RO86824B - Procedeu pentru prepararea unor cefalosporine - Google Patents

Procedeu pentru prepararea unor cefalosporine

Info

Publication number
RO86824B
RO86824B RO112112A RO11211281A RO86824B RO 86824 B RO86824 B RO 86824B RO 112112 A RO112112 A RO 112112A RO 11211281 A RO11211281 A RO 11211281A RO 86824 B RO86824 B RO 86824B
Authority
RO
Romania
Prior art keywords
carbon atoms
group
compound
groups
triazolyl
Prior art date
Application number
RO112112A
Other languages
English (en)
Other versions
RO86824A (ro
Inventor
Sadaki Hiroshi
Narita Hirokazu
Imalzumi Hirovuki
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 RO86824A publication Critical patent/RO86824A/ro
Publication of RO86824B publication Critical patent/RO86824B/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 cefalosporine cu formula generala I: (vezi formula) în care R1 reprezinta o grupa de protectie a carboxilului aleasa dintre cu 1...4 atomi de carbon, difenilmetil, fenil, carboxifenil, ftalidil, aciloximetil cu 2...5 atomi de carbon în grupa alcoxi sau una din grupele (vezi formula) în care grupele alchil au 1...4 atomi de carbon si grupele cicloalchil au 3...8 atomi de carbon R2 reprezinta o grupa acilamino cu 2...7 atomi de carbon, fenil, tienil, furil, triazolil sau tetrazolil eventual substituiti cu unul sau doi substituenti alesi dintre un atom de halogen, o grupa alchil cu 1...4 atomi de carbon, hidroxil, carboxil, alcoxicarboxil cu 1...4 atomi de carbon în grupa alcoxi, cian, amino, acilamino cu 1..4 atomi de carbon în grupele alchil, grupa triazolil sau tetrazolil fiind legata de gruparea exometilen în pozitia a 3 a inelului cefem printr-o legatura carbon-azot, R3 reprezinta un atom de hidrogen, R4 reprezinta un atom de hidrogen, o grupa amino sau o grupa amino protejata aleasa dintre formilamino, cloracetalamino, benziloxicarbonilamino si tert-amiloxi-carbonilamino, R5 reprezinta un atom de hidrogen sau o grupa alchil cu 1...4 atomi de carbon, legatura înseamna ca compusul poate fi un izomer sin sau anti sau un amestec al acestora din aceea ca un compus cu formula generala II: (vezi formula) în care substituentii R1, R2, R3 si R4 au semnificatiilr de mai sus se trateaza cu un compus cu formula III:(vezi formula) sau o sare a acestuia, în care R5 are semnificatiile de mai sus, într-un solvent organic ales dintre alcooli inferiori si N,N-dimetilacetamida, la o temperatura cup
RO112112A 1980-09-25 1981-09-25 Procedeu pentru prepararea unor cefalosporine RO86824B (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
RO86824A RO86824A (ro) 1985-05-20
RO86824B true RO86824B (ro) 1985-05-31

Family

ID=27316463

Family Applications (4)

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

Family Applications Before (3)

Application Number Title Priority Date Filing Date
RO112113A RO86825B (ro) 1980-09-25 1981-09-25 Procedeu pentru prepararea unor acizi 7-amino-3-metil-substituit-delta3-cefem-4-carboxilici
RO112111A RO86823B (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) DE3152934C2 (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) RO86825B (ro)
SE (5) SE453090B (ro)

