RU98117732A - METHOD OF OBTAINING 2-HALOGENMETHILPENEM AND THEIR USE TO OBTAIN ANTIBACTERIAL FOAMS - Google Patents

METHOD OF OBTAINING 2-HALOGENMETHILPENEM AND THEIR USE TO OBTAIN ANTIBACTERIAL FOAMS

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Publication number
RU98117732A
RU98117732A RU98117732/04A RU98117732A RU98117732A RU 98117732 A RU98117732 A RU 98117732A RU 98117732/04 A RU98117732/04 A RU 98117732/04A RU 98117732 A RU98117732 A RU 98117732A RU 98117732 A RU98117732 A RU 98117732A
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Russia
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formula
group
compounds
defined above
organic
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RU98117732/04A
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Russian (ru)
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RU2175971C2 (en
Inventor
Перротта Энцо
Алтамура Мария
Original Assignee
А.Менарини Индустрие Фармачеутике Рьюните С.Р.Л.
Иституто Люсо Фармако Д'Италиа С.П.А.
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Priority claimed from IT96FI000033A external-priority patent/IT1286558B1/en
Application filed by А.Менарини Индустрие Фармачеутике Рьюните С.Р.Л., Иституто Люсо Фармако Д'Италиа С.П.А. filed Critical А.Менарини Индустрие Фармачеутике Рьюните С.Р.Л.
Publication of RU98117732A publication Critical patent/RU98117732A/en
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Publication of RU2175971C2 publication Critical patent/RU2175971C2/en

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Claims (8)

1. Способ получения 2-галогенметилпенемов формулы 1
Figure 00000001

где R1 представляет защитную группу для спиртового гидроксила, R2 представляет защитную группу для карбоксила и Х представляет галоген, содержащий в качестве промежуточной стадии образование соответствующего галогенацетилтиоазетидона V
Figure 00000002

где Х представляет галоген.1. The method of obtaining 2-halomethylpenems of formula 1
Figure 00000001

where R 1 represents a protective group for alcoholic hydroxyl, R 2 represents a protective group for carboxyl, and X represents a halogen containing as an intermediate stage the formation of the corresponding haloacetylthioazetidone V
Figure 00000002

where X represents halogen. 2. Способ по п.1 отличающийся тем, что: а) соединения формулы III
Figure 00000003

где R1, как определено выше, подвергают реакции с 2-галогентиоуксусной кислотой в органическом растворителе в присутствии органического основания и кислоты Льюиса при температуре от (-10)-(+40)oC для получения соединений формулы V, как определено в п.1; б) указанные выше соединения формулы (V) подвергают реакции с эфиром оксалилхлорида в органическом растворителе в присутствии органического основания при температуре (-60)-(+20)oC, предпочтительно (-20)-(+10)oC, для получения соединений формулы VII
Figure 00000004

где R1, R2 и Х такие, как определено выше; в) соединения формулы (VII) циклизуют в подходящем растворителе при 20-140°С в течение 1-120 ч под действием органического фосфата или фосфонита.2. The method according to claim 1, characterized in that: a) compounds of formula III
Figure 00000003

where R 1 as defined above, is subjected to reaction with 2-halogenthioacetic acid in an organic solvent in the presence of an organic base and Lewis acid at temperatures from (-10) - (+ 40) o C to obtain compounds of the formula V, as defined in paragraph one; b) the above compounds of formula (V) are subjected to reaction with oxalyl chloride ether in an organic solvent in the presence of an organic base at a temperature of (-60) - (+ 20) o C, preferably (-20) - (+ 10) o C, to obtain compounds of formula VII
Figure 00000004

