Patent number: 7384934
Abstract: Described herein are compounds of formula (I) wherein: is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, S, and O; Alk is (C1-4) alkylene or hydroxy substituted (C1-4) alkylene; X is oxygen or sulfur; R1 is hydrogen, (C1-6) fluroalkyl, (C3-6) cycloalkyl, or (C1-4) alkyl, wherein the (C1-4) alkyl is unsubstituted or substituted with hydroxy, methoxy, ethoxy, OCH2CH2OH, or —CN; R2 is H, halogen, (C1-6) fluoroalkyl, (C1-6) cycloalkyl, OR4, SR4, NO2, CN, COR4, C(O)OR4, CONR5R6, NR5R6, SO2NR5R6, NR5COR4, NR5SO2R4, optionally substituted aromatic, or (C1-6) alkyl, wherein (C1-6) alkyl is unsubstituted or substituted with a hydroxy group; R3 is hydrogen (C1-6) fluoroalkyl, (C2-6) alkenyl, Ar, (C1-4)alkyl-Ar, or (C1-4) alkyl wherein (C1-4) alkyly is unsubstituted or substituted with a phenyl; R4 is hydrogen, (C1-6) alkyl, (C1-6) fluoroalkyl, or optionally substituted aromatic; R5 and R6 are independently hydrogen, (C1-6) alkyl, or optionally
Type:
Grant
Filed:
July 28, 2003
Date of Patent:
June 10, 2008
Assignee:
Eli Lilly and Company
Inventors:
Thomas Daniel Aicher, Zhaogen Chen, Yvan LeHuerou, Fionna Mitchell Martin, Marta Maria Pineiro-Nunez, Vincent Patrick Rocco, Kevin Michael Ruley, John Mehnert Schaus, Patrick Gianpietro Spinazze, David Edward Tupper
Patent number: 7223752
Abstract: A compound of the formulae (I) or (II): wherein: Y is a moiety selected from NR or —(CH2)n; wherein R is hydrogen or (C1–C6) lower alkyl, and n is 1; represents: (1) a phenyl ring optionally substituted with one or two substituents selected, independently, from the group comprising hydrogen, (C1–C6) lower alkyl, halogen, cyano, CF3, hydroxy, (C1–C6) lower alkoxy, (C1–C6) lower alkoxy carbonyl, carboxy, —CONH2, —CONH[(C1–C6) lower alkyl], —CON[(C1–C6) lower alkyl]2; or (2) a 6-membered aromatic (unsaturated) heterocyclic ring having one nitrogen atom, optionally substituted by (C1–C6) lower alkyl, halogen or (C1–C6) lower alkoxy; represents: (1) a phenyl ring optionally substituted with one or two substituents selected, independently, from the group comprising hydrogen, (C1–C6) lower alkyl, halogen, cyano, CF3, hydroxy, (C1–C6) lower alkoxy, or (C1–C6) lower alkoxy carbonyl, carboxy, —CONH2, —CONH[(C1–C6) lower alkyl], —CON[(C1–C6) lower alkyl]2; or (2) a 5-membered aromatic (unsaturat
Type:
Grant
Filed:
November 4, 2004
Date of Patent:
May 29, 2007
Assignee:
Wyeth
Inventors:
Amedeo Arturo Failli, John P. Dusza, Thomas Joseph Caggiano, Jay Scott Shumsky, Kevin A. Memoli, Eugene J. Trybulski
Patent number: 7214673
Abstract: Described herein are antipyschotic compounds of formula (I) wherein, A is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, O, and S; Alk is (C1-4) alkylene optionally substituted with OH, methoxy, ethoxy, or F; Ar is optionally substituted phenyl, naphthyl, monocyclic heteroaromatic, or bicyclic heteroaromatic; R1 is hydrogen or (C1-4) alkyl optionally substituted with OH, OR3, or OCH2CH2OH, wherein R3 is (C1-2) alkyl; R2 is H, (C1-6) alkyl, halogen, fluorinated (C1-6) alkyl, OR4, SR4, NO2, CN, COR4, CONR5R6, SO2NR5R6, NR5R6, NR5COR4, NR5SO2R4, or optionally substituted phenyl, wherein R4 is hydrogen, (C1-6) alkyl, fluorinated (C1-6) alkyl, or optionally substituted phenyl, R5 and R6 are independently hydrogen, (C1-6) alkyl, or optionally substituted phenyl; Z is one or two substituents independently selected from hydrogen, halogen, (C1-6) alkyl, fluorinated (C1-6) alkyl, OR7, SR7, NO2, CN, COR7, CONR8R9, SO2NR8R9, NR8SO2R
Type:
Grant
Filed:
March 17, 2003
Date of Patent:
May 8, 2007
Assignee:
Eli Lilly and Company
Inventors:
Thomas Daniel Aicher, Zhaogen Chen, Joseph Herman Krushinski, Jr., Yvan Le Huerou, Marta Maria Pineiro-Nunez, Kevin Michael Ruley, John Mehnert Schaus, Dennis Charles Thompson, David Edward Tupper, Ying Chen, Margaret Mary Faul, Vincent Patrick Rocco
Patent number: 7053082
Abstract: The invention relates to new 2,3-benzodiazepine derivatives of general Formula (I), (wherein R1 stands for methyl, formyl, carboxy, cyano, —CH?NOH, —CH?NNHCONH2 or —NR5R6, wherein R5 and R6 independently from each other represent hydrogen or lower alkyl or together with the nitrogen atom, they are attached to, form a 5- or 6-membered, saturated or unsaturated heterocyclic ring optionally containing one or more further nitrogen, sulfur and/or oxygen atom(s); R2 is nitro or amino; R3 stands for hydrogen, lower alkanoyl or CO—NR7R8, wherein R7 and R8 independently from each other stand for hydrogen, lower alkoxy, lower alkyl or lower cycloalkyl or together with the nitrogen atom, they are attached to, form a 5- or 6-membered, saturated or unsaturated heterocyclic ring optionally containing one or more further nitrogen, sulfur and/or oxygen atom(s); R4 is hydrogen or lower alkyl; the dotted lines have the following meaning: if R3 and R4 are not present, the bond between positions C8 and C9 is a single bond and th
Type:
Grant
Filed:
July 4, 2000
Date of Patent:
May 30, 2006
Assignee:
EGIS Gyogyszergyar Rt.
