Ring Nitrogen In The Polycyclo Ring System Patents (Class 544/80)
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Patent number: 4838925Abstract: This invention relates to novel heterocyclic carbonyl sulfonamides which are particularly useful as agricultural chemicals.Type: GrantFiled: September 25, 1987Date of Patent: June 13, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Chi-Ping Tseng
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Patent number: 4757070Abstract: Compounds of formula I ##STR1## wherein n is 0 or 1,R.sup.1 is hydrogen or lower alkyl,R.sup.2 and R.sup.3 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, or together with the nitrogen atom form a 5-6-member heterocycle,R.sup.4 is hydrogen, lower alkyl or lower alkoxyalkyl andX is COOR.sup.6, CO--NR.sup.7 R.sup.8, or an oxadiazolyl radical of the formula ##STR2## wherein R.sup.5 is H, lower alkyl or cycloalkyl,R.sup.6 is H or lower alkyl,R.sup.7 and R.sup.8 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, orR.sup.7 and R.sup.8 together with the nitrogen atom can form a 5-6-member heterocycle,are valuable drugs, e.g., have psychotropic activity.Type: GrantFiled: December 8, 1987Date of Patent: July 12, 1988Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David N. Stephens
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Patent number: 4754034Abstract: 4,4-diaryldihydroquinazolones of the formula ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3, independently of one another, denote hydrogen, halogen, alkyl, aryl, alkanoylamino, aroylamino, heteryl, NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3, at least one of the radicals X.sup.1, X.sup.2 or X.sup.3 standing for NY.sup.1 Y.sup.2, OY.sup.3 or SY.sup.3,R.sup.1 denotes hydrogen, alkyl, cycloalkyl, aralkyl, aryl or the members of a bridge to the o-carbon of ring C,R.sup.2 denotes a radical of an acid,Y.sup.1, Y.sup.2 and Y.sup.3, independently of one another, denote hydrogen, alkyl, cycloalkyl, aralkyl aryl or heteryl or the remaining members of a 5- or 6-membered ring which reaches to one of the o-position benzene C atoms and may contain further hetero atoms orY.sup.1 +Y.sup.Type: GrantFiled: October 21, 1985Date of Patent: June 28, 1988Assignee: Bayer AktiengesellschaftInventors: Horst Berneth, Alfred Brack, Karlheinrich Meisel
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Patent number: 4741765Abstract: Benzenesulfonamide compounds such as N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl-4 -oxo-1-phenyl-indeno[1,2-C]pyrazole-5-sulfonamide and N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl- 4-oxo-1-phenyl-indeno[1,2-C]pyrazole-5-sulfonamide, agricultural compositions containing them, and their herbicidal utility are disclosed.Type: GrantFiled: April 3, 1987Date of Patent: May 3, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert J. Pasteris, Ramaurthi Muthukrishnan
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Patent number: 4731365Abstract: Compounds of formula I ##STR1## wherein n is 0 or 1,R.sup.1 is hydrogen or lower alkyl,R.sup.2 and R.sup.3 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, or together with the nitrogen atom form a 5-6-member heterocycle,R.sup.4 is hydrogen, lower alkyl or lower alkoxyalkyl andX is COOR.sup.6, CO--NR.sup.7 R.sup.8, or an oxadiazolyl radical of the formula ##STR2## wherein R.sup.5 is H, lower alkyl or cycloalkyl,R.sup.6 is H or lower alkyl,R.sup.7 and R.sup.8 each independently is hydrogen, optionally substituted lower alkyl, acyl or aryl, orR.sup.7 and R.sup.8 together with the nitrogen atom can form a 5-6-member heterocycle,are valuable drugs, e.g., have psychotropic activity.Type: GrantFiled: December 22, 1986Date of Patent: March 15, 1988Assignee: Schering AktiengesellschaftInventors: Helmut Biere, Andreas Huth, Dieter Rahtz, Ralph Schmiechen, Dieter Seidelmann, David N. Stephens
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Patent number: 4711882Abstract: A series of novel octahydro-6-azaindole dipeptide derivatives have been prepared, including their pharmaceutically acceptable salts and bioprecursors therefor. These particular compounds are inhibitors of the angiotensin converting enzyme and are therefore useful in therapy for the treatment of certain cardiovascular disorders, including heart failure and hypertension. Preferred member compounds include 1-[N-(1-S-ethoxycarbonyl-3-phenylpropyl)-S-alanyl]-2-S-carboxy-6-(N-methyl carbamoyl)-octahydro-6-azaindole, 1-[N-(1-S-ethoxycarbonyl-3-phenylpropyl-S-alanyl]-2-S-carboxy-6-methanesul phonyl-octahydro-6-azaindole and 1-[N-(1-carboxy-3-phenylpropyl)-S-lysyl]-2-carboxy-6-methanesulphonyl-octa hydro-6-azaindole, respectively. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: December 19, 1985Date of Patent: December 8, 1987Assignee: Pfizer Inc.Inventors: Simon F. Campbell, Ryszard J. Kobylecki
