Patents by Inventor Robert Deziel
Robert Deziel has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 6706706Abstract: Disclosed are compounds of formula I: wherein R2 is H, halogen, (C1-4)alkyl, O(C1-4)alkyl, NH(C1-4alkyl) or N(C1-4alkyl)2; R4 is H or CH3; R5 is H or CH3; R12 is H, halogen, (C1-4)alkyl, CF3, or NO2; R13 is H, (C1-4)alkyl, halogen, OH, or NH2, with the proviso that R12 and R13 are not both H; and R14 is COOR14a wherein R14a is H or (C1-6)alkyl; or R14 is (C2-4)alkenyl-COOR14a wherein R14a is as defined herein; or R14 is (C1-4)alkyl-COOR14a wherein R14a is as defined above; or a salt or a prodrug thereof, useful as inhibitors of HIV reverse transcriptase.Type: GrantFiled: March 4, 2003Date of Patent: March 16, 2004Assignee: Boehringer Ingelheim International GmbHInventors: Jeffrey O'Meara, Bruno Simoneau, Christiane Yoakim, Robert Déziel, William W. Ogilvie
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Patent number: 6673791Abstract: Compounds represented by formula I: wherein R2 is H, halogen, NHNH2, (C1-4)alkyl, O(C1-6)alkyl, and haloalkyl; R4 is H or Me; R5 is H or (C1-4)alkyl; R11 is (C1-4)alkyl, (C1-4)alkyl(C3-7)cycloalkyl, or (C3-7)cycloalkyl; and Q is naphthyl, fused phenyl(C4-7)cycloalkyl and fused phenyl-5, 6, or 7-membered saturated heterocycle having one to two heteroatom selected from O, N, or S, said Q being substituted with from 1 to 4 R12 substituents selected from: R13, (C1-6)alkyl, (C3-7)cycloalkyl, or (C2-6)alkenyl, said alkyl, cycloalkyl, or alkenyl being optionally substituted with R13; or a salt thereof. Compounds represented by formula I have inhibitory activity against Wild Type, single and double mutant strains of HIV.Type: GrantFiled: July 25, 2002Date of Patent: January 6, 2004Assignee: Boehringer Ingelheim (Canada) Ltd.Inventors: William W. Ogilvie, Robert Déziel, Jeffrey O'Meara, Bruno Simoneau
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Publication number: 20030195197Abstract: Disclosed are compounds of formula I: 1Type: ApplicationFiled: March 4, 2003Publication date: October 16, 2003Applicant: Boehringer Ingelheim International GmbHInventors: Jeffrey O'Meara, Bruno Simoneau, Christiane Yoakim, Robert Deziel, William W. Ogilvie
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Publication number: 20030171363Abstract: Compounds represented by formula I: 1Type: ApplicationFiled: July 25, 2002Publication date: September 11, 2003Applicant: Boehringer Ingelheim ( Canada) Ltd.Inventors: William W. Ogilvie, Robert Deziel, Jeffrey O'Meara, Bruno Simoneau
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Publication number: 20030153744Abstract: The present invention comprises 7-deaza L-nucleosides having unexpectedly high inhibitory activity against the hepatitis B virus. The invention further comprises pharmaceutical compositions comprising such compounds as well as methods of treating mammals, particularly humans, infected with HBV and other viral infections.Type: ApplicationFiled: December 20, 2002Publication date: August 14, 2003Applicant: Micrologix Biotech Inc.Inventors: Khalid Mekouar, Robert Deziel, Samir Mounir, Radhakrishnan P. Iyer
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Publication number: 20030069226Abstract: A compound of formula I: 1Type: ApplicationFiled: March 13, 2002Publication date: April 10, 2003Inventors: William W. Ogilvie, Robert Deziel, Julie Naud, Jeffrey O'Meara