Inventors:
Zoltan Greff, Geza Szabo, Jozsef Barkoczy, Zoltan Ratkai, Gabor Blasko, Gyula Simig, Gabor Gigler, Bernadett Martonné Marko, György Levay, Karoly Tihanyi, Andras Egyed, Annamaria Simo
Patent number: 6906062
Abstract: Crystalline Form I of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine characterised by x-ray powder diffraction peaks at approximately 9.94, 8.53, 8.19, 6.86, 6.35, 5.47, 4.83, 4.71, 4.53, 4.22, 4.08, 3.82, 3.75, 3.69, 3.50, 3.34, 3.11, 2.94, 2.82, 2.76, 2.59, 2.34, 2.03, 1.92 d (interplanar spacing) values; infrared absorbance bands at approximately 1456, 1365, 905, 757, 662 & 604 cm?3 and having stable colour at ambient conditions of storage; and the process of its preparation comprising at least two repetitive steps of crystallization from one or more organic solvent by dissolving 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine in said solvent and allowing crystallization to occur; wherein in at least one step the solution is purified by treating with a solid adsorbent material and filtering; and wherein in the last step the crystalline material is subjected to drying.
Type:
Grant
Filed:
December 23, 2002
Date of Patent:
June 14, 2005
Assignee:
Sun Pharmaceutical Industries Limited
Inventors:
Vijay Chhangamal Chhabada, Rajeev Budhdev Rehani, Rajamamannar Thennati
Patent number: 6903091
Abstract: A compound of the formulae (I) or (II): wherein: Y is a moiety selected from NR or —(CH2)n; wherein R is hydrogen or (C1-C6) lower alkyl, and n is 1; represents: (1) a phenyl ring optionally substituted with one or two substituents selected, independently, from the group comprising hydrogen, (C1-C6) lower alkyl, halogen, cyano, CF3, hydroxy, (C1-C6) lower alkoxy, (C1-C6) lower alkoxy carbonyl, carboxy, —CONH2, —CONH[(C1-C6) lower alkyl], —CON[(C1-C6) lower alkyl]2; or (2) a 6-membered aromatic (unsaturated) heterocyclic ring having one nitrogen atom, optionally substituted by (C1-C6) lower alkyl, halogen or (C1-C6) lower alkoxy; represents: (1) a phenyl ring optionally substituted with one or two substituents selected, independently, from the group comprising hydrogen, (C1-C6) lower alkyl, halogen, cyano, CF3, hydroxy, (C1-C6) lower alkoxy, or (C1-C6) lower alkoxy carbonyl, carboxy, —CONH2, —CONH[(C1-C6) lower alkyl], —CON[(C1-C6) lower alkyl]2; or (2) a 5-membered aromatic (unsaturated) hete
Type:
Grant
Filed:
April 11, 2002
Date of Patent:
June 7, 2005
Assignee:
Wyeth
Inventors:
Amedeo A. Failli, Thomas J. Caggiano, Jay S. Shumsky, Eugene J. Trybulski, Kevin A. Memoli, John P. Dusza
Publication number: 20030125322
Abstract: Crystalline Form I of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine characterised by x-ray powder diffraction peaks at approximately 9.94, 8.53, 8.19, 6.86, 6.35, 5.47, 4.83, 4.71, 4.53, 4.22, 4.08, 3.82, 3.75, 3.69, 3.50, 3.34, 3.11, 2.94, 2.82, 2.76, 2.59, 2.34, 2.03, 1.92 d (interplanar spacing) values; infrared absorbance bands at approximately 1456, 1365, 905, 757, 662 & 604 cm−3 and having stable colour at ambient conditions of storage; and the process of its preparation comprising at least two repetitive steps of crystallization from one or more organic solvent by dissolving 2-methyl-4 -(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine in said solvent and allowing crystallization to occur; wherein in at least one step the solution is purified by treating with a solid adsorbent material and filtering; and wherein in the last step the crystalline material is subjected to drying.
Type:
Application
Filed:
December 23, 2002
Publication date:
July 3, 2003
Applicant:
SUN PARMACEUTICAL INDUSTRIES LIMITED
Inventors:
Vijay Chhangamal Chhabada, Rajeev Budhdev Rehani, Rajamamannar Thennati