SE462096B - Dicyklohexylammonium-6 beta-brompenicillanat vilken aer anvaendbar saasom mellanprodukt - Google Patents

Dicyklohexylammonium-6 beta-brompenicillanat vilken aer anvaendbar saasom mellanprodukt

Info

Publication number
SE462096B
SE462096B SE8406201A SE8406201A SE462096B SE 462096 B SE462096 B SE 462096B SE 8406201 A SE8406201 A SE 8406201A SE 8406201 A SE8406201 A SE 8406201A SE 462096 B SE462096 B SE 462096B
Authority
SE
Sweden
Prior art keywords
dicyclohexylammonium
water
bromopenicillanate
brompenicillanate
beta
Prior art date
Application number
SE8406201A
Other languages
English (en)
Other versions
SE8406201L (sv
SE8406201D0 (sv
Inventor
Daehne W Von
Original Assignee
Leo Pharm Prod 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 Leo Pharm Prod Ltd filed Critical Leo Pharm Prod Ltd
Publication of SE8406201L publication Critical patent/SE8406201L/sv
Publication of SE8406201D0 publication Critical patent/SE8406201D0/sv
Publication of SE462096B publication Critical patent/SE462096B/sv

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D499/00Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

462 096 2 eftersom ren öflkbrompenicillansyra icke har någon inverkan på dessa enzymer, har den ifrågavarande inhibitorverkan till- skrivits 65-bromisomeren.
Saltet enligt uppfinningen kan användas för fram- ställning av 6B-brompenicillansyra i rent tillstånd (se exempel 2 nedan), något som hittills icke har varit möjligt.
Saltet enligt uppfinningen kan framställas på det sätt som illustreras i exempel 1 nedan.
Exempel 1 Dicyklohexylammonium-66-brompenicillanat Till en lösning av 10,8 g (30 mmol) 6,6-dibrompeni- cillansyra i 75 ml dimetylsulfoxid sattes 2,1 g (90-procentigt ren) natriumcyanoborhydrid; blandningen omrördes tills en klar lösning erhölls (ca 30 min). Efter att ha fått stå i 72 h utspäddes blandningen med 75 ml vatten. Härvid utfälldes oreagerat utgångsmaterial i form av dimetylsulfoxidsolvat (C H Br NO 8 9 2 med vatten och torkades. Filtratet extraherades med fyra gånger 38, C2H6OS). Kristallerna avfíltrerades, tvättades 25 ml metylenklorid, och de sammanslagna extrakten tvättades med 50 ml vatten, torkades (Na2SO4) och koncentrerades vid förminskat tryck till ca halva volymen. Sedan 2,5 ml dicyklo- hexylamin och 50 ml aceton tillsatts, koncentrerades bland- ningen ytterligare till ca 25 ml. Kristallisering' åstadkoms genom skrapning, och efter att preparatet fått stå 1 11 vid rumstemperatur avfiltrerades det rena dicyklohexylammonium- -6B-brompenicillanatet, varpå det tvättades med aceton och torkades. Föreningen uppvisade icke någon väldefinierad smält- punkt; sedan den mörknat vid ca 170°C sönderdelades den vid 280-29o°c. f

Claims (4)

1. 3 462 096
2. Exempel 2 6ß-brompenicillansyra
3. En omrörd suspension av dicyklohexylammonium-6ß-brom- penicillanat i etylacetat-vatten (1:1) (20 ml/g salt) inställ- des på pH 3 med 4 N klorvätesyra. Utfälld dicyklohexylammonium- klorid avfiltrerades, och det organiska skiktet avskildes, tvättades två gånger med vatten och torkades. Vid tillsättning av samma volym hexan och efterföljande koncentrering av lös- ningen vid förminskat tryck erhölls ren, kristallin 68-brom- penicillansyra med följande egenskaper.
4. [4]š° = +272° (C = 0,5; cHc13) 1H-NMR (cn3cN)=6 5,48 och 5,54 ppm, zd, J = 4,0 Hz, CH-5 och CH-6. Elementaranalys: Beräknat för C8H10BrNO3S: C 34,30; H 3,60; Br 28,53; N 5,00; S 11,45%. Funnet: C 34,47; H 3,81; Br 28,66; N 4,99; S 11,43%. P a t e n t k r a v Dicyklohexylammonium-66-brompenicillanat med formeln
SE8406201A 1979-05-21 1984-12-06 Dicyklohexylammonium-6 beta-brompenicillanat vilken aer anvaendbar saasom mellanprodukt SE462096B (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB7917665 1979-05-21
GB7930819 1979-09-05
GB7941252 1979-11-29
GB8006681 1980-02-27

