US4959361A
Expired / Lapsed
US
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Triazolo(4,3-A)(1,4)benzodiazepines and thieno (3,2-F)(1,2,4)triazolo(4,3-A)(1,4)diazepine compounds which have useful activity as platelet activating factor (PAF) antagonists
Assignee: Hoffmann La Roche Inc
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Filing: 1988-10-03
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Granted: 1990-09-25
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Expires: 2008-10-03
Abstract
Abstract The invention relates to compounds of the formula ##STR1## wherein X is --CH═CH-- or S; R 1 is lower alkyl, lower alkoxy or trifluoromethyl; R 2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or alkanoyloxy; R 3 and R 4 , independently, are hydrogen, chlorine, fluorine, lower alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1, R 2 cannot be hydroxy, lower alkoxy or alkanoyloxy; R 5 is a radical of the formula R 6 --(CH 2 ) n -- or R 7 --O--(CH 2 ) m -- wherein R 6 and R 7 are aryl or a heterocyclic radical, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0, R 6 must be attached through a carbon to carbon bond, and provided that R 7 is always attached through a carbon to oxygen bond, and, when at least one asymmetric carbon is present, its enantiomers and racemates, and pharmaceutically acceptable acid addition salts thereof. The compounds of formula I exhibit activity as platelet activating factor (PAF) antagonists and are, therefore, useful in disease states characterized by excess platelet activating factor or for the prevention and treatment of cardiovascular diseases, pulmonary diseases, immunological disorders, inflammatory diseases, dermatological disorders, shock or transplant rejection.
Inventors
- 👤 Armin Walser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 03:51
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D495/00; C07D495/12; C07D495/14; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812
Claims Analysis
Total Claims: 67
Claim 1
Independent Claim
221 words
A compound of formula ##STR89## wherein X is --CH═CH-- or S; R 1 is lower alkyl, lower alkoxy or trifluoromethyl; R 2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or acetyloxy; R 3 and R 4 , independently, are hydrogen, chlorine, fluorine, lower alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1, R 2 cannot be hydroxy, lower alkoxy or acetyloxy; R 5 is a radical of the formula R 7 --O--(CH 2 ) m --C.tbd.C-- wherein R 6 and R 7 are naphthyl, phenyl or phenyl or naphthyl mono-, di- , or trisubstituted by chlorine, fluorine, lower alkoxy or lower alkoxy or a heterocyclic radical selected from the group consisting of pyridinyl, imidazolinyl, thienyl, furyl, pyrimidinyl, oxazolinyl, ##STR90## which can be substituted by one or two substitutents selected from the group consisting of lower alkyl, lower alkoxy, chlorine and fluorine, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0R 6 must be attached through a carbon to carbon bond, and provided that R 7 is always attached through a carbon to oxygen bond, or, when at least one asymmetric carbon is present, an enantiomer or racemate thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
221 words
A compound of formula ##STR89## wherein X is --CH═CH-- or S; R 1 is lower alkyl, lower alkoxy or trifluoromethyl; R 2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or acetyloxy; R 3 and R 4 , independently, are hydrogen, chlorine, fluorine, lower alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1, R 2 cannot be hydroxy, lower alkoxy or acetyloxy; R 5 is a radical of the formula R 7 --O--(CH 2 ) m --C.tbd.C-- wherein R 6 and R 7 are naphthyl, phenyl or phenyl or naphthyl mono-, di- , or trisubstituted by chlorine, fluorine, lower alkoxy or lower alkoxy or a heterocyclic radical selected from the group consisting of pyridinyl, imidazolinyl, thienyl, furyl, pyrimidinyl, oxazolinyl, ##STR90## which can be substituted by one or two substitutents selected from the group consisting of lower alkyl, lower alkoxy, chlorine and fluorine, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0R 6 must be attached through a carbon to carbon bond, and provided that R 7 is always attached through a carbon to oxygen bond, or, when at least one asymmetric carbon is present, an enantiomer or racemate thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
11 words
A compound in accordance with claim 1. wherein s is 0.
Claim 4
Dependent Claim
11 words
A compound, in accordance with claim 1, wherein s is 1.