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NZ198350A (en) * 1980-09-25 1985-02-28 Toyama Chemical Co Ltd Cephalosporins and intermediates;pharmaceutical compositions
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US4576938A (en) * 1981-12-08 1986-03-18 Tanabe Seiyaku Co., Ltd. Cephalosporin compound and process for preparing the same
US4618606A (en) * 1982-11-17 1986-10-21 Toyama Chemical Co., Ltd. Antibiotic 7-(thiazolyl)-3-(pyrazinylmethyl) or (pyridazinylmethyl) cephalosporins
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JPS6064986A (ja) * 1983-09-20 1985-04-13 Toyama Chem Co Ltd セファロスポリン類の製造法
JPS60190783A (ja) * 1983-12-21 1985-09-28 Sumitomo Seiyaku Kk セフエム系化合物
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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
AT397086B (de) * 1984-05-25 1994-01-25 Toyama Chemical Co Ltd Verfahren zur herstellung von neuen 2-(2-aminothiazol-4-4yl)-2-(syn)-alkoxyimino- acetamiden
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US4692517A (en) * 1986-03-20 1987-09-08 American Home Products Corporation C-3' acylaminooxy-7-[(2-aminothiazol-4-yl)-α-(substituted-oximino)acetyl]cephalosporin derivatives
EP0265185A3 (en) * 1986-10-21 1990-03-28 Beecham Group Plc Cephalosporins, processes for their preparation and pharmaceutical compositions containing them
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JPH0699443B2 (ja) * 1989-09-29 1994-12-07 ファイザー製薬株式会社 セファロスポリン化合物
US6800756B2 (en) * 2002-05-03 2004-10-05 Orchid Chemicals And Pharmaceuticals, Ltd. Method for the preparation of ceftiofur sodium and its intermediates
DE602004028111D1 (de) * 2003-04-16 2010-08-26 Sandoz Ag Verfahren zur herstellung von cefepim
US7847093B2 (en) * 2003-04-16 2010-12-07 Sandoz Ag Processes for the preparations of cefepime
JP2007530589A (ja) * 2004-03-26 2007-11-01 アンフォラ ディスカバリー コーポレーション 特定のトリアゾールを基礎とする化合物、組成物、およびそれらの使用
US8198434B2 (en) 2008-05-07 2012-06-12 Idexx Laboratories, Inc. Process for preparing cefsulodin sodium
CA2828114A1 (en) * 2010-02-26 2011-09-01 Gary Igor DMITRIENKO Cephalosporin derivatives useful as .beta.-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
SG11201600108PA (en) 2013-07-17 2016-02-26 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
PT73727B (en) 1982-12-30
ATA55483A (de) 1985-03-15
SE468479B (sv) 1993-01-25
ES8301998A1 (es) 1983-01-01
FR2511377A1 (fr) 1983-02-18
NO161117B (no) 1989-03-28
AU558649B2 (en) 1987-02-05
RO86825B (ro) 1985-05-31
AU568033B2 (en) 1987-12-10
RO82689A (ro) 1983-11-01
US4879381A (en) 1989-11-07
ATA55683A (de) 1984-11-15
IN159126B (ro) 1987-03-28
GB8402249D0 (en) 1984-02-29
RO82689B (ro) 1983-10-30
FI870153A (fi) 1987-01-15
RO86823A (ro) 1985-05-20
NL8104386A (nl) 1982-04-16
DE3152935C2 (ro) 1992-07-16
CA1200541A (en) 1986-02-11
GB2089339A (en) 1982-06-23
ES514671A0 (es) 1983-05-01
SE8105658L (sv) 1982-05-05
AT378961B (de) 1985-10-25
CH652129A5 (de) 1985-10-31
KR860000932B1 (ko) 1986-07-19
FI75575B (fi) 1988-03-31
SE8600195D0 (sv) 1986-01-16
NO161117C (no) 1989-07-05
SE8600194L (sv) 1986-01-16
FR2509310B1 (fr) 1985-08-02
PH18484A (en) 1985-08-02
GB8402250D0 (en) 1984-02-29
FI870153A0 (fi) 1987-01-15
ATA55583A (de) 1985-03-15
IN158589B (ro) 1986-12-13
RO86825A (ro) 1985-05-20
DK163877B (da) 1992-04-13
NO813252L (no) 1982-03-26
ES505760A0 (es) 1983-01-01
DE3137854C2 (ro) 1987-06-19
PH19147A (en) 1986-01-15
RO86823B (ro) 1985-05-31
GB2135304B (en) 1985-03-27
FR2509310A1 (fr) 1983-01-14
GB2136420B (en) 1985-05-01
SE468476B (sv) 1993-01-25
MX155025A (es) 1988-01-20
SE468477B (sv) 1993-01-25
ES8306155A1 (es) 1983-05-01
IT8149348A0 (it) 1981-09-23
NZ198350A (en) 1985-02-28
ES8306157A1 (es) 1983-05-01
ES8306156A1 (es) 1983-05-01
AU4986185A (en) 1986-03-20
AT375082B (de) 1984-06-25
HU185850B (en) 1985-04-28
IN155375B (ro) 1985-01-19
DD202436A5 (de) 1983-09-14
DE3152934C2 (ro) 1990-01-18
CH652130A5 (de) 1985-10-31
SE453090B (sv) 1988-01-11
GB2136420A (en) 1984-09-19
CH652128A5 (de) 1985-10-31
SE8600193D0 (sv) 1986-01-16
DE3152932C2 (ro) 1990-02-08
GB2135304A (en) 1984-08-30
LU83650A1 (fr) 1982-01-21
AU550330B2 (en) 1986-03-20
SE8600192L (sv) 1986-01-16
DD208351A5 (de) 1984-05-02
AU4986285A (en) 1986-04-24
ES514669A0 (es) 1983-05-01
SE8600192D0 (sv) 1986-01-16
SE8600193L (sv) 1986-01-16
RO86824A (ro) 1985-05-20
DE3137854A1 (de) 1982-04-15
DE3152931C2 (ro) 1989-10-05
PH19251A (en) 1986-02-17
US5144027A (en) 1992-09-01
DK421881A (da) 1982-04-15
US4673738A (en) 1987-06-16
FI812980L (fi) 1982-03-26
GB2089339B (en) 1985-04-24
US4489072A (en) 1984-12-18
EG17373A (en) 1990-12-30
PH18072A (en) 1985-03-18
SE8600195L (sv) 1986-01-16
CA1204735A (en) 1986-05-20
ES514670A0 (es) 1983-05-01
AR240645A1 (es) 1990-07-31
DK163877C (da) 1992-09-14
FI80041B (fi) 1989-12-29
PT73727A (en) 1981-10-01
AU7543881A (en) 1982-04-01
ATA410981A (de) 1983-11-15
SE8600194D0 (sv) 1986-01-16
FI75575C (fi) 1988-07-11
IN158590B (ro) 1986-12-13
FI80041C (fi) 1990-04-10
AT378193B (de) 1985-06-25
SE468478B (sv) 1993-01-25
PH20221A (en) 1986-10-23
FR2511377B1 (fr) 1985-12-13
IT1172201B (it) 1987-06-18
AT378962B (de) 1985-10-25
CH651837A5 (de) 1985-10-15

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