RU97108157A - ANTIMICROBIAL PHENYLOXAZOLIDINONES - Google Patents

ANTIMICROBIAL PHENYLOXAZOLIDINONES

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Publication number
RU97108157A
RU97108157A RU97108157/04A RU97108157A RU97108157A RU 97108157 A RU97108157 A RU 97108157A RU 97108157/04 A RU97108157/04 A RU 97108157/04A RU 97108157 A RU97108157 A RU 97108157A RU 97108157 A RU97108157 A RU 97108157A
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RU
Russia
Prior art keywords
optionally substituted
alkyl
alkoxy
hydroxy
phenyl
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RU97108157/04A
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Russian (ru)
Other versions
RU2134692C1 (en
Inventor
К.Хатчинсон Дуглас
Р.Барбачян Майкл
Танигути Микио
Мунесада Киетака
Ямада Хироеси
Дж.Брикнер Стивен
Original Assignee
Фармация Энд Апджон Компани
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Priority claimed from PCT/US1995/010992 external-priority patent/WO1996013502A1/en
Publication of RU97108157A publication Critical patent/RU97108157A/en
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Publication of RU2134692C1 publication Critical patent/RU2134692C1/en

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Claims (11)

1. Соединение формулы I
Figure 00000001

или его фармацевтически приемлемые соли, где Q выбирают из формул I, II, III, IV, V:
Figure 00000002

Figure 00000003

Figure 00000004

Figure 00000005

где R1 представляет (a) H или F, (b) OR7, (c) SR7, (d) NR8R9, (e) CN, (f) C1 - C4-алкоксикарбонил, (g) карбоксамид, (h) C1 - C4-ацил, произвольно замещенный одним или более заместителем, выбранным из фтора, гидрокси, C1 - C4-алкокси, C1 - C4-ацилокси; (i) NHO(C1 - C6-алкил), NHOCH2Ph; (j) NSO2R, где R представляет C1 - C6-алкил, произвольно замещенный одним или более F, Cl, C1 - C6-алкокси или фенилом;
каждый R2 независимо выбирают из (a) H или F; (b) OH, (c) OR, где R является C1 - C6-алкилом, (d) C1 - C4-алкила, (e) Ph;
каждый R3 независимо выбирают из (a) H, (b) C1 - C3-алкила, который может быть произвольно замещен F, Cl, гидрокси, C1 - C3-алкоксикарбонилом, C1 - C3-ацилокси, C1 - C3-алкокси или N(C1 - C4-алкил)2, (c) фенила, (d) пиридила;
R4 независимо представляет H, OCH3F или Cl;
R5 представляет (a) водород, (b) C1 - C8-алкил, произвольно замещенный одним или более заместителем, выбранным из F, Cl, гидрокси, C1 - C8-алкокси, C1 - C8-ацилокси, (c) C3 - C6-циклоалкил, (d) амино, (e) C1 - C8-алкиламино, (f) C1 - C8-диалкиламино, (g) C1 - C8-алкокси;
R6 представляет (a) O, (b) S, (c) NR10, (d) CR11R12, (e) (OR)2, где R = C1 - C6-алкил, (f) O(CH2)mO, (g) (SR)2, где R = C1 - C6-алкил, (h) S(CH2)mS, (i) чтобы заполнить валентность OH и H, H и H, H и F или F и F;
R7 представляет (a) водород, (b) C1 - C8-алкил, произвольно замещенный одним или более заместителем, выбранным из F, Cl, -CN, гидрокси, C1 - C8-алкокси, C1 - C8-ацилокси, C1 - C8-алкоксикарбонила, фенила, (c) C1 - C8-ацил, произвольно замещенный одним или более заместителем, выбранным из гидрокси, C1 - C8-алкокси, C1 - C8-ацилокси, (d) C1 - C8-алкоксикарбонил, (e) карбоксамид, произвольно замещенный C1 - C4-алкилом или фенилом на азоте карбоксамида, (f) фенил, произвольно замещенный одним или более заместителем, выбранным из галогена, CN, C1 - C3-алкокси, C1 - C3-алкоксикарбонила, C1 - C4-алкила, произвольно замещенного одним или более F или C1 - C3-алкокси;
R8 и R9 независимо выбирают из (a) H, (b) C1 - C8-алкила, произвольно замещенного одним или более заместителем, выбранным из F, Cl, -CN, гидрокси, C1 - C8-алкокси, C1 - C8-ацилокси, C1 - C8-алкоксикарбонила, фенила, (c) C1 - C8-ацила, произвольно замещенного одним или более заместителем, выбранным из гидрокси, C1 - C8-алкокси, C1 - C8-ацилокси, амино, C1 - C4-ациламино, амино-C1 - C4-ациламино, (d) бензоила, произвольно замещенного одним или более заместителем, выбранным из F, Cl, гидрокси, C1 - C8-алкокси, C1 - C8-ацилокси, амино, C1 - C4-ациламино, C1 - C4-алкоксикарбониламино, (e) C1 - C8-алкоксикарбонила, бензилоксикарбонила, трет-бутоксикарбонила, (f) карбоксамида, произвольно замещенного C1 - C4-алкилом или фенилом на азоте карбоксамида, (g) трифторацетила, (h) CO(C1 - C6-алкил);
R10 представляет (a) H, (b) OR7, (c) NHR7, (d) C1 - C8-алкил, произвольно замещенный фенилом;
R11 и R12 независимо выбирают из (a) H, F, (b) C1 - C4-алкила, произвольно замещенного галогеном, гидрокси, C1 - C4-алкокси, C1 - C4-алкоксикарбонилом, фенилом; (c) C1 - C8-ацила, (d) C1 - C4-алкоксикарбонила, (e) CN;
R17 представляет (a) O, (b) S;
R18 и R19 независимо выбирают из (a) H, (b) C1 - C4-алкила, произвольно замещенного галогеном, гидрокси, C1 - C4-алкокси, (c) OH, (d) C1 - C4-алкокси, произвольно замещенного гидрокси- или C1 - C4-алкокси, (e) NR8R9, (f) -OC(O)C1 - C4-алкила;
R20 представляет (a) H, (b) CH3;
n равен 0 или 1 и m равен 2 или 3.1. The compound of formula I
Figure 00000001

