Chalcogen Bonded Directly To Ring Carbon Of The Five-membered Hetero Ring (e.g., Phthalimidines, Etc.) Patents (Class 548/472)
  • Patent number: 5114952
    Abstract: A series of novel alkanesulphonamidophenyl-N-alkyl-N-(heterocyclic-alkyl)alkylamine derivatives have been prepared, including their pharmaceutically acceptable salts. These compounds are useful in therapy as anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrhythmias. Said sulfonamide compounds are of the formula: ##STR1## wherein R and R.sup.1 are each C.sub.1 -C.sub.4 alkyl; X is --CH.sub.2 --, --CO-- or --CH(OH)--; n is two, three or four; and "Het" is a nitrogen-containing heterocyclic group wherein said heterocyclic group is preferably 2H-3,4-dihydroisoquinol-1-on-2-yl or 2H-isoquinol-1-on-2-yl, each optionally substituted with halogen or C.sub.1 -C.sub.4 alkyl.
    Type: Grant
    Filed: November 21, 1990
    Date of Patent: May 19, 1992
    Assignee: Pfizer Inc.
    Inventors: John E. Arrowsmith, Peter E. Cross, Geoffrey N. Thomas
  • Patent number: 5112846
    Abstract: The present invention includes N-hydroxyamide, N-hydroxyurea, N-hydroxythioamide, and N-hydroxythiourea derivatives of fenamates, indomethacin, cicloprofen, oxepinac, and indoprofen as dual inhibitors or selective inhibitors of cyclooxygenase and 5-lipoxygenase.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: May 12, 1992
    Assignee: Warner-Lambert Company
    Inventors: Thomas R. Belliotti, Wiaczeslaw A. Cetenko, David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, James B. Kramer, Jagadish C. Sircar
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5095119
    Abstract: A compound of the formula: ##STR1## wherein A is ##STR2## in which X is .dbd.CH-- or .dbd.N--; R.sup.2 is hydrogen, alkyl, phenyl, benzyl or phenethyl; Y is --CH.sub.2--, --NH-- or --O--; and Z is --H.sub.2 or .dbd.O; B is His, Leu, Ile, Nva, Nle, Ala or Val; and R.sup.1 is hydrogen, alkyl, phenyl or phenylalkyl; or a pharmaceutically acceptable salt thereof are renin inhibitors.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: March 10, 1992
    Assignee: American Home Products Corporation
    Inventors: Timothy D. Ocain, David D. Deininger
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5047552
    Abstract: Disclosed herein are novel benzopyrans having pharmacological activity, to a process for preparing them, to pharmaceutical compositions containing them, and to their use in the treatment of hypertension.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: September 10, 1991
    Assignee: American Home Products Corporation
    Inventors: Dominick A. Quagliato, Leslie G. Humber
  • Patent number: 5047400
    Abstract: The invention relates to the compounds of general formula: ##STR1## in which: X denotes either an oxygen atom, or two hydrogen atoms;Y denotes either a hydrogen atom, or a hydroxyl group;or Y denotes an amino group on condition that X denotes two hydrogen atoms;R denotes a hydrogen atom, or a straight- or branched-chain alkyl group having 1 to 6 carbon atoms, optionally substituted with one or more hydroxy, amino, mercapto, methylthio or carboxy groups, or aryl groups such as phenyl, pyridyl or thienyl; ##STR2## denotes a polycyclic nitrogenous structure; their enantiomers, epimers and diastereoisomers, as well as their addition salts with a pharmaceutically acceptable acid or base.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: September 10, 1991
    Assignee: Adir et Cie
    Inventors: Michel Vincent, Georges Remond, Bernard Portevin, Claude Cudennec
  • Patent number: 5024694
    Abstract: Herbicidal and plant growth-regulating N-aryl heterocycles of the formula ##STR1## where A represents one of the groupings ##STR2## where R.sup.1 and R.sup.2 in each case independently of one another represent hydrogen, halogen, halogenoalkyl or alkyl,Y.sup.1 and Y.sup.2 in each case represent oxygen or sulphur andZ represents hydrogen, hydroxyl or chlorine, R represents in each case optionally branched alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl or cycloalkenylalkyl in each case interrupted by at least one oxygen atom and in each case substituted by at least one fluorine atom,X represents hydrogen or halogen andY represents hydrogen or halogen.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: June 18, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Schallner, Michael Negele, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt, Birgit Krauskopf
  • Patent number: 5025033
    Abstract: A cholinesterase inhibiting agent which contains an alkylene diamine of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently is a hydrogen atom or a hydrocarbon residue which may optionally be substituted, or R.sup.1 and R.sup.2 combinedly form, together with the adjacent nitrogen atom, a condensed heterocyclic group, R.sup.3 is a hydrogen atom or a hydrocarbon residue or an acyl group which may optionally be substituted and R.sup.4 is a hydrogen atom, or R.sup.3 and R.sup.4 combinedly form a group of the formula ##STR2## or --(CH.sub.2).sub.m+1 -- (m being 0, 1 or 2), A is --(CH.sub.2).sub.l -- (l being 0, 1 or 2) or --CH.dbd.CH--, X is a substituent or substituents and n is an integer of 4 to 7, or a salt thereof, which are useful as cerebral function improving agents for the prevention or treatment of senile dementia, Alzheimer's disease, Huntington's chorea, hyperkinesia, mania and so forth.
