PL88867B1 - - Google Patents

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Publication number
PL88867B1
PL88867B1 PL1970172425A PL17242570A PL88867B1 PL 88867 B1 PL88867 B1 PL 88867B1 PL 1970172425 A PL1970172425 A PL 1970172425A PL 17242570 A PL17242570 A PL 17242570A PL 88867 B1 PL88867 B1 PL 88867B1
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PL
Poland
Prior art keywords
deoxy
formula
water
ice
once
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Application number
PL1970172425A
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Polish (pl)
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Publication date
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Publication of PL88867B1 publication Critical patent/PL88867B1/pl

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

Przedmiotem wynalazku jest sposób wytwarza¬ nia 14-dezoksy^l4-tosyloksyacetaksymutyliny o wzorze 1. Sposób wedlug wynalazku polega na tym, ze pleuromutyline o wzorze 2 poddaje sie re¬ akcji z p-toluenosulfochlorkiem.(Reakcje prowadzi sie korzystnie w obojetnym rozpuszczalniku organicznym, takim jak toluen lub benzen, korzystnie w rozpuszczalniku dzialajacym równoczesnie jako srodek wiazacy kwas, takim jak pirydyna. Reakcje- prowadzi sie w temperatu¬ rze —15° do —"10°C w ciagu 2—4 godzin.Otrzymana 14-dezoksy-14-tosyloksyacetoksy(mu- tyline mozna wyodrebniac z mieszaniny reakcyjnej i oczyszczac w znany sposób. Otrzymana sposo¬ bem wedlug wynalazku 14-dezoksy-14-tosyloksy- acetoksymutylina stanowi produkt posredni do wy¬ twarzania na przyklad wartosciowych leków we¬ terynaryjnych.Nastepujacy przyklad blizej ilustruje sposób we¬ dlug wynalazku.Przyklad. 14nDezoksy-14-tosyloksyacetoksy- -mutylina. 95 g pleuromutyliny rozpuszcza sie w 350 ml pirydyny. Roztwór chlodzi w ciagu 20 mi¬ nut do temperatury —15°C, traktuje sie 65 g chlor¬ ku p-toluenosulfonylu w jednej porcji i wytrzasa do calkowitego rozpuszczenia. Wsad przy czestym wstrzasaniu utrzymuje sie w ciagu 2 godzin w temperaturze —.16°C i w ciagu 1 godziny w tem¬ peraturze lodowatej wody. W przeróbce koncowej wylewa sie do 300—400 ml lodowatej wody i eks¬ trahuje sie 350 ml chloroformu. Chlodny roztwór organiczny wytrzasa sie jednorazowo z lodowata woda, trzykrotnie ze wczesniej ochlodzonym 3 n kwasem siarkowym (ogólem okolo 1 litra), jedno¬ razowo z woda i jednorazowo z nasyconym roz¬ tworem wodoroweglanu sodu. xo Faze chloroformowa oddziela sie, osusza siarcza¬ nem sodu i odparowuje. Pozostalosc traktuje sie benzyna {frakcja heksanowa) i krystalizuje po krótkim pocieraniu. Pozostawia sie na noc, nastep¬ nie odsacza sie, suszy i przekrystalizowuje z oko- lo 350 ml izopropanolu, przy czym otrzymuje sie 14-dezoksy-14-tosyloksyacetoksymutyline o tempe¬ raturze topnienia 146—148°C. Po ponownym prze- krystalizowaniu z mieszaniny aceton-heksan tem¬ peratura topnienia wzrasta do 147,5—149,5°C. Ana- liza C i H: obliczono: 65,39% C, 7,57% H; otrzy¬ mano: 65,02% C, 7,70% H.: Bltk 2109/76 r. .110 egz. A4 Cena 10 zl PLThe subject of the invention is a process for the preparation of 14-deoxy-14-tosyloxyacetaximutilin of formula 1. The process of the invention consists in reacting a pleuromutylline of formula II with p-toluenesulfchloride. (The reaction is preferably carried out in an inert organic solvent, such as toluene or benzene, preferably in a solvent which simultaneously acts as an acid binding agent, such as pyridine. The reaction is carried out at -15 ° to -10 ° C for 2 to 4 hours. The resulting 14-deoxy-14 -tosyloxyacetoxy (mutilin can be isolated from the reaction mixture and purified in a known manner. The 14-deoxy-14-tosyloxyacetoxymutilin obtained according to the invention is an intermediate product for the production of, for example, valuable veterinary drugs. The following example follows. illustrates the process of the invention. Example 14n-deoxy-14-tosyloxyacetoxy-mutiline. 95 g of pleuromutilin are dissolved in 350 ml of pyridine. temperature -15 ° C, 65 g of p-toluenesulfonyl chloride are added in one portion and shaken until completely dissolved. The batch is kept shaken for 2 hours at -16 ° C and for 1 hour at the temperature of ice-cold water. In the final work-up, 300-400 ml of ice-water are poured and extracted with 350 ml of chloroform. The cool organic solution is shaken once with ice water, three times with pre-cooled 3N sulfuric acid (about 1 liter in total), once with water and once with a saturated solution of sodium bicarbonate. The chloroform phase is separated off, dried with sodium sulphate and evaporated. The residue is treated with gasoline (hexanes) and crystallizes on brief rubbing. It is left to stand overnight, then filtered, dried and recrystallized from about 350 ml of isopropanol, giving 14-deoxy-14-tosyloxyacetoxymutylline, mp 146-148 ° C. After recrystallization from acetone-hexane, the melting point rises to 147.5-149.5 ° C. C and H analysis: Calculated: 65.39% C, 7.57% H; Received: 65.02% C, 7.70% H .: Bltk 2109/76 r. 110 copies A4 Price PLN 10 PL

