US4820834A
Expired / Lapsed
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Benzodiazepine analogs
Assignee: Merck and Co Inc
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Filing: 1987-03-16
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Granted: 1989-04-11
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Expires: 2007-03-16
Abstract
Abstract Benzodiazepine analogs of the formula: <IMAGE> I are disclosed which are antagonists of gastrin and cholecystokinin (CCK).
Inventors
- 👤 Ben E. Evans
- 👤 Roger M. Freidinger
- 👤 Mark G. Bock
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 19:06
CPC Classifications
C; C07; C07D; C07D403/00; C07D403/02; C07D403/04; C07D243/00; C07D243/06; C07D243/10; C07D243/14; C07D243/16; C07D243/18; A; A61; A61P; A61P1/00; A61P1/04; A61P25/00; A61P43/00; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/18; C07D209/20; C07D209/44; C07D209/48; C07D243/20; C07D243/22; C07D243/24; C07D401/00; C07D401/02; C07D401/12; C07D403/06; C07D403/12; C07D405/00; C07D405/02; C07D405/06; C07D405/12; C07D409/00; C07D409/02; C07D409/04; C07D409/06; C07D409/12; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06078; C07K5/06139; C07K5/06191; C07K5/08; C07K5/0821; A61K; A61K38/00
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
631 words
A compound of Formula II: ##STR130## wherein R 1 is H, C 1 -C 6 linear or branched alkyl, loweralkenyl, lower alkynyl, --X 12 COOR 6 , --X 11 -cycloloweralkyl, --X 12 NR 4 R 5 , --X 12 CONR 4 R 5 , --X 12 CN, or --X 11 CX 3 10 ; R 2 is H, loweralkyl, substituted or unsubstituted phenyl (wherein the substitutents may be 1 or 2 of halo, loweralkyl, loweralkoxy, loweralkylthio, carboxyl, carboxyloweralkyl, nitro, --CF 3 , or hydroxy), 2-, 3-, 4-pyridyl, ##STR131## --X 12 SCH 3 , --x 12 SOCH 3 , --X 12 SO 2 CH 3 , or --X 12 COOR 6 ; 3 is ##STR132## with the priviso that R 10 is not H or --CH 3 when R 3 is ##STR133## R 4 and R 5 are independently R 6 or in combination with the N of the NR 4 R 5 group form an unsubstituted or mono or disubstituted, saturated or unsaturated, 4-7 membered heterocyclic ring, or benzofused ,4-7 membered heterocyclic ring wherein said heterocyclic ring or said benzofused heterocyclic ring may contain a second heteroatom selected from O and NCH 3 and the substituent(s) is/are independently selected from C 1 -C 4 alkyl; R 6 is H, loweralkyl, cycloloweralkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted phenylloweralkyl wherein the phenyl or phenylloweralkyl substituents may be 1 or 2 of halo, loweralkyl, loweralkoxy, nitro, or CF 3 ; R 7 is α- or β-naphthyl, substituted or unsubstituted phenyl (wherein the substituents may be independently 1 to 2 of halo, --NO 2 , --OH,--X 11 NR 4 R 5 , loweralkyl, CF 3 , CN, SCF 3 , C.tbd.CH, CH 2 SCF 3 , ##STR134## OCHF 2 , SH, SPh, PO 3 H, loweralkoxy, loweralkylthio or COOH), 2-, 3-, 4- pyridyl, ##STR135## R 8 is H, loweralkyl, cycloloweralkyl, --X 12 CONH 2 , --X 12 COOR 6 , --X 12 -cycloloweralkyl, --X 12 NR 4 R 5 , ##STR136## R 9 and R 10 are independently H, --OH, or --CH 3 ; R 11 and R 12 are independently loweralkyl or cycloloweralkyl; R 13 is H, loweralkyl, acyl, O, or cycloloweralkyl; R 14 is loweralkyl or phenylloweralkyl; R 15 is H, loweralkyl, ##STR137## or --NH 2 ; R 16 alpha or beta naphthyl or 2-indolyl; R 18 is H or loweralkyl; p is 0 when its adjacent --- is unsaturated and 1 when its adjacent --- is saturated except that when R 13 is O, p=1 and --- is unsaturated; q is 0-4; r is 1 or 2; X 1 is H, --NO 2 , CF 3 CN, OH, loweralkyl, halo, loweralkylthio, loweralkoxy, --X 