KR830001969B1 - 6- ｛D-(-) α- (4-ethyl-2.3-dioxo-1 piperazinocarbonylamino) phenyl (or hydroxyphenyl) acetamido peniclanic acid and a method for preparing the salt thereof - Google Patents

6- ｛D-(-) α- (4-ethyl-2.3-dioxo-1 piperazinocarbonylamino) phenyl (or hydroxyphenyl) acetamido peniclanic acid and a method for preparing the salt thereof Download PDF

Info

Publication number
KR830001969B1
KR830001969B1 KR1019810003767A KR810003767A KR830001969B1 KR 830001969 B1 KR830001969 B1 KR 830001969B1 KR 1019810003767 A KR1019810003767 A KR 1019810003767A KR 810003767 A KR810003767 A KR 810003767A KR 830001969 B1 KR830001969 B1 KR 830001969B1
Authority
KR
South Korea
Prior art keywords
ethyl
acid
dioxo
formula
phenyl
Prior art date
Application number
KR1019810003767A
Other languages
Korean (ko)
Other versions
KR830007675A (en
Inventor
김영설
Original Assignee
김영설
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.)
Filing date
Publication date
Application filed by 김영설 filed Critical 김영설
Priority to KR1019810003767A priority Critical patent/KR830001969B1/en
Priority to JP57005306A priority patent/JPS5867694A/en
Priority to FI820760A priority patent/FI820760L/en
Priority to BE2/59617A priority patent/BE892370A/en
Priority to AU82675/82A priority patent/AU8267582A/en
Priority to ES511709A priority patent/ES8307816A1/en
Priority to IN502/CAL/82A priority patent/IN155630B/en
Priority to NO822870A priority patent/NO822870L/en
Priority to DK435682A priority patent/DK435682A/en
Priority to IT68169/82A priority patent/IT1157064B/en
Priority to ES521036A priority patent/ES521036A0/en
Priority to ES521035A priority patent/ES8404792A1/en
Application granted granted Critical
Publication of KR830001969B1 publication Critical patent/KR830001969B1/en
Publication of KR830007675A publication Critical patent/KR830007675A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/141—Esters of phosphorous acids
    • C07F9/146—Esters of phosphorous acids containing P-halide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Abstract

내용 없음.No content.

Description

6―｛D―(―) α-(4―에틸-2.3-디옥소-1 피페라지노카보닐아미노) 페닐(또는 하이드록시페닐)아세트아미도 페니실란산 및 그 염의 제조방법6- ｛D-(-) α- (4-ethyl-2.3-dioxo-1 piperazinocarbonylamino) phenyl (or hydroxyphenyl) acetamido peniclanic acid and a method for preparing the salt thereof

본 발명은 다음 구조식(I)로 표시되는 페니실린 유도체의 새로운 제조방법에 관한 것이다.The present invention relates to a novel method for preparing a penicillin derivative represented by the following structural formula (I).

Figure kpo00001
Figure kpo00001

여기서 R은 수소이거나 수산기이며, M은 수소, 나트륨, 칼륨, 칼슘 등의 무기염이거나 탄소수 1-4인 저급알킬아민이다.Wherein R is hydrogen or a hydroxyl group, M is an inorganic salt of hydrogen, sodium, potassium, calcium or the like or a lower alkylamine having 1-4 carbon atoms.

본 발명의 목적물인 구조식(I)의 화합물은 벨기에 특허제828,692호, 불란서 특허제7,514,159호, 독일특허제2,519,400호, 일본특허 공개공보 소 52-106,883호 등에 의해 페니실린 유도체로 공지된 바 있으며, 이들 선행기술의 제조방법을 살펴보면 다음과 같다.The compound of formula (I), which is the object of the present invention, has been known as a penicillin derivative by Belgian Patent No. 828,692, French Patent No. 7,514,159, German Patent No. 2,519,400, Japanese Patent Application Publication No. 52-106,883, etc. Looking at the manufacturing method of the prior art as follows.