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Patent number: 4710510Abstract: The present invention provides new pyrrolobenzimidazoles of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl, alkenyl or cycloalkyl radical; R.sub.2 is a hydrogen atom, cyano group or alkyl or alkenyl radical or a carbonyl group substituted by hydroxyl, alkyl, alkoxy, amino, alkylamino, dialkylamino or hydrazino or together with R.sub.1 forms a cycloalkylene radical or R.sub.1 and R.sub.2 together form an alkylidene or cycloalkylidene radical; R.sub.3, R.sub.4 and R.sub.Type: GrantFiled: December 10, 1985Date of Patent: December 1, 1987Assignee: Boehringer Mannheim GmbHInventors: Alfred Mertens, Jens-Peter Holck, Wolfgang Kampe, Bernd Muller-Beckmann, Klaus Strein, Wolfgang Schaumann
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Patent number: 4668966Abstract: The invention relates to bisquinazolines of the formula ##STR1## wherein the ring A is unsubstituted or substituted by cyano, nitro, halogen, lower alkyl, phenyl, benzyl, lower alkoxy or lower alkoxycarbonyl,Q is an aliphatic radical with a molecular weight of 28 to 450, or is a cycloaliphatic or araliphatic radical,Y is the radical of the formula (2a) ##STR2## or of the formula ##STR3## wherein B, D, X.sub.1, X.sub.2, X.sub.3 and Z are as hereinafter defined. These compounds are particularly suitable as colour formers in pressure-sensitive or heat-sensitive recording materials and give strong yellow or orange colours of excellent fastness to light, especially fastness to sublimation.Type: GrantFiled: April 11, 1985Date of Patent: May 26, 1987Assignee: Ciba-Geigy CorporationInventors: Rudolf Zink, Ian J. Fletcher
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Patent number: 4621082Abstract: Pyridopyrimidines of the formula ##STR1## in which R.sup.1 is optionally substituted aryl or heterocyclic,exhibit circulation active properties, especially renal vasodilating and diuretic action.Type: GrantFiled: January 7, 1986Date of Patent: November 4, 1986Assignee: Bayer AktiengesellschaftInventors: Horst Meyer, Egbert Wehinger, Bernward Garthoff, Stanislav Kazda
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Patent number: 4567256Abstract: 9a-Methoxymitosane derivatives having the amidino group at one or both of the 7-position and the carbamoyl-N positions are prepared by reaction of mitomycin A, mitomycin C, or an N.sup.1a -substituted analog thereof with an amide acetal, iminothioether, halomethyleniminium halide, or iminohalide salt.Type: GrantFiled: October 5, 1984Date of Patent: January 28, 1986Assignee: Bristol-Myers CompanyInventors: Dolatrai M. Vyas, Takushi Kaneko, Terrence W. Doyle
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Patent number: 4532237Abstract: Novel substituted and bridged pyridine compounds useful as calcium channel blockers, pharmaceutical compositions thereof, and methods of treatment are disclosed.Type: GrantFiled: July 30, 1984Date of Patent: July 30, 1985Assignee: Merck & Co., Inc.Inventors: George D. Hartman, Brian T. Phillips
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Patent number: 4503050Abstract: Imidazo[1,2-c]pyrimidines which are bronchodilators. Pharmacological methods of using these compounds, pharmaceutical compositions containing these compounds, and synthetic intermediates for preparing these compounds are also described.Type: GrantFiled: June 2, 1983Date of Patent: March 5, 1985Assignee: Riker Laboratories, Inc.Inventor: James J. Wade
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Patent number: 4503227Abstract: The invention relates to chromogenic dihydroquinazolines of the general formula ##STR1## wherein the ring A is a monocyclic or polycyclic, unsubstituted or substituted heterocyclic radical which may contain further heteroatoms as ring members,each of X.sub.1, X.sub.2 and Y independently of one another is hydrogen, halogen, lower alkyl, lower alkanoylamino, or a group of the formula ##STR2## X.sub.3 is hydrogen, halogen, lower alkyl or lower alkoxy; each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, Z.sub.1 and Z.sub.2 independently of one another is C.sub.1 -C.sub.12 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or is cycloalkyl, phenyl, or phenyl or benzyl each substituted by halogen, nitro, lower alkyl or lower alkoxy, and the radicals R may also be hydrogen; oreach pair of substituents (R.sub.1 and R.sub.2), (R.sub.3 and R.sub.4) and (Z.sub.1 and Z.sub.Type: GrantFiled: April 18, 1983Date of Patent: March 5, 1985Assignee: Ciba-Geigy CorporationInventors: Heinz Balli, Sigmund Gunzenhauser, Ian J. Fletcher, Davor Bedekovic
