KR830009110A - 6-베타-히드록시메틸페니실란산 1,1-디옥시드와베타-락탐 항생제로써 1,1-알칸디올류의비스-에스테르류를 제조하는 방법 - Google Patents
6-베타-히드록시메틸페니실란산 1,1-디옥시드와베타-락탐 항생제로써 1,1-알칸디올류의비스-에스테르류를 제조하는 방법 Download PDFInfo
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- KR830009110A KR830009110A KR1019820001220A KR820001220A KR830009110A KR 830009110 A KR830009110 A KR 830009110A KR 1019820001220 A KR1019820001220 A KR 1019820001220A KR 820001220 A KR820001220 A KR 820001220A KR 830009110 A KR830009110 A KR 830009110A
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- Prior art keywords
- phenylacetamido
- acetamido
- thienyl
- acid
- group
- Prior art date
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- 239000002253 acid Substances 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 4
- 239000003782 beta lactam antibiotic agent Substances 0.000 title 1
- 239000002132 β-lactam antibiotic Substances 0.000 title 1
- 229940124586 β-lactam antibiotics Drugs 0.000 title 1
- -1 2-phenylacetamido, 2-phenoxyacetamido Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 8
- 238000013329 compounding Methods 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- JQEHQELQPPKXRR-LLVKDONJSA-N (2r)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetic acid Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@@H](C(O)=O)C1=CC=CC=C1 JQEHQELQPPKXRR-LLVKDONJSA-N 0.000 claims 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-O 1,2,3,4-tetrahydroquinolin-1-ium Chemical compound C1=CC=C2CCC[NH2+]C2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-O 0.000 claims 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- OIJPSMYQMUNKSB-UHFFFAOYSA-N 2-thiophen-2-ylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)C1=CC=CS1 OIJPSMYQMUNKSB-UHFFFAOYSA-N 0.000 claims 1
- DPPJUNQLKVGLNY-UHFFFAOYSA-N 3-chloro-3-oxo-2-phenylpropanoic acid Chemical compound OC(=O)C(C(Cl)=O)C1=CC=CC=C1 DPPJUNQLKVGLNY-UHFFFAOYSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 206010010071 Coma Diseases 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Chemical group 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 229950006191 gluconic acid Drugs 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000005304 joining Methods 0.000 claims 1
- 239000011591 potassium Chemical group 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
Classifications
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cephalosporin Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 하기 일반식(I)로 표시되는 화합툴과 약리학적으로 허용되는 이들 화합툴의 염류를 제조함에 있어서,(상기 일반식에서, R는 2-페닐아세트아미도, 2-페녹시아세트아미도, D-2-아미노-2-페닐아세트아미도, D-2-아미노-2-(4-히드록시페닐)아세트아미도, 2-카르복시-2-페닐아세트아미도, 2-카르복시-2-(2-티에닐)아세트아미도, 2-카르복시-2-(3-티에닐)-아세트아미도, D-2-(4-에틸-2,3-디옥소피페라지노카르보닐아미도)-2-페닐아세트아미도 또는 2,2-디메틸-4-페닐-5-이미다졸리딘온-1-일이고 R'는 수소원자 또는 메틸기 임), (a) 하기 일반식(II)로 표시되는 합합툴을 하기 일반식(III)으로 2표시되는 카르복실산염과 반응시키고,(상기 일반식에서, R'는 수소원자 또는 메틸기이고, X는 클로로, 브로모, 요오도,(C1-C4)알킬술포닐옥시, 벤젠술포닐옥시 또는 툴루엔술포닐옥시이며, R'"는 2-페닐아세트아미도, 2-페녹시아세트아미도, D-2-(4-에틸-2,3-디옥소피페라지노카르보닐아미노-2-페닐아세트아미도, 2,2-디메틸-4-페닐-5-이미다졸리딘온-1-일, 2-벤질옥시카르보닐-2-페닐아세트아미도, 2-벤질옥시-카르보닐-2-(3-티에닐)아세트아미도, 2-벤질옥시카르보닐-2-(2-티에닐)아세트아미도, 또는의 n-형이고, (여기서, Y는 수소원자 또는 수산기이고 Z는 아지도, 벤질옥시카르보닐아미노 또는 1-카르보메톡시-1-프로펜-2-일-아미노기임), M은 나트륨, 칼륨, 칼슘, 바륨, 트리메틸암노늄, 트리에틸암모늄, 트리부틸암모늄, 