KR830009020A - 새로운 베타-락탐초산 유도체의 제조방법 - Google Patents
새로운 베타-락탐초산 유도체의 제조방법 Download PDFInfo
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- KR830009020A KR830009020A KR1019820001103A KR820001103A KR830009020A KR 830009020 A KR830009020 A KR 830009020A KR 1019820001103 A KR1019820001103 A KR 1019820001103A KR 820001103 A KR820001103 A KR 820001103A KR 830009020 A KR830009020 A KR 830009020A
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- -1 beta-lactam acetate derivative Chemical class 0.000 title claims 13
- 238000000034 method Methods 0.000 title claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 239000007858 starting material Substances 0.000 claims 4
- LQXNIPLTFRANDL-UHFFFAOYSA-N 1-azabicyclo[3.2.0]hept-2-ene Chemical compound C1=CCC2CCN21 LQXNIPLTFRANDL-UHFFFAOYSA-N 0.000 claims 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 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 claims 3
- 229930194542 Keto Natural products 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 claims 2
- 159000000003 magnesium salts Chemical class 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 230000001681 protective effect Effects 0.000 claims 2
- 150000003952 β-lactams Chemical class 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- CFLAHQSWDKNWPW-UHFFFAOYSA-N 3-(benzyloxy)-3-oxopropanoic acid Chemical group OC(=O)CC(=O)OCC1=CC=CC=C1 CFLAHQSWDKNWPW-UHFFFAOYSA-N 0.000 claims 1
- RIGFMUNSTCPGNP-UHFFFAOYSA-M 3-[(4-nitrophenyl)methoxy]-3-oxopropanoate Chemical compound [O-]C(=O)CC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 RIGFMUNSTCPGNP-UHFFFAOYSA-M 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000006264 debenzylation reaction Methods 0.000 claims 1
- 150000008049 diazo compounds Chemical class 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- PLLAGNDLRNXFLU-UHFFFAOYSA-N methyl 3-phenylmethoxypropanoate Chemical compound COC(=O)CCOCC1=CC=CC=C1 PLLAGNDLRNXFLU-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000012286 potassium permanganate Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 claims 1
- ITDJKCJYYAQMRO-UHFFFAOYSA-L rhodium(2+);diacetate Chemical compound [Rh+2].CC([O-])=O.CC([O-])=O ITDJKCJYYAQMRO-UHFFFAOYSA-L 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 238000006276 transfer reaction Methods 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/02—Preparation
- C07D477/04—Preparation by forming the ring or condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 하기 구조식 II의 화합물을 산화시켜 하기 구조식 I을 갖는 β-락탐 아세트산 유도체 및 그 유도체를 제조하는 방법.상기 식에서, R은 알킬, 아미노로 치환된 알킬, 보호아미노, 모노- 및 디-알킬아미노, 히드록시, 보호히드록시, 또는 알콕시 및 알케닐이다.
- 제1항에 있어서, pH 4-9에서 완충된 수용성 과망간산칼륨을 산화제로서 이용하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 구조식 II의 화합물이 하기 구조식(IV)의 트랜스-4-치환-2-부텐-1-알의 에놀-아세테이트를 출발물질로 하여 클로로설포닐이소시아네이트와 반응시켜 하기 구조식(V)를 갖는 2-아제티디논을 얻은 다음, 상기 2-아제티디논(V)를 환원적 가수분해시켜 얻은 하기 구조식(VI)의 2-아제티디논(VI)을 수소첨가 및 아세틸제거반응시켜 얻은 것을 특징으로 하는 방법.여기서, R은 상기에서 규정한 바와 같다.
