US2013316953A1PendingUtilityA1
New uses for amino acid anticonvulsants
Individually held — no corporate assignee on recordPriority: Aug 25, 2000Filed: Jul 29, 2013Published: Nov 28, 2013
Est. expiryAug 25, 2020(expired)· nominal 20-yr term from priority
Inventors:Robert H. Harris
A61P 43/00A61P 25/00A61P 25/04A61P 25/28A61P 29/00A61P 25/06A61P 25/14A61P 25/18A61K 31/40A61K 38/05A61K 38/04A61K 31/44A61K 31/165A61K 31/195A61K 31/16
60
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Claims
Abstract
The present invention is directed to the use of compounds of the formula: for treating pain, in particular neuropathic pain, bipolar disease and migraine headaches.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A method for alleviating pain in a patient suffering from chronic pain comprising administering to said patient an analgesic effective amount of a compound of the formula:
wherein
R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl, aryl lower alkyl, heterocyclic, heterocyclic lower alkyl, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, and R is unsubstituted or is substituted with at least one electron withdrawing group or electron donating group;
R 1 is hydrogen or lower alkyl, lower alkenyl, lower alkynyl, aryl lower alkyl, aryl, heterocyclic lower alkyl, heterocyclic, lower alkyl heterocyclic, lower cycloalkyl, lower, cycloalkyl lower alkyl, each unsubstituted or substituted with an electron donating group or an electron withdrawing group; and
R 2 and R 3 are independently hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl lower alkyl, halo, heterocyclic, heterocyclic lower alkyl, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, or Z—Y wherein R 2 and R 3 may be unsubstituted or substituted with at least one electron withdrawing group or electron donating group wherein the electron donating group or electron withdrawing group is acyclic; and wherein heterocyclic in R 2 and R 3 is furyl, thienyl, pyrazolyl, pyrrolyl, imidazolyl, indolyl, thiazolyl, oxazolyl, isothiazolyl, isoxazolyl, piperidyl, pyrrolinyl, piperazinyl, quinolyl, triazolyl, tetrazolyl, isoquinolyl, benzofuryl, benzothienyl, morpholinyl, benzoxazolyl, tetrahydrofuryl, pyranyl, indazolyl, purinyl, indolinyl, pyrazolindinyl, imidazolinyl, imidazolindinyl, pyrrolidinyl, furazanyl, N-methylindolyl, methylfuryl, pyridazinyl, pyrimidinyl, pyrazinyl, epoxy, aziridino, oxetanyl or azetidinyl;
Z is O, S, S(O) a , NR 6 ′, or PR 4 ;
Y is hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, lower alkynyl, heterocyclic, heterocyclic lower alkyl, and Y may be unsubstituted or substituted with an electron donating group or an electron withdrawing group, or
ZY taken together is NR 4 NR 5 R 7 , NR 4 OR 5 , ONR 4 R 7 , OPR 4 R 5 , PR 4 OR 5 , SNR 4 R 7 , NR 4 SR 7 , SPR 4 R 5 , PR 4 SR 7 , NR 4 PR 5 R 6 or PR 4 NR 5 R 7 ,
R 6 ′ is hydrogen, lower alkyl, lower alkenyl, or lower alkynyl and R 4 may be unsubstituted or substituted with an electron withdrawing group or electron donating group;
R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, or lower alkynyl, wherein R 4 , R 5 and R 6 may be unsubstituted or substituted with an electron withdrawing group or an electron donating group; and
R 7 is COOR 8 , COR 8 , hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl or lower alkynyl, which R 7 may be unsubstituted or substituted with an electron withdrawing group or electron donating group;
R 8 is hydrogen or lower alkyl, or aryl lower alkyl, and the aryl or alkyl group may be unsubstituted or substituted with an electron withdrawing group or an electron donating group; and
n is 1-4; and
a is 1-3.
2 . The method according to claim 1 wherein one of R 2 and R 3 is hydrogen.
