Patents Assigned to Bio-Mega/Boehringer Ingelheim Research Inc.
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Patent number: 5672586Abstract: Disclosed herein are compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or (1-4C) alkyl, R.sup.2 is (1-4C) alkyl or a therapeutically acceptable salt thereof. The compounds are useful for treating herpes infections.Type: GrantFiled: June 18, 1996Date of Patent: September 30, 1997Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.Inventors: Jean Andre Gauthier, Neil Moss
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Patent number: 5648337Abstract: Disclosed herein are pentapeptide derivatives of the formula (SEQ ID NO: 24) XNR.sup.1 --CH(R.sup.2)--C(O)--NH--CH(R.sup.3 --C(O)--NR.sup.4 --CH(CH.sub.2 Y)--CO--NH--CH[CR.sup.5 (R.sup.6)--COOH]--C(W)--NH--CH(R.sup.7)--Z wherein X is a terminal group, for example, alkanoyl or phenylalkanoyl radicals, R.sup.1 is alkyl or phenylalkyl, R.sup.2, R.sup.3 and R.sup.7 are selected from the side chains of amino acid or derived amino acid residues, R.sup.4, R.sup.5, and R.sup.6 are hydrogen or lower alkyl, W is oxo or thioxo, Y is carboxy, carbamyl or 5-1H-tetrazolyl and Z is carboxy or 5-1H-tetrazolyl. The derivatives are useful for treating herpes infections.Type: GrantFiled: July 13, 1993Date of Patent: July 15, 1997Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Julian Adams, Pierre Louis Beaulieu, Pierre Lavallee, Raymond Plante, Sumanas Rakhit
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Patent number: 5614533Abstract: Disclosed herein are compounds of formula 1 ##STR1## wherein X is a terminal group, for example, an aryloxycarbonyl, an alkanoyl or an optionally mono- or disubstituted carbamoyl; B is absent or an amino acid residue, for example, Val or Ash; R.sup.1 is hydrogen or a ring substituent, for example, fluoro or methyl; R.sup.2 is alkyl; and Y is a ring substituent, for example, phenoxy, 2-pyridinylmethoxy, phenylthio or 2-pyridinylthio. The compounds inhibit the activity of human immunodeficiency virus (HIV) protease and interfere with HIV induced cytopathogenic effects in human cells. These properties render the compounds useful for combating HIV infections.Type: GrantFiled: November 9, 1994Date of Patent: March 25, 1997Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.Inventors: Paul C. Anderson, Fran.cedilla.ois Soucy, Christiane Yoakim, Pierre Lavall ee, Pierre L. Beaulieu
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Patent number: 5574015Abstract: Disclosed herein are peptide derivatives 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 or alkyl and R.sup.3 is alkyl, or 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: October 17, 1994Date of Patent: November 12, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Pierre L. Beaulieu, Robert D eziel, Neil Moss, Raymond Plante
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Patent number: 5565476Abstract: Disclosed herein are compounds of the formula:A'--N(R.sup.1')C(O)CH.sub.2 CHR.sup.2 C(O)--Bwherein A' is, for example, HO--CR.sup.5 (R.sup.6)CH.sub.2 wherein R.sup.5 and R.sup.6 together with the carbon atom to which they are attached form a 1,1-(lower cycloalkanediyl); R.sup.1' is R.sup.7 R.sup.8 NC(O)CH.sub.2 wherein R.sup.7 is lower alkyl and R.sup.8 is pyridinyl-(CH.sub.2).sub.n wherein n is the integer one or two; R.sup.2 is, for example, 4-thiazolylmethyl or (2-amino-4-thiazolyl)methyl; and B is a renin substrate transition state mimic, for example, [1(S)-(cyclohexylmethyl)-2(R), 3(S)-dihydroxy-5-methylhexyl]amino. The compounds inhibit renin activity and are indicated for the treatment of hypertension and congestive heart failure.Type: GrantFiled: May 1, 1995Date of Patent: October 15, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Paul C. Anderson, Teddy Halmos, Grace L. Jung, Marc-Andr e Poupart, Bruno Simoneau
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Patent number: 5554634Abstract: Disclosed herein are compounds of the formula:A'--N(R.sup.1')c(O)CH.sub.2 CHR.sup.2 C(O)--Bwherein A' is HO--CR.sup.5 (R.sup.6)CH.sub.2 wherein R.sup.5 and R.sup.6 together with the carbon atom to which they are attached form a 1,1-(lower cycloalkanediyl); R.sup.1' is R.sup.7 R.sup.8 NC(O)CH.sub.2 wherein R.sup.7 hydrogen or lower alkyl and R.sup.8 is lower alkyl; R.sup.2 is, for example, 4-thiazolylmethyl or (2-amino-4-thiazolyl)methyl; and B is a renin substrate transition state mimic, for example, [1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino. The compounds inhibit renin activity and are indicated for the treatment of hypertension and congestive heart failure.Type: GrantFiled: May 1, 1995Date of Patent: September 10, 1996Assignee: Bio-Mega Boehringer Ingelheim Research Inc.Inventors: Paul C. Anderson, Teddy Halmos, Grace L. Jung, Marc-Andr e Poupart, Bruno Simoneau
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Patent number: 5552405Abstract: Disclosed herein are compounds of formula 1 ##STR1## wherein X is a terminal group, for example, an aryloxycarbonyl or an alkanoyl; B is absent or an amino acid residue, for example, Val or Asn; R.sup.1 is alkyl; and Y is a ring substituent, for example, benzyl, benzyloxy, phenylthio or 2-pyridinylthio. The compounds inhibit the activity of human immunodeficiency virus (HIV) protease and interfere with HIV induced cytopathogenic effects in human cells. These properties render the compounds useful for combating HIV infections.Type: GrantFiled: July 31, 1995Date of Patent: September 3, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.Inventors: Vida Gorys, Fran.cedilla.ois Soucy, Christiane Yoakim, Pierre L. Beaulieu
