-04-12 | Meiji Seika Kaisha Ltd | Crystalline dihydrochloride of cephalosporin derivative and production thereof |
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 |
EP0638573A1 (en) * | 1993-08-10 | 1995-02-15 | Lucky Ltd. | Crystalline hydrates of cephalosporin and process for preparation thereof |
JP4616844B2 (en) | 2003-12-23 | 2011-01-19 | サンド・ゲーエムベーハー | Production process of intermediates for use in the synthesis of cephalosporin |
WO2008056221A2 (en) * | 2006-11-06 | 2008-05-15 | Orchid Chemicals & Pharmaceuticals Limited | Crystalline sulfate salt of cephalosporin antibiotic |
DE102012101680A1 (en) * | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Pharmaceutical preparation containing an antiviral dihydroquinazoline derivative |
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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 (en) * | 1984-05-22 | 1985-11-28 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING CEPHALOSPORINES |
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 |
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1986
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- 1986-08-04 IT IT21409/86A patent/IT1197067B/en active Protection Beyond IP Right Term
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1992
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Title |
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Па тент.. US № 4406899. кл. 424-246, опублик. 1985.., . * |
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