    Type: Grant
    Filed: January 25, 1989
    Date of Patent: June 18, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Giichi Goto, Akinobu Nagaoka
  • Patent number: 5023338
    Abstract: A compound of the formula: ##STR1## wherein A is ##STR2## in which X is .dbd.CH-- or .dbd.N--; R.sup.2 is hydrogen, alky, phenyl, benzyl or phenethyl; Y is --CH.sub.2 --, --NH-- or --O--; and Z is --H.sub.2 or .dbd.O; B is His, Leu, Ile, Nva, Nle, Ala or Val; and R.sup.1 is hydrogen, alkyl, phenyl or phenylalkyl; or a pharmaceutically acceptable salt thereof are renin inhibitors.
    Type: Grant
    Filed: March 8, 1990
    Date of Patent: June 11, 1991
    Assignee: American Home Products Corporation
    Inventors: Timothy D. Ocain, David D. Deininger
  • Patent number: 5013627
    Abstract: Positively charged electrophotographic toners contain, besides customary resin and pigment particles, an additive which increases the cationic charge and has the general formula(X.sup.1).sup.- K.spsp.+.sup.1 -Y.sup.1 -A-Y.sup.2 -K.spsp.+.sup.2 (X.sub.2).sup.- (I)wherein the symbols have the meaning mentioned in the description.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: May 7, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Harnisch, Roderich Raue
  • Patent number: 4999355
    Abstract: Compounds of formula: ##STR1## in which: either R.sub.1 represents 4-phenyl-1,2,3,6-tetrahydro-1-pyridyl or 4-(4-fluorophenyl)-1,2,3,6-tetrahydro-1-pyridyl, R.sub.2 represents hydrogen, alkoxy of 1 or 2 carbon atoms, hydroxyl, alkyl, alkylthio, alkylcarbonyloxy, phenylalkylcarbonyloxy, phenylalkyl or --NR.sub.4 R.sub.5 in which R.sub.4 represents hydrogen or alkyl and R.sub.5 represents alkyl, phenyl, monohalogenated phenyl or pyridyl, and R.sub.3 represents a hydrogen atom, or else R.sub.2 represent phenyl and R.sub.3 represents hydrogen or hydroxyl;or R.sub.1 represnets 4-phenyl-1-piperazinyl whose phenyl nucleus has a substituent halogen atom or hydroxyl radical in the 4-position, R.sub.2 represents alkoxy and R.sub.3 represents hydrogen;it being understood that when R.sub.1 represents the 4-phenyl-1,2,3,6-tetrahydro-1-pyridyl radical, R.sub.
    Type: Grant
    Filed: March 6, 1989
    Date of Patent: March 12, 1991
    Assignee: Rhone-Poulenc
    Inventors: Marie-Therese Comte, Claude Gueremy, Gerard Ponsinet
  • Patent number: 4990669
    Abstract: The invention relates to new optically active .alpha.-amino aldehydes of the formulae ##STR1## in which R.sub.1 represents an optionally substituted alkyl, alkenyl, aralkyl or aryl radical, andR.sub.2 and R.sub.3, independently of one another, denote an optionally substituted alkyl, alkenyl, cycloalkyl or aralkyl group, together form an optionally substituted phenylene-(1,2)-bis-methylene radical, or R.sub.2 is an optionally substituted, alkyl, cycloalkyl or aralkyl radical, and R.sub.3 forms together with R.sub.1 a 1,3-propylene radical.a process for the preparation thereof, and the use thereof for the stereoselective preparation of optically active .beta.-amino alcohols.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred T. Reetz, Mark W. Drewes
  • Patent number: 4908378
    Abstract: Disclosed herein are novel benzopyrans having pharmacological activity, to a process for preparing them, to pharmaceutical compositions containing them, and to their use in the treatment of hypertension.