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Patent number: 6313095Abstract: Disclosed herein are tetrapeptide derivatives of the formula X—NH—CHR1—C(W1)—NR2—CH[CH2C(O)—Y]—C(W2)—NH—CH[CR3(R4)—COOH]—C(W3)—NH—CHR5—Z wherein X is a terminal group, for example, alkanoyl or phenylalkanoyl radicals, R1 and R5 are selected from amino acid or derived amino acid residues, R2 is hydrogen, alkyl or phenylalkyl, R3 and R4 are hydrogen or alkyl or R3 and R4 are joined to form a cycloalkyl, W1, W2and W3 are oxo or thioxo, Y is, for example, an alkoxy or a monosubstituted or disubstituted amino, and Z is a terminal unit, for example, hydrogen, COOH or CH2OH. The derivatives are useful for treating herpes infections.Type: GrantFiled: October 6, 1994Date of Patent: November 6, 2001Assignee: Boehringer Ingelheim (Canada), Ltd.Inventors: Julian Adams, Pierre Louis Beaulieu, Robert Déziel, Neil Moss
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Patent number: 6242439Abstract: A compound of formula I wherein R1 is hydrogen, methyl, ethyl, methoxy or methylthio; R2 and R3 each independently is hydrogen or lower alkyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy or benzyloxy; R5 is lower alkyl, lower cycloalkyl, (CH2)mC(O)OR6 wherein m is the integer 1 or 2 and R6 is lower alkyl, phenyl optionally substituted; optionally Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with C(O)O-benzyl or with phenyl optionally substituted with C(O)OR7 wherein R7 is lower alkyl or (lower alkyl)phenyl; and Z is lower alkyl or optionally substituted phenyl or Het; with the proviso that when Z is (CH2)p-(Het), then R2 and R3 each is hydrogen; or a therapeutically acceptable acid addition salt thereof which compound is useful in the treatment of HCMV infections.Type: GrantFiled: October 6, 1998Date of Patent: June 5, 2001Assignee: Boehringer Ingelheim (Canada) Ltd.Inventors: Christiane Yoakim, Robert Déziel, Jeffrey O'Meara, William W. Ogilvie
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Patent number: 6239125Abstract: A compound of formula 1: wherein Y is S or O; R1 is C1-6 alkyl; (C0-6 alkyl)aryl; (C0-6 alkyl)Het; or R1 is an amino acid analog or dipeptide analog of the formula: wherein R2 is H, C1-10 alkyl; or an amide or ester group; A is C6-10 aryl, Het or CH—R3 wherein R3 is C1-6 alkyl or (C0-4 alkyl)aryl; and Z is H, C1-6 alkyl, or an acyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy, or benzyloxy; and R5 is alkyl, cycloalkyl, carboxyl group; an aryl; Het or Het(lower alkyl); or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with phenyl or C(O)OCH2-phenyl, said phenyl ring optionally mono- or di-substituted with among others C(O)OR7 wherein R7 is lower alkyl or phenyl(lower alkyl); or a therapeutically acceptable acid addition salt thereof which compounds are useful in the treatment of HCMV infections.Type: GrantFiled: October 6, 1998Date of Patent: May 29, 2001Assignee: Boehringer Ingelheim (Canada) Ltd.Inventors: Eric Malenfant, Jeffrey O'Meara, Robert Déziel, William W. Ogilvie
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Patent number: 6211170Abstract: A compound of formula I: wherein R1 is hydrogen, methyl, ethyl, methoxy or methylthio; R2 and R3 each independently is hydrogen or C1-3 alkyl; R4 is hydrogen, lower alkyl, methoxy, ethoxy, or benzyloxy; R5 is lower alkyl, lower cycloalkyl, (CH2)mC(O)OR6 wherein m is the integer 1 or 2 and R6 is lower alkyl, phenyl optionally substituted with C(O)OR7 wherein R7 is lower alkyl or phenyl (lower alkyl); or R6 is Het or Het(lower alkyl; or R4 and R5 together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with benzyloxycarbonyl or with phenyl optionally substituted among other group with C(O)OR7 wherein R7 is lower alkyl or (lower alkyl)phenyl; X is selected from the group consisting of O, S, SO, SO2, NR8, wherein R8 is H or lower alkyl; and Y is C1-10 non-cyclic or cyclic alkyl; [(CH2)0-1]-phenyl, said phenyl ring optionally substituted; Het or Het(lower alkyl); or when X is NR8, wherein R8 is lower alkyl and Y is lower alkyl orType: GrantFiled: October 6, 1998Date of Patent: April 3, 2001Assignee: Boehringer Ingelheim (Canada) Ltd.Inventors: Christiane Yoakim, Robert Déziel, Stephen Kawai, William W. Ogilvie, Jeffrey O'Meara, Catherine Chabot
