YU46151B - Postupak za dobijanje 7-/2-(5-amino-1, 2,4-tiadiazol-3-il)-2-(supstituisani)iminoacetamido/3-/3-(kvaternerni amonio)-1-propen-1-il/-3-cefem-4-karboksilata - Google Patents

Postupak za dobijanje 7-/2-(5-amino-1, 2,4-tiadiazol-3-il)-2-(supstituisani)iminoacetamido/3-/3-(kvaternerni amonio)-1-propen-1-il/-3-cefem-4-karboksilata

Info

Publication number
YU46151B
YU46151B YU60085A YU60085A YU46151B YU 46151 B YU46151 B YU 46151B YU 60085 A YU60085 A YU 60085A YU 60085 A YU60085 A YU 60085A YU 46151 B YU46151 B YU 46151B
Authority
YU
Yugoslavia
Prior art keywords
formula
hydrogen
amino
group
protecting group
Prior art date
Application number
YU60085A
Other languages
English (en)
Other versions
YU60085A (en
Inventor
H. Yamashita
M. Oka
J. Okumura
T. Naito
Original Assignee
Bristol-Myers Squibb 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
Application filed by Bristol-Myers Squibb Co. filed Critical Bristol-Myers Squibb Co.
Priority to YU118987A priority Critical patent/YU46213B/sh
Publication of YU60085A publication Critical patent/YU60085A/xx
Publication of YU46151B publication Critical patent/YU46151B/sh

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
    • 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
    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption

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)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

opšte formule u kojoj je R1 vodonik ili amino-zaštitna grupa kao što je tricil; R2 je vodonik, C1-4alkil, C3-6cikloalkil, C3-6cikloalkenil, ili grupa formule: gde je R3 vodonik, C1-4alkil ili karboksi, X je halogen, hidroksi ili C1-4alkoksi, i R4 i R5 su svaki nezavisno vodonik, metil ili etil, ili R4 i R5, uzeti zajedno sa ugljenikovim atomom za koji su vezani, grade cikloalkilidenski prsten sa 3-5 ugljenikovih atoma; i kvaternerna amino grupa; i njihovih netoksičnih farmaceutski prihvatljivih soli i estara koji hidrolizuju pod fiziološkim uslovima, naznačen ti me, što obuhvata reakciju jedinjenja formule: u kojoj je R2 isto kao R2, ili predstavlja grupu formule: gde su X, R4 i R5 kao što je definisano gore, B1 je karboksi-zaštitna grupa kao što je benzhidril ili t-butil, B2 je vodonik ili amino- zaštitna grupa kao što je tricil, Z je hloro, bromo ili jodo i m ima vrednost 0 ili 1, u rastvaraču kao što je etil acetat, dimetilsulfoksid, acetonitril ili metilehn hlorid, na temperaturi od oko -5 C do sobne temperature, sa tercijarnim aminom formule: Q N nakon čega se, ukoliko m ima vrednost 1, vrši redukcija sulfoksida pa se dobijeni zaštićeni intermedijer tretira kiselinom, kao što je mravlja kiselina, da bi se uklonile zaštitne grupe i dobio željeni proizvod; i što se, po potrebi, proizvod formule (I) prevodi u svoju netoksičnu farmaceutski prihvatljvu so ili estar koji hidrolizuje pod fiziološkim uslovima. Prijava sadrži još 2 zahteva.
YU60085A 1984-04-09 1985-04-09 Postupak za dobijanje 7-/2-(5-amino-1, 2,4-tiadiazol-3-il)-2-(supstituisani)iminoacetamido/3-/3-(kvaternerni amonio)-1-propen-1-il/-3-cefem-4-karboksilata YU46151B (sh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
YU118987A YU46213B (sh) 1984-04-09 1987-06-25 Postupak za dobijanje 7-/2-(5-amino-1,2,4-tiadiazol-3-il)-2-(supstituisani)iminoacetamido/-3 -/3-(kvaternerni amonio)-1-propen-1-il/-3-cefem-4-karboksilata

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US59794184A 1984-04-09 1984-04-09

Publications (2)

Publication Number Publication Date
YU60085A YU60085A (en) 1987-12-31
YU46151B true YU46151B (sh) 1993-05-28

Family

ID=24393575

Family Applications (2)

Application Number Title Priority Date Filing Date
YU60085A YU46151B (sh) 1984-04-09 1985-04-09 Postupak za dobijanje 7-/2-(5-amino-1, 2,4-tiadiazol-3-il)-2-(supstituisani)iminoacetamido/3-/3-(kvaternerni amonio)-1-propen-1-il/-3-cefem-4-karboksilata
YU118987A YU46213B (sh) 1984-04-09 1987-06-25 Postupak za dobijanje 7-/2-(5-amino-1,2,4-tiadiazol-3-il)-2-(supstituisani)iminoacetamido/-3 -/3-(kvaternerni amonio)-1-propen-1-il/-3-cefem-4-karboksilata