디이소프로필에틸암모늄, N-메틸모르폴리늄, N-메틸피페리디늄, 1,2,3,4 테트라히드로퀴놀리늄 및 테트라부틸암모늄으로 구성되는 군에서 선택된 카르복실산염 생성 양이온이며), R'"가 2-벤질옥시카르보닐-2-페닐아세트아미도, 2-벤질옥시(3-티에닐)아세트아미도, 2-벤질옥시(2-티에닐)-아세트아미도 또는일때 그 중간 화합툴을 수소화시키며, (b) 하기 일반식(IV)로 표시되는 화합물을 하기 일반식(V)로 표시되는 화합물과 반응시키고,(상기 일반식에서, R', R'", M 및 X는 위에서 정의한 것과 같음), R'"가 2-벤질옥시카르보닐페닐-2-아세트아미도, 2-벤질옥시(3-티에닐)아세트아미도, 2-벤질옥시(2-티에닐)-아세트아미도 또는일 때 그 중간화합물을 수소화시키며, (c) 하기 일반식(VI)으로 표시되는 화합물 (여기서, R'는 수소 또는 메틸기임)을 2-페닐아세트산, 2-페녹시아세트산, D-2-(4-에틸-2,3-디옥소피페라지노카르보닐아미노)-2-페닐아세트산, 또는의 D-형(여기서 Z는 위에서 정의한 것과 같음)의 산염화물 또는 혼수무수물, 카테보디이미드와 결합한 전기산들 중의 한가지, 2-페닐말톤산 모노산염화물, 2-(3-티에닐)말톤산모노산염화물, 또는 2-(2-티에닐)말톤산 모노산 염화물과 아실화시키고, 그 산이 t-9 일 때 생성된 중간체를 수소화시켜서 R가 2-페닐아세트아미도, 2-페녹시아세트아미도, D-2-아미노-2-페닐아세트아미도, 2-카르복시-2-2-페닐아세트아미도, 2-카르복시-2-(2티에닐)아세트아미도, 2-카르복시 2-(3-티에닐)아세트아미도 또는D-2-(4-에틸)-2,3-디옥소피페라지노카르보닐아미노)-2-페닐아세트아미도인 일반식(I)도 표시되는 화합물을 제조하거나,(d) R가 d-2-아미노-2-페닐아세트아미도인 일반식(I)로 표시되는 화합물을 아세톤과 반응시켜서 R가 2,2-디메틸-4-페닐-5-이미다졸린은-1-일인 일반식(I)로 표시되는 화합물을 제조하고, 필요할 경우에, 산기 또는 염기기를 함유하는 일반식(I)로 표시되는 화합물을 각각 약리적으로 허용되는 양이온 또는 산부가염으로 전환시키는 것을 특징으로 하는 1,1-알칸디류의 비스-에스테르류를 제조하는 방법.
- 특허 청구의 범위 제1항 기재에 있어서, R'가 수소인 것이 특징인 제조방법.
- 특허 청구의 범위 제2항 기재에 있어서, R'가 D-2-아미노-2-페닐아세트아미도기인 것이 특징인 제조방법.
- 특허 청구의 범위 제2항 기재에 있어서, R가 2-카르복시-2-페닐아세트아미도기인 것이 특징인 제조방법.
- 특허 청구의 범위 제2항 기재에 있어서, R가 D-2-아미노-2-(4-히드록시페닐)아세트아미도기인 것이 특징인 제조방법.
- 특허 청구의 범위 제2항 기재에 있어서, R가 2-페닐아세트아미도기인 것이 특징인 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US246,505 | 1981-03-23 | ||
| US06/246,505 US4342768A (en) | 1979-10-22 | 1981-03-23 | Bis-esters of 1,1-alkanediols with 6-beta-hydroxymethylpenicillanic acid 1,1-dioxide and beta-lactam antibiotics |
| US246505 | 1981-03-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830009110A true KR830009110A (ko) | 1983-12-17 |
| KR860000425B1 KR860000425B1 (ko) | 1986-04-19 |
Family
ID=22930958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8201220A KR860000425B1 (ko) | 1981-03-23 | 1982-03-22 | 6-베타-히드록시메틸페니실란산 1, 1-디옥시드와 베타-락탐항생제를 이용한 1, 1-알칸디올류의 비스-에스테르류의 제조 방법 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4342768A (ko) |
| EP (1) | EP0061313B1 (ko) |
| JP (1) | JPS57169492A (ko) |
| KR (1) | KR860000425B1 (ko) |
| AT (1) | ATE11291T1 (ko) |
| AU (1) | AU527895B2 (ko) |
| CA (1) | CA1201709A (ko) |
| CS (1) | CS228921B2 (ko) |
| DD (1) | DD203723A5 (ko) |
| DE (1) | DE3261898D1 (ko) |
| DK (1) | DK126982A (ko) |
| ES (1) | ES510656A0 (ko) |
| FI (1) | FI74285C (ko) |
| GR (1) | GR76107B (ko) |
| GT (1) | GT198274394A (ko) |
| HU (1) | HU186487B (ko) |
| IE (1) | IE52812B1 (ko) |
| IL (1) | IL65306A (ko) |
| NO (1) | NO820897L (ko) |
| NZ (1) | NZ200068A (ko) |
| PH (1) | PH18040A (ko) |
| PL (1) | PL130110B1 (ko) |
| PT (1) | PT74624B (ko) |
| SU (1) | SU1122230A3 (ko) |
| YU (1) | YU61882A (ko) |
| ZA (1) | ZA821901B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU559689B2 (en) * | 1981-09-22 | 1987-03-19 | Kureha Kagaku Kogyo K.K. | Penicillin derivative |
| US4452796A (en) * | 1982-06-14 | 1984-06-05 | Pfizer Inc. | 6-Aminoalkylpenicillanic acid 1,1-dioxides as beta-lactamase inhibitors |
| EP0084730A1 (en) * | 1982-01-22 | 1983-08-03 | Beecham Group Plc | Esters of penicillin derivatives with beta-lactamase inhibitors, their preparation and their use |
