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RU2011120822A - METHOD FOR PRODUCING SUBSTITUTED PHENYLALANINES - Google Patents

METHOD FOR PRODUCING SUBSTITUTED PHENYLALANINES Download PDF

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Publication number
RU2011120822A
RU2011120822A RU2011120822/04A RU2011120822A RU2011120822A RU 2011120822 A RU2011120822 A RU 2011120822A RU 2011120822/04 A RU2011120822/04 A RU 2011120822/04A RU 2011120822 A RU2011120822 A RU 2011120822A RU 2011120822 A RU2011120822 A RU 2011120822A
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RU
Russia
Prior art keywords
compound
formula
arylalkyl
salt
heterocycle
Prior art date
Application number
RU2011120822/04A
Other languages
Russian (ru)
Inventor
Хью Альфред Бергун
Раманаиах К. Канамарлапуди
Айан Фрейзер ПИКЕРСДЖИЛЛ
Чжи-Цай Ши
Вэньсюэ У
Хаймин Чжан
Мэттью Манчжу Чжао
Original Assignee
Лексикон Фармасьютикалз, Инк.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by Лексикон Фармасьютикалз, Инк. filed Critical Лексикон Фармасьютикалз, Инк.
Publication of RU2011120822A publication Critical patent/RU2011120822A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1. Способ получения первого соединения формулыили его соли, включающий контактирование второго соединения формулыс третьим соединением формулыи основанием в растворе, где в указанных формулахРпредставляет собой R, арилалкил, гетероарилалкил или -C(O)R;Рпредставляет собой арилалкил, гетероарилалкил или -C(O)R;Rпредставляет собой водород или необязательно замещенный алкил, алкиларил, алкилгетероцикл, арил или гетероцикл; икаждый Rпредставляет собой независимо алкил, арилалкил, арил, гетероцикл, алкокси, арилокси или арилалкокси.2. Способ по п.1, где Рпредставляет собой водород.3. Способ по п.1, где Рпредставляет собой трет-бутоксикарбонил (Вос).4. Способ по п.1, где основание представляет собой карбонат цезия.5. Способ по п.1, где раствор включает диоксан.6. Способ получения соединения формулыили его соли, включающий контактирование первого соединения по п.1 с кислотой.7. Соединение формулыили его соль.8. Соединение формулыили его соль.9. Способ получения соединения по п.8, включающий контактирование соединения формулыс 2-амино-4,6-дихлорпиримидином в условиях восстановления.10. Соединение формулыили его соль, где в указанной формулеРпредставляет собой R, арилалкил, гетероарилалкил или -C(O)R;Рпредставляет собой арилалкил, гетероарилалкил или -C(O)R;Rпредставляет собой водород или необязательно замещенный алкил, алкиларил, алкилгетероцикл, арил или гетероцикл; икаждый Rпредставляет собой независимо алкил, арилалкил, арил, гетероцикл, алкокси, арилокси или арилалкокси.11. Соединение по п.10, которое представляет собой соединение формулы1. A method for preparing a first compound of the formula or its salt, comprising contacting a second compound of the formula with a third compound of the formula and a base in a solution, where in these formulas P is R, arylalkyl, heteroarylalkyl or -C (O) R; P is arylalkyl, heteroarylalkyl or -C (O ) R; R is hydrogen or an optionally substituted alkyl, alkylaryl, alkylheterocycle, aryl or heterocycle; and each R 2 is independently alkyl, arylalkyl, aryl, heterocycle, alkoxy, aryloxy, or arylalkoxy. 2. The method of claim 1, wherein P is hydrogen. The method of claim 1, wherein P is tert-butoxycarbonyl (Boc). 4. The method of claim 1, wherein the base is cesium carbonate. The method of claim 1, wherein the solution comprises dioxane. 6. A method for preparing a compound of the formula or its salt, comprising contacting the first compound according to claim 1 with an acid. A compound of the formula or a salt thereof. 8. A compound of the formula or its salt. 9. A method for preparing a compound according to claim 8, comprising contacting a compound of the formula with 2-amino-4,6-dichloropyrimidine under reduction conditions. A compound of the formula or a salt thereof, wherein, in said formula, P is R, arylalkyl, heteroarylalkyl, or —C (O) R; P is arylalkyl, heteroarylalkyl, or —C (O) R; R is hydrogen or an optionally substituted alkyl, alkylaryl, alkylheterocycle heterocycle; and each R is independently alkyl, arylalkyl, aryl, heterocycle, alkoxy, aryloxy, or arylalkoxy. 11. A compound according to claim 10, which is a compound of the formula

Claims (11)

