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Details for Patent: 7,238,834

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Details for Patent: 7,238,834

Title:Piperidine derivatives and process for their production
Abstract: The present invention relates to substantially pure piperidine derivative compounds of the formulae: ##STR00001## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2 is hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2; R.sub.3 is --COOH or --COOR.sub.4; R.sub.4 has 1 to 6 carbon atoms; A, B, and D are the substituents of their respective rings each of which may be different or the same and are hydrogen, halogens, alkyl, hydroxy, alkoxy, or other substituents. A process of preparing such piperidine derivative compounds in substantially pure form is also disclosed.
Inventor(s): D'Ambra; Thomas E. (Wynantskill, NY)
Assignee: AMR Technology, Inc. (Manchester Center, VT)
Filing Date:Oct 14, 2005
Application Number:11/250,924
Claims:1. A process of preparing a substantially pure regioisomer of the formula: ##STR00042## wherein R.sub.3 is --COOR.sub.4; R.sub.4 is chosen from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 5 carbon alkyl, and 6 carbon alkyl; A is a substituent of its ring selected from the group consisting of hydrogen, halogens, alkyl, hydroxy or alkoxy, said process comprising: providing a mixture of regioisomers of the formula: ##STR00043## recovering from the mixture of regioisomers the substantially pure regioisomer of the formula: ##STR00044## esterifying the substantially pure regioisomer to yield: ##STR00045##

2. A process according to claim 1, wherein said providing the mixture of regiolsomers comprises: acylating a starting compound of the formula: ##STR00046## wherein R.sub.5 is --OR.sub.6, --N(R.sub.6).sub.2, and --SR.sub.6, and R.sub.6 is an alkyl with 1 to 6 carbons, with a compound of the formula: ##STR00047## wherein X is a halogen, under conditions effective to produce a mixture of regioisomers of the formula: ##STR00048## hydrolyzing the first mixture of regioisomers under conditions effective to form the second mixture of regioisomers of the formula: ##STR00049##

3. A process according to claim 2, wherein said acylating is carried out by a Friedel-Crafts reaction using an AlCl.sub.3 catalyst.

4. A process according to claim 1, wherein said providing the mixture of regioisomers comprises: acylating a starting compound of the formula: ##STR00050## wherein R.sub.5 is --OR.sub.6, --N(R.sub.6).sub.2, and --SR.sub.6, and R.sub.6 is an alkyl with 1 to 6 carbon atoms, with a compound of the formula: ##STR00051## under conditions effective to produce a first mixture of regioisomers of the formula: ##STR00052## hydrolyzing the first mixture of regioisomers under conditions effective to form a second mixture of regioisomers of the formula: ##STR00053##

5. A process according to claim 1, wherein said recovering comprises: crystallizing from the second mixture of regioisomers a substantially pure regioisomer salt of the formula: ##STR00054## wherein X.sup.+ is a Lewis acid; isolating the substantially pure regioisomer salt; and converting the substantially pure regioisomer salt to the substantially pure regioisomer of the formula: ##STR00055##

6. A process according to claim 5, wherein X.sup.+ is an alkali metal salt or an ammonium salt of the form NR.sub.7, R.sub.8, R.sub.9 wherein R.sub.7, R.sub.8, and R.sub.9 are individually hydrogen or a straight or branched alkyl of 1 to 6 carbon atoms, or an alkyl substituted at any position with a phenyl ring or a substituted phenyl ring.

7. A process according to claim 6, wherein X.sup.+ is cinchonidine and A is hydrogen.

8. A process of preparing a substantially pure regioisomer of the formula: ##STR00056## wherein R.sub.3 is --COOR.sub.4; R.sub.4 is chosen from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 5 carbon alkyl, and 6 carbon alkyl; A is a substituent of its ring selected from the group consisting of hydrogen, halogens, alkyl, hydroxy or alkoxy, said process comprising: acylating a starting compound of the formula: ##STR00057## wherein R.sub.5 is OR.sub.6, --N(R.sub.6).sub.2, and --SR.sub.6, and R.sub.6 is an alkyl with 1 to 6 carbons, with a compound of the formula: ##STR00058## wherein X is a halogen, under conditions effective to produce a first mixture of regioisomers of the formula: ##STR00059## and converting the first mixture of regioisomers to the substantially pure regioisomer of formula: ##STR00060##

9. A process of preparing a substantially pure regioisomer of the formula: ##STR00061## wherein R.sub.3 is --COOR.sub.4; R.sub.4 is chosen from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 5 carbon alkyl, and 6 carbon alkyl; A is a substituent of its ring selected from the group consisting of hydrogen, halogens, alkyl, hydroxy or alkoxy, said process comprising: acylating a starting compound of the formula: ##STR00062## wherein R.sub.5 is --OR.sub.6, --N(R.sub.6).sub.2, and --SR.sub.6, and R.sub.6 is an alkyl with 1 to 6 carbon atoms with a compound of the formula: ##STR00063## under conditions effective to produce a first mixture of regioisomers of the formula: ##STR00064## and converting the first mixture of regioisomers to the substantially pure regioisomer of formula: ##STR00065##

10. A process of preparing a substantially pure regioisomer of the formula: ##STR00066## wherein R.sub.3 is --COOR.sub.4; R.sub.4 is chosen from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 5 carbon alkyl, and 6 carbon alkyl; A is a substituent of its ring selected from the group consisting of hydrogen, halogens, alkyl, hydroxy or alkoxy, said process comprising: acylating a starting compound of the formula: ##STR00067## with a compound of the formula: ##STR00068## wherein X.sub.1 is a halogen, trialkyl tin, triflate, or substituents useful in organometalic coupling reactions under conditions effective to produce the substantially pure regioisomer.

11. A substantially pure regioisomer having the formula: ##STR00069## wherein X is a halogen; R.sub.3 is --COOR.sub.4; R.sub.4 is chosen from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 5 carbon alkyl, and 6 carbon alkyl; A is a substituent of its ring selected from the group consisting of hydrogen, halogens, alkyl, hydroxy or alkoxy.

12. A process of preparing a second substantially pure regiolsomer of the formula: ##STR00070## wherein X is a halogen; R.sub.3 is --COOR.sub.4; R.sub.4 is chosen from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 5 carbon alkyl, and 6 carbon alkyl; A is a substituent of its ring selected from the group consisting of hydrogen, halogens, alkyl, hydroxy or alkoxy, said process comprising: providing a first substantially pure regioisomer of the formula: ##STR00071## halogenating the first substantially pure regioisomer under conditions effective to form the second substantially pure regioisomer.
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