| DE3302335A1 (de) * | 1982-01-26 | 1983-07-28 | Leo Pharmaceutical Products Ltd. A/S (Loevens kemiske Fabrik Produktionsaktieselskab), 2750 Ballerup | Ss-lactamverbindungen, ihre herstellung und sie enthaltendes arzneimittel |
| US4462934A (en) | 1983-03-31 | 1984-07-31 | Pfizer Inc. | Bis-esters of dicarboxylic acids with amoxicillin and certain hydroxymethylpenicillanate 1,1-dioxides |
| US4536393A (en) * | 1983-06-06 | 1985-08-20 | Pfizer Inc. | 6-(Aminomethyl)penicillanic acid 1,1-dioxide esters and intermediates therefor |
| US4503040A (en) * | 1984-02-27 | 1985-03-05 | Pfizer Inc. | 6-(Aminoacyloxymethyl)penicillanic acid 1,1-dioxides as beta-lactamase inhibitors |
| US4591459A (en) * | 1984-12-03 | 1986-05-27 | Pfizer Inc. | Intermediates for 6-(aminoacyloxymethyl) penicillanic acid 1,1-dioxides |
| US4675186A (en) | 1985-04-18 | 1987-06-23 | Pfizer Inc. | 6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives |
| US4762921A (en) * | 1985-04-18 | 1988-08-09 | Pfizer Inc. | 6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives |
| JPS63144296U (ko) * | 1987-03-12 | 1988-09-22 | ||
| CN108107120B (zh) * | 2017-12-12 | 2020-12-01 | 山东鑫泉医药有限公司 | 采用高效液相法测定中间产物6,6-二溴青霉烷酸的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4207323A (en) * | 1975-11-21 | 1980-06-10 | Merck & Co., Inc. | 6-Substituted methyl penicillins, derivatives and analogues thereof |
| IE49881B1 (en) | 1979-02-13 | 1986-01-08 | Leo Pharm Prod Ltd | B-lactam intermediates |
| US4244951A (en) * | 1979-05-16 | 1981-01-13 | Pfizer Inc. | Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide |
-
1981
- 1981-03-23 US US06/246,505 patent/US4342768A/en not_active Expired - Fee Related
-
1982
- 1982-03-17 GT GT198274394A patent/GT198274394A/es unknown
- 1982-03-18 NO NO820897A patent/NO820897L/no unknown
- 1982-03-19 DE DE8282301413T patent/DE3261898D1/de not_active Expired
- 1982-03-19 NZ NZ200068A patent/NZ200068A/en unknown
- 1982-03-19 CA CA000398885A patent/CA1201709A/en not_active Expired
- 1982-03-19 EP EP82301413A patent/EP0061313B1/en not_active Expired
- 1982-03-19 AT AT82301413T patent/ATE11291T1/de not_active IP Right Cessation
- 1982-03-19 DD DD82238312A patent/DD203723A5/de unknown
- 1982-03-22 ES ES510656A patent/ES510656A0/es active Granted
- 1982-03-22 DK DK126982A patent/DK126982A/da not_active Application Discontinuation
- 1982-03-22 IE IE656/82A patent/IE52812B1/en unknown
- 1982-03-22 KR KR8201220A patent/KR860000425B1/ko active
- 1982-03-22 PT PT74624A patent/PT74624B/pt unknown
- 1982-03-22 FI FI820992A patent/FI74285C/fi not_active IP Right Cessation
- 1982-03-22 AU AU81761/82A patent/AU527895B2/en not_active Ceased
- 1982-03-22 YU YU00618/82A patent/YU61882A/xx unknown
- 1982-03-22 HU HU82854A patent/HU186487B/hu unknown
- 1982-03-22 SU SU823408648A patent/SU1122230A3/ru active
- 1982-03-22 ZA ZA821901A patent/ZA821901B/xx unknown
- 1982-03-22 GR GR67670A patent/GR76107B/el unknown
- 1982-03-22 IL IL65306A patent/IL65306A/xx unknown
- 1982-03-23 CS CS822016A patent/CS228921B2/cs unknown
- 1982-03-23 PH PH27042A patent/PH18040A/en unknown
- 1982-03-23 PL PL1982235576A patent/PL130110B1/pl unknown
- 1982-03-23 JP JP57046183A patent/JPS57169492A/ja active Granted
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