DK2635551T3 - Fremgangsmåde til fremstilling af substituerede n-(benzyl)cyclopropanaminer ved hjælp af iminhydrering - Google Patents

Fremgangsmåde til fremstilling af substituerede n-(benzyl)cyclopropanaminer ved hjælp af iminhydrering Download PDF

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Publication number
DK2635551T3
DK2635551T3 DK11778894.3T DK11778894T DK2635551T3 DK 2635551 T3 DK2635551 T3 DK 2635551T3 DK 11778894 T DK11778894 T DK 11778894T DK 2635551 T3 DK2635551 T3 DK 2635551T3
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Denmark
Prior art keywords
haloalkyl
general formula
alkyl
benzyl
halogen atoms
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DK11778894.3T
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English (en)
Inventor
Norbert Lui
Wahed Ahmed Moradi
Thomas Norbert Müller
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Bayer Cropscience Ag
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Publication of DK2635551T3 publication Critical patent/DK2635551T3/da

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (5)

1. Fremgangsmåde til fremstilling af N- (benzyl)cyclopropanaminer med den generelle formel (II)
(il) hvor Z er hydrogen, Ci-Cs-alkyl, Ci-C4-halogenalkyl eller C3-C7-cycloalkyl, Xi er halogen eller Ci-Cs-halogenalkyl, der har op til 9 identiske eller forskellige halogenatomer, X er Ci-C8-alkyl eller Ci-Cs-halogenalkyl, der har op til 9 identiske eller forskellige halogenatomer, n er 1, 2, 3 eller 4, der er kendetegnet ved, at N- [(aryl)methylen]cyclopropanaminderivater med den generelle formel (I)
(i) hvor Z, X, Xi og n har betydningerne anført ovenfor, gennemgår katalytisk hydrering, og hvor hydreringskatalysatoren er en platinkatalysator.
2. Fremgangsmåde ifølge krav 1, der er kendetegnet ved, at katalysatoren baseret på den anvendte imin med formel (I) anvendes i en koncentration på ca. 0,01 til ca. 30 vægt-%.
3. Fremgangsmåde til fremstilling af N- [(aryl)methylen]cyclopropanaminderivaterne med den generelle formel (I)
(i) hvor
Z er hydrogen, Ci-Cs-alkyl, Ci-C4-halogenalkyl eller C3-C7-cycloalkyl, Xi er halogen eller Ci-Cs-halogenalkyl, der har op til 9 identiske eller forskellige halogenatomer, X er Ci-C8-alkyl eller Ci-Cs-halogenalkyl, der har op til 9 identiske eller forskellige halogenatomer, n er 1, 2, 3 eller 4, der er kendetegnet ved, at cyclopropylamin kondenseres med carbonylforbindelser med den generelle formel (III)
(III) hvor Z, X, Xi og n har betydningerne anført ovenfor.
4. Fremgangsmåde til fremstilling af N- (benzyl)cyclopropanaminer med den generelle formel (II)
(II) hvor Z er hydrogen, Ci-Cs-alkyl, Ci-C4-halogenalkyl eller C3-C7-cycloalkyl, Xi er halogen eller Ci-Cs-halogenalkyl, der har op til 9 identiske eller forskellige halogenatomer, X er Ci-C8-alkyl eller Ci-Cs-halogenalkyl, der har op til 9 identiske eller forskellige halogenatomer, n er 1, 2, 3 eller 4, der er kendetegnet ved, at cyclopropylamin i et første trin [proces (B)] kondenseres med carbonylforbindelser med den crenerelle formel (III)
(III) hvor Z, X, Xi og n har betydningerne anført ovenfor, og de resulterende N- [ (aryl)methylen]cyclopropanaminderivater
med den generelle formel (I)
(I) hvor Z, X, Xi og n har betydningerne anført ovenfor, gennemgår katalytisk hydrering i et andet trin, hvor hydreringskatalysatoren er en platinkatalysator [proces (A)].
5. N-[(aryl)methylen]cyclopropanaminderivater med den generelle formel (I)
(i) hvor Z er hydrogen, Ci-Cs-alkyl, Ci-C4-halogenalkyl eller C3-C7-cycloalkyl, Xi er halogen eller Ci-Cs-halogenalkyl, der har op til 9 identiske eller forskellige halogenatomer, X er Ci-C8-alkyl eller Ci-Cs-halogenalkyl, der har op til 9 identiske eller forskellige halogenatomer, n er 1, 2, 3 eller 4.
DK11778894.3T 2010-11-05 2011-11-04 Fremgangsmåde til fremstilling af substituerede n-(benzyl)cyclopropanaminer ved hjælp af iminhydrering DK2635551T3 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US41051710P 2010-11-05 2010-11-05
EP10190077 2010-11-05
PCT/EP2011/069426 WO2012059585A1 (en) 2010-11-05 2011-11-04 Process for the preparation of substituted n-(benzyl)cyclopropanamines by imine hydrogenation