Family Applications After (1)

Application Number Title Priority Date Filing Date
YU118987A YU46213B (sh) 1984-04-09 1987-06-25 Postupak za dobijanje 7-/2-(5-amino-1,2,4-tiadiazol-3-il)-2-(supstituisani)iminoacetamido/-3 -/3-(kvaternerni amonio)-1-propen-1-il/-3-cefem-4-karboksilata

Country Status (31)

Country Link
JP (4) JPS615084A (sh)
KR (1) KR870002166B1 (sh)
AR (1) AR244694A1 (sh)
AT (1) AT388735B (sh)
AU (2) AU580990B2 (sh)
BE (1) BE902148A (sh)
CA (3) CA1276929C (sh)
CH (1) CH669197A5 (sh)
DD (3) DD249024A5 (sh)
DE (1) DE3512225A1 (sh)
DK (1) DK155985A (sh)
ES (4) ES8607318A1 (sh)
FI (1) FI84830C (sh)
FR (1) FR2563832B1 (sh)
GB (3) GB2157293B (sh)
GR (1) GR850883B (sh)
HU (2) HU193750B (sh)
IE (2) IE58408B1 (sh)
IL (1) IL74826A (sh)
IT (1) IT1190353B (sh)
LU (1) LU85840A1 (sh)
MY (1) MY101940A (sh)
NL (1) NL192925C (sh)
NZ (1) NZ211659A (sh)
OA (1) OA07985A (sh)
PT (1) PT80246B (sh)
RU (1) RU2056425C1 (sh)
SE (4) SE466205B (sh)
SU (4) SU1436882A3 (sh)
YU (2) YU46151B (sh)
ZA (1) ZA852236B (sh)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61145186A (ja) * 1984-12-20 1986-07-02 Meiji Seika Kaisha Ltd 新規セフエム化合物及びその製造法
US4708955A (en) * 1985-06-24 1987-11-24 Bristol-Myers Company 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof
DE3650157T2 (de) * 1985-12-26 1995-05-04 Eisai Co Ltd Cephalosporin-verbindungen.
AU614723B2 (en) * 1986-10-13 1991-09-12 Eisai Co. Ltd. 3-propenylcephem derivative
IL84128A (en) * 1986-10-13 1992-12-01 Eisai Co Ltd 3-propenylcephem derivatives, their preparation and pharmaceutical compositions containing them
JPH085897B2 (ja) * 1986-11-06 1996-01-24 エーザイ株式会社 ３−プロペニルセフェム誘導体
FR2622585B1 (fr) * 1987-11-03 1991-04-19 Roussel Uclaf Nouvelles cephalosporines comportant en position 3 un radical vinyle substitue, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus
EP0612751A3 (en) * 1988-03-16 1994-09-21 Eisai Co Ltd Compounds for the preparation of cephem derivatives.
JPH0699449B2 (ja) * 1988-03-16 1994-12-07 エーザイ株式会社 セフェム誘導体の合成中間体
FR2655042B1 (fr) * 1989-11-29 1994-01-21 Adir Cie Nouvelles benzothiazolinones substituees, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
FR2663332B1 (fr) * 1990-06-15 1997-11-07 Roussel Uclaf Nouvelles cephalosporines comportant en position 3 un radical propenyle substitue par un ammonium quaternaire, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus.
US5126336A (en) * 1990-08-23 1992-06-30 Bristol-Myers Squibb Company Antibiotic c-3 catechol-substituted cephalosporin compounds, compositions and method of use thereof
AT396108B (de) * 1991-08-21 1993-06-25 Biochemie Gmbh Neues verfahren und neue zwischenprodukte zur herstellung von 7-aminocephalosporansaeurederivaten
JPH0741484A (ja) * 1993-07-29 1995-02-10 Katayama Seiyakushiyo:Kk セフェム化合物及び抗菌剤
KR100248851B1 (ko) * 1994-08-16 2000-04-01 이치로 키타사토 신규 세펨 유도체
JP4033630B2 (ja) 1998-06-22 2008-01-16 バジリア ファルマスーチカ アーゲー プロペニルセファロスポリン誘導体
US7507812B2 (en) 2003-09-09 2009-03-24 Nippon Chemical Industrial Co., Ltd. Process for producing 3-chloromethyl-3-cephem derivatives

