Abstract: N-R-N'-R'-N-[4(or 5)-PY-2-pyrimidinyl]ureas (I) or salts thereof, where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, R' is hydrogen or methyl and R is methyl or ethyl when PY is attached to the 4-position of the pyrimidine ring or R is hydrogen, ethyl or n-butyl when PY is attached to the 5-position of the pyrimidine ring are useful as cardiotonic agents. The preparations of I and their cardiotonic use are shown.
Abstract: 8-Q-2-PY-9H-purin-6-amines (II), salts thereof, their preparation via 2-PY-4,5,6-pyrimidinetriamine and cardiotonic use are shown, where PY is 4-pyridinyl or 4-pyridinyl having one or two lower-alkyl substituents, and Q is methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, methylthio and ethylthio. Also shown as intermediates for the compounds where Q is methylthio or ethylthio are the corresponding 6-amino-2-PY-9H-purin-8-thiols.
Abstract: Alkaline paint stripper compositions contain either a fibrous material or a combination of a xanthan gum and hectorite clay so as to provide a pellable skin over a painted surface.
Abstract: Novel 1-R-1,4-dihydro-4-oxo-6-fluoro-7-(Z.dbd.N--)-quinolinecarboxylic acids and esters thereof, where R is amino, lower-alkylamino, 2-propenylamino or di-lower-alkylamino, R" is hydrogen or lower-alkyl, and Z.dbd.N is a heterocyclic group, useful as antibacterial agents, are prepared by reacting the corresponding 7-chloroquinoline derivatives with the appropriate heterocyclic compound, Z.dbd.NH. A preferred group of compounds are those where Z.dbd.N is 1-piperazinyl or 4-lower-alkyl-1-piperazinyl.
Abstract: Novel hydroxyphenylaminobenzenealkanols, useful as antiasthmatic agents, are of the formula ##STR1## wherein R is hydrogen, lower-alkyl, lower-alkoxy or halo; R' is hydrogen or lower-alkyl; R" is hydrogen, lower-alkyl or halo; and Y is C.sub.n H.sub.2n wherein n is 1-2. The compounds are prepared by de-etherification of the corresponding phenol alkyl or benzyl ethers; by reduction of the corresponding benzoic acids or esters thereof; or by reduction of ketones wherein --Y--OH is replaced by --COCH.sub.3.
Abstract: Mono and bis substituted (arylsulfonyl)alkanes useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of the appropriate aldehyde or dialdehyde with the appropriate aryl or heterocyclic moiety and the appropriate phenylsulfinic acid in the presence of a catalyst.
Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
Abstract: 4,5-Dihydro-4-R-6-(4-pyridinyl)-3(2H)-pyridazinone (IA) or pharmaceutically-acceptable acid-addition salt thereof, where R is hydrogen or methyl, is shown as the active component in cardiotonic composition and method for increasing cardiac contractility in a patient requiring such treatment. Also shown is the preparation of IA by reacting a lower-alkyl 2-R-4-(BN)-4-cyano-4-(4-pyridinyl)butanoate with hydrazine, where R is hydrogen or methyl, and BN is 4-morpholinyl, 1-piperidinyl or 1-pyrrolidinyl.
Abstract: 3-[(Alkoxy)(aryl or heteroaryl)methyl]-1H-indoles which are useful as color formers in pressure-sensitive carbonless duplicating systems and thermal marking systems are prepared by reacting 3-[(arylsulfonyl)(aryl or heteroaryl)methyl]-1H-indoles with alcohols in the presence of a base.
Abstract: N-acetyl-para-aminophenyl N'-acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenol. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.
Type:
Grant
Filed:
April 2, 1979
Date of Patent:
November 13, 1984
Assignee:
Sterling Drug Inc.
Inventors:
George Margetts, Roderic S. Andrews, Jean Legros
Abstract: Mono-, bis- and tris-indolyl-substituted furanones useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared respectively by: the interaction of an indole with mucochloric acid; the interaction of an indole with a 4-mono(indolyl)-substituted 4-oxo-2-butenoic acid; and by the interaction of an indole with a 2,4-bis(indolyl)-substituted 4-oxobutanoic acid or with a 3,5-bis(indolyl)-substituted furanone.
Abstract: A method for controlling two-stage combustion furnaces having a first stage operated with sub-stoichiometric airflow and a second stage operated with excess air, whereby the first stage airflow is controlled such that the ratio of first stage airflow to total airflow is maintained less than ##EQU1## where N lies between zero and unity.
Abstract: 8-Q-2-PY-9H-purin-6-amines (II), salts thereof, their preparation and cardiotonic use are shown, where PY is 4-pyridinyl or 4-pyridinyl having one or two lower-alkyl substituents, and Q is methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, methylthio and ethylthio. Also shown as intermediates for the compounds where Q is methylthio or ethylthio are the corresponding 6-amino-2-PY-9H-purin-8-thiols.