1-에칠-2,3-디옥소피페라진을 포스겐이나 트리클로로메칠클로로 카보네이트와 반응시켜 얻은 4-에칠-2,3-디옥소-1피페라지노카보닐클로라이드를 암피실린이나 아목실린과 반응시켜 목적물을 제조하거나 4-에칠-2,3-디옥소-1-피페라지노 카보닐클로라이드를 D(―)-α-페닐 글리신과 반응시켜 6-D(―)-α-(4-에칠-2,3-디옥소-1-피페라지노닐)-페닐글리신을 제조하고 이를 분리하여 에칠클로로카보네이트와 반응시켜 산무수물을 제조한후 6-아미노페니실란산과 아실화반응시켜 목적물을 제조하였으나, 이들 방법은 산염화물이나 산무수화물의 제조공정이 용이치 않은 결점이 있었다.4-ethyl-2,3-dioxo-1piperazinocarbonylchloride obtained by reacting 1-ethyl-2,3-dioxopiperazine with phosgene or trichloromethylchlorocarbonate was reacted with ampicillin or amoxiline. Preparation of the desired product or reaction of 4-ethyl-2,3-dioxo-1-piperazino carbonylchloride with D (-)-α-phenyl glycine to yield 6-D (-)-α- (4-ethyl- 2,3-dioxo-1-piperazinyl) -phenylglycine was prepared and separated and reacted with ethylchlorocarbonate to prepare an acid anhydride, followed by acylation with 6-aminophenic silane acid to prepare a target product. These methods have the drawback that the manufacturing process of an acid chloride or an acid anhydride is not easy.

본 발명은 상기 공지방법과는 달리 공업적으로 용이하게 실시할 수 있는 방법으는, 구체적인 제조방법을 설명하면 다음과 같다.The present invention is a method that can be easily carried out industrially, unlike the above known method, the specific manufacturing method will be described as follows.

본 발명은 공지의 방법에 의해 다음 구조식(II)의 D(―)-α-(4-에칠-2,3-디옥소-1-피페라지노카보닐)-페닐(또는 하드록시페닐) 글리신을 제조하여 다음 구조식(III)의 N-하드록시산아미드의 반응시켜 다음 구조식의(IV)산 무수물을 제조한다. 이때 촉매로는 다음 구조식(V)의 디싸이클로헥실카보디아미드를 사용하므로 쉽게 좋은 수율로 다음 구조식(IV)의 산무수물을 제조하여 다음 구조식(IV)의 6-아미노페니실린산과 반응시키므로 좋은 수율로 상기 구조식(I)의 목적물을 제조한다.The present invention relates to D (-)-α- (4-ethyl-2,3-dioxo-1-piperazinocarbonyl) -phenyl (or hydroxyphenyl) glycine of the following structural formula (II) by a known method. To prepare a (IV) acid anhydride of the following structural formula by reacting the N-hydroxy acid amide of the following formula (III). At this time, since the dicyclohexyl carbodiamide of the following structural formula (V) is used as a catalyst, an acid anhydride of the following structural formula (IV) is easily produced in a good yield, and then reacted with 6-aminophenicylic acid of the following structural formula (IV) to obtain a good yield The target object of the said Formula (I) is manufactured.

여기서 N-하드록시산아미드는 N-하이드록시썩신아미드, N-하이드록시푸탈아미드 또는 N-하이드록시글루타아미드를 말한다. 즉, 본 발명을 반응식으로 표시하면 다음과 같다.N-hydroxy acid amide here refers to N-hydroxy lysineamide, N-hydroxyfutalamide or N-hydroxyglutaamide. That is, the present invention is represented by the following reaction scheme.

Figure kpo00002
Figure kpo00002

여기서 R과 M은 전술한 바와 같고,Where R and M are as described above,

Figure kpo00003
Figure kpo00003

일반적으로 페니실란이나 세파로스도란산 유도체를 제조하는 과정에서 아실화반응을 시키기 위해 산무수물이나 산염화물을 제조하는 것이 통상적인 방법으로 잘 알려져 왔으나, 산염화물이나 산무수물을 제조하는 과정이 까다롭고 복잡하기 때문에 목적물의 수율을 저하시키는 요인이 되어왔다.Generally, it is well known to prepare acid anhydrides or acid chlorides for acylation in the process of preparing penicsilane or sepharose dolan acid derivatives, but the process of preparing acid chlorides or acid anhydrides is difficult and complicated. Therefore, it has become a factor which lowers the yield of the target object.