    Type: Grant
    Filed: April 12, 1989
    Date of Patent: March 13, 1990
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 4904798
    Abstract: Isoindolenines of the general formula (I) ##STR1## where R.sup.1 is hydrogen, unsubstituted or chlorine-, hydroxylphenyl- or cyano-substituted C.sub.1 -C.sub.12 -alkyl or C.sub.5 -C.sub.8 -cycloalkyl or unsubstituted or chlorine- or methyl-substituted phenyl,R.sup.2 is hydrogen or unsubstituted or chlorine-, hydroxyl-, phenyl- or cyano-substituted C.sub.1 -C.sub.6 -alkyl, or is morpholino, pyrrolidino or piperidino, andR.sup.3 is hydrogen or methyl and the benzene ring A may be substituted by from 1 to 4 chlorines, 1 or 2 C.sub.1 -C.sub.4 -alkyls or 1 nitro,are obtained by condensing 3-aminophenols of the formula (II) ##STR2## with 3-amino-1-oxoisoindolenines of the general formula (III) ##STR3## in the presence of acids, and are hydrolyzible in very good yields into benzoylbenzoic acids (IV) ##STR4## which are very difficult, if not impossible, to prepare by prior art methods.
    Type: Grant
    Filed: January 10, 1989
    Date of Patent: February 27, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Kranz, Bernd Landmann, Udo Mayer
  • Patent number: 4879293
    Abstract: The compound of the formula ##STR1## wherein X is a cyclic group which may optionally be substituted; Y is a carboxyl group which may optionally be esterified or amidated; Z is --CH.dbd.CH--CH.dbd.CH--, --S--(CH.sub.2).sub.l --S-- is an integer of 1 to 3), --N.dbd.CH--CH.dbd.N-- or --(CH.sub.2).sub.m --(m is an integer of 3 to 5); ring A may optionally be substituted with halogen, nitro, amino, alkanoylamino, alkoxycarbonyl, carboxyl or carbamoyl; and n is an integer of 1 to 3, and salts thereof. The compounds display a strong antianxiety effect to mammalian animals and are useful for the prevention or treatment of a disease such as psychoromatic disease and anxiety neurosis.
    Type: Grant
    Filed: September 8, 1988
    Date of Patent: November 7, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kentaro Hiraga, Yoshiaki Saji
  • Patent number: 4871735
    Abstract: The present invention relates to new naphthyl derivatives of general formula ##STR1## wherein N represents the number 1 or 2,A represents a --CH.sub.2 --, --CO--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## while the atom marked with an x is linked to the phenyl nucleus, E represents a straight chained alkylene group optionally substituted by an alkyl group,G represents a straight chained alkylene group optionally substituted by an alkyl group,L represents a bond or an oxygen atom, if G represents a straight chained alkylene group with 2 to 5 carbon atoms optionally substituted by an alkyl group,R.sub.1 and R.sub.2, which may be identical or different, represent alkyl or alkoxy groups or R.sub.1 and R.sub.2 together represent an alkylenedioxy group,R.sub.3 represents a hydrogen atom, or an alkyl or an allyl group,R.sub.4, R.sub.5 and R.sub.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: October 3, 1989
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Joachim Heider, Manfred Psiorz, Andreas Bomhard, Norbert Hauel, Berthold Narr, Klaus Noll, Christian Lillie, Walter Kobinger, Jurgen Dammgen
  • Patent number: 4863948
    Abstract: A series of novel alkanesulphonamidophenyl-N-alkyl-N-(heterocyclic-alkyl)alkylamine derivatives have been prepared, including their pharmaceutically acceptable salts, wherein the heterocyclic moiety is a 5- or 6-membered nitrogen-containing heterocyclic group which is attached to the adjacent carbon atom by a carbon or nitrogen atom and optionally contains a further heteroatom selected from oxygen and nitrogen, said nitrogen-containing heterocyclic group being either (i) substituted by a phenyl or benzyl group or (ii) fused at two adjacent carbon atoms to a benzene ring, with the resulting heterocyclic ring moiety also being optionally substituted. These particular compounds are useful in therapy as highly effective anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrythmias. The most preferred member compound of the series is 2-hydroxy-2-(4-methanesulphonamidophenyl)-N-methyl-N-[2-(6-chloro-2H-isoin dolin-1-on-2-yl)ethyl]ethylamine.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: September 5, 1989
    Assignee: Pfizer, Inc.