Publications (3)

Publication Number Publication Date
SE8406201L SE8406201L (sv) 1984-12-06
SE8406201D0 SE8406201D0 (sv) 1984-12-06
SE462096B true SE462096B (sv) 1990-05-07

Family

ID=27449123

Family Applications (3)

Application Number Title Priority Date Filing Date
SE8003722A SE452465B (sv) 1979-05-21 1980-05-19 6 beta-halopenicillansyraderivat och kompositioner innehallande desamma
SE8406202A SE462097B (sv) 1979-05-21 1984-12-06 Foerfarande foer framstaellning av en i huvudsak ren 6 beta-halogen penicillansyra
SE8406201A SE462096B (sv) 1979-05-21 1984-12-06 Dicyklohexylammonium-6 beta-brompenicillanat vilken aer anvaendbar saasom mellanprodukt

Family Applications Before (2)

Application Number Title Priority Date Filing Date
SE8003722A SE452465B (sv) 1979-05-21 1980-05-19 6 beta-halopenicillansyraderivat och kompositioner innehallande desamma
SE8406202A SE462097B (sv) 1979-05-21 1984-12-06 Foerfarande foer framstaellning av en i huvudsak ren 6 beta-halogen penicillansyra

Country Status (19)

Country Link
US (3) US4446144A (sv)
JP (1) JPS55154977A (sv)
AU (3) AU534754B2 (sv)
BE (1) BE883390A (sv)
CA (1) CA1265787A (sv)
DE (3) DE3051038C2 (sv)
DK (2) DK158669C (sv)
FI (1) FI801618A (sv)
FR (2) FR2457294A1 (sv)
GR (1) GR68372B (sv)
IE (2) IE49770B1 (sv)
IL (1) IL59948A0 (sv)
IT (1) IT1133091B (sv)
LU (1) LU82468A1 (sv)
NL (1) NL8002911A (sv)
NZ (1) NZ193597A (sv)
PH (2) PH17959A (sv)
PT (1) PT71273A (sv)
SE (3) SE452465B (sv)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4432970A (en) * 1979-11-23 1984-02-21 Pfizer Inc. 6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors
IE51846B1 (en) * 1980-11-17 1987-04-15 Leo Pharm Prod Ltd Pharmaceutical preparation for veterinary use and an appliance containing it
US4521533A (en) * 1984-07-12 1985-06-04 Pfizer Inc. Salts of 6-alpha-(aminomethyl)penicillanic acid 1,1-dioxide esters and beta-lactam antibiotics
GB8522156D0 (en) * 1985-09-06 1985-10-09 Leo Pharm Prod Ltd Producing chemical compounds
US5589354A (en) * 1994-12-20 1996-12-31 Biopure Corporation Halogenation of cephalexin with haloperoxidase from Rathayibacter biopuresis
US5695951A (en) * 1994-12-20 1997-12-09 Biopure Corporation Chlorination of cephalexin with chloroperoxidase from Rathayibacter biopuresis
NZ336153A (en) 1996-12-18 2000-06-23 Bimeda Res & Dev Ltd Antiinfective free intramammary veterinary composition comprising a gel and a heavy metal compound for the prevention of mastitis
US20020035107A1 (en) * 2000-06-20 2002-03-21 Stefan Henke Highly concentrated stable meloxicam solutions
ES2265590T3 (es) * 2002-10-25 2007-02-16 Intervet International Bv Composicion farmaceutica de liberacion prolongada.
EP1568369A1 (en) 2004-02-23 2005-08-31 Boehringer Ingelheim Vetmedica Gmbh Use of meloxicam for the treatment of respiratory diseases in pigs
DE102004025324A1 (de) * 2004-05-19 2005-12-08 Boehringer Ingelheim Vetmedica Gmbh Flüssige Zubereitung für die Veterinärmedizin, Verfahren zu deren Herstellung und deren Verwendung
WO2014014364A1 (en) * 2012-07-17 2014-01-23 Bayer New Zealand Limited Injectable antibiotic formulations and their methods of use
PL2874624T3 (pl) 2012-07-17 2020-07-27 Bayer New Zealand Limited 3 Argus Place Hillcrest, Auckland 0627 / NZ Wstrzykiwalne formulacje antybiotykowe i sposoby ich zastosowania
WO2014098624A1 (en) * 2012-12-20 2014-06-26 Alleva Animal Health Limited Veterinary injectable formulations
EP4265241A1 (en) * 2022-04-20 2023-10-25 Bilim Ilac Sanayii Ve Ticaret A.S. Tablet formulations for the treatment of urinary system infections and method for the preparation of such formulations

