KR840007009A - 1,1-디옥소 페니실라노일옥시메틸 6-β-아미노 페니실라네이트의 제조방법 - Google Patents
1,1-디옥소 페니실라노일옥시메틸 6-β-아미노 페니실라네이트의 제조방법 Download PDFInfo
- Publication number
- KR840007009A KR840007009A KR1019830005159A KR830005159A KR840007009A KR 840007009 A KR840007009 A KR 840007009A KR 1019830005159 A KR1019830005159 A KR 1019830005159A KR 830005159 A KR830005159 A KR 830005159A KR 840007009 A KR840007009 A KR 840007009A
- Authority
- KR
- South Korea
- Prior art keywords
- temperature
- preparing
- formula
- mentioned
- penicilanoyloxymethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000002140 halogenating effect Effects 0.000 claims 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 2
- 150000003512 tertiary amines Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- -1 imino halide Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- 150000003138 primary alcohols Chemical class 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/28—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with modified 2-carboxyl group
- C07D499/32—Esters
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Cultivation Of Plants (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims (9)
- 일반식(Ⅱ)의 화합물을 무수 상태하 -70 내지 20˚C의 온도에서 반응 불활성 유기용매 및 3급 아민의 존재하에 할로 겐화제와 반응시켜 이미노 할라이드를 제조하고 생성된 이미노 할라이드를 -70 내지 0˚C의 온도에서 일반식 R2OH의 1급알콜과 반응시켜 이미노 에테르를 제조하고, 생성된 이미노 에테르를 -70 내지 0˚C의 온도에서 물과 반응시킴을 특징으로 하는 하기 구조식(Ⅰ) 화합물의 제조방법.
-
- 상기식에서,
- R1은 C6H5CH2또는 C6H5OCH2이고, R2는 1 내지 4개의 탄소원자를 갖는 알킬이다.
- 제 1항에 있어서, R1이 C6H5CH2이고, 언급된 할로 겐화제가 포스포러스 펜타클로라이드이며, 언급된 3급 아민이 피리딘 또는 N,N-디메틸아닐린인 방법.
- 제 1항에 있어서, 각 단계에서 반응 온도가 약 -40 내지 -20˚C인 방법.
- 제 1항에 있어서, 언급된 용매가 디클로로메탄인 방법
- 제 1항에 있어서, R2가 메틸, 에틸 또는 n-부틸인 방법.
- ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US438,228 | 1982-11-01 | ||
| US438228 | 1982-11-01 | ||
| US06/438,228 US4530792A (en) | 1982-11-01 | 1982-11-01 | Process and intermediates for preparation of 1,1-dioxopenicillanoyloxymethyl 6-beta-aminopenicillanate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840007009A true KR840007009A (ko) | 1984-12-04 |
| KR860001494B1 KR860001494B1 (ko) | 1986-09-27 |
Family
ID=23739781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830005159A Expired KR860001494B1 (ko) | 1982-11-01 | 1983-10-31 | 1,1-디옥소페니실라노일옥시메틸 6-β-아미노 페니실라네이트의 제조방법 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4530792A (ko) |
| EP (1) | EP0108545B1 (ko) |
| JP (1) | JPS5998090A (ko) |
| KR (1) | KR860001494B1 (ko) |
| AT (1) | ATE24322T1 (ko) |
| AU (1) | AU541962B2 (ko) |
| CA (1) | CA1204736A (ko) |
| CS (1) | CS235986B2 (ko) |
| DD (1) | DD213926A5 (ko) |
| DE (1) | DE3368417D1 (ko) |
| DK (1) | DK163515C (ko) |
| EG (1) | EG15987A (ko) |
| ES (1) | ES526942A0 (ko) |
| FI (1) | FI76576C (ko) |
| GR (1) | GR78943B (ko) |
| GT (1) | GT198303898A (ko) |
| HU (1) | HU189769B (ko) |
| IE (1) | IE56179B1 (ko) |
| IL (1) | IL70095A (ko) |
| NZ (1) | NZ206108A (ko) |
| PH (1) | PH19573A (ko) |
| PL (1) | PL142735B1 (ko) |
| PT (1) | PT77580B (ko) |
| YU (1) | YU43989B (ko) |
| ZA (1) | ZA838091B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01139584A (ja) * | 1987-11-25 | 1989-06-01 | Yoshitomi Pharmaceut Ind Ltd | ペニシラン酸化合物の製造法 |
| GB2231049A (en) * | 1989-04-14 | 1990-11-07 | Yoshitomi Pharmaceutical | Method for producing diester compounds |
| US5399678A (en) * | 1990-04-13 | 1995-03-21 | Pfizer Inc. | Process for sultamicillin intermediate |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3896110A (en) * | 1971-10-04 | 1975-07-22 | American Home Prod | Process for preparation of 6-aminopenicillanic acid |