이와같은 결점을 보완하기 위하여 본원 발명에서는 산무수물제조시 생성되는 물을 쉽게 흡수하여 다음구조식(VII)의 디싸이클로헥실우레아로 변하는 촉매를 사용함으로써 정량적으로 산무수물을 제조하여 6-아미느페니실란과 반응시키므로 높은 수율로 목적물을 제조하였다.In order to make up for this drawback, the present invention quantitatively prepares acid anhydride by using a catalyst which easily absorbs the water produced during acid anhydride production and then converts to dicyclohexylurea of formula (VII). The target product was prepared in a high yield because it reacted with.

Figure kpo00004
Figure kpo00004

본 원발명에서 산무수물을 제조하는 과정에서 사용되는 용매로는 테트라하이드로후란, 염화메칠렌, 아세톤, 아세토니트릴 등이 좋으며, 테트라하이드로후란을 사용한 경우가 가장 좋았으며, 반응온도는 20-25℃에서 가장 좋은 수율을 나타냈다.In the present invention, tetrahydrofuran, methylene chloride, acetone, acetonitrile and the like are preferable solvents used in the preparation of acid anhydride, and tetrahydrofuran is best used, and the reaction temperature is 20-. The best yield was obtained at 25 ° C.

아실화반응시 사용된 용매로는 테트라하이드로후란 수용액이나 초산에칠수용액속에서 반응시키는 것이 가장 좋으며, 반응온도는 보통 20-25℃에서 반응시켜 감압하에서 용매를 제거하고 초산에칠을 가하고 용액의 pH를 1.5정도로 조절하고 초산에칠층을 분리하여 물로 세척한 후 망초로 건조하여 초산에칠을 감압하에서 농축시키면 결정이 석출되고 이 결정을 에테르에서 재결정화시키면 87%의 높은 수율로 목적물을 얻는다.The solvent used in the acylation reaction is best reacted in tetrahydrofuran aqueous solution or acetic acid acetic acid solution, and the reaction temperature is usually reacted at 20-25 ° C. to remove the solvent under reduced pressure, and added acetic acid acetate solution. The pH of the solution was adjusted to about 1.5, the ethyl acetate layer was separated, washed with water, dried with forget-me-not, and the ethyl acetate was concentrated under reduced pressure to precipitate crystals. When the crystals were recrystallized from ether, the target product was obtained in a high yield of 87%. .

[실시예 1]Example 1

6-[D(―)-α-(4-에칠-2,3-디옥소-1-피페라지노 카보닐아미노)-페닐아세트아미도] 페니실란산의 제조 D(―)-α-(4-에칠-2,3-디옥소-1-피페라지노카보닐)페닐글리신 1.9g을 테트라하이드로후란 20ml에 현탁시킨후 N-하이드록시썩신아미드 0.67g과 디싸이클로헥실카보디이미드 1.2g을 가하면 맑은 용액이 된다.Preparation of 6- [D (-)-α- (4-ethyl-2,3-dioxo-1-piperazinocarbonylamino) -phenylacetamido] peniclanic acid D (-)-α- ( 1.9 g of 4-ethyl-2,3-dioxo-1-piperazinocarbonyl) phenylglycine was suspended in 20 ml of tetrahydrofuran, followed by 0.67 g of N-hydroxylysinamide and dicyclohexylcarbodiimide 1.2. Adding g gives a clear solution.

실온에서 2시간 교반하면 다량의 침전이 생성된다. 침전물을 여과하고 여액을 5℃로 유지해둔다.Stirring at room temperature for 2 hours produces a large amount of precipitate. The precipitate is filtered off and the filtrate is kept at 5 ° C.