3 . The method according to claim 1 wherein n is 1.
4 . The method according to claim 1 wherein one of R 2 and R 3 is hydrogen and n is 1.
5 . The method according to claim 1 wherein R is aryl lower alkyl and R 1 is lower alkyl.
6 . The method according to claim 1 wherein
R 2 and R 3 are independently hydrogen, lower alkyl, heterocyclic, heterocyclic loweralkyl, or ZY;
Z is O, NR 4 or PR 4 ;
Y is hydrogen or lower alkyl; or
ZY is NR 5 R 6 R 7 , NR 5 OR 6 , ONR 5 R 7 ,
7 . The method according to claim 6 wherein
R 2 is hydrogen and R 3 is hydrogen, lower alkyl, heterocyclic, heterocyclic loweralkyl or ZY;
Z is O, NR 4 or PR 4 ;
Y is hydrogen, lower alkyl; or
ZY is NR 5 NR 6 R 7 , NR 5 OR 6 , ONR 5 R 7 ,
8 . The method according to claim 6 wherein
R 2 is hydrogen and R 3 is lower alkyl, which may be unsubstituted or substituted with an electron donating or electron withdrawing group, NR 4 OR 5 , or ONR 4 R 7 .
9 . The method according to claim 8 wherein R 3 is lower alkyl which is unsubstituted or substituted with hydroxy or loweralkoxy, NR 4 OR 6 or ONR 4 R 7 , wherein R 4 , R 5 and R 7 are independently hydrogen or lower alkyl, R is aryl loweralkyl, which aryl group may be unsubstituted or substituted with an electron withdrawing group and R 1 is lower alkyl.
10 . The method according to claim 9 wherein aryl is phenyl.
11 . The method according to claim 6 wherein one of R 2 and R 3 is heterocyclic.
12 . The method according to claim 11 wherein heterocyclic is heteroaromatic.
13 . The method according to claim 11 wherein R 3 is furyl, pyridyl, thienyl or thiazolyl.
14 . The method according to claim 9 wherein aryl is phenyl and is unsubstituted or substituted with halo.
15 . The method according to claim 1 wherein the compound is
(R)—N-Benzyl-2-acetamide-3-methoxy-propionamide;
O-methyl-N-acetyl-D-serine-m-fluorobenzylamide;
O-methyl-N-acetyl-D-serine-p-fluorobenzylamide;
N-acetyl-D-phenylglycinebenzylamide;
D-1,2-(N,O-dimethylhydroxylamino)-2-acetamide acetic acid benzylamide;
D-1,2-(O-methylhydroxylamino)-2-acetamido acetic acid benzylamide.
16 . The method according to claim 1 wherein the pain is neuropathic pain.
17 . The method according to claim 6 wherein the pain is neuropathic pain.
18 . The method according to claim 1 wherein the pain is nociceptive pain.
19 . The method according to claim 6 wherein the pain is nociceptive pain.