| GB1382736A (en) * | 1971-11-16 | 1975-02-05 | Yamanouchi Pharma Co Ltd | Process of producing semi-synthetic penicillin |
| FR2275460A1 (fr) * | 1974-06-20 | 1976-01-16 | Schmoller & Bompard | Procede pour la preparation de l'acide 6-aminopenicillanique |
| US4234579A (en) * | 1977-06-07 | 1980-11-18 | Pfizer Inc. | Penicillanic acid 1,1-dioxides as β-lactamase inhibitors |
| IE49880B1 (en) * | 1979-02-13 | 1986-01-08 | Leo Pharm Prod Ltd | Penicillin derivatives |
| US4244951A (en) * | 1979-05-16 | 1981-01-13 | Pfizer Inc. | Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide |
| US4364957A (en) * | 1979-09-26 | 1982-12-21 | Pfizer Inc. | Bis-esters of alkanediols as antibacterial agents |
| US4376076A (en) * | 1981-03-23 | 1983-03-08 | Pfizer Inc. | Bis-esters of 1,1-alkanediols with 6-beta-hydroxymethylpenicillanic acid 1,1-dioxide |
| US4359472A (en) * | 1981-12-22 | 1982-11-16 | Pfizer Inc. | Bis-hydroxymethyl carbonate bridged antibacterial agents |
| US4375434A (en) * | 1982-06-21 | 1983-03-01 | Pfizer Inc. | Process for 6'-amino-penicillanoyloxymethyl penicillanate 1,1-dioxide |
-
1982
- 1982-11-01 US US06/438,228 patent/US4530792A/en not_active Expired - Lifetime
-
1983
- 1983-10-21 PH PH29750A patent/PH19573A/en unknown
- 1983-10-25 EP EP83306460A patent/EP0108545B1/en not_active Expired
- 1983-10-25 DE DE8383306460T patent/DE3368417D1/de not_active Expired
- 1983-10-25 AT AT83306460T patent/ATE24322T1/de not_active IP Right Cessation
- 1983-10-26 CS CS838030A patent/CS235986B2/cs unknown
- 1983-10-28 YU YU2162/83A patent/YU43989B/xx unknown
- 1983-10-28 CA CA000440002A patent/CA1204736A/en not_active Expired
- 1983-10-28 FI FI833961A patent/FI76576C/fi not_active IP Right Cessation
- 1983-10-28 GT GT198303898A patent/GT198303898A/es unknown
- 1983-10-28 PT PT77580A patent/PT77580B/pt unknown
- 1983-10-28 PL PL1983244352A patent/PL142735B1/pl unknown
- 1983-10-28 IE IE2539/83A patent/IE56179B1/en not_active IP Right Cessation
- 1983-10-31 GR GR72828A patent/GR78943B/el unknown
- 1983-10-31 DD DD83256136A patent/DD213926A5/de not_active IP Right Cessation
- 1983-10-31 IL IL70095A patent/IL70095A/xx not_active IP Right Cessation
- 1983-10-31 NZ NZ206108A patent/NZ206108A/en unknown
- 1983-10-31 ZA ZA838091A patent/ZA838091B/xx unknown
- 1983-10-31 KR KR1019830005159A patent/KR860001494B1/ko not_active Expired
- 1983-10-31 ES ES526942A patent/ES526942A0/es active Granted
- 1983-10-31 HU HU833735A patent/HU189769B/hu unknown
- 1983-10-31 AU AU20821/83A patent/AU541962B2/en not_active Expired
- 1983-10-31 DK DK497483A patent/DK163515C/da not_active IP Right Cessation
- 1983-11-01 JP JP58205706A patent/JPS5998090A/ja active Granted
- 1983-11-01 EG EG681/83A patent/EG15987A/xx active
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| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19831031 |
|
| PA0201 | Request for examination | ||
| PG1501 | Laying open of application | ||
| G160 | Decision to publish patent application | ||
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19860830 |
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| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19861210 |
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| GRNT | Written decision to grant | ||
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Comment text: Registration of Establishment Patent event date: 19870109 Patent event code: PR07011E01D |
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