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БИБЛИОТЕКА ПАТЕНТОВ НА ИЗОБРЕТЕНИЯ

Synthesis of phenolic esters of hydroxymethyl phenols (патент US № 7985873)

Официальная публикация
патента US № 7985873

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Классы МПК:C07C69/035 ..этерифицированной оксисоединением, содержащим этерифицированную оксигруппу, связанную с атомом углерода шестичленного ароматического кольца
Автор(ы):Ennis, Seth C. (Limerick, IE)
Drews, Roland (Monheim, DE)
Meese, Claus (Monheim, DE)
Патентообладатель(и):UCB Pharma GmbH (Monheim, DE)
Приоритеты:
подача заявки
05.06.2007
публикация патента
26.07.2011

РЕФЕРАТ (Abstract)

The present invention provides a process for the production of a compound of formula (I) or a salt thereof, wherein R is hydrogen, a straight, branched or cyclic C1-C6 alkyl group or an aryl group which may optionally be substituted. This process comprises: (a) reacting a compound of formula (II), with a compound of formula (III), wherein R is as defined above and X is a leaving group, in the presence of N,N-di-isopropylethylamine.

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ФОРМУЛА ИЗОБРЕТЕНИЯ (CLAIMS)

The invention claimed is:

1. A process for the preparation of a compound of formula (I) or a salt thereof embedded image wherein R is hydrogen, an optionally substituted straight, branched or cyclic C1-C6 alkyl group or an optionally substituted aryl group, comprising (a) reacting a compound of formula (II) embedded image with a compound of formula (III) embedded image wherein R is as defined above and X is a leaving group, wherein the reaction is performed in the presence of N,N-diisopropylethylamine.

2. The process of claim 1, wherein X is a halogen atom selected from the group consisting of chlorine, bromine and iodine.

3. The process of claim 1, wherein the reaction is performed at a temperature of −20° C. to 10° C.

4. The process of claim 3, wherein the reaction is performed at a temperature of −10° C. to −0° C.

5. The process of claim 1, wherein the reaction step (a) is carried out in methylene chloride.

6. The process of claim 1, wherein the molar ratio of the compound of formula (III) to the compound of formula (II) is not more than 1.10.

7. The process of claim 1, wherein the molar ratio of the compound of formula (III) to the compound of formula (II) is between 1.00 and 1.05.

8. The process of claim 1, further comprising one or more washing step(s) (b), wherein the reaction mixture obtained from step (a) is contacted with an alkaline solution.

9. The process of claim 8, wherein the washing steps (b) comprise successive washing steps using (i) an alkaline solution, (ii) an acidic solution and (iii) another alkaline solution.

10. The process of claim 8, wherein the washing solution(s) is/are aqueous.

11. The process of claim 1, further comprising a salt formation step wherein a salt of the compound of formula (I) is obtained.

12. The process of claim 11, wherein the salt of the compound of formula (I) is obtained in a crystalline form.

13. The process of claim 12, wherein methyl ethyl ketone is used as a solvent for the compound of formula (I) in the salt formation step.

14. The process of claim 13, wherein the crystallization of the compound of formula (I) in methyl ethyl ketone is initiated by the addition of cyclohexane.

15. The process of claim 1, wherein the compounds of formulae (I) and (II) are the R-enantiomers.

16. The process of claim 1, wherein R is hydrogen, an unsubstituted straight, cyclic or branched C1-C6 alkyl group or wherein R represents a phenyl or naphthyl group, which are unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, C1-C6 alkyl, C1-C6 alkoxyl, nitro and hydroxyl.

17. The process according to claim 1, wherein R is isopropyl.

18. The process of any one of claims 11-14, wherein the salt of the compound of formula (I) is isobutyric acid 2-((R)-3-diisopropylammonium-1-phenylpropyl)-4-(hydroxymethyl)phenylester hydrogen fumarate (fesoterodine hydrogen fumarate).


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