한편, 6-아미노페니실란산 1.16g을 물 15ml에 현탁시킨 후 온도를 3℃로 조절하고 트리에칠아민 1ml를 가하여 맑게 용해시킨다. 이 용액에 위에서 제조한 산무수물용액을 한꺼번에 가하면 온도가 10℃로 상승되며 붉은색깔로 반응액이 변하며, 시간이 경과하면 연한노란색으로 바뀐다.Meanwhile, 1.16 g of 6-aminophenic silane acid was suspended in 15 ml of water, and then the temperature was adjusted to 3 ° C., and 1 ml of triethylamine was added to dissolve clearly. When the acid anhydride solution prepared above is added to this solution at once, the temperature rises to 10 ° C., and the reaction solution turns red, and the color turns to light yellow over time.

실온에서 2.5시간 반응시킨 후 감압하에서 용매인 테트라하이드로 후란을 제거한후 잔유물에 초산에칠 20ml를 가하고 5℃에서 묽은염산으로 pH를 1.5로 조절한 후 초산에칠층을 분리하여 물로 2회 세척한후 망초를 가하여 건조시킨 후 여과하여 여액을 감압하에서 제거시킨다. 잔유물에 에테르 30ml를 가하여 결정화시키면 목적물 2.46g을 얻는다.After 2.5 hours of reaction at room temperature, tetrahydrofuran was removed under reduced pressure, 20 ml of ethyl acetate was added to the residue, and the pH was adjusted to 1.5 with dilute hydrochloric acid at 5 ° C. The ethyl acetate layer was separated and washed twice with water. After adding dried forget-me-not, filtered to remove the filtrate under reduced pressure. Crystallization by adding 30 ml of ether to the residue gave 2.46 g of the desired compound.

분석결과 비선광도는 +165.5°였고, 미생물학적 역가는 889.4㎍/mg였다.The specific light intensity was + 165.5 ° and the microbiological titer was 889.4 µg / mg.

[실시예 2]Example 2

6-[D(―)-α-(4-에칠-2,3-디옥소-1-피페라지노카보닐아미노)페닐아세트아미도]페니실란산의 나트륨염의 제조Preparation of the sodium salt of 6- [D (-)-α- (4-ethyl-2,3-dioxo-1-piperazinocarbonylamino) phenylacetamido] phenylanic acid

6-[D(―)-α-(4-에칠-2,3-디옥소-1-피페라지노카보닐아미드)페닐아세트아미도]페니실란산4.0g을 물 20ml에 현탁시키고 중조(0.62g을 물 5ml에 녹인 용액)을 가하여 완전히 용해시킨 후 무균여과하여 냉동건조시키면 3.8g의 목적을 얻는다.4.0 g of 6- [D (-)-α- (4-ethyl-2,3-dioxo-1-piperazinocarbonylamide) phenylacetamido] phenylanic acid is suspended in 20 ml of water and neutralized (0.62 g is dissolved in 5 ml of water), completely dissolved, and then sterile filtered and freeze-dried to obtain the purpose of 3.8 g.

분석결과 비선광도는 +178.4°였고, 미생물학적역가는 902.3㎍/mg였으며, 요오드적정으로 88.7%였다.As a result, specific light intensity was + 178.4 °, microbiological titer was 902.3µg / mg, and iodine titration was 88.7%.

Claims (3)