1. Способ получения первого соединения формулы1. The method of obtaining the first compound of the formula
Figure 00000001
,
Figure 00000001
, или его соли, включающий контактирование второго соединения формулыor its salt, comprising contacting a second compound of the formula
Figure 00000002
Figure 00000002
 с третьим соединением формулыwith the third compound of the formula
Figure 00000003
Figure 00000003
 и основанием в растворе, где в указанных формулахand a base in solution, where in these formulas Р1 представляет собой R1, арилалкил, гетероарилалкил или -C(O)R13;P 1 represents R 1 , arylalkyl, heteroarylalkyl or —C (O) R 13 ; Р2 представляет собой арилалкил, гетероарилалкил или -C(O)R13;P 2 represents arylalkyl, heteroarylalkyl or —C (O) R 13 ; R1 представляет собой водород или необязательно замещенный алкил, алкиларил, алкилгетероцикл, арил или гетероцикл; иR 1 represents hydrogen or optionally substituted alkyl, alkylaryl, alkyl heterocycle, aryl or heterocycle; and каждый R13 представляет собой независимо алкил, арилалкил, арил, гетероцикл, алкокси, арилокси или арилалкокси.each R 13 is independently alkyl, arylalkyl, aryl, heterocycle, alkoxy, aryloxy or arylalkoxy. 2. Способ по п.1, где Р1 представляет собой водород.2. The method according to claim 1, where P 1 represents hydrogen. 3. Способ по п.1, где Р2 представляет собой трет-бутоксикарбонил (Вос).3. The method according to claim 1, where P 2 represents tert-butoxycarbonyl (Boc). 4. Способ по п.1, где основание представляет собой карбонат цезия.4. The method according to claim 1, where the base is cesium carbonate. 5. Способ по п.1, где раствор включает диоксан.5. The method according to claim 1, where the solution comprises dioxane. 6. Способ получения соединения формулы6. A method of obtaining a compound of the formula
Figure 00000004
Figure 00000004
 или его соли, включающий контактирование первого соединения по п.1 с кислотой.or its salt, comprising contacting the first compound according to claim 1 with an acid. 7. Соединение формулы7. The compound of the formula
Figure 00000002
Figure 00000002
 или его соль.or its salt. 8. Соединение формулы8. The compound of the formula
Figure 00000005
Figure 00000005
 или его соль.or its salt. 9. Способ получения соединения по п.8, включающий контактирование соединения формулы9. A method of producing a compound of claim 8, comprising contacting a compound of the formula
Figure 00000006
Figure 00000006
 с 2-амино-4,6-дихлорпиримидином в условиях восстановления. with 2-amino-4,6-dichloropyrimidine under reduced conditions. 10. Соединение формулы10. The compound of the formula
Figure 00000007
Figure 00000007
 или его соль, где в указанной формулеor its salt, where in the specified formula Р1 представляет собой R1, арилалкил, гетероарилалкил или -C(O)R13;P 1 represents R 1 , arylalkyl, heteroarylalkyl or —C (O) R 13 ; Р2 представляет собой арилалкил, гетероарилалкил или -C(O)R13;P 2 represents arylalkyl, heteroarylalkyl or —C (O) R 13 ; R1 представляет собой водород или необязательно замещенный алкил, алкиларил, алкилгетероцикл, арил или гетероцикл; иR 1 represents hydrogen or optionally substituted alkyl, alkylaryl, alkyl heterocycle, aryl or heterocycle; and каждый R13 представляет собой независимо алкил, арилалкил, арил, гетероцикл, алкокси, арилокси или арилалкокси.each R 13 is independently alkyl, arylalkyl, aryl, heterocycle, alkoxy, aryloxy or arylalkoxy. 11. Соединение по п.10, которое представляет собой соединение формулы11. The compound of claim 10, which is a compound of the formula
Figure 00000008
.
Figure 00000008
.
RU2011120822/04A 2008-10-24 2008-10-24 METHOD FOR PRODUCING SUBSTITUTED PHENYLALANINES RU2011120822A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2008/081054 WO2010047712A1 (en) 2008-10-24 2008-10-24 Process for the preparation of substituted phenylalanines

Publications (1)

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EP (1) EP2358685A1 (en)
JP (1) JP2012506427A (en)
KR (1) KR20110074875A (en)
CN (1) CN102203069A (en)
AU (1) AU2008363274A1 (en)
BR (1) BRPI0823136A2 (en)
CA (1) CA2741563A1 (en)
IL (1) IL211996A0 (en)
MX (1) MX2011004168A (en)
RU (1) RU2011120822A (en)
WO (1) WO2010047712A1 (en)

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* Cited by examiner, † Cited by third party
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WO2015089137A1 (en) * 2013-12-11 2015-06-18 Karos Pharmaceuticals, Inc. Acylguanidines as tryptophan hydroxylase inhibitors
SMT202200134T1 (en) 2018-03-08 2022-05-12 Incyte Corp Aminopyrazine diol compounds as pi3k-y inhibitors
US11046658B2 (en) 2018-07-02 2021-06-29 Incyte Corporation Aminopyrazine derivatives as PI3K-γ inhibitors

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* Cited by examiner, † Cited by third party
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CA2635531C (en) * 2005-12-29 2014-06-17 Lexicon Pharmaceutical Inc. Multicyclic amino acid derivatives and methods of their use
UA99270C2 (en) * 2006-12-12 2012-08-10 Лексикон Фармасьютикалз, Инк. 4-phenyl-6-(2,2,2-trifluoro-1-phenylethoxy)pyrimidine-based compounds and methods of their use

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BRPI0823136A2 (en) 2015-06-16
AU2008363274A1 (en) 2010-04-29
JP2012506427A (en) 2012-03-15
EP2358685A1 (en) 2011-08-24
KR20110074875A (en) 2011-07-04
CA2741563A1 (en) 2010-04-29
IL211996A0 (en) 2011-06-30
WO2010047712A1 (en) 2010-04-29
MX2011004168A (en) 2011-05-23
CN102203069A (en) 2011-09-28

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