11 COOR 6 , or --X 11 NR 4 R 5 , X 2 and X 3 are independently H, --OH,--NO 2 , halo, loweralkylthio, loweralkyl, or loweralkoxy; X 4 is S, O, CH 2 , or NR 8 ; X 5 is H, CF 3 , CN, --COOR 6 , NO 2 , or halo; X 6 is O or HH; X 7 is O, S, HH, or NR 15 with the proviso that X 7 can be NR 15 only when R 1 is not H; X 8 is H, loweralkyl; X 9 and X a 9 are independently NR 18 or O; X 10 is F, Cl, or Br; X 11 is absent or C 1-4 linear or branched alkylidene; X 12 is C 1-4 linear or branched alkylidene; --- is a saturated or unsaturated bond; with the proviso that when X r 1 is Cl in the seven position, R 1 is H and R 2 is unsubstituted phenyl, then R 3 is not NHCO(CH 2 ) 2 C 6 H 5 or NHCOC 6 H 5 or pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
631 words
A compound of Formula II: ##STR130## wherein R 1 is H, C 1 -C 6 linear or branched alkyl, loweralkenyl, lower alkynyl, --X 12 COOR 6 , --X 11 -cycloloweralkyl, --X 12 NR 4 R 5 , --X 12 CONR 4 R 5 , --X 12 CN, or --X 11 CX 3 10 ; R 2 is H, loweralkyl, substituted or unsubstituted phenyl (wherein the substitutents may be 1 or 2 of halo, loweralkyl, loweralkoxy, loweralkylthio, carboxyl, carboxyloweralkyl, nitro, --CF 3 , or hydroxy), 2-, 3-, 4-pyridyl, ##STR131## --X 12 SCH 3 , --x 12 SOCH 3 , --X 12 SO 2 CH 3 , or --X 12 COOR 6 ; 3 is ##STR132## with the priviso that R 10 is not H or --CH 3 when R 3 is ##STR133## R 4 and R 5 are independently R 6 or in combination with the N of the NR 4 R 5 group form an unsubstituted or mono or disubstituted, saturated or unsaturated, 4-7 membered heterocyclic ring, or benzofused ,4-7 membered heterocyclic ring wherein said heterocyclic ring or said benzofused heterocyclic ring may contain a second heteroatom selected from O and NCH 3 and the substituent(s) is/are independently selected from C 1 -C 4 alkyl; R 6 is H, loweralkyl, cycloloweralkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted phenylloweralkyl wherein the phenyl or phenylloweralkyl substituents may be 1 or 2 of halo, loweralkyl, loweralkoxy, nitro, or CF 3 ; R 7 is α- or β-naphthyl, substituted or unsubstituted phenyl (wherein the substituents may be independently 1 to 2 of halo, --NO 2 , --OH,--X 11 NR 4 R 5 , loweralkyl, CF 3 , CN, SCF 3 , C.tbd.CH, CH 2 SCF 3 , ##STR134## OCHF 2 , SH, SPh, PO 3 H, loweralkoxy, loweralkylthio or COOH), 2-, 3-, 4- pyridyl, ##STR135## R 8 is H, loweralkyl, cycloloweralkyl, --X 12 CONH 2 , --X 12 COOR 6 , --X 12 -cycloloweralkyl, --X 12 NR 4 R 5 , ##STR136## R 9 and R 10 are independently H, --OH, or --CH 3 ; R 11 and R 12 are independently loweralkyl or cycloloweralkyl; R 13 is H, loweralkyl, acyl, O, or cycloloweralkyl; R 14 is loweralkyl or phenylloweralkyl; R 15 is H, loweralkyl, ##STR137## or --NH 2 ; R 16 alpha or beta naphthyl or 2-indolyl; R 18 is H or loweralkyl; p is 0 when its adjacent --- is unsaturated and 1 when its adjacent --- is saturated except that when R 13 is O, p=1 and --- is unsaturated; q is 0-4; r is 1 or 2; X 1 is H, --NO 2 , CF 3 CN, OH, loweralkyl, halo, loweralkylthio, loweralkoxy, --X 11 COOR 6 , or --X 11 NR 4 R 5 , X 2 and X 3 are independently H, --OH,--NO 2 , halo, loweralkylthio, loweralkyl, or loweralkoxy; X 4 is S, O, CH 2 , or NR 8 ; X 5 is H, CF 3 , CN, --COOR 6 , NO 2 , or halo; X 6 is O or HH; X 7 is O, S, HH, or NR 15 with the proviso that X 7 can be NR 15 only when R 1 is not H; X 8 is H, loweralkyl; X 9 and X a 9 are independently NR 18 or O; X 10 is F, Cl, or Br; X 11 is absent or C 1-4 linear or branched alkylidene; X 12 is C 1-4 linear or branched alkylidene; --- is a saturated or unsaturated bond; with the proviso that when X r 1 is Cl in the seven position, R 1 is H and R 2 is unsubstituted phenyl, then R 3 is not NHCO(CH 2 ) 2 C 6 H 5 or NHCOC 6 H 5 or pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
