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RO86825B - Procedeu pentru prepararea unor acizi 7-amino-3-metil-substituit-delta3-cefem-4-carboxilici - Google Patents

Procedeu pentru prepararea unor acizi 7-amino-3-metil-substituit-delta3-cefem-4-carboxilici

Info

Publication number
RO86825B
RO86825B RO112113A RO11211381A RO86825B RO 86825 B RO86825 B RO 86825B RO 112113 A RO112113 A RO 112113A RO 11211381 A RO11211381 A RO 11211381A RO 86825 B RO86825 B RO 86825B
Authority
RO
Romania
Prior art keywords
acid
group
amino
methyl
preparation
Prior art date
Application number
RO112113A
Other languages
English (en)
Other versions
RO86825A (ro
Inventor
Sadaki Hiroshi
Narita Hirokazu
Imaizumi Hiroyuki
Konishi Yoshinori
Inaba Takihiro
Hirakawa Tatsuo
Taki Hideo
Tai Masaru
Watanabe Yasuo
Saikawa Isamu
Original Assignee
Toyama Chemical Co.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP55132253A external-priority patent/JPS5758689A/ja
Priority claimed from JP55158184A external-priority patent/JPS5782393A/ja
Priority claimed from JP55175263A external-priority patent/JPS6052755B2/ja
Application filed by Toyama Chemical Co. filed Critical Toyama Chemical Co.
Publication of RO86825A publication Critical patent/RO86825A/ro
Publication of RO86825B publication Critical patent/RO86825B/ro

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/48—Methylene radicals, substituted by hetero rings
    • C07D501/56—Methylene radicals, substituted by hetero rings with the 7-amino radical acylated by carboxylic acids containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Inventia se refera la un procedeu pentru prepararea unor acizi 7-amino-3-metil-substituit-delta cub-cefem-4-carboxilici cu formula generala I: (vezi formula) în care R1 reprezinta un atom de hidrogen sau o grupa p-nitrobenzil, etil sau difenilmetil, R2 reprezinta o grupa triazolil sau tetrazolil eventual substituita cu unl sau doi substituenti alesi dintre un atom de halogen, o grupa alchil cu 1...4 atomi de carbon, tioalchil cu 1...4 atomi de carbon, alcoxi-carbonil cu 1...4 atomi de carbon, cian, amino, acilamino cu 1..4 atomi de carbon, fenil, difenilmetoxicarbonil sau alcoxicarbonilalchul în care grupele alchil cu 1...4 atomi de carbon, grupa triazolil sau tetrazolil fiind legata la grupa exometilen printr-o legatura carbon-azot, constînd din aceea ca un compus cu formula generala II: (vezi formula) în care R1 are semnificatiile de mai sus si Z reprezinta S sau S-O reactioneaza cu un triazol sau tetrazol, eventual substituit cu sunstituientii radicalului R2, într-un solvent organic ales dintre sulfonat, acid trifluoracetic, acetat de etil, nitrometan, acid acetic, cloracetat de etil si acetonitril, în prezenta unui acid sau complex cu carcater acid ales dintre acid sulfuric, metansulfonic, trifluormetansulfonic, fluorsulfonic, trifluorura de bor si trifluorura de bor-eterdietilic, la o temperatura cuprinsa între între temepratura camerei si 60 degree C, grupa amino putînd sa fie eventual protejata în timpul reactiei, dupa care, daca se doreste, compusul cu formula I obtinut poate fi transformat într-o sare, un ester sau un acid liber, prin metode în sine cunoscute.
RO112113A 1980-09-25 1981-09-25 Procedeu pentru prepararea unor acizi 7-amino-3-metil-substituit-delta3-cefem-4-carboxilici RO86825B (ro)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP55132253A JPS5758689A (en) 1980-09-25 1980-09-25 Novel preparation of 7-substituted or unsubstituted amino-3-substituted methylcephem carboxylic acids
JP55158184A JPS5782393A (en) 1980-11-12 1980-11-12 7-amino-3-(2-(1,2,3,4-tetrazolyl)methyl)cephem-4-carboxylic acid
JP55175263A JPS6052755B2 (ja) 1980-12-13 1980-12-13 新規セファロスポリン類

