US2005209279A1PendingUtilityA1
Process for production of piperidine derivatives
Est. expiryDec 21, 2015(expired)· nominal 20-yr term from priority
A61P 37/08C07D 211/22A61P 37/00C07D 211/46C07D 211/20C07D 211/14A61K 31/445
59
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Abstract
The present invention relates to a process for preparing piperidine derivative compounds of the formulae: wherein n is 0 or 1; R 1 is hydrogen or hydroxy; R 2 is hydrogen; or, when n is 0, R 1 and R 2 taken together form a second bond between the carbon atoms bearing R 1 and R 2 , provided that when n is 1, R 1 and R 2 are each hydrogen; R 3 is —COOH or —COOR 4 ; R 4 is an alkyl or aryl moiety; A, B, and D are the substituents of their rings, each of which may be different or the same, and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents, The process comprises providing a regiosomer of the following formula: wherein Z is —CG 1 G 2 G 3 , m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ; G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ; R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ; and R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety and converting the regioisomer to the piperidine derivative compound with a piperidine compound.
Claims
exact text as granted — not AI-modified1 . A process of preparing a piperidine derivative compound of the formula:
wherein
n is 0 or 1;
R 1 is hydrogen or hydroxy;
R 2 is hydrogen;
or, when n is 0, R 1 and R 2 taken together form a second bond between the carbon atoms bearing R 1 and R 2 , provided that when n is 1, R 1 and R 2 are each hydrogen;
R 3 is —COOH or —COOR 4 ;
R 4 is an alkyl or aryl moiety;
A, B, and D are the substituents of their rings, each of which may be different or the same, and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents;
said process comprising:
providing a regiosomer of the following formula:
wherein
Z is CG 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ; and
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety and
converting the regioisomer to the piperidine derivative compound with a piperidine compound.
2 . A process according to claim 1 , wherein said providing the regioisomer comprises:
acylating an α,α-disubstituted-methylbenzene derivative having the formula: wherein
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions
with a compound having the formula:
wherein
X 2 is a halogen; an alkali metal oxide; a moiety having the formula —OR 10 ; a moiety having the formula —SR 10 ; or an amine; and
R 10 is selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety
under conditions effective to produce the regioisomer.
3 . A process according to claim 2 further comprising:
reacting an α,α-diunsubstituted-methylbenzene derivative having the formula: with a methylating agent under conditions effective to produce the α,α-disubstituted-methylbenzene derivative.
4 . A process according to claim 3 , wherein Z has the formula:
and further comprising
reacting an α,α-diunsubstituted benzylic acid derivative having the formula:
with an aminoalkyl derivative having the formula:
H 2 N—(CR 6 R 7 ) m -Q-H
under conditions effective to produce the α,α-diunsubstituted-methylbenzene derivative.
5 . A process according to claim 2 , wherein Z has the formula:
and further comprising:
reacting an α,α-disubstituted benzylic acid derivative having the formula:
with an aminoalkyl derivative having the formula:
H 2 N—(CR 6 R 7 ) m -Q-H
under conditions effective to produce the α,α-disubstituted-methylbenzene derivative.
6 . A process according to claim 1 , wherein said providing the regioisomer comprises:
reacting a 4-(α,α-disubstituted)-toluic acid derivative having the formula: wherein
X 2 is hydrogen; a halogen; an alkali metal oxide; a moiety having the formula —OR 10 ; a moiety having the formula —SR 10 ; or an amine; and
R 10 is selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety
with a compound having the formula:
wherein
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions
under conditions effective to produce the regioisomer.
7 . A process according to claim 6 , further comprising:
reacting a 4-(α,α-diunsubstituted)-toluic acid derivative having the formula: with a methylating agent under conditions effective to produce the 4-(α,α-disubstituted)-toluic acid derivative.
8 . A process according to claim 7 , wherein Z has the formula:
and further comprising:
reacting a 4-(α-carboxy-α,α-diunsubstituted)-toluic acid derivative having the formula:
with an aminoalkyl derivative having the formula:
H 2 N—(CR 6 R 7 ) m -Q-H
under conditions effective to produce the 4-(α,α-diunsubstituted)-toluic acid derivative.
