US6180632B1
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US
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Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1998-11-24
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Granted: 2001-01-30
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Expires: 2018-11-24
Abstract
Abstract This invention is directed to quinoline/quinoxaline compounds which inhibit platelet-derived growth factor or p56 lck tyrosine kinase activity, to pharmaceutical compositions comprising these compounds, and to the use of these compounds for treating a patient suffering from or subject to disorders/conditions involving cellular differentiation, proliferation, extracellular matrix production or mediator release and/or T cell activation and proliferation.
Inventors
- 👤 Michael R. Myers
- 👤 Wei He
- 👤 Alfred P. Spada
- 👤 Martin P. Maguire
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 07:49
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/38; A; A61; A61P; A61P17/00; A61P17/06; A61P19/00; A61P19/08; A61P29/00; A61P35/00; A61P35/02; A61P43/00; A61P9/00; A61P9/10; C07D215/20; C07D241/00; C07D241/36; C07D241/38; C07D241/40; C07D241/42; C07D241/44; C07D241/50; C07D241/52; C07D241/54; C07D403/00; C07D403/02; C07D403/04; C07D405/00; C07D405/02; C07D405/12; C07D453/00; C07D453/06
Claims Analysis
Total Claims: 80
Claim 1
Independent Claim
372 words
A compound of formula I wherein X is L 1 or L 2 Z 2 ; L 1 is (CR 3a R 3b )r or (CR 3a R 3b ) m -Z 3 -(CR 3′a /R 3′b ) n ; L 2 is (CR 3a /R 3b ) p -Z 4 -(CR 3′a /R 3′b ), or ethenyl, Z 1 is N; Z 2 is cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted beterocyclyl, heterocyclenyl or substituted heterocyclenyl; Z 3 is O, NR 4 or SO; Z 4 is O, NH, S, SO S 2 or a bond; m is 0 or 1; n is 2 or 3, and n+m=2 or 3; p and q are independently 0, 1, 2, 3 or 4, and p+q=0, 1, 2, 3 or 4 when Z 4 is a bond, and p+q=0, 1, 2 or 3 when Z 4 is other than a bond; r is 2, 3 or 4; R 1a and R 1b are independently alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, hydroxy, acyloxy, alkoxy, substituted alkoxy, cycloalkoxy, substituted cycloalkyloxy, heterocyclyloxy, substituted heterocyclyloxy, heterocyclylcarbonyloxy, substituted heterocyclylcarbonyloxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, cyano, R 5 R 6 N- or acylR 5 N-, or one of R 1a and R 1b is hydrogen or halo and the other is alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, hydroxy, acyloxy, alkoxy, substituted alkoxy, cycloalkyloxy, substituted cycloalkyloxy, heterocyclyloxy, substituted heterocyclyloxy, heterocyclylcarbonyloxy, substituted heterocyclylcarbonyloxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, cyano, R 5 R 6 N- or acylR 5 N-; R 1c is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, hydroxy, acyloxy, alkoxy, substituted alkoxy, cycloalkyloxy, substituted cycloalkyloxy, heterocyclyloxy, substituted heterocyclyloxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, halo, cyano, R 5 R 6 N- or acylR 5 N-; R 3a , R 3b , R 3′a and R 3′b are independently hydrogen or alkyl; R 4 is hydrogen, alkyl or acyl; and R 5 and R 6 are independently hydrogen or alkyl, or R 5 and R 6 taken together with the nitrogen atom to which R 5 and R 6 are attached form a heterocyclyl, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
372 words