- 제1항에 있어서, 구조식 II의 화합물은, 염기촉매화 조건하에서 벤질 또는 치환된 벤질알콜을 메틸아크릴레이트에 첨가하고, 얻어진 3-벤질옥시-프로피온산 메틸에스테르를 비누화한 다음, 얻어진 산을 할로겐화제와 반응시켜 3-벤질옥시프로파노일 할로겐화물을 얻고, 얻어진 산할로겐화물을 하기 구조식(A)를 갖는 말론산 모노-저급알킬 에스테르의 마그네슘염과 축합시킨 후, 얻어진 하기 구조식(IX)의 케토에스테르를 환원전 아민화시켜 하기 구조식(X)의 아민 유도체를 얻은 후, 아민유도체(X)를 그리나드시약 R1MgX1(R1는 저급알킬기이며 X1는 염소, 브롬 또는 요오드이다) 또는 리튬시약 R11-Li(R11는 알킬, 알케닐 또는 아릴기이다)으로 처리함으로써 하기 구조식(XI)의 β-락탐으로 전환시킨 다음 촉매적 탈벤질화에 의해 제조되는 것을 특징으로 하는 방법.상기 식에서,R은 상기 규정한 바와 같고,R1은 수소, 저급알킬, 저급알콕시 또는 니트로이다.
- 제1항에 있어서, 구조식 I의 시스 및 트랜스 이성체의 혼합물이 얻어질때, 에틸 아세테이트로 결정화시켜 시스와 트랜스 라세미산염으로 분리하는 것을 특징으로 하는 방법.
- 제1항에 있어서, 2 및 3위치의 수소원자 트랜스 입체화합물인 구조식 II의 화합물이 출발화합물로 이용되는 것을 특징으로 하는 방법.
- 제5 및 6항에 있어서, 산 I의 트랜스 라세미산염이 종래 방법에 의해 단일 에난티오머로 분리되는 것을 특징으로 하는 방법.
- 제1 내지 7항중 어느 하나에 있어서, R이 알킬인 구조식 I 화합물을 제조하기 위한 방법.
- 제8항에 있어서, R이 에틸인 구조식 I 화합물을 제조하기 위한 방법.
- 하기 구조식의 I의 β-락탐 아세트산 유도체를 출발물질로 하여 이미다졸일 유도체로 이전시킨 다음 모노벤질 또는 모노-p-니트로벤질 말론산염의 마그네슘염과 반응시켜 하기 구조식(XIII)의 p-케토에스테르를 얻은 다음, 얻어진 화합물(XII)을 디아조 전이반응시켜 하기 구조식(XIV)의 α-디아조-β-케노 에스테르를 얻고, 로듐(II)-아세테이트와 같은 적당한 촉매 존재하에서 구조식(XIV)의 디아조화합물을 분해시켜 이환식 케토 에스테르(XV)를 얻은 다음, 중간체(XV)을 디페닐 클로로포스페이트와 반응시켜 하기 구조식(XVI)의 에놀 포스페이트로 전환시킨 후, 에놀-포스페이트(XVI)를 적당히 선정된 구핵 R'"SH(R'"는 여러가지로 치환된 탄화수소 잔류기이다)와 반응시켜 하기 구조식(XVII)의 에스테르를 얻은 다음, 마지막으로 에스테르(XVII)를 촉매적으로 보호해제시켜 하기 구조식(XVIII)의 1-아자비시클로[3,2,0] 헵트-2-엔(XVIII)을 얻는 것을 특징으로 하는 항생제 1-아지비시클로[3,2,0] 헵트-2-엔 및 그 염을 제조하는 방법 :상기 식에서,R은 알킬아미노, 보호아미노, 모노- 및 디-알킬아미노, 히드록시, 보호히드록시 또는 알콕시로 알케닐로 치환된 알킬 그리고 알케닐이며R4는 벤질 또는 p-니트로벤질라디칼이며는 알카리 금속 양이온이다.
- 제10항에 있어서, 2 및 3위치에 수소원자가 트랜스 입체화합물인 구조식 I의 β-락탐 아세트산 유도체가 출발화합물로 이용되는 것을 특징으로 하는 방법.
- 제11항에 있어서, 트랜스-입체화합물인 3-[[2-(아세틸아미노)에틸]티오]-6-에틸-7-옥소-1-아자비시클로[3,2,0] 헵트-2-엔-2-카르복실산 알카리 금속염을 제조하기 위한 방법.
- 제12항에 있어서, (5R, 6R) 트랜스 3-[[2-(아세틸아미노)에틸]티오]-6-에틸-7-옥소-1-아자비시클로[3,2,0] 헵트-2-엔-2-카르복실산 알카리 금속염을 제조하는 방법.
