KR840006663A - 1-옥사-β-락탐의 제조방법 - Google Patents
1-옥사-β-락탐의 제조방법 Download PDFInfo
- Publication number
- KR840006663A KR840006663A KR1019830005407A KR830005407A KR840006663A KR 840006663 A KR840006663 A KR 840006663A KR 1019830005407 A KR1019830005407 A KR 1019830005407A KR 830005407 A KR830005407 A KR 830005407A KR 840006663 A KR840006663 A KR 840006663A
- Authority
- KR
- South Korea
- Prior art keywords
- protected
- alkyl
- group
- carboxy
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- -1 1,4-cyclohexadienyl Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 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
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000000087 stabilizing effect Effects 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- SWBGAVUCSRMXBR-UHFFFAOYSA-N 2-oxoazetidine-1-sulfinic acid Chemical compound OS(=O)N1CCC1=O SWBGAVUCSRMXBR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B3/00—Ohmic-resistance heating
- H05B3/20—Heating elements having extended surface area substantially in a two-dimensional plane, e.g. plate-heater
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; 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
-
- D—TEXTILES; PAPER
- D03—WEAVING
- D03D—WOVEN FABRICS; METHODS OF WEAVING; LOOMS
- D03D1/00—Woven fabrics designed to make specified articles
-
- D—TEXTILES; PAPER
- D03—WEAVING
- D03D—WOVEN FABRICS; METHODS OF WEAVING; LOOMS
- D03D13/00—Woven fabrics characterised by the special disposition of the warp or weft threads, e.g. with curved weft threads, with discontinuous warp threads, with diagonal warp or weft
-
- D—TEXTILES; PAPER
- D03—WEAVING
- D03D—WOVEN FABRICS; METHODS OF WEAVING; LOOMS
- D03D15/00—Woven fabrics characterised by the material, structure or properties of the fibres, filaments, yarns, threads or other warp or weft elements used
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B3/00—Ohmic-resistance heating
- H05B3/10—Heating elements characterised by the composition or nature of the materials or by the arrangement of the conductor
- H05B3/12—Heating elements characterised by the composition or nature of the materials or by the arrangement of the conductor characterised by the composition or nature of the conductive material
- H05B3/14—Heating elements characterised by the composition or nature of the materials or by the arrangement of the conductor characterised by the composition or nature of the conductive material the material being non-metallic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 일반식(Ⅰ)의 아제티딘-2-온 설핀산 몰당 납테트라아세테이트 약 1몰 내지 약 2.5몰을 불활성유기용매중 약 -25℃ 내지 약 0℃의 온도에서 혼합, 반응시킴을 특징으로 하여 일반식(Ⅰ)의 화합물과 일반식(Ⅲ)의 이성체 화합물을 제조하는 방법.상기식에서, R은 수소, C1-C4알킬, 또는 일반식의 α-(보호된 아미노)-4-카복시부틸그룹 [여기서 R′는 카복시-보호그룹이고 R″는 보호된 아미노그룹], 또는 일반식의 그룹 [여기서 R″′는 티에닐, 푸릴, 테트라졸릴, 1,4-이클로헥사디에닐, 사이클로헥세닐, 페닐 또는 일반식의 치환된 페닐그룹(여기서 a와 a′는 각각 수소, C1-C4알킬, 플루오로, 클로로, 보호된 아미노, 보호된 아미노메틸, 보호된 카복시, 보호된 카복시메틸, 카바모일, C1-C4알콕시, 또는 하이드록시이다)이며 ; Q는 수소, 보호된 아미노, 보호된카복시, 또는 보호된 하이드록시이다], 또는 일반식의 아릴옥시메틸그룹 [여기서 a와 a′는 상기 정의한 바와 같다], 또는 일반식 R″′-0-의 알콕시 또는 치환된 알콕시 그룹 [여기서 R″″는 C1-C5알킬, C3-C6사이클로 알킬, 벤질 ; 또는 C1-C4알킬, C1-C4알콕시, 또는 염소로 치환된 벤질]이고 R1은 카복시-보호그룹이다.