    Inventors: John E. Arrowsmith, Peter E. Cross, Geoffrey N. Thomas
  • Patent number: 4849441
    Abstract: Isoindolin-1-one compounds represented by the following formula (I); ##STR1## {wherein n represents an integer of 1 to 6; m represents 0 or 1; R.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen or lower alkyl, and when m is 1, R.sub.1 and one of R.sub.2 and R.sub.3 may form a five-membered or six-membered ring over N atom; X represents hydrogen or hydroxy; Ar represents naphthyl, pyridyl or substituted phenyl represented by the formula (II); Ar and X may form a lactone ring; ##STR2## [wherein Y represents carboxyl, lower alkoxycarbonyl, carbamoyl, N,N-lower alkyl-substituted carbamoyl or amino represented by the formula (III): ##STR3## (wherein R.sub.6 and R.sub.7 are each independently hydrogen, lower alkyl or lower alkanoyl); R.sub.4 and R.sub.5 are each independently hydrogen, lower alkyl, cyano or halogen]} or a pharmaceutically acceptable acid addition salt or metal salt thereof have an excellent antiarrhythmic activity.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: July 18, 1989
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Kei Okazaki, Etsuo Oshima, Hiroyuki Obase, Yoshimasa Oiji, Masaaki Nito, Kazuhiro Kubo
  • Patent number: 4730056
    Abstract: A process for preparing [1H]-isoindolin-1-one-3-carboxylic acid comprising the steps of (1) reacting phthalaldehydic acid in an alkanol with ammonia, (2) contacting the resulting solution with an alkali metal cyanide, (3) removing the alkanol, (4) adjusting the pH to 1.0, (5) heating the resulting reaction mixture until product formation is substantially complete and isolating the product.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: March 8, 1988
    Assignee: Pfizer Inc.
    Inventor: John A. Lowe, III
  • Patent number: 4628085
    Abstract: A process for selective preparation of lactams which comprises contacting, in the vapor phase, an aliphatic or aromatic aminonitrile having the formula HR.sub.1 N--D--CN wherein D is a divalent organic moiety and wherein R.sub.1 is (C.sub.1 -C.sub.4) alkyl or hydrogen with an effective amount of a silica catalyst, in the form of substantially spherical beads having a BET surface area greater than about 250 m.sup.2 /g, preferably between 300 and 500 m.sup.2 /g, and an average pore diameter less than about 20 nanometers preferably 8-10 nanometers at a temperature in the range of about 200.degree. to about 400.degree. C. and at a hydrogen or inert gas flow with a pressure in the range of about 0 to about 300 kPa, in the presence of: (a) ammonia in an amount equal to from 0 to about 50 mole percent of the molar amount of aliphatic or aromatic aminonitrile present; and (b) water in an amount from at least about 1.
    Type: Grant
    Filed: September 3, 1985
    Date of Patent: December 9, 1986
    Assignee: Allied Corporation
    Inventors: Frank Mares, Reginald T-H. Tang, James E. Galle, Rose M. Federici
  • Patent number: 4627852
    Abstract: In a therapeutic system such as a plaster for administration of an active compound through the skin and comprising a covering layer which is essentially impermeable to the active compound, an active coupound reservoir layer and a protective layer which can be pulled off and which is essentially impermeable to the active compound, the improvement wherein the reservoir layer contains about 1-30% of active compound in an elastomer mixture comprising a diene rubber which can optionally be copolymerized with an .alpha.-olefin, mixed with from 0 up to about 70% by weight of a polyisobutylene, polybutadiene oil and/or paraffin oil, and a tackifying resin. Thereby the active compound can be released in regulated relatively large quantity over a prolonged period of time.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: December 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Miklos von Bittera, Rolf-Volker Meyer
  • Patent number: 4625023
    Abstract: Process for the selective conversion of dinitriles into the corresponding lactam by treating the dinitrile with an effective amount of a hydrogenation catalyst such as copper chromite in combination with a co-catalyst, such as titania, at a temperature in the range of from about 200.degree. C. to about 400.degree. C. and at a pressure of at least 50 kPa in the presence of water and hydrogen.