Claim 5
Dependent Claim
10 words
A compound, in accordance with claim 2, wherein X is
Claim 6
Dependent Claim
11 words
A compound, in accordance with claim 2, wherein X is S.
Claim 7
Dependent Claim
9 words
A compound, in accordance with claim 4, wherein ##STR91##
Claim 8
Dependent Claim
9 words
A compound, in accordance with claim 4, wherein ##STR92##
Claim 9
Dependent Claim
9 words
A compound, in accordance with claim 5, wherein ##STR93##
Claim 10
Dependent Claim
9 words
A compound, in accordance with claim 5, wherein ##STR94##
Claim 11
Dependent Claim
14 words
A compound, in accordance with claim 8, wherein R 6 is a heterocyclic radical.
Claim 12
Dependent Claim
11 words
A compound, in accordance with claim 9, wherein R 7 is
Claim 13
Dependent Claim
36 words
A compound, in accordance with claim 10, wherein R 1 , is methyl or ethyl, R2 is hydrogen, R is fluorine or chlorine, R 4 is hydrogen, s is 0 and n is 1 or 2.
Claim 14
Dependent Claim
46 words
A compound, in accordance with claim 10, wherein R 1 is methyl, R 2 is hydrogen, R is fluorine or chlorine at the 2-position of the phenyl moiety. R 4 is hydrogen. s is 0, n is 1 and R 6 is hetero-bicyclic or hetero-tricyclic group.
Claim 15
Dependent Claim
68 words
A compound, in accordance with claim 10, wherein R 1 is methyl, R 2 is hydrogen, R 3 is chlorine and at the 2-position of the phenyl moiety, R 4 is hydrogen, n is 1 and R 6 is selected from the group consisting of ##STR95## which can be substituted by one or two substituents selected from the group consisting of lower alkyl, lower alkoxy, chlorine and fluorine.
Claim 16
Dependent Claim
29 words
A compound, in accordance with claim 11, wherein R 1 is methyl or ethyl. R 2 is hydrogen, R 3 is fluorine or chlorine and R 4 is hydrogen.
Claim 17
Dependent Claim
57 words
A compound, in accordance with claim 11, wherein R 1 is methyl, R 2 is hydrogen, R 3 is fluorine or chlorine at the 2-position of the phenyl moiety, R 4 is hydrogen, m is and R 7 is phenyl, naphthyl or phenyl or naphthyl mono-, di- or trisubstituted by chlorine, fluorine, lower alkyl or lower alkoxy.
Claim 18
Dependent Claim
42 words
A compound, in accordance with claim 9, wherein R 1 is methyl, R2 is hydrogen, R 3 is chlorine and at the 2-position of the phenyl moiety, R 4 is hydrogen, n is 1 and R 7 is phenyl, naphthyl or pyridyl.
Claim 19
Dependent Claim
8 words
A compound, in accordance with claim 1, 1-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3.2-f][1,2,4][4,3-a][4,1]diazepin-2-yl]-2-propynyl]-benz[cd]-indol-2(1H)-one.
Claim 20
Dependent Claim
9 words
A compound, in accordance with claim 1, 5-{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazol 4,3-a][4,1]diazepin-2-yl]-2-propynyl}-phenanthridin-6(5H)-one.
Claim 21
Dependent Claim
8 words
A compound, in accordance with claim 1, 4-(2-chlorophenyl)-2-[3-(1,2.3,4-tetrahydro-9H-carbazol-9-yl)1-propynyl]-9-methyl-6H-thi®no-[3,2-f]1,2,4]triazolo[4,3-a][1,4]diazepine.
Claim 22
Dependent Claim
8 words
A compound, in accordance with claim 1, 1-{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]-2-propynyl}-3,4-dihydro2(1H)-quinolinone.
Claim 23
Dependent Claim
8 words
A compound, in accordance with claim 1, 4-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl]-2H-4,1-benzoxazin-3(4H)-one.
Claim 24
Dependent Claim
8 words
A compound, in accordance with claim 1, 1-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl]-1H-indole2,3-dione.
Claim 25
Dependent Claim
9 words
A compound in accordance with claim 1 1-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl].1,3-dihydro 2H-indol-2-one.
