Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
Type:
Grant
Filed:
July 15, 1983
Date of Patent:
May 8, 1984
Assignee:
Glaxo Group Limited
Inventors:
Eric W. Collington, Harry Finch, Roger F. Newton
Abstract: Method of preparing antimicrobial compounds of the formula: ##STR1## comprising the following steps: (1) halogenating allyl halide to form 1,2,3-trihalopropane; (2) dehydrohalogenating the 1,2,3-trihalopropane to form 2,3-dihalo-1-propene;(3) treating the 2,3-dihalo-1-propene with a Grignard reagent of the formula R--MgHal, where R is as defined above, followed by treatment with magnesium, to form 3-(R-substituted)-2-magnesiumhalide)-1-propene;(4) treating the 3-(R-substituted)-2-(magnesiumhalide)-1-propene with cyanogen to form 3-(R-substituted)-2-cyano-1-propene; and(5) brominating the 3-(R-substituted)-2-cyano-1-propene to form the desired product.
Abstract: Antimicrobial compounds of the formula: ##STR1## where R is C.sub.3-12 alkyl, straight or branched chain C.sub.3 -C.sub.8 cycloalkyl; C.sub.3-8 cycloalkylC.sub.1-3 alkyl; or saturated heterocyclic radical selected from the group consisting of pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, isoxazolidinyl, oxazolidinyl, isothiazolidinyl, pyrazolidinyl, imidazolidinyl, piperazinyl, and piperidinyl.
Type:
Grant
Filed:
December 22, 1981
Date of Patent:
April 10, 1984
Assignee:
Merck & Co., Inc.
Inventors:
John E. Engelhart, Marshall R. Angeles, Michael J. D'Errico
Abstract: Novel cyanoguanidine derivatives, and acid addition salts thereof useful as medicines which have pharmacological actions such as anti-secretory effect, local anesthesia action and the like; and process for the preparation thereof.
Abstract: Mammalian collagenase is inhibited by compounds of the formula ##STR1## or salts thereof, wherein R is hydrogen, alkanoyl of 2 to 10 carbon atoms or arylcarbonyl;R.sub.1 is of 3 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, aryl or arylalkyl;R.sub.2 is hydrogen, ##STR2## R.sub.3 is ##STR3## R.sub.4 is hydrogen, methyl, ethyl, or ##STR4## R.sub.5 and R.sub.6 are each independently selected as --OCH.sub.3 or --OCH.sub.2 CH.sub.3 or are combined as --OCH.sub.2 CH.sub.2 O-- or --O--(CH.sub.2).sub.3 --O--;R.sub.7 and R.sub.8 are each independently selected as hydrogen, methyl or ethyl or are combined as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 --;R.sub.9 is hydrogen, methyl, ethyl ##STR5## m is an integer from 0 to 7; p is an integer from 1 to 3; AA.sub.n is an amino acid chain of from one to three amino acids; n is 1 or 1, 2 or 1, 2, 3;when p is 1, AA.sub.n is AA.sub.1 ;when p is 2, AA.sub.n is AA.sub.1 -AA.sub.2 ;when p is 3, AA.sub.n is AA.sub.1 -AA.sub.
Abstract: A series of organic diamine base compounds derived from either an aromatic, alicyclic or heterocyclic ring and possessing, for the most part, an intervening methylene group between the ring and the aforesaid basic moiety have been prepared, including their pharmaceutically acceptable acid addition salts as well as oral pharmaceutical compositions containing same. These particular compounds are found to be useful in therapy as oral hypoglycemic agents. Preferred member compounds include 1,1'-[1,2-phenylenebis(methylene)]bispiperidine, 2,3-dihydro-2-[2-(1-piperidinomethyl)phenylmethyl]-1H-isoindole and 2,3-dihydro-2-[2-(4-morpholinomethyl)phenylmethyl]-1H-isoindole. Alternate methods of preparation are provided and the two principal synthetic routes leading to these compounds are described in some detail.
Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.
Type:
Grant
Filed:
November 10, 1982
Date of Patent:
October 11, 1983
Assignee:
Glaxo Group Limited
Inventors:
Eric W. Collington, Harry Finch, Roger F. Newton, Christopher J. Wallis
Abstract: Quaternary ammonium salts of certain phenylpropylamines and phenylbutylamines are useful antiarrhythmic drugs. A method for treating arrhythmia and prolonging the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such quaternary ammonium salts are disclosed.