9 . A process according to claim 6 , wherein Z has the formula:
and further comprising:
reacting a 4-(α-carboxy-α,α-disubstituted)-toluic acid derivative having the formula:
with an aminoalkyl derivative having the formula:
H 2 N—(CR 6 R 7 ) m -Q-H
under conditions effective to produce the 4-(α,α-disubstituted)-toluic acid derivative.
10 . A process according to claim 1 , wherein said providing the regioisomer comprises:
providing an α,α-diunsubstituted regioisomer precursor having the formula: and methylating the α,α-diunsubstituted regioisomer precursor under conditions effective to produce the regioisomer.
11 . A process according to claim 10 , wherein said providing the α,α-diunsubstituted regioisomer precursor comprises:
acylating an α,α-diunsubstituted-methylbenzene derivative having the formula: wherein
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions
with a compound having the formula:
wherein
X 2 is a halogen; an alkali metal oxide; a moiety having the formula —OR 10 ; a moiety having the formula —SR 10 ; or an amine; and
R 10 is selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety
under conditions effective to produce the α,α-diunsubstituted regioisomer precursor.
12 . A process according to claim 10 , wherein said providing the α,α-diunsubstituted regioisomer precursor comprises:
reacting a 4-(α,α-diunsubstituted)-toluic acid derivative having the formula: wherein
X 2 is hydrogen; a halogen; an alkali metal oxide; a moiety having the formula —OR 10 ; a moiety having the formula —SR 10 ; or an amine; and
R 10 is selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety with a compound having the formula:
wherein
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions
under conditions effective to produce the α,α-diunsubstituted regioisomer precursor.
13 . A process according to claim 1 , further comprising:
reducing the piperidine derivative compound under conditions effective to form a hydroxylated piperidine derivative compound of the formula:
14 . A process according to claim 13 , wherein the hyrdroxylated piperidine derivative compound has the formula:
15 . A process according to claim 13 , wherein the hydroxylated piperidine derivative compound has the formula:
16 . A process according to claim 1 , wherein the piperidine derivative compound has the formula:
17 . A process according to claim 1 , wherein the piperidine derivative compound has the formula:
18 . A process according to claim 1 , wherein said converting comprises:
halogenating the regioisomer of the formula: under conditions effective to form a first intermediate compound of the formula: wherein X 3 is a halogen or a hydroxy, alkoxy, or aryloxy moiety.
19 . A process according to claim 18 , wherein said halogenating comprises sequentially:
decyclizing the regioisomer to produce an oxobutyl derivative having the formula: and then converting the oxobutyl derivative to the first intermediate compound.
20 . A process according to claim 18 , wherein said converting further comprises:
reacting the first intermediate compound with a piperidine compound of the formula: under conditions effective to form the piperidine derivative compound of the formula:
21 . A process according to claim 18 , wherein said converting further comprises:
esterifying the first intermediate compound to the ester thereof, having the formula: and reacting the ester with a piperidine compound of the formula: under conditions effective to form the piperidine derivative compound of the formula:
22 . A process according to claim 21 , further comprising:
hydrolyzing the piperidine derivative compound of the formula: to a piperidine derivative compound of the formula:
23 . A process according to claim 18 , wherein n is 1 and wherein said converting further comprises:
reacting the first intermediate compound with 4-hydroxypiperidine under conditions effective to produce an N-substituted hydroxypiperidine having the formula: and reacting the N-substituted hydroxypiperidine with a diarylhalomethane having the formula: wherein X 4 is a halogen under conditions effective to form the piperidine compound derivative of the formula:
24 . A process according to claim 1 , wherein said converting comprises:
decyclizing the regioisomer of the formula: under conditions effective to form an oxobutyl derivative of the formula: wherein X 3 is a halogen or a hydroxy, alkoxy, or aryloxy moiety.
