KR840003257A - Method of manufacturing penam derivatives - Google Patents

Method of manufacturing penam derivatives Download PDF

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Publication number
KR840003257A
KR840003257A KR1019830000223A KR830000223A KR840003257A KR 840003257 A KR840003257 A KR 840003257A KR 1019830000223 A KR1019830000223 A KR 1019830000223A KR 830000223 A KR830000223 A KR 830000223A KR 840003257 A KR840003257 A KR 840003257A
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South Korea
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group
formula
compound
alkyl
hydrogen
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KR1019830000223A
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Korean (ko)
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찬더 코우라 아아런 (외 1)
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로늘드 스미자아
비이참 그루우프 피이엘시이(전에는 비이참 그루우프 리미팃드임)
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Publication of KR840003257A publication Critical patent/KR840003257A/en

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    • 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
    • C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Display Devices Of Pinball Game Machines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음No content

Description

페남유도체의 제조방법Method of manufacturing penam derivatives

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (11)

하기 구조식(Ⅱ)의 화합물을 메탄올과 반응시킨후 필요에 따라 하기 과정중 하나 또는 그 이상을 수행하는 것으로 구성된 하기구조식(Ⅰ)의 페남유도체의 제조방법.A process for preparing the phenam derivative of formula (I), consisting of reacting a compound of formula (II) with methanol and then performing one or more of the following processes as necessary. (ⅰ)보호기나 차단기의 제거. (ⅱ)m이 1인 화합물을 m이 0인 화합물로 전환. (ⅲ)기 Rx를 기 R¹으로 전환. (Ⅳ)생성물을 그의 제약상허용가능한 염이나 에스테르로전환.(Iii) Removal of protectors or breakers. (Ii) converting compound of m to compound of m to zero. (Iii) converting group R x to group R¹. (IV) conversion of the product to its pharmaceutically acceptable salts or esters. 상기 식들에서, RA는 수소 또는 하기구조(la)의 기이며In the above formula, R A is hydrogen or a group of the following structure (la) 여기서 X는 -CO₂R¹또는 SOIR₁이며;R은 C1-6알킬, 아릴, 헤테로사이클릭이며; R¹은 수소 또는 제약상허용되는 염형성이온 또는 에스테르형성기이며; R²는 수소 또는 제약상허용되는 염형성이온이나 생성체내 가수분해되는 에스테르형성기이며 RB는 아미노가나 하기 구조(Ⅱa)의 기Wherein X is —CO 2 R 1 or SOIR;; R is C 1-6 alkyl, aryl, heterocyclic; R¹ is hydrogen or a pharmaceutically acceptable salt forming ion or ester forming group; R² is hydrogen or a pharmaceutically acceptable salt forming ion or ester forming group hydrolyzed in the product, and R B is an amino group or a group of the structure (IIa) 를 보호하는 제거가능한 아실기이며; 여기서 Y는 -CO2RX또는 -SO3RX이며;n은 1이고 m은 0또는 1이며 구조식(Ⅱ)의 R은 상기 구조식(Ⅰ)에서 정의한 바와 같으며 여기서 어떤 반응성 기도 보호될 수 있으며 RX는 에스테르 형성기이며 RY는 수소, 염형성기 또는 카복실차단기이며, R³는 알킬, 벤질, 또는 아릴기를 나타낸다.A removable acyl group that protects; Wherein Y is —CO 2 R X or —SO 3 R X ; n is 1 and m is 0 or 1 and R in formula (II) is as defined in formula (I) above, wherein any reactive group may be protected R X is an ester forming group, R Y is hydrogen, a salt forming group or a carboxyl blocking group, and R³ represents an alkyl, benzyl, or aryl group. 제1항에 있어서 R¹이 수소 또는 염형성이온인 방법.The method of claim 1 wherein R¹ is hydrogen or a salt forming ion. 제1항 또는 제2항에 있어서 RX가 카복실차단기인 방법.The method according to claim 1 or 2, wherein R X is a carboxyl blocker. 제1항 또는 제3항에 있어서 R¹이 제약상허용가능한 에스테르 형성기인 방법.4. A process according to claim 1 or 3 wherein R¹ is a pharmaceutically acceptable ester forming group. 제1항 내지 제4항중 어느 하나에 있어서 R이 C1-6알킬; 산소, 유황 및 질소로부터 선택된 하나 또는 2개의 헤테로원자를 함유하는 임의로 치환된 5원 헤테로사이클환; 페닐;치환분이 할로겐, 하이드록시, C1-6알콕시, 니트로, 아미노, C1-6알킬, C1-6할로알킬, C1-6알킬카보닐옥시 또는 C1-6알킬설포닐아미노(예-NHSO₂CH₃)인 모노치환페닐; 또는 치환분이 하이드록시, 할로겐, 메톡시, 아세톡시 및 아미노로 부터 선택된 이치환페닐인 방법.The compound of any one of claims 1-4 , wherein R is C 1-6 alkyl; Optionally substituted 5-membered heterocycle ring containing one or two heteroatoms selected from oxygen, sulfur and nitrogen; Phenyl; substituents are halogen, hydroxy, C 1-6 alkoxy, nitro, amino, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkylcarbonyloxy or C 1-6 alkylsulfonylamino ( Mono-substituted phenyl, eg, NHSO 2 CH 3); Or the substituent is a disubstituted phenyl selected from hydroxy, halogen, methoxy, acetoxy and amino. 제1항 내지 제5항 중 어느 하나에 있어서 R이 페닐 ; 치환분이 불소, 염소, 하이드록시, 메톡시, 니트로, 아미노, 아세톡, 시트리플로로메틸인 모노치환페닐; 치환분이 아세톡시, 하이드록시 및 메톡시로부터 선택되는 이 치환페닐인 방법.The compound according to any one of claims 1 to 5, wherein R is phenyl; Monosubstituted phenyl whose substituents are fluorine, chlorine, hydroxy, methoxy, nitro, amino, acetok and citrifluoromethyl; The substituent is a substituted phenyl selected from acetoxy, hydroxy and methoxy. 제1항 내지 제6항중 어느 하나에 있어서 R이 2-아미노티아졸릴 또는 2-나 3-티에닐인 방법.The method of claim 1, wherein R is 2-aminothiazolyl or 2- or 3-thienyl. 제1항 내지 제7항중 어느 하나에 있어서 R³가 C1-6알킬인 방법.8. The method of claim 1 , wherein R 3 is C 1-6 alkyl. 제1항 내지 제8항중 어느 하나에 있어서 R³가 메틸인 방법.The method of any one of claims 1-8, wherein R 3 is methyl. 하기 구조식(Ⅲ)의 화합물을 산화시켜 구조식(Ⅱ)의 화합물을 제조하는 방법.A process for preparing the compound of formula II by oxidizing the compound of formula III. 상기식에서 RB,RY및 R³는 구조식(Ⅱ)에서 정의한 바와 같다.Wherein R B , R Y and R 3 are as defined in formula (II). 제10항에 있어서 산화제로서 유기 과산을 사용하여 산화를 일으키는 방법.The method of claim 10, wherein the oxidation is effected using organic peracid as oxidant. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019830000223A 1982-01-22 1983-01-21 Method of manufacturing penam derivatives KR840003257A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8201754 1982-01-22
GB8201754 1982-01-22