Claim 26
Dependent Claim
8 words
A compound, in accordance with claim 1. 2-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl]-1,2,4triazolo[4,3-a]pyridin-3(2H)-one.
Claim 27
Dependent Claim
9 words
A compound, in accordance with claim 1, 2-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl]-1,2-benziso-thiazol-3(2H)-one 1,1-dioxide.
Claim 28
Dependent Claim
8 words
A compound, in accordance with claim 1, 4-(2-Chlorophenyl)-2-[3-(1H-indazol-1-yl)-1-propynyl]-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepine.
Claim 29
Dependent Claim
8 words
A compound, in accordance with claim 1, 2-[3-(1H-Benzimidazol-1-yl)-1-propynyl]-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine.
Claim 30
Dependent Claim
10 words
A compound, in accordance with claim 1, 2-[3-[6-(2-Fluorophenyl)-1-methyl-4H-[1,2 4]triazolo [4,3-a][4,1]benzodiazepin-8-yl]-2-propynyl]-1H-isoindole-1,3(2H)-dione.
Claim 31
Dependent Claim
9 words
A compound, in accordance with claim 1, 4-[3-[6-(2-Fluorophenyl)-1-methyl-4H-[1,2,4]triazolo [4,3-a][4,1]benzodiazepin-8-yl]-2-propynyl]-2H-4,1-benzoxazin-3(4H)-one.
Claim 32
Dependent Claim
9 words
A compound, in accordance with claim 1, 4-(2-chlorophenyl)-9-methyl-2-[3-(3-pyridyloxy-1-propynyl)-6H. thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepine.
Claim 33
Dependent Claim
243 words
A pharmaceutical composition comprising an effective amount of a compound of formula ##STR96## wherein X is --CH═CH-- or S; R 1 is lower alkyl, lower alkoxy or trifluoromethyl; R 2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or acetyloxy; R 3 and R 4 , independently, are hydrogen, chlorine, fluorine, lower alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1 , R 2 cannot be hydroxy, lower alkoxy or acetyloxy; R 5 is a radical of the formula R 6 --(CH 2 ) n --C.tbd.C-- or R 7 --O--(CH 2 ) m --C.tbd.C-- wherein R 6 and R 7 are naphthyl, phenyl or phenyl or naphthyl mono-, di- or trisubstituted by chlorine, fluorine, lower alkyl or lower alkoxy or a heterocyclic radical selected from the group consisting of pyridinyl, imidazolinyl, thienyl, furyl, pyrimidinyl, oxazolinyl, ##STR97## which can be substituted by one or two substituents selected from the group consisting of lower alkyl, lowr alkoxy, chlorine and fluorine, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0, R 6 must be attached through a carbon to carbon bond, and provided that R 7 is always attached through a carbon to oxygen bond, or, when at least one asymmetric carbon is present, an enantiomer or racemate thereof, or a pharmaceutically acceptable acid addition salt thereof, and an inert carrier material.
Claim 34
Dependent Claim
243 words
A pharmaceutical composition comprising an effective amount of a compound of formula ##STR96## wherein X is --CH═CH-- or S; R 1 is lower alkyl, lower alkoxy or trifluoromethyl; R 2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or acetyloxy; R 3 and R 4 , independently, are hydrogen, chlorine, fluorine, lower alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1 , R 2 cannot be hydroxy, lower alkoxy or acetyloxy; R 5 is a radical of the formula R 6 --(CH 2 ) n --C.tbd.C-- or R 7 --O--(CH 2 ) m --C.tbd.C-- wherein R 6 and R 7 are naphthyl, phenyl or phenyl or naphthyl mono-, di- or trisubstituted by chlorine, fluorine, lower alkyl or lower alkoxy or a heterocyclic radical selected from the group consisting of pyridinyl, imidazolinyl, thienyl, furyl, pyrimidinyl, oxazolinyl, ##STR97## which can be substituted by one or two substituents selected from the group consisting of lower alkyl, lowr alkoxy, chlorine and fluorine, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0, R 6 must be attached through a carbon to carbon bond, and provided that R 7 is always attached through a carbon to oxygen bond, or, when at least one asymmetric carbon is present, an enantiomer or racemate thereof, or a pharmaceutically acceptable acid addition salt thereof, and an inert carrier material.
