Patents Assigned to McNeilabs, Inc.
  • Amidine benzodiazepines, methods for their use and intermediates
    Patent number: 4587244
    Abstract: Fused tetracyclic benzodiazepines of the formula (I): ##STR1## where R.sup.1 is a cyclic amine such as 1-piperazine and R.sup.2 is H or a substituent as defined herein are useful as antiovulatory and contragestational agents. Also, methods for their synthesis, intermediates used in such synthesis, methods for use as medicaments and pharmaceutical compositions are described.
    Type: Grant
    Filed: April 10, 1985
    Date of Patent: May 6, 1986
    Assignee: McNeilab, Inc.
    Inventor: Chih Y. Ho
  • 1-amino-or nitro-benzyl)indoles useful as intermediates
    Patent number: 4587349
    Abstract: Compounds of the present invention are of the formula (III): ##STR1## wherein R.sup.2 is a substituent as disclosed, R is alkyl and Y is NO.sub.2 or NH.sub.2. The invention compounds are useful as intermediates for tetracyclic benzodiazepines which may be used in treating hypertension.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: May 6, 1986
    Assignee: McNeilab, Inc.
    Inventor: Chih Y. Ho
  • Pyrrole-2-acetylamino acid derivative compounds
    Patent number: 4585784
    Abstract: Novel pyrrole-2-acetylamino compounds of the formula: ##STR1## and salts thereof, wherein R" is H, alkyl, (CH.sub.2).sub.n CO.sub.2 H, CH.sub.2 CH.sub.2 SCH.sub.3, (CH.sub.2).sub.4 NH.sub.2 or (CH.sub.2).sub.2 CONH.sub.2 ; and n is 1 or 2, which have the same analgesic and antiinflammatory utility as zomepirac, but with reduced liability toward gastrointestinal irritation, and esters of the compounds of the above formula which are useful as intermediates to make said compounds.
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: April 29, 1986
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • Methods for the treatment of ventricular dysrhythmia and prevention of ventricular fibrillation
    Patent number: 4584302
    Abstract: Various indole and benzothiophene compounds having a pendant pyrrolidinylidene amino or piperidinylideneamino group are useful in the prevention of ventricular fibrillation, e.g., in humans. The invention comprises methods for the treatment of ventricular dysrhythymia or the prevention of ventricular fibrillation.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: April 22, 1986
    Assignee: McNeilab, Inc.
    Inventors: William E. Hageman, Michael J. Zelesko
  • Chlorosulfate and azidosulfate esters of tetrahydro-2H-pyran-2-yl-methanol
    Patent number: 4582916
    Abstract: Sulfamates of the following formula (I): ##STR1## wherein X is O or CH.sub.2 and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as herein defined have been found to exhibit anticonvulsant activity and are thus useful in the treatment of conditions such as epilepsy. Further, pharmaceutical compositions containing a compound of formula (I) as well as methods for their use and intermediates form part of the present invention.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: April 15, 1986
    Assignee: McNeilab, Inc.
    Inventors: Bruce E. Maryanoff, Joseph F. Gardocki
  • Octahydroindolizine compounds useful as analgesics
    Patent number: 4582836
    Abstract: Octahydroindolizidines of the formula (I): ##STR1## where A is a 3-7 carbon or hetero-containing ring, R.sup.1 is a substituent and x is 0-3. Also, pharmaceutical composition for treating pain and methods for synthesis and use as well as novel intermediates in the synthesis.
    Type: Grant
    Filed: January 9, 1985
    Date of Patent: April 15, 1986
    Assignee: McNeilab, Inc.
    Inventors: Richard J. Carmosin, John R. Carson
  • Anxiety alleviating compositions containing loweralkyl-N-[amino(arylaminocarbonyl)-iminomethyl]-N-methylglycinates
    Patent number: 4575514
    Abstract: Compounds of the class of loweralkyl N-[amino(arylaminocarbonyl)iminomethyl]-N-methylglycinate acid addition salts are useful as antianxiety agents.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: March 11, 1986
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • Hexahydroindolinzine compounds, pharmaceutical compositions and methods and intermediates
    Patent number: 4572911
    Abstract: Hexahydroindolizines of the following formulae (I) and (II): ##STR1## are novel and have been found to possess antisecretory and antidepressant properties. Methods of preparation, intermediates thereto and use are also disclosed.