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1342241A (en) * 1970-01-23 1974-01-03 Glaxo Lab Ltd Cephalosporin compounds
US4390534A (en) * 1978-12-29 1983-06-28 Fujisawa Pharmaceutical Co., Ltd. Cephem and cepham compounds
EP0025017A1 (de) * 1979-08-28 1981-03-11 Ciba-Geigy Ag Polyazathiaverbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend solche Verbindungen und Verwendung von letzteren
US4409214A (en) * 1979-11-19 1983-10-11 Fujisawa Pharmaceutical, Co., Ltd. 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof
GR75644B (sh) * 1980-06-18 1984-08-02 Fujisawa Pharmaceutical Co
GR78245B (sh) * 1980-09-12 1984-09-26 Ciba Geigy Ag
US4521413A (en) * 1981-09-14 1985-06-04 Fujisawa Pharmaceutical Co., Ltd. Cephem compounds
US4486586A (en) * 1983-02-10 1984-12-04 Bristol-Myers Company Cephalosporin derivatives

Also Published As

Publication number Publication date
SE8901226L (sv) 1989-04-06
GB2157293B (en) 1988-10-05
SU1487814A3 (ru) 1989-06-15
SE8501680L (sv) 1985-10-10
HU204277B (en) 1991-12-30
GB2157293A (en) 1985-10-23
IE850866L (en) 1985-10-09
ATA103985A (de) 1989-01-15
SE8501680D0 (sv) 1985-04-03
DK155985D0 (da) 1985-04-03
SU1436882A3 (ru) 1988-11-07
AU580990B2 (en) 1989-02-09
GB8721347D0 (en) 1987-10-14
NL192925B (nl) 1998-01-05
IT1190353B (it) 1988-02-16
DD251752A5 (de) 1987-11-25
AU4086285A (en) 1985-10-17
JPH0350754B2 (sh) 1991-08-02
ZA852236B (en) 1985-11-27
ES8800949A1 (es) 1987-12-01
DD236735A5 (de) 1986-06-18
GB2194789A (en) 1988-03-16
RU2056425C1 (ru) 1996-03-20
ES8706155A1 (es) 1987-06-01
SE8901225L (sv) 1989-04-06
GB8721346D0 (en) 1987-10-14
SE8901226D0 (sv) 1989-04-06
NZ211659A (en) 1988-11-29
SE470259B (sv) 1993-12-20
DE3512225A1 (de) 1985-10-17
ES542013A0 (es) 1986-06-16
GR850883B (sh) 1985-11-25
CA1340638C (en) 1999-07-06
CH669197A5 (de) 1989-02-28
FI851379L (fi) 1985-10-10
JPH0262557B2 (sh) 1990-12-26
DE3512225C2 (sh) 1990-02-22
IE58403B1 (en) 1993-09-22
IE58408B1 (en) 1993-09-22
ES551550A0 (es) 1987-06-01
DK155985A (da) 1985-10-10
FI84830C (fi) 1992-01-27
SE466205B (sv) 1992-01-13
GB2194789B (en) 1988-10-12
PT80246A (en) 1985-05-01
IL74826A (en) 1990-01-18
AT388735B (de) 1989-08-25
ES8706694A1 (es) 1987-07-01
JPH0357106B2 (sh) 1991-08-30
CA1276929C (en) 1990-11-27
HUT37622A (en) 1986-01-23
JPS61143390A (ja) 1986-07-01
BE902148A (fr) 1985-10-09
AU610278B2 (en) 1991-05-16
HU193750B (en) 1987-11-30
JPS615084A (ja) 1986-01-10
GB2194790B (en) 1988-10-05
IL74826A0 (en) 1985-07-31
FR2563832B1 (fr) 1989-08-18
ES551551A0 (es) 1987-07-01
YU60085A (en) 1987-12-31
SE470260B (sv) 1993-12-20
SU1367858A3 (ru) 1988-01-15
IT8520267A0 (it) 1985-04-05
YU118987A (en) 1988-10-31
FI84830B (fi) 1991-10-15
ES557060A0 (es) 1987-12-01
JPH0351716B2 (sh) 1991-08-07
GB8508846D0 (en) 1985-05-09
KR870002166B1 (ko) 1987-12-14
AU2504188A (en) 1989-03-02
OA07985A (fr) 1987-01-31
DD249024A5 (de) 1987-08-26
FI851379A0 (fi) 1985-04-04
PT80246B (pt) 1987-10-20
KR850007424A (ko) 1985-12-04
SE8901224L (sv) 1989-04-06
JPS61143387A (ja) 1986-07-01
FR2563832A1 (fr) 1985-11-08
JPS61143391A (ja) 1986-07-01
YU46213B (sh) 1993-05-28
CA1340672C (en) 1999-07-20
LU85840A1 (fr) 1985-12-16
NL192925C (nl) 1998-05-07
SE8901225D0 (sv) 1989-04-06
GB2194790A (en) 1988-03-16
AR244694A1 (es) 1993-11-30
SU1375140A3 (ru) 1988-02-15
SE8901224D0 (sv) 1989-04-06
NL8501002A (nl) 1985-11-01
SE505256C2 (sv) 1997-07-21
MY101940A (en) 1992-02-15
ES8607318A1 (es) 1986-06-16

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