SE462096B - Dicyklohexylammonium-6 beta-brompenicillanat vilken aer anvaendbar saasom mellanprodukt - Google Patents
Dicyklohexylammonium-6 beta-brompenicillanat vilken aer anvaendbar saasom mellanproduktInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs 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
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)
| 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)
| 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 |
-
1980
- 1980-04-29 IE IE2559/84A patent/IE49770B1/en unknown
- 1980-04-29 IE IE868/80A patent/IE49768B1/en not_active IP Right Cessation
- 1980-04-29 IL IL59948A patent/IL59948A0/xx unknown
- 1980-05-01 NZ NZ193597A patent/NZ193597A/en unknown
- 1980-05-05 PH PH23982A patent/PH17959A/en unknown
- 1980-05-12 GR GR61906A patent/GR68372B/el unknown
- 1980-05-19 SE SE8003722A patent/SE452465B/sv not_active IP Right Cessation
- 1980-05-20 LU LU82468A patent/LU82468A1/fr unknown
- 1980-05-20 IT IT67790/80A patent/IT1133091B/it active
- 1980-05-20 AU AU58584/80A patent/AU534754B2/en not_active Ceased
- 1980-05-20 DE DE19803051038 patent/DE3051038C2/de not_active Expired
- 1980-05-20 DK DK218580A patent/DK158669C/da not_active IP Right Cessation
- 1980-05-20 DE DE19803051037 patent/DE3051037C2/de not_active Expired
- 1980-05-20 FI FI801618A patent/FI801618A/fi not_active Application Discontinuation
- 1980-05-20 FR FR8011263A patent/FR2457294A1/fr active Granted
- 1980-05-20 JP JP6768580A patent/JPS55154977A/ja active Granted
- 1980-05-20 CA CA000352237A patent/CA1265787A/en not_active Expired - Fee Related
- 1980-05-20 BE BE0/200687A patent/BE883390A/fr not_active IP Right Cessation
- 1980-05-20 NL NL8002911A patent/NL8002911A/nl not_active Application Discontinuation
- 1980-05-20 DE DE19803019244 patent/DE3019244A1/de active Granted
- 1980-05-20 PT PT71273A patent/PT71273A/pt unknown
- 1980-11-17 US US06/207,614 patent/US4446144A/en not_active Expired - Lifetime
-
1982
- 1982-03-04 FR FR8203636A patent/FR2499575A1/fr active Granted
-
1983
- 1983-08-26 AU AU18486/83A patent/AU541322B2/en not_active Ceased
- 1983-08-26 PH PH29453A patent/PH19005A/en unknown
- 1983-08-26 AU AU18487/83A patent/AU541323B2/en not_active Ceased
- 1983-12-23 US US06/564,901 patent/US4594246A/en not_active Expired - Fee Related
-
1984
- 1984-12-06 SE SE8406202A patent/SE462097B/sv not_active IP Right Cessation
- 1984-12-06 SE SE8406201A patent/SE462096B/sv not_active IP Right Cessation
-
1986
- 1986-03-31 US US06/845,941 patent/US4672114A/en not_active Expired - Fee Related
-
1989
- 1989-11-10 DK DK562589A patent/DK158670C/da not_active IP Right Cessation
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