Publications (2)

Publication Number Publication Date
RO86825A RO86825A (ro) 1985-05-20
RO86825B true RO86825B (ro) 1985-05-31

Family

ID=27316463

Family Applications (4)

Application Number Title Priority Date Filing Date
RO112111A RO86823B (ro) 1980-09-25 1981-09-25 Procedeu pentru prepararea unor cefalosporine
RO112112A RO86824B (ro) 1980-09-25 1981-09-25 Procedeu pentru prepararea unor cefalosporine
RO81105405A RO82689A (ro) 1980-09-25 1981-09-25 Procedeu pentru prepararea unor cefalosporine
RO112113A RO86825B (ro) 1980-09-25 1981-09-25 Procedeu pentru prepararea unor acizi 7-amino-3-metil-substituit-delta3-cefem-4-carboxilici

Family Applications Before (3)

Application Number Title Priority Date Filing Date
RO112111A RO86823B (ro) 1980-09-25 1981-09-25 Procedeu pentru prepararea unor cefalosporine
RO112112A RO86824B (ro) 1980-09-25 1981-09-25 Procedeu pentru prepararea unor cefalosporine
RO81105405A RO82689A (ro) 1980-09-25 1981-09-25 Procedeu pentru prepararea unor cefalosporine

Country Status (27)

Country Link
US (4) US4489072A (ro)
KR (1) KR860000932B1 (ro)
AR (1) AR240645A1 (ro)
AT (4) AT375082B (ro)
AU (3) AU550330B2 (ro)
CA (2) CA1204735A (ro)
CH (4) CH652129A5 (ro)
DD (2) DD202436A5 (ro)
DE (5) DE3137854A1 (ro)
DK (1) DK163877C (ro)
EG (1) EG17373A (ro)
ES (4) ES505760A0 (ro)
FI (2) FI75575C (ro)
FR (2) FR2509310B1 (ro)
GB (3) GB2089339B (ro)
HU (1) HU185850B (ro)
IN (4) IN155375B (ro)
IT (1) IT1172201B (ro)
LU (1) LU83650A1 (ro)
MX (1) MX155025A (ro)
NL (1) NL8104386A (ro)
NO (1) NO161117C (ro)
NZ (1) NZ198350A (ro)
PH (5) PH18072A (ro)
PT (1) PT73727B (ro)
RO (4) RO86823B (ro)
SE (5) SE453090B (ro)

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GB2161476B (en) * 1984-05-25 1988-01-27 Toyama Chemical Co Ltd 2-aminothiazolyl-2-methoxyimino acetamides and their use in preparing cephalosporins
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US7847093B2 (en) * 2003-04-16 2010-12-07 Sandoz Ag Processes for the preparations of cefepime
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WO2011103686A1 (en) * 2010-02-26 2011-09-01 Viswanatha , Sundaramma CEPHALOSPORIN DERIVATIVES USEFUL AS β-LACTAMASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF
CN102351886B (zh) * 2011-09-07 2013-10-16 山东罗欣药业股份有限公司 头孢特仑新戊酯晶体、其制备方法及含有该晶体的组合物片剂
MY184572A (en) * 2013-07-17 2021-04-05 Otsuka Pharma Co Ltd Cyanotriazole compounds
CN106046026B (zh) * 2016-06-30 2018-07-06 济南康和医药科技有限公司 一种头孢特仑新戊酯的制备方法
CN112645842B (zh) * 2020-12-25 2022-08-19 复旦大学 一种氰乙酸叔丁酯的连续流制备方法

