EP1771434A2 - Procede pour produire des derives de 3-amino-5-(hydroxymethyl)cyclopentane-1,2-diols - Google Patents

Procede pour produire des derives de 3-amino-5-(hydroxymethyl)cyclopentane-1,2-diols

Info

Publication number
EP1771434A2
EP1771434A2 EP05706975A EP05706975A EP1771434A2 EP 1771434 A2 EP1771434 A2 EP 1771434A2 EP 05706975 A EP05706975 A EP 05706975A EP 05706975 A EP05706975 A EP 05706975A EP 1771434 A2 EP1771434 A2 EP 1771434A2
Authority
EP
European Patent Office
Prior art keywords
formula
mirror image
acid
acetyl
compounds
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP05706975A
Other languages
German (de)
English (en)
Inventor
Gareth-John Griffiths
Silvia Lange
Walter Brieden
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lonza AG
Original Assignee
Lonza AG
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.)
Filing date
Publication date
Application filed by Lonza AG filed Critical Lonza AG
Priority to EP05706975A priority Critical patent/EP1771434A2/fr
Publication of EP1771434A2 publication Critical patent/EP1771434A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
    • C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D419/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems

Definitions

  • the invention relates to a process for the preparation of acetals and ketals of 3-amino-5- (hydroxymethyl) cyclopentane-1,2-diols, and their derivatives and salts of organic acids such as 2,3-isopropylidenedioxy-4- (methoxymethyl) cyclopentan-1-amine hydrogen oxalate, starting from 2-acetyl-2-azabicyclo [2.2.1] hept-5-en-3-one of the formula
  • enantiomerically pure compounds are understood to mean mixtures of enantiomers with an enantiomeric excess (ee) of at least 90%.
  • Ci -e-alkyl is understood below to mean a linear or branched aliphatic alkyl group having 1 to 6 carbon atoms, such as, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl.
  • C 3-8 cycloalkyl is an alicyclic alkyl group with 3 to 8
  • a solution or suspension of at least one organic compound in any mixture is made from an alcoholic solution or suspension
  • the process is equally suitable for producing enantiomerically pure compounds or mixtures of any enantiomer composition.
  • the enantiomer not shown in each case, is said to be in the Structural formula representations can also be included by adding “and / or mirror image” or “or mirror image”.
  • Substituted cyclopentylamines such as (1R, 2S, 3R, 4R) -2,3-isopropylidendioxy- 4- (methoxymethyl) cyclopentan-l-amine hydrochloride, are intermediates for the production of pharmaceutically active adenosine motifsates, which among other things for the treatment of coronary arteries Circulatory disorders, heart failure and high blood pressure can be used (US-A-5364862 and WO-A-95/28160).
  • WO-A-00/23447 turns (-) - 5,6-isopropylidenedioxy-2-azabicyclo [2.2.1] heptan-3-one into a correspondingly protected product using the very expensive and hydrolysis-sensitive compound di-tert-butyl dicarbonate Implemented N-BOC derivative.
  • the synthesis of the starting material (compound of the formula vi) starting from 5,6-dihydroxy-2-azabicyclo- [2.2.1] heptan-3-one is disclosed in WO-A-95/28160.
  • the BOC protective group is cleaved off using HCl gas.
  • hydrochlorides are obtained which, however, are not specified in terms of purity, yield or chemical-physical properties. The substances obtained are used directly in the next synthesis stages without further processing.
