CA1235414A - 7-acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof - Google Patents

7-acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof

Info

Publication number
CA1235414A
CA1235414A CA000364436A CA364436A CA1235414A CA 1235414 A CA1235414 A CA 1235414A CA 000364436 A CA000364436 A CA 000364436A CA 364436 A CA364436 A CA 364436A CA 1235414 A CA1235414 A CA 1235414A
Authority
CA
Canada
Prior art keywords
carboxy
group
formula
aminothiazol
amino
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.)
Expired
Application number
CA000364436A
Other languages
English (en)
French (fr)
Inventor
Takao Takaya
Hisashi Takasugi
Takashi Masugi
Hideaki Yamanaka
Kohji Kawabata
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujisawa Pharmaceutical Co Ltd
Original Assignee
Fujisawa Pharmaceutical Co Ltd
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
Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd
Application granted granted Critical
Publication of CA1235414A publication Critical patent/CA1235414A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (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)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA000364436A 1979-11-19 1980-11-12 7-acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof Expired CA1235414A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
GB7939985 1979-11-19
GB7939985 1979-11-19
GB8004335 1980-02-08
GB8004335 1980-02-08
GB8012991 1980-04-21
GB8012991 1980-04-21
GB8022920 1980-07-14
GB8022920 1980-07-14

Publications (1)

Publication Number Publication Date
CA1235414A true CA1235414A (en) 1988-04-19

Family

ID=27449150

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000364436A Expired CA1235414A (en) 1979-11-19 1980-11-12 7-acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof

Country Status (22)

Country Link
US (6) US4409214A (show.php)
EP (3) EP0123024B1 (show.php)
JP (1) JPH0710870B2 (show.php)
AR (1) AR248139A1 (show.php)
AT (3) ATE37028T1 (show.php)
AU (1) AU543301B2 (show.php)
CA (1) CA1235414A (show.php)
DE (3) DE3072207T2 (show.php)
DK (1) DK491780A (show.php)
ES (2) ES8204739A1 (show.php)
FI (1) FI74970C (show.php)
GR (1) GR71596B (show.php)
HK (1) HK11888A (show.php)
HU (1) HU186753B (show.php)
IE (1) IE53271B1 (show.php)
MX (2) MX158337A (show.php)
MY (1) MY101359A (show.php)
NL (1) NL930045I2 (show.php)
NO (1) NO160921C (show.php)
PT (1) PT72079B (show.php)
SG (1) SG61787G (show.php)
SU (1) SU1186087A3 (show.php)