A compound of formula I wherein X is L 1 or L 2 Z 2 ; L 1 is (CR 3a R 3b )r or (CR 3a R 3b ) m -Z 3 -(CR 3′a /R 3′b ) n ; L 2 is (CR 3a /R 3b ) p -Z 4 -(CR 3′a /R 3′b ), or ethenyl, Z 1 is N; Z 2 is cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl, substituted beterocyclyl, heterocyclenyl or substituted heterocyclenyl; Z 3 is O, NR 4 or SO; Z 4 is O, NH, S, SO S 2 or a bond; m is 0 or 1; n is 2 or 3, and n+m=2 or 3; p and q are independently 0, 1, 2, 3 or 4, and p+q=0, 1, 2, 3 or 4 when Z 4 is a bond, and p+q=0, 1, 2 or 3 when Z 4 is other than a bond; r is 2, 3 or 4; R 1a and R 1b are independently alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, hydroxy, acyloxy, alkoxy, substituted alkoxy, cycloalkoxy, substituted cycloalkyloxy, heterocyclyloxy, substituted heterocyclyloxy, heterocyclylcarbonyloxy, substituted heterocyclylcarbonyloxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, cyano, R 5 R 6 N- or acylR 5 N-, or one of R 1a and R 1b is hydrogen or halo and the other is alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, hydroxy, acyloxy, alkoxy, substituted alkoxy, cycloalkyloxy, substituted cycloalkyloxy, heterocyclyloxy, substituted heterocyclyloxy, heterocyclylcarbonyloxy, substituted heterocyclylcarbonyloxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, cyano, R 5 R 6 N- or acylR 5 N-; R 1c is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, hydroxy, acyloxy, alkoxy, substituted alkoxy, cycloalkyloxy, substituted cycloalkyloxy, heterocyclyloxy, substituted heterocyclyloxy, aryloxy, substituted aryloxy, heteroaryloxy, substituted heteroaryloxy, halo, cyano, R 5 R 6 N- or acylR 5 N-; R 3a , R 3b , R 3′a and R 3′b are independently hydrogen or alkyl; R 4 is hydrogen, alkyl or acyl; and R 5 and R 6 are independently hydrogen or alkyl, or R 5 and R 6 taken together with the nitrogen atom to which R 5 and R 6 are attached form a heterocyclyl, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
198 words
The compound of claim 1 wherein L 1 is (CR 3a R 3b ) m -Z 3 -(CR 3′a R 3′b ) n ; L 2 is (CR 3a R 3b ) p -Z 4 -(CR 3′a R 3′b ) q ; Z 2 is cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heterocyclyl or substituted heterocyclyl; Z 3 and Z 4 are O or NH; m is 0; n is 2 or 3; p+q=0 or 1; R 1a and R 1b are independently alky, substituted alkyl, alkoxy, substituted alkoxy, cycloalkyloxy, substituted cycloalkyloxy, heterocyclyloxy, substituted heterocyclyloxy or R 5 RN-, or one of R 1a and R 1b is hydrogen or halo and the other is substituted alkyl, alkoxy, substituted alkoxy, cycloalkyloxy, substituted cycloalkyloxy, heterocyclyloxy, substituted heterocyclyloxy or R 5 R 6 N-; R 1c is hydrogen, alkyl substituted alkyl, alkoxy or substituted alkoxy; R 3a , R 3b , R 3+a and R 3′b are independently hydrogen or lower alkyl; and R 5 and R 6 taken together with the nitrogen atom to which R 5 and R 6 are attached form a heterocyclyl, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
115 words
The compound of claim 1 wherein X is L 2 Z 2 ; L 2 is (CR 3a R 3b ) p -Z 4 -(CR 3′a R 3′b ) q ; Z 2 is cycloalkyl, substituted cycloalkyl, cycloalkenyl or substituted cycloalkenyl; Z 4 is 0 or NH; p is 0; q is 0 or 1; R 1a and R 1b are independently alkyl substituted alkyl, alkoxy, substituted alkoxy, cycloalkyloxy, substituted cycloalkyloxy heterocyclyloxy or substituted heterocyclyloxy, or one of R 1a and R 1b is hydrogen or halo; R 1c is hydrogen; and R 3′a and R 3′b are independently hydrogen; or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
11 words
The compound of claim 1 wherein L 1 is lower alkyl.
Claim 6
Dependent Claim
10 words
The compound of claim 1 wherein Z 1 is N.
Claim 7
Dependent Claim
13 words
The compound of claim 1 wherein Z 2 is cycloalkyl or substituted cycloalkyl.
Claim 8
Dependent Claim
13 words
The compound of claim 1 wherein Z 2 is alkyl substituted monocyclic cycloalkyl.