where R 1 , R 2 and X are as defined above; c) Compounds of formula (VII) are cyclized in a suitable solvent at 20-140 ° C for 1-120 hours under the action of an organic phosphate or phosphonite. 3. Способ по п.1, отличающийся тем, что в нем получают производные общей формулы 1, где защитную группу R1 выбирают из группы, содержащей трет-бутилдиметилсилил, триметилсилил, аллилоксикарбонил, п-нитробензилоксикарбонил, и группу R2 выбирают из группы, содержащей аллил, бензил, возможно замещенный метокси- или нитрогруппой, СH2OCO(O)mR4 где R4 представляет C1-6алкильную группу и m равно 0 или 1; органическое основание предпочтительно представляет собой триэтиламин или диизопропилэтиламин, кислоту Льюиса выбирают из группы, содержащей иодид цинка, бромид цинка, хлорид цинка, хлорид алюминия, и органический фосфит или фосфонит представляет собой триметил-, триэтилфосфит или диметоксиметилфосфин.3. The method according to claim 1, characterized in that it produces derivatives of general formula 1, where the protective group R 1 is selected from the group containing tert-butyldimethylsilyl, trimethylsilyl, allyloxycarbonyl, p-nitrobenzyloxycarbonyl, and the group R 2 is chosen from the group containing allyl, benzyl, possibly substituted by a methoxy or nitro group, СH 2 OCO (O) m R 4 where R 4 is a C 1-6 alkyl group and m is 0 or 1; the organic base is preferably triethylamine or diisopropylethylamine, the Lewis acid is selected from the group consisting of zinc iodide, zinc bromide, zinc chloride, aluminum chloride, and the organic phosphite or phosphonite is trimethyl, triethyl phosphite or dimethoxymethylphosphine. 4. Способ по п.1 или 2, отличающийся тем, что 2-галогентиоуксусной кислотой является 2-хлортиоуксусная кислота. 4. The method according to claim 1 or 2, characterized in that the 2-halogenethioacetic acid is 2-chlorothioacetic acid. 5. Способ по п. 3, отличающийся тем, что полученное соединение 1 является соединениeм формулы 1 по п.1, где R1 = трет-бутилдиметилсилил, R2 = аллил, Х = Сl.5. The method according to p. 3, characterized in that the obtained compound 1 is a compound of formula 1 according to claim 1, where R 1 = tert-butyldimethylsilyl, R 2 = allyl, X = Cl. 6. Соединение формулы V
Figure 00000005

где R1 и Х такие, как определено выше.6. The compound of formula V
Figure 00000005

where R 1 and X are as defined above. 7. Соединение формулы VII
Figure 00000006

где R1 и R2 и Х такие, как определено выше.7. The compound of formula VII
Figure 00000006

where R 1 and R 2 and X are as defined above. 8. Соединения по пп.5 и 6, где Х = хлор. 8. Compounds according to claims 5 and 6, where X = chlorine.
RU98117732/04A 1996-02-27 1997-02-19 Method of preparing 2-halogenmethyl penems and 2-azitidinone derivatives as intermediate compounds RU2175971C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITFI96A000033 1996-02-27
IT96FI000033A IT1286558B1 (en) 1996-02-27 1996-02-27 PROCESS FOR THE PREPARATION OF 2-HALOGENOMETHYL-PENEMS AND THEIR USE FOR THE PREPARATION OF ANTIBACTERIAL PENEMS

Publications (2)

Publication Number Publication Date
RU98117732A true RU98117732A (en) 2000-10-20
RU2175971C2 RU2175971C2 (en) 2001-11-20

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RU98117732/04A RU2175971C2 (en) 1996-02-27 1997-02-19 Method of preparing 2-halogenmethyl penems and 2-azitidinone derivatives as intermediate compounds

Country Status (12)

Country Link
US (1) US6153747A (en)
EP (1) EP0883620B1 (en)
CN (1) CN1116298C (en)
AU (1) AU1792397A (en)
CA (1) CA2247269A1 (en)
DE (1) DE69715158T2 (en)
ES (1) ES2180926T3 (en)
IT (1) IT1286558B1 (en)
PL (1) PL328435A1 (en)
RU (1) RU2175971C2 (en)
WO (1) WO1997031922A1 (en)
ZA (1) ZA971471B (en)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1193922B (en) * 1979-02-24 1988-08-31 Erba Farmitalia ANTIBACTERIAL AGENTS AND BETA INHIBITORS - LACTAMASE AND THEIR PREPARATION
GB2118181B (en) * 1982-04-08 1986-07-30 Erba Farmitalia Substituted penem derivatives and new process for their preparation
US4794109A (en) * 1982-11-16 1988-12-27 Ciba-Geigy Corporation 6-hydroxy-lower alkylpenem compounds, pharmaceutical preparations that contain these compounds, and the use of the latter
JPS59152387A (en) * 1983-02-10 1984-08-31 Shionogi & Co Ltd Novel penem compound
GB8321677D0 (en) * 1983-08-11 1983-09-14 Erba Farmitalia Preparation of penems
GB9110507D0 (en) * 1991-05-15 1991-07-03 Smithkline Beecham Plc Chemical compounds

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