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RU2002111333A - METHOD FOR PRODUCING 4 '' DERIVATIVES 9-DEOXO-9A-AZA-9A-HOMOERITHROMYCIN A - Google Patents

METHOD FOR PRODUCING 4 '' DERIVATIVES 9-DEOXO-9A-AZA-9A-HOMOERITHROMYCIN A

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Publication number
RU2002111333A
RU2002111333A RU2002111333/04A RU2002111333A RU2002111333A RU 2002111333 A RU2002111333 A RU 2002111333A RU 2002111333/04 A RU2002111333/04 A RU 2002111333/04A RU 2002111333 A RU2002111333 A RU 2002111333A RU 2002111333 A RU2002111333 A RU 2002111333A
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Russia
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formula
compound
interaction
compounds
temperature
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RU2002111333/04A
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Russian (ru)
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RU2233287C2 (en
Inventor
Константин СКЛАВОУНОС
Джон Ллойд ТАКЕР
Лулин ВЕЙ
Керри Питер мл. МЭЙХОН
Филип Дитрих ХАММЕН
Джоанна Тереза Негри
Ричард Шелтон ЛЕНЕР
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Пфайзер Продактс Инк.
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Claims (15)

1. Способ получения соединения формулы 11. The method of obtaining the compounds of formula 1
Figure 00000001
Figure 00000001
 или его фармацевтически приемлемой соли, который включает: взаимодействие соединения формулы 2or its pharmaceutically acceptable salt, which includes: the interaction of the compounds of formula 2 с амином формулы HNR8R15, в органическом растворителе, содержащем изопропанол; где взаимодействие проводят при температуре, по крайней мере, около 40°С;with an amine of formula HNR 8 R 15 in an organic solvent containing isopropanol; where the interaction is carried out at a temperature of at least about 40 ° C; гдеWhere R3 представляет собой –CH2NR8R15;R 3 represents –CH 2 NR 8 R 15 ; R8 представляет собой C1-С10 алкил; иR 8 represents C 1 -C 10 alkyl; and R15представляет собой Н или C1-С10 алкил.R 15 represents H or C 1 -C 10 alkyl. 2. Способ по п.1, где органическим растворителем является изопропанол.2. The method according to claim 1, where the organic solvent is isopropanol. 3. Способ по п.1, где R8 представляет собой пропил, а R15 представляет собой Н.3. The method according to claim 1, where R 8 represents propyl and R 15 represents N. 4. Способ по п.1, который включает в себя получение соединение формулы 1а4. The method according to claim 1, which includes obtaining a compound of formula 1a
Figure 00000003
Figure 00000003
 или его фармацевтически приемлемой соли, путем взаимодействия соединения формулы с н-пропиламином в органическом растворителе, содержащем изопропанол;or a pharmaceutically acceptable salt thereof, by reacting a compound of the formula with n-propylamine in an organic solvent containing isopropanol; где взаимодействие проводят при температуре, по крайней мере, около 40°С.where the interaction is carried out at a temperature of at least about 40 ° C. 5. Способ по п.1, где температура ниже 95°С.5. The method according to claim 1, where the temperature is below 95 ° C. 6. Способ по п.5, где температура находится в области от около 50°С до около 76°С.6. The method according to claim 5, where the temperature is in the region from about 50 ° C to about 76 ° C. 7. Способ по п.1, где взаимодействие проводят при атмосферном давлении.7. The method according to claim 1, where the interaction is carried out at atmospheric pressure. 8. Способ по п.1, где молярное количество амина, по крайней мере, в пять раз больше, чем молярное количество соединения формулы 1.8. The method according to claim 1, where the molar amount of the amine is at least five times greater than the molar amount of the compound of formula 1. 9. Способ по п.1, который дополнительно включает кристаллизацию соединения формулы 1 в виде свободного основания.9. The method according to claim 1, which further comprises crystallizing the compound of formula 1 as a free base. 10. Способ получения соединения формулы 210. The method of obtaining the compounds of formula 2
Figure 00000004
Figure 00000004
 который включает в себя: (а) взаимодействие свободного основания соединения формулы 3which includes: (a) interaction of the free base of the compounds of formula 3
Figure 00000005
Figure 00000005
 с ионом метилида сульфония; (b) гашение реакционной смеси со стадии (а) водным раствором слабой кислоты и распределение продукта в неводном растворе; и (c) удаление защитных групп продукта со стадии (Ь) с получением соединения формулы 2; где R4 представляет собой гидроксизащитную группу.with sulfonium methylide ion; (b) quenching the reaction mixture from step (a) with an aqueous solution of a weak acid and distributing the product in a non-aqueous solution; and (c) removing the protective groups of the product from step (b) to give a compound of formula 2; where R 4 represents a hydroxy protecting group. 11. Способ по п.10 где R4 представляет собой безилоксикарбонил.11. The method according to claim 10, wherein R 4 is becyloxycarbonyl. 12. Способ по п.10, где соединение формулы 3 в виде свободного основания получали из соли добавления кислоты соединения формулы 3.12. The method according to claim 10, where the compound of formula 3 in the form of a free base was obtained from an acid addition salt of a compound of formula 3. 13. Способ по п.10, где соль добавления кислоты соединения формулы 3 представляет собой соль добавления трифторуксусной кислоты.13. The method of claim 10, wherein the acid addition salt of the compound of formula 3 is a trifluoroacetic acid addition salt. 14. Способ по п.11, где стадия (с) включает каталитическое гидрирование.14. The method according to claim 11, where stage (C) includes catalytic hydrogenation. 15. Соединение формулы 215. The compound of formula 2
Figure 00000006
Figure 00000006
 которое представляет собой моногидрат.which is a monohydrate.
RU2002111333/04A 2001-04-27 2002-04-26 Method for preparing 4''-substituted derivatives of 9-deoxo-9a-aza-9a-homoerythromycin a RU2233287C2 (en)

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