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Patent number: 5846941Abstract: Disclosed herein are peptidomimetic compounds of the formula A--B--D--CH.sub.2 CH{CH.sub.2 C(O)R.sup.1 }C(O)--NHCH{CR.sup.2 (R.sup.3)COOH}C(O)--E wherein A is a terminal group, for example an optionally substituted phenylalkanoyl, and B is a N-methyl amino acid residue; or A and B together form a saturated or unsaturated alkylaminocarbonyl; D is an amino acid residue; R.sup.1 is alkyl, cycloalkyl, a monosubstituted or a disubstituted amino; R.sup.2 is hydrogen and R.sup.3 is phenylalkyl, or R.sup.2 and R.sup.3 are joined to form a cycloalkyl; and E is a terminal unit, for example, an alkylamino or a monovalent amino acid radical such as NHCH(alkyl)C(O)OH. The derivatives are useful for treating herpes infections.Type: GrantFiled: June 5, 1995Date of Patent: December 8, 1998Assignee: Boehringer Ingelheim (Canada) Ltd.Inventors: Pierre Louis Beaulieu, Robert Deziel, Montse Llinas Brunet, Neil Moss, Raymond Plante
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Patent number: 5830864Abstract: Disclosed herein are peptide derivatives of the formulaA--B--NHCH{CH.sub.2 C(O)R.sup.1 }C(O)--NHCH{CR.sup.2 (R.sup.3)COOH}C(O)--Dwherein A is a terminal group, for example, an alkylaminocarbonyl or a phenylalkylaminocarbonyl; B is an amino acid residue; R.sup.1 is alkyl, cycloalkyl or a disubsubstituted amino; R.sup.2 is hydrogen or alkyl and R.sup.3 is alkyl, or R.sup.2 is hydrogen and R.sup.3 is phenylakyl, or R.sup.2 and R.sup.3 are joined to form a cycloalkyl; and D is a terminal unit, for example, an alkylamino or a monovalent amino acid radical such as NHCH(alkyl)C(O)OH. The derivatives are useful in treating herpes infections.Type: GrantFiled: July 17, 1995Date of Patent: November 3, 1998Assignee: Boehringer Ingelheim (Canada), Ltd.Inventors: Robert Deziel, Neil Moss, Raymond Plante
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Patent number: 5700780Abstract: Disclosed herein are peptide derivatives of the formula X?--NR.sup.1 --CH(R.sup.2)--C(W.sup.1)!.sub.n --NH--CR.sup.3 (R.sup.4)--C(W.sup.2)--NR.sup.5 --CH?CH.sub.2 C(O)--Y!--C(W.sup.3)--NH--CR.sup.6 --?CR.sup.7 --(R.sup.8)--COOH!--C(W.sup.4)--NH--CR.sup.9 (R.sup.10)--Z wherein X is a terminal group, for example, alkanoyl or phenylalkanoyl radicals, R.sup.1 is hydrogen, alkyl or phenylalkyl, R.sup.2, R.sup.4 and R.sup.10 am selected from amino acid or derived amino acid residues, R.sup.3, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are hydrogen or alkyl, or R.sup.7 and R.sup.8 are joined to form a cycloalkyl, W.sup.1, W.sup.2, W.sup.3 and W.sup.4 are oxo or thioxo, Y is, for example, an alkyl or a cycloalkyl, Z is a terminal group, for example, COOH or CH.sub.2 OH, and n is 0 or 1. The derivatives are useful for treating herpes infections.Type: GrantFiled: October 11, 1995Date of Patent: December 23, 1997Assignee: Boehringer Ingelheim (Canada), Ltd.Inventors: Pierre Louis Beaulieu, Robert Deziel, Pierre Lavallee