401 words
A compound of claim 1 wherein: R 1 is H, C 1 -C 6 linear or branched alkyl, --X 12 COOR 6 , --X 11 -cycloloweralkyl, X 12 NR 4 R 5 or --X 12 CONR 4 R 5 ; R 2 is substituted or unsubstituted phenyl (wherein the substitutents may be 1 or 2 of halo, loweralkyl, loweralkoxy, loweralkylthio, carboxyl, carboxyloweralkyl, nitro, --CF 3 , or hydroxy), 2-, 3-, or 4- pyridyl, ##STR138## R 4 and R 5 are independently R 6 or in combination with the N of the NR 4 R 5 group form an unsubstituted or mono or disubstituted, saturated or unsaturated, 4-7 membered heterocyclic ring, or benzofused 4-7 membered heterocyclic ring wherein said heterocyclic ring or said benzofused heterocyclic ring may contain a second heteroatom selected from O and NCH 3 and the substituent(s) is/are independently selected from C 1 -C 4 alkyl; R 6 is H, C 1-4 straight or branched-chain alkyl or C 3 -C 6 -cycloalkyl R 7 is α- or β-naphthyl, substituted or unsubstituted phenyl (wherein the substituents may be 1 to 2 of halo, --NO 2 , --OH, --X 11 NR 4 R 5 , loweralkyl, CF 3 , CN, SCF 3 , ##STR139## SH, SPh, loweralkoxy, loweralkylthio, or carboxy), 2-, 3-, 4-pyridyl, ##STR140## R 8 is H, loweralkyl or cycloloweralkyl; R 9 and R 10 are independently H, --OH, or --CH 3 ; R 13 is H, loweralkyl, acyl, O, or cycloloweralkyl; R 18 is H or loweralkyl; p is 0 when its adjacent --- is unsaturated and 1 when its adjacent --- is saturated except that when R 13 is O, p=1 and --- is unsaturated; q is 0-2; r is 1 or 2; X 1 is H, --NO 2 , CF 3 , CN, loweralkyl, halo, loweralkylthio or --X 11 COOR 6 ; X 2 and X 3 are independently H, --NO 2 , halo, loweralkylthio, loweralkyl, or loweralkoxy; X 4 is S, O, or NR 8 ; X 5 is H, CF 3 , CN, --COOR 6 , NO 2 , or halo; X 6 is O or HH; X 7 is O, S; X 9 and X a 9 are independently NR 18 , or O; X 11 is absent or C 1-4 linear alkylidene; X 12 is C 1-4 linear or branched alkylidene; --- is a saturated or unsaturated bond or pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
292 words
A compound of claim 2 wherein: R 1 is H, C 1-3 linear or branched alkyl, --X 12 COOR 6 , --X 12 CONR 4 R 5 , R 2 is substituted or unsubstituted phenyl (wherein the substitutents may be 1 or 2 of halo, loweralkyl, carboxyl, nitro or --CF 3 ); --X 12 COOR 6 ; 2-, 3-, 4- pyridyl; R 3 ##STR141## R 4 and R 5 are independently R 6 or in combination with the N of the NR 4 R 5 group form an unsubstituted or mono or disubstituted, saturated or unsaturated, 4-7 membered heterocyclic ring, or benzofused 4-7 membered heterocyclic ring wherein said heterocyclic ring or said benzofused heterocyclic ring may contain a second heteroatom selected from O and NCH 3 and the substituent(s) is/are independently selected from C 1-4 alkyl; R 6 is H, C 1-4 straight or branched-chain alkyl; R 7 is α- or β-naphthyl, substituted or unsubstituted phenyl (wherein the substituents may be 1 to 2 of halo, --NO 2 , --OH, --NR 4 R 5 , loweralkyl, CF 3 , CN, or loweralkoxy), 2-, 3-, 4-pyridyl, ##STR142## R 9 and R 10 are independently H, or --OH; p is 0 when its adjacent --- is unsaturated and 1 when its adjacent --- is saturated, the p of (R 13 ) p is 0; r is 1 or 2; X 1 is H, --NO 2 , CF 3 , loweralkyl or halo; X 2 and X 3 are independently H, --NO 2 , halo, loweralkyl, or loweralkoxy; X 4 is O or NR 8 ; X 7 is O or S, X 12 is C 1-2 linear or branched chain alkylidene; --- is a saturated or unsaturated bond; or the pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