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Patent number: 4472578Abstract: There have been prepared novel benzo[a]phenazine derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen or methoxy, R.sup.2 is hydrogen, methyl, acetyl, haloacetyl or substituted aminoalkyl, and R.sup.3 is ethoxy or substituted amino. These compounds are useful as antimicrobiological agents.Type: GrantFiled: March 23, 1983Date of Patent: September 18, 1984Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Noriichi Oda, Kazuhiro Kobayashi, Isoo Ito
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Patent number: 4466965Abstract: The present invention relates to new compounds of the formula ##STR1## alkylene, or --S-- where R.sub.1 is hydrogen, alkyl, or aryl; W is hydrogen, hydroxy, amino, alkyloxy, aryloxy, O-alkyl, or O-aralkyl; (Y).sub.A is --CH.sub.2 NR.sub.2 R.sub.3 where R.sub.2 and R.sub.3 may be hydrogen, substituted alkyls, aryls, or together with N form a 5 to 7 membered heterocyclic group; and Ar is a substituted or unsubstituted heteroaryl. These compounds are useful in the treatment of various cardiac arrhythmias.Type: GrantFiled: July 26, 1982Date of Patent: August 21, 1984Assignee: American Hospital Supply CorporationInventors: David M. Stout, William L. Matier
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Patent number: 4466972Abstract: Compounds of formula I, ##STR1## wherein X is oxygen or sulphur, and R.sub.1 -R.sub.6 are various substituents.The compounds are useful for treating coronary insufficiency, intermittent claudication, cerebrovascular insults, spasms in muscles and hypertension.Type: GrantFiled: March 19, 1982Date of Patent: August 21, 1984Assignee: Sandoz Ltd.Inventor: Peter Neumann
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Patent number: 4444770Abstract: The invention relates to imidazoazole-alkenoic acid amides of Formula (I) and methods for their production. Also included in the invention are compositions containing said alkenoic acid amides and methods for the use of said alkenoic acid amides and the compositions containing them. In addition, the invention includes the intermediate carbonyl compounds of Formula (II) and the intermediate alkenoic acids of Formula (V) as well as methods for their preparation.Type: GrantFiled: May 13, 1981Date of Patent: April 24, 1984Assignee: Bayer AktiengesellschaftInventors: Horst Meyer, Harald Horstmann, Eike Moller, Bernward Garthoff
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Patent number: 4435566Abstract: Novel thiopyranopyrimidine compounds and the pharmaceutically acceptable acid addition salts thereof having excellent hypoglycemic activity, platelet aggregation inhibitory activity, antihistamine activity and anti-allergy activity useful for prevention and treatment of various disorders caused by diabetes, allergy and the like are disclosed.Type: GrantFiled: February 25, 1983Date of Patent: March 6, 1984Assignee: Maruko Seiyaku Co., Ltd.Inventors: Sachio Ohno, Kiyoshi Mizukoshi, Osamu Komatsu, Hajimu Yamamoto, Yasuo Kunou
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Patent number: 4424230Abstract: Disclosed are 6-(1'-hydroxyethyl)-3-substituted amino-1-azabicyclo?3.2.0!hept-2-en-7-one-2-carboxylic acids (I): ##STR1## wherein R' and R" are independently selected from H, substituted and unsubstituted alkyl and aralkyl groups, or together form a substituted or unsubstituted cyclic group. Such compounds and their O- and carboxyl derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.Type: GrantFiled: July 11, 1980Date of Patent: January 3, 1984Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Ronald W. Ratcliffe
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Patent number: 4408047Abstract: Novel imidazopyridines, -pyrazines, -pyrimidines and -pyridazines having a 3-amino-2-OR-propoxy substituent, are disclosed. The compounds have .beta.-adrenergic blocking activity.Type: GrantFiled: November 19, 1981Date of Patent: October 4, 1983Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, William C. Lumma, Jr.