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Also Published As

Publication number Publication date
IT8149348A0 (it) 1981-09-23
RO82689B (ro) 1983-10-30
GB8402250D0 (en) 1984-02-29
FI812980L (fi) 1982-03-26
GB2089339A (en) 1982-06-23
AU568033B2 (en) 1987-12-10
CA1200541A (en) 1986-02-11
RO86825A (ro) 1985-05-20
AU550330B2 (en) 1986-03-20
ES8306155A1 (es) 1983-05-01
SE468476B (sv) 1993-01-25
SE453090B (sv) 1988-01-11
HU185850B (en) 1985-04-28
MX155025A (es) 1988-01-20
SE468477B (sv) 1993-01-25
SE8600195D0 (sv) 1986-01-16
ES514671A0 (es) 1983-05-01
FR2509310B1 (fr) 1985-08-02
ATA55683A (de) 1984-11-15
LU83650A1 (fr) 1982-01-21
PH18072A (en) 1985-03-18
SE8600195L (sv) 1986-01-16
GB2135304A (en) 1984-08-30
ES8301998A1 (es) 1983-01-01
SE8600193D0 (sv) 1986-01-16
PT73727B (en) 1982-12-30
NL8104386A (nl) 1982-04-16
PH18484A (en) 1985-08-02
NO161117C (no) 1989-07-05
AU4986185A (en) 1986-03-20
NO161117B (no) 1989-03-28
DE3137854C2 (ro) 1987-06-19
FR2511377A1 (fr) 1983-02-18
SE468478B (sv) 1993-01-25
ES8306156A1 (es) 1983-05-01
ES514670A0 (es) 1983-05-01
ATA55483A (de) 1985-03-15
GB2136420A (en) 1984-09-19
IN158590B (ro) 1986-12-13
RO86824B (ro) 1985-05-31
CH652130A5 (de) 1985-10-31
AU7543881A (en) 1982-04-01
CH652129A5 (de) 1985-10-31
AR240645A1 (es) 1990-07-31
DD202436A5 (de) 1983-09-14
AU4986285A (en) 1986-04-24
FI80041B (fi) 1989-12-29
DE3152934C2 (ro) 1990-01-18
AT378962B (de) 1985-10-25
SE8600194L (sv) 1986-01-16
AT378193B (de) 1985-06-25
AT378961B (de) 1985-10-25
GB8402249D0 (en) 1984-02-29
GB2135304B (en) 1985-03-27
FR2511377B1 (fr) 1985-12-13
ES505760A0 (es) 1983-01-01
US4489072A (en) 1984-12-18
DE3152931C2 (ro) 1989-10-05
DE3152932C2 (ro) 1990-02-08
IN155375B (ro) 1985-01-19
PH19251A (en) 1986-02-17
PH20221A (en) 1986-10-23
AT375082B (de) 1984-06-25
DD208351A5 (de) 1984-05-02
FI80041C (fi) 1990-04-10
SE8105658L (sv) 1982-05-05
SE8600192D0 (sv) 1986-01-16
SE8600193L (sv) 1986-01-16
NO813252L (no) 1982-03-26
CH652128A5 (de) 1985-10-31
US4879381A (en) 1989-11-07
IN159126B (ro) 1987-03-28
RO82689A (ro) 1983-11-01
GB2089339B (en) 1985-04-24
FR2509310A1 (fr) 1983-01-14
IT1172201B (it) 1987-06-18
FI75575C (fi) 1988-07-11
DE3137854A1 (de) 1982-04-15
CH651837A5 (de) 1985-10-15
GB2136420B (en) 1985-05-01
PT73727A (en) 1981-10-01
KR860000932B1 (ko) 1986-07-19
DK163877C (da) 1992-09-14
FI870153A0 (fi) 1987-01-15
FI870153A (fi) 1987-01-15
CA1204735A (en) 1986-05-20
RO86823A (ro) 1985-05-20
ES8306157A1 (es) 1983-05-01
DE3152935C2 (ro) 1992-07-16
RO86824A (ro) 1985-05-20
AU558649B2 (en) 1987-02-05
IN158589B (ro) 1986-12-13
SE8600194D0 (sv) 1986-01-16
ATA410981A (de) 1983-11-15
DK421881A (da) 1982-04-15
FI75575B (fi) 1988-03-31
US5144027A (en) 1992-09-01
ATA55583A (de) 1985-03-15
PH19147A (en) 1986-01-15
RO86823B (ro) 1985-05-31
SE8600192L (sv) 1986-01-16
DK163877B (da) 1992-04-13
NZ198350A (en) 1985-02-28
EG17373A (en) 1990-12-30
ES514669A0 (es) 1983-05-01
SE468479B (sv) 1993-01-25
US4673738A (en) 1987-06-16

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