    Type: Grant
    Filed: August 2, 1984
    Date of Patent: February 25, 1986
    Assignee: McNeilab, Inc.
    Inventors: John R. Carson, Bruce E. Maryanoff
  • Aryl fatty acid leukotriene synthesis inhibitors
    Patent number: 4564476
    Abstract: Aryl fatty acid compounds of the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, and Y are as defined herein are novel and useful in the treatment of allergic and inflammatory disorders.
    Type: Grant
    Filed: October 29, 1984
    Date of Patent: January 14, 1986
    Assignee: McNeilab, Inc.
    Inventor: Chih Y. Ho
  • Amidine benzodiazepines, methods for their use and intermediates
    Patent number: 4547497
    Abstract: Fused tetracyclic benzodiazepines of the formula (I): ##STR1## where R.sup.1 is an acyclic amine or cyclic amine such as 1-piperidine, 4-morpholine or 1-piperazine and R.sup.2 is H or a substituent as defined herein as useful as antiallergins. Also, methods for their synthesis, intermediate used in such synthesis, methods for use as medicaments and pharmaceutical compositions.
    Type: Grant
    Filed: April 11, 1984
    Date of Patent: October 15, 1985
    Assignee: McNeilab, Inc.
    Inventor: Chih Y. Ho
  • Anticonvulsant N-aryl-N'-(2-thiazolidinylidene)ureas
    Patent number: 4542144
    Abstract: N-aryl-N'-(2-thiazolidinylidene)urea compounds of Formula II ##STR1## wherein: R is CH.sub.3, C.sub.2 H.sub.5, or H;R.sub.1 is CH.sub.3, C.sub.2 H.sub.5, Cl, Br, F, CF.sub.3, OCH.sub.3 or H, provided that R.sub.1 is not H where R is H;R.sub.2 is CH.sub.3 or H, provided that R.sub.2 is not H when R is H;R.sub.3 is H or F or CH.sub.3 ;R.sub.4 is H or CH.sub.3 ;R.sub.5 is CH.sub.3, C.sub.2 H.sub.5, Cl, Br, F, CF.sub.3, OCH.sub.3, have anticonvulsant activity and are useful in the treatment of epilepsy.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: September 17, 1985
    Assignee: McNeilab Inc.
    Inventor: Chris R. Rasmussen
  • 6H-indolo[2,1-c][1,4]benzodiazepines and 12-oxo derivatives useful as antihypertensives
    Patent number: 4529724
    Abstract: Compounds of the present invention are of the formula (I): ##STR1## wherein X is oxygen or two hydrogens, R.sup.1 is a variety of substituents or hydrogen and R.sup.2 is hydrogen, alkoxy, alkyl, CF.sub.3, halogen, NO.sub.2, OH or dialkylamino. The compounds are useful as blood pressure lowering agents and may be used in the treatment of hypertension. Also, part of the invention are pharmaceutical compositions and uses and intermediates for compounds of formula (I).
    Type: Grant
    Filed: October 11, 1983
    Date of Patent: July 16, 1985
    Assignee: McNeilab, Inc.
    Inventor: Chih Y. Ho
  • Imidoyl substituted pyrroles
    Patent number: 4528382
    Abstract: Novel compounds, which are aryl-pyrrolyl-imine derivatives of the Formula I ##STR1## and acid addition salts thereof are disclosed; which compounds may be prepared by the acid catalyzed condensation of an imidoyl chloride with a lower alkyl pyrrole-2-acetate; and which compounds are useful as intermediates to form by hydrolysis, the known useful ketone analogs which have anti-inflammatory and analgesic activity; and certain of which compounds have antisecretory, anti-irritable bowel, antidiarrheal and general behavior effect on the CNS properties.
    Type: Grant
    Filed: November 16, 1982
    Date of Patent: July 9, 1985
    Assignee: McNeilab, Inc.
    Inventor: John E. Mills
  • Heteroaromatic derivatives of iminomethyl piperidines and use to inhibit gastric acid secretion
    Patent number: 4528293
    Abstract: Compounds of the following formula (I): ##STR1## wherein Alk is a straight or branched chain alkylene of about 1 to 12 carbons and R.sup.1 is a heterocyclic ring system, have been found to possess potent antisecretory activity and are thus useful in the treatment of hyperacidity.