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Patent number: 4374984Abstract: Compounds of the formula ##STR1## wherein the substituents A, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, n and m are defined hereinbeloware effective photoinitiators, especially for the photopolymerization of ethylenically unsaturated compounds and for the curing of printing inks.Type: GrantFiled: March 4, 1981Date of Patent: February 22, 1983Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Jurgen Eichler, Claus Herz, Karl-Heinz Neisius, Gregor Wehner
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Patent number: 4373102Abstract: Novel dyes of the formula ##STR1## where A is cyano, carbo-C.sub.1 -C.sub.4 -alkoxy, carbamyl, N-C.sub.1 -C.sub.4 -alkylcarbamyl, N-phenylcarbamyl, acetyl, benzoyl, 4-nitrophenyl or 4-cyanophenyl,X is hydrogen, chlorine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, and if n is 2 the substituents may be identical or different,n is 1 or 2,R.sup.1 is hydrogen, methyl, ethyl or 2-hydroxyethyl andR.sup.2 is phenyl or cyclohexyl, orR.sup.1 is hydrogen andR.sup.2 is C.sub.1 -C.sub.4 -alkyl, orR.sup.1 and R.sup.2 are C.sub.1 -C.sub.6 -alkyl, allyl or phenyl-C.sub.1 -C.sub.4 -alkyl orthe group ##STR2## is a saturated heterocyclic five-membered or six-membered ring which may additionally contain an oxygen or a further nitrogen as ring members,Y is hydrogen, hydroxyl, methyl or ethyl; ##STR3## where R.sup.3 is linear or branched C.sub.1 -C.sub.12 -alkyl, or is phenyl; ##STR4## where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.5 is hydrogen, linear or branched C.sub.1 -C.sub.Type: GrantFiled: March 7, 1980Date of Patent: February 8, 1983Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Wolfgang Elser, Gustav Bock, Wolf-Dieter Kermer
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Patent number: 4369326Abstract: Carbazolylmethane compounds of the formula ##STR1## wherein one of Y.sub.1, Y.sub.2 and Q represents a 3-carbazolyl radical of the formula ##STR2## and each of the other two independently represents an amino-substituted phenyl radical of the formula ##STR3## a 3-indolyl radical of the formula ##STR4## These compounds are particularly suitable for use as color formers in pressure-sensitive or heat-sensitive recording material.Type: GrantFiled: October 2, 1980Date of Patent: January 18, 1983Assignee: Ciba-Geigy CorporationInventors: Jean C. Petitpierre, Peter Burri
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Patent number: 4344946Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.1 ', which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 2 carbon atoms;R.sub.2 and R.sub.2 ', which may be identical to or different from each other, are each hydrogen or ##STR2## but other than both hydrogen at the same time, where A is alkylene of 1 to 2 carbon atoms,R.sub.5 is hydrogen, lower alkyl, lower alkylamino-lower alkyl, lower alkoxy-lower alkyl, hydroxycarbonyl-lower alkyl, cycloalkyl of 5 to 8 carbon atoms, lower alkyl-cycloalkyl of 5 to 8 carbon atoms, phenyl or morpholino;R.sub.6 is hydrogen, lower alkyl, lower alkylamino-lower alkyl or lower alkoxy-lower alkyl; orR.sub.5 and R.sub.Type: GrantFiled: August 28, 1980Date of Patent: August 17, 1982Assignee: Boehringer Ingelheim GmbHInventors: Ernest Cullen, Genus Possanza, Patrick B. Stewart
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Patent number: 4316036Abstract: A benzopyranothiazole of the formula ##STR1## wherein each of R.sub.1 and R.sub.2 independently represents hydrogen, alkyl of not more than 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or represents cycloalkyl, phenyl, benzyl, or phenyl or benzyl which is substituted by halogen, lower alkyl or lower alkoxy, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical or a N-carbazolyl radical, Q represents hydrogen, lower alkyl, benzyl or groups of the formulae (1a) or (1b) ##STR2## each of X, X.sub.1 and X.sub.2 represents hydrogen, halogen, lower alkyl or lower alkoxy, each of Y.sub.1, Y.sub.2, Y'.sub.1 and Y'.sub.Type: GrantFiled: September 11, 1978Date of Patent: February 16, 1982Assignee: Ciba-Geigy CorporationInventor: Jean C. Petitpierre