  • the process according to the invention can be carried out using (-) - 2-acetyl-2-azabicyclo [2.2.1] hept-5-en-3-one or (+) - 2-acetyl-2-azabicyclo [2.2.1] hept-5 -en-3-one, and any mixture thereof.
  • the process uses conventional and inexpensive protective group technology. Compared to the BOC protective group used in the prior art, the use of the acetyl protective group in the process according to the invention is characterized by easier handling.
  • the acetyl group can easily be removed again in an alkaline hydrolysis step, while the process from WO-A-98/01426 relies on the use of HCl gas for the elimination of the BOC protective group.
  • the method according to the invention represents a significant step forward.
  • the salts which can be prepared by the process according to the invention can in principle be obtained from the anion exchange and reprecipitation corresponding hydrochlorides can be obtained.
  • they are not available as a direct hydrolysis product from the N-BOC compound mentioned in WO-A 00/23447, since the BOC protective group must first be split off with a strong acid.
  • the reprecipitation of an HCl acid salt with an organic acid is not favored.
  • a compound of the formula III is converted into a ketal or acetal by reaction with a ketone or an aldehyde of the formula R 2 -CO-R 3 or by reaction with 2,2-dimethoxypropane or 2,2-dimethoxybutane of the formula
  • R 1 , R 2 and R 3 have the meanings given.
  • DMAP 4-dimethylaminopyridine
  • the cw-hydroxylation of the double bond is carried out using an inorganic oxidizing agent such as, for example, osmium tetraoxide, potassium osmate or potassium permanganate.
  • an inorganic oxidizing agent such as, for example, osmium tetraoxide, potassium osmate or potassium permanganate.
  • the hydroxylation is carried out in a further preferred embodiment using a 2 to 10% aqueous solution of osmium tetraoxide or with osmium tetraoxide fixed on an organic or inorganic support.
  • osmium tetraoxide is used in an amount of 0.1 to 2 mol% with respect to 2-acetyl-2-azabicyclo [2.2.1] hept-5-en-3-one, preferably in an amount of 0.2 up to 0.9 mol%.
  • the osmium tetraoxide can advantageously be regenerated during the reaction in the presence of at least one organic N-oxide such as N-4-methylmorpholine-N-4-oxide and / or a secondary or tertiary amine and at least one inorganic oxidizing agent such as hydrogen peroxide.
  • organic N-oxide such as N-4-methylmorpholine-N-4-oxide and / or a secondary or tertiary amine
  • at least one inorganic oxidizing agent such as hydrogen peroxide.
  • Suitable co-oxidants for the regeneration of osmium tetraoxide during the reaction are sterically demanding N-oxides such as N-4-methylmorpholine-N-4-oxide, di- and trialkylamine N-oxides such as trimethylamine-N-oxide, or mixtures of the above secondary and tertiary amines with organic or inorganic oxidizing agents such as tert-butyl hydroperoxide, magnesium monoperoxyphthalate, 3-chloroperbenzoic acid, hydrogen peroxide, sodium and / or potassium perchlorate, periodate or permanganate.
  • N-oxides and mixtures of the amines mentioned with hydrogen peroxide is particularly preferred.
  • enantiomerically pure (-) - 2-acetyl-2-azabicyclo [2.2.1] hept-5-en-3-one is obtained by cw-hydroxylation with osmium tetraoxide in (1R, 4S, 5R, 6S) -2 acetyl-5,6-dihydroxy-2-azabicyclo [2.2. l] heptan-3-one of the formula