20 . A method for the prophylaxis or treatment of migraine headaches in a subject, comprising administering to said patient a headache relieving effective amount of a compound of the formula:
wherein
R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl, aryl lower alkyl, heterocyclic, heterocyclic lower alkyl, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, and R is unsubstituted or is substituted with at least one electron withdrawing group or electron donating group;
R 1 is hydrogen or lower alkyl, lower alkenyl, lower alkynyl, aryl lower alkyl, aryl, heterocyclic lower alkyl, heterocyclic, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, each unsubstituted or substituted with an electron donating group or an electron withdrawing group; and
R 2 and R 3 are independently hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl lower alkyl, aryl, halo, heterocyclic, heterocyclic lower alkyl, lower alkyl heterocyclic, lower alkyl heterocyclic lower cycloalkyl, lower cycloalkyl lower alkyl, or Z—Y wherein R 2 and R 3 may be unsubstituted or substituted with at least one electron withdrawing group or electron donating group;
Z is O, S, S(O) a , NR 4 , or PR 4 ;
Y is hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, lower alkynyl, heterocyclic, heterocyclic lower alkyl, and Y may be unsubstituted or substituted with an electron donating group or an electron withdrawing group, or
ZY taken together is NR 4 NR 5 R 7 , NR 4 OR 5 , ONR 4 R 7 , OPR 4 R 5 , PR 4 OR 5 , SNR 4 R 7 , NR 4 SR 7 , SPR 4 R 5 or PR 4 SR 7 , NR 4 PR 5 R 6 or PR 4 NR 5 R 7 ,
R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, or lower alkynyl, wherein R 4 , R 5 and R 6 may be unsubstituted or substituted with an electron withdrawing group or an electron donating group; and
R, is COOR 8 or COR 8 , hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl or lower alkynyl, which R 7 may be unsubstituted or substituted with an electron withdrawing group or electron donating group;
R 8 is hydrogen or lower alkyl, or aryl lower alkyl, and the aryl or alkyl group may be unsubstituted or substituted with an electron withdrawing group or an electron donating group; and
n is 1-4;
a is 1-3;
wherein
heterocyclic contains from 3 up to 18 ring atoms and up to a total of 17 ring carbon atoms containing 1 to 4 hetero ring atoms selected from the group consisting of nitrogen, oxygen and sulfur.
21 . The method according to claim 20 wherein one of R 2 and R 3 is hydrogen.
22 . The method according to claim 20 wherein n is 1.
23 . The method according to claim 20 wherein one of R 2 and R 3 is hydrogen and n is 1.
24 . The method according to claim 20 wherein R is aryl lower alkyl and R 1 is lower alkyl.
25 . The method according to claim 20 wherein R 2 and R 3 are independently hydrogen, lower alkyl, aryl, aryllower alkyl, heterocyclic, heterocyclic loweralkyl or ZY;
Z is O, NR 4 or PR 4 ;
Y is hydrogen, lower alkyl, aryl, aryl loweralkyl, heterocyclic or heterocyclic lower alkyl; or
ZY taken together is NR 4 NR 5 R 7 , NR 4 OR 5 , ONR 4 R 7 ,
and
R 4 , R 5 and R 7 are independently hydrogen, lower alkyl, aryl or aryl lower alkyl.
26 . The method according to claim 25 wherein R 2 is hydrogen and R 3 is lower alkyl, aryl, aryllower alkyl, heterocyclic or heterocyclic lower alkyl, or ZY;
Z is O, NR 4 or PR 4 ;
Y is hydrogen, lower alkyl, aryl, aryl loweralkyl, heterocyclic or heterocyclic lower alkyl; or
ZY taken together is NR 4 R 5 R 7 , NR 4 OR 5 , ONR 4 R 7 ,
and
R 4 , R 5 and R 7 are independently hydrogen, lower alkyl, aryl or aryl lower alkyl.
27 . The method according to claim 26 wherein
R 2 is hydrogen and R 3 is lower alkyl, which may be unsubstituted or substituted with an electron donating or electron withdrawing group, NR 5 OR 6 , or ONR 5 R 7 .
28 . The method according to claim 26 wherein R 3 is lower alkyl which is unsubstituted or substituted with hydroxy or loweralkoxy, NR 4 OR 5 or ONR 4 R 7 , wherein R 4 , R 5 and R 7 are independently hydrogen or lower alkyl, R is aryl loweralkyl, which aryl group may be unsubstituted or substituted with an electron withdrawing group and R 1 is lower alkyl.
29 . The method according to claim 26 wherein R 3 is heterocyclic.
30 . The method according to claim 29 wherein heterocyclic is heteroaromatic.
31 . The method according to claim 30 wherein R 3 is furyl, pyridyl, thienyl or thiazolyl.
32 . The method according to claim 28 wherein aryl is phenyl.
33 . The method according to claim 28 wherein aryl is phenyl and is unsubstituted or substituted with halo.
