KR840001581A - 베타-락타마제 억제제 2-베타-치환-2-알파-메틸-(5r)펜임-3-알파카복실산 1,1-디옥사이드 및 그 중간체의 제조방법 - Google Patents
베타-락타마제 억제제 2-베타-치환-2-알파-메틸-(5r)펜임-3-알파카복실산 1,1-디옥사이드 및 그 중간체의 제조방법 Download PDFInfo
- Publication number
- KR840001581A KR840001581A KR1019820004161A KR820004161A KR840001581A KR 840001581 A KR840001581 A KR 840001581A KR 1019820004161 A KR1019820004161 A KR 1019820004161A KR 820004161 A KR820004161 A KR 820004161A KR 840001581 A KR840001581 A KR 840001581A
- Authority
- KR
- South Korea
- Prior art keywords
- reaction
- compound
- formula
- inert solvent
- protecting group
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 5
- 238000000034 method Methods 0.000 title claims 5
- 239000003781 beta lactamase inhibitor Substances 0.000 title 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 11
- 239000012442 inert solvent Substances 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 3
- 238000005886 esterification reaction Methods 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 3
- 238000001727 in vivo Methods 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000002140 halogenating effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal salt Chemical class 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (17)
- 하기 일반식(B)의 화합물을 반응 불활성 용매중에서 금속퍼망간에이트로 산화시킴을 특징으로 하는 하기 일반식(A)의 화합물의 제조방법.
-
- 상기 식들에 있어서, R6는
-
- 로서, X는 수소 또는 히드록시이고, Y는 아지도 또는 아미노이며; R7는 카르복시보호기이다.
- 제1항에 있어서, -20℃에서 +50℃의 수성 용매중에서 2-10몰당량의 금속 퍼망간에이트를 사용하여 산화반응을 수행함을 특징으로 하는 방법.
- (a) 하기 일반식(A)의 화합물을 산 수용체 존재하의 반응 불활성 용매중에서 할로겐화제와 반응시킨 다음 수득되는 산할라이드를 산 수용체 존재하의 반응 불활성 용매중에서 하기 일반식(G)의 화합물과 반응시키거나; 또는 (b) 하기 일반식(A)의 알카리 금속염을 반응 불활성 용매중에서 알킬화제와 반응시킨 다음, 필요에 따라서는 (a)′ 접촉 가수소 분해 반응에 의해 카르복시 보호기를 제거하고, (b)′반응 (a)′의 카르복실산의 에스테르화 반응을 행하여 생체내에서 용이 가수분해성 에스테르를 제조함을 특징으로 하는 하기 일반식 (c)의 화합물의 제조방법.
-
- 상기 식들에 있어서, R7은 카르복시보호기이고; Z는 C1∼C4알콕시, W-하이드록시 (C2∼C4)알콕시 3-6개의 탄소원자를 갖는 카르보 알콕시메톡시 또는 W-아세트아미도(C2∼C4)알콕시이다.
- 제3항에 있어서, Z가 탄소원자수 1 내지 4의 알콕시인 방법.
- 하기 일반식(F)의 화합물을 제3급 아민염기 존재하의 반응 불활성 용매중에서 5산화인, 옥시염화인 또는 5염화인으로 처리한 다음; 필요에 따라서는 (a) 접촉가수소분해 반응에 의해 카르복시 보호기를 제거하고, (b) 반응 (a)의 카르복실산의 에스테르화 반응을 행하여 생체내에서 용이 가수분해성 에스테르를 제조함을 특징으로 하는 하기 일반식(E)의 화합물의 제조방법.
-
- (R7은 카르복시 보호기이다),
- 하기 일반식(A)의 화합물을 산 수용체 존재하의 반응 불활성 용매중에서 할로겐화제와 반응시킨 다음, 필요에 따라서는 하기의 1개 이상의 반응, 즉 (a) 접촉 가수소분해 반응에 의해 카르복시 보호기를 제거하는 반응, (b) 반응 (a)의 카르복실산의 에스테르화 반응을 행하여 생체내에서 용이 가수분해성 에스테르를 제조하는 반응, (c) 하기 일반식(D)의 화합물과 암모니아 또는 디(C1∼C4)알킬아민의 반응, 또는 (d) 반응 불활성 용매중에서의 하기 일반식(D)의 화합물과 CH3MgBr의 반응을 수행함을 특징으로 하는 하기 일반식(D)의 화합믈의 제조 방법.