    Type: Grant
    Filed: October 11, 1983
    Date of Patent: July 9, 1985
    Assignee: McNeilab, Inc.
    Inventor: Malcolm K. Scott
  • 2-Amino-4,5-dihydro-1H-imizole-1-carboxanilides
    Patent number: 4513140
    Abstract: Novel 2-amino-4,5-dihydro-1H-imidazole-1-carboxanilides, which are made by reacting 2-amino-4,5-dihydroimidazole with an aryl isocyanate, are made stable to rearrangement when converted to acid addition salt form, and are useful either as antihypertensive agents and/or antisecretary agents, as well as being intermediates to prepare known pharmacologically active N-aryl-N'-(4,5-dihydro-1H-imidazol-2-yl)ureas.
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: April 23, 1985
    Assignee: McNeilab, Inc.
    Inventor: Leonard R. Hecker
  • Process for production of methyl 2-tetradecylgycidate
    Patent number: 4499294
    Abstract: An improved process for producing the hypoglycemic compound, methyl 2-tetradecylglycidate, by reacting methyl .alpha.-chloropalmitate with lithium methoxide in the presence of formaldehyde in a dipolar aprotic solvent such as DMF or DMSO.
    Type: Grant
    Filed: January 21, 1983
    Date of Patent: February 12, 1985
    Assignee: McNeilab, Inc.
    Inventor: Cynthia A. Maryanoff
  • Process for preparation of substituted formamidine and substituted N-iminomethyl piperidine
    Patent number: 4499274
    Abstract: An improved process for preparing fenoctimine, which is 4-(diphenylmethyl)-1-[(octylimino)methyl]piperidine by: (1) reacting dimethylformamide with dimethyl sulfate to form a complex; (2) reacting the resultant dimethylformamide/dimethyl sulfate complex with n-octylamine and optionally with dimethylamine; (3) thereafter treating the reaction with aqueous base to form N,N-dimethyl-N'-octyl-formamidine; and (4) reacting said formamidine, without need for further purification, with 4-(diphenylmethyl) piperidine to obtain 4-(diphenylmethyl)-1-[(octylimino)-methyl]piperidine.
    Type: Grant
    Filed: March 17, 1983
    Date of Patent: February 12, 1985
    Assignee: McNeilab, Inc.
    Inventors: Georg Feth, John E. Mills
  • Saturated leukotriene derivatives as antiallergens
    Patent number: 4469705
    Abstract: Hydroxythioether fatty acid derivatives of formula (I) ##STR1## wherein n is 2-5, m is 8-12, R.sup.1 is OH, O-loweralkyl, NH.sub.2, NH-loweralkyl or NH-carboxyalkyl; R.sup.2 is OH or O-loweralkyl; X is H or NH.sub.2 or ##STR2## and salts thereof are useful in preventing or alleviating asthma or other allergic diseases.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: September 4, 1984
    Assignee: McNeilab, Inc.
    Inventors: Kerry G. Stanley, Winston Ho
  • N-aryl-N'-(1,4,5,6-tetrahydropyrimidin-2-yl)ureas for intestinal disorders
    Patent number: 4466966
    Abstract: N-(substituted phenyl)-N'-(1,4,5,6-tetrahydropyrimidin-2-yl)ureas and pharmaceutically-acceptable salts thereof are disclosed to be useful in relieving the symptoms associated with irritable bowel syndrome, and as anti-diarrheal agents.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: August 21, 1984
    Assignee: McNeilab, Inc.
    Inventor: Chris R. Rasmussen
  • Hydroxythioether fatty acid derivatives
    Patent number: 4461775
    Abstract: Hydroxythioether fatty acid derivatives of formula (I) ##STR1## wherein n is 2-5, m is 8-12, R.sup.1 is OH, O-loweralkyl, NH.sub.2, NH-loweralkyl or NH-carboxyalkyl, R.sup.2 is OH or O-lower-alkyl, X is H or NH.sub.2 or ##STR2## and salts thereof are useful in preventing or alleviating asthma or other allergic diseases.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: July 24, 1984
    Assignee: McNeilab, Inc.
    Inventors: Kerry G. Stanley, Winston Ho