구조식(II)의 D(―)-α-(4-에칠-2,3-디옥소-1-피페라지노카보닐)-페닐(또는 하이드록시페닐)글리신과 구조식(III)의 N-하이드록 시산아미드를 유기용매 중에서 구조식(V)의 디싸이클로헥실 카보디이미드 촉매하에서 반응시켜 구조식(IV)의 산무수물을 제조한 후 구조식(VI)의 6-아미노페니실란산과 반응시키는 구조식(I)의 6-[D(―)-α-(4-에칠-2,3-디옥소-1-피페라지노 카보닐아미노)-페닐(또는 하이드록시페닐)아세트아미도]페니실란산 및 그 염의 제조방법.D (-)-α- (4-ethyl-2,3-dioxo-1-piperazinocarbonyl) -phenyl (or hydroxyphenyl) glycine of formula (II) and N-hydride of formula (III) Roxy amide is reacted in an organic solvent under a dicyclohexyl carbodiimide catalyst of formula (V) to prepare an acid anhydride of formula (IV), and then reacted with 6-aminophenicsilane acid of formula (VI) Of 6- [D (-)-α- (4-ethyl-2,3-dioxo-1-piperazinocarbonylamino) -phenyl (or hydroxyphenyl) acetamido] phenic acid and salts thereof Manufacturing method.
Figure kpo00005
Figure kpo00005
 여기서, R은 수소, 수산기이며, M은 수소, 나트륨, 칼륨, 칼슘등 무기염이거나 탄소수 1-4인 알킬아민이고Here, R is hydrogen, hydroxyl, M is inorganic salts such as hydrogen, sodium, potassium, calcium, or alkylamine having 1-4 carbon atoms
Figure kpo00006
Figure kpo00006
 제1항에 있어서, 유기용매로서는 데트라히드로후란, 염화메칠렌, 아세톤, 아세토니트릴로 구성된 군중에서 선택하는 방법.The method according to claim 1, wherein the organic solvent is selected from the group consisting of detrahydrofuran, methylene chloride, acetone, and acetonitrile. 제1항에 있어서, 실온인 조건에서 산무수물을 제조함을 특징으로하는 방법.The method of claim 1, wherein the acid anhydride is prepared under conditions of room temperature.
KR1019810003767A 1981-10-06 1981-10-06 6- ｛D-(-) α- (4-ethyl-2.3-dioxo-1 piperazinocarbonylamino) phenyl (or hydroxyphenyl) acetamido peniclanic acid and a method for preparing the salt thereof KR830001969B1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
KR1019810003767A KR830001969B1 (en) 1981-10-06 1981-10-06 6- ｛D-(-) α- (4-ethyl-2.3-dioxo-1 piperazinocarbonylamino) phenyl (or hydroxyphenyl) acetamido peniclanic acid and a method for preparing the salt thereof
JP57005306A JPS5867694A (en) 1981-10-06 1982-01-16 Manufacture of 6-(d-(-)-alpha-(4-ethyl-2,3- dioxo-1-piperadinocarbonylamino)-penyl( or hydroxypenyl)acetamide)penicillanic acid and salt of same
FI820760A FI820760L (en) 1981-10-06 1982-03-04 NY PROCESS FOER FRAMSTAELLNING AV PENICILLIN- OCH KEFALOSPORINDERIVAT
BE2/59617A BE892370A (en) 1981-10-06 1982-03-05 Alpha 2,3-di:oxo-piperazino-carbonyl-amino phenyl-acetamido-penicillin - and corresp. 3-1-methyl-tetrazolyl-thiomethyl cephalosporin(s) prepn. using tri:methyl-chloro-silane activated di:oxo piperazine
AU82675/82A AU8267582A (en) 1981-10-06 1982-04-16 Process of producing beta-lactam antibiotics
ES511709A ES8307816A1 (en) 1981-10-06 1982-04-26 Alpha 2,3-di:oxo-piperazino-carbonyl-amino phenyl-acetamido-penicillin - and corresp. 3-1-methyl-tetrazolyl-thiomethyl cephalosporin(s) prepn. using tri:methyl-chloro-silane activated di:oxo piperazine
IN502/CAL/82A IN155630B (en) 1981-10-06 1982-05-05
NO822870A NO822870L (en) 1981-10-06 1982-08-24 PROCESS FOR THE PRODUCTION OF PENICILLIN AND CEPHALOSPORIN DERIVATIVES
DK435682A DK435682A (en) 1981-10-06 1982-10-01 PROCEDURE FOR PENICILLIN AND CEPHALOSPORINE DERIVATIVES
IT68169/82A IT1157064B (en) 1981-10-06 1982-10-05 PROCEDURE FOR THE PRODUCTION OF PENICILLIN AND CEPHALOSPORIN DERIVATIVES
ES521036A ES521036A0 (en) 1981-10-06 1983-03-28 NEW PROCEDURE FOR THE OBTAINING OF D - (-) - ALPHA- (4-ALKYL-2,3-GOD-PIPERACINACARBONYLIC) -PHENYL (OR PARA-HYDROXYPHENIC).
ES521035A ES8404792A1 (en) 1981-10-06 1983-03-28 Alpha 2,3-di:oxo-piperazino-carbonyl-amino phenyl-acetamido-penicillin - and corresp. 3-1-methyl-tetrazolyl-thiomethyl cephalosporin(s) prepn. using tri:methyl-chloro-silane activated di:oxo piperazine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019810003767A KR830001969B1 (en) 1981-10-06 1981-10-06 6- ｛D-(-) α- (4-ethyl-2.3-dioxo-1 piperazinocarbonylamino) phenyl (or hydroxyphenyl) acetamido peniclanic acid and a method for preparing the salt thereof