Abstract: This invention is directed to 2-chloro-6-nitro-aniline compounds of the formula ##STR1## wherein A represents hydrogen, a straight or branched alkyl radical having from 1 to 6 carbon atoms a cycloalkyl radical having from 3 to 6 carbon atoms, a chlorine-substituted or hydroxyl-sustituted alkyl radical having from 2 to 6 carbon atoms, or an allyl or trifluoroacetyl group,B represents hydrogen or a methyl, ethyl, n-propyl, or isopropyl group, orA and B represent together an alkylene radical optionally interrupted by oxygen, .dbd.NH or, .dbd.NCH.sub.3, and having up to 5 members, or the group .dbd.CH-N(CH.sub.3).sub.2,R represents hydrogen, fluorine, chlorine, or bromine or a trifluoromethyl, methyl, or methoxy group, and X represents oxygen or sulphur,and novel herbicidal compositions containing these compounds as active ingredients.
Type:
Grant
Filed:
March 13, 1981
Date of Patent:
July 19, 1983
Assignee:
Celamerck GmbH & Co. KG
Inventors:
Wolfgang Buck, Richard Sehring, Gerbert Linden, Sigmund Lust
Abstract: The invention relates to 3-phenoxymethylene-anilines of the formula ##STR1## wherein R is a ##STR2## radical or C.sub.1 -C.sub.4 alkoxy, R is halogen or C.sub.1 -C.sub.2 haloalkyl,R.sub.2, R.sub.3 and R.sub.4, each independently of the other, are hydrogen or halogenR.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkylR.sub.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl, andR.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, while R.sub.5 and R.sub.6, or R.sub.6 and R.sub.7, together with the nitrogen atom to which they are attached, can form a heterocyclic ring system which may be interrupted by further hetero-atoms.Where R is a --NR.sub.6 R.sub.7 radical, the salts with acids also fall within the scope of formula I. These compounds have excellent selective herbicidal properties.
Abstract: This invention relates to a method of using compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, alkyl or alkenyl; R.sup.2 is hydrogen, alkyl, cycloalkyl or mononuclear aryl or R.sup.1 and R.sup.2, taken together with the carbon atom to which they are attached, form a cycloalkyl or cycloalkoxyalkyl; R.sup.3 is hydroxy, alkyl, alkoxycarbonyl, hydroxy lower alkyl or a radical of the formula: --C(.dbd.Y)NR.sup.4 R.sup.5 wherein R.sup.4 is hydrogen, alkyl, alkenyl, R.sup.5 is alkyl, alkenyl, alkoxyalkyl, carbalkoxy, mononuclear aryl, or R.sup.4 and R.sup.5 may be joined together with the nitrogen atom to which they are attached to form a 5 to 7 membered heterocyclic ring having from 1 to 3 hetero atoms; Y is O or S; X is alkyl, alkoxycarbonylalkyl or cyano; m is an integer of 0 to 2 and n and n' are integers each having a value of 1 to 2 and the dotted line indicates an optional double bond anywhere in the ring, compositions containing said compounds as insect repellents and to novel compounds.
Abstract: Sulphonanilides of formula ##STR1## and salts thereof, wherein R.sup.1 represents alkyl or certain other groups;R represents alkylene or alkenylene;A represents --COR.sup.12 or a carbonyl derivative or addition compound thereof, where R.sup.12 represents hydrogen, alkyl or certain other groups; andR.sup.2 -R.sup.6 represent hydrogen, alkyl, halogen or certain other groups;are pesticides and plant growth regulants, especially herbicides and fungicides.
Type:
Grant
Filed:
December 14, 1978
Date of Patent:
September 14, 1982
Assignee:
FBC Limited
Inventors:
Geoffrey R. Cliff, Russell G. Hunt, Albert Percival
Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7-C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.
Abstract: An N-alkenyl-2-aminomethyl-pyrrolidine is prepared by firstly reacting tetrahydrofurfurylamine with gaseous hydrochloric acid and thionyl chloride to produce 2,5 dichloropentylamine hydrochloride. This is acetylized, possibly by acetyl chloride in dichloroethane in the presence of triethylamine, into N-acetyl-2,5-dichloropentylamine which is condensed with an alkenylamine into an N-alkenyl-2-acetylaminomethyl pyrrolidine from which the acetyl group is separated, for example by boiling with concentrated hydrochloric acid.
Abstract: Meta-sulfonamido-benzamide derivatives of the formula: ##STR1## [wherein R is a hydrogen atom or a lower alkyl, cyano, or lower alkanesulfonyl group;R.sup.1 is a lower alkyl, phenyl, amino, lower alkylamino, di(lower)alkylamino, or C.sub.4 -C.sub.5 alkyleneamino group;R.sup.2 is a hydrogen or halogen atom or a lower alkyl, di(lower)alkylamino, or lower alkoxy group;R.sup.3 is a hydrogen atom or a methyl or methoxy group;R.sup.4 is a hydrogen or halogen atom;R.sup.5 is a lower alkyl, lower alkenyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl, or halogenobenzyl group; andn is 1 or zero]or their acid addition salts, showing pharmacological activity such as anti-emetic or psychotropic activity, are provided via several routes.