    Type: Grant
    Filed: September 3, 1985
    Date of Patent: November 25, 1986
    Assignee: Allied Corporation
    Inventors: Frank Mares, Reginald Y. Tang, James E. Galle, Rose M. Federici
  • Patent number: 4581463
    Abstract: Halonitroarylacetic acid esters are prepared by reacting a halonitroaromatic compound with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base. The halonitroarylacetic acid esters formed by the process can be readily converted into derivatives, such as pharmaceuticals.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: April 8, 1986
    Assignee: Ethyl Corporation
    Inventors: G. Patrick Stahly, Barbara C. Stahly
  • Patent number: 4551453
    Abstract: The 2-(.omega.-alkylaminoalkyl)- and 2-(.omega.-dialkylaminoalkyl)-3-(4-X-benzylidene)phthalimidines are useful as local anesthetics. For the preparation, the adduct is formed between the suitable 3-(4-X-benzylidene)phthalide and a substituted amino-alkylamine, the adduct being then reacted with acetic anhydride; the X substituent at the position 4 of the benzylidene group then can be suitably converted according to the requirements.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: November 5, 1985
    Assignee: Laboratori Baldacci SpA
    Inventor: Antonio Marsili
  • Patent number: 4546110
    Abstract: Compounds which are .beta.-farnesene derivatives obtainable as a Diels-Adler adduct of .beta.-farnesene and a dienophile or by a modification of such an adduct in a manner as defined herein are of value in pest control, particularly in the control of aphids.
    Type: Grant
    Filed: January 20, 1983
    Date of Patent: October 8, 1985
    Assignee: National Research Development Corporation
    Inventors: Glenn W. Dawson, David C. Griffiths, John A. Pickett
  • Patent number: 4530843
    Abstract: Heterocyclic amidoxime derivatives of the general formula: ##STR1## wherein R' represents hydrogen or the methyl radical, and R represents the 1-oxo-1H-isoquinolin-2-yl, 2-oxo-2H-quinolin-1-yl, 2,3-dihydro-1H-indol-1-yl, 1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl, 1H-indol-1-yl, 1-oxo-1,3-dihydro-2H-isoindol-2-yl, 2-oxo-3,4-dihydro-2H-quinolin-1-yl, 5-chloro-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl, 5-chloro-2-oxo-3-phenyl-2,3-dihydro-1H-benzimidazol-1-yl, 4-chloro-1-oxo-1H-isoquinolin-2-yl or 3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl radical, and--when R' represents the methyl radical--racemates and enantiomers of such compounds, are new compounds useful in therapy, and especially for the treatment of complaints of the central nervous system and for the treatment of depression.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: July 23, 1985
    Assignee: Synthelabo
    Inventor: Daniel Obitz
  • Patent number: 4505911
    Abstract: The invention provides 3-oxoisoindole compounds useful as diuretics of the general formula ##STR1## wherein X is halogen or trifluoromethyl, A is alkylene (C.sub.2 -C.sub.4), R.sub.1 is alkyl, R.sub.2 is alkyl or phenylalkyl, or R.sub.1 and R.sub.2 taken together with nitrogen are piperidino, morpholino or pyridinyl.
    Type: Grant
    Filed: October 13, 1983
    Date of Patent: March 19, 1985
    Assignee: Mead Johnson & Company
    Inventors: Terence M. Dolak, Tellis A. Martin
  • Patent number: 4505921
    Abstract: New sulfonylurea compounds of the formula: ##STR1## in which n is 1 or 2,R is thienyl, furyl, pyridyl or phenyl optionally mono or disubstituted,R.sub.1 and R.sub.2, the same or different, each are hydrogen, halogen, (C.sub.1 to C.sub.5)-alkyl, (C.sub.1 to C.sub.5)-alkoxy, or trifluoromethyl, or together represent --CH.sub.2 --O--CH.sub.2 --,R.sub.3 is hydrogen, or hydroxy, andR.sub.4 is (C.sub.1 to C.sub.5)-alkyl, (C.sub.3 to C.sub.8)-cycloalkyl or azacycloalkyl of the formula: ##STR2## in which p is zero or an integer from 1 to 5, or azabicycloalkyl of the formula: ##STR3## in which m is 1, 2, or 3. These new compounds and physiologically tolerable salts thereof may be used as medicines especially in the treatment of diabetes.