- 제1항에 있어서, 아제티딘-2-온을 납 테트라아세테이트와 카보니움이온 안정화 화합물존재하에서 혼합시키는 방법.
- 제2항에 있어서, R이 벤질옥시이고 카보니움이온 안정화 화합물이 이산화황인 방법.
- 제1항에서 3항중 어느 한항에 있어서, R이 벤질 옥시 또는 페녹시메틸인 방법.
- 제1항에서 4항중 어느 한항에 있어서, 반응이 구리(Ⅱ)이온 존재하에서 진행되는 방법.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/442,080 US4458071A (en) | 1982-11-16 | 1982-11-16 | Process for 1-oxa-β-lactams |
| US442080 | 1982-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840006663A true KR840006663A (ko) | 1984-12-01 |
Family
ID=23755471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830005407A KR840006663A (ko) | 1982-11-16 | 1983-11-15 | 1-옥사-β-락탐의 제조방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4458071A (ko) |
| EP (1) | EP0109302A1 (ko) |
| JP (1) | JPS59104390A (ko) |
| KR (1) | KR840006663A (ko) |
| DK (1) | DK518883A (ko) |
| GB (1) | GB2129803A (ko) |
| GR (1) | GR79030B (ko) |
| HU (1) | HU189774B (ko) |
| IL (1) | IL70220A0 (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4574153A (en) * | 1985-03-01 | 1986-03-04 | E. R. Squibb & Sons, Inc. | 8-Oxo-2-oxa-1-azabicyclo(4.2.0)octane-3-carboxylic acids |
| US4983732A (en) * | 1987-07-31 | 1991-01-08 | Eli Lilly And Company | Method of deprotection of 3-amino azetidinones |
| US5142039A (en) * | 1987-07-31 | 1992-08-25 | Eli Lilly And Company | β-lactam antibiotics |
| JPS6463567A (en) * | 1987-07-31 | 1989-03-09 | Lilly Co Eli | Deprotection of 3-aminoazetidinones |
| US5239068A (en) * | 1987-07-31 | 1993-08-24 | Eli Lilly And Company | Bicyclic β-lactam antibiotics |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150156A (en) * | 1975-11-21 | 1979-04-17 | Merck & Co., Inc. | 7-(Substituted methyl)-3-(substituted thio)-cephalosporins, derivatives and pharmaceutical compositions containing them |
| AU514377B2 (en) * | 1977-02-15 | 1981-02-05 | Shionogi & Co., Ltd. | l-OXADETHIACEPHAM COMPOUNDS |
| US4293493A (en) * | 1980-04-07 | 1981-10-06 | Eli Lilly And Company | Azetidinone alcohol disulfides and process for cyclization |
-
1982
- 1982-11-16 US US06/442,080 patent/US4458071A/en not_active Expired - Fee Related
-
1983
- 1983-11-13 IL IL70220A patent/IL70220A0/xx unknown
- 1983-11-14 JP JP58215910A patent/JPS59104390A/ja active Pending
- 1983-11-14 EP EP83306941A patent/EP0109302A1/en not_active Withdrawn
- 1983-11-14 GR GR72975A patent/GR79030B/el unknown
- 1983-11-14 GB GB08330282A patent/GB2129803A/en not_active Withdrawn
- 1983-11-14 DK DK518883A patent/DK518883A/da not_active Application Discontinuation
- 1983-11-15 HU HU833924A patent/HU189774B/hu unknown
- 1983-11-15 KR KR1019830005407A patent/KR840006663A/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59104390A (ja) | 1984-06-16 |
| HU189774B (en) | 1986-07-28 |
| GR79030B (ko) | 1984-10-02 |
| US4458071A (en) | 1984-07-03 |
| EP0109302A1 (en) | 1984-05-23 |
| IL70220A0 (en) | 1984-02-29 |
| GB2129803A (en) | 1984-05-23 |
| DK518883D0 (da) | 1983-11-14 |
| GB8330282D0 (en) | 1983-12-21 |
| DK518883A (da) | 1984-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SUBM | Surrender of laid-open application requested |