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Patent number: 4314061Abstract: This disclosure describes compositions of matter useful for inducing the regression of tumors in warm-blooded animals and for enhancing the immune system, and the method of treatment of tumors and enhancing the immune response in mammals therewith, the active ingredients of said compositions of matter being certain 3,6-bis(aminoalkoxy)acridines or the pharmacologically acceptable acid-addition salts thereof.Type: GrantFiled: September 2, 1980Date of Patent: February 2, 1982Inventors: Keith C. Murdock, Martin R. Damiani, Frederick E. Durr
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Patent number: 4301281Abstract: 7,8-Dihydro-2,5,8-trisubstituted-7-oxo-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide derivatives are gastric anti-secretory agents for treatment of peptic ulcer disease and generally anti-allergic agents useful in the treatment of atopic immediate hypersensitivity reactions.Type: GrantFiled: February 28, 1980Date of Patent: November 17, 1981Assignee: American Home Products CorporationInventors: Anthony C. Scotese, Robert L. Morris, Arthur A. Santilli
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Patent number: 4296114Abstract: There are described compounds of formula I, ##STR1## in which R.sub.1 is phenyl substituted by halogen, alkoxy, alkyl, carboxy-alkyl, --NR.sub.4 R.sub.5, carboxy or alkoxy carbonyl,R.sub.3 is hydrogen, alkyl, mono- or di-carboxy alkyl, halo, alkoxy, phenyl, halo-phenyl, hydroxy, phenoxy, thiol, thioalkoxy, thiophenoxy, --NR.sub.4 R.sub.5, cyano, --COOH, carboxyureido, --CF.sub.3, --COR.sub.6, hydroxyalkyl, aminoalkyl, or alkoxy substituted by NR.sub.4 R.sub.5,ring A is a benzene or a pyridine ring which optionally carries up to 4 substituents R.sub.3, which may be the same or different,R.sub.4 and R.sub.5, which may be the same or different, each represent hydrogen, phenyl, halophenyl or alkyl, the alkyl optionally being substituted by alkoxy or by a mono- or di-alkyl or unsubstituted amino group; or R.sub.4 and R.sub.5, together with the nitrogen atom to which they are attached, form a piperidine, morpholine or an optionally alkyl substituted piperazine ring, andR.sub.Type: GrantFiled: August 2, 1979Date of Patent: October 20, 1981Assignee: Fisons LimitedInventors: Richard A. Appleton, David Johnston
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Patent number: 4252803Abstract: Compounds are disclosed of general formula (I): ##STR1## wherein R.sub.1 and R.sub.2 each independently represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl, fluoroalkyl or alkyl group, which alkyl group is optionally substituted by an alkenyl group or by a group -OR.sub.7 or by ##STR2## where R.sub.7 and R.sub.8 each independently represents a hydrogen atom, an alkyl, aryl or aralkyl group; or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz--O--, --NH or ##STR3## R.sub.3 and R.sub.4 have the same meanings as R.sub.1 and R.sub.2 and may together form an aralkylidene group;R.sub.5 represents a hydrogen atom or an alkyl or aralkyl group;R.sub.6 represents a hydrogen atom or an aryl or C.sub.1 -C.sub.3 alkyl group;Alk represents an C.sub.1 -C.sub.4 alkylene group optionally substituted at one or more of its carbon atoms by one to three C.sub.1 -C.sub.Type: GrantFiled: October 10, 1979Date of Patent: February 24, 1981Assignee: Glaxo Group LimitedInventor: Colin F. Webb
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Patent number: 4244954Abstract: 9-Phenyl(or benzyl)acridines, 9-phenyl(or benzyl)-9-acridinols and acridinium compounds, useful as trypanosomacidal and antibacterial agents, are prepared from aminoalkoxy substituted 9-acridinones via reaction with the appropriate Grignard reagents or aryllithium. The intermediate aminoalkoxy substituted 9-acridinones, prepared from the corresponding halo or hydroxy substituted 9-acridinones, are useful as antiviral agents.Type: GrantFiled: October 2, 1978Date of Patent: January 13, 1981Assignee: Sterling Drug Inc.Inventor: John W. Schulenberg
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Patent number: 4215216Abstract: 7,8-Dihydro-2,5,8-trisubstituted-7-oxo-pyrido[2,3-d]pyrimidine-6-carboxylic acid derivatives are gastric anti-secretory agents for treatment of peptic ulcer disease and generally anti-allergic agents useful in the treatment of atopic immediate hypersensitivity reactions.Type: GrantFiled: April 18, 1979Date of Patent: July 29, 1980Assignee: American Home Products CorporationInventors: Anthony C. Scotese, Robert L. Morris, Arthur A. Santilli