Claims (2)

1. Zastrzezenie patentowe Sposób wytwarzania H-dezoksy-iH-tosyloksyace- 25 toksymutyliny o wzorze 1, znamienny tym, ze pleuromutyline o wzorzeClaim 1. Process for the preparation of H-deoxy-iH-tosyloxyacetoxymutilin of formula 1, characterized in that a pleuromutylline of formula 2 .poddaje sie reakcji z p-toluenosulfochlorkiem. 88 86788 867 OCO-CH2-0-502-f __ Wzór 1 OCO-CH2-OH CH=CH 9 Wzór 2 :zYTF.f.::, • ;' Ur*edi* Pni**--'*; PL2. Reacts with p-toluenesulfchloride. 88 86788 867 OCO-CH2-0-502-f __ Formula 1 OCO-CH2-OH CH = CH 9 Formula 2: zYTF.f. ::, •; ' Ur * edi * Pni ** - '*; PL
PL1970172425A 1969-07-25 1970-07-23 PL88867B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AT722369A AT301753B (en) 1969-07-25 1969-07-25 Process for the preparation of new pleuromutilin derivatives

Publications (1)

Publication Number Publication Date
PL88867B1 true PL88867B1 (en) 1976-10-30

Family

ID=3593920

Family Applications (2)

Application Number Title Priority Date Filing Date
PL1970172425A PL88867B1 (en) 1969-07-25 1970-07-23
PL1970142234A PL79777B1 (en) 1969-07-25 1970-07-23

Family Applications After (1)

Application Number Title Priority Date Filing Date
PL1970142234A PL79777B1 (en) 1969-07-25 1970-07-23

Country Status (13)

Country Link
JP (2) JPS5010590B1 (en)
AT (1) AT301753B (en)
CA (1) CA986102A (en)
CS (1) CS172913B2 (en)
DE (2) DE2066118C3 (en)
ES (3) ES382075A1 (en)
FR (1) FR2059559B1 (en)
GB (1) GB1312148A (en)
IL (1) IL34980A (en)
NL (1) NL7010444A (en)
PL (2) PL88867B1 (en)
SE (1) SE369712B (en)
ZA (1) ZA705091B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4107164A (en) * 1971-10-05 1978-08-15 Sandoz Ltd. Certain pleuromulilin ester derivatives
US4208326A (en) * 1971-10-05 1980-06-17 Sandoz Ltd. Pleuromutilin esters
BE789629A (en) * 1971-10-05 1973-04-03 Sandoz Sa NEW DERIVATIVES OF PLEUROMUTILINE, THEIR PREPARATION AND THERAPEUTIC APPLICATION
CY1353A (en) * 1979-01-12 1987-04-24 Sandoz Ag New pleuromutilin derivatives, their production and use
GB0017031D0 (en) * 2000-07-11 2000-08-30 Biochemie Gmbh Antimicrobials
GB0308114D0 (en) * 2003-04-08 2003-05-14 Glaxo Group Ltd Novel compounds
EP2014640A1 (en) * 2007-07-13 2009-01-14 Nabriva Therapeutics AG Pleuromutilin derivatives
EP2014645A1 (en) * 2007-07-13 2009-01-14 Nabriva Therapeutics AG Pleuromutilin derivatives and their use as antimicrobials
WO2021219399A1 (en) * 2020-04-28 2021-11-04 Nabriva Therapeutics GmbH Novel 12-epi-mutilin compounds, process for preparing the same and uses thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT261804B (en) * 1964-04-17 1968-05-10 Biochemie Gmbh Process for the production of new water-soluble, antibiotic compounds

Also Published As

Publication number Publication date
ES388613A1 (en) 1974-02-16
IL34980A0 (en) 1970-09-17
CA986102A (en) 1976-03-23
FR2059559A1 (en) 1971-06-04
IL34980A (en) 1974-09-10
DE2036027B2 (en) 1980-10-23
ES388614A1 (en) 1974-02-16
DE2036027A1 (en) 1971-02-18
FR2059559B1 (en) 1973-08-10
JPS5010857B1 (en) 1975-04-24
AT301753B (en) 1972-09-25
CS172913B2 (en) 1977-01-28
DE2036027C3 (en) 1981-12-17
DE2066118B1 (en) 1980-08-28
ZA705091B (en) 1972-02-23
JPS5010590B1 (en) 1975-04-22
NL7010444A (en) 1971-01-27
ES382075A1 (en) 1973-04-01
SE369712B (en) 1974-09-16
DE2066118C3 (en) 1981-07-16
PL79777B1 (en) 1975-06-30
GB1312148A (en) 1973-04-04

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