Claim 9
Dependent Claim
12 words
The compound of claim 1 wherein Z 2 is methylcyclopentyl or methylcyclohexyl.
Claim 10
Dependent Claim
11 words
The compound of claim 1 wherein Z 2 is multicyclic cycloalkyl.
Claim 11
Dependent Claim
12 words
The compound of claim 1 wherein Z 2 is [2.2.1]bicycloheptanyl(norbornyl) or [2.2.2]bicyclooctanyl.
Claim 12
Dependent Claim
12 words
The compound of claim 1 wherein Z 2 is optionally substituted cycloalkenyl.
Claim 13
Dependent Claim
12 words
The compound of claim 1 wherein Z 2 is cyclopentenyl and cyclohexenyl.
Claim 14
Dependent Claim
12 words
The compound of claim 1 wherein Z 2 is [2.2.1]bicycloheptenyl(norbornenyl) or [2.2.2]bicyclooctenyl.
Claim 15
Dependent Claim
11 words
The compound of claim 1 wherein p and q are 0.
Claim 16
Dependent Claim
7 words
The compound of claim 1 wherein p+q=1.
Claim 17
Dependent Claim
10 words
The compound of claim 1 wherein Z 4 is O.
Claim 18
Dependent Claim
16 words
The compound of claim 1 wherein Z 4 is O, and p and q are 0.
Claim 19
Dependent Claim
13 words
The compound of claim 1 wherein Z 4 is O, and p+q =1.
Claim 20
Dependent Claim
12 words
The compound of claim 1 wherein Z 4 is NR 4 .
Claim 21
Dependent Claim
18 words
The compound of claim 1 wherein Z 4 is NR 4 , and p and q are 0.
Claim 22
Dependent Claim
14 words
The compound of claim 1 wherein Z 4 is NR 4 , and m+n=1.
Claim 23
Dependent Claim
10 words
The compound of claim 1 wherein Z 4 is S.
Claim 24
Dependent Claim
16 words
The compound of claim 1 wherein Z 4 is S, and p and q are 0.
Claim 25
Dependent Claim
12 words
The compound of claim 1 wherein Z 4 is S, and p+q=1.
Claim 26
Dependent Claim
36 words
The compound of claim 1 wherein R 1a and R 1b are independently lower alkyl hydroxy substituted lower alkyl, hydroxy, lower alkoxy, cycloalkyloxy, heterocyclyloxy, or one of R 1a and R 1b is hydrogen or halo.
Claim 27
Dependent Claim
20 words
The compound of claim 1 wherein R 1a and R 1b are independently heterocyclylcarbonyloxy lower alkoxy or substituted lower alkoxy.
Claim 28
Dependent Claim
13 words
The compound of claim 1 wherein the lower alkoxy is methoxy or ethoxy.
Claim 29
Dependent Claim
14 words
The compound of claim 1 wherein R 1a and R 1b are lower alkyl.
Claim 30
Dependent Claim
13 words
The compound of claim 1 wherein the lower alkyl is methyl or ethyl.
Claim 31
Dependent Claim
27 words
The compound of claim 1 wherein one of R 1a and R 1b is lower alkoxy, and the other of R 1a and R 1b is halo.
Claim 32
Dependent Claim
20 words
The compound of claim 1 wherein the lower alkoxy is methoxy or ethoxy, and the halo is chloro or bromo.
Claim 33
Dependent Claim
28 words
The compound of claim 1 wherein one of R 1a and R 1b is lower alkyl, and the other of R 1a and R 1b is lower alkoxy.
Claim 34
Dependent Claim
21 words
The compound of claim 1 wherein the lower alkoxy is methoxy or ethoxy, and the lower alkyl is methyl or ethyl.
Claim 35
Dependent Claim
27 words
The compound of claim 1 wherein one of R 1a and R 1b is lower alkoxy, and the other of R 1a and R 1b is cycloalkyloxy.
Claim 36
Dependent Claim
20 words
The compound of claim 1 wherein the lower alkoxy is methoxy or ethoxy, and the cycloalkyloxy is cyclopentyloxy or cyclohexyloxy.