  • the acetal or ketal formation is carried out with acid catalysis.
  • sulfuric acid and / or p-toluenesulfonic acid are used for acid catalysis.
  • the (1 R, 4S, 5R, 6S) -2-acetyl-5,6-di-hydroxy-2-azabicyclo [2.2.1] heptan-3-one is reacted with acetone or 2, 2-Dimethoxypropane in the (IS, 2R, 6S, 7R) -8-acetyl-4,4-dimethyl-3,5-dioxa-8-azatricyclo [5.2.1.0 2,6 ] decan-9-one ( IVa) transferred.
  • the reducing ring opening is carried out with a complex metal hydride such as LiBH 4 , NaBH 4 , NaAlH 2 (OCH 2 CH 2 OCH 3 ) 2 or LiAlIL, preferably with NaBFL ;.
  • a complex metal hydride such as LiBH 4 , NaBH 4 , NaAlH 2 (OCH 2 CH 2 OCH 3 ) 2 or LiAlIL, preferably with NaBFL ;.
  • the (IS, 2R, 6S, 7R) -8-acetyl-4,4-dimethyl-3,5-dioxa-8-azatricyclo [5.2.1.0 '] decan-9-one by reaction with a complex metal hydride in the (lR, 2S, 3R, 4R) -N- [2,3-isopropylidendioxy-4- (hydroxymethyl) cyopentan-l-yl] acetic acid amide of the formula
  • the formation of the ether of the formula VI with R methyl with DMS in acetone is carried out in the presence of a strong base, for example NaOH and / or KOH, particularly preferably with a water content of less than 1%, based on the solvent ,
  • a strong base for example NaOH and / or KOH, particularly preferably with a water content of less than 1%, based on the solvent ,
  • the ether formation is carried out with a C I - O - alkyl or C 3 - cycloalkyl halide in the presence of AgOH.
  • the (IR, 2S, 3R, 4R) -N- [2,3-isopropylidene-dioxy-4- (hydroxymethyl) cyclopentan-1-yl] acetic acid amide is reacted with DMS or methyl iodide in the (IR , 2S, 3R, 4R) -N- [2,3-isopropylidenedioxy-4- (methoxymethyl) cyclopentan-1-yl] acetic acid amide
  • the alkaline hydrolysis is carried out with at least one alkali metal or alkaline earth metal hydroxide, selected from the group consisting of LiOH, ⁇ aOH, KOH, Mg (OH) 2 , Ca (OH) and Ba (OH) 2 , in aqueous and / or alcoholic solution or suspension.
  • at least one alkali metal or alkaline earth metal hydroxide selected from the group consisting of LiOH, ⁇ aOH, KOH, Mg (OH) 2 , Ca (OH) and Ba (OH) 2 , in aqueous and / or alcoholic solution or suspension.
  • the alkaline hydrolysis is carried out at a pressure from 1 to 10 bar, particularly preferably from 1 to 2 bar, and at temperatures from 50 to 150 ° C., particularly preferably from 80 to 100 ° C.
  • the alkaline hydrolysis is carried out with ⁇ aOH and / or KOH in methanolic and / or ethanolic solution, at a pressure of 1 to 2 bar and at a temperature of 80 to 100 ° C.
  • alkaline hydrolysis with NaOH and / or KOH in methanolic and / or ethanolic solution preferably under a pressure of 1 to 2 bar and temperatures of 80 to 100 ° C.
  • the (IR, 2S, 3R, 4R) -N- [2,3-isopropylidenedioxy-4- (hydroxymethyl) cyclopentan-l-yl] acetic acid amide into the (IR, 2S, 3R, 4R) -2,3-isopropylidenedioxy-4- (hydroxymethyl) cyclo- pentan-1-amine or
  • the salt formation in the optional final reaction step with an organic acid selected from the group consisting of crystal water-free or crystal water-containing oxalic acid, (+) -, (-) - or meso-tartaric acid, (+) - or (-) - Malic acid, tartronic acid, mesoxalic acid and oxaloacetic acid are carried out.
  • salt formation is carried out with oxalic acid which is free of water of crystallization or contains water of crystallization, (+) -, (-) - or meso-tartaric acid, (+) - or (-) - malic acid.