Families Citing this family (96)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4409214A (en) * 1979-11-19 1983-10-11 Fujisawa Pharmaceutical, Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
US4731443A (en) * 1979-11-19 1988-03-15 Fujisawa Pharmaceutical Co., Ltd. 7-acylamino-3-vinylcephalosporanic acid derivatives
IE53429B1 (en) * 1981-08-03 1988-11-09 Fujisawa Pharmaceutical Co New cephem compounds and processes for preparation thereof
US4443374A (en) * 1982-02-01 1984-04-17 E. R. Squibb & Sons, Inc. Process for preparing (3S)-3-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]-acetyl]amino]-2-oxo-1-azetidinesulfonic acid, and 4-substituted derivatives
US4546101A (en) * 1982-09-10 1985-10-08 Fujisawa Pharmaceutical Co., Ltd. New cephem compounds useful for treating infectious diseases in human being and animals and processes for preparation thereof
DK162718C (da) * 1982-09-30 1992-05-11 Fujisawa Pharmaceutical Co Analogifremgangsmaade til fremstilling af 7-substitueret-3-vinyl-3-cephemforbindelser
US4618606A (en) * 1982-11-17 1986-10-21 Toyama Chemical Co., Ltd. Antibiotic 7-(thiazolyl)-3-(pyrazinylmethyl) or (pyridazinylmethyl) cephalosporins
US4609730A (en) * 1982-11-22 1986-09-02 Fujisawa Pharmaceutical Co., Ltd. 7-[substituted imino-2-(2-aminothiazol-4-yl)-acetamido]-3(2,2-dihalovinyl or ethynyl)-3-cephem-4-carboxylic acid (syn isomers), having antimicrobial activities
ZM884A1 (en) * 1983-01-28 1984-10-22 Bristol Myers Co Substituted vinyl cephalosporins
US4520022A (en) * 1983-01-28 1985-05-28 Bristol-Myers Company Substituted vinyl cephalosporins
US4486586A (en) * 1983-02-10 1984-12-04 Bristol-Myers Company Cephalosporin derivatives
CA1276929C (en) * 1984-04-09 1990-11-27 Masahisa Oka Cephalosporin antibacterial agents
GB8411954D0 (en) * 1984-05-10 1984-06-13 Glaxo Group Ltd Cephalosporin antibiotics
US4699979A (en) * 1985-04-22 1987-10-13 Bristol-Meyers Company 7-amino-3-propenylcephalosporanic acid and esters thereof
FR2580652B1 (fr) * 1985-04-22 1989-01-06 Bristol Myers Co Acide 7-amino-3-propenylcephalosporanique et ses esters
US4874856A (en) * 1985-06-24 1989-10-17 Bristol-Myers Company 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof
US4708955A (en) * 1985-06-24 1987-11-24 Bristol-Myers Company 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof
US4659812A (en) * 1985-08-20 1987-04-21 Bristol-Myers Company Cephalosporin intermediates
US4684722A (en) * 1986-01-06 1987-08-04 E. R. Squibb & Sons, Inc. Monosulfactams
US5194604A (en) * 1990-06-29 1993-03-16 E. R. Squibb & Sons, Inc. Process and intermediates for beta-lactams having aminothiazole(iminooxyacetic acid)acetic acid sidechains
US5143911A (en) * 1990-08-23 1992-09-01 Bristol-Myers Squibb Company Antibiotic c-3 di-hydroxyphenyl substituted cephalosporin compounds, compositions and method of use thereof
AU644518B2 (en) * 1991-04-29 1993-12-09 Labsphere, Inc. Integrating sphere for diffuse reflectance and transmittance measurements and the like
US5523400A (en) * 1993-04-16 1996-06-04 Hoffmann-La Roche Inc. Cephalosporin antibiotics
US6468995B1 (en) 1993-09-09 2002-10-22 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds
CH688319A5 (fr) * 1994-06-03 1997-07-31 Marcham Trading & Investment L Procédé pour la préparation du céfixime trihydraté.
AT403049B (de) 1995-08-14 1997-10-27 Biochemie Gmbh Abreicherung von 7-adca in 3-vinyl-aca
US5883247A (en) * 1996-06-10 1999-03-16 Hoffmann-La Roche Inc. Preparation of cephem and isooxacephem derivatives
AT404251B (de) * 1996-08-14 1998-10-27 Biochemie Gmbh Neues kristallines salz von cefixim