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Patent number: 5484771Abstract: Described herein are peptide derivatives of the formula R.sup.1 NH--CO--Q--C(O)--NR.sup.2 --CH[CH.sub.2 C(O)--Y]--C(O)--NH--CH[CR.sup.3 (R.sup.4)--COOH]--C(W)--NH--CHR.sup.5 --Z wherein R.sup.1 is an optionally substituted alkyl or optionally substituted phenylalkyl, R.sup.2 is hydrogen or alkyl, R.sup.3 and R.sup.4 each independently is hydrogen or alkyl, or R.sup.3 and R.sup.4 are joined to form a cycloalkyl. R.sup.5 is alkyl, cycloalkyl or (cycloalkyl)alkyl, Q is a divalent radical, for example, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or 1,2-cyclohexanediyl, which serves as a two carbon spacer. W is oxo or thioxo, Y is, for example, an alkoxy or a monosubstituted or disubsdtuted ammo, and Z is a terminal unit, for example, hydrogen, COOH or CH.sub.2 OH. The derivatives are useful for treating herpes infections.Type: GrantFiled: March 29, 1994Date of Patent: January 16, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Pierre L. Beaulieu, Robert Deziel, Neil Moss
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Patent number: 5476841Abstract: Peptide derivatives are of the formula A--B--D--NHCH{CH.sub.2 C(O)R.sup.1 }C(O)--NHCH{CR.sup.2 (R.sup.3)--COOH}C(O)--E wherein A is a lower alkanoyl bearing two substituents, each substituent selected independently from phenyl or a monosubstituted phenyl wherein the monosubstituent is alkyl, halo, hydroxy or alkoxy; B is a N-methyl amino acid residue; D is an amino acid residue; R.sup.1 is alkyl, cycloalkyl, a monosubstituted amino or a disubstituted amino; R.sup.2 is hydrogen or alkyl and R.sup.3 is alkyl, or R.sup.2 and R.sup.3 are joined to form a cycloalkyl; and E is a terminal unit, for example, an alkylamino or a monovalent amino acid radical such as NHCH(alkyl)C(O)OH. The derivatives are useful for treating herpes infections.Type: GrantFiled: February 28, 1994Date of Patent: December 19, 1995Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Robert Deziel, Neil Moss
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Patent number: 5380727Abstract: Disclosed herein is a combination of an antiviral nucleoside analog and a ribonucleotide reductase inhibiting peptide derivative. The combination is useful for treating herpes infections.Type: GrantFiled: December 17, 1991Date of Patent: January 10, 1995Assignee: Bio-Mega, Inc.Inventors: Robert Deziel, Yvan Guindon
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Patent number: 4841043Abstract: There is disclosed a process for producing carbapenam diazo intermediates of the formula ##STR1## wherein R.sup.1 is hydrogen or a hydroxy-protecting group,R.sup.2 is a lower alkyl having from 1-6 carbon atoms, andR.sup.3 represents a conventional carboxyl-protecting group.The processs comprises alkylating a 4-substituted azetidinone with the tin enolate of an .alpha.-bromoketone, in the presence of a silver salt, iodine, or iodine salt as a catalyst, and a strongly polar solvent. The .beta./.alpha. yield of the product diazo intermediate is approximately 3/1.Type: GrantFiled: August 3, 1987Date of Patent: June 20, 1989Assignee: Bristol-Myers CompanyInventors: Robert Deziel, Masaki Endo
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Patent number: 4788282Abstract: A process is disclosed for the deprotection of allylic esters and ethers. The process comprises reacting an allyl ester of a carboxylic acid or an allyl ether of a phenol with pyrrolidine or piperidine and a catalytic amount of an organic-soluble palladium complex having a coordinating phosphine ligand to cleave the allyl moiety. The resultant carboxylic acid or phenol is then recovered.Type: GrantFiled: June 7, 1985Date of Patent: November 29, 1988Assignee: Bristol-Myers CompanyInventor: Robert Deziel