Publications (1)

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KR840003257A true KR840003257A (en) 1984-08-20

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KR (1) KR840003257A (en)
AT (2) AT381095B (en)
CA (1) CA1202959A (en)
DK (1) DK23083A (en)
ES (2) ES519191A0 (en)
FI (1) FI830193L (en)
GR (1) GR77868B (en)
JO (1) JO1228B1 (en)
MX (1) MX155039A (en)
NO (1) NO830184L (en)
PL (2) PL244195A1 (en)
PT (1) PT76127A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE811314A (en) * 1973-03-15 1974-08-20 PROCESS FOR THE PREPARATION OF CEPHALOSPORINS AND PENICILLINS
NZ195030A (en) * 1979-10-09 1983-06-17 Beecham Group Ltd Preparation of 6 -methoxy-penam derivatives

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PL240237A1 (en) 1984-02-27
CA1202959A (en) 1986-04-08
DK23083A (en) 1983-07-23
NO830184L (en) 1983-07-25
ES8407054A1 (en) 1984-08-16
ES519191A0 (en) 1984-08-16
FI830193L (en) 1983-07-23
MX155039A (en) 1988-01-22
FI830193A0 (en) 1983-01-20
JO1228B1 (en) 1985-04-20
AT381095B (en) 1986-08-25
ATA20483A (en) 1986-01-15
ES8506721A1 (en) 1985-07-16
ATA256085A (en) 1987-05-15
ES531428A0 (en) 1985-07-16
AT384611B (en) 1987-12-10
DK23083D0 (en) 1983-01-20
PL244195A1 (en) 1984-09-10
PT76127A (en) 1983-02-01
GR77868B (en) 1984-09-25

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Patent event code: PA01091R01D

Comment text: Patent Application

Patent event date: 19830121

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