  • the compounds (1 R, 2S, 3R, 4R) -2,3-isopropylidenedioxy-4- (hydroxymethyl) cyclopentane-1-amine or (1R, 2S, 3R, 4R) -2.3 -Isopropylidendioxy-4- (methoxymethyl) cyclopentan-l-amine converted into the corresponding hydrogen oxalates.
  • the invention also relates to compounds of the formula
  • the invention also includes compounds of the formula
  • the invention also includes compounds of the formula
  • the invention also includes salts of dibasic and triphasic organic acids of compounds of the formula
  • the mixture was then extracted with ethyl acetate (4 ⁇ 670 L) and the combined organic phases were concentrated at 30 to 200 mbar and a temperature of below 45 ° C. After the internal temperature had risen above 45 ° C. at 30 to 50 mbar, the distillation was stopped and 620 L of methanol were added to the residue. At 200 mbar and an internal temperature of 30 ° C, ethyl acetate and methanol up to a total of 400 L were distilled off. The reaction solution was cooled to room temperature and then directly to the next step to prepare [IS, 2R, 6S, 7R] -8-acetyl- used.
  • reaction solution was heated at 50 ° C for 1 hour, then cooled to 35 ° C and with
  • reaction solution was cooled to room temperature and ethanol was distilled off at 100 mbar and a temperature below 45.degree. 180 L of water were added to the residue and the remaining amount of ethanol was distilled off. After the distillation, there was about 270 L of reaction mixture in the reactor, which was mixed with 140 L of water and then extracted with MTBE (2 ⁇ 145 L). The combined organic phases were used directly for the preparation of (1R, 2S, 3R, 4R) -2,3-isopropylidene-dioxy-4- (methoxymethyl) cyclopentane-1-amine hydrogen oxalate.
  • the (1R, 2S, 3R, 4R) -2,3-isopropylidenedioxy-4- (methoxymethyl) cyclopentane described in Example 5 was placed in a 630 L agitator (enamelled steel) in an initial charge of 23.3 kg of oxalic acid and 210 L of ethanol -l-amine solution metered in over 30 minutes. After 60% had been added, the solution was inoculated by adding a little (1R, 2S, 3R, 4R) -2,3-isopropylidendioxy-4- (methoxymethyl) cyclopentane-1-amine hydrogen oxalate. The precipitated product was centrifuged off and washed with MTBE / ethanol (60:40) (2 ⁇ 120 L).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un procédé pour produire des acétals et des cétals de 3-amino-5-(hydroxyméthyl)cyclopentane-1,2-diols de formule (I) (et/ou image spéculaire), dans laquelle R<1> représente hydrogène, alkyle C1-6, cycloalkyle C3-8 ou benzyle, et dans laquelle i) R<2> représente méthyle et R<3> représente éthyle, ii) R<2> représente hydrogène et R<3> représente alkyle C1-6 ou phényle ou iii) R<2> et R<3> représentent conjointement un groupe de formule -(CH2)n-, n = 4 à 6, ainsi que les amines libres ou sels de diacides ou de triacides organiques, à partir de 2-acétyl-2-aza-bicyclo[2.2.1]hept-5-èn-3-one de formule (II) (et/ou image spéculaire). Indépendamment de la composition de l'éduit, ce procédé est approprié aussi bien pour la production de composés énantiomériquement purs que pour la production de mélanges présentant une composition énantiomérique quelconque.
EP05706975A 2004-01-30 2005-01-24 Procede pour produire des derives de 3-amino-5-(hydroxymethyl)cyclopentane-1,2-diols Withdrawn EP1771434A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP05706975A EP1771434A2 (fr) 2004-01-30 2005-01-24 Procede pour produire des derives de 3-amino-5-(hydroxymethyl)cyclopentane-1,2-diols

