RU2000129671A - Производные 3-(амино- или аминоалкил) пиридинона и их применение для лечения болезней, связанных с ВИЧ - Google Patents

Производные 3-(амино- или аминоалкил) пиридинона и их применение для лечения болезней, связанных с ВИЧ

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RU2000129671A
RU2000129671A RU2000129671/04A RU2000129671A RU2000129671A RU 2000129671 A RU2000129671 A RU 2000129671A RU 2000129671/04 A RU2000129671/04 A RU 2000129671/04A RU 2000129671 A RU2000129671 A RU 2000129671A RU 2000129671 A RU2000129671 A RU 2000129671A
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alkyl
pyridinone
amino
substituted
group
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Эмиль БИЗАНИ (FR)
Эмиль БИЗАНИ
Валери ДОЛЛЬ (FR)
Валери ДОЛЛЬ
Чи Хунг НГУЙЕН (FR)
Чи Хунг НГУЙЕН
Клод МОННРЕ (FR)
Клод МОННРЕ
Давид ГРИЕРСОН (FR)
Давид ГРИЕРСОН
Анн-Мари ОБЕРТЕН (FR)
Анн-Мари ОБЕРТЕН
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Сантр Насьональ Де Ля Решерш Сьентифик (Fr)
Сантр Насьональ Де Ля Решерш Сьентифик
Энститю Кюри (Fr)
Энститю Кюри
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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  • Molecular Biology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
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Claims (10)

1. Соединение формулы (1)
Figure 00000001
в которой Q означает -NR1R2 или -R0NR1R2, где R0 означает C1-6-алкандиил, R1 и R2 независимо означают C1-6-алкил или С3-6-алкенил; причем C1-6-алкил и С3-6-алкенил могут быть замещены одним, двумя или тремя заместителями, выбранными из гидрокси, C1-4-алкилокси, C1-4-алкилтио, арилокси, арилтио, амино, моно- или ди(С1-4-алкил) амино и арильной групп, или же R1 и R2 вместе могут образовывать двухвалентный радикал -R1-R2-, представляющий собой - (СН2)2-O-(СН2)2-, -(CH2)2-NR7-(СН2)2-, -(CH2)2-CH(NHR7)-(CH2)2- или -(СН2)n-, где R7 означает водород или C1-4-алкил, а n=2, 3, 4, 5 или 6;
R3 означает арил или моноциклический или бициклический гетероцикл, выбранный из пиридинила, пиримидинила, тиазолинила, фуранила, тиенила, имидазолила, бензоксазолила, бензотиазолила и бензимидазолила, причем эти моноциклические или бициклические гетероциклы необязательно могут быть замещены одним, двумя или тремя заместителями, независимо выбранными из гидрокси, C1-4-алкила, C1-4-алкокси, галоида, трифторометила, диметиленокси или фенильной групп; R4 и R5 независимо означают водород, C1-6-алкил, С3-6-алкенил, C1-4-алкокси, С1-4-алкилокси-С1-4-алкил, амино, моно- или ди(С1-4-алкил) амино, формил, C1-4-алкилкарбонил, карбоксил, C1-4-алкилоксикарбонил или C1-4-алкиламинокарбонил, где C1-6-алкил и С3-6-алкенил могут быть замещены одним, двумя или тремя заместителями, выбранными из гидрокси, C1-4-алкилокси, C1-4-алкилтио, арилокси, арилтио, амино, моно- или ди (C1-4-алкил) амино и арильной групп, или же R4 и R5 вместе образуют двухвалентный радикал формулы -R4-R5-, представляющий собой -СН=СН-СН=СН- или -(CH2)t-, где t=3 или 4;
R6 означает водород, гидрокси, C1-4-алкилокси, C1-6-алкил, С3-6-алкенил, арил, C1-4-алкил, амино, моно- или ди(С1-4-алкил) амино или алкиларил;
Y означает О или S;
Х означает радикал формулы
-(СН2)р- (а) или
-(CH2)q-Z-(CH2)r- (b)
где р=1, 2, 3, 4 или 5;
q=0, 1, 2, 3, 4 или 5;
r=0, 1, 2 или 3;
Z означает NR8, C=O, CHOH, CHNR8R9, CF2, О, S или СН=СН, где R8 и R9 независимо представляют собой водород или C1-4-алкил;
“арил” означает фенил или замещенный фенил с одним, двумя или тремя заместителями, выбранными из C1-4-алкила, C1-4-алкилокси, галоида и трифторометильной группы, или N-оксиды,
их стереохимические изомерные формы или фармацевтически приемлемые комплексные соли.
2. Соединение по п.1, в котором R1 и R2 означают метильную группу.
3. Соединение по п.1, в котором Х означает -СН2-,R3 представляет собой фенильную группу, замещенную двумя метильными группами.
4. Соединение по п.1, представляющее собой 3-диметиламино-4-(3,5-диметилбензил)-5-этил-6-метилпиридин-2 (1Н)-он.
5. Соединение по п.1 для производства фармацевтической композиции для лечения заболеваний, связанных с ВИЧ.
6. Соединение по п.1 для производства фармацевтической композиции для лечения ВИЧ-инфекции.
7. Способ получения соединений по п.1, где Х представляет собой -СН2-, Y означает О, R3 является необязательно замещенной фенильной группой, R6 -водород, включающий следующие стадии: a) взаимодействие пиридина (2), замещенного в положении 2 алкоксигруппой, в положении 3 амидоалкильной группой, с C1-C6 алкиллитием, с получением литиевого производного пиридина, b) превращение литиевого производного в медьорганический реагент путем реакции его с комплексом, образованным CuI и диметилсульфидом, c) получение пиридинона, имеющего защитные группы, путем реакции медьорганического реагента с необязательно замещенным бензилгалидом, d) гидролиз пиридинона, имеющего защитные группы, и получение пиридинона, лишенного защитных групп, e) замещение 3-аминогруппы лишенного защитных групп пиридинона, и получение требуемого соединения пиридинона.
8. Способ получения соединений по п.1, где Х представляет собой -С=О, Y представляет О, R3 является необязательно замещенной фенильной группой, R6 -водород, включающий a) взаимодействие пиридина, замещенного в положении 2 алкоксигруппой, в положении 3 амидоалкильной группой, с C1-С6 алкиллитием, с получением литиевого производного пиридина, b) взаимодействие литиевого производного с необязательно замещенным бензальдегидом, с получением замещенного пиридинона, c) окисление указанного замещенного пиридинона, с образованием пиридинона, имеющего защитные группы, d) удаление защитных групп, введенных в пиридинон, путем гидролиза с образованием требуемого соединения пиридинона.
9. Литиевое производное, имеющее следующую формулу:
Figure 00000002
в которой R4 и R5 определены в п.1 R10 и R11 независимо являются C1-С6-алкилами.
10. Фармацевтическая композиция, включающая терапевтически эффективное количество по крайней мере одного соединения по п.1 и фармацевтически применимые носители.
RU2000129671/04A 1998-04-27 1999-04-27 Производные 3-(амино- или аминоалкил) пиридинона и их применение для лечения болезней, связанных с ВИЧ RU2000129671A (ru)

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EP1073637B1 (en) 2006-08-02
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US6683079B2 (en) 2004-01-27
PL343685A1 (en) 2001-08-27
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WO1999055676A1 (en) 1999-11-04
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