Claim 37
Dependent Claim
30 words
The compound of claim 1 wherein one of R 1a and R 1b is hydrogen, and the other of R 1a and R 1b is lower alkoxy, cycloalkyloxy or heterocyclyloxy.
Claim 38
Dependent Claim
13 words
The compound of claim 36 wherein the lower alkoxy is methoxy or ethoxy.
Claim 39
Dependent Claim
12 words
The compound of claim 36 wherein the cycloalkyloxy is cyclopentyloxy or cyclohexyloxy.
Claim 40
Dependent Claim
10 words
The compound of claim 36 wherein the heterocyclyloxy is furanyloxy.
Claim 41
Dependent Claim
15 words
The compound of claim 1 wherein R 1c is hydrogen, lower alkyl or lower alkoxy.
Claim 42
Dependent Claim
13 words
The compound of claim 40 wherein the lower alkoxy is methoxy or ethoxy.
Claim 43
Dependent Claim
25 words
The compound of claim 1 wherein R 1a and R 1b are lower alkoxy or lower alkoxy substituted with alkoxy, heterocyclyl, carboxy, alkoxycarbonyl or carbamoyl.
Claim 44
Dependent Claim
37 words
The compound of claim 1 wherein one of R 1a and R 1b is unsubstituted lower alkoxy and the other of R 1a and R 1b is lower alkoxy substituted with alkoxy, heterocyclyl, carboxy, alkoxycarbonyl or carbamoyl.
Claim 45
Dependent Claim
35 words
The compound of claim 1 wherein one of R 1a and R 1b is methoxy and the other of R 1a and R 1b is [1,4′]-bipiperadin-1′-ylcarbonyloxy, 2-(ethoxy)ethoxy, 2-(4-morpholinyl)ethoxy, 2-(4-methylpiperazin-1-yl)ethoxy, carboxymethoxy, methoxycarbonylmethoxy, aminocarbonylmethoxy, N-methylaminocarbonylmethoxy or N,N-dimethylaminocarbonylmethoxy.
Claim 46
Dependent Claim
90 words
A compound according to claim 1 which is: 3-Cyclohexyloxy-6,7-dimethoxyquinoline; 2-cyclohexylamino-6,7-dimethoxyquinoxaline; 2-cyclohexylamino-6,7-dimethoxyquinoxaline; exo-bicyclo[2.2.1]hept-2-yl-(6-chloro-7-methoxyquinoxalin-9-yl)amine; exo-bicyclo[2.2.1]hept-2-yl-(7-chloro-6-methoxyquinoxalin-2-yl)amine; Bicyclo[2.2.1]hept-2-yl-(6,7-dimethyl-quinoxalin-2-yl)-amine; 2-cycloheptylamino-6,7-dimethoxyquinoxaline; 2-cyclopentylamino-6,7-dimethoxyquinoxaline; 2-cyclohexylamino-6-methoxyquinoxaline; 3-Aminocyclohexyl-6,7-dimethoxy-quinoline; (6,7-dimethoxy-quinolin-3-yl)-cis-(3-(R)-methyl-cyclohexyl)amine; 2-Cyclohexylamino-6-methoxy-7-bromo-quinoxaline hydrochloride; (6,7-Dimethoxyquinolin-3-yl)-cis/trans-(3-(R)-methyl-cyclohexyl)-amine (6,7-Dimethoxyquinolin-3-yl)-trans-(3-(R)-methyl-cyclohexyl)-amine (6,7-Dimethoxyquinolin-3-yl)-cis-(3-(R)-methyl-cyclohexyl)-amine; (6,7-dimethoxy-quinolin-3-yl)-(3-methyl-cyclopentyl)amine; Cyclohex-3-enyl-(6,7-dimethoxyquinoxalin-2-yl)-amine; 2,7-Bis-cyclohexyloxy-6-methoxy-quinoxaline; Cyclohexyl-(6,7-dimethoxyquinoxalin-2-ylmethyl)-amine; (6,7-Dimethoxyquinolin-3-yl)-isobutyl