272 words
A compound of claim 3 wherein: R 1 is H, C 1 -C 2 linear alkyl, --X 12 COOR 6 , --X 12 CONR 4 R 5 ; R 2 is substituted or unsubstituted phenyl (wherein the substitutent may be halo, loweralkyl, nitro, --CF 3 ), 2-, 3-, 4-pyridyl, or X 12 COOR 6 ; R 3 is ##STR143## R 4 and R 5 are independently R 6 or in combination with the N of the NR 4 R 5 group form an unsubstituted or mono or disubstituted, saturated or unsaturated, 4-7 membered heterocyclic ring, or benzofused 4-7 membered heterocyclic ring wherein said heterocyclic ring or said benzofused heterocyclic ring may contain a second heteroatom selected from O and NCH 3 and the substituent(s) is/are independently selected from C 1-4 alkyl; R 6 is H, C 1 -C 3 straight chain alkyl; R 7 is α- or β-naphthyl, substituted or unsubstituted phenyl (wherein the substituents may be 1 to 2 of halo, --NO 2 , NH 2 , methyl, ethyl, CF 3 , CN, or loweralkoxy), 2-, 3-, 4-pyridyl, ##STR144## R 10 is H, or OH; p is 1 of (R 10 ) p and 0 of (R 9 ) p and (R 13 ) p , --- at 4,5 is unsaturated and --- at 3,4 is saturated; r is 1 or 2; X 1 is H, --NO 2 , CF 3 , loweralkyl or halo; X 2 is H, --NO 2 , halo or loweralkyl; X 4 is O, NH, NCH 3 ; X 7 is O or S; X 12 is C 1-2 linear alkylidene; or pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
105 words
A compound of claim 4 wherein: R 1 is H, CH 3 , CH 2 CH 3 , CH 2 COOH, CH 2 COOEt, ##STR145## R 2 is phenyl, 2-F-phenyl, 4-CH 3 -phenyl, 2-, 3-, or 4-pyridyl; R 3 is ##STR146## R 10 is H or --OH; p is 1 of (R 10 ) p and 0 of (R 9 ) p and (R 13 ) p ; r is 1; X 1 is H, 7-Cl, 8-CH 3 , 9-CH 3 ; X 7 is O or S; --- at 4, 5 is unsaturated and 3, 4 is saturated; or the pharmaceutically acceptable salt thereof;
Claim 7
Dependent Claim
32 words
A compound of claim 1 which is: 3(R)-N-(4-Chlorophenyl)-N'-(2,3-dihydro-1-methyl-5-phenyl-2-oxo-1H-1,4-benzodiazepin-3-yl)urea, 3-Benzoyl-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 5-(2-Fluorophenyl)-1,3-dihydro-3-hydroxy-3-(4-methoxybenzoyl)-1-methyl-2H-1,4-benzodiazepin-2-one, N-(2,3-Dihydro-1-methyl-2-oxo-5(3-methylphenyl)-1H-1,4-benzodiazepin-3-yl)-N'-(phenylmethyl)urea, N-(2,3-Dihydro-1-ethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)urea, 3-(S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-3-(3-methoxyphenyl)-2-propenamide, 3-((((4-Chlorophenyl)amino)carbonyl)amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-propanoic acid ethyl ester, 3(RS)-1,3-dihydro-(2-indolecarbonylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one, 1-Carboxymethyl-1,3-dihydro-3(RS)-(2-indolecarbonylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-3(RS)-(2-indolecarbonylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 1,3-dihydro-1-methyl-3(RS)-[2-(1-methylindole)carbonylamino]-5-phenyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-1-methyl-3(RS)-(4-chlorophenylcarbonyl)amino-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)3(RS)-(2-indolecarbonylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-1-methyl-3(RS)-[2'-(1'-methylindole)carbonylamino]-2H-1,4-benzodiazepin-2-one, 3(S)-(-)-1,3-Dihydro-3-(2-indolecarbonylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(2-indolecarbonylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-1,3-Dihydro-3-(4-chlorobenzoylamino)-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(-)-1,3-Dihydro-3-(4-bromobenzoylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-indolecarbonyl amino)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-3-(RS)-(4-chlorophenylcarbonyl)amino-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1-Carboxymethyl-1,3-dihydro-5-(2-fluorophenyl)-3(RS)-(2-indolecarbonylamino)-2H-1,4-benzodiazepin-2-one,