Claim 35
Dependent Claim
12 words
A pharmaceutical composition, in accordance wirh claim 32, wherein s is 0.
Claim 36
Dependent Claim
12 words
A pharmaceutical composition, in accordance with claim 33, wherein s is 1.
Claim 37
Dependent Claim
12 words
A pharmaceutical composition, in accordance with claim 33, wherein X is --CH═CH--.
Claim 38
Dependent Claim
12 words
A pharmaceutical composition, in accordance with claim 34, wherein X is S.
Claim 39
Dependent Claim
13 words
A pharmaceutical composition, in accordance with claim 35, wherien R 5 is ##STR98##
Claim 40
Dependent Claim
13 words
A pharmaceutical composition, in accordance with claim 35, wherein R 5 ios ##STR99##
Claim 41
Dependent Claim
13 words
A pharmaceutical composition, in accordance with claim 36, wherein R 5 is ##STR100##
Claim 42
Dependent Claim
13 words
A pharmaceutical composition, in accordance with claim 36, wherein R 5 is ##STR101##
Claim 43
Dependent Claim
16 words
A pharmaceutical composition, in accordance with claim 32, wherein the compound of formula I is 2-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.
Claim 44
Dependent Claim
16 words
A pharmaceutical composition, in accordance with claim 32, wherein the compound of formula I is 1-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl]-benz[cd]indol-2(1H)-one.
Claim 45
Dependent Claim
16 words
A pharmaceutical composition, in accordance with claim 32, wherein the compound of formula I is 4-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl]-2H-1,4-benzoxazin-3(4H)-one.
Claim 46
Dependent Claim
16 words
A pharmaceutical composition, in accordance with claim 32, wherein the compound of formula I is 5-{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]-2-propynyl]-phenanthridin-6(5H)-one.
Claim 47
Dependent Claim
16 words
A pharmaceutical composition, in accordance with claim 32, wherein the compound of formula 1 is 4-(2-chlorophenyl)-2-[3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)1-propynyl]-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][4,1]diazepine.
Claim 48
Dependent Claim
17 words
A pharmaceutical composition, in accordance with claim 32, wherein the compound of formula I is 1-{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl}-3,4-dihydro-2 (1H)-quinolinone.
Claim 49
Independent Claim
248 words
A method which comprises administering to a host requiring a paltelet activating factor antagonist an effecting amount of a compound of the formula ##STR102## wherein X is --CH═CH-- or S; R 1 is lower alkyl, lower alkoxy or trifuloromethyl; R 2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or acetyloxy; R 3 and R 4 , independently, are hydrogen, chlorine, fluorine, lowr alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1, R 2 cannot be hydroxy, lower alkoxy or acetyloxy; R 5 is a radical of the formula R 6 --(CH 2 ) n --C.tbd.C-- or R 7 --O--(CH 2 ) m --C.tbd.C-- wherein R 6 and R 7 are naphthyl, phenyl or phenyl or naphthyl mono-, di- or trisubstituted by chlorine, fluorine, lower alkyl or lower alkoxy or a heterocyclic radical selected from the group consisting of pyridinyl, imidazolinyl, thienyl, furyl, pyrimidinyl, oxazolinyl, ##STR103## which can be substituted by one or two substituents selected from the group consisting of lower alkyl, lower alkoxy, chlorine and fluorine, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0, R 6 must be attached trhough a carbon to carbon bond, and provided that R 7 is always attached through a carbon to oxygen bond, or, when at least one asymmetric carbon is present, an enantiomer or racemate thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 50
Independent Claim
248 words
A method which comprises administering to a host requiring a paltelet activating factor antagonist an effecting amount of a compound of the formula ##STR102## wherein X is --CH═CH-- or S; R 1 is lower alkyl, lower alkoxy or trifuloromethyl; R 2 is hydrogen, lower alkyl, lower alkoxy, hydroxy or acetyloxy; R 3 and R 4 , independently, are hydrogen, chlorine, fluorine, lowr alkyl or lower alkoxy; s is an integer from 0 to 1, provided that when s is 1, R 2 cannot be hydroxy, lower alkoxy or acetyloxy; R 5 is a radical of the formula R 6 --(CH 2 ) n --C.tbd.C-- or R 7 --O--(CH 2 ) m --C.tbd.C-- wherein R 6 and R 7 are naphthyl, phenyl or phenyl or naphthyl mono-, di- or trisubstituted by chlorine, fluorine, lower alkyl or lower alkoxy or a heterocyclic radical selected from the group consisting of pyridinyl, imidazolinyl, thienyl, furyl, pyrimidinyl, oxazolinyl, ##STR103## which can be substituted by one or two substituents selected from the group consisting of lower alkyl, lower alkoxy, chlorine and fluorine, n is an integer of from 0 to 2 and m is an integer of from 1 to 2, provided that, when n is 0, R 6 must be attached trhough a carbon to carbon bond, and provided that R 7 is always attached through a carbon to oxygen bond, or, when at least one asymmetric carbon is present, an enantiomer or racemate thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 51
Dependent Claim
11 words
A method, in accordance with claim 47, wherein s is 0.