    Type: Grant
    Filed: September 6, 1983
    Date of Patent: March 19, 1985
    Assignee: ADIR, S.A.R.L.
    Inventors: Laszlo Beregi, Pierre Hugon, Jacques Duhault, Michelle Boulanger
  • Patent number: 4503043
    Abstract: Substituted acyl derivatives of octahydro-1H-isoindole-1-carboxylic acid compounds and the pharmaceutically acceptable salts thereof are produced by acylating a suitably substituted octahydro-1H-isoindole with a suitably activated substituted carboxylic acid and when desired hydrolyzing the resulting product. The compounds of the invention, their salts and pharmaceutical compositions thereof are useful as antihypertensive agents.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: March 5, 1985
    Assignee: Warner-Lambert Company
    Inventor: Clifton J. Blankley
  • Patent number: 4495353
    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.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 22, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4495193
    Abstract: A compound having gastric acid secretion reducing activity and having the formula ##STR1## wherein each V and W, independently, is H, --CH.sub.2 COOR.sup.4 where R.sup.4 is H or lower alkyl, --CH.sub.2 CN, or ##STR2## or V and W together represent .dbd.CHCOOR.sup.4 or .dbd.CHCN; A is ##STR3## R.sup.1 is H or CH.sub.3 ; L is CH.sub.2 S; Q is O or CH.sub.2 S; n is 0 or 1; 2 m 4; each R.sup.2 and R.sup.3, independently, is hydrogen, lower alkyl, lower cycloalkyl, or lower aralkyl; or R.sup.2 and R.sup.3, together with the nitrogen atom to which they are attached, form a 4, 5, or 6 membered heterocyclic ring containing 0, 1, or 2 oxygen atoms and 1, 2, or 3 nitrogen atoms and being unsubstituted or lower alkyl substituted; and Ar is a single ring aromatic group selected from aryl, substituted aryl, fused aryl, or heteroaryl; or the pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: December 30, 1982
    Date of Patent: January 22, 1985
    Assignee: Biomeasure, Inc.
    Inventors: Sun H. Kim, Jacques-Pierre Moreau
  • Patent number: 4477675
    Abstract: The process of preparing a compound of the formula: ##STR1## wherein, Y and Z are each H, alkyl, halo, alkoxy, trifluoromethyl, hydroxy, alkanoyloxy, or alkanoylamino;X is F, Cl, Br, or NR.sub.1 R.sub.2 wherein R.sub.1 and R.sub.2 are each hydrogen, alkyl, alkynyl, alkenyl, cycloalkyl, aryl or aralkyl; andR is H, alkyl, cycloalkyl, or aralkyl; which comprises the step of oxidation of the corresponding 3-desoxy compound.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: October 16, 1984
    Assignee: USV Pharmaceutical Corporation
    Inventors: Joseph Auerbach, Frederick A. Golec, Jr.
  • Patent number: 4476315
    Abstract: Nitroarylacetic acid esters are prepared by reacting a nitroaromatic compound which is devoid of halogen on the aromatic ring carrying a nitro group with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base so that the ester undergoes a nucleophilic substitution on an unsubstituted ring carbon of the nitroaromatic compound during which an alpha-substituent functions as a leaving group. Nitrobenzene acetic acids and their esters are useful intermediates for the synthesis of pharmaceuticals.
    Type: Grant
    Filed: December 23, 1982
    Date of Patent: October 9, 1984
    Assignee: Ethyl Corporation
    Inventors: G. Patrick Stahly, Barbara C. Stahly
  • Patent number: 4463176
    Abstract: A process for resolving a racemic modification of .beta.-adrenergic aryl- or hetaryl-oxypropanolamines such as (.+-.)-2-[2-hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]propoxy] benzonitrile into its individual enantiomers is described. The process comprises converting the racemic modification into a pair of diastereomeric urea derivatives by reaction with a chiral aralkylisocyanate; separation into the individual diastereomers; and facile regeneration of the starting amine by cleavage of the intermediate urea compound using hydrazine. This final step is improved by the addition of an .alpha.-keto carboxylic acid, such as pyruvic acid, which functions as a scavenger of nucleophilic by-products.