or its pharmaceutically acceptable salts, where Q is selected from formulas I, II, III, IV, V:
Figure 00000002

Figure 00000003

Figure 00000004

Figure 00000005

where R 1 represents (a) H or F, (b) OR 7 , (c) SR 7 , (d) NR 8 R 9 , (e) CN, (f) C 1 - C 4 alkoxycarbonyl, (g) carboxamide, (h) C 1 -C 4 acyl optionally substituted with one or more substituents selected from fluoro, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 acyloxy; (i) NHO (C 1 -C 6 alkyl), NHOCH 2 Ph; (j) NSO 2 R, where R is C 1 -C 6 alkyl optionally substituted with one or more F, Cl, C 1 -C 6 alkoxy or phenyl;
each R 2 is independently selected from (a) H or F; (b) OH, (c) OR, where R is C 1 -C 6 -alkyl, (d) C 1 -C 4 -alkyl, (e) Ph;
each R 3 is independently selected from (a) H, (b) C 1 –C 3 alkyl, which may be optionally substituted with F, Cl, hydroxy, C 1 –C 3 alkoxycarbonyl, C 1 –C 3 acyloxy, C 1 - C 3 alkoxy or N (C 1 - C 4 alkyl) 2 , (c) phenyl, (d) pyridyl;
R 4 independently represents H, OCH 3 F or Cl;
R 5 represents (a) hydrogen, (b) C 1 –C 8 alkyl optionally substituted with one or more substituents selected from F, Cl, hydroxy, C 1 –C 8 alkoxy, C 1 –C 8 acyloxy, (c) C 3 - C 6 cycloalkyl, (d) amino, (e) C 1 - C 8 alkylamino, (f) C 1 - C 8 dialkylamino, (g) C 1 - C 8 alkoxy;
R 6 represents (a) O, (b) S, (c) NR 10 , (d) CR 11 R 12 , (e) (OR) 2 , where R = C 1 is C 6 -alkyl, (f) O (CH 2 ) m O, (g) (SR) 2 , where R = C 1 is C 6 -alkyl, (h) S (CH 2 ) m S, (i) to fill the valencies OH and H, H and H H and F or F and F;
R 7 represents (a) hydrogen, (b) C 1 -C 8 alkyl optionally substituted with one or more substituents selected from F, Cl, -CN, hydroxy, C 1 -C 8 alkoxy, C 1 -C 8 acyloxy, C 1 - C 8 alkoxycarbonyl, phenyl, (c) C 1 - C 8 acyl optionally substituted with one or more substituents selected from hydroxy, C 1 - C 8 alkoxy, C 1 - C 8 acyloxy , (d) C 1 -C 8 alkoxycarbonyl, (e) carboxamide optionally substituted with C 1 -C 4 alkyl or phenyl on carboxamide nitrogen, (f) phenyl optionally substituted with one or more substituents selected from halogen, CN, C 1 - C 3 alkoxy, C 1 - C 3 alkoxycarbon sludge, C 1 -C 4 alkyl optionally substituted with one or more F or C 1 -C 3 alkoxy;
R 8 and R 9 are independently selected from (a) H, (b) C 1 –C 8 alkyl optionally substituted with one or more substituents selected from F, Cl, —CN, hydroxy, C 1 –C 8 alkoxy, C 1 - C 8 acyloxy, C 1 - C 8 alkoxycarbonyl, phenyl, (c) C 1 - C 8 acyl optionally substituted with one or more substituents selected from hydroxy, C 1 - C 8 alkoxy, C 1 - C 8 acyloxy, amino, C 1 - C 4 acylamino, amino C 1 - C 4 acylamino, (d) benzoyl optionally substituted with one or more substituents selected from F, Cl, hydroxy, C 1 - C 8- alkoxy, C 1 - C 8 acyloxy, amino, C 1 - C 4 acylamino, C 1 - C 4 alkoxycarbonylamino, (e) C 1 - C 8 -alkoxycarbonyl, benzyloxycarbonyl, tert-butoxycarbonyl, (f) carboxamide optionally substituted with C 1 - C 4 -alkyl or phenyl on nitrogen of carboxamide, (g) trifluoroacetyl, (h) CO (C 1 - C 6 -alkyl );