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Patent number: 4208518Abstract: Compounds which have the general formula ##STR1## and those which can be obtained from them with a Vilsmeier type reagent and have the formula ##STR2## as well as salts thereof, are useful as anti-inflammatory agents.Type: GrantFiled: December 27, 1978Date of Patent: June 17, 1980Assignee: E. R. Squibb & Sons, Inc.Inventors: Peter C. Wade, Thomas P. Kissick
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Patent number: 4207320Abstract: Amino-substituted imidazo[1,2-a:3,4-a']diquinolin-15-ium salts having the formula I: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, C.sub.4 -C.sub.6 cycloalkyl, di(lower alkyl)amino, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, methyl-1-pyrrolidinyl, methyl-1-piperidinyl, 4-morpholinyl or 2,2-dimethylhydrazino;R.sub.2 is hydrogen, lower alkyl, lower alkylamino, di(lower alkyl)amino, C.sub.4 -C.sub.6 cycloalkylamino, lower alkoxy(lower alkyl)amino, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, methyl-1-pyrrolidinyl, methyl-1-piperidinyl, hexahydro-1H-azepin-1-yl, 4-morpholinyl, benzylamino, N-methylbenzylamino or 2-phenylethylamino;R.sub.3 is hydrogen or methyl;X is an anion;with the proviso that at least one of R.sub.1 and R.sub.2 is other than hydrogen, lower alkyl or C.sub.4 -C.sub.6 cycloalkyl; and with the further proviso that when R.sub.2 is dimethylamino, at least one of R.sub.1 and R.sub.3 is other than hydrogen, and intermediates used in the preparation thereof are disclosed.Type: GrantFiled: August 28, 1978Date of Patent: June 10, 1980Assignee: Warner-Lambert CompanyInventors: David B. Capps, Mario M. Angelo, Townley P. Culbertson
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Patent number: 4191689Abstract: This invention relates to certain 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) and to the preparation thereof by reacting (a) at least 2 equivalents of (i) a 4'-OP-carbocyclic aryllithium compound wherein P is a protecting group compatible with organometallic reagents or (ii) a 4'-OP-carbocyclic arylMgE compound wherein P is a protecting group compatible with organometallic reagents and E is chloro, bromo or iodo and (b) 1 equivalent of a compound selected from a 3-chlorobenz[d] isothiazole-1,1-dioxide and a 3-chloronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide to give the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide or the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide, which compounds are useful in the synthesis of phenol and 1-naphthol sulfam(na)-phthaleins employed, for example, as photographic optical filter agents and filter agentType: GrantFiled: September 23, 1977Date of Patent: March 4, 1980Assignee: Polaroid CorporationInventors: Stanley M. Bloom, Alan L. Borror, James W. Foley
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Patent number: 4169897Abstract: Novel bis-basic ethers of 9-substituted phenanthrene and related 10-oxa and 10-aza derivatives, their method of preparation and their use as pharmaceutical agents for the prevention and inhibition of viral infections are disclosed.Type: GrantFiled: November 11, 1976Date of Patent: October 2, 1979Assignee: Richardson-Merrell Inc.Inventors: Donald R. Meyer, Arthur D. Sill, Paul L. Tiernan
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Patent number: 4154829Abstract: Racemic and optically active compounds of the formulaQ--C.sub.n H.sub.2n --NH--Rwherein Q is ##STR1## where R.sub.1 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl or amino,R.sub.2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or trifluoromethyl,R.sub.1 and R.sub.2, together with each other, are methylenedioxy or ethylenedioxy, andA is --O--, --CH.sub.2 --CH.sub.2 --, --O--CH.sub.2 -- where the oxygen is bonded to the benzene ring, or --NR.sub.3 -- where R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms,N is an integer from 2 to 6, inclusive, andR is hydrogen, benzyl or ##STR2## where R.sub.4 is hydrogen, methyl or ethyl,R.sub.5, r.sub.6 and R.sub.7, which may be identical to or different from each other, are each hydrogen, halogen, hydroxymethyl, trifluoromethyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, nitro, cyano, --CONHR.sub.3, --CONHOH, --COOR.sub.3, R.sub.Type: GrantFiled: March 2, 1977Date of Patent: May 15, 1979Assignee: Boehringer Ingelheim GmbHInventors: Anton Mentrup, Kurt Schromm, Ernst-Otto Renth, Richard Reichl, Werner Traunecker, Wolfgang Hoefke