34 . The method according to claim 20 wherein the compound is
(R)—N-Benzyl-2-acetamide-3-methoxy-propionamide;
O-methyl-N-acetyl-D-serine-m-fluorobenzylamide;
O-methyl-N-acetyl-D-serine-p-fluorobenzylamide;
N-acetyl-D-phenylglycinebenzylamide;
D-1,2-(N,O-dimethylhydroxylamino)-2-acetamide acetic acid benzylamide; or
D-1,2-(O-methylhydroxylamino)-2-acetamido acetic acid benzylamide.
35 . A method of treating a patient suffering from bipolar disease comprising administering thereto a therapeutically effective amount of a compound for treating bipolar disease, said compound having the formula:
wherein
R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl, aryl lower alkyl, heterocyclic, heterocyclic lower alkyl, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, and R is unsubstituted or is substituted with at least one electron withdrawing group or electron donating group;
R 1 is hydrogen or lower alkyl, lower alkenyl, lower alkynyl, aryl lower alkyl, aryl, heterocyclic lower alkyl, heterocyclic, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, each unsubstituted or substituted with an electron donating group or an electron withdrawing group; and
R 2 and R 3 are independently hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl lower alkyl, aryl, halo, heterocyclic, heterocyclic lower alkyl, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, or Z—Y wherein R 2 and R 3 may be unsubstituted or substituted with at least one electron withdrawing group or electron donating group;
Z is O, S, S(O) a , NR 4 , or PR 4 ;
Y is hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, lower alkynyl, heterocyclic, heterocyclic lower alkyl, and Y may be unsubstituted or substituted with an electron donating group or an electron withdrawing group, or
ZY taken together is NR 4 NR 5 R 7 , NR 4 OR 5 , ONR 4 R 7 , OPR 4 R 5 , PR 4 OR 5 , SNR 4 R 7 , NR 4 SR 7 , SPR 4 R 5 or PR 4 SR 7 , NR 4 PR 5 R 6 or PR 4 NR 5 R 7 ,
R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, or lower alkynyl, wherein R 4 , R 5 and R 6 may be unsubstituted or substituted with an electron withdrawing group or an electron donating group; and
R 7 is COOR 8 , COR 8 , hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl or lower alkynyl wherein R 7 may be unsubstituted or substituted with an electron withdrawing group or electron donating group;
R 8 is hydrogen or lower alkyl, or aryl lower alkyl, and the aryl or alkyl group may be unsubstituted or substituted with an electron withdrawing group or an electron donating group; and
n is 1-4; and
a is 1-3.
36 . The method according to claim 35 wherein one of R 2 and R 3 is hydrogen.
37 . The method according to claim 35 wherein n is 1.
38 . The method according to claim 35 wherein one of R 2 and R 3 is hydrogen and n is 1.
39 . The method according to claim 35 wherein R is aryl lower alkyl and R 1 is lower alkyl.
40 . The method according to claim 35 wherein R 2 and R 3 are independently lower alkyl, aryl, aryllower alkyl, heterocyclic, heterocyclic lower alkyl, or ZY;
Z is O, NR 4 or PR 4 ;
Y is hydrogen, lower alkyl, aryl, aryl loweralkyl, heterocyclic or heterocyclic lower alkyl; or
ZY taken together is NR 4 NR 5 R 7 , NR 4 OR 5 , ONR 4 R 7 ,
and
R 4 , R 5 and R 7 are independently hydrogen, lower alkyl, aryl or aryl lower alkyl.
41 . The method according to claim 40 wherein R 2 is hydrogen and R 3 is lower alkyl, aryl, aryllower alkyl, heterocyclic, heterocyclic lower alkyl or ZY;
Z is O, NR 4 or PR 4 ;
Y is hydrogen, lower alkyl, aryl, aryl loweralkyl, heterocyclic or heterocyclic lower alkyl; or
ZY taken together is NR 4 NR 5 R 7 , NR 4 OR 5 , ONR 4 R 7 ,
and
R 4 , R 5 and R 7 are independently hydrogen, lower alkyl, aryl or aryl lower alkyl.