Claim 8
Dependent Claim
67 words
3-Dihydro-3-(RS)-(5-fluoroindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-3-(RS)-(1-methylindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-benzofurancarbonylamino)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-1-methyl-3-(RS)-(4-chlorophenylcarbonyl)amino-5-phenyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-3-(3-Bromobenzoylamino)-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-3-(4-Bromobenzoylamino)-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(4-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(3-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-indole) carbonylamino-2H-1,4-benzodiazepin-2-thione, 3(S)-(2-Indolecarbonyl)amino-1,3-dihydro-5-phenyl-2H-1,4,-benzodiazepin-2-one, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-3-phenyl-2-propenamide, 3-((((4-Chlorophenyl)amino)carbonyl)amino)-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)-benzamide, 3-((((4-Chlorophenyl)amino)carbonyl)amino)-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, 5-(2-Fluorophenyl)-2,3-dihydro-3-((1H-indol-2-ylcarbonyl)amino)-2-oxo-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, 4-Bromo-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-bezamide, N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)-benzamide, (S)-N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)benzamide, 3-((((4-Chlorophenyl)amino)carbonyl)amino)-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 1-((3-((((4-Chlorophenyl)amino)carbonyl)amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl)acetyl)pyrrolidine, 1-((3-((((4-Chlorophenyl)amino)carbonyl)amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl)acetyl)-4-methylpiperazine, 3-(((4-Chlorophenyl)acetyl)amino)-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-phenylurea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methylphenyl)-urea, N-(2-Chlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(4-Nitrophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(2,4-Dichlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-nitrophenyl)-urea, N-(3-Chlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-Phenyl-1H-1,4-benzodiazepin-3-yl)urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-(2-nitrophenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-fluorophenyl)-urea, N-(3-Bromophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-1-naphthalenyl-urea, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(2-chlorophenyl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-bromophenyl)-urea, 1-{[3-[(((3-Methoxyphenyl)amino)carbonyl)amino]-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl]acetyl}pyrrolidine, 3-{[((3-Methoxyphenyl)amino)carbonyl)amino]-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 3-{[((2-Chlorophenyl)amino)carbonyl]amino}-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 3-N-(2,3-Dihydro-9-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1,9-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1,9-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methylphenyl)-urea, 3-N-(2,3-Dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea or (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-chlorophenyl)-urea.