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1089385B (de) 1954-06-21 1960-09-22 Biochemie Gmbh Verfahren zur Herstellung von in Wasser schwer loeslichen, besonders fuer die Oraltherapie geeigneten Salzen des Penicillins mit organischen Basen
DE1031795B (de) 1955-09-29 1958-06-12 Chimiotherapie Lab Franc Verfahren zur Herstellung eines Salzes aus Penicillin und einer Piperazinbase
US3206469A (en) * 1961-08-15 1965-09-14 Lepetit Spa 6-halopenicillanic acid
GB1297555A (sv) * 1970-09-22 1972-11-22
GB1377817A (en) * 1971-06-09 1974-12-18 Beecham Group Ltd Penicillins and cephalosporins
US4234579A (en) * 1977-06-07 1980-11-18 Pfizer Inc. Penicillanic acid 1,1-dioxides as β-lactamase inhibitors
IN149747B (sv) * 1977-06-07 1982-04-03 Pfizer
US4180506A (en) * 1978-01-18 1979-12-25 Rex Pratt 6β-Bromo penicillanic acid
US4203992A (en) * 1978-12-11 1980-05-20 E. R. Squibb & Sons, Inc. β-Bromopenicillanic acid sulfone
CA1158639A (en) 1978-12-11 1983-12-13 Eric M. Gordon 6-bromopenicillanic acid sulfone
DE3068390D1 (en) * 1979-01-10 1984-08-09 Beecham Group Plc Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds
IL59081A0 (en) * 1979-01-10 1980-05-30 Schering Corp 2-penem compounds and a method for preparing them
US4518530A (en) * 1979-03-05 1985-05-21 Pfizer Inc. 6-β-Substituted penicillanic acids as β-lactamase inhibitors
US4397783A (en) * 1979-03-05 1983-08-09 Pfizer Inc. Process for converting 6,6-disubstituted penicillanic acid derivatives to the 6-β-congeners
US4287181A (en) * 1979-10-22 1981-09-01 Pfizer Inc. Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors
US4432970A (en) * 1979-11-23 1984-02-21 Pfizer Inc. 6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors

Also Published As

Publication number Publication date
IE49768B1 (en) 1985-12-11
PH17959A (en) 1985-02-20
PH19005A (en) 1985-12-03
LU82468A1 (fr) 1980-12-16
AU1848683A (en) 1983-12-22
DE3019244C2 (sv) 1989-04-06
SE8406201L (sv) 1984-12-06
IE842559L (en) 1980-11-21
US4672114A (en) 1987-06-09
DK218580A (da) 1980-11-22
PT71273A (en) 1980-06-01
SE8003722L (sv) 1980-11-22
AU534754B2 (en) 1984-02-16
SE8406202D0 (sv) 1984-12-06
DE3019244A1 (de) 1980-12-04
US4594246A (en) 1986-06-10
AU541322B2 (en) 1985-01-03
US4446144A (en) 1984-05-01
DK158669B (da) 1990-07-02
AU541323B2 (en) 1985-01-03
AU5858480A (en) 1980-11-27
JPS55154977A (en) 1980-12-02
IE49770B1 (en) 1985-12-11
SE452465B (sv) 1987-11-30
FR2457294B1 (sv) 1984-01-13
IL59948A0 (en) 1980-06-30
DE3051037C2 (sv) 1989-03-30
FR2457294A1 (fr) 1980-12-19
FR2499575B1 (sv) 1985-03-01
GR68372B (sv) 1981-12-28
IT8067790A0 (it) 1980-05-20
JPH0140837B2 (sv) 1989-08-31
DK158670B (da) 1990-07-02
AU1848783A (en) 1983-12-22
DE3051038A1 (sv) 1986-03-20
NL8002911A (nl) 1980-11-25
FR2499575A1 (fr) 1982-08-13
FI801618A (fi) 1980-11-22
DK158669C (da) 1991-01-21
NZ193597A (en) 1985-04-30
DK158670C (da) 1991-01-07
SE462097B (sv) 1990-05-07
BE883390A (fr) 1980-11-20
DK562589A (da) 1989-11-10
SE8406201D0 (sv) 1984-12-06
CA1265787A (en) 1990-02-13
DK562589D0 (da) 1989-11-10
IE800868L (en) 1980-11-21
IT1133091B (it) 1986-07-09
SE8406202L (sv) 1984-12-06
DE3051038C2 (sv) 1989-04-13

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