42 . The method according to claim 41 wherein
R 2 is hydrogen and R 3 is lower alkyl, which may be unsubstituted or substituted with an electron donating or electron withdrawing group, NR 4 OR 5 , or ONR 4 R 7 .
43 . The method according to claim 41 wherein R 3 is lower alkyl which is unsubstituted or substituted with hydroxy or loweralkoxy, NR 4 OR 5 or ONR 4 R 7 , wherein R 4 , R 5 and R 7 are independently hydrogen or lower alkyl, R is aryl loweralkyl, which aryl group may be unsubstituted or substituted with an electron withdrawing group and R 1 is lower alkyl.
44 . The method according to claim 41 wherein R 3 is heterocyclic.
45 . The method according to claim 44 wherein heterocyclic is heteroaromatic.
46 . The method according to claim 45 wherein R 3 is furyl, pyridyl, thienyl or thiazolyl.
47 . The method according to claim 43 wherein aryl is phenyl.
48 . The method according to claim 43 wherein aryl is phenyl and is unsubstituted or substituted with halo.
49 . The method according to claim 35 wherein the compound is (R)—N-Benzyl-2-acetamide-3-methoxy-propionamide;
O-methyl-N-acetyl-D-serine-m-fluorobenzylamide;
O-methyl-N-acetyl-D-serine-p-fluorobenzylamide;
N-acetyl-D-phenylglycinebenzylamide;
D-1,2-(N,O-dimethylhydroxylamino)-2-acetamide acetic acid benzylamide;
D-1,2-(O-methylhydroxylamino)-2-acetamido acetic acid benzylamide.
50 . A method for treating a disorder in a mammal resulting from abnormal activity at the glycine b site of the NMDA receptor in neurons of said mammal comprising administering to said mammal a therapeutically effective amount of a compound to interact with the glycine b site of the NMDA receptor, said compound having the formula:
wherein
R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl, aryl lower alkyl, heterocyclic, heterocyclic lower alkyl, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, and R is unsubstituted or is substituted with at least one electron withdrawing group or electron donating group;
R 1 is hydrogen or lower alkyl, lower alkenyl, lower alkynyl, aryl lower alkyl, aryl, heterocyclic lower alkyl, heterocyclic, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, each unsubstituted or substituted with an electron donating group or an electron withdrawing group; and
R 2 and R 3 are independently hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl lower alkyl, aryl, halo, heterocyclic, heterocyclic lower alkyl, lower alkyl heterocyclic, lower cycloalkyl, lower cycloalkyl lower alkyl, or Z—Y wherein R 2 and R 3 may be unsubstituted or substituted with at least one electron withdrawing group or electron donating group;
Z is O, S, S(O) a , NR 4 , or PR 4 ;
Y is hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, lower alkynyl, heterocyclic, heterocyclic lower alkyl, and Y may be unsubstituted or substituted with an electron donating group or an electron withdrawing group, or
ZY taken together is NR 4 NR 5 R 7 , NR 4 OR 5 , ONR 4 R 7 , OPR 4 R 5 , PR 4 OR 5 , SNR 4 R 7 , NR 4 SR 7 , SPR 4 R 5 or PR 4 SR 7 , NR 4 PR 5 R 6 or PR 4 NR 5 R 7 ,
R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, or lower alkynyl, wherein R 4 , R 5 and R 6 may be unsubstituted or substituted with an electron withdrawing group or an electron donating group; and
R 7 is COOR 8 or COR 8 , hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl or lower alkynyl, which R 7 may be unsubstituted or substituted with an electron withdrawing group or electron donating group;
R 8 is hydrogen or lower alkyl, or aryl lower alkyl, and the aryl or alkyl group may be unsubstituted or substituted with an electron withdrawing group or an electron donating group; and
n is 1-4; and
a is 1-3.