Claim 9
Dependent Claim
67 words
3-Dihydro-3-(RS)-(5-fluoroindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-3-(RS)-(1-methylindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-benzofurancarbonylamino)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-1-methyl-3-(RS)-(4-chlorophenylcarbonyl)amino-5-phenyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-3-(3-Bromobenzoylamino)-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-3-(4-Bromobenzoylamino)-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(4-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(3-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-indole) carbonylamino-2H-1,4-benzodiazepin-2-thione, 3(S)-(2-Indolecarbonyl)amino-1,3-dihydro-5-phenyl-2H-1,4,-benzodiazepin-2-one, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-3-phenyl-2-propenamide, 3-((((4-Chlorophenyl)amino)carbonyl)amino)-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)-benzamide, 3-((((4-Chlorophenyl)amino)carbonyl)amino)-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, 5-(2-Fluorophenyl)-2,3-dihydro-3-((1H-indol-2-ylcarbonyl)amino)-2-oxo-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, 4-Bromo-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-bezamide, N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)-benzamide, (S)-N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)benzamide, 3-((((4-Chlorophenyl)amino)carbonyl)amino)-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 1-((3-((((4-Chlorophenyl)amino)carbonyl)amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl)acetyl)pyrrolidine, 1-((3-((((4-Chlorophenyl)amino)carbonyl)amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl)acetyl)-4-methylpiperazine, 3-(((4-Chlorophenyl)acetyl)amino)-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-phenylurea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methylphenyl)-urea, N-(2-Chlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(4-Nitrophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(2,4-Dichlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-nitrophenyl)-urea, N-(3-Chlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-Phenyl-1H-1,4-benzodiazepin-3-yl)urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-(2-nitrophenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-fluorophenyl)-urea, N-(3-Bromophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-1-naphthalenyl-urea, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(2-chlorophenyl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-bromophenyl)-urea, 1-{[3-[(((3-Methoxyphenyl)amino)carbonyl)amino]-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl]acetyl}pyrrolidine, 3-{[((3-Methoxyphenyl)amino)carbonyl)amino]-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 3-{[((2-Chlorophenyl)amino)carbonyl]amino}-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 3-N-(2,3-Dihydro-9-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1,9-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1,9-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methylphenyl)-urea, 3-N-(2,3-Dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea or (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-chlorophenyl)-urea.