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Patent number: 4136033Abstract: Compounds of the formula ##STR1## wherein K.sup..sym. is a cationic group, preferably heterocyclic,R is hydrogen or an organic radical, preferably alkyl, phenyl or acyl,R.sub.1 is hydrogen, hydrocarbyl, substituted hydrocarbyl, heterocyclyl, substituted heterocyclyl, amino or substituted amino, andA.sup..crclbar. is an anion,Are useful as intermediates in the synthesis of azo dyes of the formula ##STR2## wherein D is an aromatic carbocyclic or heterocyclic diazo component radical, andK.sup..sym., r, r.sub.1 and A.sup..crclbar. are as defined above.Type: GrantFiled: June 25, 1974Date of Patent: January 23, 1979Assignee: Sandoz Ltd.Inventor: Willy Steinemann
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Patent number: 4132714Abstract: A new process for the manufacture of a chromenoindole compound of the general formula ##STR1## which process comprises reacting a carbinol compound of the general formula ##STR2## with a (2-(2'-hydroxyphenyl)-indole compound of the general formula ##STR3## and oxidizing the reaction product to a compound of the formula (1).Type: GrantFiled: May 20, 1977Date of Patent: January 2, 1979Assignee: Ciba-Geigy CorporationInventor: Jean C. Petitpierre
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Patent number: 4126620Abstract: 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as antisecretory and anti-ulcer agents are prepared by hydrolysis or thiohydrolysis of the corresponding 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitriles or, in the case of the thiocarboxamides, by reaction of the 4-carboxamide with phosphorus pentasulfide.Type: GrantFiled: February 25, 1977Date of Patent: November 21, 1978Assignee: Sterling Drug Inc.Inventors: Malcolm R. Bell, Rudolf Oesterlin
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Patent number: 4082773Abstract: Compounds are provided of the structure ##STR1## WHEREIN X--Z--Y together with two carbons of the cycloalkyl ring form a 5- or 6-membered ring, wherein R.sup.1 is hydrogen, aralkyl or acyl, n is 0, 1 or 2, and n' is 0, 1, 2 or 3, R.sup.2 is hydrogen, lower alkyl or aralkyl, R.sup.3 is hydrogen, acyl, lower alkyl, aralkyl, lower alkoxy, carboxy, halo, alkenyl, nitro, cycloalkyl, amino, acylamino, R.sup.2 O(CH.sub.2).sub.n 2 where n.sup.2 is 0, 1 or 2 or dihydroxyalkyl, X and Y may be the same or different and can be --CH.sub.2 --, .dbd.N--, --O--, --S--, --NR.sup.4 --, --O--CH.sub.2 --, --S--CH.sub.2 --, or --NR.sup.4 --CH.sub.2 -- where R.sup.4 is hydrogen, lower alkyl or aryl, Z can be ##STR2## where R.sup.5 and R.sup.6 can be hydrogen, lower alkyl, cycloalkyl, aryl, haloalkyl, amino or substituted or unsubstituted aminoalkyl; ##STR3## and --X--Z--Y-- can be taken together to form ##STR4## and ##STR5## These compounds are useful as anti-fibrillatory agents, disinfectants and water-softeners.Type: GrantFiled: July 3, 1972Date of Patent: April 4, 1978Assignee: E. R. Squibb & Sons, Inc.Inventor: Frederic Peter Hauck
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Patent number: 4072679Abstract: New derivatives, and their salts, of 1,4- and 4,10-dihydro-4-oxo-pyrimido[1,2-a]benzimidazole-3-carboxylic acids, esters and carboxamides have the general formulas ##STR1## They are useful as central nervous system depressants and anti-inflammatory agents.Type: GrantFiled: June 15, 1976Date of Patent: February 7, 1978Assignee: E. R. Squibb & Sons, Inc.Inventors: Theodor Denzel, Hans Hoehn
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Patent number: 4071525Abstract: This invention is directed toward pharmacologically active compounds of the formula ##STR1## wherein A represents a nitrogen atom which may be substituted by a methyl, cyclopropylmethyl, di(C.sub.1-4 alkyl) aminoethyl, methoxymethyl or hydroxyethyl group and B represents a carbonyl group or A and B together represent a grouping of the formula ##STR2## in which R.sup.a represents a hydrogen atom or a lower alkyl or hydroxymethyl group and X represents a nitrogen atom or C--R.sup.b wherein R.sup.b represents a hydrogen atom or a lower alkyl or hydroxymethyl group; R represents a halogen atom or a nitro or trifluoromethyl group; R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents an acyl group derived from a naturally occurring amino acid (all such groups which contain an asymmetric carbon atom having the L- or D,L-configuration) and R.sup.3 represents a phenyl, halophenyl or 2-pyridyl groupAnd acid addition salts thereof.Type: GrantFiled: November 11, 1976Date of Patent: January 31, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Cedric Herbert Hassall, William Henry Johnson, Antonin Krohn, Carey Ernest Smithen, William Anthony Thomas