Abstract: N-Terminal L-prolyl or D-prolyl hexapeptide amides useful as Substance P agonists and/or antagonists and as analgesics and/or antihypertensives and a process for preparing them are disclosed.
Abstract: 3-Q-4-R.sub.2 -5-(2-Q'-5-R.sub.3 -4-thiazolyl)-6-R.sub.1 -2(1H)-pyridinones (I), where R.sub.1 is alkyl having from one to four carbon atoms, R.sub.2 is hydrogen or methyl, R.sub.3 is hydrogen or alkyl having from one to three carbon atoms, Q is amino, carbamyl, carboxy, cyano or hydrogen, and Q' is alkyl having from one to four carbon atoms, amino or R.sub.4 NH where R.sub.4 is alkyl having from one to four carbon atoms, or acid-addition salts thereof where at least one of Q and Q' is amino or Q' is R.sub.4 NH, are useful as cardiotonics (I where Q is amino, cyano or hydrogen) and/or as intermediates (I where Q is cyano, carbamyl or carboxy). Also shown as intermediates are 1,2-dihydro-4-R.sub.2 -5-[R.sub.3 CH(Br)CO]-6-R.sub.1 -2-oxo-3-pyridinecarbonitriles (II), and, also, processes for preparing I and II.
Abstract: One aspect of the invention resides in the three step process for preparing cardiotonically active 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles or 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinamides which comprises reacting a pyridinylmethyl lower-alkyl ketone with tri-(lower-alkyl) orthoformate, acetic anhydride and acetic acid to produce 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketone reacting the latter with cyanoacetamide or malonamide in the presence of a basic condensing agent and neutralizing the reaction mixture, where pyridinyl is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents. Other aspects of the invention reside in the intermediate 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones, their salts and their two step conversion, as described above, to 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)-nicotinonitriles or corresponding nicotinamides.
Abstract: Disclosed and claimed is the cardiotonic use of 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (II), where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl or hydrogen, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or where R' is nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salts thereof where at least one of R' and R" is amino. Also disclosed and claimed are 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (I), where R.sub.1, R' and R" are defined as above and R is lower-alkyl and acid-addition salts thereof where at least one of R' and R" is amino. Also shown and claimed is the process which comprises reacting 1-R.sub.1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R.sub.
Type:
Grant
Filed:
April 26, 1982
Date of Patent:
August 14, 1984
Assignee:
Sterling Drug Inc.
Inventors:
George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page, Ruthann M. McGarry
Abstract: 2-(R.sub.1 O)-3-Q-5-PY-6-R-pyridine (I) or pharmaceutically acceptable acid-addition salts thereof are useful cardiotonics, where R.sub.1 is methyl or ethyl, R is hydrogen or lower-alkyl, PY is 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents, and Q is hydrogen, chloro or COOR' where R' is lower-alkyl, or Q is cyano only when R is hydrogen. The preparation of I and their cardiotonic use are shown.
Type:
Grant
Filed:
November 10, 1982
Date of Patent:
July 31, 1984
Assignee:
Sterling Drug Inc.
Inventors:
George Y. Lesher, Chester J. Opalka, Jr., Baldev Singh
Abstract: An apparatus for injecting a mixture of pure oxygen or oxygen-enriched air (at least 25 percent oxygen) and purge water into a wet oxidation reactor operating at elevated temperature and pressure. An annular space between the oxygen carrying pipe and a second, larger pipe is filled with heat transfer resisting material, either maintained static or passed through the annular space to remove heat therefrom. The temperature of the oxygen and purge water is maintained at less than 250.degree. F., preferably less than 150.degree. F. to minimize evaporation of the purge water. Thus, backflow of organic matter into the oxygen pipe is prevented; plugging of the oxygen pipe by salts is also prevented.
Type:
Grant
Filed:
February 8, 1982
Date of Patent:
July 24, 1984
Assignee:
Sterling Drug Inc.
Inventors:
Ajit K. Chowdhury, Gerald L. Bauer, Richard W. Lehmann
Abstract: A genus of dipeptide amides including as the preferred subgenus the dipeptide amides having the structural formula R.sub.1 TyrR.sub.2 D-Q-NR.sub.4 R.sub.5 wherein Q is Met, Met(O), Gln or Ser, R.sub.1 and R.sub.2 are each hydrogen or alkyl, R.sub.4 is phenylalkyl or substituted-phenylalkyl and R.sub.5 is hydrogen, alkyl, phenylalkyl, substituted-phenylalkyl or X-alkyl wherein X is an electronegative group are prepared by condensing the dipeptide with the amine or the amino acid with the amino acid amide and are useful as analgesics.