amine; Cyclohexyl-(6-methoxy-7-morpholin-4-yl-quinoxalin-2-yl)-amine; (±)-Bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine; exo-bicyclo[2.2.1]hept-5-en-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine; Cyclohexyl-(6,8-dimethyl-quinoxalin-2-yl)-amine; Endo-bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine; (6,7-Dimethoxyquinoxalin-2-yl)-(4-methoxy-cyclohexyl)-amine; Exo-bicyclo[2.2.1]hept-2-yl-(6-methoxyquinoxalin-2-yl)-amine; exo-2-(Bicyclo[2.2.1]hept-2-yloxy)-6,7-dimethoxyquinoxaline; (Bicyclo[2.2.2]oct-2-yloxy)-6,7-dimethoxy-quinoxaline; Endo-2-(bicyclo[2.2.1]hept-2-yloxy)-6,7-dimethoxy-quinoxaline; exo-2-(Bicyclo[2.2.1]hept-5-en-2-yloxy)-6,7-dimethoxyquinoxaline; (Bicyclo[2.2.1]hept-5-en-2-yloxy)-6,7-dimethoxyquinoxaline; 2-Cyclohexyloxy-6,7-dimethoxyquinoxaline; 2-cyclopentylthio-6,7-dimethoxy-quinoxaline; 6,7-dimethoxy-2-cyclopentyloxy-quinoxaline; 2-cyclopentylmethyloxy-6,7-dimethoxy-quinoxaline; 6,7-dimethoxy-2-tetrahydropyran-4-oxy-quinoxaline; exo,exo-6,7-dimethoxy-2-(5,6-epoxy-bicyclo[2.2.1]beptan-2-yloxy)-quinoxaline; cis/trans-4-(6,7-Dimethoxyquinoxalin-2-yloxy)-cyclohexanecarboxylic acid; 6,7-Dimethoxy-2-(4-methoxy-cyclohexyloxy)-quinoxaline; (1R,2R,4S)-(+)-Bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine; (1S,2S,4R)-(−)-Bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine; (6,7-Dimethoxy-quinoxalin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one; Cis/trans-4-(6,7-Dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid methyl ester; Cis/trans-4-(6,7-dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid; Cis-4-(6,7-dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid methyl ester; Trans-4-(6,7-dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid methyl ester; (6,7-dimethoxy-quinoxaline-2-yl)-cis/trans-(3-(R)-methylcyclohexyl)amine; (6,7-dimethoxy-quinoxaline-2-yl) -trans-(3-(R)-methylcyclohexyl)amine; (6,7-dimethoxy-quinoxaline-2-yl)-cis-(3-(R)-methylcyclohexyl)amine; or methyl cis/trans-4-(6,7-Dimethoxyquinoxalin-2-yloxy)-cyclohexanecarboxylate, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 47
Dependent Claim
24 words
A compound according to claim 1 which is 2-cyclohexylamino-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 48
Dependent Claim
24 words
A compound according to claim 1 which is exo-bicyclo[2.2.1]hept-2-yl-(6-chloro-7-methoxyquinoxalin-2-yl)amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 49
Dependent Claim
9 words
A compound according to claim 1 which is exo-bicyclo[2.2.1]hept-2-yl-(7-chloro-6-methoxyquinoxalin-2-yl)amine.