Claim 10
Dependent Claim
24 words
A compound of claim 6 which is: 3(RS)1,3-Dihydro-(2-indolecarbonylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one, 1-Carboxymethyl-1,3-dihydro-3(RS)-(2-indolecarbonylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-3(RS)-(2-indolecarbonylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 1,3-dihydro-1-methyl-3(RS)-[2-(1-methylindole)carbonylamino]-5-phenyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-1-methyl-3(RS)-(4-chlorophenylcarbonyl)amino-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3(RS)-(2-indolecarbonylamino)-1-methyl-2H-1,4-benzodiazepin-2one, 1,3-Dihydro-5-(2-fluorophenyl)-1-methyl-3(RS)-[2'-(1'-methylindole)carbonylamino]-2H-1,4-benzodiazepin-2-one, (S)-(-)-1,3-Dihydro-3-(2-indolecarbonylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(2-indolecarbonylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-3-(4-chlorobenzoylamino)-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, (S)-(-)--1,3-Dihydro-3-(4-bromobenzoylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-indolecarbonyl amino)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-3-(RS)-(4-chlorophenylcarbonyl)amino-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1-Carboxymethyl-1,3-dihydro-5-(2-fluorophenyl)-3(RS)-(2-indolecarbonylamino)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-3-(RS)-(5-fluoroindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-3-(RS)-(1-methylindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one,
Claim 11
Dependent Claim
30 words
3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-benzofurancarbonylamino)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-1-methyl-3-(RS)-(4-chlorophenylcarbonyl)amino-5-phenyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-3-(3-Bromobenzoylamino)-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-3-(4-Bromobenzoylamino)-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(4-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(3-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-indole) carbonylamino-2H-1,4-benzodiazepin-2-thione, (S)-(2-Indolecarbonyl)amino-1,3-dihydro-5-phenyl-2H-1,4,-benzodiazepin-2-one, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-3-phenyl-2-propenamide, 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-2-amino-4-chlorobenzamide, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)-benzamide, 5-(2-Fluorophenyl)-2,3-dihydro-3-((1H-indol-2-ylcarbonyl)amino)-2-oxo-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, 4-Bromo-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-benzamide, N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)-benzamide, (S)-N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)benzamide, N-(2-Chlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(2,4-Dichlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(2-nitrophenyl)-urea, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(2-chlorophenyl)-urea 3-N-(2,3-Dihydro-9-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1,9-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-urea, 3-N-(2,3-Dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea,
Claim 12
Dependent Claim
30 words
3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-benzofurancarbonylamino)-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-1-methyl-3-(RS)-(4-chlorophenylcarbonyl)amino-5-phenyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-3-(3-Bromobenzoylamino)-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-3-(4-Bromobenzoylamino)-1,3-dihydro-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(4-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, (S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(3-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 1,3-Dihydro-5-(2-fluorophenyl)-3-(RS)-(2-indole) carbonylamino-2H-1,4-benzodiazepin-2-thione, (S)-(2-Indolecarbonyl)amino-1,3-dihydro-5-phenyl-2H-1,4,-benzodiazepin-2-one, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-3-phenyl-2-propenamide, 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-2-amino-4-chlorobenzamide, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)-benzamide, 5-(2-Fluorophenyl)-2,3-dihydro-3-((1H-indol-2-ylcarbonyl)amino)-2-oxo-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, 4-Bromo-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-benzamide, N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)-benzamide, (S)-N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)benzamide, N-(2-Chlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, N-(2,4-Dichlorophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(2-nitrophenyl)-urea, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(2-chlorophenyl)-urea 3-N-(2,3-Dihydro-9-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1,9-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-urea, 3-N-(2,3-Dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, N-(3-Methoxyphenyl)-N'-(2,3-dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea,
Claim 13
Dependent Claim
32 words
A compound of claim 6 which is: 3-((((4-Chlorophenyl)amino)carbonyl)amino)-5-2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, 3-((((4-Chlorophenyl)amino)carbonyl)amino)-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, 3-((((4-Chlorophenyl)amino)carbonyl)amino)-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 1-((3-((((4-Chlorophenyl)amino)carbonyl)amino)-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl)-acetyl)pyrrolidine, 1-((3-((((4-Chlorophenyl)amino)carbonyl)amino)-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl)acetyl)-4-methylpiperazine, 3-(((4-Chlorophenyl)acetyl)amino)-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetic acid ethyl ester, N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-phenylurea, N-(4-Nitrophenyl)-N'-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)N'-(3-methoxyphenyl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-bromophenyl)-urea, 1-{[3-[(((3-Methoxyphenyl)amino)carbonyl)amino]-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl]acetyl}pyrrolidine, 3-{[((3-Methoxyphenyl)amino)carbonyl)amino]-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 3-{[((2-Chlorophenyl)amino)carbonyl]amino}-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methylphenyl)-urea, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-chlorophenyl)-urea.