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP04002055A EP1574508A1 (fr) 2004-01-30 2004-01-30 Procédé pour la préparation d acetals et cétals de 3-amino-5-(hydroxymethyl)-cyclopentane -1,2-diols et leur derivés sels
PCT/EP2005/000643 WO2005073213A2 (fr) 2004-01-30 2005-01-24 Procede pour produire des derives de 3-amino-5-(hydroxymethyl)cyclopentane-1,2-diols
EP05706975A EP1771434A2 (fr) 2004-01-30 2005-01-24 Procede pour produire des derives de 3-amino-5-(hydroxymethyl)cyclopentane-1,2-diols

Publications (1)

Publication Number Publication Date
EP1771434A2 true EP1771434A2 (fr) 2007-04-11

Family

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Family Applications (2)

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EP04002055A Withdrawn EP1574508A1 (fr) 2004-01-30 2004-01-30 Procédé pour la préparation d acetals et cétals de 3-amino-5-(hydroxymethyl)-cyclopentane -1,2-diols et leur derivés sels
EP05706975A Withdrawn EP1771434A2 (fr) 2004-01-30 2005-01-24 Procede pour produire des derives de 3-amino-5-(hydroxymethyl)cyclopentane-1,2-diols

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP04002055A Withdrawn EP1574508A1 (fr) 2004-01-30 2004-01-30 Procédé pour la préparation d acetals et cétals de 3-amino-5-(hydroxymethyl)-cyclopentane -1,2-diols et leur derivés sels

Country Status (5)

Country Link
US (1) US7417153B2 (fr)
EP (2) EP1574508A1 (fr)
JP (1) JP2007538001A (fr)
CN (1) CN1922166A (fr)
WO (1) WO2005073213A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2009292269B2 (en) * 2008-09-09 2012-11-01 Astrazeneca Ab A process for preparing [1S- [1-alpha, 2-alpha, 3-beta (1S*, 2R*) 5-beta] ] -3- [7- [2- (3, 4-dif luorophenyl) -cyclopropylamino] - 5- (propylthio) -3H-1, 2, 3-triazolo [4, 5-d] pyrimidin-3-yl] -5- (2- hydroxyethoxy) cyclopentane-1, 2-diol and to its intermediates

Family Cites Families (11)

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Publication number Priority date Publication date Assignee Title
ATE147074T1 (de) * 1990-09-25 1997-01-15 Rhone Poulenc Rorer Int Verbindungen welche antihypertensive und antiischemische eigenschaften besitzen
US5561134A (en) 1990-09-25 1996-10-01 Rhone-Poulenc Rorer Pharmaceuticals Inc. Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties
FR2677019B1 (fr) 1991-05-27 1994-11-25 Pf Medicament Nouvelles piperidines disubstituees-1,4, leur preparation et leur application en therapeutique.
US5670649A (en) 1995-05-30 1997-09-23 Rhone-Poulenc Rorer S.A. Derivatives of 2-azabicyclo 2.2.1!heptane, their preparation and their application
US5684159A (en) * 1995-05-30 1997-11-04 Rhone-Poulenc Rorer S.A. L-tartaric acid salt of a (1R) diastereomer of a 2-azadihydroxybicyclo 2.2.1!heptane compound and the preparation of 2-azabicyclo 2.2.1!heptane compounds
FR2734822B1 (fr) 1995-05-30 1997-07-04 Rhone Poulenc Rorer Sa Nouveaux derives du 2-azabicyclo(2.2.1)heptane, leur preparation et leur application
AU6489896A (en) * 1995-07-10 1997-02-10 Rhone-Poulenc Rorer Pharmaceuticals Inc. N-(acyloxymethyl or hydroxymethyl) (optionally (oxa or thia) substituted)bicyclo({2.2.1} or {2.2.2})azalk(an or en)one compounds
UA51716C2 (uk) 1996-07-08 2002-12-16 Авентіс Фармасьютікалз Продактс Інк. Сполуки, що мають гіпотензивну, кардіопротекторну, анти-ішемічну та антиліполітичну властивості, фармацевтична композиція та способи лікування
US6376472B1 (en) 1996-07-08 2002-04-23 Aventis Pharmaceuticals, Inc. Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties
DK1095160T3 (da) * 1998-07-09 2004-05-17 Lonza Ag Fremgangsmåde til fremstilling af (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-on-derivater
MXPA03009946A (es) 2001-05-10 2005-03-07 Aventis Pharma Gmbh Nuevos procedimientos para la preparacion de compuestos de adenosina e intermedios para los mismos.

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Also Published As

Publication number Publication date
US20070043225A1 (en) 2007-02-22
JP2007538001A (ja) 2007-12-27
EP1574508A1 (fr) 2005-09-14
US7417153B2 (en) 2008-08-26
WO2005073213A2 (fr) 2005-08-11
WO2005073213A3 (fr) 2005-11-24
CN1922166A (zh) 2007-02-28

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