EA022785B1 - Стереоселективный синтез производных пиперидина - Google Patents

Стереоселективный синтез производных пиперидина Download PDF

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EA022785B1
EA022785B1 EA201170822A EA201170822A EA022785B1 EA 022785 B1 EA022785 B1 EA 022785B1 EA 201170822 A EA201170822 A EA 201170822A EA 201170822 A EA201170822 A EA 201170822A EA 022785 B1 EA022785 B1 EA 022785B1
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compound
formula
alkyl
heteroaryl
aryl
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Шань-Ень Чоу
Чи-Син Ричард Кинг
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Тайджен Байотекнолоджи Ко., Лтд.
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    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
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    • C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
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    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
    • C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/50—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
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    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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Abstract

Изобретение относится к соединениям динитрила формулы (I), которые применимы для стереоселективного синтеза производных пиперидина, пирролидина и азепана.

Description

Данная заявка на изобретение заявляет приоритет предварительной заявки на патент США № 61/122461, поданной 15 декабря 2008 г. Содержание предшествующей заявки настоящим включается ссылкой во всей своей полноте.
Уровень техники
Пиперидин представляет собой шестичленное циклическое соединение, содержащее пять атомов углерода и один атом азота. Его производные широко используются в качестве структурных элементов при синтезе пиперидинсодержащих органических соединений для фармацевтического и другого использования.
Стереохимическая конфигурация атомов в цикле пиперидина может быть критичной для фармацевтической активности пиперидинсодержащих органических соединений. Таким образом, эффективный и стереоселективный синтез производных пиперидина является крайне важным.
Сущность изобретения
Один аспект данного изобретения относится к соединениям диальдегида или динитрила, которые применимы при получении стереохимически чистых производных пиперидина. Соединения по данному изобретению имеют формулу I
К2 ΝΗΡ1

Claims (14)

  1. ФОРМУЛА ИЗОБРЕТЕНИЯ
    1. Соединение формулы I
    Ρ2 ΝΗΚ χΑ-όχ
    Формула I где К1 представляет собой С(О)ОК, где К представляет собой С1-С6-алкил; К2 представляет собой Н, С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил, С3-С8-циклоалкил, С1-С7-гетероциклоалкил, арил или гетероарил; X представляет собой СЫ и η равно 1 или 2;
    где арил относится к 6-углеродной моноциклической, 10-углеродной бициклической, 14углеродной трициклической ароматической кольцевой системе, гетероарил относится к ароматической 5-8-членной моноциклической, 8-12-членной бициклической или 11-14-членной трициклической кольцевой системе, содержащей один или несколько гетероатомов, выбранных из О, N или 8.
  2. 2. Соединение по п.1, где К2 представляет собой С1-С6-алкил.
  3. 3. Соединение по п.2, где К1 представляет собой С(О)О1-Ви.
  4. 4. Соединение по п.1, где соединение представляет собой ~ ΝΗΚ1
  5. 5. Соединение по п.4, где К1 представляет собой С(О)О1-Ви; К2 представляет собой Н или С1-С6 алкил и η равно 1 или 2.
  6. 6. Соединение по п.4, где соединение представляет собой
    И2 ΝΗΚ1
    ΝΟ ΌΝ
  7. 7. Соединение по п.6, где К1 представляет собой С(О)О1-Ви и К2 представляет собой С1-С6-алкил.
    - 16 022785
  8. 8. Соединение по п.1, где соединение представляет собой
    Ме ΝΗΒοο
  9. 9. Способ получения соединения формулы III, включающий проведение реакции циклизации соединения формулы I
    К2 ΝΗΗ хЛэ^х
    Формула I где К1 представляет собой С(О)ОК, где К представляет собой С1-С6-алкил; К2 представляет собой Н, С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил, С3-С8-циклоалкил, С1-С7-гетероциклоалкил, арил или гетероарил; X представляет собой СN и п равно 1 или 2;
    с соединением формулы II η2νε\
    Формула II где К3 представляет собой Н, С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил, С3-С8-циклоалкил, С3-С7гетероциклоалкил, арил или гетероарил;
    с образованием соединения формулы III !ΎΗίϊΓΝΗρ1
    Формула III где К1, К2, К3 и п являются такими, как определено выше.
  10. 10. Способ по п.9, в котором К1 представляет собой С(О)О!-Ви; К2 представляет собой Н или С3-С6 алкил; К3 представляет собой Н и п равно 1.
  11. 11. Способ по п.9, в котором соединение формулы I представляет собой χΝΗΡ1 и соединение формулы III представляет собой “б
    N
  12. 12. Способ по п.11, в котором К1 представляет собой С(О)О!-Ви; К2 представляет собой Н или С3С6-алкил; К3 представляет собой Н или СН2Рй и п равно 1.
  13. 13. Способ по п.9, дополнительно включающий перед реакцией циклизации соединения формулы I обработку дегидратирующим веществом соединения формулы V
    ΝΗΚ1
    Η,Ν зЛДг о о
    ΝΗ,
    Формула V где К1 представляет собой С(О)ОК, где К представляет собой С1-С6-алкил; К2 представляет собой Н, С1-С6-алкил, С2-С6-алкенил, С2-С6-алкинил, С3-С8-циклоалкил, С1-С7-гетероциклоалкил, арил или гетероарил и п равно 1 или 2, для получения соединения динитрила.
  14. 14. Способ по п.13, в котором соединение динитрила представляет собой соединение формулы V представляет собой
EA201170822A 2008-12-15 2009-12-14 Стереоселективный синтез производных пиперидина EA022785B8 (ru)

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