25 . A process according to claim 24 , wherein said converting further comprises:
reacting the oxobutyl derivative with a piperidine compound of the formula: under conditions effective to form the piperidine derivative precursor of the formula:
26 . A process according to claim 25 , further comprising
converting the piperidine derivative precursor to the piperidine derivative compound of the formula:
27 . A process according to claim 25 , further comprising
reducing the piperidine derivative precursor under conditions effective to form a hydroxylated piperidine derivative precursor of the formula:
28 . A process according to claim 27 , further comprising
converting the hydroxylated piperidine derivative precursor to a hydroxylated piperidine derivative compound of the formula:
29 . A process according to claim 24 , wherein n is 1 and wherein said converting further comprises:
reacting the oxobutyl derivative with 4-hydroxypiperidine under conditions effective to produce an N-substituted-hydroxypiperidine having the formula: and reacting the N-substituted hydroxypiperidine with a diarylhalomethane having the formula: wherein X 4 is a halogen under conditions effective to form the piperidine derivative precursor of the formula:
30 . A process according to claim 29 , further comprising
converting the piperidine derivative precursor to the piperidine derivative compound of the formula:
31 . A process according to claim 29 , further comprising
reducing the piperidine derivative precursor under conditions effective to form a hydroxylated piperidine derivative precursor of the formula:
32 . A process according to claim 31 , further comprising
converting the hydroxylated piperidine derivative precursor to a hydroxylated piperidine derivative compound of the formula:
33 . A regioisomer having the formula:
wherein
Z is —CG 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ;
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and
A is the substituents of its ring, each of which may be different or the same and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents.
34 . A regioisomer according to claim 33 , wherein Z is
R 6 and R 7 are each methyl, and R 12 and R 13 are each hydrogen.
35 . A process of preparing a regioisomer of the formula:
wherein
Z is G 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ;
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and
A is the substituents of its ring, each of which may be different or the same and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents,
said process comprising
acylating an α,α-disubstituted-methylbenzene derivative having the formula:
wherein
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions
with a compound having the formula:
wherein
X 2 is a halogen; an alkali metal oxide; a moiety having the formula —OR 10 ; a moiety having the formula —SR 10 ; or an amine; and
R 10 is selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety
under conditions effective to produce the regioisomer.
36 . A process according to claim 35 further comprising:
reacting an α,α-diunsubstituted-methylbenzene derivative having the formula: with a methylating agent under conditions effective to produce the α,α-disubstituted-methylbenzene derivative.
37 . A process according to claim 36 , wherein Z has the formula:
and further comprising
reacting an α,α-diunsubstituted benzylic acid derivative having the formula:
with an aminoalkyl derivative having the formula:
H 2 N—(CR 6 R 7 ) m -Q-H
under conditions effective to produce the α,α-diunsubstituted-methylbenzene derivative.
38 . A process according to claim 35 , wherein Z has the formula:
and further comprising:
reacting an α,α-disubstituted benzylic acid derivative having the formula:
with an aminoalkyl derivative having the formula:
H 2 N—(CR 6 R 7 ) m -Q-H
under conditions effective to produce the α,α-disubstituted-methylbenzene derivative.
39 . A process of preparing a regioisomer of the formula:
wherein
Z is —CG 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ;
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and
A is the substituents of its ring, each of which may be different or the same and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents,
said process comprising:
reacting a 4-(α,α-disubstituted)-toluic acid derivative having the formula:
wherein
X 2 is hydrogen; a halogen; an alkali metal oxide; a moiety having the formula —OR 10 ; a moiety having the formula —SR 10 ; or an amine; and
R 10 is selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety
with a compound having the formula:
wherein
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions
under conditions effective to produce the regioisomer.
40 . A process according to claim 39 further comprising:
reacting a 4-(α,α-diunsubstituted)-toluic acid derivative having the formula: with a methylating agent under conditions effective to produce the 4-(α-α-disubstituted)-toluic acid derivative.
41 . A process according to claim 40 , wherein Z has the formula:
and further comprising:
reacting a 4-(α-carboxy-α,α-diunsubstituted)-toluic acid derivative having the formula:
with an aminoalkyl derivative having the formula:
H 2 N—(CR 6 R 7 ) m -Q-H
under conditions effective to produce the 4-(α,α-diunsubstituted)-toluic acid derivative.
42 . A process according to claim 41 , wherein Z has the formula:
said process further comprising:
reacting an 4-(α-carboxy-α,α-disubstituted)-toluic acid derivative having the formula:
with an aminoalkyl derivative having the formula:
H 2 N—(CR 6 R 7 ) m -Q-H
under conditions effective to produce the 4-(α,α-disubstituted)-toluic acid derivative.