Publications (2)

Publication Number Publication Date
KR830001969B1 true KR830001969B1 (en) 1983-09-29
KR830007675A KR830007675A (en) 1983-11-04

Family

ID=19221907

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019810003767A KR830001969B1 (en) 1981-10-06 1981-10-06 6- ｛D-(-) α- (4-ethyl-2.3-dioxo-1 piperazinocarbonylamino) phenyl (or hydroxyphenyl) acetamido peniclanic acid and a method for preparing the salt thereof

Country Status (3)

Country Link
JP (1) JPS5867694A (en)
KR (1) KR830001969B1 (en)
BE (1) BE892370A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1282955B1 (en) * 1996-05-03 1998-04-02 Abres Associated Biotechnology PROCESS FOR THE PREPARATION OF UREIDE DERIVATIVES AND SYNTHETIC INTERMEDIATEs
IT1283530B1 (en) * 1996-07-26 1998-04-21 Ribbon Srl PROCEDURE FOR THE PREPARATION OF PENICILLINS
WO2008093650A1 (en) * 2007-01-31 2008-08-07 Toyama Chemical Co., Ltd. Novel crystal of piperacillin sodium

Also Published As

Publication number Publication date
KR830007675A (en) 1983-11-04
BE892370A (en) 1982-07-01
JPS5867694A (en) 1983-04-22

Similar Documents

Publication Publication Date Title
USRE29650E (en) Phthalide penicillin ester intermediates
JPH02311483A (en) Preparation of ceftriaxone
RU2134265C1 (en) Bicyclic complexes beta-lactam/hydroxybenzoic acid, methods of beta-lactams synthesis
SU628821A3 (en) Method of producing 3-methyl-3-cephem-carbonic acid derivatives
US4003896A (en) Method of preparing a sparingly soluble complex of cephalexin
KR830001969B1 (en) 6- ｛D-(-) α- (4-ethyl-2.3-dioxo-1 piperazinocarbonylamino) phenyl (or hydroxyphenyl) acetamido peniclanic acid and a method for preparing the salt thereof
EP0084611A1 (en) Crystalline, solvate-free D-(-)-4-hydroxy-phenylglycyl-chloride hydrochloride
US3284451A (en) Activated esters of 7-amino-cephalosporanic acid
US4193918A (en) Process for the preparation of hydroxy-alpha-amino-benzyl penicillin
SU574158A3 (en) Method of preparing cephalexine or salts thereof
SU499812A3 (en) The method of obtaining derivatives of cephalosporin
SU563918A3 (en) Method of producing cephalosporane derivatives,or their salts,or esters
KR830001970B1 (en) Method for preparing cephalosporin derivative
SU501676A3 (en) The method of obtaining 7-aminocephalosporanic acid
US4237280A (en) Intermediate for cephalosporin type compound
US4204058A (en) Process for obtaining cephalosporin C and the salts and derivatives thereof from culture filtrates or culture solutions
US3715347A (en) Process for acetylation
KR100472048B1 (en) Novel method for producing Aztreonam
JPH06104670B2 (en) New manufacturing method of chemical compounds
US4366098A (en) Process for preparing aminopenicillins
US4458085A (en) Preparation of 3-benzothienylglycines
CA1157850A (en) PROCESS FOR THE PREPARATION OF .beta.-LACTAM ANTIBIOTICS
KR830001657B1 (en) Method for preparing penicillin and cephalosporin derivatives
KR810000637B1 (en) Process for preparing cephalosporin compounds
KR970004041B1 (en) Benzothiazine derivatives quinolone