-
- (R7은 카르복시 보호기이다),
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/301,995 US4356174A (en) | 1981-09-14 | 1981-09-14 | Beta-lactamase inhibiting 2-beta-substituted-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxides and intermediates therefor |
| US301,995 | 1981-09-14 | ||
| US301995 | 1981-09-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840001581A true KR840001581A (ko) | 1984-05-07 |
| KR860001361B1 KR860001361B1 (ko) | 1986-09-16 |
Family
ID=23165806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8204161A KR860001361B1 (ko) | 1981-09-14 | 1982-09-14 | 베타-락타마제 억제제 2-베타-치환-2-알파-메틸-(5r)펜암-3-알파-카복실산 1, 1-디옥사이드 및 그 중간체의 제조방법 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4356174A (ko) |
| EP (1) | EP0074783B1 (ko) |
| JP (1) | JPS5859990A (ko) |
| KR (1) | KR860001361B1 (ko) |
| AT (1) | ATE14585T1 (ko) |
| AU (1) | AU532401B2 (ko) |
| CA (1) | CA1212378A (ko) |
| CS (1) | CS236681B2 (ko) |
| DE (1) | DE3265082D1 (ko) |
| DK (1) | DK407882A (ko) |
| ES (1) | ES8308566A1 (ko) |
| FI (1) | FI823165L (ko) |
| GR (1) | GR76726B (ko) |
| HU (1) | HU186575B (ko) |
| IE (1) | IE53819B1 (ko) |
| IL (1) | IL66776A (ko) |
| IN (1) | IN159366B (ko) |
| NO (1) | NO823093L (ko) |
| NZ (1) | NZ201895A (ko) |
| PH (1) | PH19442A (ko) |
| PL (1) | PL139272B1 (ko) |
| PT (1) | PT75548B (ko) |
| SU (1) | SU1272995A3 (ko) |
| YU (1) | YU205182A (ko) |
| ZA (1) | ZA826687B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4760058A (en) * | 1984-08-29 | 1988-07-26 | Farmitalia Carlo Erba S.P.A. | Penam derivatives |
| US4861768A (en) * | 1986-02-27 | 1989-08-29 | Taiho Pharmaceutical Company, Limited | 2 β-substituted thiomethylpenicillin derivatives and their preparation and use |
| TW383308B (en) * | 1993-08-24 | 2000-03-01 | Hoffmann La Roche | 2-beta-alkenyl penam sulfones as beta-lactamase inhibitors |
| US6156745A (en) * | 1997-12-29 | 2000-12-05 | Research Corporation Technologies, Inc. | 2β-substituted-6-alkylidene penicillanic acid derivatives as β-lactamase inhibitors |
| US6407091B1 (en) * | 1999-04-15 | 2002-06-18 | Research Corporation Technologies, Inc. | β-lactamase inhibiting compounds |
| US6916801B2 (en) * | 2001-07-24 | 2005-07-12 | Alamx, Llc | 7-Alkylidene-3-substituted-3-cephem-4-carboxylates as β-lactamase inhibitors |
| JP2005525399A (ja) * | 2002-04-04 | 2005-08-25 | アラムクス エルエルシー | セリンおよびメタロ−β−ラクタマーゼの阻害剤 |
| KR100796131B1 (ko) * | 2005-04-06 | 2008-01-21 | 후지쯔 가부시끼가이샤 | 휴대형 전자 기기 |
| CN104650119B (zh) * | 2015-02-10 | 2017-04-05 | 中国科学院长春应用化学研究所 | 一种β‑内酰胺化合物的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1541832A (en) * | 1976-02-11 | 1979-03-07 | Beecham Group Ltd | 2-substituted penam derivatives methods for their preparation and compisitions containing them |
| US4234579A (en) * | 1977-06-07 | 1980-11-18 | Pfizer Inc. | Penicillanic acid 1,1-dioxides as β-lactamase inhibitors |
| US4241050A (en) * | 1978-09-01 | 1980-12-23 | Pfizer Inc. | Penam 1,1-dioxides as beta-lactamase inhibitors |
| US4244951A (en) * | 1979-05-16 | 1981-01-13 | Pfizer Inc. | Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide |
| US4256733A (en) * | 1979-09-26 | 1981-03-17 | Pfizer Inc. | Acetoxymethyl penam compounds as β-lactamase inhibitors |
| US4287181A (en) * | 1979-10-22 | 1981-09-01 | Pfizer Inc. | Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors |
| IL61880A (en) * | 1980-01-21 | 1984-11-30 | Bristol Myers Co | 2beta-chloromethyl-2alpha-methylpenam-3alpha-carboxylic acid sulfone derivatives,their preparation and pharmaceutical compositions containing them |
-
1981
- 1981-09-13 ZA ZA826687A patent/ZA826687B/xx unknown
- 1981-09-14 US US06/301,995 patent/US4356174A/en not_active Expired - Lifetime
-
1982
- 1982-08-11 IN IN616/DEL/82A patent/IN159366B/en unknown
- 1982-09-08 EP EP82304691A patent/EP0074783B1/en not_active Expired
- 1982-09-08 DE DE8282304691T patent/DE3265082D1/de not_active Expired
- 1982-09-08 AT AT82304691T patent/ATE14585T1/de not_active IP Right Cessation
- 1982-09-10 ES ES515649A patent/ES8308566A1/es not_active Expired
- 1982-09-10 PL PL1982238200A patent/PL139272B1/pl unknown
- 1982-09-13 SU SU823494115A patent/SU1272995A3/ru active
- 1982-09-13 FI FI823165A patent/FI823165L/fi not_active Application Discontinuation
- 1982-09-13 GR GR69264A patent/GR76726B/el unknown
- 1982-09-13 PH PH27864A patent/PH19442A/en unknown
- 1982-09-13 AU AU88339/82A patent/AU532401B2/en not_active Ceased
- 1982-09-13 CA CA000411274A patent/CA1212378A/en not_active Expired
- 1982-09-13 PT PT75548A patent/PT75548B/pt not_active IP Right Cessation
- 1982-09-13 IE IE2232/82A patent/IE53819B1/en unknown
- 1982-09-13 IL IL66776A patent/IL66776A/xx unknown
- 1982-09-13 DK DK407882A patent/DK407882A/da not_active Application Discontinuation
- 1982-09-13 YU YU02051/82A patent/YU205182A/xx unknown
- 1982-09-13 NO NO823093A patent/NO823093L/no unknown
- 1982-09-13 NZ NZ201895A patent/NZ201895A/xx unknown
- 1982-09-13 HU HU822915A patent/HU186575B/hu unknown
- 1982-09-14 CS CS826610A patent/CS236681B2/cs unknown
- 1982-09-14 KR KR8204161A patent/KR860001361B1/ko active
- 1982-09-14 JP JP57160711A patent/JPS5859990A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3265082D1 (en) | 1985-09-05 |
| FI823165L (fi) | 1983-03-15 |
| PT75548A (en) | 1982-10-01 |
| YU205182A (en) | 1985-03-20 |
| NO823093L (no) | 1983-03-15 |
| PT75548B (en) | 1985-12-09 |
| IE822232L (en) | 1983-03-14 |
| US4356174A (en) | 1982-10-26 |
| JPS5859990A (ja) | 1983-04-09 |
| PH19442A (en) | 1986-04-18 |
| AU532401B2 (en) | 1983-09-29 |
| JPS6153354B2 (ko) | 1986-11-17 |
| PL238200A1 (en) | 1985-02-13 |
| GR76726B (ko) | 1984-08-30 |
| PL139272B1 (en) | 1987-01-31 |
| HU186575B (en) | 1985-08-28 |
| ES515649A0 (es) | 1983-09-16 |
| KR860001361B1 (ko) | 1986-09-16 |
| EP0074783B1 (en) | 1985-07-31 |
| ATE14585T1 (de) | 1985-08-15 |
| DK407882A (da) | 1983-03-15 |
| IL66776A (en) | 1985-07-31 |
| IN159366B (ko) | 1987-05-09 |
| ES8308566A1 (es) | 1983-09-16 |
| IE53819B1 (en) | 1989-03-01 |
| FI823165A0 (fi) | 1982-09-13 |
| CS236681B2 (en) | 1985-05-15 |
| SU1272995A3 (ru) | 1986-11-23 |
| ZA826687B (en) | 1983-07-27 |
| AU8833982A (en) | 1983-03-24 |
| NZ201895A (en) | 1985-03-20 |
| CA1212378A (en) | 1986-10-07 |
| EP0074783A1 (en) | 1983-03-23 |
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