AT404727B (de) * 1997-01-16 1999-02-25 Biochemie Gmbh Kristallines salz von cefixim und verfahren zu dessen herstellung
TW538045B (en) * 1997-01-16 2003-06-21 Biochemie Gmbh Process for purifying cefixime
JP4157177B2 (ja) 1997-06-04 2008-09-24 大塚化学ホールディングス株式会社 ３−アルケニルセフェム化合物の製造法
US6407124B1 (en) 1998-06-18 2002-06-18 Bristol-Myers Squibb Company Carbon substituted aminothiazole inhibitors of cyclin dependent kinases
KR100392409B1 (ko) 2000-03-20 2003-07-22 한미정밀화학주식회사 신규한 티아졸 화합물을 이용한 세팔로스포린계항생물질의 제조 방법
US20060040915A1 (en) * 2002-04-26 2006-02-23 Yatendra Kumar Process for the preparation of cefdinir
ITMI20020913A0 (it) * 2002-04-29 2002-04-29 Acs Dobfar Spa Nuova forma cristallina del cefdinir
US6800756B2 (en) * 2002-05-03 2004-10-05 Orchid Chemicals And Pharmaceuticals, Ltd. Method for the preparation of ceftiofur sodium and its intermediates
US20040002600A1 (en) * 2002-06-20 2004-01-01 Orchid Chemicals And Pharmaceuticals Limited Process for the conversion of penam ring system to cepham ring system
JP2006500356A (ja) * 2002-08-13 2006-01-05 サンド・アクチエンゲゼルシヤフト セフジニル中間体
JPWO2004085443A1 (ja) * 2003-03-24 2006-06-29 ア・チ・エツセ・ドブフアル・エツセ・ピー・アー ７−［２−（２−アミノチアゾール−４−イル）−２−ヒドロキシイミノアセトアミド−３−ビニル−３−セフェム−４−カルボン酸（シン異性体）の新規結晶およびその製造方法
US20050137182A1 (en) * 2003-06-02 2005-06-23 Ramesh Dandala Novel crystalline form of cefdinir
US20040242556A1 (en) * 2003-06-02 2004-12-02 Ramesh Dandala Novel crystalline form of cefdinir
US7098329B2 (en) * 2003-06-19 2006-08-29 Orchid Chemicals & Pharmaceuticals Ltd. Process for the preparation of a cephalosporin antibiotic
US20050113355A1 (en) * 2003-09-12 2005-05-26 Duerst Richard W. Cefdinir pyridine salt
US20050059819A1 (en) * 2003-09-12 2005-03-17 Duerst Richard W. Cefdinir pyridine salt
US20050059818A1 (en) * 2003-09-12 2005-03-17 Duerst Richard W. Polymorph of a pharmaceutical
US20050059820A1 (en) * 2003-09-17 2005-03-17 Debashish Datta Method for manufacture of ceftriaxone sodium
US20050059821A1 (en) * 2003-09-17 2005-03-17 Debashish Datta Method for manufacture of ceftriaxone sodium
US20050209211A1 (en) * 2004-03-16 2005-09-22 Devalina Law Trihemihydrate, anhydrate and novel hydrate forms of Cefdinir
US20060069079A1 (en) * 2004-09-27 2006-03-30 Sever Nancy E Stable amorphous cefdinir
US20050245738A1 (en) * 2004-05-03 2005-11-03 Lupin Ltd Stable bioavailable crystalline form or cefdinir and a process for the preparation thereof
JP2007536378A (ja) * 2004-05-10 2007-12-13 ルピン・リミテッド 生体利用性が強化されている新規セフィキシム医薬製剤
MX2007006018A (es) * 2004-11-30 2007-06-07 Astellas Pharma Inc Suspension farmaceutica oral novedosa de cristal de cefdinir.
WO2006067806A1 (en) * 2004-12-21 2006-06-29 Lupin Limited Process for the preparation of cefixime
EP1863822B1 (en) * 2005-03-29 2009-10-14 Hetero Drugs Limited An improved process for the preparation of cefixime
US20070128268A1 (en) * 2005-12-07 2007-06-07 Herwig Jennewein Pharmaceutical compositions comprising an antibiotic
WO2007119249A2 (en) 2006-04-13 2007-10-25 Lupin Limited Pharmaceutical compositions of cefixime
US9233112B2 (en) 2006-04-13 2016-01-12 Lupin Limited Pharmaceutical compositions of cefixime
TR200909786A1 (tr) 2009-12-25 2011-07-21 Bi̇lgi̇ç Mahmut Sefiksim içeren efervesan tablet ve granül formülasyonu.
TR201000687A1 (tr) 2010-01-29 2011-08-22 Bi̇lgi̇ç Mahmut Aktif madde olarak sefiksim ve klavulanik asit içeren efervesan formülasyonlar
EP2568957A1 (en) 2010-05-14 2013-03-20 Mahmut Bilgic Pharmaceutical composition comprising cefixime and clavulanic acid derivative compound
JP6266978B2 (ja) 2010-08-10 2018-01-24 レンペックス・ファーマシューティカルズ・インコーポレイテッド 環状ボロン酸エステル誘導体およびその治療的使用