R 10 represents (a) H, (b) OR 7 , (c) NHR 7 , (d) C 1 -C 8 alkyl optionally substituted with phenyl;
R 11 and R 12 are independently selected from (a) H, F, (b) C 1 -C 4 alkyl optionally substituted with halogen, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkoxycarbonyl, phenyl; (c) C 1 -C 8 acyl, (d) C 1 -C 4 alkoxycarbonyl, (e) CN;
R 17 represents (a) O, (b) S;
R 18 and R 19 are independently selected from (a) H, (b) C 1 -C 4 alkyl optionally substituted with halogen, hydroxy, C 1 -C 4 alkoxy, (c) OH, (d) C 1 -C 4- alkoxy optionally substituted with hydroxy or C 1 -C 4 alkoxy, (e) NR 8 R 9 , (f) -OC (O) C 1 -C 4 -alkyl;
R 20 represents (a) H, (b) CH 3 ;
n is 0 or 1 and m is 2 or 3. 2. Соединение по п.1, в котором Q представляет структуру (I). 2. The compound according to claim 1, in which Q represents structure (I). 3. Соединение по п.1, в котором Q представляет структуру (II). 3. The compound according to claim 1, in which Q represents structure (II). 4. Соединение по п.1, в котором Q представляет структуру (III). 4. The compound according to claim 1, in which Q represents structure (III). 5. Соединение по п.1, в котором Q представляет структуру (IV). 5. The compound according to claim 1, in which Q represents structure (IV). 6. Соединение по п.1, в котором Q представляет структуру (V). 6. The compound according to claim 1, in which Q represents structure (V). 7. Соединение по п.1, в котором каждый R4 является фтором.7. The compound according to claim 1, in which each R 4 is fluorine. 8. Соединение по п.1, в котором один R4 является фтором и другой является водородом.8. The compound according to claim 1, in which one R 4 is fluorine and the other is hydrogen. 9. Соединение по п.1, в котором R5 является водородом, метокси или метилом.9. The compound according to claim 1, in which R 5 is hydrogen, methoxy or methyl. 10. Соединение по п.1, в котором R6 является кислородом, OCH2CH2O, HOH, NOCH3.10. The compound according to claim 1, in which R 6 is oxygen, OCH 2 CH 2 O, HOH, NOCH 3 . 11. Применение соединения структурной формулы I по п.1 для получения лекарственного средства, полезного для лечения микробных инфекций у теплокровных животных, включая людей, путем введения пациенту фармацевтически эффективного количества соединения. 11. The use of a compound of structural formula I according to claim 1 for the manufacture of a medicament useful for the treatment of microbial infections in warm-blooded animals, including humans, by administering to the patient a pharmaceutically effective amount of the compound.
RU97108157A 1994-10-26 1995-09-12 Antimicrobial phenyloxazolidinones RU2134692C1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US32971794A 1994-10-26 1994-10-26
US08/329,717 1994-10-26
PCT/US1995/010992 WO1996013502A1 (en) 1994-10-26 1995-09-12 Phenyloxazolidinone antimicrobials

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RU97108157A true RU97108157A (en) 1999-06-10
RU2134692C1 RU2134692C1 (en) 1999-08-20

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