- 제3항에 있어서, 트리알킬아민, 촉매량의 피리딘, 디메틸아미노피리딘 또는 N-메틸이미다졸의 존재하에서 트랜스-4-치환-2-부텐-1-알을 무수초산과 반응시킴으로써 구조식(IV)의 에놀-아세테이트를 제조하는 방법.
- 제10항에 있어서, 하기 구조식의 β-락탐 아세트산 유도체로부터 티엔아미산을 제조하는 방법.상기 식에서, R은 수산기가 보호되는 1-히드록시에틸기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8107865 | 1981-03-12 | ||
| GB8107865 | 1981-03-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830009020A true KR830009020A (ko) | 1983-12-17 |
| KR880001847B1 KR880001847B1 (ko) | 1988-09-22 |
Family
ID=10520350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8201103A KR880001847B1 (ko) | 1981-03-12 | 1982-03-11 | 새로운 베타-락탐초산유도체의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4576746A (ko) |
| EP (1) | EP0060416B1 (ko) |
| JP (1) | JPS57159761A (ko) |
| KR (1) | KR880001847B1 (ko) |
| AT (1) | ATE21509T1 (ko) |
| AU (1) | AU548727B2 (ko) |
| CA (1) | CA1185244A (ko) |
| DE (1) | DE3272660D1 (ko) |
| DK (1) | DK103982A (ko) |
| ES (2) | ES8308540A1 (ko) |
| IE (1) | IE52609B1 (ko) |
| IL (1) | IL65232A (ko) |
| PH (1) | PH23415A (ko) |
| ZA (1) | ZA821252B (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU187424B (en) * | 1982-11-05 | 1986-01-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing new azetidinyl-acetic acids |
| JPS60224672A (ja) * | 1984-04-23 | 1985-11-09 | Sumitomo Chem Co Ltd | β−ラクタム誘導体の製造法 |
| JPS62209079A (ja) * | 1986-03-11 | 1987-09-14 | Sanraku Inc | 二置換アミノカルバペナム類 |
| JP2618271B2 (ja) * | 1989-04-26 | 1997-06-11 | 日本化薬株式会社 | モノｐ―ニトロベンジルマロネートマグネシウム塩の結晶変態及びその製法 |
| WO1994006764A1 (en) * | 1992-09-18 | 1994-03-31 | Merck & Co., Inc. | Preparation of beta-methyl carbapenem intermediates |
| US5516934A (en) * | 1994-08-05 | 1996-05-14 | Nippon Kayaku Kabushiki Kaisha | Process for producing mono-P-nitrobenzyl malonate |
| US20040148868A1 (en) * | 2003-02-05 | 2004-08-05 | 3M Innovative Properties Company | Methods of making ceramics |
| CN101098970B (zh) * | 2004-12-10 | 2010-05-12 | V.B.医疗保险私人有限公司 | 通过在6-乙酰基-4,1',6'三氯半乳蔗糖和4,1',6'三氯半乳蔗糖的有机溶剂提取物的浓缩过程中直接加入碳酸盐和碳酸氢盐来调节pH的方法 |
| PE20161560A1 (es) | 2009-09-03 | 2017-01-11 | Pfizer Vaccines Llc | Vacuna de pcsk9 |
| WO2011048583A1 (en) * | 2009-10-23 | 2011-04-28 | Ranbaxy Laboratories Limited | Process for the preparation of carbapenem compounds |
| CN103483202B (zh) * | 2013-06-26 | 2015-01-21 | 华北水利水电大学 | 一种对硝基苄醇丙二酸单酯镁的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1570278A (en) * | 1975-10-06 | 1980-06-25 | Fujisawa Pharmaceutical Co | O-substituted-2-azetidinone derivatives and the preparation thereof |
| US4138400A (en) * | 1975-12-20 | 1979-02-06 | Hoechst Aktiengesellschaft | Omega-alkoxy derivatives of lactams |
| GB1584762A (en) * | 1977-04-01 | 1981-02-18 | Beecham Group Ltd | Azabicycloheptenes |
| EP0017992A1 (en) * | 1979-04-19 | 1980-10-29 | Merck & Co. Inc. | 2-Substituted-6-substituted-1-carbadethiapen-2-em-3-carboxylic acids, processes for preparing them, antibiotic pharmaceutical compositions containing same and process for preparing intermediates |