WO2013033461A1 (en) 2011-08-31 2013-03-07 Rempex Pharmaceuticals, Inc. Heterocyclic boronic acid ester derivatives and therapeutic uses thereof
PT3616695T (pt) 2011-09-09 2024-11-18 Merck Sharp & Dohme Ceftolozano/tazobactam para tratar infeções intrapulmonares
WO2013109229A1 (en) 2012-01-18 2013-07-25 Mahmut Bilgic Tablet formulations comprising cefixime as active agent
US9156858B2 (en) 2012-05-23 2015-10-13 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
US10561675B2 (en) 2012-06-06 2020-02-18 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
US8809314B1 (en) 2012-09-07 2014-08-19 Cubist Pharmacueticals, Inc. Cephalosporin compound
US8476425B1 (en) 2012-09-27 2013-07-02 Cubist Pharmaceuticals, Inc. Tazobactam arginine compositions
KR20150103269A (ko) 2013-01-04 2015-09-09 렘펙스 파머수티클스 인코퍼레이티드 보론산 유도체 및 그의 치료적 용도
US9241947B2 (en) 2013-01-04 2016-01-26 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
EA201591004A1 (ru) 2013-01-04 2016-02-29 Ремпекс Фармасьютикалз, Инк. Производные бороновой кислоты и их терапевтическое применение
US9101638B2 (en) 2013-01-04 2015-08-11 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
WO2014126541A1 (en) 2013-02-14 2014-08-21 Bilgiç Mahmut Pharmaceutical compositions used in treating bacterial infections
CN104004003B (zh) * 2013-02-22 2016-05-25 广州白云山医药集团股份有限公司白云山制药总厂 头孢克肟衍生物及其制备方法和用途
US9872906B2 (en) 2013-03-15 2018-01-23 Merck Sharp & Dohme Corp. Ceftolozane antibiotic compositions
CN110279698B (zh) 2013-03-15 2022-10-28 默沙东有限责任公司 头孢特咯瓒抗生素组合物
US20140274990A1 (en) 2013-03-15 2014-09-18 Cubist Pharmaceuticals, Inc. Ceftolozane pharmaceutical compositions
ES2800603T3 (es) 2013-09-09 2021-01-04 Merck Sharp & Dohme Tratamiento de infecciones con ceftolozano/tazobactam en sujetos con insuficiencia renal
US8906898B1 (en) 2013-09-27 2014-12-09 Calixa Therapeutics, Inc. Solid forms of ceftolozane
PL3604316T3 (pl) 2014-05-05 2024-04-29 Melinta Therapeutics, Inc. Synteza soli boronianowych
US9687497B1 (en) 2014-05-05 2017-06-27 Rempex Pharmaceuticals, Inc. Salts and polymorphs of cyclic boronic acid ester derivatives and therapeutic uses thereof
EP3145936B1 (en) 2014-05-19 2020-09-30 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
CN103980293B (zh) * 2014-05-21 2016-08-17 广州白云山医药集团股份有限公司白云山化学制药厂 3-乙烯基-7-（噻唑甲氧亚氨基）头孢烷酸的制备方法
CN104045655B (zh) * 2014-06-23 2016-08-17 山东普洛得邦医药有限公司 一种抗菌素头孢母核的合成方法
JP6700203B2 (ja) 2014-07-01 2020-05-27 レンペックス・ファーマシューティカルズ・インコーポレイテッド ボロン酸誘導体およびその治療的使用
CN104193765B (zh) * 2014-08-12 2016-08-17 浙江普洛得邦制药有限公司 一种头孢克肟的合成方法
WO2016081297A1 (en) 2014-11-18 2016-05-26 Rempex Pharmaceuticals, Inc. Cyclic boronic acid ester derivatives and therapeutic uses thereof
ES2761778T3 (es) 2014-12-19 2020-05-21 Rempex Pharmaceuticals Inc Aparato y proceso de flujo continuo para la producción de derivados de ácido borónico
WO2016142902A1 (en) 2015-03-11 2016-09-15 Lupin Limited Cefixime with reduced surface area and high stability
US20180051041A1 (en) 2015-03-17 2018-02-22 Rempex Pharmaceuticals, Inc. Boronic acid derivatives and therapeutic uses thereof
WO2017046756A1 (en) * 2015-09-18 2017-03-23 Lupin Limited Proxetil and axetil esters of cefixime
JP7060245B2 (ja) 2016-06-30 2022-04-26 キューペックス バイオファーマ， インコーポレイテッド ボロン酸誘導体およびその治療的使用
BR112020007138B1 (pt) 2017-10-11 2023-03-21 Qpex Biopharma, Inc Derivados de ácido borônico, métodos de síntese, composição farmacêutica e uso dos mesmos
CA3097127A1 (en) 2018-04-20 2019-10-24 Qpex Biopharma, Inc. Boronic acid derivatives and therapeutic uses thereof
CN110041346B (zh) * 2019-04-17 2022-06-07 广东立国制药有限公司 一种低成本的头孢克肟的制备方法
CN111592471B (zh) * 2020-06-12 2023-03-21 济南大学 一种溴化反应合成头孢活性酯中间体的方法