    Type: Grant
    Filed: September 13, 1982
    Date of Patent: July 31, 1984
    Assignee: Mead Johnson & Company
    Inventors: Ronald D. Dennis, Terence M. Dolak, William E. Kreighbaum
  • Patent number: 4423232
    Abstract: Tricyclic isoindole derivatives characterized by having a 1,2,3,4,6,10b-hexahydropyrazino]2,1-a]isoindole or 1,3,4,10b-tetrahydropyrimido[6,1-a]isoindol-6(2H)-one nucleus are disclosed. The foregoing compounds are useful antihypertensive agents.Claimed compounds include those of the formula ##STR1## in which R.sup.3 and R.sup.4 each is hydrogen, lower alkoxy, lower alkyl, trifluoromethyl, halo or hydroxy, or R.sup.3 and R.sup.4 together form an OCH.sub.2 O chain; and R.sup.14 and R.sup.15 each is hydrogen or lower alkyl.
    Type: Grant
    Filed: February 19, 1981
    Date of Patent: December 27, 1983
    Assignee: American Home Products Corporation
    Inventors: Christopher A. Demerson, Leslie G. Humber, Jean-Marie Ferland
  • Patent number: 4400520
    Abstract: A process for the preparation of an isoindoline derivative of the following general formula (II): ##STR1## wherein R.sup.2 is a hydrogen atom or lower alkyl group and X is a carboxyl group, carboalkoxy group, amide group or cyano group, which comprisescycling a benzylidene derivative of the following general formula (I) ##STR2## wherein R.sup.1 is a hydrogen atom or lower alkyl group, and R.sup.2 and X are as defined above, in the presence of a reducing agent such as sodium boron hydride. In one embodiment, the benzylidene derivative may be substituted by a reaction mixture containing the same, the reaction mixture being prepared by reacting o-phthalaldehydic acid or its ester with an aniline derivative.
    Type: Grant
    Filed: September 4, 1981
    Date of Patent: August 23, 1983
    Assignee: Hisamitsu Pharmaceutical Co., Inc.
    Inventors: Kanji Noda, Akira Nakagawa, Toshiharu Motomura, Hiroyuki Ide
  • Patent number: 4379091
    Abstract: The present invention concerns tetraethylene glycol monoesters with 2-arylpropionic acids (known as anti-inflammatory agents). Said esters, while being endowed with the characteristics of low toxicity and gastric injuring effects shown by the related acids, differ advantageously from the latter because their anti-inflammatory activity is much more prolonged, and their bioavailability markedly better.
    Type: Grant
    Filed: February 11, 1981
    Date of Patent: April 5, 1983
    Assignee: Ausonia Farmaceutici s.r.l.
    Inventors: Paolo Ferruti, Ferdinando Danusso, Maria C. Tanzi, Giuseppe Quadro
  • Patent number: 4366312
    Abstract: 1:1 metal complexes of azines of the formula ##STR1## in which the ring A can be further substituted, R is an H atom or an alkyl or aryl group, B is an isocyclic or heterocyclic aromatic radical or an alicyclic radical, R.sub.1 is the OH or SH group and Y is a radical of the formula ##STR2## in which Z is an O or S atom, n is the number 1 or 2 and R.sub.2 is an alkyl, aralkyl, cycloalkyl or aryl radical or an amino group which is unsubstituted or substituted by an alkyl, cycloalkyl, aralkyl or aryl radical.In plastics and surface coatings, the novel pigments give intense pure orange to violet colorations with good fastness properties.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: December 28, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Abul Iqbal
  • Patent number: 4331600
    Abstract: Compounds of the formula ##STR1## wherein, Y and Z are each H, alkyl, halo, alkoxy, trifluoromethyl, hydroxy, alkanoyloxy, or alkanoylamino;X is F, Cl Br or NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 are each hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl or cycloalkyl; andR is H, alkyl, cycloalkyl or aralkyl; and salts thereof.The compounds have utility as anti-hypertensive and diuretic agents and as intermediates for the preparation of other anti-hypertensive and diuretic agents.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: May 25, 1982
    Assignee: USV Pharmaceutical Corporation
    Inventors: Frederick A. Golec, Jr., Joseph Auerbach