51 . The method according to claim 1 wherein the electron withdrawing group and electron donating group are selected from the group consisting of halo, nitro, carboxy, lower alkenyl, lower alkynyl, formyl, carboxyamido, trifluoromethyl, lower alkoxy carbonyl, hydroxy, lower alkoxy, lower alkyl, amino, lower alkylamino, diloweralkylamino, mercapto, loweralkylthio, and lower alkyldithio.
52 . The method according to claim 20 wherein the electron withdrawing group and electron donating group are selected from the group consisting of halo, nitro, carboxy, loweralkoxy carbonyl, lower alkenyl, lower alkynyl, formyl, aryl, arylloweralkanoyl, carboxyamido, hydroxy, loweralkoxy, lower alkyl, amino, lower alkylamino, diloweralkylamino, aryl, aryl lower alkanoyl, trifluoromethyl, aryloxy, lower alkylthio, mercapto, and lower alkyldithio.
53 . The method according to claim 35 wherein the electron withdrawing group and electron donating group are selected from the group consisting of halo, nitro, carboxy, loweralkoxy carbonyl, lower alkenyl, lower alkynyl, formyl, aryl, arylloweralkanoyl, carboxyamido, hydroxy, loweralkoxy, lower alkyl, amino, lower alkylamino, diloweralkylamino, aryl, aryl lower alkanoyl, trifluoromethyl, aryloxy, lower alkylthio, mercapto, and lower alkyldithio.
54 . The method according to claim 50 wherein the electron withdrawing group and electron donating group are selected from the group consisting of halo, nitro, carboxy, lower alkenyl, lower alkynyl, formyl, carboxyamido, trifluoromethyl, lower alkoxy carbonyl, hydroxy, lower alkoxy, lower alkyl, amino, lower alkylamino, diloweralkylamino, mercapto, loweralkylthio, and lower alkyldithio.
55 . The method according to claim 1 wherein the carbon atom which is substituted by R 2 and R 3 is in the D configuration.
56 . The method according to claim 20 wherein the carbon atom which is substituted by R 2 and R 3 is in the D configuration.
57 . The method according to claim 35 wherein the carbon atom which is substituted by R 2 and R 3 is in the D configuration.
58 . The method of claim 1 wherein the compound is of the formula:
wherein
Ar is aryl which is unsubstituted or substituted with an electron donating or electron withdrawing group, and
Q is loweralkoxy.
59 . The method according to claim 56 wherein Ar is unsubstituted aryl or aryl substituted with halo.
60 . The method according to claim 56 wherein Q is methoxy.
61 . The method according to claim 56 wherein Q is methoxy and Ar is unsubstituted aryl or aryl substituted with halo.
62 . The method according to claim 56 wherein the carbon atom which is bonded to CH 2 Q is in the D configuration.
63 . The method according to claim 20 wherein Ar is unsubstituted aryl or aryl substituted with halo wherein the compound has the formula:
and Q is lower alkoxy.
64 . The method according to claim 63 wherein Q is methoxy.
65 . The method according to claim 63 wherein Q is methoxy and Ar is unsubstituted aryl or aryl substituted with halo.
66 . The method according to claim 63 wherein the carbon atom which is bonded to CH 2 Q is in the D configuration.
67 . The method according to claim 63 wherein the carbon atom which is bonded to CH 2 Q is in the D configuration.
68 . The method of claim 35 wherein the compound is of the formula:
wherein
Ar is aryl which is unsubstituted or substituted with an electron donating or electron withdrawing group, and
Q is loweralkoxy.
69 . The method according to claim 68 wherein Ar is unsubstituted aryl or aryl substituted with halo.
70 . The method according to claim 68 wherein Q is methoxy.
71 . The method according to claim 68 wherein Q is methoxy and Ar is unsubstituted aryl or aryl substituted with halo.
72 . The method according to claim 68 wherein the carbon atom which is bonded to CH 2 Q is in the D configuration.Join the waitlist — get patent alerts
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