Abstract: A process for the preparation of 1,6-dichloro-1,6-dideoxy-.beta.-D-fructofuranosyl-4-chloro-4-deoxy-.alpha. -galactopyranoside comprising the steps of (a) reacting sucrose with a tritylating agent; (b) acetylating the tritylated reaction product; (c) detritylating the acetylated reaction product; (d) isomerizing the resulting penta-acetate; (e) chlorinating the isomerized product; and (f) deacetylating the chlorinated reaction product.
Type:
Grant
Filed:
October 20, 1986
Date of Patent:
January 31, 1989
Assignee:
McNeilab, Inc.
Inventors:
William Tully, Nicholas M. Vernon, Peter A. Walsh
Abstract: Hexahydropyrrolizines of the formula (I): ##STR1## wherein A is a 3-7 carbon or hetero-containing ring,R.sup.1 is a substituent, andx is 0-3.Also, pharmaceutical compositions for treating pain and methods for synthesis and use as well as novel intermediates in the synthesis.
Abstract: A method for the synthesis of the 2-propanone (I) is described starting from alkoxide (II) through the lactone (IV). ##STR1## Excellent control of the location of the substitution on the phenyl ring is achieved and the reaction proceeds in high yield.
Type:
Grant
Filed:
September 21, 1987
Date of Patent:
January 17, 1989
Assignee:
McNeilab, Inc.
Inventors:
David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
Abstract: Sulfamates of the following formula (I) are anticonvulsants and are useful in the treatment of epilepsy: ##STR1## wherein R is one or more substituents such as alkyl, halo, alkoxy, CH.sub.3 or nitro; andx is 0-3.
Abstract: Chlorination of carbohydrates and alcohols utilizing a chlorinating reagent selected from triphenylphosphine oxide/thionyl chloride, thiphenylphosphine oxide/phosgene, triphenylphosphine sulfide/thionyl chloride and triphenylphosphine sulfide/phosgene.
Type:
Grant
Filed:
October 20, 1986
Date of Patent:
November 8, 1988
Assignee:
McNeilab, Inc.
Inventors:
Eleanor A. O'Brien, Thomas O'Connor, Mathew R. J. Tuite, Leroy B. High
Abstract: An efficient synthesis of quanidines, e.g. of the formula (III), by oxidizing a thiourea, e.g. of the following formula (II): ##STR1## with H.sub.2 O.sub.2 and a molybdenum catalyst to yield an aminoiminomethane sulfonic acid which can then be reacted with an amine followed by optional transamination steps.
Type:
Grant
Filed:
November 24, 1986
Date of Patent:
November 1, 1988
Assignee:
McNeilab, Inc.
Inventors:
Cynthia A. Maryanoff, James N. Plampin, Robin C. Stanzione
Abstract: A method for synthesizing a tri-substituted phenyl compound (I) by using a 1,2-addition followed by a 1,4-addition to 1,4-benzoquinone (II): ##STR1## wherein X is hydroxy, alkoxy or alkanoyloxy, Ar.sup.1 is an organic group and R is an unsubstituted or substituted alkyl group.
Type:
Grant
Filed:
March 19, 1987
Date of Patent:
September 20, 1988
Assignee:
McNeilab, Inc.
Inventors:
Dennis C. Liotta, Cynthia A. Maryanoff, Vasken Paragamian
Abstract: Propylamines of the formula (I): ##STR1## and isomers thereof, particularly those enantiomers and racemates relative to the chiral carbon indicated by an asterisk (*). The propylamines can be used for the treatment of hypertension or angina in humans. A is pyrrolidine, piperidine or morpholine and B is an aromatic heterocycle, aromatic carbocycle or saturated carbocycle.
Abstract: A tamper-resistant vessel which contains a liquid is provided with a non-adherent multi-walled construction having, in one embodiment, at least two adjacent non-adherent layers for providing a void in between to enable tamper indication by discoloration indicative of gross spoliage. In one embodiment, the container or vessel has an opaque inner wall and a closely spaced transparent outer wall, with a void in between. Puncture from the outside through the two walls provides seepage of the interiorly-carried liquid between the multiple walls to provide the look of spoilage.
Type:
Grant
Filed:
May 20, 1987
Date of Patent:
July 5, 1988
Assignee:
McNeilab Inc.
Inventors:
Arthur A. Massucco, E. Joseph Stilwell, George E. Pickering, Richard E. Merrill
Abstract: Novel D-arabinose-1,5-diphosphate salts of the formula (I): ##STR1## wherein n is from about 3 to 4 and M.sup.+ is a cation as well as racemic and isomeric mixtures of the so-defined and forms of formula (I) are useful as hypoglycemic agents for the treatment of diabetes, e.g., in man.
Abstract: A process to prepare retinoyl chlorides, e.g., of the following formula (I): ##STR1## under very mild chlorinating conditions by the action of a reagent amount of dimethylchloroformamidinium chloride on a corresponding retinoic acid.
Abstract: Dihydropyridine compounds having 1,4,4-trisubstitution of the following formula (I): ##STR1## wherein R is one of --COR.sup.3, R.sup.3 being a group such as phenyl or benzyl; R.sup.4 where R.sup.4 is a heterocycle; --(CH.sub.2).sub.n NR.sup.5 R.sup.6, with R.sup.5 and R.sup.6 being alkyl or joined to define a ring; or --(CH.sub.2).sub.n COOR.sup.7, with R.sup.7 being alkyl or benzyl.R.sup.1 and R.sup.2 are alkyl, phenyl or substituted phenyl.The compounds are useful for the treatment of hypertension in mammals, e.g., in humans.
Abstract: Four decapeptides found to be analgesics and have antagonist activity to Neurokinin B which is also known as Neuromedin K. The decapeptide are of the following formula (I):A.sup.1 -D-Pro.sup.2 His.sup.3 -D.sup.4 Phe.sup.5 D-Trp.sup.6 Val.sup.7 -D-Trp.sup.8 -Leu.sup.9 -Nle.sup.10 -NH.sub.2 (I)wherein A.sup.1 and D.sup.4 are Asp or D-Asp amino acids. Also described is an opthalmic solution to treat pain or inflammation and an HPLC separation method using piperidine.
Abstract: Acetylenes of the formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, q, Alk, R.sup.3 n and R.sup.4 are as defined herein and Ar.sup.1 and Ar.sup.2 are aromatic, including the salts and ammonium derivatives of formula (I), in treating angina, hypertension and cardiac arrhythmias. Pharmaceutical compositions, methods of use and synthesis and novel intermediates are also part of the invention.
Abstract: A removable U.V. light array assembly for use in a photoactivatable agent, patient treatment system wherein photoactivatable agents, in contact with patient blood cells, are irradiated extracorporeally and then returned to the patient.
Type:
Grant
Filed:
May 22, 1987
Date of Patent:
April 12, 1988
Assignee:
McNeilab, Inc.
Inventors:
Kyu H. Lee, Vernon H. Troutner, Jack Goss, Martin J. King