Claim 14
Dependent Claim
27 words
A compound which is 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1,9-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-3-phenyl-2-propenamide, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(2-chlorophenyl)-urea, (S)-N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)benzamide, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(2-indolecarbonylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(3-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(-)-1,3-Dihydro-3-(2-indolecarbonylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-2-amino-4-chlorobenzamide, 4-Bromo-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-benzamide, 1,3-Dihydro-5-(2-fluorophenyl)-1-methyl-3(RS)-[2'-(1'-methylindole)carbonylamino]-2H-1,4-benzodiazepin-2-one, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, 1,3-dihydro-1-methyl-3(RS)-[2-(1-methylindole)carbonylamino]-5-phenyl-2H-1,4-benzodiazepin-2-one, 1-Carboxymethyl-1,3-dihydro-3(RS)-(2-indolecarbonylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one, or 3(S)-(+)-1,3-Dihydro-3-(4-chlorobenzoylamino)-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
27 words
A compound which is 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-(p-tolyl)-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1,9-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, 3-N-(2,3-Dihydro-1,8-dimethyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-3-phenyl-2-propenamide, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(2-chlorophenyl)-urea, (S)-N-(5-(2-Fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl)-4-(trifluoromethyl)benzamide, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(2-indolecarbonylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(+)-1,3-Dihydro-5-(2-fluorophenyl)-3-(3-iodobenzoylamino)-1-methyl-2H-1,4-benzodiazepin-2-one, 3(S)-(-)-1,3-Dihydro-3-(2-indolecarbonylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 3-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-2-amino-4-chlorobenzamide, 4-Bromo-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-benzamide, 1,3-Dihydro-5-(2-fluorophenyl)-1-methyl-3(RS)-[2'-(1'-methylindole)carbonylamino]-2H-1,4-benzodiazepin-2-one, (S)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methoxyphenyl)-urea, 1,3-dihydro-1-methyl-3(RS)-[2-(1-methylindole)carbonylamino]-5-phenyl-2H-1,4-benzodiazepin-2-one, 1-Carboxymethyl-1,3-dihydro-3(RS)-(2-indolecarbonylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one, or 3(S)-(+)-1,3-Dihydro-3-(4-chlorobenzoylamino)-5-(2-fluorophenyl)-1-methyl-2H-1,4-benzodiazepin-2-one, or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
16 words
A compound which is 3-{[((3-Methoxyphenyl)amino)carbonyl)amino]-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 1-((3-((((4-Chlorophenyl)amino)carbonyl)amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl)acetyl)pyrrolidine, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)-urea, 3-{[((2-Chlorophenyl)amino)carbonyl]amino}-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-bromophenyl)-urea, or (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methylphenyl)-urea, or pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
16 words
A compound which is 3-{[((3-Methoxyphenyl)amino)carbonyl)amino]-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, 1-((3-((((4-Chlorophenyl)amino)carbonyl)amino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-yl)acetyl)pyrrolidine, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)-urea, 3-{[((2-Chlorophenyl)amino)carbonyl]amino}-N,N-diethyl-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-1-acetamide, (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-bromophenyl)-urea, or (R)-N-(2,3-Dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(4-methylphenyl)-urea, or pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
15 words
A compound of claim 1 which is 3(S)-(-)-1,3-dihydro-3-(2-indolecarbonylamino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, or (R)-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)urea, or pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
9 words
The compound 3(S)-(-)-1,3-dihydro-3-(2-indolecarbonyl amino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, or pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
9 words
The compound 3(S)-(-)-1,3-dihydro-3-(2-indolecarbonyl amino)-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, or pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
8 words
The compound (R)-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)urea, or pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
8 words
The compound (R)-N-(2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)urea, or pharmaceutically acceptable salt thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1992-04-10 | 1992-10-10 | 1993-04-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-04-10 | 1996-10-10 | 1997-04-11 | $3760.00 | Window Closed / Lapsed |
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