Claim 50
Dependent Claim
24 words
A compound according to claim 1 which is Bicyclo[2.2.1]hept-2-yl-(6,7-dimethyl-quinoxalin-2-yl)amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 51
Dependent Claim
24 words
A compound according to claim 1 which is 2-cycloheptylamino-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 52
Dependent Claim
24 words
A compound according to claim 1 which is 2-cyclopentylamino-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 53
Dependent Claim
24 words
A compound according to claim 1 which is Cyclohex-3-enyl-(6,7-dimethoxyquinoxalin-2-yl)-amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 54
Dependent Claim
24 words
A compound according to claim 1 which is 2,7-Bis-cyclohexyloxy-6-methoxy-quinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 55
Dependent Claim
24 words
A compound according to claim 1 which is (±)-Bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 56
Dependent Claim
24 words
A compound according to claim 1 which is exo-bicyclo[2.2.1]hept-5-en-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 57
Dependent Claim
24 words
A compound according to claim 1 which is Endo-bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 58
Dependent Claim
24 words
A compound according to claim 1 which is Exo-bicyclo[2.2.1]hept-2-yl-(6-methoxyquinoxalin-2-yl)-amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 59
Dependent Claim
24 words
A compound according to claim 1 which is exo-2-(Bicyclo[2.2.1]hept-2-yloxy)-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 60
Dependent Claim
24 words
A compound according to claim 1 which is 2-(Bicyclo[2.2.2]oct-2-yloxy)-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 61
Dependent Claim
24 words
A compound according to claim 1 which is Endo-2-(bicyclo[2.2.1]hept-2-yloxy)-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 62
Dependent Claim
24 words
A compound according to claim 1 which is exo-2-(Bicyclo[2.2.1]hept-5-en-2-yloxy)-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 63
Dependent Claim
24 words
A compound according to claim 1 which is 2-(Bicyclo[2.2.1]hept-5-en-2-yloxy)-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof; solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 64
Dependent Claim
24 words
A compound according to claim 1 which is 2-Cyclohexyloxy-6,7-dimethoxyquinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 65
Dependent Claim
24 words
A compound according to claim 1 which is 2-cyclopentylthio-6,7-dimethoxy-quinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 66
Dependent Claim
24 words
A compound according to claim 1 which is 6,7-dimethoxy-2-cyclopentyloxy-quinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 67
Dependent Claim
24 words
A compound according to claim 1 which is 2-cyclopentylmethyloxy-6,7-dimethoxy-quinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 68
Dependent Claim
24 words
A compound according to claim 1 which is 6,7-dimethoxy-2-tetrahydropyran-4-oxy-quinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 69
Dependent Claim
24 words
A compound according to claim 1 which is exo,exo-6,7-dimethoxy-2-(5,6-epoxy-bicyclo[2.2.1]heptan-2-yloxy)-quinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 70
Dependent Claim
24 words
A compound according to claim 1 which is 6,7-Dimethoxy-2-(4-methoxy-cyclohexyloxy)-quinoxaline, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 71
Dependent Claim
24 words
A compound according to claim 1 which is (1R,2R,4S)-(+)-Bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 72
Dependent Claim
24 words
A compound according to claim 1 which is (1S,2S,4R)-(−)-Bicyclo[2.2.1]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 73
Dependent Claim
27 words
A compound according to claim 1 which is Cis/trans-4-(6,7-Dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid methyl ester, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 74
Dependent Claim
27 words
A compound according to claim 1 which is Cis-4-(6,7-dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid methyl ester, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 75
Dependent Claim
27 words
A compound according to claim 1 which is Trans-4-(6,7-dimethoxy-quinoxalin-2-ylamino)-cyclohexanecarboxylic acid methyl ester, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 76
Dependent Claim
24 words
A compound according to claim 1 which is (6,7-dimethoxy-quinoxaline-2-yl)-cis/trans-(3-(R)-methylcyclohexyl)amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 77
Dependent Claim
24 words
A compound according to claim 1 which is (6,7-dimethoxy-quinoxaline-2-yl)-trans-(3-(R)-methylcyclohexyl)amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 78
Dependent Claim
24 words
A compound according to claim 1 which is (6,7-dimethoxy-quinoxaline-2-yl)-cis-(3-(R)-methylcyclohexyl)amine, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 79
Dependent Claim
25 words
A compound according to claim 1 which is methyl cis/trans-4-(6,7-Dimethoxyquinoxalin-2-yloxy)-cyclohexanecarboxylate, or an N-oxide thereof, hydrate thereof, solvate thereof, prodrug thereof, or pharmaceutically acceptable salt thereof.
Claim 80
Dependent Claim
20 words
A pharmaceutical composition comprising the compound of claim 1 , or pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2004-01-30 | 2004-07-31 | 2005-01-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2008-01-30 | 2008-07-31 | 2009-01-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2012-01-30 | 2012-07-31 | 2013-01-30 | $7700.00 | Window Closed / Lapsed |