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Patent number: 4056537Abstract: Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[3,4-b]indole or thiopyrano[3,4-b]indole nucleus are disclosed. The amino portion of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives having the amino(lower)alkyl radical only at position 9 possess two substituents at position 1 and may be optionally substituted at position 3, 4, 5, 6, 7, and 8. The derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7 and 8.Type: GrantFiled: October 18, 1976Date of Patent: November 1, 1977Assignee: Ayerst McKenna and Harrison Ltd.Inventors: Christopher A. Demerson, Leslie G. Humber, Andre A. Asselin, Ivo Jirkovsky, Thomas A. Dobson
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Patent number: 4056538Abstract: Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[ 3,4-b]indole or thiopyrano[3,4-b]indole nucleus are disclosed. The amino position of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives having the amino(lower)alkyl radical only at position 9 posses two substituents at position 1 and may be optionally substituted at position 3, 4, 5, 6, 7, and 8. The derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7 and 8.Type: GrantFiled: October 18, 1976Date of Patent: November 1, 1977Assignee: Ayerst, McKenna & Harrison LimitedInventors: Christopher A. Demerson, Leslie G. Humber, Andre A. Asselin, Ivo Jirkovsky, Thomas A. Dobson
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Patent number: 4048312Abstract: 2,4-Diaminoquinazolines are employed as antithrombotic agents and have the following general formula: ##STR1## wherein R.sub.1 and R.sub.2 are monovalent groups independently selected from the group consisting ofA. ##STR2## wherein R.sub.4 and R.sub.5 independently are selected from the group consisting of hydrogen, alkyl, and cycloalkyl, with the proviso that both R.sub.4 and R.sub.5 cannot be cycloalkyl,B. ##STR3## wherein R.sub.6, R.sub.7, and R.sub.8 independently are selected from the group consisting of hydrogen and alkyl, and A is a divalent organic group having from two to about six carbon atoms such that the two nitrogen atoms are separated by at least two carbon atoms, andC. heterocyclic-amino, andR.sub.3 is a monovalent group selected from the group consisting of hydrogen, halogen, and alkyl.Type: GrantFiled: December 4, 1975Date of Patent: September 13, 1977Assignee: Eli Lilly and CompanyInventor: William B. Lacefield
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Patent number: 4039540Abstract: Compounds of the formula ##STR1## wherein X is a 6- or 7-position substituent selected from the group consisting of hydrogen, halogen, lower alkoxy, trifluoromethyl, methyl, lower alkyl sulfide, lower alkyl sulfoxide and lower alkyl sulfone; Y is S, SO or SO.sub.2 ; R.sub.1 is carbamyl(lower alkyl), carbo(lower alkoxy)lower alkyl or monosubstituted alkyl having from 2 to 4 carbon atoms in the alkyl group wherein the substituent is selected from the group consisting of hydroxy, lower alkoxy, amino, mono(lower alkyl)amino, di(lower alkyl)amino, mono(lower alkyl)carbamyl, di(lower alkyl)carbamyl, halogen, mercapto, sulfo, lower alkyl sulfide, lower alkyl sulfoxide, lower alkyl sulfone, acetoxy, pyrrolidino, piperidino, morpholino, thiomorpholino, piperazino, N-(lower alkyl)piperazino, N-hydroxy(lower alkyl)piperazino, N-(lower alkanoyl)piperazino and N-carbo(lower alkoxy)piperazino; R.sub.2, when taken separately, is hydrogen or lower akyl; R.sub.Type: GrantFiled: November 17, 1975Date of Patent: August 2, 1977Assignee: Pfizer Inc.Inventor: John P. Dirlam
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Patent number: RE32761Abstract: 3-Arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles, useful as analgesic, anti-rheumatic and anti-inflammatory agents, are prepared by reacting a 3-arylcarbonyl- or 3-cycloalkylcarbonylindole with an aminoalkyl halide in the presence of an acid-acceptor; by reacting a 1-aminoalkyl-1H-indole with an arylcarboxylic acid halide or a cycloalkanecarboxylic acid halide in the presence of a Lewis acid; or by reacting a 3-arylcarbonyl- or 3-cycloalkanecarbonyl-1-tosyloxyalky- or haloalkyl-1H-indole with an amine.Type: GrantFiled: March 23, 1987Date of Patent: October 4, 1988Assignee: Sterling Drug Inc.Inventor: Malcolm R. Bell