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US6180632B1 Expired / Lapsed US ⏱️ 0.0 years remaining

Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases

Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1998-11-24
•
Granted: 2001-01-30
•
Expires: 2018-11-24
📄 Original PDF 🌐 Google Patents

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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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

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