| US4290947A (en) * | 1979-04-27 | 1981-09-22 | Merck & Co., Inc. | Process for the preparation of thienamycin and intermediates |
| US4262010A (en) * | 1979-12-03 | 1981-04-14 | Merck & Co., Inc. | 6-(1-Hydroxyethyl)-2-(2-aminoethylthio)-1,1-disubstituted-1-carbadethiapen-2-em-3-carboxylic acids |
| US4312871A (en) * | 1979-12-03 | 1982-01-26 | Merck & Co., Inc. | 6-, 1- And 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids |
| US4287123A (en) * | 1980-01-14 | 1981-09-01 | Merck & Co., Inc. | Synthesis of thienamycin via (3SR, 4RS)-3-((RS)-1-acyloxyethyl)-2-oxo-4-azetidineacetate |
| US4269772A (en) * | 1980-01-14 | 1981-05-26 | Merck & Co., Inc. | Synthesis of thienamycin via trans-3-carboxymethylene-4-carboxy-5-methyl-Δ2 -isoxazoline |
| US4282148A (en) * | 1980-01-14 | 1981-08-04 | Merck & Co., Inc. | Synthesis of thienamycin via esters of (3SR, 4RS)-3-[(SR)-1-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid |
-
1982
- 1982-02-24 AU AU80765/82A patent/AU548727B2/en not_active Ceased
- 1982-02-25 ZA ZA821252A patent/ZA821252B/xx unknown
- 1982-02-26 EP EP82101463A patent/EP0060416B1/en not_active Expired
- 1982-02-26 DE DE8282101463T patent/DE3272660D1/de not_active Expired
- 1982-02-26 AT AT82101463T patent/ATE21509T1/de not_active IP Right Cessation
- 1982-03-04 PH PH26950A patent/PH23415A/en unknown
- 1982-03-04 US US06/354,572 patent/US4576746A/en not_active Expired - Fee Related
- 1982-03-10 DK DK103982A patent/DK103982A/da not_active Application Discontinuation
- 1982-03-11 ES ES510336A patent/ES8308540A1/es not_active Expired
- 1982-03-11 KR KR8201103A patent/KR880001847B1/ko active
- 1982-03-11 CA CA000398140A patent/CA1185244A/en not_active Expired
- 1982-03-11 IE IE554/82A patent/IE52609B1/en unknown
- 1982-03-12 JP JP57039284A patent/JPS57159761A/ja active Pending
- 1982-03-12 IL IL65232A patent/IL65232A/xx unknown
- 1982-10-25 ES ES516808A patent/ES516808A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1185244A (en) | 1985-04-09 |
| ATE21509T1 (de) | 1986-09-15 |
| IE52609B1 (en) | 1987-12-23 |
| IL65232A (en) | 1986-01-31 |
| ES510336A0 (es) | 1983-09-01 |
| KR880001847B1 (ko) | 1988-09-22 |
| JPS57159761A (en) | 1982-10-01 |
| PH23415A (en) | 1989-08-07 |
| ZA821252B (en) | 1983-01-26 |
| EP0060416A1 (en) | 1982-09-22 |
| EP0060416B1 (en) | 1986-08-20 |
| ES8402590A1 (es) | 1984-02-01 |
| ES8308540A1 (es) | 1983-09-01 |
| DK103982A (da) | 1982-09-13 |
| IE820554L (en) | 1982-09-12 |
| AU8076582A (en) | 1982-09-16 |
| DE3272660D1 (en) | 1986-09-25 |
| ES516808A0 (es) | 1984-02-01 |
| AU548727B2 (en) | 1986-01-02 |
| IL65232A0 (en) | 1982-05-31 |
| US4576746A (en) | 1986-03-18 |
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