43 . A process of preparing a regioisomer of the formula:
wherein
Z is G 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ;
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and
A is the substituents of its ring, each of which may be different or the same and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents,
said process comprising:
providing an α,α-diunsubstituted regioisomer precursor having the formula:
and
methylating the α,α-diunsubstituted regioisomer precursor under conditions effective to produce the regioisomer.
44 . A process according to claim 43 , wherein said providing the α,α-diunsubstituted regioisomer precursor comprises:
acylating an α,α-diunsubstituted-methylbenzene derivative having the formula: wherein
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions
with a compound having the formula:
wherein
X 2 is a halogen; an alkali metal oxide; a moiety having the formula —OR 10 ; a moiety having the formula —SR 10 ; or an amine; and
R 10 is selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety
under conditions effective to produce the α,α-diunsubstituted regioisomer precursor.
45 . A process according to claim 44 , wherein said providing the α,α-diunsubstituted regioisomer precursor comprises:
acylating a 4-(α,α-diunsubstituted)-toluic acid derivative having the formula: wherein
X 2 is a halogen; an alkali metal oxide; a moiety having the formula —OR 10 ; a moiety having the formula —SR 10 ; or an amine; and
R 10 is selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety with a compound having the formula: wherein
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions
under conditions effective to produce the α,α-diunsubstituted regioisomer precursor.
46 . An α,α-disubstituted-methylbenzene derivative having the formula:
wherein
Z is —CG 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ;
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety;
A is the substituents of its ring, each of which may be different or the same and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents; and
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions.
47 . An α,α-disubstituted-methylbenzene derivative according to claim 46 , wherein Z is
R 6 and R 7 are each methyl, R 12 and R 13 are each hydrogen, and X 1 is bromine.
48 . An α,α-diunsubstituted-methylbenzene derivative having the formula:
wherein
Z is —CG 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ;
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety;
A is the substituents of its ring, each of which may be different or the same and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents; and
X 1 is a halogen, trialkyl or triaryl tin, trialkyl or triaryl borate, trialkyl silicon, alkylhalo silicon, a substituted sulfonic ester, or substituents useful in organometallic coupling reactions.
49 . An α,α-disubstituted-methylbenzene derivative according to claim 48 , wherein Z is
R 6 and R 7 are each methyl, R 12 and R 13 are each hydrogen, and X 1 is bromine.
50 . An oxobutyl derivative having the formula:
wherein
Z is —CG 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ;
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety;
A is the substituents of its ring, each of which may be different or the same and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents; and
X 3 is a halogen or a hydroxy, alkoxy, or aryloxy moiety.
51 . An α,α-disubstituted-methylbenzene derivative according to claim 50 , wherein Z is
R 6 and R 7 are each methyl, R 12 and R 13 are each hydrogen, and X 3 is a halogen.
52 . A piperidine derivative precursor having the formulae:
wherein
n is 0 or 1;
R 1 is hydrogen or hydroxy;
R 2 is hydrogen;
or, when n is 0, R 1 and R 2 taken together form a second bond between the carbon atoms bearing R 1 and R 2 , provided that when n is 1, R 1 and R 2 are each hydrogen;
Z is —CG 1 G 2 G 3 ,
m is an integer from 1 to 6;
Q and Y are the same or different and are selected from the group consisting of O, S, and NR 5 ;
G 1 , G 2 , and G 3 are the same or different and are selected from the group consisting of OR 8 , SR 8 , and NR 8 R 9 ;
R 6 and R 7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR 8 , SR 8 , and NR 8 R 9 ;
R 5 , R 8 , and R 9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety; and
A, B, and D are the substituents of their rings, each of which may be different or the same, and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents.
53 . A piperidine derivative precursor according to claim 52 , wherein Z is
R 6 and R 7 are each methyl, and R 12 and R 13 are each hydrogen.
54 . A method of treating allergic reactions in a patient comprising:
administering to the patient an effective amount of a piperidine derivative precursor according to claim 53 .
55 . A method of treating allergic reactions in a patient comprising:
administering to the patient an effective amount of a piperidine derivative precursor according to claim 52.Cited by (0)
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