Publications (1)

Publication Number Publication Date
DK2635551T3 true DK2635551T3 (da) 2018-08-06

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DK11778894.3T DK2635551T3 (da) 2010-11-05 2011-11-04 Fremgangsmåde til fremstilling af substituerede n-(benzyl)cyclopropanaminer ved hjælp af iminhydrering

Country Status (12)

Country Link
US (1) US9260378B2 (da)
EP (1) EP2635551B1 (da)
JP (1) JP2014503481A (da)
KR (1) KR101874659B1 (da)
CN (1) CN103402970B (da)
BR (1) BR112013010990B1 (da)
DK (1) DK2635551T3 (da)
ES (1) ES2680546T3 (da)
IL (1) IL226132B (da)
MX (1) MX2013004881A (da)
TW (2) TWI622573B (da)
WO (1) WO2012059585A1 (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI630191B (zh) 2012-04-26 2018-07-21 拜耳作物科學公司 用於製備ｎ-（５-氯-２-異丙基苄基）環丙胺之中間體、其製備方法及用途
CN107428675A (zh) * 2015-03-11 2017-12-01 三菱瓦斯化学株式会社 新型多胺化合物及其制造方法，以及使用其的环氧树脂用固化剂、环氧树脂组合物和环氧树脂固化物
JP6711104B2 (ja) * 2015-04-24 2020-06-17 Jsr株式会社 レジスト下層膜形成方法及びパターン形成方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
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US3083226A (en) * 1961-10-18 1963-03-26 Abbott Lab N-benzyl cyclopropylamines and carbamates
US3153093A (en) * 1961-11-22 1964-10-13 Abbott Lab Amino derivatives of nu-cyclopropylbenzylamines
US6252090B1 (en) * 2000-08-29 2001-06-26 Allergan Sales, Inc. Compounds having activity as inhibitors of cytochrome P450RAI
CN1332942C (zh) 2002-10-11 2007-08-22 埃科特莱茵药品有限公司 磺酰基氨基－乙酸衍生物及其作为阿立新受体拮抗剂的应用
GB0428250D0 (en) 2004-12-23 2005-01-26 Novartis Ag Organic compounds
AR056882A1 (es) 2006-02-01 2007-10-31 Bayer Cropscience Sa Derivados del fungicida n- cicloalquil- bencil- amida
MX2009002921A (es) 2006-09-15 2009-04-01 Schering Corp Derivados de azetidinona para el tratamiento de trastornos del metabolismo lipidico.
JP2010503675A (ja) * 2006-09-15 2010-02-04 シェーリング コーポレイション 疼痛、糖尿病および脂質代謝の障害の治療に有用なスピロ縮合アゼチジン誘導体
JP5070067B2 (ja) 2007-01-15 2012-11-07 参天製薬株式会社 ＩκＢキナーゼβ阻害活性を有する新規インドール誘導体
EP2155643B1 (en) * 2007-06-08 2016-08-10 MannKind Corporation Ire-1a inhibitors
SG192543A1 (en) * 2008-05-05 2013-08-30 Merck Canada Inc 3, 4 - substituted piperidine derivatives as renin inhibitors
TWI630191B (zh) * 2012-04-26 2018-07-21 拜耳作物科學公司 用於製備ｎ-（５-氯-２-異丙基苄基）環丙胺之中間體、其製備方法及用途

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Publication number Publication date
EP2635551A1 (en) 2013-09-11
US9260378B2 (en) 2016-02-16
EP2635551B1 (en) 2018-05-02
CN103402970A (zh) 2013-11-20
JP2014503481A (ja) 2014-02-13
IL226132B (en) 2018-02-28
MX2013004881A (es) 2013-07-02
KR20130115290A (ko) 2013-10-21
TW201700451A (zh) 2017-01-01
TW201249780A (en) 2012-12-16
KR101874659B1 (ko) 2018-07-04
IL226132A0 (en) 2013-06-27
BR112013010990A2 (pt) 2016-08-30
US20130217910A1 (en) 2013-08-22
TWI562977B (en) 2016-12-21
CN103402970B (zh) 2017-02-15
TWI622573B (zh) 2018-05-01
BR112013010990B1 (pt) 2019-03-26
WO2012059585A1 (en) 2012-05-10
ES2680546T3 (es) 2018-09-10

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