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Patent number: 5552384Abstract: Disclosed herein is a combination of an antiviral nucleoside analog and a ribonucleotide reductase inhibiting peptide derivative. The combination is useful for combatting herpes infections.Type: GrantFiled: June 6, 1994Date of Patent: September 3, 1996Assignee: Bio-Mega Boehringer Ingelheim Research Inc.Inventors: Robert D eziel, Yvan Guindon
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Patent number: 5550291Abstract: Disclosed herein is a stereospecific synthesis amenable to the large scale preparation of a hydrochloric acid addition salt of a chlorohydrin of the formula ##STR1## wherein R.sup.1 and R.sup.2 are amino protective groups and R.sup.3 is an amino acid side chain or a protected amino acid side chain. The synthesis involves reacting an aldehyde of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined hereinbefore with (chloromethyl)lithium at -20.degree. C. or below and contacting the resulting diastereoisomeric mixture of lithium alcoholates with aqueous hydrochloric acid to obtain a separable mixture of the hydrochloric acid addition salts of the chlorohydrin and its corresponding hydroxy diastereoisomer. The hydrochloric acid addition salt of the chlorohydrin is transformed readily into corresponding optionally amino-protected aminoepoxides; for example, 3(S)-(tert-butyloxycarbonylamino)-l,2(S)-epoxy-4-phenyl-butane.Type: GrantFiled: May 4, 1995Date of Patent: August 27, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.Inventors: Pierre L. Beaulieu, Yvan Guindon, Dominik M. Wernic
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Patent number: 5541163Abstract: Disclosed herein are compounds of the formula:A--N(R.sup.1)C(O)CH.sub.2 CHR.sup.2 C(O)--Bwherein A is R.sup.3 R.sup.4 NC(O)CH.sub.2 wherein, for example, R.sup.3 is hydrogen or alkyl and R.sup.4 is hydrogen, alkyl or a substituted alkyl such as 2-(2-pyridinyl)ethyl, or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino, morpholino or thiomorpholino; R.sup.1 is, for example, benzyl, alkyl or a substituted alkyl such as cyclohexylmethyl; R.sup.2 is, for example, alkyl, cycloalkylmethyl, 1H-imidazol-4-ylmethyl, 4-thiazolylmethyl or (2-amino-4-thiazolyl)methyl; and B is a renin substrate transition state analog, for example, [1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino. The compounds inhibit renin activity and are indicated for the treatment of hypertension and congestive heart failure.Type: GrantFiled: September 17, 1993Date of Patent: July 30, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Pierre Lavall ee, Bruno Simoneau
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Patent number: 5523315Abstract: Disclosed herein are compounds of the formula:A--N(R.sup.1)C(O)CH.sub.2 CHR.sup.2 C(O)--Bwherein A is various oxygen-bearing radicals; for example, HO--CH(R.sup.3)CH.sub.2 wherein R.sup.3 is, inter alia, hydrogen, lower alkyl, lower cycloalkyl or phenyl; or HO--CR.sup.5 (R.sup.6)CH.sub.2 wherein each of R.sup.5 and R.sup.6 is lower alkyl, or R.sup.5 and R.sup.6 together with the carbon atom to which they are attached form a 1,1-(lower cycloalkanediyl); R.sup.1 is, for example, benzyl, alkyl or a substituted alkyl such as cyclohexylmethyl; R.sup.2 is, for example, cyclo-alkylmethyl, 1H-imidazol-4-ylmethyl, 4-thiazolylmethyl or (2-amino-4-thiazolyl)methyl; and B is a renin substrate transition state mimic, for example, [1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl]amino. The compounds inhibit renin activity and are indicated for the treatment of hypertension and congestive heart failure.Type: GrantFiled: September 20, 1993Date of Patent: June 4, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Paul C. Anderson, Teddy Halmos, Grace L. Jung, Marc-Andre Poupart, Bruno Simoneau
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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: 5376635Abstract: Disclosed herein are derivatives of atrial natriuretic peptides which are characterized by having (at positions 106 and/or 124) a phenylalanyl residue bearing a fluoro or trifluoromethyl substituent on the aromatic portion thereof. Optionally, the exocyclic N-terminal peptide segment and the first cystienyl residue (at position 105) are replaced by an optionally substituted thioalkanoyl residue. The derivatives possess useful diuretic, natriuretic and antihypertensive activities.Type: GrantFiled: October 23, 1991Date of Patent: December 27, 1994Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Sumanas Rakhit, Mahesh H. Goghari
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Patent number: 5258493Abstract: Disclosed herein are cyclic peptide derivatives of the formula ##STR1## wherein A is absent or the tripeptide radical Thr.rarw.Gly.rarw.Ala, R.sup.1 is benzyl or benzyl monosubstituted at position 4 of the aromatic ring with halo, hydroxy, lower alkyl or lower alkoxy, R.sup.2 and R.sup.4 each independently is hydrogen or lower alkyl, R.sup.3 is lower alkyl or lower alkyl monosubstituted with a hydroxy, R.sup.5 is lower alkyl, Y is oxo or thioxo and Z is hydroxy or NR.sup.6 R.sup.7 wherein R.sup.6 and R.sup.7 each independently is hydrogen or lower alkyl. The derivatives are useful for treating herpes infections.Type: GrantFiled: March 16, 1992Date of Patent: November 2, 1993Assignee: Bio-Mega/Boehringer Ingelheim Research Inc.Inventors: Julian Adams, John DiMaio, Raymond Plante