Claim 52
Dependent Claim
11 words
A method, in accordance with claim 47, wherein s is 1.
Claim 53
Dependent Claim
11 words
A method, in accordance with claim 48, wherein X is --CH═CH--.
Claim 54
Dependent Claim
11 words
A method, in accordance with claim 48, wherein X is S.
Claim 55
Dependent Claim
9 words
A method, in accordance with claim 50, wherein ##STR104##
Claim 56
Dependent Claim
9 words
A method, in accordance with claim 50, wherein ##STR105##
Claim 57
Dependent Claim
9 words
A method, in accordance with claim 51, wherein ##STR106##
Claim 58
Dependent Claim
9 words
A method, in accordance with claim 51, wherein ##STR107##
Claim 59
Dependent Claim
15 words
A method, in accordance with claim 47, wherein the compound of formula I is 2-[3-[4-(2-Chlorophenyl)-9-methyl6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]-2propynyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.
Claim 60
Dependent Claim
15 words
A method, in accordance with claim 47, wherein the compound of formula I is 1-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-proponyl]-benz[cd]indol-2(1H)-one.
Claim 61
Dependent Claim
15 words
A method, in accordance with claim 47, wherein the compound of formula I is 4-[3-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl]-2H-4,1-benzoxazin-3(4H)-one.
Claim 62
Dependent Claim
15 words
A method, in accordance With claim 47, wherein the compound of formula I is 5-{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl}-phenanthridin-6(5H)-one.
Claim 63
Dependent Claim
23 words
A method, in accordance with claim 47, wherein the compound of formula I is wherein the compound of formula 1 is 4-(2-chlorophenyl)-2-[3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-1-propynyl]-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[-triazolo -4,3-a][4,1]diazepine;
Claim 64
Dependent Claim
15 words
A method, in accordance with claim 47, wherein the compound of formula I is 1-{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno-[3,2-f][1,2,4]triazolo[4,3-a][4,1]diazepin-2-yl]-2-propynyl}-3,4-dihydro-2(1H)-quinolone.
Claim 65
Dependent Claim
10 words
A compound in accordance with claim 1, 1-{3-[4-(b 2-chlorphenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepin-2-yl]-2-propynyl}-1,3-dihydro-3-methyl-2H-benzimidazo -2-one.
Claim 66
Dependent Claim
10 words
A compound in accordance with claim 1, 1{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo triazolo [4,3-a][1,4]diazepin-2-yl]-2-propynyl}-1,3-dihydro-3-methyl-2,4(1H,3H)-quinzolinedione.
Claim 67
Dependent Claim
10 words
A compound in accordance with claim 1, 1-{3-[4-(b 2-chlorphenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepin-2-yl]-2-propynyl}-1,3-dihydro-3-phenyl-2H-benzimidazo 2-one.
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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) | 1993-09-24 | 1994-03-26 | 1994-09-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-09-24 | 1998-03-26 | 1998-09-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-09-24 | 2002-03-26 | 2002-09-25 | $7700.00 | Window Closed / Lapsed |