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1241657A (en) * 1967-08-21 1971-08-04 Glaxo Lab Ltd Improvements in or relating to cephalosporin compounds
US3994884A (en) * 1970-01-23 1976-11-30 Glaxo Laboratories Limited 3-Vinyl-7β-(2,2-disubstituted acetamido)-cephalosporins
GB1342241A (en) * 1970-01-23 1974-01-03 Glaxo Lab Ltd Cephalosporin compounds
US4107431A (en) * 1970-01-23 1978-08-15 Glaxo Laboratories Limited Δ3 -3-Vinyl or substituted vinyl-4-carboxy cephalosporins
US4110534A (en) * 1970-01-23 1978-08-29 Glaxo Laboratories Limited Process for the preparation of 3-vinyl and substituted vinyl cephalosporins
US4024134A (en) * 1971-01-29 1977-05-17 Glaxo Laboratories Limited Syn isomers of cephalosporins having α-hydroximino- or α-acyloxyiminoacylamido groups at position-7
GB1389194A (en) 1971-01-29 1975-04-03 Glaxo Lab Ltd Antibiotics
GB1445979A (en) 1972-10-25 1976-08-11 Glaxo Lab Ltd Cephalosporin derivatives
GB1399088A (en) * 1971-05-14 1975-06-25 Glaxo Lab Ltd Cephalosporin compounds
DK154939C (da) * 1974-12-19 1989-06-12 Takeda Chemical Industries Ltd Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf
GB1575803A (en) * 1976-03-09 1980-10-01 Fujisawa Pharmaceutical Co 3,7 disubstituted 3 cephem 4 carboxylic acid compounds andprocesses for the preparation thereof
US4166115A (en) * 1976-04-12 1979-08-28 Fujisawa Pharmaceutical Co., Ltd. Syn 7-oxoimino substituted derivatives of cephalosporanic acid
PH17188A (en) 1977-03-14 1984-06-14 Fujisawa Pharmaceutical Co New cephem and cepham compounds and their pharmaceutical compositions and method of use
SE439312B (sv) * 1977-03-25 1985-06-10 Roussel Uclaf Sett att framstella nya oximderivat av 3-acetoximetyl-7-aminotiazolylacetamido cefalosporansyra
DE2714880A1 (de) * 1977-04-02 1978-10-26 Hoechst Ag Cephemderivate und verfahren zu ihrer herstellung
US4255423A (en) * 1977-07-27 1981-03-10 Merck & Co., Inc. Cephalosporin compounds
IT1192287B (it) * 1977-11-14 1988-03-31 Fujisawa Pharmaceutical Co Derivati di acido cefalosporanico ad azione farmaceutica e relativo procedimento di preparazione
DE2758001A1 (de) * 1977-12-24 1979-07-12 Hoechst Ag Cephalosporinderivate und verfahren zu ihrer herstellung
FR2387235A1 (fr) * 1978-01-23 1978-11-10 Fujisawa Pharmaceutical Co Procede de preparation de composes d'acide 3,7-disubstitue-3-cephem-4-carboxylique et nouveaux produits ainsi obtenus, ayant une forte activite antibacterienne
SE448379B (sv) * 1978-03-31 1987-02-16 Roussel Uclaf O-substituerade oximderivat av 7-amino-tiazolyl-acetamidocefalosporansyra
US4284631A (en) * 1978-07-31 1981-08-18 Fujisawa Pharmaceutical Co., Ltd. 7-Substituted cephem compounds and pharmaceutical antibacterial compositions containing them
US4305937A (en) * 1978-08-17 1981-12-15 Fujisawa Pharmaceutical Co., Ltd. 2-Lower alkyl-7-substituted-2 or 3-cephem-4-carboxylic acid compounds and antibacterial pharmaceutical compositions containing them
US4703046A (en) * 1978-09-08 1987-10-27 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds and processes for preparation thereof
GB2033377B (en) * 1978-09-11 1983-05-05 Fujisawa Pharmaceuticalco Ltd Cephem compounds and processes for preparation thereof
EP0009671B1 (en) * 1978-09-12 1984-06-13 Fujisawa Pharmaceutical Co., Ltd. Starting compounds for preparing cephem compounds and processes for their preparation
US4220761A (en) * 1978-09-12 1980-09-02 Fujisawa Pharmaceutical Co., Ltd. 7-[Substituted oximinoacetamido]-3-[hydroxy alkyltetrazolo]cephalosporin derivatives
US4409214A (en) * 1979-11-19 1983-10-11 Fujisawa Pharmaceutical, Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
US4266049A (en) * 1980-02-20 1981-05-05 Eli Lilly And Company Process for 3-iodomethyl cephalosporins
DK162718C (da) * 1982-09-30 1992-05-11 Fujisawa Pharmaceutical Co Analogifremgangsmaade til fremstilling af 7-substitueret-3-vinyl-3-cephemforbindelser
GB8323034D0 (en) * 1983-08-26 1983-09-28 Fujisawo Pharmaceutical Co Ltd 7-substituted-3-vinyl-3-cephem compounds

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MX158337A (es) 1989-01-26
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